I've had a couple encounters. I'll start with the ""non-escorting"" encounters, which were really escorting encounters.
#1
The very first time was with this black TS escort that lived across the street from me. This was years back, pre-pandemic. Anyway I was selling w33d at the time and I thought it would be a bright idea to tap into the dating apps as I heard a lot of ppl would cop from apps. I installed most but got banned pretty quickly except for POF and Grindr. I ended up getting hit up by this TS that lived across the street from me. First couple of times they would cop from me was no problem and they asked for my number and even thank'd me and said the weed was good. One day they hit me up late as hell, like 2 or 3am, I should've known what was up because majority of the time they would msg me would be around 6 or 7, even sometimes at 9 or 10 but never this late but money is money. I usually also made them meet me downstairs in front of my building, but this time they told me come across the street to their building. I get there and then she texts me to come upstairs. So I go up 5 flights, no elevator and I'm kinda pissed at this point I just want my money and to leave. I give her the stuff and I'm just standing there waiting, she tells me I can sit down and that she gotta look for the money, red flag #3 now at this point. I'm thinking they're gonna try and rip me off but they come back but of course they're short. She asks if I'd be down to settle up the rest with some head. Now I've been through this song and dance before on the app. I've had countless people offer but I swear on everything I love I've always turned them down as I was about my money but that was over the app...it's 3AM....in person...and I've already wasted my time coming here. And I'm not stranger to transporn so I figure this is probably going to be my one chance to actually experience what its like...so I say fuck it. I stand up, they drop down and give me some of the coldest head I've ever had...at least at that time. Now I will say, I attribute this one encounter that led to a full fledge campaign of pure degeneracy on Grindr, POF, and escorting sites. I kept selling them weed but there were also a few late nights, I'd hit them up for some throat in exchange for weed. I eventually ended up calling them over to my house once and fucking them and it was easily the tighest ass I've ever experienced in my life. This went on for a couple months but I just kept it to getting head because one night I came over and the security guard for their building was grilling me. I told them I had to give up something to them but the grilling made me think maybe he was fucking her too. I think they eventually moved away because I stopped seeing them and they stopped hitting me up.
#2
Now my second encounter was very similar to the first. There were these 2 trans chicks that lived together in a building behind my apartment. A lightskin one and a dark skin one. The lightskin one was super passable...look really good. Terrible voice though that kinda gave it away but off looks alone you really wouldn't have been able to tell. Anyway she had an awful attitude. I only knew her because I used to see her ads online and even though she was trans she would post in the women section. Dudes would leave comments saying she was trans and how she stole deposits, gave them the run around, arguing in the comments with them, etc. Now the other one isn't anywhere near as good looking as the one with attitude. She had a fat ass and big tits but facially wasn't it. I would say she was a doppleganger for pornstar Mz. Booty....like she legit looked exactly like her, same face, same tits, same ass. Anyway, I'm back on the app the dark skin one, we can call her Mz. Booty, hits me up for weed. I give them my add, quick exchange no problem as they live around the block from me. 2nd time, they tell me I gotta come to them because they don't have the key and don't wanna get locked out...it's literally right around the corner, so I don't mind. I see the lightskin chick with her but I don't say anything, I just give her the stuff, get the money, and go. Me and her are cool at this point, she's copped from me at least 10 times at this point with no problem at all, either me going to her or her coming to me with no issues. Now it's around spring time and she shows up to cop but she's wearing these tight ass leggings that's hugging the shit out of her ass. As she turns to leave, I can't help but let out a "DAMN" as she's walking away, but before the door closes she comes back in and says "damn what". I wasn't expecting that at all lol so I was like oh nah, I was just damn cause you was walking away. So she asks me "so what you tryna do", I'm like HUH? And she just goes oh okay....and walks out. Now at that point I should've known she was game but I didn't