Your First Time

danielbroq

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I've been looking for a thread for people to write about / explain their first time (sex), but couldn't find it. If I'm wrong, please let me know and reply with a link to the (original?) thread. But basically, I'm curious for everyone's first time. Let me know! :)

I'll go first. It's not all that exciting, but can't open a thread and then don't tell my story. Basically, I was on Grindr (I'm gay if you couldn't tell already lol), as I was a lot. My original plan to lose my virginity with someone who'd mean something to me. Or at least to have something of a connection with that person. But I got in touch with a really nice guy, looked great and was very sweet. I told him i was still a virgin and he was all okay with it and didn't mind. I stepped on my bike and went over to his place. It was in an old convent, renovated to have studio apartments in it.

At first we just talked for a bit and eventually we started feeling each other. After like five or ten minutes of feeling each other, we moved to his bed and started doing the real work. I bottomed, he topped. But it was too painful, so eventually he stopped fucking me and we jerked off to cum.

Looking back at it, I don't look at it with regret. But I'm curious to see if I'm the only one who's had a disappointing ending. Probably not, but I have barely talked to any other gay man about their first times.
 

Thom Hewson

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well I was very much of age. 54 to be exact. Married 26 years with two teenage sons. I married in search of a different life than the one i was terrified would end tragically too soon in the throes of the AIDS crisis. But even though when i told my wife of my desires early on and she said, I love you anyway, i was blind to how different we were as people... her volatility and better right than sorry kind of attitude in life was wearing on me to the point of breaking. Throw in a headstrong teenage in the midst of applying to college.. well i was a mess.

the catalyst was a totally unexpected encounter with a clothing salesman who came on to me full on in the dressing room. I will skip the details except to say i was obviously unprepared, terrified of catching HIV, and and not totally up for the moment, but it was the first time i had sucked a cock since grad school and i was floored by the randomness of the encounter.

Fast forward to a moment of self reckoning, signing up for a couple man sites with the intent of talking with guys to help decide if i really knew what i was getting into throwing in the towel on the marriage, and a then late 30s Polish software engineer found me on silverdaddies. it turned out he worked literally next door to my downtown office. After a couple awkward conversations ...he wanted to know what i liked to do, etc, well i had done none of really... we met for drinks in the park facing our office towers.

Now just imagine you are meeting the type of guy you have pretty much dreamed about and jerked off to... he was very much all that. Rugged masculine looks, an inch or two taller, broad shoulders, very white smooth skin wrapped tightly over bulges and hardness in all the right places. He told me to unbutton the top of my shirt as we drank some wine so he could have a better look at my chest hair. Proposed i meet him at a nearby hotel the following week when he was downtown for an evening meeting and staying over.

I wasnt prepared for what would come next, but he knew i was virgin with another man and took it slow. Seeing him naked with his thick uncut 8 inches erect and almost upright, pointed cockhead just built for fucking, running my hands over his muscled ass tattoed with POLONIA on the right cheek, feeling his hard chest on top of me as he kissed deeply, was overwhelming for a first carefree encounter. We made out for a good hour until our balls ached and jerked each other ... i hit him in the face with my load. Driving home i remember saying out loud to the rearview mirror , Finally i can breathe....

He told me i needed to learn how to clean out, so i did my own research. He told me buy fiber powder to make the job easier. I bought a disposable enema to douche and made sure i was squeaky clean when we planned to meet a couple weeks later (he travelled a lot for work).

What i remember of that "first" time he penetrated into me was there was alot of lube, he took it very slow and coached me to breath, backed in and out a few times until i was comfortable with him going in, and then turned me on my stomach to lay under the hard heavy blanket of his muscles. I imagined his glutes turning to stone with every long slow thrust. He continued kissing over my shoulder, breathing deeply into my ear as he nibbled on my ear lobe.

Then suddenly stopped and said, "ok your turn" ! Flipped on his back with his legs up so i could see his eyes roll back as i went in balls deep. This first experience of being with a vers man completely molded me sexually.

