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I Am a Male And I Had Anal Sex With a Man

Personal Stories, Advice, and Support 1,860 People

    Used In Leather

    The first time I had anal sex with a man was when I was a student in the 1980's. I never considered myself gay and, apart from sucking *****, I fancied women. However, I have a thing for wearing leather and on this particular occasion I was dressed in leather trousers and my long...
    drewleather drewleather 46-50, M 1 Response Nov 2, 2013

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    I Had Anal Sex With My Cousin

    One random day when my cousin came over (we're both guys. 14 and 12) we were talking about gay people. We were like "I don't understand how any one could take someone's **** up their ***". We continued to talk about it for a couple more minutes until he said he had to go pee. He...
    Thecumbucket Thecumbucket 22-25, M 3 Responses Nov 10, 2013

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    Starbucks Delight 2 Michael had done a number

    on my heard, for sure. He was such a hot and exciting lover. I found myself thinking about him a lot- all the time, actually. But, we are both married and have not been able to see each other a lot since our first weekend together. He called me and said he had a plan. I was...
    charleybi2 charleybi2 61-65, M 1 Response Dec 26, 2013

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    It Happened So Naturally And It Was So Intimate!

    It happened so naturally and it was so intimate! I'm a bi-male married and came into my bisexuality awareness only 6 years ago. I'm a bottom by nature and had, at the time, just started to get interest in anal sex. On prior anal adventures I most always had a hard time getting a...
    bottomspace bottomspace 56-60, M 32 Responses Apr 23, 2012

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    Doctors Appointment

    I went to the proctologist and he told me I had a really loose anus and that there were traces of ***** in it. He asked me what I've been doing. I told him I've been have a lot of butt sex. The situation seemed awkward after that. I was his last patient for the day and he asked...
    Thecumbucket Thecumbucket 22-25, M 1 Response Nov 24, 2013

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    My First Time With A Man

    I want to start this story by saying that i am a happily married guy. I love my wife very much and have been married now for 32 years. The problem is that my wife has no real interest in sex. Now don't get me wrong, its not completely sexless, we have sex around once every two to...
    Sportjeff Sportjeff 51-55, M 10 Responses Oct 27, 2013

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    The First Time It Happened.......

    .....it was with a roommate. He was straight as far as I knew. He would walk out of the shower, in our apartment, with a towel, around his body. I approached him, wanting to give him head. He let me. That turned into me, walking away, and him chasing me, pushing me over, and...
    Michael5280 Michael5280 36-40, M 8 Responses Oct 25, 2013

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    Start Of My Uncut Obsession

    I was driving home late one night and saw a hitchiker. I decided to give him a lift. He looked cold so I figured it ws my good deed for the week. The problem was that he needed a lift ten miles out of my way. I was a bit shocked when he offered a ******* for payment if I drove...
    0ldGriz 0ldGriz 56-60, M 14 Responses Jul 27, 2011

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    More about Christopher

    and me. -This story will follow below in the response section. I hope you enjoy it as much as I did the experience!
    charleybi2 charleybi2 61-65, M 1 Response Feb 6

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    First Time For Everything

    So my first post was about the two oral experiences I had. I guess this one is going to be more in tune with the subject title. The first time I had anal sex with another man, I was 26 years old. We'd been best friends in junior high and though we went to different high...
    JLBetts JLBetts 46-50, M 3 Responses Feb 9, 2013

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    elchefe72 elchefe72 41-45 Jan 20

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    only once giving and

    once receiving . . . both good and something I'm sure to repeat in the future.
    jman73 jman73 36-40, M 2 Responses Apr 4

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    I am almost 45 years old.

    I've dressed like a woman since I was quite young. I've loved being on the receiving end since my first time. I was broken in well as my first was with several guys at once. One of them became my bf and a couole others were regulars. It began a lifetime of near daily...
    Simone1969 Simone1969 41-45, T 6 Responses Mar 16

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    Losing My Gay Virginity - After 20 years of

    fantasizing about it, more and more ravenously as the years went on, I have just lost my gay virginity, just a few days ago on Dec 4, 2013. And it was awesome! I can't believe this has finally, finally happened. ...Oh...My...God...! My progress in exploring by bi-curiosity...
    theslayer3762 theslayer3762 46-50, M 3 Responses Dec 8, 2013

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    My First Time. If you've read my other stories,

    you know I like to suck a guy's **** and swallow his ***. It took me a lot longer to learn the pleasures of anal sex with a guy. So let me tell you how that first happened. About ten years ago, I went to my first sex club (what they used to call bathhouses). I was really nervous...
    kryvj kryvj 51-55, M 6 Responses Dec 18, 2013

