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Anything Goes
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Straight Male / 33
So this happened about 3 years ago. I just want to get it off my chest. It's not a torrid sex story either.
Long story short I was having an emotional affair with a co-worker. She was 26, and I had recently turned 30. I guess I was going through a mid mid-life crisis. I had been married for 4 years, after dating for 5 years. Things just got so predictable that my co-worker's interest in me set me afire. She had been dating a guy for 8 years; at the time he was a first year med resident, clearly more interested in being a doctor than paying attention to the hot piece of ass he had at home.
So my co-worker and I started to go to happy hours, and the talk always de-evolved to sex. For example, at the first happy hour on the way to our cars she asks "I bet your wife doesn't swallow" I nodded to confirm and she replied, "I always swallow, it's no worse than drinking a shot." Meanwhile the texting during and after work was so much I was going over my text message limits. Eventually we made out and groped each other after discarding most of our clothes at my house. But we never had sex or oral. Just before we would have crossed that line the doctor-in-training noticed the change in his girlfriend and professed his love again to her and took her engagement ring shopping. At this exact same time I was going to Cincinnati for a work conference. This is where the story takes a turn.
As I'm in the airport, my co-worker has the gall to text me engagement ring pictures. "Do you like this one??" This sends me to the airport bar. Aircraft problems caused a de-planing and I hit the bar again. I continue to drink on the plane ride. Once in Cincinnati it was so god-damn hot the only thing to do was stay indoors and drink. I settled in at Rock Bottom Brewery and continued my drinking. 2 guys at the bar remarked about the table of 14 girls in the bar area celebrating a birthday. They wished they could get in, but the numbers were against them. In my happy drunk state, I exclaim "Challenge: Accepted! Follow my lead." I proceeded to the birthday girl, introducing myself politely. I could feel 26 girl eyes just burning holes through me as they looked on. I asked if I and my 2 new buddies could buy the next couple rounds to keep this party going. She said sure and I pull my 2 new friends aside and tell them it's all on me and then grab the waitress and give her my credit card and say the rest of the night is on me. I chatted up the birthday girl for an hour, taking one for the team, while my 2 new friends chatted up a couple of the girls. Eventually I started talking to a few other girls and hit it off and made arrangements to meet up at a Reds game in 2 nights, which was part of my conference. In the end the bill was $530, and I wrote in a $100 tip. I said my goodbyes. My two new friends shook my hand and said thanks, it looked like one or both might get lucky tonight.
I stumbled back to the hotel. Took a shower and headed back down to the street to have a cigarette. That's when I met Britney, a tiny yet totally cute tomboy who was also smoking. I asked if it was always this hot and humid here at 11 PM, she wasn't sure, she was from nearby Cleveland but thought it was. We hit it off instantly, she had a Southern accent that she later admitted came from growing up in Southern Kentucky. I told her I grew up in Nashville, but now called Colorado Springs my home. I invited her to the swanky hotel bar and she agreed with a big smile. I remember ordering a whiskey sour with Makers Mark, but the rest of the night was a blur, a total black out.
I woke up in my room at 7:45, naked next to Britney who was sleeping in her teal bra and panties. My stirring woke her up. She smiled and said "Don't worry, we didn't have sex... well, I guess we tried, but it wasn't happening for you... just the tip if you now what I mean." I nodded and spooned her for a few minutes. She said, "Oh, now you're romantic" I wondered what that meant. She got up a short while later, put her clothes on, and said she was worried about me last night and that's why she spent the night. I guess she thought I would choke on my own vomit or something. She hugged me and said she had to go and left.
Afterwards, I showered and got a coffee around the corner and signed in for my conference. I got a text at 10 AM from one of the girls from Rock Bottom asking how I fared last night and invited me across the river that night to go to the Hoffbrau Beer Garden. I said sure.
I texted my co-worker a little later, "Crazy night last night". She replied "What happened??1??!" I explained how I woke up next to a girl in my bed. She went ballistic, "I didn't think you were that type of guy!!". I replied, "You've with Matt now, what does it matter what I do?? Unless you still have feelings for me." She replied, "Of course, I have feelings for you!" I contemplated this: she had just said things were over and that she was going to stick it out with her doctor and they were picking out an engagement ring. I typed in "F-U, Gold Digger." I looked at it for a few minutes and eventually erased it. I spent the rest of the day thinking how to explain this away to my co-worker and, if necessary, my wife, while looking forward to the Hoffbrau that night.... To be continued??
