Me and Deneese have been friends through highschool, though we were never really close during school days, we often chatted or texted one another all day long. I guess you could say we weren’t comfortable being physically together. We were obviously different people, she was a cynic, I was an optimist. I was the avid gamer, she was the intrepid bookworm. But the thing was, she was always, how you say, available. Just being able to have someone to constantly talk to was enough for me back then, a fixed point.
She had a boyfriend by the last couple of years of highschool, though they never really did it, on account of the conservatism of the guy, I assumed that that was the reason they broke up by the end, and probably the reason why we got together not long after.
It started with the pressure of highschool soon being over, and she wanted to at least experience it before heading off to college. It started with a simple question, then a simple agreement, and then it became a lot more.
A month before graduation was when we both lost our virginity with each other, as an only child to a single parent, it wasn’t uncommon for her to be the sole occupant of the house every now and then, and that was our usual window of opportunity from then on.
Looking back now, It was awkward, relatively bad and was over before you could say premature ejaculation. But to two highschoolers who had just done it for the first time in their lives, it was an incredible experience, one that we repeated on and on again since then.
One of my most memorable experiences in our early years was the day after graduation, all the seniors had to return the togas and square hats to the school’s guidance office, on a saturday, at the beginning of summer. Even though school was out at the time, we were still required to wear uniform to get in, which was a pain in the ass.
Deneese told me to meet with her before turning in the grad outfit, and she dragged me along to a bathroom at the other side of the school. With there being no people in school other than the other seniors on the other side of school, the part we were in was practically deserted.
”Put on your toga” she said, as she did so with hers. Curiously, I asked, to which she just told me off again to put it on.
When we were all dressed up the same as we were during the graduation ceremony, she told me ”I wanted to do this yesterday, but I guess this could be the next best thing”
I don’t know for the life of me what I was thinking at the time, but I do know that I was absolutely clueless until the point where she bent over on the sink counter in front of the whiteboard sized window, and asked me to fuck her from behind. I wasted no time at all.
Skipping the details of putting on the condom whilst awkwardly trying to keep the toga from covering my cock up, I pulled up her skirt and toga from behind her and onto her waist. No panties, why was I not surprised? I slid myself inside of her easily and wasted no time being gentle.
She loves fucking in bathrooms, more specifically, in front of mirrors such as the one we were in front of. Something about watching herself getting fucked from behind that turns her on even more.
Deneese had a very small body frame, but with well rounded hips, which was easy to grab hold of, I thrusted in and out of her, enjoying her sweet pussy while her sweat dripped down her thighs.
She’s a screamer, these days she brings along a mouthpiece with her, like the ones boxers use so that she’d have something to bite on, but on that day I remember seeing her biting on her forearm to keep herself from screaming. As deserted as the school was, there was no telling who might be close by.
It didn’t take long for me to reach climax with the sight of her biting down hard from ecstasy, I remember cumming down so hard I thought the condom would break.
That same day, we returned the graduation outfits, not too worse for wear, but had the vague scent of sex on it, just enough that you can smell it if you’re looking for it, but not enough that just anyone would notice.
We still had an entire summer ahead of us back then, and it was incredible. Our entire relationship was based on sex, discussing, experimenting, practicing, heck, even studying it sometimes. We talked about preferences, likes and dislikes, roleplaying fantasies and whatnot.
We got better at it, or so I’d like to think, as time passed on. By the time we were about to go to college, I helped her convince her mom to let her get a condominium closer to the campus of the college we both applied to, saying that she’d be spliting it with a friend.
Of course, I told my parents the same thing. And for the first couple years of college, we were living together. Needless to say, we kept ourselves busy.
While I could go on for hours of our adventures of exhibitionism and experimentation, Those weren’t even the highlights of it. In fact, it was after we broke up over 2 years after we got together that things started to heat up.
When a relationship is based on sex, you can’t expect it to last forever. Soon things become repetitive and unexciting. The thrill becomes ordinary. At least, that was why I thought we broke up. She just went and said that we should, and I agreed without arguing. The last few months seemed monotone, an insanity-driven serenity.
I opted to move out, I got into a dormitory still not far from campus. We kept in touch, same as we were before we got together. Since then I’d like to think that it was just a hormone driven fling.
