tagAnalPortly Penelope Becomes Popular

Portly Penelope Becomes Popular

byVeryDirtyMind©

"You?" Ellen Doppler exclaimed when Penelope Smith corralled her in the back room of the EZ Mart and told her what had just happened. "Robert Redford asked you out?"

"Yes!" Penelope squealed happily, savoring the moment that always happened to other girls, not her. "He asked me last Saturday night too but I thought he was kidding."

"You sure he's not screwing with your head girl?" Ellen repeated, not believing that the older man who the help at the store referred to as Robert Redford was asking the chubby cashier out instead of somebody way prettier, like her for example.

"I said yes, or at least I think I did. I'm so nervous I don't remember," Penelope babbled. "Omigod. I can't believe this. I don't know what I'm supposed to do."

"It's a date for crying out loud. You've been on dates before," an annoyed Ellen spat.

"Yeah," Penelope lied. "But this is a man. A businessman..."

"I know I know," Ellen said as she turned to get back to her register. "He's older than white dog crap."

"Jealous," Penelope mumbled under her breath, and it was such a crazy feeling that she enjoyed it because it was true - somebody was jealous of her for once.

******

Penelope stood in the driveway of the modest home she shared with her mother after sneaking out the back, trying to stay out of sight in case her Mom peeked out. Penelope was tempted to just let her mother know what she was doing because after all, she was 18 and chipped in half of her check to the household, but she decided it wasn't worth it.

So what if Mr. Baxter was older than her? It wasn't like he was a wheezing old man getting around in a walker. He was tall and thin and very handsome, with flowing silver hair and the sweetest smile, and if Mom ever saw him she would want to be with him, even if Mr. Baxter was older than she was too. How old? 60 something? Who cared?

Then Mr. Baxter's car came down the street, a shiny black Lincoln Continental that sparkled in the moonlight, and Penelope tried not to faint as the car glided up to her. She fumbled with the door which seemed locked, but then she saw Mr. Baxter gliding around to open the door for her.

"Oh Penelope, you look even more beautiful away from work," He cooed, kissing the back of her hand before opening the door, and as the elegant man came around to the driver's side she decided he really did look like Robert Redford.

***

"We'll have bottle of the Alamos Cabernet Savignon with dinner too please," Mr. Baxter told the server as he handed her back the list, and then asked Penelope "Is that okay dear?"

The teen mumbled something as the server left, and when she was out of sight the young woman reminded her date that she wasn't old enough to drink and that they probably wouldn't let her have any but Mr. Baxter shook his head.

"Nonsense. You're very mature for your age, not to mention that you're the most beautiful woman in the restaurant. You look radiant tonight," he added, reaching over and patting her hand with his before letting his fingers slide up her arm a bit, causing the fine down that graced her forearms to stand at attention.

Penelope blushed at that comment, remembering how she struggled to find something to wear since the dress she was planning on wearing was tight in the belly and made her look pregnant, ending up having to wear a lavender top and black slacks. None of that mattered now since Mr. Baxter liked the way she looked and the teen only wished that somebody she knew was at the restaurant to see her with the handsome man.

***

"Oops," Penelope giggled as they left the restaurant, her gait a little off even though she had only had one glass of wine, but Mr. Baxter had her in hold and got her to the car safely.

"That was the most wonderful dinner," Penelope gushed.

"I agree. Wonderful food and charming company make for a wonderful dining experience," he agreed. "Would you like to go to my place for a cocktail before I take you home?"

"Er - um - I," Penelope mumbled as she panicked, but Mr. Baxter waved her off.

"I'm sorry. Rushing things here I guess," the senior said. "Next time maybe?"

"Um yes. Sure. Thank you Mr. Baxter," Penelope said with a sigh of relief.

"Mr. Baxter?"

"Sorry. Lyle."

"That's better," Mr. Baxter said with a smile, and as he tooled the car around the dark fringes of Penelope's neighborhood he asked, "You don't have to be home just yet though do you dear? Maybe we could find a place to - you know - talk for a bit?"

"Sure," Penelope responded and her date reached over and gave her thigh a squeeze, and when he suggested she slide over a bit she did as the car pulled into a dark one way street and Mr. Baxter turned off the engine.

"I don't think anybody will come by here to bother us," he observed as he pushed a button and the steering wheel swung to the side, and after he hit a switch to turn on soft music while he swiveled to face the teen.

