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Gay Male / 32

Our First Times...

I am putting this question out to all gay or bi males...
HOW WAS YOUR FIRST TIME BEING ON THE BOTTOM AND TAKING A NICE COCK???

I mean was it a nice romantic love making situation? Or maybe just happened and was unplanned? Or did you get BROKEN IN and your ass got torn to pieces! Mine was the latter...

In my case I was in my senior year of high school. I was flipping a coin between girls and boys. Leaning toward gay and boys. My high school was so close to home walking was way quicker than the school bus. There was a small city park I walked by and I learned it was a hookup spot for gay men. One day I stopped there on my way home. I walked into the bathrooms and got quite a surprise. A man was on his knees sucking another mans cock. They quickly jumped up and tried to cover up. I nearly ran going back out. A few days later I went back and hung out for a bit. Guys were coming in and out. yes I got hit on several times but I was too nervous at the time to do anything. I watched and saw several sexual acts between guys. After a time or 2 back I finally joined in and gave a blowjob to an older guy. I REALLY LIKED IT! I started going back and was very popular with the older guys.
Well the day came. One day I was standing outside the bathroom area when a person I had never seen before drove up in a big SUV. He got out and I was immediately interested. He was maybe 30 and really hot. As he approached the bathroom he spoke to me and we chatted. He invited me to go for a ride and find a more private area. I rubbed his cock until we got to a secluded spot. We made out and finally he unzipped and pulled my head down in his lap. I was in heaven. i was sucking on a perfect, thick 8 inch cock! He stopped me and suggested we get in the back seat. Actually he ordered me to get in the back and take my clothes off. I did it without question. he joined me and stripped. I wanted to go back to sucking him but he told me to lay don. I thought he was going to suck me but he pulled out a bottle of lube. He poured it all over my cock and started stroking me. It felt great! When I was rock hard he ordered me to roll over. Again he applied a healthy portion of lube to the crack of my ass and began fingering me. I was totally into it when he got on top of me. I felt his cock line up with my asshole and I was still OK with it. But... (not a pun) He started shoving that thick 8 inches inside me and DAMN it hurt! He shoved inside me hard and began fucking me like hooker with a loose c**t. I was screaming and trying to crawl away but nowhere to go. He apparently love me wiggling because he just fucked me harder. He was very verbal, calling me a "fag" and "c**t". The pain kind of partially went away. At least I wasn't agony like the first few minutes. After I started fucking back he pulled my up a little and reached around to grab my cock. He stroked me for only a minute when I shot the biggest load of my life on his back seat. Just a minute later he unloaded in me. WOW! It was a strage feeling as the cum unloaded 8 inches inside me.
OK, that was my story. I got broken in. Tell me about your first time???

That's Juicy! 20
Remove It! 3

# 68619 - by Guy / November 13, 2023

Comments

by Anonymous on Nov 13, 2023 at 5:44 PM

Got a new ass out of it.

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by Anonymous on Nov 14, 2023 at 1:11 AM

Got railed in a booth at adult bookstore. Hurt at first but relaxed and breathed and enjoyed it.

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by Anonymous on Nov 14, 2023 at 5:28 AM

I was 14 at the time. The old dude that lived on the 3rd floor promised me a Nintendo, but I never got it. I guess you could say I really got fucked on that deal.

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by Anonymous on Nov 14, 2023 at 8:37 AM

