With 1 being the hottest. I was asked this by a friend of mine that I am involved with, so I made a list. Might as well share it here.
1. I had sex with my best friend's girlfriend. I cheated on my girlfriend at the time, and she cheated on my best friend. For some crazy reason it was the best sex I had ever had. Maybe it was the danger of being caught, because my best friend was also my roommate. Maybe it is how well we meshed when it came to sex. For whatever reason we had sex for about two hours and it was good....real good
2. Same girl as above, lets call her E, the next day we went to watch a movie in the theater, she started touching me, un-buttoned my pants and gave me a handjob / blowjob until I came really hard
3. Months later after she had broken up with her bf, and I had broken up with my gf she came by my room. I was actually woken up by her so I ended up falling asleep right next to her. Somewhere, somehow I woke up and we had sex for a good three hours. There were scratches all over my back, a few bruises from bite marks. God it felt good
4. Same girl, we are in her neighbor's jacuzzi. Her cousin is there, she was about two years younger than us. We are all naked in the jacuzzi, Erin started turning me on, she started massaging my dick and I got really hard, so she straddled me and we starting having sex right in front of her cousin. She did not do anything just watched. I also learned that sperm floats that day...
5. Youngest girl I have ever had sex with, she was 17, I was 20. She was really really skinny, probably the skinniest girl I have ever been with. She worked at Denny's with me and had her own apartment, she had left home when she was 16 so she was totally independent. In any case, we went out on a date, first date and we ended up in her house. We started making out on her couch, at some point I just lifted her up and took her to her bedroom. We got naked and I went down on her, as I was licking her clit she started rubbing my dick with her feet. It was the first time I realized how much feet rubbing against me turned me on.
6. Same girl, same night, we started having sex in missionary position, as I said she was very light, so as I was having sex with her she was being pushed higher on the bed to the point that her head started hitting against the wall. So I would pick her up and bring both of us lower down the bed. After it happened three time I just did not move her, we were fucking, her head was slamming against the wall..and for some reason I felt like fucking her even harder..I bet she had a headache the next day.
7. The reason why E and I ended up cheating on our bf/gf respectively was because we were in an Italian restaurant. My best friend and Erin were sitting on the other side of the table. Erin jokingly played footsie with me, as she moved her foot to my knee and then my thigh she realized I was already hard...instead of pulling away she continued rubbing my dick. I did not even cum, but god it was so hot.
8. My last official girlfriend, she had a wine bottle and started drinking it from the bottle instead of a glass For some reason that really turned me on, she let me fuck her while she was drinking from the bottle. We ended up finishing up the entire bottle while having sex. I do not remember the entire night, but there was a lot of hard sex.
9. Same girlfriend as above. My old apartment was right next to a main street on the second floor, we were having sex and I grabbed her by the hair and pressed her against my window, cars and people would be passing by while her face and tits were pressing against the glass
10. The second girl I ever had sex with, it was in the dorms, my roommate would never leave our room...so after a while I would be having sex under the covers with music playing, quiet sex while my roommate would be sitting about 5 yds away on his computer. We did that so many times.
11. One of the girls I was working with about 6 years ago started flirting with me, after a couple of months we ended up in my car talking. I ended up going down on her in the back seat of my car and bringing her really really close to cumming. At that point I stopped and told her that our break was over and that we had to go back to work. Three hours later we were done with work. We ended up in the back seat of my car and she said "you better make me cum a lot cause you owe me". So I did.
12. Perhaps this will sound a bit weird. When I was 19 I was attracted to the BDSM lifestyle. I went online on IRC and ended up having regular online talks with this 47 year old Domme (as in female that is dominant). She ended up calling me one day, for whatever reason I ended up deciding to let go, totally let go of myself. She had me squeeze my balls to hurt and then she would tell me to stop. She did that a bunch of times, after half an hour of self torture I ended up having one of the biggest orgasms I have ever had, there was cum all over my keyboard, my computer screen, hands and stomach and I even fell of my chair to the ground.
13. Another ex of mine, we were in her room that was pretty big. I was on her bed and she was by the door, she turned off the lights and yelled "find me". From the lights been changed I could not see a thing. I managed to find her and we started making out right on the floor. I started teasing her, getting her very wet and then whispered in her ear find me and run off.
14. A lesbian friend of mine, she had not been with a guy for 13 years. We were really good friends and one day she told me she wanted to have sex with me. She had never had an orgasm with a guy and she was curious about me. We ended up having sex for a good four hours. It was interesting because she was so experienced with girls but at a loss when it came to me. At some point I realized that she was pretending I was a girl so she could deal with it. I found that hot....she was also the first girl to tell me that I kiss like a girl...but not the last
15. A Canadian friend of mine came to visit me while I was in college. From previous talks i had with her I knew that she had never had an orgasm in her life and that she always faked it. We ended up having sex, I figured that perhaps either the men she was with did not know how to please her or that maybe did not turn her on enough. I went down on her, and slowly licked her, I wanted her to get hot and bothered. I slid three fingers inside of her while my tongue was licking her clit. I was getting ready to stand up and have sex with her and to my surprise she came. I looked up thinking that maybe she was faking it, but the look on her face was of pure amazement. It was the face you get when you get your first orgasm ever. We ended up having sex, taking a break to eat some pasta alfredo and then having sex again
16. A bunch of my friends and I went to Denny's. One of my friends started rubbing my thigh which progressed to giving me a handjob at Denny's while my other friends where unaware. I want to return the favor, but girls are much harder to get off properly in a restaurant setting. She excused herself while signaling to me that I should not follow. A few minutes later she came back and underneath the table handed me her panties that she had already taken off in the bathroom. I made sure I returned the favor.
17. One of my girlfriends was doing a lot of theater, she was trying to decide what dress would look better for the part that she was auditioning so she started trying on skirts and dresses. One of them looked like a school girl dress, with a black and white criss cross pattern on it. She straddled me wearing and and that is when I realized she was not wearing anything underneath, she was dripping wet, making a wet trail on my stomach. She un-did my belt and used it to tie my hands against the bed post. She fucked the shit out of me, let me cum inside of her. Got up, untied me, wore her panties and went to her audition
18. A girl I dated when I was a senior, she was a freshman and a virgin. We ended up on my bed, but I did not do any moves on her. She ended up un-doing my pants and giving me one of the best handjobs of my life. She was basically lick her thumb to get it moist and use it to rub the tip of my dick while she was cupping my balls and massaging them.
19. There were two girls I would regularly have threesomes with, the best part was when one of them would be on top while the other one would be controlling the action, how fast and hard
20. I went to a strip club in Greece, there was a hot hot hot dancer from Ukraine that had obviously done ballet. In any case she came by and asked to give me a lap dance. I said no, but she whispered in my ear "you do not understand...I really want to give you a lap dance". I figured she just wanted my money but I thought to myself, what the hell its a strip club. She took me to the furthest booth available and started dancing, only she started kissing me while she was playing with herself. She straddled my face and move her panties on the side, I started licking her and she stood there grinding my face until she came. Then she helped me cum, kiss my cheek and took none of my money.
