Training Lolita Ch. 02

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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-- From the last story

John sat on the couch and the naked little vixen sat to his right and cuddled up to him. "Based on the amount of cum I just swallowed, I think you liked that scenario."

"Who wouldn't? That was fantastic Dana. I assume you got that idea from the videos I sent?"

She grinned. "Yep. And then I watched some other ones like that with Mel and Debra."

"And did you guys play a little?"

"Of course. I used one of Mel's dildos that is almost the same size as you. Debra used a vibrator, but then Mel got down and ate Deb's pussy until she came. I watched and got really turned on by that, but I didn't do anything."

"Why not?"

"I don't know. I'm still getting used to sex. I just want to fuck you right now."

They sat quietly for a while, then Dana spoke up again.

"I think Deb knows I am doing something with you."

"Why do you say that?"

"I forwarded the emails you sent with the babysitter videos in them and forgot to strip your email address out of one. I think she saw it before I hid it and opened the link."

"Did she say anything?"

"No. She wouldn't."

"Okay, but if you have to tell her, I don't mind. Just try to keep it quiet and not get to anyone else."

"Yes, sir." She snuggled closer. "I don't want to lose my lover when I just started."

John liked the sound of that. He pulled her close. "Me neither."

They were sitting there recovering, John in just a shirt and Dana completely naked when there was a knock at the door.

-- And the story continues

John quickly moved to put his pants back on and dressed himself. Dana grabbed her clothing and moved to the kitchen to stay out of sight. John then moved to the door.

When John opened the door he was quite surprised to see Dana's friend Debra standing there. Deb was a cute, pixie of a girl who probably stood about 5' tall. She was a petite brunette with a great lean shape and enough tits and ass that still showed she was a girl. He took in what she was wearing. It was yoga pants and a t-shirt that was long enough to go to the center of her ass. He couldn't tell if she was wearing a bra.

"Hello, Debra. How are you?"

"Uh -- hello Mr. T. I'm fine. I was just looking for Dana."

"What makes you think that she's here?"

She smiled a small, shy smile and looked down to the floor. "Uh -- she told me to meet her here."

"Well," was all the start of a denial that John could get out before Dana made herself known.

"Hi, Deb, come on in." Dana walked up next to John. "Let her in, Mr. T."

John turned to let her in and when he did he gave Dana a hard stare. Dana just grinned.

"Hold on just a second." Dana grabbed Deb by the hand and led her to the kitchen. She was in there a couple of minutes and then came back, alone. John looked at her questioningly.

"Come over to the couch, Mr. T." She led him to the center cushion of the couch by his hand and he sat. "I haven't told you something important Mr. T. so I misled you a little. I need your help." She stood in front of him in that outrageous outfit and he hoped he could be logical and not think only with the small head. "I invited Deb over here today so that she could be with us and become comfortable with a real cock." John's eyes opened a little in surprise so Dana smiled. "You see, Deb was almost raped about a year ago by a date and has been wanting to get over it, but it's hard for her. She needs some help with somebody safe and reliable. I think it's you."

"So you want me to do what?" John was trying to figure out how far this would go.

"I just want her to get comfortable seeing and touching a man. Is that okay?"

John's little head was screaming "Yes!" but he tried to be rational. "Are you sure this is okay and that you are alright with her being here with us? You sure you want to share me?"

Dana smiled and leaned over and kissed him. "Yes, I'm sure, Mr. T. This is for a very good cause."

"Okay."

"Good, take off all your clothes and sit back down."

How could John refuse that? So John stripped as Dana disappeared back into the kitchen. He shook his head at such a turn in luck. Just last month he was bemoaning his lack of sex and female companionship. Then he thought he was pushing a youngster into having sex with him and it turned out she was working to have sex with him. And now she had brought her friend over for what, physical sex counselling? He was sitting there nude for about 60 seconds before they came back. Dana led Deb back into the room and Deb grinned as she saw John naked.

When they got in front of John, Deb tried not to stare at his cock -- unsuccessfully. Dana stripped off her clothes and Deb stared at her. "What are you doing?"

"I like being naked here. Mr. T. and I go naked a lot." Dana said that like she was ordering a soda it was so matter-of-fact. She knelt in front of John and motioned to Deb to do the same. "You can't get a feel for it from up there." They both giggled at her pun.

