The Setup - Cover

The Setup

by AutumnWriter

Copyright© 2006 by AutumnWriter

Romantic Sex Story: College student and her best friend/roommate thinks she should lose her virginity, and they hatch a plan to make that happen

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic   Heterosexual   First   Slow   School   .

© copyright 2006 All rights reserved

"I'm still not sure that this is such a great idea, Tracy." Steven chose to stare into his coffee as he spoke, rather than look at his girlfriend.

"I already told Jennifer that you would." She replied. I know that you don't like her, but she's really sweet if you get to know her."

"I don't understand why this doesn't bother you, Tracy. Don't you want me to be loyal to you?"

"It's only this one time, Steven. When I get back, we'll pick up where we left off. Jennifer is my friend and she needs this. Who else would you want me to ask? She's ready for it this weekend, even got on the pill just for this. I have to go home for the weekend, so it all works out. You'll have the room all to yourself. Just be the same... sensitive person... that you always are."

"Alright Tracy", Steven said. "I promised that I would do this and I will, I just want you to know that I have my doubts."

"That's what I want to hear, Stevie. Remember that Jennifer will be waiting for you to have dinner. Now, I've got to catch my ride. Don't worry. 'Luv ya'." Tracy leaned over for one of those quick 'see you later' smooches and left the dining hall. Steven continued to brood over his coffee alone.

Steven hated it when Tracy called him 'Stevie'. When she did, it meant that he was being lassoed into something that he didn't really want to do. Usually, it meant taking her to a shopping mall, or to some disco that he was hoping to avoid. Steven did it because Tracy was an expert at repaying favors. When they met earlier in the school year it was Tracy who had been the more sexually experienced of the two. Steven had learned quickly under Tracy's tutelage. Their fun times together covered over the rough spots.

Steven's task for the weekend was to introduce Tracy's roommate and best friend, Jennifer, to the pleasures of sex, or 'lovemaking' as the girls had insisted on calling it. Steven was at a loss about why he had been chosen for Jennifer's contrived deflowering. It was true that she had very few (actually zero) dates. He knew the reason why. Jennifer was as socially inexperienced as she was sexually naïve. She was someone who would always say the wrong thing or get in the way at precisely the wrong moment. Steven knew that she didn't mean it. She only wanted to be part of what was happening, but just didn't know how to do it.

Steven knew that his and Tracy's playtime in their dorm room piqued Jennifer. She would always hint to them to tell her details. Sometimes Tracy did after Steven left. The recounting excited Jennifer and made her dream of her own future encounters. Once, Jennifer asked if she could watch them. Tracy had agreed, but Steven turned her down. When Steven and Tracy concluded their sexual activity for the night, they would all sleep in the same room, Jennifer in her bed, and Steven and Tracy in the other across the room. All of this made Jennifer try even harder to find a young man who would be willing to become her boyfriend. Jennifer pressed, and it distanced candidates from her. It had been Tracy's view for a long time that Jennifer would be happier if she found a young man to bed her. It became obvious that it would not happen soon if nature was relied on to take its course.

Steven looked at his watch. It was getting late. He didn't have time for his coffee. He picked up his books and hurried to class.


As Steven strolled across the quad to Jennifer and Tracy's dorm he had to admit that he felt a little nervous. He slowed his pace a little to give him more time to think. Surely, he did not lack experience. He had no feelings for Jennifer, either. He didn't dislike her, as Tracy insisted. Jennifer could be a pain in the rump at times, but he knew that she only realized that she was after committing the offending deed. Anyway, it was never out of malice or spite, just bad timing or over-exuberance. She was seldom an obstacle between Tracy and him. She was just always 'there'. She was a footstool without a chair, always in the way without a purpose, decorated with plainness, potentially useful but lacked the proper setting.

Steven was taking Jennifer to "dinner" at the campus dining hall. On Fridays most of the student body left campus to visit home. The dining hall would serve steak as an inducement to get the students to stay over the weekend. It didn't work very well, but steak was still on the menu. It gave Steven and Tracy some advantages: a nice meal where the price was right (it was covered by the meal plan); a nearly empty dining hall where they could sit and talk without attracting a crowd. Best yet, casual student-mode dress would be the order of the day.

