Tamara's Apprenticeship - Day 02

Tamara put her face between the voluminous pair of buttcheeks in front of her. She set her tongue on the tight ring deep inside the crack between them. It had a faint taste of sweat on it, familiar and feminine, not entirely unpleasant. She had never done this before. She wondered whether she was doing it right. She pursed her lips and rested them on the opening, moistened it with her tongue, as she had seen other girls do in videos on the internet. The soft buttocks that were now firmly squished against her face quivered in response to her first tentative movements.

Whoever designed these cycling shorts had a weird sense of humor, putting the inflating nozzle right in the middle at the back.

Tamara drew a deep breath then squeezed the full contents of her lungs out and into the shorts. Just like she had seen the demonstrators do in the instructional videos on the manufacturer's website.

It took surprisingly long to get the inflatable padding as full as it had been before her ride home the previous evening. Tamara recalled how Miss Millie had inflated the shorts in just one long breath. The woman's apparent physical prowess was one of many intriguing details about her. Along with her exotic accent, that curious out-of-the-way cottage dwelling she lived in, and the strange plants in her greenhouse. Not forgetting the impressive wound on her back. She had said she got it in a fight of some sort. Tamara had difficulty imagining Miss Millie fighting with anyone. She was sturdy, and assertive, for sure, but she also gave off a reassuring aura of compassion despite her imperious manner. Sort of... motherly.

Tamara was smitten. And she knew it. After just one day working for Miss Millie, she had the most aching, embarrassing crush on her beautiful new employer. And so here she was, about to embark on a 30-minute uphill cycle ride at six in the morning to milk a cow. For Miss Millie.

So off she went.

Despite their ridiculous appearance, the shorts did a spectacularly good job of cushioning her backside as she cycled. It was almost comfortable. For her legs, however, the ride was even more grueling than she remembered from the previous day. Perhaps it was because she was tired. After having stayed past closing time at the games store chatting to Andie, then lain in bed until late unable to get to sleep, then finally having dreamed vague and fitful dreams until morning, she was missing a good night's sleep. Alternate-universe Tamara who had never met Miss Millie would be blissfully unconscious for another five hours or so.

She shuddered. It didn't bear thinking about alternate-universe Tamara.

When Tamara finally wheeled up outside the garden gate, there was a little note pinned to it, written in a spidery flourish. Tamara's imagination conjured the memory of Miss Millie's brash, husky voice as she read:

Tamara dear girl,

I have had to depart on urgent business and shall only be back at midday.

Once you are done with milking time,

Malkin will show you the remainder of your tasks for the morning.

I look forward to surveying the results of your sterling work upon my return.

Tamara felt a little throb of disappointment at the thought that she would not get to spend time with Miss Millie that morning. But it was replaced by a sudden sinking feeling in her early-morning coffee-lined stomach when she saw the final lines:

Yours,

Miss Milfy

Tamara thought back to the previous afternoon and the dreadful Freudian slip she had blurted out while sitting in the front room of the cottage. Tamara had been sure that Miss Millie hadn't heard her. Or she had perhaps convinced herself of it since. Or maybe, just maybe, Miss Millie didn't know what MILF meant, and she was just repeating what she thought was an amusing mispronunciation of her name, as an affectionate joke. Yes, that was sure to be it.

Or... Oh God. Was Miss Millie being intentionally flirtatious with the note? Was it even an attempt at seduction? Tamara's imagination hurried off ahead of her, already drafting a reply that she could leave for Miss Millie to read on her return.

Yours, Tam the Temptress?

Nah.

Love, Tam-tits?

Maybe a bit... trashy.

Titty-titty-Tam-Tam?

Stop with the tits already!

Sincerely, your hot Tamslut?

Whoa, Tam! Just stop. Anyway, that one doesn't even alliterate.

Tamara shook herself from her brief bout of fantasy. She leaned her bicycle against the inside of the fence, as she had done the previous day. Miss Millie had said the cow was at the bottom of the garden.

As she made her way around the house, Tamara passed the front door. Something occurred to her. Though she had been very glad of the inflatable cycling shorts on the ride over, they probably weren't going to be particularly convenient for working in the garden. They were a little bit bulky. And like an idiot, she had forgotten to bring a change of clothes. If she took off the shorts, she would be walking around in just her underpants and today's superhero t-shirt.

