Crossdressing to Bi-Curious, Did I Miss Something?

Transgender symbol
Credit: Wikipedia

For as long as I can remember, crossdressing has given me a feminine side that I truly couldn’t live without. Also, as long as I can remember, I’ve always been what they would call “hetero” with typical vanilla relationships with women.

Being the coward I am, I’ve never been able to share my alter ego with any of my past girlfriends. God forbid their reactions or, gasp, laughter if they reject my inner woman. Worse, what if one of them let the cat out of the bag to one of my friends? I’d have some explaining to do.

In that time, though, the inner woman grows up and wants more out of herself, to look more passable, be more sexy.

Not to mention feel more like a woman would too.

Ok, that is somewhat difficult since there is that matter of male genitalia getting in the way even though it’s used to enhance the “female” pleasure. Let’s not lie though. Wanking it is about as male as it gets and, after years of rinse and repeat, is about as vanilla as the hetero relationships too.

It’s time for a new way to express myself sexually but in the context of a women. So fantasies of being a slut or porno star and getting gangbanged enter the picture. In other words, how sexy would it be to be fucked for a change? Or suck the proverbial golf ball through the garden hose?

I’ve pondered this bi-curiousness over and over and I just couldn’t help myself. The thought consumed me enough to force me to buy a lovely silicone dildo for practice (and pleasure). At least it was a sort of try-out before I actually consider the real-deal sex with another thrusting (ideally transvestite) male.

Yet there was always that one question continuing to linger that had to be dealt with. Won’t this make me gay or, more correctly, bisexual and would that change me?

I’ve concluded that, fuck yeah, I hope it does BUT it wasn’t exactly easy to come to terms with this.

Being raised to be hetero confined me to those bounds pretty much all my life and was a part of my belief system. Sure, crossdressing went against that but that is just my little secret fetish. I was still only attracted to girls. Changing that belief is kind of hard if you live it your whole entire life.

So what changed? Self acceptance. I am who I am just like you are who you are. When you really think about it, too, aren’t we are all weirdos with skeletons in our closets of some form?

So, after stopping to think about my own perversions and broken taboos for a second and beginning to realize that most people have a dark side to them, I came to a realization: why even fuss with my own sexuality?

Don’t get me wrong. I’m not trying to rationalize my bi-curious self to you, the public. Surely, other crossdressers and transvestites out there must have gone down the same path (and then “went down” it ;)).

Now moving on to sex with that transvestite…

19 Comments on “Crossdressing to Bi-Curious, Did I Miss Something?

  1. Same dilemma, different person, I understand all too well. I always crossdressed, loved the feminine feel and look too but all the while I felt that I was a 100 percent hetero guy and that dressing up and sex had nothing to do with what gender I was dressed as. I told my wife long before we married about dressing and the thrill I got but that I was not bi or gay, trust me she asked me about it and I really believed I was straight and that when I told her that I was telling the truth. It wasn’t until I was about 40 that I started imagining myself being dressed and finding myself attracted to men. When I am not “en femme” I am not attracted to men all that much but when I dress up I am all woman and want what a woman wants, a man! I find myself able to have sex with my wife when she needs it but what I really want is to dress up and go out. As far as the “most crossdressers/transvestites are straight” statement that I have always heard all my life I highly doubt that, I bet the truth is that most of us are bi and some are straight and some are gay. I know I am bi/gay, perhaps 75 percent gay since I still can do it with my wife even though my preference is men. Frankly I would be surprised if almost all crossdressers weren’t bi, just my two cents.

  2. Hi Sheery,

    Great article and as ever eloquently written! Also, good answer, Charlie!

    My sexuality is also quite complex, I had my first sexual experiences with a 14 year old boy when I was 8 which left me feeling very screwed-up until just 4 years ago when I finally accepted I was bi…To add to this, my pantyhose fetish started when I was 11 and up until just last month when I told my wife(she accepted my bisexuality when I did) about my fetish and she has also been completely accepting. I have also had a lifetime of feeling guilty about this too..I think all of us have gone through the “collect and purge” cycle??

