Housemaid Drinks Teen's Milk

"Your extra towels, Ms. Miller," she said, laying them neatly on the table near the pool.

It was Kathleen's third day on the job. She was a maid for the upper class, and at the age of 36, her resume was already impressive. It included service for the financial elite, celebrities, and even a brief stint in the White House.

Now here she was, working proudly for a wealthy family at their manor in San Diego. It was the ideal job. The Millers were wonderful people; titans of the tech industry. It was estimated they were worth nearly a billion dollars.

A family like that required the services of a person like Kathleen. Someone who looked the part, had the mannerisms of a 1950's housewife, and who understood the true value of loyalty. So far, things were off to a great start.

What made this day different, however, was that Mr. Miller and his wife had departed for a weeklong vacation to visit with family. They left behind their bombshell of a daughter due to her last minute commitments. She was a 19 year old socialite who happily lived life in the public eye.

Kathleen had just brought extra towels to the backyard pool area of the large estate. They had met a few times in passing, and Madison didn't seem particularly interested in a formal introduction even now, as the socialite tanned on the recliner. In her oversized sunglasses, she looked quite glamorous.

God, what a beauty. Madison had a movie star face and the body of a fashion model. Long and thin. Her breasts seemed a cup size bigger than they should have been, likely because of her recent pregnancy.

"Thanks," the socialite said flippantly, taking a sip of freshly squeezed smoothie.

Kathleen neatly placed the towels down, then pressed them so that they'd look perfect. The two women were a stark contrast to each other. Madison wore a skimpy bikini and flaunted her goods.

On the other hand, Kathleen wore a nice housemaid uniform, consisting of white shoes, a blue skirt, and a short sleeve button down blouse. Kathleen's long hair was in a ponytail and she wore little makeup. As a consequence, she looked older than she actually was. But without a doubt, Kathleen was an attractive woman in her own right.

For the first time, the socialite glanced at the maid, then pulled her sunglasses down to get a better look.

Madison cracked a smile and removed her sunglasses completely. "We've never formally met, in private I mean, with just the two of us."

While still laid back, Madison extended her hand like a princess who expected a servant to kiss the ring. Kathleen didn't play that game, and instead gave a sincere handshake and a polite smile in return.

"It's a pleasure. Your family is lovely."

"Speaking of which, have a seat," Madison said, gesturing to the lounge chair beside her. "Lay down for a moment. I've been meaning to talk to you about something."

Lounging around on the job was never Kathleen's style. It might make her look like a nonchalant worker, which couldn't have been further from the truth. She prided herself on being precise at all times. So she compromised with herself and sat upright on the corner of the lounge seat.

"I'm fine like this," Kathleen smiled politely, sitting uncomfortably.

Madison's fingertips gently rubbed along her own belly. "You know about my situation, right? It's appeared in the tabloids once or twice, assuming you read that stuff. Do you read the tabloids?"

"Can't say that I do. I tend to stay away from that sort of gossip."

"That's too bad," Madison shrugged. "Tabloids are like my Holy Grail. But you know what I'm talking about, right?"

Kathleen nodded. "Of course, your parents told me about it. As an employee of the residence, I would be happy to help. It's no issue at all."

"Being a single mother at my age wasn't something I planned. I mean, I love my kiddo with all my heart and I know I'm lucky to have rich parents to support me. But that's life."

"You don't have to explain anything to me, Madison."

"Please, call me Maddy."

"Maddy. Pretty name," Kathleen smiled.

"Anyway, I took a peek at your resume. Impressive. I've also noticed that you have a lot of experience with prominent families."

"Correct," Kathleen said proudly. "Like I said, I can manage anything you need."

Madison raised an eyebrow. "Anything?"

There was a slightly naughty look on the socialite's face, which Kathleen hadn't seen from any of her previous clients. For a moment, she wondered if the upcoming request would be sexual in nature. It was just a hunch, or maybe intuition. As an attractive career woman, Kathleen had dealt with her fair share of sexual harassment in the workplace, usually from men, sometimes women. But she quickly pushed that idea away. Surely, there was no way someone like Madison would ever have such thoughts about her.

"It's just us here," Kathleen said, almost in a motherly way. "You can tell me anything. I'm discreet. What's on your mind?"

