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first time I've ever "talked" about it, ever mentioned it, ever let it leave my own mind.... 1997, was underway, on patrol in the military... wife and I had been married since 90 and going through a bit of a rough patch, pulled into a port in the Caribbean and there happened to be a cruise ship in port at the same time.. met a girl in a bar who was on vacation, on the cruise, and had a hotel room for the weekend.... I didn't even try, but she apparently had a goal to get fucked on her vacation.... she was well above average looking... long curly brown hair, small waist, full tits... fucked her every way possible that night... throat fucked, fucked her ass, pussy til it was too sore to go on, I remember fucking her from behind and pulling out to shoot one of the biggest loads of cum I ever have across her ass and back... that was the only time.
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ShortFuse Professional Jackinchatter

1248 posts since 2019-11-03
52 year old bisexual male from Nashville, TN
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My wife has never had a high sex drive. Even when we first started dating she wouldn't let me fuck her for over a month. When we finally did fuck she didn't cum. She was just too nervous I guess. When we finally started fucking we did it almost every day, but she was never really into it. It was mostly just me using her pussy to get myself off. I called it charity sex. Over the years we did it less and less and eventually got to a point were we only fucked once every 2 to 3 months.

I decided to get a prostitute when I was on a business trip. Then I hooked up with several woman and men on Craigslist. I had a few female fuck buddies over the years. I confessed to my wife that I had stepped out on her and she was very hurt. We almost got divorced, but we reconciled because we had a 1yo daughter at the time.

That was 16 years ago and while she doesn't condone me having sex with others, she has zero interest in sex and she doesn't ever ask me if I cheat on her. I think she assumes I do. She has a friend who's husband has regular affairs and she always says, "I don't know why she stays with him". Then I tell her, "Because she loves him and maybe she wants him to be happy".

To be fair, I am 100% positive my wife has fucked around on me with at least one man and possibly two women. She has a "best friend" now that is a bad builder and very manly. I thought she might be a lesbian but she's married and has kids. But my wife spends a lot of time with her. They go out every Friday night.
Small dick chronic masturbator
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ChiefH Skilled Jackinchatter

865 posts since 2018-07-30
74 year old bisexual male from Florida, Panhandle
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1977 with a bar girl while my ship was in Subic Bay! Thus my love for Asian pussy when ever I can get it!
ChiefH, love uncut cocks and bald pussies
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Cincyfun Amateur Jackinchatter

254 posts since 2016-07-14
44 year old heterosexual from Cincinnati
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The first time was before we were married. It was about 3am and a buddy of mine called for a ride from a party. When I got there, he was trying to score with some chick so I went outside to smoke a cigarette. There were two girls outside talking about dick sizes. They kind of hushed up when a total stranger came out. I said, "Go on, this conversation sounds interesting." They asked me how big my dick was and I extended my thumb and middle finger saying, "about this big which is probably 6 1/2 inches" They said there was no way because my hands were big so it was more like 8 from finger to thumb.

I said, "See that Toyota over there, you can measure and if it's 8 inches you can have it." One girl said, "Measure your fingers or your dick?" I said, "If either are 8 inches the car is yours." She said, "I'll get the tape measure" and went next door because apparently she was the neighbor. The other girl took me to the bathroom and she grabbed a tape measure on the way. She measured finger to thumb and it was 6.5 inches. I then pulled out my hard cock and showed it's the same length. She grabbed it and we started getting clothes off. A couple minutes later, she was riding my cock when we heard her friend knocking on the door. The girl riding me said "Don't answer it." I really wanted a 3some but I swear the pussy was so good I didn't dare say a word. We ended up fucking doggystyle with her up against the bathroom door and when she started to cum, I pulled out and blew a huge load all over her ass.

She sent me out of the bathroom because she was done with me and wanted to clean up. Her friend was standing there looking pissed but turned on. Apparently, she was listening at the door the whole time. At the time, I thought she was pissed at me but in hindsight, she was pissed that she didn't get to fuck me.

Then I saw my buddy in the next room waiting patiently to leave, he did not score. Looking back, I wish I had stopped on my way out and instead told the other girl that it was her turn and told my buddy to join in or wait a little longer.
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Sabonis7 Professional Jackinchatter

1584 posts since 2020-04-05
male from US
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Oh yes, mine was quite unforgettable...
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