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First time you had anal sex

Long before I ever had anal sex for the first time, I was sticking things up my ass. I started with polish sausages (wrapped in a condom), used my fingers, and eventually bought a couple of dildos. I can't say it ever hurt, though. Somehow, I just learned how to relax my sphincter before I ever penetrated myself.

By the time I had honest-to-god anal sex, I was ready to enjoy it, and I did. The guy asked me afterwards whether I had been honest when I said that I had never been fucked. He was impressed that I didn't just lay there, but moved around and squeezed and relaxed my ass as he pounded me. He said 4 words that I'm extremely proud of: "You're a natural bottom." I felt so good when he said that.

I've never been with a huge guy - I think 8-1/2" was about the biggest cock I've taken - but I'm sure I can take almost any cock.
 
Long before I ever had anal sex for the first time, I was sticking things up my ass. I started with polish sausages (wrapped in a condom), used my fingers, and eventually bought a couple of dildos. I can't say it ever hurt, though. Somehow, I just learned how to relax my sphincter before I ever penetrated myself.

By the time I had honest-to-god anal sex, I was ready to enjoy it, and I did. The guy asked me afterwards whether I had been honest when I said that I had never been fucked. He was impressed that I didn't just lay there, but moved around and squeezed and relaxed my ass as he pounded me. He said 4 words that I'm extremely proud of: "You're a natural bottom." I felt so good when he said that.

I've never been with a huge guy - I think 8-1/2" was about the biggest cock I've taken - but I'm sure I can take almost any cock.

This was me, too. I was sticking things up my ass from a young age, enjoying the feeling, before I even thought about taking a cock. I grew up in a rural small town that was so homophobic, I didn't dare think about it. We were all kind of conditioned to be straight.

It wasn't until I moved to a city for college that I was able to buy a Dildo and started wondering what the real thing would feel like. My ass was so accustomed to relaxing and receiving, the first time I had anal sex, I felt complete.
 
Long before I ever had anal sex for the first time, I was sticking things up my ass. I started with polish sausages (wrapped in a condom), used my fingers, and eventually bought a couple of dildos. I can't say it ever hurt, though. Somehow, I just learned how to relax my sphincter before I ever penetrated myself.

By the time I had honest-to-god anal sex, I was ready to enjoy it, and I did. The guy asked me afterwards whether I had been honest when I said that I had never been fucked. He was impressed that I didn't just lay there, but moved around and squeezed and relaxed my ass as he pounded me. He said 4 words that I'm extremely proud of: "You're a natural bottom." I felt so good when he said that.

I've never been with a huge guy - I think 8-1/2" was about the biggest cock I've taken - but I'm sure I can take almost any cock.
I started out doing the same thing !!
 
Growing up, we would move every 3-5 years. Each move was to a slightly bigger place, village/town/city. The place we lived when I went to first grade wasn't much more than a crossroad, with a gas station/general store/post office, on state route 7 in Oho. By the time I graduated high school, 4 of the 5 places we'd lived were along Ohio route 7, from rural to urban.

That was the 50s and 60s. "Lassie" and "Leave It To Beaver". To say the information I was getting was somewhat "protected" would be an understatement. I was also a preacher's kid, so that just added to my bubble.

Getting fucked in the ass was one of the very worst things that could ever possibly happen to a guy! The pain would be indescribable! Your standing in the community would be destroyed forever! You would be an outcast leaving a trail of blood behind you! Your undies would always be smeared with poop! Your best hope would be that it would kill you!

Those were my impressions as I went off to college! Of course, not everything you learn is in a classroom ...

My teens and twenties perfectly synched with the 60s and 70s. "Free Love", "Flower Power", and all the Hippie stuff. I was away from home, freed of my family's public, and sex was all around me! I had more than my fair share of luck with the ladies! There were also a few guys tossed in, scattered here and there, on the DL. I was still "knee jerk" concerned about my social rep.

I fucked my first guy spring quarter of junior year. We had a small history of sucking each others' dicks, that wasn't very often, given conflicting schedules, and changing living arrangements. He also happened to have been the first guy I'd ever sucked off (winter quarter of freshman year).

I was surprised when he asked me to fuck him. I was worried about hurting him! I had NO idea that getting fucked could be pleasurable! He was tighter than any chick I'd fucked!
He was on his back, so I got to watch all of him as I plowed his ass. After I came in his butt, he told me to stay put while he jerked off. Dude shot over his head! His butt was squeezing my dick with each spasm of his orgasm. I nearly came again!

That was also the last time I ever saw or heard from him. Not because of what we'd been doing. Life simply moved on. Something I'd grown very (too) used to. Leaving people in the past was something that had been trained into me.

Fast forward about 3 years ... Leaving out tons of details ...

We were on the pool shooting team at our local bar. He was the same size as me, about 5'6", except he had muscles! We were "drunk as skunks" after a night of pool, ending up in his parents' down stairs shower, using his dad's Prep-H for lube, as he introduced me to having something (in this case it was his dick) put up my virgin asshole for the very first time.

He had let me fuck him first for a bit, to show he didn't mind taking it, then it was my turn to assume the position, with my hands on the back wall of the tub/shower. There was the feeling of a little pressure when he slipped his dick past my pucker, butt no pain! Not even a hint! It was likely a combination of too much beer, and the Prep-H bit of numbing (maybe). He slid right into me, started going slow, then picked up his pumping pace, 'til he came inside me, held on for a bit, his chest heaving on my back while he hugged me tight, then slipped out saying, "Now you get to cum in me!" So ... we switched positions, and I fucked him to climax (mine).

