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. It's morphed, after some reader comments to where John is living with the mother of Dana (the former 18, now 19 year old next door neighbor). Sherry is a voluptuous beauty who was a teenage mother. So she's still younger than John, and knows about him and Dana and, even better, approves of their relationship. She feels that as long as Dana is in charge of and exploring her sexuality, then she has done what Sherry could not.

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- From the last story

John and Sherry had a discussion about relationships where John recognized that he was a little jealous of Sherry going out and that he was in love with her. He decided that he was going to propose. He did and she accepted. John had invited some friends over for a poker party as his bachelor party, but no women. However, Bob, his friend who was living with an ex-stripper and who had had a threesome with John and Deb, had secretly invited his ex-stripper girlfriend, Candy, and her stripper friend, Jasmine, to show up unexpectedly. They were going to fuck everyone so two guys left, being decent about their wives and their marriages, but one invited his hotwife, Gaby, over. She joined in and fucked John in front of her husband and seemed to enjoy teasing him about fucking John while Candy gave her husband a tit-fuck.

When it was over, Gaby went with John to Sherry's house and there John learned that they had met and made a deal. Here is how the last chapter ended.

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The two of them headed next door and although he had permission to enjoy himself, John was concerned about what would happen.

The two of them traipsed up to the front door and, even though he had a key, John knocked. They waited only a couple of seconds before Sherry opened the door in a nice, fluffy robe. She looked at the two of them and stepped back. "Please come in."

Sherry stood back and John let Gaby go first and then followed. They went into the living room and then Sherry came round in front of them. John held his hand out toward Sherry. "Gaby, this is my fiancée, Sherry. Sherry, this is Gabriella, Jake's wife, who goes by Gaby."

The two shook hands and seemed to size each other up, Sherry in her robe and Gaby in her coat.

Suddenly Sherry broke into a grin. "Did you fuck John?"

"Oh, yes. John was quite a good fuck."

John looked at the two of them questioningly. "Did I miss something?"

Sherry went to him and snuggled up against him. She smiled up at him. "After Jake called, Gaby actually was just a few blocks away shopping. She drove over here and came and discussed it with me. We came to an agreement. She undressed here and, in case you hadn't noticed, is wearing one of Dana's sexy little G-strings."

John looked over at Gaby. She opened her coat and flashed them the panties. "Oh, I see that they are a skimpy pair, but I did not know Dana had a pair like that." He looked back at Sherry and she was grinning. "Wait, what was the agreement?"

"As payment for having fun with you, she has to come over here and make it up to me."

"Wow! Can I watch or take pictures?"

Sherry gave him a playful slap on the chest. "Silly, she's going to make it up to me with you there. I told her she had to take care of all three of us."

"Three?"

"Well, I couldn't leave out Deb, right?"

John looked down at Sherry. "God, I love you woman. How did I get so lucky to find someone so open minded at my age."

Sherry leaned up and kissed him. "I love you, too. I got lucky as well. You are a compassionate, loving, tender man who truly cares about people. If we have sex with others, that's just for fun and doesn't change our love." She leaned against him.

Gaby watched and shook her head. "You guys are great together. Now, the night's not that late and I'm still horny. Shall we adjourn to someplace more comfortable?"

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Sherry grinned at her and nodded. "Let's go to the bedroom with the King sized bed."

Sherry dropped her robe to reveal she was only wearing a thong, like Gaby. Gaby then dropped her coat to be only in her thong and followed Sherry as she headed for the stairs. John was in heaven.

They all went up the stairs to the bedroom. Sherry led the way, followed by Gaby, followed by John, who was staring at the ass candy in front of him. He couldn't resist reaching up and grabbing a handful of Gaby's ass. She stopped quickly and stuck it out. It almost hit him in the face, so he leaned forward and buried his face in her crack, licking along the thong. She giggled.

Gaby pulled away and they went into the bedroom. Deb was there, reclining in the chair, also in nothing but a thong, texting on her phone. She looked up. "Are we ready?"

Sherry looked back at John and Gaby. "Yes, we are." She turned to Gaby. "Do you have an iPhone with Facetime on it?"

"Yes, why?"

"We're going to call your husband and I'm going to narrate as we ravage you."

Gaby groaned. "Oh my god, he will absolutely love that."

"Well, you told me he really gets off on seeing you with other people, so I'm going to show him how we take advantage of his wife and make her our personal slut."

