a few times, yeah. first was in high school...met this girl online who went to another nearby school. we chatted online, then on the phone, decided to meet in real life. turned out i wasn't all that attracted to her, but she was VERY into me so she kept in contact and over the years seemed to pop up when i was feeling my most insecure, particularly in college. once, we made out in my Jeep but it didn't go any further. then she showed up at my house when i was feeling pretty low over a break up and she wound up going down on me while i fingered her and let me cum on her tits. a little while later, i had moved to a different place but was still reeling from the break up and she was in the neighborhood so swung by and showed me her new vibrator, which was about my size and i used it to get her off in my living room. and finally, one night after a party where i'd had to deal not only with my ex but a couple of crushes that weren't happening, i got home drunk and she IMed me and invited me over to her place...so i sobered up enough to drive (but enough to realize this was going to be a bad idea), headed over there and fucked her brains out while the sun came up. she came several times and we fell asleep in her bed...woke up around noon, fully sober and decided it would be best to get the hell out of there. we talked for a bit, i got dressed and drove back home. we talked a few times after, but i never saw her again and we haven't spoken in years. guess i haven't felt low enough to pop up on her radar since.
when i first started college, i met this girl in a chat room who lived in the same town and was actually going to the same college as a grad student. we chatted a bit, traded pictures and i invited her to come see a show i was in. we flirted for a bit after and decided to go on a proper date later that week. i didn't have a car at the time, so she picked me up on campus and we started to head out on our date...but then she asked, "do you just want to go back to my place?" i'm 18 and i've got a pretty hot somewhat older girl asking me back to her place...i don't think the word "yes" came out fast enough. lol! we got there, talked for a bit in her living room then started making out. she asked, "do you mind if i suck your cock?" again, i would think the answer to this was obvious. she was amazed at my size and that i was already rock hard...then i went down on her for a while and had some fun with her piercings.
we fucked for an hour or two on her couch and it was incredibly hot, and then she drove me home. she decided it would be a bad idea to date me because of the age difference and since i was a student and she was technically a teacher (even though we were in different departments)...but we got together on and off (taking breaks whenever one of us wound up in a relationship) for the next year or so to just go wild on each other. it was fun and intense. my friends knew about her because she'd still come to see my shows from time to time, but her friends only knew me as "the good sex guy" and i never met any of them. after a while, i started to feel bad because it was just physical with no real emotional component so we called it off. still chatted every now and then, and she found another guy shortly thereafter and the last i heard they'd gotten engaged. but then i didn't see her online anymore and lost her number and haven't spoken to her since...
a few years later in college, after i'd slept with the first girl i talked about and was still feeling low from that same break up (seriously, that one fucked me up for a while...), i met another girl online and pretty much the same thing...chatted, flirted, traded pics. she lived in another city a couple of hours away but came to mine fairly often. and on Halloween, we decided to meet up. i picked her up from where she'd been partying with some of her friends but they'd ditched her there...she was already pretty drunk at that point. she was cute, but i wasn't incredibly attracted to her but figured we could hang out anyway, see if there was any chemistry, that kind of thing. took her to a friends' party and she started acting very obnoxious towards everyone, which didn't help. i decided since she couldn't find her friends and wasn't sober enough to tell me how to get back to their place i'd take her back to mine, let her sleep it off and take her in the morning. but she got very amorous on the way home and started kissing me and rubbing my crotch...so by the time we got home, i was a bit more pliable to the notion of sleeping with her. we got to my room, she excused herself to go to the bathroom, then came back and started to go down on me. it wasn't very good, but it was something and i was low enough at that point to settle for anything. i decided to go down on her...took off her panties to find the WIDEST bush i'd ever seen. not necessarily thick, but spread out over a good amount of acreage.
i persevered and took my first lick...let's just say she hadn't been too thorough after she'd gone to the bathroom. but, again, i powered through and got her off a couple of times before she asked me to fuck her. she seemed to be having a marvelous time and came quite a bit...but for being that vocal, she also just kind of lay there so i was pretty much doing all of the work and felt kind of bored after a while. i finally came and got off of her. by the time i had thrown away the condom and come back, she was dead asleep and snoring. i watched some TV for a few hours until morning came, then i woke her up and drove her to her friends' place. several months later, she came back into town and asked if i wanted to come out with her and her friends...enough time had passed, i decided to see if that first time had been a fluke and maybe we could get along in real life like we did online. met them at a bar, things were nice and flirty and kind of touchy feely, which was nice. but by the time we left the bar, she was drunk again, obnoxious again and i knew then i wasn't going to sleep with her again. but i helped her friend get her back to his place...where, mere yards from his front door, she decided to squat on the sidewalk of his apartment complex to relieve herself. which pretty well doused any remaining sexual attraction or chemistry between us. i helped her inside, she changed clothes and passed out...and i stayed up with her friends, drinking and watching cartoons. so that evening ended MUCH better, lol. and i never saw or spoke to her again.
(continued in next post...)