Sissy Boyfriend Caption Stories Stories

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CFnm Adventure - 2nd Visit

by lovelicker99 on Sep 13, 2017
Fetish

Note: This is the second story involving encounters between me as a submissive male and a Dominant BBW who responded to an ad I ran online. These stories are fantasies, but some of the specific acts are things I have done and enjoy doing. If you are a woman or a couple that enjoys doing any of these things I would like to hear from you regardless of where yo...

D Cup Blues Again

by YDB95 on Aug 26, 2019
Novels and Novellas

PRELUDE: SPRING "You're so adorable with your glasses," Caryn sighed between moans as she humped Dave with delightful abandon in his narrow bed. "I feel silly wearing them when I'm not wearing anything else!" Dave replied. "Oh, you know you love seeing these as well as you can feel them!" Caryn placed both her hands over his hands, which were massaging...

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

Lucky Jack Ch. 02

by GreenFingers2015 on Sep 19, 2017
Novels and Novellas

LUCKY JACK Being the misadventures of one of life's losers. Chapter Three: Jack in Clover WARNING TO NEW READERS- This is a rambling, VERY British episodic part work which was originally published as a series of short stories in the 1990s but has recently been modernized and brought into the 21st century. The main character, Lucky Jack, some readers may r...

Snugglebunny Ch. 11: Remote Control

by saddletramp1956 on Oct 5, 2020
Mature

Snugglebunny Ch. 11: Remote Control This is the eleventh chapter in the saga of Chris and Chloe Weber. While the story can be read separately, I suggest you read the earlier chapters to understand the full context of what is happening here. It would also help to read "No Greater Love." This story takes place about 4 years after the events in "Snugglebunny C...

Lady in Red Pt. 02 Ch. 03

by Harddaysknight on Sep 25, 2017
Novels and Novellas

"We can't leave without my two daughters!" cried a very distraught woman just as Steve gave the order for the helicopter to take off. Steve motioned for the pilot to continue before he turned to face the hysterical mother. "We searched the compound. We have everyone. There's no one left. They must be on the other chopper," yelled Steve over the drone of the...

I Put on A Cock

by ndeavour on Jan 6, 2020
Erotic Couplings

Hi, my name's Liz. I'm not about to tell you how old I am -- but I have a 25 year old son, so that should give you a sense. I've only just stopped coloring my hair and begun letting a whole lot of silver to emerge. I no longer have the slim figure I did before having my son; I gained nicely in the boob department, but picked up some extra padding all over. I...

Twenty-Two More Questions

by silkstockingslover on Jan 20, 2020
Reviews & Essays

Twenty-Two More Questions Summary: 22 questions asked by readers answered. NOTE: Thanks to Tex Beethoven and Robert for editing. I wrote the essay Twenty Questions in December 2017 and Twenty-one More Questions in 2018. I answered the following questions, in case you want to read them. 1. Are you really a teacher? 2. How often do you wear nylons? 3. Wh...

Huntress of the Fallen

by GayTripper on Oct 6, 2020
Erotic Horror

+++++ Huntress of the Fallen +++++ The following tale is my entry in the 2020 Halloween Story Contest. It acts as both a sequel and the final act of a trilogy that began with the 2016 Halloween Contest First-Place Winner "Sisters of the Fallen" and continued in the 2019 Halloween Contest First-Place Winner "Redeemers of the Fallen". I hold no expectation of...

I Spy On Love

by FantasyXY on Sep 13, 2017
Romance

My name is Gunn... James Gunn. I am a spy. To be more accurate, my life's work is in intelligence, if you actually want to call what I do intelligent. I guess you could say I'm a spy, but it's not what you might think. My profession is actually pretty pedestrian. It's just a job, not unlike any other line of work. Sure there are more cloak and dagger jobs...