"Sounds goood." Gaby grinned and ran back downstairs naked. She returned after a few seconds with her phone. She held it up. "Okay, how do you want to do it?"

Sherry went to the bed and lay back, sitting up against the headboard. She pulled her legs up, raised her knees, and let them fall open, spreading herself wide open. One leg fell to the bed and the other she lef drape off the side at the knee. "Deb, plug her phone in to that really long charging cord so that it won't go dead and so that it will reach everywhere." Deb quickly did that. "Now hand me the phone. I want Gaby on her knees eating my pussy, I want you lying next to Gaby playing with her tits, but lying on your side with your pussy up here near my head so that I can show it to Jake. I want John standing next to the bed with his cock ready for Gaby to suck." Gaby gave the phone to Sherry.

Sherry then handed the phone to Gaby. "Call him and then hand the phone back to me and be ready to start eating my pussy. Just wait until I tell you."

Gaby poked at her phone and dialed her husband on Facetime. She handed the phone to Sherry, who took it in her right hand and took her left and put it on Gaby's head, grabbing her by the hair. When Jake answered, Sherry grinned and said hello. "We just wanted you to be able to enjoy your wife's ravishment. Do you want to see that?

"Absolutely," Jake said excitedly.

"Did you know Gaby was such a slut that would fuck men and women when you got married?"

"No, but it became apparent pretty quickly. She is insatiable. I love my fucking slut and we have a lot of fun with others."

"Okay. You ready?" Sherry grinned into the phone.

Jake said he was, so Sherry switched the camera to use the lens on the other side. She looked through it and then started narrating.

"Can you see my pretty, little pussy, Jake? Your wife's face is just above my delicious tasting pussy. Gaby is going to show you how much she loves my pussy." She pushed on Gaby's head and Gaby connected with Sherry's pussy and started licking her.

"I'm so wet, Jake. She is going to love eating that tasty peach I have." Then Sherry used her left hand to pull Gaby up. She came up like she was disappointed to be taken from that tasty pussy.

"Look at that pout. I think your wife loves my pussy, Jake." Sherry paused and looked up at me. "Now John is going to come close enough to allow your wife to suck his cock. It's almost as delicious as my pussy."

John pushed up against Sherry's draped leg and his cock appeared just to Gaby's right. Gaby moved her head over there and started sucking on John's nice fat cock. She slurped away until Sherry pulled her off.

"Well, Gaby? Don't my pussy and John's cock taste great?"

Gaby stared into the phone. "Yes, they do. I made a promise to come back here before I came to the poker party, Jake. I had to come back here and eat this delicious pussy and suck this tasty cock. I'm sorry, but I'm such a slut." She said that with a grin.

"Yes, you are an insatiable sex loving slut. Now do what they tell you." Jake's voice showed that he loved this whole thing. Not that anybody cared about what he had to say. We were here to fuck his wife, no matter what.

"Back to my pussy, slut." Sherry pulled Gaby back down. "Get your fingers in there and work to make me cum. I want to cum, you little bitch."

Gaby went to town on Sherry's pussy, licking her lips and clit while she slowly inserted two fingers into Sherry's very wet pussy. Sherry then panned over to show Deb. "Oh, and Jake, we have a cute little submissive who lives with us and she is playing with Gaby's tits. Check out the cute little pussy on this 19-year old." Sherry let the camera linger on Gaby's pussy while she took her left hand off Gaby's head and ran a finger up and down Deb's slit.

Finally, with John standing there watching and Deb playing with Gaby's tits while Gaby ate Sherry's pussy, Sherry came. "Oh, fuck, here it comes, Jake. I'm going to cum on your wife's face. Get that clit, you slut. I'm gonna cum!!"

And Sherry did. She bucked under Gaby's hard work, the licking and finger-fucking keeping her going until she had had enough. John wondered if Jake could see much the way she was thrashing around with the phone, but he surely got the idea.

Finally, Sherry pushed Gaby away and collapsed against the headboard. "Jesus, I want you to come eat my pussy a lot."

Gaby just grinned and licked her lips.

Sherry pulled her right leg out and rolled over to put her feet on the floor. She got up and pointed the phone at the bed. "Now, Jake, my other two fuckers are going to enjoy your little slut. Gaby, lay down on the bed."

Gaby lay down, her nice tits bouncing, and pulled her legs back.

