That Time I Considered a Sleepover and Got Paid For Sex


Featuring an appearance by that damn country song he sang to me!

So another Wednesday rolls around and I started calling our hangs “Dentist Appointments” and I’d share some laughs with Jeanie and Larissa (and eventually others but we’ll get to that soon enough) over this. I can’t remember why we didn’t hang out shortly after The Dentist was done work but it ended up being later in the evening. I do remember going to the airport with my mom to pick up my dad so maybe it had something to do with that, or maybe he had something on the go. The important part was that I got to see him because you know, I wasn’t falling for him or anything…

I’m a creature of habit, I like tradition and I hate to be inconvenienced by things. It was a slight inconvenience that Wednesday was becoming our day because Wednesday is also my TV night; Arrow, Survivor, and Empire. Throw in sex with The Dentist and you’ve got yourself a conflict of interests. Our first Wednesday happened in the afternoon which didn’t conflict with TV and the second did go a bit late but I don’t think Arrow was on that week. It was also an inconvenience to have this family time airport pick-up as well.

While texting The Dentist that day and making plans for later that night, I said something about how Arrow would be on and he said he would watch it. This shocked me a little; why was he willing to watch a show I wanted to watch when I was fairly certain he would not be interested in it? I mean, he was already in my pants… The Dentist did one better and shocked me even more though when he suggested we watch Arrow, fuck (not necessarily in that order) and I sleep over. HE WANTED ME TO SLEEP OVER?!?!?! Flashback to several posts ago and recall that I went on about how I feel like cuddling is the most intimate thing you can do with someone; well sleeping with, and I mean actually sleeping with someone is way, way, up there too.

I remember reading those words in the message and being really thrown off and not knowing how to respond. (I think I literally wrote “Oh! Um…Oh…” as my first response). What was I going to do?! I wanted to stay the night. I did like being with him and being next to him, but he had someone. Why would he want to do this with me? I didn’t want to say no because I didn’t want to hurt his feelings and I didn’t want to say yes because I knew I would enjoy it too much.

I consulted Jeanie as she was my Go-To and usually accessible to chat online during the day. (Larissa lives in like the furthest time zone away which is not conducive to needing up to the minute advice on whether or not I should spend the night with the bro I like who has someone else). I believe I sent her a screenshot of the text exchange between myself and The Dentist and after she called me “Rain Man” for my “Oh! Um… Oh…” response she told me to go for it and see how it plays out, I could always go home if I wanted to.

I couldn’t make up my mind. I was trying to decide between being selfish and being a good person and also not trying to screw myself up even more. Truth be told I was still pining over The Kid as well and would often write him as he told me we would hang after he got back from Montreal and got some school work straightened away. I knew I was developing feelings for The Dentist, and I knew that was silly because it had only been three weeks but he was so nice to me and adorable. I knew I’d be going over there but I didn’t know if I would be staying. I also worried about the Wet Blanket finding out and asking where I was.

So I’m sitting at this restaurant that specializes in wings with my mom, brother, and niece while I’m trying to decide what I’m going to do and then as if it was some weird gay sign from the Heavens, “Stuck Like Glue” by Sugarland starts to play; the country song he sang to me in bed that first Wednesday. Now maybe that was a sign, maybe it was a not so fluke (the restaurant does tend to play a lot of country music since apparently wings are “country”?). Either way, I took it as a sign and thought “fuck it… go for it…”

So after the airport, I get dropped off at the library because again, asking your parents to be dropped off at a guy’s house you are about to bang when they don’t know you are up to that sort of thing is in bad taste. I mean, even if they did know that, it probably still wouldn’t be your typical family activity. I don’t think I actually even went to the library, I just went and brushed my teeth (because I was going to see The Dentist…) and offered to pick up some beer. I walked to a nearby gas station and cabbed it from there (his car was still broken).

I got to his house and we banged just in time for Arrow. He popped popcorn for us and we cracked a few beer. He sat down next to me and was actually watching. Sadly, they had to air the most over the top and ridiculous episode of maybe the entire series on this night. Usually, Arrow is fairly grounded but this episode introduced Hawkman and Hawkgirl and how they are immortal ancient Egyptian royalty with super powers and they keep getting reincarnated and finding each other through history while running from their immortal arch nemesis Vandal Savage. The Dentist was not feeling this but he watched anyway (possibly because he thought Hawkman was hot…which I was a little annoyed about).

Since Arrow didn’t go over well I didn’t suggest we watch Empire. On my way over, he informed me that he didn’t have any cash to pay for a cab home which kind of sucked but luckily I had some extra on me. We went to bed, but before that, he proceeded to write me a cheque for fifty dollars because I had “taken so many cabs”. I joked that I was now a hooker (though also sort of felt like one). FIFTY DOLLARS. Well… We joked about that for a bit and definitely banged again as well. I told him I wasn’t sure about sleeping over because I never sleep when I’m in a new place and sleeping with someone is also a big deal to me, plus I might have to work in the morning and didn’t know for sure.

We cuddled for a while and I decided I should go home. He was falling asleep so I called a cab and got my things (and by things I mean pants). I remember him saying something about not leaving without saying goodbye and so I went back into his room and kissed him goodbye/goodnight. Typing this makes me want to throw up because I hate showing affection and I hated that I was doing this with a person who had a person but said person was a person I wanted to do these things with. After all, he watched Arrow, fed me popcorn and paid me $50 for sex.


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