Training Lolita Ch. 10

Categories: Genel.

May 26, 2021 // By:admin // No Comment

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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 story

John and Sherry went to visit Dana for her freshman parents’ weekend. She introduced us to her dorm roommate, a petite young thing named Jean. Jean was a youngster who had had a sheltered up-bringing and was ready to explore. She and Dana did just that and were having sex. However, she was a virgin and asked Dana if she could use John to remedy that. Jean had been told by Dana about her exploits with John, so she wanted to lose her v-card. And together, Dana and John took care of that.

The next day, Sherry also enjoyed the young Jean and so Sherry and John made good use of the obedient young lady.


One night in October when Sherry got home, John was in his own house doing some work. When he saw she was home, he walked over and went in to talk to Sherry. As soon as he appeared at the kitchen entrance, Sherry turned from the counter where she had poured herself a glass of wine. She was still in her nursing scrubs, but looked delicious just the same.

Sherry raised her eyebrows at him. “So Dana tells me that she wants to invite you up to display you to a few cute, young things, merely as a teaching implement. What do you think?”

“I’d love to do it. Both heads think so. But what do you think?”

Sherry shook her head and grinned. “Of course they do. What man would pass up that opportunity?” She turned and put her wine down. “But I do have some stipulations.”

John immediately started thinking about what they might be. Things had been changing between them lately. He felt more and more like they were a couple. But maybe she was tired of him having sex with her daughter and friends. She had initially wanted it to stop with her daughter, but then had let it continue. Maybe she was getting tired of him herself, while after just a few months he was feeling like he was falling in love with her. He stood there and realized that she was waiting for him to say something.

“Of course. I wouldn’t want to do anything to get between us.”

Sherry rolled her eyes. “That’s only one of the heads talking.” She then grinned. “I don’t mind you going up there because I can take an extra shift this weekend and make some more money. One of the other nurses wants a weekend off with her family and I could cover for her. Also, that means that you had better leave me sated and satisfied before you leave, got it?”

John laughed. He could see the twinkle in her eye and hear her slightly jesting tone. “I’ll leave you exhausted and a boneless mass in the middle of your bed.”

Sherry laughed, too. “You do that and I’ll allow just about anything.”

“I believe you are also thinking with the wrong body parts.”

“Right now, my pussy is controlling all my thoughts, so if you want to talk to my brain, do so through my pussy.”

John walked toward her, shaking his head in mock disbelief. “Are all nurses as open and vulgar as you?”

Sherry chuckled. “Absolutely. We are up to our elbows every day in pussy and cock and many other body parts. Sometimes you don’t even want to see someone’s junk when you come home. I know another nurse whose husband is a gynecologist. She says that sometimes she comes home and he says he is tired of looking at pussy. Now, I can’t imagine that. So, anyway, yes we are open and talk about everything.”

John reached down and grabbed her ass and pulled her up against his body. “Then tell me what you want right now. Do you want me to strip off your clothes, throw you on the table, eat your pussy until you cum, and then fuck you until I fill you up? Or do you want the slow seductive method where I take you upstairs and make slow, passionate love to you?”

Sherry grinned and rubbed her curvy body against me. “If you are going to leave me sated, then it’s going to take both.”

He grinned and pushed her away. She looked a little confused at first, but John quickly handled that. “Strip off those scrubs, Miss Sherry, I’m going to feast on that hot, sexy, fucking body of yours.”

Sherry immediately started stripping. She wasted no time shedding the top and bottom of her scrubs. She was wearing a beige colored bra and panty set that was a little sexy, but mostly functional. She unhooked the bra and dropped it onto the pile she was building on the floor. Then she grinned and wriggled her hips as she put her hands into the waistband of her panties. free spin When she did, her tits went to bouncing and jiggling and John watched closely as his cock started getting hard. Sherry turned around and lowered her panties, keeping her legs straight and giving him a peek at her pussy as she did so. Damn! This woman new how to get someone’s motor running!

When Sherry turned back around John looked her up and down. “What a woman!”

Sherry blushed at that, even though she had stripped in front of John many times and they had been together for a while now. “Thank you.”