"Scary to walk past here at night," Penelope observed.

"But you aren't scared now, are you dear," he asked, and although she said no it was without conviction.

"Let's see if I can make this a little brighter in here," Mr. Baxter suggested as he fiddled with a switch to make the dashboard light up a bit. "There. No fun sitting with a pretty girl if you can't see her. Let's see, right now you would be getting ready to close the store up, wouldn't you?"

"Yeah."

"You look so adorable in that uniform top they make you wear," Mr. Baxter observed. "But I like your blouse better. Let me see. Your little badge that says PENELOPE? That would be right about here, wouldn't it?"

The senior's long bony finger pressed into the blouse just above her right breast, and Penelope gasped when she felt the finger while Mr. Baxter leaned over towards her, his breath fresh from the after dinner mint from the restaurant.

"Your lips are so lush and full - I've wanted to kiss you from the moment I saw you," were Mr. Baxter's last words before he pressed his lips to hers, and after he leaned back a bit to see the girl's frightened reaction he asked, "You've done this before, haven't you honey?"

"Sure," came the jittery reply from the teen, hoping that the one time in the woods with Wayne Strait counted, and then Mr. Baxter's lips pressed down again, only this time with a lot more passion and the addition of his tongue slipping between Penelope's lips and dueling with hers.

"You're so sexy honey," Mr. Baxter murmured in between kisses that went down to her collarbone and back up, and when he took her hand and put it around his neck she didn't fight it. "That's it."

Penelope's head was spinning as she was kissed in a way she had never experienced before, and she thought of all the times she had practiced on her pillow late at night, pretending it was a boy. She barely noticed Mr. Baxter's hand moving up under her blouse, only realizing it when his fingers slid up her side, and the teen flinched when she felt the senior's finger under her upraised arm, stroking the moist peach fuzz that coated her armpit.

"So sexy," Mr. Baxter kept saying as he leaned Penelope against the back of the car seat, his hand slipping over to first cup her breast through the padded brassiere which was designed to make her pear-shaped body seem more symmetrical, and then smoothly worked under the cup to push the harness up to her collarbone.

Penelope's chest started heaving when she felt her date's hand on her bare breast, and while Lyle Baxter was a bit shocked when he learned how small the chubby girl's breasts were, barely filling his hand, he lovingly kneaded the orb as he felt her plump nipple swell into his palm.

"That's it. Relax honey, this feels good doesn't it?" Mr. Baxter asked before resuming his kissing, and although the teen was scared the necking and the petting were having an effect on her, so much so that when the senior brought Penelope's right hand down to the bulge in this trousers and squeezed his hand over hers her trembling paw did not pull away.

"Feel how excited you've made me?" Mr. Baxter told her as she tentatively held the bulge while his hand left her breast and went down, and although Penelope squirmed when she felt him trying to push his hand between her slacks and her soft belly, his strength won out and he worked his way down.

"It's okay - it's really okay," Lyle insisted as the girl writhed into the leather when his fingers got under the elastic of her panties. "Ooh! I knew you'd have a lot of hair down here."

"Sorry," Penelope croaked apologetically, knowing from gym class how much pubic hair she had compared to her classmates, but her date hushed her quickly.

"No dear. You're perfect. Ooh, the hair is so soft and dense," Mr. Baxter moaned as his fingers slid through the thicket until he felt the increasing dampness at the opening, and as his seasoned digit slipped in between the plump labia he declared, "and you're so wet too honey. You're as excited as I am."

"No please," Penelope whimpered inaudibly as the man's finger pushed into her while he implored her to relax.

"It's okay Penelope. Just spread your legs for me a little," Mr. Baxter insisted as he brought another finger to the fold, and as he began working the fingers in and out he was all over the girl, kissing her hard as he leaned over the teen.

It was over quickly as the senior used his experienced fingers and talented tongue to make the girl writhe and buck in the seat, and when Mr. Baxter felt Penelope's sex clamp down around his fingers as if she was trying to break them he leaned away and watched the girl cum hard, her feet kicking the underside of the dashboard as she bounced around like a puppet on a string until the convulsions finally ebbed.

"Oh sweetie, I don't even have to ask to tell that you liked that," Mr. Baxter declared after he pulled his handout from her slacks and looked at the dazed girl with the flushed face, and the way her glasses had been knocked a bit askew made her look even more out of it. "That was so sexy. It was like you never had an orgasm before."

