tagAnalLiking the Naughty Girls

Liking the Naughty Girls

byMisterNatural©

Alan Winter wasn't in the Shop and Save to buy anything but that didn't mean he wasn't doing some shopping as he pushed the empty cart up the aisle. The middle aged divorcee did put a bag of carrots in the cart just so he didn't look stupid, but his eyes were on the girl who he had noticed coming into the market as he was leaving the bank next door.

To most men the chunky brunette would have little appeal since she was rather ordinary looking and wore nerdy glasses in addition to carrying about 30 extra pounds on her 5'4" frame, but as he had been told many times, most recently by his now ex-wife, Alan Winter was not most men. Besides, the 51 year old insurance agent had a very intimate knowledge of the girl he was tracking through the produce section.

Actually, his intimate knowledge was not gained by him directly but through his son, who had dated the portly girl until he went off to college a few months ago. What he knew about Peggy Preston he had learned by being a good father, and in this case what he knew about Peggy he discovered through his through parental skills which included some snooping and eavesdropping.

His boy Ricky, while a good kid was not all that mature, and he had a habit of talking a lot on the phone to his friends. Not only did Ricky talk loudly he also was not very discreet, sharing intimate details of his relationship with Peggy Preston to the knuckleheads he had hung out with when he was living at home. Not very classy, something even an old horn-dog like Alan would admit, but it did force him to look at the seemingly ordinary teen in a different light, and the more he had found out the more he came to the same conclusion his boy had. Peggy Preston was not the right girl for Ricky, but right up his Dad's alley.

While admiring the full butt Peggy's jeans contained, he had to admit that he would never have figured the quiet girl to be - well, a bit on the naughty side. Nasty might be a better descriptor for what Peggy Preston seemed to enjoy, but one guy's nasty is another guy's nirvana. So he hadn't handed down his own preferences down to his son? No matter.

Sensing that Peggy was only picking up a few things the insurance agent decided to make his move, and as he maneuvered his cart to "accidentally" cut her off at the end of the aisle he struggled for an opening remark.

"Peggy Preston!" Alan exclaimed with fake shock, and when the girl smiled broadly he kept going. "Long time no see. I really miss you hanging around the old homestead."

"Hi Mr. Winter," the girl replied, her chubby cheeks with a healthy glow as she grinned. "I miss seeing you too although you probably got tired of me hanging around."

"Never! Your smile brightened the place and having a cute young lady around is never bad. You're looking good."

"You too sir," Peggy replied. "Have you - uh - heard from..."

"Ricky?" he asked as he finished her struggling sentence, and when she nodded e said, "Only when he needs money. I assume he communicates with his mother the same way."

"Oh. I guess you two are still apart?" she inquired.

"Separated is the term, and I guess that's just because we're too lazy to finish it off," Mr. Winter explained.

"That's too bad. Well, if you talk to Ricky tell him I - I guess tell him I said hello."

"I will," the boy's father responded, although he knew he wouldn't do that in fairness to her.

Ricky didn't care about Peggy. That was obvious because to his friends he had referred to her as "Piggy", and you didn't complain about her tits being too small, about how chubby she was and how her pussy was so hairy he had trouble finding it, not that she had ever let him in there. That was his major beef with Peggy, her rebuffing his efforts there although the way he talked, there was nothing else she didn't offer.

"Lousy weather out there," Mr. Winter offered, cursing the dampness that had Peggy in a jacket and depriving him of a glimpse of her tits, which might not have been big enough for his boy but were fine with him.

"I know, and the snow will be coming way too soon," Peggy offered as she pushed her glasses back up her nose.

"Say, I don't know if you're busy but how would you feel about going somewhere for drink?" he offered nervously, and when the girl made a face he gallantly offered her an out. "If you wouldn't mind being seen in public with a dinosaur like me that is. The Come Right Inn maybe?"

"No, they know me there," Peggy answered, and when he suggested The Outpost as an another gin mill option she shook her head again. "No, they know me there too."

"Wow, you get thrown out of a lot of bars, don't you?" he chuckled but the teen laughed and explained.

"I'm not old enough to get in. 19, just turned," she responded. "I have tried though."

"Dumb law. My bad. I forget how young you are because you're so mature for your age," Mr. Winter told her, and judging by reaction Peggy enjoyed hearing that. "Too bad. I was looking for a reason to not go back to an empty house. No fun being lonely."