Maybe Miss Millie had some spare clothes in the house. Gardening overalls, or just a long jacket or something. Tamara tried the door. It creaked open, with the same shrill, woody creak she remembered from the previous day. Miss Millie wasn't too security-conscious, perhaps. Which was curious, given that she had mentioned a break-in.

Tamara stepped inside, and narrowly missed treading on the patchwork-colored tail of Malkin, Miss Millie's cat. Malkin looked up at her, a squat blob of fur quietly purring and swishing its tail. He seemed entirely unperturbed. Tamara smiled. She reached between her buttcheeks to deflate the shorts, then wriggled them off and hung them up on a coat rack beside the door.

Unfortunately, there was nothing else on the coat rack that might serve as clothing for garden work. Tamara wondered where else she could look. At the end of the corridor was the door to the kitchen, and next to it the door to the front room. There probably wouldn't be anything suitable there. Beside the two doors there was a flight of stairs leading steeply upward. She hesitated. She didn't feel entirely comfortable exploring the house too far without having been invited to do so. And with nobody around, the place had a slightly... creepy feel to it. Even with her first few meandering footsteps towards the staircase, the old timber of the house groaned and grated all around her.

Tamara startled as something rushed past her. Then she put her hand to her chest in relief as she saw Malkin bound past, brushing against her ankle, and scamper up the stairs. Half way up, he stopped and turned back, looked though the wooden railings, and fixed Tamara with an expectant stare. That sealed her resolve. At the back of her mind was a slightly shameful, nervous excitement at the thought of walking around Miss Millie's home dressed only in her t-shirt and underpants. And if the cat seemed to be leading her on, well, then it was okay, wasn't it? If Miss Millie happened to return and catch Tamara looking around, she could always say she had been searching for Malkin.

The wooden planks of the stairs were narrow and uneven. Some of them felt loose and tipped a little to one side with the weight of Tamara's tread. At the top were two doors opposite each other. Malkin sat in front of one of them, swishing his tail. Tamara looked down at him as she put her hand to the handle. He didn't seem to be offering any sort of objection.

The door opened onto one large attic room. Its space was shaped like the inside of a tent, formed by the steep sides of the roof. The thatching of the roof was visible between wooden beams. At one end, a high window cast a square of sunlight onto the floorboards. And on one side of the room a simple metal-framed bed was wedged under the sloped ceiling.

Malkin trotted into the room ahead of Tamara and made straight for a tall wardrobe just below the window. He looked back at Tamara, then lifted one paw and placed it against the bottom drawer of the wardrobe. Tamara stepped inside after him. She had hoped, somehow, that there might just be a spare dress or a skirt or something lying around. The bed was ruffled but seemed to be devoid of clothing. There was a desk, too, but it was heaped with papers and bottles, no clothes. The many sets of shelves arranged along one wall were stocked only with books. The wardrobe looked like the only place she might find something. And it was closed.

She shouldn't do it. She was going to do it. She did it. Malkin stepped back as Tamara knelt and pulled the drawer open. The inside was a tangled jungle of gauzy scraps and straps, mostly in black, some in purple or red. It took Tamara a moment to identify any one individual item of clothing, but as she singled out a few things, it dawned on her that she was looking into an underwear drawer. Full of lacy, skimpy, sexy underwear. Miss Millie's lacy, skimpy, sexy underwear.

Tam, stop. This is private.

Malkin yowled as Tamara quickly slammed the drawer shut, catching his paw. She turned and scooped him up, murmuring apologies and stroking his head. The minor incident left her unsettled. She could hear the cat's loud yammer still ringing in her ears over the near silence of the empty house. Her heartbeat had quickened a little. This was a bad idea. She could just work in her underpants. It was already shaping up to be a warm day, and there would be time to get the shorts back on before Miss Millie returned at midday.

She was hurrying for the door with Malkin in her arms when something caught her eye. On the desk, a scrap of paper fluttered in the tiny current of air stirred by her passing. She looked over. The small sheet of paper was pinned to the desk by a candle.

Extract of an entry from the register of births

Millicent McMurdoch

Just the date. Just look at the date. That's all. Then get out of here.