Penelope said nothing as she fought to catch her breath as her heart began to bet at a more regular rate, too embarrassed to admit that while she had orgasms before, they were never with the help of anybody else and they were never anything as intense as that had been.

"As you can tell honey, it was exciting for me too," he noted as he nodded down to her lap, and even in the dashboard lights the teen could see the way the senior's baggy slacks were tenting upwards. "I love how shy you are, but don't be too shy, okay?"

The fatherly voice and the gentle gaze came along with his taking her hand and placing it on the bulge, and after using his own hand to try to guide it up and down he stopped and adjusted his seat to recline it more while undoing his belt and wiggling so his trousers and boxers went down to his thighs, exposing his very erect penis.

"What's wrong sweetie?" Mr. Baxter asked when she resisted his putting her hand on the angry looking weapon. "Surely you've seen other fellows before. Are you disappointed in what you see?"

"No," Penelope shivered.

"Then what's wrong child?"

"Nothing, it's just that - well..." the chunky gal mumbled as she recalled that what Wayne had made her hold that time in the woods was nothing like this, before she finally blurted out, "Your dick. It's so big."

"Oh, that's sweet of you to say," Mr. Baxter said as he kept his right hand on the girl's wrist while holding his erection upright with his left. "I admit that it's quite long but I'm afraid it's lacking a bit in girth. Here. Fell how slender it is."

"See," he announced proudly as he shivered from the feel of her damp palm on his vein-riddled member. "You can get your hand around it with no problem. Now just move your fist up and down. Slowly at first. That's it."

Mr. Baxter looked at Penelope's cherubic face illuminated by the dim lights, her eyes watching in wonder through the still off-center glasses as he hand went up and down the shaft of his cock, and the old man moaned in approval as he leaned back and offered a suggestion.

"You can use both hands if you want honey," Mr. Baxter suggested, and after looking over at him shyly brought her other hand over to grip him. "There you go. Oh my, that feels good."

Penelope's fists went up and down and when she giggled at one point Mr. Baxter asked her was she was chuckling about.

"Nothing. It's just that when my hands go down the skin on your dick goes down too and that makes the head appear and then disappear again when my hands go back up," the girl explained.

"Oh, I see," Lyle said with a grin as he brushed her hair from her cheek. "I take it you've never been with an uncircumcised fellow before, am I right?"

"Yeah, I guess," Penelope confessed. "Am I doing this right?"

"Splendidly dear. If you would like you can twist your hands as they go up and down," Mr. Baxter suggested.

"Don't want to hurt you."

"You won't, and if you would like you can spit in your palm too," Mr. Baxter told her. "I know that's not ladylike but..."

To his delight Penelope brought her hand to her mouth and then brought her wet hand to the swollen organ.

"Ahhh!" the senior groaned. "Wonderful. Can you see what you do to me? Do you feel me throbbing in your hands?'

"Yes."

"I haven't been this excited in years. Since my beloved passed," Mr. Baxter confessed, although in fact the excitement he got when his wife's heart gave in was not from sex but from relief.

The girl had become a bit possessed as she kept pumping the long prong, looking up from time to time to seek the old man's approval until he finally asked Penelope to give him a kiss. She did as he asked, and was shocked when he took her lower lip between his and sucked in it before doing the same to the other.

"Your lips. So full and lush and so delightful to kiss, but I think they would be even more enjoyable somewhere else," Lyle declared as he put his hand on Penelope's neck and eased her head down into his lap until her lips were at his cock which she held in her right fist. "You know what I want. What I need. Take me in your mouth honey. Watch your teeth. Open wide for me. Ahh!"

Penelope had an idea of what was going to happen the minute he pulled her head down, but while she didn't know what she was doing she let him put his dick in her mouth and allowed him to push her face down onto it. She choked a bit at first but her pulled her head back up for a second before easing it back down, and when she decided it wasn't too bad she started bobbing her head up and down by herself.

"Oh you sweet thing. Can you get your lips further down?" Mr. Baxter asked. "You're so good. I bet you've done this before," Mr. Baxter incorrectly guessed. "Faster. Suck harder. That's it. So good baby. Gonna... gonna..."

The senior citizen's body tensed as his hand clutched Penelope's hair, and although she gagged a bit when the warm seed spurted into her mouth she did't choke as the organ kept cumming until it started to go limp.

