I should have did it.

[Maria 60]

I don't know why i didn't do it but i know wished i would have. About five year ago we were waiting for our house to be built and we were living with my in laws. They are really down to earth people and love to have fun. It was halloween and we all dressed up, and you know what i dressed as. My wife and mother in law were throwing me cloths to try on and mother in law decided that i should be a hooker. When i was trying on the cloths my wife told me you must be loving this and got my heels and told me to put them on and she would tell her mother that i had the heels because i dressed as a girl a few years ago for another halloween party. My mother in law could not believe the amazing legs i had and gave me a skirt that was long down to my ankle's. I put in on and came out of the room she told me to walk over to her, she cut a slit from my ankle all the way up to my waist. She then gave me a new pair of stockings and a garter belt and both of them did my make up and finish dressing me. We then went around to our friends house's and having a laugh as we were all dressed up. We went to my sister in laws house and she had all her family there and we had a lot of fun there, everyone couldn't believe how good i looked and it felt great to be dressed. Well last weekend we went to my sister in law's houses for a BBQ and all her family were there, and after dinner her mother turned to me and said do you remember that halloween you came here all dressed up you looked great and she turned to her daughter and said you two are almost the same size get some cloth so he could dress for us again. Well my heart started rushing and everyone started encouraging her to get some cloths. I said no i can't and my sister in law went in and came out with some cloths and said go try them on. When i looked at the cloth i seen she put a pair of lacy black panties, black pantyhose a purple padded bra and a short skirt and a lacy top and she told me she has a pair of open back shoe,s that would fit, she was one size smaller then me. Everyone was pushing me to try them on and all i was doing was looking at the cloth and wanting so bad to put them on but i kept saying no. The hole time she didn't move those cloth and she kept asking me are you sure you don't want to try on my cloth's, i would love to see you wearing my cloths. It drove me crazy just thinking about it, i almost shot in my pant's. Well i didn't and now i regret it and that i may never be able to try on her cloth again. Even my wife told me that i should have did it, that i would have enjoyed it. Everyone was disappointed.

[cdinmd206]

Wow. Sure widh something like that would happen to me!!!!!

[Inna]

don't beat you self for it, we all have done what comes naturally, denial, we know it so well it becomes an instinct.

[richelle1]

Great story. Wow I couldn't imagine how I would have felt. Thanks for sharing.

[bobbie sue]

You should have dressed for them and yourself just think what a great way to come out

[Diane Elizabeth]

We are all of the shoulda/coulda/woulda wishful regrets of opportunities gone by to dress or come out to people. As Alexa says don't beat yourself over it. There may be other chances coming up with Halloweeb just a few months away.

[Danni Renee]

Like Alexia said, denial is so natural to us that your reaction is understandable. But WOW what an opportunity. However, I have a feeling you will get the opportunity again. I cannot imagine the family just doing something out of the blue like that. I get the impression that more than just your wife knows and that you are being encouraged to be more open.

[Marie-Elise]

Great story. I'm sure I would have behaved the same way and spent the rest of my life wishing I hadn't. Go with it next time, if you can.

Come to think of it: Maybe your wife has revealed this to them and this was their way of trying to urge you to come out to them? They seem cool with it.

[kimdl93]

Here's a suggestion - explain to your wife and sister that you would really enjoy dressing up for them, but that the pressure of so many people was just too much. Try to plan a get together with just your mother in law, sister and wife, and, although I think they already know, tell them that this is really something you enjoy and would like to share with them.

[Diane Douglas]

I think you did what most us would havee done given the circumstances. I also think this oppurtunity will come again. like Kim's suggestion that you should talk to your wife and make plans to dress up with mother-in-law and sister-in-law. Maybe a wine and cheese get-together.

[Brown Eyed Girl]

I know what I would do....next time you see here, tell her....I got to thinking...I would actually love to try your clothes. Is that offer still on the table?

[Intertwined]

The way around this, IF, the situation ever comes up again, just keep in mind! You will be dressing for THEM, not for Yourself. That should aleve some of the tension. Even tho I do not get excited, in a sexual manner, over dressing, I can understand your fear of, they may notice that you are " enjoying " this too much. I am really sorry you missed that opportunity, Like others have said, don't make a specific trip or occation to say this, but, next time you just visiting with them, say something like, "I am sorry I freaked out the other day, about you wanting me to dress up, I have since thought about it, and realized how silly it was, and hope I didn't hurt Your feelings by not wanting to go along with being dressed up. I remembered how much fun we had on halloween, and what fun it was being the center of attention."

