After one month and four more visits to the hotel with Teresa, Alan figured it out. Five visits at $22.50 each came to a grand total of $112.50. The two times they had dinner before retiring to their room cost him $48.00. That brought everything up to a grander total of $160.50. The depressing truth was, Alan figured, that he was well on the way to happy, well-screwed poverty.
He needed the money for his next semester at college. But he also needed sex. Alan sat in his lifeguard tower and stared down at the reflections of sunlight dancing off the pool water. She was something else. After the first time she quickly responded to vigorous, athletic sexual sessions. Her enthusiasm and desire to learn led them right through the beginning areas of sex play to recreations which made Alan's head spin.
That's what really bugged Alan. It was last night when the suspicions he'd been doing his best to ignore crystallized into undeniable evidence. For a virgin Teresa learned fast, very fast… too fast. Faster than the teacher and that was a no-no.
He closed his eyes and recalled the incident in detail to see just where it was, what it was that convinced him Teresa was faking, pretending to be a virgin, a beginner…
They'd had dinner in a restaurant she chose. Alan hadn't planned on it, but she asked if he was interested in her only for one thing and he had to prove otherwise, even though he wasn't. And the hotel, hell, that was an expense he accepted the first time because she was supposed to be a virgin and the second time because he wanted to treat her right. But after those preliminary visits he hoped they could express their mutual affection in the car, at the beach, in places where the toll didn't take the edge off the pleasure.
But no. She was against the tackiness of backseat sex and feared being seen in the more casual love spots. Alan understood that if he wanted to screw Teresa it would be in a fancy hotel or not at all.
They jumped into bed and fucked themselves to a quick climax as soon as they arrived. Then she turned on the television to watch a program while they rested. That was all right with Alan, he watched too and fondled her beautiful breasts at the same time. Then she caught him off-guard.
Alan had eaten her out the last time but she never made a move for his cock. Suddenly her hand was on it, unconsciously stroking while she watched television. He didn't mind. Then the commercial came on and she turned her soft-lipped mouth around and kissed it right on the head.
A thrill of excitement ran up Alan's spine. She wanted to learn, he realized. But before he could say or do a thing she had his cock totally imbedded inside the sweet warmth of her mouth. He felt his pecker head gouge deep and hit the back of her throat. He watched with amazement as she twisted her head to open her throat and take it inside.
She gobbled his stiff cock without a second's hesitation, without as much as a choke or gag. Right in, straight, true and deep. The slickness of her mouth and throat ran along the whole shaft, swirling, sucking, licking him crazily.
The pleasant shock threw him into a state of confusion. Could she have learned to take in a cock with such dexterity on dates? Dates where she maintained her virgin-head but sucked meat to appease the boyfriends? Was it possible she'd suck cock but not fuck? The idea seemed ridiculous to Alan but he tried to believe it.
Teresa took long, slow draws up and down his cock until it gleamed with a thin film of her saliva. The commercial ended and she turned away. Alan waited a few minutes before deciding he had to find out more.
She was on her stomach so he put both hands on the cheeks of her bare, round ass. She didn't seem to notice. He spread the buns apart and stared down at the perky pucker of the pink, tight anus. It was a beautiful, tender dot in a channel of very white, very smooth flesh.
He put his index finger against it and softly caressed. Her hips started grinding, the rump lifted up against the pressure and twisted back and forth. She was responding hungrily to the tip of his finger, spiking up to it eagerly.
Alan pushed his fingertip into the taut muscle and she jutted up. His finger slipped easily inside the tight, hot ring of her asshole.
"Mmmm," she sighed while still viewing the tube.
He was aghast. She pumped her soft fanny steadily until his finger was completely inside. Alan twisted it and made a tentative bend.
"Yes…" she groaned. Her eyes were closed, the program no longer held her interest.
Alan had to know. He brutally ran his finger in and out of the asshole at great speed. Her groans grew louder and more ecstasy-ridden with each shoving stab. She was up to her knees with her face buried in the mattress, her ass jutting high and back to receive his finger with circular, bucking motions of her hips.
The anus was expanding, the colon loose, her asshole now rimmed his finger loosely. Alan removed the index finger and pressed his thumb inside. Again she groaned. Again the muscle responded, growing loose. He squirmed two fingers deep into the clinging hole.
"Uhhh!" she grunted. But she didn't lose her jutting rhythm for a second.
Alan was frantic. His whole attitude was changing. He had to see how much she could handle. His fingers came out of the asshole and moved directly down to her hanging cunt lips. As they slid deep inside she squirmed but held the position while he arranged himself behind her.
