Your first anal experience?

[blubyuf6]

my first real penetration was with my mothers vibe when i was around 11-12, been useing things ever since

 

[suffolkengland]

Well, thanks to Penthouse Forum (a magazine with "true" stories in case you didn't have that over there) we knew that it was possible....it just took us a while to get it done, we never had any convictions or labels at that point, it was just another way to get off!

(Got to be a bit careful here of describing these 'formative years')

We had Penthouse in Britain, but almost all mags were softcore (back in the mid '70s), and I don't remember even reading about anal! Either MM or MF.

I do remember reading about 'fagging' in Tom Brown's Schooldays. I don't think buggery was directly mentioned, but I put 2 and 2 together. Found out for myself that assplay was fun, but it stayed a solo thing for years.

 

[schaum_m]

I came the first time I got fucked. He was an older guy and very hot. He was very gentle.

 

[schaum_m]

Good luck Tommix If in doubt, use more lube

I'd played with a lot of things before I ever got near a cock, so I knew how to relax and it was fine - no pain at all. He wasn't super-hung, and that probably helped.

One thing - he was amazed when I came while he was fucking me and he felt my ass squeezing around his cock. He was quite a lot older than me, but had never felt a guy come while inside.

I came the first time I got fucked. He was an older guy and very hot. He was very gentle.

 

[none2_none2]

(Got to be a bit careful here of describing these 'formative years')

We had Penthouse in Britain, but almost all mags were softcore (back in the mid '70s), and I don't remember even reading about anal! Either MM or MF.

I do remember reading about 'fagging' in Tom Brown's Schooldays. I don't think buggery was directly mentioned, but I put 2 and 2 together. Found out for myself that assplay was fun, but it stayed a solo thing for years.

By the time I was in high school 1974-78, I knew I had an attraction for guys and physically for their asses. I tried to learn about what that meant physically. There was so little gay literature. I did read up on str8 sex. From the description of female orgasm, I had the opinion that a woman's vagina was like a milking machine. I had no concept of the trusting in and out of a hole.

Anyway between religious hang ups about gayness and my own ignorance, I didn't start gay sex until I was 21.5 years old. I didn't get to top in fucking until I was about 23 -- I was under the impression that only hung guys could top. It was all very frustrating before my first fuck, because I still wanted to be close to a guy, but the sex was so poor. I started wondering if I was some kind of a freak -- wired to be str8, but hung up on the need to be close to a man.

However, when I finally got to top, then fireworks went off. I love being inside a guy that I am attracted to. It isn't all about the rush to orgasm, but for me more about the "connection" time.

The one fantasy I always had was that I wish for one time, I was so hung that I could fall asleep inside a guy and not shrivel up and slip out. A guy I had a one night stand with once, said some hung, drunk guy once fucked him and then passed out and stayed inside his ass. That always sound so hot physically and emotionally. However, others have said it can be rather uncomfortable.

 

[schaum_m]

By the time I was in high school 1974-78, I knew I had an attraction for guys and physically for their asses. I tried to learn about what that meant physically. There was so little gay literature. I did read up on str8 sex. From the description of female orgasm, I had the opinion that a woman's vagina was like a milking machine. I had no concept of the trusting in and out of a hole.

Anyway between religious hang ups about gayness and my own ignorance, I didn't start gay sex until I was 21.5 years old. I didn't get to top in fucking until I was about 23 -- I was under the impression that only hung guys could top. It was all very frustrating before my first fuck, because I still wanted to be close to a guy, but the sex was so poor. I started wondering if I was some kind of a freak -- wired to be str8, but hung up on the need to be close to a man.

However, when I finally got to top, then fireworks went off. I love being inside a guy that I am attracted to. It isn't all about the rush to orgasm, but for me more about the "connection" time.

The one fantasy I always had was that I wish for one time, I was so hung that I could fall asleep inside a guy and not shrivel up and slip out. A guy I had a one night stand with once, said some hung, drunk guy once fucked him and then passed out and stayed inside his ass. That always sound so hot physically and emotionally. However, others have said it can be rather uncomfortable.

I first started gay sex when I was 23 years old. I thought alot about it when I was younger but none of my friends wanted to do it with me. I always wanted to be the receiver even when I was a boy but it didnt happen until I was 23 that I found a man who would fuck me.

I would like to try your fantasy of falling asleep with you inside me.

 

[fingermagic]

My first was with a guy much older than I (I was 16 and he was 35). He knew what he was doing and I was so in lust that it is still so memorable. We had spent the day smoking and watching porn. We had already cum several times jacking and sucking. We had been sleeping and we woke up and did 69 for about 30 minutes. He rimmed me and I was so turned on when he slipped a couple of fingers in me I was his. I remember we were on the floor and I was on my knees in front of him as he stode before me. He took his cock out of my mouth and laidme on my back and kissed me. Then he lifted my legs up and lubed both of us up, took his cock and started to work it in. He was so gentle that when he felt me tense, he stopped and rolled me on my side and pulled my knees up and tried again. He got it in over a course of minutes and it felt pretty good, very full and felt like I needed to take a huge shit. Once he got going I was able to take it on my knees and elbows. I was hooked from that point on. I have been fucked by both men and women in all sorts of situations. I got to say that women seem to fuck better, but I like a bareback cock cumming in my ass. Can't really do that anymore unless you really trust they are d/d free. But, my first will always be the most exciting memory.

