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First time you had anal sex

Although I began having physical contact with other boys from the time I was young, all my buddies were straight and anal sex never even occurred to us. My last year in college I attended a party at a fairly liberal university that a friend of mine attended. At the party I met a guy that I thought might be gay and I went home with him at the end of the night. I was nervous as hell since I had never been with a guy that was gay. I was both drunk and horny and he asked me to fuck him. By then I had seen images of guys fucking in porn but was blown away that this guy was willing to bend over and willing to let me penetrate him. It felt amazing. I met up with him a couple of times over the next year and learned that he had been fucked often. He eventually wanted to date but I was so naive at this point that dating a male was the furthest thing from my mind. Incredibly the guy could get his nut without touching himself as I pounded his hole.
 
I am a late bloomer. Had my first male to male experience at 56.Grew up in a very religious family wherr homosexuality was a taboo.
A friend invited me camoping and Fishing. The first night we slept in Tent he rolled over closer to me and just threw his arm over me. Then his hand strayed to my cock... i woke and thought he was asleep and moved his hand...After a while he put it back then carried on rubbing me.... at first i felt disgusted that i was getting aroused....i moved hus hand away again but this time he took a firm hold of me and started stroking me. Alarm bells were ringing in my head but my body was hearing none of it... My hips developed a brain of their own and my body sold me out... i couldnt stop him...He then took off my sleeping shorts and to my horror i was actually lifting myself to assist him...He then gave me a blowjob. I cant explain what was going through my mind at the time... disgusted,excited, nervous and more... He then out a finger up me and that it. I blew my load and had the most intense orgasm of my life.He then turned me over and by this time time all resstance was gone... when he spread my butt cheeks and oked his tongue i almost got up to run..but he held there and rimmed me... i am not sure when and how but i realised i was arching my back and his tongue torally controlkung me.
Then He got on top of me and i felt something cold ( he lubed me) . I then felt his weight on me and he gad his cock just touching my ring... My butt was arched in the air..when he asked me if he must stop..i mumbled no but he asked me again... i said no.. he then ushed in me very slowly... he got in and just held it there... my body was qivering..He told me to relax... There was pain and pleasure...then he slowly started pushing in more and more until after what seemed an eternity i felt his balls against my butt checks. He then pulled out and pushed back ...just small movements... my body had already developed a mind of it own and i was responding... then he started stroking long slow strokes until he built momentum...After about ten minutes he filled me with his cum.... that was my first time.. and never stopped.
 
It was in December 2014 when I lost my anal virginity. A jock with a sock fetish that I met on Adam4Adam came over and we went into my bedroom. We sat on the side of the bed and began rubbing each other's crotches. Next thing I knew, he took his jeans and underwear off and his hard, warm cock was in my hand. I felt it pulsate as I stroked it. He seductively said, "You can suck on it if you want", and with that command, I bent down, mouth open, and began sucking his dick. It felt rubbery yet juicy, and he moaned so good. His balls were sensitive, so I kept sucking the head. He was about to cum, but I edged him, not wanting him to blow his load until he fucked me. I took my shorts and underwear off and got on all fours on the bed. He lubed up my hole, put a condom on, and slid his cock inside me. I was like, "Fuck yeah", really digging the feeling of his hard cock inside me. He slowly began to fuck my eager and hungry hole, and I begged him to fuck me harder, so he picked up speed and pounded my ass. My head was in a pillow, moaning the whole time, not wanting him to stop. He finally came and my ass was busted and sore. I didn't get to rim him, but he did let me check out his firm ass and slightly hairy brown hole (I should have licked that sweet asshole). It was a hot morning.
 
First Time Anal Sex with another Man?.............NEVER. I was always the top guy : )
with women folk in my past. I want to read the whole thread, and get some tips. But I'm
now a control freak bitch, and a submissive gay. Oh Dear, if I meet a neat guy, he'll be put off
with me telling him how I like to be tied up, how I want to be spanked, and of of course how I
want to be ass fucked. Servile Crouch, Ass in the air, face on the pillow
 
I was 24, yes that old, and he was a 33 year old bear with bright blue eyes. We had hooked up a couple of times before and finally on the third time he asked if I wanted him to fuck me. I nodded yes. He used some kind of oil, no condom and just entered me. His dick is big and thick enough to think that it will hurt but I felt no pain. I was so ready for this.
It felt good but wasn't great. He didn't know I was a virgin, I told him after that.
 
