When we last left Cal, he had just pleasured one of Mountain View Mobile Home Park’s many MILF’s, the lovely Kelley, or as he had affectionately renamed her, “my dirty little fuck princess.”
She was one of the girls of Mountain View that he had his eye on, the other was another teen that was a friend of Kaylee’s and likely in her classes in the local high school. He knew it was a little dangerous to be fucking two high school girls who probably knew each other, but what the fuck? The worst that could happen is one of them would get mad at him, and decide to stop coming over for sex. Or maybe try to get him in trouble. But the age of consent is sixteen in West Virginia. As long as he was not forcing them to have sex, it was all legal.
The teen he had his eye on was, like her friend Kaylee, sixteen and in high school. Unlike her friend Kaylee, she was not tall and did not have the tall model-like body, nor Kaylee’s generous tits, that seemed a little big for her frame. In fact, Lolly, which apparently was short for her real name, Lolita, was a very plain looking girl. She was about five foot three, with dark hair that framed her somewhat round face, and a body that looked like it had not quite fully developed. She was thin, and had a small — perhaps one would say boyish — ass, and tits that were about the size and shape of miniature muffins. It would be accurate to say she had nice puffy nipples, that each topped off just a slight mound of tit — not even an A-cup. Just a rise, to hold up that puffy nip.
Lolly seemed somewhat shy, and you might ask, how did Cal know what her tits looked like before he had even had her inside his trailer. Well, as a friend of Kaylee, the two girls sometimes came by together, and he noticed that Lolly often wore the same old and somewhat worn-out outfit. A little skirt made of a thin blue cotton material, that was supposed to look like denim, and a thin worn t-shirt, that when the weather got hot, would get damp with sweat, and stick to the enticing little puffies that were one of the few things about her that indicated she was a girl. He could only fantasize what she wore under the skirt, and perhaps that was what he found so appealing. He really wanted to find out what was under the skirt, and get a glimpse of her teen ass.
Cal was really becoming somewhat of a dirty old man, and some days it concerned him a bit. But the feeling usually went away, often when he had sunk his hard cock deep into some tight teenage or MILF pussy. So he simply followed his instincts — and his seemingly insatiable sex drive — wherever it led him.
And this fine summer day, it led him to call out a greeting to Lolly, as he saw her walking through the park, her head down looking at her cell phone, perhaps on her way to a friend’s house.
“Hi, Mr. Tipton, howya doin today?” she replied with a smile.
“I’m great, Lolly, but I need some help around my house,” he said as she approached his trailer, wearing, as usual, her blue skirt and worn white t-shirt. “I thought you might want to earn some spending money.”
Cal guessed that the reason for her repeated wearing of the same clothes was that her family was poor, which was often the case, and he hoped that she would jump at the chance to earn a few bucks, a great way to get her inside his trailer and get to know her better. If you know what I mean — and I think you do!
As expected, Lolly stepped up on Cal’s porch, pulled her arms behind her back and stood up her tallest, also pressing her little puffies as far forward as they could go, and said, “Oh, yes. I’d love to earn some money, Mr. Tipton. What kind of things do you need done?”
“Mostly just household cleaning kinds of things, Lolly,” explained Cal, “Have you ever done house cleaning chores at home?”
“Oh, sure,” she said confidently, hopping a little bit as she answered. “I’ve done floor mopping, and dishes, and even cleaned our bathrooms, and the shower.”
“That’s great, Lolly. I’m thinking of paying you about fifty dollars, if you can come over for about two hours, maybe on Friday morning, before the weekend,” he explained. “Would that be OK?”
“Wow,” said Lolly, her eyes wide. “That would be great.” and she leaned forward and gave Mr. Tipton a little peck on the cheek. As she bent forward, he could see down her shirt, and could see the lovely brown puffies underneath.
“Do you want me to show you around now,” Cal asked, “or just come tomorrow — Friday — and get started then?”
“Show me now,” she said.
Cal’s dirty mind immediately thought of the things he would show her, maybe not now, but certainly soon! “Come right in,” he said holding the door and gesturing her to enter, “and we’ll get started.”
As she passed by him, he noted that her shirt, and the skirt were a little dirty, and she had a little bit of an odor about her- not unpleasant to Cal’s nostrils. The smell was a little bit sweet, a little dusty. and a little bit like pussy, which was one of his favorite scents. As she entered his kitchen, which was just off the entry door, Cal directed her to the cabinet below the sink.
