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!!!!!:facepalm:

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!!!!! :wall:

[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!:thumbsup:
Ask her if you should bring a couple of outfits with the shoes to match.:D
Oh! don't forget the wig!:rofl:

[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!

[AvidFan]

My GF tried to do this many times. I feel stupid now for saying no all those times. Back then, I resisted all urges to dress.
Now she gets mad if I dont let her do my makeup

[Matt2Marissa]

So, this morning when I called her I told her I thought about it and changed my mind. Told her that the time before, it was due to a lost bet (and just for clarification, that never happened). Its going down Sunday afternoon.

[kimdl93]

OK, now Marissa please resist the temptation to disguise, hide or deny your interest. I know, its scarry, but with risk lies opportunity. Don't worry about presenting some fake masculine bravado...or somehow pretending it doesn't mean anything to you. Be honest and open.

A while back I had my first pedicure with my wife - my initial instinct was to deny that it was fun, pretend that I was indifferent, and refuse to chose color. fortunately, I let the guy thing go, had a wonderful time and left with the cutest pink toenails.

[Eryn]

So, this morning when I called her I told her I thought about it and changed my mind. Told her that the time before, it was due to a lost bet (and just for clarification, that never happened). Its going down Sunday afternoon.

OK, we'll accept that little white lie to save face, but please, be honest with her about your true interest. Two things might happen.

1) The relationship blows up in your face, which would have happened down the road anyway when she found out.

2) The relationship blossoms and becomes a lifelong acceptance of the true you.

I think that in this case honesty is well worth the risk!

[Haley Heather]

So, this morning when I called her I told her I thought about it and changed my mind. Told her that the time before, it was due to a lost bet (and just for clarification, that never happened). Its going down Sunday afternoon.


I hope you both have a great time. :)

[Sophie86]

We'll be expecting a complete account, Penthouse letter style. :heehee:

[Matt2Marissa]

We'll be expecting a complete account, Penthouse letter style. :heehee:

Will do, but not Penthouse letter style. I do not read, watch, or look at porn. I never have and never will.

[Misti]

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

Orchid

Besides, what the hey! It will save you lots of $$$ in your first makeup. So, what's to lose? Like everyone has said, "Do it!"

BTW Afterwards, you'll be chomping at the bit for Amy at Glamour Boutique 2 (here in Vegas) to perform her artistry on you by the time you get here! What'a thrill! HeeHee! :heehee:

[Bree in Blossom]

It sounds like a wonderful offer, I say go for it. I'd love to find a partner who offered such encouragement -- you're lucky to have someone who sees the girl inside you. I understand your nervousness, but she seems like a supportive girlfriend. On a more practical note, she's offered a complete makeover for free -- I've been pricing transformation services online, and they're not cheap -- think of the money you'll save!

[cdsteph]

A dozen years ago, my SO asked the same question..... which made it easy to 'suddenly' enjoy crossdressing as The experience caught on..... didn't need to explain about my dressing for years previous ......

Rush to the phone and accept the offer.... before every girl here beats you to it!

[Billie Jean]

The best I ever looked was when my ex wife did my makeup. I have always wishe she would do it for me again. I have the fashion sense to pick the right outfit but I haven't been able to get my makeup on as well as when she did it and I have tried to match everything she did. Billie Jean

[Raychel]

I think that you tell her about the real you. I would hope that she would accept you and then you can truely enjoy the makeup session.

Eithetr that or tell her taht you were talking to a friend about this and he wants to give it a try. PMme for my ophone number, I will volunteer:heehee:

[Sally24]

Tell her you didn't like the first time because you looked like an ugly girl. That will challenge her to make you look as pretty as she can!

[Melinda Lou]

I had this happen to me at least a couple of times--once in childhood, when a girl wanted to put me, my little brother and her little brother all in her dresses and parade us in front of our mothers, and I declined because I already knew my secret and feared I would enjoy it too much and give it away, and a time or two in college, when another girl suggested I'd look cute dressed as a girl and I declined because my then-GF, who was aware of at least my underdressing and a few other girly things I'd been trying (e.g., painting my toenails) did know my secret. During part of my college years I also had longish hair that I wore in a ponytail (a small rebellion on a conservative campus), and lived in a coed dorm--some of my female friends would occasionally French-braid it for me, which I loved because it was girlish and because I loved the attention.

Make no mistake, girls have a way of knowing when you have a feminine side you're trying to hide, so if she's willing to be playful about it and dress you up or make you up, go along with it.

[Comet]

If you're into the idea ... do it! Don't let the chance pass you by.

[Comet]

Tell her you didn't like the first time because you looked like an ugly girl. That will challenge her to make you look as pretty as she can!
And this is a brilliant way to phrase it!

[darla_g]

Well, I think you should put on yur big girl shorts on shouldn't that be big girl panties?

[gracee]

Tell her you didn't like the first time because you looked like an ugly girl. That will challenge her to make you look as pretty as she can!

Oh that's good!

And don't forget to dress pretty too.

[marissa_sissy]

the worst thing a person can do, is not take advantage of opportunity. You have to remember that this is supposed to be fun, and the best way to have some, is plug your nose, and jump right into the pool.

If you do not, your mind will wonder what could have been for years to come. She obviously noticed, and is hoping you will take her up on the offer, or she would not have asked. I would have been ready on the spot...lol.

[Kitty Sue]

No, no,

I say you made a fantastic choice. We all know how wonderful life is living alone, and feeling ashamed, in each of our proverbial closets. I look back on those missed, wonderful and exciting opportunities in my life and give myself 'an atta boy, well done' each and every day.:bonk:

Quick as you can now, call her again. Tell her that you where drunk when you said you wanted a makeover. Stay afraid, in the closet. Please, don't leave me. Oh bother. :)

[Stephanie Miller]

Originally Posted by darla_g
shouldn't that be big girl panties?"

"You say tomato, I say tomahto"

http://www.thelingeriezone.com/shorts.html

( I know what you meant though. I just didn't want to say it that way. ;) )

[Rianna Humble]

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"

Then you wonder why SO's who discover that their partner cross-dresses get upset about the deception?

You like each other, she is wiling to accept your feminine side and offers to let you take it to another level, so what do you do? You LIE to her. Why are you dating someone you are unwilling to trust after all this time?

[ashlylynn]

Tell her you had a thought that it would be HILLARIOUS to have her take PHOTOS of you as a girl, out at the mall, etc
and for them to be good enough that you could fool people into believing they are your cousin or sister ... so lets do it!

[MsGreen]

Or just tell her you're up for it again without giving a reason. Might not work for everyone, but some of us just say, we want to do it, just because. You can divulge more after you're more comfortable.

[AimeeCD]

Ohhh Marissa...please take her up on her offer and let us know how it goes! I would love to have a female allow me to dress in front of her and then have her do my makeup...it would be a dream come true. It sure sounds like it doesn't bother her at all! Go for it!

[GG Kathy]

Go for it what have you got to lose?

[Pythos]

The GG made my face up and she had a ball. She said that no other guys she knows would trust her to do that. The end results were WAAAY to girly for me though. LOL

Dude, let her do it. Don't start hiding. Be honest. If she runs away, then that is an error avoided, along with possible years of heart break.