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PornAddicted Professional Jackinchatter

1703 posts since 2012-02-13
heterosexual male from Bedford
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I just love anal and would like to know real stories please grin
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My step brother
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phiilip Professional Jackinchatter

1026 posts since 2011-05-08
68 year old bisexual from UK
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I was a young music student in London and had an end of term job in an amateur theatre props department. There were 3 other guys there, all gay. 2 were in their 20s, one 50 or so. At the time I was quite fresh faced and one day for a laugh I dressed in one of the female costumes with wig etc. It got a bit out of hand. Ended up the oldest guy dancing with me and getting very hard. I ended up sucking him off. Later we all went to his flat got very drunk and I ended up in his bed. I wasn't sure at first but he used plenty lube and made me smell stuff which I found out later was poppers. I felt a bit ashamed and next night I picked up a girl in a bar to fuck just to prove to myself that I wasn't gay. Since then I've matured and am able to accept that being bi is fine. But at the time I was young and times were different.
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lvtwojo Amateur Jackinchatter

139 posts since 2014-09-11
66 year old bisexual male from Florida
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I was still n high school, my best friend and I had been sucking each other for a couple of years. We both wanted to try anal so I fucked him first then he fucked me.
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iBalls Skilled Jackinchatter

673 posts since 2010-08-29
53 year old curious from Ottawa, Ontario
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PornAddicted said:
I just love anal and would like to know real stories please grin


Is this question for men AND women? For a person of either gender, taking a penis up one's bum hole is a bit of a stretch, as it were.
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My partner in my first LTR. He was 32, I was 22 - I wish I'd started years earlier but never met the right guy.
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grneyzma Novice Jackinchatter

91 posts since 2012-07-23
54 year old curious from western ma
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It was my old roommate/ FB... he was a little smaller so it fit well in my tight ass... I really miss it.. so tough to find a goor jack/ FB here... poppers helped...and I loved it
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A roommate back in 1987. We were both bi but when we moved I. With each other neither of us knew about the other being bi. A few months later we were sucking and fucking each other and both had girlfriends too. That was a great couple of years.
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Leliel Novice Jackinchatter

94 posts since 2008-10-05
44 year old heterosexual from Mexico City
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It was a guy I met online to have mutual masturbation. He was the first guy I did this with. He told me I was his first time too for this.

Our first session was only watching each other. It was hot to watch each other naked and enjoying.

The second session was a bit more mutual. We touched each others penis. I also used my butt plugs which sparked his curiosity and ask me if I would let him penetrate me the next time. I of course agreed.

The third session was very open. We masturbated with our bodies touching. I gave him a blowjob (My first!) and he used a butt plug on me. After all that sex play, at the end I was ready.
I laid on the floor and he was on his kness in front of me. He put his tip on my entrance and pull me by the hips penetrating me slowly. I felt so hot and so erotic. I told him "You are inside me" when he was all the way inside.
He started pumping and told me "You feel so good".
I noticed in his face he was really enjoying it. I felt in heaven too. While he fucked me I was jerking my penis and caressing my nipples. I was leaking so much pre.
We kept like that for 10 min I think and he told me he wanted to finish on my face. I agreed and he pulled off. I needed something inside me so I used my butt plug, a large one. I got on my kness and he stood in front of me. A few secs later all his cum was falling on my face and mouth.
I could not believe that I was receving a cumshot while using a butt plug.

I think that was the most erotic time of my life, that was not solo.

We just had 2 more sessions that were not as intense. Seems he lost that "first time" excitement. But well, that first time was my best time with a guy.
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petermc Novice Jackinchatter

10 posts since 2008-12-08
74 year old bisexual from Victoria BC
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I was staying in South Beach and chatted with a guy on squirt. He came over and after some stroking he rimmed my 52yo ass for a while and then eased his cock in. I started on my back and then let him inside doggie style. Made me moan and beg to be fucked more and I felt him shoot his load, his cock throbbing nicely. He finished up by rimming me while I jerked off to completion.
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PornAddicted Professional Jackinchatter

1703 posts since 2012-02-13
heterosexual male from Bedford
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iBalls said:
Is this question for men AND women? For a person of either gender, taking a penis up one's bum hole is a bit of a stretch, as it were.


I meant this for both genders
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My best friend Craig.
We were both 18.
I had been blowing him since we were 17.
I offered him my ass the night before he joined the marines.
When he would come home on leave,he would fuck my ass on the first and last nights home.
After his enlistment ended,he moved back and he fucks my ass at least once a week.
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ballsy Skilled Jackinchatter

539 posts since 2005-08-23
62 year old bisexual male from Mississippi
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i answered an ad on craigslist and talked with the guy before hand. he was much older but horny as hell. i had practiced for years with dildos of various sizes so was able to handle him easily. lots of lube and a condom. he fucked me ok and finished off in my hole. that was my first real penis in my ass but i've been fucked a lot better later on.
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It was a buddy I met here on JC. He lived 2 blocks from my house. We met a few times for mutual Jo, until one time he came to my place and we were both super horny. I agreed to let him do me doggy on my bed while he was standing behind me. I'm still trying to convince him to do it again.
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JackMcCock Skilled Jackinchatter

527 posts since 2014-06-30
42 year old bisexual male from San Diego
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Met a bi-curious guy online for a bit of mutual experimentation. He picked me up and took me to his place, put some porn on the TV and we got naked. Turned out I was mostly interested in sucking his cock and swallowing his cum but he did fuck me doggy style that night and it was good smile Was honestly surprised by how much I enjoyed it. Aside from the physical stimulation, which was very pleasant, I really started to get off when he did - when he started to grunt and groan, mutter 'yeah' and all that stuff, it turned me on like never before. I think I just enjoy providing a hole for men to pleasure themselves in ^_^

His cock was average or even on the small side but it was straight, smooth and clean which was cool. Did make slipping in to my ass easier I suppose. Got the thrill of my life when he told me he was about to cum inside megrin
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