I'd just called in to Dispatch to let them know that I was starting my shift one morning when they came back and told me that one of the local high-end hotels had called and asked if I'd be available for a 'flat rate' fare. A fare like that is one where the cab (and driver, of course) were hired for a period of time to work 'off the meter' – payment was to be a fixed amount for whatever was to be done for however long it took. Usually, a flat-rate gig is something of a crapshoot: it could be anything from just driving partiers around so none of them risks a DUI, to helping some disabled or elderly person go out and do their weekly shopping at a number of different stores. The trick was to know (or have some idea, anyway) of the who, what, and how long, and balance that against the pay. Driving a couple of partiers around for 3 or 4 hours for a hundred bucks was better than getting a granny-lady that wanted to you to spend all day taking her all over town to shop and expecting you to do all of her hauling and carrying for fifty. Too, the partiers were a lot more likely to come up with a nice tip than the granny; that's just the way things work. But the place that had asked for me was the best hotel in town, so the risk of getting a crap deal was a lot lower – almost nonexistent, even.
So I told Dispatch I'd take it, and headed that way. When I got there, the manager of the place was waiting for me at the front desk. We weren't buddy-buddy, but we had developed a liking and respect for each other. As I got close, he gestured that I should follow him a little ways away from the desk, which I did. Once we had a little quiet and privacy, he told me what the deal was.
"Jim, we've got a guest from out of town that wants to go out and do some shopping. The problem is that the car we had reserved for her from the limo service got into an accident last night, and there simply isn't anything else available – from anybody. Now, we've explained the problem to the guest, and she understands and doesn't have any problem with taking a cab. But the limo company and us, we don't want her to have to be sitting around waiting for her next ride to show up, either; she's a very special guest for us and the limo company. So what we came up with was to set her up with one cabbie, and your name was at the top of the list. I know you do good work anyway, but I want to make sure you understand that this lady is extra special."
Curious, I had to ask "What makes her so special?"
"Money. Lots and lots of it. She comes in here several times a year, stays in our best suite for a week or so, does some shopping, and then she's gone again for a while. She's a damn good tipper, if that helps any."
The subject of tips gave me the excuse to ask what the fare would be; the answer I got back would mean that I made half again what I'd normally make in a day. That, more than anything, convinced me that the manager of the hotel and the limo company were serious about wanting to keep her happy.
"Okay, she's somebody you want to keep, I understand that. But what do I do to earn this? Besides drive her around, I mean."
"Not a hell of a lot, Jim. The places she's likely to want to go shopping, they all deliver, so there won't be any carrying stuff. She might want you to keep her company in some of the places, and even ask what you think about a few things, but mostly it'll just be driving her around and making sure she stays happy with all of us."
I at least knew of the higher-end stores in town, the ones that would deliver. From what I understood, nearly all of them were clothing places that tailored purchases to a customers measurements – thus their willingness to deliver the finished item. If this woman was shopping in those stores, I could be fairly confident of getting a better than usual tip if I did my job right.
I agreed to the deal, and the manager looked pleased before he gave me the details by saying "The woman's name is Kathryn McGreevy. She's forty-ish, and her husband was some high-dollar financial type before he got killed in an airplane accident – in his private plane. She's got more money that God, but she isn't snooty or demanding or anything like that; she's pretty nice, actually. But for God's sake, Jim, don't let that make you start thinking she'll put up with anything, either. She's a good tipper for good service, but she isn't bashful about letting folks know when she isn't happy, either! There's a store in town that she won't go to any more because one of the clerks told her when she could pick up something she'd bought, instead of asking where she wanted it delivered to."
I nodded that I understood what he was telling me, and satisfied that I wasn't going to let him down, he went on to tell me "I know you're damn good, Jim, I just wanted to make sure you understood how important it is that this lady stays happy."
"Yeah, I can understand that, and I'll make sure I don't do anything to screw this up for any of us!", I assured him.
With that out of the way, he let me know that she'd be down in a few more minutes, and the two of us went back to the front desk to wait for her.
The elevators had cycled a few times when one of them opened up and a nice-looking redhead came out; the manager gave me a little nudge to let me know that she was to be my fare for the day.
When she got close enough, I could see that she was a lot nicer looking than I'd first thought, and outfitted real nice. Just a couple inches shorter than I am, she had curly hair that looked like it was made out of fine copper that someone had polished for hours on end; her face was attractive, with emerald green eyes that sparkled nicely, a small, straight nose, and full (but not overly so) lips. Her skin was pale, but not the white-with-freckles that a lot of redheads seem to have. Her bust was a trifle larger than average, and the dress she was wearing revealed an interesting amount of cleavage. Her waist was trim, and turned into a set of hips that was definitely womanly without being too wide. Her dress ended a little above her knees, and the legs that I could see were trim and muscular. There wasn't any one thing that really stood out as making her attractive; rather, it was the way that all of her fit together that made her appealing.
Though I'm not one to keep up with fashion or anything, I didn't have any hesitation deciding that the dress she was wearing easily cost as much as I took home in a month – the material and cut and attention to detail were that obvious. Seeing her, I was glad that I'd gotten into the habit of dressing better than almost all of the other cabbies in town. Not that I actually put on a suit or anything, just that the slacks and collared shirt I was wearing were nice enough that I didn't feel like some war orphan standing in front of her.
When she got close enough for the manager to introduce us, I got a whiff of the perfume that she was wearing and decided that I wouldn't mind having her in the cab with me at all: it was a soft and delicate scent that put me in mind of a field of wildflowers.
When the manager had told her who I was and that I'd be driving her that day, she gave me a pleasant smile before saying "It's a pleasure to meet you, James, and thank you for being willing to answer our call for help, and getting here so quickly."
"It's my pleasure, Ma'am", I assured her, with a smile of my own.
"Shall we get started, then?" she asked, and I hastened to let her know that I was hers to command – something that earned me a pleased smile.
It didn't take long for us to get out to my hack, where I readily opened the door for her and helped her in. Once I was behind the wheel, I told her "I'm yours for the day, Ma'am, so please don't hesitate to let me know if you want something – the windows up or down, more or less air conditioning, or whatever."
"It seems like a nice enough day, so the windows down a little would be fine."
Figuring that she wanted fresh air without having her hair blown all over hell and back, I got a couple of windows to half-open before saying "I'll adjust them so your hair doesn't get mussed once we get going, if that's okay."
"That's fine, James", she told me, then following that by giving me the first place she wanted to visit.
I got us headed that direction, and as we were moving, tweaked the windows until I could see her hair moving a little bit, but no more. The ride was quiet, and I was even more careful than usual about my driving. Normally, my goal is pretty simple: to take as little action as possible – that is, to speed up or slow down gradually, to avoid having to brake or swerve, or do anything other than maintain a nice, steady ride. To do that, I do pretty much all the things that they try to teach in Drivers Ed: plenty of room between me and the vehicle in front so I have more time to respond; staying alert to what people are doing around me – not just in front, but to the sides and even back; looking at not just the couple of cars in front of me, but watching what's going on for the next couple of blocks, in all the lanes; and using my turn signals not just for turns, but lane changes, too. I usually don't get to my destination as fast, but I definitely get there with a lot less hassle and aggravation.
Anyway, when we get to the place, I hustle out to get the door open and help her out. She hesitates a moment, then tells me "There's no need for you to come inside unless you really want to. I don't think they have anything I'd be interested in, but I still have to at least look; I doubt that I'll be in there more than half an hour, or so."
"As you said, it's a nice day, so if it's okay with you, I'll stay out here and enjoy it. I'll be watching for you when you're ready to leave, though."
She nodded, and made her way to the door to the place; once she was inside, I found a spot where I could keep an eye out for her.
Just as she'd predicted, it wasn't much more than half an hour when I saw her just inside the door, talking with someone. I quickly got my rig there, and was waiting for her when she came outside. Once she was in the back, and I was behind the wheel, I asked her where she'd like to go next. She gave me the name of a place, and I headed us that direction. When we got there, I helped her out just as I had at the first place, then waited to see whether she needed or wanted me to go inside with her. She seemed to consider it for a few moments before telling me "I think I'll be in here for a while, so you're welcome to come inside with me if you like."
With my assurance of "I'd be glad to, Ma'am", she led us inside- I got the door, of course – after I got the keys and locked my cab.
I'd never been in the place before, and was more than a little surprised at the service they gave us: leading us to a private viewing area, giving us coffee, and generally fawning over us. Well, her more than me, of course, but they didn't fail to be polite to me, too. After getting the cup of coffee they offered me, though, I kind of wished I'd stayed in my rig – the cup was some tiny little thing that had me sticking my pinkie out because there wasn't anyplace else for it. On top of that, the coffee wasn't all that good; the stuff I had in my thermos was a lot better.
But I kept my mouth shut except for saying "please" and "thank you", and stayed as much in the background as I could. The stuff they showed her all looked pretty good – at least on the models that were wearing it; I didn't figure it would look as nice on her, since she didn't resemble any of the wispy fashion models that had the stuff on. Nobody asked my opinion, though, and I damn sure didn't volunteer it.
There were a couple of things that she decided she liked, and made arrangements for them to be altered to fit her. When I heard what they cost, I damn near dropped my dinky little coffee cup; the two outfits she liked cost more than I had ever made in an entire month.
I could tell when things were getting close to being done, and quietly excused myself so I could get outside and be ready to take her to the next place. I hadn't been standing there but a couple of minutes when she came outside and saw me. I could tell that she was pleased that I'd gotten ready ahead of her, and quickly got her settled into the back again as she told me our next destination. I got us there easily enough, and she again suggested that I might want to come inside, since she didn't know how long she'd be there.
That place seemed to specialize in lingerie and filmy underthings, and the show I got made up for the tepid mediocre coffee they served us. Again, I was staying in the background, content to watch the models showing us the wares (the stores AND the models!) when Katherine turned around to ask me "What do you think, James?"
I visualized Katherine in the little bustier thing the model was showing us, and after a couple of seconds, answered "I think it looks real good on her."
Apparently satisfied, Katherine started to turn to the front again, then quickly reversed course to look at me again before saying "You said you thought it looked good on her. How do you think it would look on me, though?"
Trying not to mess things up, I tried to give her some kind of response without actually having to tell her what I really thought: that it simply wouldn't do a thing for her. Katherine wasn't having any of that, thank you, and finally told me "James, I want to know what YOUR honest opinion is."
Reluctantly, and apologetically, I answered "I don't think you would look anywhere near as good in it as she does."
Hearing that, Katherine immediately wanted to know "Why not?"
"A couple of reasons. First, that color goes a lot better with her dark hair and complexion than it would with your red hair and lighter skin tones."
She considered that for a moment, then said "And?"
"And what?"
"You said there were a couple of reasons, and you've only given me one so far."
Damn. Busted again. All I could do was reply "You've got a different figure than she does, so it would look different on you."
"How so?"
"You're, uh, shaped more like most women; she's thinner, like most of the fashion models I've seen on TV. As a guy, I just don't think that the way it looks would be the same on a different figure than hers, is all."
She must have realized that I was a bit uncomfortable about admitting that I'd visualized her in the damn thing, because she gave me a strange smile before telling me "Thank you, James. I wanted an honest opinion, and you gave it to me. Have you seen anything yet that you thought I would look good in?"
"Uh, that camisole thing a couple outfits ago, if it was in a light gray or green."
Katherine turned to the salesperson, and asked if the one I was talking about came in either of those colors. The salesperson had to go check, and while she was gone, Katherine turned to tell me "I'm not upset with you, James, for giving me your honest opinion. I asked you what you thought, and it wouldn't be right for me to be upset with you for giving it. I thought that bustier might be acceptable, but I wasn't quite sure. What you told me made me realize that it wouldn't, and saved me the bother of finding out after I bought it. In addition to what you're making driving me around, I'll be adding ten percent of what it cost, for saving me the other ninety percent."
That damn bustier would have cost her a cool grand, so she'd just told me that I'd be getting a hundred dollar tip!
Keeping my composure, I told her "Thank you, Ma'am, I appreciate that."
She gave me another strange smile before saying "If I'm going have you imagining me in something like that, or even that camisole, I think that I can let you call me Katherine."
"Thank you… Katherine."