"Okay, slut, you've got two more to satisfy. John, get up here and fuck this cunt."

John climbed on the bed and put his cock on her pussy. He slapped it against her slit, stimulating her clit with it and eliciting a moan from her. Here pussy was already very wet. Sherry kept filming and leaned in closely for a shot of John slapping his cock on her pussy.

"Deb, sit on her face and pull her legs back so John can fuck her hard."

Deb crawled up over Gaby and Gaby stared up at the cute young pussy that was descending on her face. Deb leaned forward and grabbed Gaby's legs, which were already held up a little, by the ankles and pulled them back. John shuffled forward to fuck her.

John slowly started slipping his cock into her very wet pussy and Gaby groaned into Deb's pussy as she started licking. She was really into it.

"Look at your slutty little wife, Jake. I'm surprised you can keep her home. She likes pussy and cock so much and you only have one of those. Look how she likes licking Deb. That young pussy is really good. And look at John. He's burying that nice, fat cock into that cunt. He's longer and fatter than you are, so he may be ruining her pussy for you for at least a few days. You'll have to wait for it to tighten up to get a good fuck out of this slut." Sherry chuckled at her teasing of Jake.

John was pounding her pretty hard and Deb was getting close to an orgasm. Gaby was definitely doing her job.

"Oh, I think Deb is going to cum on her face, Jake. Check it out. Go ahead, Deb, cum on her face. Let her feel you cum as she eats that pretty pussy. John, you need to hold off until after Deb gets off because I want to show Jake what a cum-sucking cock-sucker he married. She's going to suck you dry after she gets Deb off."

Deb was close. "Oh god, eat my pussy. You are a wonderful pussy-eater. Oh, fuck." Deb tilted her head back and groaned. "Cumming..."

Deb thrashed around as she came, riding Gaby's face hard, enjoying every second of her orgasm. John was slowly fucking Gaby now and watching Deb. Her chest and face suddenly became flushed and she slowed her humping of the face under her. She finally collapsed off to the side onto the open part of the bed. Sherry was still filming.

"Wow, Deb really enjoyed riding your wife's face. I think she is going to have to come over here so that we can all take turns sitting on her face. She could become our personal little cunnilingus toy."

Gaby groaned at that and closed her eyes, enjoying John's fucking.

Sherry got closer to Gaby's face and showed Jake how wet it was. "Yeah, your wife loves having pussies coming all over her face. Just look at those juices all over her." She then panned down to where John was fucking her. "And it looks like John might be getting ready to cum. He's going to make your slutty, little wife suck his dirty cock and swallow all that cum."

John pulled out of Gaby as she lay there on the bed and got to his feet to stand alongside it. He was ready to cum.

"Get down here on the floor slut. My fiancé needs to cum in your pretty, little, cock-sucking mouth. I don't want a mess in here. You still watching Jake?"

All that was heard was a mumbled "Fuck yeah!"

Gaby followed the directions and knelt in front of John, his cock pointing at her face as she stared at it. It was a loaded gun and ready to go off. John had not touched his cock since he pulled out of Gaby, so it was soaking wet with, mostly, her juices. Gaby started to reach for it, but Sherry had other ideas.

"No hands, slut. Just lean forward to lick and suck that deliciously wet cock."

Gaby leaned forward and started sucking and licking John's cock. She slurped it loudly to make a point and then went to town bobbing up and down. John put a hand on the back of her head and started a fucking motion.

"Oh, yeah, that's it John. Fuck that slut's face." Sherry put her hand on the back of Gaby's head and helped. She kept the camera close to where her mouth was sucking John's cock.

"Oh, fuck, here it comes!" John reached down grabbed his cock to jack it as he spurted. Gaby just sat back on her heels in that well known baby bird pose with her mouth open, waiting to be fed. And John did. His first spurt was well directed into Gaby's mouth, but then his knees buckled just a little and he lost control of his aim. His second and third spurts went over her mouth and across her face, painting it with his thick cream. She just sat there as he finished by putting the rest into her mouth. Gaby waited until he was done and then started swallowing. She swallowed it all, smacked her lips, and then leaned forward to clean off his cock.

Sherry laughed. "Well, Jake, you certainly have one cum-loving slut for a wife. I can see why she's out fucking around. She probably drains you dry. One man cannot provide enough spunk for this bitch." She paused as she continued to show Gaby enjoying her post blowjob swallowing. "Well, I think that's enough for tonight, Jake. We'll send your wife home tomorrow morning when we're done with her."

