Caught Dressed As A Woman

It was a weeknight and I was out cross dressed enjoying dinner. About half way through dinner a fellow from work and his wife came into the restaurant. He immediately recognized me. Well, it happens I said. Since there was no place to go I finished dinner and paid the bill. We sort of waved at each other. Perhaps, a few weeks later we bumped into each other and he said where is the green dress. Several jabs later he was still in a teasing mood. Well, you just have to laugh at yourself sometimes and can't take life too seriously. That was probably 10 years ago and the teasing continues.
jml2000 jml2000
61-65, M
15 Responses May 9, 2012

He seems to have kept it to himself.

I wish he did.

Omg that was always my worst nightmare... I was out with my wife at the casino and security approached me.. They thought I was a woman in their banned list, or so they told me, after they asked for ID and made a small commotion, an acquaintance of both of us noticed us and started to recognize my wife. I noticed this but she didn't. I couldn't get out of there quick enough. It shook my confidence a lot. We then went out for coffee and cake to get over it. It was my first time out with a new wig, a shorter bob style with natural Colour streaks through it.. But anyway tragedy plus time equals humor... I can nearly laugh about it now.

Thanks for sharing your story. It's good you can laugh about the casino incident.

What is wrong with flirting? I loved guys flirting with me when I used to go out dressed as a woman

Nothing wrong with flirting.

jmi2000 this guy sounds like a right ***. This is victimization in the U.K he could be fired from his job for what he is doing

He was teasing me sissy baby. But you're right about harrasment. It is very serious.

I used to walk the streets downtown Houston Texas with the rest of the girls. Got picked up one night by a real nervous and shy guy. He drove me around a little. Put his hand on my thigh and slowly crept up to my panties. I was getting really hard. I told him I was a transvestite and he said he knew. He pulled over and started rubbing me in my panties while he was rubbing himself. I exploded in my panties and so did he. He drove to a convenience store afterwards and dropped me off. I had to walk 4 blocks home in my soaked panties.

No he was there with one of his mates on a club night out.I no he never suspected me if he had it would have come back via his mates.

Use to go around Manchester dressed, called in one of the bars there in the village,stood next to a lad that worked in next unit to me.I never spoke to him so not to give the game away.Next day he was telling me where he had been last night and about the TVs that where there.Never mentioned the one standing next to him.

Was he in drag too? That is a great story!

Yeah - HE sounds real mature. Good God.

Thank-you Heather . Some people are that way

I agree sounds like he was flirting, wouldn't that be fun to have a sexy little tryst

Just a teaser Debbie

Sounds like he was flirting lover!

Hi Candice, He was not flirting.

Kinda reminds me of a time I cross dressed for holloween one year and went to a work party I was dressed in a white<br />
minni skirt (my girl friends at the time) a long sleave white lacey shirt and some white 6" heels with some sexy purple lacey panties and no one at the party even reconized me. But they sure were trying to get in to my panties !!!!!!!!

He was at the restaurant with his wife. He was being a pain in the ***.

Maybe you could have offered to model the green dress in private for him...

I agree with the previous replies. Why don't you see if you can find a cheap (green if possible) dress in his size at a 2nd hand store and next time he asks that question hand him the box and say, "here, I picked one up for you since you seem to want mine so badly!"<br />
<br />

That seems to be the concensus. The last few times I've seen him, he hasn't said anything. I'd rather buy me another dress rather than buy him one. That I would enjoy.

Then stand up and be proud of it. Challenge him. Dare him. He hasn't the nerve to do it and you have already.

Hi bahli, Thanks, great suggestion

Either it will get him off your back or turn him into a dress wearing budy. It's win, win. And youv'e been there done that.

Maybe he would like to try it himself or maybe he wants to try you. Have fun!!!

Perhaps, but I believe his wife would not let him.