The First Time June 12, 2017 A True Story by somefun421 Well after many years of solo anal play, I decided it was time to try the real thing. I'd had a few abortive attempts in the past via AMM - arranging a meet, but then pulling out (greatly regretted now - I still look at photos of the cock & think what may have been...). One Friday night in June a couple of years ago my GF was out & I thought fuck it, it's happening tonight. Fortunately there was a guy online & after a wink he sent me a message. He was much older, late 50/early 60's - we exchanged a few messages & he invited me over to his place. He mentioned he liked to dress up, which I said was fine. About 40mins later I knock on the door with a box of condoms in my pocket. The door opens & he invites me in. He's in a dressing gown, wig & lingerie. We sit in the lounge & we have a bit of chit chat - I'm super nervous at this point, my heart is pounding...he invites me to come & sit next to him which I do. He pulls his cock out & says to put my hand on it. It felt so awesome in my hand & after about 10 seconds I was on my knees sucking his semi hard cock. I can't believe how good it felt to suck his cock as it got fully hard to about 7ins. It was such a good feeling. He was getting into it & he must've been enjoying as he said we'd better head down to the spare room. He led me down the hallway to his spare room. I dropped my pants & he blew me a little. He went off to grab the lube & my heart was pounding even harder now...he came back & before he had a chance to put the condom on I was back down on my knees sucking his cock. After a couple of minutes he put the condom on & told me to get up on the bed. He lubed up his cock & my hole & pushed it in on the second attempt. At first it was a bit painful, but after I laid on my back with him standing it started to feel so much better. After a couple of minutes he suggested I get on top. He laid on the bed & I climbed on top...his cock felt terrific sliding in & I was grinding & riding his cock in no time. After another 5 mins or so I jumped off & went back to all fours with him standing as I wanted him to fuck me as hard as possible. He had me by the hips & I started to push back hard on his cock as he thrusted - his balls were slapping me hard...it felt amazing & all I could think to myself was I'm going to milk every drop of cum from his balls. He gave a couple of big thrusts & let out a groan & I turned around to see him pull his semi hard cock out of my arse. The condom was full & I was so turned on. He pulled it off & headed out of the room. I grabbed my pants & followed him out, cleaned myself up a bit & met him back in the lounge room. He said he knew a couple of guys who'd love to pound me & said I should find some young guys that could go all night. I had a great time & I was so glad to have tried the real thing...the next couple of days I couldn't think of anything else & kept thinking I should go back. About 6 months later I'd tee'd up a Sunday morning meet, but pulled out (another regret)...I couldn't get my mind off it & a few months later I rejoined AMM, but he'd dropped off...that was about two years ago & I often think, if only I'd gone back - I could've had his cock 100 times & hopefully have moved on to him depositing his load into my arse very regularly sans condom. Funnily enough I did see him again - it was at a dress up party (where my family was!!!) so I didn't have an opportunity to reconnect...it's given me plenty of material though as I often think what if we ran into each other in the bathroom, ducked away etc... Enjoy this story? Give us your rating. Join now and vote for the story!