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    Busted Cherry, Dripping ***

    On a trip with an aquaintance. One night all that was available was motel room with single bed.  Sounded ok to me, didn't think much about it.  At bed time we awkwardly discovered we both slept nude.  Actually I usually didn't but had ******** all the way as a joke...
    zorch2kx zorch2kx 56-60, M 18 Responses Jun 6, 2010

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    First Time Was With My Friend

    My friend and I were in our early 20's drinking at his house one night and playing darts in the basement. We were trying to distract the other while playing cricket. It started innocent enough with talking to the other while they were throwing and such. It quickly evolved into...
    martinsharp martinsharp 31-35, M 7 Responses Feb 7, 2011

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    Stranger Sex

    I really love getting brutally ****** by strangers. I was out in a bad neighborhood known for rape and I was cross dressing. I was barely out for 5 minutes before a large, black man grabbed me from behind and drug me into an alleyway. He started tearing my clothes off and I didn...
    Thecumbucket Thecumbucket 22-25, M Nov 23, 2013

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    Me And My Step-dad

    When i was around sixteen i started to question if I was straight. so like any 16 year old boy i started looking at **** but the naked females didn't turn me on so i looked at gay men ****** and i busted a nut. i was doing this for about a month when Frank, my step dad, walked in...
    Tom8ombadi1 Tom8ombadi1 22-25, M 24 Responses Feb 23, 2011

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    He Touches My **** In The Gym Sauna !

    I went to the sauna after work out last two months. It was a bit late and not many people at the sauna, that's good to use the sauna at the time because normally the tiny male sauna is full. So I was totally relaxing and nude at the sauna alone. Few minutes later, one young...
    jacky121 jacky121 22-25, M 11 Responses Jun 30, 2013

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    Bareback Sex With A Man In The Shower

    I have an intimate friend and we meet up for fun from time to time. He is a very cute and handsome young closet gay man. He doesn't come out to his family or his friends. He loves having bareback flip flop fun with me, which is fine because we both are healthy and never playing...
    jacky121 jacky121 22-25, M 3 Responses Aug 13, 2013

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    Starbucks Delight It has been a while

    since I shared any new stories. Partly because it has been a while since I have had anything to share! But, the dry spell is over. I have been kind of tied up and busy at home and work. My spouse changed jobs, so she doesn't get to go out of town as much or for as long. But...
    charleybi2 charleybi2 61-65, M 3 Responses Dec 19, 2013

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    They always identified me

    as the man who would go to bed with another man. I am not limp wristed, and do not speak with a lisp. My *** does not wiggle or twitch when I walk. But some men knew that I would allow them access to my rear. The first time was in college and I spent the night with another...
    donn2 donn2 61-65, M 2 Responses 6 hrs ago

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    More Starbucks Delight Michael

    and I spent most of the day in our cabin. Michael ****** me again, well a couple of times. He decided we should eat some fruit to get our energy level back up for when Ben and Roger came calling. Also, he said it helps to keep our *** tasting good. At about dusk, we heard the...
    charleybi2 charleybi2 61-65, M 2 Responses Dec 27, 2013

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    No Longer A Backside Virgin

    I finally decided I wanted to go all the way with a man, so I talked to one of my gay friends and told him I'd like to test my skills. He said he had no interest in intercourse since he is a bottom himself, but said he'd be more than happy to let me give him a ******* to see...
    Polyguy68 Polyguy68 41-45, M 20 Responses Oct 31, 2011

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    In The Woods

    at the time I was 13 I went with my uncle to the woods were I lived we went to this hut were he took out his **** I look on as he rub him self I just pull down my shorts and pants were he suck my rock hard **** I suck his till he came he suck me till I came
    nicholasduffy nicholasduffy 51-55, M 11 Responses Jul 9, 2011

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    Fist

    I love getting fisted in the ***. I love it. But I tried something new. It felt amazing. I got *** ****** as usual, then fisted, and double fisted. But what happened after that was the best. He stuck his foot, his whole foot up my butt. I have really lose butthole by the way.
    Thecumbucket Thecumbucket 22-25, M Nov 22, 2013

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    Change Of Pace

    I meet this man at the park a few times a week on the way to work. I enjoy sucking his **** and he has always finished so I guess he is having a good time as well. This morning I was doing my usual Tuesday BJ, and while taking a breath and ******* him a bit I said if he ever...
    JulesAnn JulesAnn 41-45, T 6 Responses Dec 7, 2010

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    Train Station Toilet

    When I was a student in the 1970s I took the train to university each day.  I liked it not just because it gave me lots of time to prepare for lectures and do the readings, but also because the toilet block at the far end of the station carpark was (and still is!) a great...
    i8mym8 i8mym8 51-55, M 4 Responses Oct 18, 2010

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    More Of Him........