[docrobbysherry]

Maria, please believe this. There's almost ALWAYS another chance in life!

U need to think of WHY u didn't want to dress the last time. Then, figure out under which conditions u would feel more comfortable dressing in front of your in laws.
The next time u see them, tell them WHY u were uncomfortable and what would make u comfortable. Then say that u would like to dress up for them in your sister in law's CLOTHES. Just remember to dress THEIR way!

[Kathy4ever]

We all have the regrets of chances that got away. I remember a girlfriend that I had after i split from from my first wife. She asked if I ever dressed. I said no. That was a big lie. To this day wish I would of come clean and who knows where that would of taken me.

[Mollyanne]

Hi Maria, As so any of the girls have said "We all(maybe not all) are in that denial mode when we are pressed into a situation like the one you mentioned and a lot of us would have jumped at the chance to dress in front of all those people;l MAYBE and I say again MAYBE!!!!!! One never knows how to react to a certain situation until it presents itself. Don't beat yourself up over it, another chance will come. Also, from what I read it appears that your wife supports your cd'ing and possibly has told her sister about it. GO WITH THE FLOW and follow your instincts.

Molly

[Genifer Teal]

Remember how you feel right now. Write it down if you have to. The next time a similar situation occurs - related to dressing or otherwise - maybe you will act differently. Every situation presents a chance to learn and grow. It is only a shame if you waste this lesson.

[danielle40I]

For me, the key word in this thread is DENIAL. I remember after being caught dressed when I was an adolescent, how my mom would come to me and ask me, "do you want to be a girl?". How I wish I'ld been honest and told her the truth..."I don't know". I so very much understand your hesitancy, Maria, and can empathise with the feelings that went through your mind.
The other girls have given you some valuable insight as to how to approach this moving forward. I for one can only wish I had the options that you have at this point. For me, I'ld try ever so hard to "go with the flow" as your wife and in-laws seem comfortable with it. I believe, as Danni predicts, the chance will present itself again in the near future.

Be sweet...Dani/Danielle

[Maria 60]

I hear a lot of other stories about members who get the chance to dress in public but refuse it for some reason. I wonder if i wasn't a crossdresser if i would've did it, am i that scared that someone will maybe figure something out about me. Thank for all you comments.

[NZ_Dawn]

A huge dillemma! I woudl have done the same as you but it would have eaten me up as well! So close and yet........
I also have similar views as Kim and Diane, Did the initial dressing at Halloween trigger a discussion or suspicion by your in-laws? and was this offer more of a "test the wtaers"?.. Go with the flow and disuss with your wife. Not knbowing your family I suggest it would have been a horrible outcome and humiliation if they had set you up. Id like to think they had your best interest in mind though. All the best.

[Sarah Doepner]

I think there is a chance here to have the discussion with your wife and explain how you feel about dressing in women's clothing, both the positive of how it makes you feel and the negative side of the fear associated with how the family will react. Get her input on what to do the next time and make sure she will be there to defend your choice.

[Chickhe]

Well, fundamentally, its not fair, you are the one taking the risk and everyone else can ridicule you. You were best off refusing, it sets a good precident so you don't end up being the jester at any gathering. If you can pull in other participants it is better because if they redicule you, you can change the attention to their escapades also. As for doing it, you need to be tottally comfortable and confident to pull it off well, if you are shy about it you will not enjoy it. Otherwise, I have to say CDing for partys can be a lot of fun!

[AlannahNorth]

Well, next time you are back for a visit, you can always say "Yeah, I should have..." and don't say no if you have another chance...

[erickka]

Never look a gift horse in the mouth! Unfortunately, hindsight is always 20/20.

[SheriM]

You undoubtedly missed an opportunity but you also must think about "after the night is over". Do you want to be outed? They might realize that you enjoy it too much. Think about what their attitude would/will be when the night is done. If you are OK with it, go for it.

[Kerigirl2009]

OMG I so would hae let them talk me into it. No doubt about it. maybe next time

[Leasa Wells]

I am not sure I would have dressed at that point, maybe it was too public and the timing wasnt presents in a way to make me feel confortable. I would discuss these feeling with your wife and then decide what the next step will be.

thank you for sharing.

