[ABFRH]

While working in Florida, after several years of being there, I placed an ad in the "casual encounters" section of craigslist. Since I am not, nor was I, a licensed massage therapist I could only ask for a donation for services. Once I had experienced my first 8 or so clients, the "body rub" business picked up by word of mouth, friends telling friends. Mostly were older ladies in their 50's and early 60's, while I was in my middle to late 40's. Once or twice one would bring a husband but he would usually wait in the living room watching TV. Mainly they would come on the weekend when they would know their husband would be on the golf course and not likely to be looking for them.
One of my clients was an older couple from the northeast who would visit Florida 3-4 times a year. He had actually contacted me thru the craigslist listing and we shared many emails regarding what expected from me and what he was looking for before ever meeting. I will call them Barbara and Bob for brevity.
Bob was one who liked to video the event. He explained that she would be naked and I could touch her anywhere but I was to remain clothed, the session should only last about 30 minutes, I could rub her pussy a little but no fingers. I asked if I could be the one to undress her prior to her taking a quick shower (said she always showered before and after). We all agreed on the parameters. They were to fly in that weekend and would let me know where they would be staying and would give me a call as to time and room number.
To make a long story short, that was the beginning. I would always dress in a pair of loose fitting shorts without underwear, and a button down collared shirt. At the first event she warned me, "nothing pervy" were her words. She was probably 65or so but very well maintained and a very nice body. Afterward she told me that she had never been undressed by a masseur but that it made her feel very special.
That event was in St. Augustine but they would also be in Daytona, or Ormond Beach. The last evening that I spent with them was in Jacksonville. Everything started out pretty much the same but she seemed much more relaxed and the lingerie she wore was a little sexier. Once she had taken her shower she sat on the bed with legs spread somewhat while I sat across enjoying the view. Bob had sat up his camera at the end of the bed so he could video my hands touching her pussy. I started the massage at her shoulders. She always made me use her Vaseline Intensive care lotion instead of my preferred almond oil. I worked across her boobs pinching and playing with her nipples which always elicited a positive response before moving down her stomach and toward the promised land. At the beginning of the massage I had positioned her legs apart so her pussy would always be on display. I placed on hand on either side of her inner thighs and squeezed the together giving her pussy that pouting look; I then would run one had behind the other across her pussy. Occasionally I would glance at Bob to check with him to see if I need to be doing something different. He was my "coach" in ways to feel up his wife. I had done the same thing with guys giving my wife massages.
I finally had her roll over on her stomach: usually I start on the back and finish on the front. I asked her if she had any issues or back problems that I needed to be aware of and asked if she minded if I did a quick check. So I had her get on her knees and bend over to see if her spine was in alignment. Of course this exposes her pussy and asshole and Bob and I just looked at that for a moment. He gave me a thumbs up for that one. Once Barbara was on her stomach I started at her shoulders working down to the small of her butt. I spread her legs as wide as she would be comfortable. I worked on her butt and would slide the side of my hand across her asshole down toward her pussy. I would do that several times and then move down her legs coming back up to run my fingertips across her asshole. After doing that several times I noticed that her ass would rise ever so slightly as my fingers crossed her asshole. While working on her legs I shortened the intervals between her legs, my fingers crossing her asshole, and my hand rubbing over her pussy. I placed a good amount of lotion on her ass so I wouldn't have to stop again. One hand was on each cheek of her ass with fingers inward as I started paying more attention to her asshole. I could hear her breathing change. Her arms were down by her sides and I was rubbing my crotch up against her left arm. I know she could feel my hard cock thru my shorts but never made any effort to move her arm. Her breathing increased even more and her ass relaxed as if wanting more pressure from my fingertips. Finally her ass arched and she moved her right hand under her body to find her pussy. Her left arm was still tight against my crotch. I looked again at Bob and he was still thumbs up.
As I was rubbing circles around her asshole with one hand, my other hand was on her pussy feeling her hand playing with her clit. While rubbing circles around her asshole, it seemed to relax and I inserted just the very tip of my finger. With that I felt her hand move down my leg to find the bottom of my shorts. Once she found the bottom it didn't take her long to find my cock and start jerking on it. It wasn't the most comfortable position to be in but Hey, she was feeling my cock. When she did that I changed fingers in her asshole from index to middle and started working it in, out, and around. The middle finger gave me a little more depth but still did not get to the first joint.
The next thing that I know, I'm rubbing her pussy, she's rubbing her pussy, and I'm fingering her asshole and she starts to shudder, squeezes the crap outta my cock, and let's out an "oh fuck". I had never heard this lady say a four letter word. She lay there motionless, still holding on to my cock. Bob was smiling and turning off the camera.
The first words out of Barbara's mouth were, "I never expected that but it was incredible." She was still shaking as she turned over and sat up. My cock was still hard as a rock and I could feel that a severe case of blue balls was going to set in soon. And it was Bob who finally helped me out. He told her that the least she could do was to give me a handjob. She had that deer in the headlights look and said she had never ever done anything like that for anybody but him. Finally she accepted and Bob told her that he wanted to video that also. While Bob changed the batteries or tape or whatever he was doing I took my shorts off and put her hand on my cock even before I lay on the bed. She started massaging my cock even before I got on the bed. I reached down between her legs to feel her pussy again and she said, "yeah, I am a little wet." A little wet didn't begin to describe how wet she was. She was stroking my cock with one hand and playing with my balls with the other. I reached around her and was going between her ass cheeks and fingering her pussy. You could see in her face that she was enjoying all of it. Bob tried to get her to suck my cock but she wouldn't do it. I came a bucket load but she never left the side of the bed, she was enjoying me finger in her pussy.
I got off of the bed and sat in the chair while we talked until Bob go up and lay her on the bed so he could lick her pussy.
I have lost track of them since then but for an older lady she was awesome. Thank you Barbara if you ever read this.