Jennifer’s new underwear made her feel sexy and confident. It was almost a shame that she would be expected to remove them before long. She could barely stand the mixture of anxiety and anticipation as the elevator rushed her to the twentieth floor. It had been exactly a week since her last visit to the grand hotel in Boston’s Back Bay.

She arrived that evening as a naïve coed and left as an expensive call girl. Jennifer had experienced a thorough fucking by an epically endowed male counterpart, far beyond anything in her experience, for the viewing pleasure of a wealthy couple. She had been expecting to meet a middle aged gentleman that evening, her maiden voyage as an escort. Instead, a nervous Jennifer was handed over to the champion stud and ravaged while they watched.

Jennifer’s two closest friends, her sorority sisters, had introduced her to the lucrative arrangement – had, in fact, talked her into it. There appeared to be no shortage of affluent men willing to pay thousands of dollars for the intimate services of well-bred, refined college coeds. Both had secretly begun seeing gentlemen months before recruiting Jennifer.

Returning to campus after that first encounter, Jennifer immediately sought out her friends. Their mouths fell open as she described the scary, demeaning, and thrilling, experience in lurid detail.

“This black guy, Jamal? So, uh… he was really hung?”

“I think I peed a little when I saw it. Then when he got hard? God, you have no idea.”

Jennifer held her hands apart and the girls screamed in naughty delight.

“I’d be so scared! The guys they’ve been sending me to see have all been forty or fifty year old rich guys. Most of them are grateful just to come once!”

More laughter and squeals.

“So you never had people watch you ‘do it’ with someone else on these dates?”

“No! But, God, that sounds hot, Jenn. Mmmm… I’m getting wet just hearing you talk about it.”

“And the wife fingering you? Did you like it?”

“It was weird, but it made me so horny. I don’t know... it was like she could do anything she wanted to me. I was in her control.”

Now Jennifer was back for her second assignment. Her contact had told her the couple were very pleased with her and wanted to book her again. Based on what Olivia, the wife, had said that night, Jennifer was expecting a return engagement with Jamal. She also had a strong impression that Olivia was interested in taking part herself.

Walking down the hallway, Jennifer remembered Jamal’s long, shimmering phallus sliding in and out of her. Yet she couldn’t stop thinking about the possibility of Olivia taking things further. She knocked on the door to Room 2010. Once again, the striking forty-something answered.

“Jennifer,” she smiled. “Please come in. Don’t you look adorable?”

Jennifer’s friends had taken her shopping at some swank shops to spend some of her new found loot. This night, she wore a black wool pencil skirt, a white silk man-tailored blouse, and a black cashmere blazer. As a personal fashion statement, Jennifer added a ridiculously expensive pair of leather cowboy boots.

“Hello, Olivia. So nice to see you again.”

Jennifer stepped into the elegant suite, the scene of the most intense night of her life.

“Drink? Scotch, isn’t it?” asked Olivia heading toward the bar.

“Oh, yes, that would be nice,” replied Jennifer looking around the anteroom.

Jennifer felt a familiar case of nerves tighten her stomach muscles. She was still new to the sex trade, after all. She took a sip of the brown liquid and exhaled.

“Jennifer, I need to speak to you about this evening.”

Jennifer smiled at Olivia, expecting Jamal to appear again with a towel around his waist. Instead, she heard muffled voices coming from the bedroom.

“My husband, John, has a special request, if you will. Well, he and his brother actually.”

Oh no. Here we go again.

“Olivia, is this another …?”

“No. Dear, just listen to me before they walk in here,” Olivia said hastily. “This isn’t at all what you think.”

Olivia hooked her arm in Jennifer’s and walked her toward the double door. Jennifer felt a tingle at her touch.

“John and I have a son who will turn seventeen next month. In a year, he will be off to university,” she explained. “John’s brother, an idiot, I’ll add parenthetically, also has a son from his second marriage. He is a few months older than Jack.”

