Dildo Sissy Stories

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Orientation
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Adventures of Wyn Pt. 02

by Lyn_Wynn on Dec 25, 2019
Transgender & Crossdressers

These stories are my fantasies and how I'd love to live my life. Everyone who interacts in sexual moments is above 18 years old. Any person or company presented are fictional. Title: "Girly Thoughts" Sun shined across my bedroom. The last thing I remember was Craig hugging me from behind and kissing my neck. Here I was, in my bedroom with a stranger I just...

Julie and Her Family Ch. 12

by Pretty_Sissy_Julie on May 4, 2020
Transgender & Crossdressers

My sister Becca and I were cuddled together in our nightgowns. Becca is 21 and I am 18. Becca is a beautiful and dominating woman. My name is Julie; I am her submissive sissy "sister." I have been living as a woman for weeks now since my Mum and sis decided I would look better as a woman and not my former life as a very effeminate man. At this point it wou...

One Step Too Far Ch. 02

by LanaChu123 on Dec 3, 2019
Transgender & Crossdressers

I must have been standing there for awhile barefoot and terry-cloth robe with my eyes fixed on Alex and my mouth open. For some reason I was still on my toes even though Alex had let go of my chin. I lowered my feet and tried to say something but some feeling of fear and some feeling of being out of control confused me and I couldn't think of what to say. Ev...

Panty Boy Ch. 03

by AussieKev1 on Mar 17, 2020
Fetish

Author's note. As with all my stories, they are largely based on fact, with some embellishments to make them, hopefully, enjoyable reading. A very kind critic proposed that I had written myself into a corner in this series and I thank them for their constructive criticism, however when writing largely based on truth you are bound by that truth. Please...

Kathy and Manny

by BJB69 on Jul 6, 2020
Erotic Couplings

Manny was always a good looking kid. His Mother had named him Manuel, but his classmates dubbed him Manny in the first grade. His Mother was second generation Mexican and his Dad was second generation Guatemalan. He was just under six feet tall and weighed 184 pounds. He wasn't muscular in a weightlifter body style, but more of a swimmer or soccer player bod...

The Reunion Ch. 02: Thai Massage

by Valtikka on Jul 15, 2020
Anal

"Krissy! Long time no see! It's so good to see you. You look great girl!" As soon as I get out of the Uber, Micky comes walking to me with wide open arms and gives me a big hug. "Come let me help you with your bags. You're the first one to arrive so you have first pick on the rooms. The rest of the gang will arrive tomorrow." Instead of the overalls I'm use...

The Tales of Crissy the Sissy Ch. 03

by EPCene on Oct 19, 2020
Transgender & Crossdressers

Chapter 03 Chris rose from his bed. He could still taste his cum on his lips. His soiled satin panties lay on his cum stained pillow. He reached down and scratched himself. His fingers ran through his sticky pubic hair. He brought his hand back up and licked his fingers. A shiver ran through his body. 'I'm going to need another shower before I head out,' h...

Adam to Addi Ch. 03: Adam Shops

by Gabbi_Erato on Oct 5, 2020
Transgender & Crossdressers

Adam couldn't fall asleep, dressed as he was and his head swimming with thoughts, replaying what he thought he remembered his neighbors saying. Would he really continue this tomorrow? Would he buy panties just for himself to wear? And when, just while he was house sitting? Or maybe whenever he visited Maya and Sky's house: Maya had called him pet. Did she r...

From Sweetie to Slutty Ch. 03

by meddlesome on Sep 26, 2017
Group Sex

It was about 3pm when we finally got checked into the suite, which was beyond huge and way luxurious. It had like seven rooms. With all the sex I had on the way up, we decided that I would take a little break until after dinner. I felt fine, but we didn't want to risk me getting too sore considering all the cock I had taken and all the cock that I was about...

Orc Masters Ch. 05

by GoldenKitteh on Sep 12, 2017
Sci-Fi & Fantasy

DISCLAIMER: The stories in the "Celebrity" section of Literotica are all fictional parodies - none are true, nor are they approved of by the celebrities named in the stories. Authors write these fictitious stories about famous people for the same reason that Larry Flynt made fun of Jerry Falwell, because they can. The Supreme Court of the United States, the...