    With my first wife, I came out as gay to her at the end of 1995, and she tried to help me to be totally gay by sending me out to the gay village near where we lived. I had a few gay experiences which I am very glad to have done though emotionally I just cannot connect with guys as I do with women. Trying to identify as being gay did not fit at all and led to severe depression which ended with the marriage breaking down as well as my suicide attempt..My first wife also knew about my pantyhose fetish, which she accepted but I guess in her mind she just saw it as a large homosexual element to my sexuality which of course it is not..

    Another element of my sexuality are my fantasies, these are always completely homosexual yet in reality there are very few men I have been attracted, my attraction is to women…I love the sight of cock though, and consider myself to be a “bottom”, according to a really good bi-forum, this seems to be quite common for bi man to be bottoms…

    I think my biggest fear was that I was a closeted gay and identifying with being bi just makes you “gay-lite”, which was a huge internal hurdle to overcome…

    The reality is that when I look back on my life and my sexuality, it has remained pretty consistent for most of my adult life.

    Now, thank God, I am now free and have a loving, accepting wife who even buys me pantyhose!!

  3. I totally agree that most CD’s are bi. I just don’t see ANY evidence to the contrary. I think the ‘statistic’ was arrived at using a very small demographic and a small small sampling at that. If a PROPER study or survey were to be conducted, across the entire country (or world) and across ALL demographics, I’m sure it would be revealed that most crossdressers are not straight but either bi or gay. Even one time will make you bi and there’s nothing wrong with being bi. I started pretty much as everyone else has, and just like everyone else, my hand just didn’t cut it anymore. I remember my first time, what a thrill…and the next two dozen times were just as thrilling as will the next time be! The thrill of pulling on my sheer pantyhose, a nice black minidress or nice top and miniskirt, strapping on my 4″ fuck-me shoes and heading out the door. Driving to his house or meeting place fully dressed, getting screwed and going home feeling so satisfied, so complete. You’ll never forget the experience and chances are you’ll be hooked and it won’t be the last time. There’s just no feeling like it, the nerves, the excitement, the thrill, the contact, the initial stretch and penetration and it doesn’t last long enough nor does it happen enough, but if you’re sitting on the fence about going all the way, my advice is, go for it. Be careful and use caution of course, but don’t let life pass you by. Believe me, sitting on a cock beats sitting on the fence!

  4. I am also a believer that most cross dressers are bi, not heterosexual. I base this on the millions of posts I have read about men who wear pantyhose since 1993. I have rarely come across a man who wears pantyhose and who has no affinity to looking at photos of other men who wear pantyhose. Many man state that they are straight but when they wear pantyhose, they become bi-curious. I think this stems from the fact that men who wear pantyhose absolutely love seeing themselves in hose: they love the sensations of sheer nylon fabric on the skin, they love stroking themselves through the sheer fabric, and anything related to sheer nylon is erotic to them. By extension, any photo of another guy wearing hose will intrigue them and they will not be averse to viewing photos of other men wearing pantyhose. To a certain degree, we love our hosed cocks so much that we start to appreciate any other hosed man and start to crave spending time with another man in pantyhose. This is not based on statistical fact, simply based on thousands of hours or surfing the internet and finding other like-minded men who love to wear pantyhose.

  5. U just described my story n e ways if ur up to fullfillin those fantasies i would love to oblige u and vise a versa.

  6. I totally agree with you all when I first started wearing tights (pantyhose) I just loved the feel of them on my legs and my c..k but I was never even thought about other guys on them until
    A few years ago then when I started dressing up with my wife
    we started watching crossdresser porn thats when I wanted to try being with another crossdresser or gay men who wore hose .my first time was with a gay guy who never wore hose before but he had them on for me when I went to his place then when I saw him in black 10 denier i just had the most amazing sex with him. I never saw him again not for the want of trying. Unfortunately where I live i dont get much opportunity to have bi or gay fun.x

  7. i feel your pain friends ,feel the same way exactly , is nylon do a chemican change to mans brain ? love ya ,Deva