Tamara leaned over and scanned the scrawly writing on the page. '74. She did the math. So she had been about right when she guessed Miss Millie might be in her forties.

She made her way back down the stairs. Once out of the front door, Malkin leaped out of her arms and pranced off into the green bushy mess of the front garden. Tamara headed round to the back of the house and then down the gentle grassy slope behind.

On the previous day, she had been busy hewing her way through the overgrown herb garden, and hadn't quite taken in the full extent of the cottage grounds. It was only after walking for several minutes, past a tall shrubbery, through some sort of stone feature with a sundial at its center, and then finally around a tall hedge, that Tamara came to a definite end. There was a tall iron fence at the bottom of the incline. And just in front of it was a little shack. Maybe it was a cowshed.

The shack had a double door, like those on a stable, with separate door panels for the upper and lower part. She undid the bolt on each panel and pushed them open.

"Hi."

"Yah!" Tamara shrieked and leaped a considerable distance in the air when she heard someone speak. She was still somewhat on edge following her little clandestine snoop around in Miss Millie's bedroom. She put her hand to her chest as if to hold on to her thudding heart, and looked around.

Sitting on a stool beside the door was a girl who looked to be about Tamara's age, maybe a little younger. Her long orangey-red hair was tied in two tightly-braided pigtails at the sides of her head. She wore a very tight, frilly white blouse and a short black skirt. She was also kind of fat. Tamara felt bad thinking it, but she could find no better term. It was an odd kind of fat, though. All on the chest and stomach. The girl's slender, freckled face could easily have been that of a skinny catwalk model.

"Sorry," the girl giggled, "Didn't mean to startle you."

"Oh, no problem," Tamara replied, "I guess you just caught me off guard there. I wasn't expecting anyone to be around."

The girl laughed, "Well, there's me. I'm Bessie. What's your name?"

"Nice to meet you Bessie. I'm Tamara."

"That's a hot name," the girl, Bessie, replied.

"Oh. Um, thanks. I'm here for, uh, milking time."

"Righto," Bessie said, and started unclasping the buttons at the front of her blouse.

Tamara looked. Then tried not to look. Then failed. Then finally she just gave in and stared. As the front of Bessie's blouse popped open button by button, Tamara realized that the girl wasn't fat at all. What she had taken to be a prominent, bulging stomach was in fact in its entirety the squished-together mass of two of the most colossal breasts Tamara had seen outside of hentai. Or inside of hentai, come to think of it.

"We have to get undressed?" Tamara ventured. She watched the final button come undone with a taut pop and spill the ill-confined contents of Bessie's blouse out onto her lap.

Bessie looked up at her, bemused, "Well I don't have much choice, do I? It's optional for you I guess. But don't let me stop you if you want to. I wouldn't mind. You're kind of cute."

"Um, alright," Tamara fidgeted with the hem of her t-shirt, hesitating. She didn't want to appear prudish.

Maybe country people always get naked for farm work? Saves on laundry, I suppose.

She rolled up her t-shirt and pulled it off over her head. She looked around for somewhere to put it, and settled for draping it over the open door.

"Ooh, nice tits," Bessie clapped her hands together excitedly.

Tamara felt rather self-conscious standing there in only her underwear, with her very petite, pointy breasts beside Bessie's mammoth rack.

Oh God. Now I've got to return the compliment, haven't I? I'm going to have to mention the elephants in the room.

"Sorry," Bessie winked at Tamara before she could say anything, "I'm being a bit too direct. I'm afraid I tend to get a bit horny at milking time."

"Right. Milking time," Tamara stammered, snatching the opportunity to bring the focus of an increasingly awkward conversation back to the task at hand, "Hang on, you get horny?"

"A bit. Just give me a hand here." Bessie heaved herself to her feet. She staggered forward a little unsteadily, pulled by the sudden lurching weight of her own unsupported chest. She grabbed Tamara's arm and clutched it tight.

Tamara started for the door, but Bessie tugged her aside, "Where are you going?"

"To, um... get the cow? Or, do we have to get something set up first?"

"I've got everything ready," Bessie let go of Tamara's arm and tottered over to one end of the room, where there was a stack of buckets and an array of a dozen metal cylinders leaning against the wall, "I've scrubbed the pails, sterilized the milk churns, everything. Normally you'd do that, but Miss Millie said a new girl was coming today, so I thought I'd help get us started quickly."

