‘A Complicated Affair: Redux’ [mF, Anal, Cheating, Cuckold & D/s] (7,500+ Words)

***

***

**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:**

[MF] Her mom asked for it.

It was going to be a very good night. My girlfriend Lisa was out of town, with her grandmother, and her mother, Lynne, had asked me to come over, to keep her company.

It wasn’t long before Lynne had confessed that she wanted to be used rough, the way she’d seen me take her daughter. It was a dark and rainy night, she was in a see-through nightgown with a frilly bra and panties, and she’d been clinging to me every time the thunder crashed. What would you have done?

We were in the afterglow of her “violation.” She was breathing heavily under me, naked and glistening with the sweat of our violent first sex, and I was holding her down by her hair, looking down into her wide eyes.

It was going to be a few minutes before I could perform again… but not THAT many minutes. It was good to be young and horny all the time, sometimes. I was going to have to find something to do to pass the time while I recovered… it was just going to take a little imagination.

Let’s choose our own adventure. [MF]

I’ve been a little slutty lately.

Sorry if that led you on, I’m a dude. But I’ve been promiscuous lately so I’d like to describe a few of my most interesting hookups. If anyone’s interested in hearing more, PM your vote and I’ll write the idea for the most popular story.

1) **My older neighbor.** My nextdoor neighbor just happens to be an incredible woman in her early forties with a great sense of humor and a marvelous ass. [Mature] [Anal]

2) **The One Nightstand** I was on Tinder one night when this cute redhead messaged me at about 11:00PM, asking me to come to her hotel room. After making sure she wasn’t catfishing me, I went over to fuck her tight pussy. [Cock-choking] [Hotel Hookup]

3) **The College Slut.** For a while, I Snapchatted this adorable college girl. She was innocent on the exterior but so incredibly slutty underneath the surface. She was inexperienced and really nervous at first, so I made sure she was comfortable. Then we had an incredibly good afternoon. [Cock-swallowing] [BBW]

MILF Wife: Mrs. Anal’s Wedding [mF, anal, oral]

(The following takes place a month after the first “MILF Wife” story. The story has now changed to third-person omniscient)

Mrs. Anal had been living with Hubby after divorcing her husband. “After a month of abstaining, it’s finally time for your MILF initiation”, he told Mrs. Anal. She had signed the contract agreeing to be his MILF wife and all that was left was for her to follow through on her fulfillments.

“Fucking finally”, she said back. “What do I need to do”? “Get your old wedding dress for starters”, Hubby told her. “I don’t care if it doesn’t fit, your massive titties and ass will look super sexy regardless. I’m going to take you somewhere special and use every single one of your holes to christen our marriage.”

A day or two later, Hubby and Mrs. Anal went to the woods at night. They went in pretty deep to assure that they wouldn’t be disturbed. Hubby set up a lone couch in the middle of a clearing. Mrs. Anal and him got out of the truck and she went to change behind a tree. After a while, she emerged from behind him.

Traded [mf]

Part of being a sub and freeuse is to do what you’re told. Don’t question, just be a good girl. I always try to remember that.

Monday morning, daddy and I did our normal routine and when he left, he said my friend (poker buddy) would be by for some fun. This made me excited. I like the poker buddy more than daddy at times.

Later when he got there, I open the door to let him in but he doesn’t want to stay. He gives me some gym shorts and a shirt and tells me to get dressed. Daddy already gave him a bag of my stuff, I was moving out but didn’t know it yet.

We get in his car and I try to figure out what’s going on. He asks me how much of a sub I am. I told him I do whatever is needed to keep my master happy. He calls daddy on the phone in the car so I can hear. When he picks up, daddy asks if he (poker friend) has me. He tells me yes and daddy tells me I’m moving in with him and no questions. Then he hangs up the phone.

[MF] u/Shibarbie and u/Kenbaku FINALLY get some dirty alone time!

Oh ho ho! So, this is a little late in the posting because life gets in the way of these things. Plus, I had to do a little busywork with some of the photos, owing to the fact that neither of us can really get “busted” right now.

So, u/Kenbaku and I have been seeing each other for 4 months and as you can probably gather by our handles (does anyone use that word anymore?!) we are pretty into the BDSM/shibari/well… anything goes really. This isn’t a post to wax lyrical as to who we are or what we ain’t. We just wanted to share some photos from the other week when we fiiiiiinally got to spend the whole night together. We’ve only managed this once before, so as you can probably imagine, we had a lot of things we wanted and NEEDED to that night.

