Sissy Cum Dump Stories

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The Blackmailed Sissy

by jmanrules on Sep 13, 2017
Transsexuals & Crossdressers

Jon walked into his roommates bedroom looking for the phone charger he loaned Eric the night before. As Jon was looking around he saw several pairs of panties, bras, and pantyhose. Not thinking anything of it Jon just grabbed his charger and left with it in hand. After he sat down it dawned on him that Eric has never brought a girl over and even if he did th...

Sissy Chantel, New Reality Ch. 09

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Nine: It's Friday, I Have a Full Shift to Pull Today and Tonight. At 7:00am sharp we are all waken up. This is our daily wake up call and soon sissy Traci as our dorm room's head sissy maid has us all up and ready to go to our morning routine which will be a group enema, group shower, shave face and when need be the rest of our body hair then to do...

A Sissy's Forced Gangbang Pt. 01

by sissy77 on Dec 3, 2017
Transsexuals & Crossdressers

I have always seen myself more feminine than most guys I grew up with. Slim and hairless throughout my body, more curvy than muscular. Until my early teens (I am 25 now BTW), being a sissy for me meant not being masculine as other guys both physically and mentally. When i reached my early twenties it turned to me brainwashing myself through sissy hypo vide...

Tales of Sub Asian Sissy Ch. 01

by subASIANsissyJADE on Apr 3, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** (I'm new here and this is my first post! I'd soooooo love to hear any feedback, questions, or comments! Many thanks, xxx, Jade) ***** I wore exactly what he demanded - he told me to dress like a regular girl... he told me he had nosy neighbors and, being a married man, he...

Sissy Chantel, New Reality Ch. 06

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Six: On My Way to My New Life at The Agency. Well the day has come for my transition in my life to becoming another sissy maid and sissy slut (aka: comfort girl) to 'The Agency'. Over the last two hard and humiliating weeks Master Camron and Sir Gage now as paid agents to my joining the team at 'The Agency' have helped me sell, give away or toss o...

A Sissy's Forced Gangbang Pt. 02

by sissy77 on Dec 8, 2017
Transsexuals & Crossdressers

This story is a continuation of the part one of the series under the same title. If you haven't read part 1 already, I highly recommend you do so before reading this part. ***** After snapping out of harsh daddy's words and contemplating what more humiliation was planned out for me, I lifted my head off the bed and was welcomed to the sight of big daddy's...

A New Spin on Role Playing Games

by shawnavinyltv on Sep 18, 2017
Transsexuals & Crossdressers

I've always been something of a geek. I love sci-fi and fantasy books and movies; I can recite countless bits of useless trivia back to you about all kinds of movies. So, it was no real surprise that I took to role-playing games, or RPGs, as we like to call them. You know the kinds, Dungeons and Whatnots, all that kind of Tolkien-esque stuff. I had a couple...

Sissy's First

by CDJessie on Mar 7, 2018
Transsexuals & Crossdressers

This is a work of fantasy. (I wish my gf would do something like this to me.) *** I'm woken up to the blinding sun after Sarah rips open the curtains to our hotel room window. We were up half the night fucking our brains out, and I was pretty hangover "Fuck, you couldn't wake me up like a normal person instead of blinding me?" I ask. "Don't take that fuck...

Natalie Learns Her Place

by natalieukcd on Oct 6, 2020
Transgender & Crossdressers

I had been fucked and i had loved it. I especially loved knowing that i had the female role instead of the male role, which was the normal one for me, historically. I loved being "beneath". I loved being the weaker of the two people. I loved being the repository instead of the one giving. I just loved the feelings of horniness and desire and need and then o...

A Friend Catches Me Ch. 02

by PinkPanties4me on Sep 16, 2017
Transsexuals & Crossdressers

So, here I am kneeling on the floor in front of my friend. I'm dressed in my mint green panties and matching camisole. I just sucked his cock off and he had exploded all over my face. The cum hadn't even dried when Karen, my wife walks in on us. "What the hell is going on?" I look up at her, the cum still on my face. Dave says," Your husband has just confe...