That was when the sales clerk came back in to let Katherine know that the camisole was available in a pale green; Katherine said she'd like to see it, on a blond, if a redhead wasn't available. It wasn't but a couple of minutes before we were seeing it on one of their less emaciated models wearing a wig that wasn't too far off from Katherine's own tresses. Seeing it that way, it didn't take me long to figure that it would look real good on Katherine. She apparently reached the same decision, and said she'd take it.
A couple more times, Katherine asked me what I thought of something they were showing her, and I politely told her what I thought of it. She ended up buying several different things, and when she was done the arrangements for getting things altered and delivered were quickly settled.
By the time we got out of the place, it was getting close to lunch time and I was starting to wonder how the heck we were going to manage that. Much to my surprise, Katherine brought the matter up by asking if I would accompany her to one of the nicer restaurants in town – her treat, of course. I'd been there exactly once, a long time before, and hesitantly agreed. Realizing what the problem likely was, Katherine told me "It'll be fine, James. Such places always have a spare jacket and tie for customers that might not have anticipated eating there. You'll see."
When we got there, I learned that she'd been absolutely correct – it wasn't but a minute or so before they'd outfitted me with a nice jacket of the correct size. It being lunch time, it was judged that my open-collar shirt was good enough that a tie wasn't necessary.
Once we were seated, I wasn't the least bit bashful about telling her "I'm sorry, Katherine, but I don't get to eat in places like this very much, so I really don't have much of an idea of what to order this time of day."
Surprising me somewhat, she gave me a look of appraisal before saying "I don't think that was easy for you to admit, was it?"
"No, not really."
"But you said it anyway. Why?"
"Because I'm not going to pretend to be someone I'm not, or that I know things I don't. You know I drive a cab for a living; so there's no point to acting like this is anything but what it is: a new and novel experience for me. You wanted my honest opinion before, and I'm going to be just as honest with you now."
She considered that for a few moments, then smiled before saying "Thank you, again, James. It's very seldom that I get to meet people that aren't trying to put up at least some kind of a front for others to see. I've been watching you, and I don't doubt that your manners and all are anything less than entirely suitable; the only concern I had about bringing you here was addressed when you admitted to not knowing what to order. If you've got the courage to admit what you did, then I won't say or do anything to embarrass you in front of others. I'll order first, and if you'll order the same, everything will be fine."
She started to say something else, but let it go because the waiter turned up with water and menus for us. When he'd gone again, Katherine asked if there was anything I didn't particularly care for, or was allergic to. Once I'd assured her that there wasn't, both of us looked over the menu. I was able to work out what was offered from the French on the menu, though the prices shocked me. When our waiter came back, Katherine was ready to tell him what she wanted; I pretended to give the menu another look before telling him that what she'd ordered sounded good to me, too. When he'd gone, she smiled and said "That was very nicely done, James. I'm glad you understand the distinction between putting on a front, and simply making the effort to fit in."
While we were waiting for our meal, Katherine and I made a little small talk – which included me having to tell her that I'd dropped out of college to become a cab driver. I got a brief reprieve from having to explain myself by the arrival of our lunch; but as soon as the waiter had left us again, I had to give her the whole story while we ate. In return, I learned that she spent a lot of time just looking for things to do. Which explained, she said, why she was spending an entire day doing nothing but shopping.
Both of us passed on dessert, but we did have a cup of coffee. While we drank it, Katherine didn't have much to say to me – though she did look at me a few times.
When she'd paid the bill, the two of us went back to where I'd parked and I got her settled into the back seat again before getting behind the wheel. I asked her where she wanted to go next, and the place she named was clear across town. As I was getting us there, she asked me a few things about myself, and I didn't have any problem with answering her.
Once we got to the place, she had me park my rig and keep her company inside the place. As they were showing her stuff, every so often she'd ask me what I thought of something or other; I'd tell her, and she seemed to actually think about what I had to say before deciding on whether or not to buy. We weren't in the place for long, though, and after we got started toward the next place she told me "James, if you think that I'm missing out on something, I want you to let me know. You seem to have a good eye for what would look good on me, and I don't want to pass on something I shouldn't."
I told her that I would, and that seemed to satisfy her, since she remained quiet until we were inside the next store.
It was another place that seemed to specialize in what I learned was called "intimate apparel" – negligees, nightgowns, and undergarments. At one point, Katherine passed on a bra and panty set, and I quietly told her "Katherine, you might want to look at those again." She turned to look at me questioningly, and I simply nodded my head that I was sure. She had them bring the model back in, and checked the items out again. After a bit, she asked if they had the things in her size, and they said they did; then she asked if it would be possible for her to try them on, as well as a few other things she'd seen. They assured her that was fine, and it didn't take long before one of the clerks brought the stuff in. Katherine asked where she could change, and they offered to show her to it. When she got up, I stayed where I was, figuring that I wasn't needed – but she surprised me by asking me to come with her. I figured she just wanted someone to stand outside the door or something to make sure she wasn't disturbed, and stood up to follow her and the clerk. We were led back to a small room that had one of those old-time privacy-screen things over in the corner. Katherine dismissed the clerk, and I started to back out of the room so she'd be alone, but she told me to stay, and close the door. I did as she said, though I wasn't real comfortable about it.
I felt a little better when Katherine went behind the screen, but I was still careful to face away from where she was. I heard an assortment of rustling noises, but didn't turn around; at least, not until I heard her tell me "No, don't do that, James. I wanted you in here so that you could look at me and let me know if this really looks as good as you seemed to think it would. So turn around, and tell me if you like it."
It took me a second to work up the nerve, but I did manage to get turned around so that I could see her – and about fell on the floor when I did.
She'd gotten out of her dress and other stuff, and was standing there wearing the bra and panty set, and not a damn thing else.
Since she'd said she wanted me to look, I did, and was glad for the chance. I saw that I'd been right about her bust being a little larger, and the bit of cleavage I'd first noticed proved to be just a sample of what the bra she was wore was displaying. The material and fit of the bra made it easy for me to tell that each of her breasts was generally shaped like half of a small melon, capped with a dark pink areola about the size of a silver dollar that sported a nipple that looked to be about the diameter of a large crayon. Each of her nipples stuck out far enough to make a distinct dent in the fabric of the bra, and unless my eyes were lying to me, looked to get a little longer and harder as I was looking at them. I couldn't help but notice that she also had a sparse dusting of pale freckles across her shoulders and upper chest.
Her belly was as flat as a woman's could be, and drew my eyes down to the small, sheer panties that matched the bra. Behind the material, I could easily tell that her pubic thatch was just a shade darker than what was on her head, and thick. It formed a small wedge that guided my eyes even lower, where I could see that the material dipped into her cleft a bit, forming something of a 'camel toe'. Bracketing her mound, her thighs were a perfect match for the bit of her legs that I'd already seen – smooth and trim, they seemed to make her legs go on forever. I was still trying to memorize the sight of her when she calmly turned around to show me how everything looked from the back, too – and I immediately fell in love with the size and shape of her ass.
I was trying to keep my cock from turning into a steel bar in my shorts when she turned to face me again. Hoping that she wouldn't notice the tenting of my pants, I managed to drag my eyes up to look her in the face as I told her "You", then clearing my throat so I could speak, "Um, you look good. I mean, real good."
Her smile and the amusement I could see in her eyes reassured me that she wasn't offended by the way I'd looked her over, and that she was pleased with the reaction and answer she'd gotten from me. She turned to look at herself in a full-length mirror on the wall, and I had the pleasure of seeing her in profile for a little while before she turned back to me to say "Yes, I think you were right – these DO look better on me than I thought they would."
Looking at me closely, she suddenly asked "You're not comfortable like this, are you?"
"Well, no."
"Why not?"
"Because even though I'm working for you, and you invited me in here and told me you wanted me to look at you, I'm still in a position where I'm not entirely able to stay completely… professional."
She looked a bit confused for a moment, then asked me "You're saying that seeing me like this makes you think of me more… personally, shall we say?"
"Yeah, that would be a good way to put it", I admitted.
She examined my face for several seconds before smiling and telling me "Again, thank you, James. I hadn't considered what affect it might have on YOU seeing me like this, but I'm not offended that you would think of me that way. If anything, I'm pleased and flattered to know that I still have that affect on men. I saw that you were looking at me more than I expected, but it simply didn't occur to me that you would be thinking of me in that way. Though now that I really think about it, that's just exactly what I wanted to happen when a man saw me in these. I apologize if my thoughtlessness has upset you, and I want you to know that I understand that you would think of me in a different way when I ask you how you think I'd look in something like these."
Then I saw as something else occurred to her, and she looked down to see that my pants were more than a little tight in one particular area. Without seeming to realize she was doing it, her hand moved to press her palm against my incipient erection. Surprised, she looked into my face and asked "I did this? I mean, letting you look at me this way made this happen?"
I couldn't help blushing slightly as I admitted "Uh, yeah, it did. Like I said, you look real good."
Closing her eyes, she released a soft moan – then surprised the Hell out of me by suddenly opening her eyes again, taking a step back, and quickly peeling the panties off. All I could do was look at the view she'd just given me: I could see that her bush was as thick as it had seemed, a luxurious patch of soft, short fur; the bottom of the vee showing a cleft where I knew her womanhood was. At the sight of her, my cock turned into a full-blown erection that not only tented the front of my pants, but felt like it would split them.
Her eyes locked onto the front of my pants, and she released another, deeper moan on seeing that I'd gotten even harder.
The two of us just stood there looking at each other that way for a full minute before she was able to move her gaze to my face, and tell me "My husband died in a plane crash several years ago. The insurance he had was outrageous, and added to the money we already had, it has made an ungodly sum. So much so that I've been afraid of having anything to do with the men that I've met – I've simply been too afraid that they were more interested in my money than in me. But now… today… knowing that you're excited because of what you see… that it's me, myself, that makes you hard… it brings out all the feelings and desires that I've had to hold in since I lost him… I had to take those off because I was getting SO excited that I was afraid that I'd stain them from how wet I could feel myself getting. And now, seeing you get even harder after I took them off… dear God, I need you!", before plastering herself against my front and starting to kiss me.
I could only stand there, stunned, for several seconds before Katherine took hold of my wrists and moved my hands around and put them on the firm globes of her ass.
That was all the prodding I needed, and it wasn't but a second before I was squeezing and massaging them as I kissed her back. I could hardly believe the desire and passion she was exhibiting, and as she started pressing her pelvis against my erection, I moved my hands from her ass in favor of caressing her back and sides – and when she pulled her upper body away from me a bit, her breasts and nipples.
It took a minute or so, but she finally decided that the bra she still had on was keeping her from really feeling my hands on her, and pulled away from me just long enough to rid herself of it before moving in again so that we could continue.
Her tits had felt pretty good through the lightweight material of the bra, but they felt even better without it. Between her age and the size of them, they did sag a bit – but only a trifle. Holding them in my hands, I could feel how warm and soft they were; and running my thumbs over the peaks of her breasts soon had her areolas crinkled in response, and her nipples standing tall and proud.
As I was becoming familiar with her body, she was getting to know mine: her hands were all over my chest and shoulders, and even down to my ass, as we shared a number of impassioned kisses. She'd been grinding her pelvis against mine, rubbing her mound against my erect cock through my pants, for a couple of minutes when she pulled away from me. The desire she was feeling was plain on her face as she told me "Now I really am worked up! If I don't get you inside me, and damn soon, I'll go crazy!"
Flabbergasted, I could only ask "Here? Now?"
"Yes, dammit, here, and now!", she declared, before turning around and dropping to her hands and knees. Looking over her shoulder at me, she exclaimed "All I need is for you to do me! God! It's been SO long, and I'm so ready!"
Below the globes of her ass, and between her smooth thighs, I could see the cleft of her womanhood – and that her labia were dark and extended, and the area between them all but dripping her essence. That view of her was all it took to demolish what little bit of resistance I had left. It wasn't but a few moments until I'd unfastened and dropped my pants, and pushed my shorts down. Kneeling behind her, I levered my erect cock down to press the end of it against her opening. Before I could do anything else, she rocked back, forcing the tight ring of her entrance over the head.
I didn't have any trouble believing that she'd been going without sex for as long as she'd said: she was definitely tight inside. But she was also amazingly wet and very hot. Putting my hands on her hips, I started to press myself into her as she moaned her pleasure at what I was doing. I had to back out a little a couple of times to keep myself coated with her abundant oils before I could get my manhood buried in her.
