Training Lolita Ch. 05

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

All four of them got up and gathered up their clothes, Deb in the kitchen. They met at the bottom of the stairs and headed upstairs. John showed Bob and Candy where their room us and told Deb to get in his bed. She scampered off quickly with a giggle.

"Just make yourselves at home."

Bob was putting his clothes on. "We left our bag in the car. I'll be right back."

Candy turned toward John. "I want one more fucking tomorrow morning, John, so don't waste it on that little girl."

"She may be young and tiny, but she's not innocent so don't think she is."

"I didn't mean it that way."

"Okay, but I have something else in mind. I want you again, but after I give Deb a little present in the morning. That okay with you?"

Candy reached down and grabbed John's cock. "As long as I get another fuck, of course."

"Good. See you in the morning."

John walked into his bedroom and Deb was in the bathroom brushing her teeth. He joined her and then joined her in bed. "That was fantastic, Deb. You are quite the sex-loving little teen."

Deb grinned. "I love having sex with you, Mr. T. I love how you like to play."

"Okay, let's get some sleep."

John turned off the light and thought about the morning. He smiled to himself at his plans.

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John awoke the next morning to the feeling of a mouth on his cock. He pulled back the sheet and found Candy staring at him. She grinned. John looked over at Deb who was still sleeping soundly. John pushed Candy away from him and she frowned.

"Just a minute. I have a plan. Go wake up Bob the same way and bring him with his hard cock in here. I am going to work on Deb. I am going to get her on top of me cowgirl and then I want you to lead Bob in here to help me DP her."

Candy grinned. "Oooh, I like that. I'll get fucked afterwards?"

"Of course."

Candy scampered into the other room and John started slowly rubbing and playing with Deb. She stirred a little as he rubbed her tits. She was on her back and he rubbed up and down her body, each time ending up at her tits where he lightly rubbed and caressed her nipples. She finally came awake with a moan.

As she woke, Deb began to groan a little. She turned toward John. "Just a second, Mr. T." Deb got up and trotted into the bathroom.

John lay there, his hard cock softening with the absence of his pretty little 18 year old plaything. He waited for her to return and wondered how she would feel about being DP'd.

Finally, after a few minutes during which time John had become a little concerned, Deb returned slowly, seemingly deflated. "What's wrong?" John was afraid it was something to do with Candy and Bob and last night's interactions.

Deb sat on the edge of the bed in his robe, which she had grabbed from the hook in the bathroom. John always thought she looked so little girlish and cute in a robe that she seemed to get lost in.

"I'm bloated and bleeding. I got my period."

John put his arm around her shoulders. "I'm sorry, Deb. That's fine. There's nothing that can be done about that and it's perfectly natural."

"But I am a nasty, snarly, bitch when I'm like this. I get cramps and it makes me cranky and leads to me being so nasty. I just feel awful for about 3 days."

John sat up a little more and hugged her tightly. "It's fine, sweetie. That's life. Things happen and we will be fine. Do you want to go home?"

Deb nodded. "Yes, I have to. I only carry one tampon and I will need to get some more." She looked up at John and gave a weak smile. "Unless you keep some in the house, just in case."

"Unfortunately, no. But maybe I should get some to stock up for you and Dana."

"But we'll be leaving for college soon, so it won't be necessary soon."

"True. Why don't you get dressed and go home. Just call me later and let me know how you are doing." John leaned over and kissed her on the top of her head.

"Thanks, Mr. T." Deb suddenly threw her arms around John and just hugged him.

After about 30 seconds, Deb pulled back. "I'll head home now."

"That's a good idea, Deb. I'll let Bob and Candy know about this."

John walked out of the room while Deb dressed to leave. He went to the guest bedroom where Bob and Candy were. When he walked in, Bob was lying flat on his back on the bed. Candy was on the side of the bed and was bent over, sucking his cock. She had her right leg on the floor and her left knee on the bed, while she had her left hand on his thigh and her right around the bottom of his shaft. She was slowly bobbing on his cock. John could see her asshole and pussy clearly as her position left her legs so widely spread.

Bob had his eyes closed and Candy was facing away from him with a mouthful of cock, so neither saw John approach. It wasn't until he placed his hand on Candy's pussy that they both realized he was there. Candy started and made a short moan onto Bob's cock. Bob opened his eyes and grinned.