Steven knocked on Jennifer's door and she appeared instantly. Steven calculated that she must have been watching for him from her window. She was dressed as usual: faded jeans, sweatshirt, sneakers, and windbreaker. The jeans were about a size too big. It made Jennifer look skinny. The sweatshirt was baggy, too. She never wore makeup, so she appeared pale and her lips were barely darker than her skin. She wore her ashen blond hair parted in the middle, falling downward aside her face and down her back to her shoulder blades. It smelled like strawberries, so Steven knew that she had shampooed it that afternoon. It was the nearest thing to perfume that he could detect.

"Hi, Jennifer" Steven said. "Are you ready?"

Her sudden look of fright struck Steven like a slap in the face.

"I meant, ready for dinner."

Jennifer looked down at her shoes, embarrassed. All at once her cheeks attained a rosy hue. Although she was just blushing from the awkward exchange, Steven thought she looked better with some color in her face.

"I'm sorry, Jennifer, I didn't mean to startle you. Are you hungry, because I know I am?"

"Oh, Steven, we've gotten off to such a bad start. I'm sorry. I'm just nervous. I'm hungry, too."

As they started for the dining hall Steven tried to reassure her. "It's okay, really, Jenn."

"He called me 'Jenn'!" she thought. "He's never used that name for me. Maybe he likes me little after all."

"Steven", she said out loud, "There are some things that I want to ask you about tonight. You see..."

Steven held up his hand to stop her. "Let's wait until we can sit down at an empty table before we talk about that." He said. "We don't need to have an audience." She was grateful that he had saved her from another faux pas.

"This is typical Jennifer." Steven thought to himself. "When she gets nervous she starts bumbling."


They didn't have much to say until they found an empty table.

"Steven, I couldn't believe it when Tracy told me that you had asked to do this. It means a lot to me."

Steven's instincts told him to throw his hands up, deny the assumption, and straighten out this would-be nymph. He retrieved the words just as they were about to pass his lips and sear themselves into Jennifer's fragile psyche. Steven thought better to listen and learn.

"I didn't know that Tracy told you that." He knew that more details would come forth if he applied the slightest amount of patience.

"Well, yes, she did. She told me not to tell you that she told me, but I guess that it just slipped out. Anyway, Steven, I think that you're really nice to do this."

"It was nice of Tracy to make it happen." Steven countered, polite but not quite truthful. He was right; details were starting to come forth.

"Tracy's such a giving person." Jennifer said. "We had been talking about how good it would be if I could find someone to do this and then she said you had just jumped at it when she was asking you for ideas on finding the right guy."

They didn't say anything for a minute while they ate. Then Jennifer started talking again.

"I would never have had the nerve to think this up for myself." She said. "Tracy really helped me. She made me realize that I had to lose my virginity to feel more confident with guys. She helped me with the birth control pills and everything."

Jennifer's discourse brought clarity to Steven. Now he realized that he and Jennifer had one thing in common in that they had been set up by Tracy. He couldn't understand why Tracy had done it. She enjoyed orchestrating people and events, but this was over the top. Steven had no desire to join in the manipulation, but now Jennifer seemed so eager. He decided to probe further.

"Why do you think that breaking your virginity will make you less nervous around guys, Jennifer?"

"Well", she answered, "I think guys have a way of knowing which girls are virgins, and it makes them act differently; then I act different towards them. That's when I open my big mouth and get into trouble. Every time a guy looks my way, I think that he's sizing me up to figure if he wants to get into my pants. I get self-conscious and go to pieces. Maybe if I know about sex, it will give me some confidence and I'll stop worrying about it all the time."

She seemed so convinced. Steven wanted to ask her if she was sure it was her idea or Tracy's, but he couldn't do so without appearing to be backing out. He tried another angle.

"You must be nervous, Jennifer." He said. "After all, even if you have good reasons, it's a big step."

"Oh, I am!" she replied. "There's so much that I want to ask you before we go back to the dorm room."

"I'm all ears." He said.

