tagIllustrated1950s: Moms & Daughters

1950s: Moms & Daughters


Summary: Two moms become Mistresses to their daughters.

Note 1: Thanks to Rebecca, the famous artist whose artwork inspired and was used for this new series. Especially her series 'Housewives at Play', 'Teens at Play' and 'Hot Moms'. Thank you for access to your entire book catalogue as well as your website for this massive series.

Note 2: This is the fifth chapter of a multi-chapter story about one woman's journey of sexual submission and lesbian exploration through the decades and through generations of family members.

In part 1, 1950s: 1st Time With a Girl, our 2015 protagonist Kimmy is given a gift of a scrapbook from her recently deceased great-grandmother, Rebecca. When Kimmy opens the scrapbook, she is shocked to find that the scrapbook is a journal of her beloved great-grandmother's sexual adventures...with drawings. Kimmy reads in awe of Rebecca's first time with a woman. Once done reading, Kimmy pleasures herself while reliving her most recent seduction of her nerdy science partner Zelda.

In part 2, 1950s: Housewives' Lesbian Society, our protagonist reads the next chapter in her great-grandmother's scrapbook. Rebecca is caught masturbating while babysitting and ends up having a sexual encounter with a MILF. Rebecca also learns of a secret lesbian society that is years old and she is offered the opportunity to be the newest submissive housewife pet. To earn the privilege to be the housewife pet for her senior year, she must meet the head mistress and service her. Lastly, Kimmy, so horny from the idea of a housewife sex club, envisions dominating one of her neighbours.

In part 3: 1950s: Housewives' Pet Training, our protagonist learns about her great-grandmother's training to be a pet to a community of housewife lesbians. Rebecca is forced to suck cock for the first time, witnesses a massive housewife lesbian orgy, gets fisted and spanked before being ordered to seduce her best friend. Lastly, Kimmy gets herself off after a long night by imagining all the different MILF's she would like to seduce.

In part 4: 1950s: Lick and Fuck Best Friends, our protagonist reads about her great-grandmother's seduction of her best friend. Rebecca becomes more brazen at school and must fulfill the task of seducing her best friend, Eleanor. Lastly, Kimmy gets herself off with a pop bottle as she fantasizes about making her good friend Camree be her public slut.

Note 3: Thanks to Robert, Wayne, and Tex Beethoven for editing.

Note 4: Normal text writing is present day; Bold is Kimmy flashing back to one of her own sexual encounters or fantasizing about one; italics is the scrapbook stories of our hero Rebecca.

Note 5: Also, please note that although I've tried to make the main characters as close as possible to look the same, the photos are taken from a massive collection from Rebecca's website. Thus, there will often be subtle differences (freckles, breast size, etc.). That said, I don't believe it should hinder the enjoyment of the story.

Note 6: Of course, all characters in the story are 18 years of age or older.

1950s: Moms & Daughters

I lasted three days without reading anymore of my great-grandmother's stories. I was trying for a week, but the temptation was too strong. It was like the scrapbook was the ring in Lord of the Rings and I was drawn to it... unable to resist its intoxicating power. This handwritten book with such expressive drawings had become my very own 'Precious'.

I had Zelda get me off each of the other days, but tonight as I gave into the temptation of what was I beginning to think of as the real thing, as even better than reality, my pussy was tingling and I had to see what was about to happen with Rebecca's best friend's mom. I know, sixty years ago and I'm using future tense.

I got undressed, grabbed a vibrator, and got into bed... it was time for a bedtime story... ironically I could recall great-grandmother reading them to me as a child... that said, the stories she had left to me in her will were not the ones she would have read to me back then!

I shook my head.

I still couldn't believe that my sweet great-grandmother, the most caring and compassionate woman I had ever known, used to be a submissive lesbian.

Yet, as I opened the scrapbook to continue reading her journey of sexual liberation in 1954, I had no idea that the shocking revelations were just beginning.


As I reached Mrs. Stroman's house, I paused.

What was I going to say?

"Hey, I'm this year's housewife pet and I'm here to serve you? By the way, Mrs. Madison would like your daughter to be a pet, too."

I realized telling her I was the pet would be easy. I assumed this happened every year and it wasn't out of the ordinary.

