<p>Welcome to Cuckolded by His College Girlfriend, a four part story exploring the thrills of sexual exploration between two college freshmen (with an affair with a professor thrown in). Though it’s usually a no-no, I’m going to utilize perspective shifts quite a bit in this story. I like the way it allows me to explore the mindsets of both Evan and Amy as they play, so I hope you don’t mind :)</p><p><img data-media-id="29807343" src="/31/02/3102563e4639f840c5fabc279401de07e886e55dd9f590589428183860ae44b4.jpg"></p><p>Evan was a college freshman, and like most 18 year old guys he was enamored with breasts. Unlike many of his classmates, Evan had not been particularly lucky with girls in high school. He’d mostly spent his four years there wishing he could find his way into a girl’s shirt.</p><p>Like almost every other guy in his freshman class, Evan showed up on campus hoping to find a girl willing to welcome his lusty intentions. He wouldn’t have admitted it, but his expectations were low based on his high school experiences.</p><p>That’s why Amy was such a revelation. She was an adorable, chipper blonde in his English class and she was totally into him from day one. He’d offered a clumsy introductory flirt and felt immediately embarrassed, but she was on board. She flirted back, he asked her on a date, and before long they were making out in her dorm room and she was happy to let his hand roam up her tight tee shirt.</p><p>Even if she wasn’t adorable, chipper, and into him, Evan would have been into Amy thanks to her remarkable big breasts. He was enamored from the moment he saw them on the first day of class. They looked so big and so perky in the tight baby blue tee shirt she had on.</p><p>It was a minor miracle Evan was able to look away from her breasts long enough to flirt with Amy. Somehow he managed to maintain eye contact despite his desperate, hormone-fueled desire to gaze at her spectacular tits.</p><p>All he wanted to do was play with them, so he couldn’t have been more delighted that she seemed to want the same thing. He’d always heard girls guarded their breasts like state secrets, but Amy was the one that grabbed his hand and put it up her shirt. She wanted him to play with her tits. She moaned as he squeezed them. She even unhooked her bra on their second date so he could fondle them in their natural state.</p><p>It was after a month of dating and fooling around that they got naked in Amy’s dorm room. Her roommate was studying at the library and she wanted to take advantage of the opportunity to be alone.</p><p>That was how Evan ended up on his back with a condom wrapped around his cock and Amy’s pussy sinking down on his dick. That was how he ended up with his hands playing with her big, gravity-defying breasts. That was how he got to watch them bounce in his face as Amy took his virginity.</p><p>That was how Evan had a mind-blowing orgasm. Unfortunately, it wasn’t so great for Amy. She couldn’t climax in the 30 seconds it took Evan to cum, so she was left feeling disappointed while he was floating off in a post-orgasmic haze, completely oblivious to the fact that his girlfriend hadn’t even approached an orgasm.</p><p>“That was incredible. You’re incredible,” was all he could manage, though Evan did say it several times.</p><p>Amy knew Evan was a virgin and she was willing to work with him. She wasn’t terribly experienced, but she knew he was likely to get better and that every guy needed a little time to improve his skill in bed. Plus, she liked him an awful lot. He wasn’t anywhere near as gross or pushy as most of the guys she’d met. He was sweet and even though he hadn’t shown much aptitude for making her cum, she was willing to try and help him with that.</p><p>After the first time, it seemed that Evan had trouble thinking about anything other than sex. Without realizing he was sharing a little too much of his inner monologue, Evan told Amy that being inside a girl was so much better than he’d imagined and that cumming during sex was so much better than masturbating and that cumming while her big breasts bounced in his face was the best thing in the world and he wanted more.</p><p>So they had more sex. Lots more sex. For the first few weeks Amy hoped that Evan would last longer and perhaps show her a little more attention. He did end up lasting a little longer, but it was rarely more than 90 seconds. He was 18 and there wasn’t much to be done about that.</p><p>He didn’t really show her more attention those first few weeks. He didn’t try and go down on her. He did try to finger her a little when they’d fool around before sex, but he was insistent on ramming them inside her and mostly ignored her clit. In short, he was an 18 year old guy.