"Hey, John. So what's the deal this morning with your cute, little friend?"

"Well, there's been a change of plans. Deb woke up and found that she started her period. She's getting dressed to head home."

Candy pulled off Bob's cock. "Oh, that's too bad." John didn't remove his hand from her pussy, however. He kept it where it was, just laying on and covering her pussy.

Bob shrugged. "She was a cute and dirty little thing. Too bad we don't get some more playtime with her."

Candy wiggled her hips. "Listen, as long as you're here, I'll go back to sucking Bob's cock and you fuck me like you mean it."

John grinned. "That sounds like a good plan."

About that time Deb came in dressed and ready to go. "Goodbye everyone. It was nice to meet you Bob and Candy."

Bob waved. "It was nice to play with you." He grinned.

Deb waved back and Candy pulled off Bob's cock. "Yes, it was fun."

Deb came over and looked down at the two of them. "Is she a good cock-sucker, Bob?"

"Yes, she's very good."

Candy pulled up off of Bob. "I love sucking cock almost as much as you do, you little slut."

Bob pushed her head back down onto his cock. "Shut up slut." Candy giggled around Bob's cock.

Deb looked down at John's cock. "You're not hard anymore. You need to get hard again and fuck Candy." Deb grabbed John's cock and it started firming up. She grinned up at him. "I'll get you hard before I go."

Deb removed her hand and moved it over to Candy's pussy. She rubbed around and gathered some wetness. Candy wiggled her hips. Deb took two fingers and slowly pushed them into Candy's pussy. Candy groaned around Bob's cock. Deb slowly started finger fucking Candy and looked up at John.

"Look at how I'm finger fucking this cock-sucking slut." She reached out and grabbed John's dick with her other hand. "I know you want to put your big, hard cock into this hot, wet pussy."

John smiled and his cock hardened. He watched Deb closely and she pulled her fingers out of Candy. "Here, let me get your cock wet with her pussy juices. She is a very wet slut. Fuck her hard for me."

Deb tugged on John's cock and he moved directly behind Candy. Deb moved back a little and pushed on John's ass. "Fuck her."

"If you insist." John grinned and centered his cock on Candy's pussy. Deb pushed again and he buried his cock into, as Deb described, a hot, wet pussy.

Deb moved behind John, plastered herself up against his back, and reached around to grab Candy's hips. She could barely do so, but she grabbed as much as she could and started rocking and pushing, trying to set a fast tempo. John put his hands over hers and complied. He started pounding Candy and suddenly Bob came.

"Fuck!" Bob groaned and filled Candy's mouth with his cum.

Candy kept sucking and swallowing until she was sure she had it all. Then she pulled off his cock with a pop and groaned. "Fuck me, baby. Fuck me hard. I want to cum in this position. Make me cum until I collapse."

John was more than happy to pound Candy. He felt Deb pull away so he took total control. He pulled his cock out about ¾ of the way each time and then buried it in Candy's sloppy cunt. He pounded her and the slapping of his hips against her nice, round ass resonated around the room. She just groaned and arched her back, trying to heighten the fucking she was getting.

Candy loved all sex and this was very exciting. She was getting pounded by a cock that was the perfect size for her and it was pushing her toward a fantastic orgasm. She decided to hurry things up and reached down to rub her clit. She just started rubbing it when John pushed his finger against her asshole and stimulated all the nerves there. That combination pushed her over the edge. She jerked and shook and groaned when it hit. "Oh, fuck yeah!"

John pounded Candy through her orgasm, watching as she jerked and moaned through it. He kept up his fucking, knowing he was close to cumming, too. Her pussy had pushed him real close when it spasmed and seemed to suck at his cock. Now he finished it off.

"I'm going to cum, too. I'm going to fill up your cunt...." John couldn't finish his last sentence. Just groan as he buried his cock in a delicious hot, wet cunt and spurted. He did that about 5 times before his desire to thrust and cum ended.

When he finished John slowly pulled out and watched as his soaked cock came out. He looked around and noticed that Deb had left at some point. He saw Candy slowly turn and lay down on the bed next to Bob.

"Whoa. I really liked that." Candy grinned.

Bob looked at her. "I could tell. You also look like you could use a little cleaning up."

