Cheating with Boyfriend's Bully

(c) 2022 by SirRender - email me if you love my stories or have future suggestions

Caitlin initially had no intention of cheating on her boyfriend. One thing just led to another and it sort of happened.

In high school she and Martin had been social outcasts. They were both fairly nerdy, preferring to quote and even to act out scenes from goofy movies over discussing fashion and hair or sports and cars. It was the mid 1990s and the new craze of collectible card games was beginning to take over from dice and paper role playing games, both of which were enjoyed by the group with whom the couple shared their lunch times.

It certainly did not help Caitlin's standing very much that she was the only girl in that group of six, so a lot of other girls at school looked down on her, and that she was a late bloomer physically, so few guys gave her even a first look. Caitlin wore eyeglasses though Martin did not--the lenses were not thick but where wide and round and she was frequently teased for wearing "teacher glasses".

But when Caitlin did finally start to grow into a woman physically in their senior year, the transformation was spectacular. In the span of about eight months she went from being a skinny girl with a toothy grin and thin lips, a flat chest with puffy nipples and no ass to speak of into a five foot six inch walking bedroom wall poster with full luscious lips and rocking a body with C cup breasts, a very nice set of hips and a firm, round ass.

But intellectually and emotionally Caitlin was still into science fiction, steampunk and goofy movies. She never let her body, nor the looks she now got from guys who wanted her and girls who despised her for drawing their boyfriend's attention, overshadow the person she was. She stayed true to Martin because, well, why wouldn't she? What they had was deeply meaningful; they shared so many interests, frequently finished each other's sentences and, although he was clearly happy to get to make out with such a hottie, he had always been good to her even before she blossomed.

Their relationship took a bit of a hit when they got accepted at different universities more than a hundred miles apart. They spent as much of summer together as they could and made plans to go home for every major holiday and spend that time together. They also decided to keep up their relationship over the phone in between holidays.

Things went well for the first trimester, though they quickly realized that long distance phone calls were expensive and so agreed to trade off being the one to make the call each week.

Caitlin missed Martin terribly in between holiday breaks which always seemed too far apart. Her roommate in the dormitory was usually out most nights getting drunk or going to concerts, and Caitlin eventually worked up the courage to ask Martin to have phone sex with her. It was a way to spice up their relationship and it also gave her a reason to masturbate. She was a knock out babe who received many propositions from guys and she always had to turn them down. She needed to release sexual tension without being with her boyfriend, so toying herself while talking to him on the phone was the next best thing.

But it took a few weeks before Martin felt comfortable with the idea, and by that time they were both home for the Thanksgiving holiday and they had real, physical sex. After returning to their respective schools they began having phone sex at least once a week.

Going into her second trimester of college, Caitlin got teamed up in a lab class with a guy she knew of from high school named Sam. Sam had handsome, rugged good looks with broad shoulders and toned muscles. He stood about six feet tall and had dark brown hair with gray eyes. He had been a staple of their high school football and basketball teams, which both went to state championships during their junior year, and he usually had his pick of girls who wasted no time in stepping in to replace whomever he had grown bored of dating.

Sam often bullied Martin for being a nerd with a stick figure girlfriend. Of course, when Caitlin grew and grew during those eight months, she became an object of Sam's desire. She was certain that he wanted to bed her for being so stunning to look at yet she also suspected that his frequent, often lewd, advances made in front of Martin were just an attempt to humiliate her boyfriend further. Caitlin turned down Sam at every turn, even getting in a verbal burn or two in front of Sam's friends which often got them ribbing him for striking out.

To run into him again around six months after graduating high school, and to be paired up with him for an entire trimester while she was feeling distant and disconnected from her boyfriend, was cruel fate.

He recognized her immediately on entering the class, and though they could technically partner with anyone from the class for their lab work, she was still too meek to approach anyone, and Sam locked on target right for her, keeping her busy until everyone else had found their partner. He was all that was left and so she was stuck with him.

"Caitlin French", Sam mused. "The one who got away."

"The one with a brain in her head," Caitlin replied.

