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I Crossdress For Sexual Pleasure

Personal Stories, Advice, and Support 1,511 People

    What I Like To Do

    I love shopping for womens clothing. Short skirts, bras, and my favorite thing shoes and boots. Once I get home or the hotel, I slide on a pair of black thigh highs with a sexy wide top, lacy panties with a matching bra. Slide up my skirt. Today it is a back and blue color...
    cdjo cdjo
    41-45, M
    3 Responses Dec 30, 2012

    Me And Mum

    After Mum had discovered my desire to wear girls clothes she gave me a kiss. Not a Mum kiss but much more loving. I could feel my body tensing under her lovely silk bikini panties. I know I clung to her, holding her, never wanting to let go. I have never wore anything since...
    steffiwindsor steffiwindsor
    1 Response Dec 26, 2011

    I have been a cross dresser

    for 2 years. I want to take it to the next level. I want to have sex if I was a woman. I want to have sex 3 different way I want one time with a condom one time without and I want to give a bj and swallow the
    bigboy90000 bigboy90000
    22-25, M
    3 Responses Jan 28, 2014

    New Panties And Sexual Toy

    just back from visiting a couple of bars in bloomington. not much going on (pretty disappointing) so i picked up a sexy panty. Then i went by the sex store and shopped awhile until a purple sexual toy caught my attention. the attendant added batteries and let me feel it. that...
    sbothro sbothro
    56-60, M
    1 Response Jul 29, 2013

    it always makes me feel more sexual

    when 'im dressed. even when i'm just on ep. racy thoughts fill my mind and my sexual desires get more intense, sometimes leaving me desiring things i never thought i would do. at this point i want to feel like this all the time.
    deleted deleted
    5 Responses Dec 12, 2013

    Dressing Up For Sex.

    I too enjoy dressing up in different sexy outfits. I don't do the makeup but sometimes wear a wig but with some facial hair it's easy to tell I'm a guy wearing stockings, garter belt, bras and thing but when I do dress up and only if I'm dressed up like a sexy who're that I like...
    56-60, M
    Jun 30, 2013

    My First Time With A Real Man

    Iposted an ad as a CD and a picture, I am not at all passable, but I have nice latex mask and chest, with a nice set of 42 DDD **** on it and their soft and pliable, anyway, I got allot of responses, I chose a nice guy that is fit and clean, a closet gay. I made arrangements for...
    deleted deleted
    2 Responses Mar 14, 2013

    I love the feel of nylons Love sexy

    slutty Want to be mature CD
    prettypatty5 prettypatty5
    66-70, M
    1 Response Oct 8, 2014

    My Cross Dressing Pleasures And Destres

    I am a bisexual person now entering my twilight years who has discovered the pleasures of cross dressing late in life - and I love it! I am now divorced but during my marriage, obviously, I often saw my ex wife in exquisitie lingerie and found that it excited me especially when I...
    barkas48 barkas48
    70+, M
    6 Responses May 24, 2012


    D, where do I start this, lets see you know about my crossdressing, and you know my anal fascination came about. Well I guess it is safe to assume that the interest in wanting to be a sissy husband was peeked after the crossdressing for so long. As technology grew and expanded...
    bendoverboy6976 bendoverboy6976
    41-45, F
    1 Response Aug 1, 2013

    I'm Dressed Up But Home Alone

    Earlier tonight I was out with a friend. We had a few drinks, but then I dropped him off. He has to work in the morning. I arrived home, but I wasn't tired. My internet was down, so I started thinking about all my clothes...I brought everything out...Wow! Have I ever built up a...
    jacobkay jacobkay
    26-30, M
    1 Response Apr 19, 2011

    I do become aroused when I wear woman's

    underwear especially if I am photographing myself to upload on to one of the various small penis web sites that I am a member although I am definitely not among the smallest on these sights I dont have a micro penis I definitely am in the smaller category and I do get excited...
    scotchbonit scotchbonit
    31-35, M
    2 Responses Dec 15, 2015

    this is very new to me I cannot explain

    why I feel so sexy in women's clothing I do like to masterbat when I'm dress up I have never been with anyone sofar I have been thinking about a lot may be one day I'm must be a virgin at this
    deleted deleted
    2 Responses Jun 5, 2015

    I Cant Explain Why

    i dont know what it is about wearing womens clothing that turns me on. all it takes is the soft feel of a nice pair of panties and im instantly turned on and relaxed at the same time. sometimes ill put on some yoga pants and its like oh yeeeeah. all you guys that have experienced...
    1nakedninja4u 1nakedninja4u
    36-40, M
    Jan 2, 2013

    Shopping For Lingerie

    I started to acquire my lingerie collection before the days of the internet. Nowadays you can buy my favoured garment, a vintage double layered nightie, for a reasonable price on eBay although the really luscious nightie and robe sets tend to be expensive. In the old days I used...
    deleted deleted
    Dec 21, 2012

