Has a Female Offered to Dress You as a Woman/Girl?

If so, what did you say? Was it for Halloween, a costume party, womanless beauty pageant, stage show, etc.?

I was asked several times as I was often told that I should have been a girl. The one time I did accept was for Halloween in college.

I got many compliments and it was a night that I will remember forever.

Another thing that I will remember is the female friend who loaned me her bra. I didnt tell her that it fit perfectly. I thought about that every time I saw her after Halloween, but never said anything. We were both a 34B and it was easier for me then to hide my breasts. Today, Im a 40B.

Looking back, I wish I said yes every time I was asked. I know my life would be different with the additional experiences.

Nope....but I've had a woman ask me to NOT dress like a woman

Yes I have three good women friends who will help me to dress. One is good with make up and has offered help when I need it.

Yes I was fortunate enough to have a great roommate years ago. She helped me get dressed for Halloween and I let the secret out. We would do each other's toes and fingers and she let me.rsid her closet many times.

That is a hard no.

I had two girl cousins that wanted to dress me up when I was in my teens. I was embarrassed and said no, I know I missed the boat and am still sorry I declined.

I let an ex girlfriend do my makeup once. I also let her put a skirt on me during sex. My now spouse once suggested dressing me as a girl for Halloween, but I declined. I?m not sure why, and I still regret it!

My Mom offered once. She talked about how when she was young, she and her sister would sometimes put a dress on their brother if he happened to be in a good mood. I secretly wanted to say yes to her, but I was too timid/bashful to participate. I also thought I might catch flak from my brother and my father. Sometimes worrying too much about what others think results in missed opportunities!

My wife helped my dress as a nurse for a Halloween party early in our marriage

Yes my mom wanted to dress me as a girl for halloween, I had a sister 3 years older. it was a free costume.

I posted this at least ten years ago. Never had any other experiences like it.


In junior high I was at a neighbor's house and she and her friend "coaxed" me into dressing. I remember a corderoy jumper style dress and clogs. I am pretty sure there was make up involved also. I don't think there was any underwear, pretty sure I would remember that.

I had been dressing in my mom's stuff for a couple of years before that but this really kicked the desire into high gear. Unfortunately it never happened again.

Here's an interesting experience I wish I had: being dressed as a girl by my sister or my mother.
When I was a child, one day she and I were home alone, but she was with her friends. I wanted to play with them, but they said they would only let me if I dressed like them. I was scared and refused. A few years later, I tried on one of her bras in secret for the first time.
One night I dreamed that my sister caught me wearing one of her bras and she and my mother "punished" me by dressing me completely as a girl full time.
Question: If we ever have sons, will we be interested in dressing them up as a girl for Halloween, a costume party, womanless beauty pageant, stage show, etc.?

When I was young, maybe an early teenager.
I went to a friends house, he wasn't home but would be back shortly.
His sisters wanted to dress me as a girl. I stupidly said no. That would have been so
much fun, His sisters were really good looking, and his mother was VERY pretty as well.
I can only dream how much fun that would have been. But I was too embarrassed and
did not accept, Little did they know how much I really wanted to.

Then much later, I was close to 50, My wife and I dressed for Halloween.
She as an old man, myself as an old woman. We went shopping and she picked out my clothes
to wear for the evening. We got a grey wig, a black skirt and a gray top. She helped with the shopping
and even did my makeup fo rthe evening.

Those were the only occasions for me.
My friend now knows I dress, and has told me at time to go put on a dress. But I haven't done it yet.
Maybe someday.......

At around age 8 or so an Aunt of mine told me and my cousin if we really wanted to win a Halloween contest going on at the time we should dress as a girl. Unfortunately did not take advantage of that suggestion.
Marie Claire to your question I never had the urge to push girl dressing on my son. I would not have a problem if he wanted to, but while there are moments of happiness I don?t think it?s an easy life. At least it seems things are improving however for the most part.

