Lisa's Lessons

Note: This is a work of fiction. All characters depicted in sexual activities are portrayed to be eighteen years old or older at the time they are engaging in those activities. Any similarities to actual persons, living or dead, or events, past or present, are strictly coincidental.

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My wife, Judy walked into my home office one morning to bring me a fresh cup of coffee and announced: "Robert I've decided to have Barbara and her daughter clean the house every two weeks. I don't have time to do a thorough cleaning as often as it should be done and I just found out that Barbara lost her job at the restaurant she's been working in because they decided to close down. She called me and asked if there was anything she could do for us to help her out until she finds a new job and I told her she could help us out by doing the things I don't want to do but need to be done on a regular basis."

"Yeah sure. I'm sorry to hear about her losing her job." Her dad had been working for us as a handy man because he has his weekdays free and wanted to pick up a little extra money. "I don't mind helping them out, especially if it helps you out as well."

Barbara's dad, Tom, had put screens in the windows of the house we were leasing. We fell into a fantastic opportunity to lease a fabulous house out in the country that a retired couple had built but couldn't live in because the wife was diagnosed with kidney disease and needed to be near a hospital for treatment.

My wife and I both had our own businesses so we could work anywhere there was a phone and an Internet connection. We loved the house and the seclusion. We had met Barbara when she drove Tom over to do the installation of the screens. She was a nice woman who had grown up in a typical country home where there was never very much money and had always had to do some kind of work to help out.

Over the two months or so that it had taken Tom to fabricate the screens we had pieced together the story of their family. Tom was a widower who had lost his wife twenty years ago to cancer. Barbara's husband was killed in an accident three years after giving birth to her only child, Lisa. Tom was also the owner and pastor of a church that advocated an obscure religious teaching that was distantly related to the Jehovah's Witnesses. Tom was extremely indoctrinated in the dogma and was fanatical about the family's adherence to what he believed was God's Truth.

He had tried recruiting us to his small congregation but we had let him know as politely as possible that we were not interested. Nevertheless, he persisted in preaching his beliefs as often as he could whenever he was around us. It was difficult to hold a normal conversation with him because he always had some Biblical reference to everything that was said to him. However, he was a skilled carpenter and craftsman who demanded perfection in his work, which is why it took so long to get all the screens finished and installed.

During this process I had been able to gain his confidence and impress him as a righteous man when I helped him with measuring the enclosures and getting the screens to fit with the hardware used to open and close the windows. My stock really went up with him one day when he had an episode that caused his legs to tingle and go numb. I thought he might be having a TIA so I had him sit on a bed in the room where he had been working and rushed to the kitchen to get him some water and a banana. I crushed a baby aspirin up in the water because I suspected he wouldn't take it otherwise. A few minutes after drinking the water and eating the banana he was OK. He couldn't stop thanking me enough for helping him.

The first day Barbara and Lisa showed up to do the cleaning, Judy spent an hour walking them around and detailing the work she wanted done with meticulous instructions as to how each job was to be performed. Judy is as much a perfectionist as Tom so Barbara and Lisa were used to having to adhere to a very high standard. After two more visits Judy had enough confidence in the girls to tell them that she trusted them enough to work unsupervised which freed her to go out and do various activities like shopping, having her hair and nails done and browsing through furniture stores. I managed to decline her invitation to join her and stayed in my office and worked.

For the next three months the girls showed up every two weeks promptly at ten and left around one. Barbara had bad knees and couldn't climb stairs very well so they had divided the two-story house up with Barbara doing the lower level while Lisa did the upstairs where my office was. There wasn't that much for Lisa to do since the only rooms on this floor were three guest bedrooms, only one of which had ever been used, a couple of bathrooms and my office but she was extremely thorough in taking care of it. I would spend some of the hour she was in my office talking to her about her life and her aspirations for the future and managed to find out a great deal about her.

