When she doesn't know & suggests you should dress

[Elsa Larson]

I was looking thru a dating site on the internet. Found a thread: "Tall Women Short Men". Thought I'd read all the posts since in male mode, I'm always on the lookout for tall women.

A woman 5'7" offered this suggestion:

Or, you could ask him to wear heels.

:o

Have you ever been invited to crossdress by a woman who did not already know of your crossdressing?

[Christina Horton]

Can't say that I had . Before I came out to every one I think I would jump at the chance. Now it the whole thing for me.

[RachelZ]

I've never been asked to dress by a girl, but one of my friends from school did offer to paint my nails once. I said no because she only had orange.

[Ras]

not yet....but I still keep hoping one would...

[TxKimberly]

Pffft . . .I wish!

[kalina]

Have you ever been invited to crossdress by a woman who did not already know of your crossdressing?

Most GGs are not turned on by the idea of their man in women's clothes, but if you're lucky enough to find a GG like that, you might get more than you bargained for... she might be a bit kinky!

[Ras]

but their are a lot of GG's that absolutely love it and would have never thought of it on their own. I agree t some will take the ball and run with it.

[Angelofsomekind]

I have! Before I was married my soon to be wife found a pair of panties at V.S. that said "sexy" on the front, she joked that she thought she should get it for me. So the next day I went out and bought them. She kinda laughed and thought it was a joke.

[Xenia]

A couple of times, but usually not with any seriousness. I had a couple of female friends in college who told me they wanted to give me a makeover and have me give them a runway show with their clothes....but then they just as quickly forgot about it. (Teases!)

I dated a girl once who told me she was going to dress me in a corset and fishnets the next time the local theater ran Rocky Horror....but we broke up before that happened.

But then, on my first date with the woman who's now my wife, she asked, completely out of the blue, if she could give me a makeover. It was my first inkling that she might be the one. :)

[StacyCD]

I've never been so lucky. It's probably one of the heterosexual crossdresser's ultimate fantasy!

[Sarah-RT]

It's probably one of the heterosexual crossdresser's ultimate fantasy!

You hit the hammer on the nail with that one, well for me anyway

[alexandracross]

Hi everyone I was asked to dress by my GF and have been into for a while. I think an understading significant other is very important.

[JamieG]

Before we were married (and before I finally opened up to her), there were three occasions where my wife suggested that I crossdress:

1) During a football game when our team was losing, I exclaimed that I would "do a dance" if they came from behind to win. She said "Yes, and you should do it in a tutu. That would be so fun." Our team lost, unfortunately...

2) When she was planning on going as Queen Amidala for Halloween, she said that she would make me her handmaiden. I laughed and said okay, but it never came up again.

3) We played a game where we got to decide what each would do if we lost. I said she would have to model a french maid costume for me. She said, okay but only if I would do the same for her if I lost. I agreed, with pretend hesitancy. I lost (without even trying to lose) and put on the french maid outfit. She asked if I was enjoying it, I lied and said no. She had me take it off after five minutes. I wonder what would have happened if I had said I liked it?

In retrospect, its hard to believe that she was so negative towards my crossdressing when I finally did open up to her. Fortunately, she has become much more accepting over time.

[Shelby]

a gg friend has made comments on occasion. Once we were just hanging around after some event and I commented on pointed her heels were and asked if I would like to try them on. I declined since the moment wasn't right and it too many people were around.

We were in a theater production once and I needed to wear a coat in a scene so she offered her coat to see if it fitted me. It was a short winter woolen type coat and to small but cute.

Just this year we were working at our theater booth at a local business expo dressed as nuns promoting our next show, a comedy about nuns. I also wore a habit and some people didn't realize that I was a guy at first. She said that with the right makeup and a closer shave I could pass as a woman.

Out of the blue, she once suggested that we go shopping and that I go as a woman. She is always hinting that I either wear something of hers or dress up. Good bet that she knows and I have always wanted to tell her but never had the chance to.

[samantha48328]

I once had a girl friend ask me to wear her wedding dress. I did and what a wild night it turned out to be! No she didn't know I was a crossdresser.

[erica12b]

i wish , and im clickig my ruby heels , please please

[suchacutie]

This one's easy! My wife saw my legs in stockings and said I needed a dress!!!

Well, that one changed my life and here I am!

tina

[Elsa Larson]

We played a game .... I said she would have to model a french maid costume for me. She said, okay but only if I would do the same for her if I lost. I agreed, with pretend hesitancy. I lost (without even trying to lose) and put on the french maid outfit. She asked if I was enjoying it, I lied and said no. She had me take it off after five minutes. I wonder what would have happened if I had said I liked it?