Madison responded with a wide, but slightly lecherous smile. "Well, since you're offering, there are things that you, and you alone can help me with. I'm not interested in any of the household staff performing this type of work."

"Sure."

"Before we get into it, let me tell you about my schedule, which you'll notice is hectic. Basically, I work a lot. Yes, you heard that right. I work! Don't be fooled, and don't believe what you hear. Behind this Hollywood face of mine, there's a brain which processes numbers, figures, and creates new ideas. I help manage my father's properties and I'm helping to open a new high-end restaurant with a few friends of mine."

Kathleen nodded and her eyes nearly sparkled. "I'm genuinely impressed. Good for you. It's always good to see savvy female entrepreneurs."

"You've got that right. This is only the beginning."

"Excellent."

"Don't get me wrong," Madison quickly clarified. "My top job is being the best mommy possible to my kiddo. I have my priorities straight. But as a figurehead in the business and social world, I'm also expected to look the part. To put it bluntly, I'm expected to be hot. Do you see where I'm going with this conversation?"

Kathleen tried to hide her confusion. "No, not really."

"First, I workout regularly, almost religiously. Second, as a mommy, I also need to have my mammary glands stimulated while my kiddo is away visiting his grandparents. If they don't get drained regularly, my milk supply will diminish. Plus my tits start to feel full and uncomfortable. So, you can help me with those two things."

A polite atmosphere remained between them, but Kathleen resisted the urge to scratch her head. It was the first time she had ever had such requests in her more than a decade long career. But then again, she had never tended to such a demanding socialite before. Well, this should be fascinating.

"It sounds like an interesting challenge," Kathleen said. "I'm definitely not a physical trainer though."

Madison laughed. "I can handle that part. You can help, you know, stretch me or whatever. It's always good to have an assistant on hand in that situation."

"And for the other task?"

Deep down, Kathleen was almost afraid of what the answer might be.

Madison's laugh turned mischievous. "I'm a spoiled brat. Don't you know brats like me can't do anything without proper help? I need you to keep my motors running, so to speak. You know, help my milk production remain regular while my kiddo is on vacation with my family. That's advice from the doctor. Use it or lose it. And I can't afford to lose my milk."

In all of Kathleen's years on the job, she had never been asked to do anything so intimate. But then again, the instructions were vague, and the request seemed reasonable, though the way it was phrased left room for ambiguity.

Kathleen put on her poker face. "That sounds doable. I'd be happy to oblige."

Their conversation seemingly came to a halt when Madison abruptly put her sunglasses back on. With a playful smile on her face, she nodded and dismissed Kathleen.

"That will be all, for now."

***

The following day, Kathleen was made to sit on the lounge chair as Madison went through a series of exercises. Pop music played loudly on the sound system as the sexy young socialite worked through choreographed aerobic moves, as if it were a dance. Sweat glistened from her fit, tanned body.

After about 20 minutes, Madison cooled down for a bit, then dove into the pool to swim several laps. Great for cardio and overall body strength.

Kathleen watched the workout filled with admiration. Never in a million years did she think her duty would be to sit around watching a young woman exercise and swim. In a way, she found the task demeaning. Frequently, she silently reminisced about the time she used to serve coffee to a sitting US President, and how he'd ask kindly about her day.

Fond memories.

Madison stepped out of the pool, water glistening off her body, and she looked like a swimsuit model. The hard work had paid off. Kathleen knew that her service was expected so she stood up, ready for action.

"Towel," Madison said curtly, wiping water away from her face.

Kathleen grabbed a large white towel, brought it to the socialite and unfolded it, holding it out for Madison.

In return, Madison held her hands up. "Dry me."

"Yes ma'am."

It was a delicate dance. Kathleen had no problem drying off someone with a towel, especially if it was a member of a family she was serving. It was all part of the job, really. But what made this tricky was that those bikini-clad breasts stood out prominently as Madison held her hands in the air. Kathleen tried to be reasonable about the task, rubbing mainly the hair, backside, and the other non-sexual parts. She only dried the breasts by softly patting them with the thick towel, but even then she could still appreciate their firm quality.

All the while, Madison gave her instructions: "The top too... a little around the side ...yeah, that feels nice, rub there a little more. Nice."

