Massage Apprentice

This is a retelling of a couple of chapters in which a massage client first received a massage from the apprentice. It might stand alone, but it would make more sense if you had read chapters 5 and 7. Or start with chapter 1 and read them all!

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My first experience with Jen’s assistant was when he observed Jen giving me a massage. I have been a regular client of hers for quite a while, and one day she asked if her assistant could observe. She let me know that the assistant was male; I had seen him once or twice around her studio. I felt a bit concerned about this, but I trusted Jen explicitly, so I agreed.

The massage started out as usual; Jen’s hands relaxed me so well that I almost forgot that there was an onlooker. Jen always used draping on me, but I felt that this time she kept me more covered than usual. Perhaps she sensed my initial discomfort.

At one point Jen hit a knot of muscle on my right side. She could tell that I was tender there and backed off, then asked me if her assistant could touch me, as a learning experience. I agreed. I have to admit that I was not 100% sure, but once he did I knew that it was the right decision. His hands were warm and his touch was gentle, even though he seemed a bit tentative. I wondered then if he would be touching me more, in that session or perhaps in future sessions.

Jen’s hands always relaxed my body, and as she continued to work on my back, then on my legs, I let my mind relax as well. I was brought back to the present when Jen moved the draping off to the side to uncover my left butt cheek. It wasn’t her usual procedure. Usually, she removed the towel completely, but then I remembered that we had another person in the room. Even though I was face down, I felt like her apprentice’s eyes were on me and it wasn’t a totally unpleasant feeling. I realized then that I was actually enjoying the idea that my body was still worthy of the glances from a young man.

As Jen worked my cheek, I let myself relax again. When she covered me back up and started to work on my other leg, I knew she would soon be exposing my other cheek, and I was thinking that I was just fine with that.

When Jen leaned in close and whispered that it was time for me to roll over, I was a bit concerned. Our established procedure was that the draping would be rolled down to just cover my privates. Prior to accepting the apprentice session, Jen had asked if I preferred to be covered on the flip, and, not knowing how I would feel, told her that yes, I’d prefer that. With her assistant discreetly looking the other way, Jen lifted the draping, I rolled over, and Jen replaced the draping, covering me from my upper chest to the tops of my thighs. She worked her magic on the back of my neck and shoulders and then moved to my upper chest. She adjusted the covering a bit, moving it down to expose the swell of my breasts, but nothing was exposed.

Jen asked her assistant for another towel. She folded it a couple of times, then held it over my breasts, above the covering. She instructed her assistant to slide the covering down to my waist, and, as he did, Jen preserved my modesty by placing the towel over me. I felt pretty exposed but didn’t mind. Jen gave me a belly rub, a part of the massage that initially I wasn’t too fond of but had grown accustomed to it.

That massage ended without any additional touches from the apprentice. I knew then that I was going to try to arrange another session with him, perhaps the following month. Hopefully, by then, he would have had enough training to get more involved, instead of just being an observer.

And indeed I did get the chance. After the massage, outside the room, Jen asked me how I thought the session went. I replied that it was fine, and Jen asked if I’d be willing to serve as a guinea pig in the future. Perhaps I agreed to quickly, as I remember that Jen got a quizzical look on her face for a second. She smiled, and we booked a session for a couple of weeks ahead while the apprentice was in the room prepping the table for the next client.

As the date of the second massage approached I found myself thinking about it on and off throughout the day. I had never had a massage from a male before, and I was surprised how much the touch from the apprentice excited me.

On the night before my appointment, I took special care of myself. I had a long warm bath, cleaning every nook and cranny and trimmed my pubic hair. In the process I started to let my mind wander, fantasizing a scenario where l was laying totally naked on the table while the young man worked his hands over me. My fingers started to wander as well, and not surprisingly, I brought myself to a quick orgasm right there in the bath.

The next day when I checked in with Jen, she said that she assumed that I would want the same amount of modesty as before, meaning to not expose my breasts and ass. I hesitated before I responded, then said I was ok with her normal procedures. She gave me a smile; I tried to clarify what I had said by telling her that I had I faith that her apprentice would act as professional as she did. Still, Jen smiled, perhaps seeing through me, then said she understood.

