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How I Lost My Virginity To A Cheater (Long) [MF]
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EN: All names are changed for obvious reasons. I always encourage reading the whole tale because I take time to craft each part to flow and tie up somewhat nicely. I recognize I could split this up into many stories, but I feel it's better having one continuous buildup and cathartic release instead of breaking it up. I did add breaks in-between for steamy moments before the big reveal.

Junior year of College. I was dumb, 20, and just moved into a new dorm Winter quarter. After suprising my new roommate, who didn't know he was getting another roommate, I moved in with the help of him and his assumed girlfriend. There was another girl there, a Japanese exchange student named Aiko. Once we settled in and got food, we got to talking in the living room.

My new roommate introduced himself, a Japanese exchange student named Daisuke, and his friend, an American named Lucy. They were quite literally unable to keep their hands off each other and at one point, Daisuke spanked Lucy in front of everyone. I asked if they were even dating, which led to an emphatic "Yes!" by Daisuke, followed by another spank. Since they were dating, my curiosity directed to Aiko. She revealed she was also dating someone, a guy she had dated for years, but since she was on an exchange program, he was back in Japan.

Later in the night, Lucy mentioned that she was kinky. I asked if spanking was one of her kinks, which she rolled her eyes at me saying "Yea, of course" silently. Then, she directed all of us to take the BDSM test. Quite odd that just a few hours ago, I didn't know these people existed, and now I'm sharing my kinkiest desires with everyone. I assume my test wasn't really accurate, since I hadn't actually slept with anyone, but I think I leaned Dom even then.

What was most surprising was Aiko's test. For such a small girl at 5'1, she had something like 80% Dom on her test. We all goaded her to send it to her boyfriend. She capitulated and sent a screencap of her test to her boyfriend who was probably just waking up at this point. None of us saw his reaction unfortunately and we all went to bed shortly after.

Aiko was a staple of the dorm for Winter. She would often come over because she and Daisuke were part of the "English as a Second Language" courses. It was a requirement for all Japanese exchange students to do these classes, so they would be often connecting outside of class to do assignments and whatever else. Lucy was also part of the program, but as a teacher. She was learning Japanese on the side, and through the program is how she met Daisuke and Aiko.

I connected with Aiko on a lot of things. From Japanese music, to food, to anime, we really got off great and I was happy to share what I knew, and learn more from her. Since she came over for English help all the time, she would specifically ask me questions about how to write or answer something with correct grammar. When she had a problem with her laptop, it was me she went to first. Not saying my life was an anime at this point, but I'm not denying it either. But she was genuinely a friend, and I liked having everyone around.

One night near midterms, Aiko is over with Daisuke, Lucy and I. They had a new friend, Daniel, over, who was also part of the ESL program. Daniel was a veteran, and was using his GI Bill to qualify for teaching ESL, so he could go back to Japan where he was stationed. There was a big project apparently, so they were all working through it and bouncing questions off me.

Throughout the night, Aiko was inching closer and closer to me. At first, she was just on the ground beside me. She got up to sit one seat away from me on the couch. But she didn't stay there for long. She steadily inched towards me, scooting closer and closer. At around half past midnight, Daniel says he's going off to go get dumplings. When he comes back, he's definitely looking at me and Aiko's lack of space between us.

I wrapped my arm around her shoulder at some point and brought her in closer. I don't remember if I was prompted, but knowing how dumb I was, she probably said "I'm cold" and I just went with it. I could feel her warmth, her sighs of satisfaction, her snuggling up even more against me. She even would tilt her head up to look at me when I would ask her a question. It felt good having her by my side. I had thoughts like "What if her boyfriend saw this?" but I pushed them away because it was easier to accept the position I was in already. And to be fair, she was making most of the moves.

At 2:30 AM or so, Daniel says he's going to bed. He's a little curt, but I chalked it up to tiredness. Lucy and Daisuke also say they're going to bed right after. Aiko and I are still close, my hand now resting just above her hip. After a couple of minutes, relishing in the shared warmth between us, she starts nibbling on my earlobe. I whispered to her "What are you doing?" and she sat up to whisper back in my ear.

"You know when Daniel left, you looked at me. I wanted to kiss you so badly. I didn't because I didn't want the others to see. But now we're all alone so..." her voice trailed off. I sit back a little, and look at her big brown eyes. She starts to lean in and I just let it happen. We locked lips. After our first kiss, we started attacking each other, furiously kissing one another.

I kissed her neck while she nibbled on my earlobes. I pushed her down on the couch so I was straddling her, continuing my flurry of kisses. My body was involuntarily humping her, grinding against her through my pants. The heavy breaths, in between our lips locking, was intoxicating. After 30 minutes of intense making out, I pulled back and said I should probably get to bed. Her face was flushed but she was very satisfied. I can still remember her sweet smile, and then saying "Shh, this is our secret". She left shortly after and I passed out on the couch.

I woke up at 5 AM and had intense nausea. Combined with not eating enough, the guilt was eating away at me for what I had done. I felt truly awful. It was a whirlwind of anxiety and throwing up, not feeling like I was ever going to reverse what I had just done. My mind was racked with moral questions. I took the day off and just focused on stabilizing myself.

