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When I was growing up I happened upon a few great opportunities to do what I always wanted to do in public. In elementary school I was asked to play the role of "the Prince" in the school play and in front of the whole class the drama teacher asked one of the girls to loan me a pair of red tights. Of course it got better when we performed in front of the parents, because under the lights for that performance I got to wear some makeup too. (just as an aside - that is when I knew I was a little different).
The second time came in high school when one day while hanging out at my girlfriends house she she suddenly said to me "let me put make up on you, I think you wound make a pretty girl." Her sister was there too and the two them started giggling and pushing me to allow them to do it. Well of course I accepted - after offering some weak resistance to hide my enthusiasm for the idea. It was wonderful of course. It was the first time I wore eyeshadow (it was the 70's so we are talking bright blue). I was amazed at what I saw in the mirror, and very excited. I kept hoping that the two them would take it to the next step and talk about a dress and pantyhose - but alas it did not happen and I did not have the courage to ask. I did once suggest to her that we do it again - but she shot me a disgusted look so had to say I was joking.
The third time was the most strange. I played high school football and as the playoffs dragged into November it got cold. Long underwear was pretty clumsy and lose fitting in those days, so one day a couple of the players started talking about wearing pantyhose under our pads and football pants to keep us warm. So of course I chimed in and agreed it was a good idea. That was the first time I went to a store and bought pantyhose for myself - and remarkably I did with four or five other guys doing the same thing. Of course in the dressing room I decided to face the wall when I put them on, not wanting to risk inadvertently demonstrating to the other players that I liked wearing pantyhose more than they did. It was a strange but wonderful thing.
Finally, when I was a waiter in a restaurant working my way through college, a co-worker who was into crossdressing and drag shows kept telling me that he would like to do my makeup - but I have written about that in other posts and don't want to repeat myself.
Anyway - what about you girls? Any unexpected opportunities to do what you wished you could do?
well I only have one but it was SO GOOD! I was in a film class in high school and teenagers hate acting and asking people to ask, so I was kind of the go to person for being in other people's films. I ended up in a group where I had to be the main character's girlfriend, I even came to the set, the director's house, in my dress. I said I borrowed my mom's dress and they bought that and they said I made a convincing girl on film 🙂
Cool - sounds like great experience. Don't you love it when great things just fall into your lap?
The first time, I don't remember how young, (early grade school?) I wanted to be a witch for Halloween. I had envisioned a black dress, pointy hat, big nose, warts, the works; but we were a poor family and my folks were the "make due with what ya got" type. My mother took her wedding dress (early 50s style) and proceeded to alter the dress to fit me. I was a bit disappointed - it wasn't what I envisioned but making due I was the white witch for that night and certainly happy.
The next and last time was in high school drama class my senior year. We were studying stage makeup. My partner was a girl 2 years younger. I did her makeup and she did mine. At the time I had beautiful hair down past my shoulder blades and of course only shaved once a week as if my beard grew that fast (yeah pathetic for a teenage boy). We had agreed that she would do my makeup to make me "look like a girl" and of course I went up on stage and flaunted it. I remember it was probably the most significant day in high school that I ever had. I was excited, and I really tried to sex it up. Of course the critique of the makeup (yeah back to class) kind of blew the wind out, but still I flaunted it.
Sad to say no makeup again until my 60th birthday.
My fifth grade year was my first time I was in a play playing a king and had yyyy o wear tights and a silk shirt I didn't want to take them off when I was done the second time I went out for Halloween as a hooked and won second prize in the customer contest only being beaten by another guy who came as a women secretary I haven't gone out since but two great memories
I hate spell check sometimes it was supposed to be to wear tights and a hooker
Until this post I forgot that in 5th grade I had a similar experience where I was in a school play and got to pull on tights for the first time. It was such a cool feeling!?. I didn't know where it was eventually leading but I definitely enjoyed it!???