But telling her about her daughter, my best friend, that seemed an entirely more awkward and uncomfortable conversation to have.

Before I could chicken out, knowing I was going to obey whatever Mrs. Madison or any other member of the secret society told me to do, including Mrs. Stroman, I rang the doorbell.

I waited.

I rang it again.

No answer.

I checked the door. It was unlocked.

I walked in, not out of the usual... I walked in and out of my friend Eleanor's house all the time... but it was out of the usual at this time of the morning. I heard the school bell in the distance. No worries, I was covered.

I called out, "Mrs. Stroman."

No response, but I could hear a blender in the kitchen.

I walked towards the kitchen still trying to figure out what I was going to say.

Yet even after all the things I had seen in the past little while, all the things I had done in the past little while, what I walked into shocked me completely.

Mrs. Stroman was on the floor, leaning against her oven, almost entirely naked, pleasuring herself in the most unorthodox way... with a blender.

She was also, obviously, near orgasm.

I watched in voyeuristic awe as she held the running blender; it seemed to be on high, hard against her pussy.

I instantly knew I was going to try the same thing when I had the chance.

I knew I should leave; it would be utterly humiliating to be caught in such a compromising position, especially by your daughter's best friend.

Yet my legs were trapped in quicksand.

My eyes were glued to what I was watching.

She moaned, "Ohhhhhh, yes."

Before she could orgasm however, I finally gained some control of my legs and tried to sneak away by backing out, but I bumped into a chair. The chair complained by emitting a penetrating squeak against the floor.

Mrs. Stroman opened her eyes, startled. Her red cheeks instantly went ghost white. "What are you doing here, Rebecca?" she asked.

"Mrs. Madison sent me," I answered, deciding to take the initiative. I walked over to her, dropped to my knees, placed a reassuring hand on her knee and asked submissively, "May I please finish you off, Mistress?"

"No way," she said, as comprehension began to form in her head.

I moved the blender away, lay on my stomach and said, my face now directly next to her pussy, "I've wanted to do you for some time, Mistress."

Before she had time to respond, I began licking her pussy.

"Oh, God," she moaned, "I can't believe you're the one."

"Are you disappointed?" I asked, and returned to licking her already very wet pussy.

"Nooooo," she said. "This is a very, very pleasant surprise, Rebecca."

"And a very delicious breakfast," I countered.

She laughed, "This is surreal."

I licked for a couple of minutes, before she cursed, "Shit, I need to stand up."

She quickly stood up and I looked up at her, as I got onto my knees.

"Sorry, leg cramp," she explained, as she moved her leg around.

I moved to her and asked, "May I?"

She looked down at me and nodded, "Yes, I think you'd better finish what you stopped from finishing on its own."

"I'm sorry, Mistress," I said, moving back to her pussy.

She laughed, "At first I was mortified, being caught in such a compromising position by Eleanor's best friend, but now that I know you're the housewife pet, well Rebecca, the possibilities are endless."

I nodded, knowing of a possibility she had not yet considered, "Oh, Mistress, you can't even imagine how endless."

I leaned forward and resumed licking her pussy.

"Oh my," she moaned, "you have a wicked tongue."

"Thank you, Mistress," I replied, as I kept licking her, looking forward to tasting her full flood of cum. Yet I was still worried about telling her about her daughter Eleanor and Mrs. Madison's delicious new idea.

"Oh, your sleepovers are going to have a whole new dimension," she said. I smiled as I thought to myself 'you have no idea'.

I kept licking. As her moans increased and I sensed she was getting close, I concentrated on her swollen clit.

"Oh yes, you secret slut, lick my clit, suck on it, bite it," she demanded, as she grabbed the back of my head.

I tried to do as I was told, but it became very difficult when she started to actually bounce my head on her pussy. So I just extended my tongue and tried to make as much contact with her pussy as I could.

Eventually she came and she held my head deep between her legs through the entire orgasm. I hungrily licked her sweet nectar. It was similar, yet subtlety different from her daughter's.

Once done, she let go and said, looking down at me, "That was one of the best surprises of my life."

Deciding she had just set herself up perfectly for Mrs. Madison's idea, I smiled, "Funny you should say that."

She pulled me off my knees and asked, "What do you mean?"

