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(s), so I just took the name "Lolita" from the Nabokov novel.

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- From the last story

John went to meet Sherry and Dana at their house where Sherry had made it clear to her daughter that they would not be sharing John. Sherry was teasingly agreeing and packing to go visit her college with her newly found grandparents.

Deb had followed John into Sherry's house and was a little down at both the prospect of her best friend going off to college and the loss of her first real lover, John.

Sherry sensed all this and, as a complete surprise to John, brought Deb into her bed and then had John join her. They all had fun and Sherry could sense that Deb was a little submissive, so she used that to have her service them and told her that Deb could only use John's cock with Sherry's permission.

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The next couple of weeks were easy for John and Sherry. They were both busy, but had a chance for some good sex, including a little play with the impressionable Deb. Deb had mostly been busy with her parents going on a short vacation and getting ready for her local community college. It was now coming up to the first weekend in October and John and Sherry were getting ready for parent's weekend at Dana's school.

Deb couldn't go, and was a little upset, so Sherry promised her a night with John when they got back. She promised a night alone for the young girl to enjoy sex with her first real lover and the guy she had always had a big crush on. She also promised a night with Dana and John over Christmas. Deb couldn't keep her smile off her face at that one.

So John and Sherry packed and headed to the school to see Dana. John waited for Sherry to say something - anything - about the situation with Dana. Instead, she seemed relaxed and playful to John. He tried to shrug it off and enjoy the ride, but he was still a little concerned about being in the room together with the two of them.

When they arrived, they had arranged to meet Dana at the hotel where they were staying, which was right next to the campus. They got checked in and were settled in the bar when Dana arrived. She had in tow a small, beautiful, blonde girl who was on the edge of womanhood, as was Dana. She was petite with the slim, athletic body of someone who took care of herself.

Dana ran to her mother and gave her a big hug. "Mom!" They hugged and giggled. Then Dana turned to her friend. "And this is my roommate, Jean."

Sherry shook Jean's hand and Dana gave John a big hug. Then John shook Jean's hand. He noticed that she give him a shy grin and blush a little. Shit! Did that mean that Dana had said something about their relationship?

The four of them went into the restaurant and had a quick lunch. Sherry was very interested in all the things that Dana and Jean had to say about their first few weeks of class. They were energetic and giggly as they described everything. It was easy to see how excited and into their classes they were. Everything was new to them.

John and Sherry also found out that Jean was a gymnast. John's cock jumped at that, his fantasies from when he was young resurfacing. He had always wondered about how many positions they could try with the flexibility they had.

After a couple of hours of catching up and talking and eating, they all strolled over to their dorm room. It was pretty small for two, but they were loving their space and had decorated it nicely. When they all got there, Dana was showing it off and she jumped back on her bed.

"And this is my bed." She grinned and when she jumped up onto the bed on her ass, her momentum carried her all the way onto her back, her skirt flying up and showing her brief thong to the entire room. She laughed and pulled her skirt back down.

Sherry rolled her eyes. "Nice show, slut."

"Hey!" Dana protested good-naturedly.

Jean just giggled.

"Okay, let's see the rest of the campus and then we'll head back to the hotel."

So the group strolled the campus, taking in the fall blooms and still green areas. It was well maintained, as were most nowadays. Well maintained grounds was a selling point for all the schools.

After all that, everyone was tired. Sherry and John went back to the hotel and the two teenagers returned to their dorm room. When they got back there Sherry turned to John.

"So what do you think about Jean?"

"She is very cute and will be gorgeous soon. She'll be a beautiful woman."

Sherry looked at him funny. "Dana tells me that she's a virgin."

John's head shot up and he looked at Sherry. "Wow. Okay, now that was either a very odd random thought or you have something on your mind."

Sherry grinned. "Well, as you have noticed with Deb, I love young fresh teenagers almost as much as you do. I didn't have much sex for a few years and I've loved getting back into it. And when I was speaking with my daughter, Dana asked me to see if we wanted to introduce Jean to the male member, so to speak."

John laughed. "As much as my male member would love to be introduced to some more teenage pussy, do you think that is a good idea?"