"Tell me about it," Peggy agreed.

"No replacement for Ricky?" he asked, and after she shook her head he did the same. "What's the matter with the guys in this town?"

"Nobody likes a fat girl. That's why Ricky dumped me."

"That's crazy. You aren't fat. A bit chubby maybe..."

"No, he wanted somebody to show off up at Delta Lake last summer," Peggy explained. "That sure isn't me. Heather McCoy? She was my replacement until Ricky went off to school."

"Don't think I saw her," Alan Winter lied, having seen the willowy blonde a couple of times and had been unimpressed. "Anyway, in the end you will think it all worked out for the best because Ricky? I love him but he's got this frat boy attitude and isn't even in a fraternity. You deserve somebody more mature."

"Maybe," Peggy shrugged.

"Speaking of mature - I have an idea. Why don't I go grab some beer and we could go out to River Road and catch up?"

"I dunno."

"It's drizzling out so nobody would see us if that's what concerns you," Alan offered with a sheepish grin. "Save you a walk home, even if it is a short one. It's daylight too so you can trust me."

"I trust you Mr. Winter," the teen replied and then after giving it a bit of thought said, "Okay."

"Great! You check out and I'll meet you out under the awning."

***

"Deserted out here," Alan Winter mentioned after he pulled into the little parking lot that was used by hikers, and after he killed the car swiveled to face her boy's ex-girlfriend while reaching into the bag to pull out a couple bottles of Sam Adams Cherry Wheat.

After cracking them open and offering Peggy one he smiled and asked whether since she still liked this, explaining that he had found empties in the trash back when she and Ricky were dating.

"Guess we weren't as slick as we thought," Peggy acknowledged.

"None of us are," Alan agreed, and as he looked at the cherubic face beside him with the faint swirl of down around her ear the sweet scent of some inexpensive perfume filled the car "So, you're 19 now?"

"Just turned last month."

"Well a belated Happy Birthday to you!" Alan chirped as they clinked bottles, and after they sipped he added, "We could have had a big party because I've got some socks that turned 19 too."

Peggy got a giggle out of that, but after they sat and sipped in silence for a minute or too the girl asked whether Ricky ever asked about her when he called.

"Look Peggy," the insurance agent said as he decided to set the kid straight so she wouldn't carry a torch forever for a guy who didn't care for her as anything but a sperm bank, but do so in a way that didn't destroy her. "I know this is tough because I've had to deal with it too, but Ricky's in your rear view mirror and he isn't coming back."

"But I really love him," Peggy insisted.

"I know. Back in college I bought a piece of crap Ford Pinto that I was crazy about, and even after it caught fire in the Interstate I still had happy memories of it, but it was over. Maybe it's not a great analogy but you need to come to grips with it. If I wasn't really fond of you I wouldn't care but I do. He just had no respect for you."

"He was nice to me - most of the time," Peggy said hesitantly.

"And after you two broke up he did nothing but run you down to his buddies," he told the somewhat shocked girl. "This things he told them about you two. What you did and what you liked? I was embarrassed for you because those things should stay between lovers, and I never really did much snooping to find this stuff out. He bragged about it and sent all sorts of graphic e-mails."

"I can't believe this," Peggy maintained as she drained the bottle and grabbed another.

"I shouldn't have said anything."

"What did he say?" Peggy asked after a moment, and when he hesitated she insisted. "I need to know."

"I really don't feel comfortable about this."

"Let me guess," Peggy offered. "He told the guys I need implants and should go on a crash diet. Get liposuction too, and I'm sure he said I should get electrolysis too."

"Look, not in so many words maybe," Alan responded. "He's an immature kid who has a kind of twisted idea of what a woman should be. He didn't get it from me, that's for sure. I shouldn't have said anything but seeing as how you still have hopes of him coming around..."

"No, you're right Mr. Winter, and I did ask for it," Peggy admitted. "He didn't send any pictures to anybody did he?"

"I don't think so," I lied. "Like I said, I didn't do any investigative work."

"Thank heaven for small favors."

"Honesty is a great trait but I guess we have to be careful about who we let into our heads. Not that I'm ashamed or anything but I know I wouldn't be crazy about my fixations or predilections being common knowledge."

"What do you mean Mr. Winter? What else did he tell them?"

