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.
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-- 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.
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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 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."
