Training Lolita

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

After Sherry's confession, Dana had convinced John to take her to her grandparents' house. He did and they met her Sherry's parents, who were overjoyed to see Dana. Things were going well, but when they started to discuss why, Dana immediately wanted to leave. She invited them over to Sunday dinner for them to see Sherry and explain to them both.

So on Sunday evening, they came over and the family, after a few tense moments, had a tearful reunion. The dinner went well and Dana went with her grandparents to spend the night and get to know them better.

John was surprised when Sherry seduced him wearing the same schoolgirl outfit that Dana had worn to his house. After John provided oral sex to Sherry, she almost collapsed from exhaustion after such a long day. She invited John to spend the night, so he did.

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John woke very early to go to the bathroom. When he came back, he crawled into bed and snuggled up to Sherry. He had eaten her delicious pussy last night but not had an orgasm himself. When he spooned up behind her, her nakedness got him hard. He didn't try anything, just enjoyed having his cock up against her ass crack while he relaxed. It had to be about 4am, so he slowly relaxed and went back to sleep.

The sensation of someone stroking his cock is what woke John up. He opened his eyes and could see that there was plenty of light in the room so it was after daybreak. He slowly looked down and saw Sherry smiling up at him as she stroked his cock.

"You can stop that - in about 20 minutes."

Sherry stopped stroking. "You think you can handle 20 minutes of this?" Sherry rolled off the bed and stood up at the end, stark naked and looking every bit like the dictionary definition of sexy.

She turned and went into the bathroom and came out in a silky robe. "So here's the deal. I have wanted to get involved with you and learn more about you for a while. But now you are sleeping with my daughter and I can't do it as long as you have a sexual relationship with my daughter. I'm not exactly upset. I have a pretty open mind and there's nothing I can do about it now except put a stop to it." She took a deep breath. "Dana leaves for college soon, so if you promise not to have sex with her again, then I will consider a relationship with you."

"We're going to have a relationship?"

"If you agree to that condition, yes. I am, after all, a very sexual woman and have had quite a dry spell. I want nothing more than to climb back in bed with you. But I will not unless you promise me you and Dana are done."

John grinned and looked thoughtful. "Well, she is leaving for college soon and I have another pretty little thing, who looks like she could be Dana's older sister, who I want to have sex with - a lot." John gave her a rakish grin.

Sherry leaned over and stared into his eyes. "Is that so? Age flattery? Trying to get you what?"

John was a little unnerved at her close up gaze. "Sex, right?"

Sherry leaned back and wiggled her shoulders back and forth, shaking her barely covered tits at him. "I certainly hope so. Now that my daughter is going off to school and I'll be alone, I have some sexual escapades to make up for. I'm a little out of practice, but I hope to make up for that."

"Well, I suppose I am ready for some sexual escapades."

"Suppose?"

"Well, if it's with you, then I should say I am more than ready."

Sherry reached down to grab John's hard cock. "Yes, I would say you are ready. Can you give me all the sex I need?"

"Or ready to die trying."

"You promise me that you will not have sex with Dana anymore?"

"I promise."

"Good." Sherry dropped the robed, crawled up over John, and centered John's cock on her pussy. She slowly moved it around and bounced until her wetness had spread around it and she slid down his cock. "Mmmmm. Let's hope it doesn't come to you giving your life to make me happy." She must have been thinking about sex for a while because she was already very wet.

Sherry started bouncing up and down and John grabbed her hips as they fucked. Damn. She looked so fantastic riding this cock. His eyes moved down to her tits. "I love your tits." He reached up and started fondling them and pinching her nipples. Sherry threw her head back and moaned, reveling in the sensation John was providing. Her body was definitely very responsive.

Sherry had just gotten started and they had been fucking for only about three minutes when she suddenly stiffened and groaned. She jerked, leaning forward and rubbing her clit against John's pubic bone, his cock buried deep in her pussy, several times. Each time she jerked, she took a deep breath and let it out with a loud whoosh of air.

When Sherry stopped she leaned forward getting within about a foot of John's face. She stared into his eyes and spoke while still panting hard. "I'll give you 50 years to stop that." Her grin was so sexy, John almost came just from that and her implication of sex for the rest of his life with this sexy woman. For a man approaching his fifties he felt like he had hit the mother lode.

