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

After a quick nosh, the two naked girls dressed and left. John sat at his kitchen table after cleaning up and thought about where his life had gone over the last couple weeks. Hell, when he was young he would have read something like this in some adult magazine and thought that it was all made up for the magazine. But now he was living it. Maybe this really did happen more than he knew.

John closed up the house and relaxed in front of the TV for a while. It was a tiring day. He had cum three times for the first time in years. Whew! These girls were going to be the death of him.

John went to bed, reliving in his head all the things he had done today. He almost got an erection, but just let himself drift off to sleep.

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On Tuesday, Dana begged off to get everything she wanted to get done for college prep. She felt she had to prepare some shopping lists, start planning her packing, and everything else. John kept thinking that it might be a bit early, but at least she was doing some planning.

John was waiting for her on Thursday when he saw her enter her house from school. He went and sat down, grinning at his luck and looking forward to a little sex. Pure sex was something he had never really done with anyone. He had always started a relationship before progressing to sex, so that part of it was new to him. So he waited, well, not too patiently, but he knew that they had time.

Meanwhile, Dana was up in her room pulling things out of a couple of shopping bags. She and Deb had been watching more porn on the net and were planning another fun day for John and themselves. They found the role playing as much fun as John did.

Dana put on the white shirt that she had bought. It was perfectly tight and she could only button it up to near the middle of her tits. It pushed the rest of her tits up and together. She grinned at her reflection in the mirror. It was hot. Next, she pulled out the plaid, schoolgirl skirt that they sold in the mall for the private, Catholic school attendees. She pulled it up. It was small and way too short. But not short enough so she folded the waistband over a couple of times and turned around. Her nice plump ass was barely covered by the shortened version. She bent over a little and watched over her shoulder as the bottom of her bare cheeks started peeking out. She shook her ass a little. John was going to love this. And she was going to love it when he lavished attention on her and fucked her silly. Damn, but she really loved showing off to him.

When the doorbell rang, Dana rushed downstairs and let Deb in. Deb came in wearing jeans and a t-shirt and carrying another shopping bag. They ran upstairs to Dana's room to finish getting ready. Dana pulled a matching schoolgirl outfit for Deb from her shopping bag and Deb stripped and got ready. They were both in the outfits with no bra or panties and turned to face the mirror side by side. They grinned at each other.

Deb reached over and slapped Dana on the ass. "John is going to love the way that skirt bumps out and frames that plump ass. I think he's in love with your ass." Then she pointed to Dana's tits. "And those tits would give any man a hard-on in two seconds. John won't be able to keep his hands off them."

"That's the point." Dana then reached over and grabbed Deb's ass. "And you look like a delectable piece of jailbait."

Deb grinned. "Yeah. If I went out like this, every underage girl pervert in the county would pay attention and get a fucking boner."

Dana turned toward Deb. "And don't think that John doesn't like your tight little body and ass. Now let's get out what you got at the adult store."

Deb grabbed her bag from the bed and upended the contents. There were two dildos, two small vibrating eggs, two sets of butt plugs, and two small bottles of lube. Each set of butt plugs came three in a package of increasing size.

Dana giggled and reached for the butt plugs. "I knew you were going to get the butt plugs, but this other stuff -- wow! It's great stuff." She checked out the other items while she held the two sets of butt plugs. "Vibrating egg?"

Deb giggled and put her hand over her mouth for a second. "Yeah, the woman at the adult store recommended it. She said she loves it."

"Well, that will certainly be interesting." Dana held up the plugs. "Now, let's get ready for John and to get really fucked." After some trying she finally ripped open the packaging and set the two sets down on the bed. "Fuck, the plastic they put things in nowadays you almost can't open!"

Dana immediately bent over the bed. "Do me first."

Deb grabbed the smallest plug from one of the sets and stood behind Dana. She reached for a bottle of lube and ripped off the cellophane covering. Deb opened it and looked down at Dana's ass. Her asshole was readily visible and her pussy lips peeked out just below it. Her ass was plump and fleshy. Deb gave it a quick slap and Dana jumped. Deb chuckled and then dribbled some lube on her ass crack just over her asshole. Dana trembled a little at the drips of the cool liquid.

