Sissy Clitty Stories

9,676 results
Orientation
Length
Source
Infinite Scroll

I Get Married

by hotdaddy9 on Mar 7, 2020
Transsexual

It is such a romantic day. Just right for some me time. I am getting married to myself today. I needed to shower. I had a terrible week at work. My boss was her typical self; bitchy, paranoid and touchy-feely. She actively questioned my manhood, my cock size and whether I had what it took. I would quit but for the fact that I am paid so much. I got home and...

Open in Reader

Joel Gets Caught by His Wife Ch. 02

by Downforeverything on Sep 18, 2017
Transsexuals & Crossdressers

This is the second fictional story written for a fan about their sex life. If anyone else has a story they'd like written for them about fact or fictional events feel free to message me. As always please leave comments or constructive criticism so I can make your pleasure better! * The next few days went by without much happening. Joel was a bit ill at ea...

The Awakening of a Sissy Pt. 03

by sissyjolie4u on Jan 20, 2020
Transgender & Crossdressers

As i was watching the video of Mistress and I for the 3rd or 4th time, my phone rang. "Hello my sweet Joey, how are you doing? I so enjoyed spending our time together, I'm so proud of you and the progress you are making. Are you still in your pink bra and pantie? That is such a sexy look for you, it makes you look so soft and feminine. Tomorrow we will build...

Lauri's First Adventure Pt. 02

by stockingsofsilk4me on Feb 25, 2019
Transgender & Crossdressers

Part II (thank you for the positive feedback on my first story ever!) ------------- From our many chats on Yahoo, Micha and I knew each other quite well, even though this was our first time meeting. I knew she was definitely the more dominant (and experienced) of our pairing and I knew there were certain things she wanted to experience with me. Being the m...

Getting Married

by hotdaddy9 on Mar 17, 2020
Transgender & Crossdressers

It is such a romantic day. Just right for some me time. I am getting married to myself today. I needed to shower. I had a terrible week at work. My boss was her typical self; bitchy, paranoid and touchy-feely. She actively questioned my manhood, my cock size and whether I had what it took. I would quit but for the fact that I am paid so much. I got home...

Little Larry Ch. 02

by pantywriter on Oct 9, 2018
Transgender & Crossdressers Stories

The transition from sleep to wake came rather early for Larry the following Monday morning. He rolled over and sat up, and winced as a blinding flash of pain hit him. "Owwwww fuck me," he moaned as he quickly adjusted his sitting position. When he stood it was slowly and carefully, and it wasn't until he had walked through his apartment getting ready for Mon...

Intruded and Blackmailed

by hosiery_cumslut on Sep 16, 2017
Transsexuals & Crossdressers

It all began this one summer, a few months after I turned 19. I had just finished my first year of university in a small "university town", as they call it. I signed a house lease with 3 other friends for the next school year, and we had to pay rent for the four months of summer even if we weren't going to live there. My three friends had all left for home...

Seducing Kevin Ch. 05

by Spango on Sep 14, 2020
Transgender & Crossdressers

Seducing Kevin Part 5 Dear Internet, Sex with Kevin was awesome. Well, awesome does not quite cover it but I am struggling to come up with a word to describe it, so maybe a phrase o two? Ok, how about mind-blowingly stupendous or, perhaps, well, that one will have to do. But you did not come here to hear me ramble on about how good it was to be fucked...

Halloween Pool Party Pt. 07

by sissymissyct on Sep 14, 2017
Fetish

I was allowed to sleep in late the next morning. Probably so there was time to get the medical room set up for the day's events. When Annie came in to get me up it was past noon. I was allowed a couple sips of water but that was all. My nipples and crotch were sore and that was to be expected. I couldn't see my sissy clit pulled back snugly and permanently b...

Khan Market Sissy

by smalltownsissy on Dec 24, 2019
Transgender & Crossdressers

An English degree was all that Lijo had when he took a train from Kochi to New Delhi. He was promised a teaching assistant's job at a University in Delhi. Though he knew that he could barely survive on the salary of a mere 16,000 rupees, Lijo still went ahead as he somehow wanted to leave behind his conservative hometown in Kerala and experience a metro life...