Learning the Hard Way - Cover

Learning the Hard Way

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Chapter 6: Lesson Three - Oral Exams

Erotica Sex Story: Chapter 6: Lesson Three - Oral Exams - Old high school friend teaches widow about sex.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   Oral Sex  

What? Oral sex? I had been hoping it would come up.

I would have had no problem discussing it with her before we went skinny dipping. But then Gwen became impatient and insisted that we start going over sexual positions before our clothes dried. Then, to add icing on the cake, she'd started getting playful while we were doing so. When that happened, any intention I had of talking to her about oral sex went straight out the window!

But sixty-nine? That was one position I didn't want to be in if she became too curious and decided to start playing around again.

Perhaps if I do a good job of explaining it to her, she won't have any questions to ask and everything will be okay?

"Where did you hear about that?" I asked, surprised.

She giggled, "Bobbie."

"When?"

She laughed, "While we were in the kitchen."

"Didn't you tell me you didn't know Bobbie well enough to talk to her about sex?"

Laughing again, Gwen answered, "That's right. That's why I let her do all the talking."

'Bobbie must have done some talking!' I thought to myself as I tried to figure out how I was going to explain oral sex to Gwen.

"What do you know about it?" I asked.

Gwen responded, "Nothing, Bobbie said I should ask you about it."

"She did, did she? Remind me to take that up with her later." I stewed for a second and then began, "'Sixty-nine', unlike intercourse, is a type of 'oral sex'. Unlike intercourse, the penis does not penetrate either the vagina or, in the case of anal, sex the anus."

She raised an eyebrow, "Anal sex?"

"Remind me to tell you about that later. Meanwhile, let's stay on subject."

I continued...

"Oral sex is not done for procreation. It's done purely for the sexual gratification of the recipient.

There are two basic types of oral sex. One is preformed on a man; it's called fellatio. The other is preformed on a woman; that's call cunnilingus.

In fellatio, the giver uses their mouth, and sometimes their hands, to stimulate the sensitive areas of the penis I was telling you about earlier.

When cunnilingus is preformed, the giver uses their mouth, and sometimes their hands to stimulate the sensitive areas of a woman's vagina.

Sixty-nine is when one person is laying down on the back with another person on top of them, usually on all fours, and each person uses their mouths to stimulate each other's genitals."

Boldly, Gwen asked, "You seem to know a lot about it. Have you done it before?"

"Yes." I confessed.

And then she asked, "And you both enjoyed it?"

"Very much so." I said honestly.

Then I heard her say, "Who's on top?" I thought I detected a bit of excitement in her voice.

"Usually the woman." I said abruptly.

Equally abruptly, she asked, "How does she get there?"

"That depends. If she's standing, she might kneel over him and then crawl backwards until her face is over his penis. Or, she could just stand directly over his face and carefully lower herself until her vagina is close to his mouth. Either way, they end up in the same position."

I could see her thinking, Gwen asked, "It sounds complicated. Couldn't somebody get hurt if she's not careful?"

"Yeah, but that rarely happens. She'd have to step on him or, even worse, bite him.

Without a second's hesitation, Gwen said insistently, "You've convinced me. It's far too complicated for words to explain. You're just going to have to talk me through it one time. Otherwise, I might end up maiming the first guy I do it with."

"Look, you're making a whole lot more out of this than you need to. It's not that hard!"

But instead of listening to reason, she crossed her arms and said defiantly, "No. I know when to admit my limitations and this is one of them. You're just going to have to show me."

Let's face it; I gambled and lost. There was nothing left to do but hope she didn't get too curious.

"As I told you before, one person is on the bottom and the other on top. Most of the time, unless the woman is bigger than the man, he's on the bottom."

She rolled off the rug giving me room to lie down.

I did, placing my head on the head of the bear and using it like a pillow. Then I said to her...

"If the person on the bottom is smart, they will use something to prop up their head."

Gwen asked, "Why do that? Why not just lay flat on your back?"

"Because it makes it easier to reach the other person's genitalia and prevents neck strain."

I'm not sure she totally understood it; but, whether she did or not, Gwen asked, "Okay, what am I supposed to do now?"

"At this point, as I told you before, you have two choices. You can either stand directly over my face and lower yourself into a kneeling position; or, you can get on top of me in a 'reverse cowgirl' position and slide yourself backwards. But if I were you, I'd do whatever I felt most comfortable doing."

