tagIllustrated1950s: 1st Time with a Girl

1950s: 1st Time with a Girl


1950s: 1st Time With a Girl

Summary: Innocent virgin is seduced into a lesbian lifestyle.

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 beginning of a multi-chapter story about one woman's journey of sexual submission and lesbian exploration through the decades and through four generations of family members.

Note 3: Thanks to Robert, goamz86, cuckdynasty and Wayne for editing this.

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

Note 5: This is a Valentine's Day 2016 Contest story so please vote.

1950s: 1st Time With a Girl

It was at the reading of my great-grandmother's will that everything changed. She left me 100,000 dollars, which was amazing. I had no idea that she had any money saved away at all. But... that wasn't the best thing she left me.

No, she also left me a diary... an illustrated diary.

And although the 100,000 dollars was awesome and life changing... it paled in comparison to the shocking to the core, life altering revelations that were revealed to me in her own words.

It affirmed things about me I was questioning.

It explained why I felt the way I did about so many things.

It allowed me to become the woman I am now.

But I'm jumping ahead.

When I first got the envelope, I had no idea what revelations I would learn about my great-grandmother's past, but about three generations of my family's women's past, including my mother.

The outside of the envelope read:


So although curious, I waited until late that night, once Mom was in bed. A chill went up my spine as I opened the envelope. Inside was what looked like a scrapbook as well as a hand written note.

I took a deep breath at the thrill of getting some final words from the woman I loved the most in my life before I read the note written in great-grandmother's own handwriting:

My dearest Kimmy,

If you are reading this, I have passed away. Don't be sad. I lived a great life. A life with NO REGRETS! A life very few women can say they have lived.

I wanted to be there for your graduation to share these secrets in person, but unfortunately I couldn't quite make it.

Before I continue I must say this: I am so proud of you. You have turned into a great young woman and will do great things in this world.

Now, it is important that you read this scrapbook with an open mind. The odds are it will shock you. You may even question if it is all true. It may at times disgust you. But please don't judge me poorly... like I said, I have NO REGRETS.

Also, every word in here... no matter how shocking... is true.

Every person mentioned is a real person (or was, God bless their souls) and each has a special place in my heart.

I have always refused to live by the standards society expected of me. Sometimes by choice, others by force, but in the end, all my decisions led me to who I became.

And you... Kimmy... you are a lot like me. And like me, I believe you are questioning your role in the world. Hopefully, this scrapbook will clear it up.

Now, like I said already, this scrapbook will likely shock you.

I wrote everything a few months ago and have since added illustrations because I have always been a visual person. Plus, I love to draw, and by creating these pieces of art I got to relive over 50 years of wild adventures.

I had hoped to have them all in colour, but my arthritis simply got too bad. I have coloured a few... some I think are the most influential in my life long journey of self-discovery. There were so many pivotal moments in my journey that I don't want to trivialize any by implying one is more important than another. Each moment is special on its own, and each moment leads to more moments. That, my dear Kimmy, is life.

Please take this scrapbook for what it was meant to be... a way to help you in your own self-discovery.

I love you Kimmy, and remember, I see a young me in you. I hope this scrapbook will be a way to remember me fondly forever and understand who I was and who, I believe, you are.

PS: Please help your mother in these dark times.

Love forever,


PSS: Use the code phrase 'Sit pet' and your mother will know that you are replacing me.

I read the letter a dozen times. I read the PSS many more. What the heck did the phrase 'Sit Pet' mean?

Well, they say curiosity killed the cat and, well, I was curious as hell as to what the strange, intriguing note could possibly mean.

So although I was tired, I got on my bed and looked at the scrapbook. There were no words or pictures on the cover... no clue of what was inside.

Giddy with curiosity (Can someone be giddy with curiosity? I don't know, but that is the only way I could describe the emotions swirling inside me as I prepared to open the scrapbook), I took one more deep breath and opened the book. I GASPED!!!

The first page was a picture of a younger version of great-grandmother.


