Your story of the first time a GG made you up?

[Lindsay blonde locks]

I would love to hear any memories of your first time coming out to a girl and their positive response. Specifically, when the girl decides to do your makeup and dress you in her nice clothes right then and there!


By the way, I'm asking this because it has never happened to me. 18 years old, so hopefully in the next year it will happen!

[abbiedrake]

Lol Keen ain'tcha?!
Maybe don't hold your breathe. Might take more than a year.
I've had it happen twice in my life, and I'm 48.
First time was my my mother-in-law during my first marriage. We were going to a fancy dress party. I went at a hooker. I bought the clothes myself, but she did my makeup. My then wife was useless at such. But then my mother-in-law went way overboard. It's worth noting though that this was 25 years before I started CDing. Lol
I also went to work in the exs wedding dress, but that was no makeup.
The second time was my current, keeper wife. Last year. I didn't start fully CDing until late 2017. And for my birthday last year my wife put me in a dress she'd outgrown, styled my hair into a Bob, and fixed my makeup. I loved it. But she only did it for me. She was not a happy accomplice. Having said that she's offered to help with my makeup more than once since, despite objecting to me shaving my beard off. Go figure.
I hope, Lindsay, that popping your makeover cherry is all you hope it might be.

[Cheryl T]

My wife was the one who did my makeup.
I had finally come out to her and we were going to a Halloween party. I borrowed a costume which was a Red off-the-shoulder dress, mid-calf, with a black sash and lace scarf. It was a Spanish dancer complete with hair comb, castanets and lace fan. I borrowed shoes and stockings from my wife in black and she did my makeup.
It took some time for anyone to recognize me and I spent most of the night with the ladies as they continually asked me about my costume, some wanted to know what I was wearing beneath it...

[Teresa]

Lindsay,
Never experienced it at your age . More recently I've had skin colour checks done and had my foundation applied in a makeup booth . It did feel odd the first time as I was in drab so it did raise a few eyebrows with passing shoppers . I must admit it was a nice feeling when another SA offered to reapply my lipstick , having an attractive girl that close did feel slightly erotic . As for dressing well I've had to ask on more than one occasion to be zipped up in a changing room .

[Micki_Finn]

This doesn’t happen. Which isn’t to say it NEVER happens, but you know, some people hit the lottery too. Most of those stories you read online are just crossdresser fantasy.

Edit: Makeovers from women are WAY overrated. Most women have no idea how to do crossdresser makeup. They use makeup to enhance their natural features whereas what we do (if done properly) is to transform our features. You really want a makeover that’s going to make you look like a woman, get a drag queen to do it.

[Lindsay blonde locks]

Abbie-
I love that phrase, "popping your makeup cherry"! Haha Great to hear that your second marriage was successful in the CD "accomplice" department.

- - - Updated - - -

Thanks for the story Cheryl. Why do any guys go with boring male costumes when Halloween is the one time of the year to not get any heat for dressing like the (more fun) fairer sex... /s

- - - Updated - - -

Teresa,
That sounds nice, almost exactly how I'd imagine it. A little scary, but not too "perfect" and not too negative and/or disappointing. But I wouldn't have my first time be in drab though!

[RADER]

My Wife was OK with my dressing; So on a Halloween, she dressed me up as a french maid.
She helped me get into some fish net Hose, and a little white apron. to hand out candy to the kids.
I look great, and hated to take it off at the end of the night.
Rader

[Sissy Sandy]

never had it
probably never will

[Teresa]

Micki,
I'm not sure if I agree but it does depend on where you plan to go when the makeup has been applied .

Professional makeup girls tend to be too heavy handed when they do wedding makeup , too much makeup doesn't photograph well in daylight but it is marginally better than no makeup at all .

The best solution is learn to do it yourself , I've finally struck a happy medium between applying it for everyday and a night out . The art is how little not how much .

[abbiedrake]

Micki,
Funny you should mention getting makeup from drag Queens. Before my wife first came over, before we'd met face to face, she had a photo shoot done as a gift for me, possibly parting (she had cancer at the time and was uncertain she'd survive. It's a different cancer this time). The makeup artist was a drag queen who did a fantastic job on her. So while store makeup artists can't even do GG makeovers well it appears drag queens can do CDs AND GGs.
There you go Lindsay. You want a girl to get girly with you it's lottery odds. You wanna look amazing get a CD to it!

[Tracii G]

When I was 15 years old. That was 1967 by the way.

[Meghan4now]

Never happened. The few times I've been made up with my wife, (or girlfriend 32 years ago) I had to do it myself. The only girls that have made me up were paid professionals.

