Training Lolita Ch. 13

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The name of this story has nothing to do with the main characters names. The story is about a now 50-something guy having sex with then 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-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.


— From the last story

John and Sherry went to the strip club where Bob’s girlfriend Candy and her friend Jasmine worked. Gabriella (Gaby) was going to dance in an amateur contest and they wanted some friends present for support. Most of the amateurs were young and not bad, but Gaby was a little older, much freer with her body, and danced out of her mind. She won. They got married and the morning after the wedding, Sherry spotted her old friend Kim. Kim was with her when she was a young mother and sharing a place with a couple of friends while they all worked and went to school. And, apparently, they were lovers. Sherry invited Kim up to their hotel room and they had a terrific threesome. Finally, a couple of months after the wedding, Sherry announced that she was pregnant. John might finally get to be a father.


The baby was born in mid-October. The 16th to be precise. John was absolutely thrilled. He was finally a father. His first wife was pregnant when she died in a car accident but now he had a second chance. It was years later and it wasn’t until Sherry announced that she was pregnant that he realized how much losing that child had hurt and been a part of his life.

They got home three days later and settled in to life with a newborn. Which means no sleep, ridiculous hours, and all the things that come with a baby.

Sherry and John were exhausted. Dana was home assisting whenever she could get away from school. Things were hectic, but everyone was overjoyed at having the baby. It was a girl that they named Ann, after Sherry’s mother. Her parents had become a fixture in their life now, and was paying most of Dana’s way at college.

John was attending to Sherry and the baby one night a couple of weeks later, Sherry just finishing with breast-feeing, when she noticed his erection poking up his robe. They had not had sex for about 6 weeks and she was laying there, nude in their bed. She was actually pleased and complemented that John could get hard seeing her body even though she was still recovering from childbirth. She looked at his barely covered erection and then up at him. He was smiling.

Sherry grinned at him. “It will be a couple of weeks before my episiotomy is healed, so no sex for you, big boy.” Then Sherry thought about it and decided it was okay to do something about it. “Thanks for everything you do. I know you are still trying to do some work and take care of me and the baby.”

“You’re my wife and it’s my baby. How could I not help?”

“I love you, too. Now get out of here and send Dana in.”

“Okay.” John left and told Dana, who was home for a short time from college, that she was wanted.

John went and told Dana that her mother wanted her. She went up and visited with Sherry and then came back down.

“John, my mother wants to see you again.” John went upstairs while he heard her on her phone talking to someone.

Sherry was falling asleep when he went up and he just watched. He didn’t want to wake her. The feedings were so close together that she found it hard to get any real rest. He just sat and watched and admired his loving wife. She was beautiful, independent, strong, very adventurous when it came to sex, and a very giving person.

It was about 15 minutes later when Sherry stuck her head around the corner. “John,” she whispered, “come into my room in 5 minutes, okay?”

John just nodded and made sure that Sherry was still asleep. He waited a few minutes and then got up and went into Sherry’s room.

What greeted John there was a surprise. Dana and Deb were laying there on the bed, supposedly studying, wearing their dress-up for sex schoolgirl outfits. Both were lying diagonally across the bed next to each other on their fronts. They had books in front of them and their very short skirts were pulled up so that the bottom of both asses were on display. John stared and grinned. This was a setup and he was so horny that he wanted to just jump on one and fuck the living daylights out of her. He licked his lips and cleared his throat, trying to see which way they were taking this.

Sherry turned back. “Oh, Deb, here’s my stepfather. He can help us with this problem. He knows all about this stuff. Right, John?”

“What is it that you need help with?”

“Itchy pussy.” Sherry giggled and Deb laughed and wiggled bahis şirketleri her ass.

Both ladies rolled out of the bed, not bothering to protect their modesty, and then Sherry pointed at Deb. “Deb needs immediate attention. She has this itch. Can you help?” She grinned and pulled Deb’s skirt up so that her pussy showed.

Deb put her hand on her pussy. “I have a really itchy pussy. I play with it and stick my fingers in, but it doesn’t work. Dana tried eating it, but that didn’t work either. I think it’s much further up in my cunt. Can you help me, please?”

John got the idea. He had to guess that Sherry had put them up to this, once she saw he quickly he got an erection and not being able to take care of it.