Sherry shrugged. "Dana admitted to me that they had already had sex, the two of them. Evidently, Jean is very open to almost anything, but couldn't really get into it at home. Anyway, Dana let it 'slip' that she had been introduced to sex with a man by you, and that you were very good and very attentive. She said that Jean just about choked on her food that they were eating at the time, but then the other day brought up the subject again. She said her sister told her to find an older man for her first foray into sex because they were better than any college boy. So she asked Dana, not very subtly I might add, if you could be her older man."

"And Dana said what?"

"She said you were a horny old bastard that would love to fuck another teenager."

"Gee, thanks."

Sherry laughed. "Just kidding. She told Jean that she would check, but she was sure she could arrange it. You see, she knows about us and Deb."

"Shit."

"Well, I guess it was inevitable. They were - are best friends and there's no way we couldn't keep them from discussing it."

"You seem okay with it."

"I told you before that I'm actually glad that my daughter is in charge of her sexuality and not letting it be dictated by a man. I want her to be in control of her own sex life. As long as she does things that are safe and consensual, I'm all for it."

"Well, she seems to be in charge. And you are more open-minded than most of the women I've met."

Sherry stopped and looked at John. "There are many younger women who hold my point of view." She gave John a nasty grin. "You're just getting old."

"Fuck you, slut." John stuck his tongue out.

"I'm all for that."

John and Sherry unpacked and before they could get to "that", the phone rang. It was Dana. She and Jean were downstairs and wanted to come up.

Sherry turned to John. "You ready to deflower another teenager."

John's eyes went wide. "Now?"

"No time like the present. They're on their way up."

John hesitated. "Are we really going to do this?"

Sherry grinned. "Not me, you." She pointed at John and then laughed her way over to the door. John ducked into the bathroom to pee before they came in.

When John came out, Sherry and Dana were in the far corner of the suite, discussing something in whispers. It seemed very private.

Jean was standing in the middle of the room and turned to look at John. She smiled, blushed, and looked at the floor.

Sherry and Dana finished their conversation and came over to John. Sherry was grinning and Dana was practically jumping for joy. John was concerned.

"Okay, here's the deal." Sherry took a deep breath. "I know what we have discussed about you and Dana, but in this case, I have to make an exception. She wants to be with you and Jean to show her the ropes since they are already lovers and Jean will be more relaxed with Dana. So Dana and Jean will have sex with you and I'll go down to the bar and have a drink or two. They'll call me when they are done."

"I'm glad you guys settled that. I wouldn't want to have any input into that decision." John was a little sarcastic.

Sherry looked at him. "And are you saying that you do not want to have sex with Dana and Jean."

"I didn't say..."

"Good." Sherry interrupted him before he could say anything else, putting a finger on his lips. She grinned. "I'll be back when they are done." Sherry turned to the two youngsters. "Now girls, please take it easy on the old man, he's getting along in years." She turned and stuck her tongue out at John.

John shook his head. "How did it come to this?"

Sherry just waved and left. Dana walked over to John. "Mr. T., let us undress you. I want Jean to see what that's like."

John smiled. "Okay." Well, that was not going to be difficult.

Dana led Jean over to John. "Just relax, Jean. Start with his shirt." Jean looked at John sheepishly and started unbuttoning his shirt. John just grinned. Dana knelt and untied his shoes so he toed them off.

With his shirt unbuttoned, John shrugged it off and then pulled his undershirt over his head. Dana pushed on his stomach. "Sit back on the bed, Mr.T." John did so. Dana grinned. "Now, let's take off his pants and see what he's hiding under there for you to play with."

Jean undid John's belt and pulled it out. Then the two of them undid his dockers and pulled them down and off. He was left laying back on the bed with tented boxers. Dana grinned and Jean stared.

"See?" Dana reached out and grabbed John's cock. "I told you it was a nice one."

Dana looked at Jean and the two of them grinned and reached for the two sides of his boxers. They grabbed and pulled and yanked them over his erection, causing it to slap up against his stomach before coming to rest at a 45-degree angle from his stomach.

Jean was captivated and looked at it carefully. Dana watched her for a few seconds and then looked up at John. He was watching Jean and Dana grinned and winked at him. "Go ahead and get closer, Jean." Dana gave Jean a little shove in the back. "Check it out."

Jean knelt between his legs and stared at John's erection. She seemed mesmerized.

