Well dressed guests milled about, no doubt waiting for hired cars to take them to dinner or the theater. The opulence set her mind at ease. Nothing bad could happen in a place like this.
Jennifer was in her third year of studies at a prestigious university in Boston, USA. She came from a reasonably well off family. Her tuition was certainly dear enough. Yet the demands of sorority life proved to be expensive – fashionable clothes, house parties, and train tickets to New York, just to name a few. The money saved from summer jobs had nearly run out and Jennifer’s parents were not frivolous when it came to stipends.
Jennifer headed for the bank of elevators, where a thirty-ish couple with two small, restless boys waited. The woman smiled at Jennifer and raised her eyebrows in mock exasperation. I wonder what she would say if she knew why I am here, she thought. She noticed that her heart was beating faster.
Recently, two of Jennifer’s sorority sisters seemed to be flush with funds. She had visited their homes during school breaks and knew that they were not particularly wealthy. Neither did they have jobs on campus. She started questioning them and, at first, their explanations were vague, even implausible. One evening in her room, the pair waited for Jennifer’s roommate to leave and then swore her to secrecy.
They revealed that they had been introduced to a woman who arranged assignations between fresh faced, educated young women and mature gentlemen of considerable means. They typically had dates about twice a month, for which they were paid $1,500 to $2,000. Jennifer squealed with shock and excitement.
“What!? You mean like escorts?”
“Exactly like escorts.”
“You have sex with them???”
“Yes, Jenn, we have sex … but it’s not like it sounds. These men are sophisticated and polite. We usually meet at a nice restaurant or theater. They’re typically traveling here on business.”
“But they’re old, right?”
“Well, yeah, forties and fifties mostly … but don’t let that fool you. They’re experienced and know how to please!”
Jennifer was astonished. Her two closest friends were, well, … call girls! She peppered them with questions. The three howled and laughed at some of their answers. Then her friends made Jennifer an offer.
The woman who made these profitable arrangements was looking for another college girl, due to increased demand for her impressive young ladies. They described Jennifer to her and she sounded interested.
“God, no! I couldn’t!”
“Please, just think about it! You’ll have so much fun – and money!”
“But what about David?”
Ah, yes, the boyfriend. Jennifer had been seeing the computer science major since sophomore year. He was attentive and reliable. Their sex life was predictable. They typically fooled around after Saturday night parties or dates. He was a gentle lover, if not adventurous. Jennifer hadn’t had many men to compare, but his equipment was, in his words, average.
“Jenn, do really think you’re going to marry David someday?”
“Well, no … but …”
“Yes, he’s nice, we know. And not bad looking. But Jenn, there’s a big world of virile, exciting men out there. You’ll see!”
That night, Jennifer could hardly sleep. She fingered herself, thinking about tall, dark, handsome strangers. The thought of being paid to get naked and fornicate – to be the object of desire – soaked her panties.
Two days and two sleepless nights later, she said she’d do it. Arrangements were made. A new email address and bank account were set up for the strictly confidential transactions. She was sent to a clinic in a swank part of town to be checked for STDs. When all that was done, she received a professional-looking questionnaire to complete. Of course, her two cohorts assisted with its completion.
Name (first only): JENNIFER
Hair Color: LIGHT BROWN
Height: 5’ 10”
Weight: 120 lbs.
Bust Size: 34-C
Orientation: STRAIGHT, BI-CURIOUS (This last answer caused no small measure of shrieking and giggling.)
Relationship: UNATTACHED (Sorry, David)
Sexual Experience (Total Number of Previous Partners): 3
Prior Same-Sex Experience? NO
List Off-Limits Activities: S&M, BONDAGE, ANAL, WATER SPORTS, ANIMALS (More hilarity ensued.)
The questionnaire went on to uncover more personal information and preferences. When completed, the trio scanned and emailed it with a head shot to the address on the form.
Two weeks later, here she was, stepping off the elevator on the twenty-first floor of a posh hotel. As she headed to room 2110, Jennifer’s heart was positively racing. She stopped before knocking on the double door and thought about turning around. Suddenly, it seemed very real. She had a sheltered childhood and this was way, way out of her comfort zone. No, she thought, her friends had done this several times. Let’s do this, she told herself.
A well dressed woman answered the door.
“Oh, I … sorry, I must have …”
“Why, yes, I wasn’t expecting …”
“A woman, I know. It’s fine. Please come in, dear.”
As the door closed, a fifty-something gentleman stood up from a wingback chair with a glass in his hand. He wore a white dress shirt, open at the collar. His dress slacks were crisply pressed.