At the bottom there was a note: This picture was taken by your great-grandfather one day. He knew of the secrets I am about to reveal and loved me anyway. He was a great man that God took too soon (many years before you were born).

Why was my great-grandmother leaving a picture of her naked for me?

Still curious, I flipped the page and tried not to judge, as she had requested, I began reading.


How it All Began

It was the summer of 1954 and I was working at the café near the lake a few miles from town. I can still remember the burger smells, the taste of old fashioned root beer (it wasn't old fashioned back then, it was just root beer), and the pure innocence of that summer before my senior year.

I was eighteen already, like many seniors were before school started back then, and innocent as could be. I had kissed a couple boys and so forth and was with Steve, a preppy rich boy (your great-great grandfather was very well off and wanted me only dating boys with good families), when things changed.

Ellie was a free spirit, born a decade too early. She would have loved to be a teenager in the sixties... although she still loved the sixties anyway. All summer, she pushed my conservative family values as well as my even more conservative views on sex.

She couldn't believe I hadn't had sex with Steve yet. She was even more shocked that I hadn't given him a hand job or a blow job.

I still remember her asking, "How big is his dick?"

"I have no idea," I said, having never touched it.

"You have been dating for five months and you have not even assessed his package?" Ellie said, in complete dismay.

"No," I said. "I'm a good Christian girl."

"Well, it's time for you to sin," she said, and leaned in and kissed me.

I was paralyzed with shock.

After a moment, I kissed her back before realizing what was happening and I broke the kiss. I stammered, "W-w-what are you doing?"

"Helping you sin," she shrugged and walked out of the work room and back to work.

My head was spinning and my vagina was tingling. (I will use a lot more vulgar words later on for my kitty, but at that moment I was still sweet and innocent).

I was confused by why she did it. I was even more confused by my body's reaction.

The next couple of weeks, she didn't mention it and I didn't have the gall to either... yet every time she walked by me, or talked to me, I got giddy with anticipation... like I would when I waited by the phone for a boy to call.

It was the second to last Friday beach party of the summer, every Friday had a beach party, rain or shine, and I drank for the first time. Now I wasn't the biggest goody-goody in the world, I had had wine a couple of times with my parents and sipped a couple of beers (but learned that beer was disgusting - a belief I will hold until I die), but I had never gotten close to being drunk.

Ellie and I drank a whole bottle of wine between us and when she suggested we should go for a walk, I nodded, hoping it would help me sober up. As we walked, she took my hand and said, "So you don't fall."

That made sense to me and we walked hand in hand.

I couldn't lie, it felt natural and exciting to hold her hand and the kiss came flashing back to me.

A few minutes into the woods, she turned around and said, "I'm going to kiss you again."

"Okay," was all I said, both excited by her words and nervous.

This time the kiss was tender and passionate. It lasted an eternity and made my knees buckle. It was so much more intimate than kissing a guy.

When she broke the kiss, I felt a little crestfallen. Yet, when I opened my eyes, I was suddenly dizzy and stumbled into her. My hands going directly onto her breasts.

She giggled, "How forward of you."

I apologized, "I'm so sorry."

She cupped my breasts and said, "There, now we are even."

"Oh, my," I moaned, not moving her hands away.

"Your breasts are huge, Rebecca," she said, squeezing them gently.

"What? I-um," I struggled to speak coherently, both because I was inebriated and sexually confused.

"Just relax, Rebecca," she said softly. "I know you want this as much as I do."

"I, um, well," I still was overwhelmed as she began to pull my sweater over my head.

Once it was off, she said, "You're so beautiful."

"Really?" I asked, getting drawn in by her words.

"Oh yes, perfection," she nodded as she unclasped my bra.

"Oh, golly," I said as my breasts were suddenly out in the open.

"Such big nipples," she said as she leaned forward and took my right nipple in her mouth.

"Ohhhh," I moaned, never having had my nipples licked. I had had them manhandled by a couple boys, Steve included, but never had I been topless in front of them. A chill went up my back at her touch and warm mouth.

