A vacation  

PappiMoresGable 64M
52 posts
7/3/2006 5:29 am

Last Read:
7/14/2006 4:41 am

A vacation


A female friend of mine agreed to go to Jamaica with me to one of those all inclusive resorts. We were just friends but we got along very well. I needed a vacation and wanted to take some golf lessons. She needed a vacation but did not want to travel too far all by herself.
She is rather tall and thin with nice long legs, small but firm breast, and a very good looking butt. I warned her that I normally sleep in the nude; she smiled and said that if it is warm she does also.
I like nude beaches and the freedom it gives you. It is not a sexual thing, but a way to feel comfortable and relaxed. She does not like nude beaches so we agreed that during the day we would both be off doing our own thing, then we would meet up for late afternoon drinks, have dinner, and go to the club.
The first two days went as planned. We slept in the same bed but respected each other privacy. I went to the nude beach and she flirted with one of the male beach employees.
While at the nude beach I went up to the beer tap to pour myself another drink and a very attractive and well proportioned female came up and started to chat. She told me that she was there for a wedding and was in a room with a “friend”. I told her that I was with a friend and she said that at least four of us were not getting any sex. We both laughed and went our own ways, although my eyes did follow her ways.
So that night Dee and I went to the club, had a few drinks, danced, and just goofed around. After a while we both seemed to quiet down so I got up my nerve and asked her if she wanted to hang around or go back to the room for some no holds bar sex.
She smiled and said “Let’s go!!”
We got back to the room, undressed ourselves as fast as we could, and started to touch and lick any place we could find on the other person. I went down on her. She has nice firm pussy lips with a light covering of hair. One thing about Dee, whenever I gave her oral and she was about to cum, she would stop me. For some odd reason she enjoyed receiving, but did not enjoy cumming that way.
She went down on me and sucked me very slowly. She positioned herself so that I could see her sucking me and I could see her long beautiful legs. Then she rode me for a while, we switched positions and I had her legs up over my shoulders. We must have fucked and sucked each other for over an hour.
We were in the missionary position when she said, “are you ready to cum?” and I told her that if she wanted me to I would. She pushed me off of her and rolled over. I started to lay on top of her to fuck her from behind but she did not get up on her knees. I am not one of those guys with a nine incher, in fact I am just average and happy with what I have. As a friend once told me, it was my play first toy and will probably be my last play toy.
So when she was laying on her stomach and did not raise her hips, I had a hard time getting myself into her.
I kept on probing trying to get into her, but the only hole that was within reach was her butt hole. Holding my cock I slowly started to put it into her ass, being prepared to have her stop me, but she didn’t. I moved it in very slowly, and the further I went in the heavier her breathing became. She let out a small squeak, and then a larger one.
All of a sudden she came, and my orgasm followed very quickly.
The next morning I felt a little guilty about it and asked her if she was alright. After all, this was our first encounter.
She then told me that that was the only pain in the ass that she really always enjoyed.
Needless to say the rest of the vacation was filled with sex and more sex. I got to know every single inch of her body over the next four days.
When we got back we became friends with benefits and enjoyed each other over the next year or so.

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