"First, I don't know exactly what to do. I mean, I think that I know the basics, but I don't want to do anything wrong. You know what I mean?"

Steven nodded in understanding.

"Jennifer, I think that you tend to worry about things that you don't need to worry about. Just let nature take over. Your body will tell you what to do. Just relax and be natural."

Steven let that sink in and continued. "It's supposed to be 'fun', you know. A lot of people keep doing it because they enjoy it. If you're thinking of this as something that you have to get out of the way, maybe it would be better to save it for another time."

"No, Steven", she retorted. "I didn't mean it that way. I'm just a little nervous."

"It would be natural for you to be nervous, Jennifer. It's mostly fear of the unknown. After we get started everything will all fall into place. In the morning we'll look back and have a laugh on it."

"The morning!" They would be waking up together. It was a thought that hit Jennifer all at once. She hadn't thought about the impending finality. She wondered how it would change her. She finally understood that what she was planning was more than an adventure like shopping at a new mall. As she and Tracy had planned out the tryst it had all seemed so matter-of fact. It was detail-oriented: the pills, the weekend alone, getting the right guy. Now it took on proportions of an important lifetime event.

Jennifer cast her eyes down to the table. Steven sensed there was more to be discussed.

"I think there you have something more on your mind, Jennifer."

"Steven", she began, "I hope that you won't be angry by my asking you this." She didn't wait for him to answer. "Have you ever taken a girl through her first time before?"

The question gave Steven a sudden alarm. He had a formula that he always relied on. One constant in the equation: never divulge what he had done with one girl to another one. He had never been guilty of it. He learned his lesson the easy way, by observation, as friends' secrets told returned in their inevitable circular path at the worst possible moment.

Jennifer saw the angst in Steven's brow. "Oh, no!" she thought, "I've done it again!"

She paused a moment, then spoke again, thinking that honesty might save the day. "I only asked you that because..." She paused again. She lifted her head up and said. "I don't know how to ask you this. Will it hurt? Tracy said that it really will hurt a lot. She thought that I should have some drinks first to, you know, dull the pain. What do you think?"

Steven lowered his defenses. He felt the fear contained in Jennifer's voice. He sought to comfort her if he could. It was wrong of Tracy to set her up with such dread expectations. Perhaps Tracy wished to limit their success.

"I had an experience before I started going with Tracy. It was nice, I think, for both of us."

Steven continued, "It won't necessarily hurt. It might, a little. I can't say for sure, but I think that it depends on the individual. Forget about the drinking, I don't know how that would help. One thing I do know: you have to relax. There's more pain involved in pushing apart muscles that are cramped up than in breaking through a hymen."

Jennifer sat pensively for a moment, summoning courage for her final confession.

"Steven, I might as well tell you everything. I don't have any experience at all. It's not just being a virgin. I've never even had a boy make out with me or had one see me with any of my clothes off. I've never even been kissed, at least the way I've seen you and Tracy kiss. I know that you must think I'm pathetic, but I had to tell you this, so that you can understand why I'm so nervous."

"Jennifer", Steven said, "I'm not that surprised. When people start making out it leads them go a little further every time, until they've gone 'all the way'. So, when I found out that you're a virgin, I really didn't expect you to have a lot of experience. You don't have to be ashamed about it. The right moment comes at different times for everyone. If you have any doubts about going through with it, just say the word. You don't have to do anything that you don't want to."

Jennifer listened to him. Steven's answer gave her some comfort. She still had a case of nerves, but was thinking that Steven would make everything alright.

Steven saw her thinking on what he'd said.

"Take it one step at a time. You'll feel some new things that you'll really like. Concentrate on those. Just remember that you can call it off at any time... and we'll still be friends."

The last part, about "being friends", made Jennifer smile. As they rose to clear their table Jennifer thought that she was taking her last walk after her last meal.

"This is it!" she said to herself. She barely heard Steven speaking.

"I'll give you awhile to get ready. I thought that I would take a shower first. I'll knock at your door at eight."