When she felt my lower belly pressing against her ass, she lowered her shoulders to the floor and muttered "Dear God, that feels so good!" before she told me "You don't have to do anything special, or try not to climax; the way I feel, just having you move in me is going to be just fine!"
Still, I didn't just start humping her. Figuring that she still might like a little time to get used to me, I took a little time to gradually work my way from simply being in her to sliding nearly the entire length of my erection in and out of her womanhood. I'd been moving in her for a couple of minutes when she had a small climax that had her clenching around me in a very interesting and stimulating way. She quickly recovered from that, and few minutes later, had another – stronger – climax that moved me a Hell of a lot closer to cumming. Still, I was able to enjoy plundering her woman's treasure for a couple more minutes; until her third, and strongest, climax had me pressing myself as far inside her as I could before trying to coat her tonsils with my cum.
When I'd finished emptying myself into her, I leaned forward and put my hands on the floor to help support myself as I got my breath back; by letting my head drop a little, I was able to give Katherine a number of soft kisses on her shoulders, and even the back of her neck as she was panting below me.
Despite how friendly she'd become, and how understanding she'd shown herself to be, I have to admit that I was still more than a little concerned about what had just happened between us. Sure, she'd invited me into the room, asked me to look at her in just the bra and panties, and been the one to grab my dick and tell me she wanted me inside her – but I still knew that 'right' didn't always match up with the way things really happened. It was well within the realm of possibility that even if she didn't kick up a fuss, she might still decide that she didn't want to have to look at the common cab driver that she'd given herself to, and either trade me out for some other cabbie or even call the whole thing off (with an option of canceling any bonuses, as well).
Needless to say, I had considerable interest in what she'd say (and more importantly, DO) when she got herself back together again.
I could feel myself shrinking inside her, and was wondering what the hell to do when I heard her tell me "You're going to slip out of me in a bit; when you do, I'd appreciate it if you could go behind the curtain in the corner, there. You'll find that they leave some small towels for the customers. If you'll bring one back for me quickly, we can avoid staining their carpet."
Figuring that I might as well do what I had to do and be done with it, I eased my hips back and stood up. After pausing just long enough to fasten my pants so I didn't fall on my face, I hustled to get her the requested towel. When I got back, I simply unfolded it and leaned over to drape it along the curve of her ass so that the end of it was in easy reach for her. She quickly reached back between her legs and pressed it against her opening before slowly raising herself up so that she was kneeling on the floor.
She didn't look at me right away, and I figured that she was embarrassed by what had just happened between us. She looked at the floor for a few moments before raising her head to look up at me and say "I don't know about you, but I'm extremely embarrassed by what just happened between us; and feeling more than a little awkward."
I looked at her as I answered "I'm not as embarrassed as I am feeling awkward. Different social level, I suppose."
She looked at me sharply before telling me "No, I don't feel that way because I'm rich and you're not, or because you're a cabbie. I'm embarrassed because I just let you have me on the floor of a shop, and because I just got too damn excited and couldn't control myself."
Hearing that, I knew that I might be able to set her mind at ease – and maybe save myself some grief, too.
Squatting down so that we were on the same level, I took her hand in mine and said "Katherine, it sounds to me like you're beating yourself up about it – and there's no reason for you to."
She snorted, and wryly said "What, I should think that you're just too damn studly for me to resist your charms?"
I patiently answered "No, I don't have enough ego to try and say anything like that. Would you give me the courtesy of listening to me for a moment?"
She nodded her head, if a bit reluctantly, and I told her "Katherine, I don't know if you remember, or not, but you said a few things before we got… distracted."
Snorting again, she muttered "Yeah, distracted!" before I continued "You said that your husband died several years ago, and that with all the money you have, you feel like you have to worry about whether a guy is interested in you or not. You also said that you've had to hold in all your feelings and desires, too, since then. Maybe I'm a little out of line, but it sure as hell seemed to me that you're a fairly passionate woman, and that you've got a healthy interest in physical pleasure. So considering how long it's been since your husband died, and how little intimacy it sounds like you've had, I don't think it's unreasonable to figure there was a lot of pent up emotion and everything in you."
Seeing that I had her attention, I continued "Something else you said was that knowing that I was getting excited by looking at you made those feelings even stronger. That sure sounds to me like seeing that I was getting excited by looking at you made you realize – consciously or not – that I could maybe be a… I don't know… safety valve of sorts for everything that you've been keeping pushed down. I mean, think about it: we're from two different towns, pretty much opposite ends of the economic spectrum, and basically just thrown together for just a single day. There isn't a chance in hell that I'd ever have the opportunity to try and wangle money out of you – even if I had the desire, which I don't. But I'm not really a complete stranger, either: you've gotten to know at least a little bit about me, after all. And because I'm a cab driver, and not some professional gigolo, you know that the reaction you got from me was true, and honest; I started to get hard not because you were paying me, but because of how you looked."
Taking a breath, I went on "That was even more obvious when you took the panties off, and then the bra – I mean, you did say that you needed me; and then later, that you'd go crazy if it didn't happen. Finally, there's the way you responded when it did happen; I already know that I'm not some great stud lover or anything, so those orgasms you had happened because you needed them – all I did was provide the necessary stimulation. I'm saying that I don't think that it was your 'fault', any more than it was mine. What I think maybe happened was just the unique match of you, and me, and here, and now. Just think about it: how many little things could have gone differently today that would have kept this from happening? That first time you asked me what I thought of something – what if I wasn't who I am, and had just said I thought it looked fine, instead of answering the way I did. Would you have gotten as interested in me as much as you did, and taken the time to learn about me, and get to know me? Would we have even been in this room together?"
I could see by the expression on her face and the look in her eyes that Katherine understood what I was saying, and was thinking about it. I simply shifted my position to rest on one knee while I waited to hear what she had to say in response.
A minute or so went by before she looked into my eyes and said "I… I think you're right. About it being just one of those freak occurrence kind of things, I mean. Except that I haven't experienced too many of those that have ended with semen leaking out of me!"
I couldn't help smiling as I replied "I don't doubt that's true. But then again, how many of them have there been where you've had orgasms?"
Giving me a surprisingly shy grin, she answered "Um… that would be the same number – just the one."
"There you go then; that just proves my point, don't you think?" I asked, grinning back at her.
"Be that as it may", she told me, "we still have something of a problem, here: how to get out of this place without them realizing that we've been in one of their changing rooms, fornicating like a couple of rabbits. This towel alone will have them talking for weeks, never mind the smell in here!"
Once she mentioned it, I realized that there was a distinct aroma of aroused female in the air. I considered things for a bit, then suggested "Would you be willing to dump some of whatever perfume you have with you right before we leave? You could claim you spilled it, and that would cover the smell."
It took her only a moment to respond "Yes, that would work quite well, I think. But this towel…"
"It goes with us, then. You obviously wouldn't have any reason to take it, so even if they notice a shortage in this room, they'll figure they just mis-counted somewhere along the line. If you'd like, I'll even be the one to take it."
"No, that won't be necessary; I have plenty of room in my handbag for it" she replied, somewhat absently – at the time, she was checking to see if all of my cum had drained out of her. Apparently deciding that it had, she moved to stand up again; I quickly got to my feet and helped her up. When she was on her feet, she finally noticed that I hadn't yet fastened my pants all the way. With a wry grin, she extended the towel to me, saying "If I'm going to be stealing this, you might as well get some use out of it, too!"
I couldn't help blushing slightly as I took it from her; as I started to turn around so I could clean up, she told me "James, this hardly seems the time to start getting bashful, after making me feel so good and dumping what felt like quarts of your semen in me!"
That only made me blush harder until I realized that not only was she not upset about what had happened, but that she was actually feeling somewhat playful. Taking what she said at face value, I simply unfastened my slacks again, and unconcernedly went about cleaning off my cock as she watched me. When I was done, I simply folded the towel over a few times so that the wettest part of it was on the inside before she gestured for me to set it next to her purse.
With our bodies more-or-less cleaned up, the next order of business was to get ready to make our exit; Katherine asked me to gather the bra and panty set while she got dressed again. I had picked them up and straightened them out so that they looked approximately like they had in the box when she asked me if I'd bring them to her behind the privacy screen. I wasn't prepared to find her wearing only a pair of stockings (sans garter belt) and pair of very brief, French-cut panties – but no bra. She was easily as attractive and appealing in her (apparently) original clothes as she'd been in the items from the shop, and I couldn't help looking her over again. She didn't seem to notice, and simply took the stuff and put it in the box with the other items after shuffling them around a bit.
My hands empty again, I took a step back so I could give her some privacy again, but she stopped me by saying "No, don't go. I could use your help with my dress."
I managed not to gawk at her too much as she stepped into the dress, then got it pulled up over her hips and her arms into the sleeves. I was still a little wrapped up in the idea that she'd been braless under it when she turned her back toward me and asked me to help her with the zipper. I did as she asked, trying not to notice that she contrived to get my hand on her ass to hold the dress steady as I ran the zipper up.
Once both of us were ready to face the world again, she had me take the box of stuff from the store and stand over by the door while she quickly poured a quantity of her perfume onto the small table behind the screen. She hurried to join me, and calmly buried the towel in the depths of her handbag. When the scent of her perfume was strong enough, she said "There, that should do it. Time for us to leave, James!"
I followed her back into the showroom, carrying the box of assorted items that she'd intended to try on. One of the clerks readily relieved me of that minor burden before asking Katherine if there was anything she was interested in. She calmly answered "Yes, I think I'd like all of them. There's no point to having you deliver them, so if you would be kind enough to wrap them, I can take them with me."
They readily agreed to that, and she paid for everything while they got it all packaged for her. Naturally, I carried the bag for her as we left.
Once we were outside, she quietly asked me "Is there someplace that we can put the towel? I'd just as soon not carry it around with me the rest of the day…"
"We can put it in the trunk, if you like. I lease the vehicle, so it goes home with me each night; I can take care of it for you this evening. If you'll watch to make sure I put this in the trunk properly, you can give it to me then."
Turning her head slightly, she gave me a smile before saying "Yes, that would do nicely. Thank you."
When we'd taken care of those two items, I helped her into the back before getting behind the wheel again. Ready to resume my duties, I asked her "Where to, Ma'am?"
She named another store, and I got us moving. I was perfectly willing to keep my mouth shut and wait to see what, if anything, Katherine had to say about what had happened between us. Sure, I'd likely gotten her settled down then, but now she had the opportunity to go back and think about it some more.
The ride to the next place was quiet, though, and she told me I could wait outside if I wanted; the place was another one she 'had' to visit without any expectation that they'd have anything of interest to her. Sure enough, she wasn't in the place an hour, and it was off to the next one. It was one where she figured to be inside for a bit, and suggested that I come in with her. I did, and got served another couple of tiny cups of bad coffee while she looked at the various evening gowns that they offered. She asked my opinion on a couple of them, and I gave her my honest answer. She ended up buying a couple of things, and by the time we got back out to my cab, it was getting toward late afternoon.
I had asked her for our next destination when she told me "Actually, I think that's it for today, James."
"Yes, Ma'am. Back to the hotel, then?"
"I'm not sure. I'm getting a bit hungry again, but I really don't want to go out, and I don't want to deal with room service, either. Is there someplace that you could recommend?"
I'll admit that I was a little surprised by the question, but told her "There are a couple of places that I like to go to, but they aren't quite up to the standards of where we went for lunch."
"That sounds perfect, then. I don't want to have to change like I would if I went anyplace I usually would."
I asked her if she was interested in anything in particular, and she said that she thought that something a little more substantial than the fettuccine we'd had for lunch would be good. It took me only a moment to decide where to go, and I quickly had us moving.
When we got there, I could see that Katherine was somewhat underwhelmed, but she didn't say or do anything to indicate she wasn't willing to at least give it a try.
It was when we got inside that she realized that although the outside of the place looked a little run-down, the inside was flawless. The hostess recognized me, and quickly showed us to a quiet spot over in one corner. As we waited for our waitress, I told Katherine that the place semi-specialized in steaks, and that her beverage choices were going to be fairly limited: water, coffee, tea, a few soft drink flavors, or one of a limited number of brands of beer. Again, I could tell she was a little surprised, but still game.
