Learning The Hard Way (Edited V. 1.10)

"What about after you got married; didn't you have any friends you could talk to?"

Her answer was, "All my friends were his friends. And in his circles, a married woman did not talk about her marital relations with anyone. "

"Books?"

She replied, "He didn't want me thinking about sex for fear I might demand more from him; so, he wouldn't allow anything remotely sexual in the house... except his journals, of course."

Not sure what Gwen was going to say next, I looked at her expectantly.

Somberly, she lowered her head and said, "You must be wondering why I decided to tell you this." She paused. "What it all boils down to is this: After twenty-four years of marriage, I know less about sex than most teenagers dating nowadays. What I need is for someone to tell me all the things about sex I don't know."

Wait a minute! Maybe I'm misunderstood her. Did Gwen just ask me to explain the facts of life to her?

Any doubt I had vanished when next she said, "Joey, if you would, I'd like you to do it?"

I looked at Gwen, studying her for a very long time trying to make up my mind if she were serious. Something about the expression on her face told me she was.

"Gwen, that's not some birds and the bees talk you asking for. Are you sure you wouldn't rather talk to a woman about this? I could get Bobbie to…"

She cut me off, "I don't know Bobbie well enough to talk to her about this. Besides, what if she told someone? I'd never live it down! You're the only real friend I have. I don't trust anyone else."

"Listen, I'm not saying no; but, have you considered reading a book on the subject? There are plenty of them out there and most of them have illustrations in them; we could get you a few?" I suggested.

But Gwen rejected the idea saying, "I considered reading a book, but a book can't answer questions the way a real person can."

Then she looked at me with those beautiful blue eyes of hers and said to me, "Please."

I hate it when a woman begs. It makes me all mushy inside.

"If you're sure that's what you want. Then I'll do it." As I said it, I wondered if I'd just made a big mistake?

Chapter Four -- The Late Night Swim

"Skinny dip?" I asked hesitantly, hoping desperately that I wasn't wrong. No! Not for the reason you're thinking. Although, the idea of seeing her naked had been going thought my mind every since she'd peeled off that dress of her and I saw her in that Carlito Bikini. It just seemed obvious to be that, having led the sheltered life that she had, it might be on her list of things to try.

Astonished, Gwen turned to me and asked, "How did you know?"

"I wasn't sure until I saw until you looked at the pool."

Cautiously, Gwen inquired, "You're not shocked?"

"Not really. It's something everyone wants to try at least once." I paused and then asked, "Mind if I share a secret with you?"

She replied, "Go ahead, I shared enough of mine with you. Besides, I've always wondered what's going on in the mind of yours."

"Did you notice how high the fence in the back yard is?"

She nodded, "It looks brand new; is it?"

"Yes; and it's that high for a reason. " The expression on her face changed and I thought she was beginning to get the picture. Just in case she didn't I explained, "I don't like wearing a swimsuit. I don't even own one!" Gwen gazed longingly at the water and I said, "Go ahead, help yourself. I won't even look."

Her response wasn't quite what I expected, "And leave me out there all by myself. I don't think so! Either someone swims with me or I don't swim at all. I don't know anything about this neighborhood."

"But I just told you I don't even have a suit to put on." I reminded her.

Giggling, Gwen said, "Don't worry, you can borrow mine if you'd like."

And then all too vivid mental image of me dressed in her biking appeared suddenly before me. Making it disappear as fast as I could, I said...

"No thanks, I think it looks better on you."

Impatiently, Gwen asked, "Is that a yes or a no?"

"Both." I told her causing a look of confusion to appear on her face. I explained, "Yes, I'll go swimming with you; and, no, I'm not going to put on your swim suit." And then, without further ado, she headed for the door with me trailing not far behind.

Seconds later we were both at poolside. I took off my shirt and began removing my shorts. But, before I had a chance to get them completely off, she jumped in sending a giant wave of water in my direction and soaking me, clothes and all, in the process. I was stepping out of my shorts at the time.

When I realized that Gwen hadn't removed her bikini, I didn't know whether to be embarrassed or not.

"Hey, I thought you said we were going to..." I began. Then splat! The top of her bathing suit hit me square in the face. Quickly, I grabbed them up and threw them back at her, missing her in the process. Splat again! This time it was the bottoms... again square in the face.