John just sat and waited to see what happened. He couldn't get over the fact that there were two 18-year olds kneeling in front of him, getting ready to play with his cock. He looked down at the voluptuous Dana as she smiled at Deb and reached for his cock. Dana's tits always drew his eyes. The petite Deb just stared at Dana's hand as Dana reached to grab him.

"Well, Deb, this is Mr. T.'s cock. What do you think?" Dana held it up as it hardened into an erection at her touch and the stare of the two teenagers. No problem getting another erection with these two at his feet!

Deb glanced up at John before answering. When they made eye contact, John smiled and nodded. "It's, well, it's cool. I've never been able to just sit and look at a live one; you know, inspect it and study it. It seems nice size, too."

Dana grinned up at John. "Of course. I told you it was a nice cock. Now, I am going to stroke it a little and then you can do it." Dana started stroking and John was in heaven at the thought of the two girls using him as a test subject. "You see how I'm doing it? Just stroke it lightly and use the light friction to stimulate it at first. You only get to the point of squeezing it harder and pulling the skin back and forth when they get ready to cum." Dana kept stroking and John stared at the way the two youngsters were so focused on this cock.

Deb looked up at John. "Can I try it Mr. T.?"

John nodded. "Of course. Just follow Dana's lead." Who would say no to that?!

Dana smiled at John. "Okay, put your hand on his cock." Deb reached out slowly and wrapped her hand around the base of his cock. "

Deb leaned forward. "I've always wanted to do this; just lean forward and look at a live penis from up close and check it out." She glanced up at John and he just grinned.

"I don't mind." No fucking way did John mind a cute little thing like that checking out and investigating his cock. She was about 12 inches away and studying it closely. She turned it this way and that as she inspected it.

Dana looked up at John and then at Deb. "Around here, we just call it a cock. And I think you are going to love playing with it as much as I do." She grinned at John lewdly.

Deb continued to stare and run her hand up and down John's cock. "Yes, I think I am. I think you and Mel have made me relax enough to be able to do this. After Jake tried to force me, I was a little afraid." She looked up at John. "I had to go to a counselor to be able to talk about that and that it was all his fault. He's just an asshole."

John looked directly back at her to make a point. "Yes, he is. Sex is a great thing and two people should both want to have and enjoy it or else it's no good for anyone. You just take all the time you need."

Deb raised her eyebrows, finally understanding something. "Yeah, I guess you don't mind having two young ladies playing with your cock." She emphasized cock, showing that she got what Dana was saying.

John chuckled. "Why would I?"

Deb turned back to the task at hand. "I like his balls, too." She grinned up at John as Dana chuckled. Deb played with his balls with her left hand while she stroked him with his right. She moved slowly up and down and John was loving it.

Dana finally leaned in close. "Yeah, but what I really like is sucking his cock. It's so much fun. I can play and suck on it and no matter what I do, he just moans and loves it. I'm totally in charge when I have his cock in my mouth." And with that, Dana leaned forward and put her lips over the head of John's cock. He took a deep breath and she sucked on his last three inches for a few seconds while Deb held it up by the base. John just took deep breaths and enjoyed having a teenager suck his cock.

Dana pulled off with a pop and gave another dirty grin. "Yum. I just love cock." When she looked at Deb she could see the conflict there. "Don't worry Deb, you don't have to do that right away. Just relax and take your time. You can do that next time or the next." She gave John a conspiratorial look at that. She had already invited Deb to come again. What a little minx!

Deb looked up at John and then at Dana again. Finally, she leaned over and lightly kissed the head of John's cock. He watched closely, enjoying the fact that this was the first cock she had ever pressed her pretty little red lips to. She left them there for a couple of seconds and then pulled back about 6 inches. She stared down at the one-eyed snake and then leaned over and put her entire mouth just over the head. She just cleared the mushroom part of the head since John was circumsized, and then licked with her tongue along the bottom. She pulled back quickly and looked at the two of them. She blushed. Yes, she actually blushed. "Wow that was really cool."

John agreed. "Yes, it was. I enjoyed it a lot."

Deb looked at John quizzically. "Why is it that young boys are in such a hurry to cum? Why does it take a few years to have patience?"

