Oasis 9

Anna opened the door. It was, as expected, her newest client. The experienced prostitute guided Tom inside her house, closing and locking the front door behind her.

Tom looked nervously around. This would be his first time having sex. Anna sensed his nervousness and used her calming voice.

"Welcome. Don't worry, I'll teach you all about sex and romance."

Tom relaxed a bit. Anna took him into the bedroom, then removed her robe. She was now naked.

"You should get undressed, too."

Tom stripped off his clothes, folding them and putting them in a neat stack on top of Anna's dresser.

"So, how much sexual experience have you actually had?"

Tom sighed. "I've done a fair bit of kissing, and a couple of times my girlfriend-at-the-time got topless and let me look at her breasts, but she didn't actually let me touch them."

Anna smiled. "Perfect. You have very little to unlearn. Now get on the bed."

Anna climbed onto the large, comfortable bed, and Tom did likewise.

"Okay, Tom. Give me a lover's kiss. Let's test out your kissing skills."

Tom placed his lips against Anna's, and the two of them twined tongues until they had to break for air.

"Not bad. Do it again."

Tom gave Anna another deep, tongue-twining kiss. She made him do three more before she was fully satisfied with his progress.

"Now kiss my neck," she instructed. "And remember to use your tongue a bit on the skin."

Tom placed his lips against Anna's neck and stuck the tip of his tongue out to touch her skin as he kissed it.

"Flicker your tongue a little and move your mouth along my neck as you kiss."

Tom did so.

"Better. Try kissing the other side of my neck."

Tom shifted his head and gently kissed Anna's neck, moving his lips and teasing the skin with his tongue. Anna made him do five additional kisses before she pronounced his technique acceptable.

"Now kiss through my cleavage."

Tom took an up-close look at Anna's soft breasts. They were huge.

"Like what you see? They're F-cups."

Tom nodded. He moved his lips up and down through the prostitute's cleavage, flickering his tongue like he had done while kissing her neck.

"You're a quick learner. Do it again."

Anna only required Tom to kiss his way up and down through her cleavage three times.

"Now lift my breast and kiss your way up from the base to the nipple."

Tom slowly kissed his way up Anna's giant orb, tracing a gentle line with his tongue.

"Now do the same for my other breast."

Tom duplicated his movements. Anna nodded approvingly.

"Now open your mouth and start sucking on one of my nipples. Use the tip of your tongue to flicker gently across it."

Tom eagerly began sucking on Anna's nipple.

"Use your hand on my other breast. Caress it and tease the nipple with your fingertips."

Tom obeyed. Anna's breathing deepened slightly as he suckled her and caressed her plump breast. He switched between her breasts several times.

"Now kiss my belly."

Anna's belly was rounded -- only teenagers have washboard-flat stomachs. Tom kissed the curve of it, then teased her belly button with his tongue. Anna giggled.

"Now my thighs."

Anna spread her legs. Tom got between them and kissed and caressed her large thighs. Anna made soft moaning sounds.

"Good boy. My pussy is getting wet."

Tom kissed his way up Anna's inner thigh. Sure enough, he could see the juices starting to leak from her slit. He stuck out his tongue and ran it along her lower lips, tasting her nectar.

"Go ahead, stick your tongue inside," Anna suggested.

Tom slid his tongue between her folds. Now he could smell her intoxicating scent. He eagerly began licking.

"Swirl your tongue."

Tom moved his tongue in a circular motion. Anna's thighs wrapped around his head as she guided his finger to a little nub.

"Rub that, very gently."

Ton brushed his fingertip against it as he continued swirling his tongue. Anna's body began shivering with pleasure. Tom licked with more enthusiasm, and Anna's love-juice gushed. He lapped up as much as he could and kept right on licking and gently rubbing the nub. Anna's thighs tightened around his face and she had a second quick orgasm. He kept licking, and after her third orgasm, she unlocked her legs from around his skull.

"Your enthusiasm is admirable. That little nub I had you brush is called a clitoris. If you very softly stimulate it while using your tongue inside a woman's pussy, she will get very stimulated, just as I did."

Tom nodded. "Good to know."

"It's more than just good to know," Anna replied. "If you can get good enough at eating pussy, you can win the body of any straight or bisexual cis woman. They love when a man knows how to properly give oral sex."

Tom's eyes grew wide as he nodded again.

"Since you pleasured me with your mouth, it's now my turn to return the favor. Lie on your back."

Tom lay on his back. Anna kissed his neck, skillfully tracing gentle patterns on his flesh with her tongue. Tom's cock stiffened fully.

"Wow," he said.

