Sissy First Stories

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The Scientific Method

by NerdySex on Apr 10, 2019
First Time

My first fuck was a disaster. I had several dates with this girl, the first two very platonic. The third we did some deep kissing and rubbing. The fourth, she fondled my cock and I rubbed her pussy. The fifth date we did the deed. It was my first time and might have been her first, not sure, but in any event she was inexperienced. I certainly was. I kissed...

Samantha Gains Experience Ch. 01

by inexperiencedsam on Sep 17, 2017
Erotic Couplings

My names Samantha but my friends call me Sammy or Sam and I'm a nineteen year old university student. I want to recount an experience I had a few weeks ago. I was on a placement for my course and was staying with my godmother Liz and her partner Dan. Liz is thirty seven and Dan's a little older at forty six. I was very lucky in finding a placement so close t...

Restoring the Castle Ch. 02

by olivias on Sep 15, 2017
Romance

She had just cleared past the grape vines of the Mountain Castle winery and knew she was back on her mother's land for the first time in nearly seven years. Ally stopped on the side of the narrow, winding, graveled road up into the mountains in a fold between the southern slope of Mount Marshall and a shorter mountain called The Peak, northwest of the small...

What Ever Lola Wants...

by Moon Glade on Sep 1, 2017
Group Sex

This is my account of how the woman who became my wife and I got back together after a separation of over ten years and how our relationship developed to the point of my proposing to her. I am writing my feelings on what happened to us and posting them on our friend Debre’s submissions to Literotica. I have not read Lola’s account of what happened (she won’t...

Getting Sofia

by SofiaMateo on Sep 16, 2017
Anal

Matt's trip to the States had been very successful. While he hated to be separated from Sofia for even a day, the trip had been unavoidable and Sofia would have been miserable had she accompanied him. With this latest business deal finalized, Matt expected be able to stay close to home for a while, close to the woman who had changed his life. As he lay in b...

Who's Who

by pantie_fan on Sep 12, 2017
Loving Wives

James and Claire had been happily married for over 10 years and still had a good sexual relationship - good, but nothing unusual. Despite having a relatively open relationship - including sharing some of their fantasies - with one another, they had never had anything other than a monogamous relationship. This, although they both admitted that - as a fantasy...

The Picnic Affair

by nudeausrunner on Jul 3, 2018
Erotic Couplings

I pull up in the car park. It's empty as hoped on this warm, sunny weekday. I have called in sick with work but my wife thinks I am still there. I am taking a big risk for hopefully a rather special sexually charged first encounter. An encounter with a special online friend, someone I have talked to but have only seen in photos. The photos though, wow, they...

Seduced and Hoodwinked Ch. 04

by walterio on Jan 7, 2018
Transsexuals & Crossdressers

SHOPPING, MASSAGES AND SEX On Tuesday morning Darin and the ladyboys passed on sex and after breakfast they went shopping. They picked up supplies first and then went to a boutique and picked up some new clothes and accessories. They stopped for lunch afterward and at the restaurant many eyes were on the three beauties. Darin was sure that people were wonde...

Jamaican Getaway Ch. 02

by Wahoo_1991 on Feb 5, 2018
Exhibitionist & Voyeur

This is the fourth in a series of stories that describe the few times my wife has uncharacteristically exposed herself in public. If you have read the previous three stories you might think she is a wanton exhibitionist, but it really is the furthest thing from the truth. In our day to day lives she goes out of her way to wear oversized clothes to disguise h...

Delayed Honeymoon Pt. 02

by SteveLee1146 on Sep 14, 2017
Erotic Couplings

I don't think that I moved the entire night. I had no dreams that I was aware of, there were no walls closing in on me – nothing! I was still lightly dozing when I felt a hand on my shoulder shaking me gently and heard Glenn's voice saying, "Wake up, Judy. You've got a tour to take." I sat up, half awake, as he went on, "Nick will be here and you'll still be...