“Ah, Jennifer, please come in! I must apologize for surprising you. You see, my wife likes to join me to observe sometimes. I hope that’s acceptable?”
“Excellent! Well, then, this is my wife Olivia. And I am John.”
Jennifer was trying to process this on the fly. Her first time out was already kinkier than she had expected. Was Olivia really here only to watch? Damn, she thought, I shouldn’t have added ‘bi-curious’ to my profile. I’m not sure I’m prepared for that. At least not yet; not with an older woman.
Olivia was younger than John. Jennifer guessed mid-forties – about the age of Jennifer’s mother. She wore an expensive looking black silk dress that wrapped around her narrow waist. A string of pink pearls hung from her neck. She was actually quite striking. Jennifer wondered why John needed the attention of other women.
“Care for a drink?”
“Sure,” said Jennifer nervously. “Whatever you’re having.”
“Great. Thank you”
Jennifer tilted the rocks glass and felt the warm, brown liquid slide down her throat. She knew that she appeared nervous despite all efforts. She looked around the room. It was a rather large suite, actually. They were in an anteroom. Open double doors revealed an enormous bed in the next room. The covers had been pulled back, leaving only white sheets on top. That’s where I’m headed, thought Jennifer uneasily.
The couple had been told it was her first assignment. They made small talk about school and career choices as they tried to make Jennifer feel more at ease. Jennifer silently appraised John. She thought that, if not for the graying hair, he could pass for a much younger man. She was relieved that he was quite handsome. The scotch and conversation began to relax her. She actually started to feel a tinge of excitement as Olivia handed her a second drink.
“Let’s move inside and get more comfortable, yes?” said Olivia.
John held out his arm, gesturing toward the door, and Jennifer preceded the pair into the bedroom. Her knees were weak. Olivia and John took seats in upholstered chairs near the bed and Jennifer stood facing them.
“You look lovely, dear,” said Olivia. “Why don’t you start by removing your top for us?”
Jennifer was startled by the frank suggestion. Her mouth was dry and she wished for another scotch. She slowly pulled her winter white cashmere sweater over her head and shook out her thick brown hair. Her pink areolae peeked through the lacy half-cup bra – the sexy one her friends had bought for her. A delicate gold chain hung from Jennifer’s neck. Suddenly, she felt cold and vulnerable.
“Isn’t she lovely, John?” said Olivia. “Oh, you can just toss your clothes on the chair next to you, dear.”
“Now slip out of those slacks, please, Jennifer,” smiled John.
Jennifer felt her face flush. She undid the button in the back of her black wool pants and let down the zipper. She stepped out of her heels before pulling her pants over her bare feet. Jennifer felt embarrassed in front of the fully clothed couple and goose bumps appeared along her arms and legs.
“Beautiful,” said John. “Now, please turn around for us.”
Jennifer knew she looked good. Her boobs, more than a mouthful according to David, were firm. Her tight buttocks were nicely round and stuck out precociously. The rest of the package, she was sure, was fit from daily exercise.
“Now, Jennifer,” said Olivia, “We want you to meet our other friend.”
Jennifer blinked at them. She didn’t understand. Did she say, meet someone? She heard a door open behind her. Out from a changing room stepped a very black, half naked, young man. Jennifer’s heart stopped. She spun around to John and Olivia. Their eyes bore holes in her.
“Jamal, this is Jennifer. She goes to college in town.” said Olivia. “You will be enjoying each other’s company this evening.”
Jennifer turned back to Jamal in alarm. He was wearing only a white bath towel exposing a thickly muscled chest. His rippling arms were heavily tattooed. Jamal was older than Jennifer, maybe 25 or so. He moved across the room toward them.
“Wait. I thought … I wasn’t …” she spurted to the couple.
“He’s really quite something, Jennifer,” purred Olivia. “Have a look”.
Olivia made a gesture with her fingers and Jamal dropped his towel to the floor. Jennifer gasped audibly. A long, thick penis hung nearly halfway to his knees. Its substantial head curled forward under a fold of foreskin and swung ominously as he moved.
Jennifer had seen ‘monster cocks’ in porn videos the sorority girls liked to play at night for laughs. Somehow, she had always assumed it was some kind of special effect. This, this was all too real. This was nothing like David’s ‘average’ dick.
“Jennifer, dear, this is what we’ve paid for,” explained John patiently. “We’d like to watch this potent stud copulate with a delicate, white sorority girl. Your profile says you haven’t had much experience. Is that right?”
“Please, I’m not ready for this. I can’t …”
“Arrangements have been made and money has changed hands, Jennifer,” interrupted John. “You may leave now but your employer will not be happy when she returns her fee.”