Sorry if that isn't as excited as a fictionmania story!

P.s. Mickie had a point, but there are some GG MAUs that specialize. Most need tips on beard coverage and brow taping.

[Lindsay blonde locks]

Micki-
The problem is unfortunately you won't find as many drag queens in your life/geographic area as you will find women, and women that you already have a trusting bond with are even more accepting and accessible than either.

[abbiedrake]

The only friend I had close enough when I was your age, and was a girl who I might have confided in (had I not taken another 30 years to start CDing) was an inveterate tomboy. Suck luck. Lol

[ellbee]

I want to say I was around 17? :strugglin

And I was a young, thin pretty-boy with long-ish hair at the time. Perfect candidate, really. :battingeyelashes:


Of course, I had started seriously dabbling in my mom's make-up well before then, at age 13. Clothes? *Much* younger, at least age 6, that I can remember.

But my GF at the time (when I was 17) didn't know about all that. :o


Don't even recall how it happened... Though I want to say it was her idea. It was earlier on in our relationship. And she was the perfect blend for this, IMO... Total girly-girl -- yet with a slight tomboy streak to her, as well. Oh, and a total hottie. :thumbsup:

Sometimes I used to flip through her issues of Cosmopolitan or whatever teen-GG magazines she was into, right in front of her, without a care in the world. Then I think one day while doing so, she just blurted out something like, "I have the perfect shade of lipstick for you... And I want to see what you'd look like with it on!"

Well, of course I'm not going to say no to that! :roflmao:


She put it on me, and she was right: It did look great on me!

And she also put some face-powder on me, as well as a bit of blush, then fussed with my long-ish hair to be a bit more girly. She was pleased with the results. At that age & weight and with that hair, I did look pretty decent, despite the minimalist look.

Of course, I wanted her to keep going. And I asked, how about some eyeliner, and mascara, and, and, and...??


No, she was having none of that. :(

And by that point, with her curiosity fulfilled, she handed me some make-up wipes to take it all off. :thumbsdn:

Sadly, it was short-lived. And she was only willing to go so far (not much, really), when it got past the point of "being fun," to being a "bit weird."



There are other subsequent CD'ing stories with her, that perhaps I'll share here another time. But that was the first experience. (And that wasn't the only time I got to dip into her make-up stash. :devil: )


Another time, I will mention now, is one day after school, a bit further along in our relationship, she & I were alone in her parents' house. She was watching TV in the living room, and I just sort of casually snuck off into her bedroom -- where I found the dress & pantyhose she wore to school that day & had since changed out of.

Oh, yeah... I was throwing those on! :GD:

I did so, checked myself out in her full-length mirror, then slowly & nervously headed to the living room, hoping for the best. I don't recall what her exact reaction was, but something to the effect of: "Ha ha! Why are you wearing my dress? And OMG, are you wearing my pantyhose, too?? Ha ha! I was wondering where you've been... Is that what you were doing?"

What originally I thought in my mind to be a good idea to "introduce" her to my CD'ing, quickly turned into a not-so-good one.

"Umm, yeah, okay... Go take those off, please. Right now." And she was no longer amused, to say the least. I complied. :(


Long story short, she eventually ended up cheating on me, and dumping me for the new guy.

I was heart-broken at the time... But with her apparent non-acceptance with all this, I gradually came to realize what a bullet I had dodged. :thumbsup:

[Teresa]

I have been surprised how many GGs that haven't had a colour check done and are basically not that good at applying makeup . It was quite amusing when my daughter saw me for the first time , she just kept gazing into my eyes , something she's never done when I've looked like dad , when I commented on what she kept looking at she had to admit I had done a great job . My sister in law is really good at makeup but she had to ask how I made mine look so smooth , I certainly didn't expect to get any compliment from her at all . It's funny now because we often chat openly about makeup , she is so comfortable with me .

[Tracii G]

Teresa I know a few women who have never worn make up just because they didn't know how and didn't want learn how.
I have one GGF who is in her 50s and she has never worn eye make up or had her eyebrows tweezed.
I have tried to get her to let me trim her brows and give her a make over but she just won't do it.
She is very attractive and with some help there is no telling how gorgeous she would look.

[valerie anne]

My aunt caught me in her bra. It was much too big for me.

She padded me out with cotton wool, and then applied bright red lipstick and lots of mascara.

She then made me parade round the garden. I think she was trying to shame me, but I loved every minute. Thanks auntie!

[Michellebej]

I was....22 or 23?

I had a girlfriend who was very open and accepting and willing to try just about anything.

