Lisa's Lessons

She spent a few more minutes playing with herself and I could tell she was letting go of the thoughts that had shackled her mind regarding sex. I wanted her to continue but it was getting close to the time she had to leave.

"Lisa, we're almost out of time but I want you to continue this at home if you can. Before you go to sleep, spend some time feeling your body and touching it. Use some lubrication if you need to when you put your fingers in your vagina. Try to revive your ability to naturally lubricate with your own juices. Now open your eyes and get dressed. You've done very well. I'm proud of you."

"Thank you Robert, you are a very kind and helpful teacher. Why hasn't anybody else ever helped me with sex?"

"That's a long story but I'm not afraid to help you because living in fear and ignorance about sex is the best way I know of to really mess up your life. And you'll mess up somebody else's life too if you don't have knowledge and open communication about your sex life. We'll have another session next time you come to clean."

When they had gone I considered what Lisa and I had done to see if continuing was a good idea. There were reasons why we shouldn't but they just didn't seem good enough to put a stop to helping her. Judy and I didn't have children and seeing somebody who had to grow up in what I considered to be an abusive environment triggered my paternal instincts.

It has been suggested that if you see something, say something. However, in some situations, saying something is not sufficient. Talk is cheap and advice is often unwelcome or ignored. In Lisa's case I was motivated not only to say something but also to do something. After all, we were both adults. If she wanted to stop all she had to do was say so. As far as Judy was concerned, what she didn't know wouldn't hurt her. She had things she liked to do when she left me here with Barbara and Lisa and I didn't mind her doing those things in the least. I could just consider my helping Lisa to be my new hobby.

It occurred to me that I needed to spend some time preparing for the next visit. I went to some porn sites and found some very stimulating videos of young women pleasuring themselves with their hands as well as dildos and assorted vibrators. I bookmarked them so Lisa could have a direct visual experience of what masturbation is all about. These videos also gave me the idea to order some toys for Lisa to use both here and at home to improve her technique and to make having orgasms a regular habit. I even found some that could be activated by remote control. A few could even be operated by cell phone. (You knew there would be an app for that didn't you) Finally, technology had produced something worth having! And they delivered them right to your door. We live in interesting times.

It blew my mind to see the incredible assortment of non-biological devices for sexual purposes that exist today. I was mainly interested in things for women and the variety of mechanical and electronic gadgets was amazing. From small, discrete battery operated personal vibrators to artificial cocks that are so lifelike they're scary (at least they are to a heterosexual man), all the way up to industrial strength fucking machines that could keep you in perpetual ecstatic sexual intercourse (in all orifices) for as long as you remembered to pay the electric bill. Videos gave undeniable evidence of their effectiveness. Some of the women appeared to have overindulged to the point of looking like they just lost a heavyweight-boxing match when the machine was finally switched off. They were all smiling though, not to mention soaking wet.

Men too had a cornucopia of sexual aids too numerous to mention here with the exception of the REAL DOLLS .com web site. It made me sad and depressed when I beheld the wonders about to become available to the human male. There will soon be robotic sex dolls so lifelike that no natural born woman can possibly compare. These dolls are already a serious alternative to a real live girlfriend but in about twenty years they will be beyond spectacular and you can program them. Even at ten thousand dollars they're a bargain compared to a divorce. I was born fifty years too early.

If you think it's impossible for an android to be superior to a biological human in sex, love and intimacy, I suggest you look up what Hiroshi Ishiguro, a Japanese professor of robotics, has been doing for the last fifteen years. It will give you a whole new perspective on human/machine interactions.

David Levy, an expert in artificial intelligence, has written in his book 'Love and sex with Robots' that we are not far from the time when humans will actually prefer androids as friends, sexual partners and even spouses. Marriage is going to disappear. Given what weddings, spouses and children cost, nobody, male or female, would even consider a conventional relationship.

I couldn't wait for cleaning day to arrive. I felt like a kid on Christmas morning anticipating his gifts. When it did, everything went according to schedule. Once Lisa came upstairs I helped her do the cleaning so we'd have more time to do her session. It was gratifying to know that she had been looking forward to it as much as I had been.