Jennifer had no idea why she was getting this tour of the family tree. She stopped and looked at Olivia.

“These boys have led a rather sheltered existence, what with nannies, prep schools, and the like,” Olivia searched for the right words. “They’ve had no real... life experiences.”

Jennifer suddenly realized where this was going. 

“John and his brother feel it is time the boys, as some might phrase it, became men.”

“Oh Olivia … you don’t mean …”

“Dear, let me just say that your fee has been doubled for this evening’s engagement,” Olivia said urgently. “And, if it means anything, you would have my gratitude. My husband is not a pleasant man when he doesn’t have his way.”

“Uh, Olivia, I’m no expert, but isn’t this the sort of thing a man would take care of? I mean, why are you …?

“John is out of town and insisted this be arranged quickly,” Olivia interrupted with a wave of her hand. “And, as you might have inferred, his brother can’t be trusted with a... a delicate arrangement such as this.”

As the doors swung open, Jennifer was horrified. Before her stood two very young-looking, very nervous, teenage boys.

Jennifer looked at Olivia and back at the teens. She felt a desire to please Olivia that she didn’t quite understand. And a double fee? She stood to make nearly four thousand dollars. Still, she’d only had four sexual partners in her life, including the estimable Jamal. And now she was to service two prep school boys? Together?

Jennifer thought for a moment.

“Wait.”

Jennifer quickly made for the bar and returned with three bottles of Heineken.

“Can’t hurt,” she said to Olivia with a shrug.

Olivia rolled her eyes and stalked into the large bedroom.

“Jennifer, this is my son, Jack.”

An athletic-looking sixteen year old shook her hand. He was handsome, like his father, with a strong jaw and a head of wavy black hair.

“…and this is my nephew, Ryan.”

The thin blonde teen smiled wanly as he was handed his beer.

Olivia moved to the double doors, motioning Jennifer to her side.

“I’ll knock on the door in ninety minutes. I can’t imagine you’ll need more time than that,” she whispered, looking the two teens up and down. “Oh, and please remember to be discreet about our previous meeting?”

Mother of the year, thought Jennifer as the doors closed. She was alone with the two young males, who regarded her warily. Jennifer’s breathing began to feel labored. She knew that, in a very short time, these horny teenage boys would be pawing her naked body.

I’ve got to stay in control.

“Drink up and stand here in front of me,” said Jennifer, removing her blazer and plopping into a cushioned chair, “We need to get to know each other. I’m Jenn, as you heard.”

Jennifer took a long pull on the beer and slouched back in the chair. She folded one leg over the other, not the ‘ladylike’ way, but rather with her right ankle resting on her left knee. My God, she thought, these guys are about my brother’s age. Maybe that is why she didn’t mind the way the boys not-to-discreetly sneaked peeks between her legs. Anyway, they would see more than her panties soon enough.

“Are you nervous?”

“No!” they answered in unison.

Jenn smiled into her beer bottle and shook her head. Men. They're all the same. She knew that, at twenty years old, with her 120 pound frame, long legs, and nice boobs, she was a walking wet dream to these two.

“So, I guess you know why we’re all here tonight?”

“Are... um... are you a prostitute?” asked James, haltingly.

Jenn froze, trying not to let them see that this eminently reasonable inquiry rattled her to the core. Strange how she had never thought to ask herself the same question. Not even after seeing nearly two thousand dollars appear in her special bank account a few days ago.

Stay... in... con... trol.

“Let’s just say that, if you don’t ask any more stupid questions, I’m the one who’s going to get you laid tonight.”

Ryan looked at his feet and tried to suppress a chuckle. Good, he has a sense of humor.

Jennifer wracked her brain to find a way to break the ice.

“Okay, let’s play a game,” she said. “You two need to undress down to your shorts. You’re not shy are you? Wait… I’m not finished,” continued Jennifer. “With each article of clothing you take off, I will ask you a question. You will answer honestly.”

