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."