“Sure, I can help. I will have to probe it a little and see what the problem is.” John dropped his robe and his half hard cock flopped out.

“Oh, Mr. Tilton, I really need to satisfy this itch I have in my pussy. Please use your probe to find the problem.”

John was amazed at the way these two thought up things to do with sex. He looked at Dana. “Dana, my probe is not quite ready to plumb the depths of her cunt. Please blow it up the rest of the way.”

Dana got down on her knees and took John’s cock into her mouth. She sucked and licked and in no time, his cock was hard.

Deb turned and crawled up on the bed. She lay down prone on her front. “Is this good, Mr. T.?”

John crawled up over Deb and put his cock in her ass crack. He started humping her ass. Dana crawled up alongside and lay on her front, as well.

Dana giggled. “It looks like he loves your cute little ass, Deb.”

John started moving back and forth. Dana leaned over and kissed Deb lightly on the mouth. “Now he’s humping your ass. Maybe if you get up on your knees, he’ll probe that itchy pussy and fix the problem. He is going to raise up off you and I want you to raise your ass up until you are on your knees. John is going to show you how he plumbs young, itchy cunts.” Dana turned to John. “Stepfather, raise up a little so that she can get up on her knees and give you good access to her pussy. I just shaved it yesterday and it’s smooth and sensitive. You should be able to get deep into her and fix that itch.”

John lifted up and sat back. Deb immediately got to her knees and looked over her shoulder. “Please probe me deep, Mr. T. Dana says you are a good prober and I need a good probe.”

John raised his eyebrows. “You two youngsters are very dirty, little girls.” He smacked both of them on the ass.

“Yes, sir.” Both replied, then giggled at their simultaneous answer.

John slowly slid his cock into Deb’s wet pussy. She was very wet. No telling how long they got themselves primed in here while waiting for him.

“Ummm, I think I know what the problem is with your itchy cunt, Deb.”

“What is it, sir?”

“It needs to have the scratch itched and some man ointment applied to it.” He chuckled to himself at the funny descriptions they were using for sex.

“Oh, please, sir, give me your man ointment.”

“I plan to.”

John started fucking Deb hard, grabbing her by the hips and plunging as deep as he could into her pussy. She was wet, hot, and loving it. She arched her back more to give him a better angle into her pussy. John was fucking her hard and decided to add something to the action.

“What about you, Dana. You have any itchiness?”

“Mother has some restrictions. I can play, suck your cock, let you eat my pussy, but no fucking. You’ll have to use Deb’s pretty little pussy, or her ass, for that.”

John ran his hand over Deb’s ass and pussy. “That is not a hardship. This is a beautiful ass and pussy, don’t you think, Dana?”

“Yes, I love it. I eat it regularly.”

John was fucking Deb’s pussy with long hard strokes and she moaned. “Well, then I think you need to crawl under her in the 69 position and I can take care of her itch and provide her the man ointment. However, we should not let any get on the bed or remain for too long. It can cause further irritation if you don’t clean it out.”

“Oh, goodie.” Dana scrambled to get into position.

John kept fucking Deb and she was groaning.

“Oh, Mr. T., I love your hard cock. You can take care of my itch anytime you want.”

“I’m going to do that.”

“Dana is a good cunt-licker, too. You guys are going to make me cum fast.”

“Go ahead and cum, baby.” John slapped her on the ass. “Your juices will make it easier for my man ointment to solve your problem.”

“Oh, yes, give me that man ointment. Fill me up, sir.”

Dana was under John licking them at their juncture and John hadn’t cum in over a month. He was ready.

“Here comes the ointment. I’m going to give it to your itchy pussy.”

Dana kept licking and sucking on the two of them. Deb was also close.

“I’m going to cum, too, Mr. T. Please give it to me.”

“Now!” John shouted and he started cumming into the youngster. She was cumming, too. The two of them were going bahis firmaları off. She was trembling and shaking and John was spurting and spurting.

When the two of them were done, John slowly started withdrawing from her. His cock was soaked with their combined juices. When his cock cleared her pussy, he leaned back and Dana immediately pulled Deb down to her mouth. She started licking and sucking and cleaning Deb’s messy pussy.

“Fuck, she’s good.” Deb was still sensitive and was therefore overstimulated by Dana’s tongue.

