This is a true story about the first and only time I slept with my buddy’s girlfriend Leila (not her real name). This happened almost 6 years ago. At that time she had dated my friend for about 2 years and we all hung out together in a large group almost every weekend. When this all happened, I had just been laid off so I was home most of the time. I was on IM a lot and one day Leila signed on and we started messaging each other. We talked on and off for days about a variety of stuff and off course eventually the subject turned to sex. I asked her if she was a virgin and she told me no. So I asked her if she had slept with her bf yet (since I knew he was a virgin) and she said she did. I asked her if she knew that her boyfriend was a virgin and she said she knew that she was his first. She told me they dated for about two weeks before they first started making out. She said that at first, they just kissed and he would fondle her tits. But that was only the first during the first two weeks, and she gave him his first blow job at around the first month. I asked her how many guys had she been with and she said that she had been with about 2 other guys before him. She said her first bf was a high school sweetheart and she dated him for a long time before they both moved to the U.S. as foreign exchange students. He was sent to a different state as her so they would only see each other a few times a year. She said things went pretty bad from there. Whenever they get together all they did was have sex and eventually she broke up with him when she found out he was seeing another girl. Then she met another guy and dated him for a few months before they broke up. I said to her that she only dated him for a few months and she already slept with him? She said Yeah, it wasn’t a big deal because it was just sex. And she didn’t have any feelings for him. I told her that it’s normal for guys to think that way but a lot of the girls we knew would have a hard time separating their emotions from sex. She said she wasn’t one of those girls. I told her I felt the same way, that there was a difference between sex with someone you love and sex just for the pleasure. I spoke with her about how her bf was before they dated and I told her that he told me about her months before they dated. I told her that he said she had a gorgeous ass and that the other waiters would always make comments about how cute her ass was. She told me that she knew he like her ass cuz she overheard him making a comment about it before. I said to her that when I first met her I made it a point to look at her ass and said that he was absolutely right about her ass. I said to her that she was pretty and had a nice body. She said she didn’t feel that way because she was self conscious about her teeth (she needed braces) and she had small tits. I told her the sweet ass and nice figure more than compensated for her small tits and that her teeth wasn’t noticeable because she had a pretty face. She must’ve liked what I said cuz she thanked me, then she told me that of all the guys in our group she thought I was the cutest one also. As you can imagine, I had gotten pretty horny during our conversation. I went and asked her how often did she and her bf had sex, and she said “Not often enough!”. I asked her why she said that and she said that her bf was kinda conservative and he felt guilty if they had sex too much. He would tell her that they weren’t married so it’s best if they didn’t have sex so often. I asked her how often did he felt they should have sex and she said once a month! I responded with the ! mark also(haha). She said that once a week was what she wanted. So I asked her what happens if he wanted to have sex but she had her period? She said if that happens she would just give him a blow job until he came. I asked her if he comes inside her mouth and she said he did. I asked her about the taste of his cum and she said she didn’t mind the taste at all. So I told her how lucky her bf was. I said to her that I always had to ask multiple times before I would get a blow job and that when I do get it, it always ended with a hand job and that it would be so nice if my bf would suck me out like a straw. She told me that I was lucky to have my gf too because she was very nice and I told her that I agree with her, but that like her I just wished my significant other would do something more of. In her case it was more sex, in mine it was more blow jobs. She agreed and said that was true. Then, I said something that I’m still surprised of. I said to her: “Hey, it just occurred to me. You don’t seem to have any problems giving blow jobs and you’re short on sex. And I never mind having sex, but don’t get enough blow jobs. We should just get together and give each what we need!” When I said that, my heart was pumping fast and I thought I had overstepped the boundaries. But to my surprise, she just said “Are you sure?”. I was shocked! I said to her that I was thinking it would just be sex and that no emotion would be involved. She just said that did sound like a good idea. I asked her when the last time she had sex and she said it had been 3 weeks already. She tried two weeks ago but her bf was out of town that week. The last week when he was back home, she had her period. Then just last night she tried to have sex with him, but he said he was busy and turned her down. I said to her, Dang. You must be really horny then if you’ve gone 3 weeks without any sex. She said she was, and I asked her if she had her period last week, did she give her bf a blow job? She said she did and I was just like ‘OMG! He came in your mouth last week and now he won’t fuck you when you ask for it? How selfish!’ She just said yeah I know. She said she was going to ask him again that night and would tell me what happened. We ended our conversation that day .