When I entered the room, the apprentice was just finishing setting up the table. He addressed me by name, with a smile, and I could tell that he was much more comfortable than the previous session. I assumed that he had partaken in other sessions, gaining confidence as he went. He left the room, saying that they would be back in a moment.

I undressed as usual but made a point of laying my bra and panties arranged on top of my clothes so that they could be seen. I had worn one of my best matching sets, with the bra being very sheer and the panties hardly anything more than a thong. They always made me feel especially sexy. I got up on the table, face down, pulled the thin sheet over me and waited.

The massaged progressed as usual. Perhaps Jen had turned the covering back further than usual, exposing a bit of my butt cleft, but I wasn’t concerned. And the apprentice was much more of a participant than before; after Jen worked on my back for a while, she asked him to do the same. I know that it was my imagination working overtime, but his hands felt so much warmer than Jen’s.

She switched up her procedure on my legs. Usually, it was one at a time, keeping the other covered. This time she pulled the sheet up, barely keeping my ass covered, and worked on one leg while the apprentice worked on the other. I could tell that he was trying to follow what she did, as he copied her movements pretty closely.

Then came one of the moments I was a bit worried and excited about. Without ceremony, Jen moved the covering up over my back, leaving my ass completely exposed. She worked it like she usually did. The apprentice didn’t take part in this which was fine with me. It was exciting enough for me just to know that he was there watching. In the process of Jen pushing and pulling my buns, I’m pretty sure my holes were at least partly exposed and if he was watching closely, he might have gotten a quick peek.

When she announced that it was time to turn over, she held the sheet up and I rolled over. The apprentice was not privy to seeing me as I turned, but at that moment I wasn’t too sure I would have minded if he had been. Jen adjusted the sheet, folding it down over my shoulders but still keeping me mostly covered.

I’ve always felt that the size of my breasts was like the fairy tale of Goldilocks. They weren’t too big or too small; they were just the right size. More than a handful, but not so much that I occasionally could forego wearing a bra without flopping around.

My nipples, however, were a different story. I feel like they were a bit disproportionate to my breast, almost as large as the areola surrounding them. If it was cold out, or I was a bit excited, their size became quite obvious. And it wasn’t cold in the room; Jen always set the temperature on the warm side. But, without looking down, I knew my nips were distended, and they had to be obvious under the thin sheet.

Jen made quick work of my neck and shoulder and then paused. She gave me look that I interpreted as ‘Are you sure about this?” I smiled at her and gave her a very slight nod. She folded the sheet down once more leaving me topless on the table. I took a quick glance over at the apprentice and caught him checking me out. I smiled, closed my eyes, and let Jen take over.

She massaged my chest, as usual, placing her hands on my collarbone and gliding between my tits, applying pressure on the insides as she went, then circling her hands underneath and back up along the outside. There was no contact with my nipples, but I wondered at the time if she noticed that they were especially ‘perky’.

After the normal belly rub, she covered me back up and went to the foot of the table to start on my legs. Jens usual routine was to fold back the covering to expose just one leg, and thigh, at a time. This time she folded both sides in towards my crotch, to allow access to both legs. She started on one and signaled her apprentice to join in the other. As they moved their hands up my legs, I found myself fantasizing a bit about having him touch me. And, while I was pretty much covered, his hands on my inner thigh were definitely pleasant. I had closed my eyes when they started on my legs but was jolted out of my fantasy by Jen.

“Is everything ok?” she asked.

I realize that she had caught me smiling. I replied that it was all good, and they continued. With a final sweep up my legs, Jen announced that we were finished.

They left the room, allowing me time to get up and get dressed. I remember that I quickly ran my hand over my pussy and, as I had expected, found that I was a little moist. It wasn’t enough to bleed through the covering, but the massage had definitely gotten my juices flowing. I knew it was because of having a male work on me. I’ve had dozens of massages, from Jen and other therapists, but never felt anything like I was feeling now. And I knew that I wanted to have him work on me again.