Our waitress greeted me by name, and let me know what that nights specials were, before leaving us to consider our options for a few minutes. When she was gone, I looked over at Katherine and pleasantly asked "You took care of me at lunch; will you let me take the lead, now?"
She gave me a smile before answering "Of course, James."
When our waitress came back, I ordered something that the place did particularly well; Katherine followed my lead, though with a smaller portion. For drinks, both of us went with iced tea. When it had arrived, and she'd had a chance to doctor it, Katherine sipped hers and exclaimed "This is excellent – much better than I've had anywhere else!"
I couldn't help grinning as I told her "They make their iced tea by starting with actual tea – not tea BAGS or instant, but real, live tea. Almost NO place does that any more, because it takes time and effort, and a lot of folks either can't tell or don't care about the difference in taste. Faster and easier to use the bulk stuff they get from whatever their supplier can provide. But if you actually like tea, it's worth the few cents more a glass."
As we waited for our meal, the two of us casually chatted about a number of different things; but neither of us got anywhere even close to the events of that afternoon.
Our meal finally arrived, and I could tell that Katherine was looking forward to finding out if the same attention was paid to the food as had been lavished on something as simple as a glass of iced tea. I couldn't help but be amused when she discovered that it was: "This is the best prime rib that I have ever had, anywhere! How in the world do they do it?!"
"For starters, the owner doesn't get his meat supplied by any of the big national outfits. He deals with a small co-op somewhere in Montana, so that he can get the kind of product and service that he wants. Just by himself, he takes nearly a quarter of their output, so they're more than happy to see to it that he gets what he wants. Again, it costs him a little more, but the business he does more than makes up for it."
"I don't doubt that for second!" she said around another bite.
After that, conversation was pretty sparse as we got ourselves wrapped around some damn fine food. When all that was left was some happy memories, I had to laugh when Katherine tried to stifle a soft belch; her ears pinked a little, but she otherwise managed to maintain her composure.
Next on the agenda was what to do about dessert; again, she followed my example of a slice of cheesecake – and found it every bit as tasty as the rest of the meal had been.
When we were finally ready to leave, Katherine was adamant about leaving the tip – half of what the meal had cost me. I tried to tell her that she didn't have to leave that much, but she told me "Nonsense. Even granting that you might have gotten some extra attention because the waitress knew you, it was still excellent service. She was there when we wanted her, but not hovering over us; she was polite and friendly and helpful, but without being cloying. The food was a damn sight better than lunch, and there was plenty of it – I was half afraid I wasn't going to be able to finish that slice of cheesecake! The place was bright and cheery and clean, and I don't doubt that we could have stayed there another hour and they wouldn't have said a word to us; at lunch, I felt like they wanted me to eat and get out so they could serve someone else."
Once we were back in my cab, I told her "I've known the waitress we had for some time now. I wasn't going to say anything in there, but you might be interested to know that she's getting close to getting a law degree – after getting away from an ex-husband that used to beat her, and abuse their two daughters. He came home drunk one night, beat the hell out of her, and was headed for the bedroom where the two kids slept when she nailed him in the head with a cast-iron skillet. She got the kids and some clothes together, and hid out in an abused women's shelter until the divorce was final. First place she had of her own was a one bedroom dump in the worst part of town, but she got a job and started getting her feet back under herself. That was ten years ago, and she graduates college the semester after next."
Katherine sat there quietly for a few seconds before asking "How do you know all that?"
"I give free rides to the shelter to women that need it, and she was one of them. After she got her divorce, we became friendly – as in friends, I mean. She used to talk to me about all the crap that happened to her and the kids, and I kind of helped her understand that none of it was anything that she should be ashamed of. With her and the kids being all alone and not having anything at first, she was in pretty bad shape, and I stayed with her, as a friend she could talk to, through it. She's getting government help with her tuition, but pays for all her books and other stuff herself from what she makes there – on top of taking care of her kids and everything else, of course."
"Why are you telling me all this?"
"So that you know that that oversize tip you left is actually going to do something to help someone that deserves it."
"But why?"
"You told me at lunch that you spend a lot of time being bored. I'm letting you know that you don't have to be bored; there are plenty of things that you could do that would not only help fill up your day, but actually accomplish something. You said that you have an 'ungodly' amount of money, and that it makes you wonder about the motives of some of the people you meet. Why not use some of the money that you don't need to help people like that woman in there? Did I mention that the lowest GPA she's had has been 3.51? And she plans to work helping other abused women when she graduates? If I'd asked, she'd have been glad to show you pictures of her girls; they're both pretty as they could be, smart, and good kids – neither one has ever been in trouble at school, or with the cops. If you've got so damn much money that you have to worry about the kinds of guys you're meeting while you kill time, how about doing something to change all that?"
Katherine considered that for several seconds before quietly telling me "I think it's time I got back to the hotel, now."
Neither one of us said anything on the trip. When we got there, I helped her out of the cab, and then hurried to get the one package that she had out of the trunk. I was waiting to see what she wanted me to do with it when she reached out and took it from me and started for the door. She was just a couple of steps away when she turned and said "James? Would you be good enough to come up to my room? I think I'd like to talk with you a little more."
The doorman heard her, and after she'd gone inside, he gave me a look of curiosity; I simply shrugged my shoulders and got back in my rig to go find a place to park it. I'd just gotten inside the lobby when the night manager spotted me and came over to me. I figured I might have some explaining to do, but he said "I know it wasn't your idea to come in here, Jim. Ed" – the doorman – "told me that Mrs. McGreevy said that she wanted you to come up, so I figure that whatever the hell you did today, she was happy about it. So there isn't going to be any trouble about you being in a guests room."
"Thanks. I gotta admit, I was a little worried about it."
"No need, Jim. We aren't going to hold it against you if a guest wants you upstairs – particularly her. Just try not to mess things up now, okay?" – that last with a grin.
"Not if I can possibly help it!", I assured him, before heading for the elevators.
I'd been told she was in their best suite, and I knew where that was, even though I'd never actually been in it myself. The elevator got me to the top floor, and the name of her suite was right there by one of the half-dozen doors on that floor.
I knocked softly, and it was only a few seconds before the door opened to show her standing there. Seeing me, she stepped aside and invited me in. Once I was, she closed the door behind me, and then led the way into the living room area. I accepted the glass of wine she offered me, then took a seat on the opposite end of the couch that she led us to.
We'd each taken a couple sips of our wine when she told me "I have to admit, that was some story you gave me in your cab after dinner, James."
"Katherine, it wasn't a story – it's the truth."
"I'm sorry; I didn't mean 'story' that way. No, I meant it was something hearing about all that woman has been able to accomplish after all she's been through. But what really surprised me was what you had to say about me, and my life."
"I hope you'll forgive me, but it was something I figured needed to be said."
"What do you mean?"
"Even before lunch, I could see that you were mostly just going through the motions at those different places. I mean, sure, they had nice stuff, and you bought some of it, but it seemed to me like you weren't really involved. I've been out shopping with girlfriends and other women, and even when they're just looking, they're a whole lot more interested than you were. Then when you told me that you spend a lot of time just looking for something to do, and about the guys you meet and everything… well, it just seemed to me that somebody needed to point out to you that there were ways of solving those kinds of problems."
"And what made you think you could say something like that to me?"
"Well, after a good meal like that, you seemed to be in a fairly receptive frame of mind; I didn't figure it was too big of a chance. And like I told you, it seemed like something that needed to be said."
She looked at me contemplatively for several seconds before saying "Well, you were right. My life has been pretty empty since my husband died, and it was something that needed to be said. When you told me that you'd been a philosophy major, but dropped out, I have to admit that I thought that it was just because you were someone that got bored with studying; I wasn't quite ready to believe what you said about your reasons. But after we were… intimate, the explanation you gave me simply made too much sense for me to think that you'd been anything but a good student. And when I started really thinking about what you'd said, I had to start thinking about everything else I've seen, and learned about you. Once I did that, it didn't take me long to realize that you really, truly are a philosopher, in the classical sense of the word."
I nodded my head in acceptance of the compliment she'd just given me, and she went on "On the ride back here, I was thinking about what I want to do to change my life. I've got a few things that I think I'd be interested in doing, but I expect that it would be to my benefit to get some input from you before I start throwing money and time at them and possibly wasting both. Then when we're done with that, there's something else I'd like you to do for me – but I want to save that until we're done with this other part, first."
"I'll be glad to do whatever I can", I assured her.
She looked at me for a few seconds before standing up; I started to get up, too, and she gestured that I should stay where I was before telling me "Before we get too far into this, I want to make sure and give you an appropriate gratuity for all you've done for me today."
She disappeared into one of the other rooms, then reappeared a few moments later with an envelope in her hand. When she was seated again, she handed it to me, saying "That is from me to you, person to person. There will be an additional sum with the payment you receive for driving me around today."
I thanked her, and simply folded the envelope in half and stuck it in my shirt pocket. She asked "Aren't you going to look to see how much it is?"
"Katherine, you have been nothing but kind and generous with me today. I know that whatever is in here is what you think is fair and reasonable, and what I have earned, for good or bad. I won't embarrass either of us by opening it in your presence."
I could see that she was pleased with my reply, and had to figure that however much was in that envelope, it was probably a fairly nice tip.
Each of us took another sip of our wine, and she started telling me about some of the things that she'd thought she might like to start doing when she got home. She also asked me a fair number of questions about different aspects of them, and sought my opinion on their relative merits; the resulting conversation lasted for well over an hour.
I thought we were pretty much done when she reminded me that there was still something else by saying "With that out of the way, all that's left is that one last thing I wanted you to do for me."
"What would that be?"
"This afternoon… when we were… intimate…"
I hastened to tell her "No one will ever hear about it from me, I assure you."
She waved her hand dismissively, saying "I'm not concerned about that. If you have the principles to say something that you thought needed saying, despite the risk that I might take offense, then I think that I can trust you not to speak out of turn, as well. No, what I was going to say was that what we did – and more to the point, what you said about it afterwards – made me face up to the fact that I am, as you said, a fairly passionate woman. I've always enjoyed sex when it has happened, but I've never been one to initiate it. At least, not before today!", the last with a wry grin.
Taking a breath, she went on "That you helped me have no less than three orgasms so closely together… well, it made me realize that I've been holding things in that I really didn't need to – and perhaps shouldn't have. But it's an area that I've held in for so long that I'm not entirely sure I can release control over it all on my own."
Seeing from the expression on my face that I really wasn't understanding where she was trying to go with all of that, she told me "What I'm trying to say is that as good as you made me feel earlier from that brief encounter, now I want to find out if you can help me learn to loosen my sexual restraints, too."
From the faint blush I could see on her, I knew that she was a bit embarrassed; but the expression on her face told me that her determination was even greater.
The idea of getting intimate with her again certainly had its appeal, but I wasn't sure that I understood just what it was that she wanted from me. The only thing I could figure to do to try and settle the matter was to say "Katherine, you're a lovely woman, and I'd consider myself fortunate to share your company. But I'm afraid that I'm not entirely sure how I can help you."
Realizing that I was generally agreeable, but that she hadn't really given me any indication of what she wanted, she told me "My upbringing was rather… conservative. While my parents weren't particularly religious, subjects like sex were only spoken of very infrequently. Similarly, the schools I went to weren't inclined toward liberal teachings, either, so the little bit of sex education that I got was pretty much limited to explaining what a menstrual cycle was, and how babies are made – using animations, no less. I was a virgin up until my wedding night; my husbands history wasn't all that different from mine, so neither of us was particularly experienced or adventurous. The entire time we were married, the only sex we had was either with him on top of me, or the way you and I did it. There wasn't a lot of foreplay, and only rarely did we ever see each other actually nude. The pleasure I had today… it made me realize that there is a lot that I've missed out on, for one reason or another. I know that I can't learn everything all at once; but as much help as you've been, and after how good you made me feel, I would like to start learning from you."
"Are you sure you really want to do this? And with me? You understand that there are going to be… challenges?"
After she'd taken a deep breath and released it slowly, I could hear the certainty in her voice when she said "Yes, to all of that. I'm nervous, and even a little bit afraid – but dammit, I want better!"
