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Kee
I was 12 and neither of us had any idea what we were doing. We did it in our mutual friend’s room on the floor (sans condom) and I didn’t actually even come. We had sex a second time in the same room a day later and never did it again. She was pretty weird, with the most frazzled hair, but I was happy that someone had an interest in me, so I went for it. I moved away and never saw her again.
Pat
I ended up not having sex again for about four years after Kee and if I remember correctly, the next time was with Pat. I’ll be honest in saying I wasn’t that attracted to her, but she had really nice eyes. I watched Friday with her for the first time and fingered her during the movie. At some point we ended up having sex on the floor and again, I came pretty quick. We were cool after that but never spoke of it again.
Si
My friends’ younger sister. I always thought she was cute, although I kind of wanted her friend a little more. We ended up doing it at a friend’s house (another friend of her brothers) while he was next to us…with the other girl. He had two twin beds pushed together and his mother was never home, so it was pretty opportune for all involved. We did it once and I remember coming pretty quickly and trying to play it off. We actually dated very briefly until she broke up with me over the intercom at her apartment. I was pretty heartbroken but I got over it soon. We’re still cool online.
JD
Cute, younger girl that I liked a little more than I liked to admit. Lots of guys wanted her and she had a reputation as being a slut (as young as she was) before me but it turns out that I took her virginity (which explained her following obsession with me.) We did it on a table, a laundry room, and an abandoned house (and usually with other people close by.) We were on and off a bit but never were official. Years later, I friended her on MySpace but her husband and my then girlfriend didn’t like it.
Bree
The first girl to give me head. I had an opportunity to get head before, but at the time I was insecure about my size so I didn’t let her do it. Bree wouldn’t take no for an answer and ended up sucking me off in the apartment building stairwell. It felt so good I returned the favor and ate her out (my first time doing so) right there on the stairs as well. I wasn’t any good but she let me do it to her a few times. She was a year or two older than me and so the sex was some of the best since I hadn’t had much experience up until then. She was only visiting so it never got awkward. She was gone in two months.
GS
She was a girl I honestly tried to avoid. She knew me through a mutual friend and kept calling my house incessantly (which pissed my parents off since we only had the one landline phone then.) Eventually, I gave in and she gave me magnificent head. I went down on her after that but she was more interested in giving me blow jobs and fucking her. She loved the sex, I loved the head, but she annoyed the hell out of me. I avoided her constantly and I’m not sure when she actually stopped bothering me, but I’m sure she got the hint when I was never home (even when I was.)
Olivia
She was an on-again, off-again pseudo-girlfriend that I had been around for about two years. Her sister and best friend were always involved with my friends but she was exclusive to me, telling me that she loved me no matter who I was with. We went forever without doing it, until one night I got in a fight and lost. Being the lovely girl that she is, she nursed my black eye, let me lie in her lap and we had some pretty nice sex in the basement. At the time this was probably the most meaningful sex I had ever had.
AC
My two best friends didn’t like her and thought she was hairy (which I could actually confirm was true, but I never actually told them.) She played on the school volleyball team and I used to show up to watch her play. Eventually I randomly talked to her (after checking her out for a few weeks prior) and we ended up dating. It turns out that she had actually noticed me before but never said anything since I was older than her. I took her virginity in the men’s bathroom at school. The next time we did it was in the girls’ bathroom and got caught after the act by a close friend of mine. She moved away about a month or two later and the friend that caught me still jokes about it when we chat online.
BRC
Gave great head but we never actually had sex. Probably one of the most important women on this list but I won’t get into it. First bisexual woman I knew and a trend happened from her going forward.
Olivia (again)
I actually cheated on AC with Olivia once. Her sister was sleeping with this guy who lived literally in the building in front of mine and she invited me over. We had sex on his couch while he was in the back with her sister. She told me that she will always love me no matter what and I believed her.
