Scroll down to the asterisks for the fun stuff*

Our second encounter takes place a few months after our first meeting. We had talked a little bit after our first encounter but after a few days the talking fizzled and I went back to business as usual. I honestly didn’t think we would meet again but an opportunity to travel to the same place came up and I decided to reach out again to try my luck since I didn’t feel like going through the tinder set up process again.

Lo and behold she responds almost immediately! We started off with spicy talk almost straight away reminiscing about our last encounter and how much fun it was. I asked if she would be willing to meet up again and she responded, “how can I resist??”. I had meetings all the way up to Friday so I decided to leave on Saturday to make my travel day lighter and to maximize my play time. With this in mind I also upgraded my usual hotel room to a room that also had an ensuite hot tub to add a bit more spice.

We made a plan to meet up at the hotel bar again and have a few drinks before starting the evening festivities. I must say the days leading up to Friday, I could barely contain my excitement! If you had asked me what was discussed during any of my meetings I wouldn’t have been able to answer.

Friday finally rolls around after what seemed like an eternity and while getting ready I started getting butterflies in my stomach. Something about the naughtiness of meeting someone and the discretion associated with it makes it that much more exciting.

We met in the hotel lobby and she looked absolutely magnificent in a black lace dress with matching black heels. The dress was short enough that I was sure if she sat down, wasn’t to going to cover much. She greeted me with a long deep kiss and I was already at half mast. If we didn’t get to the bar quickly I was going to be standing in the middle of the lobby with a full on erection.

We made it to bar hand in hand and decided to sit away from the bar in a high top table that was partially hidden from plain view. During our last encounter she mentioned that she was the submissive type and I was planning on taking full advantage of that tonight. A few things about me that are will be important later on is that I’m into exhibitionism and I LOVE anal!

We started off the night with a few drinks and as time went on we were getting friskier and friskier. It started off with making out like high school teenagers and quickly morphed into her groping my dick from the outside of my pants and me rubbing her pussy through her panties. I was already rock hard and initially was worried someone might see us but as the drinks flowed I stopped thinking about it altogether and I was getting ready to take the party upstairs.

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On the way up to my room I asked her to take her panties off in the elevator and hand them to me. She gave me a funny look and said “You are naughty!” but did as I said. From the elevator to the room was a long hallway so when we got out of the elevator I told her to hike up her dress and show off her ass and dripping wet pussy. This time she did as I said without hesitation and said good girl and gave her an encouraging ass smack. While walking down the hallway I was hoping someone would come out and see her with her butt hanging out but no such luck.

We finally get to the room and her eyes lit up when she saw the hot tub. I started running the water while we got undressed. We were now fully naked and making out and I could tell she wanted to get fucked immediately but I wanted to tease her a bit more so I made my way down to her pussy and started eating her out, the moans I heard were probably the loudest ever and I felt her first orgasm after about a minute or so of eating her out. She was grabbing at my dick but I wanted to keep teasing so I was putting the head of dick in her pussy and was just fucking her with the head for a while then went back to making out and fingering her pussy. I tried to finger her ass with one finger but she kept pushing my hand away so I stopped trying, for now.

The hot tub was almost ready so I lifted her up and walked over to the hot tub, sat down with her still in my lap and making out. I was impressed with myself for being able to lift her into the hot tub without tripping over the steps to the hot tub. The water level was a bit too high so she asked me to sit on the edge of the hot tub and started going down on me. Her deepthroat skills were just as phenomenal as I remember and I had to focus on not cumming for the first 30 seconds and the noises/moans she was making from sucking my dick almost sent me over the top. After a few minutes of being in heaven I stood her up, bent her over and started eating her pussy from behind then I switched to fingering her pussy and eating out her ass. She started going wild with the moans getting louder and louder, this gave me encouragement to go harder and harder until she came again. I continued to finger her pussy and tried to finger her ass again this time she was much more receptive so I tried to be as gentle as possible to not get swatted away again.

I was ready to fuck now so I stood up with my finger still in her ass and started teasing her with the head of my dick again until I finally pushed all the way in. She was much wetter than the last time we had sex and it felt amazing. I started to pick up the pace and really pounded her from behind with the hot tub water splashing back and forth and making a mess of the room. We then switched positions and I sat on the edge of the tub with her sitting on top and riding me. I started playing with the entrance of her asshole again and stuck my finger in, almost immediately she started moaning very loudly and I started feeling her pussy pulse on my dick, signaling another orgasm. I wanted to try anal so I hopped out of the hot tub, bent her over so that her arms were gripping the edge of the hot tub while I started pounding away while also fingering her ass. I then decided to try going for it and pulled my dick out and started fingering her pussy with my other hand and used my saliva to lube myself up and started slowly teasing her asshole with my dick. Her ass was super tight and if I had any chance of anal I was going to have to take it super slow.

After a few minutes of doing so I was able to work the head of my dick into her asshole and she let out a slow long quivering moan. I held myself in that position for a bit before trying to push in further. She started to relax a little more and managed to get about halfway in before she asked me to pull out. We did this 5 or 6 more times with more and more saliva until I was able to get my entire dick into her asshole. The tightness and the warmth of her asshole felt like heaven and I couldn't wait to started pounding. I took it slow and pulled half way out before pushing in again after taking it slow for about 10 minutes, she was comfortable enough for me to pick up the speed and it took about 30 seconds or so and I exploded deep in her asshole, or as deep as my dick would allow anyway. I came for what seemed like forever and after I pulled out, my cum started dribbling out of her asshole. It was probably the hottest experience of my life! The room and us were a mess but we barely had enough energy for a quick shower and collapsed into the bed.

There is more to this night but the story is long enough as it is so I will keep that update for another day!