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First time you had anal sex

Re: Describing the pain of first-time anal

heir-to-the-wind said:
I love to remember and try to describe the pain of the first time I felt a cock penetrating my tight ass -- like a four bladed knife ripping me open, or a red hot pipe being twisted in me. What did it feel like for you.
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my first time was with a much older guy who pretty much raped me except the I wanted him to. He pinned me down on the floor and pushed his thick cock inside me it hurt at first but after a couple of minutes the pain passed and I was loving it.
 
Re: Describing the pain of first-time anal

heir-to-the-wind said:
Did anyone ever feel guilty or ''used'' after being fucked for the first time?
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Yes, I did for sure. Being raised in a conservative Catholic family where sex was NEVER discussed, after my older buddy who was 13 and I was 12, I felt that Catholic guilt after the first time...and every time he fucked me many times after that. I felt guilty being fucked but never felt guilt when I fucked him. Our great sex sessions last til after high schollwhen he went into the service and I went to college.
 
mbamike said:
I am a late bloomer to gay sex. I was raised in a strict Pentecostal religion which taught being gay was a choice. So, I spent most of my life in denial.
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That's an amazing storry and your profile pic is so hot!
 
My First Time:
I was 26 and he was 29. He doesn't have a huge cock (5 inches or so), but it felt good. He had trouble staying hard, but got in a solid 2 minutes of nonstop ramming me and by balls kept swinging back and slapping his tight sack.


I don't often have urges to be with a guy, but if someone was nearby with a big member who wanted to top, I'd love to get a real deep fucking to try at least once!
 
Gentlemen, when recounting the "first time you had anal sex" do not reference under-aged sex. Such posts will be deleted. Thanks for your cooperation with this.
 
xyxyxy said:
Same here, never given or received anal sex. Don't think I would want to receive anal. Maybe in the heat of the moment, but I still think it is very unlikely
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I really don't think I'd want to bottom either..maybe it could happen - like you say in the heat of the moment (and the right guy)...basically, unlikely but a 'never say never' is my feelings.
If anything I see myself as more the top...though even there I doubt it'd happen. And when it comes down to it if I was in a relationship, I'd be more interested in the friendship/love part than sex.
 
MoaningMike said:
My first time taking it in the tailpipe I was [under-aged reference], he was [under-aged reference], and my best friend.
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I regret that this post needed to be deleted. But, I wasn't kidding when I stated this above:

Eagle653 said:
Gentlemen, when recounting the "first time you had anal sex" do not reference under-aged sex. Such posts will be deleted. Thanks for your cooperation with this.
Click to expand...
 
I guess I can't say how old I was but he was 4 years older. It started with him and I masturbating together. Then it progressed to him stroking me and me stroking him. We did it several times a week. Then one night when he was sleeping over he sucked me and of course I had to suck him. After the sucking started I was sucking him every day.

Then a month or so later he spent the night again. He was older than me and was half black, he was uncut but kept it clean and he was about 8 inches. This night was different, we fooled around and He sucked me a little and I got him hard. Then he had me go to the bathroom and poop, we also showered and he started to finger me in the shower. I had a shower with a hose in the basement so he figured out how to hose me out some. He got me pretty well cleaned out and we went back to my room. Then he starts fingering me with Vaseline and works up to four fingers. He had his fingers in my and was twisting them, I had never felt anything like it, I told him I like this. He then gets on top of me as I am face down and grabs my mouth with his left hand and says try not to scream then he used his right hand to guide his cock into me. He went all in with one thrust and once in he held my mouth with both hands. He moved around a little and I could feel him inside. Then as the pain was leaving he slowly started pulling out and going back in. It took about 15 minutes to get used to it but eventually he took his hands off my mouth and said it had to be this way or I would have never got it in you. He fucked me for about 20 minutes or so and came inside me. After he came he went back to fingering me and said I am going to do this to you until I have had enough which turned out to be several more times. The second time he went in with a moan and he got to fucking me. He fucked me several ways and the last one was on my back with my legs up, to this day in a sling is my favorite way, it takes me back to that night, sometimes I tell the story to the guy fucking me. When he had me on my back the last time that night we kissed and he held my legs far apart and then on his chest. Also the night I got my foot fetish when he sucked on my toes.

So I guess technically my first anal intercourse was kind of a rape because I fought but the rest of the times that night I loved what he was doing to me while he masturbated me. Later in life I found him and hooked up with him many times, about 10 years ago I flew him out here for a week where we had a week long fuck fest and relived my first time with him holding me down and forcing his way in. He also broke in my best friend who is just as gay as I am and quite a few more from what I have heard. I guess he was the gay guy deflowering guy from our town. He got a lot of use from me the two years I lived there and so did his friends.
 
