A crossdresssing conundrum

[Matt2Marissa]

So, I've been dating this girl for almost a month now, who I've been friends with since high school. She asked me if she could give me a complete feminine makeover (I have a sort of feminine body shape and a not so masculine face, which she told me made her always want to ask). I wanted to say yes, but I'm rather paranoid by nature, so I said "no, I had that done to me in high school and didn't like it". I don't want to pretend to hate it, but don't want to appear to like it too much. I'm not a very good actor.
I've always wanted to have this done, but never had because I'm always too scared I'll give my secret away unintentionally.

[kimdl93]

ok, so why would you want to torture yourself and deny a chance at something really special? If, as you say, you're sorta feminine to begin with, don't you think thats clearly something this girl is intersted in? I mean, honestly, if she was into body builders,she'd go elsewhere right?

You should NOT NOT NOT act. If you enjoy being made up, dressing up, then you really need to be honest about it. Otherwise you'll live in a cell ofyour own creation.

[AlannahNorth]

Well, you could still say 'By the way, were you serious about the offer?' and take it from there. Say thinking about it has got your curiosity... and go with it! You'll probably regret it if you don't.

[Julogden]

Oh Lord, RUN BACK AND TELL HER YES!!!!!

If you don't go through with that, you will always regret it. It's very true that the things we regret the most are the missed opportunities.

Go for it!!!!!!!!!

Carol

[Haley Heather]

I have had several girlfriends in the past try and play this game with me and everytime I have played. And I always loved that bet 'I bet you can't run in those heels'.

[donnatracey]

I'd be in heaven if a girl/woman made that offer. Do not, I repeat, do NOT turn it down......

[AlannahNorth]

Just something I wanted to add to all this: I WISH I had a GF who would make me such an offer!

[Tanya C]

Missed opportunities like that one you end up kicking yourself over. Call her and tell her you've changed your mind. She seems like she's interested in doing the makeover, and maybe this time you will like the results.

[danitvpe]

Go for it. I have always regreted to miss oportunities like those.

[darla_g]

I had an opportunity for something like that in college. Foolishly i passed it by and i still regret that. It might have been fun and it was with two girls.....oh the imagination is racing....

[Eryn]

I tend to counsel conservatism but what the heck, you're young, she offered, and you should take her up on it! It might be the start of something very special!

[Stephanie Miller]

Well, I think you should put on yur big girl shorts on and head right back to her. Just let her know that you guys have been friends for a long time and you thought about it and can handle a simple request like that. Just tell her it may have been the person and teasing that made it uncomfortable last time - but you trust her and feel this time it would be different. Possibly even fun.
Then go with the flow. Your friends after all. I doubt she'll do anything to embaress you. Maybe if you let her take the lead it'll go further than you ever dreamed.

Or don't. What the heck. You'll just end up regreting it FOR THE REST OF YOUR FRICKIN' LIFE!!!!!

[t-girlxsophie]

Get yourself back and tell her you have had second thoughts,you could always just say,you think it might be a laugh to try it.Sounds like your friend will treat you to the makeover of a lifetime,and wont do anything to make you look foolish like your last experience.Think about where it may lead

Sophie

[Shari]

Try to bring the subject up again and this time, allow Marissa to do the thinking, not Matt.
Don't blow this chance!

[erickka]

Oh My!!! I surely would not have looked that gift horse in the mouth. Soundsto me like that could be the beginning of a very special relationship .I would tactfully bring that subject up again, and REAL soon.

[Gerrijerry]

I can understand how you feel. Say yes and she might find out somehow that you enjoy it way too much. But the others are telling you the truth. Just go back when you are with her again and say yes. You may just find that this is the start of something better then just a makeover. She may be your wife one day and need you as much as you need her. Take a chance you never know when a girlfriend is the perfect match for you.

[Kathy4ever]

I agree with the others. If you like to dress then rhis might be the chance that you will have someone to share your inner self with. I would try not to show too much excitement over it. Let her lead the way and see where it takes you. Keep us updated what you decided to do and how it turned out. Go for it!!!

[KrystalA]

Have you gotten the idea that everyone here thinks you should let her do it? YES..absolutely, positively, no doubt, without question. DO IT!!!!!!

[DAVIDA]

Yep! Call and set up the appointment!
Ask her if you should bring a couple of outfits with the shoes to match.
Oh! don't forget the wig!

[Alisa]

I don't think I would do it unless I was ready to admit to being CD to her. Otherwise the deceit and paranoia will probably take away from the experience.

[sissystephanie]

When I proposed to my late wife I told her that I was a CD. She asked me who did my makeup! I told her that I did it myself, though not very well. She said, "from now on I will do your makeup and fix your wig!" She did that for the almost 50 years we had together!

Marissa, as others have said, DON'T PASS UP THIS OPPORTUNITY!! Go for it!

[BLUE ORCHID]

Hi Marissa, Run don't walk back and say yes to a makeup.

Orchid

[Kiera79]

So, I've been dating this girl for almost a month now, who I've been friends with since high school. She asked me if she could give me a complete feminine makeover (I have a sort of feminine body shape and a not so masculine face, which she told me made her always want to ask). I wanted to say yes, but I'm rather paranoid by nature, so I said "no, I had that done to me in high school and didn't like it". I don't want to pretend to hate it, but don't want to appear to like it too much. I'm not a very good actor.
I've always wanted to have this done, but never had because I'm always too scared I'll give my secret away unintentionally.

She can clearly see that you have a feminine nature to you anyway, the girls can tell, tell her now since she wants to make you over its awesome.

[Jannine]

Go for it girl,
You dont know what you're missing.
If anyone knows how to do a feminine makeover.......Its a GIRL !!!
Believe me, they get lotsa practice. AND it would be a groovy way 'break the ice' about your interest.

Jannine.X

[Cynthia Anne]

You're a sick puppy girl! ha ha! What a great way to break the ice! If you are serious about her you need to beg her for a second chance to get it right! A song comes to mind! :What was I thinking!: Hugs!