Long story short I was having an emotional affair with a co-worker. She was 26, and I had recently turned 30. I guess I was going through a mid mid-life crisis. I had been married for 4 years, after dating for 5 years. Things just got so predictable that my co-worker's interest in me set me afire. She had been dating a guy for 8 years; at the time he was a first year med resident, clearly more interested in being a doctor than paying attention to the hot piece of ass he had at home.
So my co-worker and I started to go to happy hours, and the talk always de-evolved to sex. For example, at the first happy hour on the way to our cars she asks "I bet your wife doesn't swallow" I nodded to confirm and she replied, "I always swallow, it's no worse than drinking a shot." Meanwhile the texting during and after work was so much I was going over my text message limits. Eventually we made out and groped each other after discarding most of our clothes at my house. But we never had sex or oral. Just before we would have crossed that line the doctor-in-training noticed the change in his girlfriend and professed his love again to her and took her engagement ring shopping. At this exact same time I was going to Cincinnati for a work conference. This is where the story takes a turn.
As I'm in the airport, my co-worker has the gall to text me engagement ring pictures. "Do you like this one??" This sends me to the airport bar. Aircraft problems caused a de-planing and I hit the bar again. I continue to drink on the plane ride. Once in Cincinnati it was so god-damn hot the only thing to do was stay indoors and drink. I settled in at Rock Bottom Brewery and continued my drinking. 2 guys at the bar remarked about the table of 14 girls in the bar area celebrating a birthday. They wished they could get in, but the numbers were against them. In my happy drunk state, I exclaim "Challenge: Accepted! Follow my lead." I proceeded to the birthday girl, introducing myself politely. I could feel 26 girl eyes just burning holes through me as they looked on. I asked if I and my 2 new buddies could buy the next couple rounds to keep this party going. She said sure and I pull my 2 new friends aside and tell them it's all on me and then grab the waitress and give her my credit card and say the rest of the night is on me. I chatted up the birthday girl for an hour, taking one for the team, while my 2 new friends chatted up a couple of the girls. Eventually I started talking to a few other girls and hit it off and made arrangements to meet up at a Reds game in 2 nights, which was part of my conference. In the end the bill was $530, and I wrote in a $100 tip. I said my goodbyes. My two new friends shook my hand and said thanks, it looked like one or both might get lucky tonight.
I stumbled back to the hotel. Took a shower and headed back down to the street to have a cigarette. That's when I met Britney, a tiny yet totally cute tomboy who was also smoking. I asked if it was always this hot and humid here at 11 PM, she wasn't sure, she was from nearby Cleveland but thought it was. We hit it off instantly, she had a Southern accent that she later admitted came from growing up in Southern Kentucky. I told her I grew up in Nashville, but now called Colorado Springs my home. I invited her to the swanky hotel bar and she agreed with a big smile. I remember ordering a whiskey sour with Makers Mark, but the rest of the night was a blur, a total black out.
I woke up in my room at 7:45, naked next to Britney who was sleeping in her teal bra and panties. My stirring woke her up. She smiled and said "Don't worry, we didn't have sex... well, I guess we tried, but it wasn't happening for you... just the tip if you now what I mean." I nodded and spooned her for a few minutes. She said, "Oh, now you're romantic" I wondered what that meant. She got up a short while later, put her clothes on, and said she was worried about me last night and that's why she spent the night. I guess she thought I would choke on my own vomit or something. She hugged me and said she had to go and left.
Afterwards, I showered and got a coffee around the corner and signed in for my conference. I got a text at 10 AM from one of the girls from Rock Bottom asking how I fared last night and invited me across the river that night to go to the Hoffbrau Beer Garden. I said sure.
I texted my co-worker a little later, "Crazy night last night". She replied "What happened??1??!" I explained how I woke up next to a girl in my bed. She went ballistic, "I didn't think you were that type of guy!!". I replied, "You've with Matt now, what does it matter what I do?? Unless you still have feelings for me." She replied, "Of course, I have feelings for you!" I contemplated this: she had just said things were over and that she was going to stick it out with her doctor and they were picking out an engagement ring. I typed in "F-U, Gold Digger." I looked at it for a few minutes and eventually erased it. I spent the rest of the day thinking how to explain this away to my co-worker and, if necessary, my wife, while looking forward to the Hoffbrau that night.... To be continued??
