Author: i-know-im-terrible

[MF] Business travel fun

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 4 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 »

Consoling a younger grad student leads to a year old affair [MF]

I originally met Maria on the garbage Whisper app. I don’t remember the original post, but it was just a regular venting post about nothing in particular. We started chatting though and developed a friendship. I was (and am still) married, she was engaged. We talked about relationship issues, school (we were both in grad school), and many other things. This went on for months before even a hint of anything sexual. She knew I slept with other women, but she gave no indication she was interested. Plus, she was 23 and I was 37. We did share pictures though, and Maria was very attractive. Smooth dark skin, in shape, great tits.

One day, her texts were short so I asked what was wrong. Her fiance had shared a video of her giving him a BJ with his friends, and she was very upset about it. I tried to lend a sympathetic ear, but she was too upset to hear it. Then, without asking, she shared the video with me. “Why would he share this?” I thought. I didn’t press the issue, but I could hear her crying through the text. “Sharing this without your consent is pretty disturbing” was the extent of what I was able to say just through texts. Read more »

[MF] Vegas conference – married woman with a tat of her husband’s name. [CHEATING] [ANAL]

Vegas. A cheater’s playground.

I was in Las Vegas for a conference with a number of co-workers and colleagues, many of whom knew I was married, knew my wife, and would not approve of any extramarital action. This presented a challenge, not a road block!

I was sitting through a fairly boring presentation and I fired up the Whisper app to waste some time. Usually this app is a waste of time. I saw a non-sexual post, though, that I responded to. It simply said “Vegas Whisper is way more interesting than <insert home town name> Whisper!” I replied to agree, and we started a chat that quickly moved to snap. Zoey was married, also in Vegas for a work conference, also with pious co-workers. We kept the conversation PG-13 at first. Read more »

[MF] Ashley Madison meetup

In my early days of cheating, I often turned to what used to be the gold standard – Ashley Madison. I would always use a pre-paid gift card and register that under a fake address so it could not be traced back to me without connecting a lot of dots. Thankgoodness I did this, as AM was hacked, as we all remember.

Anyway, a few weeks before a business trip, I set my location to my upcoming destination and browsed profiles, sent a few messages, and hoped to make a connection. Luckily “Amy” responded. We sent a few messages and moved the conversation to a chat application.

I had only been with a few women outside my marriage at this point, and Amy had not cheated yet. We talked a lot about anxieties about cheating, how to not get caught, things like this. We of course sexted and sent nudes. We were both leaning towards meeting, but Amy had to ensure she would not get caught.

My trip arrived and I flew to the meeting location. When I landed, I messaged Amy to let her know I was in town, and I hoped she could escape to come see me. She quickly responded “Yes! My class tomorrow is canceled so I have hours of free time!” I checked my schedule, and her free time fit perfectly into my availability. Read more »

My (33M at the time) first time cheating [MF] – hotel gym and bar encounter

I’ve cheated with a number of women. The first time was a chance encounter during a business trip. This was almost 11 years ago now, how time flies!

After a long day of meetings in downtown Chicago, I headed to my hotel room. Emails and voicemails filled my computer screen. I was stiff from sitting all day and needed to hit the gym before diving into work. I changed out of my suit and get into gym clothes and headed to the treadmill and weights. There were two other men in the gym, and one woman, who looked to be pushing 40 and also had a few extra pounds, but still had curves which made you stare a second longer than you probably should. She also had a wedding ring. She finished her workout, another anonymous man walked in, I finished my routine, and headed back to my room to shower.

I ordered room service and tackled my tasks for the evening. Before I knew it, it was 9:00pm and I was mentally shot, I couldn’t do any more work. I called home, said good night to the kids, and my wife was short with me and didn’t really want to talk. Read more »

Last night of a business trip turned into my (36m) first threesome [MF] [MFF]

I was 36 at the time, I’m a few years older now.

In the pre-Covid times, I would often meet women for extramarital fun while on business trips. This encounter was amazing! It was the first of only two threesomes in my life.

The conference ended on a Thursday, however my flight home was not until 10am the next day. I was the only one from my company on this trip, so I was alone and able to enjoy myself. I found a hookup earlier in the week, so I wasn’t necessarily looking for any more bedroom fun, but I still headed to the section of town where there were a lot of bars, and landed in one with live music and dancing.

I noticed one woman up and dancing with her friend, while I was seated and enjoying my drink near by. She was curvy in the best ways, dark hair, pretty face. Her top showed off enough cleavage, but not too much. Read more »