My First Time Stories

356,662 results
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Length
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Infinite Scroll

First, First Times

by LitEroCat on Sep 14, 2017
First Time

[This tale spans exhibitionist, First Time, Group and perhaps a little anal wrapped in a surprise.] "Are we drunk enough to play Tooth or There?" spouted Caroline. Apparently SHE was. "I think we need one more frosty pitcher before I am. THEN I'm willing." volunteered my always eager wife, Sue. All but Caroline and her new husband, Chuck, had been to our h...

Never Have I Ever

by CaffeineFetish on Sep 16, 2017
First Time

Going out to lunch with an ex has historically been a very surreal experience. Do you shake hands or hug? God forbid you both do the opposite of the other and conduct a weird desynchronized dance of handshake half hug. Callie and I ended on good enough of terms, so we hug and sit across from each other, some slight awkwardness due to her half leaning in for...

A Year Of First Times Ch. 02

by Theeeeee1 on Sep 14, 2017
First Time

Over the next few weeks, Torrie and I talked on the telephone nearly every day and we dated every Wednesday, Friday and Sunday evening. Not only did our personal dating relationship deepen during this time but our level of physical intimacy deepened as well. Before I go any further, let me tell you more about Torrie. She was an 18 year-old beauty with lon...

His Sissy Bitch Ch. 06

by keptsissy on Sep 18, 2017
Transsexuals & Crossdressers

I think about it all the way home, makes me so hot I want to masturbate right there in the back seat of the cab. I can feel the wet spot on the end of my little thing, feel it against my inner thighs, feel my small baby like penis slide around tucked up under my butt, pushed down and held between my legs as we ride toward my house. I try to keep my penis tuc...

Nora Ch. 06

by YoBiteMe on Sep 14, 2017
Fetish

Joshua and I sat and looked on as our wives began to disrobe for their rematch. Our two oldest were at a homeschool sleepover leaving us at home with just our youngest. From the moment our visitors arrived Ruth and Nora had been literally butting chests. They had been fully clothed, but the aggression and competition between the two was palpable. Nora had gr...

First Timers

by LaceyDresser on Jul 31, 2019
Mature

Prologue: The following narrative is an event that took place several years ago. I mostly forgotten about it, at least as far as retelling it, until more recent events prompted me to. Unfortunately it's a long story with an introduction that is particularly long. But it couldn't be helped as it was necessary to put everything into proper context and perspec...

Jenny's Journey Pt. 01

by Nikkiejanes on Jul 11, 2018
First Time

Authors Note:- This story is set and written in England and English spellings and terms are used throughout, Please bear this in mind when reading. ***** What have I gotten myself into? I am an eighteen-year-old shy, modest, virgin, first-year university student whose total sexual experience to date is having given three hand jobs and had my boobs felt up...

First Time for Everything

by walterio on Dec 11, 2017
First Time

PRELUDE "Let's not take out bathing suits off all the way in case somebody comes along. That way we can pull them up quickly." Those were the words that Marilynn whispered when we were standing under the railroad trestle. We had walked the mile from the community swimming pool to this discreet location. At the pool Marilyn had offered to strip for me and I...

Olivia's First Time

by BV_Quinn on Mar 30, 2020
First Time

This is the second installment (on Lit) of Overlapping Circles. OC follows the lives of four fictional characters via their journal entries. I write for fun. There are probably mistakes that make my English teachers wonder if I ever showed up for class but, whatever. - Olivia: 28-October-1989 I met a guy at a frat party and had sex for the first time! It...

I am a cocksucker, a bi cocksucker.

by Willingtobebi on Aug 20, 2019
First Time

I am a cocksucker. I discovered I am a cocksucker in my first threesome with a lovely, very hot, couple. My lust for cock confirmed. I am a bi cocksucker. I discovered that too, with certainty, in my first threesome. They are a lovely and very hot couple. It started online. He described himself as bi and he has a nice cock. She and I video chatted the mo...