Two months later, I got a different girlfriend, Christina, and even though me and Deneese were exes, I felt comfortable telling her about how I felt about another girl. She didn’t mind, there were no tones of jealousy at all. I should have known what Deneese had been planning all along.
Four months after that, was when I realized just how tethered we still were to each other. Deneese had invited me over to hang out, something we do quite often even after we had broken up.
She was wearing short shorts and a clean white blouse that her long wavy hair was resting on. It seemed so innocent at the time, small talk. She liked to talk about how my new relationship was. I should have known the moment she asked.
”So, have you two done it yet?”
I told her that we have, and then she asked how it was.
”It’s good.” I said. Aaand bingo, I gave her all the ammunition she needed. At that moment, we were both seated around a small table, we sat across from each other. She said to me.
”Just good? not great?”
”Well, it’d take some time for us to learn more of each other, took us a while, didn’t it? Good will turn into great soon.”
”Don’t you want to remember how great felt like, right now?” she said, and then I felt it, a wave of pleasure, it took me a while to register that it was her foot that was up on my crotch, rubbing softly her toes along the shaft of my cock.
”Deneese, what are yo-”
”Don’t you miss me sometime?” she said, cutting me off.
I tried to keep my composure, and in that attempt, I ended up sounding vulnerable.
”We are not doing this, I have a girlfriend for christsakes.”
”You can keep saying that, but if you really believe what you’re saying, you would have backed off by now. Yet here you still are, enjoying every second of my warm foot on your cock” she said, quite confident of herself.
I couldn’t help but hold still, she was right, a foot rub from her felt better than a blowjob from Christina. I was in her snare, she had me under her thumb, or more aptly, under her foot.
She kept talking ”I missed you and your cock for every second that we weren’t together, it was agonizing.”
”But you’re the one who broke it off, remember?”
She put down her foot, and I let out a subtle sigh of relief.
”Because you would never have done this had I just asked you to.”
”Do what?”
”Cheat on someone for me. Why do you think we broke up in the first place?”
”Wait, so we broke up because you expected me to get a girlfriend and expected me to cheat on her with you?”
”I didn’t expect it to happen, I know that it would happen.” she said with a devious look on her face. She continued ”As much fun it was to roleplay the cheating boyfriend or girlfriend, it would be so much more fun to do it for real, don’t you agree?”
She put her hand on her chest, and began single-handedly unbuttoning her blouse from top to bottom.
”I’m not doing this with you, Deneese”
”You can stand up and walk out that door any time you want.”
I couldn’t help but stare at her chest, as she finished off with the final buttons, I could see an unbroken line of skin between her unbuttoned blouse running from her chest downwards, no bra, typical.
”But you can’t, can you?” she said ”You miss me, and you just don’t want to admit it. And until then..” she stood up, took one side of her blouse and put it over the other, covering her skin back up. ”..You can just get the hell out.”
She pointed me to the door and I left, I was shell-shocked, she had rocked me to my core. The whole elevator ride down, I looked back on our breakup, how more sensible it sounded now. I didn’t know whether or not to leave or go back and talk to her.
But there I was, 5 minutes later, and I’m at her door again, I went back around, I don’t know exactly what I was hoping to do. I knocked, she opened, her blouse still unbuttoned, judging by her expression, she expected me to come back.
”Fuck it.” I said out loud, I seized the opportunity and I grabbed hold of her, her lips meeting me halfway as I pushed her up against a wall. The door behind me closes on its own as I hold her close. She lifts my shirt off and throws it to the side, I could feel her unbuckling my belt, slipping it off as soon as she does.
I could feel her smiling under the kiss, and second to second, it got a lot more intense. The feeling was all too familiar yet at the same time excitingly new. I moved downward and began kissing her at her neck, feeling her hands press me up against her smooth skin.
She says, cockily ”Took you long enough” she giggled.
I pinned her body up against the wall as I took my hand and grabbed her neck, squeezing it on the edge of pain and pleasure. I put my face right on hers and looked her in her eyes. ”Not a word of this, to anyone, understand?”