They heard Jake murmur goodnight and then it was quiet. Sherry grinned at everyone else. "John, you should probably head home and make sure Bob and his stripper sluts are okay. Gaby will sleep here with me and Deb."

John started getting dressed. "Okay. What time for breakfast tomorrow?"

"I would say that 10am should be early enough for that."

"Okay, we'll come over at 10." He walked over and kissed Sherry.

Sherry grinned. "You are so lucky."

"I really am."

She kissed him again. "So am I."

When John got home, everything was quiet so he went to bed.

Sherry let Gaby get cleaned up with a quick shower while Deb went to bed in her room. Then Sherry invited Gaby to sleep with her. Which was good, because when she woke up Sherry found that she must have been dreaming something sexual because she was soaked. She started to lightly brush her fingers over her nipples and pussy at the same time. Gaby was awake, too.

"Do you want me to eat your delicious pussy again?"

"God, yes." Sherry threw off the covers and lay back, opening her legs. Gaby crawled between them and licked her to a very nice orgasm. Then they got ready to go downstairs.

The next morning, John woke up at about 8am. That was late for him, so he hurriedly showered and dressed. He was just dressed and coming out of his room when he ran into Bob, Candy, and Jasmine coming out of the guest room, still wearing night clothes. Bob was in a pair of shorts and a t-shirt while Candy and Jasmine were in just long t-shirts, at least as far as John could tell.

"Morning." Bob grinned. "Nice party." Candy and Jasmine giggled.

"Yes, it was." John looked them over. "We are invited over to Sherry's place for breakfast at 10. Why don't you guys get ready and we'll head over as soon as you come down."

Bob nodded. "Okay, good. We'll get cleaned up and be down in a little while." He gave John a grin. "Should we save ourselves for some fun?"

"I don't know. Everyone may be a little tired. But don't expend too much energy so that you have plenty there, if needed."

"Gotcha." The three of them returned to the room.

John went downstairs and watched some news until they came down about 45 minutes later. It was 9:15 now, so he decided they should head on over.

When they arrived, Sherry and Deb were dressed, sitting at the kitchen table and talking. Gaby was standing by the stove cooking what looked like scrambled eggs wearing nothing but an apron. She had a very nice ass.

John went over and said good morning to Gaby. "Good morning, slut." He put his right hand on her ass and his left turned her head so he could kiss her. She kissed back. "I see they have you still dressed in nothing."

Gaby smiled. "Yes, of course. I agreed with Sherry on this."

"Does she have other plans for you this morning?"

"She said no. She just wanted me to stay naked as a display of the fact that she owns me until I go home to my husband this afternoon."

"Okay." I continued to fondle her ass until Dana walked in.

"Hey, don't fuck with the help until breakfast is served."

"Is she available for breakfast, or after breakfast?"

Sherry grinned at me. "No, I think we should send her home. We had a lot of fun last night, but she should head home after breakfast."

John gave her a mock salute. "Yes, ma'am."

They all had breakfast, enjoying the vision that was Gaby serving them while naked. There was some grabbing and fondling of her, but she was mostly left to just serve as eye candy. Bob, Candy, and Jasmine were going to leave after breakfast as well.

The group was having a discussion and John had stopped Gaby next to his chair so that he could run his hands over her thighs and ass and across her pussy when Bob brought up an interesting idea.

"You know, sometimes Candy and I join Jasmine back at one of the clubs where they used to dance, to participate in an amateur night. I think next time you should bring Gaby along and see how she does on the stage and doing lap dances."

John looked up at Gaby. "What do you think?"

Gaby seemed to mull it over. "I don't know. I've always loved having sex, but never considered doing something like strippers do on a stage." She turned to Candy. "Could you guys give me a quick course before we go?"

Candy nodded her head. "Oh, yes. We can do that and give you some pointers on what and what not to do with the customers, too."

"Okay, I'll run it by Jake." With that Gaby started clearing the table and everyone else just discussed the topics of the day.

John, however, grabbed a few plates and followed Gaby into the kitchen. He walked up behind her, put his hands at her waist, and then ran them up under the apron to her tits. She moaned and John started playing with her nipples. Gaby stopped working on the dishes and put her head back on his shoulder. John grinned.