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I My First Anal Sex

Personal Stories, Advice, and Support 486 People

    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 18-21, F 1 Response Oct 6, 2013

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    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 9 Responses Jun 28, 2013

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    My GF Asked Me To Try In Her Butt !

    We started from phone friends n end up in room on 1st date blind date.....1st time when I saw her I dnt like her personaly but rely on to be ******* buddy.... On 2nd date she sucked me n on 5th date she asked me to try in her butt (becz her female friends tried it with her BF, n...
    Ahmedubai Ahmedubai 26-30, M Jun 14, 2013

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    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 26-30 Aug 10, 2013

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    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 6 Responses Apr 29, 2010

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    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 25 Responses Jan 18, 2013

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    With An Older Man

    My first time was with an older man I met in a chat room. Every since I was a teenaged boy I wondered what it would feel like. When I was in my forties I decided to explore. The man in the chat room promised to go slow and invited me to his house. He started out just touching me...
    Redlicious Redlicious 51-55, M 1 Response Dec 11, 2012

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    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 36-40, M Mar 6, 2013

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    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

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    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 26-30, F 8 Responses May 15, 2013

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    "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

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    A Total Pain In The ***.

    i had my bf in my *** twice. the first time only half his head got in, on the second time the entire head got in but that's as far as it goes before i slid myself off under him. it was REALLY painful i couldn't go through with it. i even cried a little when he took it out because...
    pixiedavixen pixiedavixen 18-21, F 13 Responses Mar 9, 2013

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    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 9 Responses Aug 24, 2011

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    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 26-30 8 Responses Oct 18, 2012

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    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 18-21 1 Response Sep 8, 2013

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    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 4 Responses Dec 19, 2012

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    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 2 Responses Mar 18, 2013

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    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...
    PW1974 PW1974 36-40, F 2 Responses Dec 16, 2012

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    Throbbing

    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 41-45 1 Response Mar 5, 2013

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    Her First Anal

    I had a wonderful lover for a number of years. She was highly orgasmic, when I would go down on her she would have ****** after ****** until they merged into one continuous ******. She would even sometimes ****** when she was going down on me (by then I had already eaten her to...
    cebexp cebexp 56-60, M 2 Responses Aug 24, 2012

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    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 22-25, M 1 Response May 14, 2013

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    First Time

    my bf and i recently tried this for the first time.
    VickyBu VickyBu 18-21, F 14 Responses Oct 16, 2012

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    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 31-35, F 7 Responses Mar 10, 2012

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    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 2 Responses Dec 22, 2011

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    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

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    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

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    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 26-30, F 9 Responses Oct 27, 2013

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    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

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    Surprise!

    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 17 Responses May 18, 2011

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    Let Me Take You Stress Away...

    THERE IS NO SHAME! ANYTHING YOU WANT TO TALK ABOUT WE CAN... ANYTHING GOES! NO MATTER WHAT KIND OF FETISH IT IS! MALE OR FEMALE!!! LET ME MAKE YOU ***!!!!! CALL ME!!! FIRST 3MINS FREE! $1.99 A MIN AFTER THAT! 1-800-863-5478 ext: 10015924
    CumstressAnna CumstressAnna 22-25, F Jun 29, 2013

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    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 31-35, F 1 Response Jun 30, 2013

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    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

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    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

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    First.

    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

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    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 4 Responses Nov 20, 2012

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    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 36-40, M Jul 14, 2013

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    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 36-40 4 Responses Aug 7, 2013

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    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 22-25, F 11 Responses Jul 22, 2013

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    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 26-30 Jun 12, 2013

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    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

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    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

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    In The Army

    My first anal sex was when I was 18 and in the Army. I went to a strange ***** place just off post. It had a bunch of folding chairs in front of a projection screen and showed *****'s from an old projector. Hard to believe how primitive it seems now, but this was in the mid 70's...
    maxndayton maxndayton 51-55, M 8 Responses Jul 3, 2011

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    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 3 Responses Apr 6, 2013

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    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

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    Longing At 13

    In October of 1953, I was 13 and I was on a camping trip with my Boy Scout patrol group to a local park for an overnight campout in Gardena, California. I had a new tentmate and he was the biggest boy in the patrol even though he was only 13 too. My body had matured to the...
    imsunwyo imsunwyo 70+, M 7 Responses Jan 26, 2012

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    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

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    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 26-30 Mar 24, 2013

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    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 46-50 8 Responses Jan 19, 2013

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    Let Me Take You Stress Away...

    THERE IS NO SHAME! ANYTHING YOU WANT TO TALK ABOUT WE CAN... ANYTHING GOES! NO MATTER WHAT KIND OF FETISH IT IS! MALE OR FEMALE!!! LET ME MAKE YOU ***!!!!! CALL ME!!! FIRST 3MINS FREE! $1.99 A MIN AFTER THAT! 1-800-863-5478 ext: 10015924
    CumstressAnna CumstressAnna 22-25, F Jun 29, 2013

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    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 5 Responses Aug 7, 2012

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    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 26-30 1 Response Oct 27, 2011

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