"I have another surprise for you," I said, before adding, "two actually."

"You do, do you?" she asked, looking curious.

"Boy do I," I nodded.

"Well, share away," she said.

"Well, Eleanor and I, well, we, um," I began, but wasn't able to say the words.

"Oh my," she said, immediately getting it. "That explains her being at your house all weekend, how tired she was when she came home last night, and her odd behaviour this morning."

"How so?" I asked.

"She seemed different, happier," she said.

"I'm glad," I said.

"So what did you two do?" she asked, as she went to pour us each a cup of coffee.

I reached down to grab my hairband, which had come off during our tryst, and told her the entire story, including the seduction, the pussy pleasing and taking her virginity. I then told her my entire story.

"Wow!" she nodded.

I pondered how to add the second part of the information.

"Well, I'm happy my baby girl is finally exploring her sexuality," Mrs. Stroman said.

"I'm happy you think that," I said. "Because there is something Mrs. Madison wants me to ask you."

"What?" she asked.

"Mrs. Madison wants to have two housewife pets this year," I revealed.

After a brief pause, she said, the significance hitting her, "Oh."

"She wants me to get your approval," I continued, praying Mrs. Stroman would agree. The thought of doing this crazy thing with Eleanor aboard was super exciting!

"Okay," she nodded. "I have an idea."

"Okay, yes she can be a housewife pet?" I asked.

"Likely," she nodded, a look of deviousness on her face. "But I need to set it up."

"Okay," I nodded, unsure what she had in mind.

"Come home with her after school today and once I leave I want you to get her naked and in a sixty-nine," she said.

"Um, okay," I said, unsure what she had in mind.

"Just do it," she ordered.

"Yes, Mistress," I nodded, curious and confused.

"You should probably get to school," she said. "I have to go and have a chat with Mistress Madison."

"You're not angry?" I asked.

"Oh not at all," she reassured. "I just need some clarity on a few things."

"Oh, okay," I nodded, before heading to school.


After school, I suggested to Eleanor that we go back to her place to study for tomorrow's chemistry test and of course she agreed.

Once there, Mrs. Stroman greeted us with cookies and milk. I couldn't help but smirk at the wholesomeness of the snack... when we both knew that what I really wanted to snack on was hiding under her dress.

Mrs. Stroman asked about our day and said that she had spent the entire afternoon visiting with Mrs. Madison about some big opportunities for Eleanor and me.

Eleanor asked, "What kind of opportunities?"

"It's a surprise for now," she smiled, as she prepared to leave.

As we went to the living room to turn on a record and study, Mrs. Stroman asked, "I'm going to the market. You girls want to come?"

We both said, "No thanks," as I slyly squeezed Eleanor's ass.

The instant the door was closed, I grabbed Eleanor's hand and giggled, "I need a tasty drink of pussy juice to wash down that wholesome snack your mother gave us. What do you say?"

"Oh my God!" Eleanor giggled, as I led her to the living room. I put on the new Frank Sinatra album 'Songs for Young Lovers' which suddenly seemed so perfect.

I walked back to Eleanor and kissed her. I knew I had only ten minutes to get us in a compromising position, so I unbuttoned her blouse.

She said, "We can't do it here."

"Your mom just left, we have at least half an hour," I countered, as I removed her blouse. "That's lots of time for a yummy cocktail."

"Okay," she trembled, as I slipped her bra off.

A couple of minutes later, we were on the carpet, in a sixty-nine, hungrily licking each other.

My face was buried deep in Eleanor's pussy when I heard, "I forgot my keys and... what?"

"Mom!" Eleanor gasped.

"Exactly what is going on here young lady?" Mrs. Stroman demanded, in full actress mode.

"I, um," Eleanor stammered; I kept licking.

"Are you a lesbian?" Mrs. Stroman accused.

"I don't know," she moaned. She tried to move, but I held on to her ass. She wasn't going anywhere and I continued licking.

Mrs. Stroman ordered, "Rebecca, come to me,"

"Yes, Mistress," I obeyed, letting go of Eleanor's ass.

Eleanor stood up and watched, confused, as I crawled obediently to her mom and sat at her feet.

Acting done and gentler now, Mrs. Stroman said, "I think it's time to let you in on a secret, Eleanor."

