Training Lolita Ch. 08


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.


— From the last story

John spent the night with Sherry and woke to her stroking his cock. But she was just teasing him and waking him up. She wanted to make the point that she could not have sex with him as long as he was fucking her daughter. He agreed and they had sex.

Just before they started to relax into a nap after sex, Sherry let it slip that she had had sex with men and women. She finally admitted that she was bisexual. Then she worked out of him that Dana was also bisexual.

After sex, John went home. Sherry wanted to wait for Dana and discuss their situation. She was going to tell Dana about them and that she couldn’t have sex with John anymore.

While waiting at home, John got a visit from Deb, Dana’s friend. They had been having sex, too, and Deb wanted to have sex when she showed up. John was pretty sure that Sherry had not meant that he couldn’t have sex with only her daughter. He figured she meant be exclusive, so he only got Deb off with his fingers.

Then he got called next door to find out what had happened between the mother and daughter that he both had sex with.


Sherry opened the door, smiled at John, and waved him in.

John entered with a sigh of relief because it seemed Sherry was happy to see him. He was ushered into the living room, but didn’t see Dana anywhere. “Dana’s upstairs?”

“Yes, she’s throwing some things together and going up to visit her school with the grandparents. She wants to show them around.”

“Oh, okay.”

About that time the front door opened and Deb came in. John raised his eyebrows at her, wondering what she was doing.

“Hey, Miss Sherry.” All Dana’s friends called her that. “Dana texted me to come over.”

“Well, that was quick.”

Deb glanced at John. “I was next door talking to Mr. T.”

Sherry turned to John and raised her eyebrows at him. John grinned and shrugged, not wanting to discuss it in front of Deb. Deb interrupted.

“I’m sorry Miss Sherry. I was just waiting for a chance to talk to Dana.”

“That’s fine.” Sherry smiled at Deb, but that’s not the vibe John got when she turned and glared at him.

“I’ll just go see Dana.” Deb scampered upstairs.

Sherry rounded on John. “Well?”

“Nothing happened. She came over to have sex, but I told her about us and we didn’t do anything. I told her I was waiting to talk to you after Dana came home.”

Sherry eyed me, then smiled and shook her head. “Shit, I’m sorry. We’re not even in a relationship yet and I’m already acting like we are in a committed, exclusive relationship. I don’t mean to be that way. I just haven’t been in one in a long time.” She moved directly in front of John. “I’ll make it up to you later.” She hugged him and then kissed him. John put his hands on her ass.

“Get a room!” John and Sherry jumped at the proclamation from Dana.

Sherry jumped back quickly, not sure how Dana was going to take this blatant display of contact between her and John. “Sorry.”

Dana grinned. “Don’t be mom. He’s really good in bed.”

“Dana!” Sherry acted shocked, but in reality she was happy her daughter would continue to talk openly and honestly about sex with her. She had never felt like she could even talk about sex with her parents, even after she was pregnant.

Dana walked up to John and pulled him down and kissed him on the mouth, but only briefly. “Sorry, mom, but I learned a lot.” She turned and looked at John, her body heat ramping up at the memories of the two of the together. “Too bad I can’t have one more time before you abscond with my first friend with benefits.”

“Dana, please.” This time Sherry was actually smiling, almost proud of how her daughter was acting. She had raised her to be open and honest with things. Sherry was also hoping that Dana would be able to enjoy her sexuality before she became tied down like she herself had at so young an age.

Dana then went over to Deb, who had come down with her but had gone unnoticed until now. “Deb, promise me you’ll try to come visit. I want to show you around up there.”

“I’ll try.”

“You do well at that community college and you’ll be able to get in after a couple of years and then we can be roomies.”

“I don’t know if I can afford it.” She seemed completely lost standing there.

Dana went and hugged her and they hugged for a long time. You could see how close the two were. They were having a hard time saying goodbye, even though Dana was trying to keep it light.

“Heck, Deb, I’m only going up there for a couple of days this time. I’ll be back for 4 days before I leave for good. You’re gonna make me mess up my makeup!” She mock punched Deb in the arm and Deb gave a small smile.

Dana turned to her mother. “I’ll be back in a couple Escort Çankaya days, mom. Grandma and grandpa just want to see the place and spend some time up there.”

“I know.” A honk sounded outside as she said that. “There they are. Go ahead. You’ll be back later this week and I’ll have plenty of time to cry over your leaving.”