“Under the sink,” he said, “is where I keep all the cleaning supplies.”
Without further instruction, Lolly walked directly to the sink, pulled open the two cabinet doors, and bent over at the waist to look inside. When she did, Cal finally got a glimpse of what was under that little blue skirt. As he had hoped, she did not wear a thong, or some sexy satin or lace panties, but a plain pair of cotton panties, slightly frayed around the edges, but tightly covering the twin globes of her girlish butt cheeks. Exquisite, thought Cal. Can’t wait to peel those off. But he held back, not wanting to frighten the teen off. He preferred to move more slowly, and allow her to decide she wanted some fun.
“I know how to do cleaning,” Lolly said, still looking at the assortment of products under the sink.
“I can come tomorrow morning around 9:30, after my ma goes off to work,” she continued, standing up again and looking at Cal. “Will that be OK?”
“Sure,” said Cal, “see you then.”
And as she left, Cal began to fantasize about how he could seduce the cute teen the next morning. He thought about offering her something to wear for the cleaning, so that she would have to change clothes, and, of course, change back when she finished. Then he had a great idea: Why not offer her a little French maid outfit when she showed up? He could explain to the naive teen how that was the appropriate outfit for cleaning and that he was used to all of his former cleaning help wearing such an outfit. Once he got her into the French maid outfit, he could find ways to look at her hot body and touch her in ways that might get her turned on.
So he went out that night, and drove to the adult bookstore, halfway to the small town up the road, and looked at the sex-play costumes on display. Of course, they had a French maid outfit, one with a frilly too short white skirt, a black see-through shirt with a collar, but only one front button, and a pair of nearly see-through black crotchless panties to go under the skirt. On the little teen, he knew it would leave little to the imagination, and would make the innocent teen look like a dirty slut. Perfect, he thought, as he found the outfit in the smallest size, and took it to the front counter. It was $49, for the tiny outfit, but what the hell, thought Cal. It would be well worth the money to see little Lolly dressed in it.
Before she arrived the next day, Cal had carefully fluffed the outfit in the dryer with some scented dryer sheets, and then hung the entire outfit in a closet in his guest bedroom. Lolly was again wearing the same outfit from yesterday, and her dark hair was a bit stringy, indicating that she likely had not showered since yesterday. Again he noted her scent, which was both girlish and sexual at the same time.
“Where do you want me to start, Mr. Tipton?” Lolly asked innocently.
“Before you start, Lolly, it’s important that you wear appropriate clothes for cleaning,” said Cal. “It’s important so you don’t get your clothes dirty, and it’s also what I am used to with a girl who cleans my home.”
“But, this is really all I have to wear,” said Lolly with a little pout.
“That’s quite all right, Lolly. I knew you were new to cleaning and might not have the proper outfit, and I have the outfit my last cleaning girl wore, freshly cleaned in the guest room. Just go ahead and put on that outfit,” Cal offered helpfully. “She was about your size, and it should fit you just fine. There is a shirt, panties and a skirt all hanging in the closet — just go and change.”
“Oh, thank you, Mr. Tipton,” she said, brightening, “I’ll go get dressed.
She scampered into the guest room, opened the closet and saw the little maid outfit, and admired the frilly skirt and the nice shirt. But she was concerned that the shirt looked like it was of a see-through material, and Lolly never wore a bra. Could she wear this shirt, with her tits showing through it? Well, her tits were kind of small, and she thought that if Mr. Tipton’s last maid wore the outfit, she certainly could too. She was a big girl, and needed the money. So she slipped out of her skirt, her t-shirt and her panties, and pulled on the panties, and the ruffled skirt, and the see-through shirt. It was only after she got the panties on that she noticed that there was a large slit right up the front of the panties, and even part way up the rear. She had never seen crotchless panties, and just assumed that maybe they had been torn at some point, but she didn’t want to offend Mr. Tipton by complaining.
When she came out, Cal was immediately hard as he saw how the french maid outfit transformed the innocent teen into a sexy little tease. The outfit was slightly small on Lolly, so that her tits stretched the flimsy top, the panties tightly encased her ass, and the skirt barely covered the sexy and nearly transparent panties.
