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Tricked by a Twink

I had met a cute 18 year old twink at an all ages club and after exchanging a few calls, we finally agreed to meet up at my apartment. I was expecting more of a date, but he had other ideas, which was fine by me, because I really wanted to fuck this little twink. I was mostly topping at the time, and although I had fucked bareback before, I was using condoms pretty regularly. We went out to get food and afterwards came back to my place. He looked around a little bit and started putting the moves

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Topping and Bottoming in Washington Park

Washington Park in PDX had definitely been on my list for fucking outdoors. I had already been fucked bareback a few years prior on one of the trails there, but the guy didn’t cum inside me.  I met this guy Bobby one night at the all ages club when I was sobering up to drive back home. I was just dancing not really checking anyone out when he came up to me and started grinding his ass against my crotch. He was 6’2” at least and built like a swimmer with broad shoulders, wide lats, and a nar

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Teen Cums Hands-free

There used to be an all-ages club in Portland, and from time to time I'd go there after the bars closed to sober up and dance (they had the best music). One Saturday night I ended up there and was dancing for about 30 minutes when this teen started dancing with me. He was really cute and well-built, not too muscular but he was quite fit. We talked for a while and he asked me where I lived. I told him I only lived about a half a mile away and he asked me if I wanted to get out of there. I agreed

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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

Taking My First Anonymous Bathhouse Load

I went to Steam Portland one night looking to get fucked. I had gone a couple time before looking to bottom, but either struck out or ending up topping. I had cleaned out and lubed up with a dildo at my place before heading out. When I got to Steam it was moderately busy. I went to the steam room for a bit just to hang out, but no one caught my eye. After a bit I got up and made a circuit. I saw someone was at one of the glory holes, so I went up and opened my towel up and put my cock through. A

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Striking Out At Steam

I had gone to Steam just before midnight on a Friday night. It wasn't that busy and I spent the next 90 minutes cruising around, no one interested or catching my eye so I decided to call it a night. So it wasn't a total bust I checked Grindr when I got to my car and found a message from a headless torso that just said "bb?" I responded "pic?" and he sent a grainy photo I assumed was a few years old. He was really cute so I figured why not, his stats looked good, and I wanted to fuck. He gav

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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

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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

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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

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JamieLong

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

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Public Park Fuck

I messaged a cute 19 year old with a great bubble butt on Grindr one night, and after chatting for about an hour or so, we agreed to meet up. We didn’t specifically mention having sex, but I was pretty sure it was going to happen. We lived kinda far from each other so we arranged to meet up halfway at a park near where he used to go to high school. I got there and I saw him on a path by the baseball diamond, he was even cuter than his pictures. It was a warm night and we were both wearing just s

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Poz Guy Breeds Me

Like most of my hookups, I met Drew at one of the bars. We hit it off chatting at the bar and when we decided to call it a night I walked with him to his apartment since it was on the way to mine. When we got to his place he invited me up for a glass of wine. He had a tiny little studio in an old building, and he just had a kitchen and dining table with mattress on the floor. He poured some red wine for us and suggested we sit on the mattress as it would be more comfortable than the chairs he ha

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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,

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He Said The Condom Made Him Soft

I think it was just after midnight at the bar. I should've stayed home after getting back from my friends, but once I've had a certain amount of alcohol, I get pretty horny and wanted to get laid. I saw him from across the room, he was pretty average looking but looked like he had a pretty great body. I just remember saying hi to him, and the next thing I know we're making out in the corner of the bar. He's a great kisser and he's got one his hands on my ass. His crotch is thrusting into me. My

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He Didn't Know He Was Inside Me

Most guys will fuck bareback. Even if they say they don't, they usually will. I hooked up with a guy I had met out at the bars a few times and ended up going over to his place. We kissed for a while on his bed and things started to get hot and heavy. I stripped him and revealed a nice 6 inch cock with a slight upward curve to it. I sucked him off for a bit until he started kissing me again, then took off all my clothes and started going down on me. After sucking me for a bit he started lick

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Giving my first anonymous BB load at a Bathhouse

I had been to several bathhouses before, Club Portland, Steam Portland, but always with someone I knew or was hooking up with that night. I had even fucked bareback at bathhouses, and been fucked bareback, but always with people I went there with. We would either get a room so we could be private or go off into a corner and fuck, and if someone wanted to join I would just wave them off. The first time I went alone I was prepared to use a condom. Steam Portland has them everywhere. I got a r

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Fucking Undetected

I met Matt on Craigslist, back when they still had the personals section. He advertised as a vers bottom, and when I saw pics of his body and cock I knew I had to meet up with him. He had a massive 8.5" cock. I told him I usually topped at that point, so he was looking forward to hook up as well. He told me he was poz, but undetectable, but I could fuck him bareback if I wanted. I told him I prefer to use a condom (in those days) and he was cool with that and he had some available. He was also i

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Fucking a Stripper

In Oregon, strippers can be as young as 18 to work in bars. I was watching a cute one one night, he was short, maybe 5’2” maybe 105lbs. He kept making eye contact with me and I tipped him a couple times. At the end of the night as the bar was closing I left and saw him standing out on the street in a t-shirt, short shorts and sandals. “Good show” I told him. “You liked it?” He asked. “Made me wanna take you home,” I replied. “So take me home daddy,” he said coyly. We walked back to my

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Fuck Buddy FINALLY Breeds Me!

I've known my fuck buddy James for years. We met at a party I had at my downtown apartment. We hit it off, and he ended up being the last one at the party. We were talking in the kitchen as it was the farthest room from the bedroom where my boyfriend had gone to sleep. James and I were both leaning against the counter when we reached the inevitable lull in the conversation. At the same time we both leaned in and started kissing. He's a short Hispanic dude, wiry but muscular frame, and you'd thin

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Flip Fucking Flight Attendant.

I was visiting Waikiki for a week and was sitting at one of the local gay bars one week night when I got talking to a really cute flight attendant and his friend. He was about 5'7" with a bubble butt and a cherubic face with awesome dick-sucking lips. He was wearing a tank top and short shorts so you could just see the straps of a jockstrap hugging his ass. We hit it off and had a few drinks while chatting and eventually I invited him back to my hotel room. His friend handed him a condom and tol

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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

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JamieLong

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

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Finally Breeding The Boi

Harvey was a tease. I met him when he was 18. My friend was trying to get with one of Harvey’s friends and we ended up going back to their place. My friend ended up hooking up with the other guy in one of the bedrooms and I sat talking with Harvey on the couch in the living room. He was a slender, blonde twink with soft features and great lips. I found out he was a total bottom. He straddled me on the couch and ground his ass on my crotch. “I bet you wanna fuck me,” he said. “Of course I do,” I

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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.

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JamieLong

DPed By Married Couple

I had met Evan and Eric through my ex-boyfriend when we were still together and always thought they were really cute. About a year after my breakup I ran into them one snowy day at one of the local gay bars. Snow days are kinda rare, and the city was pretty much shut down. We made it to last call and started walking back home. I made a joke about them stopping at mine to warm up since it was on the way, and to my surprise they agreed. While we were at my place chatting someone brought up sharing

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