Anal Sissy Stories

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The Dominatrix Order Pt. 04 Ch. 04

by Jwwsmith on Apr 23, 2019
Fetish

Slave boy departed the docks and stumbled back to Femininus, dazed and in despair. He had no idea what to do. He had made the arduous journey, both physical and emotional, to becoming a slave of Femininus, suffered so much heartbreak and rejection to finally find his perfect Mistress, only to get to spend such a brief time with her before she was taken so ve...

Wife Worship

by Wifesboy on Sep 12, 2017
BDSM

Readers: I am a wife worshipper. This is how I choose to live my life as a husband. ... This morning I woke up early and walked naked downstairs to the dressing room. There as always were the garments my Wife had laid out for me in a perfect order. The panties were pink with small white polka dots and there was a matching chemise. To the right were white s...

Black Cock Smoking Sissy Slut

by Lisa_Fuckslut on Sep 14, 2017
Transsexuals & Crossdressers

I left the club early. No luck tonight in getting my ass laid. Where were all those hot young studs with their big swinging penises and cum-filled balls when you need them? I had dressed in my sluttiest gear. 6 inch 'fuck me' heels, fishnet stockings and a tight little leather dress. Heavy makeup. Long, thick false lashes to flutter at the boys. Long, sexy,...

Sissy Slut Boy

by SissyBoiToi1 on Jan 2, 2017
Fetish

You wake up in your bed, in your attic bedroom. You sigh, not wanting to get out of bed. But then, you realize 2 things--one, your alarm clock didn't go off, you overslept! You have 5 minutes to get to the bus! And two--your bed is soaked in warm, smelly liquid. Did you wet yourself? (Just a note: The "catch the bus" route leads to diaper-related c...

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Sissy Hubby

by rj1774 on Mar 18, 2020
Fetish

In case these are not the fetishes you like; this story features pegging, CEI, and sissy training. * It had been a very long week at work, but I had finally made it to Friday at 3pm and was excited to relax over the weekend. Then a text from my wife of five years came in that started the snowball rolling down a steep mountainside. "Hi! I have to run a few...

Another Weird but Satisfying Dream

by MrJimJim on Jan 22, 2019
BDSM

This story is not true. I just felt the need to get another recurring dream down in words to share with you. I hope you enjoy it! -- It was late. I was tired. I'd had one of those work days that makes you want to scream FUCK YOU to the entire world. I walk in the front door, set my keys on the table, and walk into the kitchen for some water. I go to the...

Femberly: Worth the Trip

by hobbnobb77 on Dec 23, 2017
Anal

Sunday morning as I lay awake in a strange bed going over the events of last night. I noticed I had nothing on but smeared lipstick and my choker. I wasn't surprised that the warm body next to me was a handsome young guy completely naked except some of my red lipstick smeared all over his cock and balls, and i started thinking back to my child hood. I now...

Anal Training Ch. 02

by Catchandrea2397 on Jan 20, 2020
Transgender & Crossdressers

Are you ready to be a good obedient sissy pet? Well shall we begin day 2 of training. Have you got everything I asked for last time? Good. Today you'll need: - Bra and panties - Lube - Butt Plug - Vibrator Get these things and lay them out on the bed. Go shower. I want you nice and clean. Clean now? Good. Now I want you to crawl naked to the...

Miss Johnstone's Lesbian Sissy Slut

by maturesubmale_for_F on Apr 20, 2020
Transgender & Crossdressers

1. Becoming a lesbian sissy slut I was eighteen years old when I became a girl. Or rather: When I was turned into a submissive lesbian sissy slut by my High School teacher, Miss Johnstone. She was an imposing woman, in her late fifties, tall and with short cropped grey hair. She had piercing green eyes and a well-trained body that she kept in shape by regul...

The Prostate Exam Pt. 08

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

Please do not read on unless extreme sissification and forced gay and bi scenes, watersports and cum eating, really flick your switches. I don't want to offend anyone so thought this comment might help. ***** It'd all started with a routine visit to his Doc for a simple prostate exam. His Dominant female doctor had pushed her finger just into his ring and...