BadBusinessMan5, Author at NSFW story

[MF] A wife wanted pics for her husband. I helped out.

Business trips to snowy locales are a bummer, it’s hard to get outdoors in the evenings and you start to get restless, or at least I do. On this trip, I wasted time with the whIsper app, chatting with women who were probably men, depressed people, and sometimes an actual person you want to chat with.

I found such a woman. She posted a message about work being boring, pretty mundane. We chatted about every day stuff. She’s engaged, I’m married, work, blah blah. Exchanged pics. She was very attractive, thin, cute, nice tits. After more texts, we naturally moved to sex talk.

Turns out her and her husband had an agreement – they were allowed to fuck others, as long as they shared pics or videos with each other from the encounter. Holy shit, jackpot. My concern was anything identifiable, and she understood and agreed no face or identifiable pics is acceptable.

We discussed timing, and agreed to meet early the next morning. Her husband left for work at 5am. I planned to be at her place at 6am. Got up early and headed over. Read more »

[MF] (plus M) Voyeur scenario turned around

This took place many years ago. I (I think 32 at the time) was on a business trip in San Diego, a conference, and I retreated back to my room to get some work done during one of the sessions. As I was wrapping up, I decided to check out the local CL casual encounters, as that was still a thing. All the F4M ads looked too hookerish for me, so I browsed the MF4M section, just to see what San Diego had to offer.

I sent a few emails. It didn’t take long for a few scams to return, but shortly after I did get a reply from a real couple who was looking for someone to watch them fuck. That’s not something I had done before, but hey, why not right?

We exchanged a few emails and voice verified (on my google voice account) and they agreed to come to my hotel since I was not familiar with the area. Read more »

[MF]{cheating}{squirting} First meeting of a long term LD affair

For a while, my business travels took me to Atlanta on a regular basis – 4 to 6 times a year. This frequency was perfect for a non-exclusive, on-going affair.

It started with an Ashley Madison account. While home, I set my location to Atlanta, sorted through the obvious sex workers and sent out a few opening messages. I chatted with a few women, but most were not interested in someone only in town for a few days at a time and only a few times a year. I didn’t arrange any meetups, but I also didn’t close the account.

While walking out of a restaurant one night, my phone buzzed. It was an email notification from AM, a message from Diane. I remember sending her a message, but her picture was blurred, luckily she provided a private key. She apologized for being out of town at the moment, but would be happy to chat and maybe meet up next time I was in town. We exchanged Kik names and chatted in real time. She was in LaGrange visiting her sister, so not too far away. We exchanged more pictures, and there was a mutual attraction for sure. I figured my next trip would bear fruit. Read more »

[MF]{Cheating}{Anal} I’m a jerk

So not all hookups are awesome, despite what my past posts have indicated.

I was in Baltimore on business, really nothing spectacular about this trip, however I did give Tinder a try. The risk of being seen by anyone I knew was pretty low. Anyway, I got a number of matches and chatted with a few women, but wasn’t able to find someone who could meet up that night for a one night stand, so I decided to go to an Orioles game.

Right as I sat down after the National Anthem, my phone buzzed with a match. Honestly I had just been swiping right on just about anyone who was mildly attractive with little regard for details, so when I dug deeper I saw this woman was not my type really. But I responded anyway.

I wasn’t a jerk about it right off the bat, but made it clear I was just interested in one thing. I told her I was married and only in town for the night. She claimed she could change my mind about that, that after one night with her, I’d be hooked. She claimed to be kinkier than any woman I’d ever been with before. Alright, game on! Even if she wasn’t my type, I was DTF and so was she apparently. Read more »

[MF] Pittsburgh Part 2 {cheating} {anal}

Previously, [I posted my encounter with Tara in Pittsburgh](https://www.reddit.com/r/gonewildstories/comments/arrxo0/mf_pittsburgh_part_1/). She told her friend Bethany about our adventure, calling me her human jack-hammer, which I will accept that as a term of endearment. A few weeks after our fun, Tara went dark. Shit, ghosted I thought, but then I got a new message notification in Kik. It was her friend Bethany. Tara had an OpSec failure – a twitter account that her husband discovered. Who uses twitter for anything like this? Anyway, Tara had relayed my Kik name to Bethany to let me know.