I scooted toward her, then reached out to take one of her hands in both of mine before telling her "If it helps any, Katherine, I'm not going to try and force or push you to do anything; and I'm not going to do anything that you really don't want me to. All I ask is that you be willing to at least try something before deciding whether or not you like it. The very definition of discovery is to go beyond what's already known, right?"
Somewhat reassured, she managed to smile at me as she nodded her head in understanding and agreement. Lifting her hand to my lips, I kissed it before telling her "There are a couple of things you've said that caught my attention: that you've held in your desires, and that you and your husband almost never saw each other nude. If you've been holding those desires in, then I'm taking that to mean that you haven't taken care of them yourself – or at least, not often, anyway."
Seeing the uncertainty on her face, I elaborated "You don't masturbate?"
The resulting blush was something to see before she got control of herself enough to answer "Uh, no, not… not really."
"That's okay, Katherine. You told me how you grew up, and I can understand that it would be a little embarrassing to talk about it."
"Try a lot embarrassing!", she declared, before I continued "What you need to understand is that not only is that a perfectly healthy and reasonable thing to do, it's also something that everybody does."
She looked at me a bit uncertainly, and I told her "Okay, then, how about if we start out by taking care of a couple of things: nudity and pleasuring yourself?"
The first reaction I saw was reluctance; but after a few seconds, she realized that she had to start somewhere, and nodded her acceptance before asking "Will… will it just be me?"
"If I'm not there for the nudity part of it, you aren't actually accomplishing anything, are you? As for the rest, that's really up to you. I think that I can probably help you, but if you're really that worried or nervous, then I can leave you alone. Or, if you think it would help, I'm perfectly willing to be nude and masturbate with you, to show you that it really isn't something you need to be embarrassed or ashamed about."
She considered that for a few moments before responding "I think I'd like that – you being there, too, and, um, doing it with me. I think I'd like to see how you, I mean, a man… does that."
I waited a bit, and finally realized that she was going to need a little help getting started. After standing up, I gently guided her to stand with me before moving behind her and slowly unzipping her dress, then slipping it off her shoulders. That done, I slid it down past her hips and carefully guided her to step out of it. Then I had the pleasure of rolling her stockings down her legs before I finished up by slipping my thumbs under the waistband of the panties she had on and slipping them down her legs, too.
With her standing there nude, I moved back around so that I was standing a few feet in front of her before calmly taking my own clothes off just as I would at home. I noticed, but didn't comment on, that her nipples erected as she watched me undress.
Once both of us were ready, I stepped forward again and gently guided her to sit on the couch again before taking a seat next to her. Her legs were closed, and her hands were fidgeting slightly in her lap; knowing that I needed to settle her down a bit, I took her hands in mine and held them before looking into her eyes and calmly telling her "Katherine, it's okay – really. I'm here to help you, just like you said you wanted me to. I'm not going to push you, but I'm not going to let you give up, either, okay?"
Slowly, she nodded, and finally answered "Yes, thank you, James."
Still looking into her eyes, I said "You told me that you're nervous, and even afraid – and I can understand that. I'm not going to just start grabbing you, or poking at you, or anything like that. Instead, what I want is for you to tell me what you feel and what you like, and I'll help you make it happen. If you can let go of some of that, I can help you learn to give yourself pleasure. If you can stay with me, we can help you learn what feels good and how to make yourself feel good. Do you think you can do that?"
Realizing that I was willing to take things slowly seemed to give her some comfort, and even confidence: she managed a weak smile and nodded again before closing her eyes.
"When you think about having sex, what's the first thing you notice about yourself?", I asked.
"My breasts; I can feel them get tight, and my nipples get hard."
"Do you like to have your breasts touched? How? What about your nipples?"
"Yes – I want to feel his hands on my breasts; just holding them at first, but then caressing them, and squeezing them."
I released one of her hands and moved it to her breast, cupping it from underneath, and heard her say "Yes, like that."
"Go ahead and put your hand on mine, and move it. Show me what you want", I suggested. A moment later, her hand was on mine and she was guiding my hand around on first one mammary, then the other. I continued to softly talk to her, directing her to guide my hand and change how and where I touched her. It didn't take long before we had both of her silver-dollar-sized areolas puckered, and her crayon-diameter nipples standing erect in response to the caresses and soft squeezing of her breasts, and the gentle tweaking and pulling of her nipples.
I maintained an almost continuous soft patter with her: offering encouragement, seeking and offering guidance, and giving and receiving feedback as I slowly and carefully drew out more and more detail, and helped her move along the path toward higher and higher arousal. She didn't hesitate in the slightest to let me know when she took notice of the area between her thighs, and readily parted them so that we could include her vaginal opening and labia and clitoris in her ministrations; when my hand left her breasts, she didn't hesitate to replace it with her own.
It was her hand that guided one of my fingers between her engorged labia and into the hot, slick depths of her vagina; and it was she that wetted a fingertip with her oils and began teasing and caressing her clitoris. As she became more and more involved in learning her own body and how to please it, I gradually reduced my own involvement in favor of watching her and offering her the verbal support and encouragement she needed to continue.
When I had both of my hands free again, I carefully moved myself away from her a bit, giving both of us room for what I next had in mind for us. That accomplished, I was free to enjoy being witness to all that was happening with her: the aroused flush she developed, the scent of her woman's essence, the faint liquid sounds of her finger moving in her channel, and the slow evolution of her increasing desires.
All of that was having an effect on me, too, and I was slowly stroking my cock when Katherine suddenly opened her eyes. At first glance, she seemed embarrassed to realize that I was watching her as she masturbated – but when she saw that my erect penis was in my hand, she released a soft moan as I watched the peaks of her breasts tighten even more.
"You're… you're hard – from watching me?"
"Not just that, but mostly, yes."
"But… why?"
"Because you're a very attractive and sexy woman, and seeing you excited is making me excited."
"And you're… touching yourself… because of me?"
"Yes."
Hearing that, she released another moan – deeper and louder than the first – before saying "I… I've never seen a man… do that before… it… it makes me feel so excited… knowing that I can do that…"
"Would you turn toward me? So that I can see YOU better? That would help get me more excited, too…"
It took her only a moment to decide that she was willing, and but a few seconds to get herself rearranged so that she was facing me almost straight on. Then she surprised me by spreading her legs – putting one foot on the couch and leaning her leg against the back while keeping the other foot on the floor. That left me with a clear view of the area between her thighs: the russet wedge of her pubic thatch, parted at the bottom by her long and thick labia. At the top of her furrow, I could easily make out her clitoris between the two fingers she'd been using to rub it. Even as I was looking at her womanhood, I saw her vaginal lips get a trifle darker, and the area between them get even more shiny with her oils.
Dragging my eyes upward, I saw her breasts appeared to be tighter, and her areolas more puckered, than they'd been when I'd looked at them just seconds before. The upper slopes of her breasts were tinged a light pink – but the color darkened as moved my view upward. Her face had a distinct blush to it, and I could see that her eyes were locked on where my hand was wrapped around my manhood.
It was obvious enough that seeing me erect, and masturbating, was dramatically increasing her own arousal; it was an easy decision to mirror her position, and change how I was stroking myself so that she could see more of my hard cock. It was a matter of just a couple of seconds before she was again stimulating herself under my gaze: her hand moving on her breasts, squeezing them; softly pinching and pulling on her nipples; rolling her nipples between two fingers. Farther down, her other hand was just as busy: sliding one of her fingers into her obviously wet channel, and collecting her oils to use as lubrication while she toyed with her clitoris. Without seeming to realize that she was doing it, she even moved her self-wetted finger to her mouth and sucked her own juices off of it a few times – something that further inflamed her passion and arousal.
I found the entire situation and experience incredibly erotic and stimulating: not so much because of how she looked (though she was most certainly attractive), but because of what she was doing, and that she was granting me the priveledge of watching her do it. The knowledge that she'd patently never let herself 'go' that way before, and that she was so obviously enjoying the experience, only served to amplify the effect.
Though I could feel myself moving toward my climax, I could also tell that Katherine was somehow unable to find the release that she was patently so close to. I tried to hold off, thinking that she just needed a little more time, but the sight (and scent!) of her contrived to make that more difficult. Finally, there was nothing else I could do, and with a groan of pleasure, felt my cock erupt.
Even as the first wad of my semen was landing on my belly, I saw Katherine convulse with the start of an orgasm. Each eruption of cum from my erection seemed to trigger another spasm through her body, causing her to grunt with the force of it. Being witness to such a powerful orgasm only served to intensify and prolong my own pleasure, and thus extending hers, as well.
It was my own male limitations that finally allowed things to taper off – I could only climax for so long and so hard before my body decided that enough was enough; by the time my penis was back at half-mast, Katherine was lying back on the arm of the couch, gasping for air.
Looking around, I quickly spotted the napkin that had been with the wine bottle. Grabbing it, I quickly wiped my hand and belly off before moving to sit close to Katherine. I managed to get her sitting up enough that I was able to take her into my arms and hold her as she slowly got her breath back. Her head was resting on my shoulder, and I felt her blush before she managed to softly tell me "That was absolutely amazing. I didn't know that I could get that excited, or have an orgasm anywhere NEAR that good!"
I gave her a small hug and answered "I guess now you do, don't you?"
She blushed again before telling me "I certainly do! I was really nervous and everything, there at first – but you were so gentle and patient with me; and the way you kept talking to me, and asking me how I felt, and doing what I told you would feel better for me… the next thing I knew, I was making myself feel so good! And then… when I saw that you were hard, and… what you were doing… it made it even better, and I could feel myself getting so wet inside. Dear God, I've missed out on so much!"
After giving her another hug, I told her "It doesn't matter what you missed out on before – there's nothing you can do to go back and change it. What you can do is choose to take control of your life, now. Now you know that you are a passionate woman, and that you don't have to try any hold in your feelings and desires. I'd say that you have the solution to at least part of your problems well in hand."
I felt her blush again, accompanied by a soft laugh at the somewhat bawdy pun I'd deliberately made.
She nudged me, and I readily released her so that she could sit up again. She turned to face me, and I could see from her expression that she was appreciably more relaxed about the two of us sitting there nude than she had been before. Looking into my face, she told me "Yes, I do – thanks to you. What I – we! – did felt very good to me; but when I saw that you were watching me as I did that, I started to feel nervous and even ashamed. Then I saw that what I was doing was making you excited, too, and that you weren't afraid to let me see you touching yourself, and that somehow made it all right. Better than 'all right', even – it made me even more excited than I already was. You kept doing it, and I could tell that you were getting more excited, just like I was. I could feel myself getting closer and closer, but it still seemed like nothing was really going to happen until I saw you… finish. Then it seemed like the whole world fell in on me!"
Even as she was saying that, she looked down to my belly, and saw that I'd cleaned myself up a bit. Looking up at me again, she asked "You cleaned it up? When? Why?"
"Yes, I did; a little after you fell back on the arm of the couch. I wanted to hold you, and didn't know how you'd feel about getting my cum – my semen – on you."
"Why would you worry about something like that? I've already had your… cum IN me, so why would getting it ON me matter?"
I gave her an apologetic shrug before I answered "Some women I've known… they're okay with having semen inside them, but are a whole lot more particular about getting it on their outsides. I didn't know how you would feel about it, so I just wiped it off first."
She sat there for a bit, looking contemplative, before telling me "You are much more thoughtful and considerate than I realized, or gave you credit for. Actually, it wouldn't have bothered me in the slightest, getting your semen on me – but you didn't know that before, so you took the time and made the effort to clean yourself off a bit before holding me, so that you could be sure not to bother me about it. Now I'm even more certain that I want to ask you if you'll help me finish what we've started."
"I'm certainly willing to do that, Katherine, but what you just said is pretty open-ended; I've got to ask: just what do you mean by 'finish'?"
After taking a deep breath, she answered "What we've done already… it's a start. What I mean is that I don't doubt I can find my own pleasure from now on. What I'm far less sure of is whether, or even how, I can do it with anyone else. If I do find someone that's interested in me, I don't think that he'd be satisfied with the two of us masturbating ourselves all the time. I want, even need, to learn what else feels good for me, and what I can do for him. And what happened for me this afternoon – well, that was after I'd spent years without having any pleasure like that; so I want to know if I can feel that way again, without having to wait so long, or doing it just by myself."
