Pt. 01 - I Learn About Women, Sex & Love

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Jan didn't say anything, but her eyebrows went up wondering what the hell that was all about.

My last appointment that day was set for 7:30pm.

I was never sure if the person that was supposed to come was a no-show or that Jan set me up.

Because I had to get my lab hours in, when the lady scheduled for Friday night didn't show up, Jan made what we call an Executive Decision and said to me "I'm your last client for today."

###

I'd never been around a woman who was so relaxed, or should I say comfortable in her own skin, especially when she was naked.

Jan and I walked to the back of the building and said to me "Take quick shower to get the stink off of you. Then I want you to put on a clean uniform."

I made my way quickly from the shower to the dressing room. Behind closed doors, drying myself off, I looked around and found a large pair of shorts that I assumed the other

male students wore when they were in lab, either as a client or as the masseuse.

I looked at the shorts wondering who the last guy who wore them was.

And did he go commando?

Jan knew me better than I thought.

She heard me mutter something and then she laughed and said loudly "They're clean."

I put the shorts on. They were baggy around my waist, and I had to hold them up with one hand to stay "dressed."

"Do you have anything in a smaller size?" I called out.

"No, I don't. Those will work fine Rick, just come out when you are ready."

"What about a tee shirt?" I asked.

"You won't need one Rick."

I opened the door still clutching the shorts so that they wouldn't fall to my feet only to see Jan lying face down on a massage table. No towel. No sheet. Naked.

Even at ten feet I could see I was right in my assessment that she had a great figure.

Her large breasts were squashed, and her tit flesh popped out on the sides.

Her back was taut, and it was clear she did weights.

Her ass was, well, stunning. Firm, just the right size for her frame.

Her legs were shapely, her thighs were thin, her calves were muscled but still very attractive.

Her feet were dainty and her toenails were covered in dark red polish.

The tan lines were in all the right places.

I could see as I approached her that she liked wearing thongs and apparently sun bathed topless because there was no tan line across her back or shoulders.

She lifted her head out of the cradle and turned, seeing me half naked for the first time. Her eyes smiled as she took in my toned chest, arms and legs.

She laughed when she saw me holding the shorts up.

Still chuckling she said, "Come over here and let's get started. Tick tock Rick."

#####

Her flawless naked body filled my eyes and blood flooded my cock.

At 28 years old, this was the closest I had ever been to prime pussy.

I had a "Sophie's Choice" moment when I figured out that I could either massage Jan with one hand while the other hand held up the shorts or I could massage her naked with the shorts on the floor.

(I guess I could have gone back to the changing room and put on my smelly, sweaty jock strap but why take a shower and then put back on that dirty thing?)

So, I made my own Executive Decision to drop the so-called uniform and Jan chuckled again when she saw the big, baggy shorts on the carpet beneath her as she laid with her head in the massage table cradle.

I was going to be nude for this massage.

I was hard, my cock bobbing in front of me.

I had another Executive Decision to make as Jan was lying there in front of me undraped.

Being nude was a good look on her, actually a very good look, and I had wondered since the day we met what her ass looked like.

I was tempted to reach out and cop a feel but remembered that these were actual lab hours and she was the client.

And my supervising instructor, or teacher.

So, I reached over and rather professionally put my right hand on the middle of her lower back.

Her skin was warm to my touch and it was smooth, unblemished.

I took in her entire backside and more blood surged into my cock, causing my manhood to start throbbing.

It had been a game all day long trying to keep from getting too hard while I massaged the previous female clients.

I had gone from soft to hard, down to up, up to down, so many times I couldn't keep track.

The worst part of it, or maybe it was the best part, was when I had a female client on her back, a towel draped across her lap, and a second towel was across her breasts.

Jan was a stickler for making sure that I massaged the upper chest muscles with both hands, which forced the patient's breasts up ... hardening their nipples ... but my hands could only rub a small part of the swell of the upper breast.

And these ladies liked what I was doing and wanted I am sure, for me to massage their entire breast, teasing their nipples ...

But each time before I could act on my impulses, Jan would smile at me and coyly say "That's enough Rick, time to move on."

