Guy two was a senior in college who actually lived not too far from me. His roommates were home, and my roommates were home, so we planned on meeting out and playing things by ear. He's kind of a classic Jewish frat boy, but (but? is it anti-Semitic or anti-frat to say "but" to make up for those qualities? maybe) he's super smart and when I stalked his post history after first getting his message, he had made this super supportive comment to some askReddit post where a guy wanted advice about coming out to his family and i was like awwww what a mensch. I met him out and he was immediately really flirty and forward like he had been in his messages which was cool. We made minimal conversation and then he leaned over with a bunch of people around us and was like "so when are you gonna suck my cock," which is a line that I typically wouldn't respond well to but he was so confident that I was ready to go like right then. Neither of us wanted to take it back to our place, so he suggested his car. He was parked on a side street back by his house, so we walked over there and hopped in. He mercifully turned on the heat while we made out for a while, and then my hand made its way down to his pants. He was wearing jeans and these tight boxer briefs which I couldn't pull off with him sitting down, so he pulled the whole deal down to his ankles himself and lifted up his shirt and fleece a bit. He has terrific and delightfully hairy abs and a full bush, so I ran my hands over whatever I could get to on his body before leaning my head over to the driver's seat and starting to suck. He ran his hands through my hair and moaned kind of a lot, and he's a bit smaller than guy #1 (sorry player), so i was able to take him all in and properly bury my nose in his pubes. After a bit, he started groping at my waist and stripped my entire top half, and then worked his hand down my pants and fingered, not my pussy, but my asshole. It was a pretty hot surprise and something I have verrrry little experience with, but he went slow and it was awesome, especially combined with the fact that I was totally exposed in this public situation which apparently I'm into. He grabbed the steering wheel at one point and shouted "FUCK!" which was incredibly funny and hot in the moment. When he gave me the heads up I wrapped my lips around his cock head and tugged on his balls. Dude can seriously cum. I think the average is a tablespoon or something, but it just kept coming and coming, and he kept saying "swallow it," so I did. We kissed again and he walked me home after I got dressed, because he'd had two beers and I am a responsible lady. I didn't meet up with guy #3 until the next night, Saturday. I wasn't super sure about his initial message to me, which said he was just there for a few days at a hotel in SF and he'd teach me how to take it like a good girl, which seemed infantilizing but sexy. He also was 39 and had kids and an ex-wife back on the East Coast He wasn't super in the wheelhouse of guys I was expecting to meet with, but he was attractive and in amazing shape and his dick just looked tasty if you get my meaning, so I followed up and scheduled him for last. We decided to meet at a restaurant in his swanky ass hotel, and we got a bite. Our hostess made some comment implying that we were father and daughter when she was seating us, even though he's blond and doesn't really look like me, and he played along with the comment. The naughtiness of the whole thing turned me on. Also this time, with us sitting more or less next to each other in a pretty private corner with a tablecloth over our laps, it did get a little heated under the table. I was wearing a dress despite the super fucking freezing cold, and he kept running his hand up my thigh while we were talking, eventually moving all the way up to my panty-covered mound. The conversation was what ultimately get me really ready to "take it like a good girl"; he was confident and worldly and so fucking comfortable with himself and the situation which is sometimes a nice change of pace, although I truly do love my awkward shy boys too. He quietly asked me to excuse myself and take off my panties in the restroom as if we were in an adult erotic thriller, and I happily did so. I came back with them balled up super tightly in my hand and passed them to him, and he put them in his inside suit pocket. Then the fondling began again, with the occasional slip of his finger into me. He kept having to wipe that finger off which was funny, because I was producing a lot of "fuck me" juice at that point. I returned the favor by awkwardly squeezing his big ol boner through his pants a few times. After dinner, we basically raced back to the elevator. We thankfully got into an empty one, and as soon as the door closed he turned me around and shoved two fingers into me, with the other hand on the back of my neck. If at any point this sounds like a completely fabricated porn-for-ladies erotic fiction, it's because this guy knew exactly what the fuck he was doing. We pretty much ran down the hall into his room and he opened the door, letting me through first and promptly yanking off my dress and bra with the door still open. That, by the way, is a really good move that I would highly recommend if you've got an adventurous lady with you. He quickly pulled off his suit jacket, tie, and shirt in a very non graceful way and then kicked the door shut. Adding to the exhibitionism of it all, his window was wide open and all the lights in his room were turned on. This move also worked well. We moved/made out over to the side of the bed closest to the window, and i (again, awkwardly) yanked off my heels and got down on my knees. He pulled his pants down to his ankles (no underwear, a nice touch) and i threw myself down onto his cock, which was about the same length as guy #1 and the thickest of the three. He immediately grabbed the back of my head and started skullfucking me. There was lots of gagging and drooling to be had, which got all over his suit pants and shoes. After a bit of this, he stood up, took his shoes, socks, and pants off with a few funny hops, and then picked my up by the armpits and laid me on my back on the bed with my head over the edge. He fucked down into my throat which was awesome but involved his balls slapping my face a lot. I can't say I minded though. Then he asked if I brought any condoms, which I hadn't because I had no intention of having sex sex, followed that up with asking if I wanted to fuck, to which I said "fuck yes," and then, I shit you not, walked calmly over to the phone, called down to the concierge, and asked for some condoms to be brought to his room. It was such a real-adult style power move and it was soooo fucking hot, so also keep that in mind as a future move to try with your lady. He laid back on the bed and put his hands behind his head, and I crawled over and got back to sucking him while he told me all about how hard he was going to fuck me. An excruciating maaaaybe 10 minutes later, there was a knock on the door and he hopped up like the bed was on fire, ran to the bathroom to grab a towel, and the condoms were in this little tasteful gift bag thing outside the door, which is how you truly know you're in a luxury hotel. I'm now realizing that this is becoming a novel, so long story short, he fucked me real real good, we passed out, he fucked me again in the morning, and then he politely offered me cab money but it felt hookery so I half limped my ass to the train and went home. Tl;dr: Ended up picking three guys instead of the planned one, had three super different but all quite positive experiences, down to do it again.

P.S. I told guy #3 at dinner that I had already sucked two other guys, he said "good job" and gave me a high-five.