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I Want to Try Anal Sex

Personal Stories, Advice, and Support 399 People

    I Want to Experience Anal Sex

    I am a long time cross dresser who is looking for cd guys who would be interested in trying anal sex. I think that you only go around once in this life and it is important to try different things as long as no one is hurt.
    glen glen 51-55, M 5 Responses Aug 22, 2008

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    I'm A Little Scared

    I would like to try anal one day, but I'm a little nervous. I have never had anything bigger than a finger in there. Sometimes I stimulate just the outside when I'm ************ and I like it. Maybe I could try some small anal beads. Do those hurt if you're a virgin?
    DavidMc69 DavidMc69 41-45, T Jul 24, 2013

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    Beggars Can Be Choosers...

    But she downright demanded that I always finish off in her ***. Such a nasty ****. I only say that because for one she had only really started having sex a few months prior. Not to say that this little cockslut was a virgin just a few months prior... HELL NO! I meant to...
    ckrazyp ckrazyp 26-30, M Jan 17, 2012

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    Tips For The Best Anal Sex

    These tips are derived from my anal experiences with my girl! If anyone have something to add, please comment. Firstly you must be in mood, good psychologic approach is very important, it must be a pleasure for both partners. There are various positions, maybe the most easy...
    simbian simbian 31-35, M 1 Response Mar 7, 2012

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    I've Never Quite Been There

    I've always been interested in having anal sex with a woman I'm seeing at the time. However, none of the women I've been with have been interested and I've not seen it as my place to put pressure on them to do so. If a woman ever lets me take her back door then I want it with her...
    toeyasaromansandal toeyasaromansandal 36-40, M 5 Responses Jan 7, 2012

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    Want To Try

    besides wanting to suck a ****, I want to try having a guy **** me in the ***. I just worry about how painful it might be. Should we use a lot of lube and how deep will it go in? do you stroke slow or go fast? How do I insure that everything is clear before entry? I actually...
    deleted deleted 26-30 1 Response Nov 22, 2011

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    As A Bottom

    OK, I'll admit that I have already tried anal sex with a woman. And it was good for both of us. And afterwords I felt like I was missing something. I've tried various objects in my butt, but none of them offer what I seem to be missing. And I don't think a strap on experience...
    RayanneA RayanneA 56-60, M Apr 8, 2012

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    Looking For Adventure

    Willing to try it,my best friend said it hurt like hell and it felt like a lot of pressure, her experience...but I'm sure overtime it becomes a great feeling of fullness
    Chocolategirl18 Chocolategirl18 18-21, F 7 Responses Feb 9, 2013

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    I Want To Try Anal Sex With My Gf

    Last year I got thoughts of trying anal sex. I asked my gf if she would have anal sex with me and at first she said she'll try and we've been together for 3 years, but now she doesn't and I really want the experience. I have experienced it on myself by sticking a finger in my...
    packers2012 packers2012 18-21, M Mar 18, 2012

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    Want It Bad

    I want to be ****** in the butt. I've had fingers and a couple of toys in there, but I want a real man with a big **** to just pound me up there. I want it rough and I want it to hurt. Maybe even more than one guy.
    sunnysaraA sunnysaraA 26-30, F 14 Responses Feb 28, 2012

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    I Want To Try

    I've never tried anal sex and only ever had my hole fingered... That was incredibly! I can only imagine what anal sex would be like and I think it would feel amazing! Now I just need someone;)
    Amy2877 Amy2877 26-30, F 9 Responses Sep 23, 2012

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    Small Anal Toy

    I have started to sleep with a small anal toy in mt butt the first night i could not get to sleep with it in me i was very restless on the second night i put it in again it is a bit thicker than a cigarette and about 4 inches long and i fell asleep with it in me when i woke up...
    itschrissy itschrissy 51-55, M Feb 1, 2012

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    Experience

    I have a strong desire to enjoy a very sensual anal experience with a woman I have had acouple very awesome anal moments not as sensual as I would like, with lots of kissing and rubbing, long slow grinding during daylight see all experience I truly desire
    Dagramor Dagramor 41-45, M May 29, 2012

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    Want To Try It

    I think I had one too many drinks last nite.Then I askes my girl if we could try and have anal. She`s also never done it.She let me,but I could see I was hurting her.I think its `cause of the no lubrication. So tonight I`ll suprise her with some KY and see if we could get...
    Magnito Magnito 26-30, M Feb 19, 2010

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    *****

    Someone finally brought the cast of Family Guy to life where Quagmire hooks up with Meg instead of Lois but I wonder if Stewie hooks up with Brian? LOL http://familyguyporno.org/
    Devilizer89 Devilizer89 18-21, M Mar 13, 2012

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    I Really Do Want To Try

    I'm fairly easy, but I have never really had the chance to try anal sex. A finger once in awhile, but no toys or the real thing. I would really like to experience it both ways. I could never say no to a woman with a strap on willing to do me. I only hope she would be gedntle...
    jimz2 jimz2 51-55, M 11 Responses Mar 3, 2011