"He just mentioned about how you wouldn't do a certain something because you were afraid of getting pregnant."

"Omigod."

"Hey, it's not a bad reason. It shows a level of personal responsibility you don't see much of these days, and it wasn't as if you just turned him down cold," Alan Winter said as he patted her thigh from the other side of the console. "I wouldn't mind being a grandfather some day, but only when the time is right."

"Didn't turn him down cold? What do you mean?" Peggy asked.

"Ricky said that you were kind of only interested in him doing..." Alan responded and waited for a better wording before he finished. "He told them you only wanted him to take you anally."

"Son of a bitch," the teen muttered to the fogged windshield. "Unbelievable. You don't know how many people he blabbed about this to, do you Mr. Winter?"

"I have no way of knowing," he admitted, wanting to hug the kid but the logistics made that option tough.

"It would nice to know the list of people I can't look in the eye anymore," Peggy spat out. "No wonder nobody had asked me out. Even Father Byron gave me a weird look at church one time. Thought it was my imagination but..."

"I'm sure it was. Ricky thinks the walls of St. Mary's are radioactive so he wouldn't have made confession about this."

"Still, boys talk."

"I guess, but if you do make that list of people you think have passed judgement on you, please don't put me on it Peggy. That would hurt me because I certainly don't think any less of you for anything I heard," the middle aged father said while counting his blessings he never had any girls.

"The reason I gave Ricky - about not wanting to get pregnant?" Peggy said as she shyly looked at the older man out of the corner her eye. "That wasn't - well it wasn't the main reason. That was the reason my uncle gave me back in the day when he, you know? Told me he didn't want to knock me up so he did me in the ass instead every time his family would visit ours."

"Oh."

"The main reason I wanted Ricky to have me anally was because I like it. A lot," the teen said as she paused while looking for a reaction she didn't get. "Plus, someday when I get married I'll be able to present myself to my husband as a virgin. I get the hypocrisy but it's my way of justifying what I do."

"We're all hypocrites in one way or another but just like I said before, I think nothing less of you for any of this, and in many ways I respect you even more for being so honest," Mr. Winter admitted and as the teen finally raised her eyes to meet hsm he offered a smile and a final comment. "It's not a crime you know? Enjoying anal sex I mean. If they threw all of us in jail who love it they would run out of cells."

"You mean?"

"Always have and always will," he nodded while confessing. "My mistake was in marrying a woman who was a lot more white bread than she let on at the beginning. Naomi got less and less interested over the years in what she said were my kinks so here I am."

"Wow. I wouldn't have guessed."

"That's good because it's nobody business except mine and those I choose to share it with," Alan said. "I trust you because I guess we're kindred spirits in a way, and that if I am going to be 100% honest if I was your age I would be all over you."

"Bet you wish I bought more beer," Alan Wilson said after the silence filled the air while the rain tapped on the windshield.

"No, I've had enough beer," Peggy told him as she took of her glasses which had also become fogged, and after wiping off said, "I never had a clue. All those months I was seeing Ricky?"

"I was still pretty married back then, and besides Ricky is my son and you were dating. What was I to do? Tell you I was really attracted to you? Admit that whenever you walked past me my eyes were all over your backside?" Alan explained. "You would have thought I was an old creep and told me to take a hike."

"Maybe the last part but you were never a creep. You were always nice to me, a lot nicer than Ricky's Mom was."

"That's mothers for you. Nobody is ever good enough for their baby," Alan chuckled.

"My Mom is that way with me I guess."

"If I had only known more about you back then then I not sure I would have been so noble regardless of everything else," the older man admitted, reminding Peggy that until they split up he had thought she was just a shy and straight-laced kid.

"Does that matter?" Peggy said in a stage whisper.

"You mean about thinking you were shy?"

"No, I meant the part before about you being so much older than me?" she asked, swallowing hard and starting to breathe heavier. "Does that matter?"

"To guys? I don't think so," Alan grinned. "Girls though, not that's a different story. Not many want to be seen with a fossil."

"Not me. I'm not like that. Been with some older men," Peggy suddenly shared and then added, "Too much information huh Mr. Winter?"

"No honey. Are you saying that if I called you sometime you might want to go out with me?"

"Sure. It's not like there's a waiting list."

"Well, when would be a good evening for you?" Alan said as he acted like the insurance agent he was, moving in to seal the deal before he had a chance to reconsider. "Next weekend?"