"Here." Dana took Jean's hand and put it at the base of John's cock. "Put your fingers around the base and feel how hard it is, but still has such soft skin." Jean did so and John watched as she felt her first cock. His cock throbbed under the ministrations of this first timer. It turned him on like it had the first time with Dana and Deb.

"I can feel his heartbeat in his cock." Jean looked up at him and grinned. It might have been the first time she had used the word.

"Now slowly stroke it." Dana knelt next to Jean. "Yeah, like that. Just go up and down lightly. Perfect. Now, the next step is licking and sucking. You ready to lick and suck a real cock?"

"Yes."

"Well?" Dana pushed on the back of Jean's head.

Jean leaned forward and took her first tentative lick of the underside of a cock. John just watched and Dana grinned up at him. Jean licked a couple of times and then moved forward enough to take the entire head into her mouth. She sucked lightly and Dana leaned forward to see better what Jean was doing.

"Good. Suck that cock, you little slut. I showed you how on that lifelike dildo we have. Now show Mr. T. how much you've already learned by sucking that delicious cock."

Jean started working on John's cock and he moaned and looked at Dana. "Your lessons have been effective. This little cock-sucker knows what she's doing."

Dana grinned. "Yeah, and I even have her eating pussy better than most. She's just great with everything." Dana patted Jean on the head. "You love my pussy, don't you slut."

Jean rose up off John's cock with a loud pop as she kept the suction strong. "Yes, I do. You have a delicious pussy."

Dana rose and stripped, her gorgeous curves coming into view. "Good. Now move out of the way and let me fuck John a little and then you can taste us both and clean my pussy juices off his hard cock."

Jean sat back on her heels and watched as Dana crawled up over John and guided his hard cock into her pussy. She was very wet already in anticipation of fucking John and watching her delectable roommate sucking his cock. She had seduced Jean immediately and had shown her how to eat pussy, suck cock on the dildo she had, and had gotten used to having Jean slowly eat her pussy every time she got horny. Jean was well on the way to being her sex toy.

Dana sat on the cock and moaned. "Stay back there Jean, and lick everything you can see." Dana leaned over and fed her voluptuous tits to John. She loved having her tits sucked and nibbled on.

John was more than happy to feast on the tits Dana fed to him. He licked and sucked as Dana rode his cock. She was doing that thing where women rotate their hips more than go up and down, fucking themselves with a cock and rubbing their clit as much as possible. It felt amazing to have her back on his cock. Then he felt Jean's tongue go around his balls and disappear up towards his shaft. He knew she got to Dana when she stopped rotating, leaned forward more and moaned.

Jean had licked John's balls, knowing that Dana had told her how to do that, but she was not a fan of balls. She loved the cock, and now she was zeroing in on Dana. She put her hands on Dana's ass cheeks and caused her to go still and lean forward. Jean pulled Dana's cheeks wide apart and licked from where John's cock was penetrating her favorite pussy, up over Dana's taint, and then circled that beautiful asshole with her tongue. She knew Dana loved this from their play. Dana was a bit demanding of her and Jean had fallen into a comfortable slightly submissive role. She loved playing with Dana and now Dana had provided a cock to play with and she was delighted.

John held Dana tight as Jean worked her magic. He slowly rotated his hips around ensuring that Dana had contact on her clit as Jean stimulated the already pretty stimulated young woman on his cock. Then he felt it as Jean worked a finger into Dana's ass. Dana threw her head back and moaned. She must have been really worked up because after only about two minutes of this, she suddenly started shaking and trembling and, at last, cumming. She jerked with each thrust of Jean's finger, which caused her to mash her clit on John's pubic bone, which caused her to jerk more. She came and came, like she hadn't cum in a while, until Jean pulled her finger out of Dana's ass. Then Dana collapsed onto John.

Dana couldn't stop cumming. Jean knew that she had edged every day for three days and that she had come to love anal play, so Dana knew Jean was giving her that big cum that she craved. And she really did enjoy this one. When Jean finally pulled her finger out of Dana's ass, Dana collapsed on John. She felt wonderful. She just wanted to lay there and cuddle with John, which she did for a couple of minutes, then she knew it was time to give Jean her first live cock.

