Pegging Crossdressing Stories

2,183 results
Orientation
Length
Source
Infinite Scroll

Kylie Minogue - Equilibrium Ch. 02

by Noj on May 4, 2020
Celebrities & Fan Fiction

This story is entirely fictional and is in no way connected with the subject. This story contains adult material and is only suitable for people over the age of 18. If you are under 18 please stop reading now. All characters appearing in this work are fictitious. Any resemblance to real persons, living, dead, or undead, is purely coincidental. All characters...

The Transition Ch. 01

by Quantarx on Jun 8, 2020
Transgender & Crossdressers

Greetings and thank you so much for choosing to read my story. This is intended to be a multi part series so bare with me as I try to develop the characters and lay down the backstories. As always, Your feedback is always essential in the development of the story going forward. Please leave a comment down below * I Had been Married for about eight years w...

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...

Kinky Awakening Ch. 01

by rj1774 on Oct 13, 2017
Fetish

FYI, this story features CEI and pegging if you are uncomfortable with that click to next story. ***** My husband is a high powered attorney which allows me the luxury to stay home, volunteer, and keep up my hobbies. This made what I found even more concerning at first. He left in a hurry one morning and forgot to shut down his laptop. Not thinking anythin...

Saudi MILF & Black Scholar Ch. 10

by Samuelx on Sep 16, 2017
Interracial Love

Can a guy develop prostate issues as a result of too much strap-on sex? I'm afraid to ask my doctor this question. My name is Tyrone Ferguson, and I'm a young African-American man living in the City of Ottawa, Ontario. The reason why I've got this burning question on my mind is because my gorgeous, sinfully sexy Saudi Arabian girlfriend Amina Alzahrani has b...

Femdom Training 101

by bdsmtrainer88 on Sep 13, 2017
How To

Quick and simple guides to help turn that selfish and controlling man into a loving affectionate slave Training his mind is just as important as his body. He will need encouragement. Constantly remind him how he's given himself to you and how you cherish the sacrifice -- but he needs this training to really become yours. Associating arousal with pain and f...

Several Stories from Somewhere Else

by Freyasbearn on Mar 11, 2018
Fantasy

This is the landing page that will take you to the several stories re-archiving here. I am also using this section for new stories with the same themes as my other stories. That way I don't have twenty different stories all over the place that cover the same stuff. You can get it here. If you want to add on, or take a story a different way-- please, please d...

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Fulfilling all My Fantasies Ch. 01

by classmate1119 on Apr 23, 2019
Transgender & Crossdressers

"Last chance to change your mind, Cristi," Jalen said. "It's probably the most outrageous one so far! Not that I'm worried, of course, but you never know what else might happen... " I reapplied my lipstick in the reflection of the club's glass entrance. "Hey, we spent too much time preparing for this. Don't back out on me now, Jalen!" I threw him a coy smi...

Kylie Minogue - Equilibrium

by Noj on Jan 29, 2020
Celebrities & Fan Fiction

This story is entirely fictional and is in no way connected with the subject. This story contains adult material and is only suitable for people over the age of 18. If you are under 18 please stop reading now. All characters appearing in this work are fictitious. Any resemblance to real persons, living, dead, or undead, is purely coincidental. All characters...

Black On Black Pegging: Twerking

by Samuelx on Sep 11, 2017
Fetish

When life gets boring, you need to go and make your own fun. In case you're wondering who this is, my name is Melanie Oguje and I was born in Kano City, Nigeria, and raised in the City of Ottawa, province of Ontario. I'm five-foot-eight, slim and fit ( but with a nice round butt ), with dark brown skin and short, spiky Black hair. I studied business administ...