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#41
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to echo a be at miss
for me it was a girl who my roommate had taken to a resort wedding. he had tried but had no luck and couldn't seal the deal. fast forward to present and we find this girl out one night as we are on the roommates brothers stag. I get into a fight and she proceeds to help me. one thing led to another and I end up giving her a ride hone but drop roommate off first. she had big tits and liked to play the skin flute but I could have been better off not doing her.
a near miss. met a girl on line and we went and played pool. she looked way better than her pic so we made a wager for the last game. I won and the wager was for a blow job. she was a real champ and sucked me dry swallows every drop. got back to her place and I started playing with her tits. she had great tits but they were covered in zits and scars. I suddenly got a headache and left before I went any further. |
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#42
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Years ago I was talking to my wife's friend in the street and she told me she was out of scotch and was going to buy a bottle. I replied I was going to the liquor store to buy some beer and I would get the scotch for her. I brought her a bottle and dropped it around her house later. She invited me in, she opened the bottle and had a glass. We got talking and 'things happened'. Short version, she undressed me and rubbed my cock until it was hard as I undressed her, dropped to my knees, saw her pussy was shaved smooth and I pulled her lips open and I licked her clit until she orgasmed. She pushed me on my back, sat on my cock and fucked he hard until she orgasmed a second time. As I was about to cum in her pussy, she got off my cock and rubbed it fast until I orgasmed over my chest and stomach.
She moved away about two weeks later.. Sighs... |
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#43
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I think half the women I have ever fucked are ones I shouldnt have but at the times I just didnt care
I fucked an ex girlfriend the week before her wedding to someone else, I had an affair with the HR director at a company I was working for and it was her husbands company. I had sex several times with a girlfriends mother. I had numerous affairs when I was with one girlfriend included with some of her freinds Luckily I was never caught out with most of them, the only one which was found out about was one I was seeing as she had asked me to take a load of nude boudior type pictures which ended up very explicit. I very stupidly put them on my computer and forgot to have it password protected. My girlfriend said she found them accidentally when looking for something on my computer but they were hidden so she had to snoop to find them. She packed her bags and left and on that same day I went straight round to the other woman and we were together for several months a just a sex thing. That ended after I was in a near fatal car crash and became a bit too messed up. I ended up signed off work for over a year and used the internet dating to find woman and had sex with far too many |
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#44
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For me it is my first cousin. Her dad is my mum's brother. I've been fucking her for years - over thirty. In fact it was me who popped her cherry. I also knew someone who boasted that he regularly fucked his sister. True or not? I don't know. But I suspect it is true.
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#45
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The guy who boasted to me that he regularly fucked his sister told me that she used to wank and occasionally suck her boyfriend off when they got off the bus after school; how he used to watch them; how much he got turned on and how he had to wank himself off later. He joked one night to her about having to relieve himself, and about how envious he used to get. She volunteered apparently, and that's how it started. He'd finger her sometimes and he got her to suck his cock on the odd occasion. Then, one morning when their parents went shopping, they ended up naked in bed and they fucked - using one of their parents condoms. As I said before, not sure if it's true or not, but judging by the amount of detail he gave me, I suspect what he told me had an element of truth to it
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#46
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Oh No
