She was engaged and I had a girlfriend. We met for a drink anyways ;) | 2016

In a way, this is a followup to my previous story about a FWB who reconnected with me when she had a boyfriend. Original story here, but it’s not really necessary to read/understand/enjoy this one.

So after fooling around in my car we didn’t see each other for a few years. Every couple months we’d use messenger and talk about being hot for each other and stuff but wouldn’t actually do anything about it. Mostly this was due to distance; she lived about 4 hours north of me.

One night in June we ended up chatting. We hadn’t talked for a while so we were updating ourselves on our lives. It was totally a platonic chat. I told her about my new girlfriend and she informed me she was engaged to the same guy she had been with the last time we chatted. I made a joke about whether or not she was sure she’d be able to behave herself given the last time we’d met. As soon as she said that she responded by telling me how much she wished we’d ended up fucking that night. I told her I felt the same and then told her that she’d cheated on him anyways by fooling around/sucking my cock, she might as well have made it count by fucking me too.

I knew by now that I could say basically anything to her. If I said anything that would otherwise have been too risqué she’d either just accept it or maybe fake offense for a second before responding back with agreement. I told her that it was almost as if she and I deserved one last fuck for the last one that we’d screwed up. I can’t remember most messages word-for-word, but I remember her response to this and I’m sure it’s accurate even though it was about 4 years ago: Holy fuck, I can’t believe I’m saying this. Let’s just fuck.

I told her I was down, but then she changed gears. I tried to return to the subject a few times but she would change it back. I even considered that maybe she’d gotten off right after typing the “Let’s just fuck” message and had come to her senses. She started to ask me about old high school friends and was wondering who I still spoke to. Finally she asked whether or not it would really be a secret between us. I assured her that it would since I had a girlfriend to lose.

As it happened a few weeks later I was going canoeing with friends hours north in the province. The park happened to be and hour or so away from where she was living at the time. I wrote to her before I left and said that I’d text her after the trip was done. She sorta treated it like I was joking and had a ‘I bet you won’t have the balls to actually text me after, but have fun on the trip’ attitude.

The trip went fine(I didn’t say anything to the guys about it) and I texted her as soon as I got to my car to drive back home. She didn’t respond for twenty minutes or so. She sent me a ‘Want to meet for a drink?’ message? I said sure and she told me to meet her at a Kelsey’s Steak House/Bar. She texted me the address and I GPS’ed it.

It was about 2pm when I pulled into the parking lot and immediately I saw that the bar was attached to a hotel. Up until then I think I had actually just assumed that we’d meet for a drink and then go fondle each other in the car a bit. Once I saw the hotel I actually got nervous for a bit.

I took a seat at the bar and ordered a pint of beer. I had brought a book in with me and that was a good thing because I waited for about 20 minutes for her to show up. There were very few people in the bar, but as she came in she recognized a couple who was leaving. They didn’t seem to be friends or anything, more like acquaintances. Still, it was enough for me to think that she would make an excuse and leave – she’d been seen. But once the couple left she shot right over and sat next to me at the bar.

She said something ridiculous like “Hullo chum” and gave me a side hug. She bought a bottle of beer and I did as well. We talked about the canoe trip and what she’d been up to that morning. She looked adorable as hell. She’s tiny, like 5’3 and has shoulder length dark hair. She has a super tight body and a terrific ass. She wore a grey sweater with a large neck opening (I could see one black bra strap poking out) and black yoga pants.

Eventually she said she had to go to the bathroom and I said I did as well. The washrooms were in the large corridor area connected the hotel to the bar. They were off to the side a bit in their own alcove. I went to the washroom and then waited in the alcove for her to emerge from the women’s room.

She looked at me and said “So what do you want to do?”. Like an idiot I asked “About what?”. She responded by saying “Well, I picked this location for a reason…” in a flirty way. I wrapped my left arm around her waist, put my hand on her back and pulled her in close. We kissed passionately for a few moments and she started to rub the front of my pants. We separated and both laughed. We agreed to get a room.

She used her credit card, and I insisted on shoving some cash into the open purse that dangled from her shoulder as she dealt with the front desk. There was a bowl of complementary fruit and I took an orange (not sure why I’m including this detail, but it is something I do vividly remember from the day).

We got the card key and went to the room, which was only about three rooms down from the front desk. We went into the room and she said she had to go to the washroom again. I inspected the room a bit and waited for her to come out. Once she did we attacked one another. I pulled her sweater off her head and she was undoing my pants at the same time. As my pants were falling off I spun her around and slipped my right hand down the front of her pants from behind. I began to finger her under her panties and she was rubbing my cock with her left hand. Sometimes she’d jerk my cock and then she’d press it against her ass cheek. Together we stumbled to the bed and found ourselves in the missionary position.

I asked if she had a condom. She didn’t say anything but used that time to pull my shirt off. I decided ‘fuck it’ and pulled her pink and white panties to the side (they were polka-dotted booty shorts). I looked in her eyes and we both kinda nodded. With that I plunged inside of her. “Oh fuck yeah, mmmhmmph” she moaned. We fucked and fucked and only stayed in the missionary position. It was so hot. Sometimes I had her arms pinned. We’d alternate who was sucking on whose chest. There was a little bit of face licking. Really intense. I told her to slow down because I was close to cumming. She told me to cum so I pulled out and came on her stomach. We lay there a while and collected ourselves.

She said a simple “Well, that was fun” and we both laughed again. Within a few minutes I could feel that I was going to be able to get hard again (I’m not superman – this kinda thing only happens to me on rare occasions) so I started to go down on her over top of her panties. They were already wet from before but now I was soaking them with my saliva and her own wetness. Eventually I started to take them off and the willing action of her hips and legs made me fully hard again.

We fucked again, not as intense or as long as before, but good nonetheless. Afterwards we shared a shower and it was amazing how we just regressed into small talk again. As if we were actually a couple just sharing a shower.

We got dressed and I walked her to her car. I gave her a quick kiss and that’s the last time I have actually seen her. Although we do write to each other a few times a year, just to say hello.

I drove home to my girlfriend (yes, who I had just cheated on). On the way home I threw the orange out the window to avoid any questions about it. No one ever found out about that day at the hotel (as far as I know) and I broke up with my girlfriend a few weeks later.