With his free hand he guided the thick stem of his cock against the waiting hole of her ass. As soon as the warm glans touched the wet ring she came down and back on him. Teresa took the cock inside her ass with one plunging lurch.
"Oh… I love that," she sighed.
So did Alan. The non-stop humping of her rump was driving his cock insane with the caressing friction and muscular squeeze of her anus. He slowly pulled back and felt her tighten the ring of her ass around him again and again. He had only butt-fucked once before in his life but it was nothing like this. The girl was afraid to move, petrified with the massive fill of cock grinding deep into her asshole.
But Teresa showed no hesitation, no pain, no resistance. Her pink asshole swallowed him quickly, expertly.
The sweat was dripping off his forehead as Alan woke from his reminiscence and realized his cock was straining upward in his swim trunks. The final memory of his pecker unloading viciously, poundingly inside her clipping asshole made him gulp. His reaction to her non-virginal behavior and apparent experience had angered him and he let it out on her warm torso. The terrible thing was she loved it.
It was early in the morning and few people were around. The pool area was empty. Alan climbed from his high chair and jumped into the cool water of the pool. As he emerged his mind was made up. Teresa had taken him for a fool, really played him along like a pro.
He felt stupid. Hotels, dinners, virgin bullshit, he fell for it all. And he knew why. He was playing out of his league, she must have seen right through his humbler-than-thou routine right from the start. It was a tough thing for him to admit, being taken in by a young girl, but he did it.
As far as Alan was concerned they were through. He didn't even want to tell her, just withdraw, not ask her out again, let her know she beat him. He toweled off and started up the side ladder to his chair when he heard the door open.
It was Grace Cunningham coming from the poolside membership office. She didn't smile or acknowledge his presence until standing below him on the chair. "I'd like to see you in my office, Alan."
She turned and guided her swinging body around the deck chairs back to her office. That's when Alan noticed how dressed up she was. High heels, nylons, a tight skirt around her jutting rump and business-like suit jacket. He came down from the chair and followed.
Her office was modest, a simple affair with carpeting, several palm plants and a large desk. She quietly motioned for him to sit in the chair across from the desk. Her whole attitude gave Alan the premonition that he was about to be looking for a different job.
She cleared her throat and stared directly into his eyes for several moments before speaking. "Do you like working here, Alan?" she asked.
He knew it. That was the way someone began firing you, he was sure. "Uh… Yes, Mrs. Cunningham."
Her eyes flickered for a split-second and Alan was sure she took a quick peek at his crotch. "Do you want to keep your job here?" she asked.
He swallowed. This was it. "Yes, ma'am, I do."
She didn't spare a punch. Her eyes cut into him as she said, "Then stop taking out my daughter."
The ice-cold threat of her words made Alan sit in stunned silence. There was nothing nice about the way she said it and he felt a touch of rage building. "What does my taking out Teresa have to do with my job?" he asked.
"Nothing, except that I'm her mother and your boss. I have bigger plans for her than you fill and I believe she's taking you too seriously. Therefore I want it stopped."
Alan started to boil inside. "Bigger plans than I fill?" he asked with a shrill voice.
Grace smiled. "Alan, you know what I mean. I want Teresa to go to college, a good college. I want her to have all the advantages I didn't have."
Alan couldn't believe his ears. "What advantages didn't you have?"
"That's not the subject. What I'm telling you right now is that I disapprove of Teresa running around with a lifeguard. And I want it stopped. You understand that, don't you?"
"Yes," answered Alan.
"Good. Then it's settled, no more asking her out," said Grace.
Alan looked into the pleased smugness of her eyes and said, "I'm sorry you feel this way. I'll get another job."
"That won't be necessary. Just stop showing interest in her and everything will pass."
"No. I'm still going to ask her out, Mrs. Cunningham," said Alan. "I'm not going to let you dictate who I can and can't socialize with."
The pleased pink of her cheeks became a vivid red. "Why, of all the impudence! You're a very impolite young man!"
"I'm learning fast, Mrs. Cunningham." He stood. "If it costs me my job I don't care… "
"Wait, Alan." Her manner changed. "You're in love with her aren't you?"
He shot straight. "No. No, I'm not in love with her. But maybe she's in love with me."
She inhaled. Grace hadn't expected this turn of events. She was sure their relationship was still casual enough for a split-up to be no big thing, but Alan's stubborn defiance could make it into much more than it was.
