Training Lolita

The name of this story has nothing to do with the main characters names. The story is about a 40-something guy having sex with an 18 year old girl, so I just took the name "Lolita" from the Nabokov novel.

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John looked down from his second story window at the exciting scene that was unfolding next door. He was almost 50, but still found himself routinely checking out Dana, the young girl next store. She had just turned 18, but he knew from his interaction with the neighbors that her mother tried very hard to shelter her. He had known this family for 10 years and had watched her grow into a somewhat shy, but blushing beauty.

But now he was watching as she and her boyfriend were all over each other, his window slightly cracked to hear anything that went on. They were kissing hard and the young man had his left hand holding her neck and his right hand grabbing her left tit. He was massaging it and she seemed to be reacting to it. She squirmed under his ministrations and John could hear a moan.

The young lad moved his hand down to Dana's ass and pulled her to him, probably to rub his hardening cock against her. She squirmed more and let him. Then she suddenly pushed him away a little and reached down between them. He squirmed. They turned a little and John could see that she was shoving her hand down the front of his pants.

"No, Dana, please don't." He hissed at her in a loud whisper. "Your mother is right inside." He gasped and trembled. "And I'm going to cum."

But Dana kept playing with his cock. "I want to feel it, I want to suck it, and I want to see it squirt." That put him over the top and he started jerking his hips as he filled her hand and his pants with his jism.

"Shit, Dana." Her boyfriend pulled away and ran around to the front of the house and disappeared from view. The sound of his car indicated that he was leaving.

After standing there and staring at her boyfriend's back as he walked away, Dana sat down, wiped her hand off on some paper towels, and put her head in her hands. John could hear her as she berated herself for pushing too hard.

"Everybody's doing it! What's wrong with me? Why doesn't anyone want to do it with me?" She turned and took a drink out of what appeared to be a vodka bottle that was sitting next to the paper towels. And why was there vodka and paper towels there?

John saw an opportunity. He had been friendly and a good neighbor to the Wilson's for years, and this might be a chance for some fun. She was horny trying to learn about sex, and drinking. He made his way downstairs and went around the side of the house. He acted like he just happened to be heading into his back yard. He stopped suddenly when he saw her there.

"Dana?" She looked up and he could see by her look that she was upset. "Are you okay?"

"Yes, Mr. Tilton, I'm fine." She turned to go. John could hear her slur her words a little. Had they been drinking very much? It really did look like a Vodka bottle that she had been drinking from.

"Wait!" John reached out and lightly touched her on the shoulder. "I can see something is wrong. We've known each other for years; let me help. What is it?"

Dana was in a turmoil and wanted to discuss it, but it was too personal. "Nothing."

John pulled her closer, holding her by her shoulders, and looked directly into her eyes. "I know something is wrong. I've been a teacher for many years and I know when something is wrong. Please let me help."

Dana just lowered her eyes. "It's my boyfriend."

John put his hand under her chin and lifted it up to look into her eyes. "I know that this is a tough age, does it have something to do with sex?"

Dana's eyes opened quickly and she glanced away. "What?"

"C'mon Dana. I have taught high schoolers for years and also taught sex education. I know that that is the biggest problem today."

"He and I want to have sex, but he won't even let me see his -- you know -- his thing."

John could barely hear her as her voice trailed away. He pulled Dana into a hug. "Don't worry sweetie. I know this is difficult." He pushed her arm's length away and looked directly into her eyes. "Mother nature is a bitch in this area. Due to the desire to procreate, she makes both men and women go through really tough hormonal increases during their teens. Some are not ready for sex, but their bodies are demanding the physical release. We are an enlightened society, but we still cannot properly discuss and deal with our sexuality. Do you want some help and guidance?"

Dana was looking at him and listening to his words. "I don't know if I can."

John was guiding Dana to his backyard where he had a two-person glider and some chairs on his deck. With her having consumed some alcohol, she may be susceptible to a little prodding to play with him. "Come. Let's see if we can't address some of these issues."

Dana went along, seemingly in a little daze, and sat next to John in the glider. She sat down and pulled her legs up to her chest, hugging them, oblivious to how her short skirt was showing her entire crotch. John noticed that her underwear had snuck into her pussy on one side so the left lip was showing. This was going well.