He was was my neighbor and best friend. About a year and half or so older than me. We hung out all the time - pretty much inseparable. The first time happened while we were playing and he asked if he could fuck me. Of course I said yes. We'd seen each other naked countless times so I'd say he was about 8 inches or so. I knew he liked my ass 'cause he was always finding ways and reasons to touch it. The first time was doggy and we were both super excited and nervous. He slicked his dick with Vaseline and slowly begin to slide it inside me. It hurt but felt so good at the same time. He was always rock hard and so was I. Once he got it all inside me, he rested a bit so we both could catch our breath. And then he began to thrust back and forth, both of us moaning in delight. It wasn't long before he was cumming. We didn't know to use condoms and didn't really have access to them anyway, so bare is how we always did it, and he'd just cum inside me.
 
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.
 
We had met the previous week at a magazine shop and made a date for a get together. He was about 6 or 8 years younger than me and I was a 'gay' virgin and nervous as fuck. After doing a couple of hot knives to take the edge off and a quick BJ from him, we went to the bedroom. He was also much smaller than me so when we tried missionary, he couldn't get the correct angle so we switched to doggie. He was only about 5" and slender so penetration was fairly easy with the Vaseline from the night stand. His underwear had the Superman logo on the front that I thought was comical until he screwed me bareback for nearly 30 minutes. He may have been young but he had great stamina. He finished inside me and I then jacked off into the covers shortly after. I recall the next morning having a little cramp, farting and a big gob of cum hit the carpet, at the time I thought it was funny, but now sounds disgusting. That was the first and only experience, been waiting a long time for a 're-do'.
 
My first time as a wide receiver was AMAZING! Which is a good thing, because if it had been bad, I'd never have done it a second time. Thankfully, my ass had plenty of practice with getting invaded (I had been playing with my hole long before I let someone inside me) by all the usual things guys use who haven't bought sex toys yet. Once I found my prostate (I had no idea, just that something felt incredibly good) and how having it rubbed caused a far better cumshot than usual, there was no turning back. Crisco or Vaseline were what I used, and anal play became a daily thing. Actually I wasn't really that concerned about getting a guy to fuck me because I was so in love with fucking myself, I know it sounds narcissistic, but it was (and still is) so awesome!
My first time taking it up my manhole was with my boyfriend at the time. I'm stereotypically Scandinavian looking, he was about the same height and weight, but had dark brown hair and pale blue eyes. I'd fucked his bubble but with the tan line 3 times before. He had been anal virgin until I popped his prune. It was work getting past his sphincter
 