"I know all the tricks," Anna grinned. She kissed her way to Tom's nipples and teased them with her tongue while caressing his thighs. Tom shuddered and his hips bucked slightly.

Anna moved her mouth to her client's inner thighs. She began running a fingertip up and down along his shaft as she did so. Tom let out a slight gasp.

"Watch this," Anna purred. She wrapped a hand around Tom's six-and-a-half-inch shaft and began stroking him. Her mouth moved to Tom's balls. Her tongue licked along his sac as she pumped him.

"Ooh!" Tom panted.

Anna sucked one of his balls into her mouth, continuing her hand's slow, steady movement up and down. Then she sucked the other one. She could sense they were starting to fill. Her hand slowed a bit. Her tongue sped up, tracing delicate patterns along Tom's balls. The old pro rubbed the tip of her client's cock with a fingertip. His hips bucked and he made a pleased moan. She switched hands, stroking him with her left hand now while she sucked his balls and used her right hand to rub directly at the base of his cock. His body tensed, and she could feel his cum boiling up. She slowed her hand even more, keeping him right at the edge as she teased his sac with her tongue. Then when she was ready, she sped her hand up and vigorously sucked his balls, aiming his cock backwards. Hot spurts of cum shot into the air, landing on Tom's belly and chest. Anna continued stroking and sucking until his cock started softening. She then cleaned his cum from his body with her tongue, swallowed it all down, and licked her lips.

"Let's rest a bit," Anna said. She lay on the bed, face up, and wrapped an arm around Tom, nudging his head onto her pillowy chest. They dozed off for about 20 minutes as their bodies recovered from the hot sex.

When they woke, they made pit stops and returned to bed. Tom again placed his head on Anna's comfortable chest as she held him.

"I know about you. You're a 19-year-old college freshman, and my contacts medically cleared you. Is there anything you want to know about me?"

"How did you get into this profession?"

Anna told her story to Tom. She'd always been curvy, and when she came to the college herself as an 18-year-old, decades before, she was a student by day and a stripper at the local club by night. Her curves would get her between one to three thousand dollars a night in tips, more if there was a special event -- one time the Mayor had personally tipped her ten grand. She would do "extra services" for an additional fee in the lockable club VIP rooms. She graduated college with a degree in economics, then became a stripper full-time. She was a millionaire by age thirty, bought the house with cash, and switched from stripping to being a hooker -- but only for the students at the college. (There were enough students taking summer classes that business never dropped off in those months.) Her contacts at the college would medically screen all potential clients before approving them. Local law enforcement never bothered her, because she wasn't out in public flaunting the goods, so the usual busybodies who whined about the streetwalkers ruining the neighborhood never had her as a target. Three consecutive Chiefs of Police -- two men and one woman, the current holder of the office -- had been her clients while they were students.

"A woman?"

"Yeah. I'm bisexual. If a student at the college wants my services, it doesn't matter whether they're male, female, enby, agender, cis, trans, straight, lesbian, bisexual, pansexual, aromantic, whatever. Anyone who pays gets to spend time with me. Lesbians need to learn how to pleasure a woman, too."

Tom nodded. Anna helped him off the bed, and the two of them ate a meal, then cuddled on the couch while watching a couple of movies. After another meal and a third movie, it was time to return to bed.

"One of the reasons I like young people is they recover quickly," Anna purred, stroking Tom's cock. "We've already done foreplay and oral, so now it's time for your dick in my pussy. And I want you to cum in me. When I had the cancer scare in my stripping days, the doctors did an oophorectomy on me as a precaution. Better to not be able to have kids than to die at thirty from cancer."

Anna had Tom rub her slit as she stroked his cock. When he was fully hard and she was dripping wet, she rolled him onto his back.

"Are you ready, honey?" Anna murmured.

"Yes," Tom replied.

Anna lifted her body upwards and lowered her pussy onto Tom's cock. She began sliding up and down, moving slowly at first so that Tom could get used to being in her.

"You can move your hips, honey."

Tom began moving his hips, thrusting upwards into Anna in the same rhythm she was using to fuck him. Anna leaned forwards, dangling her heavy breasts over Tom's face.

"Those are lovely," Tom observed.

"Would you like to suck on them?"

"Please."

Anna leaned even more forwards, and Tom lifted his head enough to catch one of her nipples in his mouth, He eagerly suckled on it as she sped her rhythm a bit, bouncing up and down on his cock. Her hands came down onto her bed so she could balance herself as she fucked him. Her pussy began giving his cock a squeeze every time she slid down. Then an orgasm ripped through Anna, and her pussy clamped around Tom's cock as her body shivered. His pole twitched inside of her.

"You're getting close," she observed. "Remember, I want you to finish inside me."

