I was never what you would describe as a social person. It’s not that I would avoid people but it’s more like I was never the outgoing or outspoken person in the group. I never really caused a scene and I always shied away from drama or confrontation, that’s just who I was. I guess you could consider me the classic “nice guy.”

My first exposure to being a cuckold–not that I knew that’s what it was called at the time–was when my college girlfriend at the time, J, went out to a local bar with me. We were expecting to meet up with another couple but they bailed on us, unfortunately. So J and I went out anyways since we had gotten half ready by the time the couple called and said they wouldn’t be able to make it anymore because of a family emergency.

We lived in a small- to medium-sized town and J and I both went to a local state school that was pretty much the main school in our area. It was small enough where you would run into people you know but big enough where you could live a pretty secluded life if you wanted to. So that night after our friends bailed, instead of going across town to the new dinner spot that we were planning for, we cancelled our reservations and went to a local bar. Now, the bar was still a bit of a trek but nowhere near the drive we would have needed to make for the restaurant. Once there, J and I ordered some light bar food and some beers. It was a light crowd that night so not too loud; it was more of a local crowd, just our kind of scene. Also, this bar was cool because they had several different types of “games” like a pool table, a ping pong table, darts, and even an indoor bocce ball court. Pretty awesome for some random bar…

After about 45 minutes or so in the bar, our drinks were getting low and so I walk up to the bar to get another round for us. I get J a white wine while I kept on with the whiskey. I was trying to be “cool” and try many different types of whiskey. Honestly, I don’t know what that part of my life was about but it was a thing that I was into at that point in time. Anyways, when I get back to our table, I see J is talking to some stranger who seemed to have pulled up a seat at our table. When I approached, I could tell this guy was one of those handsome types who would have his way with all the ladies and I could see that J was welcoming his attention.

He introduced himself as John. Apparently, he was a young doctor who was in town for a job interview at the local hospital. Again, our town wasn’t giant but we did have one of the biggest schools and hospitals for our state. He seemed really confident and I didn’t really like him right off the bat because it felt as if he didn’t really include me in the conversation. J could tell my attitude towards him wasn’t warm so she kind of whispered “be nice” while kissing me on the cheek, which made me relax a bit. He kept talking about his current work and why he wanted this new job. Of course J ate it up since she always wanted to go into the medical field and was about to graduate as pre-med. They clicked right off the bat and we pretty much spent our time chatting the night away–or should I say they chatted while I sat there nodding and interjecting when I could. She would laugh at all his jokes and I could tell by the look in her eyes that she was into him. Being the sulker that I was, I just passive aggressively kept ordering more alcohol and sat there and moped while they seemed to have a good time. J kissed me and squeezed my hand every now and then which was just enough attention to keep me at the bar with her. J tried to bring me into the conversation at times but by that time, I pretty much decided in my head that this guy was an asshole and I would spend the rest of the night in my own head.

Now, J isn’t your most sexually adventurous girl, but I wouldn’t say she was a prude either. Looking back now, I would say that this was the point in time in our lives when she really started coming out of her shell and “exploring” life. We had discussed things like threesomes or our past sexual history and neither of us really had much of a past. What I will say about J though was that she would get really wild when she had some alcohol in her. She also always got especially wet and would come easily if I would choke her a little bit or pull on her hair a little bit. Unfortunately, like I said earlier, I was never really an “aggressive” type of person so that didn’t really come off natural for me in bed. I was used to mostly just missionary and cowgirl and maybe try doggy style every once in a while before going back to missionary. I noticed she had a thing for cocky “bad boys” but I never really fit the bill on that front. She had on occasion asked me to be more “aggressive” and “manhandle” her but I could tell that I just didn’t do for her what she wanted. One time when she was really drunk, she told me about this night when she was really slutty with some random stranger with a big cock and how she loved it. Apparently he smacked her in the face, spanked her ass, pulled her hair, choked her, you name it. She told me how she thought I wasn’t man enough to handle her sexually and how she needed a real man to satisfy her. Naturally, we eventually both went to bed that night in sort of a mood. Unfortunately, after she sobered up the next day, she denied ever telling me any of that and acted like she never said anything. Whenever we have sex, I could always tell like she was not completely satisfied. And whenever we had drunk sex, it’s like she dropped the act completely and didn’t even bother to spare my feelings. One time we had a fight about it but we started to talk about ways to patch up our sex life like maybe have a threesome. Anyways back to that night…

So they get to talking and John tells us that the hospital flew him out for the interview and put him up in a fancy hotel suite. He invites us back to have a nightcap with him. J seemed excited to go but wanted to check in with me first. By this point, I was getting pretty buzzed and didn’t really have the energy to go to some random hotel of some stranger we just met. But he said it would be fun and J agreed for us and of course I didn’t put up a fight. I told them that I would go on two conditions: John would have to let me drink whatever I wanted from his mini bar and he’d have to pay for an uber ride because I was way too drunk to drive and I knew J hates walking in heels, even for short distances. He agreed with a smirk on his face saying that I could drink whatever I wanted so long as we would come back with him “to play”. “Whatever”, I said, again passively throwing the middle finger up at this cocky asshole.

I go to close out my tab and when I come back to the table, for a split second, I thought I saw John’s hand on J’s thigh while he was whispering something in her ear. He must’ve saw me come back though because he quickly moved his hands away and backed away a bit to a normal distance. Me being drunk, I chalked it up as me imagining things and just ignored it. Or maybe that was just my personality to avoid drama, I don’t know. Anyways, all I know is that–looking back on it now–that was a huge warning sign, especially because J didn’t do anything to stop him and even seemed like she wanted it.

J excused herself to use the bathroom and I’m stuck there with this jerk for a few minutes.

“J is a really nice girl, bud”, he said.

“Yeah and she’s my girl”, I snapped back to him.

“We’ll see about that”, he said as he laughed and walked out the door.

Wow, this guy is a bigger asshole than I thought if he literally is saying to my face that he is going to try to steal my girlfriend from me.

J came back from the bathroom and asked where John went.

“Wow, sad that your new boyfriend left you?” I said.

“Relax babe, I’m just making the best of tonight. Plus he’s going to work at the hospital where I want to work someday, you know that. It’s good to make these relationships.”

“Whatever, he’s outside. I think the Uber’s here.”

“Hey. Come on babe, don’t get upset. Relax.”

“Just don’t think we’re having a threesome or anything with this guy because I told you, our first threesome is going to be with another girl.”

“Hahaha wow babe, you’re being super paranoid. I’m not going to fuck some guy just because he’s hot and successful and funny”, she said as she walked towards the door.

Wow, flag #2.

So we both walked outside and sure enough, John was already in the backseat of a small car. J got in the back and I started to push in there when J told me it was getting too squished. Of course the driver accommodated and told us that his front seat was available too so sure enough, there I was in the front seat while my college girlfriend of two years and some stranger were in the backseat. I don’t want to call the car a sedan because it was one of those tiny cars that you get super pissed off about when they pull up. Like it should be false advertising to have that as an uber. Anyways, I say all that to describe how close J and John were sitting in the backseat. The fact that we all just had a ton of alcohol didn’t help any either. What was the cherry on top was our driver was one of those drivers who would engage in conversation with the guy in the front seat, and this gave John his opening with J.