Literotica Naive Boyfriend Stories

1,000 results
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Infinite Scroll

My Naive Boyfriend Ch. 01

by CraptainPlanet on Sep 11, 2017
Exhibitionist & Voyeur

The trouble with my boyfriend started over the summer. His name is David (I'm Natalie), and while I love him to death, he's always been a bit thick and naive. He has a habit of turning everything into a joke, which is hilarious when it's appropriate. But he has a hard time telling when things should be taken seriously. I had tried for months to get him to ma...

My Naive Boyfriend Ch. 02

by CraptainPlanet on Sep 11, 2017
Exhibitionist & Voyeur

It was a few months before I had any more trouble with Clara. Well, I was pretty sure she and David were still sending nude pics to each other regularly. He'd changed his phone notifications so that picture previews would no longer appear, so I wasn't sure exactly what they were texting each other. But they were texting each other quite a lot. I figured if i...

My Naive Fiancé at the Japanese Spa

by CraptainPlanet on Aug 21, 2018
Exhibitionist & Voyeur

This story is part of my My Naive Boyfriend series, though it's meant to stand alone. If you haven't read the other two, no worries, I've written this to be understood either way. Also, it's divided into three distinct chunks, in case it's too long for you to want to read at once. Sidenote: most of what I know about Japanese onsens comes from watching (untr...

My Naive Fiancé Goes to Prom

by CraptainPlanet on Mar 2, 2020
Exhibitionist & Voyeur

This story is part of my Naive Boyfriend/Fiance series, but works as a standalone. You can read it without having read the others. I could have submitted this story in a number of different categories, but I went with this one because the main character experiences it second-hand or as a voyeur. The story's themes also include cheating, exhibitionism, group...

Our Little Secret Ch. 05

by Midfielder86 on Aug 31, 2017
Group Sex

The SUV pulled into a nondescript business park outside of Vegas. The sun had begun to set, but the weather was still warm – mid-80s, warmer than we were used to for this time of year. The plans had changed slightly as we headed over on this Sunday evening, still a bit jet-lagged from the flight. Maria had managed to keep herself looking fresh with a brief...

The Perils of Rock n Roll Decadence

by The_shadow_rising on Nov 19, 2018
Erotic Couplings

The Perils of Rock n' Roll Decadence (SU Rules! No. 22) By The_Shadow_Rising ==DISCLAIMER== This story: is very long, and very slow. includes repetition (intentionally). has a lot of build up before the sex. is very detailed (including the sex). is not a quick jerk off story. Everything is long and detailed and meant to be rea...

Girl's Night Out

by In_Lust_We_Trust on Jul 28, 2020
Erotic Couplings

This smutty story focuses on the theme of cheating and unfaithfulness, which can entail a myriad of details and fetishes including, but not limited to, lust-based attraction, illicit acts, feelings of dominance and superiority, betrayal, corruption, humiliation, as well as thrills of a cuckold/cuckquean. If such things are not to your liking then please do...

A Tempting Vacation Ch. 15

by JackKing on Sep 26, 2017
Exhibitionist & Voyeur

I want to give you fair warning. The following is a short chapter, designed to transition Pam back on the island and firmly re-establish each characters attitude and intentions going forward. Not much sex here!...sorry. At the end, I will ask you as the reader for some feedback for a direction of the next chapter. I just haven't quite settled on how I want t...

Rin

by Global Carol on Jul 3, 2018
Mature

As much as possible, I'd worked to forget the past. And so for the last several years I'd been trying to live my life in the now. Unfortunately, it was not much of a life. I'd become mostly an island. I'd become self-contained. I reached out to others as infrequently as I needed to. I viewed change as my enemy. Ian Fleming wrote: "Once is happenstance. Twic...

Because I Care

by MrPezman on Sep 12, 2017
First Time

"David Funicelli! What did you just call me?" Miss Hatch stood, her small hands fisted at her sides, the color high on the otherwise light-olive complexion of her face as she stood at the front of the class trying to teach Literature to her seventh period full of teenagers that, for the most part, didn't want to be there, didn't give a shit about the materia...