Pauline's Pumpkins - Day 03

Story Info
Pauline gets new clothes, Conor meets her at Busick's.
17.2k words
4.22
7.7k
6

Part 3 of the 6 part series

Updated 06/09/2023
Created 11/05/2018
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

This story contains massive lactating tits with some reluctance. This story is also part of a series of stories so check out part one out first.

Third day - Sorry for another wait, and hopefully the wait was worthwhile. Not going to explain my life but things have been slow and unproductive, and as an inexperienced writer I don't know how to tackle this perfectly. But, I do plan to post more in the future, and I'm definitely going to post a different story pretty soon before day four, so send me feedback I can use in my future work. Enjoy!

*****

Pauline turned in her bed. Her floppy freckled breasts squished and squashed as she turned left and right, both ridiculous milk tanks helping her keep to the center of her bed. She mumbled in her dark thoughts.

***

This hard working farm girl was easy to pick on in school - she was the butt of many boob jokes and pranks. With her many siblings and tough resolve she eventually found her place among her peers. Getting to know Rory's friends who were all in their senior year while Pauline was in her junior year was one of the ways in which she became more popular than a pair of verbal punching bags and Rory made sure everybody knew how mature and awesome her slightly younger sister was.

It was one sunny April afternoon during her junior year after lunch where Pauline was walking with Rory and Jessie-Rae Higgens; Jessie-Rae like Pauline would be considered developed for her age, but far more modestly than her tank toting bestie. She had a flawless dark complexion with gently permed corkscrews that curled to frame her face. Unlike her sister, Rory had less fat around her body but had a stronger, thinner, taller build with short, curly brownish-blond hair. A recent legal adult despite being older for her grade period, Pauline was still a short stack with a fat rack that rested right above her hip bones.

This particular day walking down the halls, Pauline hadn't been wearing a bra and Pauline seemed very self conscious about her chest, pressing her backpack's arms into the sides of her breasts to stop them from constantly jiggling. It more or less just smooshed them together. They'd been talking about the heat of this day in particular, but Jess steered the conversation.

"Paul you still look damn fuckin slutty." She made little attempt to keep her voice down.

"Don't call my sister slutty!" Rory snapped back quietly. She followed with an even quieter "...but you do look slutty, I would just let them bounce gently and ignore it."

Pauline groaned and dropped her pack, then swung it around to the front to hide her tits, pretending to look for something in her back while she walked to class.

"You're one to talk!" Pauline was pointing her bickering at Jessie. "You're the one who convinced me it was a good idea!"

"You eventually have to be braless to do this, and you also have to be shirtless! You didn't come to school with no damn shirt!"

"You two shut it!" Rory interjected. "We're in the halls. Besides, I have a spare bra for you in my locker, follow me before you hit physics."

"I don't know if you mean you have a spare bra that you would use but I can, or if you just have one of my bras..." Pauline was slowly moving her eyes between her slightly squashed side boob and her sister's small, perkier breasts.

"I've had your yellow one in my locker since mother's day."

Jessie broke out into laughter after hearing Rory mention mother's day.

"I've been looking for that! And fuck you for saying since mother's day." Pauline was glaring at Rory, who had a slight smirk on her face watching Jess enjoy her humor.

"You would have demanded it back if I told you I had it, and after mother's day you've proven having a spare would be helpful. If you ever needed me to run and grab you something to wear again, I could just open my locker without you worrying about your locker being broken into when I... want your old food!" Rory jokingly menaced at her little sister. "Or whatever dumb reason you don't trust me with your locker. Also you said it was your least favorite bra and you mentioned donating or trashing it since you hated the color."

"It's just a privacy thing!"

They teased Pauline until they had to split at Rory's locker. Pauline had consistently been dropping hints that she was interested in Conor, but he seemed to blow them off, or he was dating somebody, or she was dating somebody and her teenage mind saw this as god dropping an invisible anti-love wall between them. Now neither of them were dating, Conor hadn't been asked to prom yet, and because of her paranoia that he wouldn't know she wanted to go to the dance as more than friends with him, she had painted and dried "P R O M?" across her fat little cow tits. She was going to ask him to stay after school and pull her shirt up right in his face - not what she thought was the most pristine or even creative way to ask him to Prom, but Jessie convinced her that he might not get the picture.