Continued: so I was scared it was going to hurt me too. He lubed my hole and finger fucked me while we kissed and I was loving it! I rolled onto my stomach and he climbed on top of me. His hard cock was rubbing my ass, I spread my legs, and he grabbed his dick and I felt it poking my hole. I gritted my teeth when his big cockhead slid past my sphincter, entry was always the worst part. He layed down on my back, held my arms in place by my head, and started slowly bumping me. He knew from me fucking him what felt good, so it wasn't long before he was power slamming my slick cunt. My dick was hard as stone and rubbing against my stomach and the bed. Every time he thrust forward and down, it caused my dick to rub the bed. We were in my twin size bed, and the narrowness of it made it feel like we were cocooned together. It was brutally cold outside and storming, and listening to the wind howling and the windows getting pelted with sleet was such a turn-on. He was whispering in my ear things like "you love taking my big dick, don't you?" and "you love being my little faggot, fucking take it bitch!" I still remember tears of joy in my eyes. If I had died at that moment I wouldn't have had any regrets. We didn't even care my parents and my sister were asleep down the hall. My bedroom door was locked, so I didn't have to worry anyone would barge in. My bed was squeaking and shaking so anyone listening at my door would've known what was going on. My orgasm hit first, I couldn't take more than 5 minutes of this level of stimulation, and I came by humping the bed. While I was shooting off he put his hand over my mouth and increased his speed. The orgasm was so intense that my vision blurred. He came not long after I did, it was like he was possessed. He was wearing a condom, but I could still feel his cum. We didn't want to sleep in the wet spot, so we went to sleep on the floor with lots of blankets. We also knew how risky it was to tempt fate again by having another loud fuck on my loud bed. He wrapped himself around me, his dick against my ass, and we went to sleep. I got woken up a few hours later before sunrise, he was fully hard and humping my butt crack. He said he wanted to fuck me doggy style, so I got on all fours. I put my head on the pillow, stuck my ass in the air, and he grabbed my hips. This time I was still slick with lube, and he just shoved it all in with one slow thrust. I was in heaven! He started plowing me hard and fast, the slick sound of his dick pistoning in and out of my slick hole filled the room. His hips and balls loudly smacking my ass. He came first, and it was epic. Right when he pulled out we heard someone going down the hall to the bathroom. We froze until they went back to bed. I figured they didn't bang on the door, so they must not have heard anything. I still hadn't cum yet, so he sucked me off. The next morning nobody said anything to us, so I figured we were home free. We stayed over each other's houses often, and he fucked me numerous times. He was the main bottom, but I was happy any which way.
When I came out to my father a year later, he told me he already knew I was gay because he had heard us fucking. He told me that he had "fooled around" with guys too when he was young so he couldn't pass judgement on me.
 
When I was 20, I really badly wanted to have my first encounter with a man, and eventually I just gave in and posted an ad on Craigslist (rip). In my ad I had stated I wanted to suck a guy off for the first time and that was it. I ended up getting two replies and my whore self lined agreed to meet both of them. One on one day, the other the next day. Both men were much older than me, but I was okay with that. I met the first guy at a gas station and then followed him back to his house. He was a sexy older daddy bear type. Once we were at his house, he told me he had a wife, and for some reason knowing that this man was cheating on his wife with me was a HUGE turn on. So he whips out his cock and I drop to my knees.

Now, this guy has a pretty thick cock! It was average in length, but definitely above average in girth. I started sucking on it and I was instantly hooked on the taste on cock and precum. And apparently I'm naturally talented in it because he was surprised at how well I was doing for my first time. He brought me to the bedroom and laid down and I climbed on top to keep sucking. He stroked the back of my head and kept complimenting me (looking back he was definitely grooming me for anal). He then asked if I had ever bottomed before (knowing damn well this was my first time with a guy) and my slutty mind just took over and without any coaxing at all I responded with "No, but I'd like to try." He smirked and told me to lay on my back.

He pulled me to the edge of the bed, lifted my legs in the air, then lubed up my hole and his cock. He slid his cock in very slowly and I immediately realized he was bare, but I didn't care. I wanted it. He slid in slowly even more, and it was such a strange sensation. There was pain, but it also felt like I was rightfully being filled. He asked if I was doing okay and after saying yes, he slowly bucked in and out and before too long, he was fucking me. He held on to my ankles for balance and he started getting verbal. He would say things like "Your ass is so tight" and "Your hole is perfect." He told me to play with myself during it and to tell him when I was ready to cum. So when I felt it coming I told him and he pulled out and came on my balls and stomach as I too blew my load on myself. He got me a towel to clean up, we had a bit of small talk afterwards, and I left as a newly born gay slut. So I absolutely loved my first time!

Unfortunately, I moved away soon after and I never hooked up with this man again. As for the second guy I met the next day, he was even older (early 60s for sure). We didn't do anything anal (he said he only did anal with people he trusted), but I did suck him off and swallow his cum.
 
shhhmypornaccount said:
When I was 20, I really badly wanted to have my first encounter with a man, and eventually I just gave in and posted an ad on Craigslist (rip). In my ad I had stated I wanted to suck a guy off for the first time and that was it. I ended up getting two replies and my whore self lined agreed to meet both of them. One on one day, the other the next day. Both men were much older than me, but I was okay with that. I met the first guy at a gas station and then followed him back to his house. He was a sexy older daddy bear type. Once we were at his house, he told me he had a wife, and for some reason knowing that this man was cheating on his wife with me was a HUGE turn on. So he whips out his cock and I drop to my knees.