  8. Im a married man been with my wife for20 years now the last five years she’s known about me cross dressing in pantyhose high heels etc. She also knows about my pantyhose fetish .IV been wearing pH since I was five years old but she don’t know is that I’m getting curios about being the women for some men want to try it . I don’t know how to tell her that hat . she does fuck me with a dildo and is cool with it

  9. Honey she has already accepted that you are curious about cock but I bet she wants to watch. I know plenty of women both gay and straight that get off watching two guys, CDs and everything in between getting oral with it. In fact you find like myself that it will get you so hard giving head that it will be a real problem to stop giving blowjobs. So buy some over the knee boots and make yourself comfortable because you will spending a lot of time sucking and swallowing. Tata for now LD69

  10. I’m a straight male that dresses as a women time to time pantyhose bra dress high heels etc. I enjoy it a lot .I’ve always worn pantyhose since I was around five .but I been for several years now fantasies bout being banged by several men at once . I use a dildo on my of often and enjoy it so much .I fantasies bout I’m being raped by several man at once. So am I bi curious

  11. Bi-sexuality is not the only thing. Cross dressers fanasize about it. Some act on it. I have thought about it and I will eventually probably act on my feelings for those who also cross dress. The idea is intriguing. One can feel at ease with another person who shares similar attributes. I am so excited about this prospect of my life as a result of this experience as a hidden cross dresser. I want to come out to another who is a good person to talk to. It is quite a exciting and wonderful experience to feel like a person who has been a long time in hiding. I have a need to express my feelings for another person who is understanding.

  12. Serum Felice you where so right she wanted to be there on my first real cock. I imagine it being great dress as women I did have doubts about about sucking it but it was part of my fantasy and having to swallow the guy I meet was cool and understanding which advice me not to swallow lot for first time if that’s what I wanted gave lot of helpful advice but I had to be forced on sucking at first then got into it and it does get you so hard I sucked for two hours straight the cock in me analy was the best feeling as well as orgasm I as well as wife was worried if I was gonna want that more than her but it’s been good our thing now if we want to spice up we find couples that goes both ways ty

  13. When Dressed…Of Course I Would Rather Be With My Man…When He Sees Me In My Bra…He Just Can’t Keep His Hands Off Of Me…And When I Am Wearing Nylons…”WOW, WOW, WOW” !

  14. I finally took the leap. I found another person to share my love of cross dressing. Having had many a blow job from women I know exactly how to best pleasure a person’s phallus. Toys are fun and Cialis is good too. The trick is too tease a bit and certainly take your time. If he has a fetish like most men, take a nylon stocking or silky panties and wrap them around his erection. Slowly slide the panties up and down his shaft using the smooth material to tittilate him. You can also have him give you a nylon “thigh fuck”. Rubbing his erection between your silky legs.

  15. I read a joke:
    What’s the difference between a Crossdresser and a trans woman? About two years…
    I have always been bi but haven’t always been able to accept that. As I’ve grown more comfortable with my own feminine expression I have also gotten comfortable with the fact that I like dick. I see more women that I’m attracted to than men but when I see a guy that I’m attracted to the attraction is WILD. There was a point when I could see sec with a guy but not intimacy, holding hands, kissing, all that, I think that was a part of the lack of acceptance of myself. If I’m attracted to a guy I get the same feeling of a desire for touch and intimacy with him as a woman.
    Now, with so much other femme behavior I’ve become accustomed to, I DO think about hormones. Being smoother, fat moved around to feminine areas, tits, that’s really appealing to me, enough so that I fantasize about having an orchiectomy. I guess the joke wasn’t too much of a joke at all

  16. @Dennis In my experience, as I’ve grown more comfortable with my femininity, I want to evolve it further in my appearance, behavior and even sexuality. I can say I am bisexual, however, I am definitely not at the stage where I can see myself taking hormones or thinking about making a permanent change to a woman. Who knows what the future holds though? So, I definitely can’t rule it out either.

    Thank you for sharing your story. You seem to be happy in your own skin which is the most important thing and I hope your future holds all the fantasies you desire which sounds like fun. You are not the only one. X

Leave a Reply

Your email address will not be published. Required fields are marked *


This site uses Akismet to reduce spam. Learn how your comment data is processed.