Lesson Plan

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Author’s note: This is a story in two parts. The second part is complete and will be submitted a few days after the first. It is quite a bit longer than anything I’ve posted here before. I’ve tried to take at least some account of what readers have suggested they’d like to see me do differently, or better. All of the characters are over 18. As always, I love hearing from you and, well, I just hope you enjoy 🙂


Dr. Drew made a quick note on the tablet in front of her, and then looked back at me.

“Have you ever performed oral sex on a man?”

I blushed to be discussing such an intimate topic with this older woman, and I wondered if I would have had this conversation with the mother I never really had.

I decided that I probably would have, and probably quite a bit sooner than this. Dr. Drew looked at me kindly and with no hint of judgment in her expression, and so with a little laugh that came from pure nerves, I blurted out, “have I ever given a blowjob, you mean?” I looked at the ceiling and pushed out the answer. “Yes,” it was barely a breath, and I stopped, remembering the whole awful thing.

We were in college, and it was in my boyfriend’s cramped, messy dorm room. It had seemed to take forever to finish — my jaw ached long before it was over — and when he finally did finish by shooting all of that stuff into my mouth, I was mortified. There was no sink or toilet in the room, of course, and I looked around furiously for some place to spit it out, finally settling on his roommate’s trash can.

Tears welled in my eyes as he hurriedly buttoned his pants. He didn’t touch me afterwards, like I wanted him to; hell, he didn’t even thank me for sucking him off.

But he told me, when we broke up about a week later, that I wasn’t very good at it.

Not surprisingly, my first blowjob was also my last — so far, anyway.

I hunched my shoulders down and waited for Dr. Drew’s next question.

I guess I should start at the beginning.

It was a couple of months before my 30th birthday. I was sitting on the couch eating a meal of coconut macaroons and staring at a blank TV screen when my brother came in. We were roommates just then, as he had talked me into moving in with him for a while after my last breakup.

“Why so glum, sis?”

I just glared at him, but, undeterred as usual, he came and sat down beside me. “I’m serious, Janie, I’m worried. What’s up?”

And then the tears came, and I couldn’t stop myself from answering him. The wall that had kept the answer inside me had finally been broken.

“Damn it, you know I’m about to turn 30. Do you have any idea what a … a black fucking hole that feels like?”

I waited for him to remind me that he was 34, but he didn’t. God bless him.

“And every fucking guy that I go out with breaks up with me pretty much right after ….” The wall might have crumbled, but I still couldn’t finish that sentence. Not in front of my brother. They always break up with me right after we have sex for the first time.

“Fuck, fuck, fuck!” I yelled the words through my tears, and I pounded the couch with my fist in time as I did it, actually making my hand sting from the force.

Daniel had always been a really good listener. It was why I was able to open up to him then.

Back in my teens, our four-year age difference was the difference between an adult and a child. Although I envied the trophies he’d won, in things like baseball and chess, we had been far enough apart that we weren’t typical rivals. With tennis and music, I had chased after his trophies, but always from afar. He might as well have been a generation older than me. And to tell you the truth, since our mother had left us when I was young, Daniel had basically raised me.

So he felt like both mother and father to me as he drew me out of my funk. And as I answered him, he started to reflect back to me what I was saying.

“OK, so, number one, you’re afraid you’re growing older and don’t have a partner yet.” I sniffed and tried not to nod in agreement. I was too angry with him for getting right to the point.

“Number two, men are mostly — strike that — only interested in sex….”

I interrupted him. “Exactly!” I thought bitterly of the men who had stripped off my clothes and then decided that what they found there didn’t rise to their standards.

“And number three, you’re not very experienced in that department.”

He had gotten right to the core of my mood. He waited for me to say something.

“I guess I’m just not all that interested in sex.” I blushed, having said it.

He was patient, and he brushed my damned wiry strawberry blonde hair from my face. He took a long time before he finally asked, “Has a guy ever made you, you know, have an orgasm?”

“No.” No embellishment. The answer to that question was “No.”

“That’s a damned shame,” he scowled, and a moment later, “have you ever had an orgasm at all?”