    Cross Dressing

    just love to crossdress and enjoy being a sissybitch! othernight i was dressed as a sissy in a short pink satin dress,pink petticoat that pushed dress up and displayed my pink satin ruffled panties,had a pink satin garter belt on and black stockings,4" pink heels and a pink...
    mandiejune mandiejune
    51-55, M
    6 Responses Oct 23, 2010

    Looking Sexy,

    I crossdress to feel good about myself, Im a very sexy woman and I love when men hit on me,
    seducedhearts seducedhearts
    22-25, M
    1 Response Aug 10, 2013

    I get excited when I slip on silky lingerie

    and even more excited as I slip stockings up both legs and fasten them to my suspenders. The final excitement is stepping into a full length silk slip and then the silk dress.
    timothy1994 timothy1994
    22-25, M
    2 Responses Feb 29, 2016

    Crossdressing For Pleasure

    I love to dress up completely in clothes and makeup and wig it make me feel so sexually arosed. When I do Iove to go on cam at a cd chat site called transvestitechatcity my name is katrinabo on that site and when I am on I love to play with myself and tease others who are...
    kate6262 kate6262
    36-40, T
    6 Responses Nov 28, 2010

    No matter what it is i'm wearing,

    it doesnt have to be a dress or lingerie. i can feel in the mood with just make up , a simple top and low rise jeans. The longer I am dressed the better it is.
    deleted deleted
    3 Responses Apr 26, 2015

    Love to crossdress but I can never get past the

    lingerie. I get so damn horny from just thinking about satin panties, slip and bra. I start to dress then i have to relieve myself way too soon!!!
    satinlover01 satinlover01
    61-65, M
    49 Responses Jan 3, 2014

    My Love For Lingerie

    I find dressing in ladies lingerie very exciting and it always leads to a ************ session for me. I first put on a corset and lace it as tightly as I can manage on my own. Next I roll sheer silk stockings up my legs and attach them to the corset. The next item of clothing is...
    deleted deleted
    1 Response Dec 14, 2012

    Love To Be The Submissive Little ****

    What can I say, when I dress it makes me want to be as slutty and submissive as possible. All I wish for is to please my partner, to take care of them in any and every way possible and of course for them to use and abuse me as they wish. When dressed I am nothing more than a...
    SexyTiffanyCD SexyTiffanyCD
    46-50, M
    Jun 23, 2013

    ************ In Lingerie

    If you look past the fact that we do enjoy the feminine side of crossdressing in lingerie and just look at the fisical stimulation we get when rubbing ourself in silky, soft, slippery lingerie. Why do so many people find this so strange? Pleasuring ourselves and ************ is...
    silkydrawers silkydrawers
    4 Responses Feb 28, 2012

    I confess that I do. I feel much more sexual

    when I let my inner gurl out. I have no bi desires as a male, but as Michele I love it all- with the right company. I am open to many things with those i feel good with. discreet but not prudish or vanilla in anyway- but you probably know that ; )
    deleted deleted
    3 Responses Oct 17, 2014

    Better Luck Finding A Unicorn

    Why is it so hard to find a transgender gurl, fem boi, or CD that is into more than being just wanting to bottom? I consider myself a cd. I am not passable (although my wife says I am, and wants to take me trans friendly bar) and I just love to dress in female clothing and enjoy...
    ForbiddenFreak ForbiddenFreak
    3 Responses Jul 28, 2013

    First Time And All The Time...

    When I was what is called a "tween" these days I discovered my sister's panties. They gave me instant pleasure and what exquisite pleasure it was! Thereafter, every chance I got, I stole her panties from the laundry and ***********; sometimes rubbing blisters on my most...
    casualwear casualwear
    66-70, M
    1 Response Aug 10, 2013

    I love to dress! OMG

    when I have an hour or more, I will always go get my clothes and start dressing. Sometimes I take a shower first. So nice to be clean and dry with powder and fresh deodorant. Next are panties and a bra. I usually prefer to choose a matching set, but I have plenty of options...
    lacychristine lacychristine
    6 Responses May 3, 2015

    I Crossdress For

    The sexual pleasure of older men. They love to use me like a woman.
    smoothfemme smoothfemme
    31-35, T
    2 Responses Nov 10, 2012

    Aroused In A Slip

    Sometimes I just get an uncontrollable urge to put on one or more slips. Usually at this point I am very horny for the slip and being dressed in such. I look at myself in a mirror and get so turned on. I feel so femmy and the delicate lace of the bodice and hem of the slip get me...
    Lori234 Lori234
    51-55, M
    5 Responses May 30, 2011

    At first the sexual thrill of being dressed

    itself was enough then going out for walks and drives and possibly being seen was enough then I began dressing to meet others; all for the enjoyment of sexual pleasure.
    amandatrane1 amandatrane1
    51-55, T
    1 Response Dec 30, 2015

    I Crossdress For Sexual Pleasure With Men

    I love to crossdress for sexual pleasure. But the sexual pleasure I refer to is when I go out with a man. I do not self stimulate myself when dressed femme. I want to give a man the greatest sexual pleasure and satisfaction I can. I have been with many guys and they seek out...
    deleted deleted
    6 Responses Feb 17, 2011

    Secretly Slip Into My Closet.....

