A formative crossdress experience

[cdstefi]

This happened donkey's years ago when I was at university.

So there was a Rag Week disco on at the students union, fancy dress themed. I knew a bunch of girls (as drinking buddy type friends, wasn't going out with any of them), and I tentatively suggested going in drag. Fay, the most outspoken and fearless of them, thought it was a brilliant idea and offered to do a full clothes swap as we were similar sizes.

They did a full makeover on me, Fay and her friends Sian and Anne. Lent me a dress, holdup black fishnet stockings, black bra (with some more stockings stuffed in to give me an outline), low heels I could walk in, and even a pair of Fay's black lace panties (I hadn't dared ask for them and was going to wear my own pants, but her attitude was go big or go home; I said she was fearless ), then styled my hair as best they could with some clips and accessories and did my makeup: foundation and blusher, eyeliner, mascara and lipstick.

I wouldn't say I was completely passable as a girl but it was close enough for an evening out, and such that I felt more comfortable using the ladies' toilets at the disco. Walking on the city streets in the evening in a summer dress, feeling the sensation of Fay's tight, brief panties barely covering my cock and balls and ass, her bra around my chest and the fishnets on my bare legs was quite something, as was walking in heels and the way they naturally seem to make one's hips sway in a more feminine way. Of course I was immensely turned on, and had to wait till I got home much later to masturbate a couple of times at the memory, but the friendship we had was of the sort where this was all just a great laugh rather than anything that would turn sexual.

 

[Easypeter]

This sounds like the Halloween that my wife dressed me up for a party we attended and it was amazing ! Guys liked feeling me up

 

[drobert44]

This happened donkey's years ago when I was at university.

So there was a Rag Week disco on at the students union, fancy dress themed. I knew a bunch of girls (as drinking buddy type friends, wasn't going out with any of them), and I tentatively suggested going in drag. Fay, the most outspoken and fearless of them, thought it was a brilliant idea and offered to do a full clothes swap as we were similar sizes.

They did a full makeover on me, Fay and her friends Sian and Anne. Lent me a dress, holdup black fishnet stockings, black bra (with some more stockings stuffed in to give me an outline), low heels I could walk in, and even a pair of Fay's black lace panties (I hadn't dared ask for them and was going to wear my own pants, but her attitude was go big or go home; I said she was fearless ), then styled my hair as best they could with some clips and accessories and did my makeup: foundation and blusher, eyeliner, mascara and lipstick.

I wouldn't say I was completely passable as a girl but it was close enough for an evening out, and such that I felt more comfortable using the ladies' toilets at the disco. Walking on the city streets in the evening in a summer dress, feeling the sensation of Fay's tight, brief panties covering my cock and balls and ass, her bra around my chest and the fishnets on my bare legs was quite something, as was walking in heels and the way they naturally seem to make one's hips sway in a more feminine way. Of course I was immensely turned on, and had to wait till I got home much later to masturbate a couple of times at the memory, but the friendship we had was of the sort where this was all just a great laugh rather than anything that would turn sexual.

Yep, you are ready to suck and get fucked.

 

[SPARTAN047]

Nice experience. It's what I felt when I dressed up but without makeup at the beginning of my journey.

 

[Terrylipstick]

This happened donkey's years ago when I was at university.

So there was a Rag Week disco on at the students union, fancy dress themed. I knew a bunch of girls (as drinking buddy type friends, wasn't going out with any of them), and I tentatively suggested going in drag. Fay, the most outspoken and fearless of them, thought it was a brilliant idea and offered to do a full clothes swap as we were similar sizes.

They did a full makeover on me, Fay and her friends Sian and Anne. Lent me a dress, holdup black fishnet stockings, black bra (with some more stockings stuffed in to give me an outline), low heels I could walk in, and even a pair of Fay's black lace panties (I hadn't dared ask for them and was going to wear my own pants, but her attitude was go big or go home; I said she was fearless ), then styled my hair as best they could with some clips and accessories and did my makeup: foundation and blusher, eyeliner, mascara and lipstick.