Candy looked down her body. She was sweaty, dirty, and had a pussy leaking cum. "No kidding. I really need a shower now."

"Go ahead. You know where everything is now." John patted Candy on the thigh and walked out. He went directly to his bedroom and picked up his cell phone. He dialed Deb and she answered immediately.

"Hi, Mr. T."

"You left quickly."

"I had to get home. Sorry I did it when you were not looking, but you looked a little busy fucking Candy."

"Yes, I suppose so." He took a deep breath. "I just wanted to make sure you were okay."

"I'm fine. I just needed to get home."

"Call me later, okay? I just want to make sure you are fine, Deb. I like you and don't want you to feel like I don't or that you don't mean anything to me."

"I will, Mr. T. Thanks. I like you, too."

John hung up and went to get some breakfast. Bob and Candy came down a little while later, dressed and ready to leave. They all had a little breakfast and then the wild couple left. John was glad when they left. He loved the sex, but there was something to be said for a nice fun fuck with just one of his teenagers. They were a fun-loving, adventurous pair. Being new to sex made everything interesting and exciting to them and he loved seeing it through their eyes. It made him feel young again.

At about 4pm, he was surprised when Dana showed up. She was supposedly very busy and getting ready for college. She walked in, kicked off her shoes, and then stripped off her shirt, bra, yoga pants, and panties. She walked while stripping, leaving a trail behind her, and then crawled up on John's lap, facing him.

"Hey, Mr. T."

"Well, hello to you, too, you vixen you."

Dana grinned. "I am, aren't I? I just love sex now that I know how fun it can be. And I can't help but be in your debt since you have been teaching me."

"Well, I know you wanted to learn, and I figured I could take some time out of my busy schedule to help you with it." He gave her a sly grin.

"Yeah, I know it's been very difficult for you to make the sacrifice and have sex with a couple of teenagers."

"Yes, it was very tough. Now, back to you. Did you come over here just because you wanted to have sex? What makes you think I want to have sex right now?"

Dana pouted and tried not to grin. "Mr. T. When have you ever not wanted to have sex with me?" Damn, she was so fucking cute and hot when she did that fake pout.

John leaned back and looked up at the ceiling, pretending to be concentrating on a difficult problem. "Uhhhhhh -- never!" He grinned and started tickling Dana. She squirmed around and laughed and giggled, trying to get off his lap. "I just love tickling naked women."

Dana finally managed to squirm free and stood in front of John with her hands on her hips. She was quite a sight. Her breathing as a little heavy and her gorgeous tits rose and fell with the motion. Her hair was disheveled and she shook it as she stood there, making those tits jiggle even more. They were so delectable. Her smaller waist gave way to nice, rounded hips and there in the middle of this view was a clean shaven pussy. John started to reach out for her.

"Uh, uh!" Dana shook her head no and waggled her finger as she backed away.

John was just starting to get up and come after her when the doorbell rang. They both stopped and stared.

"Are you expecting somebody, Mr. T?" She suddenly looked very young as she covered her body and looked a surprised.

"No." He started toward the door. "I'm going to answer it, so you'd better pick up and hide."

Dana scrambled to grab her clothing and John couldn't help but watch as such a beautiful body went through the gyrations and jiggled and shook in all the right ways. After picking up what little clothes she had worn, Dana headed up the stairs to his bedroom and he continued to watch her ass all the way up. At the top of the stairs she turned and grinned.

"Enjoying the view?"

"Fuck, yeah!"

She shook her tits at John. "Good." Then she scampered to his bedroom.

John chuckled at her playfulness and headed for the door. He got there just as the bell rang for the second time. When he got there he looked through the peephole and got a bit of a shock. It was Dana's mother. Now what was he going to do? She was supposed to be at work and here she was looking for the little minx that just stripped for him in his living room. He looked back to the area and didn't see anything amiss, so he opened the door.

"Hello, Sherry. How are you today?"

She gave John a quick smile, which always did look good on her. After all, Dana was just a younger version of Sherry. And Sherry was still younger than he was and a fine specimen of a woman.

"I'm fine. I'm looking for Dana and wondered if you had seen her or heard anything from your house."

"No, I haven't seen her or heard anything. Is there anything wrong?" He hoped he lied convincingly.

"Not really, she is, after all, 18." She looked up at John. "Can I come in for a moment?"

