Little Riding Sister-in-Law

A younger sister asks her older sister’s husbands to initiate her as a woman. Based on real events.

The story is based on real events, with just the names changed and ages adjusted a bit (but not much).

***

I met my future wife when I was 21 and she was 19. We hit it off pretty fast, and within two months I was fingering Jane like crazy, and another month later we’d both lost our virginity to each other. It turned out that we both liked sex, all kinds and poses, so soon we were fucking like rabbits, taking every opportunity. Especially good were the weekends when Jane’s parents went away and left the apartment to us. Our personal sex marathon record was about 40 hours, with breaks to sleep and a few times to eat.

Jane had a younger sister, Zoe, who looked like a carbon copy of Jane, only ten years younger. They were close, with Jane caring for her little sister and Zoe admiring her older sister and doing her best to follow her path. Me and Jane did not hide from her, we fucked and walked around naked all the time, we felt it was perfectly normal. For the first few months Zoe was extremely shy and embarrassed and would sneak past us as fast as she could, her face all red, but in time she got used to it and would hang around in just her panties.

Fast forward two years. Jane and I were married, living on our own, and exploring open polyamorous family relationships. It was all so fresh and exciting to us. We were going out to fuck with others, together or separately, or inviting them over for threesomes or foursomes. By this time we were living as a stable trio family, with Tim joining us as a co-husband. We weren’t much into threesomes with each other, so Jane would just pick which one of us she wanted to sleep with tonight.

Tim was a few years older and a little taller than me. We got along very well because we were both Jane’s loves, so we had very similar personalities.

Jane and Zoe were still very close, often visiting and helping each other. Zoe knew all about our lifestyle (unlike our parents) and was okay with it. As it turned out later, more than okay…

***

One day Zoe (she was eleven by that time) came to us all angry and upset and spent several hours locked in the kitchen with Jane, talking and grumbling. Then they came to us and announced that Zoe had had a big quarrel with her parents, so she’d be staying with us for a while. Me and Tim were perfectly fine with this, we liked Zoe and knew her well, and we had a spare sofa for her.

All three of us lived naked at home, and in a day or two Zoe joined our custom. She still looked like Jane’s younger copy, even more like her now that she was starting to grow into feminine shapes. I don’t know about Tim, but I certainly felt aroused when Zoe walked around. We did not touch her, but Jane was definitely getting a lot more fucking with us these days…

Two weeks later, at breakfast, Zoe told us (a little shyly) that she wanted to start having sex and that she trusted me and Tim to be her first. We exchanged glances. Jane shrugged.

“Okay. How do you want to start, sis?”

“Well, you sleep with either Sam or Tim every night. I could take the open spot.”

We smiled.

“Perfect! So be it.”

***

It was my turn to sleep with Zoe first. We both felt both excited and apprehensive at the same time, because she was about to lose her virginity, and she was the first sexual partner for me at such a young age. So we agreed not to rush things and to start slowly.

The first night we just cuddled naked a lot, hugged, kissed passionately (she turned out to be a great kisser, I don’t know where she learned it; maybe from Jane), and I brought her to a couple of orgasms with my fingers and mouth. Zoe tried to give me a blowjob, but she was completely inexperienced, so we ended up with her kissing and licking the tip of my dick until I came in her mouth. She tasted her first sperm and decided it was okay. We fell to sleep side by side.

I woke up in the middle of the night with Zoe snoozing peacefully next to me. I could not get to sleep, I was too excited for that, but I still did not want to jump on top of her all of a sudden. She was sleeping on her back with her legs slightly apart, so I licked my fingers and began to caress her slit gently. Soon it parted under my fingers and oh, how wet and hot it was inside!

I continued to caress and rub, and Zoe’s breathing grew deeper and louder. She did not wake up though – or at least she pretended not to, keeping her eyes closed – so I kept fingering her pussy. Zoe’s breathing was deep and erratic, she stirred and moaned softly in her sleep, spreading her legs wider, and I rubbed her harder until her breathing stopped and then came back faster. I caressed her gently for a while, then removed my hand and finally slept.

In the morning, she gave me no indication that she hadn’t slept all that time, and I didn’t ask. We never talked about this episode.

***

The next night the girls switched places so that Jane and I could hear Zoe gasping, laughing softly, crying, and moaning louder and louder from the next room. She was finally becoming a woman! We were so turned on by the sounds that we fucked like animals.

The next morning, Zoe seemed especially relaxed, smiling and blushing all the time. We all kissed her and congratulated her.

We gave her a day to heal after breaking her hymen, and finally I fucked her the next night. She was really a little copy of my wife, she even smelled very similar. She was inexperienced, but no less eager and passionate, and oh God, how tight she was!

Zoe stayed with us for a year. She made peace with her parents, but decided she liked it better with us, and they let her. We fucked every night and sometimes during the day, bringing in different partners all the time, and in a year Zoe became as experienced as her older sister. All her holes were explored, and she learned all kinds of lovemaking. She was so happy with it!

Within a year she found a boy and moved in with him, she was twelve and he was fourteen, and they somehow arranged it all with their parents. As far as I know, they are still a happy and loving couple, as she preferred not to join the polyamorous lifestyle. But that’s a story for another time.

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