We had a series of encounters like this. almost always in hotels, except the rare times I had the house to myself. I felt obliged to do something to show thanks like bringing a bite of food and some wine. He said i was crazy and thanked me for letting him use my hole. My gratitude went far beyond appreciation for him hosting in a hotel.. it was really all about lifting decades of angst, I think he understood that but to him i was just there to have the sex I wasn't getting at home.

The rest of the story has many twists and turns. There was the time I got the type of temporary amnesia you get when you overexert yourself (google TGA)... but i was in a hotel room on the other side of town and a gay friend who happened to call me as i lay in bed clueless tracked him down to go back to the hotel and get me on my way home. There was the 4 way i invited him to with a married couple after he said he was interested. There was a wonderful moment at my home, when we came downstairs in bathrobes to have some lunch, he manspread in a wicker chair in the sunroom and said, "go ahead, suck it..." after we had ate and drank, and then headed back upstairs for round two...

A couple years in, I picked up an STD from i still cant figure out where, and he bolted for a couple years. We eventually reconnected, by that time I had met someone else who was also married and lived a quiet life as a middle school teacher in a farm town 2 hours away. Long story short, I picked up an STD from this man who i realized was really quite naive even though he'd been with men most of his life. I had been with my first man, only for the third time since we reconnected, only the week after i had met up with my out of town lover. My first man developed symptoms the next week... it turned out in the interim he had been with a married guy of his own whom he occasionally saw, who promptly dumped him. I took the reins in getting my lover treated and figured out he had never really been cured the first time due to improper treatment, and had picked up a different STI from a random encounter in a gym (gonorrhea is spread by touch, a guy rimmed him. The chlamydia i discovered the first time is spread by fluids. He was given the wrong antibiotic at his clinic.)

Three days from now is my first man's birthday. I never stopped wishing him a happy birthday every year. I don't know if or when I will ever see him again, i feel like i can never apologize enough for what happened. All i have now are some very fond memories of the man with whom i feel I have been the most sexually compatible ever, a couple stolen photos of his magnificent boner and solid frame, and one picture he shared with me of his glistening cum leaking out of my hole after he bred me one of the first few times we were together.
 
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danielbroq

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well I was very much of age. 54 to be exact. Married 26 years with two teenage sons. I married in search of a different life than the one i was terrified would end tragically too soon in the throes of the AIDS crisis. But even though when i told my wife of my desires early on and she said, I love you anyway, i was blind to how different we were as people... her volatility and better right than sorry kind of attitude in life was wearing on me to the point of breaking. Throw in a headstrong teenage in the midst of applying to college.. well i was a mess.

the catalyst was a totally unexpected encounter with a clothing salesman who came on to me full on in the dressing room. I will skip the details except to say i was obviously unprepared, terrified of catching HIV, and and not totally up for the moment, but it was the first time i had sucked a cock since grad school and i was floored by the randomness of the encounter.

Fast forward to a moment of self reckoning, signing up for a couple man sites with the intent of talking with guys to help decide if i really knew what i was getting into throwing in the towel on the marriage, and a then late 30s Polish software engineer found me on silverdaddies. it turned out he worked literally next door to my downtown office. After a couple awkward conversations ...he wanted to know what i liked to do, etc, well i had done none of really... we met for drinks in the park facing our office towers.

Now just imagine you are meeting the type of guy you have pretty much dreamed about and jerked off to... he was very much all that. Rugged masculine looks, an inch or two taller, broad shoulders, very white smooth skin wrapped tightly over bulges and hardness in all the right places. He told me to unbutton the top of my shirt as we drank some wine so he could have a better look at my chest hair. Proposed i meet him at a nearby hotel the following week when he was downtown for an evening meeting and staying over.

I wasnt prepared for what would come next, but he knew i was virgin with another man and took it slow. Seeing him naked with his thick uncut 8 inches erect and almost upright, pointed cockhead just built for fucking, running my hands over his muscled ass tattoed with POLONIA on the right cheek, feeling his hard chest on top of me as he kissed deeply, was overwhelming for a first carefree encounter. We made out for a good hour until our balls ached and jerked each other ... i hit him in the face with my load. Driving home i remember saying out loud to the rearview mirror , Finally i can breathe....

