First Time Sissy Stories

351,143 results
Orientation
Length
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Infinite Scroll

Becca's New Experience

by WhO2 on Jul 4, 2018
First Time

Becca had been in the closet for over an hour. She had experienced more in that time than in any other year of her short life. Her head swirled with new concepts, questions, feelings, and uncertainties. But most of all, there was a new feeling deep inside her that would not go away. She looked out the small opening at Jenn and DJ. They were still naked; un...

A Penetrating Experience

by an235041 on Sep 1, 2017
Group Sex

The alarm clock showed a time of 11:38 p.m. as Wes turned out the lamp next to his bed. He and his wife Deborah had just finished making love, and she was already fast asleep, weary from the toils that come with being a secretary and a mother of three. He was bushed, too, from another day at the rat race that was sales. Still yet, Wes could not fall asleep...

After Hours Adventure

by sirhugs on Sep 16, 2017
First Time

She was reading by the soft glow of a lantern in the back corner of the Library, surrounded by stacks of books and papers in front of her. I suspect I've always had a " thing" for bookish schoolmarm sort of women. Well, I am a dusty academic type myself, although in my imagination , I'm like Indiana Jones- mild mannered professor , until called on for a gre...

Luanne Ch. 06

by maadmaax on Sep 15, 2017
First Time

It was a bit after ten when Luanne walked in. After she poured a cup of coffee she came over, put her arms around my neck, and we shared a morning kiss. I had noticed when she walked in that she was wearing one of her shifts and, as we kissed, I ran my hand up and down her back discovering that she was wearing nothing under it. When she pulled back I asked,...

Karen & Mitch's Story

by Oazeal on Sep 14, 2017
Group Sex

My wife Karen and I have been married 15 years and what was once an active sex life has, in recent years, taken a back seat to both our careers. We make up for it, however, by planing little romantic getaways as often as possible. During these trips we make up for lost time and missed passion. What is usually once a week becomes once an hour, if you know wha...

Rwanda Adventure

by tkoberon on Sep 17, 2017
Loving Wives

As I watched him manoeuvre in traffic, I could not help marvelling at how quickly this Kenyan had picked up things-our language, the layout of our city. He had learnt about my body's sexual responses so fast that he was soon touching me in ways my husband had never discovered in three years of marriage. Probably when I did not get pregnant soon enough he gav...

A Virgin Roughly Handled Ch. 01

by ArielRacine on Sep 13, 2017
First Time

All the characters who appear in this story are over 18. Sandy turned eighteen the month before she graduated from high school. Two months later she got caught sneaking on to Jim's computer. Jim is old enough to know exactly what he is doing. Enjoy! -Ariel Racine * I was surprised but I suppose I shouldn't have been. Sandy used the computer in the den to r...

The Sleeping Princess Ch. 06

by LaSalia on Sep 26, 2017
Sci-Fi & Fantasy

Jamie watched his wife as her tears finally began to ebb. The shaking didn't cease, however, even as she rose to sit, her fists gripping the quilt as though she would rend it in half. It was almost amusing to watch such a tiny woman in such a violent fury, but Jamie simply couldn't bring himself to feel any mirth. When her fingers finally relaxed and her pal...

Not Passing Go! Ch. 08

by Spencerfiction on Oct 14, 2017
Non-Erotic

Chapter 8: A new order "You could have been killed, Agnes." "Agnes is a dead woman." Agnes replied. "No, sweetheart, I told you I wouldn't kill you." "Danny, Agnes is already dead." I look at her. "You can't be dead. If we are talking, and if you're dead, then so'm I." "Hadn't you ever considered?" Agnes ended the conversation with a question that send...

Eustace Johnson's Private Secretary

by andtheend on Sep 19, 2017
Interracial Love

Susan's first job was working for a powerful, wealthy, albeit perverted, black man. Oblivious to the horde of Christmas shoppers in his store below and with the music of Nat King Cole's Chestnuts Roasting on an Open Fire playing so much like elevator Muzak in the background of his private office, Eustace Johnson, a big, black man, had enough of his new, whi...