Bethany and I chatted, we got to talking about our past experiences, what lead us to do this, and so on. Turns out, she was a bit of a freak…

A few weeks later and I had another trip to Pittsburgh come up. I asked Beth if Tara would be available, and she said no fucking way, that Tara was in deep shit and trying to hold it together. I jokingly (but not really) suggested Bethany and I meet up instead. She wasn’t joking when she agreed. I was worried it would affect their friendship, but Beth assured me it would not, that they had shared guys before with no issue. Score! Read more »

[MF] Pittsburgh Part 1

During a period of my career, I was flying from city to city, and sometimes I lost track of when and where I was. This happened to me on the 3rd leg of a 5 city trip, where I found myself arriving at a hotel at around 10am, with no meeting until 1pm. I was in Pittsburgh. I thought quickly, haven’t I been chatting with someone in Pittsburgh? Yes! Tara! I met her on Ashley Madison a while back, on a previous trip to Pittsburgh, but the timing didn’t work out. What were the odds she would be free right here and right now?

I sent the text. “Hey! Guess where I am!”

She replied almost right away “you are in town?!? Why didn’t you tell me ahead of time?!”

“Well, to be honest, I forgot Pittsburgh was on my agenda. But I’m free until 1, what are you up to?”

Now our chats had been very explicit, lots of boob, pussy, and dick pic exchanges, so I was very much looking forward to seeing her in person. She wasn’t traditionally “hot”. She was cute, but a smaller BBW. Definitely someone I wanted to fuck, even if she wasn’t at the top of my mind at all times. Read more »

[MF][MF] Vegas Prequel

Vegas is a great place to attend a conference, [as I wrote about before](https://www.reddit.com/r/gonewildstories/comments/appujw/mf_mf_vegas_conference_fun/). That wasn’t the only trip there where I had a bit too much fun, though. This trip was about a year prior to the last story.

Again, a vendor conference with thousands of attendees. Again, I broke out the Whisper app. This time I saw an innocent enough post from a woman saying how her coworker is such a drag to hang out with. To be honest, my coworker was too, so we had something in common. Sarah and I chatted during our meetings, hers was on the other end of the Strip though. She was also married, mother of 4, about my age. We exchanged pictures, and she was very attractive. Thin, fit, blonde.

That night, I had a few drinks then went back to my room. I texted her to see what was up. She was out with her coworker at the old strip, but her coworker was uber mormon and would not drink. I told her to ditch her and come get a drink with me, to which she replied she wished she could, but she drove her car out there and that would leave her friend stranded. Read more »

[MF] {Cheating} Snowed in during a business trip

Bill, Mandy and I were away for business, as per usual, visiting a branch office in upstate New York…in January of course. They could have sent us to our San Diego branch, but nope, this project required our presence in a winter wonderland. As the week went on, we got more and more worn out – long meetings, stressful presentations, and little to no sleep at night will do that to you. We were focused on our jobs because we really wanted to get out of there and go home. We were so focused that we missed the fact that on Thursday, when our flight was scheduled to leave, a blizzard was in the forecast.

Thursday morning I opened my hotel room curtains to see complete whiteout conditions. Fuck, what are we going to do? Checked my phone, there are two dozen emails and text messages, long story short, no final presentation and no one was going to be at the office. Bill, Mandy and I were plotting our escape to the airport when we got a message from the airline – all flights canceled.

[MF] Fucking a married woman in her office

This encounter is a bit older, but it was my introduction to cheating. It wasn’t me that was cheating though – I was 21, she was 36. This was before the whole Cougar/MILF thing was cool!

I had just finished a paper for a history class and was mentally exhausted. I signed into a Yahoo chat room to see what was up in my state’s chat room. The normal bots were posting, a few regulars…and a new woman I’d not met before. I opened her Yahoo profile, and sure enough she was in my town, which wasn’t a common occurrence. I sent her a PM, and another surprise – she replied! Our chat started off innocent. She was older and married (but no kids). Professional job in an office. As we chatted more, I learned she was unhappy in her marriage. I was single, dating but nothing serious. We exchanged pictures, and while she wasn’t the hottest woman I’d seen, she was cute and attractive. She called me cute, which was a pretty generic response I thought.