Massage Apprentice Ch. 09

Jen gave out a low, soft "Hmmm" as I was doing this, so, assuming that she was enjoying my touches, I continued to massage her breasts, with lots of attention to those hardened nipples. I openly caressed them, giving them a slight pinch, and after a while, a slightly harder pinch. Perhaps I was a bit too hard.

Jen spoke up "Ow!", and moved her hands up to cover her nipples, lightly caressing them.

I said, "I'm sorry," then leaned over her, moved her hands away, and planted a light kiss on her right nipple.

"All better?" I asked.

She smiled up at me and said "A bit.... don't forget the other one."

I smiled back and repeated the kiss on her other nipple, lingering a bit longer and giving it a light lick.

"Yes, all better now," she said, still smiling at me, and then asked, "Are we still following Sue's massage?"

I laughed and said, "No, that was a special just for you."

Jen gave me that look again, like the one earlier, then closed her eyes and replied "Thank you. Carry on."

I put my hands on her belly and started rubbing her lightly in small circles around her belly button. On each circle, I increased the area until I was bumping up against the underside of her breasts on the top of the circle and rubbing against that small patch of hair on the bottom of the circle. I wasn't in contact with her clit but would have been if I increased the circle just a bit.

So, on the last pass, I did increase it. On the bottom of the circle, I let my fingers brush right over her clit, slowing down to increase the contact time, and pushing down harder than I had been. I felt Jen shiver as I touched her. Then, before she could comment, I moved down to the foot of the table to do her legs.

Jen spoke up. "Well, that was a tease! Like Sue?"

I put some oil on my hands and started to apply it to her left leg. "I like to think that each massage is unique...customized to the client's preference."

She knew I was just kidding, so she just smiled up at me at said: "You're supposed to be able to read the client's body movements to determine if the treatment is working."

I had read the same quote in a textbook. I replied, "Your body was telling me to move on... no?"

Jen closed her eyes and said, "Not exactly right... but please do go ahead, continue."

As I did on the back of her legs, I started at her left ankle and worked up, kneading the skin from side to side. As I reached her upper thigh, I took extra care to keep firm contact and slowed down the pace. Also, as before, I went far enough up to let the back of my hand graze against her lips. I held my hands there and wriggled my left-hand fingers so that she could feel the motion and kept it up just long enough for her body to acknowledge that she felt it, then repeated the same on her right leg. This time, as I wriggled my fingers against her, Jen started lightly moaning almost immediately. I assume that was because she was anticipating the action. She tried to raise her butt off the table, into my hands, but, once again, I held her down. Then I quickly flipped my hands over so that my palms were against either side of her pussy, and used my thumbs to trace around her lips, gently and slowly. I could tell she liked that as well, so I kept it up for a bit.

Jen was pretty well worked up, even more so than Sue, so I decided to end the massage. I probably should have continued to see if she wanted me to supply her with a happy ending, but I was unsure. Looking back, there were obvious signs, but I hadn't processed them. I told her to take her time getting up, a standard phrase for indicating that the massage is over. She opened her eyes, looking me over, and then asked: "Is this how Sue's massage ended?"

"Well, she had some personal time... which of course you can have as well."

"And?"

Going on, I replied "Sue asked me to stay and watch, so I did. So...?" I handed her the bottle of oil and stepped back. She understood immediately.

"Did Sue do this?" she asked, as she poured some onto her hands and then began to touch herself. She ran her hand over her pussy and started to rub herself.

That was pretty much exactly like Sue, so I just nodded yes.

"And you just watched?"

I knew that if the massage got this far there was going to be a moment of truth for me, and this was it. I thought about it for a second then replied, "I should have left, but it was so hot watching... although not nearly as hot as it is now...so I stayed."

"And?"

"And she wanted to touch me." I move closer to Jen, as she continued playing with herself, alternating between rubbing her lips and fingering her clit.

She asked again "And?"

"And I let her."

Jen paused and then looked up at me. She smiled, murmured "Just like Sue", then rolled towards me and grabbed my extremely hard dick through my sweatpants. "Show me."

And here was another moment of truth. I stepped even closer and for the second time that day, I took off my sweatpants and dropped them to the floor.

Jen had given me a happy ending massage not that long ago, so she had seen me erect, but this situation was reversed. She was the one on the table and, theoretically, I was the one in charge. She reached over and grabbed my cock, looking up at me. Her eyes were heavy-lidded as if she had been sleeping. She murmured "Yeah" and started to jack me off.

To say I was in heaven would be understating the situation; watching her, naked, one hand in her crotch and the other on my cock was almost beyond belief. I saw that she had paused working on herself, so I moved down towards her and took over where she had left off.

