“A Complicated Affair” (7,500+ Words) [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…

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**| Introduction:**

Ex’s bubble butt baby sister. [Mf] [Anal] [Dirty talk]

First time posting here, and I got permission from my partner in DPP to post this on reddit general. The formatting is a role-play back and forth between the two of us, so it will change perspectives. Hopefully fiction isn’t frowned upon terribly.

The premise:
A man was just recently dumped, and the ex-girlfriend has sent her little sister to go pick up her things to avoid confrontation.

Part 1 – Will reply the rest in comments or a second post if people seem interested.
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Mia allowed herself into the couple’s home for at least an hour now. As soon as someone was to enter the front door, they would be greeted with the sight of suitcases, scattered clothes and boxes filled with her older sister’s belongings.

The brunette wasn’t too amused with having to go alone and pack up *all* of the sister’s belongings but someone had to do it. She was told the dumbass wouldn’t be home at this time anyway, so why not? If her sister wanted to move on from the jerk Mia couldn’t stand, she was more than happy to help her out.

Best commute EVER! [F] [public] [mast] [train]

Ladies, have you ever had one of those mornings? When every movement of the train on the tracks seems to resonate through your seat? When every vibration travels all the way up your spine, hitting all the right spots along the way? If you haven’t, I hope someday you get to experience it the way I did. Today was that day for me!

Maybe it was the way my thong moved when I shifted in my seat. Maybe it was because I feel so sexy in these soft black leggings. Maybe it had something to do with the gentleman seated directly across from me. Not one of the regulars on my train, not the standard khakis and golf shirts that I see every day. He was an older man (I’d guess late 40s), just a few specks of gray starting to appear in his short brown hair. Very distinguished looking, in a perfectly tailored blue suit. His name is David, according to the ID badge clipped to his belt. But when he answered his phone it was “Dave,” and he had a voice that would melt butter.

My boyfriend and his bud part 4 [MM]

[Part 3](https://www.reddit.com/r/gonewildstories/comments/5l73fq/my_boyfriend_and_his_bud_part_3_mm_masturbation/)

3 nights after their last session my bf and Pete went to their company Christmas party tonight and had a few drinks. After hanging out for a while Pete started asking about what I thought about the situation. When my bf asked what he meant Pete asked how far I’d let things go. My bf said he didn’t think I had a limit to how far I’d let things go between them (he’s right) and asked why.

Pete didn’t answer that but asked if he could see the video I made for him again (my bf didn’t give him a copy of it) my bf said sure soon as they left the party they could go back to our place. They hung out and mingled for another hour or two when Pete asked if he was ready to go. My bf said sure and they got an Uber home.

Soon as they got in the door they both started stripping and my bf linked his phone to the TV. He set my video to loop and they say down and stroked each other for a bit. Pete was moaning and telling my bf how much he loved hearing me moan his name, when his cock started throbbing in my bf’s hand. My bf said it felt like his cock was growing. Pete closed his eyes and told my bf to slow down.

My boyfriend and his bud part 3 [MM] [Masturbation]

[Part 2](https://www.reddit.com/r/gonewildstories/comments/5kpjzd/my_boyfriend_and_his_bud_part_2_mm_masturbation/)

A few days after the last meet up my bf decided he wanted Pete to know I was officially in on everything and that I loved them jerking off to my pics so he had me make a video for him. I made an almost 2 minute long video of me slowly fucking myself with a dildo and cumming while moaning Pete’s name. I hadn’t sent it to my bf cause I wanted them both to see it at the same time.

A few nights after that my bf text me that Pete had come over I told him where I had a flash drive hidden. It was full of pics I’d taken and the video. I told him to have fun and I wanted full details later. Around 2 am I got a call from my bf telling me every dirty detail!

My bf invited Pete over to hang and play video games as usual but decided to stay in just boxers just to make sure things were already relaxed. When Pete walked in he instantly grabbed my bf’s cock through his boxers and gave him a playful squeeze. Pete stripped to his boxers too and they got comfortable.

My boyfriend and his bud part 2 [MM] [Masturbation]

