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First time you had anal sex

He had the cutest dick, about 5", still a little slender, it slanted up at 45 degrees.
We had masturbated each other and
gone oral, I had this urge on this day to get fucked, I really wanted it, Tom
was so sweet to me, he was happy to meet my needs.
I dropped my pants and tighty whities,
he stood behind me and I bent just a little and spread my cheeks for him.
He held my hips and pushed his wonderful penis into my ass, wow!
I loved it! He was so good at fucking,
I kept telling him I wanted more and to do it harder, he did his best, harder and faster, then he quivered, thrust really hard and his precious penis exploded in me.
It was many years ago, I just got hard reliving it, thanks for the opportunity to share.
 
My neighbour took advantage of me when i was feeling quite low one night. While i was sat in my chair, he got on his knees and pulled my pants down and started to suck my cock. I felt really guilty about it at first, but my cock was so hard and really enjoyed it. He had me laying face down flat on my bed and pulled his cock out, i remember thinking it was really thick at the time, certainly thicker than mine anyway. He started to rub his thick cock between my cheeks and kiss my neck. Throughout all this time he would reassure me and tell me to just relax. He was so gentle and took such a long time getting me to relax, I will allways appreciate the way he introduced me to my first fucking. Ofcourse it hurt at first, but i got used to his big cock eventually and i absolutely loved the way he took me. He fucked me a few times and sucked my cock many more before he moved away to another city. That was at least 15 years ago and i still think of our times very often
 
We became boyfriends before ever even meeting each other. I drove 4 hours to actually meet him for the first time. It was so awkward at first. After a while we were making out non stop. Not wanting to move to fast, we watched a movie and cuddled. Afterward we started making out again and rubbing our hard dicks together through our jeans. Eventually I went down on him and was shocked to see he easily had a 9 inch dick and pretty thick. I sucked his cock with him rubbing my head and slightly pulling my hair every so often. We traded places and he did the same to me. Then he went to grab a condom which made me pretty nervous. I wanted to fuck him but I got so nervous that I couldn't stay hard (:/). So instead I got on my back and he put on the condom, spit on his hand and rubbed it on his dick, then he put my legs on his shoulders and slowly slid his cock in my ass. It hurt at first having 9 inches inside me hole for the first time, but I got used to it and it started to feel good. He started fucking me harder with each thrust. Shortly after he was really into it, my arms and legs were tingly and numb. He made my toes curl until my feet got cramps in them. I finally started to jerk off and it didn't take long for me to cum on my stomache. Then he pulled out and jerked off until he came on my stomache too. Then he licked up a little bit of our cum, swallowed it, and then kissed me. I thought it was the hottest thing ever. The relationship diminished over the next couple months cuz of the distance. But you never forget your first!
 
It was a while after I had first given Vincent his first sucking from me.

We were both young, and knew little about gay sex other than how to kiss, suck cock, and enjoy the feeling of touching each other.

I had read about straight anal sex in a Playgirl magazine I had nervously bought one time. I figured that if a guy and girl could do that, why not a guy and a guy?

Vincent was game to try it, so we did...

I gritted through the initial pain, and then enjoyed the feeling as he wrapped himself around me and pumped...(we were doing it doggy style)

He came inside me. I was jacking myself off and came on the bed.

Eventually, we figured out how to do is missionary style. And I loved looking up at his sexy face, and into his eyes as he and I were making love.
 
We had already been experimenting with oral and such for a while, and we finally decided to go all the way.

It was amazing, but we both pretty much fucked it up the first time. We knew what we were supposed to do, but lack of experience really showed. We both did it doggie style since it seemed the easiest way. Neither of us lasted very long and ended up going home with cum in our asses.

We learned quickly though, and hooked up as often as we could until both of use left to go to different colleges.
 
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.

I reached a point in my life where I could not deny my internal sexual desires any longer. I figured I would try gay sex, would not like it, and would have this issue in my life behind me. I had spent years prior to this using dildos and sticking objects up my ass when I masturbated.

Anyways, I found a guy on Adam4Adam who agreed to hookup with me. I told him I was a gay virgin and wanted to experience gay sex. I was on a business trip and we could use my motel room to hookup.

His name is Charles, but goes by Chuck. He lived in Albuquerque, but was in South Carolina pursuing another master's degree so he could counsel veterans returning from the wars. He has a PhD in education already. He has reddish brown hair, is about two years my junior, and his cock is 7.5 inches and very thick.

