What/who/where was your first time havin anal sex with another man

[hornyogre]

Talk about ur first anal experience

[joshua280964]

It was a friend who followed me in to the toilets in our local pub.Fancied him for ages.He asked me straight out if I wanted fucking.He had a massive 12 incher to give me.Tight at first but we fucked each others brains out.He then came bucket loads in my mouth and I swallowed every last drop.Fucking wet just thinking about him.

[Gearbox]

Never had anal sex with a woman, so was a total 'anal virgin' when a bloke let me. Was only having sex with one man (my first) for weeks, but he was only into oral. So I hooked up with another, desperate to try.
He was a bi, fit muscled, moustached teacher and very understanding that I was not experienced.
He got on his knees, told me to lube him up and my rubbured up cock, and to gently ease it in. He farted.LOL! Didn't put me off though. Soon I was in all the way and getting a nice easy rhythm going. Felt awesome. Could feel him squeezing my cock all around it, as he moaned and give directions. 5mins of that and he cum on my carpet.:eek2:
Thought I was fekin brilliant at it first go. But he apologised and said he'd been precumming all day.LOL TMI there!

To my shock, he didn't get up n fek off like my fuckbud always did. He stayed to finish me off.:tongue:
That was the end of my fuckbud, and the start of fucking men.

[Bisexual Explorer]

Just a few months ago. I finally got up the nerve, don't ask me why I needed any nerve, to ask a buddy with whom I had several great oral encounters, if I could fuck him. He said yes with a big smile. He lubed my cock, went down on all fours, and in I went I had one of the best orgasms ever. To say thank you, I got down on my knees and sucked him off.
Bisexual

[æonpax]

What - Anal sex, with a guy.
Who - I forgot.
Where - Party in HS.
Comment - It hurt like hell.

[alcor]

We had just bought a motor-home and was taking it out for the first time to a campground on lake Erie. We asked another couple to meet us there never having sex with them before but knew that he at least was bi with her bi receptive. Me and him did each other with both giving and receiving anal a first for me. It was GREAT liked receiving much better though. we went at it for an hour or so then let the ladies join in to finish us off. Would very much love to find another guy a little bigger cock for me to fuck.

[i_shoot_blanks]

Several years ago in Denver met a guy via underground newspaper (before internet). After a few conversations, we finally met. One precondition, we both took enemas before hand!!! We sucked each other to get things going, then I got on all fours on the edge of the bed and he stood behind me. Started with a finger, then after a while, two fingers, then finally a condom clad cock slowly slid in. He was relatively small and I had no trouble accepting his cock. He fucked me and just as he was about to cum, I squeezed my sphincter and he exploded. After clean up and a little time, he sucked me some more, then got on all fours and I stood behind him, slowly slipped into his well lubed ass. I enjoyed it and did cum, but found penetrating a pussy felt better than an ass.

[cornholejoe]

with a guy and his wife in a 3somesome while i was fucking her he put his dick to my mouth and said suck it so after a few minutes he got hard and then put it in my ass later on his wife wanted to see a 69 with me and him and then after a few minutes he got on all fours and i fucked him doggy style while she watched been bi since then

[LeeNorCal]

A girlfriend in college (we're talking 1971) introduced me to anal play after dating for several weeks. I was mainly on the "receiving end" of several of her dildos, and didn't enjoy it all that much, but she enjoyed pegging me, so I went along with it. After several months of dating, we met her next door neighbor, and invited him over for drinks. Long story short, we ended up naked with her pegging us both, then she asked which one of us wanted to be on the receiving end of the real thing. Being the Boy Scout I am, I volunteered. Wow! I hated telling her the real thing was much better than her toys.............but she completely understood. Since then, I've had numerous MMF anal encounters (always safe since the early days of AIDS) but can't get into it with just me and another guy. Wonder what Freud would have to say about that????

[redngoldpride]

my first time having anal sex with a guy was when i was 14 my gf at the time had a brother who was a couple of years older than us and he was a very passable cross dresser , the very first time i saw/met him in fem i did not even realize who it was but his very short skirt and thigh highs and beauty had me hard right away which made my gf laugh when she told me who it was i reached out and felt under her skirt to feel her panty covered ass .... we all three ended up on the bed and when i entered his ass for the first time it was so tight and hot i only lasted about 15- 20 min. it was the first time my gf let me in her ass also .... but to this day i still have never been on the receiving end of a hard throbbing cock in my ass

[jackbirdjay]

My first time I was 18 a wild gf was sucking me she put a finger in my ass. Seeing I was enjoying it she stopped said be right back got a tube of lube and her 7 in vibrator. At first I said no way she said trust me you will love it. She was right shot one of the biggest loads down her mouth. After that anal play was always in our sex lifes. My first time with a guy I was 23 it hurt like hell he was much older and didn't care he held me and jammed it in me from behind I didn't do it again till I was 28 that time it was much better. Now I get a lot of pleasure from anal.

[BiJoe696]

My first time getting anal was when I was about 23 or so and he was mid 30's. We had been meeting on a semi regular basis at a park and he really enjoyed just sucking me lots. And a great cocksucker he was. This went on once or twice a month for about a year. One day he asked me back to his place a very nice country estate in a rural area. It was about a 20 mile drive, but well worth it for sure. It was great because could get naked, relax and enjoy all the pleasure in his bedroom without worrying about getting caught as do in a park. Was enjoying his working over my cock and balls with his mouth when he lifted my legs high and started rimming me for a long time and then reaming me deep. He had often played with my ass with fingers as he sucked me so I was very cleaned up and ready for this great sensation he was giving me.
I had never seen his cock since all he seemed to want to do was suck me. He had on briefs and after a long time working on my ass with his hot tongue he slipped a couple fingers in and went to work on my cock and balls some more. I could tell he was working off his briefs and was excited that he was doing so and would get to see what his cock looked like. My head was propped up on a pillow, my legs high over his shoulders as he pulled away his mouth and knelt there stroking his cock with one hand as he stroked me. WOW, what a nice cock, bigger than mine in length and very thick. He asked if I wanted it and I moaned oh yes, pulling him close to my ass and asking him to go easy. This was wild, I had done myself with toys and enjoyed a couple fingers up there as I got oral, but I really wanted to do this and it was the purrr-fect time and setting. He took his time, knew what I wanted and gave it to me, a great long session, started off slow, build up, faster, deeper, harder the works. Stroking me as he did me, it was great.
Later when talking he said next time if I wanted we could do a 3 way and I could get oral from his friend as he fucked me again. We did it.

