I was 18. Admitted to my girlfriend that I wanted to wear a garter belt and stocking. she helped me out after she borrowed a garter from her best friend. A month or so later, her and her friend surprised me and told me they were going to dress me and put make up on me. I accepted and had a wonderful night that I still remember. Often wonder why I split up with her!
I was 18, and although the thought of wearing women's clothes and/or lipstick turned me on I knew absolutely nothing about makeup. When three girls wanted to put mascara on me I had no idea what mascara was other than it was some kind of makeup that girls used. I protested, but they finally got me to agree. They brought out their makeup bag and when they opened it I smelled the most delightful feminine smell. They started by using these scissor looking things on my eyelashes, and then they took a tube that when they pulled it apart had a brush with some black stuff on it. By the time they finished with the eyeshadow and the eyeliner I figured out that the tube with the black stuff on the brush was the mascara, but it was a little bit late to try to stop them by that time. They finished with lipstick and then put a scarf over my head and finally let me look in a mirror. That was over fifty years ago, and every once in a while when I look back on that time, I wonder what they would have done, and what I would have done if I would have asked them "Are you done now, or do I have to wear a dress too?"
I'm rubbish at my own make-up, occasionally I get one good eye.
My wife has tried to teach me a few things on every now and then she will do my eyes for me.
Would love to have my make-up done professionally to see if I could pass as a real woman but going out in drab and getting done doesn't seem worth it just to go home and take it off.
Xx
I never got a GF or SO to do my makeup.
However, I have gotten dozens of makeovers. Many were done by girls like us, But, about half were done by GGs. Several at MAC and another local makeup salon, but most were by GGs either as part of their business, or just as a sideline to make extra money.
I had a great time at all of them.
I think my favorite is when I told the girls that I wanted an over the top makeover with red sparkly eye shadow like Lady Gaga had when highlighted the Superbowl half time show a few years ago.
Last edited by Sometimes Steffi; 06-01-2019 at 07:26 PM.
Hi, I'm Steffi and I'm a crossdresser... And I accept and celebrate both sides of me. Or, maybe I'm gender fluid.
I went out dressed as my sister for Halloween when I was in 8th grade. I think my mom did the makeup (Can't remember how much she made me up).
Flash forward to my late 20's. I met Renee when I responded to her personal ad in the Riverfront Times, a weekly free paper in St. Louis. We went on some dates, and eventually became intimate (more FWB than GF/BF, even though FWB wasn't even a term then).
I'm not sure how the subject came up (I'm sure I was the instigator) but I made the comment that I had big feet and my feet were too big for woman's shoes. Renee said no, there were woman's shoes in my size and she could find some. I said something that if she found some shoes for me, I would get dressed up.
She found some black heels and eventually she did my makeup and I got dressed up. I think it was a business suit. No wig, Renee said I looked better in her clothes than she did (by her own admission, she was a bit of a tomboy). She also had a roommate who was a CD, and occasionally she would wear some of her roommate's dresses (I think I met the roommate once, but I never raised the topic). I also wore some of her lingerie from time to time.
A few months later Renee met her future (and current) husband so we stopped going out.
Fast forward to today. Renee and I became Facebook friends a couple of years ago. Then I screwed up and sent out a picture of me dressed, and Renee saw it. We connected by Messenger and she absolutely loves seeing pictures of me dressed up, and reading the posts of my times out (I email them to her). I send her pictures of me trying clothes on and she offers her opinions. She would like me to come visit and go out together with me in Dee mode. I'd love that too.
It was for a youth group Christmas party which had a crossdressing theme. I borrowed my sisters clothes and both my mother and my sister did my hair and makeup. That is the only time that somebody else has fully dressed me.
I used to share a house with 2 or 3 women (oh, the wardrobe choices available to me), and they occasionally offered to paint my nails when they were getting ready for a big night out. I let them do my toenails on a few occasions.
I spent the first part of my life homophobic yet wearing female clothing way before I knew what sex was.
When I was around 21 I was dating a female that became a stripper. I loved digging thru her clothes and high heels. We used to do a lot of drugs too so I kinda let my inhibitions go. I'm not condoning that behavior at all, it was in my past.
One night after having way too much fun, I admitted to her that I sometimes wore women's clothing. She was excited and asked if she could shave my body and dress me up, make up and all. I was very shocked and very shy.
I remember shaking like I was nervous as she taught me how to shave my body from my nose to my toes lol After that she put a black silk gown that has a slit all the way up (I still have it lol) a black g string and black high heels.
I didn't really get to enjoy the moment until the next night when I asked if she could dress me up again. She did and it was such a liberating feeling.
That was in 2000, by now I go out frequently with a padded bra under tight female clothes. I always have flip flops on to expose my painted toes and feet jewelry. I only do my makeup on special occasions but I've gotten better away application lol and my wardrobe has finally gotten to a nice size. I have way too many girly shoes lol
Have a great day luv!!!!!!
