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My Wife Crossdressed Me Then Took Me to a Halloween Party.

About ten years ago we got invited to a last minute halloween party. I said we didn't have any costumes. The people said just improvise. We scrounged through the closets and couldn't find anything, then my wife got an idea. She said why don't I goa as a man and you go as a woman. Well, she didn't have to twist my arm on that one. So the search was on. We went to the local thrift shop and told the lady there what we were looking for. She had lots of stuff. We found my wife an mans suit, pants, shirt and tie that fit her a little big, but who cares, she said it's halloween.

The lady that runs the shop asked what I was going to be for halloween. I said i had agreed to go as a woman. She laughed out loud, then said, "come on, lest's see what we can find you."Well, after just a couple of minutes she sound this light blue dress, and she said this should fit you. I said, I don't know. My wife said, try it on, and I said no way, not here. The lady said it's ok, go to the dressing room, there is nobody else here and I am just about to close, so I will lock the door. Well I went to the dressing room and took off my shirt and jeans. Just then the curtain pulled back and the lady was standing there with a bunch of items in her hand. I was embarresed standing there in only my underwear. She said your wife had to go to the grocery store before it closes and told me that I was to make sure that everything fit right, and that she would be back in less than an hour to get me. Now what I said?  She said put these on, as she handed me a pair of stretchy nylon panties and closed the curtain. "Your wife wants to to be a complete woman at that party tonight and told me to supply you with everything you need to wear."So here I am standing in the dressing room in nothing but a pair of panties with this 60 year old woman standing oursdie the door. Do you have your panties on, she asked. "Yes" I said. She quickly pulled back the curtain, Let me see how they fit. A little snug, but not too much,. thats ok. Come with me. What? Where? I asked. Out into the store she said. I can't go out there like this, someone will see me. She said no, the blinds will not let you see through them unless the lights are on. Are you sure?  Come on. She led me down the long aisle of clothing and around the corner to where the lingerie is stacked neatly in bins. You are going to need a bra. I said  whoa! No way (I really did want to)  She said your wife insists you wear everything a woman wears. Finally after some fake complaining I agreed to do what she said.  Turn around for a second. She quickly measured ariund my chest. The she said face me and put out your arms and slide them into this bra. I did as I was told. It had huge cups, like double D or bigger. Turn around and let me fasten it. I didn't want her to know that I could do it just as fast or faster than she could so I followed orders.

Next she had me sit in a chair and put on some stockings that she had gotten from another display. They were queen size dark tan with a sheen to them. they felt wonderful. Now she says you need something to hold them up, come with me. She took me down the aisle to where there were several all in one girdles and pantygirdles and openbottom girdles on display. She said" you will need some garters to hold those stockings up, but I don't have a garter belt, so you will have to wear a girdle. She said it looks like the biggest one I have is a high waisted, side hook and zipper open bottom girdle with six garters. She saw me eyeing the all in one longleg girdle and some pantygirdles, and she said those don't have garters. Too bad I said, I like them. You would have to wear pantyhose with them she said, I said, why can't I do both? hmmm she said, that could be arranged. She grabbed a hand full of girdles, went to the display and got some pantyhose. Back to the dressing roomshe said. When we got there she said give me you shirt and pants and I will hang them up so they don't wrinkle, so I did. She had me remove the bra and the stockings, then instructed me (as if I didn't already know, as how to put on pantyhose. I pretended i ws new at it and she ended up helping me, and making sure there were no twists or wrinkles as she pulled them up around my belly. Then she had me try on a couple of longleg girdles, until i found one that fit. Now the all in one girdle. I pulled it up my legs, and started to unroll it and try to put my arms through the straps (pretending again). She said what would you do with out a woman around to help you dress. You are lucky you don't have to do this every day...she said. (Oh how I wish I thought), (if she only knew how much this was turning me on. Good thing I wa wearing layers of girdles to cover me up.)

