Lisa's Lessons

Inserting the tip of the red vibrator necessitated holding it at an angle before pushing it forward because of how it was curved. When about a third of it was inside her she told me she felt the tip on her spot. I turned on the vibrator and she let out a moan that left no doubt about the efficacy of the device.

"Ohhhhh yessss, Robert that's wonderful. Don't stop!"

It was unnecessary to move the tip of the vibrator very much because the vibrations spread out to cover all of her spot. Her hips began to move slightly up and down in an involuntary way as she responded to the stimulation. I increased the speed a little and she moaned louder. It was obvious she was moving closer to another climax.

"Lisa I think you're going to cum again pretty soon. Don't try to make it happen. Just let it happen of its own accord. When you feel yourself getting really close, pick up the big vibrator and put it on your clit."

Her eyes were closed and her head was back against the pillow as she allowed the sensations in her vagina to spread all over her body. The look on her face was beautiful. She was surrendered to her body and was not allowing thoughts to interfere with her joy. After about five minutes her hand reached out for the big vibrator and she put the head between her legs where it would touch her clit and the red vibrator already inside her. Her finger flicked the switch then slid the slider to the maximum setting. In less than ten seconds she exploded in orgasm. Her whole body shook and was forcibly pressed up in the air. She seemed to be paralyzed in an arch as she experienced a massive orgasm that completely overwhelmed her.

Watching her closely to monitor her, I let her experience the full impact of what a total orgasm felt like. It must have lasted a full minute before I moved my hand over and pulled the big vibrator away from her causing her to collapse back onto the loveseat. I turned off the other vibrator and slowly pulled it out of her.

Her breathing was deep and slow as her body recuperated. Finally she tried to speak. "Robert, I....I....I don't have words to...."

"Shhhh, don't even try Lisa. That first climax was just a warm up. Now you know what a real orgasm feels like."

"I never knew sex could be like this. It was always something I more or less endured. You've shown me how to control my own sexuality and make myself feel like a woman."

"Lisa I want you to continue feeling like a woman at least once a day, ideally as many times as you can every day. You're entitled to it and now you don't have to depend on anybody else to do it for you. There are a couple of vibrating eggs in your toy box that you can insert in your pussy and operate by remote control so you can get yourself off anywhere you go and any time you feel like having an orgasm."

"But isn't sex to be shared with somebody?"

"Yes it is. Preferably someone you love but you don't have to love someone to have sex with them. There's a difference between making love and fucking. Both have their place in your life."

"Would you help me learn things to please a man?"

"I suppose I should since it's as important as pleasing yourself. You need to have confidence in knowing how to do things for a man and not be afraid that he'll think you don't know or don't care about pleasing him. I don't think we should get into that today however. Take your toys home and play with them as much as you can and the next time you come we'll work on your skills for pleasing a man."

"Oh thank you Robert. I really appreciate your helping me. I already feel so much better about sex. I don't want to stop half way. I want to be good at it."

I helped her put the toys back in the box after we cleaned them up in the bathroom and put a layer of books on top just in case her mother asked what was in the box. I told her to tell her that they were books she needed to read since she never finished high school.

After they left I thought about where this was going next. I couldn't really decline to help her learn how to do things with and for a man since it was an important part of her sexual education. It would undermine all the self esteem I had managed to build up in her if she were with a man and he said something to make her feel like she was a lousy lover. I told myself this wasn't really cheating on Judy since I hadn't gone out looking for somebody to have sex with and I had no intention of allowing Lisa to continue doing things with me once I got her to a point where she could find a boyfriend of her own. But I had to admit that having sex with a young pretty woman was a very tempting proposition.

When the next cleaning day rolled around I was really looking forward to Lisa's session. Judy had discovered another activity to add to her list of things to do out of the house while the cleaning was taking place. She had found a spa where she could get a two-hour massage from two different therapists. She would start with a man who did more intense therapeutic work on her sore spots then follow it up with a woman who did a soft, relaxing massage focusing on her face, neck and feet. I was glad she was having a good time since I was going to be enjoying myself while she was away.