"Sure," Peggy said. "Tomorrow night? Now?"

"Now?" Alan repeated, and after Peggy shrugged he went on. "Do you have to bring any of your stuff home? Need to call your folks?"

"No. I'm 19, remember?"

"Right. Where would you like to go?"

"I know I look a mess," Peggy said as she dropped down the visor and looked at the mirror, frowning and trying to fluff up her shag do. "Can't go to my house."

"Mine?" Alan offered. "Or is that too many bad memories?"

"No, I was in Ricky's bedroom, not yours," Peggy said softly, and since that answer took care of many questions the older man simply turned the engine on and waited impatiently for the defoggers to work.

***

"Different kitchen table," Peggy noted as they entered the kitchen, and as he helped the teen off with her jacket he explained.

"Lost the custody battle on that," Alan said. "Guess her new stud muffin didn't have one, but to be fair she was good about most of the stuff we had accumulated."

"12?" Alan kidded when he saw the jersey Peggy was wearing under the jacket. You don't look 12. I thought you said you were 19?"

"Ha! My Dad bought this for me for some reason," Peggy explained as she spun in place. "He likes the Patriots and Tom Brady."

"I'm a Giants fan but that's okay. You can stay," Alan said. "Can I get you anything?"

"Maybe a glass of water?" she asked, and took the bottle of spring water her host produced from the refrigerator. "Dry mouth. Is that a sign of nervousness Mr. Winter?"

Ricky's father held up a finger but said nothing until retrieving his own bottle and taking a deep swallow, and only then said, "It must be."

"Did you get taller?" Peggy asked of the man was about a head taller than she. "Hope I'm not getting shorter."

"I don't think so," the insurance man said as he read into her comment that she looked much like Ricky, except with his Dad being taller and considerably thinner, not to mention the great streaks in his hair than he hoped added an air of distinction to him.

"Anyway, since we've been so honest with each other, can I ask you for some favors before things start happening?" Peggy asked. "If you find any of this off-putting just say so, okay? I know I'm strange but, hey, you knew that already."

Peggy went through a little list of things that made it better for her, blushing a little as she spoke, but when she finished Alan Winter simply shrugged and said the specifics for what amounted to a little role playing were fine with him.

"Cool," Peggy responded. "Never been able to say that stuff to somebody right off, and if there are things you like just do them. If I have a problem with anything I'll just say, Aunt Emma!"

"I'm sure there's a story behind that but I get it."

"And if I do anything you don't like..."

"I'll use Aunt Emma too," Alan said with a nervous grin. "One thing though. You can call me..."

"Mr. Winter," Peggy interrupted. "Forgot that part but it's kind of important to me. Other than that, I'm yours to do with what you wish."

***

"You caught me, I didn't make the bed," Alan Winter said as he ushered Peggy Preston into his bedroom.

"Big bed," Peggy noted.

"Especially for one person," her host said as he led the teen over to the dresser opposite the king-size bed and stood behind Peggy as they looked at their reflections in the mirror.

"You look so cute Peggy," Alan opined as he rubbed her round shoulders before bringing his hands up to run his fingers through her slightly disheveled brunette locks, fluffing up the shag cut before letting his hands go down the shoulders of the uniform top and down her arms, savoring the feel of the down on her forearms.

"I'm scared Mr. Winter," Peggy whispered in a voice that might have been more reality than act, but the older man bought it as he kissed the back of her neck as he leaned into her backside and removed her glasses.

"Nothing to be frightened of honey," Alan assured her, and as he grabbed the bottom of the jersey he added, "We'll put your glasses back on but first let's get this off of you. Upsy-daisy."

Peggy obediently raised her arms, allowing the older man to slowly pull the garment upwards, exposing first the little muffin top above the shorts and then Peggy's thick waist before sliding up over her brassiere. With the insurance man's heart already racing, his interest rising exponentially when he started to pull the shirt up the girl's arms before she quickly pulled the shirt back down and put her hands on the dresser.

"Time out" Peggy said as her chest heaved. "Have to go to the bathroom for a sec. Won't be long."

"Wait honey. Do you need to take care of a bodily function or is it something else you're planning on doing?" Alan asked. "Because if you're planning on rummaging through the medicine cabinet for something like a razor, I'm afraid I can't let you leave."

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