"Oh, I'm sorry. Where are my manners?" John opened the door wider and stood back, allowing her to get by. "Please come in." She breezed by, smelling of the same perfume that Dana had been wearing. So Dana had been into her mother's perfume, eh?

Sherry was dressed in a nice skirt and blouse and, as John watched her, he had to admit that she looked very good. "Can I get you something to drink?" He was hoping she would say no so that he could get her out of here, but he had to be a good host or she might get suspicious.

Sherry walked into the living room and sat on the couch. "Sure. I'm supposed to be at work, but I've been worried about Dana and there was an opportunity to swap shifts with someone so I came home to talk to her."

"What would you like? Water, soda, something stronger?" John didn't think she'd accept anything else. He had never seen her drink.

"Do you have any scotch?"

John stared at her for a second. "Uh, sure. I have two very nice bottles open right now, a Macallan and a Glen Livit." He offered her the best. Part of it was to offer her a good scotch, but maybe a little of the reason was the feeling of guilt he had knowing he was fucking her daughter and she was, at this moment, up in his bedroom.

"Oh, great. The Macallan would be fine. Neat, please."

John went to his small bar and poured the two of them a small neat glass of scotch. "You know, in all the years I've known you, I've never seen you drink alcohol."

She sighed. "Well, I don't do it much. I've gone very light since Dana was born - single mother and all that."

John hadn't ever heard anything about how she came to be a single mother and had always wondered about that. John steered away from that, not wanting to get into anything too deep with Dana upstairs, and instead thought he would offer her a complement. "Well, you probably were barely old enough to drink when you had her. You look way too young to be the mother of an 18-year-old."

Sherry stared at him for a second, took a big slug of the scotch, and then fell back against the couch. "You have no idea."

John watched her closely. "Is there anything I can do?"

Sherry looked at John and gave a big sigh. "We've known each other for a long time and I think maybe I'll tell you something that would make things a little clearer to you."

John said nothing. He took a sip of his scotch, wondering where this was going. Since his chair was facing the couch and the stairway, he could see that Dana had now crept into view at the top, listening to the conversation. He'd better be careful. "Not necessary. I just always thought that you looked great for a single mother."

Sherry smiled. She sat forward and looked down at her drink. "Thank you. But you should know that I'm not as old as I tell everyone. I know that's hard to believe of a woman, but I actually started lying about my age long ago and kept it up because of Dana."

John looked up at Dana and could see she was hanging on every word. Maybe she shouldn't be listening. He suddenly stood up. "Would you like me to refresh your drink?"

"Yes, please."

"So what were your plans since you are suddenly off?"

"Are you trying to change the subject? Is this making you uncomfortable?"

"No, I just thought that maybe you didn't want to really tell me this based on how you were talking." John hoped that she wouldn't say anything with Dana on the stairs.

"Well, my plans and what I'm about to tell you go hand in hand. In fact, I was hoping that you would keep an eye out for Dana because of this."

Sherry paused and took another drink. John fidgeted and glanced up at Dana again. She was not going to miss this chance to hear her mother speak.

"Okay, here goes. It's come to my attention based on a few things, that Dana is sexually active."

John was in the middle of a drink and almost choked on his scotch.

Sherry looked at him and waited until he quieted down. "You okay?"

"Yes, yes. I was just a little surprised at the subject." He tried to cover his shock since he was the one doing the fucking.

"Well, we're all adults here. In any case, I've become aware of this and I wanted to discuss this with her, but we've been at odds lately and there doesn't seem to be a good time or place. One of the reasons is that I've been lying to her for years about my age and when I had her. You see, I was a 16 year old pregnancy." She waited for John to react.

John listened and tried to be calm and he was. He didn't let on too much, but was a little surprised and raised his eyebrows.

"I was pregnant at 16 and had to work hard to get to where I am. I know she's 18, but I want her to be careful about all this. I had to do things the hard way, getting my degree while I had a baby at home. I want her to go to college and have a better life start to her life than I had. I've had her on birth control since she was 16 and tried to protect her, but she's almost a woman now. I know she's curious and my god, with today's social media, they all know everything by this age. I just want her to be careful and talk to her about sexual activity and how it's perceived. Unfortunately, we've been at odds for a while so we never get around to having that talk."