“How do I look, Mr. Tipton,” Lolly asked innocently, smiling and turning around so he could see her in the new outfit. “I guess you can see my boobs in this shirt, but if it’s what maids wear, then I guess its OK, right?”
“It is what they wear, and you look very nice, Lolly,” Cal said, looking her over. “And you are the prettiest little maid I have ever seen. Your boobs are absolutely perfect.”
“Aww, you are sweet, Mr. Tipton,” and she reached to give him a little hug, brushing her barely covered puffies against him as she gave him a peck on the cheek.
As she gave him a hug, Cal couldn’t resist reaching down, and putting a firm hand on each of her creamy butt cheeks. As he did, his hand almost accidentally pulled the crotchless panties to the sides, and his fingers slid inside, and brushed up against the little lips of her teen pussy, covered with what felt like slightly matted downy hairs.
She gasped a little as he touched her sensitive lips, and said, “Oh, sorry, Mr. Tipton, but the panties have a big old rip in them, and I guess they need to be sewn up. You probably didn’t know about that rip, and so you probably didn’t think you’d be touching me there.”
“Oh,” Cal said, “pulling his hands back, and feigning surprise. “I am so sorry — I didn’t know those panties were torn. Let me take a look, and I’ll have them repaired for your next visit.”
“Here, sit down, and let me have a look at where they are torn. Put your feet up here on the couch, so I can see where the rip is.”
So Lolly sat on his couch, with her feet next to her, and her legs spread wide, so Cal could see where the panties were “torn”, right over her protruding pussy lips with the downy hair, and all the way back to the crack of her ass. He noticed that her sparse pubes were matted, and her pussy was sticky, and smelled strongly of sex. His cock was straining at the smell.
“See?” she asked innocently, before adding: “I’m sorry I’m a little messy down there. My step-brother Sean likes to play a massage game with me, and sometimes, he puts his big old thing in me, and squirts his love juice. He did it this morning, and I didn’t have time to clean up.”
Well, thought Cal. That explained the strong smell of sex. And it also meant the little slut was not a virgin, and might be happy to have his cock if she had already enjoyed her step-brother.
“Yes, these are torn, aren’t they,” he said as he bent over and carefully ran his big fingers along the edges of the panties, pulling them apart, and then gently massaging the full lips of her pussy, and tracing a line along her slit, down and underneath, to where he touched the little pucker of her ass.
Breathing heavily now, he leaned even further, to where his mouth was mere millimeters from the little teen’s pussy, inhaling her musk, and blowing his hot breath on the sensitive lips.
“Mmmmm…. that feels kinda good, Mr. Tipton.”
“Well,” he said, “then I’ll just have to keep doing it a little more then, won’t I?”
“I guess it would be OK,” she giggled. And she leaned back and sighed as Cal continued to finger her little love box.
Cal slowly leaned over and pulled apart the opening in the panties to place his mouth over the teen’s pussy, that was pungent with her unwashed odor. There was something very dirty, and very hot to Cal about putting his mouth on the girl’s pussy, where some other man had cum recently. The taste sweetened as she began to produce a bit of her sweet pussy nectar as he massaged her lips, and he began to try to slide a finger inside her.
“Are you sure this is OK?” Lolly asked as she let out a little moan as his tongue worked around her lips, and into her tight hole.
“It feels, OK, doesn’t it Lolly?” he replied. “And if it feels OK, then it certainly is,” he assured her with authority.
“It feels so good, I don’t want you to stop,” she said, breathing more heavily. “I love how you are touching me. My step-brother doesn’t really try to make me feel good, he just puts his big ole thing in me, and pumps until his love juice comes out. He calls me his fuck doll.”
“But you like it when he puts his thing in you, don’t you, Lolly?” asked Cal, continuing to slide his big finger in and out, and tonguing her tiny, but experienced little cunt.
“I guess so,” she smiled, moaning as Cal, continued stroking and sucking her little honeypot.
“Do you want to put your thing in me, too?” she asked, wide-eyed.
“I’d like to do that, and also show you some other things that feel good, Lolly. Would you like that?”
“Mmmm, yes, I think so,” she replied rolling her eyes back a bit.