I'm from the San Francisco Bay Area and we used to have this event called the Exotic and Erotic Ball in the City around New Years.

My gf decided to go as a school girl and I did the "traditional" ***** thingee.

When I came out all dressed she thought my makeup was on the "nice girl side". She cleaned mine off and sat on my lap facing me and put it on. It was....really nice....Nothing fun happened. We WERE going to a party, but we were both charged up all evening.

I'm going to agree that a lot of GG's don't do well with us. My ex wife sure didn't. Though she did teach me some techniques that I still use to this day on my eye lashes. And my daughter taught me to do a nice wing. Oth I have a very light beard and it is getting lighter with age, so beard coverage is not such a huge thing with me.

I think as the generations change it will happen more and often. Good luck to you!

[BLUE ORCHID]

Hi Lindsay :hugs:, That kind of thing only happens in MY DREAMS. >Orchid ..+:daydreaming:+..

[ellbee]

BTW, for those who doubt it happens?

Head on over to YouTube & search for something like "do my boyfriend's makeup" or "do my brother's makeup"


Plenty to choose from. ;)


Some take it a bit further, like with clothes and/or wig.

Sometimes they'll even go out in public afterwards.


Yeah, yeah, I know... It's YouTube, so it's "not real."

And yet, they're actually *doing* it -- in front of tons of people, at that!


Just imagine how often it's NOT filmed & uploaded.

I know my first experience wasn't. Then again, Al Gore hadn't yet invented the internet. :heehee:

[Raychel]

Back when I was like 12 years old, My friend had a couple of sisters that wanted to dress me up and do my makeup
Being young and stupid, I didn't let them. Looking back, I sure do wish I had.

the only other time, My wife did do my makeup and help me get dressed for a Halloween party one time.
I was so uncomfortable going out in public.

[Alaina R]

Not sure this is what you want but I was 21 and my college girlfriend 18. When I told her about the crossdressing I was very emotional as I felt like a total freak (this is 45 years ago). It felt very scary to tell her as a bad reaction could have really humiliated me, but at the time we really liked each other and I knew I needed to tell her for us to keep getting closer. She reacted great, was very cool with it and completely took away my guilt. I had major fantasies about being made up by a girl (that was my biggest fantasy) and she totally fulfilled those - no holding back as she just went with what turned me on. It wasn't that she was so into it, but my excitement turned her on and she wanted to make me happy. She was a very pretty girl; she was very into fashion and very comfortable and good with makeup. I still remember her happily showing me the deep red lipsticks she had bought for playtime after I told her my fantasies.
Over the years, with other women, I had more difficulties as a lot of women don't like male crossdressing but I did finally meet my current wife some 20 years ago and she totally adores male crossdressers - she has been into them since she was a kid. The odd thing is I don't even dress much anymore as it isn't quite the kick it was when I was younger although I still do like it.

[docrobbysherry]

I was over at a GG friend's last nite. She puts on her makeup in front of me if we r going out. She has to be good at it because she does a lot of live shows in Hollywood. She said mine makeup work work is terrible, (she's quite rite), and she'll do mine next time we meet!:battingeyelashes:

I would agree with Micki. But, only if u want to look like a kabuki dancer!:tongueout

[amandagurl2014]

Had makeup done at salons several times. Most of it was positive experiences and it was worth the $ spent just to get to chat with the girls. Got tired of wasting money and decided to learn how to do it myself. Spend the money on the right products and it will pay off and save lots of $$$ in the long run. Several trips to ultra later and my makeup now is comparable to what I had to pay $30-40 to have done a few years ago. Still go to a salon to keep my brows in shape. I now have a bestie, a Cato sales lady I met about a year ago. She is around 15 years older than me. We have become great friends. It shocked me that she pursued a friendship with somebody like me. We text everyday and go out for lunch or shopping every now and then. The key is that I have been upfront and honest about myself with her. She will touch up my makeup sometimes but has never fully done it for me. She bought me a nice maxi dress and flats this past Christmas. It just feels great knowing that another person genuinely cares about you and does not think your crazy because you like to dress up and feel pretty.

[MarinaTwelve200]

A about three years ago when I took part in my Church's Womanless beauty contest. Some older teenage girls did some or our makeup---mine included. I thought I would learn a tip or two about applying foundation--as it gets streaky when I do it. and whatever else I could learn.-----They did a fair job, somewhat disappointing, as I could have done better myself. It was fun experiencing a FANTASY I had dreamed about since I was a teenager though.

[Beverley Sims]

I was seventeen when some girls decided to make my face up, we were all astounded as to how well the face painting exercise turned out.

