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Sorry that this is INSANELY long, but this is more for me than it is for anyone reading, anyways :) This happened quite a few years ago when I was 25. I had been dating my now wife for a year or so at the time. We would get married 4 years later. I've never told anyone this story until now. This happened with a friend a year older than me named Lindsey, who I don't think (hope) has told anyone either. Lindsey's younger brother is my best friend, and has been since we were about 10 years old. Because they were only a year apart, Lindsey and her brother always shared a large co-ed friend group with them at the center. Their house was always the place everyone hung out. And while as kids there was plenty of teasing back and forth, and I'm sure she hated me at times, Lindsey and I became very close friends starting in high school. To this day, I'd still consider her my closest female friend. I'm Chinese, about 5'11" and slim, about 160 lbs. Lindsey is 1/2 Japanese and 1/2 white, 5'5", with an athletic body, dark brown hair, seemingly always in a ponytail, and hazel eyes, which contrasted with her tanned skin. We both played soccer in high school, attacking midfielders, and were the stars of our respective teams. She was better than I was for her gender, and ended up playing at a low level D-1 in college, while I played sparingly for a year at a D-3 a couple hours away before realizing I'd rather not make the time commitment to soccer any more. We became extra close at the end of high school, went to senior prom together (as friends) and worked out together preparing for our transition to college soccer. Friends often teased us that we would end up married because we had so many similarities. I'm not 100% sure if she ever liked me, and I mostly saw her as just a close friend. I would have phases where I thought about her as more than a friend, but they would always seem to pass, and I never told her or even consciously flirted with her. The only time I thought maybe something else was going on was during college, when we stayed in a hotel room with about 6 other people who were visiting the closest city to my college. I had planned on driving back about an hour to my school, but we had been out drinking, so I crashed in their room. There were two double beds, and Lindsey had been sharing one of the beds with a female friend the night before, but I rudely took the spot next to Lindsey when it was time to pass out. Although I really wasn't thinking it at the time, in hindsight I realize I wanted her. Lindsey and I were both in relationships at the time, but nothing serious. I was drunk and wanted some action–if my girlfriend at the time had been there I don't think I would have looked twice at Lindsey. But she wasn't, and Lindsey was laying right there, seemingly asleep. Once I thought everyone was asleep, in the least smooth way possible, I "accidentally" rolled over and put my arm across Lindsey's body, spooning her from behind, just barely touching her back with my torso. She let out an almost imperceptible sigh and shifted back into me. I still wasn't sure if she was asleep and it was just a reflex. Every minute or so, I would inch a little tighter. Then nothing. Then she would inch back, or move her ass into my crotch just once. This went on for most of the night, neither of us making a real move. We still had plausible deniability. With the six other people strewn across the other bed and the floor, we knew we couldn't actually try something. Looking back, I should have taken her to the bathroom or something and fucked her brains out, but I was still too scared. What if she didn't actually want me? This would ruin our friendship, and maybe my friendship with her brother, too. Even best case scenario, it would be really weird. Blue-balled and still drunk, I eventually fell asleep. In the morning, it was like nothing happened, and our friendship carried on from then as normal. But now I looked at her differently. It's not like I was in love with her or anything, but from then on, it was no longer asexual. I looked at her, as corny as this sounds, as a sexual being, whereas before I never even thought it was a real option. Fast-forward to a few years out of college, and I was back in school getting a master's degree. I had met my then-gf, now-wife, early in the first year of my grad program. For Winter break in the second year of my program, I went home for the holidays and my girlfriend stayed in the city my grad school was located in with her family. Lindsey and her brother were back home for the holidays, too, staying at their parents' place. For New Year's Eve that year, we pressured them into throwing a house party to avoid the hassle of going out downtown. Lindsey's parents made themselves scarce, and it was a fun party, not crazy by any stretch, but a good bit of drinking and seeing a lot of familiar faces. At the end of the night, I could have been dropped off at home, but I decided to crash there so I wouldn't have to come back to pick up my parent's car the next morning (ah, the joys of being home for break), and I was too drunk to drive myself. Other people in the same predicament began picking places to sleep, and the guest bedroom and couch were taken. I tried to head into Lindsey's brother's room, but he had gone to sleep drunk before midnight and locked the door, fearing being pranked I guess. My options were the floor or Lindsey's room, so I opened the door seeing if I could share her bed. I was excited at the though of it, thinking back to our spooning session years earlier. We had been flirting lightly throughout the night, and between that and the liquid courage coursing through my veins, I had a feeling I might get past the hump this time, so to speak. I opened the door, and saw Lindsey and her best friend, Jenelle, both laying in bed, preparing to go to sleep. God dammit, Jenelle! Not to be deterred, I said, "All the spots are taken downstairs. Let me get that spot in the middle." Despite a little bit of protestation from Lindsey, I squeezed into the middle ostensibly to go to sleep. Jenelle, drunk as could be, passed out almost immediately, snoring