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I Am a Crossdresser That Love Sex With Men

Personal Stories, Advice, and Support 361 People

    Dressed As A Women

    As a young adult I had my first experience with a man. We did have sex because I was afraid I just sucked him him and let him *** on my face and chest. In college was when I had my first sexual experience wearing panties and a bra with a man. Then I would closet dress I met a man...
    Ryan1kc Ryan1kc 31-35, M 1 Response Mar 5, 2013

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    Dressing Up And Having Sex. I'm The Girl!

    Most of you can relate to the feeling one gets when transitioning into a woman m/f.  For me, ive been doing this since i was 12 years old, growing up in home with two sisters, a mom, and an absent father.  It was inevitable that i started wearing their clothes.  It didnt help...
    Lisagurlll Lisagurlll 36-40, T 11 Responses Jan 19, 2012

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    I Love Having Sex

    I had a add online meet a guy he came over we only had 30 Minn. He rub me so nice. He pull his pants down and wow what a nice big ****. I got on right on that hot ****. I suck it then he bent me over and **** the hell out of my ***. Then I dumb one of the biggest loads I have...
    cdmary cdmary 36-40, T 4 Responses Nov 4, 2011

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    I Will Never Forget

    My first time with a man was at the age of 14 I have always liked to dress with my mom's clothe. One night I was wearing a lace thong and a white lace push up bra and a pink dress blonde wig There was some people over at the house I was just in my room alone. A friend of my moms...
    deleted deleted 26-30 1 Response Feb 11, 2013

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    My First Time

    i had been told about a place that gay and bi men go to for sex, it is not far from home, about 10 miles or so, it was a nice sunny afternoon so i drove over to it, getting changed into femme clothes en route. tights/pantyhose, short skirt, top, bra, panties and flat shoes. when...
    sallystark sallystark 51-55, M 2 Responses Nov 8, 2011

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    Dress Up And Act Like A Girl? Always.

    For me it is not a same sex attraction I am a woman and I want a man.I have been dating men as a girl for years and love it!I love men and can't live without them ... I get weak on my knees when I see a strong masculine black guy.Oh my yes men (some men) are fun to be with...
    Josie06 Josie06 56-60, F 5 Responses Oct 18, 2011

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    First Time With A Man While Crossdressed

    This isnt about how I started or why. This is just about the first time I was with another man. I had met this guy in the gay.com chatroom. He was in the next city over, a couple years older than me and similiarly inexperienced. He was fit and decent looking so we made a plan to...
    edgarallanho edgarallanho 36-40, M 5 Responses Jan 11, 2013

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    Working Trip

    It is not very often that I come out of the crossdresser closet due to my schedule and the need to satisfy my feminine urges. I won't say that I am a virgin at this game, but I haven't also have loads of experience. This is one of my most memerable. I was asked at work to go to...
    slothman2000 slothman2000 51-55, M 1 Response Mar 18, 2012

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    alexiswcd alexiswcd 56-60, T Jun 21

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    Oral Fixation

    Hi! I have had two experiences with men. The first was a roommate when I was in the military. He put on a **** and we were watching it, and when it got to a lesbian scene he began talking about how men should be so free. While I wasn't dressed...I slid to my knees and...
    GillianStepford GillianStepford 36-40, T 3 Responses Jun 10, 2013

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    My First Time In A Peep Show Booth...

    I was about 20. Had been dressing now for 8 years. Lost my virginity 6 years ago in my buddys garage. Went to this peep show. Needed a good dicken. Real bad. I was in this booth. Had the door cracked open just a bit. ( thats the sign) and this black guy walks in. At that time in...
    Tammy59 Tammy59 51-55, T 1 Response Aug 21, 2012

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    Related Group

    Just started a related group called "I'm A Trannie Who Lusts After Elderly Men". Have a look if you're interested.EP Link  (I 'm A Trannie Who Lusts After Elderly Men)
    misszaskia misszaskia 51-55, M Oct 28, 2012

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    have been dressing since 10 at 54 wanted to see

    if I was anything so I looked on craigslist (we did not have any of todays tech when I was young) found a guy he came over took his **** out the 1st time I touched another **** so I started to jerk him off, an then told my self the hell with it an went down on his...
    star16cd star16cd 51-55 4 Responses Dec 13, 2013

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    But If I'm Not Dressed I Am Not At All Interested In Men Or Sex With Them.