One girl was practicing makeup as a career.

[Nastasha]

High School ... was over at one of my friends homes and she had a friend from her old neighborhood over visiting. My friend knew I liked panties, bras, slips ... she'd caught me holding her panties up in front of me seeing if they would fit and had seen me eyeballing her panty drawer when she left it open once, even helped her fold her clothes from the laundry ... she always joked about me just wanting to see her panties so would give them to me to fold.
So, her and her friend started teasing me asking me if I liked panties, asking me if I had ever worn any, my friend told her how I like looking at and holding her panties and how she had caught me holding them up to myself. It kept going and long/weird story short I ended up in my friends panties and her friends bra, a blouse and skirt and they fixed my hair and applied makeup. When they were done they told me I was cute but was an ugly girl, we all laughed. I didn't hurry to get undressed and we goofed around for the rest of the afternoon until it was time for her parents to get home from work. Never saw her friend again, but, it wasn't the last time we had a dress and make up session.

[kaleyg]

I think the first time was sophomore year of high school for the powder puff football game. I think that same year at Halloween, a girl invited me to come over and pass out candy with her, and I somehow talked her into dressing me up to see if I could pass as a girl. I went over a few days early to try things on, but then I chickened out on Halloween. Then my junior year, I confessed to my gf about my desire to see what it would be like to dress up. We were alone at her house, and she said, "ok, let's do it!" I still can't believe how cool she was with it. She dressed me up in her clothes, did my hair and makeup. I just couldn't fit in her shoes, but I had everything else on. Everything. I think I looked in the mirror for a bit, and then we took it all off. I still remember it vividly. This was the first of many adventures with her over several years into college. She was amazing.

[Ressie]

Never had the experience myself

[Asew]

The first time I went to a girls night out, my wife and her friend did my hair and makeup. It is the one and only time I have ever worn makeup.

[Richelle423]

It happened to me about a month ago. I was on vacation and my 14 yr old non binary neighbor was a on break from school and she wanted to do my make up.she told my SO that she wanted a drag night at home with us. I let her do it. It was fun. She did my SO make up too.

[SherriePall]

Only professionally four times. Was a late bloomer with the girls, so that avenue was out when I was young.
The four times professionally, the girls were consultants who had become friends. One who worked at a major department store had worked with and been friendly with Divine and others in the city.

[CarlaWestin]

I've told this story @38 times here. Before my ex was my ex, she assured me that my desires were admired and supported.
Hence the creation of Exhibit "A". After that and further down the road, I had a fabulous makeover from Amy.

302939302940

[StevieTV]

Mine was in college. I was in a program that was typically female. We had an event where males would dress as females for a beauty pageant. Being the only genetically male in the class, I was obligated to attend. The GGs had a ball and I was elated! I wasn't out at the time, but I embraced it fully. After the event, one of my classmates asked if I was gay because I enjoyed it so much. Of course I said yes, and the rest of the semester and course was fab!

[NancySue]

My wife has, often, offered to do my makeup, but I’ve always wanted to learn to do it myself. Thanks to her advice, critiques, YouTube videos and lots of enjoyable practice, practice, practice, I’m happy, but, like most, have good and bad days. Sometimes, she feels I wear too much makeup, especially when I contour, and I agree, so I tone it down. Occasionally, I ask her to apply my eye liner.

[traciethetg]

This happens all the time in Hollywood California and surrounding areas like San Francisco where they likely have the most transformation salons.

[Sabrina133]

i was 26. She was a drag queen but has since transitioned. Does that count?

[Palaina Nocturnus]

The first Pride Festival I've ever been to I went with my girlfriend. She did my makeup and let me borrow one of her cute tops. Since then we've gone to every Pride Festival and this year hopefully will be our 4th in a row :)

[JessicasRabbit]

I went to a drag show recently. A GG friend did my makeup. I wore a rockabilly dress and got a vintage inspired updo. I'm not a performer.
It was my first trip into the wild. I got plenty of compliments and had a great evening.

[Micki_Finn]

This happens all the time in Hollywood California and surrounding areas like San Francisco where they likely have the most transformation salons.

Oh REALLY?

