Caught Dressed As A Girl Stories

361,457 results
Orientation
Length
Source
Infinite Scroll

Highwaymen Ch. 12

by hardtaskmaster on Sep 14, 2017
Novels and Novellas

It was around noon when they finally awoke. Joanna stretched her arms and legs like a cat, flexing wrists and ankles. As she moved from the bed the others stirred. Rosie looked aghast as she realised how late in the day it was already, but Joanna quickly assured the girl she would see her right with the landlord, and Terence added his own reassurance. Very h...

Sissy Gets Punished

by MsMorrigan on Sep 16, 2017
BDSM

Once upon a time there was an overly eager sissy girl. This sissy girl loved her mistress. She loved her so much she tried to anticipate her every whim before she needed to even speak the words. One day the sissy girl was vacuuming, dusting and general cleaning. She was openly lamenting on how her overly large pathetic sissy clit was getting in her way. How...

An Ever Changing Story

by Helenthemaid on Sep 16, 2017
Transsexuals & Crossdressers

Caught Out and Permanently Punished I was wearing a ultra short black leather mini skirt, a tight leopard print low cut top, which revealed my cleavage entrapped by my pink lacy bra (with matching panties). The straps of my 6 inch leopard stiletto heels were securely padlocked around my ankles. Recently I had been often going to the local park dressed in...

Working (Girl) from Home

by meowjennie on Oct 5, 2020
Transgender & Crossdressers

I woke up to the whimsical chiming of my phone alarm. It was Monday morning, and under normal circumstances, Monday mornings were the absolute worst. But the times were far from normal, and in response to the spread of COVID-19 my boss had implemented a mandatory work-from-home policy. While my coworkers bemoaned the lack of office socialization, I was secre...

Trip to England Ch. 06

by evals22 on Sep 16, 2017
Loving Wives

Lori and Tom walked to their hotel with the crisp sea breeze blowing at them. Lori's ass hurt from the session with Tad. She said nothing to Tom and he did not try to start any conversation. When they got to the room Lori dropped the coat and kicked off her shoes. She fell on the bed, face down and was too tired to remove her nylons. She felt the weight of...

Shared for the First Time

by lkg4funherenow on Sep 13, 2017
Loving Wives

It was another boring night on the road, stuck in a great hotel alone. I was passing time looking through the Craigslist post when this one caught my eye. Couple looking to be properly spanked - was the header. As I read further, they described themselves as a young fit couple with submission fantasies. They wanted to be put over the knee and spanked. It is...

Blackmailed into Submission Ch. 02

by tzleaze123 on Mar 26, 2019
Transgender & Crossdressers

How in the Hell did this happen? I am not about to let this little girl blackmail me. She is only 20 and cannot possibly know how to pull something like that off. She has already had me sucking cock (first time) in front of a guys girlfriend. I have no idea who it was because I was blindfolded. Sure she said his name was Jack and his girlfriend Kim and true...

Girl in a Miniskirt - Carla

by DaveLondon on Sep 16, 2017
Exhibitionist & Voyeur

Essentially an English telling, Carla's tale will not appeal to everyone. That said, for those with a taste for exhibitionism, voyeurism, dressing-up, and the downright rude, perhaps Carla may have something up her sleeve – er, skirt. Her story endeavours to balance plot, pace and imagery with an occasionally despicable eroticism, designed to titillate and e...

Caught In Lingerie

by hicutlover on Sep 26, 2017
Transsexuals & Crossdressers

I was driving home from work and all day I had been extremely horny. I had unbuttoned my pants and was stroking my cock in my purple nylon thong. I loved this thong. I could see the outline of my cock and the shape of my cock head in these panties. It was making me harder. All day I had been fantasizing about taking a cock in my boypussy and couldn't wait to...

Stairway Strip Game

by Eterriswolf on Jul 31, 2018
Exhibitionist & Voyeur

A/N This, as usual, did not happen and is just imagination. None of the characters are real people, except myself, and any similarities are complete coincidence. Enjoy * In my fantasy... Things were boring, it was the first few days before classes and I had just gotten back to my new dorm after lunch. My friend wasn't available so I was planning on just...