"With pleasure, dear," Tom grunted, his words muffled by Anna's nipple.

Anna locked her strong legs around Tom's hips. She wrapped her arms around him, clamping them around his head and smothering him with her massive chest. Her body trembled and quivered as she actively milked his cock with her experienced pussy. When she had another powerful orgasm, she locked the grip of her limbs even tighter. Tom was completely trapped and helpless as Anna forced every drop of his cum from his balls. Her vise-grip on his body didn't relax until her thirsting pussy had drained his cock of every bit of its essence and it was softening inside her.

Anna climbed off the completely spent young man and lay next to him. He looked dazed.

"I wasn't expecting... that," he said once he was again able to form words.

"But you enjoyed every bit of it," she smirked.

Tom nodded in agreement.

"When you make love to a woman and you really turn her on, things can get a bit out of control," Anna explained. "That's a good thing in this case. It means you made the woman very happy."

Tom smiled. He was still a bit shell-shocked by the force of the sex.

"Time to sleep," Anna said. She turned out the lights and lay sideways, wrapping her arms around Tom from behind and pressing her breasts into his back. Tom's body relaxed into her. Anna tenderly kissed the nape of his neck, and the two of them drifted off into dreamland.

When they woke, they did their morning routine and climbed back into bed.

"You have me until noon," Anna pointed out. "That's time for another sex lesson. We've covered all the basics: is there anything special you want to learn?"

Tom thought for a moment. "I heard some of the girls and boys in the dorms talking about anal sex. I should probably take advantage of being here to learn about that."

Anna smiled. "An excellent suggestion. Close your eyes for a moment while I make the appropriate preparations."

Tom obediently closed his eyes. He felt Anna secure something in his mouth and his arms being drawn behind his back. He then heard a clicking sound.

"A ball gag, and the handcuffs are padded for comfort," Anna explained. She positioned Tom on the bed, facing downwards, and spread his legs. He opened his eyes, as she told him the preparations were now complete.

Anna rubbed some lube into Tom's butt crack. "It's your first time, so I promise I'll be gentle."

Tom made an unintelligible grunt in response, as the gag in his mouth prevented him from speaking.

Anna's soothing voice was now a whisper. "Just relax, honey. Your body will adjust in a moment." With that, Anna slowly began pushing the strap-on she was wearing into Tom's virgin asshole. She moved a millimeter at a time until she was all the way inside. Then she pulled slowly back out a couple of inches, then pushed back in. Tom's body was already relaxing and adjusting. Anna continued to move slowly until she felt him start pushing backwards against her. His cock was quite hard.

"There you go, honey. Good boy." Anna pumped in and out, wrapping her arms around Tom from behind. The clitoral stimulator on the toy was doing its thing, and Anna shivered through first one, then a second orgasm. She pulled out, removed the strap-on, cleaned it, then uncuffed and un-gagged Tom.

"I think you liked your first experience with anal sex," Anna observed, staring at Tom's engorged pole. "But now you need to cum. And you need to learn about the other part of anal sex, in case the woman you're with is a sub who likes to take it in her ass."

Anna helped Tom lube up her butthole, then got on her hands and knees, jiggling her fleshy, thick, round rump at him.

"Be gentle, sweetie. Slow at first, just like when I was fucking you in the ass."

Tom pushed his dick into Anna's tight asshole. He moved slowly at first, then just like Anna had, he waited until her body had adjusted and began pumping his cock in and out steadily.

"I want you to cum in my ass, sweetie."

"Will do." Tom continued to steadily slide his dick in and out of Anna's ass. He leaned forwards and wrapped his arms around her, cupping and caressing her breasts.

"You can play with my nipples."

Tom lightly brushed Anna's nipples as he fucked her butt. She shivered with pleasure. Anna was now pushing her rear backwards, trying to get Tom as deep inside her as possible. Tom sped up his thrusting. Anna's body shuddered as she climaxed. Her ass locked around Tom's throbbing pole. The sensation was too much, and Tom injected her bumhole with hot jets of cum.

"Good job."

"Now what?"

"Now we clean up." Anna guided Tom to the shower, and the two of them thoroughly washed each other. Then they dried off, dressed -- Tom putting his clothes back on, Anna merely slipping into her robe -- and ate a meal.

"If you want another session, I would love to have you over again," Anna said as she walked Tom to the front door.

"I'll consider it," Tom replied. "You're more than three times my age. I think I'd like to use the skills I learned to find a college girl and bed her."

Anna laughed. "That is the idea. Well, you know how to contact me. Good luck."

She let Tom out the door, locked it, and checked her schedule. In two days, the Mexican girl was going to arrive...