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Thread: Sexuality and crossdressing

  1. #1
    Senior Member phili's Avatar
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    Sexuality and crossdressing

    I thought it might be useful to try to discuss the evolution of a variety of sexual feelings with respect to crossdressing.

    I started out at age 4 as a crossdresser before i understood sex as something with others. I enjoyed the sexual arousal in the smooth front of my sister's plain cotton panties, compared tto the ribs of the Y front tighty whities I was issued.

    As a 7 yr old I was more interested in the world of girls and wearing their clothes, but it wasn't sexual at all.

    At puberty I refound sexual arousal and babydoll pjs went together well. I tried to figure out what made skirts fun for girls if they didn't have an erection, and began to enjoy the swish on my thighs and begin to notice a larger variety of clothes. I began to feel the sexual tension and wish I could be on their side of the equation.

    As a 15-60 something I would say it looked more like a sexual fetish, but the details in hindsight tell more. I would find some piece or two of sexy lingerie and wear it. I would feel at peace, but needed a way to do something exciting or active or somehow engage with it. I could enjoy the arousal, and the simple unaroused comfort, and I didn't want to take it off, but it didn't work in my life as a man, so I needed a way to end the connection and hang up the call, so to speak. Orgasm worked, and I could find relief and forget about it for a bit.

    Then I retired and became an empty nester. I still wanted to wear women's clothes, and not just exotic lingerie. I wanted the simple nice filmy blouse and skirt, or even just a colorful garden party dress over the knee and swirling around. Shorts and halter top. Swimsuits! I'm on a voyage of discovery, catching up on all the clothes I never got to wear.

    The variety and beauty and style are my playground. I want to go out and share my style with others. It isn't about sex as orgasm, it is about sex, or more accurately, gender, as femininity. The background is the male/female reproductive sexual tension and interplay, but it is not the main point.

    After more hours in the dress, I might feel none of that either- just hungry or sleepy or bored, or sweaty, and my clothes are just clothes. I don't like that, but clothes need to recede from focus so I can pay attention to anything else. Then they are more of a uniform- check ourselves in the mirror and then forget about it.

    Looking back, I am now convinced that acute sexuality with arousal and orgasm was never the point. The simple sensual pleasure of a dress is enough, and the feeling of being identified as a woman, or at least a feminine member of society. Sexual play can involve clothes, and clothes can hint at sexual interest or readiness. Sexuality can be part of cross-dressing alone without it degrading the validity of our desire. It can be part of sex with others, though I found it kind of becomes irrelevant quickly if we are not objectifying each other!

    And at any age sex as an issue can also recede naturally and not be part of fully enjoying crossdressing at all!

    My post is to start a discussion that takes the guilt out of our sexual dreams.
    We are all beautiful...!

  2. #2
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    Thanks for posting that. In my normal life I don’t “feel” sexy I’m just who I am but when I put on a tight dress and lovely stockings and heels , I actually feel “sexy” and I get pleasure from that. Yes I can go around the house and feel sexy and I want to make that feeling last.

  3. #3
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    Great post
    I think you brought some great points about feeling sexy and good vs sexual
    I think probably most women understand this far more, better than men

  4. #4
    Member Chelsea B's Avatar
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    Great perspective, Phili. A very thoughtful and articulate post that resonates with me. However, when I first stated in my early teens, it was all about sexual pleasure, to the extent that I couldn’t wait to get those clothes off, in guilt and shame, after orgasm.
    It’s a far more interesting and profound ride now, in my sixties.

    Chelsea
    Not a woman, I just enjoy looking and feeling like one now and then!

  5. #5
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    For me the initial wearing of women's clothing was my mother's full slips. She hung them to dry in the sole bathroom or on a clothesline in the hallway to the bedrooms in our apartment. As a young child I had to pass through the mass of drying clothes and come into contact with those nylon slips. I was drawn to the fabric. Nylon was like no other fabric I ever felt. I would fondle the nylon slips. Finally I got the nerve to take one off the drying rack in the bathroom and try in t on. I did the same with her floor length nylon nightgowns. There was no sexual motivation. I was probably five or six years old. I was young enough that I had to stand on the edge of the bathtub to take the slips off the drying rack.