I’m sure I blushed fiercely at that. He was Escort Sefaköy basically asking me if I masturbated. “That’s none of your business.” In another instant I was bawling again.

Although I would trust Daniel to the ends of the Earth, I had to wonder where he was going with this. Was he just trying to look out for me in maybe the one department of my life we had never discussed?

He had taught me to drive, and I give him tons of credit for that: getting into a car again and again with an inexperienced, hormone-crazed sixteen-year-old girl. Was he about to suggest that he could teach me how to be a good lay?

Men. Maybe he was right after all. All they ever think about is sex.

But Daniel just sat still for a moment, looking thoughtful, before he continued. “Well, OK, look. I don’t suppose you know this, but when I was younger, just out of college, in fact, Dad sent me to Dr. Drew for a similar thing.”

I looked at him skeptically. “Dr. Drew?”

He nodded. “Dr. Drew Woodstone. It’s what they call ‘sex therapy,’ but it’s really more like a course in sexuality and, you know, sexual techniques.”

“Get out of here,” I said, and I waved my hand dismissively. “What’s he going to do, tell me to bend over and take notes?” I pictured myself in just that position, with a dirty old white-haired man unbuttoning his pants there behind me.

“She,” he answered. “Dr. Drew is a woman.”

That came as a surprise. I just looked at Daniel, and so he went on. “It’s an amazing program; I think you’d be very surprised. It all starts, and ends, really, with yourself, and by the end of it you’ll understand yourself and the opposite sex like you never imagined. The things you’ll learn from her might just be the difference for you.”

He paused and looked at me as though trying to gauge my reaction. “I think you should try it.”

He had a hand on my shoulder as he said this, and I couldn’t help thinking that my older brother was mothering me.

I looked down at my hands and mumbled, “I don’t know, it’s just, I….”

Holding his hand steady on my shoulder, Daniel waited for me to look him in the eye.

“Just promise me you’ll think about it, OK? I won’t pressure you. In the meantime, I’ll, you know, try to answer any questions you have.” Then, after holding my gaze for just one more moment, and crooking an eyebrow, he stood and went into the kitchen to see about a dinner more healthy than my plateful of coconut macaroons.

And that’s how I found myself, a few weeks later, parked on the street outside Dr. Drew Woodstone’s nondescript office. I had arrived there a good 20 minutes early for my appointment—enough to allow me to procrastinate and have a bundle of second thoughts and still, if I decided to go through with this, be there on time.

With about 10 minutes to go, the front door of Dr. Drew’s office opened and a handsome dark-haired man emerged onto the sidewalk. He turned back once to the open doorway and said something to someone inside before he nodded and smiled, and then, thrusting his hands into his pockets, he turned away from where I was sitting in my car and he walked out of sight.

Not interested in sex? I chided myself as I watched the backside of his jeans as the man strolled away from me. I was totally interested in sex. Completely, insistently even obsessively interested in sex.

My problem was that I drove men away.

I thought about Dr. Drew. If she’s a woman, I reasoned, she would have to be sensitive about this whole thing. Right? It can’t just be “OK, miss, spread your legs and we’ll get started.” A female therapist wouldn’t have anything to do with that sort of thing.

Telling myself this over and over, I finally got out of my car, although I felt as though my arms and legs were wrapped in lead weights. And my thoughts spun incessantly, trying to anticipate what I was getting myself into.

The first part of the appointment was an interview, to help her develop a “lesson plan” for me, as she said. That was what had brought us to the “blowjob” discussion. And there was more. It was all so matter-of-fact, and I was surprised at how easy it became to answer her questions.

She eventually came to a point where she had no more questions to ask. She paused for a moment, glancing over her notes, before pushing them off to the side.

“We’re going to start by getting you in touch with yourself. That’s where it all starts. You have to know what pleases you, first. And you have to be willing to take ownership of that.”

Oh great, I thought. Masturbation. Yes, I had discovered it like everyone does, back when I was younger. But my life anymore was a cycle of being with men, expectantly waiting to get intimate with them, followed by hating my body and hating everything about sex.