“Now undress me.”

Sherry smiled as she came over to John. She unbuttoned his shirt and dropped it on the same pile of clothes with hers. She unfastened his belt and pulled it out. Then she unhooked his Dockers, undid the zipper, and yanked them to the floor. John was commando, so his cock immediately bounced up and stood straight out, pointing at her. It was ready.

Sherry looked up at him. “Somebody was hoping to get lucky.”

“I don’t think luck is necessary around here.”

Sherry smiled. “Probably not.” Then she leaned forward and gave John’s cock a couple of quick sucks.

John pulled Sherry off his cock and reached to stand her up. Once she was up, he gave her a quick kiss and then led her to the kitchen table. He turned her toward him and pushed her back onto the table. She lifted her butt a little to get it up on the table and then fell back with his push. John looked down at the beautiful, naked Sherry. Her shaved pussy was on display, the inner lips almost making an appearance and her tits were magnificent. They never flattened out as much as he figured they would, but they still spread out and showed how much mass they had. The nipples were rock hard. Every man’s wet dream was lying there for his use.

And use her he did. John bent over and feasted on her pussy until she came. She was very excitable and her bare pussy was delicious. He loved how open and free she was about showing her enjoyment of that. She didn’t hold anything back, talking, moaning, and squirming under his ministrations.

After he had an orgasm from him feasting on her pussy, John lined up his fat cock and started fucking her. She reacted to each thrust and egged him on with her dirty talk. She was good at the dirty talk. John fucked her until she came a second time, going into spasms as he fucked her.

He had waited for his own orgasm, so he pulled her off the table, bent her over, and fucked her that way. He loved watching how fantastic she looked and acted being fucked from behind. She had a great ass and participated more than anyone he had ever had sex with. That included his wife. He loved sliding his cock into her very hot pussy. He fucked her until he filled her pussy with cum. By the time they finished they were both exhausted.

Sherry and John got something to drink and went upstairs. They never got to the second part, the slow, passionate love-making. They just passed out.

On Friday morning, when John was preparing to go to work, Deb showed up and they were all having breakfast. It was at this time that Sherry mentioned something that John had been worried about.

“John, can I ask you something?”


“Has Dana called you yet?”

“Not yet.”

“Well, if you go up there, you’ll be out of town this weekend and having fun with a bunch of young ladies, so I was thinking about the weekend. I have scheduled an extra shift today, but tomorrow night an old friend of mine is going to be in town and I thought that we might like to go out to dinner.”

“Just dinner?”

“Well, maybe a little more than that.” Sherry gave the two of them a big grin.

John tried not to show it but he got a little jealous at that. He had no reason to be that way considering he was fucking her daughter, her daughter’s best friend, and several other women. But that didn’t stop it from happening. He was falling for Sherry in every way, and his upbringing affected his thinking. She was a definitely a sexual dynamo, but when they were just hanging out together she was funny, had similar interests in movies and books, and they just seemed to fit. He was feeling a little attached and was thinking about asking her if she wanted to live together – or more. But this latest request might mean that she wants the same independence or more. Maybe she thought he was too old for her. Anyway, he tried to act nonchalant. “Sure. That’s not a problem.”

Sherry looked pointedly at him. “You sure?”

John shrugged. “How can I have a problem with it when I’m sleeping with Deb and your daughter regularly?”

“I don’t know, but do you?”

John looked down at his hands. “Sorry. I guess I do feel a little jealous about you being out with another man.”

Sherry laughed and John stared. What?

“Well, I really like you, too, John. I’m not going to be out with another man. This friend is female. I just didn’t mention the gender to see how you took it.”

John shook bonus veren siteler his head. “You’re mean. You were just trying to get a reaction out of me.”

“Yes. And it was the reaction I was looking for.”


“Sure. I want you to feel a little protective and possessive, just not obsessive. I feel a little bit that way with you. I want to spend more and more time with you.”

John looked at Deb and back at Sherry. “Yeah? Well, do you not want me to go to visit Dana this weekend? Should I tell her no?”

