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I My First Anal Sex

Personal Stories, Advice, and Support 512 People

    How I Made My Fantasy Of Losing My Anal Virginity Come True

    for many years i had fantasised when wanking of what it would be like to have a **** up my bum. when i was about 24 i got to know a younger boy of 17 thru a mutual freind, one night he had called around to my flat and we both started drinking vodka and coke both of us were quite...
    iadorescat iadorescat
    41-45, M
    3 Responses Dec 22, 2011


    When I was younger, I hung out with two boys from the neighborhood. We would get high and drink sometimes. We were at Jim's house and we were pretty intoxicated. Talking about sex, drugs and rock n roll. I was pretty, nieve and a lot flirty. Jim wanted to know if I ever tried...
    Gr8Find Gr8Find
    1 Response Mar 5, 2013

    My First Anal Sex

    the first time i had anal sex was with my husband .. we were at the house playing around one thing lead to other took my clothes off held me down and he put some ky on him and he put it in and it hurt but i liked it rough and injoy him cuming in side me .. i just love anal sex...
    samsarha80 samsarha80
    36-40, F
    7 Responses Mar 10, 2012

    I was studying Horticulture at University,

    when I met a lovely lady. We studied together as I had a computer and she did not. I admit I was a virgin, and as a man at University I had to keep that quiet! We had been going out with each other for about a month, but had never made love or really talked about it. After a...
    Nextime1 Nextime1
    51-55, M
    Mar 7, 2014

    Let Me Take You Stress Away...

    CumstressAnna CumstressAnna
    26-30, F
    Jun 29, 2013

    Just The Tip

    My girlfriend likes to cuddle up to me when we lie down. This usually makes me hard, because most of the time we make out or she grinds against me. A few days ago we were dead tired and lying together. We were spooning and she started to grind into me making me hard as usual. I...
    Nemacyst Nemacyst
    22-25, M
    1 Response Jul 30, 2011

    When It First Started

    im about 25 now but i have many horrible stories from when i was a little girl some have the same concept so bare with me. my fist time was when i was 4, my 15 year old bro took me to play when my parents were out but this time he did something else, he took his penis out and put...
    deleted deleted
    Mar 24, 2013

    Good Girl.

    We had been dating for a while, and we ****** any chance we got. We got home late at night, drunk and still dressed for clubbing. You were bent over the bathroom sink with your slinky black dress hiked up. I spread your cheeks and pushed it in. You loved the pain, and I loved...
    deleted deleted
    Jun 12, 2013

    Lesbian Anal

    My first anal experience was with the woman who was my first lesbian experience. We had ended up living together as I got divorced and couldn't afford my house any longer. She was a wonderful lover, so much better than my ex. She was very experienced with anal sex both with...
    deleted deleted
    6 Responses Oct 18, 2012

    Anal Virgin!

    I haven't done anal but the thought of doing it and watching **** videos, really turn me on. I would love to do this someday when I find the right guy ;)
    Flipadelphia Flipadelphia
    22-25, F
    5 Responses Apr 6, 2013

    "My First Anal Sex"

    The first time the point of penetration. I never felt that first push. it hurt but it felt so good.THE man 12 years older than me.I was 15.He brainwashed me that i was gay.He shaved my pubes,*** and pits to keep looking like a smooth boy.THE SEX WAS RAMPANT!I would hold my *** up...
    cayceher40 cayceher40
    46-50, M
    1 Response Oct 5, 2009

    My First Anal Sex

    I was in the Navy and of course if one was found having gay sex you were out. But that never happened. I was with a guy named Harold and he was around 30-35 years old. I was 20. He had been blowing me for a few months and I never gave him oral sex. Sometime later we were at his...
    oleman69 oleman69
    66-70, M
    Jul 2, 2013

    My First Anal Experiance

    I went to dinner with my best friend Phil, his girlfriend(Ann) and her friend Beth. After dinner Phil&Ann want to go dancing, but Beth didn't. So we split up, we went and had a few drinks and talked then Beth said her feet where killing from her new shoes and wanted to go to my...
    boomer58 boomer58
    11 Responses Jan 19, 2013

    Dont Wanna Admit But I Think I Like It ,

    did it first time way back with my 2nd bf, and yes i was a bit hesitant to it but it turned out to be good experience, it just completely different feeling cant explain sooo deep inside you , so full n really hotif your guy knows how to do it properly then its really hot , can...
    SluttyBitchh SluttyBitchh
    31-35, F
    9 Responses Oct 27, 2013

    Not Bad... Because I Was Ready

    The first time I had anal sex was when I was 11. It didn't hurt at all but I guess this is because I had been ************ and sticking things into my *** long before I actually had anal sex. Let me start from the beginning. I discovered internet **** when I was 10. I was...
    sierrabelle sierrabelle
    22-25, F
    23 Responses Jan 18, 2013

    First Time I ****** ***

    My first time I ****** someone in the *** was when I was about 13 years old. This took place over 45 years ago but it still happened. She was my friend's sister and she was about 10 and her name was Debbie. We were both stupid kids. At the time she was my girlfriend, belonging to...
    deleted deleted
    1 Response Oct 27, 2011

    First Anal.

    my first one was awesome, just like every other that followed after and there have been many. I was totally relaxed, in that kind of special kind of state you get into during an awesome sex, and I just felt it in my ***. The feeling was incredible. When it's entering for the...
    TinaTina5 TinaTina5
    26-30, F
    8 Responses Jul 22, 2013

    I Was Scared, But Now I Want More!