    Over the past five years I have replaced my boring BVD's and Fruit Of The Loom's, with mostly Victoria's Secret and N.Y.& Co. bikini or high-cut panties which I wear under my guy clothes everday. Sounds great but eventually you get so use to them that not only do I refuse to...
    leachera leachera
    51-55, T
    4 Responses Dec 8, 2010

    My First ******

    I found I was interested in girls clothes at about 5 or 6 years old. I had a younger sister who was always dressed in frilly dresses. I wanted to be dressed in one so bad. I would sneek one out of her room and try to put it on but it just wouldn't fit. One day my sister asked...
    silkydrawers silkydrawers
    4 Responses Jan 9, 2012

    Sucking Off My Roomate After Yoga Work Out

    This took place when i was at school. My roommate was gay I had no problem with that be because i was closet gay cross dresser at the time. His name was Dan a really cute guy very shy basicaly he not a real big talker but hot anyway. As i look back i think the main resaon He told...
    mical1234 mical1234
    26-30, T
    7 Responses Feb 11, 2011

    Sissy Gets Raped In Toilets

    My wife and daughter are away today with their horse to a jumping event and wont be back till late so i arranged with another sissy to meet at a local public toilet frequented by gay men. I dressed in my schoolgirl uniform stockings suspenders ,bra ,white blouse ,school tie...
    rachelusissy rachelusissy
    31-35, M
    4 Responses Jul 7, 2012

    Dressed And Nobody To Do Me.

    My wife is out of town the weekend, last night i just watched tv, but tonight I got all dressed up in red, heels, mask, chest, stocking, beautiful Bra and panties, with this beautiful top, it hugs my **** wonderfully, I set the ***** up and i layed back, felling my self up and i...
    deleted deleted
    2 Responses Jan 5, 2013

    Making The Most Of The Cold Weather To Underdress.

    I normally only wear panties during the day as I do a lot of climbing and stretching at work and the shape of bras and other lingerie would be too obvious. But today was a special day. I took full advantage of  the mercury dropping, and this morning after putting on a...
    femprini femprini
    56-60, M
    13 Responses Dec 1, 2010

    I Too "cross Dress" For Sexual Pleasure......

    I first started cross dressing many years ago. I was "sort of" forced to cross dress by my older sister and my female cousins. I really enjoyed that experience, and continued to cross dress when I was able to. It has allowed me to explore my feminine side, and also in...
    redbow25 redbow25
    56-60, M
    5 Responses Oct 30, 2010

    I cross dress because i love it

    and how i feel but when meeting someone special or the chance of someone it will be for sexual pleasure
    alexiswcd alexiswcd
    56-60, T
    1 Response Mar 9, 2015

    Out For A Drive And A Fun Surprise

    I posted this on my space a few years ago and thought I'd share: I’ve been dressing since I was a very young. As a teenager and into my twenties and early thirties, I didnt need much make up. I just passed with my fem/boyish qualities. Being married, I find myself having to...
    Lisagurlll Lisagurlll
    36-40, T
    5 Responses Mar 18, 2012

    Shopping As A Girl And Then To The Abs

    I woke up yesterday knowing I'd be going out as Lisa. I had the most awesome dreams the night before, because it always excites me knowing that ill be a girl in the morning! First, I took a warm scented bath so that my body would smell so girly (everywhere, if you know what I...
    Lisagurlll Lisagurlll
    36-40, T
    1 Response Dec 14, 2012

    Putting on ladies clothing is a turn on

    for me. Sexy thong and bra with a cute dress makes me want to experience more. The way it feels over my *** turns me on. Seeing **** makes me want to be in the women's position. The only time I want a man is when in cross dressing.
    deleted deleted
    1 Response May 20, 2015

    Got my new clothes !!

    !:)- Going to put on my new pink panties and white corset !!! Now
    prettypatty5 prettypatty5
    66-70, M
    2 Responses Oct 8, 2014

    Having Sex While Dressed And Watching Shemale ****

    I just shared this as a response to one of our sweet members fantasies of watching shemale **** with someone. Hope you all enjoy! I've actually done this several times! The last time was about a month ago. I went to his home after meeting him on Craigslist. I wore my white...
    Lisagurlll Lisagurlll
    36-40, T
    4 Responses Jun 4, 2012

    I have on a skimpy one piece swimsuit on.

    This swimsuit looks and feels so feminine and sexy. I'm scared I'll be seen out in my backyard patio but I'm loving being wet and outside so I'll take a chance.
    deleted deleted
    1 Response Jul 27, 2015

    Early Crossdressing Memories

    I first started crossdressing about when 8 yrs old by trying on my older sisters clothes out of curiosity and boredom, and found it great fun. But when puberty hit at about 13 yrs it was a whole new ball game (get it). I just couldn't believe the feelings and arousal a simple...
    femprini femprini
    56-60, M
    33 Responses Mar 25, 2011
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