Mr. Hilton Hotel

I was bored one night and I posted on Craigslist, and curious to see if there were any cute guys who would want to have some no-strings fun. Now, my opinions on CL, are it's really sketchy but I've always been really lucky. This was the first time I'd posted in the 'casual encounters' section though, usually I post in the regular section looking to just meet someone new. I had tons of replies, as usual (okay, I know, that sounded snotty..) but one was from a 27 year old businessman who said he was going to be staying at the Hilton that week on business.

We clicked while we chatted on AIM but unfortunately I began surfing the "crimson wave" that week and someone that eager to have fun with me was a bit scary, so we kept talking for two weeks until he returned again on business. He arrived on a Wednesday, and I met him at the Hilton that afternoon and we had lunch at the hotel, his treat. We clicked well in person too, and I aw'ed at his Western Pennsylvanian-accent. I had some place to be, and he had a meeting to go to at 2:30pm, so I hugged him goodbye and he said, "Hopefully I'll see you later!"

We were texting around 5ish and I ended up going over to the Hilton. I had recently gotten a Brazilian, and I was still a bit tender, so I was afraid it might hurt a bit. He answered the door, and I walked in. It was by-far the most outrageous thing I'd ever done... meeting a man at his hotel room, whom I hardly knew... We chatted for a few minutes and then he grabbed my arm and pulled me towards him, and started kissing me. I had made it clear that unless he was willing to make the first move, there would be no moves made. I was glad he understood that!

We kissed, hard and passionately, for a good while and then his hand made its way around to my ass, where he groped me hard, and then to the front of my skirt... finally he pulled my skirt up, revealing my thong, and stroking my smoothness and fingering me until I was more than wet. I had kept my hands around his neck and on his toned arms, while I moved my leg up and down between his legs, gently grinding into his already-rock hard cock. Finally I couldn't take it anymore and I put my hands on him. He moaned, and took it upon himself to release his throbbing package and I took him in my hand and started stroking.... which only ensued more moaning on his end.

He pushed me up against the desk in his suite, where he continued to finger me and removed my shirt. I soon found myself pressed up against a 12th floor window, my bra having been removed, my hands against the glass, gazing upon the working crowd going about their usual day while I was being seduced in a suite at the Hilton by someone who was practically a stranger. I moaned at he fingered me quickly, and kept his other hand on my breast. He kissed my ass all the while.

Finally, we moved into the bedroom. I laid down, he removed whatever articles of clothing remained and we continued kissing passionately, naked, until he kissed his way down my body to my wetness. I moaned and leaned my head back as he dove in. He licked me all around, flicking my clit with his tongue, keeping a finger inside of me, and eventually moving it to inside my ass. I let out a 'ooh!' when he did that, since that was a complete first for me. He was very gentle and eased his way in. After about 30 minutes of him sending me into pure ecstasy, he asked if I would go down on him. I said, "probably very poorly," and smiled, having told him about the smack to my confidence in performing oral by one of my past ex's. He said, "Let's just see about that," and I asked for basic instruction and went for it. Afterwards, he said I was very good and that my ex was sorely-mistaken.

We fucked briefly after, hard, and I left for my doctor's appointment... refreshed and with my head spinning a bit. We were planning on meeting again that night. And we did, around 11pm I arrived back at his doorstep... I have to admit, I felt a little bit like a hooker coming in and out of the Hilton so many times in one day.

He answered the door once again, and we made our way to the bedroom quicker this time, and more of the same as the afternoon took place. His cock was throbbing before I walked in the room, and he asked if he could come once before we started to fuck. I said yes, and I was cum on for the first time... my tits more specifically. I enjoyed it except for the fact that I hadn't been able to put my hair back before, so when he came, I was afraid of it getting in my hair. We kissed passionately, briefly, then fucked. I dressed, he kissed me goodnight and I made my way home to go to work in the morning.

Thursday night soon came... and after I got home that night from a long day of work, and he returned home from a business dinner, I made my way over to the Hilton once more. He took me in his arms a final time, and it'd be repetitive to say what we did, but this time, he'd bought lube and I supplied the condoms this time, so we were going to take a stab at anal. The only other time I'd tried anal was with my boyfriend from high school, who was also a completely virgin before we started dating, so we both had no idea what to do... so it was a horrible mess. Mr. Hilton Hotel though had done it before, and he seemed to know just how to go about loosening me up.

He put a condom on and lubed up, LOTS of lube. I got on all fours and clenched my fists, and gritted my teeth, preparing to endure the most horrible of horrible pains. It took him about 20 minutes to fully insert himself, but we fucked that way briefly, and I loosened up a bit. Finally though I pulled away, requesting that we finish traditionally. He obliged and changed his condom, answering, "if I was an asshole, I'd use the same condom. You can get infections if you use the same one," to my naive questioning of why he was changing his condom. Wow, he really was a good guy!

He was on top first, then I rode him, which engaged him and made him cum rather quickly. I kissed him and dismounted, heading to the bathroom to nurse my painful lower body. To my surprise, there was hardly any damage done. I got dressed while he disposed of the condom in the bathroom. I kissed him goodnight once again, told him to have a safe flight back, and made my way home. He left the following afternoon!

He was so good at loosening me up, in fact, that I wasn't even sore the morning after! I think he'll be back in town in a few weeks... we shall see!