We begin by just lying on the bed talking. Then after a few minutes he started touching my arm and rubbing my bare chests. I was only wearing a pair of sweat pants. Finally, I asked him if he was ready to have sex. He was of course.

I dropped my pants and was completely naked in about five seconds. It took Chuck a little longer to get naked, but he eventually got naked and climbed into bed with me.

We started out with total body contact and kissing. I don't know what came over me, but it was as if I went into automatic pilot. I began ramming my tongue down Chuck's throat and trying to climb on top of him. I caught myself and backed down. I told him I was sorry and that bottoms don't do that. He laughed!

He said I was an aggressive bottom and for me just to enjoy myself. Well, I did. One would think we were wrestling the way I was all over him.

Before I realized what I was doing, I had gone from deep kissing Chuck to sucking on his cock and licking his balls. Chuck began sucking me too.

Then he caught me by total surprise and started licking my hole and sticking his tongue inside it. WOW! My body began trembling and convulsing out of control! I had lost control of my own body at this point!

Then he asked me if I was ready to be fucked, of course I was. He put on a condom and lubed it up and lubed my ass too. He slowly penetrated me which was no problem. Then he slowly began sliding his cock in and out a bit. When it appeared my hole had acclimated to his cock, when got down to some serious fucking!

He fucked me in all types of positions; missionary, doggy style, ass up in the air, on my side, feet over my head, etc. We went at it for about four hours. I had never in my entire life had four-hour sex!

Since it was so late and we were getting along so well, I asked him if he wanted to spend the night with me. He said "Yes!"

We cleaned up a bit and put on our clothes, then went out to dinner. It turned out Chuck was a psychologist and does counseling work at one of the local hospitals. I ended up asking him a gazillion questions about being gay since this was all new to me. He was very understanding and answered each one.

We went back to the motel room after dinner. We got naked again, hopped into bed and began making out again. We would fuck awhile, take a nap, then wake up to fuck some more. Chuck was supposed to have been a one-time hookup, but we ended up spending the weekend together. My ass was plenty sore when I went home on Sunday evening.
 
I was in college and had not been with another guy prior; I was at a large house party and this guy who I knew on campus as he showed apartments for lease to students starts chatting me up at the party which was held at his house. Great night he kept bringing we beers from the keg and then about 2 am when the party was dying down..he gets out a bong and there are four of us left me, him, his girlfriend and another girl. The girls leave and it's just he and I and the usual shit you hear crap she left me hard and what can we do...i was curious he says how about you suck me and then you can fuck me...i am thinking yeah right I will suck his cock and get him off and that's it..i liked him good looking guy so what the heck..he gets naked i start sucking him..poor guy wasn't that big...while i am sucking him he rubbing my cock through my jeans and i shuck them off and he likes my cock and tells me it's my turn and to go slow he always wanted to try anal sex..so he lays down and i lay on top of him and push my cock slowly in get in all the way in and start going at it..i cum and think i can go again thus I do..we went at it for about 30 minutes neither of us that wise i just remember after the third load..he said i can take any more and got up to run to the bathroom but was a little late and farted and oh lord the cum starting flowing out
 
Describe the pain of first-time anal sex

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?
 
Re: Describe the pain of first-time anal sex

- I was thirteen and remember being completely naked and ass up, face down. An older boy and I were watching porn and we took our clothes off. I sucked his cock for a little bit and asked me to get on my knees.
- I remember how hot his cock head was when I felt it between my ass cheeks for the first time. The gentle push on my tight, brown and small star and ring kept tightening up when he pushed forward stronger. I was whimpering, squealing in pain asking him to do it slowly and gently, because of the familiar sharp pinch of my sphincter squeezing tight and being forced open with that shockingly hard erection!
- The older boy put more lotion on his cock. I felt more stinging and pain on my already tender asshole from his increasingly strong jabbing and pushing on my tight asshole! I cried out in pain and shock when he finally penetrated me. His shaft stretching my virgin anus felt like he was splitting me in half when he began to slowly pump me in and out. He started fucking me faster as I was wailing, crying and breathing deep and shallow. I am still loud when being fucked! He finally shot a huge load of cum inside my raw ass and remember the blood, semen and shit while I was tenderly wiping and cleaning myself!
- It was very painful but I was never so horny in my life being naked with another boy and watching porn on the reservation!
 