John turned toward Dana, grabbed one of her hands, and held it. "So, tell me. What happened just now that I found you out here?"

Dana stared up at him for a few seconds and John just smiled warmly, trying to get her to feel at ease. "Brad and I were kissing and he started to, you know, move his hands around."

"He put them where?"

"On my chest." She looked at the ground.

"So he started feeling your tits?"

Dana looked up a little surprised, but John kept his face non-committal. "Yes."

"And did you like that?"

"I don't know."

"Of course you do. At your age, with the hormones raging, I'm sure you liked it when he felt your tits, right? Did he stimulate the nipples? Did they harden?"

Dana hesitated. "Y-y-yes."

"Of course. The human nipple has plenty of capillaries in it that fill with blood when stimulated. For women, I think more than men, it can be very pleasurable. Was it pleasurable for you?" John kept speaking normally and matter-of-factly to keep everything under control.

"I guess so."

John continued his pursuit of this young beauty. "And then what happened?

"He put his hand up my skirt and I put mine on his - you know."

"He tried to feel your pussy?" Dana nodded. "And you started feeling his cock?" Another nod.

Suddenly, she started feeling more assured about the conversation or the alcohol relaxed her more or both. "Yeah, my friend Mel tells me how much fun they are and she even sucks them. I just wanted to feel one and feel how it throbs when it squirts. She told me that that's very fun." Then Dana looked up at John and her eyes went wide. She forgot who she was talking to.

John stayed nonchalant about it. "That's perfectly natural. Men and women want to experience the pleasure that comes with that, and it's also an amazing thing when dealing with something so new and just a little forbidden." John leaned forward. "Would you like me to provide some tutoring on this? I could help you with learning about sex. I was, after all, a sex education teacher."

Dana smiled and seemed to think this was a great idea. "Oh, yes, Mr. Tilton. Would you do that for me?"

"Of course, sweetie. I have a great plan that includes some excellent hands on sessions. But there are three rules that you must follow. Are you ready?" John snuck in the part about hands on to see what her reaction would be.

"Yes, sir." She either didn't hear it or was willing to go along.

This was going well. "First, this is just between you and me. You can never tell anyone about this."

"Yes, sir."

"Second, you must agree to do everything I say. I know from my teachings and life experiences how to do this and you must not ever disobey me."

"Yes, sir."

John thought closely about number 3. "And third, you must be here three days a week. I know that your mother works late at the hospital on Tuesdays, Thursdays, and Saturdays. You will come to my house ready for instruction each of those days. Got it?"

"Yes, sir."

"Shall we begin now?"

Dana nodded. "Yes, sir." She seemed almost eager now.

"First, what is your goal? Do you just want to be proficient in the art of sex, or do you want to be known as an expert?"

Dana looked at John with bright eyes. "I want to be an expert." She grinned.

"Fine, follow me."

Lesson 1.

John stood and held out his hand. She took it and gave him a smile that hit him right in the crotch. He led her into his house, up the stairs to the second floor, and into the master bedroom.

John reached up to his bookshelf and took down a biology book. He held it in his hands. "Now we could go into this", he waggled the book as he held it up, "and cover this subject again like in school, but I think you have already had human biology, right?" Dana nodded. "I think you need the real hands on experience, don't you?"

Dana stared at John for a second. He could see the wheels turning in her head as she considered what he was saying. "Yes, sir."

"I want you to say it." John prodded her to make her acknowledge what he wanted to hear.

Dana smiled sheepishly. "Mr. Tilton, I want hands on experience with sex."

John smiled. "Good girl." She appeared to be ready.

He slipped off his robe and his sleeping shorts and then crawled onto the bed. He lay on his back and looked at Dana. She was staring at him, looking more at his crotch then his face as her eyes travelled back and forth. "For your first lesson, you must satisfy your curiosity about seeing a man cum and squirt, so I want you to check out a real cock in the open and the light. This way you can see it and feel it get hard and enjoy it." Dana didn't say anything so John shook his hips, his slightly fattened cock flopping around.