Only then did Mr. Baxter raise her head up, smiling at the slightly fogged glasses and at the trickles of semen coming out the sides of her mouth before kissing her spunk coated lips.

"That was so good baby. I didn't think you had done that before," Mr. Baxter said in praise of the amateurish fellatio she had just performed.

"I hadn't," Penelope admitted.

"Oh. Did you like doing it?"

"I guess. It tastes kind of musty though," she said while making a face. "That's why I swallowed it fast."

"Good girl, although it would have been more comfortable if we did it inside," Mr. Baxter offered as he pulled his pants back up. "Maybe next time we could go to my place, or if you would like we could go to your house."

"My house?" Penelope asked as she tried to get her bra back in place. "What about my Mom?"

"Why? Are you embarrassed of me?" the senior asked.

"No," the girl insisted. "Gee, I was so proud to be with you at the restaurant. It's just that Mom? She's kinda - you know."

"Maybe we could sneak into your bedroom."

"Oh gee, it's right next to hers," Penelope giggled.

"Well then we'll go to my place. Tomorrow night okay?" he asked hopefully.

"Uh - sure," Penelope replied as the car started back up, and after Mr. Baxter let her off she crept into the back door of the modest house, grateful that her mother was already in bed.

After getting undressed Penelope went to the bathroom, brushing her teeth vigorously to get rid of the taste of her boyfriend's spunk.

"Boyfriend," Penelope said as she looked at her reflection before rinsing. "Mr. Baxter is my boyfriend."

Straightening up, the teen glanced to the side at her naked self in the full length mirror and made a face, looking herself over and up and down while whispering, "Sexy. My boyfriend called me sexy, and more than once too."

The girl's hands went up to her breasts, cupping them and wishing that they were bigger because they barely stuck out from her thick waist, and while her belly was smaller than it used to be to Penelope's dismay it was still there. As for below the waist, where the wild jungle of dark brown curls had been left untrimmed since the last time she had dared to wear a bathing suit, she shrugged because Mr. Baxter had seemed to like it like this and since he was her boyfriend...

***

"Are you sure this is where you want to eat?" Mr. Baxter asked as they sat in the car in front of Five Guys. "We can go anywhere you like."

"This is good. They have awesome burgers and fries. You like that stuff don't you?"

"Sure," Mr. Baxter replied, and with that they entered the somewhat upscale fast food place.

Penelope was aware of the quarter of kids sitting in the corner and could see them talking to each other and nodding in her direction while they ate, and so was the senior citizen, but neither of them said anything, and after they finished Mr. Baxter pushed a little bit away from the table and patted his stomach.

"I don't know if my doctor would have approved of what I ate, but I have to admit I enjoyed it," the older man proclaimed.

"I know I shouldn't come here because I'm fat, but it is awesome," Penelope replied, drawing a disapproving look from her dining companion.

"No more of that Penelope. I won't have it," Lyle Baxter announced. "You're a beautiful and voluptuous woman. I thought I made that clear to you."

"I know. I'm sorry, it's just that nobody ever told me that before," she apologized.

"Well you better get used to it young lady," Mr. Baxter said with a smile as he reached across the table and put his hand on the girl's wrist, letting it glide up against the grain of the fine hair on her forearm, and in response the hair stood up and goose bumps formed as Penelope shivered.

"I wanted to come here - not just for the burgers but to - well, I wanted to show you off," Penelope confessed.

"You did? You mean to those young people who sat over in the corner? Friends of yours?

"Not really. I don't have very many friends. I went to school with them though," the teen admitted with a bit of embarrassment. "I just wanted to have people see me with you."

"Well I want to show you off too honey," Mr. Baxter said. "Let's go out for a drink."

***

"It's kind of dark here," Penelope said as they entered the bar, and the girl was so shocked at the bouncer allowing her in that she didn't know what kind of a place it was until Mr. Baxter led her to a booth in the corner.

"It is. We won't stay long. I just wanted to have a drink and like I said. Show you off," Lyle said as he sat close to the girl and put his hand on her thigh as a scantily clad waitress came up and asked what they wanted to drink.

"Whatever you're having," Penelope said as she looked at the deep cleavage of the waitress, and after the woman left she whispered, "Omigod. These ladies are almost naked."

Report Story

byVeryDirtyMind© 3 comments/ 16359 views/ 7 favorites

Share the love

Report a Bug

Next
3 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel