Does she want me to dress?

[NewDresser]

I have been with my girlfriend for almost a year now and in that time she has jokingly suggested that I wear various articles of her clothing on five separate occasions. Now I say jokingly because I am about eight inches taller than her and outweigh her by at least 60lbs and there is no way I could fit into her clothes. Is there any chance she is more than just kidding around? This could be the chance of a lifetime for me but how can I test the waters without freaking her out if it turns out she was just trying to be funny? I will gladly take any suggestions.

Thanks,
Caitlin

[Billijo49504]

Just tell her the clothes she has won't fit. But we could go out shoppingfor an outfit for me....BJ

[annomusE]

Give the girl a chance! Try them on and see what you like and if they dont fit o well... then you get to go shopping!

[Paula G]

Take her up on it the next time she brings it up, see how she reacts and take it from there.

[Shananigans]

I agree with the others. Tell her you might need a bigger size and see how she responds. Sounds to me like she's testing the waters with you as much as you are testing the waters with her.

Jump in.

[Nichola]

Just go for it & enjoy it, my girlfriend did similar things early in our relationship although I think she only thought of it as a bit of a joke.

I'd would have loved for it to happen again but sadly it never did. I've made subtle suggestions over the years but she seems almost repulsed by the idea now.

Make the most of it, it could be the start of something very special between you.

Nichola
xxx

[Maryesther M.]

Does she want you to put femme things on as a prelude to lovemaking?
If so, go for it & enjoy it, but equip yourself with stuff that fits you.

[Roberta Marie]

Why ask us? The only one that knows if she is serious or joking is you girlfriend. Ask her.

Grace,
Bobbi

[Anna Maria]

Wot BobbiJo said. Take her shopping!

[Rachel Morley]

Go for it ..... better to regret something you have done, than something you haven't! Huh? :D

[Karentgny]

Hmmmmm, that's how it started forme.... my wife is a six 6 and I'm a 14... now we shop together and at times she brings home some of the sexiest outfits for me! I'm in heaven!

[AKAMichelle]

Give the girl a chance! Try them on and see what you like and if they dont fit o well... then you get to go shopping!

I was trying to figure out what to say and this was it. S-H-O-P-P-I-N-G Yeah!

[rickibarr]

If she brings it up, ask her, "What do you have in mind?"

Then you'll know for sure!

[sterling12]

I will assume that you think she doesn't know about Caitlin, at least you haven't told her about your femme -self.

Your not going to like this, but I will also assume that since she keeps "insisting" that you try on some of her clothes, that she has made a "Discovery" of some of your stuff.

But, at least so far she isn't antagonistic. And, that's a good start!

Peace and Love, Joanie

[Shananigans]

If she brings it up, ask her, "What do you have in mind?"

Then you'll know for sure!

I think this one is Perfect.

Call her out on it already, I want to know the outcome.

[Sammy777]

Maybe if you better explain how and when these 5 times came up and what happen it will give all of us here a better understanding of what your g/f might be thinking.

[Kate Simmons]

Only one way to find out for sure my friend.:)

[NewDresser]

I will assume that you think she doesn't know about Caitlin, at least you haven't told her about your femme -self.

Your not going to like this, but I will also assume that since she keeps "insisting" that you try on some of her clothes, that she has made a "Discovery" of some of your stuff.

But, at least so far she isn't antagonistic. And, that's a good start!

Peace and Love, Joanie

I am 100% sure she does not know about my little hobby. Every female piece of clothing I own is locked up and my computer is password protected.
She really hasn't been insisting that I wear anything. I tend to sleep in just a t-shirt and underwear and a couple times she tried to get me to wear her pajamas to bed, another time I was getting dressed for work and couldn't find my underwear so she gave me a sly little smile and suggested that she may have some I can borrow, and there were a couple other times that I don't remember the details of the story but involved one of her bras and another time with a camisole.
Thanks for all the suggestions. I think I like the idea of "jokingly" suggest that she/we go shopping for something in my size. Hopefully she will make another offer soon.

[Chari]

If she hasn't brought up the "wear my clothes" subject recently, tell her you thought about her request and if she still would like you wearing her clothes, you will do that! Make a date for that to happen, go slowly - maybe she has the desire to dress you too, then be open about how everything of hers fits(?) and feels. Could it be she is pushing to see how much control she has over you? She may know more about your feminine side than you think and is testing to see how much you will reveal. Soon you may be out shopping for matching or similar outfits and allowing her to give you a makeover! LOL Whatever the outcome, please keep us posted, and enjoy the adventure.