"What secret?" Eleanor asked, as I submissively caressed her mom's calf.

Mrs. Stroman snapped her fingers and pointed to her pussy. I wordlessly moved underneath her skirt and straight to her pussy, like a tracking dog on a scent.

"Rebecca! Mom!" Eleanor gasped, as I began licking her mom.

As I licked, Mrs. Stroman explained the entire secret housewife society, my recent position in it and her learning about me being the pet just today. She then added, "And Mistress Madison has requested that I allow you to become a housewife pet, too."

I wished I could have seen her face. Was she freaking out? Was she taking it all in? She hadn't said a word throughout the entire explanation which was very unlike her.

Mrs. Stroman ordered, "Come and unzip my dress, Eleanor."

"Really?" Eleanor asked, her tone still implying she was confused and overwhelmed.

"Now, Eleanor," Mrs. Stroman ordered.

"Yes, Mother," Eleanor replied.

I kept licking as I heard the zipper going down and felt the dress lift up over me, revealing my pussy pleasing activities and my shiny face.

Mrs. Stroman ordered, "Now sit over there and watch your best friend get Mommy off."

With that, Mrs. Stroman grabbed the back of my head and guided it, gently this time, deeper into her. I eagerly lapped her inner labia, really turned on by the knowledge that Eleanor was watching my every move.

In only a couple of minutes my face was being flooded with cum and my tongue went into overdrive as she moaned, "Lick up all my cum, my pet."

Once she had calmed down, she let go of my head and asked, "Rebecca, do you want Eleanor to be a pet with you?"

"Yes, Mistress, I would love that so much." As I answered, I looked beseechingly at Eleanor, who still looked completely bewildered.

"Good," she nodded. "I really do have to go and get some groceries. So please tell Eleanor your story and then at 8 o'clock you two are to go and see Mrs. Madison at Ms. Winston's home."

"Yes, Mistress," I nodded, thinking 'Ms. Winston too? How many teachers were part of this lesbian secret society?'

Mrs. Stroman caught her daughter's attention and added, "When we are home alone, or with pet Rebecca here or at a society gathering, you will answer to me as Mistress Mommy. Is that clear?"

Eleanor nodded, still looking overwhelmed.

"Say it," Mrs. Stroman firmly demanded.

"Yes, Mistress Mommy," Eleanor replied.

"Good girl," Mrs. Stroman nodded, as she added, "Now get Mommy's dress for me."

"Yes, Mistress Mommy," Eleanor again said, this time sounding more natural.

I watched from my submissive position on my knees as Eleanor respectively and carefully dressed her Mother.

Once dressed, Mrs. Stroman suggested, "You should probably continue this in your room, Eleanor. Your father will be home in under an hour."

"Yes, Mistress Mommy," Eleanor nodded.

Mrs. Stroman pulled me up from my knees and kissed me. Breaking the kiss she quipped, "Damn I taste good. See you for dinner in an hour."

"Yes, Mistress," I said.

"Yes, Mistress Mommy," Eleanor said.

Once she was gone, I took the initiative, grabbing our clothes and guiding Eleanor to her bedroom.

Eleanor said, "I can't believe it."

As I closed the door, I asked, "Which 'it' don't you believe? That there is a lesbian secret housewife society? That your mom is part of it? That Mrs. Madison is the head Mistress? That I'm a sexual pet to at least twenty housewives? That your Mom speaks and I obey without hesitation? Or that they want you to join as a pet so you can do what I'm doing?"

"All of the above," she said.

I walked over and kissed her. She didn't respond at first, but then kissed me back. When I broke the kiss, I explained, "Eleanor, just like it is for me, this is a natural transition for you. We are both people pleasers."

"I just can't fathom my mom as a lesbian," she said.

"I don't think my Mom actually is, but I don't know for sure," I said, somehow happy she wasn't a part of the club... at least I was pretty sure she wasn't. Suddenly I realized that if Eleanor's mom was in the club, so might mine be. They were best friends. I was still very new to all this, and didn't know who was in and who was not.

"And how does it work?" she asked.

I described my entire collection of experiences, as well as who had been previous housewife pets, and then said, "I'd love you to share this opportunity with me."

"Really?" she asked, taking in all she had learned.

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