“No, no, that’s not it. We were already down this road before you and I got close, so I’m not going to stop you from having sex with Dana and Deb. And I have no other man I’m interested in. You are all I need there. But remember I was single for many years and trying to hide most of this from a young daughter. So I have some things I’d like to still do and one of them is hook up again with this woman who is coming into town. She’s a lesbian, so I don’t think she’d join us together, but I still want to enjoy a couple of other women while we are together.”

John was a little surprised. “Well, there’s nothing keeping you from that. We haven’t had any type of relationship discussion at all.”

“I know. But women generally start to feel like they are in a relationship before men do. Do you think that we are in a relationship?”

“Yes, I definitely do.”

“Good. Now. Do you mind if I go have sex with my lesbian friend?”

“None at all. I have one favor, though.”

“What’s that?”

“Any chance of some pictures?” John grinned at her.

Sherry laughed and slapped him on the arm. “You’re incorrigible.”

“No, just a heterosexual male who loves watching two women have sex.”

“Yeah, situation normal for men. Always love to see naked women together, and then hoping that they get to join in.”

“Well, I’ve certainly checked that box a few times.” John looked from Sherry to Deb and back again.

Sherry grinned. “You are a very lucky man.”

John grinned, but then changed to a more serious look. “You are right and I really appreciate that. I appreciate everything with you.”

Just then John’s phone rang and it was identified as Dana. “Speak of the devil,” he said, holding up his phone.

He grinned at Sherry and Deb and took it into the other room. He really would enjoy whatever college girls that Dana had lined up, but now his situation with Sherry was more important. He wanted to make his desires to make the relationship more permanent known to her. He had pulled out his wife’s engagement ring last weekend and thought about doing something like ask Sherry to marry him. He just wasn’t sure how she would feel about it. He was about 10 years older and Sherry was still young, gorgeous, and about to be freed from being a single mother. What if she didn’t want him permanently?

He said hello and Dana spoke.

Dana was nice and said hello like she was just calling to see how things were at home, but he knew what she wanted from the discussion with Sherry.

“What is it, Dana? I can tell you have something on your mind.”

Dana giggled. “I have a homework lesson that I need your help with. I have been discussing sex with some other girls here in the dorms and I need the assistance of a man.”

John grinned. “I see. And what, pray tell, is the assistance that you require?”

There was a pause and then Dana giggled again. “I was discussing the male appendage with these young ladies and I could tell that they had not had much experience with one. I told them I knew someone who would be willing to be our model for some personal instruction. Would you, Mr. T.”

“Are you telling me that there are no college boys up there who can perform this service?”

“I’m sure there are, but I don’t know if any of them are any good. I do know you and I wanted to get you up here to college again.”

John thought about it. He was so tempted to say yes, but decided he had to discuss the relationship situation with Dana. “Dana, I think I should say no.”

There was a short pause and then she answered, sounding a little hurt. “Why, Mr. T.? I thought you would love this and I know you love me.”

“I do, Dana, but I have something important to discuss with you.” He took a deep breath. “I have become very attached to both you and your mother. In fact, I want to make my relationship with your mother more permanent and I wanted to run it by you.”

“What!? Are you crazy? I would love that! Mr. T. and my mom together. You going to ask her to marry you or just move in together?”

“Well, I’m still a little old-fashioned, so I think I’m going to have to propose.”

“Oh my god! Mr. T. I would love to have you as a step-dad and I know my mother already feels very strongly about you, even if she won’t say so.”

John turned toward the kitchen. “Well, I need to figure this out.” Sherry came to the doorway and he stared at her. “I need to get this straightened out here before I do any more deneme bonusu veren siteler visits there.”

Sherry stared at him and he could see her frown.

“I’ll have to have this discussion with your mother before I answer your question.”

Sherry suddenly seemed to get very upset and ran upstairs. John stared after her.

“I have to go, Dana. Your mother heard the last part and it upset her. I have to see what’s going on.”

“Okay, ‘Dad’, I’ll talk to you as soon as you ask her.”

Dana’s emphasis on ‘Dad’ brought on an emotional surge. He had never had anyone to call him that and he lost his only chance. “I’m sure you’re the first person she will call.”

