An interesting proposal

[jessica_brink]

Hi girls, I recently got an exciting but daring proposition from someone. It might sounds a bit strange but it's 100% true, so bear with me.

I'm a student, and recently I was at a friend's dorm where I regularly hang out. One of the people living there is a lesbian girl. She's about 30 but doesn't looks young for her age. There's a new LGBT club that she'd like to go to but is still a bit hestitant about going alone. I've got to know her pretty well and told her I'd accompany her if she'd like that. Letting the woman in me go a bit, I joked I'd even go as a girl. She lit up and loved the idea! She wanted to dress me up in her clothes, do my make-up, put a blonde wig on me (she already sent me pictures of two wigs that she owns, I can show you) and have me go with her like that. Being a closeted crossdresser I secretly loved it, but now I'm hesitant myself. I've never gone out as a woman (not even as a joke) and I don't want to incidently reveal too much of this side to others. I also get really turned on wearing women's clothes so I'll have to watch out for that too. Of course on the other hand this is somewhat of a dream come true, and she does have very nice clothes, trust me on that.

What should I do, is it worth the risk?
How should I act, both towards the dressing up and once as a girl?
What kind of outfit would be best for this occasion? Are there parts of women's clothing I definitely should(n't) wear?

Thank you all for the advice, again this is all truth

[Nikki A.]

If you don't do it you will regret it. Let her dress you and enjoy yourself.

[LeannS]

Jessica
Go for it but first do a preinspection per se. See what she would suggest and see if it would match your taste.
But have fun with it.
Leann

[docrobbysherry]

U haven't described what risks u will be taking, Jess? What r the chances someone who knows u mite attend this club meeting? If you're not out, u may be very safe if u just go there.

Let the girl dress u appropriately for this event.

I get turned on often when dressing in private.
But, in hundreds of outings dressed, I've yet to even think about sex when out with others!

This is idea situation for u in my eyes. Because neither of u have anything invested in each. Yet!

[Meghan4now]

Well, in the absence of any other details, I would definitely say go for it, but there is a chance word might get out. Depends if you care or not. I tend to agree that, if you are a crossdresser, many years from now you will either be glad you did, or regret you didnt.

As far as what to wear, that should be as much if not more fun than the actual going out. You might (should) buy your own underware. Have your friend help you size for a bra. The rest of it you may try different things. Best bet is a skirt or dress, maybe a top that doesn't show too much cleavage or arms. Remember to shave extra close and use orange beard cover under foundation. You want to do as good a job as possible. This is not a joke, and neither should you be one.

[Lana Mae]

Sounds OK to me! Go for it! Best wishes for a great time! Hugs Lana Mae

[Jodie_Lynn]

GO FOR IT!

If you are seen by anyone you know, you already have a reason/excuse: You are there to support a friend.

Once you get over the butterflies, you will have a blast. Good Luck & keep us posted on how it went.

[Roberta Lynn]

I join those that say you should do it.

Meghan has some good advice. Don't dress over the top. Wear something comfortable. Especially since this your first time out.
Now you will probably be nervous as heck. Enjoy yourself, keep your head up, own it.
If someone asks why your dressed like that just say 'Because I want To' That's all that needs to be said.
Make sure you have a safe way home if you and your friend get separated or if she wants to stay longer than you.
Again enjoy yourself!

[Stephanie47]

I say go for it. (L)(G)(B)(T), if you did go as a male and someone saw you there what would the person think you are? (G)? (B)? Neither of the two? Then with proper makeup, wig, and a pretty dress you have a chance of not being identified if there is someone there who would recognize you as a male. Now, you do run the risk of impersonating an identity you are going to try to hide or disavow. Someone may be pissed off. You may consider this as an opportunity to proclaim yourself.

[Teresa]

Jessica,
The simple, obvious answer is go out ,do it and enjoy it, you will regret it far more not doing so. Think where it will lead, it's so much fun being out dressed, the chances of being recognised are very small but after a while it won't bother you at all.

Don't forget the important item is something to get a good tuck , I find a pair of medium control panties on top of my normal ones does the job very well.

