[MF] Accidentally Matched my nephew's ex on Sugar dating site.

I have had a profile on a popular sugar dating website for about 8 years. I have had mostly great experiences and loads (pun intended) of fun. Anyway, last year, around this time, I was at my nephew's college graduation party. Among the people I saw and chatted with was his college girlfriend. I briefly met her the previous summer when she was in town for a visit and I got them into a popular night spot without waiting on the 3 hour line (my friends own it). She was gorgeous and looked really hot that night as did her friends, who I also got in. They thought I was the man for hooking them up.

So, she thanked me again when I saw her at the party, but our interaction was brief, but she told me she was moving up from Virginia to NYC and taking a job to be closer to my nephew. Fast forward a few weeks after, he decides to take a job in Boston and they had a nasty break up.

I was browsing sugar profiles and came across a really pretty girl with a clever profile and it caught my attention. She was 22 and new to the city and needed help making ends meet and was always attracted to older men. Her name was Lisa. I messaged her and we clicked over texts. I had no idea who she was and I don't put pictures on the site, so she didn't know who I was. We decided to move to text from the site and I sent her pictures. She immediately came back and said "Uncle *** is that you". I nearly shit myself! She texted again and said it was Lisa, ****'s girlfriend. OMG.

We both had a laugh and agreed to keep each other's secret. We also decided to meet for drinks platonically. We met at a rooftop bar after work. We were both in business attire, so nothing appeared out of the ordinary, like most of my sugar dates. I actually didn't think of this as a date at that point. We laughed and she cried a little about my nephew, but all in all we had a good time. I handed her an envelope with a humorous friend card with some cash to help her out. My intentions were truly to help. She was so appreciative and gave me a tight hug. She chuckled and said "I thought I would have to at least give an old dude a blow job to get a card with cash". I laughed and assured her that there were no strings attached. We were both a little tipsy, and I was horny and she looked hot. We both bot progressively more flirty so I shot my shot and said about that blow job...I will take one if you are still offering". I was shocked when she said, "where are you staying?"

I usually get a room as I live an hour from the city, but didn't plan to stay tonight. I quickly excused myself to the bathroom and quickly got on my last minute hotel app and booked something close by. When I got back to the table I told her where I was staying and asked her if she wanted to join me for a nightcap. She accepted and off we went.

We walked to the hotel and went right to the bar. I ordered us some drinks and again, excused myself to go and check in. I didn't want her to know to know that I hadn't been planning to stay there. I went back and charmed her some more before asking if she was ready to go up to the room. She was tipsy and I guess she must have been horny. Here I am nearly 40 years older, bald and carrying some extra weight. I was the shit back in the day as a college athlete and then a high powered exec, but the years have caused me to lose a bit off the fastball. I am amazed that young girls seem to be attracted to my stories and such. I know the cash is the differentiator, but they do seem to like me for real.

Anyway, we get in the elevator and she immediately grabs my shoulder and kissed me passionately, with lots of tongue! I was shocked and immediately got hard. We got to our floor and she clutched my arm as we alked to the room. She commented on my biceps and that big arms and shoulders turned her on. We got in the room and I felt more confident, so I pinned her to the wall and began to kiss her hard. She grabbed at my now rock hard cock through my pants. She pushed me back and said she had to go to the bathroom. I took the opportunity to got to the mini bar to make us a drinks. She was in there for a bit and I began to get worried until the door opened and she appeared, bare assed naked!!! Woww!!! She looked amazing naked. C- cups, tan lines, landing strip, flat stomach, gym toned body and a big smile. I thought to myself that if I died tonight, it would be OK because I have lived a great life and this helps to top it off.