She had been married when she was eighteen because she got pregnant by a boy of the same age that she thought she was in love with. The marriage didn't last long because he was extremely resentful of being forced into it by Tom and hated being constantly harangued to be part of Tom's congregation which meant going to prayer meetings and sitting through Tom's sermons every Sunday. He and Lisa got into an argument two months after the wedding because he had been drinking and their religion adamantly opposed the use of alcohol. The argument ended when he hit Lisa in the stomach causing her to miscarry. Tom had the marriage annulled and made him leave town.

This was four years ago and now she was twenty-two. One day while she was cleaning in my office I asked her, "Lisa do you have a boyfriend now?"

"No. My grandfather is very strict with me about dating because of what happened with Danny. He says as long as I'm living in his house I have to obey his rules and he has never allowed me to have another boyfriend."

"And you're OK with that?"

"I don't have much choice. I never finished high school so I can't find a job that would pay me enough to live by myself."

"Don't you get lonely?"

"Yes. Tom tells me to read the Bible when I feel lonely and ask Jesus to calm my heart."

"I don't want to contradict your grandfather but I think he is mistreating you to dictate what you can do as a young woman with needs and desires that you have every right to explore and fulfill. It's not healthy for a twenty-two year old woman to suppress her sexuality."

"Tom wouldn't like you talking to me about sex Mr. Wilson."

"Tom's not here now Lisa. You're in my house now and we can talk about anything we want to as long as it doesn't make you uncomfortable. There is nothing wrong or dirty about sex. It's a natural part of living and has a lot of emotional and psychological benefits. Besides that, it's fun."

"I'll have to take your word for that. Sex was never much fun for me. Danny only cared about his needs, never about mine. We only did it in the dark when he wanted to and I just lay there while he stuck his penis in me before I was ready and five minutes later he'd squirt his seed in me then roll over and go to sleep. Then I'd have to go in the bathroom to let his fluid drip out of me so I didn't have to sleep in a wet spot."

"I'm very sorry to hear that Lisa. It shouldn't be like that. Danny was obviously a very selfish young man and probably ignorant of any kind of real, caring lovemaking techniques. You've definitely been short changed as far as sexual fulfillment goes."

"Nobody has ever taken the time to show me what it should be like. I've seen some things on the Internet but I have to be careful that Tom doesn't find out. He would punish me for looking at sexual information."

"Lisa, he has no right to keep you from finding out how to have a pleasurable, adult sex life with as much joy and fun as you want. You're of age to look at anything you want and to ask for guidance about your sexuality. It's wrong for anybody else to deny that to you."

"Mr. Wilson, would you help me learn the things I need to know? Tom likes you and thinks you're a fine, honest man. I trust you too because you've helped me and my mother make some money when we really needed it."

"First, call me Robert. I can give you some books to read but they can only go so far. Eventually you will have to experience things to really learn about them. It's like swimming, you can't learn that from a book, eventually you have to jump in the water and get wet. Do you trust me to show you things that you might feel uneasy or embarrassed about?"

"Yes. I want to learn Robert. I'm way past the age when other girls learned about sex and I have feelings too. Tom says these feelings are evil and God will consider me a sinner for having them."

"Lisa that isn't true. God didn't make you a woman so you could be condemned for doing the very thing that created you. God wants you to celebrate life and enjoy all the things your body can do. Anything done with love and kindness in your heart is never a sin. How often do you masturbate?"

"Tom says that is a sin too and that I should never do it."

"That just isn't true Lisa. It's a normal and necessary function that everybody does. Even animals do it. It helps you to learn what you enjoy. Orgasms are great stress relievers. You have had an orgasm haven't you?"

"I'm not sure. I don't think so."

"Oh Lisa, my poor child you're missing the best experience life has to give you. You should be having them every day. That's the first thing we should work on, getting you capable of having an orgasm. You need to know how to make yourself cum and then you'll be able to tell someone else how you like to have sex so they can make you cum."

"Oh Robert please teach me that. What do you mean by make myself cum?"

"Cum is a word that when used as a verb is another way of saying you're having an orgasm. It's common for a man or a woman to announce their impending orgasm by saying 'I'm cumming' or 'I'm gonna cum' just before they climax; which is yet another word for an orgasm.