So, after managing to swing clearance to stay out all night by our SOs, we rented a room in a local hotel and planned to fuck each other senseless. I’d say we did a reasonably good job, but there’s always room for improvement ;-)

I met a guy from Craigslist. [FM]

I’ve browsed the Craigslist casual encounters before. But I’ve never actually met up with someone…until now. I saw his post last night: in town for one night, 8 inch cock. I was mesmerized by the pictures of his dick. So I sent him a message last night. We agreed to meet up early this morning. I had a hell of a time getting to sleep, nerves and excitement.

When my alarm went off this morning, I had a message waiting for me from him asking if I still wanted to come. I told him I was getting dressed and then coming over. At the last second he sent me one last message: “no panties”

On the drive there, I was nervous but I could also tell I was soaking through my jeans. He was waiting for me outside when I pulled up. He is very attractive. On the shorter side, which I like. A few days scruff on his face, very short hair. We had a cigarette and chatted for a minute, but we were both ready to get up to his hotel room.

21 [MF] – My Hot Girlfriend

I’m looking for someone who likes to write a story about me and my hot GF’s journeys. We answer all of your questions and show you what you want in exchange of your stories. We don’t like to share however my girlfriend has the fantasy of watching me fuck another girl in presence. We love showing off, fuck in public, on our balcony for example. I love knowing people fantasizing about her and jerk off to her or girls getting wet by her. We love rough sex, anal, hair pulling, foot fetish, short skirts and stockings, facial cumshot etc. So if you’re down for it, hit me up.

[MF] Unexpected anal with my fiance

It all started with some frisky slapping while we were in bed. He had taken a nap because he had morning classes and the day off. I could hardly fall asleep with him since I had just woken up so I just stayed up looking at vacation things since we are planning our 10 year anniversary trip to Hawaii.
When he woke up we hugged and talked for what seemed like hours. We always have great conversations and this morning was no exception. I wasn’t wearing a shirt and he went on to flick my already hard nipples. Then I slapped him and he slapped me back. I love it when he slaps me across the face. It always takes my breath away when he does it. Then I just suddenly turned around so he could see my plump ass. He started spanking me. He was spanking me as hard as possible on both cheeks and I moaned with pleasure each time. He grabbed me and covered my mouth and continued spanking me until my cheeks were sore. Then he pushed me against his hard dick. I always loved his dick. Its perfect. It has a freckle right below the head that I love thrusting deep into my throat. I love gagging on his dick. I don’t know how to describe the position we were in but I’ll try. I was laying down on my stomach with one leg tucked under his thigh and the other leg resting on the mattress. I know he loves fucking me like this. He could feel how wet I was through my cute cheeky underwear so he pulled then down and went to town pounding me hard into the bed. It felt so amazing to have his body on top of mine. I wanted him to slap my ass some more so I reached out and opened up my butt cheeks so he could get a clear view of my asshole. When I did that he got back and started fingering my ass. Fuck that felt so good I was moaning in pleasure. I was lost at how amazing he is at fucking me. I reached over to my drawer and grabbed the lube while he was stroking himself looking at my round ass. I knew what he wanted to do so I let him. This isn’t our first time doing anal but it was the first time he asked for it. He bent down and spit on my ass and kissed it with gentle flicks of his tongue. I was in heaven. Fuck he was always so good at making me feel good. You could tell he loved me by the way he touched me. It started gently, he put his thick head in my ass and I moaned. Yes I want more. Please put it all in. He started slowing pumping into my ass at such a pleasureable rhythm and I was meeting him at every stroke. Please don’t stop, it feels so good to be connected like this. My pussy is so wet it’s dripping onto the bed. I feel my juices going down my thigh and falling onto our sheets. I’m so turned on by pleasing you. I worship the ground you walk on. I feel you start to pulse and I know what’s about to happen, I feel you thrust into me with force and I moan because your dick feels so good inside me. We went into the shower and bathed eachother. I love feeling your expert hands all over my body gliding with that knowing ease that my body was meant for you to touch it and to hold it. We went about our day and every time I clenched my ass I could feel that little bit of pain. That little bit of pain has kept me wet all day. Can’t wait to start sucking your dick in a little bit. I want it all the way down my throat. I’m dripping now. Come and feel me.

[MF] Fulfilling her rape fantasy

(**Disclosure:** We had arranged this night ahead of time, so she knew it would be me. We had a safe word in place, as well as a list of strict “don’ts”. This had been discussed for weeks ahead of time, as I was very unsure of it, but she insisted… and then let me do anal for the first time, as a thank-you.)

I sat in my car, watching her bring in groceries. It was a warm evening, and she left the front door open, allowing the air to flow through the screen door.

She was wearing maroon scrubs, and I started getting hard thinking about what color her bra and panties looked like underneath. Maybe the warm weather and long day made a wet spot in her crotch.

The light went on in her bedroom window, and then the bathroom window next to it. I turned off my car and walked across the parking lot, into her condo, and closed the door behind me. As I slowly climbed the stairs, I heard the shower running.