Cal reached up and pulled apart the thin blouse, and put his big hands on Lolly’s delectable puffies, massaging each and kneading the firm tit-flesh on the willing teen. She moaned again as Cal bent down and began taking each tit in his mouth, savoring the feeling of the engorged nipples, and the sweet saltiness of the perspiration that clung to the breasts. He continued until Lolly was breathing hard, and writhing around, forcing Cal to grab hold of her little butt cheeks, to keep his mouth on her hot body. While he was really enjoying suckling her puffy little titties, and could have continued for hours, he wanted her cute ass.
“I want you to kneel on the couch now, Lolly. And rest your hands on the back of the couch, and brace yourself. I want you to point your butt at me, and put it right up in the air.”
“OK, Mr. Tipton,” she said, dutifully getting into place, “as long as you keep kissing and touching me like you been doing!”
Cal got on his knees behind the teenager, and began kissing and gently nibbling on the firm little cheeks of her girlish ass. She had no fat on her, and the lean cheeks were firm and nicely muscled. Each cheek had a little dimple on the side, and in her kneeling position, her lovely pussy lips protruded a bit, providing a view of the soft pink flesh inside the lips. He again mouthed her pussy, his nose pressing against the pucker of her little asshole.
Cal grabbed some lube he had handy, and slathered some on his cock, and squirted a little right on the little pucker of her ass, where it peeked from between the crotchless panties.
“I think you’ll like this,” he said, spreading the lube inside her little hole with a big finger.
And so he grabbed her little hips, and placed his raging boner at the entrance of her little brown hole, and began pressing it in. She squealed a little at first, so he reached under and massaged first her titty nubbins hanging from her chest, and then inserted a finger in her pussy, and began pumping in and out. As her sphincter relaxed, he got most of his cock inside, and she began moaning as he began to pump in and out.
“So nice and fuckin tight,” Cal grunted into Lolly’s ear, as he continued dicking the tight ass of the compliant teen.
“Don’t you love how Mr. Tipton’s cock fills up your little hole, Lolly,” he whispered into her ear, as he continued manhandling her little tits.
“Mmmm….unggh,” Lolly groaned, as his cock filled her, and his fingers alternated between her sensitive nipples and her engorged pussy. As he continued, he could feel her body tense, and she began shuddering with an orgasm, squealing with delight as he felt her pussy suddenly clench the finger he had inserted in it, and then cream in his hand as he cupped over it.
“OOOweeeee,” moaned Lolly, as the orgasm rocked her, and made her shudder with pleasure.
Moments later, Cal came with a mighty spurt, as he couldn’t take the intense tightness of her butt much longer. “Fuck,” he exclaimed, “you are one tight little fuck.” And he gave her a friendly slap on her butt.
“I’m glad you feel good too, Mr. Tipton,” said Lolly. “That was fun! Now, where do you want me to start with the cleaning?”
“Clean yourself up first, Lolly, and then you can get started with picking up around the house, and mopping the floors.” And he tossed her a little washcloth, that she used to clean off the cum from her pussy and ass.
As Lolly began working, every time she bent over, Cal got a nice view of either her pink pussy lips or her brown nipples under the see-through black top. It was enough to get him hard again, within an hour of her starting to work, and so he called her over, and asked her to sit on his lap. She did so, and he couldn’t resist fondling her lovely little titties, as she squirmed on his boner, her pussy lips exposed through the crotchless panties. He reached down and pressed a big finger into her teen quim, and she moaned again, as his finger easily entered her slick tunnel.
“I think your little pussy is really ready for some fucking, Lolly. Don’t you?” he whispered in the teen’s ear, his hot breath on her neck causing her to become aroused again, and her juices begin to flow.
“I like fucking, Mr. Tipton!” she smiled, and squirmed a bit more. “Do you want me to bend over the couch, so you can fuck me nice and hard?”
“That would be perfect, Lolly,” he replied. “Just bend right over the couch here, and let me see that pretty little pussy of yours.”
And she did so, the panties splitting wide, exposing her fat labia, and the pink flesh inside. The maid outfit was perfect, no need to remove anything to have easy access to her tight teen slit. Cal stepped behind her, placed his hand on the small of her back, and rubbed his cock around the lips of her slick and hot pussy, as Lolly sighed again with a low guttural moan.
“Your big thing feels so nice inside me, Mr. Tipton. Are you going to do me?”
“I’ll fuck you, Lolly,” he said as he began teasing her clit with the tip of his boner, “but you need to call my thing by its real name. It’s a ‘cock’ and I want you to ask for it by its real name.”
