Caught Sissy Stories

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Halloween Pool Party Pt. 06

by sissymissyct on Sep 14, 2017
Fetish

I was exhausted and slept until 5pm when I was awakened by a gentle kiss from Miss Annie. She took off my headphones and rocked my shoulder a bit. "Come on my sweet sleepy sissy, it's time to get you up and about. We have a fun evening planned for you baby girl". I rubbed the sleep from my eyes and saw Miss Annie's beautiful face looking down at me. "lets ge...

Being a Sissy for Viv Ch. 06

by Caron on Oct 31, 2017
Transsexuals & Crossdressers

Lunch was a pleasant time. I'd prepared and served the food, but we had sat together in the lounge. The blinds down against the weather and prying eyes. The time had felt much closer to friends chatting over lunch than the Mistress-sissy relationship of our previous time together. Viv probed gently about my desires. Intently interested in where and how I had...

A First Time at the OBGYN

by sissypt on Oct 19, 2020
Transgender & Crossdressers

I had been feeling under the weather but since everything had started getting into the doctors office was not an easy task. I had been staying at a friends house since i got kicked out of my mom and step dads for not "following the rules" there was more to it but that's for another time... Having had a sore throat sucked and with all the covid scare my fri...

Dreams

by DrLuverotica on Sep 25, 2017
Transsexuals & Crossdressers

"Hey! Hey! Wake up, wake up!" "What? Jo, what is it? What's going on?" "I think you should be telling me that!" "I don't understand." I was slowly coming round now, But I was still mystified as to why my wife had woken me at 2 a.m on a Saturday morning. "Erm your cock is as hard as nails and you were waving your ass in the air," Jo said, starting to laug...

Sissy College Ch. 02

by MasterJW on Sep 11, 2017
Transsexuals & Crossdressers

All Characters 18+. Sorry for the delay. Life gets in the way sometimes. This is a sissy/interracial themed story - if these themes offend you, or you are unable to separate fantasy from reality, please read no further. Special thanks to Puzziboi for all her input. I love hearing about the mess you make in your panties, so please do leave feedback. ~~~~~ L...

The Work Shower

by AnotherRandomWriter on May 2, 2018
Transsexuals & Crossdressers

Howard Bryce went to the locker room five minutes before the whistle blew. He was in a hurry, hoping to beat his colleagues so he could change into his street clothes unobserved, and protect his secret. He power walked through the factory, taking an unauthorized shortcut between two processing machines (an act that would get him suspended for three days w...

28 Days

by tinywhiteboi on Dec 2, 2019
Interracial Love

28 days. That's 4 weeks since my last orgasm. And I was so horny, to the point of constant distraction. It was all I could think about. My locked little penis was dripping into my panties, and my little balls were swollen. Six weeks ago my wife, Angie, caught me jerking off to interracial cuckold porn, a video with the cuck locked in chastity. She'd come ho...

Danni Ch. 03

by Coder3445 on Apr 21, 2020
Transgender & Crossdressers

Authors note I know it's been a few months since the last Danni came out and I am sorry for making those who want to read wait for so long. With that being said the reason for it is that I meant to write it but suffered from writers block at the time and eventually forgot about it. However I hope this does Justice as I tried to make it longer without sacrifi...

Betty Finds My Story

by JackorJill on Sep 12, 2017
Fetish

The office was quiet at this time of the morning. I came in to get some paper work done. The phones never sounded better. I had put some coffee and stopped for a bagel. The applications on my desk had been piling up and that was a good thing. I never heard Betty until she was standing behind me. "Hey, you're early. Knock'em dead big guy." She was older then...

Sarah Shows Off Her New Panties

by SarahCD on Dec 12, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. *** I was posting a picture of me wearing black ruffled panties on a "Men in Panties" website when I remembered something naughty th...