Sissy Pantyhose Stories

12,794 results
Orientation
Length
Source
Infinite Scroll

Recruiting of a Sissy Maid Ch. 13

by Sissy_Chantel on Nov 28, 2017
Transsexuals & Crossdressers

Chapter Thirteen: A Business Trip to an Adult Movie Convention, Carl and Chantel Consummate a True Loving Relationship. Carl says, "Chantel make sure you pack well but not slutty ok. I will have you travel with me as my girl friend and secretary. Dress nice but casual for our flight but of course still be an eye catcher ok?" Chantel replies, "Ok hun, I fig...

Master and Four Subs

by totk6432 on Apr 17, 2018
Fetish

This is a fantasy written by myself for fun. It contains spanking, humiliation and fetish; if this bothers you please seek other authors. All characters are 25 years old or older. ======= The rule is simple: I ring the doorbell and let myself into Master Daddy's house. Susan, my 25 year old personal assistant, is with me. She is in charge of me at work. Sh...

Ugly Duckling to Sissy Princess Ch. 02

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Part 1) My girlfriend, Carol, and I made love to each other about 2 times per week. She was also getting fucked on a regular basis by her jock fuck buddies. I never asked how many guys she was hooking up with on the side, but, I guessed it was at least five, because there were five jocks that she tutored on a daily basis. She put on skimpy c...

Sissification 101: Ch. 05

by silkstockingslover on Aug 31, 2020
Interracial Love

Sissification 101 Ch 05 Summary: Erica practices taking BBC in both of her sissy holes. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught by a very supportive girlfriend in pantyho...

The Doctor's Appointment

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

My wife Jo had been suffering with a bad back for weeks. She works as a doctor and many of the procedures she has to carry out on patients require her to stand up for hours at a time. A couple of moths ago she fell off a horse on an activity holiday we were on. And she's never fully recovered. Urged on by my insistence to get her back checked out properly...

Young Crossdress, Meets His Daddy

by Sliver02 on Sep 1, 2017
Transsexuals & Crossdressers

Well I am 28 year old male, not in best of shape. I can still run a mile in under 15 minutes, and I work 3 to 4 times a week. I try to stay in shape a little bit. Well that is enough about my physical appearance. I am also married to very beautiful wife, who I love more then the world. We have very open marriage, but there are few things she does still not k...

Sara Flies the Friendly Skies

by Sexy_SaraCD on Sep 16, 2017
Transsexuals & Crossdressers

His hands were large and firm. No callouses which indicated that he worked a keyboard rather than a hammer and nails. It didn't matter as he was just as manly as any blue collared workers I've been with. His cock wasn't long but was extremely thick. It smelled a combination of his body wash, Cologne and the muskiness of a real man. It was hard and his vein...

Sissy Awakening Ch. 01

by Torbjornson on Oct 19, 2020
Transgender & Crossdressers

- Sex Shop Glory Hole - "Hey baby, when are you coming home?" the text message buzzed quietly. Pulling the phone discreetly from my pocket, I type out, "Same time as usual, just after 5, why... what's up?" It's my lover Sarah, my best friend, and woman I'd known for over 10 years. We were dating and quite a serious item within months of meeting. Everythin...

A Cuck and Bull Story Pt. 02

by PBEnis on Jul 31, 2018
Fetish

Katie steps back into her titty top and pulls on her skirt. I grab her shoes and walk her back to my truck letting the hotel door close behind me, making sure the do not disturb sign will hang on until morning. I don't want the maids beating me back to this scene. Once I have her back in the truck I can see she's a little too far gone to get a play-by-play o...

My Instructions

by Tess_PartySlut on Sep 14, 2017
Fetish

I often travel away from home for business. I don't mind the traveling but I hate having to be away from the woman I love. But she has helped me feel better about the distance, we still don't like it, but at least there is a little joy during the time apart. You see she is also my loving Mistress, and we have a very adventurous sex life full of experimentati...