As they left the dining hall Steven and Jennifer parted to go to their separate dorm rooms. As Steven walked he thought to himself that he would have liked to have a little more time to think things over. He found himself uncomfortably in the middle. He didn't know Jennifer well enough to have deep feelings for her. Now, after their dinner together, he knew her too well to want to bed her purely out of lust. Jennifer and Tracy were expecting performance from him. If he were to back out Jennifer would think it a sign of rejection, not consideration for her.

Steven started thinking about Tracy and asked himself why she had arranged to have him and Jennifer in the positions that they were in. He wasn't sure that Tracy's motives were so altruistic. He had never known a female to relinquish a hold on a man 'unselfishly', just to give a sexually underprivileged friend a chance at bedroom bliss. Women hated comparisons of themselves with other women, particularly in matters of their nude bodies and sexual skills. This setup was sure to create just such an evaluation. Was Tracy so confident that she sought a comparison in order to reinforce Steven's preference for her? Was she so sure to hoist the bedroom trophy? Maybe Tracy had set a test for Steven. Perhaps Tracy's motive was her penchant for manipulation that Steven knew too well. In Tracy's world sex was an activity with many uses. At any rate, Steven never fooled himself that he was in love with Tracy, but he enjoyed her talents and the security that their steady relationship gave him. The importance of it seemed to be dimming in the light of the present circumstance.

As he ambled to his dorm, Steven tried to sort his way through his conflicted soul. He gazed at the prospect of a weekend of carnal delights with his girlfriend's roommate on loan. For a total commitment of forty-eight hours, he would be free to wander wherever his creative libido and persuasive talents with Jennifer would lead them. Jennifer didn't look like she would require a lot of persuading. After that, he could catch up for lost time with Tracy. Who knew, maybe Jennifer could be on call, or more. Many possibilities entered Stevens mind. Instinct told him to stop complaining. Jennifer had made her own choice.

It was the nagging whisper that irritated him. During their dinner together Jennifer had exposed her vulnerability so openly. Maybe she would lead a happier life if she allowed herself to be wooed and courted by a young man who sought to be her first lover. Maybe the young man would be as inexperienced as Jennifer, and they would learn love's delights together. Steven knew that he could do a credible job in the physical initiation of the naïve girl. How could he give her the thrill of mutual desire that every person seeks. He sought the answer, but it was not in him.

Jennifer became human during their dinner together. She had feared Steven's pity in her confessions of sexual naiveté. She was mistaken. Steven admired her bravery in opening her secrets to him. He started liking her for her honesty. Her partial innocence was a mystery. She was inexperienced, to be sure, but was responsible for the contrivance that he was now a part of. He decided that she might be a diamond in the rough. He wondered about the person hiding underneath the façade of social bumbling.

At least Jennifer rated a shower, shave and change of clothes. He had time for that, and to purchase a bottle of wine for them to share.


Steven arrived at Jennifer's room cleaned up, and with a bouquet of flowers and bottle of rose'. He wasn't sure what to expect from Jennifer or himself. It was an unusual assignation.

Steven was used to the customary baking that took place in almost any first-time date. There would be a careful testing and measuring process followed by period of mixing and kneading. He would check the temperature by gently pressing in a digit like a baker trying a loaf of bread to see if it was ready to come out of the oven. Sometimes it would be just right and ready to enjoy. At other times the loaf might need more baking. When that would happen the flavor would be all-the-better because of the longer warming time. He would never let a loaf become overdone. It would be hard and crusty. Sometimes it would be apparent that the loaf would just never be right for his palette, so he would let it go, to be finished by another baker with different tastes than he.

The contrivance to which he had agreed was a bypass of the traditional process. It was like buying a loaf of store-bought bread. It was ready to eat but with an unknown taste. He told himself to be happy that the work had been done for him. It was unsatisfying, however, and bread is always best fresh and warm from the oven, prepared in just the right way so that the eating of it yields the greatest pleasure. Perhaps he could reheat Jennifer to a golden brown toast, and she would taste good, too.

As he mounted the stairs to Jennifer's floor he wondered how he would find her. After the conversation in the dining hall he half-expected her to have run away in fright. Possibly Tracy had issued some pre-flight instructions prior to her departure. Probably, he thought, he would find her in her jeans and sweatshirt, not knowing what to do or how to start. He was determined that the final decision had to be Jennifer's. It could not be because Tracy wanted it, or that he had been promised her favor for the night. If Jennifer was unready, he would accept that she was one of those loaves better passed on to another baker.