Re: Describe the pain of first-time anal sex

nudenative said:
- I was thirteen and remember being completely naked and ass up, face down. An older boy and I were watching porn and we took our clothes off. I sucked his cock for a little bit and asked me to get on my knees.
- I remember how hot his cock head was when I felt it between my ass cheeks for the first time. The gentle push on my tight, brown and small star and ring kept tightening up when he pushed forward stronger. I was whimpering, squealing in pain asking him to do it slowly and gently, because of the familiar sharp pinch of my sphincter squeezing tight and being forced open with that shockingly hard erection!
- The older boy put more lotion on his cock. I felt more stinging and pain on my already tender asshole from his increasingly strong jabbing and pushing on my tight asshole! I cried out in pain and shock when he finally penetrated me. His shaft stretching my virgin anus felt like he was splitting me in half when he began to slowly pump me in and out. He started fucking me faster as I was wailing, crying and breathing deep and shallow. I am still loud when being fucked! He finally shot a huge load of cum inside my raw ass and remember the blood, semen and shit while I was tenderly wiping and cleaning myself!
- It was very painful but I was never so horny in my life being naked with another boy and watching porn on the reservation!
Click to expand...

Great description. Thanks.
 
When got my anal cherry popped

In 1969 I was 22 years old and living in the Lawson YMCA on the near-north side of Chicago. My dick was big, my buns cute, and I was flattered when guys followed me to my room to suck me off. Nothing ever felt so good as getting a blow job. I was “trade,” though — I didn’t suck cock and never took it up the ass.

One night in the shower I eyed an older, military-looking dude with manly (not boyish) facial features, short hair, chiseled build, and a thick dong dangling between his legs. He winked, and I knew he would follow me back to my room. I laid back on the bed, my proud dick begging to be serviced. He stroked my sensitive nipples until they were rock-hard and sucked my throbbing cock, while fingering my butthole, until I moaned and squirmed in heat.

“Ever get fucked?” he asked.

I was young and hot for this forbidden sex, but too naive to know how much it would hurt to have his long and fat cock, dripping with pre-cum anticipation, shoved up my tight and virgin ass. In my silence he perceived the answer to his question — indeed I was a wide-eyed ass-virgin. Without speaking, he positioned me on my side near the edge of the bed; laid himself down behind me; spit-lubricated his cock and pressed it against my butthole. So excited by the prospect of this anonymous and forbidden sex, I made no protest. I tensed up when I felt its huge head pressed against my butthole. He gently stroked my nipples. “Ready?” he asked. I groaned. He shoved the head of his cock inside me.

“Yeeeooow!” I felt as if a hot knife were ripping me open. Tears welled up in my eyes, I arched my back in the searing pain, and I thrashed about in a struggle to pull away – but the stronger muscled man held me tighter and forced my face into the pillow to muffle my screams of pain.

“Oh, Gawd!” I cried. “Take it out! It HURTS!”

The stranger just grabbed me tighter against his chest, licked my neck, and poked his tongue in my ear. “I know it hurts,” he whispered. “Relax and try to take it.”

He paused until I could relax a little (but just a little) to stop struggling, and then he pushed his cock in deeper, ever so slowly, ever so gently, inch at a time, as I writhed in pain and bit the pillow. He was patient but, despite my woeful pleas to “take it out,” he was determined to sigh with pleasure by penetrating my virgin ass all the way. The shock of the initial penetration of his cockhead was the most painful experience of my life.

“It hurts!” I cried. “Pleeease stop! Take it out!” He held me even tighter and slowly shoved his cock in deeper. “OOOHHHH! What a sweet tight ass!” he moaned.

Inch by excruciating inch he pushed deeper and deeper inside me. When he was all the way in, he started to pump his tool gently in and out. It still hurt. My ass burned with the sawing of his cock. His mushroomed head was smashing my guts. He began to breathe more heavily and moaned aloud as he stepped up the pace of his thrusts to a wild frenzy until, at last, he gave one final thrust of his cock as deep as it would go. I felt the head of his cock expand and explode his warm man-juice inside me. He trembled in his orgasm and groaned his satisfaction, pleasure, and relief. My ordeal was over. He nodded me a smile as he left my room as anonymously as he came. I never saw him again except in my nostalgic memory of that warm summer night when I took it up the ass for the first time.
 
