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Stonehard54 Amateur Jackinchatter

305 posts since 2010-01-07
70 year old curious from Grand junction Colorado
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When I was young, an older boy tried to fuck me. He didn't get in, but I did get hard. Didn't do anything down there, but I had my ex wife , when we were married, early in marriage, finger me, and suck me or jack me off. The orgasms are intense. Have been playing down ever since!!!
Pleasure and be pleasured
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tugga Amateur Jackinchatter

207 posts since 2006-02-05
56 year old bisexual from uk
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Not really sure when i realised playing with my arse could be fun but i do remember one day at school (must have been around 12/13) a few lads were talking about bummers and bumming ( an insulting word for gays at school). that evening having a bath i started wanking as usual and suddenly thought of being bummed. I got out the bath and lay on the floor with my legs in the air and pushed a soapy finger up my hole at the same time as wanking my cock. It felt fucking amazing...and i didnt last long before my whole body shook and i i shot the biggest load of my teenage life. Been pushing things up me ever since....
too much is never enough
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mike1475 Skilled Jackinchatter

648 posts since 2010-10-18
49 year old heterosexual from southern connecticut
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in my early 20's, saw a vid of a woman plowing a guys ass with a strapon, so i went and got a dildo and tried it the next time i jo and it was amazing so i shared this with my lady at the time and she went and bought a strapon and it was game on ever since then lol, i love my ass being played with and a woman banging my ass with her straponstroke
The More Kink the better
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marriedjacker1 Novice Jackinchatter

64 posts since 2011-07-24
42 year old curious
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Today! I've been curious to try ass play for a while now, but just today got up the nerve to go to the adult store, bought a small dildo, and fucked myself with it when I got home. It felt amazing....I liked it better than I thought I would!
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When a guy on here talked me into trying prostate orgasm. I'm str8 btw
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PornAddicted Professional Jackinchatter

1703 posts since 2012-02-13
heterosexual male from Bedford
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When a black guy put his big cock inside
Addicted To Food & Porn
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plush Omnipitant Jackinchatter

5160 posts since 2010-02-06
heterosexual male from USA
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mikejsm said:
I actually found out just a few days ago when my gf and I were messing around and decided to try it. I licked her asshole first and she surprisingly liked it, then she asked me if I wanted to see how it felt. I said yes, and it felt so good having her tongue gliding on my asshole. We do it every time we have sex now!


I loved rimming two of my wives and my last wife rimmed me too but I squirmed and had her stop as I imagined her tongue slopping around in my hairy ass crack. It felt good but I was embarrassed
old long time jacker who loves anal with woman only
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Probably once I started doing some camming. Guys were keen to see my hole and encouraged me to play with it. Don't do it always but do enjoy it. Would love someone to rim me...
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showmeyourtitties Amateur Jackinchatter

144 posts since 2012-10-26
45 year old heterosexual
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I was a late starter too. I lived in my first apartment and was ordering porn dvds and male masturbation toys monthly. I got a small purple dildo as a free gift once and was going to throw it away because "I'm not gay". Then I watched a video of a sexy nurse giving a prostate massage and the guy blew a huge load. I decided to get drunk & try it out just for kicks...wow! What I had been missing!
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bassman7 Amateur Jackinchatter

487 posts since 2015-12-28
64 year old male from Near London UK
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i was about 13/14, i read about the pleasure zones in a book. so I tried it with a thin candle and proceeded from there..... to all sorts ! Had a good play last night with carrots, bananas and even tomatoes.
started at 6 and seldom stopped. kik - martin_y85172
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NaughtyNY Amateur Jackinchatter

367 posts since 2013-08-26
heterosexual from NYC
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divorcedbiguy said:
. . . could be a source of sexual pleasure in addition to your cock? When I was a young college student, an older guy took me to his place and, instead of sucking me off like I expected, he turned my over on his bed, put a pillow under my ass, and proceeded to lick and deeply rim my hole. I was shocked at first because I only thought of my ass as what I used to "go to the bathroom". But, it felt so damned good I couldn't help but moan and groan while he totally ate out my ass and realized that my pucker hole was VERY sensitive to a tongue, finger, and eventually to a cock.

Whether you're gay, bi, or str8, how old were you when you first had your asshole used for sexual pleasure and how did it go down. Maybe you discovered it yourelf by fingering it while jackin alone?


Ugh - well the first time I sexualizes the asshole in general was when Mr Bradley fucks Annie in the ass and she verbal indicates that she is indeed getting fucked in the ass. This was also a clear example of how you should fuck the ugly girl if she will do nasty stuff- clearly Rikki is hotter. How great to make up with Rikki while fucking her ugly friend in the ass! This was a relevation.
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camwoods Novice Jackinchatter

41 posts since 2013-03-13
49 year old curious
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As I've told a few of you, I was impressed at a VERY early age by some dirty pictures I saw in a locker at a relatives health club, and likened my young ass up on tippy toes to that of the anal hotties in the pictures. And as it turned out, I LOVED the feeling, and have been dildoing myself ever since. As you can guess, the hormone- riddled teen years were crazy..!
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slerbyderby Skilled Jackinchatter

889 posts since 2013-09-24

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when i got a rimjob from a GF. i would kill to have it happen again, and would want that over any blowjob for the rest of my existence. nothing is better.
i love my meat. no one else gets to touch - unless you ask nice.
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Johnnylonlover Skilled Jackinchatter

602 posts since 2017-08-11
57 year old heterosexual male
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jenna53 said:
37


So how did that come about Jenna? By accident?
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outoftown Skilled Jackinchatter

526 posts since 2011-07-09
70 year old bisexual male from Wagga Wagga Australia
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I don't remember how old I was, but first time was when I was very young and an older neighbor fingered me. Had a school friend that I played with in primary school and that included some anal fucking, but not a lot. Had major surgery a few years ago which resulted in my arse was removed, so no more anal fun.
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