That was the first for me getting fucked in my ass, butt by no means the last! We flip fucked at different times, in different places, in different positions, even sober! I was also his supervisor at work, and was dating his fiance's sister. I was in his wedding. We fucked after his bachelor party the night before. We even messed around after he was married. Then I got a different job, and we slowly lost touch.

You never forget your first, though.
 
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This was me, too. I was sticking things up my ass from a young age, enjoying the feeling, before I even thought about taking a cock. I grew up in a rural small town that was so homophobic, I didn't dare think about it. We were all kind of conditioned to be straight.

It wasn't until I moved to a city for college that I was able to buy a Dildo and started wondering what the real thing would feel like. My ass was so accustomed to relaxing and receiving, the first time I had anal sex, I felt complete.
That was me too. I had a top once tell me "you just take it". I made him cum twice and he said I was an awesome fuck. I pride myself on that.
 
I'm always amazed at all the stories about sucking off cousins, brothers, and friends when still so young. I was never in that type of situation; only one guy I knew jerked off in front of me and that was him standing in the middle of our Boy Scount summer camp while he was screaming a banshee. I never got the chance to jerk off with somebody, or found myself with the opportunity to touch or taste somebody's cock. I'm sure if I had had that chance I wouldn't have gone through that damned 15-year straight period.
 
Growing up, we would move every 3-5 years. Each move was to a slightly bigger place, village/town/city. The place we lived when I went to first grade wasn't much more than a crossroad, with a gas station/general store/post office, on state route 7 in Oho. By the time I graduated high school, 4 of the 5 places we'd lived were along Ohio route 7, from rural to urban.

That was the 50s and 60s. "Lassie" and "Leave It To Beaver". To say the information I was getting was somewhat "protected" would be an understatement. I was also a preacher's kid, so that just added to my bubble.

Getting fucked in the ass was one of the very worst things that could ever possibly happen to a guy! The pain would be indescribable! Your standing in the community would be destroyed forever! You would be an outcast leaving a trail of blood behind you! Your undies would always be smeared with poop! Your best hope would be that it would kill you!

Those were my impressions as I went off to college! Of course, not everything you learn is in a classroom ...

My teens and twenties perfectly synched with the 60s and 70s. "Free Love", "Flower Power", and all the Hippie stuff. I was away from home, freed of my family's public, and sex was all around me! I had more than my fair share of luck with the ladies! There were also a few guys tossed in, scattered here and there, on the DL. I was still "knee jerk" concerned about my social rep.

I fucked my first guy spring quarter of junior year. We had a small history of sucking each others' dicks, that wasn't very often, given conflicting schedules, and changing living arrangements. He also happened to have been the first guy I'd ever sucked off (winter quarter of Freshmen year).

I was surprised when he asked me to fuck him. I was worried about hurting him! I had NO idea that getting fucked could be pleasurable! He was tighter than any chick I'd fucked!
He was on his back, so I got to watch all of him as I plowed his ass. After I came in his butt, he told me to stay put while he jerked off. Dude shot over his head! His butt was squeezing my dick with each spasm of his orgasm. I nearly came again!

That was also the last time I ever saw or heard from him. Not because of what we'd been doing. Life simply moved on. Something I'd grown very (too) used to. Leaving people in the past was something that had been trained into me.

Fast forward about 3 years ... Leaving out tons of details ...

We were on the pool shooting team at our local bar. He was the same size as me, about 5'6", except he had muscles! We were "drunk as skunks" after a night of pool, ending up in his parents' down stairs shower, using his dad's Prep-H for lube, as he introduced me to having something (in this case it was his dick) put up my virgin asshole for the very first time.

He had let me fuck him first for a bit, to show he didn't mind taking it, then it was my turn to assume the position, with my hands on the back wall of the tub/shower. There was the feeling of a little pressure when he slipped his dick past my pucker, butt no pain! Not even a hint! It was likely a combination of too much beer, and the Prep-H bit of numbing (maybe). He slid right into me, started going slow, then picked up his pumping pace, 'til he came inside me, held on for a bit, his chest heaving on my back while he hugged me tight, then slipped out saying, "Now you get to cum in me!" So ... we switched positions, and I fucked him to climax (mine).

That was the first for me getting fucked in my ass, butt by no means the last! We flip fucked at different times, in different places, in different positions, even sober! I was also his supervisor at work, and was dating his fiance's sister. I was in his wedding. We fucked after his bachelor party the night before. We even messed around after he was married. Then I got a different job, and we slowly lost touch.

You never forget your first, though.
You are right...you never forget the first time...
 
My first cock was still one of the biggest. So the first time he literally took it easy and only put about a third of it in while he jerked it and came inside me. I liked it cause his head was right on my prostate. Eventually after a few weeks I was able to get it all in with no issues. Thankfully he was a gentle teacher at first.
 
My first cock was still one of the biggest. So the first time he literally took it easy and only put about a third of it in while he jerked it and came inside me. I liked it cause his head was right on my prostate. Eventually after a few weeks I was able to get it all in with no issues. Thankfully he was a gentle teacher at first.
MMMM , yes , bareback of course 💓💖🥰
 
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