Madison said, with a practiced smile, "Told you, I'm spoiled."

"I don't think you're spoiled at all. You're blessed."

Madison laughed. "In more ways than one. My butt and legs are still dripping."

"Understood," Kathleen said.

She rubbed downward across the barely-covered butt, then lower to the thighs. Finally, she knelt down to rub the feet.

"Not bad for someone who gave birth a year ago," Madison boasted about her own physique.

After finishing, Kathleen took a step back. "You look quite amazing, Maddy. I can certainly imagine you being in a magazine."

Madison playfully struck a pose. "Vogue or Playboy?"

"Well, something classy," Kathleen said after becoming unexpectedly tense.

"Good answer. Now this is the part where you help me stretch. Ready?"

"Of course."

Kathleen put the wet towel away. Almost immediately, Madison struck different poses which showed off her flexibility. Each time, Kathleen was expected to help hold the stretching pose, In essence, she was required to dig her fingers into the soft, tender skin of the sexy young socialite.

In all honesty, this was the most physical intimacy Kathleen had ever shared with another woman. She was used to giving handshakes and affectionate hugs, not holding onto a woman's almost naked body. Kathleen was mesmerized by the muscles in Madison's arms and her shapely legs. When it came time to grab Madison by the rib cage, Kathleen felt her heart racing. It wasn't from just the heat.

Seeing Madison's body up close under the bright sunlight made Kathleen's breath hitch. The smoothness of her skin caused Kathleen to feel a bit light headed. Never before had Kathleen felt so unsteady around a female. But admittedly her personal life had taken a backseat while she worked long hours. She hadn't had a serious relationship in almost five years.

What made this even more awkward was that Madison was a sex bomb. She exuded confidence and seemed to sense Kathleen's misgivings. Whenever possible, Madison would lock eyes with Kathleen and raise one eyebrow, suggestively.

When the stretching was complete, Madison stood upright and smiled.

"I feel like a new woman," Madison proclaimed.

"That was... interesting for me too, shall we say. I haven't been someone's workout partner since I was in high school."

"Get used to it. Now here's the part where your job really gets interesting."

"I assume you're referring to your milk. I could feel how full your breasts were."

Madison smiled and nodded. "My tits feel like overstuffed water balloons. They're killing me right now. You've never lactated, have you?"

"I've never had the pleasure. No."

"It's a unique feeling that's hard to explain. But imagine there's a fullness inside your tits. Like they're so ripe, they might squirt if pinched. That's literally what it feels like. Actually, it's pretty cool if you think about. And it's really a bit sexy, too."

There was a lustful expression on Madison's face which made Kathleen uneasy. She reassured herself internally. Young people have very different lifestyles these days. Even though Kathleen didn't understand the intricacies of the current generation, she accepted them.

"How should we proceed?" Kathleen asked stiffly.

Madison took a moment to flash a questioning gaze. "Something tells me you're still a little hesitant."

"Not at all," Kathleen said defensively. "I'm happy to assist with anything you need."

"Hmmm... Maybe so. But I don't know if you're ready for me. As you can already tell, I'm very unorthodox, at least compared to anyone else for whom you've worked in the past. I'm not a bitch, I swear. I'm a brat! A really really wealthy one. And wealthy brats like me want to be treated like princesses. So far you're doing a great job. But there's room for improvement."

It was an odd statement. Kathleen was bewildered, and it showed.

Madison continued, "Come, let me clarify things."

They locked arms and Kathleen was guided over to where the lounge chairs were placed by the pool. The chairs were side by side and they both sat upright, facing each other.

"Is this necessary?" Kathleen questioned as they were mere feet apart. "I'm serious about what I said. I'll do whatever you require. I'm a fast learner and well-organized, so any special needs can easily be accommodated."

Madison came out of left field. "How did you feel about massaging me? Pressing your fingers on my skin. Touching me. All that stuff. How did you feel about it?"

"I beg your pardon?"

"Did you like touching me?"

Madison had narrowed her eyes to show that she meant business. She expected a serious and honest reply. Her tone, while questioning, wasn't judgmental. However, it did appear that Madison was hoping for a very specific answer.

"I don't think I understand," Kathleen said, sincerely befuddled.