Dana stared at him. John could see the indecision. "Dana, you promised you would obey. I'm giving you a chance to see it, to have that hands on experience, and to learn all about sex. You said you wanted it and wanted to be an expert. Are you ready for your instruction, or not?

"Ready." Dana spoke unsteadily, but decided to sit on the side of the bed so that she could have access.

"It's better if you kneel between my legs so that you have both hands free and can see it up close."

Dana climbed onto the bed between his legs. She stared up at John and then reached out tentatively to touch his crotch. His cock was already a little swollen, but he was not completely hard yet.

When Dana's hand touched it, it jerked a little. "Oh!" She grinned at that. "I didn't expect that."

"Dana, whenever you touch a man's cock, if it isn't already hard, it will start to harden. When it does so, it will sometimes jerk as it fills with blood."

Dana put her hand back on it and squeezed. She stared at it as she felt it. She was mesmerized. John was hoping that that was not just the alcohol.

"Okay, now notice how it's starting to harden just from you touching it. With a beautiful young girl like you just staring at it will make most cocks hard. Go ahead and explore it. Feel how it is as it gets hard. Even play with my balls."

Dana was starting to really enjoy it, so she lay down between John's legs and stared as she held his now erect cock straight up. "It's beautiful. I think I love cocks."

John chuckled. Dana had evidently been wanting to be a "woman" for a while. "Go ahead and investigate it. I'm sure you've seen a few porn shots, so you know what to do." John was loving this turn of events. He thought she might freak out, but she was now enjoying it.

Instead, Dana started stroking his cock. "Mel says that boys like stroking and that cocks are neat because they are hard and soft at the same time."

John grinned. "Men like it when women stroke it, too. And that thing about hard and soft is what many women find interesting. Some women I've known like to feel how it is just after I cum and feel how soft it is then, too."

Dana smiled and just stared at his cock.

"When you are stroking, men like the up and down movement, but the most sensitive spot is really around the crown, just on the bottom. I am circumcised, so you can see it easily."

Dana leaned over and licked his cock -- right on that spot. He moaned. "You seem to know a little about all of this."

"Yes, sir. Mel has shown me some videos and has told me all about it."

"Continue."

Dana grinned and looked up at him. "Mmm. I think I like being in charge of a cock."

"Then finish it." All this talk was really getting to him.

Dana sat up on her knees and started stroking it with her right hand and playing with his balls with her left. She stroked it better than he would have expected and watched it carefully. She had obviously seen some porn that showed this. She looked up at John. "Does that feel good?"

"Yes, it does."

Dana grinned and went back to work. She was really enjoying this and suddenly had no qualms about stroking his cock. She leaned over and took just the head into her mouth. She sucked on it briefly and then sat back up and grinned at John, proud of her adventurousness. John just smiled. Dana continued to work on his cock. She was really getting into it and John could feel his desire to cum building up. It had been a while since someone had stroked his cock and this was a fantasy come true.

"I'm going to cum," John announced.

Dana kept at it until suddenly John jerked and started cumming. His first shot went into the air and Dana squealed and giggled. She watched raptly, continuing to stroke it, as it spurted several times, the last couple just running down onto her hands.

When John was done he fell back and relaxed. Then he felt her tongue and he looked up. Dana was licking his cock and slurping up the cum around it.

Dana sat up a little. "Mel always told me that it tasted yummy. I'm not sure about that, but she said that guys like it when you swallow all their cum."

"Your Mel knows a lot for an 18 year old."

"She's 19 already. And she loves giving blowjobs. She tells me that she really loves being in control of a guy's thing."

"Cock."

"Yes, sir. Cock. I like your cock, sir."

"Good. It's getting late now. Are you horny? Do you need to get off now?"

Dana looked down and actually blushed, even though she just slurped up his cum. "Yes, sir, but I think I will do that at home." She stood up.

John stood up, too, still naked. He grabbed a small towel he had positioned by his bed, wiped off the rest of his cum, then he got behind Dana and put his arms around her. "Are you sure?" As he did that, John ran his right hand up and massaged her right tit.

"Yes." Dana said yes but she didn't sound sure of that answer.