That opportunity presented itself a couple of weeks later.

I have a friend, Sue. She was the one that first introduced me to Jen, and had been seeing her for a couple of years. We got together occasionally for lunch. She didn’t need to work and prided herself on keeping in shape, so she pretty much always looked good, and always seemed to be just coming from any one of a number of workout classes that she took.

At one of the lunches, I told her that she was glowing, assuming that she just had a workout. But she mentioned that she had just gotten out of a massage, which started a conversation about Jen and, eventually, her apprentice. While I wasn’t about to share my secret fantasies about him, Sue didn’t have any qualms. She spared me some of the details but talked about the session she had just left earlier.

It was a new offering from Jen, an experiment of a four-handed massage from Jen and her apprentice. Sue talked about the sensations she felt with all the hands working on her. I knew enough about Sue to assume the worst, so later that evening, after once again acting upon my now frequent fantasy of having a guy, or multiple guys, working on me, I called Jen. I told her that Sue had mentioned a four-handed massage and asked if she was still offering that. She was, and so we booked the session.

I remember that my anticipation for that session was even more intense than was the previous one, and on the evening prior to the session I once again let my fingers, and my most trusted vibrator, work their magic. I had shaved my pussy down to hardly anything but slight fuzz, leaving just a tuft, and trimmed it close to my lips. I had no reason to believe that it was going to be on display, but on the off chance that it was, I wanted it to be exquisite. Rubbing some conditioner into the skin after the close shave turned into rubbing my clit, already peeking out from manipulating it while shaving. After I slipped my purple vibrator in, it didn’t take long. I had a tremendous orgasm. I fell to sleep thinking, and fantasizing, about the next day’s massage.

I feel that I should explain myself. As I re-read this diary of events, I feel like I hardly recognize myself. I do not consider myself a very sexual woman. Yes, I have moments, here and there, but hardly ever act on them. Yes, I sometimes feel the need to masturbate, but I am not constantly walking around in a state of arousal. I am single and, I think, fairly attractive. I have had my share of lovers so I know my way around a man’s body. But I tend to find myself attracted to men my own age or older; I am not a cougar.

That said, I found myself thinking a lot about being touched, being massaged, by a younger man, specifically Jen’s assistant.

I was on pins and needles the next day as I arrived at Jen’s place. She must have sensed that, as she offered me a glass of wine, which she hadn’t in the past. I probably should have declined as it was early afternoon and I’m not that great with alcohol, but it seemed like a good idea. I was hoping that it might take the edge off just a bit, settle me down.

As normal, Jen led me into her studio. He was there, finishing up on setting up the table. Jen had brought in three glasses and proceeded to pour a glass for each of us. As I sipped the wine, Jen explained what the 4-hand massage was all about. Basically, I remember she said that it might feel strange at first, having an extra pair of hands working on me, but told me not to overthink it and to just relax.

They left the room to let me get ready, but Jen quickly came back in. She told me she just wanted to let me know that she would still use the normal draping practices but remembered that last time I was ok with being bare-breasted, and was I still ok with that. I might have answered yes a bit too quickly, as Jen gave me a startled look, a slight giggle, and said no problem. She left the room and I undressed and laid face down on the table, pulling the thin cover over me.

I already felt the glass of wine and was totally relaxed until I felt a hand on my back. I was jolted back to the moment, and Jen asked if I was ok. I lifted my head up off of the cradle. I answered that I was fine, and with that Jen folded the sheet down, exposing my back and, perhaps, a bit of my ass. I felt the familiar feeling of oil being applied to my back, and then the unfamiliar feeling of two pairs of hands spreading the oil and massaging my shoulders. But it was very comfortable and I let myself slip away.

Once again I was brought back to the moment when I felt the sheet pulled back up to cover my back, and then pulled off from one side to expose my thigh and cheek. I assumed that it was Jen taking charge as it was quickly followed by the other side being pulled over. I was pretty much exposed from the waist down, but I could feel the sheet partially covering my butt. Oil was applied to my lower back and I felt some of it sliding down under the cover into my crack. I tried to relax, but my mind was spinning. A pair of hands started massaging each exposed ass cheek, pushing, pulling, and molding them. It felt good, very good.

