Massage Apprentice Ch. 09

Massage Apprentice Chapter 9 -- Jen wants a Reprise

This is a continuation from a previous chain of stories. Although I feel you should probably read the them, this one can probably stand on its own.

Many thanks to Fewella. She was a great help with the editing and suggesting some changes. A great 'second pair of eyes'!

All characters participating in sexual activity in the stories are 18 or over.

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From Chapter 8: As I took a long shower, I wondered how much of what had just happened I should let Jen know; how far I had crossed over that 'ethical line' with Sue. I decided that, if she asked, I would tell her everything, but I was hoping she wouldn't ask.

I was still pondering this when, over the sound of the shower, I heard Jen call out "Hello? "

I shouted back to her "I'm in the shower...can't hear you... I'll be out in a minute."

I continued to soap myself down, washing away the evidence, when, through the translucent glass of the shower stall, I saw Jen come into the room. This wasn't the norm; we generally didn't watch each other taking showers. But, also, it wasn't unheard of. We had been in this situation before when one of us was in a hurry and we had some business to discuss. I wasn't exposed; with the make-up of the shower door and the buildup of steam I could barely make out the outline of Jen, so she wouldn't have been able to see much of me either.

"What's up?" I asked.

She had been out giving some massages at the salon that a friend owned. These weren't regular clients; Lisa, the owner, offered discount massages when a client bought a 'package' of treatments. Jen kept a portion of the payment, which ended up being much less than we'd have charged for a full hour, but the hope was that we could convert some of these new clients into becoming regulars. So far it had been mildly successful; about half of the massages given resulted in new regular clients. Lisa was fine with the arrangement, as that offer of a free massage had brought her a good number of first-time clients as well.

Jen replied "I'm beat. I was only scheduled for three sessions, but Lisa had a walk-in before I even got there and another while I was on the last client. So, there were five half-hour sessions. But I think we might be hearing from a couple of them."

She continued to talk while I finished showering. "I asked Lisa if she'd be ok with you taking some of the clients, giving some of the massages. Would you be up for that?"

I said, "Sure if she thinks her clients wouldn't mind having a guy massage them."

"The only thing is that Lisa doesn't know you. She's been here a couple of times but never when you're around. She would like to get a massage from you before she decides. Call it a test run, so to speak."

"That would be fine with me. Here, or at her place?"

Jen replied "I don't know. I'll get in touch to try to schedule something. And she's in our system, so you can check up on her beforehand."

The 'system' was our client database that I had created and, for the most part, maintained. I had taken Jen's index cards containing basic client info -- contact info, age, height, and weight -- and added other information, like health issues, last visit date, preferences, etc.

"OK, that sounds good." I finished rinsing off and opened the shower door just enough to reach out for my towel. It wasn't there, although I was pretty sure I had hung one up.

I asked Jen "Can you hand me a towel?"

"Sure," she said, and a small washcloth sailed over into the stall.

Now I knew that Jen was playing with me. "Very funny. Can you hand me a real towel?"

"It's out here if you want it. What do I look like, your maid?"

'OK, so that's how she's going to play it' I thought. She'd seen me naked before when we had spent the afternoon at a spa and had at least seen my backside multiple times on the massage table, to say nothing of the one time she had provided me with a little extra happy massage, so it wasn't a big deal. I could have played it coy and tried to cover myself with the washcloth, but instead, I just strolled out, walked past her as she leaned against the sink, and got my towel that was now hanging on the back of the door. I saw her watching me, trying to hide a grin.

As I was drying off, Jen asked: "So how did it go with Sue?"

I knew she was going to ask me about the session, but I didn't expect it would be this soon. I was hoping I'd have some time to come up with a believable explanation of what happened, without going into how far I had crossed that 'ethical boundary line'. I hesitated before I answered her, making a show of wrapping the towel around my waist.

"I think it went well. Sue seemed to enjoy it; she had no complaints."

"Was she up to her usual antics?"

We both knew that Sue almost always wanted her special 'alone time' after the session so that she could release whatever tension she still had.

"Yes, of course, she was."

I wasn't willing to open up about what really went on, and I could tell that Jen had picked up on that. I also knew that she and Sue were pretty good friends, and Sue would definitely share the experience if Jen asked about it.

