Sissy Baby Stories

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Orientation
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Infinite Scroll

My Little Slut Ch. 02

by Sweetblood03 on Sep 12, 2017
Fetish

"My apologies, Mistress." He pulls up the flimsy black knickers over his softened cock, bends his head and begins to lick the pooled cum off my sleek black boots. "You realize that this means a day with the cage on for your forgetfulness, don't you, pet?" I reach down to stroke his cheek while his tongue works over the leather catching every last drop of c...

Neighbourhood Terror to Sissy Pt. 07

by Fibaro on Apr 23, 2019
Transgender & Crossdressers

Mark regained consciousness when Stephanie pressed her lips against his and started pushing his load of cum in his mouth. He had only just sucked a load off of Linda's toes and now he was swallowing yet another one. Every time he came here he seemed to get stuck with a taste of cum in his mouth. Only made worse by the way in which he was fed the load. Well a...

Girl's Night Pt. 13

by DifferentBreed on Sep 14, 2017
Fetish

This is a culmination of an earlier story. It contains fetish themes of forced feminization, humiliation and other erotic themes that may not be to everyone's taste. If you enjoy these, please read on. Enjoy. - DB ***** Fisher minced after Eve, his skyhigh six inch heels whispering across the plush carpet of the hallway and then into the spacious living ro...

A Night For Romance

by maggie2002 on Sep 14, 2017
Romance

The night was beautiful as only spring nights can be when winter loosens its harsh hold and the soft winds blown and flowers grow. "Damn, I'm a poet and I didn't know it," laughed Sissy Littleton the Editor of the Littlestown News, as she sat at her computer trying to come up with a short story as filler for the Sunday Magazine. She had to be done by tomor...

Humiliated Sissy Husband Ch. 02

by rik581 on Sep 14, 2017
Transsexuals & Crossdressers

Max was very busy hand washing all of Tonya's underwear and lingerie in the kitchen sink. He dipped a pair of her panties in the clean rinse water dunking them several times before twisting them and squeezing out the excess water. He then placed them in the clothes basket on the counter. Tonya insisted he wear 6" heels around the house especially when doing...

Riley's Bar Ch. 07

by Just Plain Bob on Sep 15, 2017
Loving Wives

When I got back to my apartment there was a message on my answering machine to call my brother. I called him and he told me that what we had talked about at the courthouse was doable and I told him to go ahead and do it. Then I went to bed and slept like a log. Friday was a busy day at work and even though I had my hands full trying to finish the job I was...

My Girlfriend Made Me a Sissy

by libertinaXx on Sep 25, 2017
Transsexuals & Crossdressers

This is my first attempt at a story so any feedback would be greatly appreciated. Feel free to email me about anything: feedback requests or just to chat. * When I was 18, in spite of my shyness and not being in anyway incredibly attractive, I somehow landed myself a girlfriend 2 years older than me. I was quite short for a boy then, around 5'7 and very s...

The Surprise

by MissJAS on Sep 28, 2020
Transgender & Crossdressers

We started on kink, two friends seeing who could take a conversation farther. Two grown people with vastly different pasts but a mutual understanding that sex and what felt good didn't really have to make sense to anyone but you and who you were with. Not that we agreed on everything, but we agreed that if you and your partner were both consenting adult part...

Cockland Island Pt. 06

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

I woke up and I was sucking that realistic dildo cock like a soother and it was so weird and right and made me smile as I pulled it out trying to make my lips do the pop you can do sometimes with suckers. I giggled and did it a few more times then pumped it in and out of my mouth trying to get that dick lips feeling going on. That's a sexy sissy trick, all...

The Nemesess Ch. 02

by ProfessorPlums on Sep 15, 2017
Fetish

Correspondence from older (50-70), dominant ladies most welcome. * The next few weeks passed slowly for Chris. He was initially terrified of his new Mistress, - after the ordeal of his 'breaking in'! However, his new Mistress (Theresa) didn't want a simpering bundle of nerves to play with. Dominance for her was a varied and protracted feast; full of spice...