"It's not safe out here!" I exclaimed and then dived for the relative safety of the water.

Trying to keep a safe distance, I paddled around a bit and tried not to stare at the way her breasts buoyantly bobbed in the water. Gwen did the same.

As she treaded water, Gwen said, "You know, I could get used to this. It's very relaxing. I see why you like it so much."

It was a peaceful moment and I was enjoying it as much as she was. I decided not to respond for fear of spoiling it.

Believe it or not, we swam for about the next half hour and nothing happened. When it started to get chilly outside, she got out of the pool and grabbed towel so she could dry off. That's when I got my first good look at her. Taking the que from her, I got out of the water myself. I was going to put back on my shirt and pants until I realized that they were thoroughly soaked and would have to be dried. I looked at Gwen, she was holding her bikini, one piece in each hand. It too was just as soaked. Then she reached down for her dress, it was also soaking wet.

We both looked over at the table where I had placed the towels for the guest to use. The table was bare and when we looked around, it became apparent that every towel was soiled.

Seemingly unconcerned, Gwen asked, "Is your washer and dryer hooked up yet?"

"Actually, it is." I said proudly.

Cautiously, she inquired, "Got any laundry detergent?"

"As a matter of fact, believe it or not, I do. The old owners left some behind."

As soon as she heard my response Gwen picked up our clothes and put them in her bag, and in a delightfully said, "Mind if I do some laundry?"

"No, not at all." I replied. To which she responded, "Great, for a minute there, it looked as if I was going to have to drive home wearing this wet bikini. The way the temperature's dropping, I don't think that's such a good idea."

I hadn't even thought of that. But, then when I noticed how erect her nipples were and realized she was right.

Gwen suggested, "Why don't we knock out the towels at the same time?"

I looked away suddenly and secretively hoped she hadn't caught me looking. Then I said...

"I can do those later."

Her response was, "I want to; anyway, you might need them later."

And so, we gathered up our clothes and all the towels and took them into the laundry room. I was kind of surprised when she began loading the towels into the washer first; but, I said nothing about it.

Once the washing machine was running, she said to me, "Let's head into the living room where there's plenty of room; shall we?"

And so, less than a minute later, there we were sitting in the living room naked as jaybirds.

She was sitting on my bear skin rug Indian style with her legs crossed; and I was sitting about six feet away with my back against the fireplace. I remember the room seemed eerily quiet at the time.

The whole thing seemed very surreal. That's what it was... surreal! I mean think about it. I was a forty-eight year old adult male who had just asked by a forty-eight year old adult female to educate her on the intimacies of sex. Have you ever heard of such a thing?

"Don't you want to wait until our things come out of the dryer?" I asked.

She queried in response, "Why, don't you trust me?"

'Trust you? It's not you I'm worried about, I'm not sure I trust myself!' I yelled inside my head. That's not what I said though.

"No; I just thought you'd be more comfortable if you had something on?" I replied somewhat truthfully.

But Gwen just smiled and answered, "I'm quite comfortable this way; besides, that dress I wore over here is quite expensive; even if it were dry, I wouldn't want to take a chance on tearing it."

I noticed she didn't mention the Carlita Bikini she had been wearing earlier; perhaps it was just an oversight?

I decided one last time to try and be chivalrous and talk her out of it.

"Gwen honey, aren't you even a little bit concerned that I might take advantage of you?"

Confidently she replied, "If I thought that, I wouldn't asked you in the first place."

And I thought to myself, 'I wish I was as confident as you are honey.'

But Gwen had made up her mind and really put me on the spot when she said to me, "I think we are both capable of controlling ourselves, don't you?"

At that point I had two choices. One was to say 'no', which is what I was leaning towards doing, and could either have her think that I had no self-control or that I didn't think that she did. In the later case, she'd be insulted. The other was to say 'yes', which, to be perfectly honest, I wasn't sure of myself. As I saw it, answering 'no' was a lose-lose situation all the way around; and, answering 'yes' was one hell of a gamble. If she were wrong and we ended up having sex while she was most vulnerable, she might regret it later and possibly be the end of our friendship!

'Fuck!' I thought to myself in frustration. 'I guess I've gone too far now to turn back now.' And then I heard my voice say, "Alright, where do you want to start?"

Chapter Five - Lesson Two: Positions

And that's how Gwen and I ended up naked in my living room.