Steven approached the door. He knocked and waited. For long seconds there was no answer. At last the handle turned and the door slowly opened a few inches. Through the narrow opening he saw Jennifer peering at him. Her face was all that he could see. There wasn't much light shining out from the room behind her.

"It's me, Steven!" he announced.

Jennifer raised her fingers to her lips and issued a loud "Shhhh!", then opened the door all the way. She grabbed Steven's hand and pulled him into the room, shutting the door quickly behind them. Steven stood just inside the doorway. Jennifer had stepped back several paces.

The lamps in the room were turned off. A lone candle off to the side provided the only light. It took Steven's eyes a few seconds to adjust to the subdued glimmering. Before him, Jennifer stood in an amazing transformation. It was shocking and pleasant. The flickering candlelight bathed her. Steven knew it was a 'Jennifer' that had never been seen by any person. Her plain-jane aura had been discarded. Jennifer wore a satin nightgown that extended halfway between her hip and knee. Over that she wore a matching peignoir of a gauzy material that was fastened only by a single button at the neck. It exposed the nightie to view, but hid its details. Steven spied the outline of matching panties beneath the outer layer. The ensemble was blue. In the half-light it took on an aqua hue on the side nearest the candlelight and a royal blue appearance on the darker side. It was a color that complimented her blond tresses. Jennifer had redone her hair, not in a fancy contrivance, but brushed it in a way that gave it fullness and wave and held away from her face. She was barefoot, suggesting the innocence that she was soon to relinquish. A hint of perfume betrayed her carnal intentions. In all, it was a seductive presence as she stood still in the middle of the room, hands at her sides as she allowed Steven to survey her.

It took all of Jennifer's courage to remain still while Steven eyed her. She didn't know why, but a voice inside her told her that she had to do so. Although her outfit covered most of her, she felt naked. In his eyes was an emerging betrayal of the lust that he felt but did not yet speak. Her wearing the negligee was a statement that made her naked of defenses. By showing herself to him in this way she had stepped over the fence of virginity with one foot. Straddling the barrier, her display invited him to come hither to help her cross over completely.

Jennifer waited for Steven's move. He indulged himself long seconds, savoring the new creation before him. Seconds turned to hours on Jennifer's clock. The sensation of being on display was foreign to her. Many emotions flooded through her so fast that she was unable to sort through them. She was a novice tightrope walker midway between posts. She had taken irretrievable steps away from safety. Her partner awaited her at the far terminal. She was frozen, unable to retreat but with no plan for moving forward. She hoped for a safety net below, but dared not look downward to search for it.

She resolved to wait for as long as necessary. She made no movement, nor intended to, until Steven acknowledged her.

In her ears was the distant thunder of oncoming hooves, an impending stampede of events set to rush over her. Her heart was pounding to match the rhythm and intensity of the savage herd. She fought a desperate battle to stave off the outward show of panting that would signal her fear. She was naked in deed, and would soon be nude in fact. She was trembling a little, and hoped that Steven did not notice. She had recreated her visage to earn Steven's acceptance of whatever feminine charms she might possess. As she waited for his answer, she prayed for confirmation. She longed to know if Steven appreciated the presentation.

"Jennifer", Steven said softly, "I don't know what to say, except how beautiful you look."

Here, in a single sentence was placed the acceptance that Jennifer had longed for.

Steven was justified in attesting to her loveliness. He had never pictured her as she was at that moment. The bagginess of her daily apparel had so cruelly hidden her supple form. It was clear that her figure was flawless. Steven's eyes continued to roam over her. Although only medium in height, Jennifer's body appeared long and lithe. Her breasts were covered by the negligee and peignoir, but he could see that they were mounted firmly in her chest and were just ample enough to match her frame. He longed to see the nipples and imagined them stiff with excited desire. He glanced down to her partially uncovered thighs and noted her delicate, but toned muscles. Steven considered Jennifer's voluntary display for his inspection. He knew that many young maidens would be unable to stand such a test. He admired her pluck for doing it. Inspired by the work of art before him, Steven's own breathing quickened.