When Sherry stopped, John wrapped his arms around her and rolled them to the side, and eventually all the way over. John had managed to get Sherry on her back without pulling out of her pussy. He grinned at her. "My turn."

Sherry pulled his head down and kissed him. "Do it, John. Fuck me hard. It's been a long time."

John smiled at her and said in a fake Texas drawl. "I always aim to please, ma'am."

Sherry just smiled back, pulling her legs back and open for John. John scooted his knees forward until he could get good leverage on thrusting his very hard and dying to cum cock into her tight and receptive pussy.

John started pulling back and thrusting with plenty of force, causing Sherry's entire body to jerk under him. He enjoyed both the feeling and the view of her tits bouncing. He also was really enjoying the way she stared back, letting out a grunt each time he bottomed out and biting her bottom lip in anticipation of each thrust. John knew this scenario was going to lead to a major orgasm. He was going to fill her up with a lot of cum.

Sherry reached up and put her hands on John's shoulders. "Don't stop - uh - uh - keep going hard - uh - uh - I'm going to cum."

And so John did, knowing that he was close, too. He'd been hard for a while now and didn't get a chance to cum last night when he had eaten Sherry's pussy.

"Oh, God!" Sherry started thrashing and cumming under John. She threw her head back and closed her eyes as she kept cumming. He let up a little while she came, but kept fucking her.

When Sherry stopped cumming, John started hard again, knowing he was close. He pounded this fresh pussy and buried his cock into her as fast as he could, looking for that release.

"Yes!" And with that pronouncement, John started cumming. He couldn't stop thrusting and cumming in Sherry's pussy. It seemed to last forever and it wouldn't end.

But finally, it did. John fell forward on Sherry and his body almost completely collapsed.

Sherry held him and chuckled. "I think somebody just had a very big orgasm."

"No, shit."

Sherry stroked John's back. "Me, too. It was wonderful to feel that again."

John slowly pushed himself up off Sherry. She lowered her legs enough for him to climb out from between them and he flopped down beside her on his back.

"Jesus, John, how much did you cum in me?"

John looked down to see Sherry hold up her hand from where she ran it between her legs. It was covered in his cum. There as a lot leaking out of her.

"Well, I was still worked up from last night."

Sherry hopped out of bed with her hand over her pussy. "Be right back."

John lay there, his breathing returning to normal, as he thought about how good that sex was.

When Sherry came back she hadn't put anything on and John marveled at her sexy shape. She was not a skinny one, but was a perfectly shaped woman with real tits and real hips who still had a waist. This woman was so fucking hot! He noticed that she was carrying a towel.

Sherry laid the towel down where she had been, covering what must have been a wet spot, and lay back down next to John. She turned toward him and put her hand on his stomach and her head on his shoulder. "That was the best sex I've had in a long time, John."

John put his hand on her back. "It was amazing."

Sherry started relaxing and John could feel her breathing deepen. She was relaxing enough that she could go back to sleep.

John whispered lightly. "Has it been that long?"

Sherry murmured, "Yes, it's been a long time for man or woman."

John lifted his head a little, digesting that statement and Sherry's eyes suddenly popped open at what she had said and she raised her head to look at him. "Yes?" John was grinning at her confession.

"Uh - well, I - I mean," she stopped and stared at John.

"What? There's nothing wrong with that."

Sherry's eyes narrowed. "Yeah, but I know how men think about that."

"You don't know how I think about it."

Sherry stared at him some more. "Yes, but I know generally how men feel based on the comments and porn out there. Why is it that men like the idea of two women together so much?"

John looked up at the ceiling for a moment. "Well, I can't speak to the general population of men, but for me I love it because I can't understand why everyone isn't attracted to God's greatest gift to man, the woman's body. The woman's body to me is a work of art and everyone should be attracted to it."

Sherry looked at him and then smiled. "Yeah, I can see that. I've always loved both and it doubles my chances to get laid." She poked him with her elbow.

John laughed at that. "Well, it doesn't seem that you have taken too much advantage of that."