I barely got the door to my office closed before she started getting naked. As soon as her clothes were off, I told her I had something I wanted her to see first. My computer was attached to a flat-screen HD TV on the wall so I asked her to sit next to me on the loveseat and went to one of the sites I had bookmarked. I loved her reaction when the video started.

"Lisa I want you to pay close attention not only to what she's doing but also to her facial expressions. I want you to see what sexual satisfaction looks like when a woman is getting aroused and having an orgasm. Listen to the sounds she makes. I know the women in some of these videos are just putting on an act but the ones I chose to show you look pretty convincing to me. In any case, you need to see what letting go and having a good time looks like."

My attention was divided between the screen and looking at Lisa. I was delighted to see that she was not offended by what many would call pornography but was truly interested in it as a learning tool. When the first one ended I asked her what she thought about it.

"Wow Robert, I had no idea what I've been missing. Her feelings came across as pretty authentic to me. I so want to learn how to do this, how to be this free spirited and uninhibited about sex. I can't wait to get started on today's lesson."

"Before we do I want you to see another video. This one will include using toys but not the ones children should be playing with."

I went to the next bookmark and started the video. I had chosen this one based on the wide variety of toys. As each one was used to increase the arousal of the woman in the video Lisa's eyes got bigger and wider as she watched things ranging from external stimulators including a vibrator as big as a hand held vacuum cleaner to dildos as large as her forearm being inserted into her vagina. If this woman was pretending to have orgasms she deserved an award for acting.

"Robert I'm both fascinated and shocked at all the things that can be used to masturbate. Will I get to use some of those things?"

"You sure will. It's all part of today's lesson. I had spread a large beach towel on the loveseat to cover both cushions so she could lie down on it. "You look beautiful Lisa. Lie down on your back." When she did I placed one of the pillows under her head.

"Robert I've been practicing every night before I go to sleep. I take a shower and wash my pussy with a fragrant body wash and then get in bed and lie on my back like I'm lying here now. Then I spread my legs and use both hands to rub my upper thighs and my outer lips with a creamy moisturizer. I go very slowly and reach down to my vagina with my fingers then slide them back up to my clitoris. I've decided I love my pussy. It starts to feel warm in just a few minutes and I use one hand to put my finger in my vagina while the other one rubs my clitoris with little circles. I've gotten very close to making myself cum a few times but I'm nowhere near what the women in those videos were feeling."

"That's very good news Lisa. Don't worry; we'll get you there. I bought you some lube to use with the toys I got. Use some of it to show me what you do at home."

She spread her legs and pulled them up to open her crotch wide.

"Hold out your hand Lisa." When she did I squeezed some of the lube on her fingers. "Now let me see you rub your pussy."

As she started to rub the lube on her upper thighs she said, "Oooohhh Robert this stuff feels great. It's cool and tingly and very slippery."

She demonstrated her technique for a few moments then I stopped her. "How are you feeling Lisa?"

"I feel warmth in my vagina and cool on my lips where the lube is."

"Are you nervous?"

"Oh no! I'm excited. It's much better having you watch me than doing it by myself. Your approval validates my doing this and makes me feel much more comfortable."

"I'm glad Lisa. I want you to be comfortable and become as uninhibited about your body and your sexuality as the women in those videos. I want you to learn to celebrate the fact that you are a desirable sexy woman and feel really good about yourself. You deserve that Lisa. Are you ready for the next lesson?"

"Yes and thank you for doing this for me Robert. It means so much to me."

Reaching into the big box of toys beside my desk I brought out a very lifelike cock that was six inches long and about as thick as my own. It was as normal as they come and even had realistic testicles you could use to hold onto it while you used it. The balls weren't just a solid piece of rubber or plastic but looked and felt like a real scrotum with testicles squirming around inside. It was actually quite beautiful and I had no idea what material was used to make it but it felt exactly like my own and, I hate to admit, was prettier. It also did something mine couldn't, it vibrated. At variable intensities. I was jealous.