We quickly took care of the cleaning and had plenty of time to devote to her lesson. I decided to borrow the idea of a massage from Judy to introduce Lisa to learning to please a man sexually. We began with taking a shower together. She loved my playing with her body as I washed her.

When she began to wash me she lathered me up with body wash and rubbed her body against mine. Her hands bathed my ass as she pressed her breasts against my chest.

"I like being naked with you Robert. I haven't seen a real penis since my marriage ended." Her hands moved to stroke my cock and gently fondle my balls. My cock began to swell in her hand. "It makes me feel really good to know I can make your cock get hard Robert. You don't mind do you?"

"Of course I don't mind Lisa. You're a pretty and sexy woman and any man should feel happy and privileged to be with you like this. Let's get out of this shower so we can get the lesson started."

After we dried off, she was surprised when I told her I was going to give her an enema and then she was going to give me one. I wanted both of us to be thoroughly clean inside and out so she could learn how to massage me internally.

She helped me put the cushions from the loveseat on the floor to use as a massage table then we covered them with a sheet and a layer of towels. I had her lie face down so I could begin with her back. Before getting started I went to my computer to put some soft music on. An hour-long version of Pachelbel's Canon in D seemed perfect for the occasion.

"Massage is a great way to get to know another person. It's fun and very arousing to slide your hands all over their naked body."

After pouring some oil on my hands I started rubbing her neck then moved down to her shoulders and upper back. She was relaxing and I could feel her breathing change. "How does that feel Lisa?"

"Ohhhh Robert it feels wonderful. I love how your hands make me tingle everywhere you touch me. The music is beautiful, it makes me feel dreamy."

Moving down her back to her hips I incorporated the upper part of her butt into my rubbing; then straddled her legs so her ass cheeks were in reach and started rubbing and kneading the soft, firm flesh with my palms. My cock began to swell as my slippery hands slid all over her ass. She was softly moaning and breathing deeply. Putting my hands together, they moved slowly down her crack so my fingers could slide over her puckered hole and down to her slit. Without my even having to tell her, she spread her legs to give me better access.

Moving to kneel between her legs, I pushed them farther apart. "Push your butt up Lisa." She elevated her hips for me and the thumb of my left hand found its way to her puckered hole and began to rub it softly with little circles. The fingers of my right hand slid up and down her slit. I inserted one of them into her vagina and began to rub the walls of her pink channel. She was hot and wet. A second finger joined the first to massage her g-spot. She moaned louder.

Her juices were coating my fingers now so I gently began to press my thumb against her wrinkled butt hole. The oil made it easy to insert it. I pushed it all the way in and pulled it out while continuing to massage her vagina.

"Ohhh Robert that feels divine. You're going to make me cum if you keep doing that."

"Go right ahead and cum Lisa. I'll try to make it a gentle one for you so you can have another one later."

It didn't take too much longer before her vagina squeezed my fingers and her rectum did the same thing to my thumb as she climaxed. It was gentle like I told her and I knew it made her feel good.

After extracting my thumb and fingers from her holes I moved forward so my rock hard cock slid between her cheeks and snuggled up against her slit. My hands were placed on either side of her back as I began to stroke my cock against her pussy.

"Ooooohhh Robert, did I do that to you?"

"Yes Lisa you did that. Do you like it?"

"I love it Robert. It feels so hot and hard against my pussy. Are you going to put it inside me?"

"Not now but it does feel marvelous sliding against your wet pussy."

The stroking continued for a few more minutes until I felt myself getting too close to cumming then pushed back and stood up.

"OK, it's my turn now. Get up and let me lay on the cushions." When we had switched places I told her to do to me what I had done to her. She had evidently paid attention as her oily hands began to rub my neck then incorporated my shoulders into the massage. At the same time she straddled me and I felt her pussy press against my lower back. Now when her hands moved from the middle of my back to my shoulders, her hips undulated and I felt the warm wetness of her slit slide up and down my lower back. "Lisa you're doing a fantastic job. I'm wondering why we've waited so long to do this."

"I'm more than happy to add a massage to my list of cleaning tasks every time I come here. I like touching you. I've never had anybody to do things like this with and I really enjoy it."