She knew which bus he took home, and left class early to try and catch him before he boarded. As she jogged, ignoring the attention her bounce garnered, she saw that Conor had left early and was almost on an abnormal bus for his ride home. He must have gotten out of class super early, since the buses would be sitting there for maybe twenty more minutes. She had time to pull him into an empty room and ask him to prom, and could even drive him home.

"Hey Conor!" She yelled, catching her swinging breasts as she stopped at the school's back doors.

He turned around, almost aboard one of the buses. Conor was just above six foot one with straight jet black hair and a caucasian skin tone that hinted at some Spanish heritage. He was no gym monster but he was a prominent baseball player for their school, lined up to only improve by his senior year.

"Hey Pauline! What's up?"

"Hey... I really want to show you something before you head home, can you take a minute?"

"Uh, can you tell me what it is really quick? I'm about to catch a ride to baseball, maybe we can talk then." Pauline immediately realized he was wearing their school's red and white baseball uniform.

Pauline was an avid fan of the sport, at least her favorite player. However she had been focused on her own grades and agenda and had forgotten that Conor had a game today. Maybe asking after they won would be better? They were likely to win, but maybe after a long day throwing such a big question with such large implications would have been a bit much. Either way, Conor had scammed himself out of seeing her titties for now.

"Oh, well yeah it can wait." She replied, feeling defeated for the moment but certain she could show him another time.

Right behind her however, one of her friends had come to see what would happen. One of her good friends Mickey had gotten to the scene at that exact moment, having just finished smoking in the bathroom after skipping class, and saw Conor walking into the bus.

Mickey was not the brightest of Pauline's friends, but she was a loyal one no doubt. She was also an avid believer in crazy risky choice making, and believed that as long as her heart was in the right place she was doing her best. These are the important facts that lead to her immediate response to the situation.

"Wait, Conor!" Mickey screamed out.

He turned again, now confused by the strange situation. Mickey was right next to Pauline at this point and before she could react to her presence, Mickey ripped Pauline's bra and shirt up in one fast pull, an incredible feat! Conor's mouth agape and lots of faces in the slightly tinted bus glass lit up with insane reactions. Pauline jolted her eyes down at her firm funbags, plump and wider than her hips, her eraser head nipples angled down at the ground.

Pauline didn't know how to react for a few moments, looking back and forth from her friend and Conor, anger and nearly paralyzing fear. After processing everything for almost an entire second, she ran away from the buses and pushed past Mickey. The boys on board had already pulled up flip phones and taken pictures that would haunt Pauline for years. Multiple students had begun walking around the wide halls of her high school, and Pauline had no choice but to run into the unisex bathroom by the main hall, still trying to stuff her tits back into her bra. Her mind was racing to process everything still, her friend's dumb choice, how she had pictures taken of her, how he must have seen the P R O M? painted on her skin, how dumb the idea was in the first place.

Then she cried in the bathroom for almost an hour, driving home after everybody had left or gone into other rooms. Needless to say she didn't go to the game, or prom.

***

While she didn't dream often or at least remember her dreams often, she did have nightmares on occasion. Usually there was a reason however undetectable it might be, but after waking up sad and spiteful of that searing memory, she knew immediately what had made her relive that day. Besides having an unpleasant dream, this morning was infinitely better than yesterday - she felt refreshed after getting past her initial terror, feeling awake and alive.

She checked both breasts. Her milk pads were thoroughly 'used' by this point, but she hadn't made a massive mess like before, and more importantly she hadn't been hanging off her bedside. She did however find that her breasts felt slightly inflamed, not in heavy pain or overly sensitive, but hot and full. She was glad that she hadn't bloated up too big, but her chest definitely looked a little larger than usual, by a couple more inches in her bust.

Her breasts were definitely growing yesterday as she'd anticipated, and it seemed that the growth spurt was slowed down. However, she definitely felt more sensitive than average.

