Halloween Crossdressing

Two years ago for Halloween my wife Rachel and her friend Carrie convinced me to go as a flight attendant for Halloween. Carrie was going through a messy divorce at the time and they showed me the pictures of the costumes and I thought what could be worse than being dressed up with my ** wife and her girlfriend all in skimpy flight attendant costumes. The night before the party my wife had me shave my legs “you can’t have leg hair, that’s going to ruin the whole look” she said. I figured I had all winter to grow it back so what the **, right? The night of the party Carrie came over and they both did my makeup, lots of laughing at my expense. Carrie said she would go get her costume from the car while Rachel helped me get dressed. One of her old black padded bras was first, we stuffed it with socks to give the illusion of **. She asked if I wanted to wear a thong and that didn’t sound to comfortable so she gave me a pair of just regular black satin **. Pantyhose were next, they were tan, control top, Rachel found it absolutely hilarious as I struggled to put them on. Then came my flight attendant dress, it was pretty much just a cheap costume we bought online, it was pretty tight and the side under the arm had a slight tear in it when I put it on. We also ordered a cheap pair of black pumps, I was a little worried because Rachel had me try them on the night before the they barely fit but with the pantyhose on I was surprised how early they slid right on. Lastly was my brunette wig, i had brown hair anyway, I thought about going as a blond but just decided to go natural. I went downstairs to have a glass of wine while the girls finished getting ready. I was really excited to see them all dressed up, when they came down to my complete shock they were both dressed as pilots. No skimpy dresses, no high heels, no stockings, just pants and button downs with ties, Carrie has shorter hair but my wife had but hers up in a bun and had a pilot had on. My jaw about hit the floor, “but?”, I couldn’t even protest, they were laughing and they had really tricked me. I took it in stride. If you think his is the end of my plight, well that’s not the case. At the party Carrie and Rachel got pretty drunk, lots of Jell-O shots and some sort of boozy punch. Remember the tear in my dress, they kept messing with it, pulling on it tearing it a little more at a time. I kept protesting but they seemed to be having a great time (and I guess I was too). At one point in the party I was talking to another couple and the girls came up behind me and just ripped the entire dress off of me. I tried to stop them but was completed panicked as they were stripping me and all I had on was woman’s undergarments. After a couple of yanks they had completely tore the dress off. I was beat red in the face, standing there in just a bra, **, and pantyhose. After all the laughter at the party simmered down, the host Mary let me wear one of her t-shirts, of course if was two small and my **/pantyhose were completely exposed for rest of the party but at this point there was little I could do. We took an Uber home (i can only imagine what the driver was thinking) Rachel kept whispering in my ear, that she wears the pants in the marriage now, she was pretty drunk and hiccuping. Not sure she remembered that part in the morning but I think she and Carrie really got a kick out of the whole role reversal thing (and if I’m being honest, I’d do it again!)

May 15

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  • Fvck duuuude. You got problems. Talk about projecting your issues on others, ffs. That was a total gay-athon.

  • That's almost as gay as this story

  • I can't say "f@ggot" ?

  • LOL, awesome. That made me laugh...

  • Well, then get an AIDS test, 'cause your wife's a dude, **.

  • It wasn't Halloween but I was in Singapore for training before Covid.
    I went to the Zouk and met a girl dressed in a ** nurse outfit. She was asian, maybe 85lb, fake ** and short.
    We hit it off and she came back to my room and I got an amazing **. She took off her cloths and there it was. A tiny c**k half the size of my pinkie. I never gave it a second thought. I put a condom on and we went at it all night long.
    To this day I have no regrets.

  • That canoe would likely tip over if the waves are too high. This is always a problem during a storm

  • I dressed as Patsy in an Ab Fab party last year. I wore a leather skirt, leather jacket, black 10 denier tights and black high heels. The underwear I wore was pretty hot too. I enjoyed it.

  • Fvck dude. Me thinks you enjoyed it a little TOO much....Know what I'm saying? lol

  • It turned me on. All that leather, nylons, silk underwear and high heels. What's not to like!

  • Nice story. My gf wanted to do the role reversal costumes too. She dressed as a football player, I dressed as a cheer leader. She had a jock and cup for that manly look. I wore a short skirt and white **. We won second prize, $100.00

  • ...and FIRST prize for losing your 'man-card', LOL

  • And you won first prize for being a total h0m0. lol

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