    When puberty hit sexual motivation hit. As many have stated over the years of reading here there was shame and guilt. One for trying on women's clothing. I'm sure if I did it purely as a lark there would have been no shame or guilt. However, back in the 1960's crossdressing men were viewed as homosexuals. Society was not what it is today. No acceptance. It was a time of confusion for me. Was I a homosexual? It did not seem logical since I really really liked girls of my age or starlets. I drooled over Annette Funicello while watching the Mickey Mouse Club, and, then in the various Beach Party movies. Thoughts of possibly being gays drove me nuts. Damn, I wish this forum was around in the 1960's. Where was Al Gore when you needed him the most?

    Now? Wearing women's clothing is nothing more than wearing something to reflect how I feel on a given day. Some days it is my guy clothes and several days of beard growth. Like today. Some days I feel so natural wearing a dress, hosiery and heels, and all the undergarments and doing domestic chores. No sexual motivtion. No sexual enhancements. Just another day as a woman.

    A counselor who I see for PTSD war related issues is of the opinion each man and each woman has some component of the other sex's DNA in him or her. That's the best explanation I can see as to why that influence arises on some days and not other days.

    Once word or phrase I have to take exception to is "fully enjoying crossdressing." I find it is not a matter of enjoying. It is a matter of just doing something that is natural, part of my inner being even if it is a small part of who I am.

  6. #6
    Weirdest woman ever! docrobbysherry's Avatar
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    I think my case may be VERY DIFFERENT from anyone else's here, phili:

    I had NO gender issues until after age 50. At that time, I was just separated from my now ex. And, had plenty of private, alone time when the kids were at my ex's. I was despondent and seemingly had no interest in women or sex. But, I began having gender issues and to experiment with dressing. Finally, my interest in sex returned because of Sherry's appearances in my mirror!

    That was over 20 years ago and she still inspires me to--er---greater heights!
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

    Challenge yourself and pursue your passions! When your life clock runs out, you'll have few or NO REGRETS!

  7. #7
    Platinum Member Teresa's Avatar
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    Phili,
    I told my story sometime ago in the TS section.

    The early years for me were so different to your's . The clothes never attracted me , I was more ebarrassed by early erections, they were a total mystery . Then it all happened with a bang at the age of 8-9 years . I became attracted to a swimsuit , not to wear to see how it felt but something had clicked inside (I guess the T had kicked in ) , the item suggested a womans body , my mind wanted sex with it and but as young boy I didn't know why. After wearing it a few times my first orgasm happened , I found it more traumatic because it was an involuntary action I didn't induce it . I really knew nothing of why and what had happened , I describe the events as a combination lock being set in my brain with no key to unlock it . I now realise that my male side was driving me through T kicking in but the clothes were the need from the female overlay and the whole situation was bound together by sex , I also feel that it made such a deep and lasting impression because of the traumatic way it happened , many young males don't experience that situation for up to ten years later . After all these years I've finally lost the gut feeling that started at that point , it's only now I can dress freely and feel comfortable from ther legacy of those early events .
    I admit sometimes it is still sexual , but I find that an annoying distraction at times , if I'm still a fully functioning male there's not a great deal I can do about it . I did raise the question of what happens when the T finally fades away either natuarally or through hormone intervention, truthfully I admit I love my dressing now , I would hate to lose the enjoyment , comfort and happiness it gives .
    Last edited by Teresa; 07-07-2018 at 01:51 PM.
    The real me ,no going back.

  8. #8
    Stand-up Comedian En Fem❤ Alice_2014_B's Avatar
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    There is something about trying to look as passable and sexy as possible that brings me a feeling that is kind of difficult to describe.
    That being said, I'm sure at least 95% on here know what I am talking about.
    Melissa: "... and why are you dressed as a woman?"
    Coach McGuirk: "Because it's freeing."