Slowly moving my hands out from being just under the towel I heard each client silently grown as I ended that part of the massage.

And when I massaged their lower backs, their butts and thighs ... Jan moved to almost being right next to me to provide direct supervision and instruction.

Again, when my hands and fingers got too close, Jan would reach over and touch my arm and say in a low voice "Rick ..." and I would nod and move my hands away from those sensitive areas that I just knew my clients wanted to me to massage.

How did I know? Each woman had her own way of messaging me but they all spread their thighs under the draped sheets, signaling me their interest in having me rub higher up their thighs and their butt cheeks, with the ultimate objective for me to finger fuck them to an orgasm or two.

Jan knew this and knew when to step in to move the massage in a different, a legitimate way.

Between the teasing of their breasts and the denied opportunities to massage some juicy wet pussy and some tight ass, my cock went from soft to hard, back to semi in a vicious cycle. Hours later, I didn't have blue balls, but I knew that when I did come, it was going to be a very big load.

Now, at the end of the day, standing next to a nude Jan, I gulped, which seemed so loud to me that I am sure the people working in the office next door heard through the concrete wall and then I whispered to Jan "Shall I drape you?"

###

Her reply startled me.

"That won't be necessary Jack. But I need for you to get me two hand towels."

I was an accountant, certified in fact, but not too experienced in the ways of women.

Don't get me wrong, I wasn't a virgin, I had actually gotten laid a few times though not lately.

But I also knew that two people, naked, single, with nowhere else to go on a Friday night; two people who liked each other, had been touching each other, though not sexually, for the past few weeks, given the opportunity, were on the track, on course, on the trail to fuck.

At least that was how I wanted things to turn out.

####

My hard cock bobbing in front of me, I walked over to the cabinet where the towels, sheets and other supplies were stored and I was sure that Jan lifted her head up as I walked past her so she could see my bare ass for the first time.

I heard her exhale as I pulled my cheeks in, clenching, putting on a little show.

Why not? She was putting on a show for me and we both knew it.

Before I turned around, Jan had her head back in the cradle.

I took two white towels off the shelf and went back to the side of the table, taking in a magnificent view.

Jan once again lifted her head out of the cradle without turning her head and said to me "Take one the towels and fold it lengthwise so it covers my crack and then pull it down and tuck it the other end under my ass and cover my pussy."

It seemed like a reasonable request but we both knew that when I did this little task, I'd be seeing the goods.

Her goods.

And, I was not disappointed: her pussy was shaved bare, maybe even waxed; her lips were swollen in arousal and I thought I could detect the scent of a woman starting to get heated up.

I finished my task and Jan surprised me again with "Did you like what you see Rick?" and then to my amazement she wiggled her ass a bit as if my covering her ass and pussy was a warm-up for something bigger ...

Before I could respond, she said "Set the other towel down. When you finish with my back, I am going to use it to cover my titties."

And then she giggled; something I didn't know how to take so I just started in my massage.

###

I had to give the woman credit.

When I did a good job, getting the kinks out of her neck, shoulders, and back, she sang me praises.

And when I made a mistake, like not using enough oil, going too fast, or going to slow, or not getting a kink completely out, Jan let me know in no uncertain terms I was under performing and she gave me very clear instructions how to improve.

When she sang me praises, it was almost like heavenly music it was so pleasant.

The opposite feedback came across sort of icy, as if I should already know this stuff although I was truly a novice at this new occupation.

My cock, which started out hard, throbbing and in need of relief went into a semi-stage of engorgement while I was putting in the very hard work of massaging my instructor. And, just so you know, massage is hard work and this was my sixth massage of the day. Despite my youth, despite the protein shake from Jamba Juice, I was getting tired.

A couple of times I accidently pushed my fingers under the towel that was covering her crack and my fingertips slipped into her crack, pushing the towel over a bit.

Jan tensed up, initially, and said nothing to me, because I quickly corrected the error of my ways and pulled my hand back and in a flash, pulled the hand towel back over her ass crack.

When I finished with her feet, completing the first half of the massage, Jan told me stretch my legs and to use the bathroom while she rolled over and got situated on her back.