At one point I think the draping might have slipped; exposing more of me. I felt it being moved back into place, but, in the process, I also felt the back of someone’s hand rub against me very slightly and very close to my pussy. In my mind, it was the apprentices’ hand, but I really had no way of knowing for sure. They continued with a couple of more butt rubs, ending with each pair of hands pushing a cheek outwards, spreading open my asshole. I let my mind take over for a second, imagining what a sight that would be if I was totally naked.

A slight pat on the butt and the hands moved off and went to my ankles and started to massage their way up my legs.

I was already a bit on edge from the ass play, and couldn’t really calm down as I loved this part of the massage. In the past, Jen’s hands would end up high on my inner thigh, and it always felt like a bit higher and I’d be working towards a happy ending. Jen never did that of course, but I didn’t let that interfere with my imagination.

As they moved up my legs I thought that I felt the sheet slip again. It was adjusted but not immediately. My mind kicked into an even higher level of overdrive, wondering if I had been exposed to the apprentices’ eyes. If so, was he excited, or was he disgusted? I didn’t dwell very long on what his reaction might have been, as I was definitely excited just to have possibly been seen.

Once their hands reached my upper thigh, the hands on the side moved further up onto my ass, but the other hands rested on my inner thighs. The feeling of the proximity of their hands to my pussy was as I expected. I took a couple of deep slow breaths to force myself to slow down.

Jen leaned in close to me and said that it was time to roll over. The apprentice rearranged the sheet to cover me back up, and then lifted it up, blocking his view as I turned over. He folded the sheet down a bit, to just above my cleavage on the top and to mid-thigh below as Jen removed the face cradle and put a pillow under my head. Standing at the head of the table, she started working on my shoulders, neck, and scalp. The apprentice had moved off to the foot of the table, giving Jen room to work.

I realized that he might have been able to see more of me from that angle. I watched him looking, and when his eyes moved up to mine I didn’t break the contact. I made a brash decision; I admit my thinking was probably a bit cloudy. I very slowly started to slightly spread my legs a little. He continued with the eye contact for a second, but eventually broke it and looked down. I saw him take a slight step back, still looking, then caught my eye again, giving me what I took as a knowing smile. I smiled back. I don’t know if Jen was aware of this little exchange and really didn’t care.

When she finished with my scalp, he moved up to one side and she moved over to the other. There seemed to be a slight hesitation, then the apprentice reached up and folded down the draping, exposing my breasts. I felt that he might have been a bit nervous doing that, as I think he folded it back a bit too low. At that moment I was glad that I had thought ahead and groomed myself, as, if I hadn’t, the top of my bush would probably have been visible.

They both started at my neck and moved across the top of my collarbone. Their hands moved lower and ran between my breasts, gently but firmly pressing in. In the process of completing the move, Jen brushed her palm briefly across my already erect nipple. I couldn’t contain my surprise, and involuntarily let out a slight moan. Jen paused. She looked at me and then, almost nonchalantly, asked if I wanted my breasts massaged. I was surprised as this had never been part of the routine. But, after just a slight pause, I said that yes, I think I’d like that.

They started on the outside of my breasts. I then realized that this wasn’t just going to be Jen; the apprentice was joining in. For a brief second, I thought about stopping it right then, but that moment passed once they started kneading my sensitive tissue. They worked towards the underside and then up between them again. They repeated the sequence of circling around, using more pressure on each pass, but, so far, avoiding contact with my nips. I felt like they could do that for hours. But that didn’t last long as first Jen and then the apprentice each grabbed a breast with both hands and moved up and over my nipples. I couldn’t contain my now heavy breathing.

Suddenly Jen took a solid grasp on the nip on her side and gave it a bit of a pinch. He followed suit and, to my shock, I felt myself starting to build towards a climax. It built up quickly. I was too far gone to try to avoid it, so trying to hold back wasn’t an option. I reached down and grasped my pussy over the sheet, clamped my legs together and let out a moan as the feeling crept over me.