Lisa

[JenniferR771]

Happened to me when I was 21. My college roommate must have figured it out and told his attractive and fun girlfriend. They bought me a birthday present--and when I opened it --it was one of her bras. They tried to get me to put on to try it for size and shee how I looked.

[Janet Bern]

maybe its not too late.. When the time is right I would say that I enjoyed it when I did it the first time and
sorry I didnt do it when asked. Next time I wont be such a downer. good luck

[Maria 60]

The part that my wife and i can't understand was the panties, the lacy shirt and short skirt and bra and pantyhose were OK, but the lacy panties i can't understand, was she going to get a thrill knowing i was wearing her panties, i didn't expect when she got the cloth to see panties, i think that was a bit personal unless they were a old pair.

[Gaby2]

The part that my wife and i can't understand was the panties...
You might be reading too much into that, Maria - give your sister in law the benefit of the doubt!
It's a breath-taking story - I can almost hear the tumult and your heart beating!
Your reactions are so understandable.
Try not to let your regrets at "not seizing this opportunity" get you down.
They sound like a great bunch!
:)Gaby

[Maria 60]

You might be reading too much into that, Maria - give your sister in law the benefit of the doubt!
It's a breath-taking story - I can almost hear the tumult and your heart beating!
Your reactions are so understandable.
Try not to let your regrets at "not seizing this opportunity" get you down.
They sound like a great bunch!
:)Gaby

Yes they are a great punch and i do believe there intention was to have a few laughs.

[Jorja]

Maria, does your wife know you are a crossdresser or is this something you have kept from her? I am all for having a little fun with someone from time to time but it seems like they were trying to embarass you in front of the family. I hope that is not the case. I would have refused the offer as well under these circumstances.

[Nancie64]

I guess the guestion is, Were there younger people(kids) present? It all sounds like it would be great fun and I have dressed when my sister in law has visited, all by herself. Would I dress in front of other guys, I probably would have done the same thing you did. If it was my sister in law and my SO and her mom, probably. Guys can be stupid and than the next time you get together with them, it might be embrassing. They might make comments that could make make you feel bad and then you will have to ask yourself if it was worth it. Sometimes a teasing is almost as much fun,(I said almost) And maybe your SO would have gotten upset later. I thing you made a good call.

[Tina L.]

Not sure what i would do if the opportunity was presented to me. hope someday it does.

[siantv2003]

Now why dont things like that happen to me ??? No fair :sad:

Oh well, maybe if I keep my fingers crossed :daydreaming:

[Annaliese]

Great story, it is in the past now so forget it, if the chance come up again go for it.

[anonymousinmaryland]

I was disappointed just reading it. Next time, go for it. But there again, that's easy for ME to say. Best wishes.

[Victoria StJohn]

Wow, what a missed opportunity. Next time, only for the girls, no dudes allowed. LOL

[mweb015]

I think you did the right thing.

[kimdl93]

The part that my wife and i can't understand was the panties, the lacy shirt and short skirt and bra and pantyhose were OK, but the lacy panties i can't understand, was she going to get a thrill knowing i was wearing her panties, i didn't expect when she got the cloth to see panties, i think that was a bit personal unless they were a old pair.

If they just having fun, then why not include the panties. Its part of the package. I mean, without them, they'd know you had male undies on...not nearly as much fun for them or you. I'd still guess that they are in on your secret and you'd be well advised to visit with your wife, sister in law and mother in law for a more appropriate opportunity to dress up for them. Less pressure and more fun.

[JillyNylonz]

Many excellent answers. Most forums have so many people that make inappropriate comments. How refreshing to see how many nice and thoughtful people belong to this forum. There is a lot of wisdom and love in this group!

[Maria 60]

Many excellent answers. Most forums have so many people that make inappropriate comments. How refreshing to see how many nice and thoughtful people belong to this forum. There is a lot of wisdom and love in this group!

As much as many said to go for it, in the same sentence they also thought that they would have to be in the situation. The same as myself i feel i should have, given the same opportunity i may again not do it. I felt as all the comments were very honest. THANKS

[linda allen]

I think we all miss chances and later regret it. I know I have. There will be other chances.

[anonymousinmaryland]

Shoulda. Woulda. Coulda. Only if . . . I think we all have been there at one point or another. Don't beat yourself up. Get ready and prep for the next experience. Best wishes.