“Okay, go ask her. I can’t wait!”

John went up to Sherry’s room and she was sitting on the bed, hanging her head like a sad dog.

“Sherry, what’s wrong?”

“I heard you telling Dana that you couldn’t go up there until we had a serious discussion. You’re breaking up with me, right?

“Wait, what? No …”

Sherry interrupted him. She was getting worked up now.

“I know how this works, you’ve had your fun, but as soon as I mention that I want to have some, you go running off. You don’t care about me at all, do you?” Her eyes were sad and accepting of this.

John knelt in front of her and grabbed her hands. Sherry tried to snatch them away, but he held them tightly, trying not to hurt her. He felt she was still suffering some kind of self-esteem problem. “Nothing could be further from the truth. I don’t want to ever be without you and I was telling Dana that I loved you and her and was going to ask you to marry me.”

Sherry just stared at him, her mouth gaping.

John grinned. “Sherry, I know that I am 10 years your senior and you still have a lot of life in you, but I want you in every way. Will you make me whole again and marry me?”

There was a long pause and Sherry blinked a few tears away.

“Are you sure?”

“I’m as sure as I can be. But can you be with a man who is so much older?”

Sherry took a deep breath and leaned over. “Yes, I can. I can be with and love you.” She took his head into her hands and kissed him fiercely.

There was a sniffle from the door and they turned toward it. Deb. “You guys are so beautiful together.”

Sherry sat back up and put out her hand. “Come here, Deb.” Deb went to Sherry and sat next to her, holding her hand. “Deb, you will always be welcome in our family. And I mean that in every way.”

Deb leaned against Sherry. “Okay, Miss Sherry.”

Sherry turned back to John, who was still kneeling. She wiped at her eyes. “And you, you big lummox, you proposed to me without a ring? Where is my ring?”

John laughed. “I’m so sorry, but I was not prepared at the exact moment that you heard my conversation with Dana. Give me 5 minutes, okay?”

Sherry glanced at Deb. “Should we give him five minutes to make up for this gaffe?”

Deb grinned. “Yes, Miss Sherry. I want to see the ring.”

“Me, too. Okay, John, hurry back.”

John stood up and leaned over and kissed them both on the forehead and then dashed from Sherry’s house back to his. He went to the drawer where he kept the ring and looked at it. He said a short prayer to his wife and unborn child, thanked God for giving him another family this late in life, and ran back to Sherry’s. When he got up to the bedroom, Sherry was still sitting there, but Deb was gone. He immediately went to his knees and then noticed that Deb was off to one side with a camera.

“Miss Sherry, will you make an old man happy and agree to marry me?” He opened the box and showed her the ring.

Sherry stared wide-eyed at it. “You know that I have never been proposed to before. I’ve never had this experience and it’s very exciting.” She leaned over and took the ring out of the box. She held it up for John. He took the ring and slid it onto her ring finger. It seemed to fit considering he had not had it resized. Sherry held up her hand and stared at it.

Deb had moved closer and was taking short videos.

Sherry leaned over and kissed John. “We are going to be so good together.”

John smiled and nodded. “Yes, and we already are.”

Sherry turned to Deb. “Okay, you can stop taking pics and vids. Send them to Dana and my parents. I will call Dana on my phone.”

Sherry called Dana and there was all kinds of laughter and some tears and then it was over. Or at least John thought so. Then she called her parents and they were all laughing and crying. John just watched and smiled, happy with the way things were going. Then it was finally over and Sherry put the phone down.

Sherry turned to Deb and grinned. “Strip and get in bed my little plaything.”

Deb grinned back and stripped.

John was watching. “What’s going on?”

Sherry turned to him. “Now we are having an engagement celebration. You are going to fuck me and fuck me and fuck me. Whenever you cum, Deb is going to clean out my pussy and then get you hard again. How does that sound?”

“Fantastic.” He started stripping off his clothes.

Sherry turned toward Deb and she responded quickly. “I love it Miss Sherry.”

And so they did. Sherry lay back and she and John made mad, passionate love until they both came. Then John rolled to the side for Deb.

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