    I have been having anal sex for several years now. My most recent experience was with one of my boyfriends. I am 63 and bisexual; he is 65 and gay. We are both slim men. He has a thick, 7" ****. He is such a great lover. He cuddles, kisses and likes...
    rb71246 rb71246 66-70, M 13 Responses Feb 18, 2010

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    Turned On By ****... More Than The Man

    When with a man i am not 100% into kissing and cuddling.. hell I just want to suck his **** make him squirm and get super turned on that he NEEDS to ***** me.  Something so taboo and nasty about spreading my legs for a man and letting him **** me like a woman...
    russeluk russeluk 51-55, M 17 Responses Mar 6, 2010

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    Just For The Hell Of It

    I read a lot of stories on here and wish my first time had been like those, but it wasn't really. It happened about a week after I turned 16 at a lake near the town I grew up in. My mom had a friend that was openly gay, which then in a town like that was something different that...
    deleted deleted 26-30 2 Responses Dec 3, 2013

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    Final Game Of Chess (check Mate)

    I had been going down to see Bill every few weeks. We had gotten into a normal routine that consisted of us performing oral on each other and him ******* me in the ***. I would always leave very satisfied and full. The last time I went, I noticed another car in the driveway and...
    lt2s2 lt2s2 46-50, M 2 Responses May 17, 2012

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    I thought I would just write this to share my

    experience and to help anyone out there who is wondering about whether to have anal sex or not. For many years, whereas I had occasional sex with men, this was confined to oral and mutual ************, which I thoroughly enjoyed. I always refused anal sex saying I was not into...
    spangle47uk spangle47uk 56-60, M 5 Responses Feb 22

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    The Best Night Ever!

    Ok, so a little back story on me. I was a bout 22 when I first discovered that I liked watching gay ****. At first I would switch back and forth from gay to straight **** but have progressed from that to only watching gay with a little bit of bi **** in there from time to time...
    bottomslut bottomslut 22-25, M 8 Responses Jun 27, 2011

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    Gang Bang

    I once went camping with close friend of mine. When I say close I mean have had lots of gay anal sex. I'm usually in the bottom taking his big **** in my butt. If you've read my previous stories you'll know I'm a big butt ****. I'm a *** bucket. But I was going camping with him...
    Thecumbucket Thecumbucket 22-25, M 7 Responses Nov 11, 2013

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    It Started As A Joke And Became A ********

    Few years ago I was chatting with a female friend of me over skype. She is a lady I used to **** 2-3 times a year sometimes in ********** with my wife. That time she was just asking me to go over her place and **** her. I was joking to her back to use her male roommates for sex...
    eurocuck eurocuck 36-40, M 5 Responses Mar 28, 2012

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    First Bi Experience

    When I was younger 13 to 14, I discovered my dad’s **** collection. I loved to read the stories especially about anal sex. They absolutely fascinated me. As I was always supper horny, I would often beat off thinking about being on the receiving end of all the hard dicks I read...
    lt2s2 lt2s2 46-50, M 7 Responses May 1, 2012

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    Unexpected Sex

    i was out with my boyfriend one night and he was driving. we were headed back to my place when he turns into a developing subdivision. i asked him what are we doing here? he said he wanted to look at some of the houses. little did i know what he really wanted. my ***!! he pulls...
    1nakedninja4u 1nakedninja4u 36-40, M 10 Responses Oct 1, 2012

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    I ****** A Shemale

    My cousin (the one in my previous experience) brought home this really cute girl today. Us three were talking and I noticed a bulge around her vagina. She seemed really sexual about everything, talking about how she would love to have sex with to guys at once. So I was saying...
    Thecumbucket Thecumbucket 22-25, M 2 Responses Nov 10, 2013

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    Is there any other way?

    Im gay so sex with a man is part of my d.n.a. Its not only the physical gratification but the joining of two bodies and minds lost in spiritual sxertisy
    thegaychef thegaychef 51-55, M 2 Responses Jan 28

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    Safedomdaddy Is Getting Wilder

    Well friends and *******...I have learned that I too love to suck *****...I have now sucked 6 ***** in the past 2 months...I have yet to get a mouthful/or face full of *** but I did try. I .now have a few dedicated guys that like to 69 with me. I have not gone down the ABS road...
    deleted deleted 26-30 Nov 4, 2013

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    teachme383 teachme383 41-45, T 3 Responses Feb 2

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    Bottom First Timer.