Thankfully, Jen quickly changed the topic of conversation away from Sue's session.

She said "I sure could use a massage. I'm pretty sore from this afternoon" Then she asked, "Do you think you have another one in you?"

The phrasing of that caught me off guard. "You'd like a massage?" I asked.

Jen replied, "Yes, please... if you're up for it."

I would never turn down an opportunity to massage Jen. Besides being an excellent teacher, she was also an excellent subject. To be honest, I'd never turn down the opportunity to have her mostly naked on the table. And, given the playful mood that she was in, I could easily see that this might turn into something special. She had recently given me a happy ending massage -- a first for her -- and ever since then I had been looking for an opportunity to return the favor.

So, of course, I said I'd be up for it.

She said she wanted a shower first. I told her I'd get the room prepared.

I finished drying myself, then threw on my sweats and went to the studio. I had already prepared the room after the previous session with Sue so there was no work to be done. I went into the kitchen, poured two glasses of wine, and carried them into the bathroom. Jen was already in the shower. I called out that I had a glass for her. She was a bit startled and started to cover herself before she realized that I couldn't see anything. I did take the opportunity to move her towel away from the hook by the shower door, as she had done to me.

"So, "I asked, "what type of massage are you looking for? Are you sore?"

Jen replied "A bit. I just need to relax. Why don't you give me the same treatment that you gave Sue?"

OK, back to that topic. It was hard trying to think of this while I was watching her shower. Yes, I couldn't see anything specific through the shower door, but sometimes that can be pretty hot.

"Yeah, Sue just wanted to relax. And if that's what you want, I'm pretty sure I can deliver."

"Great then, just like Sue's massage!"

She turned off the water and reached for her towel, and, just as she had done to me, I threw a small washcloth over to her. I think she might have seen this coming because, without the slightest hesitation, the washcloth came sailing back over the shower door. Then Jen came out to get her towel. She half heartily pretended to cover herself, with one hand over her crotch and the other over her breasts. She had a big smile on her face; I knew she was in a playful mood.

After she wrapped the towel around herself, I handed her the wine then told her "Go on in and make yourself comfortable. I'll be right there."

I took my time, finishing my wine, and then refilling it. When I went into the studio, Jen was lying face down with her towel covering her ass, as was our accepted practice.

"Just like Sue," I said and removed her towel.

Jen lifted her head and turned to look at me but didn't say anything right away. She smiled, put her head back into the doughnut, and said "You're right. Just like Sue."

I took more than a moment to appraise the view in front of me. She had a well-toned back and shoulders. Her arms also had good definition without being overly muscular.

Have I ever mentioned how beautiful Jen's ass was? I'm sure I've mentioned it, probably more than once. But it was, and remains, one of the best ones I've seen in all my years of practice. It was full but not fat, tight and firm with some muscle tone. Of course, I'd seen it before, but more often than not with at least a cheek covered.

I enjoyed taking in the complete view.

Perhaps I lingered too long, as Jen lifted her head out of the doughnut, and turned back towards me, clearing her throat.

"You can begin anytime now," she said, with a smile.

I was about to apologize when I thought of a different tactic. "Sue didn't mind me looking," then added, "I think she wanted me to look."

Jen said, "That sounds like something she'd do."

I continued "But I'd much rather look at you."

"That's sweet but so unprofessional of you. Who trained you to act like that?"

"I have a great teacher. But I've got to admit I've taken what she taught me and added a few touches of my own."

Jen smiled, then turned back around and settled her head back into the opening, saying "Show me what you've got."

I applied some oil to my hands and started the massage, spreading the oil evenly across her shoulders and upper back.

"Finally." she muttered.

As I worked on her back, Jen spoke up again. "So, Sue likes to be looked at. Who'd have thought?"

I just smiled.

She continued. "And you obliged, of course."

"Sure. I was taught that the client is always right."

"Did she enjoy the service?"

"Yes, of course. I aim to please." I paused for a moment, thinking out my next words. "It was unlike any massage I've given before."

"How so?" asked Jen.

I was a bit hesitant but had decided I was eventually going to have to tell her all about it. If I didn't, she'd probably hear about it from Sue anyway. For all I know Sue might have called her right after the session and filled her in with all the details.

