Meeting Sydney Pt. 01

My name is Drew and as I currently write this I am in my mid 40's. A little background about myself I was married once for a couple of years no kids and we just went our separate ways. I have always been a very sexual person, and have been a very discreet bisexual since my 20s. One of my best relationships with a woman was one who actually pegged me while we dated for almost 2 years, I wish we could have had something more. From a work perspective, I am an executive and have never fooled around at the office.

And Now My story

This story takes place back in mid-2017, I was not working due to helping my company get purchased so I took a deal and took some time off to look for a new job. I was offered a C-level position with a company out of Boston that would require me to move but made a deal for the 1st couple of months to live out of a hotel while I sold my house and looked for a place to live.

About 3 weeks after I started there was a planned management meeting for sales leadership and SR management for the majority of the week, it was a great opportunity to get to meet people and get more up to speed on the company, and this is where Sydney came into my life.

On the 1st day there we had a cocktail hour before dinner and as I was meeting people I met Sydney she was a JR marketing person with the company and at the event to help run the agenda for the week, I recall meeting her when I started but I met so many people I forgot about her. Sydney at the time was 30 very pretty face blond hair down to her shoulders, bigger not fat but bigger, but she had something sexy about her. Nothing happen there or at dinner but back at the hotel a group of us were having cocktails late at night and she was hanging out, we both gave glances to each other that night. Nothing would happen but I do recall going back to my room and jerking off to her in my thoughts.

The next day was a full day of meetings and breakout sessions, I saw her again in the morning when I got there, there was a look from her that she gave me that got me hard in my pants. I didn't see her throughout the day but did think of her from time to time and had to remind myself this was stupid don't mess around with someone at work.

Later that night I saw her again at a social hour before dinner when she sought me out and we chatted, dinner was sitting where ever, and I sat at a table first and she sat right next to me. My mind went to behave but my cock went to this could be fun, followed by drinks I was having which didn't help. As we sat there talking it was loud and hard to hear so a couple of times she would have to lean in close so I could hear her, and at one point when she leaned in to talk to me she placed her hand on my leg under the table where no one could see it. I didn't know what she was saying my thoughts went to move it away don't go down this road, the other part of me listing to my hard cock in my pants and didn't say anything. Nothing more happened during dinner except for signals that there could be more to this working relationship, after dinner, I was smart and hooked up with others and went bar hopping.

Later that night I returned back to my hotel and was going back to my room which was in an area outside the courtyard section so there were some people outside the room areas having some late-night cocktails and calling me over for a nightcap. I sat down ordered a drink and a couple of minutes later Sydney appeared and sat down across from me. over the next 30 minutes, the group retired for the night, the voice in my head kept telling me to leave but the buzz I had and the looks Sydney was giving me made it hard for me to listen to those voices. Finally, it was just Sydney and I sitting there and after a couple of minutes, she got up and say next to me on the couch very close, which prompted me to move away. She asked was anything wrong and I told her if we didn't work together I would jump at this chance but in my position, I can't get into relationships with people I work with.

She said she respected that but she wasn't looking for a relationship she was just looking to fuck me, no strings attached. I got up not saying anything My room was feet from where we were sitting and I just walked back to the door and opened it looked at her and with my eyes told her to come here. I didn't have time to think of this and didn't care, within seconds she was inside my room the door was closed and I had her up against the door as we kissed hard. after a few minutes she fell to her knees and pulled my hard cock out and took me in her mouth. She proceeded to suck my cock for a couple of minutes until I pulled her up pulled her dress over her head and took her over to the bed pushing her down and pulling her panties off while she pulled her bra off. I went to get into position to fuck her but she guided my head to her pussy pleading with me and saying to eat her pussy, which I did. it didn't take long for her to cum from me eating her pussy and then yelling to fuck her which I did sliding my cock into her very wet pussy She looked into my eyes yelling fuck my brains out which I did until we both came and passed out till morning.

I was woken to her riding my cock around 6 am where we fucked changing positions for the next 45 minutes until we came again. She had to leave to get ready and as I showered I thought about how that was the most amazing sex with someone, was this a one-night stand would there be more.

I saw her as the day's events got started and she acted like normal, around lunchtime like the previous day it was buffet style and people were free to sit where ever catch up on things walk around for 90 minutes before sessions kicked back off. After my morning sessions, I made my way back to the main area where I was going to grab lunch, and Sydney approached me handing me the afternoon agenda, and walked away but this had a paper and card attached to it. It read if I was interested in a private lunch to come up to her room in 10 minutes which had her room number along with her room card, well I got my answer this was not a one-night stand.

I waited 10 minutes and went to her room and entered, and as I walked in she was naked on the bed legs spread as she fingered her pussy. Nothing was said as I started to remove my clothes, and as I approached the bed she spoke and said come eat your lunch which I dove in and ate her pussy. I ate her out for a couple of minutes until she came but instead of fucking we moved into a 69 until we both came. after we came we lay there, I thought we would fuck but she said this was just a tease I would have to wait to fuck her till tonight. We dressed and I went back for my afternoon meetings thinking of her the whole time.

That night we had dinner and like the previous night people split up and went on the town hitting different bars, but this night, Sydney was hanging in our group. The whole night she would tease me with her eyes touch my cock when no one was looking, whisper in my ear about what we would do later back at the hotel. When we finally got back to the hotel we went back to my room where we performed oral and fucked all night, we never slept. When we weren't fucking we talked about learning about each other. Finally, it was Friday morning and we had one last fuck session before breakfast and early morning flights, leaving that we would talk to see what was next, wait there was a next I thought.

Part 2 is next where Sydney and I take this relationship to the next level and explore a fetish.