In retrospect, its hard to believe that she was so negative towards my crossdressing when I finally did open up to her. Fortunately, she has become much more accepting over time.

A Wonderful story, Jamie ! Goes to show that even when we're fulfilling our wildest dreams, we sometimes can't admit that we enjoy crossdressing.
I hope this example is included when the textbook is written for Gender Studies 202: Crossdressing

[dilane]

I got started at age 6 or so when a neighbor girl who was 11 or so (and who was obsessed with transforming boys into girls) convinced me to dress up.

I was always intrigued and even fantasized about being in costume, in a completely different identity, and when she dressed me up something clicked...

[Chiana]

No. Darn it.

But, once upon a time, I was at an apartment in my late teens. There was about a half dozen girls and an equal amount of guys just hanging out. One of the girls was trying to recruit the other girls to help her dress-up one of the other guys. I was really tempted to jump up and shout "Me, me, pick me." They did do it later when almost everyone else was gone. The guy and girl eventually got married and lived happily ever after, from what I understand.

[linnea]

Like others, I wish and have wished for this to have happen, but I have had no such luck.

[urmilaaa2008]

yes, and it was my wife, that is how all this started, since until the i also didnt know that i had secret longing in my subconscious mind. This playful act of her brought that out and now i dress up but only at home and under my DRAB dress when i go out. eventhough she is not very enthuastic about it she tolerates it

[SherylynJade]

When I was still in high school, a couple of friends of mine (both girls) wanted to dress me up so badly, but I didn't give in. Oh the regrets we all have:daydreaming:

[Rachel Morley]

Have you ever been invited to crossdress by a woman who did not already know of your crossdressing?
Well yes ... kinda ... when I was living in the UK, single, and living on my own, I had a fairly large circle of friends and we used to often have costume parties. I went to a Rocky Horror party as Magenta (French Maid) the next time one of the GGs had a birthday party she asked me to come dressed as a girl. She said she though I would look cute and it would be great fun. Costumes were supposed to be optional and so I did do it. I was one of only three that was in a costume and of course I was the only person cross-dressed.

[sarahNZ]

but if you're lucky enough to find a GG like that, you might get more than you bargained for... she might be a bit kinky!

I was lucky to find one like this but she has a partner :sad: snd there is no way i will get in the middle of the relationship! So friends will do.:hugs:

[allisonrn06]

When my wife and I first started dating, she wanted me to dress as a woman for Halloween. She didn't know then that I was a crossdresser, and didn't till about a year later. But she didn't really encourage me to dress until a couple of years ago, now she frequently does - just about anytime we're home in fact! In response to what some of you have said about GG's not wanting their men to dress fem - I thik the number who would like to see their men do it at least once is pretty high, although for a lot of them, they wouldn't want their guys making a habit of it. :2c:

[Marisa_M]

Have you ever been invited to crossdress by a woman who did not already know of your crossdressing?

Unfortunately never...but I'd love it so much!

[Chrissy be good]

I've had this happen a few times. One girl I was dating was going to cosmetology school and wanted to practice putting on make up. One thing lead to another, and the next thing I know, not only am I wearing make up, but hose, a skirt and sweater. I told another girl of my nylon fetish and she said she would wear a "nice" outfit if I would do the same. I joked that she really didn't want to see that, but she insisted. That night I squeezed into a corset that was way too tight. With garters, thigh highs and heels that were 2 sizes too small.......I loved every minute of it.
I think there are some gg that do enjoy being with a crossdresser. I dated a girl who I met en femme, and only really saw me dressed. She was bi and liked that her "girlfriend" had more to offer.

[Laura_Stephens]

I wish!!!!

[MissConstrued]

Most GGs are not turned on by the idea of their man in women's clothes, but if you're lucky enough to find a GG like that, you might get more than you bargained for... she might be a bit kinky!

Ain't that the truth!



a gg friend has made comments on occasion. Once we were just hanging around after some event and I commented on pointed her heels were and asked if I would like to try them on.

Sounds like the right kind of girl... usually it's the girls asking if they can try *my* shoes on, though.... :)



Out of the blue, she once suggested that we go shopping and that I go as a woman. She is always hinting that I either wear something of hers or dress up. Good bet that she knows and I have always wanted to tell her but never had the chance to.

Holy crap! How many more opportunities are you going to piss away?

Time to man up and get girly. :heehee:

[Sammy777]

Time to man up and get girly. :heehee:

:lol2: Agreed!