I held it up for Lisa to see and she gasped. "Oh wow Robert that looks very real!"

"I want you to take it and rub some lube on it then put the tip at the entrance to your vagina and slowly insert it. We'll leave the vibrator off until you've used it a little while."

She picked up the bottle of lube and squirted out a glob onto the head of the dildo then sat the bottle down and moved the cock down between her legs holding the shaft as she positioned the tip at her entrance. She held still with the tip poised at her opening. "Robert I haven't felt this in over four years. I'm about to die from anticipation."

"Take your time Lisa. You're in control now, not Danny. Make it feel wonderful. Enjoy how it spreads your pink folds as you slide it in. Breathe deeply while you take it. Go ahead now, make yourself feel good."

I could see the lube glistening on the tip as she pressed it into her hole. She took a deep breath and continued inserting it, pausing often to experience the sensations of a cock in her cunt for the first time in years. It was fascinating to watch her do this. My cock was as stiff as a board by now. Watching a woman do this live a few inches away from you is way better than watching a video. After several minutes, the dildo was buried in her vagina and she moaned as she abandoned herself to her feelings. Her hands moved to encircle each of the testicles.

"Oooohhhh Robert, these really feel like a man's balls. Where did you get this?"

"The Internet is an infinite source of all sorts of wonders."

"I want to hold onto them but I want to feel this penis slide in and out of me. Will you do that for me while I hold onto these lovely balls?"

"I'd be delighted to Lisa." I reached down to the base of the dildo where there was a black plastic knob that was used to turn it on and vary the vibrations as well as to use as a handle for what I was about to do. I pulled back on it and began sliding it out of her. When I had it about half way out I began to push it back in again. I used a slow, steady rhythm to insert and retract it so she could get used to being fucked again. The look on her face told me she was enjoying this. Her eyes were fluttering open and shut as the tip of the cock bottomed out in her and she moaned as it was withdrawn. Her nipples were hard and distended and I was tempted to lean over and suck on one of them but managed to resist that impulse.

"Does that feel good Lisa?"

"Oh yes Robert it feels wonderful. Could you go a little faster please?"

"Of course. That's very good Lisa. You asked for what you wanted and didn't just take what I was giving. That's a very positive sign that you're taking control of your own sexuality."

I increased the speed as well as the length of my strokes and I could see the dildo beginning to get coated with a sheen of her juices. Her breathing became shallower and changed to a quicker rate. Her fingers continued to fondle the dildo's balls as if she were doing it to a live person.

"Do you like to play with a man's balls Lisa?"

"Yes, I've always been fascinated by them. A woman has her ovaries deep inside her but a man has his balls hanging down on the outside. I've always wondered what it felt like to have them dangling out like that. Do you like to have your balls fondled while you're having sex Robert?"

"Yes I do, especially if they've been sucked on first and are covered with saliva."

"Oooohhh I've never sucked on them before. I think I'd like to do that. Could I suck on your balls Robert?"

My cock throbbed when she said that. "This isn't about me Lisa, it's all about you. Maybe later we can progress to other things." I picked up the tempo of my thrusting and she began to emit little grunts as the cock pushed into her and then was pulled all the way out.

"Unnnhhh, Unnnnhh, Robert I think I'm getting close. Danny never lasted this long and I'm feeling things I've never felt before. My vagina is throbbing in a way that it never has before. Ooooohhhhh Robert, yes I....I....I...Think....I'm....Cumming!

I moved my other hand to the knob and turned it to start the vibrator then set it at about half way and could feel the vibrations in the hand I was holding it with.

"OHHHH GOD ROBERT. I'M GOING TO CUM."

I turned the vibrator off but left the dildo inside her while her vagina contracted around it as she had her first climax. She looked beautiful as an unmistakable sign she had indeed had an orgasm spread across her chest and under her neck. The red flush was irrefutable proof she had experienced a real climax.