I was 13 it was my best friend. He and I had been having oral sex for a couple of weeks. We were out in our barn in the room where we kept the feed for our horses. We had our jeans down taking turns sucking each other. He got me turned around somehow and, now he was behind me rubbing his dick on my ass. He told me he wanted to try something. I let him continue, and he had me bent over a stack of 50 pound feed sacks and was touching his dick to my asshole asking me if he could stick it in me.
It felt good so I said he could try. It took several attempts, but it went in my tight hole. We both moaned out loud and it stung really bad. I told him it hurt pretty bad, but he kept pushing. I just held on trying to take it. I felt his dick going deeper and deeper until his nuts were touching mine. He started to fuck me and it felt so good to him he came pretty fast, and shot it up my asshole. I wasn`t expecting him to cum in me but he started to fuck my asshole again. This time he fucked me good and we both liked it and he came up my ass again.
That afternoon I asked him to go down to the barn with me again and told him we could get up in the hay loft because I wanted to do it again. Once we were up in the loft, we both got naked, and he fucked me from behind while I was on my knees bent over a bale of hay. After he came in my ass he pulled out and had me get on my back. He raised my legs up and with them over his shoulders he shoved his dick back up my ass and we just looked at each other while he fucked me and came deep inside of me for the forth time in one day.
That nigh he fucked me again out in the tractor shed. The next day we spent the entire day down on the creek fucking, and sucking. He and I tried to fuck in every position possible and I sure liked taking his cum up my ass. It just felt good to let him fuck me and use my ass then feel his dick swell up inside of my asshole, then let him cum inside of me.
We were in our late 20`s when we stopped fucking. He and I moved away from each other fora few years but talked often. In our 40`s we arranged to hang out for a few days, and it was just like old times except for the fact that his dick was much bigger and he came a lot more. We stayed in a fishing cabin. Our wives thought we were fishing but we never got dressed and he fucked the hell out of me for 3 days. He shot countless huge loads up my ass, and we sucked each other dry. It was great sex and his big dick sure felt good up my ass.
I got him to try bondage with me and he liked having me tied up when he fucked me. I got him to play r**e me and be very rough with me and we had naked sex outdoors often. I let him watch as I used different things in my ass and he fucked me with a big tube of smoked summer sausage. It was hard to get it in my ass but he made me take it then I got him to fuck my mouth with it stuck up my ass. He came in my throat and the sex just got wilder after that. We did things I still can`t believe we did. I still jackoff thinking about what he and I did those 3 days. We plan on doing that again before long

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by Anonymous on Nov 14, 2023 at 10:24 AM

I was very young, too young to understand what a boy on older boy crush meant or the consequences involved. Sure it was a seduction and I was feeling great about it, I loved how he touched me, told me that I was beautiful, cute and had sweetly smooth skin. Especially when I laid before him with his knees pushing my gangly soft skinny thighs apart. My cute fleshy bottom shyly and barely covered by virgin white cotton underpants suddenly exposed by an oversexed fifteen year old with inexperienced fumbling hands. He kept re-wetting his thin boyish cocktail as he carefully tried to penetrate as I nervously clenched. He then talked me through the process of getting fucked, something he was well experienced at but virgin as a top. "Relax and push like you have to go to the bathroom" he said as he coughed up phlegm and lubed his cock and my boipussy with it..."PUSH,PUSH NOW" he said and with utter coordination he was in and squirting uncontrollably. It was only the tip but the gushing boycott was a weird experience and I kind of freaked thinking that he was peeing. He kept reassuring me it wasn't and when I calmed and relaxed he wiggled it all in till I could feel his sweat dampened boy bush and balls caressing my once cherry cheeks with an intimacy only two boy's could experience. He came again after how long I couldn't tell as my freshly being fucked tight boyc**t spasmed dry orgasms uncontrollably. I entered my teens as lovers with him and then moved. I don't think that I've ever had such a passionate lover so interested in me and how I felt about intimacy.

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by Anonymous on Nov 14, 2023 at 11:38 AM

Oh yes I recall the first time I took a cock. I was 25 and had sucked a few cocks but had not yet been fucked. I met an older stocky man around 50 in a bar not a gay bar just a regular seedy kind of place. I went home with him and sucked his cock. He wanted more and rimmed me then lubed me up. I was a bit drunk and real horny and his cock was rock hard around 6 inches. It hurt at first but God it started going in and out nice and giving me lots of pleasure. He fucked me doggy style til he blew his load in my ass. Loved it and saw him for 6 years for lots of sex and fucking. I was a full bottom after that. If it wasn't for his heavy drinking I would've stayed with him but over time he got less and less hard.

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by Anonymous on Nov 14, 2023 at 6:30 PM

My first and only time almost getting fucked I was in my twenties and followed a rabbi home from a drag show. We fooled around and sucked each others cocks and I loved it. It feels powerful to have a cock in your mouth! When he went to fuck me I thought I was ready, but was surprised by how much it hurt. The spell was broken. I got dressed and left. I've been mostly happily married to a woman for sixteen years.

Chances are that I would have settled down with a woman in any case, but I wish I would have fooled around with men more when I had the chance. I find a lit more women attractive, but that doesn't mean I don't like cock.