Jennifer thought of her two sorority sisters. If she backed out now, they most likely would never get assignments again. Can she do this? She looked at Jamal. Deep inside, she was titillated by the impressive naked man. She sometimes fantasized about black men when she played with herself. But this was no fantasy; this was very real.
She turned to John and opened her mouth, but no sound came out.
“Oh Jennifer, Jamal’s profile says that his penis is nine and one quarter inches when fully erect,” tittered Olivia. “I see no reason to doubt it, do you?”
“Jamal, why not help the young lady with the rest of her clothes?” asked John.
“Certainly,” answered Jamal.
Jennifer felt his torso press against her back. He was a couple of inches taller than she and Jennifer felt his fat snake press between her thinly clad cheeks. Jamal reached around and expertly released the catch in the front of her bra, allowing her breasts to spring free. Discarding the undergarment, he dropped to his knees and pulled Jennifer’s diaphanous panties to the floor. He inhaled deeply at the crack of her newly bare ass.
“Spread your legs please,” ordered John.
Jennifer complied, moving her feet apart. The couple stared openly at her pussy. Jennifer felt an electric wave of shame and excitement course through her body.
Back on his feet, Jamal’s rough fingers circled and squeezed Jennifer’s nipples, which responded by fattening and growing to his touch. His mouth nuzzled her slender neck and a tingle went all the way to her belly. She was paralyzed with nervousness and arousal.
“Jamal, I’d like to see those muscles at work,” said Olivia. “Won’t you do some push ups for us?”
Jamal assumed a plank position. Jennifer noted that his thick cock dangled nearly to the floor.
“How much do you weigh, Jennifer? One hundred twenty pounds, I recall? Olivia continued. “That will do nicely. Please lie on his back.”
Jennifer moved haltingly to Jamal’s side, hesitated, and placed a hand on the massive trapezius muscle between his neck and shoulder. She carefully stretched out on top of him. Jennifer’s hips bent over his boulder-like buttocks. Her sensitive breasts pressed against his muscled back as she reached down to grasp his arms.
Slowly, Jamal began to move up and down. The action of his muscles vibrated through Jennifer’s lithe body. As his buttocks clenched, she felt it in her pussy. His biceps expanded and contracted under her hands. As Jamal continued, he began to perspire. The fragrance of soap and shampoo mixed with the musky smell of his manhood. Jennifer’s chest and abdomen slid atop Jamal’s moist back. He pumped out pushups as if she wasn’t even there. The power and action of the rippling body produced a flutter deep in Jennifer’s tummy.
“Wonderful. That will do, children,” interrupted John. “Let’s get to the fucking, shall we?”
Jennifer dismounted the heaving stud and Jamal stood upright. His muscles were positively popping now and his V-shaped body glistened. Jamal’s penis was beginning to pulse with blood. He reached for Jennifer, drew her against his chest, and kissed her deeply on the mouth. Jennifer was surprised at the soft, wet movement of his lips and tongue. She felt warm and wet between her legs. Jamal slid his hand down there and began to massage her pussy with two long fingers. She collapsed against him.
Jamal stepped back; his fingers toying with the neatly trimmed triangle of hair covering Jennifer’s mons. He surveyed his quarry for a moment.
“You know what to do, girl,” he intoned deeply.
She supposed that she did. Jennifer sunk to her knees and took his rapidly hardening tool with both hands. She had no experience with anything even approximating this magnitude. She handled the cock gently at first, lifting it up and running a hand under lemon-size testicles. She beheld the weight and volume in her hands with a mixture of curiosity, awe, and dread.
“Mmmmmmmm,” he groaned.
This pleases him, Jennifer thought. She felt a flutter deep in her abdomen. She began to pump the growing tool and push the skin off the enormous mushroom. Clear liquid dripped from the slit. She looked up at Jamal’s eyes.
Jennifer knew she couldn’t take all of him in her mouth, not nearly. She tentatively drew her tongue across his glans and tasted his pre-cum before slowly sucking it into her mouth. Jamal’s hands were around Jennifer’s head and he slowly pushed his way to the back of her open mouth. She felt his magnificent shaft stiffen and elevate as Jamal withdrew and reentered multiple times. She could no longer grip the phallus completely with her hands.
“My God, he’s big,” gushed Olivia.
Jamal stood back with his proud boner pointed skyward. Jennifer ran her lips over the underside and gripped the balls that swung in front of her face. His entire body shone with perspiration. Jennifer noted with interest that his dick was darker than the rest of his skin, a rich, deep chocolate, except for the almost pink glans that had popped out of his foreskin.