When it is used as a noun it usually refers to a man's semen, which is the fluid that spurted out of Danny's penis, when you and he were fucking. When a man expels his semen it is called ejaculating. The word cum can also be used to refer to a woman's juices when her vagina gets wet because she is sexually aroused. Some women can even squirt their juices when they have an orgasm similar to the way a man does."

"I see I have a lot to learn Robert. That's why I need you to teach me. I feel like I'm not totally living my life because my sexuality has been repressed for so long. I have woken up from a dream and felt wetness between my legs. Does that mean I was sexually aroused?"

"Yes it does. Your sexuality doesn't turn off when you go to sleep. Having dreams about sex is very common and you can even cum while having a sexy dream."

"Then maybe I have had an orgasm. Maybe that was why I was wet when I woke up."

"Could be. But the goal is to have orgasms while you're awake so you can enjoy them. You know, if I hadn't met your mother and grandfather I would never have believed that you didn't just make up this story about your abysmal sex life. I mean, in this day and age of cell phones and the Internet, how could a woman your age be so naïve?"

"My life has been hard Robert and I've been deprived of a lot more than just a normal sex life. There has been a lot of pain and worry that I've had to endure and I've spent most of my life living in fear. It's not something I wanted."

"No. I'm sure it isn't and it makes me very sad to hear what you've been through with very little help or sympathy for your suffering. I'll try to help you change some of that and I won't take advantage of you or cause you any more pain. You deserve much better. You're smart, pretty and a nice person and I would be proud to help you with this important part of your life."

"So when can we start?"

I looked at the clock and saw that she still had about an hour left before they finished. "There's no time like the present. You're almost finished with the cleaning so why don't you sit on the loveseat against the wall and I'll try to teach you a little bit about masturbation."

"You mean do it with my mother downstairs?"

"Barbara never comes up here and even if she did, we can close the door so she can't just walk in on us."

"OK, what do I do now?" She asked as she took a seat on the small couch.

"Take off your pants."

"Do I have to be naked to do this?"

"It's not an absolute requirement but most sexual activity takes place with the participants naked so you need to get comfortable with it. You can leave your blouse on if you really want to for this first session."

She got up and went to the bathroom that was just outside my office and got a towel. She returned and put it down on the cushion to cover it. Keeping her back to me she undid the button on her jeans, unzipped them and slowly lowered them down to step out of them and put them on the other side of the loveseat. Then, very hesitantly, she slid her panties down and off then placed them on top of her jeans.

The T-shirt she wore came down to her lower back so her entire ass was revealed. I had never taken the time to look at her as a desirable woman before and I was quite surprised to see how cute and sexy her ass was. It was beautifully shaped and well padded and her legs were very pretty, long and toned. My cock informed me how much I liked it by beginning to swell.

"You have a very pretty ass Lisa. I haven't been this close to a twenty-two year old ass in thirty years and I had forgotten what a sexy sight it is."

"Thank you Robert. Nobody has ever told me that before. What do I do now?"

"Turn around. They may not have told you but I'll bet a few of them thought it."

She slowly turned and her hands moved to cover her pussy. "Move your hands Lisa. You don't need to be ashamed of your body. It's very lovely and you should be proud of it." She moved her hands to her side. "Tell me what you're feeling."

"I...I'm nervous and scared and a little excited."

"Why are you scared?"

"Because I've never done this with anybody before and I've been told that it's wrong."

"The people who told you it was wrong had to have been told themselves that it is wrong by somebody else. And somebody else told them it was wrong. So how do you think the idea that what you are doing is wrong originated?"

"Somebody, somewhere must have thought it was wrong to show their naked body to another person."

"You were born naked weren't you?"

"Yes, of course."

"If it were truly wrong to be naked with other people why do you suppose God or evolution or whatever you want to believe has decided that being naked is the natural state for people?"

"I don't know."

