Transgender Stories

4,333 results
Orientation
Length
Source
Infinite Scroll

Julia, Ben and Lisa Ch. 19

by chloejacobs83 on Mar 31, 2020
Transgender & Crossdressers

Ch. 19: Saturday - Monday A few quick notes: 1. this is the nineteenth and last chapter of a longish story, a novel in many chapters 2. everyone is 18+ 3. there is no safe sex here - cause it's a fantasy, not an instruction manual 4. crossdressing and gender bending, not everyone's cuppa tea - be forewarned Because Saturday, Sunday and Monday are short...

Working the Holidays Pt. 02

by es_larsson on Mar 9, 2020
Transgender & Crossdressers

My alarm woke me at 7am with an urgent beeping. Bleary eyed, I sat up in bed and swiped my phone screen to silence it. I clicked through the notifications, and within seconds was wide awake. A message from Kareem: "Don't let me down today babygirl. If you don't show up today I'll have no choice but to punish you." Disgusted, I threw the phone down on th...

Lance's Seven Sins - Envy

by Lethal_Erection on Mar 18, 2020
Transgender & Crossdressers

Author's Note: This is the first of seven chapters that will be exploring the sexual escapades of an extremely well-endowed cis bisexual male named Lance. This story is told in first person past tense, and it has semi-ridiculous proportions and cumflation. Lance is now in his late 20s, and he is a spectacle of a man. 6'3" tall (190cm), a toned athletic fram...

Red Swallow Ch. 04

by BJGoodhead on Apr 6, 2020
Transgender & Crossdressers

After completing "The Diary of Jewel Delacroix" I was approached via E-mail by Rachael Ricci Swede and asked if I would consider writing a story idea she had. After a few emails I was intrigued by her idea and agreed to write it. This is an original story by Barbara Jean Goodhead. Written in collaboration with Ideas and Plot Points by Rachael Ricci Swede....

The Virus Lock Down

by puzziboi on Apr 14, 2020
Transgender & Crossdressers

"Okay, Lionel, have your bags packed on Saturday morning," the younger brother reminded his sibling. "I will, Blaine! What time will you be here? I'll be there around ten in the morning." "Do you want me and Freeland to ride together or do one of us need to ride with you?" "You tell me what you want. Just think about it and let me know." "Okay. And you h...

Under Her Wing Ch. 02: The Next Day

by TheLifeErotique on Jan 13, 2020
Transgender & Crossdressers

The morning after prom night dawned bright and clear, like a needle made of glass and light, stabbing into Brad's brain via his eyes. He groaned and tried to hide from the harsh light streaming through the living room window, feeling like his head was going to split open like a coconut. Thud... Thud... Thud..., he found himself saying those words in his head...

Keith's Caught in a Costume Pt. 04

by gaildaniels84 on Dec 30, 2019
Transgender & Crossdressers

Once again, Keith found himself struggling to wake up. But, whereas yesterday had been his fear of what might happen, today he was exhausted because of what had happened. He reached under the sheet and felt at the plastic cage surrounding his junk. Beth, the cheer captain, had locked it on him at the end of cheer practice last night - right after she'd jerke...

Rent Money

by Quixerotic1 on Jan 28, 2020
Transgender & Crossdressers

"Victor, wake up!" Victor rolled about on the couch as he snapped to consciousness. Andrew was standing over him, glaring. "Huh? What? What is it?" "It's fucking 8:15, that's what it is," Andrew said. "You've done nothing literally all day. We had an agreement." Victor sat up. Around him, the apartment was in shambles. Piles of dishes and discarded food...

Always Read Before You Sign Ch. 08

by Reaver90 on May 4, 2020
Transgender & Crossdressers

Laura was lying in her bed on looking at her phone. She could smell her breakfast getting cooked from the kitchen. "Mmm that smells so good," she said. "I can't believe I picked up a slave who knows how to make breakfast." Rebecca walked into the bedroom with a plate and a cup of tea. "Breakfast is served, Mistress." She handed Laura the plate, and it was...

Love the One You're With

by eagle166 on May 4, 2020
Transgender & Crossdressers

All characters in this story are over 18 and fictional. Have you ever wondered how we get to a certain point? Or into a certain position and we have to make the best of it. That's me right now, Hello my name is John Albert, 42 years old 6 foot and 2 inches tall black hair and in top physical shape at 190 pounds. I am a graduate of University of Florida an...