tagTranssexuals & CrossdressersHow I Became A Cross Dresser

How I Became A Cross Dresser


Hi my name is Ted and one of the most embarrassing days of my life became a day that I will cherish forever. It opened my eyes to a whole new world for me and my wife. I am a totally straight man that has been married to my loving wife for over ten years and let me tell you I was as surprised as anyone would be by what happened.

The day started out like any other day. I took a shower and was about to get ready for work when I heard a loud bang. I called to my wife but she had already left for work. Curiosity got the best of me and I headed to check out what made such a racket. I only had a towel wrapped around me and proceeded to go to the back yard. Even though it was a nice day it was quite breezy. Just when I was about to go out side the wind sucked the door closed with a bang catching my towel in the process. I tried to open the door but the towel had jammed it shut.

So here I was standing at my back door in all my glory and I couldn't get the damn door open. I didn't know what to do. There was no way I was going to go around front naked as a Jay bird. My street was busy with everyone leaving for work. I noticed my wife had left clothes on the line so covering my genitals with my hand I looked for something to wear. Unfortunately for me all she had hanging up was her dainties. I had to cover up with something so I thought what the heck for the ten seconds it would take to get in the front door maybe the neighbors won't notice. I grabbed a pair of her more conservative silk panties and put them on then ran for the front door. When I got inside I had a quick laugh at what had happened and thanked the Lord no one stopped me to talk.

I went to start my coffee and for a moment I forgot I was still wearing my wife's panties. I forgot that was until my cock got so hard I couldn't stand it. The tight silky confines had rubbed me into a frenzy and also peaked my curiosity. I thought I was going crazy for a minute but I came to the conclusion that wearing her panties was turning me on. I had to test my theory and called in to work saying I wasn't feeling well.

The rest of the day I put on my wife's sexiest things and my nuts were so tight I thought I might cum right in her under things. I took it a step further and put on some of her silk stockings and garter belt. Then I went for it all and put on a matching bra. I looked at myself in the mirror, and because I am not a very hairy guy I didn't think it looked too bad on my lean body.

That night I told my wife about having to put on her panties and she got a laugh about me being caught in the buff outside. When I told the story my cock was hard as a rock and it didn't take her long to notice. Now my wife is a very smart woman and she started to put things together. She asked me if wearing her panties turned me on and I admitted it did. Her breathing became shallow and I swear I saw her nipples become erect.

She then asked me to put on one of her outfits for her and I did. We fucked like crazy that night and we have made it a regular thing. We have even taken it a step further. On nights when she has me dressing into her things she becomes the dominate and I become her sissy boy. We have even gone to the point of buying her a strapon and she fucks me like the slut I am dressed up as.

She has even hinted that we get me a wig and she do my makeup then head out on the town as if we are girlfriends and see if I can pass. I would love to do this for her since she was so accepting of my new found kink. I sometimes think she enjoys it as much as I do! It is funny how something as simple as a caught towel in a door can lead someone in a totally different direction in their life. I wonder if I will pass as my wife's girlfriend I will have to let you know how it went.

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bydirtyjoe69© 5 comments/ 103487 views/ 8 favorites

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by Anonymous

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by Tootight108/28/15

good short story

but begs for another chapter.

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