Missed Opportunities

[michellecd9999]

How many of you had opportunities to dress in the past, but did not take advantage of it?

For me, when I was a senior in high school, we had a "Mr. xxx (xxx = name of school) contest where the guys dressed as girls in a "beauty pageant." The event included swimsuit and formal gown presentation as well as a talent competition. I was a "band nerd" and was nominated first to represent the band. I was outgoing and known to do crazy things, but I was not thin or fem. I was embarrassed and although I would have LOVED to do it, I was afraid it would "out" me as a CDer. I refused and they nominated and elected another friend of mine (who was thin and I wonder if he was a CDer?). Anyway. I have since HS had many fantasies about going through with it and having several girls in the band help me with my look and wardrobe since I did not have a sister.

So what opportunities did you miss that you wish you had taken but did not?

[Karren H]

The High School Lettermen's club had an initiation where you had to dress as a girl for a whole school day.... and I was so looking forward to the day I could participate.... but the year I earned my first sports letter, the club dropped that from their requirements.... sigh.... some of the guys looked so amazing as girls I also wonder if they hadn't done that many times before....

also when I was in grade school my mother wanted to make me a dress for halloween .... she always wanted a girl and would tell me that a lot.... and I wanted to dress up but was afraid of what my friends would say so I didn't let her.....

[outhiking]

Wow, I could have written this post (former band geek myself). I've passed up every opportunity, even Halloween because I was always afraid someone would see how much I enjoyed it. I sure would love to go as a bride one Halloween.

[Tracii G]

I took the opportunity Junior year of HS at the prodding of a few of my close GF's One GF wanted to play a trick on her ex BF.It was his senior prom.
I had very long hair so they did my hair in an updo did my make up added a nice prom gown and off we went.
Nobody knew who I was and they thought I must have gone to a different school.Ha ha on them!
Her ex asked me to dance and my GF's started giggling like crazy when I said yes.
He was a jerk and tried to feel me up so I slapped him and walked away.They were in tears.LOL.
They told him later who he tried to feel up and he was pissed and confronted me.I said in a loud voice "dude why would you want to feel up a guy?" in a huge crowd in the lunch room.
Totally ruined his day and rest of the year too.He deserved it because he felt he could feel up any girl because he was the football team captain.

[Rikidee]

Isn't it wierd how being a crossdresser actually makes us reluctant to dress for fear of discovery in situations where people who are not crossdressers do not even hesitate. My older brother got to dress up for a club initation in high school and I thought he was the luckiest guy in the world. At the same time if I had had the same opportunity I would have never done it because I was afraid people could see I really enjoyed it! A few years ago though I did get to dress up for a Relay For Life Event in front of all the people I work with. I looked really good and really enjoyed and made money for charity as well. It is one of my favorite dressing adventures. Hugs Riki

[michellecd9999]

Wow Traci G - to be able to go to the prom, that would have been a blast. You must have passed very well. Did they do your nails? What about body hair? A prom dress exposes a lot of skin! In my dreams that is something I would have loved to do. But as Rikidee also said, being CD I would have been hesitant to to do so. I think IF I had a GG/GGs really encouraged or "pushed" me into it, I would have been more willing. I think Rikidee is also right in that even today I am fearful that if I did dress up for some public event, I would want to do it up right and people would realize that I enjoy it and walk to well in those heels! A few years ago, I decided at the last minute to dress up as a witch for Halloween. My wife was at work (I work from home) and I ran out and picked up a few things at the thrift store and wal-mart to put it together. One thing I decided was NOT to look too good, so I painted my face green and put long ugly fingertips on with a cheap witch wig and hat. Black dress, black pantyhose, black pumps with a low heel. Water balloons in a bra for shape. When I went down to a neighborhood party that night the neighbors did not recognize me and they all complimented me on my look and said they thought I was a woman. One guy (married neighbor) keep asking me all type of questions and for years he kept asking me if I was going to dress up as a woman for Halloween again. The ladies seem to like my dress and heels and several kept grabbing my boobs and asking me what I used and how good they looked! Of course I have not ever dressed up as a female character for Halloween since I fear that would also out me (I see the same neighbors every year).

[AmandaBlack]

Blew one big time! I started dressing shortly after getting married ('91)...just because my wife had lots of sexy things, just sneaking panties and hose. Sitting on the couch one day she said to me "You know, you'd probably look good dressed up as a woman"...we must've been watching some show or whatever.

A few weeks later she went away for the weekend with friends. So, home alone I dressed up fully for the first time. Wig, make up, skirt blouse even jewelry...I was surprised how good and "passing" (at the time ) I looked.

Taking account of what she said I thought, that's it, I'm going to dress for her...when she walks in I'll be sitting in the living room and surprise her. She has a great sense of humor so I figured she's see it as a joke and not as an eroticism as I do.

