When we first started "playing", Monica and I were unsure where we were going to stand on the same room / separate room decision. Monica was leaning towards same room while I was leaning towards separate room but no final decision had been made. At that time we were thinking that primarily our activities would be limited to swapping with other couples and the question seemed pretty obvious.
Fast forward to now and what we have found is that finding couples with whom to swap is hard but finding singles interested in one or both of us is, relatively, easy. So our questions and decisions are now being made from a very different perspective than the one we originally imagined.
If you have been reading the blog, you will be aware that we have been heading down the "play alone" path for some time ever since Monica began meeting guys ahead of our play sessions to give them head in anticipation of the "main event." A few weeks ago I finally got the chance for my own playing alone fun.
It was with my friend that I met online in "A Surprise Meeting", we had put our playing on hold for the holidays but we were both available now and Monica was able to stay home with the kids so that I could go out and play.
We made our plans quickly, I rented a hotel room near where she lives a town over, and headed over there around ten after the kids had gone to bed for the night. I picked up a six pack of beer just in case it was needed but left it in the car assuming that I would not want to have it with me. I also grabbed a Monster as I have been completely exhausted as of late and have energy for tonight's sessions is going to be tough.
My "date" arrived late having gotten lost trying to find the hotel. I had a book with me so I was happily reading while I was waiting. Not a big deal.
My friend came in the door and it was knock knock, "Hey, good to see you again.".... kissing standing at the foot of the bed. No time wasted there. I assure you I was ready for small talk but she jumped straight to tongue action and in under twenty seconds was stripping down ready to get it on. She left nothing for me to do, her clothes were on the floor in a flash and she was climbing in to bed.
So I got undressed and joined her in the bed. She turned on the television, I guess for background noise but with the talk shows that she was selecting it was a bit disconcerting as the television was so close to us. Not nearly as good as having porn on, that is for sure.
It only took a minute of sucking our her firm double D tits before my right hand slid down her stomach, spread her legs and was pushing a finger or two into her very wet and very ready pussy. Her pussy was shaved and eager. It was only a minute more before her first orgasm. It has been a long time since I was last with someone who comes so quickly and easily. Monica is not multi-orgasmic so I have adapted to that mode of sex which involved a long buildup and eventually a single, hopefully massive, orgasm that lasts and lasts when done right. But the orgasms tonight were fast and frequent.
Throughout the evening she probably came around twenty times. My record was making a girl come thirty-four times but that was set in around 1997 with an eighteen year old blonde that I had practice with and she only had to stop from exhaustion (hers, not mine.) It is a nice change of pace to have the rapid orgasm experience again.
And, like the blonde girl that I so adeptly pleasured all those years ago, tonight's playmate was a squirter. Now Monica is jealous. She has always wanted to play with a squirter and thinks that it is so hot that I had one fifteen years ago and she has been looking for one for a long time now. And now that I am playing with one, Monica isn't here. It will happen eventually, but she has been wanting to try it for so long now.
The squirting was not all that intense, it was just a little bit. My old squirting partner from the late 90s was a real pro which is hot and sexy but really messy and difficult to manage when you can't avoid it. But I'll cover that another time.
We had a nice time. For a women with a kid in her early forties her body was firm and her breasts were ample. She was actually taller than me as well, just by a little bit, and I am no short. I'm definitely not tall, but average for a guy.
The sex was good. I made her come from fingering her over and over and then about three times when I went down and ate her pussy. Monica will attest to the fact that my pussy licking skills have taken a leap forward in the last few weeks. Some recent stylistic changes and yielded impressive results so it was nice to get to test these out on a very willing new subject.
It was not a late night. Probably two hours of sex, tops. Once she had come... a lot, I donned my condom and put her on her hands and knees on the side of the bed so that I could stand on the floor beside the bed and penetrate her doggie style - one of my favorite positions.
Sliding my cock into her waiting, black pussy lead me to discover how small her pussy was. And I don't mean tight, it was probably average in that regards, but it was hard to fit my cock into her as her pussy interior was small and somewhat shallow. I had to work to squeeze myself in but she enjoyed it and soon I was pounding away on her.
She came once while I was pounding against her little black ass and then when I came the force of my orgasm sent her over edge into a thrashing orgasm of her own. Unfortunately she lost control of her back muscles and buckled which made it impossible for me to remain inside of her as she changed the entry angle so dramatically and squeezed me out as well with her pussy muscles.
We took a bit of a breather and talked for maybe an hour. Then she asked me to make her cum another four or five times. We called it a night and I got dressed. She wanted to stay and use the hotel, which I thought was rather odd as she meant staying in bed and watching television not showering and getting cleaned up, but whatever, we have the hotel might as well get use out of it I suppose. After I was dressed and getting ready to head out the door she grabbed my hand and slid it down under the covers and asked me to get her off one last time before I left, which I did.
And that concludes my first time playing alone. The first of many such episodes, I hope. This also was my first time having sex with a black women. And my first time having sex with someone older than myself. An adventurous night.
I got home and filled Monica in on the details. It was really late and we were tired so we fooled around for a bit in bed but didn't have sex. We saved that for the next day.
Now that both of us have managed to play alone... we can count the experiment as a success. - Steve
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