Mia
The one who got away. She was everything good and I left her pretty screwed up in the end. Our main problem (at first) was her age. She still was in high school and I just graduated. We met one day while she was walking around the neighborhood with two friends after I just moved in. We hit it off instantly and we ended up having sex pretty frequently. She was the first girl I came inside of as she was on the Depo shot (something new to me.) Every time was memorable and I fell in love with her pretty hard. For better and for worse, being with her inflated my ego to the point that I was so confident being with her that I cheated on her and broke up with her about a month later. She was pretty broken up about it but that wouldn’t be the end.
BK
The girl I cheated on Mia with. What a mistake. She was crazy in every way possible and was using me for my car. When I crashed it (coming to get her) she got distant but kept me around. We still had sex pretty often, even though she was cheating on me the whole time. We fought constantly and I was actually much cooler with her friends than I was with her. The time we spent together was memorable but total hell. Interestingly enough, we ended up being pretty decent friends afterwards.
El
A girl I met at work. Not really cute, but she was really into me (I’m noticing a pattern here.) I caved and after some good head, we had sex in my parents’ guest bedroom. She left the job after a while and I heard she got admitted. Never heard from her again.
GP
I was fooling around with her around the same time as El. She was the daughter of one of my dad’s friends and thought I was cute. She was taller than me (usually a deal breaker) but she gave incredible head and would do it almost anywhere, including once while I watched the sunrise in a drop top in front of the lake. She found out she was pregnant (by someone else, I never fucked her) and moved along. She and I were actually still talking when my wife and I first got together, and years later, she saw us in the mall, surprised to see us still together. She thought I didn’t notice or remember her but it was just too awkward to say anything.
My wife
While the list should end here, it does not and this is why all of my entries have aliases. If she came across this list, I’d be in deep shit for a few of the girls that follow that she’s unaware of. We’ve been together for ten years now, and honestly, she’s the best sex that I’ve ever had. The most gorgeous woman I’ve ever seen. I’ve had a lot of firsts with her, including my first threesome. So much has happened with us over the years, it would take forever to detail.
Mia (again)
I found out that my wife was bisexual and also that Mia was too. Mia wasn’t pissed at me anymore and we were actually good friends. I got the two of them together and we played strip poker together in my attempt to start a threesome. Unfortunately, Mia was on her period so it was not meant to be. She was playing footsie with me while my wife wasn’t looking and this is how I knew she was still into me. My wife cheated on me and as revenge, I fucked Mia again and, stupidly, told her. We got back together but she made me cut Mia off as friends, though admittedly I still interacted with her for years afterwards. She ended up going to college and is doing pretty well for herself.
Mel
I started work at a new job and met her in training. She had small feet, so I was always staring down at them. It all happened pretty quickly and we ended up having an affair so noticeable that when I announced that my wife was pregnant, my coworkers congratulated Mel. At one point, my wife found out but we still kept it up on and off for a while. She was going through her bi-curious phase as well and ended up with a few women at the time. We’re still friends online, but we both pretend she’s someone else.
Cassie
My wife ended up “going away” for a while (long story) and while she was gone, I met Cassie. A normally reserved girl, she was very southern, very sweet, and somewhat old fashioned. I broke her normal waiting period to sleep with someone and after a week, we ended up doing it on her couch and everywhere in between. She was pretty wonderful to be with and we had fantastic sex pretty much daily. I even gave her a key to my apartment. Before she went to work, she would come over, give me head and fuck me before heading out. She was the first, I think, to call me the best she ever had. It was never going to work out, though, as I expected my wife back at some point and so I forced her to leave me and actually relocate back to another state. We talked on and off for the next eight years.
G
One of the craziest women I’ve ever dealt with in my life. Immediately after Cassie left, I met G through a mutual friend at our job. She was nine years older than me and very sexually open. I made her discover her bisexual side (which culminated in a nice foursome) and she was technically the first women I made squirt.