    The longer I dressed, the more I wondered what it would really feel like to be a woman, or at least have more of the experiences that a woman does. I had always liked only women, and as a man was not attracted to other men and would have never considered sex with them. But I...
    RayanneA RayanneA 56-60, M 2 Responses Apr 12, 2012

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    I'm Not Sure...maybe

    I am not sure if I would or not but the curiosity is killing me. I dont relish the idea of going to a bar or club just pick up a guy to have raw animal sex with. Is that old fashioned? I would like to meet someone, build up a relationship, and if the mood and moment is right...
    deleted deleted 26-30 3 Responses Mar 27, 2012

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    Young And Fit Looking 41 Year Old Crossdresser In SE Wisconsin Looking For Hot Stud And/Or Daddy!!

    I am Rebecca. I lived as a transsexual woman for three full years while on hormones the whole time several years ago. I came back across to live as male, but still passionately LOVE dressing, appearing, playing the feminine role at home cooking, sexually, pleasing my man and...
    SissyRebeccaCD SissyRebeccaCD 41-45, T 7 Responses Mar 27, 2013

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    Hit Me Up Boys ;)

    im a crossdresser in southeastern michigan waiting to get ****** ;) message me if your interested ;)
    crossdresser256 crossdresser256 18-21, M 4 Responses Mar 3, 2013

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    How I started CDing and having sex with men

    I am a mature fit attractive man , who cannot pass as a woman, but I adore dressing in womens clothes makeup and heels and then being a wanton cummy faced **** and submissive twatboi for a real mans pleaseure . I was a teen CD caught in my moms bra girdle stockings and slip one...
    tammyie11111 tammyie11111 46-50 3 Responses Apr 18, 2013

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    I Love It.

    I love having sex with men but it goes will my mental state once i'm dressed up as a girl that's when i can go and go from making out to sex with any man. I can make out with guys in public not even as a girl but when its time for sex i must be dressed up and i'm always bottom. I...
    deleted deleted 26-30 2 Responses Oct 27, 2013

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    Dressing Up Just For Sex.

    I have been crossdressing since I was very young, & have always loved to dress up completely, with lingerie, skirts & blouses, high heels, wig & make up. Sex while dressed up was my main reason for doing it, I loved sucking *****, & being ****** like a woman, which happened many...
    nanna2 nanna2 56-60, M 17 Responses Sep 12, 2012

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    Men In San Antonio

    Hi! As the group tells you, I'm a closet TV who loves to be with man being as my nature says As a Girl. I love to be properly dressed and being treated and being even "used" as a Girl when we're alone. I'm always eager to complete my inner destiny of being the submissive female...
    Calientita Calientita 31-35, M 1 Response Nov 26, 2012

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    Pleaseing A Man

    peaseinga man is my pleasure when i swallow hi **** its like imtaken away. i know that im meant to be a woman
    sabrina51 sabrina51 46-50, M Aug 9, 2013

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    Feeling Like A Total Woman

    When I am in bed with a man Im dressed in lingerie and smelling of perfume and it feels just right as I look like a woman,feel like a woman and having sex with a man is wonderful especially after lots of foreplay and he gets rock hard the feeling of being penentrated is out of...
    girlynicole girlynicole 36-40, T 6 Responses Nov 20, 2013

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    Craigslist

    So wed I was finally enjoying a day of work woke up shower relax I was feeling really horny readying some of the story's from EP so I decided to post an add on Craigslist about wanting someone to come f*** me I got a few emails there was one guy that got my attention he said he...
    deleted deleted 26-30 May 14, 2013

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    Tv Who Loves Very Old Men

    Always had it. I'm a bit older myself now but even as a teen transvestite i loved to be lusted after by much older men. Love their clawlike hands on my silk encased body, their strong necks, their thick muscular tongues invading my mouth. Love to go all teenager in love on them...
    misszaskia misszaskia 51-55, M 4 Responses Oct 21, 2012

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    Related Experiences

    I love sex without protection! I'm 18, I've had sex 4 times during the age of 14. never used a condom. loved it!
    jessicatooreal jessicatooreal 16-17, F 11 Responses Jul 22

