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hetero male crossdresser has a question

Crossdresser phone sex with Mistress Olivia 1-800-601-6975

Olivia 1-800-601-6975

Are you a crossdresser?

What exactly does that mean?  It generally means that you’re a man dressing in woman’s lingerie or female clothing.  BUT, you know that I realize many of you actually ARE female and (for lack of a better term) put into the wrong body.  It’s sort of like ordering a dress in pink and getting the dress in blue.  There are many labels for men who like wearing women’s clothes.  Remember only YOU can define who you say you are.  A label is only a starting point.

Are all crossdressers gay?

Short answer … NO.  Longer answer, crossdressing does NOT mean you are gay.  YOU are unique.  Your dressing has many motivations and styles of expression.  These can and will change.  That’s part of the fun of life!  I got this email from someone who describes his love of dressing en femme beautifully and uses a great analogy!

Hi Olivia,

I’m not a big fan of labels generally, whether in this context or any other. I was having this conversation with my bro-in-law just yesterday, who’s a keen and committed cyclist. I love riding bikes too – in fact it’s my job (those legs are the result of many hard hours in the saddle! ;)) but I’d hesitate to tag myself ‘cyclist’ just as I don’t see myself as a ‘motorist’, even though I drive 20,000+ miles in a year. But I digress…
I’m not TG, because I’m happy with the male ‘me’ 99.9% of the time. I do have a need to express an inner femininity though, in this rather peculiar way that I don’t entirely understand i.e. to dress in an overtly feminine way and to allow myself to experience and explore the sensual and sexual feelings that go with that dressing. So I guess that makes me a male who likes to dress. I’m acutely conscious that dressing doesn’t make me female in any way at all – in fact, most of the things I love about women (speaking as a hetero male here) have nothing to do with what they wear. Dressing is therefore pure fantasy, but one that has a powerful hold over me. I clearly can’t change it, so it would be a good idea to come to terms with it instead.

How do you describe your crossdressing?

Does that quote resonate with you?  How do you describe who you are and why you like to wear women’s lingerie?

Ms Olivia

12 comments to hetero male crossdresser has a question

  • Peter

    I just love the soft smooth silky fabrics against my soft smooth skin. It all began with ginger & Mary Ann. They were hot I that’s where I got hard. I’d love to be on island with then and have nothing but women’s clothes to wear. As I said before it picked up when I was (younger) and I was underneath mistletoe and my (hot neighbor) kissed me. It left lipstick mark on my cheek. Then she had me sit on her lap and she kissed me. She was 32 and hot. She would sit on my lap and smother my face with lipstick kisses. When I was home alone I would sneak in her room try on her perfume & lipstick. I got so excited. I think she knew but she never said anything. Then her and another neighbor lady put rouge on me. I felt so helpless. But I couldn’t do anything. It turned me on. Later in life while waiting to do laundry I spotted my room mates girlfriends bra in basket and that did me in. I put it on and I was hooked for life. I then started buying bras/panties/lipsticks/perfumes/lotions dresses. It’s been 15 years now and I can’t nor won’t stop cross dressing. I’m hooked. I’m not going to try to find women to share it’s to much a risk. I don’t need to with you and other mistresses who like to do this. Also this is only way I can get hard and off. I really do want to get busted at Victoria’s Secret by girls I know. Then I’d come clean. I’m ready to come out but don’t want family to know. I need to do this every night. It’s healthy way to get off as I’m on pills for next 3 month cycle and pills get me hard so I’ll be getting off. I have call with Ms Cathy and Ms Violet tomorrow night and they want to have way with me in full corced feminization transformation of me. They both said once I do call they have no intention of letting me go and I’m more then fine with that as I want to do regular calls weekly for 30-60 minutes. It’s safer and better way of having hot sex and beats going to bars.

  • Peter

    How is Ms Cathy? Is she into turning guys into girls? Ms Violet told me it’s been way to long in between calls and she want to dig her hooks into me and not let go and do total transformation of me.

  • Peter

    I will. I have pink sheath along with 4 maiden form pink boy shorts,3 racerback girls tank tops, and form fitting slip coming Tuesday.

  • Peter

    I also left comment on blog in sissy vile blog where you know my cross dressing secret. Will comment on that also?

  • yvonne

    Ya know reading this it really describes how I feel about this. I really like the analogy. For myself most days I am happy to be male get with my mates and hoist a few pints. Then there is that day that I just have to feel the softness of a dress on my legs and the dangle earrings in my ears and the hair on my shoulders. It does have a strong hold on me and pretty much I am at peace with it. It is maddening sometimes but that is what makes for horse races. When you really look at our motivation for dressing it seems to be mostly about feeling the sensations and hearing the sounds and smelling the lovely aromas. Even the feel of makeup on your face has an allure. Certainly seeing the pretty picture in the mirror is a sensation. It is all very erotic. The scenes you and I talk about certainly are.


    • olivia

      LOVE your comment yvonne!! I think it’s normal for human beings to want to put labels on things, people, activities….it’s a way to quickly make sense of the massive amounts of information and sensations around us. I find the label useful … but only as a starting point. Because as we both know, there are MANY variations! 🙂

  • Sara

    Isn’t the gender fluidity thing interesting? I posted a question on a TV forum recently: what do you like most about dressing (en femme)? The responses varied a fair bit, but split fairly clearly along cross dresser / transgender lines. CDs tended to identify with the feel of the fabrics and the ‘differentness’ of female over male clothing, as well as how the sensual feelings that that created in them. TGs, on the other hand, were much more prosaic in their answers. “It stops me from getting cold” was a typical response.
    I suspect this tends to reflect how men and women react differently to female clothing. While I’m sure women enjoy many of the same things that cross dressers enjoy, female attire is more “normal” for them (natch) and not hardwired into feelings of sensuality and sexuality to the same extent.
    It’s one of the reasons why I often think it’s unhelpful to lump CDs, TVs and TGs into the same group. As you rightly point out, Olivia, everyone is unique 🙂
    As for the CD = gay thing, it’s a common misconception which, I believe, has been shown empirically to be complete nonsense. Although… again, everyone is different. I began to realise a couple of years back that I had a fantasy of sucking a dildo while dressed. Which is odd, because the thought of sucking a real cock is… just yuck (though I accept that of course that’s not the case for everyone ;)). But acting out a fantasy, doing a little role-play while pretending to be female… that was just so hot :). What made me realise this was OK, ultimately, was sharing it with my girlfriend, who reacted by buying me a lovely pink dildo for Valentine’s day ;p

    • olivia

      I love love love hearing about your relationship sara and thank you so much for still coming here to share your experiences! I think you’re spot on …. AND the love of female clothes/fabrics also happen with people who really aren’t even crossdressing — they’re wearing the clothes, sure, but don’t consider self as a crossdresser. I think life is nuanced …. and oh yeah, sexuality is even MORE nuanced!