One year my wife and I went to a Halloween party at a local bar. My wife suggested I dress as a girl, and after some coaxing, I did. Unfortunately, I looked too real, and too pretty. Two young men at the bar, seeing two single young ladies sitting alone, kept sending drinks to our table. After a while they came over and asked if we would mind if they sat with us at our table. I was nervous as hell, but before I could object, my wife said no.
I was wearing an above-the-knee, black, lycra skirt that rode up fairly far when I sat down. After pulling down several times, I gave up. The stretchy skirt would just slip back up on the silky pantyhose the next time I moved. The guy who sat next to me kept staring at my legs. Fortunately, I had shaved my legs earlier that night, at my wives insistence. The music was loud enough to cover my short, falsetto responses to their questions. My wife was having a great time. I wasn't feeling too amused! Then they asked if we wanted to dance. The situation was going too far for me. I was starting to fell very uncomfortable. I motioned to my wife and headed for the exit, walking as ladylike as I could in the three and a half inch, black, patent heels. But, these guys wouldn't give up! They followed us out to the parking lot. I whispered to my wife to keep on walking, as I wobbled along on a pair of three inch, black, patent heels.
After we got into the car, one of them came over and knocked on the window on my side. He wanted to know if we would like to go for coffee somewhere. I opened the window a crack and said no, but thanks. My wife said, "C'mon, it'll be fun!" I didn't think so. We drove off.
I was feeling very relieved we were finally headed home. But this was Halloween and we were in my wife's junky Chevette. It decided to break down. Can you believe it? Swear to God! So here we are walking along the road, ME wearing the heels and skirt and my wife in pants!!!
Think that's funny? the night wasn't over yet. It's not easy walking in gravel in three inch heels. Two guys stopped to give us a ride.
(No, they weren't the two from the bar.) I didn't want to. I was scared sh*t less. Can you imagine; I was worried they might try to rape us, or something! As far as they were concerned, they had just picked up two young ladies.
I've since decided, it is not a good idea for two girls to get into a car, on a deserted side road, at night, with two strange guys, but we didn't have much choice. It was a couple of miles to anything. The ride was uneventful, and they dropped us at a shopping mall where we went inside to call a cab.
We had been out drinking, you will recall, some time earlier. Now I had to use the restroom. I didn't know what to do. My wife was laughing hysterically, as she commented how it wouldn't be a good idea to use the men's room, dressed as I was. Eventually, I resigned myself to using the ladies room. I won't give you the details.
After I came out, my wife decided that since we were in the mall, she wanted to shop. After all, what do women like to do the most? Of course! Go, shopping!! I followed her through the racks, expecting someone to shout, ;Hey, look! It's a guy dressed like a girl. No one did. It's amazing how differently you're treated as a female.
My wife kept joking out loud, that I should try this on, and that on, and how I would look good in this and that. Ho, ho, ho. An alert sales girl heard her and came over to assist us while my wife was holding up a slinky, mid-calf, chiffon sleeved, black sequined evening gown.
It had a slit three quarters the way up the front of the thigh with a deep plunge backzipped, open back. The top hooked around the back of the neck. Then the sales girl started in, not realizing I was a guy, with, Go ahead, try it on, it'll look gorgeous on you. They just about pushed me into the dressing rooms. The sales girl wanted to know if I needed any help. I told her no. My face was beet red, I'm sure. I stood in the dressing room with the curtain pulled, wondering what the hell I should do. The sales girl stuck her head in and asked how it fit, as I hastily pretended I was unzipping my skirt. They were waiting to see the gown!
What did I do? I put the d*mned gown on!
Actually, I looked pretty good. I couldn't believe it was me in the mirror. With the padding I was wearing, all the curves were in the right spots. Then I mustered up what little nerve I had left and went out to show them. They fussed about how good it looked, and all the guys would..., you know. Laughing yet? Just wait.
While the sales girl was commenting on the dress, my wife slipped into the dressing room and grabbed my other clothes. When she came out she told the girl we would take the dress, and I could wear it out, since we were in a hurry to get to a party, anyway! Bull sh*t, I thought frantically, but there was nothing I could do. She had my other clothes and the last thing I wanted was to make a scene. She paid for the dress. and headed for the door. What was I supposed to do? The sales girl smiled and wished me a nice time at the party. As we walked through the mall I could feel the guy's eyes undressing me. I couldn't keep my stockinged leg from coming out of the high slit in the dress, with every step. One or two men made comments on the 'babe' in the killer dress, or whistled softly, just loud enough for me to hear. They couldn't get their eyes full enough. I felt just like a piece of meat.
I'm sure a girl would revel in the attention, or maybe not. I felt humiliated, but then again, no one realized I wasn't a girl. I pretended not to hear, but I'm sure my face was twenty shades of red.
After parading me around the mall a little while longer, my wife called the cab. Even the cabby bugged his eyes when I got into his car. Having never worn a long dress with a slit that went three quarters the way up the thigh, I had a hard time keeping it from sliding up around my waist. All I could do is cross my bare legs in a lady like fashion and endure his barely hidden glances in the rear view mirror.
Oddly enough, I wasn't mad at my wife. As I look back, I can even say it was exciting and fun. I know I have a much better appreciation for things women put up with from men. In the same turn I was introduced to the great things you can do as a woman, like being yourself or dressing in a sexy gown. Since that time I've been cross-dressing, and loving it. The only problem is, I wish I could do it full time, but the wife won't go for that.
So, if you ever want to teach your husband, or male friend, a lesson in humility, trick them into dressing like a woman for a night.