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Breeding

Finally Breeding the Ex

MY first dating experience was when I was 19 and I dated this guy Ken for about 3 months before he dumped me for another guy. I don't really count him as a boyfriend since we were only dating a few months, but I still call him my ex. Or first date started in the middle of the night. He picked me up and we drove around, parked for a bit and made out for a while. Then we went back to his place and fooled around. We only kissed and sucked each other, but he was the first guy to actually let me shoo
JamieLong

JamieLong in Breeding

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Breeding

An Unexpected Breeding

In my early twenties I was quite the slut. I usually topped, and didn't mind if guys wanted to use condoms. I still don't even though I prefer bareback. I met this guy Tony at a bar one night and ended up going back to his place. We made out on his bed for a while, and before we even got our clothes off I could tell he was going to try to fuck me. At that point I wasn't bottoming much, mainly because there were just so many bottoms in town, and also my first experience bottoming wasn't that grea
JamieLong

JamieLong in Breeding

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Boyfriend

Boyfriend and I Fucked by Hung Muscle Stud

The first time my cock was ever in a guys ass bareback was only for a few seconds when I was 20. I had gone home with an 18-year-old twink and after we were naked I was lying on this couch and he straddled my cock and lowered himself on to my bare cock. (No lube, it was pretty impressive.) I was, of course, paranoid about STDs so I asked him for a condom. Still ended up being a great fuck but I do regret asking for that condom. The next time was about a year later with the guy who would become m
JamieLong

JamieLong in Boyfriend

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Taking First Load

Taking My First BB Load

I had already taken a cock bareback, but the guy pulled out before he came. I had been fucked a couple times before that by guys wearing condoms, and it was fine, but it didn't really do much for me. I got off, but it wasn't anything to write home about. The first time a guy actually came in me was the first time I really got the appeal of bottoming. I was 21 at the time and we met on an AOL chat room (late 90s, lol) and I agreed to meet him at his place. He was a fit twink just a little ta

Sex in Public pt. 5

Managed another park hookup while I was house-sitting for some friends out in the suburbs last week. I was feeling really horny, but mainly wanted someone to dump a load in my ass. It was getting pretty late and I was getting ready to go to bed when a 26 year old messaged me on Grindr. Turns out he was a guy I had hooked up with before. He always insisted on using a condom with me, but the last time we hooked up, he tried to fuck me bare, but I wasn't cleaned out or feeling it. Tonight I was def
JamieLong

JamieLong

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Favorite Hookup Outfit?

Anyone have a favorite hookup outfit? I like a t-shirt or a hoodie, shorts or sweats, no underwear unless I'm bottoming in which case I wear a jock strap, and slip on shoes. I love being able to strip off in a couple seconds and be ready to fuck. I have a sleeveless hoodie that I love wearing when it's nice out; it shows of my arms nicely. I have a couple kilts as well, but I've only hooked up once when I was wearing one. I really want to get fucked while wearing one.
JamieLong

JamieLong

1

Sex in Public pt. 4

There's park that was by my house in the suburbs that I had jogged by a couple times, but never really went into, and I ended up meeting a 19 year old bottom there one night. We had been chatting on Grindr for a while (he lived less than a mile away) but he was flaky as fuck and never really wanted to meet up. One night as I hit him up he said let's meet up, and told me about the trails that this little park has. I agreed to meet him and put on sweats, no underwear of course, a hoodie, and runni
JamieLong

JamieLong

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Sex in Public pt. 3

I met another guy on Grindr while I was out in downtown Portland one night. I don't know what it is, but I went through this period in my late thirties where guys aged 18-22 were thirsty for me. This guy was 20, so he couldn't meet me at a bar, so I went down to Riverplace, on the Willamette river, where his apartment was. I was dressed for going out, and he was in a hoodie and sweats. He was shorter than me, but built like a jock. I had a condom and lube with me, but I usually don't tell people
JamieLong

JamieLong

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Sex in Public pt. 2

Turns out I've had sex in public quite a bit. I'll share a couple more here. At my old place out in the suburbs, there was a paved trail that went back behind the houses and along a greenway that ran along the freeway. There was some light coming through from the freeway, but at night, it was quite dark. One night a cute 18 year old twink messaged me from less than 1000 ft away. He was visiting his sister and was looking for some fun in the new city. After chatting a bit, he wanted to meet
JamieLong

JamieLong

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BB

I Got Stealthed

I met Dave at the bars. We hit it off immediately and spent the night talking, until the bar finally shut down. We left and decided to go to a new bathhouse that had just opened down the street. We got checked in and got a shared room. We stripped off, making out briefly, and then went out to explore. We got in the hot tub for a bit and chatted with some guys. Had a nice chat but decided to get out and roam a bit more. The club was nice but plain so we headed back to the room where we made out,
JamieLong

JamieLong in BB

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Denver Trip

I love business trips. All all-expense paid to go fuck guys in another part of the world. This time I was sent to Denver for ten days. The first night I was there I went out to a couple bars, chatted with a few guys but no one really caught my eye. The clubs eventually closed down and I was looking around the parking lot of the last bar I was at, watching my prospects dwindle rapidly, when I saw a cute little twink sitting in his car. He was probably around twenty-two. I walked up to his car and
JamieLong

JamieLong

0

First Time Bb Bottoming

I hadn't seen Jack in several months. We used to hang out at clubs, but never did anything beyond making out. Apparently he had moved out of the city, but was back visiting family and friends. We had a couple drinks and caught up. We started talking about the last time we were making out and he asked me if I wanted to do anything. I said of course, so we left the bar and headed for a nearby park. It was after midnight by the time we got there. There were a couple trails that had a reputation for
JamieLong

JamieLong

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