    I was wrestling a guy from my high school wrestling team at practice. My teammates name was Carl. It was a sweaty and rough practice. We recently lost to another school so the couch was pushing us hard during the practice. Halfway through practice I started to get really...
    ballparkdogg ballparkdogg 41-45, M 11 Responses Nov 28, 2012

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    Only twice. Once as a Chat hookup; it was a

    first time for both of us. The second was through a gloryhole--both times were with protection.
    writer732003 writer732003 41-45, M 3 Responses Mar 16

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    My Best Friend Is A Shemale!

    My best friend which I thought was a female was actually a shemale. We were in our underwear wrestling (hot, I know) and since she was a girl I go easy on her. She pinned me and sat on my chest and smiled at me. Then she pulled a **** out of her panties and stuffed it in my mouth...
    Thecumbucket Thecumbucket 22-25, M 1 Response Nov 21, 2013

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    Came In 60seconds

    I was 13 and had a sleep over with my best Patrick he had Ginger hair I slept in his bed with him as I was trying to sleep his arm came over me I did not mind I got turn on my **** got hard his hand slowly touch my **** he then pressed his body to me i felt his hard **** on my...
    nicholasduffy nicholasduffy 51-55, M 51 Responses Aug 20, 2011

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    My First Time Getting Anal

    i've been bi since my early teens,and i love to suck ****,and swallow.when i was 15 i met this trucker that lived close to my cusins house.i kinda was interested in beeing a trucker,and was admireing his rig.vic was the guys name,and he was washing his rig talking with me about...
    shelbycpl shelbycpl 41-45 5 Responses Oct 16, 2010

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    The first time I bottomed

    for another man was when I was 14. He was older and we had been playing around for a few weeks. We mostly sucked each other or jacked each other off. I would go to his apartment and he would set out a futon mattress on the living room floor since his bed was a single. We would...
    bottom63 bottom63 46-50, M Dec 12, 2013

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    Anal Sex With Other Men

    When I first realized I had a sexual attraction to other men it was strictly making out and sucking ****!  The first guy I was with did **** me twice and at first it hurt like hell until I relaxed and then it was wonderful!  I stopped having anal sex because of the...
    bimountainman bimountainman 60, M 9 Responses Mar 5, 2010

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    Bathroom Rape

    I was in a public restroom and I had just finished ******** and someone stuck their **** through a glory hole and being the ***** I am, I started sucking it. I heard him moaning from the other side. I was feeling *** horny so I crawled under the stall and he looked at me then...
    Thecumbucket Thecumbucket 22-25, M 2 Responses Nov 23, 2013

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    I Had Sex In The Cab Of A Semi-truck

    A few months ago I responded to an ad on Craigslist about a guy that was passing through the area that day and was looking to have sex with a guy in the cab of his semi. We arranged for us to meet at a rest stop on the interstate. Later that afternoon I located his truck. He said...
    rycrad rycrad 36-40, M 5 Responses Sep 28, 2013

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    Technically The Boy At My School Raped Me ...

    While in hs there were guys i'd mess with , boys who of course insisted that they were straight but wanted to know what it was like to suck a gay boys **** stuff like that , of course still swearing that they were straight and that did not make them gay or bi. So this one boy...
    clay749 clay749 18-21, M 23 Responses Aug 9, 2013

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    Nice way to Spend an Afternoon Today was one

    of those days. I was off today and my spouse had gone up to see family for a couple of days. I had such a sexy dream last night and woke up horny as hell. So, I had to do something about it. I called Michael. I knew he was working today, but thought maybe he could come by on his...
    charleybi2 charleybi2 61-65, M 3 Responses Jan 2

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    Wow, Now I'm Sore!

    Following my story yesterday, Frank arrived this morning at the time he said he would (that's the good thing about older people, they are punctual!) and i was naked as I opened the door to him. He immediately grabbed me in a hug and his mouth roughly found mine in a passionate...
    artman2 artman2 51-55, M 32 Responses Jan 27, 2012

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    Where It All Started (1)

    I was introduced to male to male sex and being a bottom in my late teens. He was a very nice older guy who never did anything without first telling me what he had in mind and asking if I wanted to try it. It started out in his photo darkroom. As he was instructing me how to...
    NotRich NotRich 70+, M 7 Responses Jul 3, 2013

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    First Time

    I'm bisexual - which I only recently figured out - and I had my first guy on guy anal sex experience (actually it was my first guy/guy experience ever) just about three weeks ago. After I had told a couple of friends (straight women) about thinking that I might be bi...
    Scott88 Scott88 22-25, M 44 Responses Jul 22, 2010