Now, this guy has a pretty thick cock! It was average in length, but definitely above average in girth. I started sucking on it and I was instantly hooked on the taste on cock and precum. And apparently I'm naturally talented in it because he was surprised at how well I was doing for my first time. He brought me to the bedroom and laid down and I climbed on top to keep sucking. He stroked the back of my head and kept complimenting me (looking back he was definitely grooming me for anal). He then asked if I had ever bottomed before (knowing damn well this was my first time with a guy) and my slutty mind just took over and without any coaxing at all I responded with "No, but I'd like to try." He smirked and told me to lay on my back.

He pulled me to the edge of the bed, lifted my legs in the air, then lubed up my hole and his cock. He slid his cock in very slowly and I immediately realized he was bare, but I didn't care. I wanted it. He slid in slowly even more, and it was such a strange sensation. There was pain, but it also felt like I was rightfully being filled. He asked if I was doing okay and after saying yes, he slowly bucked in and out and before too long, he was fucking me. He held on to my ankles for balance and he started getting verbal. He would say things like "Your ass is so tight" and "Your hole is perfect." He told me to play with myself during it and to tell him when I was ready to cum. So when I felt it coming I told him and he pulled out and came on my balls and stomach as I too blew my load on myself. He got me a towel to clean up, we had a bit of small talk afterwards, and I left as a newly born gay slut. So I absolutely loved my first time!

Unfortunately, I moved away soon after and I never hooked up with this man again. As for the second guy I met the next day, he was even older (early 60s for sure). We didn't do anything anal (he said he only did anal with people he trusted), but I did suck him off and swallow his cum.
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Always like hearing (two) first time stories that are positive. thanks for sharing.
 
I'd been with 4 or 5 straight guys in middle school into HS but it never occurred to me that any guy would let me fuck him. That was the 70's and we barely acknowledged that gay guys even existed although we all knew a few guys in HS that only hung out with girls. Still, I was very ignorant since the internet didn't exist and we were just a bunch of horny farm boys. However my last year in college I was visiting friends that attended a much larger university than my own. We ended up at a party and the friend that brought me told me that his university was very liberal and that there were several gay and lesbian students at the party. I was blown away because I was a member of a very homophobic fraternity and I can't remember a single person being out at my university. I eventually began talking to a guy that was fairly attractive and seemed very easy to talk to. We were approximately the same age and I was really enjoying the attention that he was giving me. He eventually asked me if I was straight and I told him that I wasn't as straight as I looked. At that point I sort of knew I would be going home with him. The guy was clearly out and was very straight forward about wanting me, which was unlike anything that I had experienced before then. I was so conditioned to play a cat and mouse game with my straight friends during sleepovers (middle school) or after a night of drinking (high school). After going home with the guy we got undressed and were making out in his bed. He eventually asked me to fuck him. This was maybe a full year prior to the beginning of the AIDS scare so using a condom never even occurred to us. As it was he put me inside of him and I fucked him missionary style. I can remember telling him that I couldn't believe I was inside of him. Thinking I had to be hurting him I was being as gentle as possible. Sensing my ignorance he finally told me that I could fuck him as hard as I wanted. The guy was a great teacher. I picked up my pace and was eventually pounding his hole. We had the lights on in the bedroom and I was amazed by the look of rapture on his face. Given that I had more to drink than he did he had an orgasm before me but I wasn't far behind. Fucking a guy my first time felt amazing and I went back several times until he confessed that he was falling in love. I was only 20 and I didn't have a clue that guys could develop feelings for one another other than lust. I stopped visiting him after that but I definitely appreciated his candor.
 
heir-to-the-wind said:
“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.
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If you were a girl, you coulda pretty much gotten him for rape on this...
 
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