She stretched and pulled herself out of bed, dragging her blubbery udders off the bed. She then looked at her phone on the nightstand. She had a missed call from Rory from late last night after she'd fallen asleep, and a text message saying 'Please text me when you wake up'. Pauline decided to call instead, putting her phone to speaker mode and grab her clothes for the day. She was going to wear a dark blue sweater over a lighter blue undershirt with a blue satin bra. As she fished around her laundry for some jeans and panties to complete her unicolor outfit, Rory picked up the phone.

"Hey! Pauline, sorry I thought you would have been up later last night, I should have called earlier. How are you right now? I saw that you called off work yesterday." Rory was always an early bird, and her recent dream reminded her of how she had always been overly cautious. It was still odd that she knew Pauline called work off.

"Yeah I did, how did you know? Are you spyin on me?"

"No!" Rory crackled on the phone. "I just heard from some of your people is all-" Rory's next words were plagued with even more crackling.

"Uh- I'm having trouble hearing you, what was that?"

Rory's response was cleaner but clearly the connection was weak, "I'm not getting good reception, that's on me. But I just wanted to ask if today was a good day to move the equipment over, you have anything planned with your barn for the next few hour?"

"No, I'm good."

"Awesome!-" Rory seemed to cut out for a few seconds. "I've gotta go but let me know if you still have animal problems, bye!" And with that she hung up.

After the strange call she thought back to her dream last night, and the reason she had it. Pauline was actually somewhat superstitious, not about random good luck charms or any fear of breaking mirrors but strange correlations popped up too often in her life to ignore the possibility of invisible forces. Having such a bad memory from her dream was worrying to her, definitely either a sign that things would go poorly or she had to work hard to avoid it going poorly. What would going poorly mean anyways?

These thoughts made her consider his whole situation. Conor Martin was a married man with older children, much older than many would expect compared to his age. His wife Denise was an older woman who owned the farm he worked on - she wasn't a mean or villainous woman by any metric Pauline could detect, a pretty lady who had somehow wandered upon Conor soon after he jumped out of college. Pauline didn't have any issues with Denise, but she knew she resented the fact that Conor and Pauline kept in touch - for decent reasons, considering that Pauline was younger, a childhood friend, had hefty assets and actually had a crush on Conor. Bad luck had continually stumped her efforts to be with him, and if the nail in the coffin was Conor's wedding to Denise, his efforts to appease his wife by distancing himself from Pauline was an afterthought cremation. Now, far into their own farming careers, her sister worked with the company that moved food from the fields to store shelves. This was part of why he was contacting her, business oriented re-ignition of old contacts.

Pauline was stuffing her bra cups with flesh when she realized she hadn't put her new milk pads in, rubbing her turgid nipples against the bra's hem. She was stunned for a moment, feeling her hot chest burn up from the rugged contact. As she dragged her breast back out, slowly forcing her plump areola up the wireframe.

Was it better if he just wanted to be business oriented? Would it be weird to try and be friends again? Would his wife feel comfortable with that? Should she be comfortable with that?

Was there more to this?

Before pulling her breast out all the way, she let her rugged bumpy areola slide back in and out of her bra. She let out quiet grunts as her nipples and her Montgomery glands caught the hem. Then she pulled her monstrous chest out fully and began running her fingers along her breasts, pushing in enough to feel the meat under her soft pliable skin. Milk was condensing at her nipples.

It wouldn't be right if he wanted more, but it wouldn't be something she would have a problem with, right? What would 'being right' even mean?

She sat back onto her bed and let her left breast drop against the side of her bed, making a slapping sound as it hit the wood. It hung limply between her legs, leaking into the carpet below.

Her right breast was folded in half, now pointing straight at her face. She was licking the plump bumps around her tender nipple. She bit and chewed, pulling her flesh in different directions, squirting herself in the face at times.

She left a million hints, he had his chances, and after all these years he probably didn't even deserve another chance.

"It's on him," she thought. She moved her left hand under her hanging udder to massage herself. She dug in and pulled on the flesh near her nipple with more hunger, making her teat burst milky goodness back onto her face and bed. Her nipples felt so hot and vulnerable, growing more tender to her increasing vigorosity.

