“A Complicated Affair” (7,500+ Words) [Anal, Cheating, Cuckold & D/s]

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**A COMPLICATED AFFAIR: VOLUME ONE**

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**| Table of Contents:**

> * *Plot Summary*

> * *Introduction*

> * **One:** *’as_requested.jpg’*

> * **Two:** *’An Aversion to Small Talk’*

> * **Three:** *’Susan’s Only Rule’*

> * **Four:** *’Quasi-Religious Encounters’*

> * **Five:** *’Removing the Safety Seal’*

> * **Six:** *’Loophole’*

> * **Seven:** *’Second Virginity’*

> * **Eight:** *’Instant Replay’*

> * **Nine:** *’The Close Call’*

> * **Ten:** *’Bottled & Corked’*

> * **Eleven:** *’Developing a New Routine’*

> * **Twelve:** *’Unpleasant Formalities’*

> * **Thirteen:** *’The Incident’*

> * **Fourteen:** *’Confession(s)’*

> * **Fifteen:** *’An Alarming Blur of Events’*

> * *Afterword*

> * *Uncensored Story Tags*

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**| Plot Summary:**

A young man’s affair with a middle-aged hairdresser is complicated, after her husband learns of his wife’s severe betrayal.

Expect a story with a strong sense of acceleration and consequence, sustained across multiple chapters. There’s a handful of twists that you — *hopefully* — won’t see coming…

***

**| Introduction:**

“A Complicated Affair” (7,500+ Words) [Anal, Cheating, Cuckold & D/s]

***

***

**A COMPLICATED AFFAIR: VOLUME ONE**

***

***

**| Table of Contents:**

> * *Plot Summary*

> * *Introduction*

> * **One:** *’as_requested.jpg’*

> * **Two:** *’An Aversion to Small Talk’*

> * **Three:** *’Susan’s Only Rule’*

> * **Four:** *’Quasi-Religious Encounters’*

> * **Five:** *’Removing the Safety Seal’*

> * **Six:** *’Loophole’*

> * **Seven:** *’Second Virginity’*

> * **Eight:** *’Instant Replay’*

> * **Nine:** *’The Close Call’*

> * **Ten:** *’Bottled & Corked’*

> * **Eleven:** *’Developing a New Routine’*

> * **Twelve:** *’Unpleasant Formalities’*

> * **Thirteen:** *’The Incident’*

> * **Fourteen:** *’Confession(s)’*

> * **Fifteen:** *’An Alarming Blur of Events’*

> * *Afterword*

> * *Uncensored Story Tags*

***

**| Plot Summary:**

A young man’s affair with a middle-aged hairdresser is complicated, after her husband learns of his wife’s severe betrayal.

Expect a story with a strong sense of acceleration and consequence, sustained across multiple chapters. There’s a handful of twists that you — *hopefully* — won’t see coming…

***

**| Introduction:**

My Date with the Doll – BDSM – [Mf]

Niral was a young Indian girl I had met through friends whom I was only able to play with a few times. Her fetish was in objectification. Literally being made into things that were not exactly human or living. She loved the sorts of porn that featured women used as furniture or mindless sex toys.

Dear reader. You will note that we did a bad job being safe in this story. Primarily in that at a point she was totally unable to safeword or safe-signal. I’d recommend, if you try something like this, that the sub in question has something hand held that they can hit to notify you that they need help.

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She was pretty and tiny. One of those women that you worry you might break during sexual play. One of those women whom as you fucked, you worried, how does she have room?

I tend to prefer my women curvy, but there was something fun about how small she was. An aspect she liked to include in her play as a thing.

The suitcase itself was huge. It was her overseas bag, for traveling back and forth across the ocean to visit relatives and as such it was much bigger than it needed to be and quite sturdy.

My secret crush… [M] 4 [F] [MAST]

Every afternoon I see you walking past me in the hall way after 4th period. You probably never notice, and why would you. I don’t stand out any noticeable way, never bothered to try out for any sports teams, I’m not the member of any after school clubs. I’m a social ghost who walks from class to class alone, but dreaming of you.

Brother and Sister Roleplay

I created this the other day thinking about if I had a sister. Sadly I only have brothers, I think the taboo is beyond hot! If you like it I have the other half of the story that I would love to pass on to you. Anyways, take a read:

Being home blew. So. Fucking. Hard.

Okay, I couldn’t blame my parents, honestly, they helped put me through college and in the process lost their gorgeous, three bedroom, three story country house and now live in a slummy two bedroom house in town. Since my sister is just now in her senior year of high school she still lives at home, so she’s afforded the second bedroom as my parents have the other.
Which means I’m relegated to the living room couch. Which, again, isn’t terrible, and most of this is the thesis of a first world problem, but sometimes I hate the loss of privacy.

