Jennifer Virgin Stories

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Jennifer Monroe & the Ladies Ch. 01

by corduroysissy on Dec 31, 2017
Transsexuals & Crossdressers

Jennifer Monroe & the Ladies -- Chapter one Jennifer held Debbie's hand as she led him down the stairs and into the finished basement. It was a large single room with a sofa, a few comfy chairs and a queen-sized bed at the far end. Seated on the sofa and chairs were five ladies, all of them dressed in corduroy outfits. Jennifer ignored them as she whisk...

Breaking In Sweet Jennifer...

by alexcarr on Aug 18, 2017
First Time

When Jennifer came to me it was like a new life beginning. Sweet, sweet and innocent Jenifer who - at nineteen, had never had a boy friend straight from a convent. She wanted a room to set up her independence and to get settled in with her online university studies. The owner of a hotel which had been converted into bed sitting rooms I was delighted to gi...

Jennifer at St. Ciels Ch. 1

by anbk on Sep 12, 2017
Exhibitionist & Voyeur

Jennifer was both anxious and excited as she dressed for the first day of her senior year at St. Ciels. At eighteen Jennifer had matured into a very attractive young woman. She slowly pulled the shear black nylon stockings up over her long shapely legs, fumbling a bit with the garter snaps. She had never worn stockings before,but all senior girls were requir...

Making Friends at Lake Como Ch. 07

by flashgordon562006 on Sep 14, 2017
Erotic Couplings

Jennifer spent the rest of the night with us and the three of us took turns with her. In the morning, I asked Jennifer that if she was a virgin, how did she know so much about performing all the sex acts she performed. She said, blushingly, that she watches a lot of porn. Lisa asked her if she would want to get a lot of sex from men and women. I looked ove...

Her Special Gift: The Dress

by gedda98 on Sep 2, 2017
Erotic Couplings

It was casual day at the High School were Jennifer taught and she and a few other teachers decided to wear school uniforms for a twist. Roger noticed his wife wearing the light cotton summer dress the students normally wore as she left for work and thought it was cute, however in the busy morning rush of getting their two kids ready for school, it was soon f...

Her Special Gift: The Dress... (director's cut)

by gedda98 on Sep 14, 2017
Anal

Her Special Gift: The Dress... (director's cut) It was casual day at the High School were Jennifer taught and she and a few other teachers decided to wear school uniforms for a twist. Roger noticed his wife wearing the light cotton summer dress the students normally wore as she left for work and thought it was cute, however in the busy morning rush of getti...

Jennifer

by zaksx on Sep 13, 2017
Fetish

I met Jennifer at work. She is about 40, dark hair, buxom but shapely, very well dressed and confident. She has dark mysterious eyes and she seems very flirtatious. I'm just 19 and recently started, and although she's not in my department she is very senior in the company. We were talking at the coffee machine one day, and she asked me, "Hey John, how are y...

The Babysitter

by FGL on Sep 13, 2017
Erotic Couplings

The first time Jennifer came over, I thought nothing of it. I was eighteen, moving quickly towards independence, and frankly, not the least bit concerned that my parents didn't trust me enough to watch over my seven year old brother. I don't blame them, because aside from occasionally doing some homework, all I ever did was play video games, listen to heavy...

Jennifer at St. Ciels Ch. 6

by anbk on Sep 12, 2017
Exhibitionist & Voyeur

Jennifer sat dejectly in the cafeteria eating her breakfast. It had been a week since Prof. Gilbert had told her that he was going to recommend her for the Benefactor's Dinner, but as yet she had not heard if she was selected. All week she had played with herself, jerking off to the image of Mr. Lewis slowly fucking her in the ass. Even now, as she thought o...

The First for Diane, Jen & Kim

by MichaelLakeHoughton on Sep 12, 2017
Interracial Love

As Kim walked up to her parents house carrying her suitcase she again had a feeling of distance to the experience. She had moved out of the house a few months after her older sister Jennifer had, over a year ago and returning now seemed different. They each had lives of their own away from their parents. They lived in the same city about an hour away from w...