Laughing, Gwen suggested, "On the rug?"

"I meant what position smart-ass?"

Giggling, Gwen suggested, "Why don't we begin with the other variations on missionary you told me about? What was that first one you mentioned, 'The Deck Chair'? Tell me how that goes again?"

Then, before I had a chance to say anything, Gwen laid flat on her back and asked, "Now what?"

"The woman opens her legs, pulls them backwards until her shins are parallel to whatever she's laying on and holds them there. Then, the man crawls between her legs." I said as unemotionally as I could. And as I did, just the thought of Gwen doing in that position started the blood rushing to my prick.

Then, without any hesitation at all, did exactly that. Sure enough, as soon as she pulled her legs backwards and spread her legs giving me the most splendid view of her sex. As I sat there trying hard not to look at it, and also trying not to get hard as I did, Gwen asked, "Like this?"

"Yup." I gulped, "I'd say you got it right the first time!"

I felt flush and thought, 'God don't tell me I'm blushing! For crying out loud! I'm a forty-eight year old man. It's not like I've never seen a naked woman before! It's just that I'd never seen Gwen naked before!'

She said something. What was it? Oh yes, now I remember. "Where is the man again?"

'About to have the best time of his life?' Whispered the voice inside my head.

As I felt the blood surging in my dick, the words 'This is going to be harder than I thought!' went through my mind. Talk about your bad choice of words? It was almost comical; and, had my mind not been on other things at the time, I probably would have laughed at the obvious pun. But, as you can imagine, it was; and, I didn't.

"Between your legs." I said abruptly thinking that my answer was good enough.

Unfortunately, it wasn't and she said in a chastising tone. "You're supposed to be showing me; remember?"

"You know; I'm going to have to touch you in some of these positions?"

Impatiently, she informed me, "I assumed as much."

I'm not quite sure Gwen knew what I meant by 'touch'. If she didn't, she was about to find out real fast.

I was about six inches away and stopped. When I saw her looking at me expectantly, I slowly crawled forward and into position. I could see she was wet but I couldn't make up my mind whether it was from just having gotten out of the pool or some other more sensual reason.

The moment our sexes touched she startled a little and I asked...

"Is everything alright? Are you sure you want to do this?"

My semi-flaccid manhood was pushing directly against her 'taint'.

Undeterred, Gwen replied, "Everything's fine. It just takes a little getting used to. Then, she leaned, first to the left and then to the right. It appeared to me that she was studying the placement of my legs. When she was finished, Gwen said to me. "I take it the man moves in the same way as in plain old missionary?"

"If by 'the same way' you mean thrusting his hips forward, yes." I responded.

Eager to learn, Gwen asked, "Can the woman move or does the man do all the work?"

"She can if she wants to by either raising and lowering her butt and thrusting upwards or by rocking her hips backwards and forwards." I said informatively. But, in my mind, I was thinking how much I wanted to show her exactly how it was done.

To my surprise, without saying a word, Gwen began thrusting her buttocks upwards as I had described and said, "Like this?"

As she did, her sex slid the full length of my then semi-erect pleasure pole. It was very erotic and stimulating.

"Yes!" I said and wondered to myself if Gwen really had any idea what she was doing.

As soon as I answered her, Gwen began rocking her ass gently and, at the same time pulling her legs back in the direction of her breasts. This resulted in a massaging motion that was even more pleasurable than before.

After I allowed myself to enjoy it for a few seconds, I said to her...

"You've got it all right. Maybe we better move on?" I suggested. Luckily for me, she didn't ask why. And, it's a good thing because there was no way I was about to tell her how enjoyable her movements really were.

"From here we can move into 'The Victory'." I told her.

Curiously, she asked, "Not 'The Deck Chair Folded?"

"We could." I conceded. "But all you have to do now is bend your knees until your legs are straight while I bring my knees a little closer to each other and we'll be in 'The Victory'."

Well, that's exactly what we did. But, no sooner were we in position than Gwen started pushing her pelvis against me again and said, "Am I doing it right?"

And, as if he had a mind of his own, 'Mr. Woody' kept getting bigger and bigger. It was very distracting.

"Oh yes, you're doing it just right." I said truthfully; and, I thought to myself, 'Boy are you doing it right!'