[monalisa]

You missed out on 5 opportunities so if 1 more comes go for it as it might be your last chance.

[Naomi Rayne]

Just tell her the clothes she has won't fit. But we could go out shoppingfor an outfit for me....BJ

I think this is the best way to test the waters. Half jokingly but half serious so that you can swing it either way if you need to. Pull the joke a bit farther in because that will cause her to react.



If she brings it up, ask her, "What do you have in mind?"

Then you'll know for sure!

This one is also a good one because it pushes farther into the conversation. This one puts a bit more emphasis on the fact that you are completely fine with it, but that is not necessarily a bad thing. Either option i think is a good one.

[SheriM]

The next time she asks or brings it up, tell her that it might be kind of exciting to wear her clothes and go from there. You might be going shopping with her soon. Good luck.
SheriM

[Angiemead12]

It maybe just be a joke. Thread carefully and don't take it to seriously as to now shock her when you try it out.

The giveaway is when you start enjoying it when your wearing it.

[bianca66]

Go out and buy the identical articles of clothing that she wants you to wear (but in your size). Then when she asks you to wear them switch the articles to the ones you bought...Once she sees that you fit in them she will never ask you to wear anything again. :devil:

[Yvonne York]

Ask her the next time she says it to put something on you and see her reaction. Chances are it will be lingerie or something that may well stretch to fit. And then enjoy the rest of your life together :-)

[Susan4]

it isn't a test.

In my youth I had a girlfriend who suggested I wear one of her dresses one afternoon. It was a long dress, down to my ankles. I loved it. So, of course, I put it on and we played cards in her room for the rest of the afternoon.

Originally she thought it was a lark ... or so it seemed. As the day wore on she got cranky. It was obvious, I was having too much fun. I was supposed to say 'no' ... and prove how manly I was, I suppose. Eventually, I took it off at her request. Then, things got worse, It fit but not perfectly. And, my wearing of it caused a rip in the fabric near the zipper under my shoulders.

Anyway ... then she really got mad.

Two lessons ... Don't be too eager, the purpose of the 'game' may be not to play ... if you do play, wear your own clothes (in the right size)

Regards,
Susan

[Marissa]

It maybe just be a joke. Thread carefully and don't take it to seriously as to now shock her when you try it out.

The giveaway is when you start enjoying it when your wearing it.

This is what came to my mind.. so responding about shopping or having one of the same size, may go down a wrong road. But with so many suggestions by her, it sure seems to have a foundation of wanting you to 'try' on some of her things. :heehee:

So I would have come across with my programmed man response on the second time the request was made:

"Fine, if you really want me to, I'll try it on to make you happy" :o

She will openly say it was a joke, to test you.. hahaha.. :sad:

It will fit and she will smile.. lucky you..foot in the door..:daydreaming:

It won't fit.. "it doesn't fit".. She says "maybe need to see about a larger size"... see previous comment :D

And if you can't find your undies again.. if she suggest her panties.. "fine.. I don't like the feel of too much 'freedom' for the boys in pants anyway"

Good luck in whichever path she takes you on.. it would be great to find out she is a supporter of one who ventures into this.. just tread lightly as others have suggested as it can be overwhelming to some..

Hugs,

[Sarah Doepner]

If the opportunity is presented to you again, and

If you take her up on the offer,

We are confident that you will enjoy yourself. Remember she is the one who made the suggestion and make it rewarding for her as well. Try to find out what she likes about the activity. Does she like dressing you up or is an erotic thing? Is it something totally different? If you want to continue with it you need to make sure you thank her so she knows this is an interest you can share again.

[holly_n_ok]

yeah i think you have several ways to bring it up again and not have to wait and see if she ever mentions it again. next time you see her wearing one of the things she said you should try on or one like it say hey isnt that the thing you wanted me to try on? then say you know it might not look to bad if we could find it in my size. or i was thinking i bet i could pull that off if you wanna go shopping and help me find my size. anyt number of things. maybe definately make her feel a part of what your wanting to do. like tell her well you would have to help me pick out the right color or size because i would never be able to figure that out. something like that. keep us informed!!

[NewDresser]

Thanks again for all the suggestions. I will be back at her place tonight and I will see what I can do to set her up to make another offer.

[Yvonne York]

Can't wait to hear all about it!