</p><p>Despite the sex being a little disappointing, Amy had only grown to like Evan more over those first few weeks. He was good at being a boyfriend. He got her flowers. He took her on the kinds of dates a college guy could afford. He was sweet. He wrote cute little notes and sent her texts that were about her instead of being lurid comments about her breasts.</p><p>That’s why she was determined to help him get at least a little better in the bedroom. She wanted to cum with him. She’d been with guys that could make her cum and she needed Evan to be one of those guys.</p><p>It didn’t go well the first time she tried to coach him a little. They were fooling around and he had his hand in her panties. She tried to suggest that he focus his efforts on her clit after he’d gotten his fingers wet inside her.</p><p>“No, not like that,” she said. “Just move your fingers up here. There you go, that’s better.”</p><p>Evan acted a little bit offended at her suggestion that he might not know what he was doing, though mostly he just felt like an idiot. Like so many men of all ages, his ego had taken a little bit of a blow and he didn’t like it. Amy tried to push past it and have sex with him, but Evan had a little trouble staying hard. He was even more embarrassed, though he foolishly acted like he was angry and stormed out of her dorm room. Amy cried that night and Evan spent hours feeling like absolute crap about it before he apologized.</p><p>The next time they saw each other, he was ready to make up for it. He was determined to put his fingers to good use, and it worked. He did as Amy instructed. He played with her pussy and got his fingers all wet inside her before turning his attention to her clit and rubbing it skillfully while she moaned.</p><p>He didn’t quite make her cum because Amy was hoping that would happen when they had sex. Unfortunately, Evan came quicker that night. Playing with her pussy while he sucked on her big breasts had turned him on more than usual.</p><p>As the weeks passed and late summer turned into fall, Amy continued to work with her inexperienced boyfriend. She taught him about going down on her, though she couldn’t quite get him to embrace it.</p><p>At one point he said, “Why wouldn’t we just have sex instead? What’s the point of going down on you if I’m not feeling anything?”</p><p>Amy didn’t have the heart to tell him that she wasn’t getting much out of the sex they were having. She really liked Evan, but he didn’t last nearly long enough and he wasn’t packing much in the size department.</p><p>Eventually, in early November, Amy broke up with Evan. She told him it just didn’t feel like the connection was there, though that was only partially true. She actually felt like there was an incredible connection there, it just wasn’t happening on a sexual level, and it was mostly because Evan couldn’t bring himself to put his ego aside and concentrate on her pleasure while also thinking about his own.</p><p>Evan did not handle the breakup well. He cried for the first few days. He avoided English, the class he shared with her. It was a small class with just a dozen students and he couldn’t bear being that close to her.</p><p>He texted her too often. He wasn’t threatening, but he was unquestionably bothersome. He would occasionally show up outside her dorm room or a class she was getting out of and beg her to take him back or explain why she’d really broken up with him.</p><p>Three weeks of that was enough for her. Just before Thanksgiving break Amy laid it out for Evan. She told him that she really liked him but the sex just wasn’t working for her and his complete unwillingness to make an effort at getting her off was the reason why she broke up with him. </p><p>She told him that college was supposed to be fun and she wasn’t going to waste her freshman year trying to teach a guy how to please her when he clearly didn’t care about her enough to try.</p><p>At first, Evan acted like most young men in that situation: He got angry. Not at Amy. She wouldn’t have anything to do with him. Mostly he was just surly and quiet and he would occasionally snap at someone for no reason.</p><p>It was over Thanksgiving break that the anger finally dissipated. A conversation with his older brother enlightened Evan to what an idiot he’d been. It was explained to Evan that focusing on a woman’s pleasure was the best way to ensure his own sexual satisfaction, that it was an absolute necessity.</p><p>Only then was Evan able to push aside his ego and come to grips with the fact that he’d fucked up. He returned to school feeling like a new man and he was ready to prove to Amy just how true that was.