 

[krsmaddriver1420]

.....

 

[biguy79]

I remember my first time. I had been fooling around with this guy for months. I was only curious at first but he hd a lot more experience if you know what i mean. It started out with me just giving head and swallowing. One night he said that he was going to fuck me. I simply lifted my head from his lap and said "yes".
We moved to his bedroom, I stripped off all my clothes, as well as my partners and laid out on his bed. he got on top of me and we made out while stroking each other. After he was done kissing me, he told me to get on all fours and spred my legs a bit. He grabbed the lube and applied it to the appropriate areas.
He teased my whole a bit first. just poking around with the tip of his cock. Then, suddenly, it was in. I wont lie, it was really uncomfortable at first, even with the dildo practice id been doing. But i relaxed loosened up and it felt amazing. He didnt last long, maybe only a few minutes, but it was an unforgetable few minutes.

 

[orgasmsgalore]

My first experience was only to please the man. I had no desire to do it EVER. But you know us women, we want to please the man so I did it. All I can be thankful for was he was very small. He did not work up the area first. He just put it in. He used no lube or anything. I did it with him like 3 times. I am not happy with myself for giving in to please him. I had a baby and when I did the doctor cut me down there the max amount he could and I had a 3rd degree tear on top of that. Nerves once severed don't always heal exactly right, so that area on me is kinda funky. NO man will ever go near my bottom again!

 

[mrbimystery]

all these posts makes me want cock in my ass so badly

 

[bi golly]

I just got a couple of butt plugs to try out. They are the tantus Severin small and Tulip small. I lubed my butt and tried to get them in, but they seemed to hang up and not go all the way in. I pushed and pushed and couldn't get them all the way in. I gave up and got out my dildo and slid it home. I was so turned on, I couldn't believe it.

I basically stopped stroking my cock and just stroked the dildo in and out. I came with a mind blowing orgasm. I can see why some guys like getting fucked.

I would like to try it, but I haven't found a guy to pound my ass yet.

 

[BigDanRTW]

I met him in a yahoo chat room. He lived in the dorm right next to mine. He came over when my roommate was out of town. We got on my bed and he fucked me doggy style. It definitely hurt at first, but felt awesome once I got used to it. I clinched my ass muscles around his cock as he pounded me. We were a sweaty mess after but it was so fucking awesome.

 

[iwp2011]

met a gay masseuse who catered to bi curious men and, after visiting him a few times for a massage and a happy ending, one day i asked him to fuck me. i got some lube on my finger and fingered my ass in a circular motion to get myself relaxed. he laid me on the massage table and put my legs up over my head and then proceeded to slowly and gently push his condom covered cock into me. i couldn't believe that i was finally getting fucked. it was so sexy to watch his cock and hips push in and out of me. one of the most sensual things that i've ever done. i'm getting hard just thinking about it!

 

[bitxhubby]

Wow that sounds really nice! I'm envious

 

[iwp2011]

give it a try. i think that life is short and one has to try most everything once. it's been a few years since he fucked me but i've made a date to go back to him and do it again. this time i want to try as many various positions as i can. i've only done it while i was on my back but i want to be bent over his massage table, on the floor on all fours, in his bathroom while watching us in the mirror, and then in his bed from behind, ending up with him on top fucking me as i masturbate. fun!

 

[blade_rocknut]

Started exploring my rear probably about the same time as puberty, and still love it today. I will occasionally get some help from my wife, but mostly alone. Butt plugs ( meh....) vibes, double dongs and my own fingers.... I'd love to be fisted, but we haven't made that a reality, and doubt we will.

 

[KaseDupont]

in the back of a car, at 16. it hurt, i was not ready

 

[Hitchiker69]

my first anal was great

My first anal was with an older guy I'd met while hitchiking. It was a one night stand. By the time I met him I'd had gay sex with several guys I'd met through hitchiking; usually receiving head and/or being a top. Over time curiosity got the better of me and I tried sucking, just to see what they liked about it, and I enjoyed it. So I was ready for more.
This guy picked me up late at night and asked where I was planning to spend the night. I said I had no plans, so he offered I could sleep on his couch. To make a long story short, we both knew where this might lead, and it sure did. He gave me a massage...we were both nude in bed together...and I was loving it. I rolled over and took his hard on in my mouth, and sucked his cock hungrily. Then we 69'ed each other, we sucked and groped and played and pleased ourselves and each other any way we could, in every position that fellt right. At some point he ended up on top of me, with his dick probing my ass. I decied to try letting him have my anal cherry, so I spread my legs and he probed slowly into my ass. It didn't hurt, it was a new, unusual feeling of being filled, along with being desired...he was so hot and turned on by my ass...he went wild on me, fucking deep and wildly. My ass seemed to bring out the animal in him, and I loved being taken by such a horny beast. I wrapped my legs around him, hugged him close and kissed him on the cheek. He turned and kissed me on the lips, probing with his tongue. We french kissed while we humped together like two horny sexy men, which we were.
He exhausted himself before he came, which was a dissapointment, but I loved what we did. We fell asleep after hours of sex and fucking. In the morning he wanted more but I was too hung over. I had some orange juice and a shower. I left ...he drove me to the nearest onramp..and never saw him again.
That night made me want more men, and I decided I was going to persue men and explore my Bi identity a lot more in the future.