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by Anonymous on Nov 15, 2023 at 8:20 AM

At the age of 19 in 1972, my first experience just so happened to be an actor in the original Godfather movie. He was Marlin Brando's limousine driver. By chance alone, I got behind him in a food line at a late night diner and we had passive conversation as I filled my tray behind him. After paying for my food tray, I drifted near his table and he offered to share his table as I was interested in his story and no point in setting by ourselves. I had to work the next day and didn't care to tarry but he raised my curiosity when he said he had some good smoke in his room which happened to be in the same Hyatt Regency across the street in which I was also staying. The God Father movie was a current big seller at the theaters and asked me if I wanted to go to a late night party with his friends first. He was expecting his limo to pull up in just a few minutes. I'm really starting to doubt the whole thing when sure enough, a long black limo pulls up in front. I couldn't resist his party offer and I eagerly stepped into the luxury ride separated from the driver by glass. As a Texas cowboy, Hollywood was a long way from the ranch and I was excited to tell the story back home so "Let's see where it goes"!

The party was great and we got back to the Hyatt around 3:am. I still wanted to quickly see the script before going to my own room just to say I saw the original Godfather script, if it was true at all! Sure enough, we sat on the side of his bed together as he handed me the 3" thick actual movie script. Having seen the movie, I started thumbing through the script and was truly fascinated what a script Holly wood script actually looked like, let alone a script to such a great movie. As an engineer, I was intrigued as to how every actor in the movie had an identical copy and this is what they done for a living. His hand slowly drifts up my leg to my c*ck and after hours of weed and liquor, he took the script from my lap, laid me back on the bed, took my boots off and finally my tighty-whities. My near 7" but thinner c*ck sprang free. He pushed my ankles back over my shoulders and told me to hold the pose. It seems like it took 10 minutes just to get it in going back and forth between rimming me and poking at my very virgin hole. After another hit of Poppers, his bigger stick pressed into my cowboy p*ssy with shearing pain. He held my head up for another whiff of Poppers and started ramrodding. In minutes, I was raptured to a higher level of sensation than I had ever experienced and was confused as to how something so good could be ruled so wrong, certainly in Texas in 1972. I was completely exhausted and must have dozed off only to wake up with the TV blasting and three of his friends from the party setting around his room. I came to my senses laying naked and jumped up facing his three friends with cum dripping out of my broke ass. The limo driver was in the bathroom. My clothes were on the floor between them and I was never so embarrassed trying to hunt down my clothes and dressing in front of them. Strangely, they seemed indifferent to my very presence as I waggled and dripped among them for minutes not making eye contact with them.

I made it back to my room at 4:00am and got up at 5:00am for an early business breakfast meeting. I went back to Texas a broke back cowboy knowing I had discovered a new side of life.

I've told this story many times but never confessed my broke back part now. I think 50% of you guys would have fallen for the same trap. Life is entirely perceptual as I learned that c*ck ain't bad!

Interestingly, the second guy that took my hole was a popular country singer about 6 months later. He was bigger and he definitely sized me! Nothing like the first time though and thx for asking the readers to share their first. Great thread!!

I think my cowboy boots, lanky 113 lb frame, and my Texas drawl made me a target. This is the best story but enough for now. I'll post it if I get more likes than removes on this one. It releases something inside of me to finally open up about my experience.

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by Anonymous on Nov 19, 2023 at 12:16 PM

A close friend of my parents caught me wearing makeup and my mother's lingerie when I was sixteen. My parents were away, they had asked him to look in on me. He was very nice about it all and I wound up sucking his big cock and taking his load up my ass.

by Kurtly on Dec 2, 2023 at 1:59 AM

When I was 18 our pool boy, Tony, fucked me. Actually he was in his 30's and hot looking. I had watched him do the pool for a few month's and got turned on looking at the bulge in his little short shorts.
Most times I masturbating behind my bedroom net curtains looking at him.
The day was hot and sunny and I was home alone. I wanted a nude swim so as soon as my parents left home I stripped off and got in the pool. I swam a bit then lay nude on the sun lounger, stroking my very hard cock.
I heard the gate latch click and Tony came through it. I grabbed my towel and covered up, but he had had a very good look at my hard cock.
I had never spoken to him before but said hi, sorry or something like that.
He said not to apologize. You look hot as fuck. That really turned me on so I pulled the towel of and started to stroke my cock again.
He walked over and dropped his little shorts as he neared me. Hi cock flopped out and hardened.
He stood next to the lounger and I slide off it and took his cock in my mouth.
After sucking him he pulled his cock out and told me to lie on my back.
He knelt between my legs, spread them and push them back so my ass lifted off the lounger.
He licked and kissed my hole, fingering it and opening it up.
I felt the weight of his body move between my thighs. I wrapped my legs around his back. He eased his cock into me slowly. It hurt a bit but my hole was so wet and ready that once he was in me it felt so good...he fucked me for about 10 minutes before his body shuddered and he moaned as he came in me. That was the first of a life time of anal sex...and much more.

