tagTranssexuals & CrossdressersDressing Up For My Wife

Dressing Up For My Wife


My wife and I had a bet on the football game that pitted our two rival teams against each other. It was a horrendous day for my team and hers slaughtered mine 31-0. It was the same bet we always have with each other. It is a bet where no one really loses because it ends up with us having wild kinky sex.

On earlier bets we have had, she has had to let me fuck her in the ass (I have actually cashed in on that one for a few wins because she has such a hot ass), she has let me put her over my knee and spank her silly, she has let me tie her up and have my way with her (another one of my favorites when I win a bet). For her I have done the dishes in the nude (sounds bad but when she dropped to her knees and started sucking my cock I felt as though I actually won the bet), she has tied me up, I had to give a massage for a full two hours (I think this one is her favorite because she has cashed in with that one the most), and the last bet she won she had me cover her in chocolate sauce and lick off every ounce (once again I felt as if I won).

She of course teased me that I was in for it and being a man I didn't leave well enough alone and brought up the fact that I always win even when she does. When I said those words I saw a look in her eyes that told me I was going to eat them.

That night we took our showers, my wife went first. As I came into the bedroom in my towel I noticed my wife had put her hottest outfit on the bed. It was a nice little ensemble with a black and blue lace bra with matching thong. The set also included a garter belt and stockings. When I saw the items I felt my cock get hard, I just couldn't wait to see my woman in her hot lingerie. I told her that I couldn't wait for her to get into them and that is when she dropped the bomb on me.

She told me that I was going to wear her sexy under things while we made love. She told me since her team made my team a bitch, I was going to be her little cross-dressing bitch for the evening. I must have looked like a dolt with my jaw hanging almost to the floor.

Then my wife got right into it calling me all kinds of names like sissy boy and pussy bitch and then she told me to hurry up and get dressed. As much as I didn't like the idea of dressing up a bet was a bet and she had always paid up for me so dressing up it was.

I first pulled on the silk and lace panties and was shocked at how soft and sexy they felt against my cock. Although a little tight it was still nice feeling. Next I put on her bra, now taking them off has always been easy for me but I struggled to get the damn thing on. My wife helped me and soon all I had left was the garter and stockings. I snapped the garter on then began to pull up the silky stockings; once again I was amazed at the texture against my skin. It felt really nice and my cock throbbed in the small panties while I clipped each piece of hose in place.

My wife then had me prance around and model for her. Just as I was posing for her she pulled out the digital camera and took some pictures for posterity sake.

That night we had some wild sex with her taking the lead and being the aggressor which was a nice change. And feeling her hands run over my cock through the panties was awesome. It ended with her fucking me in the ass with one of her dildos and me fucking her hot wet pussy at the same time.

I wouldn't consider myself a cross dresser but that night I was her sissy little cross dressing fuck toy and I enjoyed every minute of it. It is amazing how a little bet can lead to so much fun, even if you are on the losing end of that bet.

I will definitely have to come up with something for her the next time she loses a bet. But I can say she got the best of me on this one!

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bydirtyjoe69© 6 comments/ 203380 views/ 31 favorites

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by Anonymous

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by Easypeter05/05/18

Happy Bet

Liked the plot. Wife wins and takes him to a better place. I love wearing my wifes panties and pantyhose under my clothes. She hints to her friends that I love getting into her panties. I heard a friendmore...

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