[bi4asplay]

Talk about ur first anal experience

My late wife got me started. While giving me head, which is how she woke me every morning, she slipped a finger in my ass and I exploded in her mouth. Back then you could not go out and but a dildo. So she made her own with a plaster cast of me. She wanted to use it on me all of the time. It got her so hot and I liked it to. After about a year of this with her coming birthday I asked what she wanted. She replied that all she wanted was for me to promise to do everything she asked the whole weekend. I knew that there were 3 couples that were coming to spend the weekend that included a sail to Catalina Island. On Friday afternoon after we got out of the shower she said she wanted to tie me up( First time) and blind fold me. I trusted her and had promised her, so OK. She started sucking me, then she put the home made toy against me lips ( first time for this to). She had to remind me of my promise. After a few she changed positions and got in 69. She then slowly worked the toy into me. The phone rang and she got off of the bed and left me there with the toy still in me. I felt her get back on the bed by my head and sit on my face. It was not her, but another lady( also a first) some one took my cock in their mouth another lady. She changed with someone else and when I felt this mouth I knew that it was not a lady( a first again). The toy was pulled out of me and some one got between my legs. I had a pillow under me where she could use the toy. If I could have I would have jumped off of the bed at what I felt next ( damn sure a first) as I felt what I knew was a cock head press against my ass. I tried to get away from it. Again the reminder of my promise. I stopped fighting but could not relax so it took him a long time to get the head in me. My LW got back on my face I loved licking her so much that I at last relaxed. When I did he slipped all of the way in. When he hit my P spot a came in the mouth and one of the ladies. Before the weekend was over I had sucked the other 3 guys many times and every one fucked me. The ladies and the guys.. On our sail to Catalina all three guys fucked me on the fore deck while under sail. ( another first), just not the last. We played with the same 3 couple regularly for about 10 years after that. I still love a good hard man in me and being pegged is great as well.

[Lanny75]

Was my friend in high school,,,very awkward the first time,,,very enjoyable after that. He didnt much like being a bottom,,i gladly accepted the role.

[olmizzou42]

My teenage suck buddy tried a couple of times to fuck me, but we were young and inexperienced with no lube available so it didn't happen. But, at age 59 I hooked up with a guy who used his tongue, fingers and lots of lube to enter me and I was hooked. As someone else mentioned, I am very anally responsive. A finger in my ass while being blown will cause me to cum very quickly and intensely.

[Tim56Mn]

1970 El Paso Tx. YMCA went in to take a leak met a man ( did not know and still dont ) ended up in his room naked he rimmed me and stuck his c_ _ k in me kind of hurt but felt good he cum got dressed left have like it ever sence

[12voltman59]

I was in my mid-20s or so. I had this "out of left field" relationship pop up with another guy. I call it this because at the time--I was in the service, back before the days of "Don't Ask, Don't Tell" he was in the service too, so if caught--we would have been in it deep; I was not at all thinking about or looking for doing anything with another guy at that point because of being in the service and because I was dating a few different girls at the time----doing stuff with guys was not "even on my radar" but it happened anyway.

We had been working together for a time on a project assigned by "higher ups." He was a cool guy, fun to be with---had a great sense of humor and was a good looking guy to boot.

Without going into the whole story---it was late in the night or early in the morning, depending upon how you judge the time. We were alone along a deserted stretch of beach on an island down in the Caribbean. We were skinny dipping---suffice to say--that "one thing lead to another" as they say during the course of us "rough housing" in the water.

He was a bit bigger and stronger than I, he had tackled me and had me in a bear hug, with him behind me. We were pretty buzzed from booze, so inhibitions were down. I could feel his cock rubbing my back----at first it may not have been hard---but he started to rub my chest with his hands--it felt good----then with one hand--he grabbed my cock and just from being touched--it got hard in his hand. With that--I felt his cock go hard.

The memory is pretty hazy thanks to both drink and the passage of the years---but before long---we were in each others arms---this time face to face, kissing--he pulled me to him--and well--I felt his cock nestling in my ass crack and before long--he was pulling me down on it, entering me---and even though there was some initial pain--it actually felt good and before too much more time---he was fucking me to an inch of my life---and that was only the first of many times he would come to fuck me over a period of about ten to 12 days.

I had done some mutual jerking and oral with another guy at age 15 and a few mutual jerking/and or oral situations with a few guys in college that were "one off" spontaneous sorts of deals--but never any anal.

Once the time he and I spent together was over--I never saw or heard from him again--and did not do anal again until not all that long ago. I actually had really put this memory down deeply away, chalking it up as "one of those things" and that "I am not gay" because i had a series of long term things with some ladies in the years since.

I do have to say now though---I really wished I had allowed myself to do things with guys in those intervening years---I did get offers from several guys to do things, but actually got scared off from doing so for one reason or another.

I did enjoy being with this guy--and I now realize--it was such a good experience in more ways than just the sex----it is something that is probably going to be hard if not impossible to replicate for me at this stage of life.