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    Im Almost An *** Virgin..

    i have only tried this three times,if you count the time a teenage boyfriend "accidentally" rammed it into my butt and wouldnt stop pumping till he was done,despite the pain it was causing me. with that as a first time experience i guess i have been kind of afraid. i did enjoy it...
    ricochetwest ricochetwest 26-30, F 1 Response Apr 29, 2012

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    Getting 'sold' On Anal Sex

    To this day I don't remember what he was supposed to be selling! I was doing the odd chore around the house in a rather wet nappy and my pretty blue plastic pants and, when the door bell rang I waddled down to answer it. I was expecting a parcel delivery which I knew would be...
    jadmar jadmar 70+, M 3 Responses Nov 10, 2011

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    Mixed Emotions

    i really want to see what it is like, but something about it also scares me. like i will feel too strongly one way or the other about it.
    tstreeter tstreeter 18-21, F 8 Responses Nov 9, 2013

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    WANT to Know

         MY FIRST WIFE WOULD FINGER MY ***,WHILE SUCKING MY ****.I LOVED THE FEELING OF HER FINGERS SLIDING IN AND OUT OF MY HOLE.I REALLY THINK SHE COULD HAVE MADE ME ***,JUST FINGERING ME.SOMETIMES SHE WOULD GIVE ME A *******,AND **** MY *** WITH 2 OR 3...
    slikshaved slikshaved 51-55 7 Responses Jul 15, 2009

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    I'm Sure I'd Love It!

    I posted a photo of me on my site, ready for bed dressed in a nappy and pink plastic pants, and also in a Baby Doll nightie which I have recently bought and which I love wearing. This is evidence of the Adult Baby that I enjoy being, but, looking at it, I realise that it shows...
    jadmar jadmar 70+, M 2 Responses Feb 24, 2010

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    Knock On My Door (X Rated)

    Certified *ss Inspectors will be visiting your neighborhood. If they know you are home and you invite them in  ... you can submit your *ss to be measured. Once measurements are complete it will mean that your *ss will have been approved by a Certified *ss Inspector. Then...
    Josie06 Josie06 56-60, F 1 Response Jul 5, 2010

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    Whats The Best Way To Do This?

    My boyfriend has been wanting to, it took a long time before i could even get used to the idea, but i thought hey some people really like it, so we thought wed give it a try..WE FAILED...how are you supposed to do it and have it feel good? we didnt get to far before i was like...
    pinknailpolish89 pinknailpolish89 22-25, F 4 Responses Feb 1, 2010

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    Im Almost An *** Virgin..

    i have only tried this three times,if you count the time a teenage boyfriend "accidentally" rammed it into my butt and wouldnt stop pumping till he was done,despite the pain it was causing me. with that as a first time experience i guess i have been kind of afraid. i did enjoy it...
    ricochetwest ricochetwest 26-30, F 3 Responses Apr 29, 2012

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    Im Almost An *** Virgin..

    i have only tried this three times,if you count the time a teenage boyfriend "accidentally" rammed it into my butt and wouldnt stop pumping till he was done,despite the pain it was causing me. with that as a first time experience i guess i have been kind of afraid. i did enjoy it...
    ricochetwest ricochetwest 26-30, F 1 Response Apr 29, 2012

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    Curious

    I love exploring, and having explored with toys, I am so curious about being taken from behind. Doesn't matter if its a strap-on or a real one, I want to know how it feels like to be penetrated and ****** by someone else, to be in someone else's control. I want to know if I can...
    ClosetTrans ClosetTrans 26-30, T 1 Response Apr 24, 2013

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    Im Curious

    i have thought about doing this as well , but my husband has no interest in it..he does not like the butt thing.. i think its a sensative spot.. and i sometimes think about what it would be like to have sex there..i just think it would take trust in a guy to take his time with it...
    stacie30 stacie30 26-30, F 11 Responses Aug 28, 2011

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    Last Night

    I had the best dream! I dreamt that my GF was naked and bent over and her ******* was gaping so wide I could put my fist in it! I have always wanted to make my GF gape, even more i want to *** in her *** and have her gape so I could see my *** drip out of her ***.
    jerseyal26 jerseyal26 31-35, M 1 Response Sep 27, 2012

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    Im Almost An *** Virgin..

    i have only tried this three times,if you count the time a teenage boyfriend "accidentally" rammed it into my butt and wouldnt stop pumping till he was done,despite the pain it was causing me. with that as a first time experience i guess i have been kind of afraid. i did enjoy it...
    ricochetwest ricochetwest 26-30, F Apr 29, 2012

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    Want To Be Pounded In The ***

    I would really like to know what it's like to take it in the *** like the women do in ******. When watching **** that is something that always makes me wet and gets me going. After watching it sometimes for only a few minutes, I am ready to get off myself.
    TakenbyDan TakenbyDan 41-45, F 4 Responses Feb 2, 2012