No, but its something that I would love to happen. Id be there with bells on!!!
My wife has no interest in my quirk so its not likely to happen.

Emily xx

I was about 12 and my aunt caught me in her things.
She told me if I wanted to then just ask and she would help. I was too scared everyone would find out so I never did. Big regret.

Offered a few times over the course of my life…and had many opportunities that only needed a gentle hint or nod from me that I may want to try it…but alas - I turned down EVERY SINGLE ONE OF THEM - except for once when my mother curled my hair with rollers. I was TERRIFIED at getting caught or that someone would learn my secret. The fear of getting caught was higher than the desire to have some fun. I once suggested to my sister that it may be fun (this was in the 80s) she shot it down HARD. Thats all I needed to bury it :-(

My wife has asked me a couple times in our marriage knowing how much I would appropriate it and I did. She once surprised me with a long expensive blonde wig, and some clothes…it was years after talking about it and never really trying…so lets say it was a wonderful surprise and unforgettable experience for me

My wife feels badly that she doesnt asking me to do it more?but the truth is that shes not that girly or interested in it?she just loves me?.and tolerates me talking about it aneyseum. The things we do for our spouses :-)

Yes, once. When I first came out online here and a dating site about 20 years ago.:battingeyelashes:

I had been dressing in complete privacy for 10 years. Even tho she was a GG? When a complete stranger offered to help me dress I freaked out and said, "No"!:doh:

My ex wife used to do my hair and makeup all the time and chose outfits for me, we used to go out all the times as two girls, but when we split up she used my crossdressing as a reason to divorce me, but it was fun while it lasted

Two experiences.

1. With Renee, a woman I was dating/FWB I steered the conversation about heels. I told her that if she could find heels in my size, I'd dress up as a women. She did and it was one of my first times dressed.

We are still in contact today, she loves to see pictures of me dressed, and I flew pretty to see her in 2023, and spent 4 days dressed with her and her husband. The husband and I had a "date" and we saw The Boss play.

2. Another girlfriend, Geri, was taking the CPA exam and pretended to hypnotize me so I would dress up as her and take the CPA exam for her (this did not happen, as she was not keen about my dressing).

The short answer is no. No woman ever dressed me, like you are talking about.

However, here are some honorable mentions:
* My sister's friend asked if they could dress me like a girl for Halloween. I was probably in the 6th grade or younger. I said no.
* I was asked to dress as a girl for a costume event. I said yes. I borrowed a dress from a co-worker. My mom padded a bra for me and let me try on some of her hosiery. My new girlfriend (that I eventually married) did my makeup on the night of the event. She did not know about me at that point.
* I went shopping for a Halloween costume at a store. An employee in her 20's saw me come out of a dressing room holding a dress. She asked, "Did you try on a dress?" and smiled wryly. I bashfully said yes and said I am working on a costume. She ended up sizing me for a bra and having me try on several dresses that she or I selected. That's about as close to a YES to this question as it comes.
* There is a consignment shop where I buy some of my clothes. The owner has become a friend. She has offered me things to try on. That's happened in other stores too.
* One time, my little daughter had me put on a dress that was in our kids' dress up clothes box. It was a dress that our pastor's wife had given my wife. My daughter took me to show me off to everyone in the house. I was wearing my guy clothes under it.

No, and probably never will, I am too much of a closet case.

Ever since I can remember I have had a love of lingerie. When I was around 8 or 9 I was spending a few weeks with an aunt and she dressed me as a girl and called me her niece. She was always well dressed and always wore a dress with stockings and heels.

My wife once told me she could make me pretty. I accepted the challenge. She made me up, put me in a sundress, and finally agreed that I make one ugly woman.

OrdinaryAverageGuy, that's hysterical! And a bit sad though too, I have to admit.

My wife has experimented with makeup on me a couple of times, being a Mary Kay rep. It was more about trying different things she wanted to try, and it was easier to try on me than on herself. In the end, I was in the same category...an ugly woman :) :(