It was a crisp November day and a 45 year old, divorced MILF was planning a lover's getaway in a city out-of-state...... The MILF was me. My name is Joy and I had not dated since my divorce and was planning a weekend getaway with a new lover.....Jason. Jason was a well-built, sexy, 40 years old! We had met briefly in person when we were both away from home and then had struck up a phone/email conversation that lasted about two weeks....until we couldn't stand it anymore and had to meet!
So, we met in a strange city and got a posh hotel room to settle in for the weekend. It was everything I had hoped for.....hot sex and lots of fantasizing and talking. Then something happened the second night that we were together. We had been having sex for hours and Jason was fantasizing about seeing me with another man. This was a complete turn-on as that had been a fantasy for me, too! I could not believe that we were on the same wavelength. But, of course that would be too daring for me to actually do! Or would it?
All of a sudden, Jason literally jumped out of bed and put his pants on. He demanded that I go down to the hotel bar and pick up a guy and have sex with the guy right now! Not knowing Jason that well, I didn't know if he was kidding or what!? He was persistent until I put on my dress and heels. I said to him.....OK.....joke's over.....you made me get dressed. Now we can go back to our fantasy. To my surprise he was still insistent. So, I hatched a plan. I would go down to the bar and have a glass of wine. Then, go back up to the room and tell Jason that there were no single guys there. After all it was 1 a.m. How many people could be in there? So, down I went.
When I arrived at the bar, there were about ten people sitting around the U-shaped bar.....and they were all paired up. Whew! Off the hook. So, I relaxed at the end of the bar and had my wine. Then, a woman left and there was a man sitting alone. Maybe she went to the restroom..... But, no. Her glass was cleared away and the guy kept sitting there talking to the bartender. He looked to be about 28 and was sexy in an Adrian Grenier (Vince on HBO Entourage) sort of way. So, I thought....now or never. I gathered up my nerve and went over and sat next to him with my glass of wine. Turns out Daniel was waiting for his roommate (the bartender) to get off work so they could go home. Daniel was a waiter at a nearby fancy restaurant. So, I chatted with Daniel for a few minutes and asked how long he had until the roommate got off work. Two a.m. Had to get this plan going now! So, I simply asked Daniel if he would like to go to my room....no more explanation. He looked at me and said "yes". We headed for the elevator. The roommate looked on, with question, but Daniel did not explain.
Once on the elevator, I said to Daniel, "There is just one thing......my boyfriend is in the room and he wants to watch. Are you ok with that?" Daniel looked startled and simply said......."OK".
We arrived at the room and Jason was just as startled as Daniel was.....that I actually had put this together! We were all a bit surprised and excited, as this was the first threesome for any of us. Jason began directing me what to do to Daniel. I complied and was completely turned on! It was just like my fantasy world. Jason directed, watched and then joined in......presenting me with his cock in my mouth as Daniel fucked me doggie-style. Daniel left satisfied and I am sure had one of those awesome crazy stories to share with his friends ....for the rest of his life! Jason and I continued our sex until the early morning hours. We had a great weekend and then both went our separate ways.
I never saw Jason again, but still have a great story of my own...... A MILF Story!