She made sure it was pulled up tight in the crotch and up as high as it could go in the back. This all in one only had B cups in it, and I had enough to just fill it. She noticed that and asked if iI would mind her adjusting the straps for better effect. She shortened them about an inch, then all of a sudden she reached inside one of the cups and grabbed the flesh from under my arms and forced it forward into the cup, then did the same thing to the other side, as she squeezed my moobs into the cups. Oh that was exciting. Now she saidwe have to get that open bottom girdle on you, so lift up your right leg first, As she bent down to slide the girdle over my foot, I got a delightful site as her sweater dropped down as she bent down and I could see she was wearing a very sexy white demicup bra. Wow! An older woman wearing something like that, how sexy I thought. Actually, she looked pretty darn good for her age.  Anyway, now she helped me on with the open bottom girdle, then had to help me on with the stockings because I could hardly bend over with all the girdles I was wearing. When she rolled the stockings up my leg over top of the panythose it felt wonderful. Then she had me stand up and turn around as she fastend the side and rear garters to the top of the stockings. Then she stretched one arm  around my leg and reached one arm through my legs to fasten the front garter, then switched to the other side. After she was finished fastening them she slid her hands up and down the insides of my legs and teased me about how I needed to shave them. Next time I said. Well she said, your own real boobs are not big enough to make this look right, so she scooped up the huge bra that I had on earlier and helped me put it on again. then she stuffed the cups with water filled balloons to get the right effect. Then it was time to put the dress back on. It was a sleevless dress with a fairly tight skirt and a zipper on the back. I could not get the zipper up, so she had to do that. She then went to the back for a moment and came back with a box, inside was a blond wig, she said you will need this to finish it off, so she fit it on me. Not bad. only problem was my moustache.  I said I am not shaveing it off. Just them my wife pulled up and rattled on the door, so the lady let her in. As she did she handed my wife a bag. Whats that? She said, your clothes, and opended the door, wuickly went out tand thew them in the car. Now what am I going to do?? It's halloween, we are going home to finish getting ready. It's still light out, I protested. Too bad she said, and paid the lady who was now laughing out loud. What's so funny?  She said, your wife phoned me earlier and set this whole thing up. They had a good laugh, but inside I actually loved it. Being dressed by a woman whom I had never met, then standing there in front of her and my wife wearing only womens clothes. What a turn on. Come back and we will try some more panties and bras for you. My wife laughed, but I quickly said, you bet I will.   I quickly jumped in the car a slid down in the seat so nobody would recognize me, and we went home for supper and then get ready for the halloween party.  The fun is just beginning.  More on my next posting.

IMACD IMACD 56-60, M 9 Responses Feb 11, 2009

Your Response


I have a neighbor who insists on dragging me to parties every year. What fun. I get him on once or twice at each party. Yeah baby.

Such a great story. Would love to hear how the Halloween party went.

I would have had a huge erection as that woman was dressing me in panties, pantyhose, etc.

What a great experience. I wish i had the nerve to go into a store and do that. I guess if somebody would push me, I might. I wish I had a wife or friend that would set something like that up for me.

I have to say that it does sound like a lot of fun. I spoke to freinds to see if they celebrate and it appears that it is becoming more popular. I'll have to introduce the idea to some friends. <br />
There are lots of charities where people are encouraged to dress up and do silly things and friends and neighbourghs sponser them and it is a good excuse for having an all over waxing and cavort about in a dress and things so maybe that could be another avenue to explore.<br />
Pippa xxx

pippacd..I did not realise that you didn't celebrate halloween otver there. Too bad, it is the one time of year we can dress up and go where ever we want. Yeah some people are rude and make comments about the way we look, others laugh at us, and some that know us laugh even harder, but I don't care, I try to dress and go every halloween, although it has been a couple of years now, but I am going to do it again. I have so mush fun at those parties, all kinds of men and women trying to see up my dress, feeling my pantyhose covered legs, and some even reach up under my dress, just to find my "clitty" is tucked. The women dance with me, and feel my bra straps and ask me all kinds of silly questions, and of course they get in a few more feels as do I. Over all there is not too much better than going to a halloween party dressed as a woman and where most everyone is drinking. It as a lot of fun. Must do it again. Sorry you don't cel;ebrate ove there, you are missing out on a fantastic time.

Great story it's a pity we don't celebrate Halloween over this side of the pond

Great story. I am going out to a Halloween dance as a girl.

Wonderful story. Years ago and single i did this. Memories. Thank you for sharing.