“Moommmm!” Dana groaned, but it was obvious that she was going to miss her mother just as much. “Okay, gotta go.” Dana grabbed her bag, gave her mother a quick hug, trying to avoid too much emotion, and ran out the door.

Deb was standing there looking forlorn, her best friend for many years preparing to leave for college without her.

Sherry could see this and wanted to comfort Deb. She went over and hugged Deb and Deb leaned on her and held her. You could tell that she was already missing her close friend.

Sherry walked her over to the couch and sat her down. She put her hands on either side of her face and looked directly at her. “Don’t worry, Deb, Dana will stay close. She is a good friend and the two of you are very close. I’ll even see if you want to go up there whenever I visit her, okay?”

Deb nodded. “Thanks, Miss Sherry. I didn’t realize how hard this was going to be until I saw her with a bag on her way out. I know she’ll be back again before school starts, but it really hit me just now.”

“I know. I’m really going to miss her, too. It’s been just me and her since she was born. I’ve never been alone.” She leaned over and hugged Deb again.

Deb hugged her back. “I’m sorry Miss Sherry. I was so sad myself I forgot how hard it was going to be on you.” Deb pushed away and looked over at me and then Sherry. “At least now you’ll have Mr. T. He will keep you from getting too lonely.”

Sherry could sense that Deb was trying to inject a little humor with that comment, but that John was another person that she was going to miss.

Sherry figured she could handle this problem. She was not yet sure if she could go through with it, but she was going to find out. Maybe she could make this fun for everyone and keep everyone close. She knew that Deb was a friend of her daughter’s, but she couldn’t let that stop her. And she knew when she looked over at John and saw the look of concern on his face that he was a good person and would be reliable. She just had to trust her instincts. And this wasn’t completely altruistic. She would, after all, get to be with a man and a woman at the same time. For as long as they could all get along. And how would Dana take it? She was sure that, based on what she had seen so far, that she would be fine with this arrangement.

“C’mon.” Sherry stood and put out her hand. “Come with me.”

Deb took her hand and Sherry led her over to and up the stairs to the second floor. When they got to the top, Sherry looked back at John. “Just a second, okay?”

John nodded, not knowing what was going on. He figured that Sherry was just going to continue consoling Deb. He didn’t know how long he was supposed to sit there and wait, but he did.

Sherry led Deb into her bedroom and over to the bed. “Sit down here, I have something to discuss with you.”

Deb sat and looked up expectantly, not knowing what was coming.

Sherry took a deep breath. She was not entirely sure she about this, but she thought again about how it would kill several birds with one stone. First, by inviting Deb into her bed, she could again experience a woman. She liked both men and women and they offered different things. Secondly, she felt it would help Deb get over the loss of her best friend to college. Finally, it would allow Deb to continue her sexual relationship with John on Sherry’s terms. “Okay, here’s the deal. I know that you are hurting right now. So am I. We are both missing Dana and she hasn’t even left for school yet. And I know that you are missing John as well.” She watched Deb closely.

Deb was trying to figure out where this was going.

Sherry hesitated, but then blurted it out. “If you want, you can join John and me in bed.”

Deb stared, stunned at this. She had no idea this was coming. She thought Miss Sherry was going to do something else, anything other than that, to console her. To invite her to have sex with her and Mr. T. was surprising. She didn’t even know that Sherry was bisexual. “I – uh – I would like that. Is it okay? You don’t have to do that just for me.”

Sherry grinned. “Honey, this is not just for you.” She moved closer and put her hand under Deb’s chin. “I like women, too, and since you have already had sex with John and are bisexual, this means we can all have fun. I could tell that you had become attached to John, so this is a good resolution, right? We will both be missing Dana and we could help each other and enjoy, John, too.” Meanwhile, Sherry’s motor was already running as this had become one of her go-to fantasies when she masturbated. She loved the idea of seducing one of her daughter’s friends and had read many stories about it online.

Deb started smiling. “Oh, yes, Miss Ankara Escort Sherry. That’s a great idea.” Then she thought once again that maybe Miss Sherry was just doing this to make her feel better and her smile faded. “But you don’t have to do that just for me.”

Sherry grinned wider and sat next to Deb. “Oh, this isn’t just for you. I just told you that. I like women, too, and you are cute as a button. I think I will enjoy having sex with you.” Sherry put her hand on Deb’s leg and rubbed it.