In the old home during my late, sleepless nights I’d splay out on my king sized bed, basking in the light of my laptop screen with my basement bedroom door closed, away from everyone, fervently jacking off to whatever erotic videos I could find on the internet. Sometimes I’d even get daring and hope on cam and let some lucky lady see my youthful stomach clench up as I softly moan and spray cum all over my happy trail, and chest.

Brother and Sister roleplay

I created this the other day thinking about if I had a sister. Sadly I only have brothers, I think the taboo is beyond hot! If you like it I have the other half of the story that I would love to pass on to you. Anyways, take a read:

Being home blew. So. Fucking. Hard.

Okay, I couldn’t blame my parents, honestly, they helped put me through college and in the process lost their gorgeous, three bedroom, three story country house and now live in a slummy two bedroom house in town. Since my sister is just now in her senior year of high school she still lives at home, so she’s afforded the second bedroom as my parents have the other.

Which means I’m relegated to the living room couch. Which, again, isn’t terrible, and most of this is the thesis of a first world problem, but sometimes I hate the loss of privacy.

In the old home during my late, sleepless nights I’d splay out on my king sized bed, basking in the light of my laptop screen with my basement bedroom door closed, away from everyone, fervently jacking off to whatever erotic videos I could find on the internet. Sometimes I’d even get daring and hope on cam and let some lucky lady see my youthful stomach clench up as I softly moan and spray cum all over my happy trail, and chest.

[MF] That one time I jerked a pervert’s huge cock on the train.

My description:

>I know you perverts (I’m one too, no judgment) are wondering.. so here’s me: I’m not “hot”, or at least I don’t think so. Dudes have told me I’m pretty, girls I’ve been friends with (and those I have been more than friends with) have told me that I have unfair eyes. I’m heavy for my height – probably 10-15 lbs. overweight. I’m pretty lazy about it, because I can be. I have had standard-deviation-breaking bras since 13; getting guys in bed hasn’t been hard except times when I get picky. Hips are clearly meant for baby making.. thanks, Mom.

I was taking a train from one coast of the USA to the other one spring. It was just something I always wanted to do, and I had booked the ticket with my ex. We had a destination in mind, but we hadn’t planned anything when we got there. I had a friend to meet, and another one of my exes lived in my destination city. So when my ex and I broke up a couple of weeks before the trip, traveling by myself was the obvious course of action. It was a little bit of a bummer, though, as I was hoping to cross “get fucked on a train” off my bucket list. The trip was gorgeous, and I can’t recommend it enough. I even got a big surprise amenity about halfway through the trip.

Married co-worker [F] and the young man [M]: an affair (LONG)

Everything I’ve written previously has been about my collegiate experiences–my first time with an older woman ([1](https://www.reddit.com/r/gonewildstories/comments/598ol8/late_40s_f_and_the_college_boy_m_a_first_for_both/), [2](https://www.reddit.com/r/gonewildstories/comments/59xwkg/late_40s_f_and_the_college_boy_m_a_first_for_both/)) and about [an experience with an ex girlfriend, where I gave her an orgasm in front of her dad without him realizing](https://www.reddit.com/r/gonewildstories/comments/5aykbh/orgasm_in_front_of_girlfriends_unknowing_dadmf/) (most of the commenters believe he knew–but I still naively don’t think so!). I have to confess the following experience does come with a little bit of guilt because she was married (it’s so weird how the married also makes it exponentially sexier, which she did specifically mentioned quite a few times). Our first interaction was last March and we decided to chill out recently.

As a reminder, I was a tall, gawky kid growing up, with glasses and an overbite. Then I wrestled throughout high school, got contacts, and dental work fixed my alignment to where I’m actually a pretty good looking guy (I’m told I look like the senior in Sixteen Candles), but I still have the perception of myself as a gawky kid with glasses and can still be somewhat shy until engaged, and alternate between overconfidence and no confidence.

[mf] reddit gives me my first on-line submissive PART 2 HER SIDE continued

FRIDAY: While I was at work and sitting at my desk, I knew I needed to climax, and I was determined to do what it took to make that happen. I messaged back and forth and was finally sent a set of instructions late in the day that were mind blowing. I almost came when I read them, and I was at work!!! I had some things to do and I have never had this much anticipation in my life. It was like Christmas day, my birthday and hitting the lottery all in one. I was so wet……. During the conversation, he told me that I was to think about all the things I was being MADE to do. My pussy was pulsing as I read his messages and it was torture to have to wait until I could go home.

After what seemed like a week, I finally made it home that night, I reread the instructions and just couldn’t wait any longer. That night I had to wear panties with my garter belt so I put on a matching thong. I “presented” myself as I did the other nights, on all fours, head down legs spread wide. I spanked myself on my left cheek first and counted 1. I repeated it, a little harder this time, and said 2. I continued this until I got to 5 and smacked my ass as hard as I could. I repeated this on my right cheek.