"Problems of being a single mother." Sherry was suddenly serious. She looked up at him. "Did Dana ever say anything to you about this?"

"About what?"

"About noticing anything about my sex life."

"No, not really."

"Good. I don't think she needs to know too much about it. I bought those outfits thinking that we could share them; me with you and her with her older man. I just didn't realize that it was you in both cases. I wanted her to learn about sex, and since she's an adult, I wanted her to think open and freely about it. Not like me and my parents. It was always hidden and unspoken in my house and therefore, as a rebellion, I opened up my legs for the wrong man. I wasn't even close to being ready for sex."

"You are fine now, though."

"Thanks. I just wonder about Dana and her friends sometimes. Dana has been guessing lately at my past sex life. You'd think she had the same interests the way she and her friends seem to talk about sex and giggle and tease each other." She looked up at John and when he didn't say anything she seemed to guess it. "She is, too, isn't she? Bi-sexual."

John looked at her. "I don't think I should talk about your daughter's sex life."

"That means that you know something. Don't be evasive."

"I really don't think it's a good idea to tell you anything about your daughter and me. That's a little private and between me and her."

"Well, I think that she and her girlfriends have been doing some experimenting."

"Yeah, well, I guess it's fair to say that I believe she is bi-sexual."

"She told you?"

John looked a little uncertain and Sherry again guessed at it.

"Oh, my god. You had a threesome with my daughter and a friend?" She sat up.

"Yes." John looked a little sheepish.

"Who was it?"

"I really don't think I should say. It's not nice for me to tell you about what we did or reveal anything about it. I really do believe that I shouldn't discuss this with her mother."

Sherry stared at John for a long time, scrutinizing him closely. "Okay. We'll let it go for now."

Sherry lay back down and put her head back on his chest. "I think even though I just woke up, that I could use a nap."

John grinned. "Me, too. However, I have some chores I need to get done today."

Sherry lifted her head back up. "Like what?"

"Well, I have been planning to do some work along the right side of my house for a while. I need to do some tree pruning and bush trimming and stuff like that."

"And that's more interesting than helping me catch up on my lack of sex for the last 18 years?"

John smiled. "Definitely not." He relaxed. "I think the bushes and trees will keep for another day. But what about Dana?"

Sherry suddenly sat up. "Oh, shit. I forgot that she'll probably be coming home soon."

"So you don't want her to know about me and you?"

Sherry looked at him. "Not until I can explain that she needs to move on to another guy and leave you for me. That is what you want, too, right?" Sherry looked at John with what appeared to be apprehension.

John pulled her in close. "Yes, that's what I want."

Sherry relaxed. "Good. We'd better get dressed and straightened up."

John and Sherry got up and John dressed quickly and snuck out. He showered and changed and waited for Sherry's call.

Sherry also got ready. She found that she was actually a little afraid of what Dana might say when she told her. She didn't know if Dana had become emotionally as well as physically attached to John. They had both talked about what a good man he was over the years, always helpful and a good neighbor. But now things were a little different. They had both slept with him. This might be difficult.

John waited at home impatiently for Sherry to call. He was pacing a little and having a beer when there as a knock on his door. He jumped and stared. This couldn't be one of them, right?

John answered the door and was both relieved and surprised. It was Deb. She was dressed in very tight shorts and a tank top, with no bra as was evident by her nipples sticking out.

"Deb? What are you doing here?"

Deb had been smiling, but then frowned, recognizing his impatience. "What's wrong, John? I just came over for some fun."

John pulled her into the house. "Deb, I have something to tell you." He took a deep breath. "We found Dana's grandparents, Sherry's parents, and Dana's with them right now. While that was happening, with Dana going away to college, Sherry and I, well, we had sex. She wants to become involved and that means that I can't be with Dana. You understand?"

Deb hugged John. "Yes, I do." She pulled back and looked up at him. "But we can still have fun, right? I mean I understand about Dana since Sherry is her mother, but I really want to keep having sex with you. I'm really attached to you. I don't know about love, but I really want to keep having sex with you. We can do that, right?"

John ran his hands through his hair. "I don't know if we can. I think Sherry may not like that. I think she implied that I should have sex only with her." He looked down at the scared 18 year old in front of him. He took her back into his arms to comfort her. "But we have to find out. I'm not just going to abandon my favorite little cock-sucker." He pushed her back and gave her a nasty grin.

