Jerking Off Wearing Lingerie Stories

339,936 results
Orientation
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Infinite Scroll

Step by Step Sissification Ch. 01

by satinmarabana on Sep 16, 2017
Transsexuals & Crossdressers

Over the years, I've been with a few different sissies who were in different stages of their exploration and this gave me the opportunity to participate with them and learn a lot. I've also spoken with a couple dozen sissies on literotica who shared their own fantasies and desires. This story is sort of a distillation of my favorite stuff. -- It all star...

Caught in a New Life Pt. 02

by Fibaro on Jun 15, 2020
Transgender & Crossdressers

(Hello everyone, here is part 2 of the story requested by one of my readers.) Chapter 3 While Monroe was having breakfast the next morning Lena passed by on her way out wearing a white body con designer dress with a black belt at the waist, black sheer pantyhose, a pair of white patent leather heels, big rounded sunglasses and a wide floppy white hat with...

Caught with Porn

by jon227 on Sep 12, 2017
Loving Wives

Shit, I realized I forgot to delete my browsing history. I couldn't do anything about it now, I was still at work and would not be home until late that night. Sarah generally uses the computer but maybe she might not today, or might not pay attention. I tried to convince myself there was nothing to worry about, but the more I did the more I remembered the ra...

Sissyhood of Travelling Panties Ch. 02

by daddyslittlebitch on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 2: Blake Blake hurried back to his bedroom and closed the door behind him. In his hand he held a very sexy pair of red satin boyshort panties with lacy details, the panties he had just taken from the laundry basket. At 19, Blake still lived with his parents and there was very little he enjoyed more than the sight or fantasy of his mother's still hot...

My Life as a Sugar Daddy Pt. 01

by frenchie789 on Jul 11, 2018
BDSM

Main themes: public humiliation, small penis humiliation, cuckold, forced bi, blackmail, financial domination, light racial play, sugar daddy, sugar brat. ***** "I just love the presents you brought me, Chris! I'm impressed you followed all the requests in my ad. Our first date is going to be amazing. Most people that contact me thru my website are so lam...

Caught in Ex-GF's Underwear Pt. 01

by HiddenThoughtz on Oct 6, 2020
Transgender & Crossdressers

Hello everyone...welcome to my crazy kinky life lol. This origin story takes place right before my 21st birthday. This all started when I finished my junior year at college. School had ended and I was taking summer classes so my workload senior year would be easier and I could enjoy my last semester. My two roommates had gone back home to work for the summe...

Addiction to Lingerie

by grgy56 on Sep 19, 2017
Transsexuals & Crossdressers

My girlfriend Lora was the most perfect girlfriend. Her pretty face and rocking hot body were the envy of other women. When we were dating, Lora would do almost anything for me. Sex anywhere; any time; in public or private. But one of the hottest things was seeing her dressed in sexy lingerie. Lora wore it under her business suits to work, out to dinner and...

Desparate Times

by HirstWood on Sep 16, 2017
Toys & Masturbation

John tried not to make the stairs creak as he made his way up to bed. It had gone midnight and his wife had gone up nearly two hours ago. Opening the door to their room, he saw the light from the phone in her hand. "You and your games. Sweety Crush is it?" he asked. "Level 19." she said, without looking away from the screen. He took off his clothes, lett...

Sissy Housewife Learns to Eat Cum

by tiffanyfoxe on Sep 12, 2017
Transsexuals & Crossdressers

Only a few days after Miss Jennifer agreed to let me be her housewife, she informed me that now that I was "pretending to be a girl" and was required to always be dressed completely as a girl, she expected me to service her the way one girl would service another, with my mouth and tongue. At least three times every day (always in the morning before she left...

She Caught Me...

by LuvStockings on Sep 26, 2017
Fetish

She Caught Me And Made Me Do It! This is another story of fiction: She found out that I'd been authoring these hot fantasy stories when I left my computer on and my "secret" files were there. She used my computer to check for something on the internet and I had left my word file open to a story. She read it and then read others – she was shocked at my stor...