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    My New Toy

    I recently bought an imitation penis. It is all flesh pink, quite realistically shaped with a mushroom head and faint tracings of veins in the shaft and about half of a sac containing the balls which enabled the **** to be held. The morning after it arrived, before I had my...
    jadmar jadmar 70+, M 2 Responses Sep 20, 2012

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    Want It Bad

    Want it bad but my husband does not seem interested
    Sl118 Sl118 41-45, F 4 Responses Jul 7, 2013

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    This Is A New Goal

     I set this as a new goal with a deadline of may 2010.  I would dress up as the sissy i am for you, any takers i have never had a real one inside any of my holes. Tanya
    deleted deleted 26-30 Nov 9, 2009

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    Back Door

    I would like to experience anal sex with another woman. Me entering her and turn about is fair play and her entering me. Not sure how or ever this could happen but it is a dream.  
    deleted deleted 26-30 Sep 23, 2009

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    The First Time

    This is just a story. It didn't happen to me but I surely wish it, or something like it, would. I got considerable sexual enjoyment writing it, and I hope you get as much reading it. We had met at a party hosted by a mutual friend and, finding ourselves together in a corner of...
    jadmar jadmar 70+, M 3 Responses Mar 5, 2011

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    Any Tips On Anal Sex??

    my boyfriend loooves my *** an we try to do it anal but it feels so weird to me. I try to enjoy it but it is a very strange feeling. we did use lube. any tips girls? how did you get through your first few times? I want to do this for my man.. he always gets what he asks for. so...
    cheergal24 cheergal24 18-21, F 7 Responses May 28, 2013

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    Not Right Now, But I Shall Get There In The End

    She paused, looking at the slightly uneven landing *****, and a girlish giggle escaped her lips.  Then she told me an interesting fun fact about vending machines and made a rather rude joke about eating ***.    I teased her that she’s hollered at me for talking about...
    milkynips milkynips 46-50, F 2 Responses Dec 28, 2011

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    I Really Want It!

    I don't know why, it just sounds so erotic and would please me like nothing before. I get so wet just thinking about it, but don't have the nerve to ask someone to do it to me
    pessimist pessimist 18-21, F 1 Response Nov 2, 2009

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    LOVE It

    Years ago my GF would lay me on my stomach and lick my ***, then she would finger it, she would then flip me over getting as many fingers in as she could! ******* my *** as hard as she could, and when I came it was the best ever! A few times she actually came too, and I never...
    jerseyal26 jerseyal26 31-35, M 1 Response Aug 18, 2009

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    Related Experiences

    I want a sex change more and more and more than I have ever wanted anything else. I would love to be a woman for the rest of my life and it pains me that I can not be a woman right...
    wtbwoman wtbwoman 41-45 4 Responses Mar 24

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    As I prepare to go as Lucy full time, I find myself reflecting on the road ahead. I have wanted a sex change operation for many years now and I know it is the right decision...
    LucyTG LucyTG 26-30, T 3 Responses 1 day ago

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    Sexy chat with sexy people is totally sexy
    annamaria88 annamaria88 22-25, F 6 Responses Apr 3

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    This may be very picky of me, but it irritates me when people try to work up to sexy chat. I get that they're trying to not appear senseless and creepy, but if the only reason you...
    ArguablyLonely ArguablyLonely 18-21, F 6 Responses Apr 2

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    I've never sexted before.. Is that bad
    seanc9 seanc9 18-21, M a week ago

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    i'v been cross dressing for 8 years now. when i was little if you asked me if i wanted to be a girl i would of said yes. but now being 18 there are a few things that is stopping me...
    voltinfinity voltinfinity 18-21, M 3 Responses Mar 24

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    Who wants to JO together hmu
    Bman1981 Bman1981 31-35, M 2 Responses Apr 2

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    Any women out there that want to have a no strings attached good time via the internet? ;)
    thehoppa1991 thehoppa1991 22-25, M Apr 4

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    Hello, I am 16, male, and have a relatively masculine body, am strong (by muscle) but weak (by emotion). Since I was about 6 or 7 years old I would think to myself, especially when...
    WarHammer40000 WarHammer40000 16-17, M 2 Responses Apr 6

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    A quickie to recharge a mundane tuesday
    annamaria88 annamaria88 22-25, F 6 Responses Mar 25

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    Slaves or Asians looking to get off together ;)
    franchiuser320 franchiuser320 18-21, M Mar 27

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    Anyone who would like to se*t just send me an inbox... Im really h***y and could use some help ;)
    9inchjunk 9inchjunk 18-21, M Mar 27

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    Im so horny right now ;) <3
    imjustlookingforadvice imjustlookingforadvice 16-17, F 14 Responses Mar 31

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    Any girl who's down to have fun(; message me up
    jacob9826 jacob9826 18-21, M Apr 1

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    Hey anyone up for some fun?;)
    15andrew 15andrew 18-21, M 2 Responses Apr 2

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    Message me right now ;) ;)
    sn00zer sn00zer 18-21, F 9 Responses Apr 4

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