First Time Sissy Stories

351,143 results
Orientation
Length
Source
Infinite Scroll

While The Wife's Away

by SingerBabe on Sep 17, 2017
Loving Wives

Don't get me wrong. I don't want you to read this thinking I go cheating on my husband every time his back's turned. What happened between Phil and I last month was the first time I'd been with a man other than Kyle since we'd been married five years ago. It's not - as you're thinking - that Kyle is a bad lover. He's great in bed. He pleases me whenever I wa...

Father Daughter Swap Club Ch. 02

by amyhboo on Jun 9, 2020
Erotic Couplings

First of all, despite the title this story will not contain any incest. All characters are 18 and over. Please read chapter 1 first as it contains all of the scene setting and world building- I don't really want to repeat myself so will somewhat rely on you remembering what Sarah and Richard look like and what the club is all about. Just a quick recap on the...

First Time Pet

by littlemissnaughtygal on Sep 17, 2017
BDSM

"Be upon my doorstep completely naked on hands and a knee at Two O'clock sharp is that understood?" was the first thing said upon my ears as she answered the phone. "Yes Ma'am" I replied with a tremble in my voice. "Are you nervous my pet?" For a moment I sat in silence. I didn't want her to know that I was infact nervous yet excited at the same time. "I a...

My First Blow Job

by acuriousguy2 on Aug 18, 2017
First Time

My first blow job.... I don't know when I first became curious but knew I was for quite some time. I think it had to do with the enormous amount of pleasure it brought to me and seemed like such a cool thing to do, I wondered why women didn't seem to like it. I was always fascinated with porn. The sight of a woman's breasts sent me and I used to sneak my bro...

Satisfied With Love Ch. 12

by MDSW on Sep 14, 2020
Romance

Author's Notes: Keep the comments coming. I read each one. I do hope you are enjoying the novel. MDSW ******** Brad appears to be better now and he is looking forward to working a full schedule throughout the training, even though Kristi is still nervous about it. Terry has no problems with it so Kristi relents as Brad accuses her of being over protective...

The Turning Pt. 06

by LiteroticaScribe on Nov 20, 2018
Loving Wives

The next morning, I woke to the covers being pulled back and my beautiful wife's hand stroking up and down my hard cock using cock lube. She was just jacking me with her head on my chest, watching her hand move up and down in a smooth stroking motion. "Good morning baby." She said, seeing me awake. "Well, what have we here?" I asked. "I just wanted someth...

Finding my Place Ch. 03

by Lost_Yonder on Sep 17, 2017
Mature

I never had much of a conversation with Mr. Alexander before, but when he was paying me for babysitting Melissa over New Year's eve, he gave me a good ole male pat on the back, congratulating me and telling me what a wonderful girl Katie was, while she and Mrs. Alexander, Olivia, were in the kitchen chatting. He had a big smile on his face, welcoming me into...

Steak and Blowjob Day Ch. 01

by Shavvy3100 on Sep 25, 2017
BDSM

I'm still looking for a volunteer to review and edit my stories before they get posted here on literotica. I'm not a native English writer and my writing experience is also limited. If you feel you can improve my writing skills, eliminate typos, awkward wording, grammar mistakes... please send me a message. Advantage for you would be that: - you'll be able...

In the Back Row

by kinky shy girl on Sep 12, 2017
Exhibitionist & Voyeur

Alan agreed to meet me at a coffeeshop first. Neither of us was new to the online hook-up scene, so meeting in a public place was the natural first step. I was a little nervous, but I think that's normal. We had exchanged photos, and I knew the attraction was mutual. Our phone conversations had worked for the both of us, so meeting in person was long overdue...

The First Time

by warotto on Jul 15, 2020
Group Sex

It was Saturday, and we were having a get together that night. Good friends, a cookout, fire pit going after dark. Everyone brought a little alcohol to share-not because we needed it to relax and have fun, but to help defray the costs a little bit. The first to arrive was Tina. She had become a regular on our Saturday night ventures as her husband was a mu...