A few nights after my bf and his best friend jerked each other of I got a call at work from my bf telling me that about 15 minutes after I left for work Pete text him and asked if it was cool for him to come over. My bf text back right away it was cool. He said when Pete showed up the sexual tension was thick, but they settled quickly and things got back to normal right away. They started playing Watchdogs and quickly got back in their groove and comfortable. That’s when Pete said he was glad things weren’t awkward after what happened and he’d been thinking about it a lot since. My bf admitted that he had been thinking about it a lot as well. Pete said he gets hard just thinking about it and said he’d been jerking off to the pics my bf sent him. My bf asked which ones were his favorite and Pete said he loved stroking to my big tits, but always cums to a pic of me bent over with my panties pulled down to my thighs. My bf said he loves that pic too, that’s when Pete asked if there were more pics he could see or if he could see the videos again. My bf said “yeah but only if you let me stroke your cock to them” Pete agreed right away and added only of he got to stroke my bf’s cock at the same time. They had their cocks out right away and wasted no time. My bf synced his phone to our TV and they were stroking each other while pictures of my naked body played on the screen. They went slow Pete said he wanted to cum right away but wanted it to last. My bf said they talked about how sexy I am then my bf asked Pete if wants to fuck me. Pete said yes and my bf said Pete’s cock throbbed hard in his hand when he said it. He knew Pete wouldn’t last much longer so he told him they should strip so they don’t mess up their clothes and then put on the video of me and my Hitachi. Once the video was on they stroked each other faster. My bf kept telling me how good Pete’s cock felt in his hands. He said Pete stroked his cock so good he knew exactly what he liked. Pete moaned out he was gonna cum and my bf said he played with his balls for a bit then started stroking him faster he said he told Pete to cum for him to blow his load all over his hand. Pete couldn’t take it and came a huge load this sent my bf over the edge and he told Pete he was gonna cum too. Pete stroked his cock faster and used his free hand to play with my bf’s balls. My bf said he almost screamed when he came. Pete kept going milking my bf’s hard cock. After that they cleaned up but decided to stay naked. They were talking about my pics and the video they watched. Pete asked my bf why he asked if he wanted to fuck me and my bf said “I know you think she’s hot I’ve seen you checking her out and now we have been jerking each other off to her pics. You never know what can happen.” my bf said Pete moaned out loud when he said that and he saw Pete getting hard again. He put up some more pics and they started stroking each other again, this time facing each other. My bf said he was stroking Pete’s cock and said “I want you to fuck her.” “do you want to use my gf like your personal slut?” he said Pete moaned and said yes. He said they kept talking dirty. Pete said he wanted to fuck me so bad that he would do anything to fuck me. My bf told him they were going to take turns fucking me. They are going to use me all night and fill all my holes. He told me they kept going back and forth talking about all the dirty things they wanted to do to me. They both came almost simultaneously on each other’s cocks my bf said they coated each other. They kept stroking each other till they were soft and stopped to clean up. After that they went back to playing and a few hours later Pete said he was horny again he asked my bf if he could stroke his cock for him while he played and my bf said yeah. Pete grabbed my bf’s cock and started stroking him slowly getting him hard and playing with his balls. He said Pete got really close to his ear and started telling him “I want to fuck your gf so bad” “I want to fuck her in front of you”. He wanted to dp me so they could both fuck me and feel each other’s balls rubbing while they did. My bf said it was too much and he came hard. He said Pete looked like he wanted to lean forward and catch it in his mouth but stopped and just kept whispering in his ear “that’s it cum for me” Then it was my bf’s turn to stroke Pete and he did the same thing. He stroked him slowly and told him he knows how bad he wants to fuck me and how bad he wants to see me act like a slut. He told Pete he wants him to make me beg for his cock and make me beg to cum. He said Pete lasted longer than he thought and he was getting hard again while stroking him. Thats when he told me he wanted to suck Pete’s big cock. He said it looked so good and he wanted to make him cum so bad, and he wanted to see how Pete would react. He told me he was whispering in Pete’s ear they were going to turn me into a slut and Pete came hard all over my bf’s hand and almost got it on his face. After that they cleaned up again played for a while longer and Pete left.

Alex and Elle and the Week of Sexting, Part 2 [MF] [masturbation]

[Part One](https://www.reddit.com/r/gonewildstories/comments/5kewuq/alex_and_elle_and_the_week_of_sexting_mf/)
 

I made a huge mistake: I told Alex how ridiculously horny I was from his texts, how badly I needed to cum for him. This information in hand, he asks how I want to imagine us, and I respond:

 

Oh, fuck, Alex. Everywhere. You bending me over a table. Or me pressed against your window, on full display should a neighbor happen to look up. Your hands grabbing my tits and rubbing at my clit as I steady myself on the glass, make eye contact with someone across the way. Watching him watch me. Watching him watch you play with your toy. Turning us sideways so he still gets a profile shot of me, kissing down your body, my ass out and back arched as I kneel in front of you, taking your cock in my mouth, tasting you, swirling my tongue around the head, licking long lines up the whole of your shaft.

He responds: I’m nice and hard just thinking about it. ;)

[M]y [f]ourth time watching Deadpool

I had known this girl Vicki for a while. We had fooled around at her place and mine but mostly vanilla stuff. When the Deadpool movie came out, I loved it (closet nerd). However, she hadn’t seen it. So one night we decided to go watch it at this theater in Oak Park late at night.

A little about me. I’m 24 and about 5’11” with a dad bod. Vicki is about 6’1″ and curvy in the right places, a DD cup and thick ass (a PAWG, if you will).

I see her walking to the theater and I can’t help stare down her shirt. She catches me staring and winks, “After the movie, my place?” We walk in and enjoy the movie, laughing in this empty theater. Afterwards, we begin to leave and both go to the restrooms in the basement. I came out first and Vicki comes out with a twinkle in her eye “I can’t wait to get home, I just smoked a quick bowl in the bathroom”. I asked her, “Was it really that empty? Maybe I should check?”

How I had the best sex of my life, and the moral implications of it [MF]

Long time lurker. Throwaway for reasons that will be obvious later. This is a story that I’d likely take to my grave were it not for this subreddit. Even though I don’t condone what happened, I want to write this story down lest the memories and details fade. There’s a fair amount of buildup to give some context, so bear with me. Names have been changed to protect the innocent and the guilty. Jump to the break for sexy times. TLDR: met a chick who was a friend of a friend. Grappled with moral conflicts and had the best sex of my life.

I moved to a new city at the start of 2016. This story had its genesis not long after that when my buddies who live semi-close organized a ski trip for a bunch of friends, and I tagged along, not knowing too many other people in my new city. One of my buddies was dating this girl named Lanh (no, the story is not about her), who hung out with us all the time, and was pretty much another guy in the group. Lanh had a large contingent of Vietnamese friends that we knew in passing through her, and frankly, my buddies and I weren’t too thrilled to be sharing the cabin with all of them as they tended to keep to themselves and always took forever to reach a group consensus for everything.