Literotica Sis Costume Ass Big Dick Stories

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One Scary Good Night Ch. 02

by Themaskedman on Sep 15, 2017
Group Sex

Bang! Bang! Bang! I was jerked out of my sleep and I looked around the unfamiliar room. My eyes focused on the door where the banging was coming from. Then my attention was drawn to this naked, adorable, sexy woman in my arms with a Harley Quinn jester hat on. The banging was reviving her and she started to unwrap herself out of my arms. Then the memories o...

Marilyn's a Working Girl

by BrettLynn on Sep 16, 2017
Transsexuals & Crossdressers

"Hey there, college man!" "Shari!" Marilyn screamed at a whisper before pulling her sister in her room and shutting the door behind them. "People in here don't know about my, um, secret. Gimme some time to let people know!" "OK, OK. I get your point. But you are a college MAN, right?" Shari replied, emphasizing her point by grabbing her sister's crotch and...

Sissy Son Taken to Costume Party

by JD2100 on Sep 26, 2017
Transsexuals & Crossdressers

I was making my way to my moms and dads house to house sit for them as they were going to a party that night and I had agreed to be there to watch the house and hand out candy. I was going to be alone in the house. I loved being all alone as it gave me a chance to partake in my fetish of dressing up in girls clothes. My sister still lived there and she had s...

Angel & Naughty: The Hotel Ch. 03

by Steven_Dessmir on Sep 12, 2017
Group Sex

Angel & Naughty: The Millennium Hotel Lisa lifted the phone. "Hi honey," she said. She held a hand over the receiver. "You have to be quiet baby. It's Todd." "Oh shit," Loretta said. My lips curled in devious delight. "You know what I want?" Lisa shivered. "Ohhh, I have an idea." "What?" Loretta asked. "What's she gonna do?" I petted Loretta's head. "...

Blackmailed

by cdsissybambi69 on Sep 18, 2017
Transsexuals & Crossdressers

My name is Jonathan. I am by all means your average 18 year old kid. I get pretty decent grades, I am on the school soccer team, and I just got a new car for my birthday. Things were great until that one day that would change my life forever. Being a normal 18 year old boy, I did what every single kid my age does: masturbate. I typically did this every day...

Jake's senior year in highschool.

by Tinylittlecocked on Apr 29, 2025

Jake was 18 going into his senior year of highschool. He is one of the most popular guys in highschool. However he is a bully. Jake liked to make fun of or play jokes/pranks on others to humiliate them. Although a lot of people fear Jake pulling a prank on them, they all love hanging out with them. Even thought everyone was afraid of Jake Playing a joke or p...

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Halloween Celebration

by Son_of_Hat on Sep 12, 2017
Group Sex

Hello, my name is Dan. Last year, my wife Kelli & I decided to throw a Halloween costume party with some friends of ours. A lot of preparation was put into both the party as well as in deciding on our costumes. I put together a great Scottish highlander outfit, complete with a kilt. Kelli went with the traditional "sexy cat" outfit that was comprised of cat...

The Fairy Ring Ch. 02

by dowd_elwood_p on Dec 2, 2019
Sci-Fi & Fantasy

This story depicts incest, non-consensual sex, and abuse of authority as part of a fantasy tale, but it does not promote or endorse these behaviours in real life. All characters are the age of consent or older for their species. As the story makes references to plot and character elements from earlier chapters, reading the story from the beginning is recom...

A Treat for a Trick

by BookWurm on Sep 17, 2017
Mature

Ted was in a rush to get back to the apartment and get out of there before Greg got home. He should have taken his time. Greg was there waiting for him. "Trying to get out of the bet, Ted?" Greg taunted. "Of course not," Ted lied. The bet was one of those stupid things the two of them (along with several of their friends) were always setting up. Althou...

Halloween Surprise

by Darrin And Beth on Sep 13, 2017
BDSM

"You've got mail." That's the message the subbies see. Knowing it could be orders they open it right away. Four subs, four different computers but the same invitation. Message reads, "Please Come! Its Halloween Costume Party! You MUST be here at 8:00pm sharp! DON'T BE LATE!" The only differences were in the sender. lil'tude and Dara received their invites (...