tagAnalAlley Anal

Alley Anal


His cock was pumping like a slow piston in and out of my ass and my face was pressed up against a brick wall in the alley. Both of my nipples were being pinched and rolled to excruciating delight. My new friend had only been at it for about two minutes and I was already on the edge of a mind-blowing orgasm, but let me rewind a little.

I work for a small manufacturing company and we were interested in some new cutting edge software for the business. So being that I am in charge of automation, I was voted by the other managers as the most likely to understand the new tech. Since we are such a small company, there was not enough money to take a second person, so I was on my own.

I was to fly out late Friday afternoon, check in to my hotel and get ready for the craziness that these conventions usually are. Fortunately I had done significant research and narrowed the field of software developers down to four. The problem was that I would have to sit through a demonstration of each of the products before I could get a one-on-one with the reps.

Saturday morning came and I was off walking to the convention center. It was only a few blocks from my hotel and walking was much easier than trying to get a cab or bus. I had reviewed the schedules and was able to get to all four of my presentations today, even if I couldn't meet with all the reps. The first presentation was slow to start but the pace picked up quickly as did my note taking. Before long I was near the end of the third presentation, it was one thirty and I was starving.

Knowing that my last presentation wasn't until three thirty, I remembered a little eat-in deli from my walk over and decided to go there for lunch. I just needed a little time away from the crowd to review my notes while it was all still fresh in my head. The deli was fairly busy but I managed to get a table to myself off in the back and had a great sandwich while I went over everything.

As I was finishing up I glanced down at my watch and saw that it was three fifteen and I needed to get back for my last presentation. Sitting down, I was pretty sure that I was going to go with the company that did the second presentation, unless of course these guys really blew my socks off. When this one came to an end it was a toss-up in my mind as to whether to go with these guys or the second one. So I needed to sit down with some reps and get more details.

I got an appointment with a rep from company four at about five, so I quickly went over to company two to get an appointment with one of their reps. Unfortunately they were already booked up for the day according to the scheduling secretary, so I set one for Sunday at eleven in the morning. Turning to leave, I literally bumped into one of their reps and just stared.

Have you ever seen someone that, after that initial glance, you couldn't tell whether they were male or female? They were either a very feminine male or a slightly masculine, but attractive female.

While I was stuck in some sort of trance, Steven apologized for bumping into me and reached out to shake my hand. Coming out of my daze, I grabbed his hand and, shaking it, extended my apologies as well. Steven asked me if there was anything he could help me with and I told him that I was hoping to meet with a rep from his company today.

He said that he was all booked up until seven this evening but maybe we could meet up later if I was going to be around tonight. He was planning on meeting some of the other employees at the bar in the hotel next door at around nine thirty. I told him that I would try to make it but that I still had a lot of notes to transcribe.

The truth is that I really dislike bars and I'm not much of a night person. I did however, feel very attracted to him and was pretty sure I would be there.

I went back to meet with the rep from company four and, after the thirty minute meeting, was almost positive that they were the one. Their software was more user friendly and expandable, so that as our company grew it would too.

Heading back to my hotel all I wanted was some dinner and to take a nap before going over the rest of the paperwork. I decided on room service so that I could relax as I worked. As I entered the hotel I went over to the front desk and placed my room service order so that I wouldn't have to bother with it later.

Before my room door even closed behind me I was stripping off my work clothes and kept going until I was completely naked. Thinking that it may not be a good idea answering the door for room service that way, I remembered that there were complimentary robes in the closet. After slipping one on, I spread my papers over the bed and got to work.

The room service came and I ate while finishing my paperwork and at some point drifted off to sleep. Waking from my thirty minute nap, I felt refreshed and quite horny due to a rather vivid dream. Knowing that there was almost no way that Steven's company could match the offer I already had did not deter me from going to meet him at the bar. If anything I was more excited knowing that the business conversation would be short.

At nine fifteen I entered the bar and spotted Steven almost immediately. He waved me over and introduced me to a few of his colleagues before leading me to a corner table for two. He said since it was late he would just give me the short version of his presentation and for me to ask questions as needed. As he spoke he slid his chair over to mine so that we were nearly touching as he began.

Other than being that close physically, he was very professional and rattled off his sales pitch as if he was speaking to a full room. Within ten minutes he had hit all the highlights of his software package and paused, waiting for me to respond. There was an awkward silence for almost a minute as I stared into his beautiful blue eyes, before he finally asked me if I had any questions.

Deciding to be blatantly honest, I told him the only reason I was there was to see if he would fuck me. It was now his turn to be silent, but quickly his left hand wandered into my crotch and his right pulled my face into his for a long sloppy kiss. As the kiss continued I rubbed his cock in earnest through his pants and felt it harden quickly.

When our lips finally parted he asked if I wanted to move this to the bathroom. I said outside would be better since it was getting very hot in the bar. Grabbing my hand, he pulled me to my feet and we headed out the front door. Once we were outside I spotted an alley to the right of the building and we walked that way briskly.

After a quick glance we determined that it was relatively clean and quite vacant. We moved down the alley about fifty feet just past a couple of dumpsters. It was there that I dropped to me knees and freed his cock just lock enough to stuff it in my mouth. After about a minute of coating his cock to the root with my saliva, I stood up and quickly removed all my clothes.

Steven took the hint. Pushing me towards the wall he spread my legs and started rubbing his cock across my ass. He quickly pushed himself into me a few inches before pulling back out and adding some of his own saliva to the mix. Upon entering me again, he slowly went deeper on each stroke until he was bottoming out in my ass, which brings us back to the beginning.

Within a couple of more minutes I starting cumming and my contractions started his orgasm. Steven held me tightly while we both felt the spasms of his cock until it came to its unfortunate conclusion. We still stayed in that position for a few more minutes as his cock and cum slowly left my ass.

Still naked, I turned to kiss him and fondle his softening cock. As our lips parted he asked me if I would like to go again in his hotel room. I told him that I was rather tired tonight, but that I would be here until tomorrow afternoon if he was still interested.

Pulling on my clothes to leave, I told him that I really enjoyed morning sex and gave him my hotel info as I walked out of the alley.

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by Anonymous

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by latecomer9136409/04/17

You shameless vixen!

Loved it, you naughty wench! Business sex with a stranger in an alley far from home is such a delicious fantasy. Bonerville Express!

More, please...

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