Sissy Glory Hole Stories

127,566 results
Orientation
Length
Source
Infinite Scroll

Trixie's Chastity 02

by trixie47cd on Sep 13, 2017
Transsexuals & Crossdressers

Tammy, the maid took me away to shower quickly in an upstairs bathroom. I was only given about 3 minutes to scrub off the caked on sperm from the guests at the party, then Tammy helped towel me off and completely re-do my makeup. Goddess had packed a dark brown wavy wig that gave me a secretary or teacher look, but the navy pleated skirt was short enough t...

Sammi Gets Adventurous

by Sissy_Sammi_ on Dec 3, 2017
Transsexuals & Crossdressers

Sammi has been doing cam shows and posting photos online for a few months now. She's gotten into a steady rhythm with it, and loving every second of it. She has never felt so alive as when she's fully dressed up and putting on a show for some perverts online. And the money that she brings in from her shows certainly doesn't hurt either. Over the time she's...

Neighbourhood Terror to Sissy Pt. 24

by Fibaro on Sep 14, 2020
Transgender & Crossdressers

Chapter 26 Marcy was a nerve wreck walking out in public dressed as she was carrying the big pink bags stuffed to the brink. The street was relatively calm yet coming out of the outrageous store with those bags she instantly drew everyone's attention. The bus stop was right outside the store and yet those few steps towards it were the most embarrassing step...

Whore for Succubus Ch. 01

by Mixedwritings1993 on Sep 15, 2017
NonHuman

David has turned 20 few months back. In spite of his age and 6' height, his body is not at all developed. He is still hairless on the body like a little boy. His dick is tiny, grows to only about 3" when it is largest. He still wet his pants sometimes, while sleeping and a thumb-sucker. But he has a cute face which turns every girl on when they see it for...

Night One

by Tess_PartySlut on Sep 16, 2017
Transsexuals & Crossdressers

I spent the day with nervous jitters, after you told me what you wanted to do. I was to be your sissy slut and venture to the glory holes to suck cock for you. I rushed to the hotel after work, to begin getting ready. I knew I really needed you to complete the Tess transformation, but I would do my best. Three razor blades later, a good portion of the fur wa...

Re-tooled

by Sissyhalo on Mar 13, 2018
Transsexuals & Crossdressers

Re-tool your life. Re-tool yourself. Sick of not getting what you should? Sick to fucking hell of all these assholes getting with hot people they really don't deserve? Sick to hell of Liberals and Feminists making impossible to jump through hoops so that only the privileged people get to be happy? Sick of being a goddamned incel? Look we all know that...

Allyson the Sissy Whore Ch. 02

by sissymaidallyson on Sep 13, 2017
Transsexuals & Crossdressers

Kevin woke up with his head swimming. Kevin...or was he Kevin any more? Was he just Allyson? He looked down at himself and saw his name badge and decided that for now he should just think of himself as Allyson. Think of herself as Allyson. Oh it was just too confusing. As he started to come to terms with what was happening he saw the door of the jail buildin...

Kimmy the T-girl

by sissy_in_denial on Sep 16, 2017
Transsexuals & Crossdressers

Introduction: Hello. My girly name is Kim, but in my every day life, I am known as Ken. I am 5"5, 135 lbs. I'm eighteen years old, and this story begins on the last day of school before spring break. I have been a closet cross dresser for the past two years. I started off from stealing my sister's panties and bras and wearing them when I was home, alone, an...

My Neighbor is My Daddy Pt. 02

by sissyrulez on Jul 13, 2020
Fetish

(Continued from My Neighbor is My Daddy Pt. 01) I sat in my living room, covered in Daryl's cum. I really should say my Daddy's cum. I couldn't believe I had let this happen. God I'm such a little bitch. I'm Daryl's bitch. Daddy's bitch. I looked at the list he gave me. I needed to buy panties, a butt plug, and a dildo with balls and a suction cup. How am...

The Making of a Mistress Pt. 05

by EiryCGar on Sep 14, 2020
BDSM

Author's note: Marie has married and taken possession of Charles, now known by his initials as Cunt. She has become an official Hotwife; Cunt is now a true cuckold. This chapter deals with their honeymoon on Felicity's island, and the momentous decision that is taken when she and Cunt return home. As always in my fictional stories, all sexual acts take plac...