First time posting on here, sorry for any formatting issues – Characters are me, (6’6, lanky build, brown hair) my girlfriend (description below), and Ashley (ditto)
At the time of this story, my girlfriend (now ex) and I had been dating for a year and a half, and lived together for about six months of that. Our sex life was great in the beginning; I like to give it rough, and she was a more than willing recipient to my, shall we say, ministrations. She was a cute 5’3 brunette, with a pair of the biggest fits I’ve ever seen in person adorning her chest, over a flat stomach and decent, if not outstanding ass; overall she had a good body, but her tits were by far her standout feature, and I loved nothing more than to suck and maul them during our lovemaking/wild fucking sessions. Over time though, the spark faded, as it unfortunately sometimes does, and by the time we hit the one-year mark we had dwindled down to having sex once, maybe twice a week.
Enter Ashley.
Ashley was the one sorority girl in my first university creative writing class; she was a blonde beauty, with a striking yet soft face and an ass to die for. She was off limits from the beginning; I had a girlfriend, and cheating was wrong. However, as the semester progressed, we got closer; we were the two least stereotypical English nerd types in the room, and whether it was that or some other reason unbeknownst to me, we gravitated to each other. One of my friends from that class told me later that everyone could tell there was sexual tension between us from the very beginning; I for one agree. Aside from that, however, our relationship was purely platonic, though I certainly enjoyed the teasing glimpses I would get of her across the room when she would (obviously, looking back, but at the time I didn’t read into it) stretch her arms back when she was sitting across from me, lifting her entirely too-small shirt up just high enough to show off a tantalizing bit of underboob. I was a good boyfriend though, and (for the most part, anyways) managed to fight off the fantasies of slipping into an empty classroom with her, bending her over a desk and ravaging her from behind while she fought to muffle her moans. One day was particularly rough; she was wearing see-through black tights, with an extremely tiny yet extremely visible pink thong teasing me from one seat over every time she stood up; and I regret to say I went directly home at the end of the day and jerked off furiously to the memory. Other than in my head, our only interactions outside of class happened afterward, when we would walk to lunch together and go our separate ways – innocent enough, but I felt guilty for how much I looked forward to those few moments of conversation two or three times a week. Eventually, however, the class ended and I figured that would be the last of my temptation. I was wrong.
Ashley and I weren’t in contact for several months, and to be honest I had mostly forgotten about her, until one day the next semester when I happened to run across her on my way to another class. We exchanged greetings, and I couldn’t help but notice how good she looked in her white crop top and jean shorts, especially in light of the recent drop in both frequency and passion of my times with my girlfriend. The image of her tight ass swaying as she walked away plagued me for hours, and finally, against my better judgement, I texted her. We made small talk back and forth over messaging for a few days, and I was wracked with conflicting feelings the entire time. On the one hand, guilt, for obvious reasons; and on the other, excitement at finally getting to have regular conversation with my forbidden crush from months before. Finally, I made what I knew in the back of my mind would be a fatal error in judgement, and accepted her offer to come hang out at her apartment and have a few drinks. I halfway convinced myself that nothing would happen, but well…yeah.
I got to her place, already a little tipsy, and she greeted me at the door in some of the tiniest booty shorts I’ve ever seen, and we went to her room. I sat down on her futon and she sat on the bed, and to our credit the conversation was as innocent as it could be as we got deeper into our drinks. Eventually after an hour or two I decided to call it a night; I had a horrifically guilty conscience because of the whole situation, and decided I should salvage what I could of it and head home. Which was my full intention, until she gave me a hug at the door. It was the first time we’d touched, other than accidental hand brushes, and it was like a shock went through my entire body. I looked down at her, her green eyes looking back at mine irresistible in the moment.
I bent down and our lips met.
That was the point of no return. If the hug had been a shock, feeling her soft and forbidden lips pressed against mine after months of self-denied lust was an explosion. We kissed softly for a moment, and then all inhibitions went out the window as our lips and tongues swirled together and danced that timeless dance. I couldn’t keep my hands off of her, couldn’t get enough; every inch of her body was fair game. Eventually, they settled to her ass and I squeezed it, hard, through those tiny goddamned shorts and pulled her into me. She let out a whimper and kissed me back even harder as she felt my unmistakable erection pressed against her. We stood like that for probably five minutes, locked in embrace and drinking in the pleasure that we apparently both had wanted for so long.
Soon though, I couldn’t take it any longer and carried her to the bed, relishing the feel of her body against mine, all thoughts of my girlfriend pushed to the back of my mind, though a nagging feeling that this was wrong wouldn’t quite go away. I ignored it though, and we collapsed on the bed into a tangle of limbs. My hands found their way to her tits, and while they weren’t as big as my girlfriend’s, they were a perfect handful, soft and topped with tiny round nipples that at that moment were hard enough to cut glass. I couldn’t resist, and broke away from kissing her lips to suck on them, feeling them grow if possible even harder in my mouth. She let out a moan as I continued to lick and kiss all around them, and I felt her hands pushing me down to her body, where I could already smell the sweet and slightly musky scent of her arousal.