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  9. #9
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    After being dressed up by my elder sisters at a very young age, perhaps about 5 or maybe 6, I embarked on a journey of sexual discovery through dressing up in lingerie. Feminine clothing, especially lingerie, had an extremely strong sexual connotation with me and I was regularly achieving orgasm through dressing and using the physical stimulation afforded by those soft materials well before puberty.
    So, for many years after I was able to read about transvestism I believed that I just had a fetish for lingerie, especially full slips. Later in life I discovered the pleasure and comfort of dressing fully in female attire and wearing wigs and makeup to make myself the best facsimile of a female that I could manage.
    Even now I slide back and forth between the wonderful feelings of comfort and well-being that I get from dressing and the sexual charge that comes with it.

    We all have had very different experiences and so our cross dressing journeys are many and varied. But I hope that the members of this site remain open to the wide range of experience and expression in our community and remember that when we expect tolerance we should also practice it .

  10. #10
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    Yes Alice exactly the feeling I was trying to explain

    JAS

  11. #11
    I accept myself as is Gillian Gigs's Avatar
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    Phili, like you, I had my first experience at the age of 4, but mine was not a pleasant one at the time. Before puberty set in I went back to it for unknown reasons (I know why now) and experienced a euphoria that kept me going back. Then, with puberty setting in things changed. CD'ing became a very sexual thing until my mid 40's. At that time, the lingerie wearing became just as important, and at times more important than the sexual release. This has grown to the point of the clothes being way more important today (90%). I would be a liar to say that there is still not a sexual aspect to dressing. That tactile feel of nylon against the skin still has a strong pull for me. Today, I love skirts, but why wear a skirt if you are not going to wear hose of some type at the same time. This evolution has gone from a guy with a fetish to a guy who likes feminine under clothes. Maybe they are the same to some people, but I am the one who accepts myself, and I see a difference. My lingerie dressing is such a second nature to me that I don't think about it much anymore.
    A comment made says, " My post is to start a discussion that takes the guilt out of our sexual dreams." Funny I haven't had a sexual dream in a long time. When I did have sexual dreams they were usually about wearing bras and panties. With wearing panties all of the time and bras as I choose, it kind of takes the wind out of the sails! Suits me fine now.
    Last edited by Gillian Gigs; 07-07-2018 at 04:49 PM. Reason: spelling
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  12. #12
    Aspiring Member Rayleen's Avatar
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    Philli.

    Starting at a young age, I was admiring some of women visiting my Mom. looking every detail of their nice soft and colored blouse and skirts.

    I wondered why women dressed a lot prettier than our grey trouser and dull colored shirts.

    Sometimes, our neighbours kids were at the house on Saturday and we got to go in Mom closets and play dress up. Wow what fun and sexual excitements.

    At puberty, began exploring wearing lingerie and it was sexual arousal every time.

    Then it was a quit time, going to college and being intern with a group of boys.

    It was after in my thirties that the passion reappeared, now it was more female gender appearance in dressing, it was stimulating without sexual arousing every time.


    Then I started going shopping , and it continued to today as it is a hobby and a de stresser .


    Now hooked on the wonderful world of CD .


    Rayleen.
    Wanting something is a fantasy which on a long time period clouds your mind and makes you think you need it.

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  13. #13
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    LuvTights - agree 100%. When I am in a bodycon dress, hosiery and stilettos, I feel absolutely sexy from the neck down. Dressed in regular man clothes and I do not feel sexy at all.

  14. #14
    Aspiring Member TheHiddenMe's Avatar
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    My wife always says I'm a walking contradiction.

    My urged to wear a dress date back to when I was 7 or 8, and had zero sexual connotations. I just wanted to wear the clothes.

    Fast forward to around the age of 14 and I tried on a pair of my sister's pantyhose--and all of the sudden I am ejaculating, which is the first time I can remember that happening.

    These days, I don't get aroused when I dress--but the idea of dressing is highly stimulating.

    Guy's sexuality can be weird.

  15. #15
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    I've gotten to a point in my life where I feel attractive both ways. I've noticed that I can turn heads dressed or not dressed. I still have the sexual feelings that come with quite a few crossdressers. They don't get in the way. Those feelings add more to the experience, at least for me. The build up to becoming Eboni is a feeling I can't replicate anywhere else.