When Dana had gotten as much as she could, she pushed up on Deb and Deb rolled over onto her back next to Dana. Her pussy looked swollen, red, and wet.

“Yum. That was delicious, Mr. T. Come here and let me clean off your probe.”

John moved forward and fed his cock to Dana. She cleaned if off.

“I think my itch has gone away for a while.” Deb was slowly rubbing her pussy.

“I’m sure it has,” said John. “However, you may need daily injections of the ointment in order to keep it away. The injections can be administered to any of your orifices, as long as it is kept internally for a certain period of time.”

Dana grinned and stopped playing the game. “Mr. T., you were really funny with that probe and ointment shit.”

“Well, you guys came up with the itchy pussy idea.”

They both laughed and Deb said. “I always have an itchy pussy.”

John shook his head and finished getting dressed. “I need to check on mommy.”

He left and walked into the master bedroom. Sherry was awake and smiling. “From what I heard, that went well.”

John walked over and kissed Sherry. “Yes, it did. Thank you for that. I really needed it, and I hate the idea of masturbating with all these hot women around.”

“Well, you don’t have to. I will be able to fuck soon. I just didn’t want to give you a blowjob and get all hot and bothered and not be able to get off myself.”

“I understand. It was difficult, but I was able to take care of business with Deb.”

“Yeah, it sounded really difficult.”

John smiled and went downstairs to get something to eat.

Sherry had a doctor’s appointment the first week of December and when she came back, she was grinning from ear to ear. “Guess who got cleared for sex?” She was juggling the baby as she came in.

John looked up from doing a crossword puzzle. “Uh, I don’t know, Gaby?”

Sherry gave him a playful smack on the shoulder. “Smartass. I can have sex now, so you have about 15 minutes to get your ass upstairs and take care of mommy. Hopefully, Ann will sleep until you finish giving me, oh, I don’t know, maybe three or four orgasms.”

John stood up. “I’m at your command, m’Lady.” He bowed and waved his hand toward the stairs.

“Oh, I like that.” Sherry headed upstairs, the baby acting pretty well for now.

But the doorbell rang and she stopped halfway up, the baby still in her arms.

“I’ll get it.” John said, as if Sherry could.

John answered the door to find Sherry’s parents, Ann and Don. They had been travelling through Asia when Sherry had the baby and hadn’t seen it yet, so this was going to take a while.

They came in and, not even knowing the name since Sherry had kept it from them, they met Sherry at the bottom of the stairs and starting cooing over the baby. Sherry handed it to her mother and waited for her mother and father to both be examining the precious little bundle.

“Mom, Dad, I want you to meet Ann, your granddaughter and Mom’s namesake.”

Ann was now cooing and lightly crying at the same time as she held baby Ann.

Finally, they all sat down and John got everyone something to drink. The discussion centered about the raising of another daughter, considering that Sherry was almost 20 years older than the last time she had a baby. They discussed Dana and her relationship with it and welcomed me again into the family.

It was approaching 4pm now and the grandparents made their goodbyes and left. John looked over at Sherry, who started breastfeeding the baby. “Well, that was a cock block.”

Sherry laughed. “Don’t worry, as soon as we get this one fed, she’ll sleep for a while and it will be time for Mommy to get taken care of.”

“If you say so.” John grinned.

About that time the doorbell rang again. Sherry sighed. “Can we pretend we’re not here?”

John shook his head. “I can see Gaby through the side window and she can see us.”

John answered the door and Gaby rushed to Sherry and the baby to inspect them and pronounced them a beautiful mother and baby. They talked about the delivery and other things and then Sherry leaned over and whispered something to Gaby. She laughed. John frowned.

“What are you two scheming over there?” John asked.

“Nothing.” Sherry answered and Gaby just grinned. “We are going to go upstairs to put Ann down, she’s going out like a light now, and then we are both going to retire to our bedroom. You can stay here, you can come up and watch, or you can try to get kaçak bahis siteleri involved.” She stood and waved her hand at John. “Whatever.”

John grinned at that. He kept his patience and waited until he heard them get the baby down and enter his and Sherry’s bedroom. He restrained himself a little longer and then walked upstairs as calmly as he could. When he got to the bedroom door, he was greeted with one of the better views he had seen in a long time.