"You still with... was it Nate? You know, you can do so much better. You got it going on, girl!"

"It's Martin and yes we are still dating." She didn't know why she then added, "I'm going to marry him." It was probably true, but why did she blurt it out?

Sam made a bit of a show of looking around. "Where is he?"

Caitlin stopped herself just short of saying that Martin was out of state attending a better college, as she realized that would be putting herself down. She was in no way dissatisfied with her choice of college. It was the best school she could afford and they offered the major course of study she wanted. "He's... away, at another school."

"Tsk. He didn't love you enough to come to the same school as you. That's a shame."

The teasing continued that way for two weeks, with lecture twice a week and labs in between days. Then Sam began to change his tactic with her. He told her he could really use her help with their homework because the material was just too far out there for him to wrap his head around. He seemed genuine enough, and he didn't have any of his old friends around to show off for, so she agreed to help him study. He still kept commenting on Martin's absence, and more than a few times she caught Sam studying her body when he should have studying the text book, but if he was playing for sympathy he was doing a good job of making it appear that he needed her help. She also reasoned that since he probably spent very little time studying throughout high school he probably was a bit in over his head in college.

One afternoon they were just chatting while walking out of class and kind of just kept walking aimlessly until they reached her dorm. She didn't really think anything of it--it was a coed dorm and for all she knew he lived in one of the other wings or on another floor, but they chatted all the way to her room. She didn't invite him in, and he didn't barge in per se, but he saw the shelf above her desk which was full of steampunk gear which she had built in her free time. He asked, "What the hell is all that stuff?" and strode into the room to inspect and poke at it.

"It's steampunk!" she said with perhaps a bit too much enthusiasm. Then she added more somberly, "It's just a hobby. I build stuff."

"Out of brass and... is this real leather? And what's with all the little gears? Half of them are just stuck on, they don't turn and aren't connected."

"It's just fun! It's goofy."

He looked her square in the eyes, crinkling up his forehead, and asked, "Do you want to live your life just being goofy? Don't you want more?"

She was mulling over her response when the phone, which her roommate had provided and whose cord just barely stretched from the jack beside their dorm room door along the wall to the edge of Caitlin's desk at the head of her bed, rang. Glancing at her 1970's era flip clock also on her desk, she remembered that it was Martin's week to call her for their phone sex.

"Oh, Sam, I have to take this. I'll see you in class tomorrow." She wanted to wait until he was gone before answering, but he was still taking his time fiddling with her handmade steampunk items. She did not want to miss the call as long distance was pricey and she wouldn't want to need to call Martin back--that was the main reason they switched turns making the call. After the third ring she lifted the receiver, a tad too quickly, and the phone base tumbled off the desk and hit the floor with a clang. "Oh god!" she cried, kneeling to retrieve it. She asked several times in a hurried voice whether Martin was still there and was relieved that he was.

As she began to stand, a hand slapped across her butt. She yelped, bounced upright and lost her hold on the phone's base. It clanged on the hard floor again. Her eyeglasses lurched upward and came down almost at the end of her nose, very nearly dropping off her face and to the hard floor as well. She turned her head and snarled at Sam then knelt again to retrieve the phone, asking again for confirmation that Martin was still on the line.

"Yeah, I am, but what was all that? Did you drop the phone or something?"

"Yes, sorry. You remember I told you the cord only barely reaches my desk."

This time as Caitlin stood, rather than slapping her butt Sam cupped both of her cheeks in his large, muscular hands.

"Oop!" a startled Caitlin cried but managed to keep her hold on the phone. She turned to snarl again at the jock and he planted a kiss on her lips.

Then Sam called out loud, "Hey, nice ass." Still gripping her butt cheeks, he gave them a jiggle.

Martin heard and asked, "Who is that talking? And what does he mean?"

Caitlin tried to sound chipper and carefree while replying, "Oh, just some dork who lives in the dorm who thinks he's funnier than he is. He saw me bend over to pick up the phone." Then motioning angrily toward the door for Sam's sake she said, "I'm about to shut my door so we can talk in private."