Lil
A friend that I had known for years. We actually worked at another job together first and then I referred her to my new job. I was always into her, but I never knew she was into me until we started working together again. I fingered her in her car on the ride home from work one day and I ended up coming over late to watch a movie. We had sex on her couch and upon putting it in her, she told me, “Damn, you’ve got a big ass dick!” She would later tell me that I was the greatest lover she had been with (#3).
SJ
One day, out of the blue, my wife was propositioned by this couple to have a threesome. We ended up in our living room and I ended up getting head from the girl but never got to fuck her. Funniest part: her boyfriend was there the entire time, and for some reason, couldn’t get it up after he popped some ecstasy. After a couple of hours of watching us, he finally got up, fucked my wife for all of 30 seconds and came. It was all his idea and he got the least out of it outside of the visual.
Cybil
My supervisor at work. I sat directly next to her and after a ton of text messages, we ended up at her apartment with her blowing me on the floor and eventually us fucking on her couch. We banged a couple of times after that and I can honestly say that I probably kept my job longer than I should have due to the fact that she wouldn’t fire me because of the sex.
WS
At some point, my wife and I broke up and she left me for another man. As a rebound, I hooked up with this girl at my new job who talked to me a lot about the situation and fucked me to console me. It was the ultimate friends-with-benefits situation as she knew I was looking towards winning my wife back, which I obviously did.
Denise
A friend from work. She’s older than me and I wasn’t aware that we had actual sexual tension until our flirting culminated in her blowing me on my couch. She proceeded to give me some of the best compliments I’ve ever heard about my dick. She’s still a really great friend and every time my wife has cheated on me, left, or gives me problems, Denise always tells me how dumb she must be to give up dick like mine. Talking to her gives me an ego boost like you wouldn’t believe.
KJ
Wow. This went further than it should have. My wife and I were going through a hard time and I started talking to a lot of girls on MySpace. This one won my attention and it bled into real life. She lived across the country so it was initially supposed to be nothing. Then it got to be something and my wife left me again. I actually flew out to see her, only to find out that she played men online on the regular and didn’t expect me to actually show up.
Joan
Right before my wife and I got married (yes, this whole time we were just boyfriend/girlfriend, off and on) I hooked up with Joan. We sat next to each other at work and exchanged text messages. She found out she was pregnant with her on-again, off-again boyfriend and then got fired from her job. That didn’t stop her from sending me a picture of her down-there one day, and so I came and screwed her on my lunch break. This happened a few times and was pretty enjoyable, albeit short lived.
The Devil
Sorry, but after what happened with us, I had to designate her with this title. She approached me at work while my wife was pregnant again and proceeded to pretty much destroy her. The bad thing is, as attractive as I thought she was, she wasn’t any better than my wife. I made her come with my hands, mouth, dick, and in every position you can think of. She was always down for sex when my wife wasn’t and willing to do it anywhere (cars, the woods, bathrooms, etc.) and at anytime when her boyfriend wasn’t around (and sometimes when he was.) It was supposed to be an affair with an end date, but it went on for about eight months. She took some things too far and lets just say if I see her again, my wife and I may end up in jail.
Shorty
This was a short lived few encounters. It had been over a year since The Devil incident ended and I innocently started talking to this girl at work who is about ten years younger than me. She has a really possessive boyfriend, so her time was limited and she mainly ended up giving me fantastic head three times, swallowing every one.
Ali
Another work encounter, she technically worked for me and we didn’t approach each other that way at first, as I was always talking about my wife and showing off my kids. Eventually we broke down that barrier and one day I met up with her in the parking lot and she blew me. We slept together a few times, each more memorable and lasting longer than the last. I accidentally hurt her the last time to the point that she was sore the next day. My wife and I were going through a rough patch yet again and this time it took a toll on me. Ali and I decided to stay friends and put any sexual history behind us and I worked on my relationship.
My wife and I are fine again and have stopped cheating on each other (I would submit her list, but it’s three times as long as my own and a lot of it happened after we got together.) She does everything I need her to and on top of her still being the best sex I’ve ever had, she thinks the same as me. I’m lucky to have her and I’m cool with the list ending her.