Gwen massaged me a few more seconds and then asked, "How do we switch to "The Deck Chair Folded' from here?"

As the blood continued rushing into my penis, I answered...

"I'll move my arms out of the way and then you rest your calves on my shoulders. When you do, I'll bring my knees a little closer together for leverage."

Two seconds later, when we were in 'The Desk Chair Folded' position Gwen asked again, "The man moves the same way?"

"Uh huh." I replied.

Then Gwen commented, "It doesn't seem as if there's much room for the woman to move in this position. About the only thing I can think of to do is this..." and then, as she used her ankles for leverage, Gwen began rolling her ass upwards. Each time she did, my rod rode atop the furrow of her womanhood like a shuttle sliding in a grove.

It wasn't too many repetitions later she had me fully erect. I was astounded that, while I was somewhat embarrassed, Gwen didn't seem to be at all. Could it be that she was enjoying herself and knew what she was doing? Should I say something to her about it? While I was trying to decide, without stopping Gwen asked, "I still don't see how my moving is supposed to make things more enjoyable. Maybe we should move on to another position. Why don't we try 'Cowgirl'?"

But I was too busy enjoying myself to pay her any attention.

"Huh?" I asked as I tried to snap out of it.

She smiled and paraphrased herself, "Wasn't the next one called 'Cowgirl'? How do we do that?"

At that moment, I'd have told her anything as long as she kept dry fucking me the way she was.

"You'll have to move and let me be on the bottom for that one." I said informatively and began backing away from her.

As soon I was out of the way Gwen rolled over making room for me to lay down in her place.

I had barely gotten into position when I heard her saying, "Wow! So that's what one looks like!"

"Excuse me?" Then it sunk in what she'd said and I found myself asking, "You mean you've never see one before?" Then I got the 'excited' part of what she'd said and know I must have turned red in the face.

Without hesitation, Gwen confided, "No, not really. I asked Patty to show me his but he refused. I even tried sneaking into the bathroom only several occasions while he was showering only to find the door that each time the door to his bath room was locked."

"What about when you two made love, surely you saw it then."

Given the circumstances, her answer made perfect sense. "Saw it? I wish I had; then, I would know for sure what had been going inside me all those years."

"Excuse me?"

Given the circumstances, her answer made perfect sense. "On those few occasions he came into my bedroom and we did it, he always made sure the lights were off. Then, once he was finished, he'd get up, go to his to his bathroom, and I hear the shower running for at least an hour. Since we slept in separate bedrooms, I wouldn't see him again until breakfast the next morning.

After he died, I found some sort weird device locked in a box in his closet. I had to break it open to find out what was inside. When I did, I couldn't believe my eyes. It was some kind of a harness. Attached to it was a soft rubber penis shaped device that was about three inches long.

The thought occurred to me, 'My God! It's possible that she's never actually been with a man!'

Her voice interrupted my thoughts. "Tell me about it please."

"From how you described it, I'm reasonably sure it was a strap-on." I explained.

With an exasperated look on her face, Gwen said, "No. I mean tell me about sex."

A lot of things went through my mind at that time… pity for her, fascination with her story, and, a deeper sense of how things might have been different had I pursed her more back in high school. I raised myself up on my elbows and said...

"Where do you want me to start?"

She thought a second and then asked, "Tell me as much as you can. For example, what's the difference between one that's been circumcised and one that's not and which do you have?"

"I may have one but I certainly no expert. Still, I'll tell you what I know."

I probably shouldn't have but I chuckled a little causing her to frown.

"Don't worry, you're not the first woman to ask me that question." It seemed to make her feel better. I continued, "Mine is circumcised. That means that the foreskin was removed. It used to cover most of the glands here. They're very sensitive, by the way." I pointed to the head of my cock.

She had moved into a sitting position facing me. "I remember reading something about it in the bible but never did understand what it was talking about. Did it hurt?"

"Probably, I really don't know, I was a baby at the time." Trying my best to do as she asked, I said, "You see this here?" I pointed towards the fleshy ring surrounding the base of the glands. "That's the 'Corona' or more commonly known as the crown. It's another sensitive area." As I moved my finger parallel, up and down, the strip of flesh on the underside of my penis running from crown to the base of my cock, I said to Gwen, "Lastly, this is the 'Frenulum' also known as the 'Frenum'. It too is very sensitive. Any questions?"