Deb took the plug and ran it all around the lube that was slowing running down Dana's ass. She used her left hand to capture some that was starting to run all the way down Dana's pussy and rubbed it back up and over Dana's asshole. Dana moaned so Deb slowly worked a well-lubed finger in. Dana arched her back and moaned more.

Deb pulled out her finger and centered the slick butt plug on Dana's asshole. Then she pushed. Dana tried to relax and Deb pushed hard enough to get the plug past the largest part. It slipped into Dana's ass and the flat end came to rest up against the hole. Dana groaned.

"Wow, that feels weird."

Deb slapped Dana on the ass again. "It looks super-hot." She ran her hand over Dana's ass and wiggled the butt plug. That made Dana jerk and she took a quick breath.

Deb laughed and then patted Dana's ass. "My turn."

Dana stood up. "Oooh. It feels even weirder to move around in it." She walked back and forth. "And walking is really strange. It's actually a little stimulating to think about having something in your ass as you walk."

Deb lay on the bed on her back and, being the flexible dancer that she is, pulled her legs back and hooked them under her arms. She had exposed her entire crotch. She framed her ass with her two hands. "I'm ready."

"Nice view." Dana grinned at Deb and slapped her pussy lightly.

Deb flinched. "Hey! If you're going to play with it, then play with it, otherwise, stick that butt plug up my ass, bitch."

Dana laughed. "You are turning into such a slut."

"Me? Are you kidding? You're the one who seduced the older man next door and are coming up with all these ideas for role playing."

"Shut up!" Dana said it good-naturedly and slapped Deb's pussy again. "Get ready, slut."

Deb grinned. "I'm ready. I've been wearing a small one off and on for a week, so use the middle size. I want to be able to be fucked in the ass."

Dana shook her head. "And I'm the slut?"

Deb stuck her tongue out at Dana as Dana retrieved the middle size from one of the sets. She looked down at how Deb's pussy was opening up, the outer lips just barely parting, but already showing some wetness. Her asshole was nice and pink. Dana picked up the lube and squirted some directly on Deb's asshole as she held her left hand, the one with the plug, just under Deb's asshole. She rubbed it up and around Deb's ass, which caused Deb to smile and squirm a little.

Dana then worked her index finger into Deb's ass. It went in pretty easily. She wiggled it a little, eliciting a moan from Deb, and then removed the finger. She lined the plug up with Deb's asshole, lightly touching the pink ring. "Ready?"

"Fuck, yes." She took a deep breath.

Dana pushed on the plug and it went in easily until the widest part. Then she had to push a little and Deb pushed back to get it to go in. When it reached the widest part, her asshole seemed to just swallow up the rest and it seem to get sucked right out of Dana's hand and into Deb's ass. Dana leaned back.

"Wow! Your ass really wanted that plug."

Deb grinned. "I love it. I walked around for about 30 minutes with the smaller one in my ass and it felt amazing. You're going to love it. It was also exciting when I looked around and realized that nobody knew. I was walking around and nobody knew that I had a plug up my ass and was so wet it almost showed on my jeans."

Dana laughed at Deb. "See, you are the slut." She picked up her cell phone. "Now, let's tell Mr. T about our little game."

She typed in a text and hit send. "Let's go."

John was sitting on his couch and wondering what was taking so long when his phone buzzed in his back pocket. He took it out and saw he had a text. It was from Dana. He opened it and was floored.

"Mr. Principal. I am sending Dana and Deb to your office for punishment. They have dressed and acted in a most unladylike manner. They are dressed inappropriately and the boys in the class cannot stop making rude comments. Please discipline them in any manner you feel necessary."

John grinned. Really? They were coming over as two schoolgirls being sent to the principal's office. He couldn't wait to see what they had cooked up now.

Suddenly, there was a light rapping at his back door. He got up and went to see the two youngsters there in their outfits. He was hard instantly.

He steeled himself to be what -- tough? Hard-nosed? A disciplinarian?

He opened the door. "Please come in ladies." He waved them with his hands. He couldn't help but notice Dana's big tits pushed up and out to put them on display for him. Then, as they went past him, he stared at their legs and barely covered asses. Fuck, these two were hot!

They stopped once they were in the kitchen, so John moved to the front. "Please follow me ladies."