    My boyfriend and I just tried this for the first time. I was actually the instigator in the situation. He was afraid to hurt me, and I was a little scared too. A few drinks and some good lube later, and he was slowly pushing it in. I was already turned on, but I immediately got...
    Jan 30, 2013

    Just Me

    only on my own, with my finger and some ky jelly the pleasure was something I have never felt before......don't think I will be able to stop myself from doing it again
    harda harda
    41-45, M
    May 5, 2013


    My first time having anal was in high school with the boyfriend of a friend (I know I'm bad). He took it slow and was gentle. He reached around and stimulated me and I had a big time ******. He came inside me. I was a little sore the next day, but it was a great experience.
    OpenCallie OpenCallie
    26-30, F
    2 Responses Dec 24, 2012

    First Time Wasn't The Worst Time

    My husband's wanted to have anal for years. I had been an anal virgin before him (although I had a fair amount of sex in my youth), but he was persistent so I finally gave in. The first time we did it, he had truly worked me up by eating my *****, fingering my ****, and bringing...
    MontrealCouple MontrealCouple
    36-40, M
    3 Responses Nov 20, 2012

    At The Beach

    I was with a bf in Mexico for a vacation while in college. We had been having sex for some time and he had asked me about it before. Neither one of us had ever tried and I figured you should try everything once. We had been at the pool all day and had gone to the room to...
    officegirl28 officegirl28
    26-30, F
    3 Responses Jun 15, 2011

    First Taste........ Addicted For A Lifetime

    I was a 16 yr old with my friends 55 yr old aunt, I thought I knew what I was doing but now looking back I'm so lucky I was used for her entertainment, it gave me super confidence as I explored with girls my age. She used to bathe me and massage me, rubbing my body all over...
    Begentlewithme Begentlewithme
    4 Responses Aug 7, 2013

    Remeber My First Anal

    me n my gf wer in the shower, i asked if we can try anal, then at first i kinda massaged her hole with my glans, then i got it in. anal is fun bout good if you take it easy..we got super kinky after i shot my load in her i kinda stood still with my still in her, then as i got...
    ogscko132 ogscko132
    26-30, M
    1 Response May 14, 2013

    Anal: The Truth?

    You say it was awesome, it felt great, the pain wasnt bad, no lube. Tell me about the real stuff. Was it weird? Did it smell? Was it disgusting? Did it hurt for you to go to the bathroom after? Like someone tell the ******* truth because i dont believe all these pretty...
    Fishsnap Fishsnap
    1 Response Sep 8, 2013

    Not Painful At All

    Happened just yesterday. He told me one day with him I'd beg for it, and after completing 3 times, I wanted it. I told him he could do anything to me, which he already has done everything but that. He demanded I get on my knees and put my head down. Using, my juices and saliva...
    femme1278 femme1278
    36-40, F
    1 Response Jun 30, 2013

    Not Bad At All

    The first time I did it was for my boyfriend on his birthday. I wanted to do something special for him and this was it. I was very lucky that he didn't just ram it in. He massaged my butt and then my anus and slowly introduced a single lubricated finger. As I relaxed he...
    Marcette88 Marcette88
    31-35, F
    9 Responses May 15, 2013

    Never Thought I Would Do It Or Like It

    I am 35 happily married. My husband and I never talked about this ever(anal sex) . It was forbidden . We both are very serious and shy about sex.We never had sex until we got married. It was 5 years into the marriage that we were spooning obviously very horny and started to make...
    ramei ramei
    31-35, F
    7 Responses Aug 24, 2011

    Craving And Training

    I want your **** buried deep inside my ***. I want your balls. dripping wet with my ***** juice. to slap against my **** as you **** me hard. Ahh, but how to get there. Everytime your fingers wander back to that forbidden area, I clench up tighter than a clam. I want it so...
    deleted deleted
    2 Responses Dec 16, 2012

    First Time Anal Sex

    It was by far the greatest sexual experience of my entire life. My girlfriend and I had been dating for 3 years and she had absolutely no interest in anal sex. I never even asked her for it because i thought it was a lost cause. Then out of the blue she told me that she was...
    shyguy9788 shyguy9788
    26-30, M
    1 Response May 12, 2013

    A Little Different Than I Expected.

    When I was pretty young, about 11 years old, my friend would sneak out his older brother's dirty magazine. They were not the typical Playboy or Penthouse magazines so they showed a bit more graphic content. This is when I first learned the term anal sex. I didn't lose my...
    Doctorz Doctorz
    41-45, M
    Jul 14, 2013

    My First Time In Her ***.

