Clitty Stories

3,910 results
Orientation
Length
Source
Infinite Scroll

Those Shoes Double Date

by cd_donna on Sep 16, 2017
Transsexuals & Crossdressers

** Getting Ready ** It takes me three days to fully recover from great sex, even if the love session ends in an ideal sex nap like it did with Rex and Jennifer. I put out so much energy on the bed, my mind and body are slow the next day. I felt lucky that we were not able to do a double date with Mike the next evening. The plan was for a week from that nig...

Caught In Lingerie Ch. 02

by hicutlover on Mar 5, 2018
Transsexuals & Crossdressers

As I awoke, I found myself on my side, with Tim's arm wrapped around me. He too was sleeping. I looked at the clock and figured I was out for 30 minutes or so. My bed sheet was covering the two of us and all I had on was my bra and thigh highs. Tim was still naked. My sissy clitty was hard; my horniness woke me up and I wanted more cock in my boypussy, right...

My First Meet

by Rosecd on Sep 16, 2017
Transsexuals & Crossdressers

This is a true story about the first time that I had a meeting with another cross dresser. It was a Saturday morning in the summer of this year, we had been sending messages for a few weeks online and had arranged to meet. As a closet dresser I had to be careful as although my wife knows that I dress, (she does not approve), she does not know about my de...

Discovering Amber Ch. 06

by Ms_Allison on Feb 12, 2019
Transgender & Crossdressers

Mistress notes: Once you understand them sissies are rather easy to manipulate and control. It's just a matter of finding which buttons are the ones that need to be pressed and when to press them. amber has a weakness for lingerie, heels, and humiliation. Additionally, she was very easily brought to her knees at the promise of an orgasm. Getting dressed up...

My Girly Fantasy

by libertinaXx on Sep 14, 2017
Transsexuals & Crossdressers

I wake up and smile, remembering where I am and who I'm with. I'm warm and comfortable, wrapped in your arms as you sleep. I think back to last night, finally showing you my girly side. We've been best friends for ages but I always had a crush on you.Finally, drunk on wine, I decided to do something about it. I came into the living room we share and straddl...

Yesterday Afternoon

by allourdesires on Jun 10, 2019
Transgender & Crossdressers

A lunchtime call; I was to leave work immediately. Once home I would find everything laid out on the bed: nightie, bralette, cotton panties, hold-ups, lipstick, silver choker and...a blindfold? When I was ready I rang her as ordered, covered my eyes and began to toy with my nipples in anticipation of what was to come. My little clitty jumped inside my panti...

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...

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...

The Office Sissy XX

by pennyjonestv on Sep 15, 2017
Transsexuals & Crossdressers

It had been one of those days where you wish you had chosen flats and support tights. But no, that wouldn't have felt appropriate for the new head of human resources. Impressions are everything in this business. Back to back meetings from nine am to seven pm had taken its toll on my calves, my back and for that matter my mood. It was one of those days I get...

Mandy Sucks

by LilLindaMelons on Sep 16, 2017
Transsexuals & Crossdressers

I've written this fictional story in a POV style depending on what feedback I receive I may write more like it. I've been chatting to an older man for several ages and finally get up the courage to meet him. I dress up in one of my sexiest outfits and meet him at the appointed time and place. He drives me to a warehouse on an industrial estate before I kn...