by Anonymous on Aug 11, 2024 at 4:47 AM

We were 16 at my house while my parents were gone for the weekend. He and I got very drunk and I told him I liked looking at his dick in the showers after football practice. He laughed and we wee so drunk he told me he would show it to me if I wanted to check it out. I told him to pull it out. So he did. His jeans were unzipped and his big meat was list hanging there about half hard.
I looked at it a few seconds then when I put my hand around it his eyes got really big and I started to jack him off and he asked me what else I had in mind. Then I put it in my mouth and he told me it felt good. Right away I tasted his pre cum and I just sucked harder his dick was very big and I gagged on it several times and by then his pants were down around his ankles and my hands were on his bare ass and he was holding my head fucking my mouth. His dick got even bigger and he started to cum and pull my mouth down on his big dick and his cum was going down my throat and I was gagging again.
I couldn’t stop sucking and licking on his big dick and he asked me to suck on his nuts so I did. He asked me how long I had been thinking about sucking his dick. I told him a long time but what I thought about most was how it would feel in my ass. He laughed out loud and said no shit !! You want me to fuck you? I told him yes I want to try it. He got real quiet then said we can do that if you really want to. I told him I don’t know if we can or not but I want to try it.
I got some Vaseline and stuck a bunch if it up my asshole like I did when many times before when I stuck other things up my ass. I will never forget how it felt to be naked with him as I bent over the side of my bed with my ass sticking up just waiting for him to try and get his big hard dick in me.
It was not easy at all and after getting it started up my ass a few times I had to get him to take it out it hurt so bad. Finally I told him to stick it in me and let me take it slow and to let me push my ass back on it as I could. It hurt like hell for awhile but I took it very slow. My asshole was getting stretched out like never before and I took most of it but at one point it hit a dead end up inside of me. I wanted all of it but something deep inside of me was stopping me from taking all of it.
I remember cum dripping out of my dick as I pushed back and finally something popped derp inside of me and the rest of his huge dick went up my ass. He wanted to fuck me but I had to ask him to wait a minute. I could feel his pulse beating inside of me and then I tried to move my ass and let it slide in and out of my asshole. After doing that a few times he took over and started to fuck me. I remember me being very loud as he fucked me and how his big dick felt going in and out of my ass. By the time he was ready to cum my asshole was numb and I had stomach cramps from having him so far up inside of me.
He tightened his grip on my hips and rammed his big dick up my asshole then started to cum. I couldn’t hold it all and it started to leak out of my ass as he kept shooting his cum up my ass.
I ended up on my stomach on my bed and him on top of me his dick balks derp in my asshole and his cum running across my nuts. He kept jumping on me and then asked me if I wanted some more. All I could do was nod my head yes. He started to fuck me and right away I could feel a lot of cum all over my nuts and between my legs as his big mushroom head was dragging his cum out of my asdhole as he fucked me.
He pounded me and fucked my ass really hard for a very long time then with his balls pressed hard against mine he filled my asshole up with cum again and I came all over myself again. He left his dick in me until it got soft and slipped out then a flood of cum poured out of my wide open asshole.
I just laid there with cum running out of me as he laid on his back next to me. It was very quiet for awhile then I asked him if he would ever do that to me again. He laughed and said just as soon as I get another hard on if you want it. I told him I think I want it when ever you are ready again.
We spent the rest of that weekend buck naked trying to see just how much he could fuck me. I think we fucked in every room of our house and several times in front of a mirror so I could see his huge dick fucking my asshole.
For several years I took his huge dick every time he wanted to fuck me which was every day. A lot of days at lunch during school he and I would drive out to this spot in the country and he would fuck me and cum up my ass then we would go back to school
He and I worked together cutting firewood in high school to make extra money and I can’t even begin to tell you how many times he fucked me out in the woods. I was bent over the tailgate of his pick up or mine many times taking it up my add with cum dripping off my nuts and I remember how it felt when he fucked me and I could feel his cum dripping down the inside of my thighs.
He liked sucking my fick and I sucked his but mostly it was all about him fucking me and me taking his big thick loads up my ass. We were up in our late 20’s both of us married the last time he fucked me on a fishing trip together.
We moved apart and started our families and are still friends but hardly ever see each other. But if he ever asked me I would gladly take that huge dick again. My first time was wonderful and every time after that was great

by thebigeasy69 on Feb 4, 2025 at 11:20 PM

Mine was a friend of the family I grew up calling uncle. He had me sucking his cock at 14 and fucking me by 15. Went on for years and I loved it. I still jerk off thinking about it.

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