"To do that, it could be even more difficult than before – you won't be just touching yourself. And if you really want to know what can be done, then it's almost certainly going to involve more than just hands."
Hearing that last part seemed to throw her off balance, but she quickly understood what I was getting at. She didn't seem to have any problem with telling me "What we just did… it wasn't the actually doing that was so difficult for me, as it was just getting started. You've shown me that you can be as patient and gentle and considerate as I could possibly want, or need; so I think that I'll have a much easier time keeping things moving than I did getting them moving in the first place. As for the rest of what you said… well, I've already learned that a lot of what I thought I knew wasn't entirely correct; I'm perfectly willing to let go of a lot of other misconceptions, as well. As you said, discovering something new means going beyond what's already known."
I nodded my acceptance of what she said, and asked her "Where and how would you like to start?"
Hesitantly, she said "When I was first married, sometimes my husband would… want me more than just one time. Of course, both of us were a lot younger then…"
I couldn't help smiling as I told her "That won't be a problem – at least, not much of one. I'm not as young as I used to be, either, but given time to recover, and a little inspiration, I can still go more than just once."
Though she tried to hide it, I couldn't miss seeing that she was both pleased and relieved at hearing that. She tried to cover both by telling me "In answer to your questions, the 'where' is someplace that both of us can be comfortable, like the bed", the last with a faint blush before she continued "As for the how… considering how little it turns out that I know, I think I'd better start with the basics: I've never really gotten to look before, and I'm still feeling a bit… bashful about just being naked with someone else."
Again, I had to smile as I told her "The bed sounds like a fine idea, and if that's how you want us to begin, then that's how we'll do it."
The next order of business was the when; I certainly wasn't going to rush her, so I simply sat there. Once she realized that I was literally waiting for her to make the first move, she gave me a wry smile before standing up. I followed her example, and she led the way to the bedroom; I had a fine time watching her walk ahead of me.
As we approached the bed, I told her "You said that you'd like to look, and that you'd like to get comfortable being nude with someone else. I think both of those would be a little easier and more pleasant for you if I could finish wiping myself off with something like a damp washcloth."
I was rather surprised when she responded by telling me "I… I think I'd like to do that for you – if you don't mind, of course."
"That's fine with me, Katherine. Really, you don't have to be afraid to ask me things like that, or tell me if there's something you want me to do, or just do something yourself. One of the best things you can do to make being intimate with someone else is to simply relax, and enjoy yourself."
Nodding her head in understanding, she smiled as she replied "Okay, James, I'll try."
I stopped, and she did, too, before turning to face me. Taking her hands in mine, I told her "Katherine, it's okay to call me Jim, if you like – that's part of relaxing. If you have a nickname that you'd like me to use, I'd be happy to hear it. And while we're at it, I'll tell you that I'm not going to take it as anything more serious than as a term of affection and friendship if you want to call me 'dear' or 'honey' or anything else like that. I'll likely say such things to you, and mean them just that way."
The expression on her face told me that she was both pleased and relieved at what I'd just said before she told me "Yes, I'd like that, Jim – to hear words like that, and to have you call me Kat. That was what my friends called me when I was younger, and I'd like to hear YOU use it, too, because I do think of you as a friend."
I brought her hands up to my lips and kissed them; she responded by smiling and telling me "Now, let's get you cleaned up, okay?"
Releasing her hands, I grinned and answered "Yes, dear" – making her smile before she turned and led us off again.
Once in the bathroom (which was almost as large as the living room in my apartment), she didn't hesitate to take a washcloth, wet it with some warm water, and kneel down to begin wiping off the residue of my climax. She found a small blob of my semen that I'd missed, and readily collected it on the tip of her forefinger. She gave it a tentative sniff, then used her thumb to test its texture; she hesitated a moment, then looked up at me. Before she could say anything, though, I asked "You want to taste it?"
After she gave me a small nod of her head, I told her "Go ahead, then, if you like. It isn't going to bother me any, and I'm certainly not going to be afraid to kiss you if you try it."
On hearing that, she tentatively stuck her tongue out and touched it to what she'd been examining. Her tongue didn't explode or fall off, and she apparently decided that the taste wasn't outright offensive, because she then stuck her thumb and forefinger in her mouth and sucked them clean. A couple of seconds later, she crinkled her nose and told me "It didn't taste like I thought it would. A little salty, but bland. Not like me…"
Realizing what she'd just said, she blushed furiously and looked up at me to see what my reaction would be.
I just smiled and told her "It's okay, Kat. I saw when you did it, and it didn't bother me. In fact, I thought it was pretty sexy."
"You saw, and you don't mind? You don't think I'm… strange?"
"No, I don't think you're strange. I think all of us wonder what our various secretions and fluids taste like, at some point or other. I can't fault you for being willing to taste yourself, because the way you smell makes me want to taste you, too."
"You don't think that I'm some kind of lesbian or something?"
"I don't think that you CAN be a lesbian – at least, not as long as you're willing to have sex with men. Until or unless you ever have sex with another woman, I really don't think you can know if you like women; then you'll have to decide if you like women ONLY, or if you like them more or less than men. But whether you choose to try another woman or not, and what you decide if you do… that's up to you – not me, or anyone else."
"Have you ever…"
"Been with another guy, or tasted myself?"
She nodded, and I said "Like most kids, I had a couple of experiments with another guy, but it really didn't do anything for me. As for tasting myself – well, not in any quantity, but I've gotten enough at various times to know what it's like. It was mine to start with, so I really don't worry about it all that much."
"You… you said that the way I smell… that it made you want to taste me, too. You do that?"
Grinning, I answered "I sure do. I actually like the way most of the women I've done that to taste."
"You said 'most' of the women – why not all of them?"
"The ones that I didn't like, it turned out that they weren't as careful about their… grooming as they should have been."
Satisfied with my answers, she went back to what she'd been doing and soon had me as clean as I could be. She stood up, and after setting the washcloth aside, told me "If you want to go ahead and lie down, I'll be with you in just a bit."
I closed the door to the bathroom behind me, and after turning the covers down, made myself comfortable on the bed. I was lying there with my hands behind my head when Katherine made her reappearance. As she walked over to join me, her breasts swayed in a way that absolutely fascinated me; when she got close enough, she could see where I was looking, and teasingly asked "Bottle baby?"
I grinned and answered "Damned if I remember. Yours look good, so I looked – what else can I say?"
Once she'd gotten onto the bed, she moved to lie on her back next to me; I repositioned myself so that I was on my side, then propped myself up on my elbow so that we could see each other. Putting my hand on her stomach, I told her "I already know that it's going to take a little time, probably an hour or so, before we can get involved again. You want to look at guy workings, and that's fine – but our stuff just isn't all that complicated. So we have plenty of time to talk, or cuddle, or both, if you like. We can touch as much or as little as you're comfortable with, in whatever way makes you happy. If it helps any, I like cuddling; and just touching you the way I am now, or just caressing you. Okay?"
Seeing that she was both reassured and pleased by what I'd said, I slowly lowered my head and gave her a soft, chaste kiss on the lips. When I pulled back again, I could tell that she was a little surprised at what I'd done – and perhaps a little concerned about it, too. Looking into her eyes, I said "Something else you might be interested in knowing is that despite what happened earlier today, it really isn't my way to become intimate with a woman unless there's at least a little bit of care and affection involved. I'm not saying that I'm falling madly in love with you, or anything like that – just that I am interested in you as another human being, and that I'd like to be able to express that interest and affection."
Having said that, I lowered my head to kiss her again – and she kissed me in return.
When I was looking down at her again, she told me "I have to admit that there are parts of this that I've been a little concerned about; I didn't think that you were after my money, but I have to confess that after you kissed me just now, it did cross my mind that you might be feeling that there was more between us than there really is. But what you said about being interested in me, and having just some affection for me… I'm far less apprehensive than I was before. I'm perfectly fine with having you touch me, too – it's been entirely too long since I've had that kind of contact with a man. In fact, if you'd be kind enough to lie down again, I would like to just cuddle for a while."
I didn't bother saying anything in response; I just lowered myself back down to the bed and rolled over onto my back. Katherine readily rolled onto her side to rest against me before putting her leg across mine and her arm on my chest. Once she'd settled her head into the hollow of my shoulder, I put my arm around her, resting my hand on her hip.
Until or unless she indicated she wanted to talk, I was content to just lie there and hold her for as long as she wanted us to stay that way. After a few minutes, I started caressing her body – just from her hip to her waist, at first, but gradually expanding my touch until my hand was tracing slow, soft patterns from her shoulders all the way down to include her delightful ass. Her only response was to wriggle a little closer to me, and release a gentle sigh of content and happiness.
We must have stayed like that for the better part of an hour before she started doing anything herself. At first, she simply held her hand in place on my chest while slowly drawing her fingertips across my skin; but as the time passed, she began to increase and expand her efforts to touching my chest and belly much the same way I was doing to her. After she finally reached my pelvis, she seemed a trifle hesitant about actually touching my cock, and balls – but once I casually told her "You said that you've never really had a chance to learn about guys, so if you want to touch, or even look at me, that's fine", she didn't delay any longer in getting her hand on my equipment.
She was as careful as I could have wanted about not doing anything to cause me any pain or discomfort – but that doesn't mean that the manual examination she gave me was any less thorough, either. I couldn't help growing a little bit as a result of her manipulations, and that only seemed to prompt her to continue. Along the way, I calmly let her know what the common and slang terms were for things.
Once she was satisfied with the tactile part of the exam, she sat up and pivoted around so that she could have a closer and better view of me as she continued her lessons. The first couple of questions she had were asked a little hesitantly, but after I'd answered them as matter-of-factly as I could, the rest came much more easily. When she was done, she readily moved to lie down next to me and resume her previous position before telling me "Thank you, Jim."
"You're welcome, but what for?"
"For being as patient with me as you were while I was doing that, and for answering my questions the way you did. I'm still a bit embarrassed about being as ignorant as I've been, at my age."
I gave her a gentle hug before saying "It's okay, Kat. You told me why, and you decided to correct that ignorance; I'm glad I was able to help."
"Still, it means a lot to me. I think that I was very lucky to get you, today."
Not figuring that there was much I could say to that, I simply gave her another brief hug before starting to caress her again.
Several minutes had gone by when she surprised me by raising up enough to give me a kiss on the cheek and tell me "You're being such a dear, Jim."
Looking at her, I asked "How so?", a little confused.
Seeing that I didn't know what she was talking about, she smiled and answered "By just being who you are, I think. For being honest with me, but polite about it. For your willingness to help me, but not taking advantage of my ignorance. For your patience and understanding. For your gentleness, and your tolerance. For your caring about me, and interest IN me."
I raised an eyebrow in question, and she elaborated by saying "After we were together this afternoon, you helped me to understand why I did something that was so incredibly out of character for me. Then, later, having the courage to tell me something that you perceived that I really DID need to hear. Earlier this evening, you did just what I needed to get me to understand that it was okay to bring pleasure to myself, and helping me to to find it. And now that we're naked and in bed together, you're willing to give me the time to get used to our being together like this without rushing me, and patient with me while I learn things that I should have been exposed to long before now. I don't doubt that you would like for us to be intimate again, but you're not doing anything to try and make it happen before I decide that I'm ready for it – even when you're touching my ass, I know it's because you like it, and nothing more. You're a patient, generous, thoughtful, and above all considerate individual; and I'm letting you know that I appreciate those traits tremendously. Particularly under these circumstances!"
"Kat, it just isn't who I am to be any other way – at least, not without damn good cause. You tell me that I've shown you all those good traits, but I've only responded to the way that you acted toward me. Instead of treating me like a hired lackey today, you were gracious and considerate. Rather than barricade yourself behind your money, you chose to be courteous and friendly. You could easily have made yourself unapproachable, but instead, you let me know that you would welcome my thoughts and opinions. I've driven other wealthy people who made it more than clear to me that they thought they were somehow 'better' than I am – and if you'd acted that way, I'd have willingly let you continue in that fantasy. But because you dealt with me as another human being, I was happy to respond in kind. So any good will I showed you was only my reciprocating what you showed ME."
