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 two stories
John had a bachelor party that was supposed to just be a poker party with some friends, but his old buddy Bob invited his significant other Candy and her friend Jasmine to arrive late. Candy was a former stripper and Jasmine had performed with her and was still stripping. They provided more entertainment than was planned and John called to make sure Sherry was okay with these strippers fucking the guys who stayed. A couple guys left, not wanting to violate their marriage vows for a quick fuck.
Jake, one of the guys who stayed, called his wife Gabriella. Gaby showed up and joined in. It seemed that she and Jake liked to play around. When the party was over, John went next door and Gaby followed. He found out that Gaby had been to Sherry's house before she came to the bachelor party and had made an agreement with Sherry. The agreement was that she owed Sherry a good time for partying with John. John, Sherry, and Deb all partied with Gaby while facetiming with Gaby's husband, Jake.
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It was the Friday before the wedding between John and Sherry. They were just having a small ceremony performed by the local judge on Saturday at 4pm. They were relaxing on Friday, neither one having to work that day, when they got a call from Bob's girlfriend, Candy.
Apparently, the strip club where Candy and Jasmine had taken Gaby for practice was having their amateur night that night. Candy knew someone who worked there and they had taken Gaby there when it was closed to teach her how to use the pole and work with the customers. They wanted us to come down and be there to see her and vote for her. There was a cash prize, but they just wanted her to feel like she could win. Bob, Candy, and Jasmine would be there and they wanted a couple of others who knew Gaby.
John looked at Sherry. "You okay going to a strip club?"
Sherry looked a little thoughtful. "Well, you know I'm not afraid of sex and I like sex with women, too, so I won't be shocked by it. I've just never been to one and only know anything about them through what they show in movies. Are they any real indication?"
"Well, I haven't been to one in a few years myself, but if I remember correctly, movies don't really capture everything. You'll see. There are some that are very nice, the girls are excellent, and they know how to tease. That's all it is, really. But there are also places where they let the girls get away with providing a little extra in the private dance areas. I've seen them offer blowjobs and even a quick fuck for a few hundred dollars."
Sherry looked thoughtful. "Hmmm. It sounds like they are probably pretty desperate for that money if they offer sex in that manner. It's certainly not fulfilling. Well, anyway, I say we go and have some fun."
John grinned. "If you insist. We'll have to see if Gaby is offering any extras in the private areas to her close friends."
Sherry slapped John on the arm with a chuckle. "Oh, stop it. You can fuck her back here if you really want to. I enjoyed her last time, too. We are just there to support her tonight."
John nodded and agreed.
At about 8pm, John and Sherry headed for the club. The competition started at nine.
In the club, Gaby was sitting in front of one of the mirrors in the stripper's dressing room, getting ready. Candy and Jasmine were applying her makeup to make it visible in the low lights of the club. They had already been through her training on how to dance on stage, how to use the pole, and how to perform lap dances. Now, they were just giving her last-minute instructions as they got her ready. There were ten women performing for the amateur night competition. She had drawn number eight.
When John and Sherry arrived, the place was not packed, but pretty full. There were more women than they thought they would see and they took a place not far from the stage.
About that time Candy came bouncing out from the back, literally, as her voluptuous body was packed into a tight top and pants. She came over and sat at their table.
"The show will start shortly. There are ten women here for the amateur night and Gaby is number eight."
Sherry leaned over closer since she was on the other side of the table and the music was loud. "Are there always this many women here? It looks like 15% of the clientele is female."
"No, never. There are always a few around, but on amateur night it seems like the amateurs performing always try to get some friends out for support. That's who most of them are."
Sherry nodded and sat back.
John leaned over and asked about Bob. Candy explained that he was called in to work on a job he was consulting for.
They all got drinks and then Jasmine also came out to join them. She just grinned and gave everyone a thumbs up since the music was so loud.
At 9pm the dancing started. The first three girls were a little skittish, as was expected, but they did strip down to their g-string and dance around displaying themselves. The fourth girl was excellent. She knew how to dance, use the pole, and tease the men at the railing. Evidently, the group of three girls and one guy sitting over to the left of the stage was her support group. They cheered and yelled for her above everyone else. She grinned and was really good at playing up to the crowd.
Fifth through seventh were again skittish. Many of these young ladies looked like they were probably just old enough to dance. They were between eighteen and twenty years old. But Gaby was next and she was no novice. She was a sexual being who loved everything about sex, so John was expecting her to be good.
