Post
This experience may contain mature content, as flagged by the community. Please click away if you do not want to see this content, or if you are not of age. To report inappropriate content, please email us.

I Am a Crossdresser That Love Sex With Men

Personal Stories, Advice, and Support 374 People

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel
    alexiswcd alexiswcd 56-60, T Jun 21

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 Aug 21, 2012

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    I am transgender i love sex with men i

    though i was Bi but i thinking that i am Gay i cant keep my eye off guys to be honest women dont turn me on anymore i love older men they know how to treat you like a lady and they are wonderful in bed
    AliciaSissy AliciaSissy 51-55, T 2 Responses 6 days ago

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 5 Responses Nov 4, 2011

    Your Response

    Cancel

    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 9 Responses Mar 27, 2013

    Your Response

    Cancel

    Related Experiences

    I love sex without protection! Love to feel every ridge and vein. Ask me more in the comments and I'll answer... Gotta avoid those that watch since they are blocking my stuff now...
    catiemae87 catiemae87 26-30, F 27 Responses 6 days ago

    Your Response

    Cancel
    I love sex without protection, love being inside a women, and feeling every sensation....
    red1235 red1235 41-45, M 1 Response 23 hrs ago

    Your Response

    Cancel
    I have never had sex with a condom simply because me and my man wants to start a family. We haven't had sex in 3 years due to log distance but hoping he comes soon from South...
    roselani2005 roselani2005 26-30, F 6 Responses Aug 17

    Your Response

    Cancel
    I have always had sex without condoms. It feels better and is natural. This year it finally all caught up to me and now I'm 5 months pregnant. However that won't stop me and I'm...
    wanting1992 wanting1992 18-21, F 12 Responses Aug 18

    Your Response

    Cancel
    I used to like most when you first start having sex you go on the protection band wagon untill one night me and my bf was out all night and we was very horny and we rushed home to...
    xKayleighBabesx xKayleighBabesx 22-25, F 10 Responses Aug 23

    Your Response

    Cancel
    It's the best type of sex and the most natural I believe
    Jamiereturns Jamiereturns 22-25, M 2 Responses Aug 6

    Your Response

    Cancel
    My legs are going to be sore tomorrow. My bf and I had sex outside. He likes to ride me from behind so I had to bend over and get on my knees on concrete! I think he was really...
    mamafy mamafy 26-30, F 8 Responses 1 day ago

    Your Response

    Cancel
    There is no other feeling than him going in me raw with extra risks of pregnancy.
    FeralKittenx FeralKittenx 18-21, F 13 Responses Aug 15

    Your Response

    Cancel
    Hooked up with a girl for the first time in a while, but she was the first girl that told me to *** inside her. So I did. First time I've ever did, and can't stop thinking about...
    calek89 calek89 22-25, M 1 Response Aug 15

    Your Response

    Cancel
    I don't really like using condom until my gf told me to. I often *** inside her since it's making me feel really good and she also loves it too.
    cjcj0967 cjcj0967 18-21, M Aug 17

    Your Response

    Cancel
    I love the feeling of warm *** oozing out of my vagina when he pulls out. #noprotection
    isabelle69 isabelle69 18-21, F 19 Responses Aug 20

    Your Response

    Cancel
    I love the feeling of her inside when I'm all the way in there and our nerve endings stimulate a mutual ******
    Ilove2hav3s3x Ilove2hav3s3x 18-21, M 1 Response Aug 23

    Your Response

    Cancel
    How many of you ladies love an uncut **** ? Is the foreskin a turn on for you ?;)
    Staraces898 Staraces898 26-30, M 3 Responses 4 days ago

    Your Response

    Cancel
    This is true... But I'm too smart and fertile to actually do it without protection. It simply feels better... I like the feeling when a man finishes inside too. I know this sounds...
    kel25 kel25 26-30 8 Responses 4 days ago

    Your Response

    Cancel
    I love when my husband ***** me with no condom its the best thing ever even more so when he fills me up and its drips from me ;)
    sweety7268 sweety7268 18-21, F 13 Responses 4 days ago

    Your Response

    Cancel
    My cousins from Germany came to visit last year. It was amazing. There brothers and it's hot on what they do with each other. I have cammed with both alone and together. So they...
    GayJohn98 GayJohn98 18-21, M 1 Response 3 days ago

    Your Response

    Cancel
    I want to have sx right now my d is so hard
    Dloveski Dloveski 36-40, M 2 Responses Aug 2

    Your Response

    Cancel
    I wanna feel a nice thick cocck! But I wanna put it in my mouth first! Suck it tasting the precum, feeling the veins pulsing in my mouth
    Arussia Arussia 26-30, M 3 Responses Aug 3

    Your Response

    Cancel
    A nice thick c.ock in my tight, wet p.ussy! Seriously one of the most incredible feelings ever.
    Kenja92 Kenja92 22-25, F 17 Responses Aug 5

    Your Response

    Cancel
    I want to suck on a hard cockk and taste all the icing:)
    Arussia Arussia 26-30, M 4 Responses Aug 13

    Your Response

    Cancel
    My girlfriend want to have anal what to do for anal ?? Tips
    rezgarov rezgarov 22-25, M 7 Responses Aug 14

    Your Response

    Cancel
    How to have s*x stamina please I really *** quick ? Help
    rezgarov rezgarov 22-25, M Aug 14

    Your Response

    Cancel
    Hey whatever happens happens. It's a lot more natural that way.
    Rayven1997 Rayven1997 16-17, F 10 Responses Aug 14

    Your Response

    Cancel
    the way it feels is like no other feeling
    tinman45 tinman45 36-40, M Aug 15

    Your Response

    Cancel