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DirkM22 Professional Jackinchatter

1475 posts since 2019-01-29
26 year old bisexual male
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Luv these stories! stroke
always ready to JO
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amatsubu said:
Hey guys,

Been curious to try getting fucked in the ass for a while now. Would love to hear about some of your first times! What was it like? What was the setting? Kinda nervous about trying it. Hope to get some feedback before I decide!


I have never been with a male, but have been curious for years, and have always wondered what it would be like to get treated like a girl, and let a man put his cock in my mouth and eventually get it up my ass too, I have always said girls do definitely have more fun. Might be worth getting forced into a dress to be a man's girlfriend lol.
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jackbird Skilled Jackinchatter

686 posts since 2017-09-21
66 year old bisexual male from Dover /Rochester New Hampshire
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looking for my first time. I want it bare and hard to. I have used all kinds of toys on my hungry hole. It needs the real one.
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GraysAnatomy Omnipitant Jackinchatter

26681 posts since 2015-04-06
81 year old bisexual male from Central US
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My first time was around 60 years ago. I was a teenager and my friends and I experimented fucking each other. I was fucked, probably 100 times over about a four year period. None of the guys had a cock over 6 inches so it was no problem. I enjoyed it all but preferred doing the fucking. Probably fucked my buddies a 100 times during that period, as well. Since then I have been strictly a top.
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. . . . . . . . . . Surely no one is so naive they really believe a 5.2 inch erection is considered average . . . . . . . . . . . . . . . . . . . . . . .I see more 5.2 inch flaccid cocks than I do of little 5.2 inch erections. . . . . . . . . . .
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goofy_gopher Amateur Jackinchatter

121 posts since 2006-07-07
58 year old homosexual from Upstate NY
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I was almost 32, through my 20s I had a bottom fuck buddy as well as a suck buddy. I sucked or topped but over time I was getting jealous of the fun my bottom bud was having.

I then ran into a guy I hadn't seen in a few years. He was 21 (we never talked anything improper when he was younger) and we got to talking and catching up, he shared so much sucking he did while in high school and had both fucked and gotten fucked, and I was just so eager...

Then he invited himself over to my place one Saturday afternoon. We made out, sucked each other, he had me on my back sucking me, then lifted my legs and licked the back of my balls....and kept going until he had his tongue in my hole. I was in heaven. I'd tried taking a cock before but stopped due to pain...but his tongue made me feel so horny and ready for him.

He just looked down at me, our eyes locked as if it was our moment ... and he slid that cock into me and fucked me pretty good, I was amazed at how good it felt.

He spent the night and we fucked before going to sleep, but I woke him up twice to fuck me one more time each...yeah, you can say he turned me into a bit of a slut....
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I was 15 and had started hooking up with an older, only started with me basically giving him oral whenever he wanted it.

But the first time he fucked me, he set it up for me to be at his place alone with him for the day.

Had my first beer, he took his time, sniffed my first poppers. Definitely hurt at times and I was walking funny the next day for sure.
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DirkM22 Professional Jackinchatter

1475 posts since 2019-01-29
26 year old bisexual male
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DirkM22 said:
I was busily beating my own stiffie when I felt him go in. It hurt a bit, but his dick was thin and well lubed with his slippery precum. He didn't last long. After only two thrusts he pulled his dick out and shot all over my butt cheeks.

"Oh man, I'm sorry," he said, " I didn't mean to." I told him it was OK and it didn't feel too bad. (The truth was I kinda enjoyed it.). Then we traded places. He got on his knees and I humped his butt until I shot off on his back. I was going to penetrate him....but I chickened out. A couple days later I got my "revenge."


A couple days later we were in my bedroom "studying." It started the usual way, jacking off together in our underwear with our dicks sticking out. We took off our briefs and started pumping each other's young dicks until we were both slippery with precum.