Deb grinned back. "Damn right!" She lightly slapped him on the chest. "And I can eat pussy well, too. Tell her that!"

John laughed. "Not sure how that will go over, but I promise to try."

Deb walked over and sat on his couch. "Okay, so what's happening right now?"

"Sherry is waiting for Dana to come home from her parents' house and then she's going to tell Dana that she and I have gotten involved and that Dana is not supposed to have sex with me anymore."

"Interesting. You and Dana's mom. It's almost like a porn movie. You get the daughter and then the mother." Deb raised her eyebrow at me and I could tell she was joking.

"Gee, thanks."

"Well, Dana and I have been watching porn and having sex for a while now. So don't think we haven't seen some of those. She's young, too. She always had us call her Sherry. And let's face it, Sherry is fucking hot." Deb leaned back and rubbed her hands over her nipples. "And I get horny so much more quickly now that I have had a regular cock to play with."

John shook his head. "Please don't. You are so irresistible that I may not be able to stay away."

"Who said you had to?"

"Let me see how things go with Sherry today, okay?"

"Okay." Deb spread her legs and rubbed her pussy. "Maybe you could just go down on me for now? My pussy really needs a cock or a tongue."

John shook his head. "Damn, you are insatiable."

"No, just horny at this moment." She continued to rub her pussy and then started pulling on her nipples with one hand. She was definitely horny and hot. "Well, maybe a little."

John moved to sit beside her and put his hand on hers, over her pussy. "Well, maybe I can just help you rub one out. That's not really having sex with you, is it?"

"No, it's just lending a helping hand. I appreciate it Mr. T."

John lifted his hand up and Deb lifted her hips and stripped off her little white shorts as quick as she could. She wasn't wearing panties.

"I see you came prepared for being naked quickly."

"Yes, sir." Deb yanked her shirt over her head and was naked. "Now do me, Mr. T. I need some attention from something other than my own hand."

John leaned over Deb and whispered in her ear as he put his right hand on her right tit. "I'm going to stroke you until you cum, little girl. I'm going to stroke your tits slowly, like this." John did that. He lightly stroked, pinched, and rubbed her tits and nipples. Deb kept her right hand on her pussy, rubbing it, getting it wet. Her head was back with her eyes closed as she paid attention to the sensations rolling through her body.

"Then I'm going to run my hand down and play with that little bald pussy." John ran his hand down there and Deb moved hers. "I'm going to play with that hungry, wet pussy and make you cum."

John ran his fingers through her gash, feeling the wetness. "You are a sopping, wet, horny little bitch."

Deb groaned. "I told you!"

John worked his fingers into Deb's pussy. "Such a beautiful, tasty pussy. I love your pussy, Deb." Deb just slouched further down while John stroked her. "I'm going to make you cum soon." John then ran two fingers into her pussy, reaching for and finding her g-spot, which he was already familiar with.

"Oh my god." Deb was rolling her hips now, helping John bring on her orgasm.

John rubbed her g-spot with two fingers and moved his thumb in circles over her clit. Deb was in full thrust mode, now, really close to orgasm.

"Fuuucccckkkk!" Deb jerked under John's ministrations, her orgasm washing over her. She arched her back, bringing her legs up tight to her chest as she came. Her toes curled and her eyes closed as she continued to jerk and spasm.

Finally, she was done. Her entire body relaxed. Her legs went down and her head fell back. She started taking deep breaths. "Oh, god, I really needed that."

John shook his head. "I really didn't have to work too hard. You were already so worked up it was easy."

"I know. I've been horny for a couple of days. What I really need is your cock." Deb reached for his crotch.

"It will have to wait, sweetie." John patted her on the stomach and then brought his wet fingers up to his mouth. He sucked on them briefly. "Yum. Delicious."

"You can have some right now." Deb lifted and opened her legs again.

John laughed. "You are such a horny, insatiable slut. I didn't know there were girls like you when I was young."

"Some of us are always horny, just like the boys."

"Yes, well, you'd better get dressed. I'm expecting a call from next door soon."