"Lisa making somebody feel that it's wrong to be naked is a way to make you ashamed of your body. Shaming somebody is the sin, not being naked. You now have the chance to make up your own mind about it. Don't let somebody you don't even know convince you that it is wrong.

Try to drop the nervous and scared feelings. There is nothing to be nervous about and there is nothing to be afraid of. I won't hurt you or judge you. If you really don't want to do something just say so. Concentrate on the excitement you're feeling. Think about this as something fun to do even though it's new to you and you don't feel comfortable because you haven't done it before. I'm not nervous and I'm not scared but I am excited too. Sit down." She sat on the towel with her back all the way against the loveseat. "Move forward so you're sitting close to the edge."

She scooted forward until her ass was on the edge of the cushion. There were two pillows on the other side of the loveseat and I told her to take one and place it behind her back. She held her legs tightly together.

"Now Lisa, I want you to close your eyes and breathe deeply in and then exhale through your mouth. This will help you to feel less nervous. Keep doing it until I tell you to stop." I let her do this for a couple of minutes then told her to stop. "Keep your eyes closed and spread your legs open."

She slowly moved her legs apart a few inches. "Wider." She increased the distance between her legs until her pussy was fully exposed. It was adorable. As pink and pretty as a young pussy can be. "Keep your eyes closed and tell me how you feel."

"I don't feel as nervous as I did but knowing you're looking at me is making me more excited."

"Does it bother you that my looking at you is making me excited?"

"No. In fact it makes me more excited that you like what you see. Nobody has ever admired me like this before and it makes me feel appreciated. I like knowing that I can make you feel excited."

"Put your hands on your breasts. Use your thumb and finger to lightly pinch your nipples."

"Do you want me to take my shirt off?"

"Only if you feel good about doing it."

"It seems silly to keep it on if I don't have any pants on."

Without a second's hesitation she lifted her T-shirt up and over her head then reached behind her to undo the clasp on her bra and placed each garment on top of her pants before moving her hands up to do as I had told her. She fondled her soft mounds for a moment then began to pinch her nipples. She breathed in sharply and moaned softly.

"Does that feel good Lisa."

"Yes it does. It makes me tingle all over."

"That's good. Do you think you would like it if I were the one doing it to you? Imagine for a moment that my hands are cupping your breasts and massaging them. Then feel my mouth kiss your nipple and lick it with my tongue. Would that feel good to you?"

Eyes still closed, her head tilted back as she said, "Oooooh yes Robert. Kiss it. Do you like my breasts Robert? Are they big enough?"

"They are exactly the right size for you and they have a teardrop shape that is perfect. They're beautiful Lisa. You like showing them to me don't you?" She didn't speak but nodded her head to let me know she did indeed like me admiring her breasts.

"Now move one of your hands down between your legs."

Her right hand moved down her stomach to cover her mons.

"What do you call what's between your legs?"

"I call it my female parts."

"I want you to call it your pussy. Do you think you can do that."

"Yes. I've heard it referred to by that name before but my mom told me to call it my female parts."

"Pussy seems like a much better name for it don't you think; all warm and cuddly and furry. Slide your finger from your clitoris down through your lips and feel your vagina."

Her hand moved down as her finger slid through her slit until she reached her vagina.

"Put your fingertip in your vagina and tell me what you feel."

"It feels warm."

"Is it wet?"

"A little."

"Slide your finger in and out. Use the fingers of your other hand to rub your clitoris. Go slow, this isn't a race. Don't think about anything but making yourself feel good."

"Oh Robert, it's not easy to make myself feel good doing something I've been told is a sin. I've had to block these feelings for so long that I can't even remember what feels good."

"Lisa what you are doing is not a sin. You have every right to explore and discover what gives you sexual pleasure. If you don't do this you won't be able to tell your lover what to do to please you. In fact, you can't love another person if you don't love yourself. Sex is a very beautiful way to demonstrate your love for another person so you need to know how to do it. You have a lovely body and it's very sexually appealing. Embrace your sexuality Lisa. It's your birthright. Claim it."