Small Penis Sissy Stories

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My Week with Laurie

by robbie3 on Sep 14, 2017
Fetish

Laurie was a co-worker who had recently been appointed the training officer in our government agency. As such, she had acquired a nice private office, in which I found myself spending more and more time. We had always been friendly, but lately were exchanging comments of a more personal nature. I'd call it meaningless flirting. Laurie was a year or two young...

Bewitched, Bothered and Bewildered Ch. 03

by trevorm on Aug 30, 2017
Fetish

Part Three RULES OF THE GAME Where Vivian's mother lays out exactly what she expects from her son if he wants to keep her onside and help him to achieve his dream. Vivian went into the bedroom with a towel wrapped around his waist. He was whistling, there was a spring in his step. "You've been ages... hello, what's this?" His mother indicated the towel....

Sissy Gets Punished on His Birthday

by NSEW1 on Jul 3, 2019
Fetish

My lovely goddess of a wife had promised me a memorable treat for my birthday. I stayed on my best behavior that week, in anticipation of an exciting climatic night of pleasure. During the day she texted me 'hope u are ready for treats.' I wrote back to confirm and then told her I was doubly thrilled to get not just one but multiple treats. She responded bac...

Man Disciplines Sissy Ch. 05

by LanaBehave on Oct 21, 2019
Transgender & Crossdressers

This is a fantasy. Scenes in reality should be built on consent, safety, and communication. No character in this story is less than 21 years of age. * I was jittery all the next day. I hadn't slept well, at first, either. As I lay in bed thinking about Daddy, the things he said, what we had done, alone in the locker room, I squirmed, tossing and turning....

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...

Miss Jennifer Fucks Little Tiffie

by tiffanyfoxe on Sep 12, 2017
Transsexuals & Crossdressers

The Saturday after Miss Jennifer had her boyfriend fuck my pussy/bottom, she called to me while I was doing her laundry and told me to come to her room. As I entered, she told me to come and stand in front of her, where she was lying on her bed. I was, of course, dressed like a proper little housewife, with my pink lace bra stuffed with my big 54DD falsies...

The Cuckold's Babysitter

by yumacd on Sep 26, 2017
Loving Wives

Hi, I haven't written in a while. The set-up for the sex is probably too long. I'm thinking of continuing the story. Hope you enjoy it. YumaCD === My wife, Tami, has been cucking me for a couple of years now. Most of you Literotica readers have heard the story before... - It started when I revealed my fantasy of watching her with another man one night...

Mistress Morgan's Sissy Husband

by corduroysissy on Dec 10, 2017
Transsexuals & Crossdressers

Morgan Ashley was a very pretty lady, not movie star glamorous mind you, but far prettier than anything her wimpy husband Robin would normally attract. Having just stepped out of the shower she was wearing a red mid-wale corduroy bathrobe and her long red hair was wrapped in a towel. She was seated in the living room armchair with a cigarette perched between...

From Husband to Man's Sissy Wife Ch. 03

by Pantypansy on Jul 15, 2019
Transgender & Crossdressers

'So how was it, sweetie,' Hamish asked me as I opened the door. I was still shivering with desire from licking up my wife's lover's cum off her huge, oiled tits in 'their' bedroom downstairs (actually my marital bed).. I felt a sudden wave of emotion, after being so overcome with desire to watch my wife's lover come all over her. I had helped him by pushing...

A Well Groomed Sissy Boy

by keptsissy on May 15, 2018
Transsexuals & Crossdressers

"If I receive any complaints I'll diaper you and put you in your dog cage for 48 yours, no exceptions. Do you understand?" He looks down at me. I feel his dominance over me. I see the look on his face. I start to cry hard. "Please, Daddy, no. Don't do that to me, please...I'll be good...please..." I stammer through sincere tears. "Well then, all you have...