The next day I messaged her and asked her if she had sex last night. She said they made out a lot and he fingered her, but he had to leave early so they didn’t have sex, and that he told her he probably has to work late the following and won’t be able to really be with her until the weekend. So I said to her. “Well, I didn’t get my blow job either so you want me to come over?” She said “YES!”. So I ended up driving over to her place that day. It was about 1pm on a weekday. It was real awkward at first, especially since it’s the same place we hang out at as friends. I parked my car on another street a couple of blocks away in case someone drives by and recognized my car. She had on a pair of sweats and a thin blouse.(She’s 5’5” and weighs about 100 lbs, 32A). We sat on her bed and talked a little bit. We went into more details about her sex life, I was feeling very awkward at this point since I’ve never done anything like this before. I think she knew I was feeling this way cuz then she told me about a THIRD guy she slept with before she dated her bf. She said she met him at a bar with her other friends. They never really dated, but one day they hung out together and he drove her home. She invited him in for a little while and she ended up sleeping him. I asked her if she gave this lucky guy a blow job and she said no. It was just straight sex. So I guess that loosened me up a bit so I just thought to myself. “I’m here. If I want it, I can have sex today. And it’s just sex, nothing more! When I finally convinced myself, I went and turned her around so that her back was facing me. I leaned her against my chest and cupped her small tits underneath her shirt. I concentrated on the feeling of her body next to mine because I knew this will probably be the only time we would do this. Then, I started kissing the back of her neck and she started to moan slightly. I took her blouse off and unhooked her bra and started fondling her tits under her bra. She arched her head back and placed her hands on the back of my head and I began rubbing both her nipples with my fingers. She started moaning a bit more and she moved one of her hands down and started groping my penis through my jeans. I got real hard and I turned her around started sucking on her nipples. I recall that she had big hard nipples. Then I pulled her sweats off and started fingering her. She unzipped my pants and started giving me a hand job. I was on top of her at this point sucking on her tits and licking her nipples with my tongue, then I slowly started moving up and she started sucking on my nipples. I went up a little bit more and soon, my dick was in front of her face and I saw her looking at my dick as she was stroking it. I guess she was getting a good look at it first, then she just put my dick in her mouth and started sucking away. I enjoyed every moment of it, I went and put a finger on the shaft and felt her lips moving up and down on it. I started to head fuck her and I held both her hands on the pillow as I shoved my dick deeper into her throat. But she was pretty good and was able to take my whole dick in. She did gag when I started moving faster though. I didn’t want to turn her off so I didn’t go much deeper into her throat. Shortly afterwards, I mounted her and stuck my dick inside her. It went in real easy, she was wet and loose. I was so horny at this point I just wanted to fuck her brains out. I started pounding her in all these different positions. I think the doggie style was her favorite though cause she moaned the most when I did this. I held on to her hips and just pounded away. I didn’t know how hard I was pounding her till I started feeling pain at the spot where her ass was hitting my skin. I wanted her to beg me to stop the way my gf does. But she took it all without complaining. She was really enjoying it. When my knees got tired, I flipped her around and put her legs on my shoulders and pounded her again while I crouched. I almost came a couple of time but I have always been good a controlling it and I stopped for a break each time I got close. My breaks usually involved sucking her tits and playing with her nipples. Then , I stood her up and with her hands against the wall I fucked her from behind standing up. She had a wall mirror right across from the bed and I looked at myself while fucking her. I’m just over 6 feet tall so I had to bend down a little bit and she had to stand on her toes. I fucked her as hard as I could while looking at myself in the mirror. I started to wonder if her bf fucked her in this very position like I was now. So I asked her if he fucked her in this position and she said no. I asked her if she likes it, and she said Yes! Keep going! I had her go down on me in the 69 position but instead of eating her out I just fingered her. Her tits were firmer than my gf, so I had her get on top and she rode me as I fondle her tits. Her tits didn’t bounce like my