My sister's best friend, "Margaret" was just one of my "shouldn't haves." At the time, I was young and free and irresponsible, sleeping on my sister's couch for a few weeks. Margaret was much older than I was, 30ish...a magnificent divorcee MILF... before the term MILF existed. That first meeting, the three of us had run errands in town together. Although I was pretty naive at the time, I sensed there was something very horny about Margaret. We finished the day back at Margaret's apartment. My sister saw all the flirting and later commented on it. I told her Margaret seemed like a fun person and left it at that. Days later, in a bold move on my part, I showed up at Margaret's apartment, alone. "I was just in the neighborhood and wanted to say Hi" was my excuse. Margaret invited me in. She seemed friendly, but a little nervous. We sat down on the couch together and talked for a while. Eventually a simple touch led to a kiss and a kiss led to necking. The problem was, Margaret's two kids kept walking in on us. Funny as hell, the song: "Just the Two of Us" was playing on the stereo. Well, since it WASN'T just the two of us, Margaret and I decided to continue our activities at my sister's place. My sister was at work. We ended up fucking...on my sister's bed. Years later, when I told my sister about it, she was more angry at Margaret than at me. (Hey...we changed the sheets. Get over it, Sis!) It was a "shouldn't have" because Margaret ended up getting married to a guy named Paul. That same week, Margaret and I wound up in bed again. It was my first experience being "the other man." Shortly after, I started bleeding out of my cock. I went to a young female doctor who diagnosed "something like a bladder infection" and gave me drugs to clear it up. That was it, for Margaret and I. I shouldn't have slept with Margaret during her wedding week. I felt bad for her new husband. My sister thought we "shouldn't have" fucked in her bed. Margaret remained best friends with my sister up until my sister's death a couple of years ago. I saw Margaret several times over the years when we'd wind up visiting my sister on the same day. It was always cordial. Although I've never cheated on a lover, I've been in three cheating relationships as "the other man." Strange but true, in all three cases the husband's name happened to be Paul. Now, if I meet a guy named Paul, I'm tempted to say..."Paul, huh? What's your wife look like?"
__________________
“This is my problem with modern-day monsters, Scully. There’s no chance for emotional investment.” |
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#47
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...the girl who gave me Chlamydia. It was a one-night stand.
I shouldn't have used an expired condom. |
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#48
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Best Friend’s Sister
It was when we were in college. She had come to visit for a weekend and was two years older then me. He was out of the room at a party and she came in and used the shower. No big deal, I wasn’t much of a party guy and I stayed in. Then she walked out fully naked and not even caring. She had big natural breasts and a nice round fit ass, so I go turned on. She saw my boner, smirked, and started kissing me. We then had sex, on his bed, and he never found out. It was my first time, it was great, but it didn’t lead to anything and it could have broken a friendship I still have today apart.
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#49
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My first wife...
But only the very last night I was with her. She told me she had been fucking someone else. It took me all night to find out the whole story. It turned out that she was climbing out of bed and leaving me and our kids alone at night to meet my boss for sex. I could not abide by her sneaking around and cheating on me, but I fucked her that night anyway. It was a reclamation of sorts but it was also a hate-fuck, but unfortunately, she got the last laugh...
A week later, while on National Guard duty, I had to take a leak and when I was standing at the urinal, it felt like I was pissing hot sand! When I checked, I found the front of my tighty-whities full of yellow discharge. The b*tch had given me Gonorrhea! One hell of a parting gift! |
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#50
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Third year of college I went out drinking with my high school friend Dan, and his beautiful half-Chinese friend Siu. After a few shots Siu was all over me and Dan was the nonplussed third wheel. We went back to Dan's share-house and the three of us chatted on the couch, then he was ready for sleep. As he walked to his room, Siu emerged in just a thin white tank-top and white panties leaving little to the imagination. We started making out standing up and were getting hot & heavy Elaine style.
I realised things were weird when Siu yelled out to Dan "you don't need your bed tonight, you take the couch" grabbed my hand and led me to his bedroom door. I could see he wasn't happy with that proposal so we took the couch and had a good 30 minutes of finger-banging and other near-sex. I held back despite the drunken urges because something felt off about the situation. Turns out I was right. Dan had come out as gay to his close friends the previous year, including me. Siu was a newish friend who didn't believe him and was convinced she was the woman to fuck him straight. A few weeks before, she had got him drunk enough for his only ever fuck with a woman. For him, it confirmed he was gay. For her, it was a sign he could be converted. Coming on to me was part of the plan to get him jealous and interested in her. It messed up my friendship with Dan, mainly he lost respect for me even though I held back a bit with Siu and didn't know about his drunken sex with her. I was also seeing another woman (more friends with benefits) back home at the time and he thought I'd cheated on her. Thinking, drinking, and lust can be an uncomfortable mix. |
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