Sissy, Heels, Cuckold Stories

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Helen, my Wife and Cuckoldress

by siscuc on Sep 12, 2017
Fetish

She stood before me, eyeing me up and down shaking her head. "So this is what really turns you on, hey?" she said mockingly as she slowly ran her fingernails over my cock through the lacy panties she had told me to wear. "Look at you getting all excited but your dicky is so small it can't even escape from those panties!" She laughed as she turned on her heel...

A Sissy Cuckold to another Sissy

by Gemsissy on Sep 26, 2017
Fetish

"Christ, Bob!" snaps Julie. You just sigh as you feel your skinny cock throb and spurt into the condom next to her bottom. "What about me?" "I'm sorry, honey. You're just too sexy! I came so fast!" you say, blushing in embarrassment that you couldn't fuck your own wife for more than 30 seconds. "Are you some fucking teenager dweeb?!" She spits as she glare...

3 AM: She Finally Comes Home

by siscuc on Sep 16, 2017
Fetish

I had nervously been awaiting my wife's return for the last two hours after finishing all my chores. The house was spotless and i had done all the washing and ironing she had left for me to do. I was ready to greet her at the doorway with a curtsey just as she had told me to. I was still wearing my new maids outfit, with fishnet stockings, lacy black pantie...

Sissy Cuckold Husband

by bisissystephenie on Sep 16, 2017
Fetish

If you don't like sissy, cuckold, bisexual men stories, then please don't read it only to complain. You look stupid! ***** Like many husbands, I've wanted to see my wife fuck other men. I like the idea of being a cuckold. I had thought my wife Pam had been fucking a man but I had never seen it. One afternoon a friend of ours came over while my wife was at...

From a Husband to a Dutiful Sissy Ch. 03

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Three: My sissy maid lifestyle becomes more set in reality. Morning comes and I carry on my new sissy morning ways, shower, shave, makeup and dress up in my maids dress, this morning a pink satin one over pink pantyhose and pink patent 5 inch spike heel pumps. I dutifully prepare breakfast for my Mistress Helen and get a bowl plain porridge for myse...

Erin Ch. 15: Perfect Sissy Cuckold

by Graves94 on Nov 16, 2020
Fetish

Erin Ch. 15: A Perfect Sissy Cuckold By Jonathan Quincy Graves {Note: This is the fifteenth in a multi-part story series cataloging the progressive evolution of a relationship between a dominant woman who provides leadership and discipline for her husband. Each installment can stand alone, but they read much better if you start at the beginning. Go to: Eri...

Becoming Her Whore

by ecdilettante on Sep 19, 2017
BDSM

Last time we parted, you told me that you were going to fuck me when we next met. You loved the fact that I've never been taken with a strapon and you promised to be gentle, in the beginning. It sent a shiver of excitement and fear through me, which made you smile. I can imagine heading to your small apartment, anxious and excited. I haven't cum for days a...

The Sexy Cuckold Couple Pt. 03

by cuckcpl4play on Sep 19, 2017
Fetish

Initial Fucking of My Wife part 3 It was 2:00 when we arrived home and suddenly Jen received a text from Master. Excited we are moving forward my owned little slut. I would like you both to arrive just after the sun goes down. The reason for the change is that I want you both to walk to my place and will do so in the same under garments you wore to my offic...

She Forces Me into Cuckoldry

by hismasterdivine on Sep 25, 2017
Loving Wives

This is my first fiction and features many aspects of cuckolding and BDSM. Forced feminization, spanking, body worship etc play a part in this tale, where a deluded subby boyfriend's thoughts run riot. If the story is a success, I might write a follow up, particularly due to its frustrating climax! ***** Dominant girlfriend wants a black lover, deluded b...

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...