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

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.

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.

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.

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.

Only in my most erotic fantasy

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!

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

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.

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.

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.

Please send me the website

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.

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.

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.

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.

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.

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.

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

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.

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.

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?

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