He led them into the den. He pointed to the area in front of the couch. "Stand here." They stood directly in front of the couch. He sat down in the middle of it. "One of the teachers tells me that you are dressed inappropriately and behaving unladylike. I can already see the first is true. Now stand there while I consider punishment."

They stood there, grinning, trying not to, but failing.

He looked them up and down slowly and deliberately. "Dana, your shirt is entirely too small for those big tits. No wonder the boys were making rude comments. They can't help but stare at those full, beautiful tits. I bet all the boys got erections what with how teenage hormones rage. And you are both wearing skirts way too short. Turn around." They did so. From his position, John leaned over and looked up under them. The cheeks were almost visible without doing so, but looking under the skirts, he found that there didn't appear to be anything at all under them.

"Dana, are you wearing any bra or panties?"

"No, sir."

"Deb? You?"

"No, sir."

"Bend over and touch your toes." The two girls obeyed immediately. John was amazed as he found himself staring at two gorgeous 18 year olds bent over. The skirts hiked up over their delicious asses. Dana's was round and plump, Deb's tight and bubbly. He could see their pussies between their legs and most interesting was the flat portion of butt plugs up against their assholes.

"You two are complete sluts. You have worn white shirts too small for your tits, skirts too short for your asses and pussies, and to top it all off, you have the audacity to wear butt plugs to school! No wonder the teacher was appalled."

John stood up behind them and placed a hand on each ass. "Now, ordinarily I would send you to detention or suspend you. However, since you are about to graduate and colleges have been known to change their acceptance of individuals who are suspended for being sluts, I am thinking of giving you two a break. But I think we have to have something for you to do for you to make amends. Do you two find that amenable?" He grabbed and wiggled the two butt plugs and elicited a sharp intake of breath from each of them.

"Yes, sir." The two of them answered almost unison.

"Stand up and turn around." The two stood up and turned toward John. "Now, Dana, what do you think that means?"

She grinned at John. "Sir, I think that means you want us to have sex with you."

"I didn't suggest that at all. But since you brought it up, why don't you tell me what kind of sex you had in mind. I need you to be specific. Dana?"

"Sir, I want to suck your big, hard cock and then have you put it into my tight, little pussy."

"I think we can arrange that. Deb?"

"Sir, I want to suck your big, hard cock and then have you put it into my very tight and very hot little asshole."

"Mmmm. I like the way you two sluts think. I think I can live with this kind of punishment. Now, unbutton your shirts, but leave them and the skirts on. I'm going to let you girls fuck me like you just said."

As they unbuttoned their shirts, John took off all his clothes. He sat down on the middle of the couch. "Now, Dana, I'm going to let you suck my cock just like you said you wanted." John gave her a sly grin and waggled his cock with his hand as Dana knelt in front of him. "Oh, and since you want me to fuck your tight, little pussy after you suck my big, hard cock for a while, I want Deb behind you getting you ready." John turned to Deb. "Suck and finger that pussy to get it nice and wet."

"Yes, sir."

John looked down as Dana put her right hand around his cock.

"You looking forward to your naughty schoolgirl student sucking your cock, Mr. Principal?"

"Absolutely. If you do a good job, I'll let you come back and do it whenever you want, as least until you graduate."

Dana bent and took about half John's length into her mouth. He just watched in awe at the sexual playfulness of these two young things. Was he teaching them anything? Or were they both just using each other for sex?

Dana took half John's cock and then pulled back a little and licked around the head. She was finding that she loved the effect it had on a man when she was sucking his cock. She felt like she had complete control of the situation when she was sucking cock. She licked all around and then went down to kiss and suck on his balls. It was at that moment that she felt Deb start to lick her pussy. It felt wonderful to have someone eating her pussy while she was sucking cock and she moaned. She was looking at up John and saw him also react to her moaning and applying vibration to his balls. Then she felt her ass being fucked by the butt plug. This was heaven.

Deb stared briefly at Dana's beautiful pussy before leaning in and licking it. She loved eating pussy, and Dana's shaved slit was delicious. She had only eaten two, but the way Dana shaved her lips and tasted was better than she could have imagined before eating pussy. She parted Dana's lips, ran her tongue through the gash, and flattened it to go up and over her butt plug. But that was in the way so she pulled on it and fucked Dana's ass with it briefly, watching her ass and pussy both pulse in reaction to that. But she wanted to lick her ass, too, so she pulled it all the way out and laid it aside.