We both preferred being submissive, so we had made it a thing long before that to alternate roles every now and then, to keep it fun. It got to the point where we could do it seamlessly. She was like that due to her daddy issues, I was like this because I look intimidating by nature, and it was hot as fuck that the only thing that could intimidate me, was her.
”Yes” she said under a soft innocent breath. Looking back at me, she whispered ”Please, fuck me.”
I lifted her up, she held on to me, with her legs wrapped around me. I carried her into the bedroom and I threw her on the mattress. She was happy, under that innocent face I could sense her smugness at the situation, she was turned on by the fact that she was going to fuck someone else’s man, even though in truth, I was hers, She made it clear that day.
I climbed on the bed, propping myself on top of her. I leaned down and went back to caressing her neck with my tongue. I slid my hands from her hips upward, clearing her blouse out of the way, stopping as I cupped her breasts.
Her breasts weren’t that big, but I always loved them, they felt full enough in my hands, which made them fun to play with. Not too small, not too big, just like fucking goldilocks’.
I kissed her downwards, running my tongue down her chest, making a rendezvous with my hands. I gave attention to her left nipple first, sucking her areola until it grew stiff, and when It did, I moved on to her right.
She moaned and groaned the entire way, she was louder than usual. I continued downwards, working around her belly button, and finally reaching her shorts, at this point I was halfway off the bed. I looked back up at her, and she was looking back at me, waiting anxiously.
I went lower, sticking my nose under that useless zipper, and I took one long whiff. Behind the thick fabric, I could smell her wetness, It was almost enough to drive me insane, I hadn’t realized how much I missed it. I pulled her legs together as I helped her off of those shorts. She just laid there to watch it all unfold.
I began slipping off her underwear, a small dark red piece of cloth, it was as wet as you’d imagine. I dug in on her waist, her legs propped up against my shoulders as I begin gently licking her pussy’s lips.
After every other pass, I make sure to slip the tip of my tongue just enough to tease her to want more. I go on, deeper and deeper. I could feel her body arching back as I bury my face on her pussy. I twist and curl my tongue the way she always liked it, and she moaned the way I always liked it.
When I felt that she gotten teased enough, I stopped, gave her pussy a kiss, and stood up in front of her. I unbuttoned my jeans and slid it along with my underwear down with it.
She stared at my cock with a lustful smile, biting her lip, knowing what’s coming next. I climb back onto the bed with her and nestled the shaft of my cock on her pussy, rubbing the length of it on her.
”Are you gonna fuck me the way you fuck Christina?” she asks me, as she looks into my eyes.
”No, I’m going to fuck you like the little slut you are.” I pulled back my hips, and guided the tip of my cock inside of her, and I thrusted inward. I felt the warmth of her pussy for the first time in 6 months, I felt like I was home again. I leaned down on her as I kept moving my hips back and forth, rubbing the head of my cock on the walls of her vagina.
She locks her feet together behind me, pulling me inward with every thrust, going deeper and deeper as it goes on. I grab hold of one of her tits as I suck onto another, I could just feel her fingers on my bare back, digging in for the long haul.
She screamed and moaned as I grunted in with every push inside of her. I kept going, keeping a pace and rhythm, turning her disjointed string of moans and screams into a melody, It was like playing an instrument. I could hear her panting in between the choruses, and going louder with each crescendo.
I felt her hand on the back of my neck, pulling me to look at her. Her eyes locked onto mine, and mine hers, as she mouthed the words every man wanted to hear. ”Cum inside me.”
I felt it tinge down my body, and I felt it rushing up from the base of my cock. I bucked into her as her legs pulled me in. I came inside her, I felt my cum filling her inside as she responded in pleasure.
We stayed in that position as the rush began to calm down, more and more I notice how out of breath I was, how sweaty we both were, and I began trying to comprehend what had just happened. I pulled myself out of her, and some of my cum flowed out. I collapsed on the bed beside her and she, in turn, cuddled up at my side as I stared in the ceiling in disbelief.
”So, what do you think?” she asked me, genuinely curious, waiting for me to respond.
”You were right, that was great.”
I am a horrible boyfriend.
Source: reddit.com/r/sexystories/comments/44rs4d/i_am_a_horrible_boyfriend_mf_cheating