"In that case, I have an idea. Put some of the oil on your chest and stomach." When she had rubbed the oil on her I told her to lean over and lie on my back and slide her whole body over my back.

"Oh Robert this feels great. Do you like feeling my tits slide up and down your back?"

"Don't ask stupid questions Lisa. It feels wonderful." I could feel her hard nipples as she dragged her breasts slowly up and down my back. Her pussy was getting wetter and the heat from her slit sent shivers up and down my spine as she ground her crotch into my lower back. What she was doing combined with the beauty of the music just about put me into a meditative state. I'd never felt this relaxed in my life. I hoped Judy's massage was as good as mine.

"Lisa if you keep doing this you'll put me to sleep and that's not what were here for. Move down and start massaging my ass."

Before she slid back she told me to spread my legs so she could get between them. She sat on her haunches rubbing my upper thighs and my butt. I was pleasantly surprised at how well she picked up doing a massage. I had had them before at spas but nobody had ever done my butt. This felt really good. It was soon to get much better. She put her hands together and slid them slowly through my ass crack several times.

"Raise your butt up Robert."

As soon as my hips were elevated one of her hands moved down to encircle my balls. She began to gently fondle them with her fingers while continuing to rub her other hand up and down my crack. It didn't take much of this to get my cock rock hard. The hand on my balls slid forward to stroke my erection in addition to my testicles.

"Lisa put your middle finger in my ass."

She quickly complied with my request and I felt her oily finger press against my puckered hole then slide easily inside me until it was fully inserted. "Press down and see if you can feel my prostate. I'll let you know when you've found it." Her finger moved slowly around inside my rectum until I felt the tip press against my sensitive gland. "Right there Lisa! Now put another finger in and massage that spot."

Her forefinger stretched my hole as it joined its partner and she began to rub the tips against the thin membrane that shielded my prostate. The sensitive gland felt like a mild electric current was flowing through it. I groaned as the sensations spread throughout my lower body. "OH FUCK Lisa! That feels fabulous. Do you want to make me cum?"

"Oh Yes Robert I'd love to make you cum. Is this something all men like to have done?"

"I can't speak for all men Lisa but this man is definitely a fan of what you're doing. I don't think my cock has felt this hard since I was eighteen. Just keep massaging my prostate and rubbing my cock and balls and I'll tell you when I'm about to cum."

The combination of her natural talent for this and her youthful enthusiasm took me quickly to the point of feeling that old familiar tingling that said I was about to blow my load. "Lisa cup your hand around the head of my cock and I'll cum for you."

Her hand moved to the end of my cock and wrapped around the head. Her other hand kept massaging my prostate until she drove me over the edge. Hot cum began to gush into her hand in multiple spurts until she had completely drained me.

"Damn Lisa that was fantastic! I can't remember when I've had an orgasm that powerful."

She slid her arm back from between my legs and opened her hand. "Wow Robert you filled my hand up with your cum. It looks so good and creamy."

"Taste it Lisa." She moved her hand to her mouth and tentatively stuck out her tongue to lick some of my cum from her hand.

"It's warm and a little salty but also kind of sweet."

"Do you think you can swallow the whole handful?"

"Do you want me to?"

"Your next lesson is going to be oral sex. If you are going to be good at giving a man a blowjob you're going to have to learn to like the taste of cum because most men are going to want you to swallow it when they cum in your mouth."

"In that case I'd better learn to like it." She raised her hand up to her mouth and tilted it so that my load slid from her hand onto her outstretched tongue. She gulped as she swallowed it then used her tongue to lick off what remained on her hand before swallowing again. "There, that wasn't too bad."

"I've heard it's an acquired taste like Scotch Whiskey or anchovies. Some women love it and others learn to tolerate it."

"It's not bad for you is it? I mean aren't there about a million little sperms swimming around in my stomach now"

"No, not at all. If it were, there would be considerably fewer people in the world today. It's mostly protein and water of course. It's also low calorie so you can have seconds. As far as the sperm is concerned, you don't have to worry about that with me. I've had a vasectomy. But your stomach acid will take care of any sperm from a fertile man's ejaculation."