I got dressed, waited around...and then got really nervous about the whole thing! I decided against it and quickly changed out of her things, got cleaned up and thought "never again" (haaa haaa).

I've been a closet CD since and regret that I didn't go through with it as I look back on it, that would have been the perfect time to "come out" to her.

[Victoria StJohn]

Yes, I'm another member of the 'Missed Opportunities' club. One year I dressed for Halloween and a friend's lady friend saw some photos of me. She called me up and invited me to her place where she lived with another lady and the male landlord. She wanted me to visit in my feminine attire. I told her the 'borrowed' dress, wig, heels, etc. had been returned. What did I miss with an opportunity like that??? Oh well!!!

[Tabitha_Lynn]

I remember a couple big missed opportunities.

One was in High School. Way back when I was in school and "initiation fun" was still allowable, the Beta club used to initiate new inductees for a school week. One of the usual initiation rites was to go to school for the day dressed as a girl. As bad luck would have it, the year I was inducted they got a new sponsoring teacher and decided not to do the initiations. It would have been awesome to hace my sisters' help to get pretty for the day.

The other big miss was when I was caught dressed by my mom one time. I should have come clean with her at the time about myself and true desires.

[Tracii G]

Michelle back then I didn't have much body hair but they did shave my shoulders and back.
They did my nails too both feet and fingers.Remember I was 16-17 years old.
They thought I looked great with my hair up too so after that they always wanted to do my hair in pig tails or braids.I let them because I liked it.
Barbara was my best friend and she said you should have been a girl because you act like one.
I did hear from Barbara 5 years ago by phone and we laughed about that time.
I sent her a pic of Tracii and she said you are still doing that dress up thing? That is so cute.

[Ashley D.]

Back when I was in grade school late years. I had been dressing in privet for some time but never got to dress from head to toe. I tried for two years in a row to tell my mom I wanted to go to dress up day as a girl. But couldn't get the nerve finly the third year I did. She helped me get dressed I acted like I didn't know about anything. After I was fully dressed I looked in the mirror and I look just like a girl! I looked great. Then I started thinking and got scared then I froze up I couldn't do it. To this day I think what if I did maybe it wouldn't have taken another ten years to finly go out in femm.

[Kelli Ca]

Nothing has ever happened like that forme although I wished and still wish something would. I think I would jump at the chance, my wish would be for an office party or Halloween where we were to dress as opposites sex I would love to dress in front of all the people I know with out being out all the way

[JamieG]

I am the queen of missed opportunities. Two in particular come to mind.

1) My high school had an annual Powderpuff Football game where there girls would play and the guys would cheer. The guys would go all out, with skirts and makeup. My senior year, my best and friend and I were "joking" about signing up for it, and one of the cute girls in class said, "That would be so cool! You should really do it." We agreed that we would meet at my locker at the end of school and go to the first (after-school) meeting for Powderpuff cheerleaders together. I waited at my locker until the last minute before buses left for home, but my friend didn't show. I didn't have the guts to do it on my own and ran to the buses, where I saw him. When I asked what happened, he said "I forgot!" I was so jealous of the guys that actually did it. Just like the real cheerleaders, they wore their uniforms to class all day on the day of the game, and they wore them again for another pep-rally.

2) When I was about 22, I was working closely with a woman about my age. As we were working, she mentioned that she was throwing a Halloween costume party and asked if I wanted to come. I said, "I don't know what I would wear." She then said, "We could dress you up as a girl." For a moment, my heart stopped and I stammered. Then before I had a chance to say anything, she changed the conversation back to work. I didn't have the courage to bring up her suggestion again, but I often wonder what it would have been like if I had taken her up on her offer.

Jamie

[Pexetta]

I've taken every opportunity I've had, except in a dream I had once, where I was back at school and a cross-dressing day was being held. Everyone else was going wild with fabulous outfits, but I was determined wasn't going to be made to dress. Eventually I chose a nun's habit with a veil that covered me from head to toe.

As my mother would say 'You'd cut off your nose to spite your face.'

[Jadedflames]

Ugh. Yes. I was one of those band nerds too, one year for halloween, I even brought the dress to school, because the marching band was going to be playing in costume for the halloween football game. It was a lovely purple shimmery prom dress. And then.... I chickened out. So my best friend told me he would wear it. And he did.

...

I still contend that I looked better in that dress than he ever would. I did eventually wear it to the afterparty, which led to some funny conversation with people who wondered how we had both ended up buying the same dress. I never told them it was actually the exact same one. "What a coincidence!"

[NathalieX66]

Yep. ....absolutely!......makes me so mad at myself.

About 13 years ago, I was living in northern Massachusetts, Haverhill area specifically.
There was an LGBT club on the Merrimack river called the Rainbow Lounge that had trans night every Wednesday. The place was walking distance from my house.