[kimdl93]

I am 100% sure she does not know about my little hobby. Every female piece of clothing I own is locked up and my computer is password protected.
She really hasn't been insisting that I wear anything. I tend to sleep in just a t-shirt and underwear and a couple times she tried to get me to wear her pajamas to bed, another time I was getting dressed for work and couldn't find my underwear so she gave me a sly little smile and suggested that she may have some I can borrow, and there were a couple other times that I don't remember the details of the story but involved one of her bras and another time with a camisole.
Thanks for all the suggestions. I think I like the idea of "jokingly" suggest that she/we go shopping for something in my size. Hopefully she will make another offer soon.

I don't know...repeated hints and sly smiles suggest to me that she's at least a tad suspicious. As others have suggested, next time, take the bait...maybe even say "I'd love to, but I don't want to ruin your clothes..."

[anonymousinmaryland]

When you get the green light, don't stomp it. Take off slowly and gain your confidence (and hers). Make sure you read and follow all the signs. In plain english, go S-L-O-W.

[JulieC]

STOP taking counsel of your fears!!!!!

You are in an extremely fortunate position. You are not married or engaged to her. I assume you love her, but that doesn't mean your life will be destroyed if she's no longer in it. You also have multiple clues before you that she not only would accept crossdressing, but would gladly support it.

If you tell her, the absolute worst that can happen is she breaks up with you. Maybe add on outing you to some of your friends. But, after a year I think you'd probably be able to trust her not to do that.

If you don't tell her, and stick with her, you're going to eventually face a choice of asking her to marry you. Do you want her to say 'yes' to marrying you when she doesn't know ALL of you? Do you want to get married only to find out later (via discovery or some such) that she hates the idea? Be left knowing you married the wrong person?

There are many of your sisters here on this forum who would die for the ability to rewind and tell their now wives BEFORE they got engaged.

NOW is the time to tell her.

Now, in telling; you have got to accept yourself as best you can. You can't expect her to accept you if you can't accept yourself. Be PROUD you are a crossdresser. Be PROUD of who you are! Don't lord it over her or something, but do NOT treat it as something you should be ashamed of. If you treat it like a sickness, psycho failing, whatever negative you care to think of, she'll view it that way too probably.

Be confident, and not ashamed. You are who you are. If she won't accept you, tough. Time to move on. If she will accept you, a whole new life has been opened up before you. The rewards are IMMENSE. The penalties of not telling are hellish.

[Naomi Rayne]

it isn't a test.

In my youth I had a girlfriend who suggested I wear one of her dresses one afternoon. It was a long dress, down to my ankles. I loved it. So, of course, I put it on and we played cards in her room for the rest of the afternoon.

Originally she thought it was a lark ... or so it seemed. As the day wore on she got cranky. It was obvious, I was having too much fun. I was supposed to say 'no' ... and prove how manly I was, I suppose. Eventually, I took it off at her request. Then, things got worse, It fit but not perfectly. And, my wearing of it caused a rip in the fabric near the zipper under my shoulders.

Anyway ... then she really got mad.

Two lessons ... Don't be too eager, the purpose of the 'game' may be not to play ... if you do play, wear your own clothes (in the right size)

Regards,
Susan

This i thought was a very good point. But if the women didnt wanna play then she should have suggested it.

[Veronica Lacey]

Let her choose what and when and "reluctantly" give in. Maybe she wants to lead for a while?

Good luck. :)

[Vicki-Z]

I agree with the others. Tell her you might need a bigger size and see how she responds. Sounds to me like she's testing the waters with you as much as you are testing the waters with her.

Jump in.

I agree with Shananigans I think she is the one testing the waters. I would just tell her that you'll do anything she wants but that her stuff won't fit you. Then see if she goes out and buys something for you that will fit. If she does then definately jump in, but take it slow and follow her lead. Good Luck! :D

Vicki :hugs:

[kimdl93]

OK, I'm dying to know if you this has come up again! What's the scoop?

[NewDresser]

Well it didn't happen the other night, we both had a bit to drink and passed out kind of early. This isn't over yet though. I just have to wait until the next time I stay the night at her place.

[satincandies]

Why not find lingerie matching hers in your size, then the next time she suggests a dressing event, you will be prepared. If you have her lingerie in your size you can easily slip into charecter and the 2 of you will have a wonderful time together.

Satincandies:battingeyelashes:

[NewDresser]

Why not find lingerie matching hers in your size, then the next time she suggests a dressing event, you will be prepared. If you have her lingerie in your size you can easily slip into charecter and the 2 of you will have a wonderful time together.

Satincandies:battingeyelashes:

As fun as that would be I would rather her think this was all her idea and not something I have been into since long before I met her.