Re: When got my anal cherry popped

My first try was a disaster -I couldn't take it so he stopped. Actually my partner was my first - I snuck him into the house where I rented a room upstairs. He saw some Vaseline on the night stand lubed up and entered me. He did so very slowly but it still hurt a lot. Then he crept back downstairs and left ! We could have been caught but luckily were not. It became much easier when we started living together. BTW we've been together 49 years.
 
Re: When got my anal cherry popped

IowaGuy said:
My first try was a disaster -I couldn't take it so he stopped. Actually my partner was my first - I snuck him into the house where I rented a room upstairs. He saw some Vaseline on the night stand lubed up and entered me. He did so very slowly but it still hurt a lot. Then he crept back downstairs and left ! We could have been caught but luckily were not. It became much easier when we started living together. BTW we've been together 49 years.
Click to expand...

Even though my first time hurt, as I described in the OP, it is a pleasant memory for me. I get hard thinking about it, and all of the other times I took it in the ass, always with pain, because I felt obligated to reciprocate for a good blowjob. I am predominately a top and get turned on when a guy screams, ''It hurts. Take it out.'' I act like the stranger who fucked me for the first time.
 
Re: Describe the pain of first-time anal sex

I was 19 at the time, been on 3 or 4 dates with this guy, I knew he was the one who I wanted to bust my cherry. We'd fooled around once before, blew each other off, I was ready for the next level, but I made him promise that I could fuck him as well if he fucked me first. He was kind of a small/skinny dude, shorter than me at 5'7", but damn he had a big old fat dick. I had fooled around with a small butt plug, my fingers, tried to loosen up the sphinxter, but damn it felt like he was putting a hot iron up my ass that first time. He fucked me while I was on my back, legs spread, kissed me all over, did all kinds of crazy things with his hands that as a result I got off before he did, but most importantly he made eye contact the whole time, despite the pain I will say it rates as one of the most erotic encounters I've ever had.

The next date I fucked him, but it wasn't his first time. Employed a few of those tricks he taught me, although I did fuck him doggy style at his request, seriously fucking hot though. That first guy, man its special and something you never forget. Hell even after breaking up and not talking to each other for over a year, a mutual friend kind if mediated and now we have a totally different sort of friendship going on 10 years strong now, something both of us hold dear that we would never violate with a night of passion.
 
Re: Describe the pain of first-time anal sex

It seems to hurt more when lying on your back. Despite the pain, it is indeed very erotic.
 
Re: Describing the pain of first-time anal

The first few times were excruciating, like I was being ripped in two, but then I had just turned 16 and hadn't finished growing. Over the next couple of years I tried it a handful of times always with the same result. That was also true for the guys I tried to top. No one got to cum :(

I didn't do it for a couple of years. The summer of between my junior and senior years I was living in New York. It was the first time I was around a lot of gay men (I had been pretty DL up until then). I joined a gym, and I was aware that at least a third of the members were gay. The second time I went, I noticed this one guy, really good looking, great body, but older. He had salt-and-pepper hair, great body. I didn't think of him sexually. I was more like 'I hope I look that good when I'm his age!'. He must have seen me checking him out because the next night he came over and introduced himself. I told him about my school, my summer internship. He seemed impressed. He was a securities lawyer. Then he asked me if I wanted to grab a cup of coffee. I said of course. I was so pumped: three days in New York and I'm already networking!

We walked about a block, continuing the school/career chit-chat. When we passed his apartment said he wanted to drop off his gym bag. When I came down over an hour later I was completely transformed! I don't have a clear memory of it since it seemed to happen so fast and everything he did felt so good and it just went in! And he wasn't small, by any means. I don't know if he was on blue pills or what but he stayed hard after he nutted for the first time and kept on banging me. And that was how the summer started. I went on to make some great gay friends who showed me around. It was always there, I could always have it, and I loved doing it! Between Pride and and a couple of weekends in the Pines I racked up some pretty impressive numbers!
 
Re: Describing the pain of first-time anal

We were in the band room and I asked my friend to fuck me, we had done a mutual j/o before, I hate to disappoint you, but it was one of the most satisfying feelings I ever had, maybe some of us are just meant to take it?
 
Re: Describing the pain of first-time anal

I was rimmed for about six minutes and wanting it in me badly, so I was ready. If you are prepared with lube and a good top you shouldn't be in too much discomfort?
 
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