We continued to masturbate each other. I most likely would have cum much quicker, but I had already cum earlier and could now hold off for a while. Eventually, she stopped pumping me and put her hand over mine, pushing it harder into her pussy. I put my middle finger into her, curved upward as she stroked her clit. I sensed she was near her climax.

I was right. Jen went into overdrive, rubbing herself at a frantic pace, alternating between moaning and trying to catch her breath. I followed her lead and increased pumping my finger in and out. Then, with an even louder moan and a gut-wrenching spasm, Jen came. I had never seen a woman cum that hard before, or since, for that matter. She clamped her muscles down on my finger and stopped her rubbing for only a moment before she started up again. I also started pumping in and out, now with two fingers in her. It didn't take her long at all; she came again, for the second time, quickly and only slightly less violent as the first. And she didn't stop rubbing, so I didn't either, causing her to cum once more, this one quietly, more likely an aftershock from the previous ones.

When the moment had passed and she was through the spasms, she stopped rubbing herself. I gently removed my fingers. Her one hand was still on my erection and, after a while, she gave it a gentle squeeze, her eyes still closed. She got her breath back, opened her eyes, and smiled at me.

Jen softly said "Well I guess I needed that. Thanks."

I replied, "Believe me, it was my pleasure."

Jen, still with a smile, pulled me even closer. She sat up a bit and leaned over to give my cock a kiss. The kiss turned into a lick and just as quickly my cock was between her lips. As good as it felt, I was just as excited about watching her.

She attempted to get all of me in her mouth. I am not huge by any standards, but still a mouthful. She gagged, then pulled her mouth off me.

Jen looked up at me and asked if I still had that little gift from her. She didn't need to explain any further; she had given me what I had thought was a gag gift of a half dozen condoms, before having my one on one with Sue. They were in a drawer on the side table. I went over and got one.

Walking back to her still on the massage table I took a moment to soak her all in. She was wet with oil and sweat and looked like she had already been well fucked. I guess she wanted more than anything to return my favor and I, of course, was up for it, literately and figuratively.

"Is this what you're looking for?" I asked, knowing full well that it was.

When I got within range she reached out once again and grabbed me, pulling my cock towards her mouth. She gave me a quick lick up and down, then took the condom from me, unwrapped it, and slid it on without an issue. I moved back to the end of the table, grabbed Jen's hips to scoot her down towards me, and aimed my wrapped cock towards her opening. I was going to go slow and enjoy every moment, but Jen was not having any of that. I had just slipped the tip in when she wrapped her legs around my waist and pulled me closer, forcing my cock all the way in. She sat up a bit towards me and, almost in a growl, said "Fuck me!"

This was a side of Jen that I hadn't seen before, many sides actually, and I liked it. A lot. I had thought earlier that I would be able to hold off for a long time, but now, even with the condom deadening some of the sensation, I knew I wasn't too far off. I wondered if I could coax another orgasm out of Jen. I made up my mind to try to hold off.

Jen didn't make it easy. She made it clear that she wanted to be fucked fast and hard. After the initial entry, I pulled almost completely out, but Jen once again drew me back in with her legs. I gave up on pretending to tease her; she wanted to be fucked as much as I wanted to fuck her.

She kept encouraging me to give it to her and I kept pounding at her, giving her everything I had and then pulling almost all the way out. I looked down to watch my now oily dick disappearing into her folds. When I looked up, Jen was watching me through her heavy-lidded eyes. I plunged deep once again then paused and leaned forward to kiss her. She opened her mouth and we swapped tongues for a while, then she pulled back and said "Fuck me, now. Just fuck me. I want to feel you come."

I pulled back out and continued. I sensed that she was on the edge of yet another orgasm, so I gave it everything I had. At that rate, it didn't take long before I was also on the edge. I almost timed our releases perfectly; as soon as she cried out and clamped down on me, I pushed deep into her one last time and shot a load into the condom. I stayed there inside of her until the moment passed. Then I carefully pulled out and peeled off the condom, throwing it into the nearby wastebasket.

Jen continued to lie on the table, soaking in the afterglow. She had a silly smile on her face, and I couldn't stop myself from leaning back over her and giving her another kiss. This time was no less intense, but every bit as passionate as before. When I broke off the kiss, Jen looked up to me and said, "You don't know how long I have been wanting this."

I was a bit dumbfounded, as I had no idea. Even so, I had to respond. "I've been wanting this since we first met."

She smiled and said, "I guess we're both pretty good at hiding our feelings." And then added, "But no need to anymore, right?"

I had to agree.

Jen sat up, not bothering to cover herself. "I think I need another shower." She held her hand out to me. "Care to join?"