softly behind me. Lindsey had changed into some old soccer shorts and a t-shirt. Lindsey and I laid there in silence for what seemed like forever, motionless. Once I was convinced Jenelle was out, I scooted forward and slowly put my arm on Lindsey's hip. This was purposeful. There was no more plausible deniability. But I was still terrified. One drink less and there's no way I would have done that. But I couldn't stop myself. In that moment, I wasn't thinking about my girlfriend across the country, even though I really liked her at the time. I was only thinking about Lindsey–that I needed to take it further than I had in college. To my relief, she scooted back, again sighing deeply as she had 4 years prior. She started slowly grinding her ass into me, moving no more than a centimeter per second so as not to wake Jenelle. I leaned my head forward and breathed warmly on her neck. She tilted her head down and brought a hand up to move her hair out of the way, inviting me to kiss her neck. I obliged, kissing and gently biting her neck and earlobe. My cock started to stiffen through my jeans. She pushed back against it with her ass harder, but still moved achingly slow. I reached up through the bottom of her t-shirt to feel her breasts. They were on the small side, a B-cup at the most, but were perky. I brushed my hand across her already hard nipples, and she responded with another quiet sigh, this time right into my ear so I could hear it. We spooned like that for what seemed like hours, but was probably no more than a couple minutes. My cock was now completely hard, and Lindsey moved her ass forward off of it and reached behind her to start stroking me slowly through my jeans. In turn, I moved my right hand down across her flat, toned, stomach, and easily ducked my fingers below the waistband of her shorts. She tilted her hips up encouragingly, and I felt the top of her trimmed pubic hair. I was still conscious of Jenelle behind me, and was moving much more deliberately than I wanted to. I finally reached her pussy, and slid my fingers over her clit and then my middle finger through the slit between her lips. It was soaking, and my hand glided effortlessly back up across her clit. She breathed in hard, and I froze, scared that she would wake up Jenelle. Lindsey seemed startled at her own reaction, and momentarily stopped rubbing the outside of my pants. As if to tell me to get back to my job, she moved her hand up behind her back and started trying to undo my belt. I started rubbing her clit in circles with the pads of my fore, middle, and ring finger, lubricated with the juices that seemed to be flooding out of her. She started moving her hips up and down slowly in rhythm with my hand, then began picking up the pace. She had stopped stroking me and put her hand over her mouth. She started breathing hard and thrusted her hips back and forth in short, fast thrusts. She let out an audible, deep, "uhh!" and then pushed her hand tighter against her own mouth. I thought about stopping to not wake Jenelle for a second, but I knew Lindsey was cumming so I kept the pace up with my hand until her breathing and hip-thrusting slowed. Lindsey took her hand down from her mouth and squeezed my right forearm a couple times as I slowed the pace as if to thank me. She then reached behind her again and started to work on my belt. She was mostly failing, so I moved up and forward to guide her back to my cock. She again started rubbing slowly but strongly, gripping my hard cock though my jeans. I reached over a little further and slipped my middle finger into her warm, wet pussy. Soon, I moved my ring finger inside as well, and started curling them back toward me inside her. Lindsey's g-spot was the most prominent I've ever felt. I don't know if it was larger in area or just more engorged or what, but I immediately felt the different texture. Every time I brushed my fingers against it, she would tense and squeeze my cock harder. If we weren't trying to stay so still and quiet, I could have made her cum in no time. Unfortunately, in the position we were in, I couldn't really reach, and flexing my fingers forward to reach her g-spot was absolutely killing my forearm. Lindsey was reaching back toward my belt with her hand behind her, trying to get to my cock. With my left hand trapped underneath her body, I took my right hand out of her shorts and used it to help her undo my belt and unzip my jeans. She immediately reached inside my boxers and gripped my cock. If I was completely sober I might have cum just from that, I was so turned on. I moved my right hand back to her pussy and started rubbing in circles, slipping in a finger or two sporadically. She started to stroke my shaft, but again, the angle was awkward and she couldn't really get a good rhythm going behind her back. She slowly rolled onto her stomach away from me and put her right foot on the ground. Then, again, slowly, she continued turning and moved her left foot to the ground. Now standing, facing the bed, she made eye contact with me for the first time since I had gotten in bed. With just dim light from a streetlamp outside her second story window, I could see her eyes tell me how bad she wanted me. I knew what she wanted me to do, so I veeeeerrrry sloooooowly moved out of the bed and she took my hand in hers. We tip-toed across her room into her bathroom. She went to lock the door that led into a hallway. I closed the door that led to her room. We didn't turn on the light, but I could see the outline of her body with my eyes fully adjusted to the darkness and some ambient light coming from the small bathroom window. We met in the middle of the bathroom and kissed passionately for the first time. It was hot, but weird, and for the only time that night, I felt not entirely "in it," conscious of all the baggage this might bring. I broke off the kiss. The feeling was fleeting, though. I quickly grabbed her shirt and lifted it over her head. She pulled down my jeans and boxers, and I stepped out of them as I worked on the buttons on my shirt. She knelt down and grabbed the base of my cock, then sank her mouth over it as far as she could go, almost to the end. I let