Sam leaned in close to Caitlin's ear and whispered, but loudly, "Oh I love you baby. You make me so horny. Let's talk in private."

Martin again asked who was with Caitlin.

"Like I said, some dork from the dorm who thinks he's funny. He's not. He is leaving now." She motioned once more toward the door with the hand which was holding the base of the phone while simultaneously putting the side of her foot on Sam's ass to goad him in that direction. He did leave, but turned to make one last smoochy face at her, and she used her foot to push the door closed in his face.

Once he was out, she fumbled with the door lock, still holding one part of the corded phone in each hand, then flicked off the single overhead light in the room. It was dark now save for her roommate's computer monitor with the colorful flying toasters screensaver which ran constantly when she was not using it for school work.

Caitlin removed her over-sized round eyeglasses and set them on her desk, then sat herself down on the foot of her bed, cradling the phone between her ear and shoulder while quickly stripping out of her clothes. Once nude, she laid back on the bed, lifted her knees and spread her legs and began to rub and then to finger her moist pussy while her distant boyfriend told her over the phone what he wanted to be doing with her.

Caitlin was getting pretty into it, wriggling her hips and moaning encouragement to Martin, with her eyes closed and her head turned sideways while she imagined him suckling her tits and sliding three fingers in and out of her pussy. She heard a click and the groan of an old door hinge. She raised her head and her eyelids snapped open. Evidently she had not quite managed to lock the door after all, and a figure now stood in the open doorway with light from the hall outside streaming around them making an ominous silhouette. By the stature and build, she knew that it must be Sam, though the light behind him dazzled her eyes and without her glasses he was out of focus.

He let out a long, low whistle before stepping into the room and shutting the door behind him. Caitlin was stunned at his sudden reappearance. She lay there for a moment, motionless and speechless, spreadeagled on the bed with her fingers in her furry slit while he looked her up and down. He whispered so that only she could hear, "Damn girl, you really have got it going on." He licked his lips, though she could scarcely have detected that in the dim monitor light. He came to the foot of her bed, got down on his knees, moved his hands under her butt and pulled her right to the edge of the mattress, then lowered his face into her crotch and began to lick her labia.

Over the phone Martin noticed that Caitlin's encouragement had trailed off and he asked whether she was still there. Still in shock at the hunky stud between her thighs lapping up her pussy juice, she numbly replied, "Uh huh". Then she quickly added, "Sorry, I just..." Sam's tongue grazed over her already sensitive clit, "...ohhhh goddd"

Sam went from licking all around the outer edges of her slit and swiping his tongue back and forth on her clitoris to plunging his tongue into her vaginal canal. She could feel his meaty tongue slithering deep inside and was surprised by the length of it as it probed her depths. Her head rolled back and she let out a shuddering whimper.

Here she was, an eighteen, almost nineteen, year old college freshman who until about a year earlier had been on nobody's "must fuck" list and she was being talked dirty to by her long-term but geographically distant boyfriend while another guy--the bully and tormentor of them both during high school--ate her out. Martin took her moaning and whimpering as a sign he was doing incredibly well at describing how he wanted to be fucking her and got back to his narrative. For her part, Caitlin made no effort to push away Sam and also gave no indication to Martin that she was not alone in her dorm room. That naughtiness of secretly cheating was arousing her more than she had ever been aroused. Martin was alright in bed, but of course he was her first and thus far only lover so she had no frame of reference for a comparison. But this... this was turning her on enormously.

As Caitlin felt her own passion rise, and as she believed that she was nearing climax, she encouraged Martin to talk extra dirty to her. He did so and she lay there allowing herself to breath more rapidly and to paw at her bed sheets with her one free hand. Her voice suddenly rose about an octave over the course of the sentence as she cried out, "Oh fuck yes that feels so good!" She shuddered and groaned loudly--so loudly that she became self-conscious that her neighbors in the dorm might have heard her. She bit down on the side of her hand and convulsed with Sam's hands still squeezing her butt and his tongue still buried inside her.