She giggled and said, "So how long will it take you to whip up another batch?"

"It shouldn't be too long considering what we're going to do next." I got up from the cushions and told her to lie down on them on her back. "Now pull your knees up and spread your legs." When she did I lay with my head between her legs and my face inches from her slit.

"Lisa I really like your pussy. It's so pink and perfectly constructed. And so damned youthful. We're going to start your oral sex lessons with my performing it on you. This is commonly known as going down on a woman although there are many euphemisms for this activity; rug munching, lunch at the Y, yodeling in the valley. Regardless of what you call it, it's one of the most pleasurable experiences you can have."

Moving my head forward very slowly, I began kissing her upper thigh as the tip of my tongue barely touched her skin. Inching closer to her outer lip the pressure of my tongue increased until I reached the puffy pink flesh. Resisting the urge to move laterally to her opening I dragged my tongue up the length of her lip to the top to lightly lick her clit. A soft moan told me she was enjoying this immensely. Moving over to her other thigh I repeated the same tender kissing culminating in another strong lick up her lip to her clit.

"How are you feeling Lisa?"

"Ummmhhhh Robert....I like this a lot. My insides feel like they're vibrating."

"That's good Lisa but we've only just started. I'm going to lick every inch of your pussy until it's soaking wet. Then I'm going to suck on your clit until you cum all over my face. Do you think you can do that Lisa? Can you cum really hard for me and soak my face in your juice?"

"Ohhh God Robert, Yes. Lick me all over and I'll cum for you just like you want me to."

My mouth returned to the bottom of her slit and began licking and sucking on every part of her sweet pussy. She was squirming and breathing heavily as my tongue licked her labia and my lips pulled on them to stretch them. When I stuck my tongue into her vagina she breathed in sharply and pressed her hips up to mash her pussy against my mouth.

"Ohhh Robert your tongue feels so good in my pussy. Keep sucking it. Please don't stop."

I did stop just long enough to tell her, "Use your hand to rub your clit. Make yourself cum for me while I suck you."

Her hand moved to her mound and her fingers began to rub her sensitive nub as my tongue stretched to its limit to extend into her vagina. Her sweet nectar was almost a steady flow as it coated my outstretched tongue.

"Unnnnhhhh, Ohhhhhh Robert....I'm....going to....cummmmmm!

Feeling her cum on my face was exhilarating. Moaning loudly, the pink walls of her vagina squeezed the tip of my tongue as her orgasm pulsed inside of her.

When her orgasm subsided she began to cry. "What's the matter Lisa?"

"Robert that was the most incredible thing anybody has ever done to me. I was always told that my pussy was nasty and that nobody should ever put their mouth on it. But you've shown me that you really loved doing it and you don't think it's nasty. Thank you Robert for helping me the way you have."

"Lisa rest assured that there is nothing nasty about your pussy. On the contrary, it's delicious. Your sweet juice tastes as wonderful to me as my grandmother's ambrosia. In fact, I want some more. Are you ready to go again?"

"Oh yes Robert. You can do this to me as much as you want. It's even better than the vibrators."

"OK but first I have a favor to ask of you.

"What kind of favor?"

"Would you let me shave your pubic hair off your pussy?"

"Sure, if that's what you want. It's the least I can do for all you've done for me."

We got up and went into the bathroom just outside my office where I kept a razor and some shaving cream. Her light brown hair wasn't very heavy so it didn't take long to remove it. I used a small towel with hot water to wipe her bald crotch after shaving her. She looked adorable.

She looked at it in the mirror.

"What do you think Lisa?"

"It looks nice. And sexy."

"That's what I think too. My cock's already getting hard again just from looking at you."

When we returned to the office I told her, "This time you can drive."

She gave me a quizzical look as I took her place on the cushions on my back.

"Now you straddle my face and lower that sweet pussy down onto my mouth. You just move however you want to and I'll lick and suck you until you cum again."

Her eyes were sparkling as she swung her leg over my chest and moved forward until her pussy was just inches above my face. "Lisa hold still for a minute, I want to look at your beautiful bald pussy for a while."