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nevguy Amateur Jackinchatter

105 posts since 2018-03-30
58 year old curious male from nevada
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A neighbor a while back wanted to fuck me, she said if she sucked my dick she might fall in love,, I want my cock sucked but not a crazy love triangle...
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nevguy Amateur Jackinchatter

105 posts since 2018-03-30
58 year old curious male from nevada
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Anybody u wish u would have fucked?
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David1970 Skilled Jackinchatter

540 posts since 2019-10-01
50 year old heterosexual male from Edinburgh
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Yeah my niece from my old marriage. Niece through marriage not blood. Nearly got there but if came out would have caused a up roar
Old and horny.
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Willooh Amateur Jackinchatter

106 posts since 2017-09-20
56 year old heterosexual male from Pennsylvania
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nevguy said:
A neighbor a while back wanted to fuck me, she said if she sucked my dick she might fall in love,, I want my cock sucked but not a crazy love triangle...
how did she bring it up to you
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Nicks Professional Jackinchatter

1356 posts since 2012-06-23
47 year old heterosexual from Just ask
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I was in the same situation awhile ago. Not blood related just through marriage.
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bfphawk Professional Jackinchatter

1235 posts since 2012-02-03
61 year old bisexual male from US
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I was about 20 and working in an office. There was this black girl working in my department and we went out on two dates. Just dinner and a movie. We made out but that was all we did. I can still remember the taste of her lips and what it was like touching her face and arms. She was the only black woman I ever kissed and she was so beautiful. I still masturbate thinking about her and remembering kissing her soft lips. Being with her was incredibly exciting and of course I was just a kid and really didn't know what to do.

We remained friends after the dates but obviously nothing ever developed between us and she eventually moved on from that work situation.

Missed opportunity.
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my mates ex-wife, she let me finger her and wanked me, but we never went all the way. frown
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Night before my college graduation, I could have fucked my buddy's ex girlfriend, who was still friends with him and our whole group. We made out but I stopped short of fucking her out of respect for him.
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FLscribe Professional Jackinchatter

1988 posts since 2014-06-09
55 year old bisexual male from tampa
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My friend's ex-girlfriend moved to my city, and we went out a few times. There was some question over whether they actually had broken up or left with some tension still unresolved. I really enjoyed getting to know her better, and it turns out she and I had plenty in common. One night after a very high-end dinner I took her to, to celebrate her new job, she invited me in to look at something on TV.

She fell asleep on my shoulder, and when I leaned in to tell her good night, that I had to go, Vee leaned in and gave me mouth-to-mouth resuscitation that I will never forget. We made out for about 15 minutes, and we reached the point that it was going to escalate to the magic point. She drifted off again -- not that I was offended, it was a workday that started early for her -- and I tucked her under a blanket on her sofa. I really wanted to do more. But out of respect to her, and my friend, I gave her a peck on the lips and told her good night.

She is gorgeous, and easily would have been one of the hottest women I'd ever have been with. (Think, porn star Alexis Fawx) and you'll know why I kick myself every now and then.
Open to interesting ideas
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gondo Professional Jackinchatter

1117 posts since 2008-02-09
70 year old curious male from Toronto, Canada
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JOGuyNH80 said:
Night before my college graduation, I could have fucked my buddy's ex girlfriend, who was still friends with him and our whole group. We made out but I stopped short of fucking her out of respect for him.


I had a chance to fuck my best friend's ex as well, but with great reluctance did not follow thru, because it might have cost me my friendship.

But she was so gorgeous - tall slim body, long legs, lovey face, lots of curly brown face, fantastic breasts. We were sitting in a cafe chatting. She was talking about another ex-boyfriend, who according to her, had a torso like a jellybean. She looked at me and said, "I wonder what your body looks like." Damn I wish I'd shown her.
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Subbeta Amateur Jackinchatter

342 posts since 2017-06-17
54 year old curious male from Uk
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A married woman I used to work with. She was a goddess and every time she had a drink, she would be all over me. I should have fucked her hard
Humiliate me
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Cockatrice Amateur Jackinchatter

141 posts since 2012-03-23
45 year old heterosexual
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When we had a live-in au pair we would pay her extra to do our laundry. On laundry day I made sure to leave a big cumload on our bedsheets or on my briefs right on top of the laundry bin. Twice a week for 2 years, that shy athletic big-titted Danish college girl saw and smelled and touched my cumloads and never mentioned it because she figured the money was worth it. I should have fucked her even if it meant paying extra.
Skype: marriedmeat2eat
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Ringo57 Novice Jackinchatter

87 posts since 2015-08-30
66 year old heterosexual from Canada
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Could have fucked a couple of co-workers but though it might make things awkward at work. They were about 20 yrs younger than me
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RobertG Novice Jackinchatter

31 posts since 2016-02-28
66 year old bisexual male
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Pam, my R.A. (resident assistant) in a co-ed dorm in college was a petite, very fit woman with a remarkably voluptuous body. She put a pic of herself on the bulletin board and one of the guys cut out a Playmate's nude photo and attache it (yes, I know this was wrong). She wasn't offended, though, and one of the guys remarked "it does not do you justice", and I think he was right...Pam had a much better body than the playmate!

A couple of opportunities come to mind.

I helped her hook up her stereo in her room, and she made a point of closing the door and relaxing on the bed while I was doing the work - her beautiful legs on display in shorts, and her bust stretching her t-shirt. What a fool I was to not see what might develop!

Another time at a dorm party, late in the evening, Pam and about four of us from the men's side were chatting, and the question came up - what next? John looked at Pam and said "how about group sex". Pam looked right back at him and replied "well John, how many of you do you want me to take on?". I think we were all to stunned to take it as anything but a joke, but ..damn... I think she was at least half serious. She did insist on a goodnight kiss from each of us, and the memory of her mouth on mine is still strong.

Ahh what could have been! I don't even think she ever knew how many stoke sessions she inspired!
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johnson Amateur Jackinchatter

371 posts since 2006-03-11
38 year old bisexual from Ohio
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The last serious girlfriend I had before I met my wife. I'm white, she's black. We dated off and on for almost two years. She had had sex before, but I was still a virgin. She would have had sex, but I didn't want to yet. We had regular make out sessions, heavy petting, lots of grinding, a handful of blow jobs. Even made out naked and took showers together sometimes, but never went all the way. After being single for a while after we broke up I really regretted that we never fucked. We remained friends and I actually tried to sleep with her a few times after that. Ended up staying a virgin until my wedding night, but part of me regrets never having sex with her.
Turn on. Tune in. Drop out.
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