John loved this entire idea and stared at the two role-playing schoolgirls. Could it get any better than this?

But John knew he wouldn't last long at this rate so he had to stop it. "That's enough of that, you beautiful little cock-sucker. I need that tight, little pussy."

Dana pulled off his cock and Deb rose up to her knees. Dana put her hand on her pussy and smiled at John. "You mean this tight, little pussy, sir?"

"Oh, yeah."

Deb smacked her lips. "It tastes delicious, too, sir."

John laughed and patted his cock. "Climb up here and get on board."

Dana stood and then climbed up onto John's lap. She turned and looked over her shoulder. "Deb, hold that cock up and guide it into my pussy."

Deb reached under Dana and grabbed John's cock. She loved it. Okay, it was her first, but she had seen plenty in professional and amateur porn and had also done research. She knew there were larger cocks out there, but John's was almost 7" and pretty fat. It filled up her little pussy just fine. And there was no way she was going to get a porn cock into her ass. She was even a little concerned with getting John's in there, but she was so turned on, she knew she was going to try.

Deb watched as Dana lowered her pussy onto John's cock. She aimed it right at Dana's very wet pussy and Dana sank down onto it. Deb held onto John's cock until Dana's pussy hit her hand.

Dana moaned. "Oh, yes, I love fucking."

John laughed. "Me, too, but I especially love fucking you two."

Dana started moving up and down, sliding her pussy up and down John's cock. She put both hands on his shoulders and threw her head back. "Fuck yeah."

John just held her by her hips as he fucked up into her. He was enjoying that and then he felt a tongue. Deb's tongue. She was licking his balls and he could tell that part of Dana's excitement was that Deb was licking up onto Dana's ass and probably working on her asshole. Then it was confirmed when Dana stopped for a second, leaned forward, and moaned. Deb was licking her. John held her still by her hips and fucked up into her a few times. Dana started moving quicker then and she started to grunt as he fucked her. She was going to cum.

Dana could feel it building. Deb had started licking the two of them and as she tongued Dana's ass, Dana ramped up to her orgasm quickly. She stopped and enjoyed the licking for a second and then John held her still and fucked up into her. Oh my god! This was fantastic. She held back as long as she could, letting John fuck her while Deb licked her ass. Then it was there.

"I'm cumming -- fuck!" Dana convulsed once, twice, and then just slowly jerked as John slowed his fucking and Deb stopped licking her. She finally collapsed against him, fully sated.

John felt all her muscles contract as she jerked under him. It was a miracle that he didn't cum when her pussy pulsed on his cock. He was just relaxing a little when he felt Deb licking his balls.

"You'd better not do that too much or I'll fill Dana up with cum."

Dana giggled. "I can't go around with cum running down my leg, sir. Deb, you'll just have to take the first load orally." She winked at John and lifted up enough for Deb to pull his cock out of her pussy.

"Yum." Deb pulled his cock out and ducked as Dana swung one leg over her to get off John's lap. Dana sat next to John to watch and talk about this.

Deb looked up at John and Dana with John's cock in her hand, smiled, and started licking and sucking. Dana decided to narrate and help John get off.

"She's such a cute little thing. And it appears that she really knows how to suck cock. She's only ever sucked one live one, yours sir. But she has practiced on some dildos." She reached down and put her hand on the back of Deb's head. "Now, Mr. Principal, be a good disciplinarian and give her the cum she wants, that she desires and needs. Cum in the mouth of the cute little 18-year old who just loves sucking your cock." John was getting ready. He really needed to cum, but was enjoying all this attention so much that he wanted to hold off.

John decided to talk to Deb. "What a good little slut. Suck the cock of your school principal so that you can get out of trouble. Suck it and I'll reward you with some delicious cum, too." John was ready now and got ready to blast her mouth with his spunk. "Oh, yeah. What a good little slut. Suck that cock, baby. Suck it good. Oh, fuck. Here it comes." John arched his back and then came. He thrust into Deb's hot little mouth again and again, shooting her mouth full of cum. She sucked and swallowed like she had been doing it for years. He was surprised because he felt like he dumped a quart of cum into her.