I wouldn't say I was completely passable as a girl but it was close enough for an evening out, and such that I felt more comfortable using the ladies' toilets at the disco. Walking on the city streets in the evening in a summer dress, feeling the sensation of Fay's tight, brief panties barely covering my cock and balls and ass, her bra around my chest and the fishnets on my bare legs was quite something, as was walking in heels and the way they naturally seem to make one's hips sway in a more feminine way. Of course I was immensely turned on, and had to wait till I got home much later to masturbate a couple of times at the memory, but the friendship we had was of the sort where this was all just a great laugh rather than anything that would turn sexual.

Could they see, or sense your arousal?

 

[cdstefi]

Could they see, or sense your arousal?

No idea really. There was lots of bantering and fun so it wasn't really an outright sexual thing.

 

[MeganFachs]

Did you involve any of them further with confessions, requests to do it again or go shopping together?

 

[cdstefi]

Did you involve any of them further with confessions, requests to do it again or go shopping together?

No, I was pretty shy at that age (20 or so) and Fay, the one I really fancied, was always going out with one or another of my mates.

 

[MeganFachs]

No, I was pretty shy at that age (20 or so) and Fay, the one I really fancied, was always going out with one or another of my mates.

I’m sorry she missed out on a special guy.

 

[cdstefi]

I’m sorry she missed out on a special guy.

That's sweet of you to say, but I think I was the one that missed out. I'd have loved to lose my virginity to her, she was sex on legs, very body-confident and uninhibited.

 

[MeganFachs]

My kind of girl!

 

[cdstefi]

I did find her a little intimidating although with life experience since I see no idea why.

She went out with a mate I shared a house with, and there was no mistaking when they were having sex. She was loud, and sounded almost feral when she was fucking.

 

[SPARTAN047]

Domestic housewives imply the existence of feral housewives, so I get you.

 

[CDJohnny6969]

My Mom and Grandma crossdressed me for Halloween and it changed my life…

 

[Sol41]

I did a man pageant at my college once. I was, ofc the best looking one there. Sang Shania Twain, had a fucking blast.
Afterwards I was getting a drink from a hallway fountain and one of my classmates said "You know the dress fits a little *too* well."

I had not a clue he was hitting on me lmao

 

[AlexBailey]

I was super shy and was shocked when the captain of the cheer squad came up to me during lunch at school and asked if I’d be a cheerleader for the Powderpuff football game on Friday. I knew her from class and she was always really friendly with me, but….

I had no idea she had a crush on me until I was sitting in front of a mirror in her uniform the morning before school. She finished doing my eyes, took my hair out of it’s ponytail and gave me two braids. She was gorgeous dressed in padded football uniform pants and a jersey. She sat next to me and pulled me onto her lap, then started joking around like she was the football star and I was her girlfriend.

We just played it up like that all day. By lunch the kisses were real.

 

[stargame]

I was super shy and was shocked when the captain of the cheer squad came up to me during lunch at school and asked if I’d be a cheerleader for the Powderpuff football game on Friday. I knew her from class and she was always really friendly with me, but….

I had no idea she had a crush on me until I was sitting in front of a mirror in her uniform the morning before school. She finished doing my eyes, took my hair out of it’s ponytail and gave me two braids. She was gorgeous dressed in padded football uniform pants and a jersey. She sat next to me and pulled me onto her lap, then started joking around like she was the football star and I was her girlfriend.

We just played it up like that all day. By lunch the kisses were real.

So cool Alex,
There was a time when I could go to the beach in a black bikini and do well. Of course, I got a lot of questioning looks. I admit it was very exciting.

 

[SPARTAN047]

It's mostly when I dressed with other CDs.

I've had pro MUAs put make up on me and another lovely woman who wants to try and dress me up with makeup (she's a pro too), but I didn't get time to make an appointment. Maybe one day.

I think it's different with CDs due to being the same kind of nervous.