Cuckold Sissy Stories

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Infinite Scroll

Gretel Steals Her Lover

by kingkeywriter on Aug 18, 2017
Fetish

Gretel squeezed into another white girdle, hooked on her black stockings, and slid white panties up to cover her nest. After strapping on her bra, she wiggled into a tight black satin dress. Even in the dim bedroom light, the material glimmered seductively. She stepped into black patent leather pumps, two-and-a-half inches high instead of the stilts she'd w...

Saving Matt

by manless on Aug 18, 2017
Fetish

At first it was pure lust that attracted me to Nancy. Those big green eyes, beautiful red hair down to her shoulders, soft, yet perky b cup breasts with beautiful nipples poking out behind her blouse. Her ass was perfect too; that nice round bubble shape that looks so good in tight jeans. It didn't help that she had that soft southern accent, and seemed so d...

The Humiliation of Mistress Penny

by accidentalmistress on Sep 14, 2017
Fetish

My daughter and my husband were out shopping, and I was eagerly anticipating a long evening to myself. Ali had just come home from college, having completed her first year, and she and Robert wanted to spend some father-daughter time together shopping. It was obvious that she was helping him pick out just the right gift for our 25th anniversary, which was on...

Cornholed

by LaBlancheTraversee on Sep 11, 2017
Fetish

I'm in Tori's basement - tied to a chair, blindfolded, naked and gagged. My hands are cuffed behind me and my rock-hard cock is locked in the plastic cup of a chastity belt, engorged and aching for the feel of her delicate skin. Fantasies of her jacking me off with her hand send a jolt of electricity rushing down to my cock as thoughts of our earlier phone c...

Another Day at the Office Ch. 02

by mslstoy on Sep 12, 2017
Transsexuals & Crossdressers

This is the second of I hope many parts, many thank to everybody who gave feedback on chapter 1 (and voted!) and to E who has inspired me to continue. This is an ongoing story so I recommend reading chapter 1 first. ************************** "What do you think you're wearing panty boy? You seem to have men's underwear on today, not sure you count as a man...

My First Pair Of Ladies Kid Gloves

by Classygloves on Sep 16, 2017
Fetish

I could not wait to get home to check out my new purchases and try them on all together. My cock was trembling with excitement with every package. When I opened the glove package and took out the box that held those beautiful black kidskin gloves, I noticed that there was a note inside the box with the gloves. I had not noticed her putting the note in the bo...

Out of Gas Ch. 02

by Pantyboy1204 on Sep 13, 2017
Transsexuals & Crossdressers

Pt. 2: Heather I had just been through quite an ordeal, accepting help from a stranger had not gone at all like I thought it would and now here I was in a strange city being held by one of the men who had just gave me a serious fucking while wearing baby pink silky boy shorts with pink lace all over them waiting for a girl that was supposedly going to he...

Annie's Tits

by Just Plain Bob on Sep 14, 2017
Loving Wives

It was supposed to be a joke. Every year, a couple of months ahead of time, my wife will ask me what I want for my birthday, or for Christmas, or our anniversary. Every year she gets the same answer, "I don't know. Whatever is fine by me." This has gone on for twenty years now and it's always the same, it has never, ever changed. One day we were sitting in o...

The Dominasstrix

by naughtygurl30 on Sep 16, 2017
Fetish

Part I I like to fuck guys in the ass. Nothing excites me more than to take one of those big macho kinda guys and turn him into my own little sissy slut. I get all wet thinking about when their cries of pain turn to moans of pleasure and they go from saying, “Stop! Stop!” to “Don’t Stop!” There is nothing more erotic that the power that a good ass fucking...

The Blue Diamond Club Ch. 02

by MiloDeLaJolla on Sep 16, 2017
Transsexuals & Crossdressers

Subtitle: A Crossdresser's Misadventures A couple of weeks had gone by since my introduction into the Blue Diamond Club. I'd been too busy with work to pursue anything more; at least, that was my excuse. If I'd been honest, I feared how much further I'd be willing to go. I hadn't dressed in anything fem since that night. Instead, I masturbated in the dark o...