He could be doing this, all day.

Her hand was now moving deeper into her slit. She took it out for a moment to help her legs remove the rest of her clothes. As soon as she was fully naked, her hand flew back between her legs. She moaned into her massive chest, experiencing an incredible sensation of satisfaction. She hadn't been pleased with such ease or passion in so long, and for whatever reason her pussy felt like hot iron enduring her molding finger tips.

Yeah, this feels great without him. I don't need him for this, and he won't get to enjoy this.

She was picking up speed, and her sensitive state made her sex organs quiver uncontrollable. She was heating up so quickly, and her biting and sucking on her breast felt like hot knives of sexual energy digging into her doughy milk bags. She couldn't slow down, but her senses were overwhelming her.

Why does this feel so amazing?

After teasing herself for so long, she was done holding back. She stopped holding her breast folded from the under curves and dragged her nipple to her mouth. She held herself by her fat nub, feeling so sensitive to her tugging hand. She slowed her masturbating down to enjoy some of her hot milk, and with how pleasureful her nipple grip felt she knew she would be spoiling herself too quickly.

Pauline snapped down hard like a mouse trap on her boob but recoiled immediately. Her left hand uncontrollably dug deeper into her vagina, a response to the burning sensation of touching her untouched nipple. Her senses felt heightened while her self control had disappeared.

Fuck that felt so good!

She closed her eyes and screamed passionately, clenching everywhere. Her legs crushed her hand deeper into her slit, but her gigantic milk jug suffered the most of her leg's pressure. She hadn't seen the drenched carpet before, but she could feel what it must have looked like as her breast burned with sensitivity. She felt her milk torrenting against the inside of her nipple, only fueling her excitement.

As she was clenching up, her other breast was still aimed at her face. She was covering her own face with milk until she sucked her nipple back into her mouth. Like before it still felt almost painful to touch but she couldn't help herself, feasting on her juicy udder. She couldn't drink her own milk quantities but the struggle to contain her milk forced her off of her nipple and she moaned into her areola.

She lay on her bed, crushing her breasts with her legs and face, hand locked between her thighs.

Why was that so good?

She took a moment to cool down from her milking but that only meant she could endure more. She rolled flat on her back and used both hands to lift her right breast above her face. Her boob sagged on top of itself because of her sheer size, and now it was right in her face. Dug in and began sucking her own tit again. She sucked and pulled her nipple to the back of her throat, letting her tongue dance in across her flesh. Her changing position pulled her left breast further up onto the bed and now she could feel her milk spurt against her legs as she teethed her fat tit.

***

"Should we say something?" somebody asked.

There were four strong working men sitting in the back of a truck, and two men up front. The driver was another strong looking man, but he wasn't dressed like the men in the back, as he was in fact a foreman for the operating party. Shotgun was Mr. Jeremy Gittergut, a smaller man dressed in a suit and tie. While the foreman was in charge of operations usually, Jeremy was specifically asked by Rory to attend the delivery of the equipment.

"We shouldn't have too, and if she doesn't come out we're fine. I think." Jeremy responded.

They were all sitting in a massive delivery truck, repositioning farming equipment from one farm to the other. This was usually a quick and painless operation, but for whatever reason his superiors (specifically Rory) had asked that the owner of the farm they were delivering to be notified of their presence. Mr. Gittergut was not a fan.

"Listen, just start unloading the equipment." Jeremy yelled out.

As everybody began moving, he saw Danny Briggens with his eyes closed, getting tapped awake by his coworkers. Not the most interesting person in the world, but Jeremy pulled him out here to help get the job done quicker. Usually Danny worked the night shift, but he worked into the mornings of most days and it couldn't have hurt him to work one extra job.

Unfortunately, he looked dead, and even though Jeremy thought he wasn't important enough to have his well being factored into his plans, he didn't want to over work him too hard.

"Danny, go up to her front porch and let her know we're here."

They all began leaving the truck, preparing the large machines that carried the equipment for motion. Danny had to be shouted at a couple times to wake up, but once he was lucid he jogged up to the front door.