"You are a beautiful woman and you can play with my cock any time you want." John ran his left hand down and under her skirt. He moved it to the front of her panties and stroked her pussy through them.

Dana moaned. "Please, Mr. Tilton, not tonight." As adventurous as she was, she was still a little reticent to get naked with Mr. T.

John stopped and stepped back from Dana, resisting his desire to attack her so that she would be more apt to return. "Okay, Dana. I understand."

Dana turned toward John. "I'm sorry."

John smiled and lifted her face from staring at the floor. "Don't be sorry. This is all new to you. Don't worry. I'll make sure you are well trained before we are done." John took her hand and put it on his cock. "Now say good-bye to your new best friend."

Dana giggled and squeezed his cock. "Good-bye cock."

They went downstairs and John let her out of the house. He went back up to his bedroom and lay on the bed. This was working out great and he couldn't wait until Thursday.

Aftermath

When Dana got back to her bedroom, she stripped and crawled onto her bed. She was ecstatic. She had always had a crush on Mr. Tilton and had worked hard to find a way for him to want her. He was a decent man, and always nice, so she had a feeling that nothing would come of it until she was legal. And she was right.

And he finally did notice and come on to her. She even sat with her legs pulled up to her chest, knowing that her tiny thong was on display and probably pulled up into her pussy. She didn't care. She was pushing him. She didn't know if she should tell him, but she knew she was so horny that she had to take care of it.

She reached into her bedside drawer and pulled out the small vibrator that Mel had given her. She turned it on low and slowly ran it over her pussy lips. She didn't really need any preparation because she was already very wet, but she enjoyed drawing it out slowly, building her orgasm until she couldn't take it anymore.

With the vibrator in her right hand, she started lightly playing with and rolling her nipples with her left, moving back and forth every few seconds. But she was so primed she wanted to get it over with, so she did.

Dana ran the vibrator up her pussy, parting the lips and then holding it up against her clit for a few seconds and then moving it away. She continued to manipulate her tits as she did so and she put herself over the top quickly. She went through her orgasm spasms and ended up curled up on her side.

She took a deep breath when done and smiled. She had started down the road to losing her virginity to Mr. T. She couldn't wait for Thursday.

Lesson 2.

On Thursday, Dana showed up almost as soon as she got home. John watched her closely. She went inside her home next door for only about 30 minutes and then came over, having changed clothes. She had worn the standard jeans and some kind of top and sweater to school, but now she was wearing a skirt and t-shirt.

John waited as patiently as he could for her to ring the doorbell. He was dressed in only his robe.

When John answered the door, Dana looked him up and down and said hello. John invited her in.

"Mr. Tilton?" Dana began in a manner that worried John.

"Yes?"

"I'm not sure about all this -- stuff." Dana was concerned that he might not want to continue and was looking for a way to give him a way out.

John smiled warmly, but inside he was grinning lewdly. Why then did she change clothes in this manner? "How do you mean, Dana?"

"Well, I'm not sure I should be, you know, having sex with my neighbor."

"Well, Dana", John put his arm on the small of her back and slowly led her into the kitchen, "I think it is perfectly fine for a young inquisitive woman to want to learn about sex; and to do so from an older man is not so unusual."

Dana had let him lead her into the kitchen, but now stopped. "No?" She was hoping he would say something like that.

"No, it isn't. Many women do so. And, for your edification, many young men get their first real sexual experience in the same manner, an older woman."

Dana seemed to be studiously considering this. She wore a look of concentration on her face as he said this. "Okay."

That seemed quick, but John knew that she had changed clothes just before coming over because she was still very curious and, he hoped, horny. "Then shall we get started?" John held out his hand and Dana took it without complaint. It was warm and she let him lead her up to the bedroom again.

This time John had his laptop on the bed and several videos cued up. "First, I want you to look at a couple of videos. These clips show the kinds of things men love when it comes to sex, and will make you an expert in the eyes of all men. This first set of videos is all about blowjobs."

"Okay." Dana plopped down, sitting on the bed in front of the laptop, almost like they were just sitting down to view some YouTube videos. John leaned over to start the video and caught a whiff of what was most likely an expensive perfume. Dana was definitely interested in this whole idea.