"Just relax, Rebecca," she purred. "I'm going to teach you what real pleasure is."

And she did.

She duplicated that attention on my other nipple.

She then lowered herself to her knees, lifted up my skirt, and tugged down my panties.

I stood there in awe.

I mindlessly lifted up my foot to allow her to take my panties off. She moved them to her nose and said, "Mmmm, you smell heavenly."

I blushed even more as I watched her put them in her purse and then ask, "So I assume you haven't had your dillypot licked?" (Dillypot was a slang term for pussy that started in the 1930s I believe, but was still around in the 1950s)

"No," I nodded as I watched her on her knees move under my skirt.

"Well, let's change that answer," she said before I felt her tongue on my vagina.

"Ooooooh," I moaned as an intense pleasure, unlike anything I had ever felt before, coursed through me.

"Wait till I get you off, sweetheart," Ellie said as she kept licking.

My head went to mush. I knew this was wrong. Good girls did not let other girls lick their vaginas. Yet, the pleasure that came with the act overrode my moral code.

My breathing got heavy in a matter of seconds and before I knew it, I felt fireworks go off inside my body as I had the first orgasm of my life. My body twitched, my legs buckled, and my pussy flooded as I learned what it meant to be a woman. "Oh my God," I moaned loudly, realizing I had used the Lord's name in vain, but was so far gone with reaching heaven that I didn't care.

"So yummy," Ellie said as she kept licking me.

Eventually, she stood back up and kissed me again.

I could feel my own juice on her lips.

"We should probably get back," Ellie said. "Steve will wonder where you went off to."

I asked, "Shouldn't I return the favour?"

"I'd love that," she smiled. "But I want you to make that decision when you are completely sober."

I laughed, "I think I'm sober now."

"Well, I did cleanse your system," she joked, taking my hand and leading me back down the trail.

It wasn't until the next day that I realized she had kept my panties.

Due to a plethora of problems, everything from my own guilt of committing such a sin and cheating on Steve, to Ellie missing a few days of work with the flu, to my inability to talk to Ellie about it, I thought that I may never get to return the favour.

That said, almost every night, I woke up with my hand in my panties as a vivid dream played over and over in my head. A dream where Ellie and I became lovers.

Remember, it was 1954 and women were not lovers.

Even though I felt guilt, I couldn't stop thinking about the pleasure Ellie had given me. I wanted to feel that pleasure again and I wanted to give Ellie a similar pleasure.

I had finished my shift and was waiting for Steve, when Ellie gave me a note while Steve was in the bathroom.

I read the note:

Ladies room in a couple of minutes.

A chill again went up my spine and I felt a gush of wetness hit my panties. The forest was a bit risky, the party and a hundred teens were not far away. But the ladies room was a much greater risk. Plus, how long could I leave Steve waiting for me?

Steve returned a moment later, my head spinning with indecision. I knew I shouldn't go, but I was curious. And although they say curiosity killed the cat... curiosity forever changed my life.

Ellie came back and asked, "May I take that for you?"

I replied, feeling nervous and excited, "Uh, sure. I'm going to powder my nose, Steve."

"Okay," he said, used to me going to the washroom. I had a small bladder and always liked to look presentable.

I waited a second and got up adding, "I may be a few minutes Steve, I'm suddenly not feeling all that well."

"Okay," he nodded.

I walked to the ladies room and paused. I turned around to see Ellie almost right behind me, a sexy smile on her face.

I went into the bathroom as Ellie put a sign in front of the door saying 'closed for cleaning'.

She followed me in, locked the door, and said, "I have been craving a taste of your dillypot every day since our little secret rendezvous last Friday."

"You have?" I asked, still shy and insecure.

"Have you thought about that night at all?" she asked, now directly in front of me.

My cheeks went red as I admitted, "Only when I am awake or asleep."

"So not often," she joked, before kissing me.

