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

[JackieD85]

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.

[audreyinalbany]

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

[Georgina]

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.

[jenn]

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.

[alwayshave]

That is a hard no.

[Crissy 107]

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.

[SDress22]

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!

[JoyceAnn]

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!

[bridget thronton]

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

[Connie D50]

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

[fireandlace]

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.

[marieclaire]

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.?

[Raychel]

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.......

[JesseVF]

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.

[EmilyShy]

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

[Cheryl T]

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.

[DTelia]

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 :-)

[docrobbysherry]

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:

[emma-louise]

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

[TheHiddenMe]

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).

[jjjjohanne]

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.

[BrendaPDX]

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

[cdinmd206]

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.

[OrdinaryAverageGuy]

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.

[JulieC]

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 :) :(

[BLACK STOCKINGS]

Well never got dressed by another women, but 4 years in a row had a lady from work come over my house and do my makeup for Halloween. She loved the outfits I wore. I am so bad at makeup. Was happy to have her do it for me.

[Traci H]

Only close incident was at a neighbors/friends house with my parents as a nine year old. My friend and his older sister challenged me to try on her shoes. They were basic female flats and unlike anything I had ever worn. Well, I slipped them on and they felt so nice. They then tried to push me into the living room wearing her shoes so the parents could see. I do believe I successfully got out of them before that happened. I sure enjoyed those few minutes and wonder if that played any role in my cding today.

[GraceH]

When I was 5, and just entered kindergarten, we had a costume day for Halloween. My mom dressed me as a witch. I had no inkling that that was crossdressing until much later.

[HollyGreene]

When I was 17 there was a girl, Rita, I used to sit with and talk to on the school bus every day. She was in the year above me at school. One day she invited me to come to her house on the Saturday to listen to some music by a band we both liked.
When I got there, it turned out that her parents were away for the weekend so she was the only one at home.
We listened to the music as planned, and chatted.
Then she said, out of the blue, that I would have made a good girl. I had longish hair and at the time a fairly androgynous face. She asked me if she could practice makeup on me. At first, I was reluctant, but eventually gave in to her wily charms. Once made up, she restyled my hair as best she could, and then immediately went and took a dress from her wardrobe and told me to put it on.
She had no idea that I was a CDer, and I couldn't believe my luck, but I made it look as if I wasn't that keen.
The dress fit really well, and I loved it. It's probably the most feminine I've ever looked in my life. I remained dressed and made up for the next couple of hours before having to take it all off to go home.
I was really scared that she would tell people at school, but she never did. It was our little secret, and every time her parents went away for the weekend we'd do it again.
I lost touch with her when she went to university, and have never seen her again since. Pity really, thinking back. She would have made the ideal supportive wife.

[Lacey New]

Only in my most erotic fantasy

[Jasmine23]

Had a few half opportunities that I wish I'd taken, but, didn't which I regret now. When I was 8 or 9, my sister who was about 14 or 15, wanted to style my hair like her friends new hairstyle, I reluctantly agreed, she started to style my hair, then said she'd have to dress me up too, to complete the look, I secretly wanted this, but, then realised that my brothers or father might see me dressesd as a girl and that ended that, I stopped her from styling my hair and let the room.

Next time I was about 15 or 16, for a school play the drama teacher suggested that the boys would play the female roles and the girls play the male roles, the girls thought this was hilarious and were all for it, the boys as you can imagine were all against it, I was hoping I would be " forced " to do it, eventually the idea got canned as none of the boys would agree to it.

The last opportunity was when I was about 20 or 21, at work due to a few guys leaving and getting replaced by girls I ended up being the only guy in a group of about 15, half the women were about my age, so I ended up getting close to them and they treated me " like one of the girls " and even invited me on " girls nights out", I eventually agreed to go with them and on more than one occasion they wanted to give me a makeover, but, I was too scared that they would find out I liked dressing as a girl so turned them down. Looking back I really regret not letting them give me a makeover and going out as a girl with them, and often fantasise about what might have been, it's probably my biggest regret in life!

[Sabine Janus]

Had my first girlfriend say the gay couple in the next apartment (Friends) were putting on Drag/fashion shows

I was too young, to male and too closeted to act on the hint.