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    Right after I lost my virginity I got on birth control. It didn't take much to talk me into sex without condoms. It's super messy to clean up and I'm scared of getting STD's but it...
    cuteshyginger cuteshyginger 16-17, F 24 Responses Jul 18

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    I've never had sex without a condom before . But I heard it's so much better . Idk I'm nervous about that kinda stuff .
    oabutler oabutler 18-21, F 19 Responses Jul 7

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    I really can't stop thinking about what just happened hours ago. He fd me so good. ... All I can think about is sex. No condoms were invited it was all raw and it felt pretty damn...
    evilsickslut92 evilsickslut92 22-25, F 15 Responses Jun 30

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    Sex is so good that way...
    annettebon annettebon 18-21, F 14 Responses Jul 5

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    I had sex all night with my guy...literally 2 feet away from my sleeping best friend and her guy...it was super hot.
    orangecrayons orangecrayons 18-21, F 21 Responses Jul 7

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    nothing more than a good load rushing inside my friend earlier.....I had to do it for the sake of hot steamy sex :p
    jonnygoode74 jonnygoode74 36-40, M 4 Responses Jul 8

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    Raw p.ussy feel soooooooooooooooo much better. But you have to eliminate ransoms out if your sex life lol
    trynaKEEPmyHEADup trynaKEEPmyHEADup 26-30, M 3 Responses Jul 15

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    Is sex actually that good? I've always thought about it but too scared ../:
    Jodiii14 Jodiii14 13-15, F 15 Responses Jul 17

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    I'm craving morning dessert. I'm hungry but not for food. I want sex for breakfast!! I wanna deep in me!
    Arussia Arussia 26-30, M 6 Responses 6 days ago

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    Would love to talk to mare ladies about this! Hit me up
    Dt2112dt Dt2112dt 22-25, M 2 Responses Jul 7

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    I lost my first time with a rubber and then went to see him again in two days. We just kinda moved quickly and I can't stop thinking about him. He ****** me without protection and...
    PureRain PureRain 18-21, F 17 Responses Jul 12

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    Love feeling it inside me! Hate protection. Love feeling his stuff drip out of me afterward. Of course I am in a monogamous relationship.
    Yumyumnips Yumyumnips 26-30, F 13 Responses Jul 17

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    There is just something delicious about the knowledge the that my lover and I are foregoing protection and taking that big risky step... the possibilities that we'll end up...
    nascent45 nascent45 46-50, M 4 days ago

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    I just love to feel a man finish in me it is great knowing that I did that
    honey2828 honey2828 26-30, F 22 Responses 1 day ago

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    Got on birth control so I can do it without any barrier between me and boyfriend. I love feeling him c0me especially when he's as deep as he can go.
    fyeahmilfy fyeahmilfy 26-30, F 12 Responses 1 day ago

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    I need to get laid ASAP I don't care who with
    hornyharry123 hornyharry123 22-25, M 4 Responses Jul 7

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    I want to get fuccked so bad. I'm craving to suck on a diick and get it all wet with my saliva and taste the precum before slide in
    Arussia Arussia 26-30, M 1 Response Jul 7

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    It's way better without protection👌
    Jenqui96 Jenqui96 18-21, F 20 Responses Jul 14

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    I started messaging a young lady here then my phone goofed up and not only did I lose our conversation I lost all the interaction I had with her . I am so pissed at this phone...
    Jake966 Jake966 46-50, M 2 Responses Jul 20

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    Did it in the pool with my neighbor last week. That was fantastic!
    itsbigT itsbigT 16-17, M 3 Responses 2 days ago

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    Put your hot icing in my cake
    Arussia Arussia 26-30, M Jul 5

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    Pls do this only if your good at it lol
    Rifkyroshan Rifkyroshan 26-30, M Jul 15

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    My girlfriend likes to pee on my dicky
    blackdicky blackdicky 36-40, M 2 Responses Jul 19

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    I usually love sex. I'm a very sexual person and I would do it multiple times a day if I could but right now, I'm so sick of sex. Anything about sex I just feel nauseous because of...
    sunflowerpet sunflowerpet 18-21, F 4 Responses Jul 16