I finished my client and ushered her out after her weekly massage. She was an attractive woman about my age. She had started seeing me for massage after her husband died. She didn't share a lot. She seemed very reserved and a bit shy. Or maybe sheltered. I did know that she had been married for a long time and was initially very nervous about massage. Over time though, she learned to relax and allowed me to work on more than just her back and shoulders. We said our goodbyes and confirmed her time for next Friday.
I needed to pack up my table and supplies and get ready to go. I was going to be providing massage and more at a woman's retreat this long weekend. Through a friend of a friend in the massage world, I had gotten connected with a woman who ran retreats for women. She had several different types of retreat, but they all revolved around sensuality, pleasure and sometimes sexuality. In the past I had just been a massage therapist on staff, providing massage to clients or her staff as needed. This time, I was going to do more. This was a weekend devoted not only to relaxing in the company of other women with fine food at a beautiful, wooded retreat. It was also about learning to accept and take pleasure. I would be a masseuse as usual, but also I would take part in some of the demonstrations as well. Plus, I was going to be a Service Bottom for the weekend. She had a staff of Sexological Body Workers who would do their magic with the clients. I was not one of them. I would be available for therapeutic or relaxation massage during set times in the schedule. The rest of the time I would be a support staff member.
I got to the resort and set up my table and supplies in my work area. Then I pitched in setting everything else up. Because of the nature of the retreat, we replaced the normal staff with our own. We had our own cook and brought our own supplies. It was a busy day getting ready and soon it was time for the guests to arrive. I was working for the cook helping her prep and I heard the guests coming in. I stayed in the kitchen and the cook went out to talk about the food choices and dietary choices and she and I prepared the big cart of snacks and drinks to take out.
I knew there was a lot of admin to take care of the first evening. Discussions about the container, privacy, interactions with SBW, et cetera. Pamela, the organizer, called for the drinks and I helped the cook take everything out to the main room. I was wearing yoga pants and a t-shirt. And a steel collar. And a chastity cage. Pamela had already introduced the SBW's and co-facilitators. Now she introduced the cook and me. She told the assembled women that I was available at scheduled times for therapeutic or relaxation massage and how to sign up. She also said that I would be a demonstrator for some of the events and was generally available to help out and serve in any way needed. I made a little wave and looked around the room. Oh shit. There was my client. Louise. She was looking at me with an unreadable expression. I quickly kept looking and Pamela took control of the room again. I left and went back with the cook to prepare dinner. There was a short staff call before dinner and I mentioned to Pamela that I knew someone in the group. I couldn't say who, because HIPAA applied to my massage clients. Pamela asked if it was a problem for me and I said it wasn't, but I didn't know about her. Pam said that it must not be a problem since part of the discussion included whether I would work the weekend nude. I knew that was an option for the weekend when I signed on. Pamela said the vote for me to be nude was unanimous, so it seemed we were ok all around.
I stayed dressed for serving dinner. That was a rule, no nudity at meals. I helped serve and clear and then worked cleaning up in the kitchen. The evening sessions were already going when I finished. They were on a short break and Pamela came back to the kitchen.
"We could use your assistance now," she said.
She made a motion for me to strip, so I took everything off and followed her out to the main room. I have to say I was really excited. Being naked, collared and caged for a woman was my number one fantasy. Now I was in front of a dozen women. Including Louise. Tonight Pamela was demonstrating how she received different types of sensation as pleasure. I mainly just brought items from the toy table over to the SBW who was demoing with Pamela. When not actively helping I knelt as a submissive on the edge of the stage. The session ended and the ladies had a closing circle. I puttered around putting things away and cleaning up. Louise was fully involved in the event and I finished my chores and went back to the staff cabin.
The next morning I was up putting out coffee and fruit for the early risers. My instructions were to work silently and not interact with the clients unless they spoke to me. Women drifted in and had their coffee and enjoyed the quiet. Some of them watched me. I overheard some comments about how they would like that service at home and some laughter. Louise came in. She looked at me for a moment and joined a table. I looked at the massage sign up and saw that I had a couple of clients later in the day. I helped serve breakfast and then worked in the kitchen for the morning. After an opening circle and demo, the ladies had their first session with their SBW. Since there were more clients than SBWs, the other clients had options on what to do. Guided meditations, yoga, discussion groups, and also massage. I checked the list and had clients. I gave two massages in the morning, fulfilling a long time fantasy of mine. I worked nude and it was very erotic for me.
After lunch the groups split and I had two more massages. I was sexually excited by now. Besides just fulfilling my fantasy, some of the women made it hotter. One woman with a great body threw off the top sheet and I worked on her while she was nude. That made me really hard it my cage and she knew it. Another woman made lots of little pleasure noises while I worked. I then had to shift to kitchen and serving work. I got dressed to serve and then ate my meal in the kitchen. When the meal was finished and the ladies gathered for the evening session, Pamela came to me.