[Angie G]

They were my clothes but my granddaughter did my makeup for Halloween one year. it wasn't coming out as far as she knew it was just for the Halloween costume, But it did feel good having my makeup done by someone other the myself. :hugs:
Angie

[StacyPump]

Had makeup done at salons several times. Most of it was positive experiences and it was worth the $ spent just to get to chat with the girls. Got tired of wasting money and decided to learn how to do it myself. Spend the money on the right products and it will pay off and save lots of $$$ in the long run. Several trips to ultra later and my makeup now is comparable to what I had to pay $30-40 to have done a few years ago. Still go to a salon to keep my brows in shape. I now have a bestie, a Cato sales lady I met about a year ago. She is around 15 years older than me. We have become great friends. It shocked me that she pursued a friendship with somebody like me. We text everyday and go out for lunch or shopping every now and then. The key is that I have been upfront and honest about myself with her. She will touch up my makeup sometimes but has never fully done it for me. She bought me a nice maxi dress and flats this past Christmas. It just feels great knowing that another person genuinely cares about you and does not think your crazy because you like to dress up and feel pretty.


Hello Amanda - what kind of a salon did you go to for your makeup? How did you know they would be CD/Trans-friendly?
So nice that you have your bestie to have fun with!
Your profile picture is beautiful, by the way! : )

[amandagurl2014]

Thanks! I just looked up some salons in a town I was going to visit in 2014. Same year I joined here. Was very nervous just hitting button to make the call. I would ask if they done makeup and if they would be willing to allow somebody like me to come in. Was turned down a few times. Most were receptive. I visited one stylist several times over a three year period. Some just tolerated me to get the $. Those were one time deals. Eventually I learned how to apply a presentable look and stopped going in for it. Most salons I called don't specialize in makeup and just offer it for prom girls and weddings. Some welcomed me in. I had to go this route as I had no tolerating GG friends and nowhere else to go to learn. I'm very fortunate to have a close GG platonic friend now. The profile pic was what I showed the MUA on my first visit. She got me very close to it.


Hello Amanda - what kind of a salon did you go to for your makeup? How did you know they would be CD/Trans-friendly?
So nice that you have your bestie to have fun with!
Your profile picture is beautiful, by the way! : )

[suchacutie]

My wife and I discovered Tina together, suddenly realizing she had always been there, so everything started with my wife making up Tina, showing her how to do everything one step at a time until Tina could be on her own. It was, and still is, intensely emotional!

[Desiree2bababe]

My wife, then girlfriend, dressed me up one Halloween. This after I'd come out to her as a transvestite. Of course I had all the clothes, she provided the makeup. She remarked on how good I looked. We had a blast going to a disco bar. Floored me when she suggested we go find some men, wish I'd taken her up on it but I was scared at the time she was just trying to find out if I was gay ( which I guess I was as I'd been with many men ) just always loved women too.

[Amy Lynn3]

The first real makeover was done by a artist who does makeover for TG's only. She was very good and when I first look into a mirror it surprised me with how much I looked like my older sister. You can see the results of the makeover in my Avatar picture.

[Dena]

When I was 22, I went out of town to Halloween party. When discussing costumes, a girl in the group that I had a crush on, suggested dressing me
up as a woman. Even saying she had a dress I could wear. I laughed it off and didn't persue it. Regretted doing so ever since!

[BTWimRobin]

When I was around 19ish the girl I was dating asked me if I would mind her putting makeup on me. Naturally, I said yes since I was always curious what I looked like all made up. When she was done, I looked in the mirror and there was this pretty young woman looking back. I remember her dog doing a double take when he looked at me. Anyway, one thing lead to another and she was having me wear her bra, panties, pantyhose. I really wished I could fit into her shoes. The whole experience was intoxicating and I was hooked. Long story short, we eventually broke up. The only regret I had was not asking her to teach me how to do my own makeup.

[Sallee]

I have had it done a few times professionally and had some makeup done at the makeup counter in department stores but never done by a girl friend although I would love it but I think most GFs want their guy not another GF.
the professional makeup applications were wonderful. I do love playing with makeup and applying different colors and moods. I wish there were more makeup saloons for CD's here in So Cal. There is one in OC that I know of but haven't been there. Some saloons here in San Diego will do CD's or so I have been told but I haven't been for a full make over. I have been in and tried different products just haven't had the opportunity to have the full monty at one of them

[April T]

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!

[nvlady]

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?"

[Melissa_Me]

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

[Sometimes Steffi]

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.

[TheHiddenMe]

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.

[Tania75]

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.

[Palaina Nocturnus]

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!!!!!!

[baldy1]

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

[Connie D50]

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 :battingeyelashes:

[Hogrom]

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 :)

[Manasi]

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).

[Kate Jennings]

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.

[HollyGreene]

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.

[VS Fan]

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* ;)

[Helen_Highwater]

I have been surprised how many GGs that haven't had a colour check done and are basically not that good at applying makeup.

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

[MonicaPVD]

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.

[dana digs sweaters]

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.