"I'll see that you get a raise," she offered.
"Money? Now you're trying to buy her out of it?" he asked. Suddenly Alan knew he wasn't interested in maintaining a relationship with Teresa, it was Mrs. Cunningham's self-assured manner that angered him. He wanted her to squirm.
"I'm trying to buy you out of it!" she snapped back.
"Sorry. I'll get a job elsewhere and just keep taking her out," he quietly said.
"I won't allow it!"
"How can you stop it? If she wants to see me she'll find a way."
Grace knew he was right. Teresa had ways of getting what she wanted, stubborn ways, just as stubborn as this young man's. "What can I offer you to make you see it my way?" she finally asked.
Alan shrugged. "Nothing, I guess."
Grace was in a panic. The little bastard was putting himself above the offer of money, he didn't seem upset about losing his job, what was his price? She stood up and walked to the window of the office. Slowly she pulled the drawstring on the curtain until it closed.
When she turned Alan saw the dead seriousness in her face as she said, "What if I offer you something better than my daughter?"
He knew exactly what she meant but asked anyway, "What do you mean?"
"I mean me." Her statement was level, serious.
"You?"
She removed, her suit jacket and undid five buttons one after the other down her white blouse. Without hesitation she opened the blouse to reveal the lusciousness of her bare, large-nippled breasts.
"Yes, me."
Alan stared at the soft, meaty tits and felt his cock growing swiftly in his swimsuit. They were absolutely beautiful jugs with pure white triangles of untanned flesh framed by the gold of her chest and stomach. The nipples were a lush pink and appeared pulpier than Teresa's. The breasts tantalizingly swayed before him.
"You mean…?"
"Exactly," she interrupted. "Promise me you'll leave her alone and I'll show you a time you never imagined possible."
"And my job?"
"You can keep that too. Just promise me you'll stop asking her out, stop paying attention to her."
Alan's cock was about to rip through his swimsuit and she knew it. It couldn't be missed. The thick spike was obviously aroused. Grace finally felt she was bringing the situation back under control. She didn't like the idea of screwing this young buck but he drove a tough bargain. If it meant getting Teresa back onto the proper social level it would be worth it.
"Okay," Alan said.
"Fine."
Alan watched as she walked to the office door and locked it. The swaying volumes of breast rocked from side to side but didn't once sag. Somehow her older body was turning him on much more than Teresa's ever did, perhaps it was the unusual situation, the cold businesslike attitude of Grace. Whatever it was, Alan realized he had never felt so eager, so hungry to get his hands on a body.
Grace smiled warmly now and let it be known the bartering was over. Any bruised feelings or hurt egos would be forgotten now that the time of pleasure had arrived. She stood beside the office sofa and kicked off her high-heeled shoes. Then she reached up underneath her skirt to expose the length of her long legs and grab the tops of her panty hose. She rolled them down the smooth, tan flesh of her legs.
As she undressed Grace kept a good eye on Alan. She liked his looks, his clean, simple manners and unaffected personality. He was a raw man without the complicated socialization of the men she was more accustomed to. No wonder Teresa goes for him, she thought, he's a breath of fresh air in an otherwise stuffy atmosphere.
While she unzipped her skirt she thought about Mr. Cunningham, Walter. Dear Walter, hard-working Walter. He was a doll of a man but boring. His world consisted of profit columns and production schedules Grace had no desire to understand or even ask about. And he seemed happy in his world of high finance, happy with his beautiful wife and daughter, content enough to not even be aware of his wife's extramarital activities.
Alan knew what her legs looked like, he knew what ninety-percent of her body looked like but now, now as she removed the endless array of garments it all seemed so different. The red lines around her waist where the panty hose had gripped gave her a human, vulnerable quality. The simple act of undressing before his eyes made Alan fidget with anticipation and a small amount of nervousness.
After all, he was about to join bodies with a fully mature woman of wide experience and some knowledge. The fear he might not perform up to par was undermining his self-confidence. He wasn't about to initiate a virgin, fake or not; no, this was a total woman.
Her high patch of ebony-black pubic hair glistened with health in her crotch as Grace sat on the sofa and smiled. She was waiting for him to remove his swimsuit. Alan's eyes traveled from her breasts to her crotch, to the sleek legs and back to the beige-pink nipples. He slid his hand inside his trunks and worked them over his erection and down his legs.
