How Do You Know?

  • Creator
  • #36920
    Tiffany Sweetness

    Hi everyone,

    I am a 26yo male. I have had the desire to crossdress as long as I could remember.

    Here are a bunch of kind of stream-of-consciousness memories that have been on my mind as of late: When I was growing up, I wanted to imitate the way my grandma and mom talked and sat. My first crush was Ariel the Little Mermaid, but I also kind of wanted to be her. Also, growing up when I played “Batman” with my brother, I always wanted to be Batgirl. When I was 7 and through most of elementary school, I would have dreams of the other girls in my class turning me into a girl. When I was in 6th grade I would day dream in class of somehow being transferred into my female teacher’s body. In 8th grade, at track practice, a young girl said I was “pretty” and it made me feel like I was on cloud 9.

    I went to an all-boys school in high school and I hated it. I never felt like I “fit the bill” and I desperately missed having female classmates. When I was 17, I dabbled with some of my moms makeup and clothing. A year ago, I started buying some female clothing and makeup and attempted to dress myself up. This past year, I have gone for my first 2 professional makeovers, and both times I felt absolutely incredible. I ended going out this last time after my makeover. First, I went to a crowded Wal-Mart to buy a clutch bag. Next, I went to a trans bar. The girls there were super friendly and were talking a lot about transitioning. I had never truly considered transitioning before. I had always known that I liked to crossdress and hoped to have it be a part of my life, but now transitioning is on my mind near constantly.

    Any thoughts on what this all means? Am I really a woman inside?

Viewing 5 reply threads
  • Author
    • #83935

      Hello Tiffany,

      I completely agree with the advice of see a gender therapist. I can tell you for my personal experience that is the only one person can help you and guide you to know who you really are. As I read many of the answers as your own post too, I saw some experiences that I share, like the horrible feeling of was a “pervert”; but others I didn’t share, as early childhood knolewdge of “being a girl trapped inside a boy’s body”. The real problem in gender, is it is so diverse that everyone is a world in self so you are the only one who can answer the question you made.

      Best luck on your journey



    • #83889

      I don’t know.

      It’s something that has apparently been floating around in the background for a very long time, but I’m only just beginning to awaken to it.

      I’m a guy. I was born a guy, both physically & psychologically. I never really questioned it. But, the Universe seems to have a different take on it.

      I realised a while ago that I’m Bisexual. No issue there. But what I’m beginning to realise is that while I find women & men equally attractive, women seem to treat me more like a ‘girlfriend’ while many men want me to be their ‘girlfriend’. Some guys are gay or bi, & that’s all good with me, but others seem to see me as far more feminine than I ever realised, & treat me more like a woman than a man. Right down to doing the ‘Chivalrous’ things guys traditionally do for girls. And I don’t mind it at all.

      While I apparently walk in a feminine way (not at all by intent), have curves which are more akin to a woman than a man, & have hair & eyelashes that my sisters envy, my voice & face are both obviously those of a man.

      And while I’m quite happy living as a ‘guy’, I can’t say I’m terribly fond of what’s hanging down below, & the more I think about it would much rather have something more functional & fit for purpose for the role I enjoy playing for my boyfriends. And I’m now warming to the idea that having breasts wouldn’t be a terrible thing either. So, perhaps I’m something of a TG Tom Boy?

    • #82771

      When I was young, I was constantly admiring the girls, everything about them.  But mostly was interested in their clothes.  Where I went to school, all girls had to wear dresses, not the same outfit, but dresses of their choosing.  I was a leg admirer.  The more leg I saw the more interested I was in them.  It was that time when miniskirts were a big thing as well.  Once in a while I’d notice the edge of some girls’ panties under her tights or her pantyhose.  It put me in a spin, a locked memory of that sight which I recalled later at home while masturbating.  Back then the Sears catalog lingerie section was also a ‘porn’ section in my mind.  I masturbated a lot while admiring all that delicious lingerie and hosiery.  At the same time, I was ‘borrowing’ my sister’s lingerie and hosiery for personal ‘sessions’.  What a turn on it was, wearing it as well.  I thought for many young years it was just a fetish, but when I was on my own, wearing it was more of a requirement than a need to be turned on.  Throughout my youthful years, I tried several times to feel a girl’s nylon legs.  I was successful a few times, though only a few thought I was just a pervert.  In the 8th grade, the most beautiful girl in my class cornered me and allowed me to feel as much of her body as I wanted to all the while french kissing her.  I don’t know why, but it only happened once, and that was for about 20 minutes.  I was in awe of her sexy body, I was truly enjoying feeling her nylon legs and finally over her nylon-covered crotch which became moist.  I felt her breasts through her sweater and bra.  How I wanted it to never end, but also, how I wanted to wear what she had on.

      As I got older, the need to be turned on diminished, but my urge to be dressed grew.  I wanted to wear girls clothing all the time.  It felt right.  When I had the chance to get all dolled up and looked at myself in a full length mirror, I knew what I was, what I should be.   I wanted to be a gorgeous girl, admired.  And I was [past tense].  I invited some guys to meet me and was treated so nice, it only cemented my desire and need.   By this time, I had a wardrobe that would put most women to shame.   I was on my way.

      1 user thanked author for this post.
    • #53277

      CC Webb is giving you great advice!! Only you know who you are and what you want from life. I strongly suggest you STOP listening to other people’s opinions and go see a gender therapist!!! I too felt as you do at your age and I did not seek help eventually ending up on drugs, mixed up and in trouble. Find a therapist who specializes in gender and talk with them!!!!!!

      1 user thanked author for this post.
    • #52330
      Hey Sorry

      I’m having the same issue as well, my mum knows that I’ve had difficulty with my gender before and has helped me a lot when going through school. I questioned it when I was very young at around age 7 and asked my mum if I could be a boy, she explained to me how transitioning works and what I can do to question whether it’s what I truly want and everything she described… I felt. I’m worried about my dads friend as he has thoroughly expressed his dislike to the trans community and I guess I’m worried if I come out to my dad, he may tell his friend and his son is one of my best friends. I guess I just want to know before I mess up everyone around me, I’m questioning it again and I don’t want to be laughed at as I have severe public anxiety, I spend nights questioning myself because of it. Any advice?

    • #36944
      Miss Cloé

      It means you’re thinking about things along the gender spectrum.  Only you can tell who you are inside.  You do seem to be questioning things, but I caution that you don’t let others actions, choices and lives be the guide for yours.  You have the answer within yourself and the power to find it.  We’re here to support you as you do.

      Hugs, Ambassador Cloe

      4 users thanked author for this post.
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