Put them big girl panties on and just do it .

[jenniferj]

Many years ago, shortly after we were married and before I worked up the courage to tell her, DearSweetWife dressed me up a little. She had unpacked a longish knit dress that I hadn't seen before and I told her that I really liked it - she said, "If you like it so much, why don't you try it on?"

"Oh no, I couldn't do that...". "Yes you can - here strip down". She slipped me into a pair of panties, and pulled the little guy back between my legs, and quickly hooked a bra behing my back. An urolled pair of socks in each cup, and the dress was pulled down over my head and down most of the way to my ankles. "OK - that's enough" I said... "Nope, nope"- She grabbed a hairbrush and fluffed up my hair (it was chin length as was the style in the early 70s) and was getting up up get her make up, when she looked at me and saw something that disturbed her. I assume that I looked a little less unwilling-embarrassed-guy than she expected, but she kindof shuddered and said " You're right - that's enough" . She pulled all the girl clothes off of me and we got gressed normally and went out for a cheap Italian dinner.

It was a few months later that I finally realized that the crossdressing was not something that I would grow out of now that I had regular female company and I "had the talk" with her. I don't think anything has scared me more than that day, but she was pretty cool about it - accepting but not encouraging. And it has stayed the same for 37 years.

-jj

[diannecourtney]

As I sit at the key board in my4" heels and knee high skirt with all the lovely undies I can only wish for understanding....

[denisecdfl]

If you can't do it at home, you can always pay to go to a dressing service. Put youself in the hands of an expert who loves to experiment on a new client, trying on different wigs and outfits and taking pictures. Plus, you can learn a few makeup tricks.

[NathalieX66]

When my wife and I first started dating, she wanted me to dress as a woman for Halloween. She didn't know then that I was a crossdresser, and didn't till about a year later. But she didn't really encourage me to dress until a couple of years ago, now she frequently does - just about anytime we're home in fact! In response to what some of you have said about GG's not wanting their men to dress fem - I thik the number who would like to see their men do it at least once is pretty high, although for a lot of them, they wouldn't want their guys making a habit of it. :2c:

Let's just face it....she's a modern woman with an open mind, a sense of humor, and a good heart:battingeyelashes:.

[Sara82]

I agree, I think most girls as some point will want to see their BF, guy friend, or husband, dressed up in girls clothes as a joke, then there are a few extra special wants, who are really into it!

I knew this guy who's GF forced him to dress up, and he had no interest in it whatsoever, but did it just to please her. GO FIGURE!!

[Andy66]

I was in a lingerie shop with a past boyfriend many years ago. As he was looking at things for me to wear, it occurred to me that some of it might also look good on him. It took some convincing, but once he tried it he decided he liked it. :)

Just recently my co-worker (a very pretty lady) and I were talking with a guy at the store fitting room near quitting time. The guy playfully took a sexy nightie from a clothes rack and held it in front of himself. We tried to convince him to model it for us, but he chickened out. Too bad for him, he might have had a very interesting night. ;)

[Aurora Rosas]

Hi


I had a girlfriend who did put me on make up as a woman and she got turned on by doing so. I was so excited. A week later I took one of her miniskirts and wore it around the house. She caught me and she was anoyed.

Some years later, another girlfriend painted my toes with red nail polish and I told her I wanted to keep them for some days and I did so. Now she knows I corssdress.

Aurora

[AmiFL]

I am married and my wife absolutely does not approve of my dressing, ergo I have not for years. It is always in the back of my mind what she will do when the time comes. Once in anger she outed me to my teen son who blew it off and did not care........... that is another story.

However years ago, I had a GG friend who I became far too close with. We had talked about everything including crossdressers. But. she did not know at the time about my proclivities. Finally, I told about my situation and she became intrigued about my crossdressing. So much in fact she wanted to see me dressed. After much prompting I agreed. She was amazed at my transformation. I was much younger and thinner at the time and had gotten pretty good at the whole thing. It was one of the most pleasurable experiences of my life. She was very supportive and used to buy me dresses, new underwear and shoes. Unfortunately when she was discovered by my wife I had to let her go...... sometimes I wonder if I did the right thing.

[ifitfeelsgood]

2 times. I was so self conscience about it though, i did not dive in. The first time i did it, and it was awesome, but I held back. The second time I said no but later came out to this girlfriend. I stayed with her longer than I should have because she accepted my dressing.
I came out to my wife a month in to dating, years before we married.
Always come out before you plan to marry, always!

