Wig Stories

6,038 results
Orientation
Length
Source
Infinite Scroll

Mommy Adriana Makes Greta Become...

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

Dear Readers, it took me a while because reality caught up with me, but now the next chapter is ready. I simply hope you don't get bored and enjoy also the 6th installment of my little story. * Finally I lay in bed. I heard Mommy Adriana was sound asleep while I tossed and turned. I simply couldn't sleep after today's events. I would never be the same man...

Just Look at Me Now Ch. 03

by GFfan on Apr 13, 2020
Transgender & Crossdressers

Eager as I am to tell you about my first crossdressed Halloween with Jude and Becky, I must save that for a later chapter and fill you in on some major developments that occurred as my first summer of feminization ripened into autumn. Surrounding these landmark events were patterns of submission we had established early on. I wore panties 24/7, and I shoppe...

A Brief History of Tina

by BethanyJ on Sep 13, 2017
Transsexuals & Crossdressers

********** A series of stories with transgender themes which I hope will be of interest to those who like women, or would like to be a woman. Which includes me! ********** 1 - Monday It really has been one hell of a week and more to come maybe, though I really am not sure how this is all going to work out. An awful lot has happened since last Monday, I...

Rest Stop Romance Ch. 02

by Dark_Rose90 on Sep 15, 2017
Transsexuals & Crossdressers

~The following is entirely fictional and just a fantasy of mine. Any likeness to actual persons or events is unintentional and coincidental. Due to the Pilot receiving a high rating and getting so many views in just a few days, here's chapter 2!~ I woke up early this morning. I wanted to make a nice breakfast for the devilishly handsome trucker that was st...

My Wife's Night Class Ch. 05

by Calvin427 on Sep 26, 2017
Exhibitionist & Voyeur

My Wife’s Night Class Ch. 5: Arranging a Photo Shoot I called in sick Thursday because I felt like spending a leisurely morning with my wife, who had put on such a good sex show for me with her classmate John the night before. Also, there were some stirrings of jealousy I needed to deal with. After getting massaged and briefly fingerfucked by the ridiculous...

My Secret Revealed Ch. 05

by jealouscuck on May 30, 2018
Transsexuals & Crossdressers

The trip to New York was indeed the watershed moment in our relationship. Karen was showing me off as her submissive husband. I could have been resentful of the way she had me come out, but I was enjoying the excitement too much to complain. She had made such a show of chastising me when she found out about my fetish because we were not to have secrets from...

What Just Happened? Ch. 03

by annie_00 on Sep 12, 2017
Transsexuals & Crossdressers

03 – Lessons I followed Beth downstairs to the living room being careful not to fall in my new marabou heels. It felt odd but enjoyable as my new breast forms were bouncing in my bra. It was also embarrassing walking around as a girl in front of my sister. I liked the security of no one knowing I liked to crossdress when I was alone, but after today, too m...

Jeff Crossdresses More & More

by TurningintoCD on Sep 12, 2017
Transsexuals & Crossdressers

My name is Jeff. I date girls every now and then but I always masturbate about dressing up as a hot chick and seducing a hunky guy. My biggest turn on is putting on women's clothes and makeup. I never really had a chance to explore it much when I was growing up. In college I had a secret stash of 1 stick of lipstick, and when I felt really dangerous, I wou...

Becoming Cassie Ch. 02

by TGJamie on Sep 25, 2017
Transsexuals & Crossdressers

When the fall came around, my opportunity to babysit was reduced a bit. I still wanted to, especially with the Warrens, but it looked like it was going to be on a once a month basis with them as there were less events and less nights out for them. September is like that. They called me in late September call and it was a real busy time for me. With sports a...

How I Became Sissy Willow Ch. 04

by willow619 on Sep 12, 2017
Transsexuals & Crossdressers

It was now Saturday afternoon. Last night, after I'd returned home from work I had been dressed in women's clothes by my wife, Allie; introduced to her lover, Mike; been made love to by him myself; been subjected to physical and emotional torture by the two of them; and had it all captured on video. This morning I had had all my body hair removed and had pa...