Jan was on her back when I finished my business. I was thinking that I would whack off while I was in the toilet but decided that I would just suck it up and take care of business when I got home.

Still nude, my cock now soft, I found Jan on her back, with towels covering her pussy, her tits and a third towel across her eyes. She'd also dimmed the lights even further.

"This is the final exam for today Rick. Take your time, be professional, and make your instructor happy."

I wasn't too sure what she meant by "make your instructor happy" so I just figured that I would give her the best massage I could and let it go at that.

I did just that, and all of the iciness and corrective commentary and instructions when I was doing her neck, back, butt, thighs, calves and feet disappeared from her script.

I was professional, competent and got the job done without hearing a word from her.

All I heard were sighs and all I could see were smiles. Not big smiles, but she had a nice, pleasant smile on her face the whole time. Like the cat who ate the canary.

I took my time on her neck, and pulled her back muscles up. I massaged her upper arms, her lower arms, her fingers, popping her knuckles as I pulled on each finger in turn.

Next, I worked on her upper chest, being careful not to put my hands under the towel but I was mesmerized by the rise and fall of her breasts and in no time flat her nipples rose up under the towel creating nice pokies for me to think about.

I folded her hands over her upper chest and worked on her abdomen being generous with the oil as my hands swept in ever widening circles around her flat belly, expanding out so that my fingers would go just slightly under the towel covering her under boob and when I moved south my fingers went under the edge of the towel covering her pussy.

Massaging a back is one thing; I didn't think it was very erotic at all. But rubbing the tummy of a hot babe and brushing your fingers, even slightly on some under boob and then under some remaining pubic hairs just north of a pussy, well, that got me hard again quickly.

Plus as I rubbed both of these towels, they moved so that I was seeing more skin than I think Jan intended.

She just sighed and smiled a bit more.

When I started on her feet, Jan spread her legs a bit, probably to get more comfortable.

When she did this, I could see right up Jan's now spread thighs to her hairless pussy.

I took my time on her feet because there is a lot of tension there.

As I started in on her arches, she winced and actually moved her foot away to avoid the pain, but she didn't say anything.

When this happens, the masseuse is supposed to slow down, get the client calmed down, rub another part of the body and then return to the pain point only this second time around, go slower.

I massaged her ankle and then went back to her arch, and I went slow and soft that Jan started laughing, kicking at me to stop.

When she did this, she did it with such force that the towel covering her pussy fell to the carpet.

Of course, I expected Jan to tell me to go get another towel, a clean one, and cover her with it.

Instead, with an even bigger smile, she said "Finish the job Rick" and with that I quickly wrapped up the foot massage.

Getting up on the end of the massage table, my hard cock swaying, my balls in a very tight sack, I started in on her calves, and I pushed her legs apart as I got to her knees, where I paused before heading north up her tanned toned thighs.

Jan aided and abetted me as she spread her thighs in anticipation of my hands getting there.

As my hands reached her apex, my face was just a few inches above the object of my desire.

I could smell her arousal and I was sure she was damp with anticipation.

Her pussy was swollen, her labia was nearly ready for sex.

She was bare except for her tits which were still covered with the towel.

The towel that had been covering her eyes was on the floor.

With heavily lidded eyes and a smile, Jan spread her legs even wider.

In a move that surprised me, Jan lifted her calves onto my shoulders, and gave me an order I had never thought I would hear her say: "Eat me Rick."

###

28-year-old guys often think with the wrong head, but I didn't think twice about not following Jan's instruction.

I figured this was a prelude to having sex with her, so with a shit eating grin, I lowered my head and licked her hairless pussy from the bottom of her slit to the top and Jan shuddered at the anticipated but unexpected pleasure of my tongue on her cunt.

Her right hand found its way to my head, directing my oral activities.

The second lick, slower, teasingly slower, and with my tongue flat with the goal of separating her slit through the most pleasurable means possible, earned me a loud groan from Jan. She was worked up. She wanted this.

I could sense her wetness increasing.