[Laura-uk]

I wish my SO had that fun view of CDing, you've got a rare opportunity to be yourself here! Sieze the moment
Take the chance some may never have, I takeevety ounce of tolerance from my SO and push it

[Amanduhrob]

Personally I'd either
1) Wait for her to bring it up again, if you bring it up out of the blue, you will cause suspicion.
or
2) Wait for Halloween in 2 months, and ask her about costumes while holding something feminine of hers, if she doesn't connect the dots, she's not serious about it, and you should let it go, or tell her the truth about yourself.

[kimdl93]

As fun as that would be I would rather her think this was all her idea and not something I have been into since long before I met her.

If she's hinting around its probably because she already suspects that you might be interested. And besides, why try to kid her. She may also be aware that CDing isn't something we just pick up on a whim. Giver her some credit and be honest with her once it comes up.

[NewDresser]

If she's hinting around its probably because she already suspects that you might be interested. And besides, why try to kid her. She may also be aware that CDing isn't something we just pick up on a whim. Giver her some credit and be honest with her once it comes up.

I would probably be a little more honest in the future when I am a little more confident that we will last as a couple but until then if I play along with her and try to make it seem like its her idea I have some deny-ability insurance if things don't work and she tries to out me to friends. I can claim it was all her idea.

[JulieC]

As fun as that would be I would rather her think this was all her idea and not something I have been into since long before I met her.

I've seen that approach go badly (well, seen, as in posts on this forum). It works fine at first, but when she finds out via overt enthusiasm, etc., that he's really not her idea so much anymore, it can cause distrust, etc.

Honesty works well. If being honest with her DOESN'T work, she's not the one you want to be with anyway.

[NewDresser]

I've seen that approach go badly (well, seen, as in posts on this forum). It works fine at first, but when she finds out via overt enthusiasm, etc., that he's really not her idea so much anymore, it can cause distrust, etc.

Honesty works well. If being honest with her DOESN'T work, she's not the one you want to be with anyway.

I have also read several posts about the being totally honest way not working out so well either. If she doesn't like it maybe it means I should have quit dressing instead of risking losing her, I enjoy dressing but I love her.

[kimdl93]

If you love her, I'd suggest that you be more open. Yes, there is a risk...but there is a greater risk if you hide your interest in dressing from her...especially when she has seemingly opened up the door for an honest conversation...perhaps she really is hinting to give you that chance to come clean.

I would caution against "quitting" as a solution in any case. I suspect that most of us have stopped with the intention of never dressing again. But we all seem to be drawn back because it is so fundemental to our identities.

[JulieC]

I would caution against "quitting" as a solution in any case. I suspect that most of us have stopped with the intention of never dressing again. But we all seem to be drawn back because it is so fundemental to our identities.

Some CDers also have a notion that if they just found the right woman, they would lose all interest in CDing. This always fails.

[NewDresser]

I set her up to make another comment and she took the bait. Her, a couple friends, and I were all at her place watching a movie. After the movie our friends went home and she went into her bedroom to change. When she came out she was wearing a sexy little outfit for me. After staring with my mouth open for a few seconds and telling her how good she looks our conversation went something like this.
ME: That's not fair, I don't have any sexy outfits to wear for you.
HER: You can borrow something of mine.
ME: What do you have that would fit me?
HER: Probably nothing.
ME: Well I guess we will have to go shopping for something in my size.
HER: (giggle with a little grin on her face)

After that.....well after that is private.

So at this point I think it could still go either way, she was just joking or maybe I will go to her house one day and she will have something lying around that is a bit too big for her.

[Veronica Lacey]

:thumbsup: Nice!

[Greymancd]

If it was me I would put her clothes on and go wherever she suggested :)

[Naomi Rayne]

That still could be somewhat of a joke, but taking the bait u set up does seem a bit like something that someone wasent interested in dressing you up wouldsay. So maybe the next time you guys are joking around like that u can be like so pick a day and well go shopping. lol It all depends on how you want to play it out.

[kimdl93]

As a CDer with a supportive SO, I have to be careful about projecting what I hope will be true into the situation. That being said, I think the next step should be a trip to the mall. I wouldn't be coy about it either...just say, "Remember last night - well, I really do want something sexy of my own."

[Carey2bcd]

I wish I had to worry about this issue, it's a situation to die for, I would love to be in your heels...haaha

Carey

[t-girlxsophie]

Personally I would stop the pussy footing about and come out with It,im pretty sure If you revisited that last nights conversation and added your desire to "have a go at it" you may find that your relationship may go in allsorts of fabulous avenues,but thats only my opinion only you will know whether to go for it or not,good luck to you

:hugs:Sophie xx