Make sure you keep the upper hand, Jenn.

“There’s a reward at the end.”

The young men loosened and pulled off their school ties.

“Ties don’t count. Get rid of them,” ordered Jen. “Shoes and socks either. Get them off and we can start.”

This might be fun.

The cousins did as instructed and faced Jennifer.

“Shirts”

The boys began unbuttoning their white shirts and pulling them out of their dress trousers.

“Okay… have either of you gentlemen ever had sex before?” asked Jenn. “Don’t worry; Jack’s mother isn’t here now. You can be honest.”

The tee shirt clad preppies mutely shook their heads no.

No surprise there.

“Okay, fine. Tee shirts,” she continued. “Ever gotten to third base? You know, fingered a girl’s cooter?”

The two bare-chested lads answered by examining their toes.

“Pants now guys… that’s it. Okay, let’s see… ever feel a girl’s boobs?”

Jack perked up as he stepped out of his grey trousers.

Hmmm, nice legs.

“I felt up a girl from Sacred Heart at a dance last semester!” he reported. “She wouldn’t let me put her hand under her shirt, though.”

Bitch.

Jennifer finished her Heineken and wished she had another.

“Okay, what about you, Romeo?”

“Well, no… but… Jack’s older sister did let me look at her boobs twice last summer.” He looked at his partner. “Sorry.”

“S’okay. She showed half the football team."

“Alright guys, it’s the moment of truth. If you really want to do this, it’s time to slide off those undies… C’mon, don’t be shy,” purred Jenn. “Now, I am going to ask you a question.

I have a brother your age, so I’ll know if you lie to me. If you tell the truth, you can help me get undressed.”

I want to see the merchandise first.

Jennifer stood up now and focused her gaze from one set of blue eyes to the other. The boys held their breath in anticipation.

What would they least want to admit? Oh, of course…

“How often do you masturbate?”

Ryan’s eyes widened in alarm. Jack’s face went beet red. Jenn looked down.

“The shorts, gentlemen. NOW. How often, Ryan?”

And show me your cock.

Ryan pulled his jockeys over his feet and straightened up. His flaccid penis and balls were cradled in a nest of curly brown hair. His dick was covered with folds of soft skin. As thin as he was, Ryan had nice, broad shoulders and was lightly muscled over his chest, arms and legs. He definitely had potential.

Embarrassed, the teenagers avoided looking at each other.

“Well … I … I like to do it whenever I shower.”

Jenn began to feel a warm glow on her skin. She turned to Jack, who was shaking slightly. She appraised his genitals just as his parents had done to Jennifer in this very same room. His dick looked meatier than his cousin’s, and his testicles hung low. About the same height as Ryan, Jack had a sturdier build, a flat stomach, and a narrow waist. He reminded Jenn of a lacrosse player she had dated in high school.

“You?”

“I don’t maaa… I mean… uh… I guess about twice a day,” he said resignedly.

“Maybe more, huh?” Jennifer smiled. “Okay, good. You guys are honest, at least,”

Jennifer shuddered slightly. Their nakedness was beginning to have an effect on her.

They seem like decent kids. I think I can enjoy this if I can just relax.

“Alright Jack, you can unbutton my blouse. Ryan, my skirt has a zipper in the back.”

Jennifer felt a flutter in her tummy as the naked youth shakily undid the ivory buttons on her silk top. He smelled really nice. She looked down and gently took Jack’s slightly plump cock in her hand and began to squeeze it slowly. Jack’s body jerked and he began to breathe through his mouth.

“Feel good?” Jennifer asked quietly.

It feels good to me, Jack.

Jennifer felt Ryan fumble clumsily with the catch on her new skirt before hearing the zipper being lowered. Her shirt was now open, covering her breasts, but affording Jack a partial view of her lacy bra. She felt a tug and a surge of adrenaline as Ryan pulled her skirt down to the floor.

