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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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Lets hear about the first time you got fucked
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FLscribe Professional Jackinchatter

1988 posts since 2014-06-09
55 year old bisexual male from tampa
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Most recent occasion was about a month ago. I was at a swing party, open to bisexual men, and I spent about an hour in a dark group room where all hands were everywhere. As I was going down on a hot wife, an older guy (about 60) came over and started rimming me, which I loved. After I made the wife orgasm, I rolled over to allow her to get up and leave. The guy started sucking my cock and jerking himself near my face. He was thrusting his hips while he was jerking his cock, and it was obvious he wanted to fuck.

So I asked what he wanted. He didn't answer immediately, so I asked, "Do you want to fuck me? Just get some lube." He nodded and found a bottle of lube. He applied it to my ass and I was ready for him. I got on my knees, ass in the air, and he slipped his hard cock between my cheeks. It wasn't big enough for him to penetrate my hole, but he loved grinding against me. And I loved feeling his balls slamming against my ass. It took him less than five minutes before he shot his wad in my ass. The guy collapsed in exhaustion, and I felt like a good Samaritan for letting him get off that way. It was nice. I've been fucked before, and it felt good, but this guy was so eager to get off that when he put his hands on my hips, I thought it wouldn't take long for him to come. And it didn't.
Open to interesting ideas
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touching_allowed Amateur Jackinchatter

487 posts since 2016-11-13
curious from Europe
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Same kind of party for me. I knew the guy and that his penis was a frequent visitor to my wife's vagina, so 'pre-qualified' and no call for condoms.
He asked if I wanted to discover what it felt like, I propped myself on elbows and knees, making my hole as accessible as I could. There was just some baby oil lying around, but he wasn't that big, so I guessed it would do.

I know from anal sex with my wife that there are two stages to this (at least for uncut guys). The initial penetration is with the head, with the foreskin rolling back and still outside my hole. Then it's time for the insertion to complete; with some thrusting his complete penis with rolled-back foreskin entered me, and I let out a slight yelp.

He didn't push and pull vigorously. The movement was more one of tensing and relaxing his muscle while deep inside me.
Then everything stopped. I thought my first anal fuck was all over. But after 10 seconds or so I started to feel a powerful discharge inside me. It was as warm as all the sex reports say it should be,and at a depth I didn't think possible.

He maintained position, holding my hips, almost lifting me and taking the weight off my knees. Then more movement, and he orgasmed again.

I was mentally so occupied with this new experience; I didn't even ask for or give myself anything. As the night went on, I could feel something seaping out of my hole into my panties. I wasn't sure if this was poop-related or his cum. Finger tests showed it was his cum. Cum from anal sex seems to take an eternity to re-emerge; something I know from doing it with my wife. I'm sure that most of his cum is stiil somewhere inside me.
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I first realized I was bisexual in junior high, when I started fantasizing about having sex with my best friend Mark. I'd also developed my outdoor nudity fetish by then.

I knew that Mark was well hung because I'd seen him naked in the showers after gym class. Even limp he was bigger than the rest of us. And whenever he'd put on his jockstrap, his balls would invariably spill out the sides because they were just so large. Looked very uncomfortable as he tried stuffing them back in the jockstrap! Needless to say, it was all I could do to keep from popping a boner in the locker room shower!

I never made a move on Mark while we were in high school, nor while we were in college. After graduating college, however, when we were both working but still living with our parents, we'd go out drinking on the weekends. It was then I decided to let Mark in on my outdoor nudity fetish. We'd cruise around the old hometown and I'd have him drop me off in front of some girl's house that we'd both wanted to fuck in high school. I'd take off my clothes in Mark's car and walk around the girl's yard in the nude. Mark never joined me...he just watched and laughed.

Until one weekend when his parents left him home alone to go on a short trip...

We did the usual drinking and driving around town routine. Only this time Mark dared me to walk naked all the way from our old high school back to his house, a distance of about two miles. I took the dare. Mark dropped me off at the high school naked around 2:00 a.m. to start my walk. Luckily I wasn't going to have to cross any main roads. I could stick to poorly lit residential streets. Bare feet, no mask of any kind. I was nude and fully erect walking along the sidewalks.

It took me about 45 minutes to get to Mark's house. When I walked in the front door, the house was dark. In the living room to the right of the foyer, I saw the glow of Mark's cigarette. I walked into the living room just when Mark turned on the lamp next to couch he was sitting on.

He was naked, sporting a 9" erection.

"I can't believe I asked you to walk naked halfway across town and you did it," he smirked. Then, taking a long drag on his smoke, he added:

"Care to give a friend a hand?"

I shot him a sleazy smile and replied:

"Everybody knows it melts in my mouth, not in my hands."

I immediately dropped to my knees in between his legs and started licking at his churning nut sack, running my tongue up down the length of his shaft, tickling his pee hole with my tongue. But Mark didn't want to cum that way tonight. He rubbed out his cigarette in the ashtray and grabbed me by the hair, pulling me up onto my feet and dragging me into his parent's kitchen. Told me he was going to have to do something about my "hot faggot ass." Ordered me down onto my elbows and knees (see avatar). He then took his mom's Crisco Shortening out of the pantry and used this to lubricate my asshole. He spent a good 15 minutes greasing me up until he could get all four fingers inside of me. And he wasn't the least bit gentle about any of this. I loved it.

Then he mounted me. Yeah, I felt it!

We're both married now, wives are clueless. I still struggle with with him orally, but I'm proud to say that I can take every fucking inch of him up my ass.
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My first time was my first wife and a strap on. Looked like a real dick. About 9 inches and normal big around. Lots of KY and slow slide in. Then she fucked me until I shot all over the bed without touching my dick
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JDee that was hot ! stroke
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here2CUM Novice Jackinchatter

44 posts since 2019-08-05
27 year old
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he was a JO bud , 9 +inch and much taller than me , one da y we got together for a wank, right inside his front door. i had cleaned up before going over . i lube up his monster and asked him to just stick the tip in, so he did.

i wish he had railed me balls deep and pumped his man seed in.
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no fucked but had a full on prostate massage a few times
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jjerismo Amateur Jackinchatter

238 posts since 2013-10-21
76 year old curious from Northern OhioUSA
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I've played with my hole over the years and always enjoyed myself.

I've never been fucked by a real cock, but about ten years ago I built my own wooden dildo and one evening while wife was away I got down on all fours and proceeded to give myself a good fucking. I made such gutteral sounds I never knew a man would make from having a dildo in your ass.

I've since experimented without touching my cock and simply enjoying what I feel as my dildo enters my body and then how good it feels deep inside rubbing up against my prostate. I also warm it up too before taking my wooden cock.

It's unreal how much we can enjoy if only we allow ourselves to relax and enjoy the wonderful anal sensations we all have.
Enjoy all.
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