"Oh Robert I did it didn't I. I had my first orgasm. Oh thank you for doing that for me. I've never felt anything so glorious, so powerful and wonderful."

"Lisa it's been my experience that problems with orgasm are mostly in your mind. When you can let go of the thoughts that keep you from enjoying sex your natural functions activate to produce the orgasmic state. This is true for men as well as women. You've taken a big and important step by giving yourself permission to have an orgasm. Once you could do that, the actual mechanics are easy. Your body has a built in craving for having orgasms. You just have to remove the blocks."

"I feel like this is the most important day of my life Robert. I can't tell you how grateful I am for your help. I'm never going to allow anyone to take away my right to enjoy sex again."

"Are you ready to do it again?"

"Can I do that?"

"Lisa women have an enviable ability to have multiple orgasms. Sometimes they happen one after another. In any case, it doesn't take much time for a woman to achieve another climax after having one. Men, especially men my age, need time to recover from one orgasm before they can have another one but it depends on the circumstances and what kind of stimulation he receives in order to be ready to go again."

"OK let's see how long it takes me to have another one."

"I'm going to remove this dildo from you and we're going to use some different toys." I walked to the bathroom outside my office and put the dildo in the sink to wash it as well as my hands. When I returned to my office I looked in the box of toys and brought out two devices. The first was a pretty red vibrator about five inches long that was curved and tapered toward the end to a blunt point. It appeared to have a thin layer of very soft silicone covering it. The little diagram that accompanied it said it was very effective for stimulating a woman's g-spot as well as a man's prostate when inserted in his ass. Drawings illustrated both activities.

The second device was a large vibrator that looked like what you would use to beat a big drum with in a marching band. It was obviously not for insertion unless you had experienced natural childbirth or spent a lot of time gradually increasing the size of objects shoved into your vagina. Or god forbid, your ass. The head was about the size of a coffee mug and the handle contained an array of buttons, lights and rocker switches to vary the intensity, frequency and speed of the vibrations. It was complicated enough to have a user manual included with it.

I studied it and realized that the basic operation was really quite straightforward. The controls were for after you got the primary use down pat. I turned it on and even at the factory setting the vibrations were quite intense. The soft white cylindrical head made my whole leg buzz when I put it on my knee to test it. I turned it off and handed it to Lisa. "Here, put the head of this thing on or near your clitoris and flick the top rocker to turn it on."

She put the big head on her clitoris and turned it on. "OH MY GOD! Robert this thing is incredible."

"You can slow it down a little with the slider next to the on/off switch if it's too much for you." She played with the slider and set it to the lowest setting then laid back and let it do its thing. "Unbelievable! I could never have imagined what effect vibrations could have on my sex organs."

"OK, turn it off for now. Here's another one you're going to like. I'm going to have to use this on you until we find your g-spot."

"What's my g-spot?"

"It's a little patch of tissue at the top of your vagina that is very sensitive to being touched. Some women can cum better from having their g-spot rubbed than they can from having their clitoris played with. The good news is you don't have to choose. Lay back and I'll see if I can locate it."

She laid her head back on one of the pillows so she could watch what I was doing even though neither of us could see what we were looking for. I was encouraged to see she had lost all her shyness about spreading her legs wide apart and I had to pause to admire her freshly fucked pussy. Before using the vibrator I stuck my finger into her vagina to see if I would need to use the lube. I was very happy to discover that she was more than sufficiently wet from her own juices after her orgasm.

I smiled at her and she seemed to know why because she gave me a look of smug satisfaction that her parts were in excellent working condition. I had a fleeting urge to replace my finger with my tongue but managed to control it. I added my middle finger to the first one and began probing around to find her spot. She moaned as I curved my fingers up and began tickling her upper wall like I was scratching her. I moved them in a little further and her quick intake of breath told me I had located the sensitive spot. I continued to tickle it and her moaning increased.

"Does that feel good Lisa?"

"It sure does, but I'm really pissed that nobody has ever shown me that I have this magical little spot before."

"Well you know about it now. Let's see if this little gadget is as good at stimulating it as my fingers are."