</p><p>He was going to talk to her after English, but something changed during class that first day after Thanksgiving break. Evan was paying particularly close attention to his ex-girlfriend and he noticed that something was definitely going on between her and Professor Anderson. At least that’s what it seemed like.</p><p>Amy hung on Professor Anderson’s every word. She laughed a little louder than everyone else at his jokes (most of which were actually funny). She wore a tight, soft, feminine sweater, which wasn’t quite her style. Her hair was even done up a little more than usual.</p><p>Evan was convinced that something was going on. He wasn’t sure if it was as simple as Amy having an unrequited crush or if she was actually involved with Professor Anderson.</p><p>It felt a little crazy, but he decided to follow her after class. He kept his distance, but thanks to the crowds of students on the sidewalks he had no trouble tailing Amy.</p><p>The crowds thinned out as Amy walked further from campus, but Evan kept close enough to see where she was going without being discovered. It was when she got into a black Audi that he thought he’d discovered the truth he was looking for.</p><p>Evan walked by the car and quickly glanced inside as he walked past. He saw Amy and Professor Anderson kissing eagerly. He was sure he saw the professor playing with his ex-girlfriend’s big tits just like he used to.</p><p>As he walked back to his dorm, Evan felt crushed. Not only had Amy dumped him, but she’d quickly moved on to the young (for a professor, at least) and exceptionally handsome Professor Anderson. She’d moved on to a man that could no doubt give her the kind of sexual pleasure she craved, the kind that Evan had repeatedly failed to provide.</p><p>Evan moved through the rest of the day like a zombie. He barely paid attention in his remaining classes as he tried to cope with the overpowering sense of sadness that engulfed him. He’d had a plan. He was going to win Amy back. He was going to show her that he’d grown, that he was willing to learn how to please her.</p><p>Sometime after his last class Evan was wandering around campus when he was struck by a thought: Why not do it anyway? Why not just ask? What was the harm? It’s not like she could tell him something more hurtful than what she’d said before Thanksgiving break.</p><p>That’s how Evan ended up sitting on a bench outside her dorm. He parked himself on the slightly uncomfortable wood and waited for four hours before Amy showed up.</p><p>“Go home, Evan,” was the first thing she said.</p><p>“I’m sorry about the way I behaved before Thanksgiving break, and I’m sorry for being a shitty boyfriend,” Evan said as he stood up. “I really am. I should have been better. I should have made more of an effort.”</p><p>He didn’t want to say that he should have worked harder to make her cum while standing on a public sidewalk, so Evan hoped she understood what he was saying.</p><p>Amy’s hardened, annoyed stance softened as she listened to Evan apologize.</p><p>He finished his apology with a simple statement, “I’m ready to learn if you’re willing to teach me.” Again he avoided mentioning anything explicitly sexual, but he was certain Amy knew what he was talking about at that point.</p><p>She did. Of course she did. She couldn’t forget how much of a disappointment Evan had been, mostly because she liked him so much and wanted him to be able to meet her needs so badly. That’s why she wanted to say yes. That’s why she wanted to invite him up.</p><p>Amy knew something that Evan didn’t know, though. She knew that Professor Anderson had just fucked her for the second time that day. She knew that his cum was still leaking out of her. </p><p>“You can say no, Amy,” Evan said. “You really can. I just…I just wanted to let you know that I really like you and that I’m sorry, and that I really am willing to learn. I just don’t know what I’m doing. I need your help.”</p><p>He looked so cute and he seemed genuine and if he wasn’t Amy could kick his ass out of her dorm room in an instant.</p><p>“Would you still be willing to learn if I said you couldn’t have sex with me?” Amy asked.</p><p>“Absolutely,” Evan replied instantly.</p><p>“Good. My roommate is with her boyfriend tonight. Why don’t you come up,” Amy said.</p><p>Evan couldn’t hold back his joyful smile. He practically jumped into the air with excitement as Amy unlocked the door and led him to her room.</p><p>She was excited to see Evan again. She liked him a lot, but things had changed since she and Professor Anderson started seeing each other before Thanksgiving break. He’d shown her a kind of sexual pleasure no man had ever approached and she wasn’t willing to accept anything less from a guy, and she wasn’t going to stop seeing him, either.