His nervousness flooded away the instant he realized Grace had moved. As soon as the flared, red head of his cock popped into sight Grace slid from the sofa to her knees and came to him like a praying sinner. Her mouth was wide open as she tilted her head up to engulf the dazzling beauty of his young, firm rod.
She sucked the meaty column into her lips with one-inch lurches and paused for air. Bit by bit she chomped down the length of his pounding-hot cock until it disappeared totally inside her. She washed her head back and forth to grate the head of the giant against her stuffed throat.
"Mmmm!" she moaned with total delight.
Alan's knees felt weak as she inhaled his cock with complete abandon. The sophistication had left Grace Cunningham with her clothes. Now she was nothing more than a woman going insane with desire for his cock.
He could feel her tits caressing his thighs as she energetically pumped her sucking mouth up and down. Her hands came up behind him to cup and snuggle into the crack of his ass. The thrilling shudders of joy rippled up and down his back as her fingers probed into his warm crack to find his asshole.
Alan didn't have a chance. Her index finger found the mark and started following the ring of his ass around and around. It felt too good for him to do anything but enjoy it. Then the probe dug inside the tight muscle and he felt her slipping deep into the exploding regions of his ass.
She sucked hard and pulled back with her teeth softly grating his cock as her finger dipped and twisted to drive him up a sudden wall. Alan's body went tense and she plummeted down hard on his cock just as it gushed. The thick honey of his balls filled her mouth, coated her tongue, ran in streams down her gulping throat.
She kept gouging with her finger as lurch after involuntary lurch came from Alan's hips. He swore he was still pumping juice in her mouth long after his usual climaxes ended. But the finger was driving him, causing him to make jerk after jerk into her sperm-dripping lips.
Grace took each glorious cram of cock like her mouth was a pussy. As he withdrew she sucked hard with her lips to draw all the delicious cream back to her gulping throat. She devoured him, licked hungrily at his scrotum as if she were urging it to pump out more of the delicacy, kissed up, down and around the glistening muscle.
Her finger slowly eased from the depths of his anus and Alan whispered, "Wow… "
She grinned. The spot of sperm on her cheek destroyed anything that was left of the overbearing boss-lady image. She was greedily waiting for more of the steel-hard pecker. Grace slowly rose, brushing her tits against his cock, his stomach, his chest on her way up. Finally she wrapped her arms around his neck and thrust the flat of her stomach against his. Alan could feel the soft fur of her cunt tantalizing his cock.
It was still up. Erect, stiff, ready. She wrapped a hand around the massive base and slowly urged him to the sofa.
"I want to feel this beautiful cock inside me," she said with a deep-throated voice.
She sat with her legs far apart, the gleaming red lips of her heated, wet pussy stretched up and out to give Alan a good look. It was the full-fledged cunt of a woman; strong, muscular tissue heaped alongside the folds of redness let him know she could work her cunt any way she pleased.
"I want to feel the inside of your pussy," he said.
Her legs parted even wider as he reached down and put a finger into her juicy heat. The soaked lips slid easily apart to expose the boiling pinkness of her inner tissue. Alan slipped a finger deep into the hole and touched the super-soft lining of her smoothness.
"Yes," she sighed. "Oh yes… "
He came back out and worked up to the lumped knob of her clitoris. As he pressed hard against it she shivered, the nipples of her breasts immediately started to draw up to puckered cones. He worked the clitoris back and forth as his mouth came down to suck at each taut nipple, to draw it in deep and bounce it between his teeth.
Grace's hand was pumping with terrific speed along his cock but Alan knew he had nothing to worry about now. He had climaxed once, it would be quite a while before he did it again. And this experienced woman had somehow managed to keep his tool stiff, keep it up there where it belonged.
"Eat me," she was hissing in his ear. "Eat my cunt, please. Eat me…" she begged.
Alan moved his face down to her thighs and felt the cooking heat of her crotch. The odor of ripeness filled his nostrils as his tongue came out to touch the pussy lips.
"Umm… " she groaned, Grace loved nothing more than to have her box sucked. It was the one thing she went berserk over and the one thing she couldn't get enough of. Even the times her husband did it, or one of the select gentlemen she met with, never seemed to really satisfy her. But this youth, this child was making her cunt cry tears of anticipation even before his tongue was inside.
Alan brought his flat tongue upward in a wide sweep across the drooling gash and felt her hips rise and push to him. The hair was tickling his nose, her thighs were brushing against his shoulders as she gave him wide berth. He stabbed in far enough to find the clitoris and rolled it from side to side with increasing speed.