First time was with my brother. 5 inch cocks or less at that time in our lives. It felt amazing like I didn't know such feelings were possible. I was bottom, and at that time I could get hard. We used lube. Better than I imagined, it led to a decades long sexual relationship.
 
I met this guy on hornet. His cock was large and he wasn't very good using it on a first timer. He did apologize after he masterbated though lmao.

When we got into the room I could tell he was horny to death when he locked the door and started kissing me immediately. His amount of hornyness was so stressing for me and kinda made me feel uncomfortable XD we didn't spend so much time having oral. He told me to turn around and lay on my stomach then he started. It was very uncomfortable to me and I was so nervous I had to jerk off for 10 minutes to masturbate after he did. We kept meeting and had sex more but he never improved. Ugh
 
BlakeV said:
I met this guy on hornet. His cock was large and he wasn't very good using it on a first timer. He did apologize after he masterbated though lmao.

When we got into the room I could tell he was horny to death when he locked the door and started kissing me immediately. His amount of hornyness was so stressing for me and kinda made me feel uncomfortable XD we didn't spend so much time having oral. He told me to turn around and lay on my stomach then he started. It was very uncomfortable to me and I was so nervous I had to jerk off for 10 minutes to masturbate after he did. We kept meeting and had sex more but he never improved. Ugh
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I'm just glad I never had experiences like this.
 
I think I was 19 and had hooked up with my first guy on a trip to London. He was a bit older than me, taller and muscular. I remember we were both quite drunk and I think we passed out when we got to his hotel room before anything really happened. I remember waking up in the morning feeling a bit stuck. I was face down and he was on top of me and I could feel he was fucking me. I tried to move but he was pinning me down and holding my hands so I couldn't move. I don't know how long he had been fucking me, but he must have started when I was still asleep.

He spoke in my ear and asked If I wanted it, He told me not to struggle or he would make it hurt more. I of course said yes! He started fucking me deeper and I remember him talking in my ear saying he was loving my hole and he was going to fuck me till he came. Even back then I was submissive and it was so hot being held down and used. He kept talking at me all the time and telling me to beg for it harder, which he obliged. He kept telling me he was come in my faggot pussy and kept asking if I wanted his load. I remember those last few thrusts as he pushed his load inside me so well. Ever since then that physical and emotional sensation of taking a guys load in my pussy has been the way I prefer to get fucked.
 
On my hands and knees in the doggy position, I was very nervous, excited, and scared. My brother and i had been sexually experimenting with each other, jerking off, jerking each other off, and I had recently begun giving him oral only three days before this. Now, I was about to take my brother's cock in my ass-- my first sexual experience. I had made sure I was "clean" before the act. My brother had already acquired lube and had it with him. I found it very sexy that he had previously decided he'd be fucking my ass and bought a bottle of lube. I KNEW this was going to be an intense and pleasurable experience. (Rectal thermometers were bliss to me, so this was definitely going to be intense.)

My brother at that time was only about 4.5 inches or so, which made "taking it" easy. The moment he entered me i gasped in surprise at the intensity of the pleasure!! I had no idea pleasure like this was possible. I had to rub my own cock, but it was hard. We both quickly came, me all over the floor, while my brother pumped me full of cum. We both LOVED it. That's what I was fearing-- LOVING this and being unable to stop. Would this make me "gay?"

TWICE DAILY..once after school and once again before bed my brother fucked my ass and filled me with cum. This happened EVERYDAY for YEARS.
 
I was 18. I had a friend a couple of years older than me, with a mutual interest in aviation. One night after a long msn session he told me he was bi curious. To which I told him I was gay (wasn't quite out to my family at that point). Then we arranged a meeting at his plane while his parents were out. We started in the bedroom before moving to the shower. First we kissed, then he blew me (which to be honest I didn't quite enjoy, he wasn't that skilled), then he fucked me and it felt amazing. I briefly fucked him but it was mainly him fucking me. One awkward thing I remember was as much as I enjoyed it I couldn't cum at all.

Nowadays I just get Joey and Chad to keep me satisfied
 
My first boyfriend just out of highschool and I were house sitting for my parents. One night, we were on the couch watching movies. I told him I thought I was ready, so we started making out and got naked. He knew I was nervous so he let me have a little control and I sat slowly on his firm, 7" dick. It hurt at first and he pulled out then we tried again. It felt so good after we got into it. There's a reason why I still keep putting things up my ass.
 
met a guy in a gay bar. he took me back to his place, and fucked me for about 20 mins over the end of a couch. It hurt like hell but also felt so good.
 
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