For the more literary among you, my apologies. I had hoped to polish this more, but I wanted to get it written and out there before I ran out of steam.
I've known for a long time that, sometimes, sticking something in my arse while I'm wanking makes me cum harder and faster, but it wasn't until I was in my early 20's that I made the next step - discarding improvised 'toys' for the real thing.
I didn't have any clue how to find a partner for this, until I saw that my local rag had a 'seeking friends' section in the Personals. It was filled with people seeking fuck buddies (although, obviously, they didn't put it in those words), including guys seeking other guys. Striking up my courage, I answered the ad of a bi guy seeking other bi or bi-curious guys.
He didn't take long to reply to my voicemail message, and before I knew it, I was heading to his place.
As he lived with friends that didn't know that he 'hopped over the fence' regularly, he didn't waste any time. I had barely gotten in the door when he asked me where I wanted to start. I replied that I didn't know, whereupon he grabbed at my cock through my jeans and asked me:
"How about here?" I was almost instantly hard. He rubbed my jeans-clad package for a bit, and then took my boxers and jeans down. He asked me if I'd been given head by a guy before. I told him no, then he proceeded to show me what I'd been missing, right there in the hallway of his house. I moaned and ran my hands through his curly hair as he gave me the best suck-job of my life to date. He was a master deep throater, and I could feel my sensitive cock-head scrape the roof of his mouth as he took me all the way into his mouth.
After a couple of minutes, he stood up.
"This is what you taste like," he said to me, kissing me full on the mouth. I could taste my pre-cum on his hot breath.
Taking his semi-hard cock out, he told me to play with it for a while. I went one better than that, kneeling in front of him to return the favour. As to be expected, I wasn't the best at sucking cock- it didn't help that he wanted me to deep throat him - and I kept gagging on his fuck-stick, although I didn't flinch from his request to suck his balls.
He offered to show me how cock sucking was done again, by demonstrating on me, and got me to have another turn on him. Again, I couldn't match his display of oral prowess. He asked if he could fuck me. I readily accepted (as that was what I wanted to do all along), at which point he disappeared into a room.
When he came out he was naked, and carrying a condom and lube. He got me to help him get fully hard again, by briefly sucking him. He then sat down in a chair, and beckoned me over in front of him. He told me to stand in front of him and spread my legs slightly. While he took my cock in his mouth again he put the condom on, and spread some lube on his sheathed cock. Then, taking me by surprise, he parted my arse cheeks slightly with one hand and started to spread lube around the rim of my arsehole.
I gasped at the touch of his finger sliding over the entrance to my back passage. I thought THAT felt fucking awesome, but when he slid his first finger inside my tight arsehole my knees buckled and I moaned loudly. He kept sucking me while he continued to ready my arse for his cock - eventually he had three fingers in me - and I was transported to cloud nine.
Soon I was ready for him (not that I wasn't to start with!) and he got me to 'assume the position,' hands on the hallway wall, legs spread, my arse sticking out. He stood behind me, and eased his cock into my now 'non-virgin' arsehole.
It felt fucking fantastic to start with, but there was a little pain mixed in with the pleasure as he thrust his cock all the way into me. It didn't take long for him to build up the pace. It was a bit awkward, though, as I still had my jeans around my ankles - so I couldn't spread as wide as I wanted.
I got him to stop. He admired the view as I bent over to take my shoes off first.
"Stay like that," he told me, and put his cock back into its new-found home. As I leant against the wall, bent over fully, I could feel his cock go seemingly deeper as he continued to fuck me. The pain gone, I was really starting to enjoy the feel of his hard, thick snake burrowing its way into my hole.
We switched to a doggie-style position, which allowed me to push back on him, my arse meeting every in-thrust. I didn't know how long he had been pounding me for, but I felt like I could go as long as he could hold out for.
We changed position for a final time, me bouncing on his lap as he knelt on the floor. He told me he wanted to cum on my chest. I agreed, and got off his lap to let him get up. I stripped off my shirt as he stripped the condom from his almost ready-to-explode cock. I knelt in front of him as he wanked furiously. It wasn't long before he came, his dick shooting out fat splats of jizz which landed on my chest and face.
When he came back to earth he noticed that I hadn't cum yet, but - disappointingly - didn't offer to help. I tried to finish off, producing copious amounts of pre-cum. However, I'd wanked myself off at home earlier - in excited anticipation of the evening's events - and I couldn't get there.
Now mindful of his housemates' expected return, he hurried me to clean up and leave. As I stepped out the door, his parting words to me were to avoid married guys, as they didn't use condoms.
I never saw him again. Pity, because even though I didn't get off, I loved almost every minute of it. I guess that was all the encouragement I needed, because I had many more encounters 'on the other side of the fence,' until I got married.