</p><p>She’d gotten hooked on what Professor Anderson offered. The first time his exceptionally large cock sank into her pussy she had an orgasm. It felt that good. She came two more times before he finished. Most guys couldn’t make her cum once and he’d gotten her off three times in one sitting.</p><p>Evan had an awful lot to live up to, though Amy knew his cock wasn’t nearly as big as what Professor Anderson had between his legs. She knew Evan would have to work harder with his tongue and fingers to even come close to providing the same kind of pleasure.</p><p>She liked him though. Amy kept coming back to that. She liked him. Professor Anderson was nice, but Amy knew it wasn’t much more than sex. As charming as he was, the age difference made it awfully hard to have an actual relationship. His big cock and exceptional skill made it easy to have a sexual relationship, though.</p><p>Amy pulled Evan into her bed when they got to her room. She honestly wanted to fool around with him. She wanted to feel his eager hands and mouth on her tits. She wanted to feel his desire, which she’d grown so fond of when they were dating.</p><p>Most of all, Amy wanted to see if Evan was true to his word. She wanted to see if he really was eager to learn.</p><p>As they kissed Amy could feel how tentative he was being. Evan didn’t want to come off like the orgasm-driven 18 year old he’d been when they last hooked up. He wanted to seem like a man that was willing and eager to learn.</p><p>Amy ended up offering him her breasts, just like she’d done when they first dated. She unhooked her bra and pulled his hand up her shirt. She moaned when he played with her nipples. She lifted her shirt and urged him to kiss, lick, and suck her breasts.</p><p>“Take my pants off,” she finally said. “Let’s see if you’re really willing to learn.”</p><p>Evan wanted desperately to make Amy feel good. He wanted to prove to her that he was worthy of her, so he did as he was told. He pulled her pants off and when she told him to remove her panties he did that too.</p><p>Soon she was naked in front of him. She looked perfect. Her breasts were as impossibly perky as ever.</p><p>“Come here,” Amy said as she pulled Evan’s mouth to hers. They kissed again as she directed his hand between her legs.</p><p>Evan took the direction given to him and soon his fingers slipped into Amy’s pussy.</p><p>“You’re so wet,” he said.</p><p>Amy smiled and said, “Shut up and kiss me.”</p><p>Evan did as he was told. He kissed Amy and played with her pussy. He was rock hard, but he did his best not to think about his boner. He tried to remember his brother’s words. He focused on Amy’s pleasure above all else even though it drove him a little crazy to be so rock hard and not be able to do anything about it.</p><p>“Play with my clit, Evan. Gently, play with it gently,” Amy instructed him.</p><p>Evan had watched instructional videos over Thanksgiving break and he tried to remember the advice they’d given as he moved his fingers from inside Amy’s pussy to her clit. He used the exceptional wetness inside her as lubrication while slowly moving the tip of his index finger in a circular motion around her clit.</p><p>“That’s good, Evan. That’s so good,” Amy said as she pulled Evan’s mouth to hers for a kiss.</p><p>Amy was amazed that Evan was doing a good job. He was putting in a genuine effort to make her feel good. He wasn’t complaining about not getting to fuck her. He wasn’t acting like it was an inconvenience to pleasure her.</p><p>He was better, too. Even when he’d tried to pleasure her before, his efforts had been lacking in skill. This was different. He was actually going to make her cum.</p><p>Try as she might, Amy couldn’t deny that the presence of Professor Anderson’s cum in her pussy turned her on. For some reason she really liked that Evan was unknowingly using someone else’s semen as lubrication. His fingers were covered in another man’s cum and he was clueless.</p><p>That thought was rushing through her head as Amy came thanks to Evan’s fingers. He gave her an orgasm for the first time.</p><p>Afterwards, Evan made no move to try and pull his dick out. He was true to his word. He just wanted to learn.</p><p>Amy let him play with her breasts more. She knew he loved them and his eager tongue felt awfully good on her nipples even after she’d climaxed.</p><p>As Evan continued to play with her tits, Amy wondered if her relationship with Professor Anderson could be a source of pleasure when playing with Evan. It had been far more arousing than she figured it would be to know that Evan was unwittingly playing with another man’s cum. Was there more fun to be had there? What would Evan think if he found out?</p><p>Amy suspected she’d soon find out. She’d enjoyed her evening of pleasure with two different men far too much to forgo future installments.</p>