Breaking the kiss, she lowered herself to her knees and said, "I can't wait any longer. I need a sample of your perfect poon tang."

Another term I hadn't heard before (and has since evolved into a more vulgar term), but I leaned against the sink counter.

She pulled my panties down and again put them in her purse.

I joked, "I'm going to run out of underwear at this rate."

"Souvenirs," she smiled before adding, "You can have mine in a few minutes."

"Oooooh, okaaaaaay," I replied with a moan as her tongue made contact and sent electric waves of pleasure to the very core of my being.

"God, you should bottle this taste," she purred as she licked me.

I moaned, "Do you think there would be a big market for poon tang?"

"It would be a best seller," she nodded.

"It may be tough to market," I pointed out.

"Yes, maybe we would just have you travel the country and have women get the addictive drink directly from the source," Ellie suggested as she kept licking me.

Her tongue felt great, but I wasn't coming as quickly. Maybe because I was sober, or maybe because of where we were and the risk of getting caught, but I couldn't come.

I said, after a couple of minutes, "let me do you, Ellie."

"Be careful," she smiled as she stood up and hopped up onto the counter. "One lick and you will be a lifelong lesbian."

I laughed, "I don't think so."

She hiked up her dress, spread her legs, and purred, "Come and join the feminist movement."

"Licking vagina is a feminist movement?" I asked as I stared at her pussy.

"Of course," she shrugged, "its women looking after themselves. We no longer need men."

"We do to reproduce," I pointed out.

"Someday even that will change," she said, before adding, "Come and lick joy-trail."

I moved into position even as I smiled at the newest name for her vagina. One that seemed to make the most sense.

I took a deep breath and was drawn instantly by the exotic scent that reminded me of my family trip to Hawaii, although I couldn't explain why... other than it was unique, musky, and exotic.

I then extended my tongue and licked.

I had always thought Romeo & Juliet was absurd, because you can't fall in love at first sight.

Yet, one lick and I was forever changed.

The scent that was captured in her pubic hair, the taste that was better than the sweetest wine, and I knew then, that I was definitely a lesbian.

Her hand on my head, her moans of pleasure, and I was hooked.

I also couldn't explain how natural I felt on my knees serving. A position I would be in at least a thousand more times in my life.

"So good, Rebecca," she moaned, before adding, as if reading my mind, "you're a natural."

I licked and licked, and when her breathing increased, I moved to her swollen clit and flicked it with my tongue.

"Oh God, yes, more, more, more," Ellie demanded.

I kept doing it until she grabbed my head and pulled me roughly into her vagina. I kept licking and was soon rewarded with a complete face wash. Her wetness coated my entire face and I eagerly lapped up whatever juice I could.

It was like the nectar of the Goddesses and I was ready to be forever a servant to it.

She pushed me away a moment later and ordered, "Bend over."

"I should get back to Steve," I said.

"You're not leaving until you come," she said, as she bent me over and began fingering my now very wet vagina.

"Oh my," I moaned.

"Come for me, Rebecca," she purred, kissing my ass as I used the wall for support.

"Oh yes, so yummy," I whimpered, my orgasm building quickly.

"You're so wet," she said, as I literally heard sloppy sounds coming from down below.

"So good," I moaned, as she continued pumping her fingers in and out of me.

"Come now, baby," she demanded. "Come for Ellie."

And as I did, I said the most meaningful words in the relationship world, ""I love you."

She kept pumping her fingers in and out of me as she gave me the second orgasm of my life while I leaned onto the wall for dear life.

I was still coming when we heard someone try to open the door.

Pulling her fingers out of me, Ellie said, "I guess that means our time is up."

"I'm not sure I have the strength to walk," I said, still feeling the intense pulsations that were coursing through me.

She put her fingers to her mouth, "Fuck, you taste amazing."

"As do you," I said, trying to make myself look presentable.

"So are you a lesbian now?" she asked.

"I officially am not just into boys anymore," I answered, knowing I would definitely do this again in a heartbeat given the chance.

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