    She was a few years older than me and we had been acquaintances but not really friends for years until we both wound up being divorced. We chatted online one night and decided to become friends with benefits to fulfill our sexual needs untill we found love again. For some reason...
    islander0286 islander0286
    41-45, M
    Mar 8, 2013

    My First Anal Sex Experience Was Wonderful!

    I always like to start off my stories by saying that they are all 100% true and, unless I say otherwise, they have all happened within the last week. I am a married woman and have a younger lover, and he truly has the body of a Greek God. I have never seen a body like his...
    Jezibell Jezibell
    46-50, F
    10 Responses Jun 28, 2013

    Amazing Redhead

    My first time was in college. I was a late bloomer anyway, not having lost my virginity until I was 18. In the short few years afterwards I made up for lost time. My final days at school were drawing to a close and I was living in this small efficiency apartment right off campus...
    storyjourney storyjourney
    41-45, M
    Mar 6, 2013

    My First Anal Sex With My Wife

    Last friday me and my wife were having a few drinks when my wife went in 2 the bed room and called me in she was standing there in full stockings and ask me what would i like 2 do 2 her to night so i said how about anal sex we have not done that yet so my wife said ok but first...
    startreksex startreksex
    41-45, M
    5 Responses Apr 29, 2010

    My First Ever Anal Experience

    I live recently in , for some of you strange, but for us three a wonderfull relationship. I know my boyfriend since I'm 16 and I live with him about 2 and a half years. He knows that I am bisexual and I even involved him in some of my girl - girl affairs. So it came that one of...
    nemtudom69 nemtudom69
    18-21, F
    4 Responses Dec 11, 2012

    First Time

    I was making out with my boyfriend one night when things started to get far more intimate as they usually do. He took my shirt and bra off then fondled my breasts. In return I took his pants and boxers off and gave him a loong, wonderful *******. Eventually he decided that...
    Fox88 Fox88
    26-30, F
    2 Responses Oct 24, 2013

    First Time

    my bf and i recently tried this for the first time.
    VickyBu VickyBu
    18-21, F
    12 Responses Oct 16, 2012

    She Was My Big Brother Secrtery

    im from arab coutries where girls virgin untill they got mirrage ....... when i was in college i used to go on summer to work with my brother company as trainer , she was his assisatnce 24 Y.O i like her and we start some jokes turned to s e x y jokcs , one time my brother was...
    ashrafcairo2011 ashrafcairo2011
    31-35, M
    Feb 8, 2013

    Oh The Pain!

    It was with one of my boyfriends who I was visiting at college. He had talked about it a lot, but i never felt like doing it at all, but the more we would have sex the more he would ask and the times we would 69 he would lick my *** which at first i thought was really weird, but...
    KelseyBB KelseyBB
    18-21, F
    4 Responses Aug 7, 2012

    Only Tried It With Toys

    Since I first became sexually active I had always said that anal play would never be a part of my sex life. When I started dating my husband he brought it up a few times and talked about how he liked it but I always shut that subject down immediately. I thought he had dropped it...
    jellowtf jellowtf
    22-25, F
    1 Response Mar 18, 2013

    He Came Inside Of Me...

    The first time I had anal sex was with my first boyfriend. I believe I was 15 or 16. For months, we'd been "fooling around," i.e., petting, kissing and he'd fingered me to intense, squirting ******* (usually in his car towards the end of our date). Eventually, I was able to...
    Sandra45 Sandra45
    36-40, F
    3 Responses Dec 19, 2012

    Let Me Take You Stress Away...

    CumstressAnna CumstressAnna
    26-30, F
    Jun 29, 2013

    Never really tried it before,

    but I want to lol, any advice????? I have like you know messed around back there, but i want the real deal... If anyone has some solid advice or exp pm me
    JimMorrisonsGhost JimMorrisonsGhost
    18-21, F
    4 Responses Mar 6, 2016


    Me and this guy I was seeing were fooling around in bed. I was laying on my back he was on top of me. He had his **** in my ***** and he was pumping quite hard. It felt good, but I wanted him even deeper. So I lifted my knees up to my chest. He started pumping even harder. It...
    xAmber xAmber
    18-21, F
    16 Responses May 18, 2011

    My First Anal

    It started few months ago. My husband was acting weird when we have sex, I always felt it but never talked about it. Until one time when we were at it, i was laying on my back he brushed his **** on my anus. It felt weird but somehow i was thrilled about it. It happened after...
    Noss88 Noss88
    1 Response Aug 10, 2013

    Friday Night

    I had always thougt of having anal sex with my bf i knew he would love it! I believed after being together for 4 years he deserved to have a first & i did too. It started this friday night , i got off the shower & we were both so turned on ready for a good night . We had...
    Cyndyarcia Cyndyarcia
    22-25, F
    1 Response Oct 6, 2013
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