John shook his head. "It's a hormonal, biological, and experience thing. When it's all brand new, it's very exciting to a young man and that adds to the hormonal arousal. Together those mean that his senses are completely overloaded. Mother nature is really tough in this area. After a few times, they do get better and some also realize how important it is to take care of the woman, too."

Deb shook her head slightly up and down. "I guess that makes sense. But how long before you cum?"

Deb was still lightly stroking his cock and John shrugged. "Well, I have already cum once today, so the second one may take some time."

As soon as he said that, Deb's head swiveled toward Dana and she gave her a slightly mocking scolding. "You little slut, you've already fucked him today, haven't you?"

John noticed that she certainly didn't talk like she was all that innocent. That must be because they have been playing and studying videos for a while.

Dana nodded. "Oh, yes. When I showed up like this and did my little baby-sitter routine, Mr. T. fucked the shit out of me bent over the arm of this couch."

Deb gave her a light punch on the arm. "You little slut!"

Dana shrugged. "What can I say? I love sex, I love cock, and Mr. T. here has a nice one. He's also older, experienced, and a very nice guy. That means he gives me great orgasms."

Deb stared at Dana. "Wow, you really do love this."

"Oh, yeah. Right Mr. T.?"

John decided to give Deb a little dirty talk. "Yes, it appears so. I'll tell you Deb, I've slept with a lot of women over the years and Dana is already one of the best. She is a very fast learner when it comes to sucking cock, she has a great tasting pussy and ass, and her pussy is so tight it milks the cum from my balls. Plus, she has some things that many do not. A desire to be the best and an imagination to make things interesting."

Dana beamed at his praise.

Deb just seemed to stare at him for a few seconds. Then she came out of it. "I want to learn how to suck cock and fuck, too." she almost seemed competitive about it.

John just sat there in awe. These two beauties were going to kill him if this kept up. And heaven forbid the third one of the Weekly Masturbation Group should come over, too.

Dana finally leaned toward Deb. "Okay, here's what I have learned." She pointed to the underside of John's cock, just under the head. "I don't know what this is called, but cocks are very sensitive here. Cocks love the feel of your lips sliding up and down over them because it's just like a tight pussy, but the feeling of your tongue here really gets them going. Right, Mr. T.?"

"That's correct." He stared at the two of them as Dana used him for a training prop. He could put up with being a prop for any young ladies that Dana wanted to bring around.

"Since Mr. T.'s cock is nice and fat, you may have to work hard to open your mouth wide enough for him. You are very petite, but you can try. If you get it in there, keep your hand around the base unless you are into gagging, like we saw that one porn star do the other night." Dana looked up and winked at John. Deb just stared at his cock.

And then she dove down onto John's cock, taking the part exposed above her hand, about 4 inches of it, and began bobbing and at the same time licking the bottom of his cock. John stared wide-eyed at Dana because of Deb's history and how this happened. Dana just smiled and put her hand on the back of Deb's head.

"Do you want him to cum in your mouth, Deb?"

Deb rose up off John's cock. "No, I don't think so."

Deb sat back and Dana grinned. She reached out and grabbed John's cock. It was so blood engorged that it was looking a little purple and the big vein that ran along the side and top was standing out. "I know what to do with this."

Dana stood up and pushed John's legs together. Then she turned around, her back towards John, straddled his legs, and hovered over his cock. "Are you ready for some hot pussy?" She gave Deb a wink and a dirty grin. Deb smiled and stared.

"When am I not ready for your hot pussy, you little sex fiend."

Dana chuckled. "I guess I have become one, haven't I?"

And with that Dana reached between her legs and guided John's cock into what really was a very steamy, hot, and wet pussy. She eased herself down onto it and moaned. She finally got fully seated and leaned back against John.

John had watched, almost in awe, at how open and sexual this young woman was considering she just started having sex. He put his hands on her hips as she sat down on his cock and her moan triggered one of his own. When she was seated she leaned back against him and he put his hands on her tits and spread his legs, which spread Dana's wide open.

Dana could see Deb staring at where her pussy was impaled on John's nice cock. "Like the view?"

Deb blushed a little. "Yes. It's just like all the porn that we watch with Mel, only live and better."

