Small Penis Chastity Stories

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Finishing School for Shemales

by Imogen_TS_2020 on Sep 25, 2017
Transsexuals & Crossdressers

Mistress K looked at the school report and smiled. She wouldn't describe herself as an evil bitch, but plenty had. She was proud of her position. Headmistress of the Finishing School for TGirls. So many beautiful shemale girls had left her careful administration and gone on to happy lives, or sometimes porn careers. Sometimes they had been bought outrigh...

Arabian Nights Pt. 05

by MicheleNylons on Sep 26, 2017
Transsexuals & Crossdressers

Defiled ***** Sadan pulls his cock from Michele's anus with an audible plop. Semen mixed with lubricant run in a rivulet from Michele's anus down her thigh and soak into her tattered stockings. Sadan wipes his cock on the remains of her ripped panties and then pushes Michele facedown on the bed. "You have performed well my pretty putta; better even than t...

Seitensprung

by History Nut on Sep 17, 2017
Mature

Seitensprung: An Adulterer's Experience Seitensprung is the German term for an adulterous affair. Literally, it means a jump to the side, or in this sense, to the outside of a marriage. Now, let me tell you about my initiation into the ranks of those who made that leap. Ruby was a neighbor who lived about four houses south of the house my wife and I lived...

JoJo Meets Diane

by polishjoe on Sep 16, 2017
Transsexuals & Crossdressers

We met in the Florida Keys and soon became friends and lovers. His male name was Eddie but he preferred to be called Diane. She was great fun to be with, about 5'-9," black hair with deep black eyes, beautiful full lips who could easily pass as a woman. As we walked around town, hand in hand, we looked like two woman in love. I stand 5'7" and looked up to he...

Breakfast in Bed

by DawnR on Dec 24, 2019
Erotic Couplings

A Mike and Melanie story I was awakened by the sound of a door opening. Where was I? I had my sleeping mask on as I hate being wakened by the early morning daylight. At home we have blackout blinds. I heard nothing but the gentle swish of the ceiling fan and then I heard a whispered exchange. Of course, we were celebrating our third wedding anniversary wi...

Best Girl Ch. 03

by afstories on Sep 14, 2017
Transsexuals & Crossdressers

TO BE READ BY ADULTS AT LEAST 21 YEARS OF AGE ---------- The bed creaked and Todd opened his eyes. He longed for the disorientation he woke up with the previous day. This morning each of the events of the last couple days were seared into his memory. He didn't need the slick, cool feeling of the satin babydoll he was wearing to bring him back to reality....

Valentines...

by Dr_Impervious on Sep 16, 2017
Exhibitionist & Voyeur

Chapter One We are strolling through the city contemplating whether or not we should go to the movies. There's nothing playing that either of us desperately want to see so we stroll around aimlessly chatting about friends and how good we have it. You thank me graciously for your morning treat and breakfast. I am feeling proud and so I query, "Tell me about...

Breakdown Service

by pandsal on Sep 15, 2017
BDSM

Erratic steering told its own story: a puncture. Thirty miles from home, late on a chill night after a business dinner as unproductive as it had been boring. When I called the breakdown service they were sympathetic to the plight of a woman alone but said the best they could predict was forty-five minutes. It was a surprise to see a vehicle pulling in behin...

Bob, Barbara, Bart

by Montana1947 on Sep 1, 2017
Group Sex

I'm in my early 60s but still think like a 25 year old. I've kept myself in pretty good shape, considering my loose living and carousing, heavy drinking and smoking, in my younger years. I could still hold my own with the younger crowd today. I was into self-defense, combat training, boxing, and when I served in the military I was in a Special Forces Unit. I...

Deep Throat Wife Pt. 02

by pfanv on Sep 5, 2018
Fetish

As it says in the title just a wild fantasy. I hope you enjoy it. Pfan. ***** I woke slowly sun streaming into the room. Still buried in Sam's hot ass. I started to pound away still turned on too much to hold back on my orgasm, so I came quickly. Pumping a massive load of cum into Sam's bowels. I slowly worked my semi-hard cock out replacing it with her...