He told me i needed to learn how to clean out, so i did my own research. He told me buy fiber powder to make the job easier. I bought a disposable enema to douche and made sure i was squeaky clean when we planned to meet a couple weeks later (he travelled a lot for work).

What i remember of that "first" time he penetrated into me was there was alot of lube, he took it very slow and coached me to breath, backed in and out a few times until i was comfortable with him going in, and then turned me on my stomach to lay under the hard heavy blanket of his muscles. I imagined his glutes turning to stone with every long slow thrust. He continued kissing over my shoulder, breathing deeply into my ear as he nibbled on my ear lobe.

Then suddenly stopped and said, "ok your turn" ! Flipped on his back with his legs up so i could see his eyes roll back as i went in balls deep. This first experience of being with a vers man completely molded me sexually.

We had a series of encounters like this. almost always in hotels, except the rare times I had the house to myself. I felt obliged to do something to show thanks like bringing a bite of food and some wine. He said i was crazy and thanked me for letting him use my hole. My gratitude went far beyond appreciation for him hosting in a hotel.. it was really all about lifting decades of angst, I think he understood that but to him i was just there to have the sex I wasn't getting at home.

The rest of the story has many twists and turns. There was the time I got the type of temporary amnesia you get when you overexert yourself (google TGA)... but i was in a hotel room on the other side of town and a gay friend who happened to call me as i lay in bed clueless tracked him down to go back to the hotel and get me on my way home. There was the 4 way i invited him to with a married couple after he said he was interested. There was a wonderful moment at my home, when we came downstairs in bathrobes to have some lunch, he manspread in a wicker chair in the sunroom and said, "go ahead, suck it..." after we had ate and drank, and then headed back upstairs for round two...

A couple years in, I picked up an STD from i still cant figure out where, and he bolted for a couple years. We eventually reconnected, by that time I had met someone else who was also married and lived a quiet life as a middle school teacher in a farm town 2 hours away. Long story short, I picked up an STD from this man who i realized was really quite naive even though he'd been with men most of his life. I had been with my first man, only for the third time since we reconnected, only the week after i had met up with my out of town lover. My first man developed symptoms the next week... it turned out in the interim he had been with a married guy of his own whom he occasionally saw, who promptly dumped him. I took the reins in getting my lover treated and figured out he had never really been cured the first time due to improper treatment, and had picked up a different STI from a random encounter in a gym (gonorrhea is spread by touch, a guy rimmed him. The chlamydia i discovered the first time is spread by fluids. He was given the wrong antibiotic at his clinic.)

Three days from now is my first man's birthday. I never stopped wishing him a happy birthday every year. I don't know if or when I will ever see him again, i feel like i can never apologize enough for what happened. All i have now are some very fond memories of the man with whom i feel I have been the most sexually compatible ever, a couple stolen photos of his magnificent boner and solid frame, and one picture he shared with me of his glistening cum leaking out of my hole after he bred me one of the first few times we were together.
Thanks for sharing @Thom Hewson !
 

Thom Hewson

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Age restrictions keep me from telling mine but it was a taboo situation. Then his brother caught on and I wanted me as well.
I can relate. My very first experiences were with a cousin of almost identical age at an age i can't mention. Not much action at all, can't even say it planted a seed. But the spark was lit.
 

Adventure86

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Nice! Tell more, how did it happen?
I caught my date having sex with someone during prom and I left with the limo driver leaving my date. The limo driver saw that I wasn't happy and upset, so he took me to the beach and we sat down and talked. After a long conversation one thing led another and I opened up after he said that he can see that I had a secret and I was holding it in. Well after I told him I secretly liked guys and one thing led to another he kissed me and I liked it. That night he took my virginity in a hotel room and I saw him a few more times after that and kept in contact. PM me if you want to know more
 

Adventure86

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Hey. I’m 29, from California.
I’m straight but I wanna try with man
But I’m afraid of a first sex
I can honestly say that I was definitely afraid and nervous my first time because I didn't know what it was going to be like. Just take it slow when you get a chance to have your first time with a man and tell the guy to take it slow and let you get use to it.