out a moan under my breath as she took long strokes on me with just her mouth. She had her hands on my hips, guiding me in and out of her mouth. Once I had my shirt off, I gently pulled her up with my hands on either side of her head. The blowjob felt amazing, but I needed to fuck her. She dropped her shorts in a flash and turned around, putting her hands on the counter. She bent over and stuck her ass up. I rubbed the head of my cock against her pussy, planning on teasing her a little, but I couldn't help myself, and plunged inside. That moment, sliding inside her tight, warm, pussy, feeling it clench around me, with the faint light bouncing off her ass, seeing her look of pleasure in the mirror in front me–with the circumstances what they were, and the forbidden nature of it all–that was the craziest, best, most pleasurable I had ever felt. I started slowly thrusting deeper into her, and on the fifth or sixth thrust, I was in as far as I could go. I grabbed her hips and started thrusting harder into her. She bent her knees so my dick was pointed down a little and started kind of bouncing as I fucked her. "Keep going, I'm gonna cum," she whispered. I did as I was told and looked into the mirror as she started cumming. She closed her eyes tightly and stopped breathing. I kept going at a constant pace and her legs started to shake, which felt amazing. "I'm cumming, I'm cumming," was all she could say. I slowed my pace as she came down from her orgasm. Then she turned around and hopped up onto the counter. Her arms were supporting her body, which was at about a 45 degree angle. I put my arms underneath the backs of her knees and held her legs open as I entered her. We made deep eye contact, but didn't say a word. After a few seconds, she grabbed a towel to put underneath her ass. I assume the counter hurt, but she didn't say anything. She just sat back on the towel and opened her legs, inviting me in. With her pussy hanging just off the counter, I went back to fucking her. She moved one hand down to her clit and started rubbing it, which really turned me on. Watching her rub herself with me inside her, seeing her open her mouth in pleasure but remaining silent, had me ready to cum. I didn't want the night to end, so I pulled out. I sensed some disappointment, but I quickly plunged two fingers inside her pussy and put my mouth on her clit, moving her hand out of my way. I stroked my fingers back toward me inside her across her g-spot and started to suck on her clit. Within seconds, she was grunting in a hard whisper, and I felt her squirting all over my chin and hand. As I came up, she gave me an embarrassed smile. With her juices dripping down my forearm to my elbow, I wiped it off on the towel she was sitting on, sarcastically acting like it was a chore and I was annoyed. She reached down and stroked my cock, seeing right through me, then guided me inside her pussy once more. She felt amazing, and any restraint I had exhibited throughout the night was gone. I fucked her like I was shipping off to war the next morning, thrusting as hard and as deep as I could. Less than a minute later, there was no more holding out. I whispered, "I'm gonna cum," and Lindsey pushed my stomach back and hopped off the counter. She quickly took the head of my cock in her mouth and stroked my shaft with her hand. As I started cumming, I pulled the back of her head so that she deep throated me. She took her hand off my cock and grabbed both of my ass cheeks, pulling them into her so I could get my dick as far down her throat as possible. All I could do was grunt. My knees weakened as I shot a huge load into her mouth and down her throat. I hadn't seen my girlfriend in two weeks by this point, so this was intense to say the least. I shuttered and moved her head back and forth just a little until every drop of cum had been emptied from me. She had swallowed most of my load, but some of it had crept out and was running down her chin and onto her tits. She got up and used the towel on the counter to clean herself up, then ran the faucet into her cupped hand and swished some water into her mouth. I moved behind her and rubbed my softening cock against her ass and pussy slowly. She turned around and just leaned her head onto my shoulder, her body pressed against mine, feeling blissful. After a few seconds, we got dressed in silence and snuck back into bed, with Jenelle none the wiser. In the morning, I got up before her and got out of bed. I'm not sure if she didn't wake up or did but just pretended to sleep to avoid awkwardness. Normally, I would have stayed to help clean up and grab some food with Lindsey, her brother, and any other stragglers, but I was feeling a strange mix of guilt, fear, and awkwardness, so I left early while everyone was still passed out. The next day, after a nap, was the most guilty I've ever felt in my life. But I also was just not able to process what had happened. I vacillated between thinking I should break up with my girlfriend and try to pursue a relationship with Lindsey, to chalking it up to a one-time thing, to feeling that maybe I had taken advantage of Lindsey and that she would hate me, to telling my gf and begging forgiveness. In the end I decided to just take it to the grave and swore to myself I'd never cheat again. I wanted to talk to Lindsey about what happened before I left my hometown, but we could never meet up with just the two of us. Seeing her in a group was awkward to say the least, and we didn't really talk. I ended up leaving her a short voicemail where I just apologized to her for putting her in a bad situation while I was at the airport 2 days later waiting to fly back to school. We haven't spoken about it at all since then. I still find myself thinking about that night maybe once a month, even though I'm happily married now. Lindsey is now in a long term relationship with a good guy. He's lame and she could do better, don't get me wrong, but maybe that's just jealousy :) Every now and then I think about bringing that night up with her, just to see what she thinks about it, but I never do. 1T4sG5D Gws-throw 1C7NZyR 1C7NZyR[2 comments]

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