Sissy Milking Stories

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Orientation
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Infinite Scroll

Kim's Facial Abuse

by Master Jim on Sep 16, 2017
Transsexuals & Crossdressers

Kim wanted his cock in her mouth so bad, she could taste it. She had hardly been able to sleep the past few nights. She was waiting for Thursday afternoon, when she knew he would be coming over to use her. Master Jim had been wanting to put his cock in her mouth so bad, he was about to explode. He had hardly been able to sleep the past few nights. He was go...

Dr. Gaylove Pt. 01

by switchhitter420 on Sep 13, 2017
Transsexuals & Crossdressers

Dr. Gaylove, or How I Learned to Stop Worrying and Love the Black Load Pt. 1 ***** As I came back up for air, gasping and gagging and spitting all over the 10", stiff, glistening black cock in front of me - standing erect and proud for the whole world to see like a dark pillar of dominance, a symbol of manhood and all that is virility, dripping potent see...

Sex therapist

by qaz on Sep 1, 2016
Miscellaneous

Who do we follow?What's next? A boy A girl What's next? A boy A girl...

Open in Reader

Ms. Alexandria - Interview No. 02 Pt. 02

by gasissynora on Dec 3, 2019
Transgender & Crossdressers

This is the third part of the Ms. Alexandria series and part two of The Second Interview. I believe it will stand alone, but will make more sense if you read the earlier parts of the story, particularly Part 2a. This part starts with the last paragraph of the previous part. Ms. Alexandria: The Second Interview -- A day out. Part 2b Mistress walks up behind...

Discovering Amber Ch. 08

by Ms_Allison on Apr 23, 2019
Transgender & Crossdressers

Mistress notes: After 8 or so months of going to the club twice a month amber became a welcome regular and a great dancer. Actually, she danced better in 5" heels than in men's dress shoes, which I obviously teased her about often. I also made sure to keep her embracing her comfort level with being groped while dancing. Her dance partners soon learned her li...

The Unsuspecting Candidate Ch. 03

by missvicky53 on Sep 11, 2017
Fetish

I awoke at 6:00 A.M. and set about preparing for my sissy's surprise. I opened the door to see him there on the bed, his ankles and wrists still cuffed to the four corners of the bed. His head was still encased in the bondage hood and he lifted it as I shut the door and approached the bed. "I trust my sissy slept well," I cooed as I began to release him fr...

Finding Claire

by Sissyhalo on Nov 26, 2017
Transsexuals & Crossdressers

*Before... I get cleaned up and instead a drink I have a big mug of coffee and a long, long shower. Thinking on all of it a lot. Then I check my bank accounts twice online. I go outside after slipping into sweats and walk around my house and the yard and the garage, the big barn one out back. It's my second house here actually with Roxanne getting the f...

Daddy's Little 'Girl'

by keptsissy on Sep 16, 2017
Transsexuals & Crossdressers

The noises he makes, the sound of it all, it's my favorite part. I love the feel of him in my hand but to hear him moan, grunt, make all the 'man sounds' men make when they are being driven sexually crazy makes my little thing wet. The slippery sound of him sliding back and forth through my hand, I love all of it. Masturbating him is one of the most erotic...

A Deal Offered

by LockedSissySubmissive on Sep 25, 2017
Fetish

I was sitting in the kitchen drinking coffee wearing my dressing gown when Emma left for work. We'd had a pleasant morning chatting about the various inconsequential matters that married people chat about but she had to leave for a meeting and looked fabulous in a smart dress suit and jacket. Even after almost two years of marriage I was still totally smitte...

A Toy Party Story

by lushusboobs on Sep 11, 2017
Transsexuals & Crossdressers

Toy Party Story Recently I met with a person whose sole desire was to be fully dressed and transformed for me. We spent quite a bit of time on the phone discussing why feminization was such a powerful fantasy for him. He explained that he felt so vulnerable and powerless as a woman and that it was exactly the opposite of his everyday life where he held mu...