When I saw her next, a couple days later and in between classes, I told her that we shouldn't have done what we did. She questioned, "Why not?". I was shocked I had to answer, "You have a boyfriend and I feel awful". She then comes closer to me and softly said, "He doesn't need to know". She smiled and ran off to class.


2 weeks later, she's over again. It's the evening time and I'm showing her videos on Youtube. Her and I are having a great time, just like good friends. She's laughing and asking questions. I'm answering and just geniunely really enjoying the vibe. Then, she sits on my lap for a few videos. My arms wrapped around her stomach, "to make sure she stays on", I justified in my head. I started having those feelings from before though. After a while, she asked if we could be more comfortable, and I point to my bed. Her and I climb up and I have about as much resolve as a sand castle against a wave.

She kissed me again. We are really into each other, just like that late night session. My body moved against her again, signalling for her to keep going. She's panted while I kissed her neck and bit her earlobes. My shirt and pants come off for me to "get more comfortable". Her shirt and pants come off swiftly after. My hands rub against her black bra, squeezing her cute tits. My cock was leaking with precum, soaking through my underwear. We were facing each other and the intensity kept ramping up in a positive feedback loop. Her body was pressed against mine, and my hips rocked into hers as her leg swung over my hip. This position granted even more friction and pleasure. We could feel each other's heat, while the tension spun out of control.

My cock couldn't handle being trapped anymore. I asked Aiko if it was ok to take off my underwear, and she said it was ok to. We were spooning now, my cock pressing against her ass, kissing her neck with my arms wrapped around her stomach. I felt so pent up, so incredibly horny, that I was pushing against her underwear right onto her pussy.

Now, I don't condone this action from past me, but I also didn't know what could happen physically. I pushed her underwear to the side and I asked "Is this ok?". She responded affirmatively, and I rubbed my cock right against her bare pussy. It felt electric getting that first touch, feeling her bush against my bare, throbbing cock. In doing so though, I may have accidentally slipped in the head of my cock.

She pulled away and turned to face me. She whispered, "It doesn't feel right to do that right now. You're a virgin", but before I could respond, my roommate walked in. He told us that dinner was ready before he saw us, me clearly shirtless, and left with a smirk on his face. We were covered by the sheets, but he knew what was going on. We got dressed and shared dinner with the other roommates.

A day later and the swirling anxiety returned. I couldn't believe I did it again. I found her on campus and I tried to establish an even stricter boundary. "No more cuddling" I demanded. She complied... for a couple more weeks.


She slept over one night. Her excuse? Her roommate was fucking her boyfriend, and she didn't want to be in the room. She would rather sleep with someone she trusted anyways, and it wasn't cuddling cause we were "just sleeping". Like clockwork, we got up to no good. This time, it was in the morning, around 10 AM. We wore shorts and baggy t-shirts for sleeping, and it was nice to have another person in bed. My roommate was out by the time we woke up, so we got back to making out. The flame had rekindled and I felt an animal inside of me. I was dry humping her like I needed to fuck.

I mounted on top of her, trying to get out my sexual energy while her legs were spread and she just looked at me. I was making out with her while I humped against her. My bedframe was knocking against the wall with how hard I was humping into her. It couldn't have felt very good for her, but the sexual desire was overflowing and I grunted with each thrust. I flipped her into doggy, stripping off my shorts and hers, and the hunger to have her grew. I humped against her, grabbing her ass and digging in my fingers. I was so desperate to feel insider her, but I didn't pull my move from last time. I gave up after 10 minutes, exhausted and huffing.

As I got off her, I told her we shouldn't do anything like this anymore. "I feel so guilty every time", I said to her. She nods, looking down somewhat sad. I don't see her for another 2 months.

We randomly stumbled into each other at midnight during Spring. I had turned 21 a few weeks earlier, so I shared that I was finally able to drink. I asked her why she was out so late, and she told me she was getting job interviews for businesses in Japan. Early morning interviews require staying out somewhat late due to the time zone difference. I offered to walk her back to her dorm, partially to keep talking with her.

When we get back to her front door, I asked her about her boyfriend. She said they're still together, and that she really does love him. I pressed her on that, using my own situation with her as proof. She again brought up that "he doesn't know, and what he doesn't know can't hurt him". I told her sincerely, "I wish you the best then, and I still don't want to be like that for you." She does the same sad nod, before we hugged and I walked off to my place.


Middle of May. Aiko showed up again. She used that same excuse as before, that her roommate's boyfriend is having too much fun in their room. I don't mind though, because it is nice to have a friend over again to talk with. Daisuke, Aiko, and I have a little drink, and eventually discuss relationships. Daisuke is a bit lonely because Lucy is in an exchange program in Japan, the opposite of what is happening to Aiko. Apparently, Lucy and Daisuke discussed opening up their relationship, and how it wouldn't be considered cheating if Daisuke has some needs he has to take care of. She just wanted to know if it were to happen. Lucy wouldn't ever indulge herself, but she accepted that Daisuke might, so he might as well be free to do so with good communication.