But Dr. Drew broke my negative train of thought. “Today, you’re just going to have a massage, just like you would get at a spa. In fact, for this afternoon I’ve borrowed a massage Yenibosna escort bayan therapist from a spa that a friend of mine owns. His name is Roland. So, let’s go ahead and get you ready.”

She led me to a little room beside her office that resembled a large bathroom. It had a sink and a mirror and a commode off to the side, but in the center of it was a bench and a large cupboard for clients to hang up their clothes. A very comfy-looking white robe hung on a hook in the cupboard.

Everything about the room was pleasantly bright, clean and inviting.

“Go ahead and get completely undressed, and put on that robe, and then we’ll go on in,” she instructed. I hesitated for a moment, expecting her to leave me in privacy.

She saw my hesitation and immediately answered it. “Oh no, I’ll be with you throughout this entire process, you know, so we might as well start here tonight. In fact, the first thing I want you to learn is to be happy in your own skin.” Then she smiled easily. “Come on, show me what you’ve got. From what I can see, you’re a perfectly attractive young woman.”

I blushed. Dr. Drew stood there, arms folded, not brooking any objection. I was either going to strip naked in front of her or I was going to get up and leave, never to return.

OK, it’s just a massage, I told myself. I don’t have to go on beyond that, not if I don’t want to. I avoided making eye contact with her as I took off my clothes.

I had never undressed in front of a grown woman before. When at last I peeled my panties down and off, I quickly folded them and set them in the cupboard with my other clothes, and just as quickly reached for the robe. Of course, in my haste, my hands fumbled with the damned thing but I finally got it wrapped around my bare body.

She then led me into the hall and on into the next room. It was set up just like a bedroom, although there was a small utility cart with towels and lotions next to the bed. A radio on an end table was playing what I would not exactly call music, but a series of sounds that were surprisingly, almost immediately relaxing.

She gestured for me to take off the robe, which she took from me and placed on a chair in the corner. She had me stretch out face down on the bed. Then she covered my midsection with a light blanket that was surprisingly warm.

She moved out of my field of view as I heard the masseur step into the room, although I was vaguely aware, at least at first, that she was still there as the massage began. But I overcame the slight disappointment that Roland wasn’t the handsome dark-haired man I had seen leaving here a little while before, and it wasn’t long before my world shrank down to the masseur’s hands and my body.

I had never had a professional massage before. Going into it, I was worried that I would be ticklish, and that worry was all I could think about as Roland started with my scalp and my neck.

What I wasn’t prepared at all for was how intensely erotic the experience was, especially in a few unexpected places.

Roland never once touched me inappropriately, let me just get that out at the start. He was clearly a well-trained professional who respected the boundaries of his art.

But once he had taken the time to let me relax, to get my mind and body into simply having this experience, he did what I am afraid was the most intimate — the most erotic, and yes, the most arousing — thing any man’s hands had ever done to this woman’s skin.

He took his warm, oiled hands away from my neck and my shoulders, and he used them together to stroke ever-so-slowly down the length of my right arm, pausing here and there to attend to a tightness. When he reached my hand and my fingers, oh my God, yes, my fingers, I was tingling so insistently that I was sure I was positively flooding with moisture, you know, down there.

I was intensely aware that, although I was barely covered by a blanket, I was lying here naked, being touched by a strange and reasonably attractive older man. I was afraid I would have an orgasm right there on the massage bed, and if I had moved in just the right way I had no doubt I could have, but I closed my eyes and let myself relax into the symphony of pure sensual feeling.

The rest of the massage was largely like that, although nothing ever equaled the feeling of his hands touching mine. Not even when he was working on the outside of my thigh, up under the edge of the blanket, and I wondered if his hand hadn’t reached maybe an inch or two higher on my curves than was quite strictly proper.

I have to admit that, by then, I wanted him to go two inches more.

But he didn’t. Not on that leg, nor on the other.

In fact, that massage kept me so close to the edge of sexual arousal that I have little doubt I would have invited, no, encouraged him, to go on ahead and touch me in a private place, had he shown any sign of trying to go there. But he never even came close.

And, you know, that very fact Halkalı escort might have been the hottest of all.