 

[coastguy1]

My first time anal was while I was with an ex-girlfriend that introduced me to the joys of cocksucking. She had bribed me into sucking cock during a threesome and I became instantly addicted. Bi threesomes became a very regular occurance, mostly with me giving oral and only very occasionally recieving it. A few months after my introduction to cock sucking we were at home, watching a bi porn video while playing with eachother. A scene came on where this hot guy is burying his face in a beautiful shaved pussy, it slowly zooms out to reveal that while he is licking, he is getting rammed in the ass by another hot guy. It looked so hot, I turned to my girlfriend and told her that I wanted to try getting fucked.
She was very excited, she had wanted to try anal play with me for some time and I had always turned her down. She went to our bedroom and got her vibrator and the lube. My cock was rock hard in anticipation, although I really wanted the real thing, not this rubber substitute. I slumped in the couch, my ass just hanging over the edge and brought my knees up to my chest, exposing my ass for her. She lubed me and the vibe up and started pushing it in. I never found it painful, just a little uncomfortable. She slowly worked it in and then stated using it to fuck me, shoving it in and out of my tight ass. Everytime that vibe hit my P spot I was in ecstasy. Soon I was begging her to fuck me harder and harder with it, then she wrapped her lips around my cock and it was all over, I exploded in her mouth in the most intense orgasm.
A couple of weeks later we arranged another threesome, it was a guy we had not previously been with. My girlfriend and I took turns sucking on his cock as usual, a really beautiful cock, 7", straight, shaved and rock hard. I had to have it in my ass. I asked him to fuck me but told him it was my first time so go easy on me. I laid down and spread my ass wide for him, he got between my legs and my girlfriend lubed up my ass and his cock. He pushed it in roughly and then held it deep while my ass grew accustomed to his presence there. As soon as he felt me begin to relax he started thrusting in and out of my ass. My girlfriend stated rubbing my cock, I had to tell her to stop because I didn't want to cum that quickly. His cock on my p spot proved to be too much anyway and in a few minutes I was cumming hard, all over my stomach.
He didn't let up, pounding away at me. He told me to play with his nipples to make him cum. I reached up and teased his nipples in my fingers and sure enough he exploded violently in my ass, filling me with his hot load.
Incredible night and we spent the rest of it pleasing my girlfriend.

 

[bunbun8]

Wow!
That last post is hot!
It has given me a raging erection which i will have to take care of....while dreaming of that 3some...

 

[redman1985]

Well it was with my first gay experience. He was my friend and I had just got done blowing him he fliped me over and started licking my asshole. This just made me even more aggressive. He spit a big wade on my hole and lined up for entry. I was so god damn hot and horney that I grabbed his ass and pulled him in. The pain was great but by the third or forth stoke I was way to much out of control to care. He was not big by any means but he had some girth. After 15 minutes I shot my load on our chests and bellys and that was all he needed he unloaded in me. After catching our breaths I kissed him and went out and went back to my apartment and sleeped like a baby.

 

[Seamen]

My first didn't hurt at all ... well not really. He was much older than me, and he lived on our street, so he had known me a long time before we started having sex. He had made me cum twice before he penetrated me, so I was pretty much limp as he fucked me. The first time he came inside me while we were doing it doggy style, and the second me up on the edge of the bed on my back with my knees drawn up.

We kissed before and after too - in fact he was my first kiss ever. We had fooled around many times before, but that was the first time we kissed and cuddled. I was very comfortable with him, and I think the relationship was the more gratifying because of that.

 

[mywayyourway100]

My first time was with a wild ex girlfriend whom a lot of my stories are based on. She was always hinting that she wanted to explore anal play but I was young and oblivious. I was raised to believe that if you ever had your partner even touch your ass, let alone stick something in it, that you had serious issues and were probably gay.

One of the last times we had sex before we broke up, my ex was 69in on top of me and she just all of a sudden jammed her finger in my ass. Neither one of us said anything about it either during the act or after. I certainly wasnt gonna complain, it felt great!

Anyways, we broke up within a few days after that and I've yet to find another woman who is willing to explore that side. Im slowly working on my wife, Im too much of a wuss to just blurt it out but I will eventually get my true desires out in the open. Im pretty sure she'll be into it.....pretty sure.

 

[mrbimystery]

still sad that I haven't had my second experience