Training Lolita Ch. 12

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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.


– 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.


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 almanbahis giriş 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 almanbahis yeni giriş 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.”


“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.”

Sherry put her head back on his chest. “Good. I haven’t taken my birth control pills the last three days in anticipation of getting that out of my system and having another baby.” Sherry giggled.


“Can you imagine what Dana is going to think? Her face will be priceless when I tell her that I’m pregnant. I can’t wait.”

John continued to stroke Sherry’s back while she lay against him. “Should we start now?”

Sherry raised her head. “Horny?”

“A little.”

“Good, let’s wait for our wedding night and enjoy it.”


They slowly relaxed and slept. John did wake in the middle of the night, thoughts of having a child running through his head. He was fine with the idea, but thought that maybe they should discuss the risks. He would have to remember tomorrow.

They woke on their wedding day and John didn’t get a chance to discuss the baby that morning. Sherry rushed home to get with Dana and make sure she could get ready in time. The wedding was being performed at the County Courthouse, so she was not wearing a typical wedding dress, but a nice beige cocktail dress. She was also going to have her hair and nails done this morning. She wanted to look good. After all, it was to be her only wedding. Her parents were going to be there, too. She was grinning as she got ready.

Dana was fixing breakfast when John came over to see how things were going. She was wearing only a pair of bikini panties and an apron. John whistled at her.

“Nice ass.” Dana shook it back and forth, the cheeks jiggling beautifully. John grinned and continued, “I can see a lot of your mother there.”

Dana laughed. “You pervert. Fucking both mother and daughter. I should’ve known with the way you introduced me to sex.”

“What? You didn’t like that method?”

“On the contrary. Deb and I both loved it.”

“If I remember correctly, you were practically begging for it and then you brought Deb into it.”

Dana smirked. “Maybe. But, since we are discussing these arrangements now that you are going to marry my mom, I think you and I should stop.”

John looked at her and nodded. “Agreed. I’ll miss that sexy body of yours.”

Dana grinned. “And I will miss the way you make me cum. Anyway, are you ready to marry my mom?”

“Yes, I am. Has she left yet?”

“Yes. She went to have her nails done in that strip mall just down the road and then to the shop next door to have her hair done. She’ll be back at about 2pm. That should give you plenty of time to get to the courthouse by 4pm.”

“True. Okay, I’m going to go get shaved and dressed. I’ll see you at about 3pm. We can all car pool down to the courthouse.”


As John left, he walked over to Dana, who had turned to face the range, where she was cooking some scrambled eggs. He reached around and put his hands under the apron to grab her tits. Dana was a little startled and jumped, but then settled down and let him grab and feel her tits.

“I just wanted to feel those wonderful tits one more time.”

“Any time you want. I just said I wouldn’t have sex with you.”

John smiled and shook his head. “You have turned into a first-class tease.”

“I learned it from you.”

“Okay, I have to go.” almanbahis John turned and left.

At 3pm, John returned to find Sherry, Dana, and Deb dressed and ready to go. They all looked lovely, but he was absolutely stunned by how Sherry looked. Her hair had been partially swept up away from her face, her makeup highlighted her features perfectly, and her dress made her look like a goddess.

“Wow! Gorgeous.”

“Thank you.” Sherry actually looked a little surprised by the complement.

“Let’s go.”

They all piled into John’s car and went to the courthouse. They were met there by Sherry’s parents and several friends of the two of them. They waited until it was their turn, went through the ceremony, and then walked down to the restaurant where John had made reservations for a quiet reception. There were only about 15 people and they enjoyed the menu that John had set up for them.

As the reception wound down, John and Sherry thanked everyone and then headed across the street to the hotel where they were staying for the remainder of the weekend.

When John and Sherry got to their hotel room, Sherry excused herself and went into the large bathroom in the honeymoon suite. John waited and took off his jacket and tie. He sat. He didn’t know exactly what was going on, but he was getting a little restless when the door finally opened.

When Sherry came out of the bathroom John just grinned and stared. She was wearing the schoolgirl outfit. The shirt was tied tightly under her tits, her nipples showing that there was no bra and the skirt was rolled up enough to almost be able to see her pussy from the front. John could imagine what it looked like from the back. He raised his hand and gave her the twirl that meant turn around. She did, the entire bottom of her ass was pushing up the back of the skirt and showing below it.

“Holy shit. You look like a wet dream and like you need a good fucking, little girl.”

Sherry slowly walked toward him. “I’m just a naïve little schoolgirl who doesn’t know what to do on her wedding night and needs some instruction, sir.”

John laughed. “Jesus, Sherry, you still surprise and amaze me.”

Sherry broke into a wide smile. “Just a little something to get you fired up to fuck me pregnant.”

“That won’t be a problem tonight.” John took Sherry’s hand and put it on his crotch. His erection was prominent.

“I think I’m going to get fucked,” Sherry purred.

John stood and pulled her against his hard cock and grabbed her ass cheeks in both hands. “Hard. And more than once.”


And they did fuck hard and more than once. John first took her bent over the bed, still in that schoolgirl outfit. He fucked her long and hard and they both had good orgasms. They then lay on the bed and rested for about 30 minutes. Then Sherry sucked his cock hard and he crawled on top and they made more conventional, missionary, slow and steady love. John filled her again and then they lay and rested. It was a good day.

The next morning, Sherry and John slept in until about 11am. They got up, wandered the area around the hotel, did a little shopping, had lunch, and got back to the room about 5pm. John started working on Sherry with little touches, knowing that that usually led to sex. But Sherry was having nothing to do with it.

“We need to get ready for dinner. I want to get downstairs to the hotel bar by about 6, then to our reservations at 7. After that, I want an after-dinner drink. I want to enjoy tonight here at the hotel.”

“I understand. This is our short honeymoon, after all. We will take the longer one later.”

They got ready and went to the bar for a drink. They then went to dinner where they both had steaks. It was good.

When they got to the bar, they found that it was not too busy, but had a decent crowd. Sherry and John picked out a table near the back corner and ordered a drink.

They were just sitting there talking, watching the other patrons when Sherry suddenly grinned and stood up. John looked at where she was looking and saw a well-dressed Asian woman heading their way with a big smile. She and Sherry met a few feet away from the table and hugged. They talked for a second and then Sherry led the woman over to their table. The woman was about 5’2″ and dressed in a nice little black dress. She filled it out well and was very pretty.

“John, this is one of the women I lived with when I was young and going to school. This is Kim.”

John stood and shook her hand. “Hi, Kim. It’s really great to meet you.”

“Hi, John. I’ve heard a lot about you the last few days. When I told Sherry that I was going to be back in town, she invited me to meet you.”

They sat down and Sherry explained that this was one of the women who was also young and trying to make it through school that she shared an apartment with back when she was a young mother. There were several women who passed through there over the time Sherry lived there trying to get on her feet and raise Dana.

Sherry and Kim were sitting next to each other with John on Sherry’s left. Sherry grabbed Kim’s hand and spoke to John. “Kim was there when I was just getting started with my nursing degree and she helped me with Dana. We lived together for two years and she still sends Dana a birthday card.”

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