New Acquaintance

This story is based on true events.

It was a cool fall evening. I had just arrived into town for a family get together at my parents' house. I arrived earlier than everyone else, as I wanted to see if I could hit up the bars with old friends from high school or even just grab a coffee and catch up with old friends. Even my parents weren't back in town yet, as they were on vacation and wouldn't be returning for a few more days. I figured I had several nights to myself to do whatever I wanted to.

I was in the stage of my life where everything was coming together and my outlook on life was looking great. I had a new girlfriend, whom I had only known for a couple of months. Everything was going great with her, and I felt affection, love, and extreme attraction to her. We had some of the most spontaneous and amazing sex. Her beautiful little body turned me on and I got hard just thinking about her. Her body was so smooth and shaped so nicely I easily could just think about her and jack myself off to completion. I knew she had been with a few boyfriends before me, and I would just get excited thinking about her getting fucked even if it wasn't by me. She was a very sexual woman, with a beautiful body, and an amazing tight little pussy that squeezed my dick so well. I would miss her for about a week, as I felt I hadn't known her well enough to introduce to my family just yet. I knew I would crave her pussy the whole time.

I had booked a cheap hotel for a few nights before all of the rest of the family would arrive. It was an older hotel, and to be honest, I wasn't all that impressed with it. That made me want to get out even more and try to find some old friends to hang out with.

I laid down on the bed, pulled up my phone, and started looking at my friends list to see who might still live in the area. As I started to scroll through, I thought to myself, should I try to find an old lady friend or guy friend? Since I was really happy with my new girlfriend, I thought it might be best to find an old high school buddy. Out of my buddies that I had stayed in contact with, none of them were available these next few nights, so I figured I'd be drinking with someone I might know just a little. That was fine by me, I was in a very social mood and wanted to talk about life with someone.

I began to message a handful of old high school buddies, but none of them were really available to catch up with a drink. I was a bit bummed out, so I decided what the hell, I'm going to just have a few beers to myself this first night in my hotel room, by myself.

I was feeling lethargic, so I ordered a 12 pack delivery of some strong IPA. I was chatting with my girlfriend on my phone, watching the edited version of Spaceballs on TV, and relaxing. After a few hours, I realized I had a strong buzz going, but I was almost out of beer. I didn't want to run out of alcohol, and I also didn't want to pay another delivery fee, so I put my shoes on, and started my one mile walk to a Seven Eleven.

After about half an hour, I arrived. A beautiful black Porsche SUV caught my eye in the parking lot, with the lights on, and the owner just idling away inside. Dark tinted windows made it so I had no idea who was in there.

I grabbed a 12 pack of IPA, paid, and walked back outside. I knew that I was buzzed and if anyone had been watching me, they would have known this. I wasn't sloppy drunk, but definitely impaired. I made eye contact with the Porsche again, and noticed the driver window was now down about halfway and I heard a faint, feminine "hey" come from the driver window. There was no one else walking in the parking lot, so I figured they must be calling at me. The "hey" sounded very friendly and inviting, so I didn't think I could be in any danger if I approached the driver and said "hi" back.m

I walked over and noticed a nice fit looking cross dresser had called at me. He had a wig on that made him look very feminine, and a cute all white women's shirt and jean shorts on to go with his outfit. I'm not going to lie I got a little excited at first sight. I was well under the influence and feeling very loose for the night. He said to me "would you like a ride home?" I said "sure!" excitedly. I felt like a little fooling around or something may happen, and in my state of mind, I was looking forward for that to happen. He said "Ok, come on in, I'll get you home, you look like you need a ride."

I hopped in, and he started driving. A few minutes in, he suggested "would you like to have a few drinks with me?" I replied "Sure!" He then said "can we please stop by somewhere else so I can pickup what I like to drink?" "Absolutely."

We stopped at a liquor store, and he got some seltzers. He bought me 2 airplane shots, and he said "here have them."

I asked him "is it ok if I drink these now?"

"Yes!" he said.

So I drank them quickly, one after the other, and started to feel really loose. I knew I was way past the point of good decisions anymore. After having those two, my recollection starts to fade out. The next thing I remembered was him telling me "we're here" and he helped guide me through the side of his house, to the back, where he had me sit down on his bed.

I remembered at this point that he had asked me if I wanted to drink with him, and I was still comfortable with him because I had remembered we were supposed to drink together. He offered me a Seltzer, after which point I remembered him telling me that I could go to sleep and he would take me home in the early morning.

At some point in the middle of the night, I woke up with only my shirt on, bent over doggy style on his bed, while he was gently fucking my ass. I looked back and I could see him shoving his thick cock in my tight little asshole. I was on all fours on my hands and knees. I knew that at some point in the night he must have taken my underwear off, and positioned me doggy style all while I wasn't conscious. I had a quick jolt of mild shock that he had done this to me while I wasn't aware of anything, but then I quickly got over that and realized I was experiencing pleasure. He was being gentle enough with me that it was enjoyable. In my youthful, experimental college years, I had been fucked before and it was mostly just pain. But this was absolutely enjoyable. He had his strong hands holding onto my waist, as if to secure me and make sure that I couldn't wriggle out of the situation easily. I laid down my elbows closer to the bed, to raise my butt up a little more, as he kept thrusting his rock hard cock slowly in and out of me.

I was so comfortable and I felt so good; I knew he had earned this so I started pushing my ass further over his cock. I myself had a semi hard on, pointing at the bed, but that was no concern as of now, as him fucking me was the main focus.

I started to think how this feels so good and how I could relate now to how it must feel to my girlfriend when I'm dominating her from behind. It was now my turn to get this feeling.

I ended up blacking out again after some time of enjoying being fucked.

I woke up to sunlight coming in through his window, both of us naked just laying in his bed. I thought to myself how exciting and pleasurable the night had been for the both of us. I was finally in a completely conscious state of mind and I could now thoroughly appreciate his thick beautiful cock. I put my hands around his cock and squeezed a little, while he had his hands cupped around my balls, gently squeezing them, to the point where I started to get hard. I could feel his cock getting hard too. His gentle squeezing of my balls felt so incredible that I started to get really hard and I could tell he was do this for a reason. He reached over to his nightstand and grabbed a tube of lube. He squeezed some out onto his hand and began lubing up my cock. We hadn't said any words to each other since the night before and this is how I liked it. He then sat up, slowly sat on my cock and opened up his ass cheeks, and my cock slid easily into his ass with the generous amount of lube on it. He rode up and down trying to get the cum out of me. It took him a while but his efforts paid off and I came inside of him. I could feel my hot throbbing cock spurt out cum all inside of him. I knew he felt it too, as he slowly pulled himself off of my cock.

He took me home as he said he would, we exchanged numbers, and we encountered each other a few more times. At some point, he changed his number and didn't let me know, and so that was the end of things with him. To this day, I think back to this night and my deep fantasies wish for a time like this again.