Last edited by char GG; 06-01-2019 at 07:50 AM. Reason: This is a PG forum. TMI
My wife and I were at a friends house drinking and having fun when I fell asleep and our female friend put make up on me and I awoke just as I felt the lipstick being dragged across my lips my finger nails were also varnished.
Then I was encouraged to put on a night dress, well who am I to argue.
The following day she told me she had deleted the photographs that were taken, drat.
Anyway since then she has painted my nails, given me under wear and clothes and allowed me to dress whenever she is around at our house.
Bliss
When I was young on two occasions my mom dressed me as a girl. One for Halloween ( baton twirler) and one for a boy scout ( a Beatles screaming Fan) skit. She didn't know I was trying on my sister cloths at the time.
Or maybe she did
I come out with a friend girl of mine not so long, specialist of make up.
She accepts without hesitation my crossdressing, and was impressed by my make up.
She even wants someday to do the make up to me. Maybe one day
My best friend did my makeup the first time I ever went out in public as a girl.
I had to visit the US for work, near where she lives, so I visited her for a weekend. I found out that another friend from grad school was going to be in the city at the same time. I had come out to her some time ago, so we decided to go out for dinner and drinks, with me going as a girl. Sadly my bestie had other plans and couldn’t join us, but she took me shopping, and did my full make up (we are similar in skin-tone so her colours worked for me).
I wouldn't call it a "make over" but when I was 22, my girlfriend and I decided to read Penthouse letters [Remember those?] to each other and we'd try to reenact anything we read that sounded hot. Of course, we read a letter about crossdressing and so we decided to crossdress each other.
She wore a suit of mine, she dressed me up in one of her outfits. I knotted her/my tie for her, her slipped me into one of her skirts and a blouse.
When both of us were dressed, she said, "Let's try some makeup on you"...And she proceeded to apply mascara, eye shadow and lipstick. It was obviously a huge turn on...But, by that time I had been secretly crossdressing for years, and, honestly, I did a better job!
To this day, I'm not much into makeovers...I think I do a better job and I love the process.
When I was about 16, a girl I befriended on the school bus once said that I would look good as a girl. It was the 1970s and longish hair was popular amongst boys, and I was no exception.
She and I lived in different villages, and one time she invited me to her house at the weekend.
Little did I know that she wanted to dress me in her clothes and do makeup. She also restyled my hair to look more feminine. At the time I pretended to be very reluctant, but was secretly enjoying every minute.
Her parents were out of the house, but her mother came back while I was still dressed up. She had no idea that I was a guy, and I had to stay dressed because she wouldn't have approved of what we had done. It definitely wasn't acceptable back then.
When it was time for me to leave, I had to put my own clothes in a bag and leave wearing what was a rather nice floral dress.
Luckily, I was able to find a place to change and wash the makeup off my face before I went home.
I never told her, but I did wear her clothes a few times before I returned them to her.
Unfortunately, she never did ask me to do the same again on subsequent visits.
I’m 44 and about a year ago I “came out” to my girlfriends at the massage and day spa that I went to frequently for massages, facials, pedicures and even waxing... (it was shocking that they didn’t have a clue really lol)
anyway one of the aestheticians there also did makeup and so they told her about me (with my ok) and she totally agreed to give me lessons. We only did it maybe 3 times but I’ve never felt so amazing as I did the first time we worked together ... not just the makeup but the realization of this particular dream. She is of course amazingly beautiful and that didn’t hurt either.
Ive since moved away and have been largely ignored by the other girls (we were friendly and all but I think my generous tips were a big part of that) but I have kept in touch with my makeup artist via Facebook. I doubt I will ever have the same opportunity again so I’m grateful for the experience and acceptance on those occasions. *sigh*
Kelly a.k.a. VS Fan
Teresa,Originally Posted by Teresa
I think for many GG's it's the same. They too learn by trial and error. They however have the advantage over us in that they start early and get help from their girl gang. As you pointed out, now you're full time you're learning the less is more lesson.
As one of those who've like you had a colour match that for me is the closest I've come to having a GG do my makeup. I must admit it's on my bucket list to get the full treatment somewhere like MAC but looking for instruction on day makeup rather than evening. Good daytime makeup is a subtle skill
Who dares wears Get in, get out without being noticed
A few years ago I made an appointment with one of those beautiful local makeup artists who have popped up all over the place thanks to Instagram. You know, the kind who pile layers of makeup on middle age women and wedding parties. So, she was very nice but she didn't listen to me when I suggested orange corrector over my freshly shaved beard area. Sure enough, an hour later I had a lovely blue shadow showing though the $100 makeup job. On the other hand, it was the first time my eyes were done up properly and it was glorious.
Seven years old by an older sister for Halloween.
Her idea and of course I wouldn't dare to refuse!
But as an adult? Nope, never. Not even after I showed them a pic of me.
Posting Permissions
