Shemale On Guy Stories

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Riding the Boss

by Brian70 on Nov 1, 2017
Transsexuals & Crossdressers

Tonight wasn't a spontaneous, spur of the moment act. Tracey, a close 'girlfriend' had really wanted to go out dressed. The more she talked about it the more I was in. We often dress together but it has always been at her place or mine. We have never gone out dressed. Our neighbors haven't seen us either as far as we know. We decided to go to the C & C ABS....

Forever Came Early

by gracie_loves on Sep 15, 2017
Mature

It happened one chilly October night. I always liked the company of my dads friends. They had a sense of comfort and caring to them I liked. There was one that I partially favored more than the others. He was medium height maybe two inches taller than my 5'8. He had black soft hair that every time I saw him his hair was that wind blown way I found attractive...

Susie Suckit

by Bowzer on Nov 25, 2017
Toys & Masturbation

I'm a Pro writer, wrote the novel 'Pack,' among others. First love always porn. The comments people leave on these stories always help me. Good or bad, tell me what you think. BTW, a good writer has a thick skin, takes bad comments and sees if there is any truth. A bad writer gets upset. Have a great day! ***** My name is Susie Sogit. I'm sure you see the...

My First Time as Sara... Pt. 04

by Sexy_SaraCD on Sep 18, 2017
Transsexuals & Crossdressers

I love being Sara and everything it has awakened in me. In the months since I have been with Steve and becoming Sara, I have slowly shredded away my old self like a snake looses its skin. The only time I even dress up as John is when I'm at work. Even then, I have a little bit of Sara with me by either wearing panties and sometimes pantyhose under my khaki p...

My First Time as a Gurl

by Etaindarcy on Jun 4, 2019
Transgender & Crossdressers

By my first year of college, I had been dressing secretly almost every night for close to 7 years. I had stopped, purged, and restarted a few times - usually I stopped dressing whenever I had a girlfriend I was fucking. Ever since I began dressing, my late nights in my room would be consumed with dressing in my collection of lingerie and working myself into...

Katie's Place Pt. 02

by AndreaJordan on Sep 26, 2017
BDSM

That night, in complete darkness, he had removed his suit and shirt and laid them down carefully on the floor. He didn't have his phone and the complete lack of any light made his watch as good as useless. She had effectively left him in complete sensory deprivation, unable to hear or see anything. He lay down and was soon asleep. He woke at various times bu...

A Weekend Away

by daddylongcue on Feb 26, 2019
Exhibitionist & Voyeur

John's younger sister was Madi. She was 19 and blonde. The kind of girl who would wear a thong to an EDM concert and post it on Instagram. She was here with a guy, Jackson, who was a nice enough guy. He was short and stocky. We had all smoked a joint, and still had one in rotation. In the smoky half light, Madi and Jackson were tangled up with each other. I...

The Bus Home

by TENCHI_AKIRA on Sep 25, 2017
Anal

It was a late and tiring night for my Mother and I. We've were just leaving the bus port to home, back in the US. I sort of hated Canada in the winter because it was too fucking cold it made me paranoid that if something flicked one of my nipples hard enough that it would surely break off. Of course the blizzard didn't help anything either, which is the reas...

Butt... Butt...

by possum on Sep 16, 2017
Toys & Masturbation

I woke up to gentle kisses on my neck. I turned my head to look at the person that was kissing me, but it was too dark (or maybe I was too hung over) to make out anything more than a silhouette. I closed my eyes and laid my head back down, deciding just to enjoy it, as I thought about the fun I had the night before... It was our 17th month anniversary, and s...

Take My Picture?

by Gstack on Sep 16, 2017
Interracial Love

reetings Lords and Ladies of Literotica, it’s me, Gina and I am back with the second installment of my tale. I wanted to thank all of you who read and responded to my first story. Thank you for the praise, comments and yes the occasionally criticism. It may not always be pretty, but I promise to keep it true. Well as close as I can recall on some things.......