Dana rolled off, John's cock coming free, covered in Dana's cum. Jean stared at it. "Wow, Dana, you really soaked his cock." Jean leaned forward and took a lick and smacked her lips. "Yummy."

Dana lifted her head, just now catching her breath. "Well, my little cum slut, clean it off."

Jean grinned and looked at John who had risen onto his elbows. She leaned over, grabbed his cock with two fingers, and engulfed as much as she could with her mouth. She sucked and licked for about 30 seconds then pulled off and looked at Dana. "Your cunt tastes delicious on a real cock."

Dana grinned. "Who taught you to be such a potty mouth?"

Jean smiled. "You did, you dirty whore."

Dana laughed. "Shut up or I won't let you have my pussy for a week." Jean pouted dramatically. "Now get up here on this bed and lay down. I'm going to have John pummel that pussy of yours."

Jean scrambled up onto the bed and spread her legs wide. She watched as John got up and stood between her legs. She stared down at the nice sized cock that was going to fuck her. She grinned and looked up at John. "Fuck me, John. Dana already got me ready for your big, fucking cock."

John smiled. Such beautiful playthings. They were so playful in the bedroom. He moved to put his cock into Jean. He put his hands on her thighs and pushed them back. Her ass was right at the edge of the bed, so he could stand on the floor and fuck her.

John centered his cock and rubbed it up and down her pussy. She was very wet and the head of his cock got wet instantly. He figured she was ready. He centered his cock on her pussy hole and pushed. Like a hot knife through butter. Jean moaned and John pushed until he was buried in her hot cunt. She was damn tight.

Jean threw her head back and groaned. She had been fucked by Dana's dildo, but this was real and it felt so different to have a man thrust his cock into her. She loved the feeling.

Dana watched and grinned. Her two favorite sex people were fucking. Well, she had to admit that she had to put Deb in there somewhere. She was a great, submissive little cunt who really knew how to lick her. Of course, Jean was such an attentive student that she was near the top as well.

John started fucking Jean hard. He put his hands on her hips and started thrusting, his hips slapping up against her ass.

"Oh, fuck. That's so good." Jean was bucking her hips as he thrust into her, enjoying the fucking. "Oh, god, I love fucking."

John kept fucking Jean and watching her writhe as they fucked. Then he watched as Dana reached down and started rubbing Jean's clit. Jean moaned and started bucking harder. John fucked her harder, the slapping sound echoing around the room. He felt a like such a stud. He had fucked Dana to an orgasm and he was fucking Jean there quickly and his cock felt like steel and that he could fuck all night. It was like it had gone a little numb.

Dana watched John fuck Jean and rubbed her clit. She wanted to Jean to cum hard and then get her to have her first swallow of cum. She leaned over and latched onto Jean's right nipple, sucking and nibbling while John fucked her and she rubbed Jean's clit. She could tell Jean would cum soon.

Jean's system was on overload. Her pussy was being drilled by a hard cock that filled her up and hit all the right places. Her clit was being rubbed and one of her tits mauled by Dana. Dana, the very sexy roommate who had introduced her to so much about sex. Oh, fuck, she was going to cum.

"I'm cumming!" Jean started thrashing under all the stimulation she was receiving.

John watched the cute young thing he was fucking cum and cum. Dana pulled off her tit and slowed her rubbing of Jean's clit. Eventually, as he slowed down, so did Jean. She fell completely limp after about 30 seconds of cumming.

"Fuck, now I know why people like fucking so much."

Dana laughed. "Yes, that is exactly why. Now rest for a second and get ready to get a cum shot. You have to get on your knees and suck John's cum-soaked cock until it explodes in your mouth. He's going to cum in your pretty mouth and after a couple of shots, pull out and paint your pretty little face. He's going to cum on your face like in the porno movies and I'm going to take a video on my phone for you to see and enjoy later. Got it?"

Jean looked up at John and his now very angry looking cock. It looked like it was looking for any orifice it could find to fill with cum.

Jean slowly got up and knelt before John. She looked up at him as she leaned forward and without using her hands lowered her mouth over his cock. She started licking and sucking.

John watched closely as this young thing sucked his very hard cock. It had collected so much blood that it felt like it was ready to burst. "You are very good at that for someone so young and inexperienced. It shows that you enjoy it."