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Thread: I need to share my crossdressing history and need input

  1. #1
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    I need to share my crossdressing history and need input

    I am 29 years old and have been crossdressing since about the age of 10 or so. I started out by trying on bras and panties I stole from my mom's drawer. I don't know why but I even stole a few panty liners that I wore just because it felt feminine I'm not even sure. Eventually, I tried on other pieces of clothing including dresses, tight pants, stockings and high heels. I also did try out makeup, lipstick and the like.

    I eventually came to realize that my obsession with crossdressing came down to a few items I REALLY needed. Bras, lace panties and stockings. Over the years, I would continue wearing them under my clothes at school or later at work. It wasn,t so much the thrill (because it was there) but the feeling that it felt just right. Fast forward a few years and I am coming out of a bad relationship that lasted five years.

    During this relationship, I would still crossdress in secret when my girlfriend was not around but I would never be able to wear them when I felt like it. After we broke up, the first thing I did was go on the shopping spree of my life. I had never shopped for women's underwear by myself since I always stole or borrowed them. I walked into victoria's secret with a huge "I don't give a damn" in my head. I bought so much stuff it was insane.

    I was there looking at the bra's padding, holding panties in the air to see how they looked gauging the size I would need and that would be appropriate for me. When I left the place, I felt too good, like a kid that just walked out of the toy store with an unlimited credit card. I just felt so good that day and couldn't believe I had actually done it. I had no regrets after and wore the stuff I felt like around the house alone and had fun matching clothing and just going on with my day.

    About a year later I met another girl and we started dating so I obviously stopped crossdressing because I really liked her and thought it would put her off. Eventually, I came out to her and told her everything. I won't post the details right now to not derail my post but I will explain after my story.

    I was VERY surprised by her reaction. She understood and was fully supportive. She asked me if I wanted to try on one of her bras and wear it during the day and I nervously said yes, I could hardly even believe what was happening. Things went on and I would basically wear panties and bras whenever I felt and we even went shopping together to buy some things for me that would actually fit.

    A problem rose a while later. I asked her during forecourse if I could slip on some lingerie. She accepted (probably in the heat of the moment and not because she genuinely wanted me to). We had sex but something struck me after the act: I enjoyed sex so much more if I was dressed.

    (post will continue, sorry for doing this but I am on my phone and I'm afraid of losing the post if I do it all in one shot)
    Last edited by Katey888; 12-18-2014 at 05:50 AM. Reason: Consecutive posts merged - please use edit post to add to existing post rather than adding a successive post...

  2. #2
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    Keep the info coming..I might have been where you are now Krystale!

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    We eventually came to the discussion about the fact that I might be gay. Of course, I know I am not gay but I do know I am not 100% hetero. Long story short, I don't even know where I stand right now. I feel like the man I should be yet I constantly think about wearing women's underwear yet this all goes away after sex. I also realized that I constantly look at other girls not because of their butts but because I am actually jealous of how they look and how I would like to go around looking like that.
    Last edited by Katey888; 12-18-2014 at 05:53 AM. Reason: TMI and prohibited content

  4. #4
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    Krystale:
    Just because you like to ear womans cloths, does not make you gay.
    I am 67, and have been a dresser since I was 4 or so.
    My first wife hated the idea of me wearing anything feminine, so after 9 years we split.
    I was single for 15 years, then met a real nice woman who was totally OK with me wearing
    female clothes. She even picked out things for me to wear. I never go out, I have a mustache,
    so that is a dead give-away.
    Show your GG friend this forum, she will see that there are a lot of people with similar
    notions of wearing fem clothes, and we are not all gay
    BTW Welcome to the forum, glad you found us.
    Rader

  5. #5
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    I came to realize that I don't even know who I am anymore. Am I really meant to be a man? Am I this way because of what I've done? Is crossdressing really all I want? The sexual side tends to tell me it's purely a fetish but when the fetish becomes your main thought through the day you start to ask yourself questions. I just feel like this whole thing is never going to stop, like it creeps up on you and doesn't let go. I'm at the point where I'm fantasizing about being a woman and having sex with a man. I just want to feel him inside me, I want to feel that warmrth, the feeling of being "his girl" and just let him do what he has to.