"I was planning on just giving her my standard massage. And, afterward, if she wanted her private time, so be it. At least this time I was going to be prepared for it."

I was referring to the time that we had given Sue a four-hand massage, which was a first for us. After we had finished and left the room, Jen asked me to go back in to give her some extra towels. I walked into quite a scene. Sue was still lying on her back but was deep into a masturbation session. When she saw me, she pleaded with me to stay and watch... and of course, I did. Jen had set me up, knowing the Sue often follows up a massage with a little self-satisfaction.

I continued to work on Jen's back.

"But then a couple of things happened that made me change my mind about the massage. She started teasing me, almost taunting me. At least that's how it felt to me."

"How so?" asked Jen once again.

"Well, to start, before the massage I offered her a glass of wine, as you suggested. When I came back into the room with the wine, she had already undressed down to her undies."

Jen spoke up "A matching set, I presume."

"You do know her pretty well. Yes, actually a very pretty, and very skimpy, pale blue set, but that's beside the point. She knew better than to get undressed while I was there."

"So what did you do?"

"I tried to act nonchalant about sitting drinking a glass of wine with a mostly naked lady. But as we talked, she started teasing me more, telling me she wanted a hard massage, about how much she likes it long and hard."

I heard Jen chuckle. "So far, it sounds just like her. You know she was joking, right?"

"Yeah, but for some reason, it got to me. So, at that point, I decided to turn the tables on her and give her a taste of her own medicine."

"And?" Jen asked.

"I decided I was going to give her the best possible massage I could but include some 'almost' intimate touches to get her going, without actually following through."

"Quite a tease, but not that different from the time we worked on her together," said Jen.

"Oh, I was going to go a lot farther than we had."

"How so?" Jen asked one more time.

I momentarily paused, then moved my hands from her back down off to her sides, around her waist. I slid them up a bit, to where her breasts were flattened against the table.

As I massaged the sides, I said: "I knew that Sue liked to be touched here." I cupped my hands around her exposed flesh. Jen apparently liked it as well, as she lifted herself off the table a little, which allowed me better access. I briefly ran my fingers over her nipples, then pulled my hands away, saying "But I wasn't going to let her enjoy herself quite yet."

I went back to her lower back, working my way down to right about where her butt crease started. I poured some more oil into my hands and spread it over both of her cheeks, leaving some excess in the small of her back. With a hand on each cheek, I spread them apart, using my thumbs to push the excess oil down into her. In a normal massage, draped or undraped, the 'anal fissure' was off-limits. If she had any doubts before, I'm pretty sure Jen knew at this moment that the massage was going to be anything but normal.

"Remember when we did this to her before?" I asked as I worked the oil deeper into her crevice. "How you were tempted to touch her?"

"MMM'' was all I got from Jen.

"How, afterward, we both thought how smooth she was?" I continued rubbing around her ass hole. "You're pretty smooth as well." Holding her apart with the heels of my hands, I used my index fingers to circle closer around.

"So, with Sue, I went a little bit farther."

As I said this, I rotated my hands so that my thumbs were in her crack. I brushed them around her hole again, and then put my right one directly on her little rosebud. I applied a slight bit of pressure. Not enough to enter her, but enough for her to realize that with the slightest extra push I would be in her.

Jen was moaning lowly throughout this; she was enjoying my touches. She had raised her ass off of the table a bit. I could have continued down past her ass to her taint, but instead, I removed my hands from within her ass, and gently push her back down onto the table, giving her cheeks a final squeeze before I moved on.

I moved down to the end of the table, breaking contact with Jen. That seemed to have startled her, as she once again raised her head and turned to look at me. She was smiling, but it was a different type of smile, one that I hadn't seen before. Without saying a word, she turned and put her face back into the cradle.

I took some oil and spread it on both legs, from her ankles to just below her ass cheeks. Before I could go any farther and work deeper, Jen spoke up and asked if I could do her feet; "I feel like I've been standing all day." I don't usually work on the client's feet. No real reason, it's just a body part that I skim over. But of course, with Jen, I was more than willing.

I took her left leg and bent her back at the knee so that her leg was perpendicular to the table and her foot parallel, giving me easy access. I applied just a bit of oil and worked on her sole, pressing hard into her with my thumbs.