“Okay, Mr. Tipton,” she said. “Please put your COCK in me.”- emphasizing the word, in her high-pitched voice.
Cal stood behind her, and inserted his fat index finger into her little pussy, which was slick with her juices, and moved it around inside of her little love canal.
“And tell me just where you want it, Lolly. Because you have this creamy pussy, where I have my finger, and you have that tight little butthole, that I fucked this morning.” Cal explained. “So you need to tell me exactly where you want my cock.”
“Mmmm. I want your cock in my little pussy, right now!” Lolly said, wiggling on his finger in front of him.
“Gimmee your big cock, Mr. Tipton. Put it in where you got your finger now!” she whimpered.
Cal’s dick was by now raging hard, and was waving in the air as he stood behind the teen, occasionally bouncing down on her firm butt.
He removed his finger, lifted it to his nose, and inhaled the sweet musk of the teenager’s cunt, arousing him even further. He slid the tip of his cock up and down her slick slit, and began slowly pressing into her, as he pressed down on her lower back, holding her squirming body in position for the invasion of his man-sized dick.
“Ungggggh, ohhhh fuck!” Lolly moaned as the rock hard shaft forced apart her tight cunt slit. Cal could feel the tight walls of her pussy grip his cock, as the member pressed up against the inside of her pussy. It seemed to grip harder as he slowly pulled back, and then rammed forward again, his balls slapping up against her.
As he increased the pace of his cock slamming into her, his in and out movement was matched by Lolly’s little cries of pleasure, that she uttered each time the big cock was inserted to its fullest into her smallish pussy.
“Ughh….ohhh…..Ughh…..ohhh……It…. feels…. sooo…. fuckin…..good.” She breathed out each word and moan with each stroke of the big cock.
Cal reached under her, and under the front of the flimsy shirt, and roughly gripped her sensitive nipple puffies, as he reached the point of climax himself. With a final massive thrust, he forced his dick in to its hilt, and pulled the teen against him, using her tiny titties as his handholds.
She screamed with something between pain and pleasure.
“Owww…….oooooooh……FUCK!” Lolly screamed, and her body shook.
At the same time, he felt her cunt contract around his cock, as if milking it. He could feel his balls release a load of cum deep into her pussy, and his throbbing cock felt super sensitive.
As he held her still shaking body, he slowly pulled his now spent cock out, feeling her pussy attempt to hold it in place. Cal felt the wet slime of his cum mixed with her vaginal secretions follow as he slowly pulled out. As he did, a stream of goo leaked from her pussy, and down her thighs, soaking the transparent panties, that now clung to her sweating body. He reached down and scooped up a handful of the goop, and reached under and wiped it all over her puffy nipples, massaging the sticky mess on her tiny boobs.
“Now stand up and look at me, Lolly,” said Cal, as he pulled her up, and spun her around, so he could see her in her exhausted state, with the filthy maid outfit sticking lewdly to her tits, and her flushed body. He loved the look of the cum dripping down her legs, and her dark hair clinging wetly to her head, her body perspiring from head to toe form the wild exertion of the vigorous fucking he had administered.
“Here’s your $50, Lolly. I’d like to see you every Friday morning from now on, for a good cleaning, OK?” Cal said, handing her a crisp $50-note.
“Sounds good, Mr. Tipton. I’ll just change out of these cleaning clothes, and see ya later!” Lolly said, as she scampered off to the bedroom.
“Don’t you want to shower first?” asked Cal, as she stepped past him.
“Sure,” Said Lolly, “that would be great. Sometimes it’s just too crowded at my trailer for me to get a shower.”
“Feel free to use the shampoo and soaps and lotions that are in the bathroom there, Lolly,” Cal told her, assuming that she did not have access to such nice items at her own home.
And, minutes later, the teen emerged from his bedroom, her dark hair wet and stringy, and wearing her thin cotton t-shirt that hid her puffy tits, and her slightly dirty blue skirt again covering her tight teen ass. And she smelled clean and fresh, like the sixteen-year-old girl she was.
“See you next Friday,” Cal said brightly.
“I can’t wait!” Lolly replied, as she skipped out his front door and bounded down the steps from his trailer, the fresh scent of the fruity shampoo she had used trailing behind her.