Sherry was on her hands and knees, her bare ass pointing toward him in the doorway. She had her face buried in the pussy of Gaby, who was lying back with her head on the pillow and had her hands buried in Sherry’s hair. She was looking at John and grinning.

“Fuck, John, she really is good at pleasing women.”

Sherry raised her head. “I’m good at pleasing everyone.” She looked back over her shoulder at John. “Now, get behind me and give me that cock. I haven’t had cock in a couple of months and I want it now.”

John grinned. “That’s one request I can gleefully fulfill. I’ve also been waiting for a couple of months to fuck my lovely wife and new mother.”

John was naked in seconds and Gaby pulled Sherry’s face back into her pussy. She was starting to moan and talk dirty to Sherry. She was a very dirty talker.

“Oh, yes, Sherry. Lick my pussy and suck my clit. I want you to make me cum. Then I’m going to watch your husband dump a load of cum in that cunt of yours and I’m going to suck it out.”

It seemed to spur everyone one. John had his dick in Sherry quickly. She was wet and ready, her incision healed and her desires very ramped up. Gaby, the slut that she was, was always into sex and ready to suck and fuck.

John started a steady stroking into Sherry as she ate Gaby. He was fucking her slow and deep, watching the ripples on her slightly larger ass as his hips slapped up against her. It was only about two minutes later that Gaby yelled she was cumming. Once she calmed a little from that, she slipped out from under Sherry.

“Let me see you two really fuck. I want to see you guys really get into it.” Gaby was apparently as much a voyeur as a participant.

John pulled out and slapped Sherry on the ass. “On your back.”

Sherry flipped over and threw her legs in the air, wide open. John settled in between. “That’s it my pretty wife. I haven’t fucked you in a while and I really need to get back in the saddle between those great legs.”

Sherry grinned. “Yes, John, make me cum, baby.”

John centered his cock on Sherry and slowly thrust into her again. She groaned. Gaby sat next to them and watched.

“It’s so good to have my favorite lover back.” John leaned over and kissed Sherry. Then he lay on top of her in the basic missionary position and gave her little thrusts. “You know that I love you more than anything.”

It had suddenly gotten serious. Sherry responded. “I have never loved someone like I do you.”

John kept thrusting. “I’m going to cum inside you my wife, my lover, mother of my child.”

“Yes, Yes, please do.”

Sherry started humping back and suddenly the spasms of her orgasm hit. It was enough to make John cum, too. It had taken all of about 8 minutes total. They were too hungry for each other and too overcome with the desire to again make love.

“Whew,” came from Gaby as they both relaxed, “that was very cool. You two were very into each other and it was really good to see a couple that in love.” Gaby patted John on the ass. “However, I still need to clean the delicious cum out of that delectable pussy, so roll over.”

John and Sherry both laughed and Sherry put her legs down so that John could roll off to the side. His cock came out of Sherry’s pussy with a wet smack. Gaby looked at the mess of the two of them and giggled. “Let’s see. What do I want first? The tasty cock or the scrumptious pussy.”

Sherry grabbed her by her head and shoved her toward her pussy. “Shut up and eat me, slut.”

Gaby laughed. “I beg your pardon. Are you saying that I’m a — well, okay, I’m a slut. But I don’t avoid it. I embrace my slutiness.”

“That you do. Now eat my pussy. I could use another orgasm.”

And Gaby did. She lay down between Sherry’s legs and began to lick and slurp on her wet, messy pussy. She licked and sucked and worked on getting all of John’s spunk out of there and then worked on giving Sherry an orgasm. Which she did.

“Fuck, here it comes,” was all that Sherry said up to her orgasm. She grabbed Gaby’s head and worked it all over her pussy as Gaby tried to maintain contact. Once Sherry relaxed, she flopped back down. “That was great. I haven’t had orgasms in a long time. Thanks, Gaby.”

John had been watching closely and rubbing his cock. He wasn’t hard yet, but a little chubby again. Gaby moved over between his legs. “Now, let’s see what we can do about this nice cock.” She got on her knees and looked up at Sherry. “Are you good for a while? Can I suck him off and get a fresh load?”

Sherry giggled. “You insatiable slut. Of course. I’ll be good for a while and then John and I can fuck for the rest of our lives. You go ahead and suck my man off. Oh, but remember, every time I let you suck him off, you have to give me two orgasms. Got it?”

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