Transgender Stories

4,333 results
Orientation
Length
Source
Infinite Scroll

Casino Weekend Ch. 02

by Lindseycd4rp on Feb 12, 2019
Transgender & Crossdressers

Will woke up as usual, without an ounce of grogginess, and ready to start the day. Except unlike most mornings, he took some extra time to reflect on what had happened the evening before he got onto his daily routines. With smiling eyes he stretched, feeling the silk nighty slip easily on the bedspread and stretch across his skin. The lace of his panties c...

X-Change, X Change, Xtreme

by Grabenork on Feb 26, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. * * * * * Monthly meeting of X-CHANGE Marketing Department: Sam Donasen: "People, sales are down. We have to do something to increase sales. These pills are expensive to make, and expensive to buy. We have to do something to get more people to try them, and to get our existing customer...

Hubby's Sissy Training Day!! 02

by Red10Dog on May 20, 2019
Transgender & Crossdressers

I get a text from my wife reading "Clean your ass and get dressed up cause your cum slut training is happening tonight!" It was a month ago when we had our weekend getaway with the wife training me to be her cum slut. Our sex has been fantastic since then. Our love for each other has gotten stronger. A few weeks ago we laid in bed and I rolled over and kiss...

Neighbors Delight Ch. 05

by gummidurango60 on Apr 10, 2019
Transgender & Crossdressers

I wake up next to my wife; I was so tired and distraught from yesterday I never heard her come in last night. Still, I have to put my best effort into giving everything into my marriage and family and leave my rendezvous with Aaron behind me; far behind me. Lynda's back was toward me and I put my arm around her as I snuggled up to her. "No, it's uncomforta...

The Photographer's Trap

by ElizzyViolet on May 21, 2019
Transgender & Crossdressers

Elizabeth here; this is part one of a two part story, and is my only story without speculative elements (apart from whatever magic is keeping Timothy's dick in his panties). This story might not be for everyone (see tags), but I hope you like it. ~~~~ ~~~~ There was only one laundry room in the entire apartment complex, and someone kept leaving their cloth...

My Sissy Bucket List

by _pdy_ on Apr 3, 2019
Transgender & Crossdressers

Just want to open up this piece with a little apology for my hiatus from continuing to document my time serving J. Life has just been so busy, and it's tough to find some time to write. Anyway, as you can probably clearly tell by the title of this piece, it is not a part of the Panty Boy Diaries series that I've previously started, and you do not have to hav...

Pretty in Pink Pt. 02

by secretLace on Apr 8, 2019
Transgender & Crossdressers

Chris awoke as the sun played across his face. He closed his eyes again and just enjoyed the warmth of the spring sun. He could hear Thea talking on the phone in the adjoining room, probably work related by the sound if it. With a content smile he listened to her talk. When she was in work mode she was so forceful and decisive, so different to when they wer...

Mistress Valeria Pt. 03

by BootyAllDay on Jun 25, 2019
Transgender & Crossdressers

This is part 3 of my Mistress Valeria series and I truly suggest reading parts 1 and 2 before this one if you have not done so. Thanks all for the support and feed back on the first 2. I believe this should be the best part. This is still around 90% accurate and I am looking to drag it out a little more by being more descriptive and let the story come to me...

Uncovering the Sissy Beneath Pt. 03

by jefferyscott745 on Jun 25, 2019
Transgender & Crossdressers

Disclaimer: This story contains extreme fetishes including BDSM and forced seduction. It is also purely fictional. This is part three of my previous work. Be sure to read parts one and two if you wish to understand the background of this section. *** I hesitate to follow him out of the bedroom, as my anxiety is out of control. "Have I just been kidnapped...

The Photographer's Trap Ch. 02

by ElizzyViolet on Jun 25, 2019
Transgender & Crossdressers

Elizabeth here; lots of people wanted another one, so this is the second part of "The Photographer's Trap". Reading the first part is probably a good idea. You'll see some toys and butt stuff in this one, unlike in the previous. Happy reading! ~~~~~ ~~~~~ Since that Saturday morning, Timothy started to find himself wearing panties underneath his ordinary c...