I found some money I forgot I had so I decided to spend most it on junk food and prostitutes.
I visited the escort after work yesterday and we hung out for a few hours and smoked weed and stuff. She didn't have any weed when I got there so we went to her dealer to get some and spent a lot of time sitting around on a thrown out couch on the sidewalk and we kinda just talked for a while.
She sat on my face for a bit and at one point I tapped out but she stayed on me for a few more seconds, and I started to panic but at the same time it felt kinda good I guess. I told her and she asked if I'd be interested in having her make me pass out. I was pretty hesitant at first because I knew how dangerous it could be and it also just didn't sound very fun, but eventually I agreed. So she started sitting on me and after about 30 seconds or so it started to become physically painful. I felt like my head and chest were going to explode and I was kinda scared honestly. After like a minute (at least I think it was a minute, it felt like forever) my arms and legs started contracting and twitching and just as I was starting to feel everything fade I pushed her off. I felt pretty drained and lightheaded afterwards so we stopped and she got me some water. So that was an experience.
Anyway we kept talking and she told me that when she was on me she felt a throbbing feeling in her vagina and asked if I wanted to ever have sex with her. While she was telling me this she started blushing and talking about how embarrassed she is. Now ever since I met her she's been telling me how cute/sweet/adorable I am but I kept telling myself that she was just pretending to like me to get me to keep paying her, but at this point I started considering that maybe she's not acting. I kept thinking about it over the course of the next hour or so and eventually we were upstairs in her room and she was showing me her bras (I forget why but that's not important). At some point I decided to just go for it and see what happens, so as she's standing near the wall looking perpendicular to me I do what must have been the smoothest thing I've ever done in my life and put my hand on her shoulder and gently push her up against the wall so that we're facing each other. I sort of rested my chest against her boob and kind of nuzzled her ear/forehead with mine and she put her hand on my chest and told me that my heart was racing. I put my hand on her chest and told her that hers was too. I think she may have said something afterwards but I forget what it was because a few seconds later I sort of leaned my head sideways and kissed her. She started like sucking on my lip with her teeth and all this cool stuff and it was awesome. We hung out some more and around 10:30 PM we started saying goodbye and she grabbed my face and we made out some more. Then I left and jerked off when I got home and went to bed.
So... the first girl I ever kissed happened to be a prostitute. At least I'm pretty confidant I didn't catch anything, she gets tested regularly and never has sex without a condom. Also I could be misremembering but I think at some point she's said that she doesn't normally kiss clients.
But I think she's genuinely into me. When we first met she was telling me about how when she was younger she had a habit of having sex with shy awkward guys, and in case I haven't mentioned it before I happen to be a shy awkward guy. She's constantly laughing at all the awkward stuff I say and do. Also blushing and a fast heartbeat aren't something you can fake easily, so those seemed pretty genuine.