I was still deeply in the closet, and I was also afraid that there were people from work that go there, and I was afraid of rumors a work. It was kind of a toxic work environment then, and i couldn't risk anything for the sake of preserving my job.

I look back on it, and I can't believe how irrational the thought was. Today, I'd be there in a nanosecond. Times have changed, and so did I.....quoting lyrics of a song from an old '70's band the Guess Who.

[Stephanie47]

I never had the opportunity. I truly do not know how I would react to a suggestion to attend a party en femme, if there were people who would know me. My wife knows I dress, although it's a DADT deal. She does NOT remember when we ran into her father and his girlfriend in an Eagle Club parking lot, en femme! He really did NOT look good, but, nobody recognized him. I have always found it interesting my wife does not remember.

[Lady Slipper]

Several years ago my niece wanted a ponies and princesses birthday party. Most of my GG cousins and aunts came as princesses and several of my uncles and male cousins did too! NOBODY FREAKING TOLD ME !! Of course I probably would have chickend out anyway, lols.

[5150 Girl]

We had a thing at out HS called "Beef Line",,, and it was a simular deal to waht the OP said.... Anywho, I wish now I had taken the oprituity to come out! THere was this one girl, openly butch lesbian, but she did clean up nice. And she was actualy one of the "cool kids"... Anyway, I heard she said I was cute. YEs, it was the 80's and that would have been a dangerous time for "our people", but if I had hooked up with her, I would have been protected. (cool by association) It would have mademe Mr.K's (what we called her) bitch.
Also, we had a dress rehasal before school the day of the show, and alot of the others sugested that I just spend the day dressed to advertise the show. Again, it was the 80's and I was a member of teh nerd clan, and so I figgured I'd better change, as I already caught enough hayzing as it was.

[Vee]

Funny how a thread can bring back a forgotten memory. Back in the '50's there was an occasion that wasn't a missed opportunity, but rather an unappreciated one. Our Cub Scouts planned a night at the elementary school for each den (Cub Scout group) to put on a skit on stage. I got picked to do a girl role. My mom borrowed a nice gown from my best friend's sister and I did my part for the skit. It was fun but not like being "all dressed up" because the outfit didn't include any shoes, makeup or silky undergarments. It just felt like a costume.

My mom used to talk about wanting a daughter. Looking back, I wonder if she made sure I got the girl part. Hmm..?

[UNDERDRESSER]

No real "opportunities" that I can remember, but you are all making me think seriously about my GF's suggstion that i go to work on halloween dressed. Her idea is "Classy English lady" maybe tweed, sensible skirt, pearls? I can do a "Cut Glass Accent" semi believably

Yes she knows I'm a CD. I've never tried to dress fully before.

[outhiking]

Wow, I suddenly remembered when in High School how my mom and sister pestered me to let them dress me up for a Halloween party. Man, what a miss that was.

[michellecd9999]

Thanks, ladies for sharing. I know that I had several opportunities I did not fully utilize. Another one was when I was visiting my aunt and cousin in CA one summer with my mom. I was the only male there (I was 14 and my cousin was 17). One day she was buying a bra and the discussion got around to wearing bras and pantyhose, etc and how uncomfortable they were in the hot CA heat. My cousin was open and I think if I had brought it up she would have let me wear her bra and panties and hose to see how "uncomfortable" they were. Of course in the heat, I agree that pantyhose are hot, but I would have put up with it to be able to prove her wrong. I would have also challenged her I I could wear her heels for a few hours. It would have been fun and I in the spirit of good fun, even in front of my mom!

[Beverley Sims]

One girlfriend I had wanted me to be her girl cousin from interstate.
Too much testosterone in me then.
Nah! I am not going to do anything poofy like that.
It was a dress up party and there were six hot chicks there all great lookers and all men.
BOY! DID I MISS OUT.

[Shelby]

Back in HS as part of a Homecoming week, we had a Xdressed Day. Naturally many of the girls dressed as boys but only one guy wore a skirt to school that day and changed before the first class hour. I wanted to participate and asked a female friend about borrowing her Cheerleader uniform. Now I had a crush on her and the thought of wearing her clothes was exhilarating but I was in denial about our difference in size as she was a cute lean girl and I was, well...not lean. I asked her quietly and she put her hands on my hips to judge my size and told me that she didn't think it would fit me but if I came over after our theater practice I could try on some of her clothes. OMG, dream come true! Unfortunately, I was getting a ride home to the next town with my cousin and uncle. If I went to her house, I would have needed one of my parents to pick me up at a girls house. Just explaining what I was doing at a girls house would have been difficult to do, imagine if I told them the truth. I declined the offer and didn't dress for the day, which in hindsight was probably a good idea since nobody else did either. That dress up event was never held again btw.