For the third lick, I skipped the slit and focused exclusively on her love bump while my right index finger gently probed her slit in search of her g-spot.

Jan responded with some grunts and her calves pulled my head even closer to her crotch as my tongue and fingers performed oral and digital magic.

She was already worked up and after just a minute or so of doing my ice cream cone lick, Jan came for the first time.

It wasn't a big O, it wasn't enough to satisfy her pent-up need for a nice strong release, and she didn't relax her calves or take her right hand away from my head so I simply kept at it.

What that first little O did was loosen up her pussy so that I could get two of my fingers in and without hesitation I curved them up so that I could play the piano on her g-spot while my tongue continued its nonstop attention on her clit, now standing at full attention.

Her pussy flowed.

My left hand left her thigh and I snaked it under her in search of a puckered asshole that I had briefly seen but had not yet touched.

Jan groaned and grunted as I finger fucked her wet pussy, teased the shit out of her clit and when I found that tiny rear entry hole, I didn't bother to lube it but probed it bone-dry with my left index finger. It was a nice, tight, and I wondered the last time a cock had been in it, or was she an anal virgin?

I couldn't possibly give this lady any more attention in the position I was in and she responded with a series of quick large, shuddering orgasms that had her screaming, humping my fingers and gushing all over the sheet on the massage table.

She ended up pushing me away from her tasty pussy because she was on sexual overload.

I got off the table as Jan rolled over in the fetal position, sort of sobbing, sort of laughing, trying to get back to normal.

My cock was still throbbing and I was in need of some relief.

In a couple of minutes, rolling onto her back, Jan got centered with the pillow on her head, looked up at me and smiled.

She spread her legs and said "Come on up here" and I thought, holly fuck, I am going to get laid.

I climbed up on the table my cock wagging like the tail of a dog, and I knelt between her thighs, read and eager for penetration of her still wet and now wide-open pussy.

I was ready. Ready to fuck. Read, more than ready, to cum into that pussy that was still glistening from my oral assault.

My hands on my thighs I bent over, my hard cock ready to be buried inside of her.

My carnal thoughts were interrupted by Jan's voice: "You aren't going to fuck me tonight Rick. It isn't safe."

That news didn't go over so well and I am sure my disappointment showed on my face and she continued with "And I'm not going to blow you and I'm not going to give you a hand job either."

My options were running out but my cock still needed some attention and she followed that with "I want you to show me what you've got. You have a very big cock and I want you to cum all over my body."

I looked at her and said "You want me to jack off on you?" which sounded sort of lame but it was better than jacking off in the shower at home.

Jan's eyes had never left my hard cock and mine had never left tits or pussy either.

She nodded, slowly, her mouth breaking out in a smile, a genuine smile.

"You have a big cock Rick, and I knew it was big from the moment I met you. You've been massaging hot naked women all day and now I want you to jack off for me. I want you to think about fucking me while you jack yourself off and I want your big load all over me."

With that she pulled her heels in, sort of pulling the back of my thighs and at the same time she pushed her large breasts together teasing me.

I hesitated for a second or maybe two and Jan pushed me over the edge by saying "This is our first step to fucking Rick. Take it or leave it."

It was late, I was tired, my cock needed attention and the hottest woman I'd ever been naked with just told me that we'd be fucking soon.

Jan pushed me a bit further by teasing me with "I want to you look at me while you're playing with yourself and imagine what it would be like if I was sucking that big cock of yours."

I was so worked up my first load came after maybe a minute of stroking myself while Jan watcher, her eyes wide in amazement at not only my length but my girth but how far I shot my hot cum.

The first blast hit her tits, the second landed on her forehead and the third one landed on her left arm.

She loved it!

"Keep stroking yourself Rick" she commanded me and the second load came a few minutes later, not as much juice but the force was just as strong, my shots landing on her tits, right under mouth and then on her belly.

As I collapsed on the massage table Jan quietly got up and got hot towels. I watched as she washed herself clean of my seed and then she rolled me over on my back and gently washed my still hard cock and all around my pubes, paying extra special attention to my balls. For good measure and because she said it would feel good, she gently teased my anus with a hot towel.