How I Became A Cross Dresser

Story Info
A simple accident turns his world around.
798 words
4.17
133.4k
22
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
dirtyjoe69
dirtyjoe69
971 Followers

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.

dirtyjoe69
dirtyjoe69
971 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
7 Comments
4Leather4Leather7 months ago

Loved the short story but there has to be more to it.

Love to see we’re you take it.

Please the next chapter

AnonymousAnonymousover 2 years ago

It was,only half a story.

Tootight1Tootight1over 8 years ago
good short story

but begs for another chapter.

AnonymousAnonymousover 16 years ago

When I was younger My mother found some womens clothes that i had collected. She told me that she wanted to see me in the clothes. She handed me a black leotard and tols me to go put in on and come back when i did. I still think of that moment, i loves the feeling and i loved the feel of the leotard and the way it felt, i was hooked for life.

AnonymousAnonymousalmost 17 years ago
I dressed in my mom's bra.

I was fascinated by boobs, at the age of 12-13,i used to stare at women's breasts. One fine day, while alone, i undressed and snapped my mom's bra, filled it with her kercieves, to look full, and stood in front of the mirror, caressing my boobs! Slowly and gradually, i progressed towards other garments, and this is how i turned into a full fledged cross dresser.

Show More
Share this Story

Similar Stories

Dressing Up For My Wife Husband loses a bet & becomes a cross dresser.in Transgender & Crossdressers
Birthday Present Pt. 01 He becomes his wife's lovely lesbian lover.in Transgender & Crossdressers
Cocksucker Straight married man submits to a young stranger at airport.in Gay Male
The Pills He orders penis enlargement pills... with side effects.in Transgender & Crossdressers
The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
More Stories