[kimmy p]

Most GGs are not turned on by the idea of their man in women's clothes, but if you're lucky enough to find a GG like that, you might get more than you bargained for... she might be a bit kinky!


And the problem with that would be?!?!?!?

[shayleetv]

YES!
My best friend in college was a GG. We did a lot of things together, we were like brother and sister. She had just broken up with her boyfriend and had wanted to go to the Jr. Prom at the University. I suggested that I would like to take her. We were at her work at the time which was a drop and pick up store for a Dry Cleaners. She got joking about me being the girl and her the boy. She got the idea because a customer had dropped off a long prom like gown and she was tall like me. She held it up to me and said see this would fit you. I said sure with a joking like laugh. Janet didn't know then that I crossdressed. Regrettably, she chickened out and we went to the prom as a real boy and a real girl. A few weeks latter I was coming home from a class that I had attended enfemme and dropped by her work. Then she really regretted chickening out. We talked too long because she had a million questions but accepted me and it didn't hurt our relationship at all.

[boardpuppy]

No but I sure wish a GG would ask.

Hugs,
Alice

[jenny01]

I am slowly working into this with my GF. One day after a shower at her house, she had a pair of panties on the bed and asked if I wanted to wear them. I couldnt believe how lucky I was at this point. I said yes and pulled them on. She loved it!
She since has gave me several pairs of her panties, and said she is going to empty my drawer of my mens undies.
She does on a regular basis paint my toes. Some times she picks the color sometimes I do.
I am letting her take this at her pace and we are progressing forward into my feminine side.
This woman is a true keeper.

[Charla McBee]

Quite a few times when I was in high school but I always said no or backed out. I hadn't been doing this very long at the time. I deeply regret not taking even one of those oppurtunities.

[Lara Smith]

Many years ago, shortly after we were married and before I worked up the courage to tell her, DearSweetWife dressed me up a little. She had unpacked a longish knit dress that I hadn't seen before and I told her that I really liked it - she said, "If you like it so much, why don't you try it on?"

"Oh no, I couldn't do that...". "Yes you can - here strip down". She slipped me into a pair of panties, and pulled the little guy back between my legs, and quickly hooked a bra behing my back. An urolled pair of socks in each cup, and the dress was pulled down over my head and down most of the way to my ankles. "OK - that's enough" I said... "Nope, nope"- She grabbed a hairbrush and fluffed up my hair (it was chin length as was the style in the early 70s) and was getting up up get her make up, when she looked at me and saw something that disturbed her. I assume that I looked a little less unwilling-embarrassed-guy than she expected, but she kindof shuddered and said " You're right - that's enough" . She pulled all the girl clothes off of me and we got gressed normally and went out for a cheap Italian dinner.

It was a few months later that I finally realized that the crossdressing was not something that I would grow out of now that I had regular female company and I "had the talk" with her. I don't think anything has scared me more than that day, but she was pretty cool about it - accepting but not encouraging. And it has stayed the same for 37 years.

-jj

Not knowing how you looked dressed, I can only speculate. But perhaps you were suddenly looking a little too good! It may have stirred up all kinds of things in her that she didn't want to deal with. Even women who are willing to participate in CD on some level or another can still feel uncomfortable on many levels with a male that can look pretty and presentable, especially if she might feel he has a particular fem feature that she isn't thrilled with on her own body. For many women it doesn't take much for them to feel less than. Just as you have to be man enough to wear a pair of panties, she has to be woman enough to feel good about you doing it, especially if you look good in them and she is turned on by it, whether she lets you know or not. As you got prettier, God only knows what kind of thoughts might have been racing through her head. Even my spouse who participated with me to a level even I had never dreamed of or fantasized about, suddenly decided one day that “she was only doing it because she loved me” and didn’t ever want it to happen again, (after 25 years of mostly her initiating) to the point that she doesn’t even want to have boy/girl sex now because it may be in the back of my mind and she will never really know if it is. This from a woman who took me places I had never even been in MY mind yet. Who I never pressed or requested dressed sex with except for a few times because I never wanted to push that part of myself on her. I will never know the answer to the conundrum and you probably never will yours either.

[SatinSarah]

have been given opportunities to dress to have a laugh with girlfriends/ groups but as I am also quite macho?! I have been afraid to do it in case I looked like I enjoyed it too much. I htink my ability to walk in heels I see women struggle with would be a dead give away. But then I have always regretted missing the opportunity to dress legitmiately!!

[BonnieJG]

My wife tells me all the time I should a been a girl . . . I like girl things dose this meen that I should dress and be a girl around her ?