Dana started bouncing up and down on John's cock. She closed her eyes and moaned. "God, I love sex so much. I didn't know how much until I started fucking John. It's amazing."

Deb continued to stare. She could see how Dana's inner lips clung to John's cock as Dana rose up, and then how her pussy seemed to hungrily swallow it back up. She could feel a tingling in her own nether regions as she watched. She wondered what it would feel like, to be bouncing up and down on a real cock. She had used the dildos that Mel kept and she liked that. She really liked it when Mel ate her pussy and she had tasted Mel's, too. And now, watching this live show her pussy was getting really wet. She decided that she really liked watching Dana get fucked and she wanted to feel that, too. Deb finally reached down and rubbed her pussy through her thin yoga pants while she continued to watch from about 2 feet away as Dana's pussy was pierced by a nice cock. She was horny as fuck. She finally looked up and found Dana was staring at her.

"Why don't you take them off so you can get to your hot, wet pussy."

Deb took a quick breath at the way Dana said that, but had to admit that it was true. She was very turned on and she knew she was very wet. She could see John looking at her over Dana's shoulder as he continued to fuck her and feel Dana's big tits. Oh, fuck it! They were naked and fucking and she had sucked John's cock. She and Dana had arranged all this so that she could see what sex was all about and get over her near rape at the hands of some misogynistic asshole.

Deb stood up and shoved her yoga pants and thong to the floor in one quick motion. She kicked them to the side and went back to her knees on the floor.

"The top, too. It's too hot in here for clothes." Dana pushed her again.

Well, that's what she was here for, so Deb ripped her t-shirt off over her head, revealing her small b-cup tits. John stared at them and Deb blushed a little again.

"Beautiful. You are a beautiful woman, Deb."

Deb smiled at John's words. She really needed that ego boost right now. Dana - voluptuous Dana with the round ass and big tits that the guys always stared at, was fucking right in front of her and she felt a little left out.

Dana and John were fucking pretty well now and Deb continued to stare. Finally, Dana put her hand out toward Deb, asking for her hand, as John continued to thrust up into her. Deb reached out and took the hand. Dana smiled and pulled it toward where she and John were coupled. Deb let her. Dana pulled Deb's hand up against John's balls and Deb knew what Dana wanted. When Dana let go, Deb started feeling John's balls. It was an odd feeling as she felt how they were a little pulled up toward his body. She stared at them as John stopped moving and just helped Dana bounce up and down on his cock. Deb then moved her hand up and felt his shaft and Dana's pussy as it banged into her fingers. She looked up at Dana and Dana nodded. Dana seemed to know what she wanted to do, so Deb did it.

Deb moved forward and brought both hands to work. She put one hand on John's balls and continued to feel them and the bottom of his cock. She put her other hand on the top of Dana's pussy and worked Dana's clit.

"Oh, god, that's so good." Dana threw back her head and moaned. She was in heaven and just kept her eyes closed and her head back as she bounced up and down on John's cock and Deb rubbed her clit.

Dana's eyes popped wide open when she felt the first flick of a tongue on her pussy. She looked down at Deb and Deb was licking the two of them from John's balls, up his shaft as it appeared, and over her very stimulated pussy.

Deb looked up at her, saw her looking, and winked.

"Oh, fuck, I'm going to cum." Dana was on overload now. John was pinching her nipples, fucking his nice cock into her pussy, and Dana was licking and sucking on her clit. "Fuck! Here it comes!"

Dana's entire body jerked and she let out a grunt. It did so a second time, a third time, and even a fourth time before she seemed to settle down to small movements and finish off her orgasm. John had still not come, but was close.

Dana was leaning back against John and catching her breath. She leaned her head forward and looked down at Deb. "That was fucking fantastic, Deb. I didn't know you wanted to lick my pussy, you little slut." She grinned and glanced back at John.

Deb was still only about a foot away from where John and Dana were coupled. She looked up at Dana as she said that and sighed. "I've been wanting to do that for a while at Mel's."

"Well, thank you." She turned again toward John. "You ready to cum, you teenage slut fucker?"

John smiled. These two had been watching a lot of porn and seemed to love the dirty talk. He didn't mind. It turned him on to no end to have these teenagers, so young and new to sex, talk dirty to him. "Yes, I'm ready to cum, you teenage slut."