Jamal extended a hand and helped Jennifer to her feet. She regarded the nine-plus inch erection with alarm. Her vagina leaked despite herself. Before she could even think, Jamal had swept her up into his arms. Her long legs wrapped around his narrow waist as he held her effortlessly. She grasped his muscled upper arms as he tilted her thin body back, nearly parallel to the floor. Jamal’s hands supported her shoulders and back.
Olivia and John were standing as Jamal moved closer for their viewing pleasure. Jennifer saw that Olivia was now wearing only a see-through black bra and panties. Jamal’s thick erection pointed upward against Jennifer’s tingling pussy. He rocked his pelvis and slid the shaft up and down her groove, pushing apart her pink lips. Each time his head neared her opening, Jennifer was afraid he would impale her.
“Ohhhhh … God …. Ohhh,” was all Jennifer could utter.
John simply watched stoically but Olivia reached over and very gently circled one of Jennifer’s nipples with a thin finger. Her touch was so soft, so different from Jamal’s calloused fingers! She lightly rubbed the tip of the erect flesh. The sensation, combined with Jamal’s cock rubbing over her clitoris, produced in Jennifer an orgasm that racked her body. Jamal suppressed a smile as she melted in his hands.
Jennifer was still in a semi-euphoric state when she felt herself being laid face down on the bed. These sheets are so clean and fresh, she thought. Now, large hands pulled up her hips and Jennifer was on her knees, head still on the sheets. She felt her cheeks being separated and held open. Jamal and Olivia stood behind her.
“She has a gorgeous ass, doesn’t she?”
“You bet, Olivia,” replied Jamal.
The familiar thin finger tapped and tickled Jennifer’s puckered button and slid gently up and down her wet slit. That’s nice, thought Jennifer. The finger slowly pushed into her vagina and moved around slowly before easing back out. Jennifer found herself aroused by the attentions of another female.
“She’s all yours,” said Olivia.
A flat, warm tongue bathed Jennifer’s anus with saliva. No one had ever done this to her before! It felt so dirty and wrong. Jamal’s full lips moved lower to suck softly from Jennifer’s drenched pussy. She ground it into his face. There was some movement behind her now and soon Jamal’s prodigious head presented itself at her gate. Jennifer straightened her arms, bracing herself with her hands against the bed. She widened her legs for the assault she knew was coming.
Jamal’s monster was already slick with pre-cum and Jennifer’s juices. Jennifer looked sideways at the bureau mirror and watched as Jamal rocked his pelvis. She saw a long, thick column of dark sinew sink into her. She lost all her breath as she felt the phallus stretch the walls of her vagina and fill her up. It tunneled insistently forward into previously untraveled places, testing her limits.
Jamal paused and her discomfort began to subside; leaving Jennifer feeling the only word she could think of – full. REALLY full. Soon Jamal began slow, steady strokes – then faster and longer. Jennifer couldn’t believe what pleasure the huge cock could create. Size does matter after all, she thought, smiling inside. David is definitely history. She felt another orgasm start to build inside her
Suddenly, Jennifer found herself thrown onto her back with Jamal kneeling between her legs. He pulled her forward by the hips as he sank down, sitting back on his feet. He raised her by the ass and re-entered her cunt. Jamal thrust his invader upward, over and over again, electrifying her G-spot. Pleasure rang every nerve in Jennifer’s body and she heard herself scream. I never scream, she thought.
“Jamal, I want to see you come,” urged John.
Jamal withdrew in time to shoot spatters of semen over Jennifer’s chest and face. Olivia held his wet, pulsating penis until the convulsions stopped.
A few minutes later, Jennifer and Jamal slipped on fluffy hotel robes.
“That was extraordinary, thank you” breathed Olivia.
John stood up and headed for the other room.
“I would like to engage the two of you again, soon,” whispered Olivia, looking toward the door. “Without John next time.”
Jennifer glanced at Olivia’s generous breasts and the huge nipples that were hardly concealed by the sheer bra. She recalled Olivia’s talented fingers and smiled at Jamal.
“I think that can be arranged.”
After the couple had left, Jennifer and Jamal shared the luxurious, multi-head shower before dressing. They had no reason for modesty, after all. Jennifer could not help playfully pulling at Jamal’s soapy swinging dick as hot water poured over them. They wound up fucking on the bathroom floor – for fun this time – with Jennifer riding her stud, cowgirl style.
Later, as they headed for the elevators, Jennifer turned to Jamal.
“Thank you for not hurting me back there. They were really looking for a show and I got pretty scared.”
“Aw, ain’t-no-thing, Jennifer,” smiled Jamal. “Call it professional courtesy!”