    I used to have that shame/guilt feeling after release. Now its just a "I'm tired, or bored now" feeling. I may stay enough femme or change depending how I feel at the moment.

  16. #16
    Member Ronnie38's Avatar
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    This is an interesting and unusally apropriate topic to me as i have been dealing with stress and depression these past 4-5 weeks as a result of my dressing. I too started very young at around 3 or 4 and was met with imidiate rejection by my family. The desire and alure never went away.

    At around 12 or so it became for me a sexual thing. Givin my upringing in a homophobic family it became more of a confusion that i could not accept in myself.

    Later in life at around 16 i decided maybe i was gay and explored that possibility. The boy i was dating rejected me because i was a crossdresser. But the desire never went away. I explored with boys and girls but was met with a lot of rejection. I always felt that wanting to be femmenine was wrong and stupid because of it.

    I got married to a girl who explored crossdressing but more as a reason or excuse to cheat on me repeatedly. Fast forward to my current wife. I told her from the start and she and i explored in the bedroom for quite a few years. I began to realise then that it was more than a sexual thing for me and that i wanted to play the female role so to speak so i stopped dressing around her.

    Recently we had some talks, and still do, and i have started dressing every so often and trying different types of clothes and things like shoes wigs and makeup.

    There is still a desire to be sexual but its more about feeling sexy desirable and wanted. For me i just want to feel pretty. And not feel guilty about it. Its still a struggle because i dont want to become a woman. Its not sexual for me but being intimate while dressed is more exciting for me than when not.

    My shame guilt and embarassment never goes away though so it is still a struggle dressing with my wife or sharing my thoughts and feelings about it. My "girly" desires i have realized are not sexual but i enjoy being "sexualized" as a girl.

    I hope that makes sense.

  17. #17
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    Phili,

    My first experience with wearing female clothing came at about the age of 10 or 11. My sister, 3 years older, was in junior high school and had a nice selection of dresses and lingerie, which she wore for dances and a few other occasions. I wanted to be like her - i.e. experience dresses, skirts, blouses, stockings, etc. I would sneak into her room and try on her clothes. It did result in sexual arousal, but a seed was planted. Yes, I was ashamed but the desire to wear women's clothes drew my back to her closet and dresser. As I grew I explored my mothers clothes, etc.

    Looking back, I was not looking for orgasm, but rather it was about the clothes. Doing my marriage, I did dress in sexy lingerie with the intent to make love with the wife, whom I had told about my CDing before we were married. At some point during our love making, I took the submissive position and experienced attention getting orgasm. It became my favorite position during love making, and it probably was an indication of my trans-feminine identity.

    Underlying my life's journey I had a simple desire to wear female clothing. I have considered that I am curious about bi-sexual, but at this point I have no desire to explore any further. So today, wearing ladies clothing is not for sexual reasons, but rather to be authentic.

  18. #18
    Silver Member IleneD's Avatar
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    Quote Originally Posted by Alice_2014_B View Post
    There is something about trying to look as passable and sexy as possible that brings me a feeling that is kind of difficult to describe.
    That being said, I'm sure at least 95% on here know what I am talking about.
    This is a question my beloved wife has asked about my CD and motivations. What does it mean? WHO am I dressing for? Why am I trying to be pretty and WHO am I trying to be pretty for? Am I trying to attract other men?
    Maybe it's a question I can't answer or don't want to answer. Yet there is and has been a strong "F me" [in a good way], when I'm fully dressed and feeling pretty. "Take me! I feel beautiful". Somewhere in the back of a crossdresser's mind there's that underlying woman wanting to be taken into a man's arms. I think this happens even among the fully affirmed heterosexual CD-ers. "Take me. Pamper me. Make love to me." Come on..... confess that you feel it once in a while.
    There resides within me a Woman, and she is powerful.
    She has been my Grace and Bearing on the stormiest seas.
    I could no more deny Her than I would my own soul.