She thanked Martin for the call, told him she was exhausted and ready to go to sleep and they hung up. She lay there in the darkness and cold shivering while Sam stood up. Then she heard the unmistakable sound of a zipper being dragged down. "Yes" was all she said, and Sam mounted her and began to screw her brains out while groping her big tits. She felt inch after inch of his cock slide inside her pussy. After what she guessed was six inches, she figured she must have lost count, or that he pulled back out and pushed back in. He kept going and she felt the head of his cock--thick and round, maybe the size of a racquetball, maybe slightly less--pressing deeper inside her than anything had ever been before.

Then he for sure pulled out and pressed back in, and she certainly felt more than six inches, more than seven and just possibly more than eight inches push back inside her, then about halfway out before plunging in again. He picked up speed and thrust into her deep and fast, quickly relieving his own built-up tension and blasting a load of thick, hot semen into her womb. He bent over and kissed her on the lips; she tasted her own juices on his lips, as she had done previously on her own fingers. Then he left and she lay in the darkness wondering what the hell she was going to do now.

* * *

Caitlin skipped the class which she shared with Sam the following Tuesday. She was angry with him for creating the situation and angry with herself for allowing him to bed her just because she was already horny and it seemed like a quick way to get relief. When she did return to class and had to deal with his presence, he seemed unaffected, like it was something which happens every day--which, she reasoned, probably was true for a guy like him. After class he walked out with her, much like before, and she attempted to intellectualize her displeasure with him. She found, very much to her surprise, that he had an answer for nearly every point which she made. He was no expert orator, but his responses were straightforward and sound, including the fact that if she had not wanted to have sex with him, she could have said no, could have told him to stop, could have shouted for help since there was a dorm wing full of students just beyond her door, but that she instead made no effort to resist and then encouraged him to continue. This truth made her even more angry with herself, and she dug in her position but soon realized that she was arguing from a position of relative weakness.

They had been walking and talking with no stated destination and before she realized it Caitlin found that they were back at her door. Sam leaned with one elbow against the wall and his head supported by his hand, and asked point blank whether she wanted to do him again or just play with herself in loneliness.

"You are an ass," she told him.

He gave her backside a look and replied, "And you've got a fine ass."

"I have a boyfriend."

"Who is like three hundred miles away and you won't see him again for like three months. College is about trying new things and testing yourself. How do you know whether you truly love him if you don't see what else is out there? Allow yourself to be a woman, let yourself be loved, and if you still want to be with Marty then you know it's real."

"I don't have time for this tonight. Goodbye Sam," Caitlin said before turning her key in the door lock.

Sam's tone was teasing and dripping with innuendo when he asked, "Oh, are you talking with him again tonight?" Caitlin did not reply but she paused halfway through the doorway. "You are. And you're okay with just laying there alone in the dark using your fingers to get off?"

Caitlin entered her room and pushed the door closed behind her. She turned and made sure to engage the lock. She stood there for about a minute controlling her breathing, then she silently counted to ten, unlocked the door and pulled it open. Sam was leaning with his back against the wall across from her door with his hands in his jeans pockets. She left the door open as she turned and walked to the center of her room, stopping only briefly to turn on her radio, then she began to pull off her shirt over her head.

Either she or her roommate had left their curtains open, though the crank-open windows were closed, and with it being dark outside but bright inside, the windows acted as a mirror as she watched herself with him looking in over her shoulder. She unbuttoned her knee-length flowing skirt, unwrapped it around her waist and allowed it to drop to the floor. She stood now in only her baby pink plain cotton bra and black satin panties, pink socks and sneakers. She struggled to maintain control of her breathing and heart rate. The next move was his. Would he be a gentleman and leave or be a slimeball and enter her room?

"A slimeball, naturally," she said quietly while watching him push himself off of the far wall with both elbows, reach up to sweep back his hair and then step across the hall and through her open doorway. Caitlin turned her head sideways so she could just watch Sam in her peripheral vision. Aloud she commanded, "Lock the door."