A couple of seconds passed before she told me "And that is a lesson that I'm never going to forget: that a person's worth as a human being is NOT determined by their social or economic status, but by what's inside them. You can be sure that I won't tolerate any of that nonsense when I get home and get my projects started – the waitress we had is simply too much of an example why not to."
With that, she let me draw her down so that she was lying next to me again, and I gladly put my arm back around her.
Several minutes later, she softly nudged my arm out of the way so that she could roll over onto her back. I didn't realize that she wanted anything more than a change of position until she reached over to take hold of the wrist of my arm that was away from her and use it to get me to roll over onto my side, facing her. That done, she put my hand on her breast and quietly told me "I'm ready to have you teach me the rest, now, Jim."
I got myself propped up on my elbow again and, looking down at her again, asked "You're sure?"
She didn't have any problem with looking into my eyes as she confidently answered "Yes, I'm sure."
Lowering my head, I gave her a soft, brief kiss on the lips; when our lips touched again, she made it more than clear that she wanted to learn what I had to offer.
Even as our next kiss was growing longer and more passionate, I was using the hand she'd put on her breast to gently squeeze it, and toy with its nipple; when she softly moaned her pleasure, I traced a path over to the other, and happily gave it much the same treatment.
I'd gotten both of her nipples hard and erect when Kat opened her mouth slightly and tentatively touched her tongue to my lips. I didn't hesitate to open my mouth in return, and send my tongue out to welcome hers to the neighborhood. Once they'd introduced themselves to each other, they began playing a game of 'tag' that ranged from her mouth to mine, and back again.
With her willing to to take things that far, I figured I'd find out what else she was agreeable to – and slowly moved my touch farther and farther down her body, giving her plenty of time to let me know if I was trying to advance things too quickly for her. When my fingertips found the lush forest of her pubis, she moaned softly and parted her thighs in invitation for me to continue. Even with her opening herself to me that way, I still had to take a little time to marvel and delight in the thick softness covering her mons. When I finally progressed to the area between her thighs, I found that she was well along the path of arousal: her labia were full and extended, and the area between them slick with her oils; at the top of her cleft, her clitoris was starting to make its appearance.
Though we had to come up for air every so often, our kisses continued as I used my hand and fingers to not only learn more about her particulars, but to increase her excitement. Wetted with her essence, my fingertip teased and toyed with her clitoris to ratchet up her passion and desire; a bit later, she arched her hips in welcome when I patiently worked a finger into her hot, slick channel.
It wasn't long before kissing her was all but impossible – she was simply panting and moaning too much. Moving my head lower on her, I found something else to do to keep my lips and mouth and tongue busy – well, two things, actually.
Using what I'd learned and witnessed while the two of us were on the couch, I had a wonderful time with her breasts while my hand and fingers stayed busy even farther down. I knew my efforts were appreciated when she held my head in her hands as the duration and intensity of her sounds of pleasure increased. She seemed to particularly enjoy it when I gently chewed on her areolas and softly bit the hard erasers of her nipples.
The scent of her arousal was thick in the air when I decided that it was finally time I found out if she tasted as good as she smelled. Moving my body over hers, I covered her shoulders and throat in small, soft kisses, with brief side trips to softly nibble her earlobes before slowly kissing my way down her body. I delayed at her breasts long enough to freshen the coat of saliva I'd left on her nipples, and cover her breasts with small 'bites' from my lips; then it was time to continue my journey.
She readily spread her legs to make room for mine, and didn't show even the slightest nervousness or concern about what I was going to do – not even when my lips reached the edge of her pubic thatch. In fact, when I first kissed the inside of one of her thighs, she spread them even farther before pulling her knees up to open herself to me even more. My kisses started near her knees, and alternated from one leg to the other, each kiss a trifle higher as I slowly worked my way closer and closer to the core of her womanhood. After I'd finally kissed her on each of the creases between her pelvis and thighs, I got the opportunity I'd been waiting for: the chance to have an up-close, clear, and unimpeded look at her fully aroused womanhood.
And was damn glad that I did.
Her labia weren't particularly long or short, or thick or thin – what they were was as young-looking as if she were still a teenage virgin: smooth and straight, without the outer edges of them looking like dried-up old shoe tongues. They were visibly soft, and dark with her arousal. Between them, the opening to her sex was visible, the entire area glistening with her essence; at the top, her pea-sized clitoris was almost completely exposed.
It took me all of a zillionth of a second to decide that hers was the single best-looking pussy I'd ever seen.
Then, after I'd had the chance to extend my tongue and trace it along her cleft to sample her nectar, I decided that hers was the best-tasting pussy, as well: her oils were light and thin, fresh, and tasting vaguely spicy. I could only mourn the fact that I'd likely never get the chance to see and taste her again, and resolve to make the best of the opportunity that a particularly kind and benevolent Deity had given me.
The next pass of my tongue delved a little deeper, and extended a little farther to include her clitoris – and earned myself a deep, passionate moan from her in the process.
Over the course of the next several minutes, she couldn't have been left with any doubt that not only did I enjoy what I was doing, but that I particularly enjoyed doing it to her.
I knew that she liked what I was doing, too, from the variety of noises that she made and the way she arched her hips up in welcome each time my tongue dipped into her womanhood or fluttered across her clit. As wet as she was getting, and from the sounds that she was making, I knew that I was getting her close to an orgasm – and quietly resolved to make it a damn good one for her.
Softly sucking on her clitoris brought her to the edge, and I suddenly gave that up in favor of licking up the copious oils that she was producing, and then softly 'chewing' her labia with my lips. When she'd fallen back a little, I went after her clit again by gently 'milking' it with my lips until I'd again taken her to the brink – only to abandoning that to collecting her oils again, then trying to see how far I could get my tongue into her vagina. Only when she was nearly whimpering with frustrated arousal did I have mercy on her: gently fluttering my tongue across her clitoris, gradually slowing my actions as she got closer and closer to her climax. I managed to hold her on the verge for several seconds before a furious tongue-lashing pushed her into a deep, deep release that had her almost convulsing with the power of the spasms coursing through her body.
With her thighs all but fused to the sides of my head, I delighted in lapping up the waves of fluids that her vagina was pushing out to me, and prolonging her orgasm in the process.
When her legs finally fell away from my ears, I moved up to hold my body over hers so that I could softly kiss her on the forehead; once I'd done that, I waited patiently for her to get her breath back. It took a couple of minutes, but she eventually opened her eyes, and when she saw me, it took only a moment for her to wrap her arms around me and pull me down for a long, passionate kiss. After our lips had separated, her voice held a trace of awe as she told me "That was incredible – I had no idea that someone doing that to me could make me feel like that!"
I couldn't help grinning at her as I answered "Well, you certainly seemed to enjoy it. I like doing it, and you certainly tasted as good as you smell!"
"Would… would it be okay if I tried doing that for you, too? I've never done it before, but I want to learn, if I can make a guy feel that way, too – I mean, if you don't mind having to teach me…"
Gee, there's a question: would I mind teaching an attractive woman how to give blowjobs by letting her learn and practice on me?
"Kat, you don't have to do that on my account; but if you really want to, then yes, you can learn with me."
"What do I do first?"
"I think it would be easier and more comfortable for you if you let me lay down on my back. Then you can start however and whenever you want, and go however fast you decide you're ready to."
Smiling, she nodded her understanding, and waited patiently for me to move off of her and get myself repositioned. Once I was lying on my back, she didn't hesitate to sit up and get herself situated so that she was again face-to-face with my manhood. She wasn't the slightest bit reluctant to reach out and take me in her hand, but before she could go any farther, I told her "There are a couple of things that you need to know before you get started."
She turned her head to look at me, and I explained "First, I am not going to be upset or anything if you decide that you don't like doing that for any reason. If that happens, then just go ahead and stop, and we'll figure something else out. Second, it's been long enough that I can conceivably climax again if I'm stimulated enough – which brings us to the last thing: I'm perfectly willing to let you do that as long as you want to, so it's going to be up to you if you want to take it all the way and wait some more before we can actually make love, or if you want to stop before then so that we can make love. Again, I'm fine with either one. If you want to take it all the way, I'll let you know when I'm going to climax so you can decide what you want to do; otherwise, you can stop whenever you're ready for us to go on."
She smiled her understanding before turning her head to look at where she had my penis in her hand. After only a momentary hesitation, she lowered her head and softly kissed the end of my cock. A moment later, she opened her mouth and took the head between her lips before giving me a tentative lick.
Over the course of the next several minutes, I patiently and gently told her some of the things that she could do to please and arouse the male of the species. She was a willing student, and wasn't the slightest bit reluctant to at least try the different things that I brought up. Most important to me was that she was most careful about not doing anything that would hurt me – she didn't need to be told that teeth were a Bad Thing, she didn't squeeze or pull or or poke anything to excess, and as she began to get the desired results, her enthusiasm increased proportionately.
She'd brought me to full erection and was taking her time to practice the different things she'd learned when she finally let me slip from between her lips again. Sitting up, she turned and told me "I'd like to keep going so that I could taste you, but I'm just getting too damn excited to want to wait until you can get hard again afterwards – I want you IN me!"
That seemed like a particularly fine idea to me, and I readily told her "I'd like that, too. It's up to you if you want to start with something more familiar, or try something new…", with a Significant Look toward where my erect penis was waving in the air.
It took her a couple of seconds to realize what I was suggesting, but when she did, she got a delighted look on her face before asking me "Which way do I face?"
Keeping my grin to an only slightly lecherous level, I responded by asking "Which side do you want me to be able to touch the most?"
She made her choice known by moving to straddle my hips so that she was facing my head – a decision I welcomed, since I wanted to get my hands on her delightful breasts again.
When she'd leaned forward slightly, she asked "What now?"
"When you're ready to take me inside" – "I am ready!" she declared – "you just raise up. One or the other of us holds me steady, and you just kind of sit down on me however fast you're comfortable with."
She nodded her understanding, and lifted herself over me before reaching between us to take my erect penis in her hand. Angling it up, it took her only a moment to realize that we weren't quite lined up, and she quickly scooted herself 'up' a bit until she could position me at her opening. I reached up and cupped her breasts in my hands and began running my thumbs over her nipples as she slid the end of my cock along her cleft a few times. With the head of my cock wetted, she lowered herself so that I was pressing against the entrance to her vagina. I paused in my ministrations to her mammaries long enough to tell her "Kat, there's no need to hurry on my part. Take however much time you need so that it feels good for you. Okay?"
She nodded her head before telling me "Sometimes my husband would want to be inside me before I was completely ready – but because we couldn't, or wouldn't, talk to each other, I never felt like I could say anything to him about it, even though it was uncomfortable, or even hurt sometimes."
"We don't want that to happen, now or ever again, Kat. Sex, and making love, should feel as good at the beginning as it does later", I told her.
She smiled in reply, and I felt her begin to press herself down onto my erection. When I felt myself start to enter her, I also got an idea of just how aroused and excited she was: her core was delightfully hot and wet; I didn't think that she'd have any trouble getting me inside.
Doing as I'd suggested, she took her time getting herself wrapped around my manhood; it was probably a couple of minutes before the firm globes of her ass settled onto the tops of my thighs as she released a pleased sigh and looked down at me with an expression of self-satisfaction on her face. I was back playing with her breasts again, and simply smiled up at her before gently pinching her nipples and telling her "If you'll raise up so that I'm just barely in you, and then slowly sit back down again, I think you'll like it. And if you want to lean forward a little bit, you can see what it looks like, too."
Knowing that I was trying to help her enjoy something new, she readily did as I said: leaning forward and resting her hands on my chest, she watched as her labia clung to my penis as she slowly lifted herself off of me. Then, when she had only the tight ring of her opening clenched behind the glans of my cock, she just as slowly lowered herself back down again – accompanied by a deep moan, and followed by the soft comment "Dear God! I never knew it could look so sexy, or feel this incredible!"
She repeated her actions several more times before looking into my eyes and telling me "It used to feel good, sometimes, at first – but never like this. And to watch while it's happening… it's just amazing!"
With that, she leaned forward and kissed me; I readily wrapped my arms around her so that I could prolong it, and build on it. It wasn't long before our tongues were happily playing 'tag' in each others mouths as the flames of our passion and desire blazed higher and higher.