We were moaning and grunting when he said, "your turn. I want you in me," and got on his knees on the bed with his soft, round ass sticking up. I got behind him, fingered his hole a little, then slowly slid my wet dick into him. He moaned and pushed back into me until my dick was fully inside him. "Move," he moaned as he stroked his dick, "fuck me." I held his butt and rammed my dick into him. OOOOOH it felt good! As he loosened up I humped him harder and faster, getting closer with each thrust. I heard him grunt as he shot off and the sound pushed me over the edge. With a loud groan I squirted my young sperm into his tight ass. As I pulled out my last squirt went on his back.
always ready to JO
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veterin Amateur Jackinchatter

367 posts since 2017-09-25
58 year old from Texas
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awesome
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here2CUM Novice Jackinchatter

44 posts since 2019-08-05
27 year old
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omg I am so horny from that story , i had to rub my ass a little , cock is so hard...mmm
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arizona_mikey Novice Jackinchatter

99 posts since 2019-05-17
73 year old bisexual male from Tucson, AZ
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my first time was my best friend when I was 12 and he was 13. He couldnt get it in me. I was so disappointed because I really wanted to have sex. When I was 23 my neighbor asked me over to his room to watch tv. I thought that was what we were going to do but he started touching my leg. I was thinking I should stop him but I was enjoying it. When he opened my pants and started fingering me, I felt more sexy than I had ever felt before. I sucked him and he asked me if he could fuck me. It kind of hurt when he was putting his cock inside me but when he got it all the way in and started humping me I came harder than ever before.
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bijackn Amateur Jackinchatter

436 posts since 2016-02-15
57 year old bisexual male
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DirkM22 said:
A couple days later we were in my bedroom "studying." It started the usual way, jacking off together in our underwear with our dicks sticking out. We took off our briefs and started pumping each other's young dicks until we were both slippery with precum.

We were moaning and grunting when he said, "your turn. I want you in me," and got on his knees on the bed with his soft, round ass sticking up. I got behind him, fingered his hole a little, then slowly slid my wet dick into him. He moaned and pushed back into me until my dick was fully inside him. "Move," he moaned as he stroked his dick, "fuck me." I held his butt and rammed my dick into him. OOOOOH it felt good! As he loosened up I humped him harder and faster, getting closer with each thrust. I heard him grunt as he shot off and the sound pushed me over the edge. With a loud groan I squirted my young sperm into his tight ass. As I pulled out my last squirt went on his back.



oh man thats hot
throbbing is the best way thru the day
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staples2287 Skilled Jackinchatter

640 posts since 2011-04-25
49 year old heterosexual from US
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I was 17 and in military school in Florida, one of the staff an older Cuban guy with a thin mustache used to like to watch me in the shower. I thought it was weird but really couldn't do anything about it. One weekend when I was showering alone he was there, he caught me in the changing area and had his penis out and he was hard. He pushed me into one of the lockers and held me there while he worked it in. It hurt at first until he was all the way in. He pumped into me hard a few times and then he grunted and I felt him cum in me.
I couldn't believe what had just happened, he just zipped up and walked away.

I could feel him in me and running down my inner thigh, when I caught my breath I realized that my penis was partially erect. I went back into the shower room to wash him out of me.

Then I got dressed and went as quickly as I could to the gym and hid in one of the storage closets for a long time. I was worried that if anyone found out they would call me queer and I'd never get a girlfriend. I was also really confused and mad at myself for getting semi hard while he did it to me. I know I cried for a bit but can't remember how long.
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histdoc2000 Amateur Jackinchatter

240 posts since 2007-07-07
80 year old male
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I was 18 hitchhiking home from college; picked up by an older guy. He talked about sex and showed some cartoon porn. I was so hard and horny when he asked to suck me I agreed. drove to a secluded road, got out of car, dropped my pants and he sucked me dry. came in 30 seconds. Then he had me lean over the car hood and spread my legs. He put his finger in my ass and worked it there, adding lube. then he got up and pushed the head of his cock in my ass. pain and ecstasy. slowly he pushed it in and out until he was fully in. I jacked my cock at the same time. It didn't take long before I felt his cum shoot in my ass. I came all over the ground. The first time, but not the last.
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histdoc2000 said:
I was 18 hitchhiking home from college; picked up by an older guy. He talked about sex and showed some cartoon porn. I was so hard and horny when he asked to suck me I agreed. drove to a secluded road, got out of car, dropped my pants and he sucked me dry. came in 30 seconds. Then he had me lean over the car hood and spread my legs. He put his finger in my ass and worked it there, adding lube. then he got up and pushed the head of his cock in my ass. pain and ecstasy. slowly he pushed it in and out until he was fully in. I jacked my cock at the same time. It didn't take long before I felt his cum shoot in my ass. I came all over the ground. The first time, but not the last.


Wow what a turn on, had me getting so hard. Thank you wish you had wrote more.
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