Deb threw her arms around Sherry and hugged her. “Thank you, Miss Sherry. This is a great idea. I’ve always liked and been attracted to you.”


“Yes, ma’am. And you should know that all Dana’s friends call you a MILF behind her back.”

“Really! That’s interesting.” Sherry turned her attention back to the task at hand, but definitely enjoyed the little ego boost that that comment provided.

It was time to take the plunge. “Okay, so here’s what we are going to do. John is downstairs wondering what the hell we are doing up here. He thinks I am consoling you, which I am, but not in the way he thinks. So we’ll both get undressed and when we are ready, we’ll lay back and call him up to join us. Sound good?”

“Yes, Miss Sherry, I like that idea.” Deb was already much more upbeat and happy.

Sherry stood up and started undressing. When Deb stood up, she stopped her. “Wait, let me do that.”

Sherry quickly stripped off her clothes and Deb stared at the still gorgeous woman and well-formed body. Sherry’s ass was fantastic and she had nice full tits “Wow.”

Sherry grinned. “Thanks. Now let’s do you.” Sherry went to Deb and pulled on the bottom of her t-shirt. Sherry pulled it up over her head and bared her torso. She immediately put her hands on Deb’s tits and felt the nipples. “Nice tits.” Deb just grinned and twitched little at the stimulation as Sherry then went and yanked her shorts down to the floor. “No underwear at all, huh?”

Deb shrugged and was a little shy to admit it, but did. “I was going to Mr. T.’s house and wanted to be ready to fu — uh — have sex.”

Sherry grinned at Deb’s little slip and ran her hand over Deb’s pussy, pushing a finger through the slit. “And I think you will be in a few seconds. Now sit back on the bed.”

Deb scooted back on the bed and Sherry got between her legs. She stood over this slip of a girl who was so beautiful, but didn’t know it and stared like a hungry wolf. “What do you want now, you little minx?”

Deb looked up at Sherry. “Will you eat my pussy, Miss Sherry?”

Sherry smiled. She had always known that Deb gave in to her friends and now she could feel the submissiveness. “I think first you should taste me.” Sherry crawled up over Deb and put her pussy directly over Deb’s face. “Now taste Miss Sherry’s pussy and make me wet.” Sherry had always liked how when she told Dana’s friends to call her by her first name that they called her Miss Sherry.

“Yes, ma’am.”

Sherry grabbed Deb’s head and moved her hips back and forth slightly, shoving Deb’s face into her crotch and moving it back and forth from her ass to her pussy. Deb licked and sucked like a pro. “Mmmmmm, nice.”

Sherry let Deb get her motor running and then released her head. Deb didn’t stop. Sherry chuckled at her energy and willingness. She finally pulled away, rolling to one side.

Deb looked at Sherry. “Was that okay, Miss Sherry?”

Sherry lay against Deb, running her hands over Deb’s tits, the nipples hard as stones. “It was excellent, Deb. I think you are a very good pussy eater.”

Sherry rolled off the bed. She got between Deb’s legs again and put her hands on the inside of Deb’s thighs. Deb immediately spread her legs and pulled them up, giving Sherry unrestricted access to her pussy. Sherry watched and decided that she and John were going to have lots of fun with Deb. She had to be careful to make sure Deb understood what was going on, but it would be fun having this little sexual dynamo in her bed.

Sherry got down on her knees and stared at the beautiful young pussy in front of her. She had had a female lover for a couple of years and missed this. She enjoyed everything there was about sex with men and women, so she was looking forward to this. Sherry leaned forward and kissed Deb’s right thigh just below the juncture with her pussy. Deb took a deep breath. Sherry kissed the other side and got the same result. She then leaned in and pushed her tongue into the bottom of Deb’s pussy near her ass. Deb pulled her legs back further, begging for more attention. Sherry ran her tongue all the way up Deb’s slit until she went over her clit, eliciting a groan from Deb. Sherry could see that Deb was already pretty wet.

Sherry sat back. “Well, I think we are ready for John now, don’t you?”

“Yes, ma’am.” Deb was all breathy and her eyes were wide.

“What do you want him to do? And be specific.”

Deb took a deep breath and put her head back. “I want him to put his big, hard cock in my tight, little Sincan Escort pussy and fuck me until I cum.”

Sherry laughed. “Well, at least you know how to say it.”