  19. #19
    Transgender Person Pat's Avatar
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    Quote Originally Posted by IleneD View Post
    This is a question my beloved wife has asked about my CD and motivations. What does it mean? WHO am I dressing for? Why am I trying to be pretty and WHO am I trying to be pretty for? Am I trying to attract other men?
    It's a question you have to answer for yourself before you can know where you're heading, but in my case, the answer is that I dress for me. Yes, I do feel the sense of looking fabulous at times, but it's all so I feel great, I don't really care what anyone else is feeling. The fact I'm dressing for me makes me pretty bullet-proof to others' opinions.
    I am not a woman; I don't want to be a woman; I don't want to be mistaken for a woman.
    I am not a man; I don't want to be a man; I don't want to be mistaken for a man.
    I am a transgender person. And I'm still figuring out what that means.

  20. #20
    Platinum Member Teresa's Avatar
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    Ilene,
    This was a question I asked some time ago .
    I agree it's not a simple answer , my conclsion was part of the equation was AGP . I know I don't dress to attract men but I know there is an element of dressing to please and attract a woman . I can't honestly answer what role I would play in a relationship like that if it ever were to happen at all . Unlike others I'm not saying never !

    I have to agree with Pat looking fabulous at times feels great in those circumstances I'll happily take the comments no matter who makes them .
    Last edited by Teresa; 07-08-2018 at 01:35 PM.
    The real me ,no going back.

  21. #21
    Gold Member Alice Torn's Avatar
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    Ilene, I know what you mean there. Only when i am dressed op, do i feel that way, pretty, sexy, gorgeous, and part of me wanting to be appreciated for it. But, NEVER, when in normal guy mode.
    IT TAKES A REAL DRESS TO WEAR A MAN.

  22. #22
    Weirdest woman ever! docrobbysherry's Avatar
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    I think Pat makes a good point. And, like her, I and I believe most here, dress for themselves. In my case, to the extreme. Compromising what I wear out is NOT something I enjoy doing. I really hate, "dressing to blend"!

    Apparently, (altho I don't really care), a lot of people seem to like Sherry's looks. I delete on the average, 3 to 5 "Friend" requests on FB every day!
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

    Challenge yourself and pursue your passions! When your life clock runs out, you'll have few or NO REGRETS!

  23. #23
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    I think , for me , it is about looking and feeling good . If you will having pride in what and who you are .
    Some are overlooking the fact that one can be appealing , appreciated by those ofopposite or same gender , but not necessarily in a sexual way .

    JAS

  24. #24
    Aspiring Member StarrOfDelite's Avatar
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    Quote Originally Posted by docrobbysherry View Post
    I think my case may be VERY DIFFERENT from anyone else's here, phili:

    I had NO gender issues until after age 50. At that time, I was just separated from my now ex. And, had plenty of private, alone time when the kids were at my ex's. I was despondent and seemingly had no interest in women or sex. But, I began having gender issues and to experiment with dressing. Finally, my interest in sex returned because of Sherry's appearances in my mirror!

    That was over 20 years ago and she still inspires me to--er---greater heights!
    I don't know whether we are both unusual, or whether there are a lot like us, but my story is very similar to yours, even to similar time frames. With the wisdom of hindsight i can remember incidents or moments in the past where I didn't look or react in a typically "masculine" manner, but those were isolated, and since I had no frame of reference from growing up in the 50's and 60's I never recognized that I was Trans. The incidents I'm talking about almost never involved sexual thoughts, they were just situations where I noticed that my reactions to siuations and events was different from "the guys." By the time I was separated, divorced, over 50, and not particularly interested in dating, I basically felt little drive to have a sexual relationship. I found, however, that I enjoyed the feeling of being intimate conversationally and socially with a woman was liberating, and I finally realized that it was because I identified with women, and really wanted to be a woman more than I wanted to have sex with a woman. It took me a while to adjust to that intellectually, and even longer to pursue the paths where that realization took me. I just feel more complete embracing that I am androgynous, and probably more female than male in my basic psyche and sexuality.

  25. #25
    Gold Member Alice Torn's Avatar
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    Starr, I am very much the same way.
    IT TAKES A REAL DRESS TO WEAR A MAN.

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