[Tracii G]

You're 24 hell yeah go for it !!!
If you get "found out" well so what you have a way now to tell your friends you are a CDer.
I did something similar in high school and went to a prom enfemme.
Had a blast and my friends never knew who that girl was.
The girls who made me up said I was from another school and my date never showed up so I was hanging out with them.
Danced with a few boys and some girls and had the time of my life.

[Brie84]

I agree with the others, this is a great opportunity for you and you should definitely go for it!

[Dana44]

Yes let her dress you and go with her. It is a great time together and if your don't do it. You will highly regret it later.

[NancySue]

Jessica...this is a "no brainer". Go, go, go. You'll regret it if you don't. Let her take the lead and let her dress you as completely as you and she want. You already know what you like. This is your big chance to go out. She sounds very open minded. Several,years ago, a local NFP had a fund raiser vaudeville show. They asked four of us to dress as women for a skit. They, to my delight, wanted us to dress as realistically as possible rather than slap stick. My wife was totally supportive and helped. So, no stones unturned...shaved legs, false eyelashes, hose, heels...the whole 9 yards. We brought the house down. I remember it often and smile. Go for it and don't hold back...trust me. Take pictures.

[Hell on Heels]

Hell-o Jessica,
You'll have to make your own risk assessment, but you've
already told your friend that you'd accompany her.
She seems so excited about the idea, I don't see an
option for you to back out now.

As far as "how to act?"...don't think about acting any way
other than just being yourself. I don't mean for you to go
sitting on the club couch doing your best "man spread",
a few slight mannerism adjustments are nessisary!
What I do mean is more about personality, just relax and be yourself.

What to wear? I'd let your friend help decide that.
If the two of you are about the same size, have her
model the outfits for you first, then pick what you
think works best for you.

Much Love,
Kristyn

[Sometimes Steffi]

It's a dream come true.

To be honest, if I had this opportunity when I was 20, I wouldn't have done it being too afraid someone would find out.

However, if I was 20 today, I would definitely do it. Things have changed a lot in the past 40 years.

Of course, you need to go by her place before the big event to try on some of her clothes to see what fits and what looks good on you.

[TheHiddenMe]

If you don't do it, there will be about a thousand volunteers from this board to take your place.

Pick up your phone, text her that you will do it, that it sounds like fun, and arrange a time when you can do a "test drive".

Just do it, take pictures, and come back and tell us all about your adventures.

[CynthiaD]

Definitely do it. I just got back from dinner at a fancy restaurant, completely en femme. I couldn't even imagine going out in drab.

[Becky Blue]

I would go for it. Life is too short for regrets. It is a wonderful opportunity to go out to a fun place in a safe environment with a friend. Most of the people on here would kill to have had such an easy start for their first time out. There is a fairly strong chance that you will land up going out one day anyway so why not now?

[JenniferR771]

Sounds like a fun experience! Oh my, Yes!
However...its mysterious...most lesbians do not own a dress. Nor a wig. Nor makeup. Pantyhose--not likely.
High heel shoes--not a chance. Bring your own.
Does she know the truth? Will she guess the truth about your "hobby"? Are you ready for that?
Will your deep voice be a problem at the venue?
When you go to the bathroom--sit down.

[Joanne Curl]

Absolutely do it! If you're on this website then of course you've already considered it. This is your chance. A perfect opportunity to do what you've already been thinking about. GO FOR IT!!!!!

[Sara Jessica]

From personal similar experience, DO IT!!!

For whatever reason, SOME girls/young women like to dress & make up guys. For whatever reason, SOME guys are cool with it. MANY/most aren't and they either don't play the game or protest throughout.

Go with the flow as you have a chance to have this experience with what you desire, a nearly flawless cover. Who knows where that might lead? More out & about experiences that you will cherish or retreat back into the closet. Either way, you'll have this experience to always look back on with fondness.

[baldy1]

Sound like a trial dress is in order before commiting yourself?

Julie

[chelyann]

go for it
it will be your first outing, most of us only dreamed of this chance for our first time.

[jennifer0918]

Don't worry just do it you will have so much fun.