Deb raised her head back up and looked at Sherry. “Mr. T. told us that a lot of guys like dirty talk in the bedroom and Dana and I practiced it.”

Sherry held up her hand. “Okay, let’s keep Dana out of this.” She got up on the bed. “Let’s both get up here against the headboard and I’ll call John.”

They scrambled up against the headboard, their legs spread and wet pussies on display.

Sherry called out. “John? Could you come up here please?”

Meanwhile, John had been waiting impatiently in the living room. What the hell was going on up there? Surely, they had things under control by now. He sat and fidgeted, wondering if he was going to come out of this back where he started, with no sex at all.

Then, he heard his name called. He went to the stairs and made his way up. He heard his name again and could tell that it was coming from Sherry’s bedroom. He went down to the bedroom to see how the two sad women were doing.

When John got to Sherry’s bedroom the sight that greeted him stopped him in his tracks and he gaped. There they were, Sherry and Deb. They were both sitting up with their backs against the headboard, their naked bodies on display. Sherry’s voluptuous one, large tits and nice shape on the right, wet pussy being stroked by one finger. On the left, the tiny sexually charged Deb was in the same position. She was also stroking her pussy and looked flushed and ready for sex already. John could only stare.

“See anything you like?” Sherry teased John.

John grinned and stepped further into the room. “I see everything I like.”

Sherry sat up. “Then get undressed and get in bed with us. We are in need of a large male appendage.”

John undressed quicker than he had in years. “I think I have one of those.”

Sherry stared at his cock when he was done. “Yes, and I think it’s ready for us.” She turned to Deb. “What was it you said you wanted?”

Deb stared at John’s cock. “I said that I wanted him to put his big, hard cock in my tight, little pussy and fuck me until I cum.”

Sherry looked up at John. “Well, I think you have your first task for today.”

John grinned. “I could get used to this.”

“I hope so.”

Sherry got off the bed and John watched as she walked around to Deb’s side. He didn’t move toward Deb until he could see what Sherry was going to do. Sherry got to the head of the bed and said to Deb, “No, skootch down and spread your legs like you did for me when I wanted to lick your pussy.”

Sherry watched John as she said this and saw that she got the reaction she wanted. It turned him on greatly to think about these two women having sex. She was going to enjoy this as much as he did. She hoped that Deb would enjoy it, too. She seemed raring to go when it came to sex – just like Sherry was when she was young. “Good, now get ready to be fucked.”

John decided this wasn’t the position he wanted, laying in the bed in the missionary position on top of Deb. Instead, he moved to the side next to Sherry and grabbed Deb by her hips. He pulled her sideways so that her pussy was available to him as he stood on the side of the bed. He wanted to fuck her like this. “There, that’s better. I’m going to fuck that tight pussy while I stand here.”

“That works for me, too.” Sherry clambered back on the bed and positioned her pussy over Deb’s face. “I’m going to enjoy my first threesome in many years.”

John’s eyebrows went up and Sherry grinned back at him. That was new information to John.

John decided to get down to business so he took his cock and rubbed it up and down Deb’s pussy. She moaned and started working Sherry’s pussy. John ran it down to her opening and started slowly fucking her, feeding her an inch at a time as her juices wet his cock. Soon he was thrusting in and out strongly and he marveled at the view he had.

He could look down and see his cock sliding in and out of a fully shaved, 18-year old pussy. It was tight and she was loving it. He could see and feel her small hips as he thrust and ran his eyes up over her barely visible tits. They were partially masked by the legs of the woman sitting on her face. He ran his eyes over the junction of Sherry’s pussy and Deb’s mouth and could occasionally see a tongue appear as she lapped at Sherry’s delicious pussy. His could then look up past Sherry’s nice waist to her full, ripe tits. They were so well formed and perfect he was amazed that she was not also only 18. He looked up into her face, a pretty one, and Sherry had her eyes closed, enjoying the pussy-eating that Deb was providing. Then she opened her eyes and grinned at John. He leaned forward and they kissed while they each used the 18 year old Deb for their sexual pleasure.

“You are one hot fucking mom.”

Sherry smiled. “Thanks. I like this position.” She moaned as Deb continued to work on her. “Deb’s very good with her tongue and it looks like she has a nice tight pussy for you.”

“Yes, she does.” John gave a forceful thrust at that. Deb moaned and Sherry smiled. John leaned foward close to Sherry, but not to kiss her. He looked her straight in the eyes. “I’m going to cum.”

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