  6. #6
    Senior Member Gretchen_To_Be's Avatar
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    Krystale: You say you are certain you are not gay but then say you are not 100% hetero? Do you like men and find them attractive? Or do you say you are not 100% hetero because you like anal sex from your girlfriend? There is a difference...

  7. #7
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    I would consider myself as a bisexual but heteromantic. I crave sexual relationships with the same sex but would not consider actually being in a relationship with them.

  8. #8
    Senior Member Gretchen_To_Be's Avatar
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    OK then. I guess you need to be who you are and not agonize over it, there is nothing wrong with feeling the way you feel. I love to dress like a woman and would like to look completely like one, but I have zero attraction to men. May I gently suggest that you be completely honest with your girlfriend about this?

  9. #9
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    I would love to, but besides telling her "honey, I would just really like a man just once, just to see how it would feel", I don't know how to tell her. I am also afraid of the fact that I might like the experience and she obviously won't be able to replicate it.

    The part about the origins of my crossdressing I talked about earlier are about to follow. When I was about 6-7 (I think) my "stepdad" meaning my mother's boyfriend, would make me wear girl's clothing while abusing me. He would also force me to sleep as dressed. All of this happened while my mother was out working for the night. I also remember my pantyliner fetish coming out of this as I'm pretty sure he made me wear those so his "dripplings" woudln't stain the panties I was wearing.
    Last edited by Katey888; 12-18-2014 at 05:57 AM. Reason: TMI and prohibited subjects

  10. #10
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    I'm struggling here wondering if I've always been this way inside of me. Does the abuse actually mean anything? Has it changed anything? Would I be where I am today if nothing of this had happened?

  11. #11
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    If you were single, I'd suggest you have sex with a male to see how it feels. My SO went through an experimental stage years before I met him and this is how he was able to determine that sex with men didn't do it for him. But he definitely went through a phase of loving to have sex with me while dressed and trying all sorts of things.

    In the many threads we've had about whether members wanted to have sex with men, only a few have said that they have, they enjoyed it, and they consider themselves gay or bisexual; they have sex with men whether they are dressed or not. And if you read all the posts carefully, the majority do not say they've had sex with men. They rather like to keep it at the fantasy level and say they are attracted only when they are dressed, or they say they think they might be bi-curious (although why they just don't go out and determine whether they are bi or not is a mystery). I suspect that deep down they know that actual sex with a real man would be a turn-off since the experience of being one of two male-bodied individuals in bed would break the fantasy of being a woman, so it's a lot more fun to keep it as a fantasy.

    Consider the possibility that you are not turned on by men as much as you are turned on with the fantasy of having a female body and being a sexually attractive female, so the male in the scenario serves as a mere faceless prop with male body parts, to accentuate your fantasy. Or, go out and give it a try when you are single to determine how it really feels.

    You are definitely not alone here. I think that many (most?) CDers have shared your thoughts at one point, even if the dressing is no longer sexual for them, if I consider my SO to be pretty average.
    Reine

  12. #12
    Senior Member Nikkilovesdresses's Avatar
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    Hi Krystale, thanks for sharing your (ongoing) story and don't feel bad about the breaks, it's almost easier to digest having it a piece at a time like that.