think she heard me and I wasn't expecting them to be so forward, so I completely bitch'd up lol now fast forward at least a week, they hit me up saying they need some again. So I go over to their spot. I'm waiting downstairs and they're like "hey can you come up", they live on the 2nd floor so not a 5 flight trek but whatever, now I immediately know something is up because every transaction up until this point has been in their lobby or in my lobby. No games, no BS, no shorts, nothing. Just come and go, no problem besides the last time with the leggings. I come upstairs, I give them the w33d, and sit down on the couch. They tell me one sec and they're start rummaging through their purse. This goes on for at least a legit 5 mins. They leave, go in the room, come back, then go in another room, then come back, then rummaging through the purse again. I ask them if they're good and they say yeah they just need to find the money. After like 5 more mins of this, they just walk over to where I'm at on the couch, pull down my pants and starts sucking me off. I stop them and ask what the fuck are they doing and she goes "idk" and goes right back to sucking my dick. Now I'm not gonna lie this shit was amazing, like I felt like I was in a porno, I've never experienced anything like this before...not even with ex-girlfriends. She sucked me up for a good 10 mins straight, I pick her up and bend her over the couch, and before I could get inside that fat black ass she stops me and tells me she hasn't cleaned herself out. I immediately nope'd out because there is no way I'm getting shit on the dick, so I just sit back on the couch and just settle for head. The only problem is that as soon as I came, she stopped sucking and just jerked me, which was weak as fuck. After that though they never hit me up for weed. I went online to see if I could maybe find their ad but nothing at all. I did see them as a recommended friend on Facebook one time, added them but they never accepted lol and yes I was thirsting because I wanted to hit that ass at least once. I don't know if they moved away or what but I never saw them again after that.
#3
Now that I'm remembering I actually lied, my first encounter was way back when I was a teen...although no actual sex happened so I'll make these stories quick as they aren't really juicy. But this was back in the AIM days. I used to talk to this chick named BigBootyChick2006. Now keep in mind I'm a horny teen, this was the early to mid 00s, I was still jerking it to those shitty 30 sec trailer ads on AssParade/40inchPlus/40ozBounce. We were still on dial up...I was down bad horrendously. Anyway, I would talk to this chick and eventually the convo would turn sexual and maybe it was because I was horny I didn't notice at the time but somehow the convo would always turn to anal. Like we'd be talking about head or what we like or what we'd do to each other and she would ALWAYS somehow turn it back to fucking her in the butt. Never talked about being fingered. Never talked about being eaten out or getting her pussy ate or fucked or anything. It was always butt butt butt. Again I was so horny and dumb that I never even put 2+2 together back then but looking back on it now that was most definitely a trans or dude behind that AIM. They also never shared or sent pics, although they did have a profile pic of a chick with a big butt in jeans and a denim jacket I remember vividly. But yeah most likely I was cybering with a trans or a dude, years later and I refuse to belive that was an actual woman.
And then there was another chick that I talked to on AIM back then. We chopped it up and was talking for about 2 weeks. Exchanged pics and she was this really cute lightskin chick but she was sorta hiding her face in the pics. Like she was doing the Wiz Khalifa hiding face meme, where you cover your face with your hand and shit in a lot of her pics, which made me kinda worried but I still agreed to meet her. So I'll say right before she comes over, she says she has to tell me something and drops the bomb that she has a dick and that she doesn't know how comfortable I am and that she doesn't want to get beat up. Now keep in mind this is my very first encounter, I'm absolutely stunned but I tell her it's fine that I'm not going to hit her. She comes over and we just sit on the couch watching a basketball game. Like it was so fucking awkward. She was really cute though. I think she was waiting for me to do something but I was so fucking nervous I just sat there watching the game. After like 15 mins, she says she's just gonna go and I say okay and walk her to the door. She left and that was it lol very anticlimatic but I legit felt paralyzed and didn't know what to say or what to do. As I got older that obviously changed but that was legit my first IRL encounter. I have so more stories I could post.