Jack pushed the blouse off Jennifer’s shoulders. As it fell to the floor, she sensed her nipples push against the sheer cup of her bra. She reached back, found Ryan’s hands, and pulled his arms around her. He caressed her flat tummy and drew his shaking hands over her hips. Jennifer felt his taut body press against her panty-clad behind.

Mmmmmm…

“Remember to breathe, boys.”

Remember to breathe, Jenn.

Jennifer stood between the astonished teens, clad only in her skimpy undies and her new cowboy boots. Jack was growing in her hand. He let out a low moan when she began to rub a thumb over the head of his penis.

“Ryan, there is a clasp in the back of my bra,” she said hoarsely.

After some fidgeting, the flimsy garment fell away, causing Jennifer’s boobs to bounce freely in front of Jack. He stared at the soft, round beauties as if in a trance. Then, without waiting for instructions, he grasped the material over Jennifer’s hips and carefully lowered her panties to the floor. Jack crouched in front of her neatly trimmed bush, staring at her little slit. Jennifer felt her skin tingle and a release of wetness in her vagina as the two teens stripped her naked.

Oh God… Okay, I need to stay in charge here.

Jennifer took a few steps away, and turned to face the two, before doing a slow 360 degree turn for them. Her long, slightly bowed legs seemed tailor-made for the leather cowboy boots. Jack stood up. He made no effort to hide his growing erection.

Jennifer tried to execute a sexy smile and got on her knees, motioning with her index finger for Jack to come forward.

Time to show me what you’ve got, Jack.

“Ryan, I’m going to suck you cousin’s dick and make him come in my mouth,” she said, looking at his dangling, semi-hard member. “I expect you to have a nice stiffy by the time I’m finished, okay?”

So I can deflower you.

Jennifer turned her attention to Jack. He had a pretty cock, she thought. It had grown out nicely and fattened up. It was smooth and moist looking with a ring of dark pigment around a pink shaft. Most importantly, it was rock hard.

There’s nothing like a quality erection to make a girl feel appreciated.

Jack flinched when she closed her fingers around his rod and licked beads of clear liquid from his slit. Jennifer pushed her moist lips over the juicy bulb and onto his stiff shaft. Her nipples ached with arousal and she became aware of her pussy. She experienced a sort of primal sexual response to being on her knees as the virile young male slid his turgid penis in and out of her mouth. Jack reached down to feel her breasts and squeeze the erect buds. Jennifer moaned.

Oh, I love that, you idiot …

Not surprisingly, Jack didn’t last long. His body stiffened and convulsed as his warm teenager cream pumped into Jennifer’s mouth. Jennifer sucked on his sensitive glans, refusing to release him until she swallowed the entire rich, salty load.

Ryan stared wide-eyed at the exhibition.

“Are... are you gonna do that to me?”

He was lightly stroking his hardened tool. Jennifer gave it a careful inspection. The erection stood up at a forty-five degree angle. It was straight as an arrow and longer than Jack’s, but noticeably thinner. Like Jack, he was circumcised.

“No, not yet, Ryan. I’ve got a job for you,” she answered. “Get over here.”

I need to get off so I can stop trembling.

Jennifer sat on the bed and pulled off her bootsand socks. She leaned back on her hands. As Ryan cautiously approached, she spread her legs wide. Both boys stared open-mouthed at the pink ribbon between her slightly open labia.

“You can see that I’m wet now, right? And how my pussy lips are kind of dark and swollen?” asked Jennifer, slightly out of breath.

The teens nodded dumbly, transfixed by the vision of the Holy Grail.

“Somehow, you two virgins have managed to make me horny.”

I want to get fucked as much as you want to fuck me.

Jennifer slid further back onto the bed and motioned Ryan forward.

“I’m going to teach you how to eat my pussy now,” she said. “Some day, you’ll both thank me for this.”

