{This one is from way back, just something that popped back into my old head. Thinking about it, this was the start of my learning about different relationships. Just take a moment to think about all of the people we all see each and every day.
Every single one of them have some very naughty stories to tell.}
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That session with Cindy was a kick, of course by then I had worked on several dozen housewives. Housewife types are typically a bit chubby and all concerned about that, of course. My client base consisted of ages from middle 20's to well into the 50's, just one lady was even older.
The income stream from my work was barely enough to keep me in food and the bills paid, still I was doing better than the few other guys I knew that worked free lance doing massages. I had roughly 8-10 clients each week, by the time I worked on Cindy that first time my record was three in one day.
Anyone who really works in the massage therapist field will tell you, three clients, when you add in everything like, booking, dealing with a few no shows, the visit before and after, laundry, making up the table, answering the phone etc makes it close to an 8 hour day if you stop to grab a bite to eat.
There is no such things as 9 to 5, either. There as everything from 8 in the morning to a few that were after midnight. I did enjoy all of them though, and at that stage of my life, Cindy was by far the best looking lady I worked on. Plus it became clear that she was interested in the more intimate type of touch that normally I reserved for after several sessions.
There has to be trust, of course. Even back then, when the laws would best be described as foggy, it paid to be careful. Small town and all of that, stories get told. But being a small town, word also got around, women tend to talk far more than most of you guys might think.
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It was a bit of a surprise when my phone rang about 4 on a Saturday, maybe two weeks after I worked on Cindy that first time. I answered, it was her husband, Jim.
"Hey, Dan." He opened with.
"Hi, Jim. What's up?"
"Oh, I was just wondering, Cindy and I were talking. We were wondering if maybe you had time to work on her again? She isn't hurt or anything, it's just that.. you know.. that was kind of fun."
"Sure, happy to. When would you like?"
"Maybe later today, or this evening?"
"I can do it at tonight if that works." I told him. I had glanced at the clock, I knew I would need to hustle, my sheets needed washed and I needed to get the room ready like always.
The side work is a pain in the ass in the massage profession, I was always behind.
"Great! And I was thinking, you know, can it be like we talked about?" He asked.
"Talked about?"
"Yeah, like maybe I could be there? I could watch and.. uhh.. learn, she told me you are really good. I am just curious about Cindy's reactions."
"Well.. I guess so, I don't see any reason why not." I told him.
"OK, good. I won't get in the way or anything."
"Sure, see you at eight tonight." I told him.
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The knock came at almost exactly 8 PM, by then I had my table set up and ready to go. Normally I worked in my spare room but it was tiny, more like a big closet than a room, so after thinking about it, I moved the table out into the living room. There I had a couch, an easy chair, and lots more room to move around the table.
I let Jim and Cindy in, he shook my hand, then asked where I would like him to sit. I told him anywhere he felt comfortable. I was already thinking that this session was going to be way more conservative, for one thing, I was not really sure just how much Jim knew, since the last session with Cindy had gotten pretty erotic. Towards the end I had her completely naked, and she had her legs wide open, exposing her bare pussy, her overly soft breasts, by that point any hint of being shy was long gone.
Doing that to her in front of Jim was something I was thinking perhaps I best not do. After all, she being his wife and all.
Jim and I chatted about bowling mostly as Cindy went in and used my shower, she came out with one of my huge bath towels wrapped around herself. She appeared slightly hesitant and bashful about being nude under the towel, so I excused myself and went to the bathroom to wash up. She was face down on the table when I came out, the sheet pulled up over her body.
"Warm enough?" I asked her as I got my oil bottle.
"Uh huh." Was her quiet response. I glanced at Jim, he was sitting on my couch, he gave me a grin but said nothing. I started at her shoulders, working them out sideways, then each arm carefully. As I reached to tug the drape down halfway, Jim sat up a bit straighter but said nothing.
When it came time to lower the drape, I asked her, just like the first time.
"Uh, huh." She responded in that tiny voice. Then still not completely sure, I glanced at Jim who was watching intently, so I pulled the drape towards myself, baring the entire side of her body. Jim stood up, I paused but he just moved over to the end of the couch and sat on the arm rest. I realized he wanted to be higher so he could see, so I went back to work. Cindy was not moaning like she had the time before, so I spent quite a bit more time working on her nice behind. I didn't do any of the trickling fingers stuff, and stayed out of the cleft.
Next I moved to the other side, and bared her other butt cheek, glancing at Jim I could see he was really leaning forward to see, as this placed me between him and Cindy partially. I moved sideways slightly to he could see, and began to quietly explain the motions and what I had learned in class.
I was trying to appear and sound as professional as possible.
Now at that time, the only massages I had ever done with someone watching was in class. Normally the sessions were between myself and the client, but now with someone watching, plus it being the client's husband? I was mildly uncomfortable, not wanting anyone to get upset. So, I was carefully not taking any real liberties.
Then it came time to turn over, I held up the drape to block my view, Cindy rolled over easily onto her back. I began at her neck, after a few minutes I moved to her side and pulled the drape back to bare her abdomen.
"Aren't you going to do her titties?" Jim asked, which were the first words he had said at this point.
"I.. well, I can if...?" I glanced at Cindy, who didn't even open her eyes, she just reached up and pulled the drape to her waist. That made this portion quite clear, so I spent the next few minutes working them carefully. Again I noticed how very soft her breasts were, I figured one day gravity was going to win there but she was still young enough that she only sagged little bit.
Her nipples were like needles, I reached out with oily fingers and gently rolled each of them, getting a shudder from her. I could hear Jim's quick intake of breath and realized he was getting turned on by this. Cindy had her eyes squeezed tightly shut. I again used the trick with the rolled up towel which barely rested on her nipples.
"Cindy's boobs sure are sensitive, aren't they?" Jim said then.
