Craigslist hook up

I’m not ever going in chronological order with any of my stories that are true or partially true. Everybodies over 18 by a damn sight.
I had some experiences in my youth playing with guys, but I considered myself only slightly bi, and even then only secretly.
My most successful sexual relationship with a female was when she occasionally fucked me in the ass with a strap-on. I had hot girlfriends from time to time but I had a hard time ever making relationships work. The few encounters I’d had with guys were usually mild disasters. I had fucked around quite a bit in gloryhole booths in my 20’s back when they existed, but had to get d***k enough to have the courage to go in. I was scared as hell of being outed which was stupid because I couldn’t be judged by anyone who knew, because they would’ve maybe already had my cock in their mouth or vice versa. I was still pretty scared going in the booths, more like , intimidated, because sometimes it was a pretty aggressive crowd. I liked to get in a booth and chill for a few and get my courage up to respond to the finger coming through the hole in the wall, or the jiggling of the door latch. Whether I did respond or not was never sure, but if I sat down and picked a good movie, and started jerking, I might not need any other involvement to get off. Sometimes, because I wouldn’t respond right away, guys wanting to play must’ve assumed I wasn’t interested and left me alone.
But if I was d***k before 11 on a Saturday night but still sober enough to drive 2 blocks, watch out.
The butterflies of fear in my belly made me more susceptible to my buzz and by the time I got settled in a booth I was ready for anything. I’d open the door occasionally and let some guy in, and we’d do, whatever. One time I eased my door open just a crack to see who was trying to get in, and when I saw a black hand I shut the door quickly. All the guys cruising around my booth were laughing. After that I couldn’t open my door again so I got myself off and scuttled out of there embarrassed as hell. It wasn’t that I was racist, I just didn’t think there was any way I could anatomically do anything with their great big dicks! I thought there was noway they would ever fit.
One time I opened my door and a good looking white dude told me he would do anything I wanted. I let him in and after we’d sucked eachother and played with eachothers asses in the booth, we split back to my apartment and fucked and sucked and did poppers for like 4 hours. That was probably the only good gay sex I’d ever had but I was so d***k I don’t remember it well.
I craved cock a lot after that but never really got anything else. I cruised a local gay bar a few times and never really got picked up. One older guy was staring at me for hours and never had the sense to buy me a drink or start a conversation. I loved the trannys at the club and thought at the time that my ultimate fantasy was to get fucked by a guy that looked like a girl. That never happened but I never really got anyone interested in me enough to go have sex.
A bunch of stupid shit happened after that, suffice it to say I was locked up for a few years.
And no, I never touched a dick the entire time I was locked up, despite what everyone says goes on there, because it doesn’t pay in there to advertise that you might be up for it.
Anyway I had a few brief encounters that weren’t great. One guy I met had a horsecock but after sucking him off and making him finish himself off, for some reason I never had the courage and opportunity to call him again.
I met a crossdresser through a personals ad but he hid his clothes in his work van, and they smelled. I was excited about that at first but he also stalled about doing anything that first night so I lost his number.
Nothing ever panned out for me until years later, when I started cruising craigslist.
A few hits, misses, and foul tips later, I still hadn’t really found anything that worked. I got my dick sucked a few times but mostly nobody was able to really get me off. A lot of the time, guys would flake before the hook up so you’d drive a half hour with a hardon for nothing.
One morning, I called in sick to work, and answered a couple early a.m. ads. One guy said he wanted to suck dick, but when I responded saying I was vers and wanted to suck him and lick his ass as well as get my dick sucked, he eagerly returned my email.
He was close by in the city. When I got to his apartment I knew which one it was because there was a huge sunflower growing in front. He let me in and told me his name. We sat and chatted for a minute and smoked for a while.
When he finally asked me if I wanted to see his cock I told him fuck yeah. He stood in front of me and pulled his jogging pants down and let his cock flop out. It wasn’t exceptionally huge but real nice, with the head somewhat bigger than the shaft. I immediately grabbed it and started stroking it back and forth. He suggested we move to the couch. We stripped on the way, and he knelt on top of the couch so I could get at his ass. I crouched behind him, started tongue fucking him and sometimes smothering my face between his cheeks. After a few minutes of this he flipped over and sat down and I began to suck on his hard cock. When I started going really fast, he told me to take it easy. I explained to him that I wanted to try and take his load. He confessed to me that he had already come this morning so he thought that was impossible. I slowed down and then lifted his legs and licked his ass some more.
After feasting on his ass, he asked me if I wanted to fuck him. I was way into it by now, loving the way his ass felt on my face. He rubbed some lotion on his ass, and I got some on my dick. As I started to ease my dick in, I asked him if he was ok and he kinda snapped at me about a lot of big cock being in there before me and he was sure it was no problem. I took that as an invitation to press on so I pushed in all the way, and sure enough, as soon as I got past the ring of outer muscles, I felt the bottom drop out, and I was able to easily pump in and out. He had a nice little body, as I confirmed when I grabbed him by his curvy hips and drove as far into him as my 5 inch penis would allow. I felt so free driving my dick into his hot asshole. I alternated between holding his hips and shoulders while I fucked him. I tried to reach around and play with his dick but he pushed my hand away. I finally pushed him flat on the floor and because his ass tightened when I did that I had a nice big shuddering orgasm inside him, and totally bareback. He got out from under me and we both sat and had a smoke. When I started sucking on his dick again, he asked me if I was ever going to come. I laughed and told him I just did, and he asked me where. I said I came inside him, and he frowned at me for a second until I returned to sucking his cock. Instead of thrashing on his dick like I did before, I slowly worked it further and further down my throat and slowly sucked him in harder and harder. I got a good rhythm going, sucking it in, down my throat, and squeezing it out with my tongue and lips. He complimented me on my skills, saying I was a natural. I just really liked his cock and tried to do to it what I’d like to be done to mine. He was so hard as I sucked him I thought maybe I could still bring him off even though he’d assured me more than once that he couldn’t come again soon. He asked me if I wanted him to fuck me and I said hell yeah.
He asked me if I’d been fucked before and I told him a long time ago. He was afraid I wouldn’t be able to take him all the way but I told him I used to masterbate anally with a few fairly large toys so I was pretty sure I could take him. We did the lotion again and he slipped his head in my ass. I relaxed to let him in further. He pushed a little further and somehow he bumped into something that hurt. I told him to ease up a little and he asked me if I wanted to stop. I said fuck no I want your cock. I said I just think the angle is slightly wrong. He suggested I arch my back a little up and down until it feels better. Sure enough, when I bent at the waist slightly his cock went the rest of the way in. It hit that spot deep inside that makes me want to come, and he started bumping into it over and over again as he fucked me. As I jacked my cock I got really comfortable with his dick in my ass and started backing up into him in time with his thrusts to keep his head pounding my hot spot. I worried that I would come before he was satisfied and I hoped he would come inside me. I told him to grab my hips and fuck me hard. I told him to let me know when he was coming so I could try and come at the same time. He then reminded me again that there was no way he could come again so I just keep pushing my ass back at him and jacked off in my hand while he continued to fuck me. As soon as I came, he got off me and asked how it was. I told him I loved it and wanted more cock. He apoligized when he told me he needed some sl**p since he had worked all night, which was why he was able to hook up in the a.m.
I told him I wanted to see him again but since our work hours were so far fucked up, and I would be out of sick days for a while, there probably would be no way. I left his place and went back home and napped, basking in the glow of finally getting fucked right, and I loved it. I still jack off thinking of that encounter and wished we had stayed in touch.
The funny thing was , his ad said he wanted to suck cock, and he never actually did, but I got all the cock I wanted.