First Ryan, and then Jack, followed Jennifer’s quiet instructions. They kissed her warm belly softly, while lightly running their hands over her shoulders, breasts and hips. They nibbled at her toes and slowly worked their hungry mouths down each leg to lick and tease her inner thighs. One by one, they planted light kisses all around her pussy before inserting a tongue between her labia. She taught them how to torture her with their fingers and let them know how and when to attend to her charged clitoris. Jennifer stretched out on the bed and climaxed elaborately as Jack finished his lesson.

Mmmmmm… can I take you two home?

Jennifer opened her eyes to see Ryan standing next to the bed, his rigid pole still at attention. It looked irresistible.

Right. I owe you a blow job.

Jennifer scooted around on her back and hung her head over the side of the bed. She had never tried this position but her sorority sisters said that guys really got off on it.

Ryan widened his stance and, with his hand, pointed his dick down toward Jennifer. She slipped her tongue over her lower lip to accept him into her open mouth. Ryan groaned as he slid easily to her throat. She fought the urge to gag and began to suck. Ryan leaned over Jenn with his hands on the bed. She inhaled his male musk while his balls bumped into her nose when his hips rocked forward.

That’s right, come for me, baby.

“Spread your legs, Jenn.”

Unseen hands pulled Jennifer’s legs apart and she felt an instant of panic. She knew she was completely vulnerable. She couldn’t lift her head to see, with Ryan’s phallus in her mouth. There was some movement and Jennifer could sense Jack kneeling between her legs.

Ohhhhhhh, baaaad boy…

Then came the inevitable and unmistakable sensation of a cock head moving between her dripping labia. It slid up and down, which felt lovely, but Jennifer knew what Jack was trying to accomplish. She reached down to position him at her opening. He pushed deeply into her cunt in one powerful stoke.

“Ooooh, this feels so good Jenn.”

Ooooh, this feels so good, Jack.

The tide had finally turned and Jennifer reveled in it. She stretched her arms up to grab Ryan’s cheeks and lifted her ass off the bed. Ryan fucked her mouth, while Jack fucked her tingling cunt with impunity.

Jennifer felt hands exploring her body, touching everywhere and squeezing her sore nipples. Fingers dove between her cheeks to probe her wet anus. Her engorged clitoris was teased without mercy. Jennifer had no will to stop them and she gave herself completely to the young studs. She came in waves when she felt Jack shudder and shoot his hot load into her. Seconds later, Ryan filled her mouth with semen and she drank dutifully.

The three collapsed together in a heap of flesh. No one moved or spoke for several minutes.

“So, do you feel like men now?” Jenn wondered lazily.

“Jenn, do we have time to fuck some more?”

Jennifer laughed and looked at the clock on the nightstand. They still had about forty-five minutes before Olivia would break up the party.

Yes, they fucked some more. She particularly enjoyed being held across the large oak desk by Jack while Ryan took her from behind. They were still naked when Olivia knocked on the door to collect the cousins.

“My dear God!” barked Olivia, surveying the wrecked room that smelled of sex and sweat. “Put on some clothes and meet me in the lobby, you two.”

Jack and Ryan grabbed their things and scurried around the room while trying to cover themselves. When they retreated to the master bath, Olivia turned to Jennifer.

“I really did not need to see my son’s erection,” said Olivia. “So… it appears that everything went satisfactorily?”

“Everything is definitely in working order.”

Olivia openly gazed at Jennifer’s lithesome body before holding open a fluffy bath robe. Jennifer slipped into it and tied the string around her waist. She had that funny,‘Olivia’ feeling again.

Take me home with you.

“You know, Jennifer, you and I may not be as different as you might think,” mused Olivia. “I was not always… the way you perceive me now.”

Jennifer was intrigued by this but remained silent.

“I told you last time that I want to see you again, and I do,” said Olivia, brushing stray locks from Jennifer’s face. “We must get to know each other better.”

With that Olivia smiled radiantly. It was like a ray of sunlight breaking through a cloudy sky. Jennifer melted.

“Until next time, then.”