"We had to change tonight's plan and need to fill in a class. Are you up for being my assistant tonight?"
"Of course," I answered. "What do you need?"
"I'm going to do an impromptu class on Femme Domme and how to condition a Bottom."
I sucked in my breath.
"I'm ready," I managed to say.
Pamela smiled. I quickly undressed and followed her out to the main room.
"Tonight's new class is How to Train your Bottom."
You could hear the capitals in her voice.
"I'm going to demonstrate how you properly lead your bottom into the type of submission you want. I'll show you several different protocols and ways for a Bottom to properly serve his Woman."
Pamela spent the next 3 hours putting me into different positions, leading me on all fours on a leash, using different terms of address, showed a range of control from loose to very formal and so on. Some of the women were very interested, some were giggling, Louise looked to be in the former group. For the final hour, Pamela offered the leash to other women to practice. Some women drifted off to get more dessert, some stayed to play with me. Louise stayed but did not take the leash at any time. During the closing circle. I knelt behind Pamela in a waiting position. When everyone was dismissed I went to bed. I was definitely aroused from being topped all evening in front of all those ladies.
The next day was largely the same. I assisted and served breakfast and lunch. I had two massage clients in the morning. I loved giving massage nude in my steel collar and cage. In the afternoon, Pamela was demonstrating classes on sensation. One of the SBWs would show how to use various items from feathers to sandpaper or whatever to stimulate Pamela. I was blindfolded at the beginning of the class so that the participants could practice on me and not feel like I was watching them. It was certainly an experience. The ladies took turns using all the sensation implements on me. At first it was all soft and sensual. Silk cloths, feathers, fingertips. As the afternoon went on the sensations got stronger. Clothespins, steel finger claws, pointy things. I wasn't bound or restrained but I had to try to stay as still as I could as they experimented. I was squirming, moaning and sweaty by the end. Not to mention my cock bulging against the cage. After dinner was more of the same, but dedicated to impact play. Paddles, bare hands, canes. Also over the lap spankings. I was bent over several different ladies laps and spanked. I wished I could have told who they were, but the blindfold was very expertly tied and I couldn't see even a hint of whose lap I was over.
I had a rough night sleeping. All my buttons were being pushed. Spending a long weekend naked collared and caged in front of women exploring their sensuality was a dream come true. Add in all the sensation play and being publicly Topped and I was one big bundle of arousal. I spent the day serving and massaging as usual and finally dinner was over. Tonight was the final night and Pamela checked in with me one last time to see if I was ready for the finale. I was. She led me on a leash in front of all the clients.
"Tonight, we have two events planned. The Sexological body workers are available for any type of class or play that the group wants in the main room. In the private room we have a special treat. Tim is offering to let one of you peg him. If you don't know, pegging is a woman using a strap on cock to fuck someone else, male or female. Tim has wanted to be pegged for a long time and is offering his virgin ass to one person tonight. In a few minutes we will break up into groups. You choose which room you want to go to. For those who choose to go with me and Tim there is a bowl in the room on the table. If you wish to be the one who pegs Tim, write your name on a slip of paper and put it in the bowl. I will draw a name and the winner gets to wear the strap on. Any questions?"
Pamela led me down the hall. I entered the room and about half the women came in. Pamela helped me get into the swing and fastened the restraints around my wrists and ankles and got me comfortable. I could hear activity behind me at the table, but I couldn't see anything. Pamela gave a class on pegging. She talked about preparation, going slow, maintaining communication, lubrication, et cetera. Now it was time.
"Everybody ready?" she asked.
I could hear her swirling her hand in the bowl.
"Louise!" she announced.
I gasped and jerked in the swing. I couldn't believe it. I didn't know she was even in the room, much less in the raffle. I heard some chatter from the ladies behind me. Pamela adjusted the lights so that most of the room was in darkness. There was a spotlight on me hanging in the swing. I could make out the ladies standing to both sides of me in the semi-darkness. I could make out Pamela and Louise talking in the background. There was quiet for a few moments and then Louise and Pamela stood in front of me. Louise had changed her clothes and was now wearing a black body stocking and a matching sheer robe. Pamela helped her step into the straps of the harness and adjusted it. Louise wiggled around and shifted it a bit till she was comfortable. Pamela guided her to stand between my legs. Pamela and another woman adjusted the straps on the swing, so I was at the right height. Louise moved closer so my calves were resting on my shoulders.
"Most important is communication," Pamela said.
Louise had one hand on her "cock" and put her other hand on my thigh. I had been massaging her weekly for months, but she never touched me.
"If you have been pegging someone regularly or are both experienced then you will do this without thinking or speaking. But for now we want to be clear."