"Ah, right. Thank you. Of course, the equipment," Tamara went over to take hold of one of the milk churns and began carrying it towards the door.

When she noticed Bessie wasn't following her, Tamara looked around. Fixed into the plaster of the far wall at about chest height was an iron ring. Bessie was bent over at the waist, her hands clutching the ring. Beneath her, her enormous heavy breasts hung free, swaying and jiggling as Bessie settled herself into position.

"Okay. Ready."

"Er, ready for...?"

"Milking time, of course."

"Ohh," Tamara groaned, "You're the cow?"

Bessie rolled her eyes. Then she frowned and reached up with one hand to feel around on the top of her head, "Ah crap. Forgot the accessories. Silly me. I wondered why you were taking so long to figure it out."

"Accessories?"

Bessie stood up and fetched two items down from a shelf. One was a hairband sporting a pair of plastic cow horns, the other was a leather collar from which hung a metal cow bell. She put them on, then resumed her bent over position holding the iron ring.

"Okay, now I'm really ready."

"Right," said Tamara with a dry gulp of trepidation, "So... milking time."

Oh boy. What the fuck is this? What sort of a job have I gotten myself into?

No, Tam. Don't overthink this. Focus on the facts:

A) You have a serious lactation and cowgirl fetish. You just do. It's nothing to be ashamed of.

B) A hot girl who looks like she maxed out the boob size slider several times over during character creation and is wearing cow horns and a bell is asking you politely to milk her.

C) There is no (C).

With a quick glance around, Tamara assessed what equipment she would need. She grabbed the stool that Bessie had been sitting on, and in her other hand took one of the metal buckets. She set the stool down beside Bessie's dangling bust and positioned the bucket underneath it, then sat down.

Bessie looked down at her, "That's right. Now go for it."

Tamara put one hand under the nearest breast. The nipple, though quite petite in comparison to the main bulk of the boob itself, still filled a good part of Tamara's palm. It was stiff, but with a little give to it. She hefted the breast, or as much of it as she was able. It was extremely heavy, and sloshed out of her grip as she lifted her arm, like a sack full of warm water.

Tamara scrunched her fingers together in a delicate grip, placing them around the darkened skin that surrounded the nipple, and squeezed. "Like this?"

"Mm-hmm," Bessie nodded. Her eyes were closed and she seemed to be concentrating.

Tamara watched a single tiny drop of white fluid fall from the tip of the nipple where it poked out of her clenched fist. The drop fell into the bucket with a just audible plip. It was working! Excited, Tamara squeezed again, wringing a longer, more squirt-like drop from the teat.

"Ooh, not too hard," Bessie winced. She opened her eyes and winked at Tamara, "At least, not yet. Got to get me going first."

"Oh, sorry," Tamara let go suddenly, "Did I hurt you?"

"Nah," Bessie shook her head, the cowbell jingling, "Don't worry."

"So how do I best, er... get you going?"

"You can talk to me."

"Talk to you?"

"You know, sexy stuff. Horny talk."

"That helps?" Tamara stalled, trying to think. She didn't have much experience with sex talk. Over the course of her life she had probably produced more of it by accident than by intention.

"Hell yeah," Bessie grinned, "It would help a lot. If that's not too weird for you."

"No, it's fine," Tamara said hurriedly. She squeezed again, gently, "You like that, huh? You, um... sexy... cow."

Bessie burst into a loud fit of giggling. Her laughter rippled down through the jiggly flesh of her breast, and Tamara felt it shake against her hand.

"Sorry," said Tamara, feeling a bit foolish, "I shouldn't call you a cow."

"No, no," Bessie sighed as she recovered her composure, "That was a good start. Call me a cow. That's good. I'm sorry I laughed. You're just... really cute, that's all."

Tamara squeezed again, carefully, "How about that... cowtits?"

"Mm, yes," Bessie murmured. Her eyes fluttered closed, "Better. Now tell me what you want to do to my big fat cowtits."

"What I...? Oh, okay." Tamara squeezed again, a little harder, working her fingers down over Bessie's prominent nipple. She gave a little inner squeak of triumph when a proper squirty jet of milk spattered down into the bucket.

"I'm going to... to... milk these beautiful big tits until..."