We naturally segued into talking about cheating in general. Specifically, what action would broadly be considered cheating, if it were to happen to any relationship. Everyone agreed that blowjobs are 100% a step too far. Most people do consider kissing cheating too, but we noted that some people are ok with their partner kissing others, or it could be an honest mistake when you're way too drunk.

Daisuke and Aiko continued the conversation in Japanese, while I just sat there. It was normal for them to discuss like this, and I was used to not knowing what they were saying. After it ended, Daisuke said he wanted to call Lucy and talk with her for their daily check-up in the living room. It was around 1 AM at this point, and I was starting to fall asleep. Aiko seemed to have the same idea, so she joined me in getting into bed. She said something in Japanese, wanting me to repeat it verbatim, which was something like "I want another drink". I did it despite my best wishes, and we shared an ale before getting snuggled up into bed. I wasn't exactly feeling great about the situation, but the drink certainly helped.

The night was restless. I constantly woke up, to kiss, grind, hump, grab Aiko in bed. It was like the spark never left and we slowly shed our clothes through the night. It had gone on for 2 hours, a mix of sleeping and playing with each other. At some point, I was completely naked, humping against her while spooning, kissing her neck while she softly moaned. She rolled over and asked me that fated question, "Do you have a condom?"

My heart started to race. Immediately, I jumped out of bed to go to my backpack. The day before, my friends had given me a condom because I wanted to know what brand it was and how it felt on me. I fished it out and well, I was still a little drunk and had never put on a condom properly. I struggled before Aiko noticed I wasn't coming back to bed and said "Do you need some help?" I weakly said, "Yeah, that would be nice," before she got out of bed and rolled it onto me. I was rock hard and so excited to finally be doing this.

I laid down on the bed, my cock standing at full attention and pointing straight up. The window provided our only light, and I could see her black bush slowly come down onto my cock. That moment of insertion was incredible. She was very tight, and she needed time to get adjusted to me (I'm average and I know it). I felt my cock head, and then my shaft, get squeezed by her. She slowly slid down, before she finally bottomed out. She was fully in control, and held that position for a second. I could see that she was wincing, before she lifted her hips back up and slowly rode me.

Our breaths were escaping our mouths with each slow thrust. I held onto her hips as she rode up and down on my shaft. Her pussy was clearly wet, and it was making little squelching sounds as she sank back down onto me. She always made sure to take all of my cock inside her with each thrust down. Her pussy was so warm, and even though I wore a condom, I felt her body reacting to me every time I slid back in. Her tightness opening up to welcome my cock with the best hug ever, before releasing its grip on me as I slid back out.

I was too horny to let her lead though. I wanted to be in control. I asked if we could get into a different position and she suggested missionary. We flipped over and I watched my cock slide in between her puffy lips. I kissed her as my cock slid in and out.

My thrusting technique in this position wasn't very good though. Whereas she had control and a steady rhythm, I had a binary thrust - All in or all out, no in-between. It was stilted and definitely needed improvement. However, she elicited tiny moans, encouraging me to keep going. At some point, when I was fully inside her, I asked how it felt. She said "Really full" and then I went back to my hard thrust action. It was nice to feel her in this position, but after 5 minutes or so, I told her to get back on top of me.

We flipped back around, but the dynamic was firmly in me leading, despite me clearly not knowing how to fuck. She slid down again, but I held her hips in place. I thrusted from underneath her, in that same stilted manner, but she was seemingly getting more pleasure. I could feel her pussy was reacting more too. I kept it up, fucking her from underneath, and her breaths got shorter. I moaned out a soft "fuck" while she started to whimper. She says she came shortly after, but I was too naive to know if this was really true.

She got off and rolled over next to me. We both passed out and I woke up to the sun shining through the window at 6 AM. I wrapped my arm around her, and she woke up. We kissed and I looked down at my stiffening cock. The condom was somehow still on it, and she looked into my eyes with a devilish smile. "I guess this is how I can treat you for last night", she said as she slid down the bed and put my cock in her mouth. Her technique for blowing is about as good as mine for fucking, but the moment was hot.

It was also the cheating line we set up earlier that she was intentionally crossing. I knew that we had sex, but the act of doing something we both knew was 100% cheating and doing so consciously, not in our weird, sleep deprived state, meant so much more.

She later told me that she felt comfortable taking my virginity after that second make out session where I pulled her underwear aside. She reasoned that I basically had fucked her already, so she might as well go all the way. It was a stupid decision still, but it worked out I guess? And just like our make out sessions, we fucked 3 times too. The second one was the hottest, and I could write about it another time. Lemme know if there's interest, and it wouldn't be as long as this one.

Anyways, we eventually broke it off. It didn't feel right fucking her, even though my dick loved to. It was just not where I wanted to be, and I knew she was going back to Japan to see her real boyfriend. I was merely the sex that got her through America and I haven't talked to her since. She did get married to him in the end.

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