Sissy Wedgie Stories

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Sailor Moon Ch. 02

by embarrassednakedmale on Feb 3, 2020
Transgender & Crossdressers

The alarm had been buzzing for a solid two minutes when a bleary-eyed Scott finally rolled over and slammed his hand down on the offending device. The harsh noise ceased immediately, and Scott groaned as he rolled back again and cautiously stared at the ceiling. It was still dark in his bedroom, although a single beam of light cut through a tiny gap in his...

House-Sitting Panty Lover Pt. 01

by sissydn on Sep 15, 2017
Transsexuals & Crossdressers

Finally Friday! The day I have been waiting for, for so long. A month ago my sweet and hot neighbours, Megan and Sophie, knocked on my door and asked if I would watch their house and feed their dog when they left for an extended weekend. I immediately replied yes and suggested I could do some house chores since I had no plans that weekend and were low on m...

Sissy Secrets

by DawnCutie on Feb 26, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Every Sissy is just a cross-dresser until someone stronger takes advantage of them. Either they give themselves to a Dom or a Dom takes control of them. This is my story of how my dom found me and turned my life into what it is now. If you're not a sissy let me tell you how we...

Ballet Erection

by pixiemuledonkey on Sep 14, 2020
Fetish

Author's Note: Long ago, I roleplayed a play-by-post erotic fantasy with a girl named Christine, who amazed me with her deviously humiliating responses. What follows is a reconstruction of the scenario we roleplayed, which has ever since remained a favorite erotic fantasy. Wherever you are now, Christine, i hope you're enjoying powerful orgasms! You gave thi...

Panty-Wearing Tease Gets... Pt. 02

by prollybadtodo on Sep 16, 2017
Transsexuals & Crossdressers

The funny thing about being trailed by two men into my bedroom while wearing slutty girl clothes creates the desire not to disappoint. The last thing in the world I would want to be seen as is un-sexy. If I'm going to play the part of a desirable little nymph I'm going to do it right. I made it to the top of the stairs as the two horny men slapped at and pla...

Mistress Encounter

by WellBehavedMan on Sep 15, 2017
Fetish

Eva gets back to her hotel room from her business meeting, glad to be back, the meeting went ok, could've been better, they could all be better she reminds herself, as people don't give everything for nothing. As she flicks on the main lights she jumps as she see's you on her soft double bed, right where she left you before she went out, however she did not...

Tinder Pt. 02

by TwistedPanties on Jan 22, 2020
Transgender & Crossdressers

I appreciate you all asking me for more of the story - It would be hotter if you begged ;) Sissies can be so over-eager... (Keep the feedback coming please, Sweeties) Background: Bryan's roommate Caitlin has just discovered his crossdresser girl Tinder profile, while her friend Allison was swiping for a new girlfriend. Bryan is in the kitchen with a baby...

Panty Posers Ch. 03

by EROTICbearscribe on Sep 14, 2020
Transgender & Crossdressers

It was early on Sunday morning. I awoke needing to pee and slipped out of bed, doing my best not to wake Daphne. I could hear him breathing deeply next to me most of the covers on his side as usual. My roomie was lying on his stomach, his head under his pillow. He looked so sexy lying there. I felt the warm rays of the sun on my back as I breathed in his cu...

Caught Relaxing Pt. 01

by StephaniePlayland on Aug 6, 2019
Transgender & Crossdressers

This is going to be a short series of stories. This one really starts the journey out, they won't all be in exact order or have a proper linear flow to them. Just depends on what's has caught my interest that day, and needs to flow out of me. It's Friday night, no plans or anything to do a perfect night to dress up. Hangout have a drink and relax being Ste...

Chronicles of Heather Maureen Ch. 06

by HeatherMaureen on Sep 14, 2017
Transsexuals & Crossdressers

Life After Marty The loss of Marty's guidance left a huge hole in my life. Still living at home while continuing my education I now had little opportunity to dress and feel feminine. I became depressed and more withdrawn, which mom put down to the loss of my friend Jason, (Marty's 'son'). Losing Marty was more then the mere loss of a friend, much more, but...