John was wrong. She was amazing. Gaby danced around, taking off her top, spinning on the pole, and doing the moves that everyone in the club, especially the men, loved. She bent over away from the crowd and ran her hand up between her legs and over her barely covered pussy. Her string was extremely light and thin. She lay on her back, raised her legs up in the air, and parted them back and forth, slapping her heels together at the top. Her pussy was almost visible and she was loving the attention. The crowd had been told from the beginning to cheer for the amateurs and the crowd roared its approval for her. She finished with a flourish and left the stage to deafening cheers.
The last two women could not compare to Gaby and at the end, Gaby was declared the winner and called back on stage to accept the winner's check. Gaby appeared in the g-string and a gauzy, transparent kind of wrap. She accepted the $300 check to applause and grinned. Suddenly, Gaby took the check and put it on the floor, reached for her g-string, which she pulled off and quickly over her stripper heels, and tossed it into the audience. The guys around where it landed fought for it more than any group of women had ever fought for a bouquet.
With that she disappeared into the back and things started settling down. After about a minute, the DJ announced a name and one of the regular strippers took the stage to work. The amateurs started making their way out of the back and most of them met their supporters and left the club. A couple stayed and partied and number 4 stopped when someone asked for a lap dance to do so. Gaby finally came out and came straight to our table.
Gaby immediately went to John and sat on his lap.
"Hello, Mr. T." Gaby grinned and was acting playful.
"Well, hello to you, too."
"Do you want a private dance in the back?"
John was surprised by this and looked around at the others. He was not sure they could hear, but he figured that they would definitely understand if he went with her. He looked up at Gaby. "Well, what is it going to cost me?"
"Private dances are $25 per song. In your case, I'll give you 5 for $100."
"Not giving me much of a break, eh?"
"Well, that depends on what happens when we get back there."
"What does that mean?" John was fishing for information.
Gaby put her chin in her hand like the famous Thinker sculpture. "Well, I need your beautiful fiancée to join us and make me do whatever she is willing to pay for."
John looked over at Sherry. She was watching the current dancer, who was working the pole very well. Then he looked back at Gaby. "What are the prices?"
"For $50 I'll eat her pussy or suck your cock. For $100, I'll fuck you, but for $200 I'll eat her pussy while you fuck me." Gaby grinned at that.
John reached over and tapped Sherry on the shoulder to get her attention. She leaned toward him. "Gaby is offering us the chance to buy some dances in the private room. What do you think?"
Sherry looked at Gaby and grinned. "Gaby, you need to look over there," and Sherry pointed to a table near the stage. "That guy over there has your g-string and is waving it towards us." They could all see that the guy was waving it and trying to get Gaby's attention. "I want you to go over there and offer him the blowjob option while I take my fiancé home and get ready for my wedding tomorrow, okay?"
Gaby grinned and leaned forward, putting an arm around John and Sherry both. "Okay. I understand. You guys make a great couple. Just go home and get ready for your big day. I'll go take care of the panty-man."
Gaby got up and headed that way and Sherry asked John to take her home.
When they got home, Sherry asked John if they could go to his house. John agreed, knowing that Dana was home from school for the wedding. He didn't know if Sherry preferred not do anything while Dana was there tonight or if she thought Dana and Deb might be having their own fun.
When they got up to John's bedroom, Sherry quickly undressed and got into bed. John thought that a little unusual since she normally liked to play a little or do a teasing strip tease before getting into bed.
John undressed and joined her. As soon as he was in the bed, Sherry rolled him onto his back and cuddled up to his side. John could tell that there was something on her mind. He could not think of anything except maybe cold feet or nervousness about the wedding.
"The wedding scaring you?"
Sherry looked up. "What? No. That's not it. I have been thinking about something over the last few days and now I need to discuss it with you."
"Okay."
"You never had your own children and I'm only just turned 37, so I can still have children. Do you want one?"
John was a little stunned. He was totally blindsided by this. He had not even thought about it. He was 47 and would be retired by the time a child got out of college. "To tell the truth, the thought had not even entered my mind. I guess I thought that that was all over with. I was getting too old to have children."
Sherry smiled and put her head on John's chest. "No, actually, you are not. I am almost too old and there are some risks, but I want to have your baby. Do you want that?"
John lifted her head up and leaned down to kiss her. "I would love to have a baby with you. That's an amazing and generous idea. Thank you."