    You're going to get a ton of feedback here, but just so you know you're not going through this alone- I have an almost identical set of fantasies, though I never experienced the abuse you describe - or if I did I've no memory of it. Unlike you I have experienced the mindblowing feeling of feeling like a girl being taken by a man, and from all you say I've little doubt you would enjoy it. I admit I hope to experience it again, but I find myself married to a wonderful woman who I have no intention of leaving and I'm a monogamous sort of guy. FWIW I went through years of being obsessed with this myself, but that need has more or less vanished now (I'm mid-50s) and I'm pretty much at peace with my straight sexuality. But at your age your hormones are in mid-flight and I can well imagine what you're going through. It may be that you just have to break away and experiment with guys for a while. You mustn't feel bad about that- it's perfectly natural. Your body will soon tell you what your heart truly desires. Another thing- it may or may not be that your fantasies are rooted in the abuse, but it isn't like you suppressed the memories- you know exactly what happened to you. You could go the counselling route, or you could just say- this is me, this is what I am, now where do I go from here?

    Hugs, Nikki
    Last edited by Katey888; 12-18-2014 at 05:59 AM. Reason: Prohibited subjects edited

  13. #13
    Aspiring Member LelaK's Avatar
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    If you follow Reine's advice and try to have sex with a guy, I'd go for "virtual reality" sex. That's the safest. Watch some porn of a guy doing it. Does the guy feel good to you there?

    Are you and your girlfriend monogamous? Would she approve of you having sex with others? Are you willing to risk losing her?
    T-shirt says: "Hi, I Crossdress!"

  14. #14
    New Member pinkDOT's Avatar
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    Wow... as I was reading your post, your dillemas, problems and uncertainties felt so strange and familiar. 50% of your post could be copied and posted under my name.

    -my exs did not fully understand that I wanted to wear their panties 24/7 or shop with them for the stuff I could actually wear. It was more of a "silly thing" -Dotty in panties, followed by "now take them off".
    -my last ex, who knows that its not a silly thing for me, wasn't thrilled and did not want to help me transform and enjoy my new lifestyle. That was a bummer...
    -as I am single now, I am having a problem with my orientation. I am bi curious and just like you, I would love to explore and have sex with a guy. But I have no idea if this is pure curoisity or something that my body wants.
    - i needed it like air but it would be silly to break up over something like that in a heartbeat.

    Take it easy, enjoy your life you're not the only one with thoughts like that.

    Xoxo DOTTY
    Last edited by Katey888; 12-18-2014 at 06:01 AM. Reason: TMI and prohibited subjects

  15. #15
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    Hi Krystale,

    Human sexuality and gender identity although they may seem linked/intertwined they tend to be two separate things. You have feelings/fantasies about being a woman "taken" by a man but in this fantasy you are a "woman" not a man having sex with a man. I am not saying you are not "gay" but it does not seem (from what I read) that you are 100 percent sure yourself as it all revolves around "fantasy play and being dressed". However, you have had a lot of trauma in your young life and this may be coming into play and, to be honest, I doubt anyone here is qualified to help you make sense of that and how it has shaped who you are today. My question to you is . . . Have you sought out therapy to talk through the abuse you suffered? If not, you may want to start there in order to bring a better perspective on how this is playing into the mix before trying to make sense of your sexuality and gender identity.

    Hugs

    Isha

  16. #16
    Martini Girl Katey888's Avatar
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    Hi Krystale,

    It does sound like the traumatic childhood experiences you have had must be playing a part in this... No wonder with all these feelings going on you are having a hard time to understand who you really are underneath all this - I have to say, I suspect you won't find the answer here, but the advice to seek counselling to help you come to terms with your past must be the best...

    You clearly have been the victim of some quite awful treatment - there is no shame in seeking help with that, and I would implore you to do so as soon as possible.... then you can try to understand whether there is more at play here or you are just exhibiting symptoms of the abuse...

    Good luck...

    Katey x
    "Put some lipstick on - Perfume your neck and slip your high heels on
    Rinse and curl your hair - Loosen your hips, and get a dress to wear"
    Stefani Germanotta

  17. #17
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    An interesting story and I am wishing for a very happy ending for you both. Let us know the next part.

    As I read this post and the comment about enjoying sex more while dressed, I was reminded of a scene from the film "Just like a Woman". If members have not seen this film I recommend it. The ending is rather contrived but many of the scenes about cross dressing got it right.

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