gf’s. Then it was her turn. I lied down on the bed and she went down on me again. I laid there telling her what to do. She definitely wasn’t afraid of my dick. She was licking up and down my shaft and fondling my balls. She probably blew me for 30 minutes before I started fucking her again. We went at it for about three hours. She came several times, but I controlled myself so that we could fool around longer. Suddenly the door bell rang and it freaked me out cuz I thought it might be her bf. Turned out it was only the mailman. It scared us quite a bit. She told me her bf usually doesn’t drop by until 6 but there have been times when he came by earlier. It was now a little past 4pm so I decided to leave. As I was getting dressed, she took the bed sheets to wash. I saw that there was some blood stains on the sheets so I asked her why was she bleeding if she’s had sex before. She just said, the others weren’t as big and they didn’t go as deep. When I got home, I was still horny as hell so I finished myself off. That night she IM me and told me she enjoyed herself. I asked her how she liked it and she said it was the best that she’s ever had. She said she never had an orgasm before and that it was her first. I asked her if my dick was bigger than her bf, and she said it was. I asked her by how much but she said she didn’t know. She said that she can tell because when she was sucking my dick she felt it hit the back of her throat and his does not. She asked me if I came inside her and I told her no. She asked if I was sure and I told her absolutely. She’s usually have sex with a condom and this was the first time she went without. I told her not to worry because I’ve been dating my gf for 5 years and never have sex with a condom and had an accident. I told her I finished myself off when I got home and She was relieved at this but she said she was disappointed that she didn’t make me cum. She asked if I wanted to do it again tomorrow. At this point, my dick had just gotten what it wanted and my real brain was working. I told her I didn’t think we should do it again since we were both committed to a relationship and didn’t want our significant other to find out. She agreed and we didn’t spoke of that day until a couple of weeks later when I went over to her house to drop some things off. (We had a dinner party a couple of days before and I took some Tupperware home) . I stayed over for a bit and she was doing some chores. I was watching her and when she bent over and I could see that she was wearing a black thong. I walked up behind her and pressed my hard penis up behind her ass and started feeling her tits. I asked her if she wanted to do it again. She just smiled and said we shouldn’t. I was horny as hell and kept trying to convince her. Then a couple of kids from next door came over and I had to keep my distance since they knew her bf as well. They were in her room playing on the computer and I was in the living room watching TV. Every once in a while my friend would come out to keep me company and I would grab her ass and put my hands up her shirt. When the two kids finally left she came over and sat next to me. She said she knows that I’m really horny but she thought I was right when I said we shouldn’t do it anymore. I told her I knew that was best too, but right now I’m so horny I can’t help myself. She finally gave in and said. “Let me do this for you then”. She leaned over and started sucking my dick. So I sat on the couch just feeling her little tits while she sucked me off. It didn’t last long. I felt that I was about to cum after about 30 minutes. Just before I was about to cum, I tapped on her head and told her I was almost there. She nodded and continued sucking my dick. Suddenly, I exploded and I quickly tapped on her head thinking that she was going to pull out. But instead she sucked on my dick even harder. I can feel all my juice squirting into her mouth, but she just kept on sucking. She timed it where each time my dick pumped she would suck up. She literally sucked my dick like a straw just the way I had said to her in IM before. When I was done, she pulled out and spit everything into a napkin. I just looked at her and said WOW.
Shortly afterwards we stopped messaging each other because the tension was too high and eventually we stopped hanging out together .We don’t see each other anymore, we found new friends and drifted apart. We both ended up marrying our significant other and attended each others wedding. Last year we all met up again. She has two boys now, and I have a daughter. When we see each other at the parties we sit down and talk but we’ve mentioned that day or even hinted that it occurred. It’s been on my mind again though especially after I came across this site. I’m wondering if she’s thought about that day at all.
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Buddy’s Girl
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