The faster he went the more animated she became. Her ass was lifting off the sofa and her thighs were clamping closed around his head then whipping wide back as his tongue vibrated the core of her cunt for endless minutes. Then Alan made the deep digging probe inside her flowing hole to feel the gushing softness.
He came out and went back to her clitoris and again she reacted with total abandon. He knew he had the key to her happiness in his mouth, the most sensitive spot. Alan worked diligently on the crystallized pecker of her cunt until her thighs crashed in on him to muffle her screams of delight.
"Oh! Oh! Uhhhhhh!"
Her soft ass was rubbing up hard against his chin, her hips were smashing hungrily at his sucking face as a passionate climax enveloped her. His whole head was buried between her humping legs as the payoff of sweet wetness gushed happily from her clamping cunt.
Finally everything was still and Grace dropped back on the sofa with flushed cheeks and heaving chest. The white areas of her body now beamed with hot pinkness, a smile Alan never saw before came across her face.
"Oh, I underestimated you, my fine friend," she whispered. "But you've shown me a whole new perspective."
He didn't know what she meant and didn't feel like asking. Alan was eager to sink his cock into the oiled cunt, to send it deep and take his time working up to an explosion. He lay upon her body, their feet on the floor and squirmed the head of his cock in tight against the welcoming yawn of her sighing box.
"Wait," she whispered. Then she rolled over until she was on her back.
Alan crawled into position between her legs and saw she was smiling that smile again. "It's your show, Alan. I'm bushed," she said.
He eased his cock into the firm grip of her cunt. It felt as tight, as small as Teresa's, only much softer. When she raised herself up to take more cock, the movement was smooth, exact, precisely what he wanted to feel. The head of his pecker slid all the way in and she grimaced with pleasure as it touched deep.
"Oh… that's good, that's the way it should be," she sighed.
Alan started slow, very slow. He wanted to feel the tender kiss of her vagina all along his rod. She was motionless for several minutes before making her first move. That was a high lift and sideways jerk. Alan's cock sank deep and rammed hard into one wall. She groaned.
He kept directing his plunges into the one wall and felt it grow amazingly hot, felt the friction increase as he smeared away the lubricating fluids. Now she was clipping at him from the side to help. Each stab hit right on target, right into a soft patch of tissue that was growing hotter and more sensitive each time.
Alan imagined a blister forming on the spot, wondered if it was a favorite spot of hers or if she just picked one at random to batter silly. But it was a gas carrying on the precision movements, he loved it. So did Grace. Her guts erupted with another orgasm to send the whole length of her twat into clapping spasms along his spike.
It was like a thousand tiny hands jacking him off, digging into the rim of the glans, punching, kicking, hugging his cock like a welcome hero.
"God! I can't believe it!" she screamed out loud.
Alan's ass was moving fast now, sending his pole deep and fast as the infection of her climax spread to him. He was proud as hell to have such a dignified lady going crackers under him, proud as punch. And punch he did. His fat-headed cock was jamming into her like the fist of a heavyweight prizefighter to ring the final bell.
Alan's back was aching from strain when he finally felt his second climax coming. It started off as a thought in the back of his mind and just grew. His head was reeling, sweat dripped from his temples, each breath was a lurching gasp as the thought became a true physical feeling somewhere down by his knees.
It spread upward to numb his thighs and make his nuts feel ten times their normal size. That's when he realized the ringer was in his ass again. He couldn't remember her sticking it in there, it was just there, twisting, rolling, stabbing down to inflame his guts.
He frothed over with one constant pumping action that didn't end until he was empty. Alan remembered the wonderful cushion of her breasts as he collapsed onto them, the comfortable hug of her happy arms around his shoulders. The cream seeped from his pecker to glue them together.
He could hardly hear her speaking. "You were wonderful, Alan, just wonderful… I'm so glad I stopped you before you got to Teresa… She'd never let you go if she felt as good as I feel now… "
Alan shook his head and tried to swallow the dryness in his throat. "Huh?"
"Oh, nothing, just relax, my dear, just relax."
"What did you say about Teresa? About getting to her?"
"It doesn't matter anymore, Alan. Forget about her. Now you're mine," she whispered.
"Yours?"
"Yes, dear, there's no reason we can't get together again," she said.
The idea didn't seem bad to Alan and anyway he was tired as hell. The last thing he remembered was Grace telling him not to worry about guarding the pool for a few hours, she'd get one of the other guys to watch. He needed his rest and should take a nap.
Like a well-fed Cheshire cat, Alan went to sleep.