He turned and locked the door behind him with a loud click that made Jennifer startle as the single sound signaled their isolation from the world. Steven reached out his hands.

"These are for you;" nodding at the flowers, "and this is for us later on", raising the bottle of rose'.


Jennifer grasped the flowers to her breast and thrust her face into them. Their scent and softness were a salve for her soul, a simple piece of truth and beauty.

"Thank you, Steven. That was very sweet of you." She peered out at him from the cradle of the bouquet. Although the flowers covered her nose and mouth, Steven thought he detected a smile in the crinkles around her eyes.

Steven mused over whether Jennifer meant the gift of the flowers, or his compliment. The bottle of rose' remained unattended in his outstretched arm, so Steven fit it into the mini-refrigerator in the corner of the dorm room so it could chill for later refreshment. He stripped off his jacket and set it aside.

Steven stood and faced Jennifer who was still holding the bouquet to her face watching him. He slowly approached her, gently pried the bouquet from her hands, and set it on the chest of drawers nearby. Her smile disappeared with the protective flowers. In its place appeared a doe-eyed girl whose fear was refreshed by the imminence of the long-awaited action.

Steven stepped a little closer. With a gentle palm he cupped the side of her face, a test of her acceptance. He leaned in, still with his hand gently upon her face, and kissed her tenderly on the lips. Jennifer was pliant enough, but offered no return initiative. He released the kiss and caressed her from the line of her brow to her chin. He wrapped his arm loosely about her shoulder and tried the kiss again. This time she parted her lips a little. He enjoyed the softness that he found, the gradual yielding to his advances. He swirled the other arm about her. He probed her parted lips with his tongue. She yielded more. Steven felt her absorbing the first time pleasure.

As Steven took her over, Jennifer realized that she was crossing another line. She felt his tongue enter her. She gave in to it. His man's size and strength, his insistence and his tenderness were promises to her of awaiting pleasures if she could force herself over the final barrier.

He released her and moved back one step. Steven reached to her throat and undid the single button of the peignoir. He ceremoniously peeled it down her arms that had fallen to her sides, finally removing it from her altogether and setting it aside. He raised his hands back to her bare shoulders. She gasped slightly, expecting him to push down the straps of her nightie for a quick exposure. Instead, with a practiced gentleness, he retraced his earlier path. This time he stroked down her shoulders to her bare arms, ending in her palms.

It was a touching that made Jennifer thrill with sensuality. She longed for him to repeat the journey. She let out a quiet "mmm" to show her approval and encourage him. Steven understood the hint and stroked down her arms again. For Jennifer, it was not new like the first time; it gave a different pleasure because she sensed that her reaction had prompted him. Steven embraced Jennifer again and kissed her. This time Jennifer threw her arms around his shoulders and kissed back. She breathed into him through flared nostrils. She wanted him to know that she enjoyed his pleasuring her.

Steven felt aroused and in command. He broke the kiss and looked into her eyes searching for permission. She was looking back with anticipation. He placed his hand on the lacy strap on her shoulder and began to push it to the end of her shoulder.


Jennifer became aware of Steven's intent and let out a stifled whimper. She trembled, an involuntary reaction. She had so relished his attention to her senses a few seconds ago. She wanted to continue but the onrush of progress re-sparked her fear.

Steven removed his hand. "It's alright, Jennifer. Don't be afraid."

"I'm so sorry Steven!" She replied, with tears flowing freely and the trembling unabated. "I know you must be upset with me. You've been so kind. Just give me a minute and we can get back to it. I'm just so nervous!"

"It's alright." Steven repeated. "You should know how beautiful you are right now."

Steven spoke the truth. In the candlelight, clad only in the blue negligee, Jennifer emitted a special beauty. Her bare shoulders had a sculpted look, with classic lines in white marble. The bare arms flowing from them were delicately supple. The bodice of the gown covered her breasts, but their forms could be discerned beneath the shiny blue fabric. It made the viewer yearn all the more for their unveiling.

 
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