Very carefully, Gwen climbed on top of me. She was facing away from with her legs were straddling my hips.

As she sat atop me with her womanhood pressing my shaft down onto my belly, Gwen asked, "Now I'm supposed to start sliding backwards, right?"

"Yup!" I said as I looked at her well rounded ass.

'You know if you rise up a little I could... '

Her voice brought me back to reality, "What?"

"I didn't say anything." Did I?

She leaned forward on all fours and began slowly moving towards me, Gwen said, "I thought I heard something. It must have come from outside."

As she did, the furrow of her pussy ran the entire length of my sex. I could have sworn she was rubbing her clit on it the whole time.

My arms were at my sides forcing her to widen her legs and swat lower every time she moved.

"You're getting awful close back here." I informed her when her clit was about two inches away from my mouth. I thought that maybe she might stop.

However, instead she continued, saying, "But my head's not quite over it yet. I'm almost there ... just a little bit farther."

Finally Gwen stopped. However, after she did, her pussy was so close to my mouth that I could have stuck my tongue out and licked it from top to bottom without even moving my head.

"Satisfied now that you know how to do it without killing anyone?" I asked.

Hesitantly, she replied, "Yes. But..." and stopped.

"But what?" I asked wondering why Gwen hadn't climbed off me yet.

Finding her voice, she continued, "It's just, like I told you, I've never seen one this close before. I'd kind of like to examine it for a while. If you don't mind that is?"

Okay, so what was I going to say. You can't blame her for being curious, can you? As long as she doesn't touch me, everything will be fine.

"Go ahead. Take your time."

Elation in her voice, Gwen said, "Thanks. Okay, let me see if I remember what you told me. This part is the 'Frenum' right?" Then I felt what I thought was a finger gently run from the top of it to the bottom.

Even though it tingled a little, I thought to myself, 'That wasn't so bad. I can handle that.'

Next she said, "This is the 'Corona' or crown, right?"

Once more, I felt the same gentle touch circle around it. And again I thought to myself, 'That was nice, but nothing to worry about.'

Innocently, Gwen asked, "Hey, is it okay if I touch it? I just want to see what it feels like for a second?"

Since she hadn't done anything that I considered sexual, I said...

"Just don't squeeze too hard, okay?"

As I felt her hand gingerly wrap around the base of my cock, she said reassuringly, "Oh, don't worry, I'll be very gentle."

Gwen held me there like that for several seconds.

To which Gwen responded, "And the gland is too?"

"The gland too!" I repeated.

When I felt her hand moving me around like a video game joystick I realized she was trying to examine it from all angles.

She stopped and said, "Tell me, what's did you mean by stimulation?

I took another deep breath and reminded myself that the only reason Gwen wanted to know was because she'd never had anyone explain it to her before. After I counted to ten, I answered...

"Friction, like when something rubs it gently."

Her hand still wrapped around me, Gwen asked, "What's it feel like?"

Then, for the tiniest fraction of a second, I thought I felt something lightly caress the tip of my cock. However, it happened so fast that I could be sure. She was waiting for my answer but I didn't know quite what to say.

"It's kind of hard to explain." I wasn't trying to be evasive. I really didn't know how to describe it too her.

Then she asked, "What's it look like while it's being stimulated?"

"I don't know, I wasn't looking at the time."

Impatiently she demanded, "If you can't describe it to me, how am I supposed to know whether or not what I'm doing it right?" She paused. It was almost a dramatic pause. Then she said, "Alright then, you tell me when I'm doing something wrong and I'll stop."

And before I could say anything one way or the other, she began moving her hand slowly from the base of my cock to the crown.

For the first time all night, I was speechless. One reason was because somewhere in the back of my mind I didn't think she'd do it; and, the other was, after all that teasing, it felt so good I didn't want to say anything that might make her stop.

I heard her say, "How does that feel? I'm not hurting you am I?"

"No, that feels good." I told her. That familiar tingling started running my pleasure pole.

She moved her hand a little faster, "How about now? Good or bad?"

"Good." I said and the tingle became stronger.

I felt her tongue rolling around the head of my cock and after a few seconds she stopped long enough to asked, "Good or bad?"

"Very good!" I told her energetically.

She did it a couple more times and as her hand continued moving up and down asked, "Can you show me what a man normally does for a few seconds? I just want to know for future reference."

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