When our lips finally parted, Katherine raised up and put her hands on my chest to steady herself as she started arching her hips to slide herself off and on my erection. She started slowly enough, but readily increased the pace of her movements until she was in rapid and constant motion on me. For my part, I was happy to keep myself occupied with the orbs of her bosom: squeezing and caressing them, teasing and softly pinching her nipples, and delighting in their warmth and heft and feel.
Raising my head, I was able to fasten my lips on the peak of one of her breasts; as I softly sucked and 'chewed' on it, Kat settled into a rhythm that clearly pleased her even as it provided the stimulation I needed to stay erect in her. As she continued moving over me, I switched from one of her breasts to the other and back again while I brought her nipples to full extension and hardness, glistening with my saliva.
Between the attention I was paying to her mammaries, and her own efforts on my erect cock, Kat's pleasure with our coupling steadily increased; it wasn't long before I could feel her tightening around me as she approached her climax. A few minutes later, I enjoyed the hell out of it when she all but slammed herself down on me before starting what was clearly a powerful orgasm. When it was over, she was visibly tired (and pleased). Running my thumbs over her nipples, I told her "I can see you're a little tired from all that. We can change things around a little, if you don't want to stop."
Several moments went by before she realized that I hadn't climaxed, and that I was still hard inside her. The look of surprise and pleasure on her face was priceless as she asked "You… you didn't… Did I do something wrong?"
Smiling, I told her "No, I didn't, and no, you didn't do anything wrong. One of the things about us guys is that after we've had a climax, it takes longer before we can have another one – and you remember what happened in the other room, so it'll be a while before it happens again for me. Besides that, I can usually hold off on letting it happen. So we can keep going for while, if you want."
There was no mistaking her delight at hearing that, and she readily told me "Oh, I want, all right! What did you want to do?"
"If you'll lie down on your back, I can be between your legs, but in a way that makes it easy for me to make love to you for a nice, long time."
Her grin threatened to wrap all the way around her head as she answered "I'd like that!" before slowly raising herself up enough to let my erection slip free of her intimate grasp.
As I sat up, she moved off of me to lie back on the bed as I'd suggested – not only leaving room for me between her smooth thighs, but giving me a view of her womanhood: the russet wedge of her pubic thatch cleaved by the entrance to her vagina, her labia dark with her arousal and visibly wet as a result of her recent orgasm. When I was finally close enough, I couldn't resist the temptation to lean forward and run my tongue along her cleft a few times (prompting her to moan and arch her hips up in response) before I continued getting the two of us positioned for what I had in mind.
That I stayed on my knees plainly confused her while I reached down and took her by the hips and guided her a little ways onto my 'lap'. Once I angled my penis down and got the head of it positioned at her opening, though, she understood what I was trying to do, and readily cooperated in getting us positioned "just so". With roughly half my erection in her, I could simply rock back and forth to slide nearly my entire length in and out of her with minimal effort; it also left my hands free so that I could continue to touch her in all sorts of interesting and pleasurable ways.
Once we were both ready, I simply had to lean down and take each of her erect nipples between my lips and gently 'chew' on them before sucking on them for a few moments – accompanied by her soft moan of pleasure, and bringing both of them to glistening hardness before releasing them again.
With my hands on either side of her body, I held my torso over hers as I slowly pressed myself into her; she responded with a deep moan, spreading her legs to let me enter her as deeply as possible while she lifted her hands to begin caressing my chest and sides. When I could feel my pelvis pressing against hers, I just as slowly eased myself back out of her until the tight ring of her opening was clenched around me just behind the glans of my erection. As I started to move into her again, she lifted her head to watch as my manhood gradually disappeared into her hot, wet channel. Her eyes widened, and I could see as the blush of her arousal deepened and extended to the upper slopes of her breasts; she groaned passionately before I heard her soft mutter "God! How much I've missed out on, not knowing how good this should feel!"
Over the next few minutes, I gradually and carefully increased the speed at which I moved in her until I found the rhythm that pleased her the most. With that accomplished, all that was left for me was to delight in the feel of her as I tried to see just what kinds of orgasms I could help her have before I either climaxed myself, or had to change positions again.
I easily saw her through three progressively stronger climaxes before I started to feel the first sensations of my own release. By the time her fourth orgasm ended, I knew that her next one would have me spilling my seed into her – and quietly resolved to make it as good of a memory for her as I could.
I started by ending each penetration into her with a little extra push of my hips, causing my pubic bone to bump against her clitoris a bit more. As I'd figured, it didn't take much of that before she was arching herself up toward me in response; from there, it wasn't difficult to slowly alter the way that I did it: from simply 'bumping' her clit at the end of a gentle thrust into her, to making the thrusts themselves more energetic. I deliberately made the transition from one to the other as gradual as I could and Kat not only accepted change, but plainly found even more pleasure from it as evidenced by an increase in her wetness inside and the amount of noise she made.
I could feel it when Kat's vagina started clenching around me, and the added stimulation moved me toward my own release a lot more quickly than I wanted it to; I was even starting to wonder if I'd started something I couldn't properly finish when she suddenly froze under me. The rippling of her vaginal muscles around my cock was a LOT more stimulating that the way she'd felt before, and it wasn't but a few more strokes before I simply had to try and stuff as much of my cock into her as I could before trying to coat her tonsils with my semen. Even as I was emptying myself into her with more force than I'd experienced in a long time, I could tell that her orgasm was far, far stronger than anything else she'd experienced thus far: between the powerful spasms that I could feel coursing through her body, it was all she could do to take deep, shuddering gasps of air before the next wave of pleasure overwhelmed her.
Well after I'd emptied my balls in her, the sensations her womanhood created around my dick were enough to keep me aroused: if I wasn't still completely hard, I was damn sure close to it!
Still, the human body has its limits, and Kat proved to be no exception. Eventually, her climax simply had to end; when she finally opened her eyes and saw that I was holding myself over her, she surprised me with how quickly she wrapped her arms around me, and the ferocity of the hug she gave me. Still panting slightly from oxygen deprivation, she managed to tell me "Dear God, that was incredible! I didn't know anything like that was even possible, never mind thinking that I could ever experience it!"
Lowering my head, I softly kissed her lips before telling her "I was trying to make it the best I could for you. I'm glad you liked it."
Amazed, she looked up at me and asked "You were trying to make that happen for me? On purpose?"
Smiling, I answered "Yes, to both. You said you wanted to find out what feels good for you; you seem to have enjoyed the other things we've done, so I figured you wouldn't mind trying one more."
Looking at me, she said "It felt real good when you started pressing yourself against me, and by the time I realized that you had changed to doing MORE than that, it simply felt too damn good. Before, when my husband did anything like that, it didn't feel good for me – but it only happened when he was almost done, so I learned to live with it. But now… tonight… somehow, you made it different. How? Why?"
After kissing the tip of her nose, I answered "I think it was probably a couple of things. First, we were making love because you wanted us to. Second, you had already learned how to enjoy sex, so when I changed from doing the one thing to the other, you didn't have any reason not to continue enjoying it. Or even enjoying it MORE, if I'm not mistaken", with a grin.
She grinned in response before telling me "Oh, yes, I enjoyed it just fine."
My shoulders were starting to get a little tired, and when I shifted my weight slightly, Kat realized that I was still inside her – and still (mostly) erect. I saw her eyes get big before she said "I… I was sure I felt you squirting in me. It made me climax even harder…"
"Yes, I did cum in you. But the way you felt around me, and the way you still feel, feels real good to me, and is helping keep me like this. Are you saying you don't want me in you now?", I asked, teasing her.
She immediately informed me "I'm certainly not saying that!" before realizing that I was teasing. Somewhat abashed, she quietly told me "No, I was just surprised, is all. It feels good having you in me like that, and it's nice how you're holding yourself over me the way you are. It's like cuddling, only better."
After kissing her lips again, I told her "I'll be happy to stay like this for as long as I can."
She crinkled her nose before she said "I know we can't stay like this for too long."
"No – but that doesn't mean that we have to make any big deal about what happens, either."
"What do you mean?" she asked.
"I mean that when I finally slip out of you, there's no reason that either of us has to jump up and run off to clean up. I liked the holding and touching and cuddling before we started making love, and I just don't think there's any reason not to do those things afterwards, too." I pretty much expected that she'd gotten up as soon as she could after sex (I didn't figure it could rightly be called 'making love') with her husband, and hoped to get her to start thinking differently about post-coitus, too.
She seemed a bit uncertain, and I remembered something she'd said earlier: "After we touched ourselves and I was holding you, you told me that after you'd had my cum in you, you weren't going to worry about having it ON you. Unless something has changed since then, is there any reason for us not to simply enjoy being together for a little longer after we've made each other feel so good?"
She considered that for a few moments before smiling up at me and saying "No, nothing has changed; and there's no reason at all we can't do that. In fact, I think I'd like that!" before lifting her head long enough to give me a kiss on the lips.
We stayed like that, with me over her, as my penis ever so slowly deflated; when I finally slipped out of her, we shared a kiss before I lifted myself off of her to see what she wanted to do. She rolled over onto her side before turning her head to look at me and ask "Hold me?"
I happily positioned myself behind her, and put my arm around her – not surprised in the slightest when she moved my hand to her breast before wriggling herself back against me. Neither of us felt the need to say anything more to each other, though I did give her an occasional soft kiss on the shoulder or the back of her neck or anyplace else that struck my fancy.
Quite a few minutes passed before I heard her say "As nice as it feels to be with you like this, I'm starting to feel a little cold and squishy. Would you be upset if I wanted to take a shower?"
I gave her a brief hug before answering "Only if you wanted to take it alone."
She turned her head to look at me, and I could see how pleased she was as she told me "I certainly wouldn't want to upset you…"
A few moments later, and the two of us were in her bathroom, holding each other as she got the shower started, and the temperature adjusted. Once that was done, we had a splendid time helping each other clean up – with a fair amount of playful molesting, groping, fondling, and general grab-assery along the way.
Dried off and dressed, she let me hold her on my lap on the couch for a little while as we chatted about the different things she planned to do when she got home. Finally, though, it was late enough that I simply had to get home. Before she would vacate my lap, though, Kat told me "Jim, I want you to know how very lucky I feel I am to have met you. You started out as a damn fine cab driver, and just kept getting better and better from there. Not only have you proven yourself to be a friend, but you've helped me find a way to give some purpose to my life. On top of all of that, you've given me the guidance I needed to turn loose of some of my fears and inhibitions – and brought me pleasure and feelings I hadn't known were even possible. You're intelligent, thoughtful in both senses of the word, considerate, patient, and too many other things for me to mention. You're the kind of person that this sorry world of ours needs more of, and I can't begin to tell you how happy and grateful I am to have gotten to know you. I don't think that it would ever occur to you to ask, so I'm going to tell you: if you ever find you need or want to stop driving cabs, there will be a job – and a good-paying one! – waiting for you at one of the foundations that I'll be setting up. There isn't a doubt in my mind that any organization that you were a part of would benefit from having you around, and listening to you."
I didn't figure that there was a whole lot for me to say in response, except "Thank you, Kat. All I've done for you is to help you find what was already inside you. You're a damn fine person, yourself, and I think you've brought as much into my life as you say I have to yours. It truly is a pleasure for me to have gotten to know you, and I'm honored that someone such as yourself would think so highly of me."
With that, the two of us stood up, and I readily let her pull me into a kiss and hug before we headed for the door. When we got there, she told me "Thank you, James, for everything", and I responded by taking her hands in mine and kissing them before saying "And thank you, Kat" before taking my leave.
It was maybe a month later when I got a letter through the cab company office. When I opened it, all there was inside was a clipping from a newspaper. Reading it, I quickly saw that it was about Katherine: it told about how she was using a surprisingly high percentage of her fortune to establish a number of non-profit groups intended to assist those that needed it. The thing that really got my attention, though, was something that she said in it: "Thanks to the example of someone very special to me, I've learned that each of us – even a cab driver – can have a positive impact on someone else's life if we have the courage and compassion to speak and act when it is needed."
I never saw Katherine again. From that time onward, though, I would continue to get the occasional envelope through the cab company; inside, there would be another newspaper clipping about her, and the good she was doing. I knew that she wasn't 'bragging' by sending them to me, but rather, letting me know that she was doing what she said she would. When I got one that turned out to be a society page announcement of her engagement, I silently congratulated her, and wished the two of them the best…