I would like to put it out there that eating a woman out is one of my favorite things to do in the world; there’s an art to it, it takes dedication, and there’s nothing more satisfying than to feel her thighs lock around your head and her pelvis bucking against your tongue while she pulls you into her in ecstasy. If you’re a man and don’t like doing it…all I have to say is that you’re missing out and depriving your girl all at once. But I digress; back to the tale at hand. I made it all the way down Ashley’s body to those fucking booty shorts, that in addition to being so tiny they left half of her extremely shapely ass hanging out, were thin enough that there was already a sizeable wet spot in the crotch. I wrapped my arms around her thighs and buried my face between them without bothering to take her shorts off, reveling in the taste of her womanhood as I ran my tongue over the damp fabric and heard her moan at even that slight stimulation. But I could only wait for so long; seconds later, her shorts were on the floor next to the bed and I was finally face to face with the pussy I had dreamed about for so long. It was tiny, pink, and her inner lips were just peeking out, already swollen with her arousal. It was gorgeous.
I ran my tongue around it a few times, savoring the moment, and then flicked it against her clit, eliciting a gasp. That was enough, and I couldn’t hold back any longer. I slipped two fingers into her depths and curled them against her already swollen g-spot as my tongue lashed her clit mercilessly. The technique was minimal that night, but the passion was not, and it seemed to make up for it, as moments later I felt a rush of fluid against my face and her legs spasmed she rode out her first orgasm of the night. She ran her hands through my hair and I looked into her eyes again, almost getting lost in their deep green. She smiled, then said the words I had been wanting to hear come out of her mouth for what felt like ages.
“Fuck me. Now.”
There was no arguing with that command, not that I was in any hurry to do so. I knelt down between her legs and propped them up on my shoulders and lined my cock up with her pink and still throbbing little pussy as she gently massaged her clit. I’m no monster, though I don’t have any complaints about my size, but next to her petite frame I felt like a goddamn animal. I ran my head between her lips a couple of times, (as is tradition) and then pushed my cock slowly into her willing vagina, feeling it stretch to accommodate my girth as I slowly pushed more and more into her. She groaned as I finally bottomed out, and I stayed still for a moment, intoxicated by the tightness and warmth enveloping every inch of me. That’s when it really hit me – I was deep inside another girl’s pussy, while my girlfriend was back home none the wiser. The taboo nature of the thing struck home, and combined with the massive guilt was a sense of twisted but incredible pleasure. Ashley must’ve sensed something, because she looked at me and said, her voice catching as I slowly pulled out and began to push inside her once more:
“She’s never going to feel as good as me”
I had known that Ashley knew about my girlfriend, but hearing her say that awakened something primal deep inside me and I suddenly felt a mixture of resentment at both her and myself rise up.
“Let’s find out” I said, pulling completely out and flipping her roughly onto all fours. She looked back at me with the most irresistible set of fuck me eyes I have ever seen and at that I pushed her face down into the pillow, and without any pretext at gentleness or teasing, shoved my cock to the hilt into a pussy that, despite my anger, felt better than my girlfriend’s ever had. She let out a moan that was almost a shriek, and reached back to spread her ass to completely open herself to my rock hard and throbbing cock. It was all I could do not to cum right then and there as her pussy was so tight it threatened to push me out with every pulse. I gathered my stamina and began to fuck her like my life depended on it as she continued to moan and clutch at the sheets, arching back to take in every bit of me that she could. I fucked her like this for probably five minutes, roughly grabbing her ass and using it as a handle to fuck her with everything in me. She was a mess at this point, moaning almost nonstop and barely able to speak, but I wanted more. I reached down and pulled her back against me, my left hand around her throat and groping her perfect tits with the other, and whispered in her ear, “You’re right. You fucking homewrecker, you’re right. You feel better than her. Happy?” She managed a smile, and then pulled away and dropped down so she was eye level with my dick, glancing at it lovingly before taking it between her lips and starting to enthusiastically blow me. I let it go on for a few minutes, then pulled her up and kissed her, tasting our mixed fluids on her lips and savoring the soft feeling of her mouth against mine, then laid her down in missionary, grasping her wrists together with one hand and pinning them to the bed behind her. She looked up at me pleadingly, her face smeared and hair a mess; I didn’t think I had never seen anything more beautiful. Three words left her mouth: “Cum for me daddy?”
I’ve never been all that into being called daddy, but for whatever reason that was all I needed to hear. I lined my cock up with her entrance again, and we fucked like nothing else existed but that room and our bed of debauchery. Her pussy squeezed me with every thrust, coaxing me closer and closer to the edge, until I knew I couldn’t hold back any longer. “Where do you want me to cum?” I asked. She responded wordlessly by locking her legs around me, pulling me deeper until I hit the brink and went over, filling her pussy to the brim with every passionate drop of cum I had ever wanted to give her. I neither wondered nor cared if she was on birth control; the pure ecstasy of unloading deep into her unprotected pussy pushed every other thought from my mind. I collapsed against her, caressing her all over as we whispered sweet nothings to each other and let everything else fade away. We just laid there for probably half an hour, basking in the afterglow, and then got up and proceeded to shower together, tenderly bathing each other and kissing and touching intimately the entire time. After, we got back into bed and cuddled up, naked, relishing the feel of our bodies pressed together until we both drifted off.
I woke up the next morning to a slew of worried calls and texts from my girlfriend, and the euphoria of the night before wore off almost instantly. I left to go deal with that, and unfortunately it ended up being the catalyst to our breakup – she never found out for sure what happened (that I know of) but I was too guilt-ridden to stay in the relationship, and things came to an end. Sadly, things fizzled out between me and Ashley; we were compatible sexually, but other than that there were too many differences for anything more to happen between us. I still look back on that night with mixed feelings; it was hot as all hell and some of the best sex I’ve ever had, but the consequences far outweighed the benefits and years later I still miss what that girlfriend and I had. Don’t throw away what you’ve got, folks.
Source: reddit.com/r/gonewildstories/comments/u22mbq/classroom_crush_mf_cheatinglong