Always remember it though

[Misty_cder]

A female friend of ours ask if she could dress me for her professional makeup lessons. She would come over the take care of our cats when we were on vacation. This was before my wife and I had kids, so we traveled a lot more than we do now. During one trip, our friend found my size 11 thigh high boots. When we returned from the trip, she confessed finding the boots and asked if I was a crossdresser and would I be willing to be her “model” for the makeup class she was taking. I wanted to do it but my wife, who was more conservative thinking at that time, did not want me doing it. We eventually had kids which brought an end to our travels and we lost contact with our friend after she moved.

[April Rose]

I'm married to a licensed cosmetologist who is starting a new career as a transition life coach, so, yeah, it's happening a lot lately.

I am not sure the rules allow me to post it here, but anyone interested can PM me for her website.

[JustineFallow]

A former girlfriend did my makeup on several occasions for fetish nights at clubs or just general fooling around. Her daughter even pitched in to help a few times.

[Rileyaz]

Please send me the website

[DivaB]

When I was in college and working part time I dated a coworker that would dress me and do my makeup. That always ended up in the bedroom. Back then I was young and thin I think I could have passed fairly easily. She always want to dress me up do my makeup and have a girls night out. I was terrified to take her up on it. She was a little rowdy in the bars and I was scared to have some guy hitting on me. I'm sure she would have encouraged any guy that showed interest in me. NOW I really wished I would have taken her up on it.

[Monique65]

As I have related several times, my mother dressed me for Halloween when I was in my early teens. She used my sister’s blouse and dress and tied a cute scarf around my head. Unbeknownst to her, I, of course, had borrowed my sister’s bra and panties to complete the process. She dropped me off at a Halloween event in a neighboring town and I spent several glorious hours mingling with the crown en femme. She picked me up and we never discussed it again.

[Julia1984]

Im not sure if this really counts: a couple of years ago, when i was considering coming out fully as trans / gender-fluid at work, I went for a personal-shopper / style-consultation at our local high(er) end department store. It was the first time my stylist - who was absolutely brilliant - had dealt with a trans customer. The session was supposed to last an hour or so but we took a whole morning over it. My budget was a bit too limited to buy everything we agreed on but I did come away with half a dozen pieces or so; some skirts, blouses and a pair of dresses. It was a fantastic time. I may do it again.

[Mercedes]

The closest story I have is that at work, the ladies decided to sign myself and another male colleague in the Walk a Mile in her Shoes event. The ladies brought heels, that didn’t fit, and gave us some tights and a tutu to wear as we did our walk. They did not know that I was wearing a thong at the time. And to top it off all the women thought I had amazing legs in the tights. The other guy did not get the complement so I feel it was true.

[Stacy Darling]

I was sort of lucky, A swimmer that got waxed by my beautician. we spoke about me being a CD one day and next we did brows and the rest. just professional.

[Rachelakld]

My coffee girl said I would look great in one of her dresses, she gave me 4 dresses of which only one would fit - I wore it into her shop (photo on my blog posing with their christmas tree).
She asked if I wore my blue dress often - I said not really and 2 days later I gifted it to her, she jumped up and down with joy.

[Corrina]

My younger sister used to blackmail me into dressing after she caught me in her hamper as a teen
My current girlfriend likes to dress me up and do my makeup then call me her pretty girl

[TrishaLake]

I have had a few cis ladies go out with me dressed but not actually dress me. I am picky about what I want on me anyway!!! It is always fun to go out with cis ladies.

[Breezy]

I have, a big yes. I worked with a woman who was about 20 years my elder. She was BEAUTIFUL and I fawned over her every chance. We went out a handful of times, she was a classic, brunette, secretary pencil skirt woman.
She asked me one time if I?d ever worn pantyhose because she wore them everyday, never without them. I?d caress her legs & always complimented her.
So, long story short she had me changing in the restroom at work to wear pantyhose she brought in for me.
That led to panties, thigh highs, slips, dresses, skirts, heels, wigs.
I did it all in the office restroom, and would wear her things under my clothes all the time,
I loved it! And so did she.
She wanted me to have sexual encounters with men as well while I was dressed, she really got off on it. So did I!
A wild time for sure. Lasted about 4 years!
Never got caught in the office.

[Natalie5004]

Well, I was in a consignment shop once and I was struggling with a zipper on a dress. I stepped out of the dressing room and asked a woman to zip me up. Does that count?

[Crissy 107]

Natalie, that’s a close call but I vote yes