My God, I simply loved being totally unclothed while he was touching me. And in my imagination, he was enjoying touching my skin, just as much as I was enjoying his touch.

And I was at once high, and tingling, and sad, when at last he whispered to me, “thank you, ma’am, it’s been my pleasure,” and with a last gentle pat on my shoulder, he turned and briskly walked out of the room.

I imagined the strength that it took for a man to touch a nude woman so completely, there under that little blanket, and then leave her, knowing, as I’m sure he knew, that the woman he was walking away from was feeling so wonderfully good.

It must have taken such powerful restraint.

After Roland left, I just lay still there on the bed for a while, basking in the warm tingling glow of every muscle he had touched.

When I finally stirred, Dr. Drew at last spoke, reminding me suddenly of her presence. And of her “lesson plan.”

Her voice was soft, but not quite a whisper. “Well, tell me how you feel, Jane.”

I let out a long sigh, and then I laughed. “That was totally awesome,” I answered her. I was starting to warm up to this whole crazy idea.

She smiled and then slowly stood. “Good,” she said. “So, go ahead and get dressed now, and I’ll see you next week.” Then she left me alone.

I stayed there under the blanket, not out of shyness but rather luxuriating in the way that my body felt. Then I climbed up out of the bed and slipped on the robe to go out in the hall. And after one wrong turn that nearly took me outside, I found the little changing room and got dressed.

Yes, I thought. I will be back next week.

When I got home to Daniel’s place, I found that I had to park in the street. A car was blocking his driveway. In my usual style, alone in my car, I let out a “what the fuck?” But as I backed up and parked at the curb, I saw an attractive woman coming out of his townhouse and heading for the offending car.

She had shoulder-length burgundy-tinged hair, and she was professionally dressed, although her clothes did seem a little disheveled.

My curse turned into a smile, as I realized that in all likelihood, at least my brother was getting some, and to my eye, anyway, he was getting it with a very classy woman.

Then my mood turned back toward its usual darker side as I thought, just my luck. The only man I know who’s not a total prick is my brother.

Daniel and I made normal small talk that evening. He made no move to acknowledge that I had been to see Dr. Drew, although he had surely figured out what my vaguely-described “appointment” really was. And as uncertain as I was about this whole Dr. Drew thing, I repaid his discretion by not mentioning the woman I’d seen leaving.

I knew without having to be told that the next week, Dr. Drew would ask me to touch myself.

“I want you to take all the time that you want — that you need. This is so important.”

I looked at her with a frown. “I just don’t get why you need to be watching me,” I objected. She was asking me to strip naked and masturbate while she sat in the room. “I could just do it at home.”

“A couple of things,” she began with her usual level and professional demeanor. “First of all, some of my clients really don’t know what they’re doing. And if that’s an issue, then, we need to get past that. But more importantly, there are just so many women who need to participate in their own orgasm, even with men who are good lovers,” she said.

“It’s just the way women are built. It will do you good to get used to being watched doing it, and that’s why it is always a part of my program.”

She paused to let the gravity of that sink it. ‘Let’s face it, whether you knew it before or not, masturbation simply has to be part of your game. And you’re going to be better off if you can do it while he’s watching you.”

It may be that the look on my face betrayed my continuing doubts, but she went on to add, “You’re going to thank me for this more than any other part of the lesson plan.”

I remembered the whole-body tingling that had stayed with me all the way home from last week’s session, and I did the best that I could to force away my doubts.

There was no robe in the cupboard this time (but then again, there would be no Roland), so my body was completely exposed as I left the little changing room and hurried out through the hall and into the bedroom.

And yes, I touched myself while Dr. Drew sat in the room. As before, she sat in a corner: out of my line of sight, if not out of my thoughts.

At first, my touching myself would be best described as mechanical. But after a while, my growing arousal took over from my conscious mind, and I let a finger slide up inside me as the fingers of my other hand stroked the soft and moistening places that lay just beneath my full strawberry-blonde bush.

Masturbating always took me a while, and it took me longer than usual that day, to get to that point where my breathing started to become ragged and my body took over from my mind, and I thrust my hips up against my fingers again and again and then waves of that uncontrollable feeling began to wash up and out through my body.

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