"Yeah, that's nice," she said.

I continued that and then moved on to her toes, giving each one a little tug while working the oil in. When I finished with that foot I released her leg back to the table, deliberately placing it farther out to the side. I repeated the same for the other foot so that by the time I was finished with her feet, Jen's legs were widely spaced apart. I was getting a view of her that I hadn't seen before, and it was something special. Her crack was glistening from the oil, and, although I couldn't be sure, it looked like she had kept herself shaved as she was at the spa.

I'm sure Jen realized how exposed she was, but before she could say anything I started working on her left leg. I massaged my way up her leg, starting at her calf. I got to the top of her thigh, where, in a 'normal' massage, I would have stopped. But, for this special massage, I kept going, higher up her thigh, until my inside hand was almost brushing against her lips. And with her spread so open, I could see exactly how close I was.

I pressed hard into her inner thigh, with the back of my hand resting squarely on her pussy. As I pressed, I rotate my hand slightly, causing my knuckles to rub across her.

I kept my hand there for a while, rotating and pressing. Once again, Jen tried to press back against me; I stopped at that point and went over to her right leg, repeating the process.

Jen, in a soft, breathless voice, managed to speak up. "And I'll assume Sue enjoyed that as much as I did."

I smiled, thinking "oh, you have no idea." But I spoke out loud "It's all just part of my special massage. Relax now."

I went back to her feet and started to work my way back up, a hand on each leg. Once again I passed my thumbs close by either side of her now fully exposed lips, pausing just slightly then continuing up onto her ass, my thumbs trailing behind, dragging across her ass hole. I left them there while I squeezed and molded her cheeks.

Jen had let out another sigh as I passed over her pussy the first time, and perhaps anticipating when I repeated the move, she once again raised her ass a bit off of the table, possibly seeking more contact. I stopped and firmly pressed her butt back down.

I murmured, "Just like Sue." Jen just sighed.

I gave her legs one more pass, with the same contact, but continued up past her ass to her back, stopping at her neck. I decided I was ready for her to flip over. I walked over beside her, leaned in very close to her ear, and whispered "It's time to turn over."

Jen slowly opened her eyes. I asked her if she wanted a cover.

She responded with "I can assume that Sue wasn't covered, right?"

When I replied "Correct.", she sat up, turned over, and laid back down. She smiled at me and closed her eyes.

I wasn't about to tell her that in some ways we'd already strayed from the massage I'd given Sue. With Sue, I came close to touching her intimate spots, but, until the very end of the session, avoided direct contact.

As I had done when she first laid face down, I took a long moment to look at the vision in front of me. I saw her looking up at me, so I made eye contact, smiled, and purposely broke contact, letting my eyes trail down her body. Jen knew I was drinking in her body and apparently didn't mind that at all.

My eyes paused at her tits. She had full, womanly breasts, but without any apparent sagging. Her pink nipples protruded. Although I had seen her topless before, I couldn't tell whether they were always that firm or if my massage was affecting her.

Continuing down, I paused to admire her belly. Not flat; there was no way anybody would consider her overweight, but she did have a small little pooch. Then, moving down, I confirmed for the first time that she had kept herself trimmed as she was at the spa. She had left a small thin patch of light, almost blonde hair just above her clit, and was bare from there down. Her lips were visible and seemed to me to be a bit engorged. Again, I didn't know if this was her normal condition or not.

I moved to the top of the table, above her head, and started by massaging the back of her neck and shoulders, reaching under her. I pulled gently, but firmly. I repeated the motion, but then continued it by bringing my hands around to her front, smoothly moving over her shoulders to her upper chest. I paused to put some more oil on my hands, then, with one hand over the other, moved down between her breasts, making slight contact on either side with my little fingers. Keeping my hands firmly pressed against her chest, I separated them and swept along the underside of her breasts, circling back around to the top. Without breaking stride, I repeated the move, separating my hands so that when I moved between her breasts I made more contact, rubbing the side of each tit. As I moved down, I raised my hands a bit so that I was almost cradling her, and then continued massaging her breasts as I moved back around and up. On the third time through this I didn't just tease her by barely touching her breasts; I deliberately massaged all over, with delicate touches on her erect nipples, and with stronger firmer pressure around them.