Madison spoke softly, just above a whisper. "Look, don't worry about your job. You're not going to be fired or anything. I'm not trying to pressure you or make you uncomfortable. I just want to know. Are you comfortable around nudity? Tits like mine? Be honest, it'll be our secret. I swear."

It was very straightforward, and Kathleen knew today would be anything but ordinary. This felt like a turning point in her employment. Working for the Miller family had already felt like a perfect match. She could easily envision herself working for them long term. Hopefully, they felt the same way, especially Madison. Kathleen was surprised at that longing.

So, Kathleen did her best to give a straight answer. "Yes. Nudity is not a problem for me. I played sports in college so I've showered in plenty of women's locker rooms. I assume you're asking because you want me to be present when you're using a breast pump. I've done that before. If you'd like, we can..."

"That's a good start," Madison said, interrupting the maid. "But I don't use breast pumps."

"Why not?"

"I hate them."

Her answer was quite mysterious, 'I hate them.' It made Kathleen wonder what this girl could possibly have in mind. It's 2017, and mothers of all ages commonly use pumps. Who would hate something so convenient?

"Why?" Kathleen inquired.

"There's no denying that I'm a new age chick, who's glued to my phone and social media like every other millennial. But I'm also a naturalist at heart, believe it or not. And breast pumps feel so... unnatural. It makes me feel like I'm some sort of lab experiment. Or a cow on a dairy farm."

It was Kathleen's turn to smile. "Okay then, Ms. Naturalist. I'm assuming you have an alternative method in mind."

"It sounds like you're questioning me," Madison said playfully. "Like you're assuming that my methods are no good."

"Not at all. Holistic approaches should always have a place in modern society."

"Well then, are you ready to step into my secret world?"

Kathleen playfully shrugged. "What's there to lose? I like keeping an open mind."

While Kathleen's answer had been honest, she never anticipated what would happen next. Madison pulled the left side of her own bikini top down, to expose the entire tit. The majority of the breast was nicely tanned, which was in stark contrast to a white triangle of untanned skin that had been hidden under the bikini top.

The breast appeared round and luscious. Firm and full. The areola was light pink and the nipple was certainly bigger and darker than average. In fact, the whole tit seemed to be straining. It was the breast of a lactating young woman.

Kathleen was caught off guard by the gesture, but Madison smiled devilishly. She obviously reveled in exposing herself to the maid.

"You said you're comfortable with nudity," Madison joked, holding out her markedly distended tit, which seemed like an offering.

Kathleen snapped out of it. "You caught me off guard."

"Do you like it? You seem a bit unsettled."

"What exactly can I do for you?" Kathleen replied, setting a more proper tone for what should have been a serious conversation. "Again, I'm happy to help, but things must remain professional."

"Oh relax, mommy and daddy won't know. This will be our secret."

"Then tell me specifically what I can do to help." Kathleen repeated, trying hard to maintain a proper tone.

Just then, the backyard door opened and they heard someone from the kitchen staff walk around the area to retrieve something. Madison made no attempt to hide her exposed tit from the staff member.

Madison smiled. "You can start by having him bring us some drinks. The chef prepares fresh smoothies for me every morning. Ask for two cups, one for each of us."

"Very well."

Kathleen attempted to get up, but Madison motioned for her to remain seated.

"No, have them bring it here."

Kathleen hesitated when it was clear that Madison had no intention of putting her tit away. Nonetheless, she asked the staff member to bring them two cups of the freshly made fruit drinks.

"Isn't this better?" Madison teased. "Instead of working, you get to sit around by the pool with me. And we get to share smoothies."

Kathleen cleared her throat. "Thank you."

"You seem tense."

"Are you going to put your breast away, Maddy?"

"Why would I?" Madison asked with a deceptively innocent grin. "My breasts are so full that they could burst at any minute. I'm just desperate for release."

It was then that Kathleen knew exactly what was planned. It nearly made her gasp as her eyes widened (a gesture that made Madison smile). Sure, Kathleen could put a stop to this. She could just walk away. After all, Madison hadn't tied her to the chair. And certainly Maddy wouldn't tell her parents about this.

Maybe it was curiosity that forced Kathleen to remain seated. Or maybe it was the unfamiliar tingling in her own nipples. Or... perhaps it was the moisture that had just pooled between her legs...