A Story of a Sissy

I was just a young man when I met Jacqueline. I'd had very few lovers before her. She showed me everything. She had a vibrator. She loved her vibrator. She made me suck her vibrator when she'd hold the base of it against her pubis. "Suck my cock," she'd say. Then she'd push my head down on her vibrator. She'd insert her vibrator into her pussy and then tell me to suck it. I had no idea this was an actual thing. I just thought it was sexy as hell. She was a voluptuous woman, the first real woman I'd ever been with and she controlled me. All she had to do was hint at something and I'd onboard with her and we'd be off to the races.

I didn't know it was "submissive". I didn't know what a sissy was. I didn't know anything except I liked playing with her. She was so open-minded.

I remember once we were taking a road trip up to my mom's place two counties over and the whole drive we were naked, playing with each other, wearing panties, or hose or nothing at all. There were truckers, drivers, women and men, who'd witnessed our game. She was so horny and pretending she didn't want to do it but in reality once the idea was planted I couldn't have stopped her.

We'd go to nude beaches and have sex. We'd fuck in national parks. We once hiked all afternoon through Yosemite in just our hiking shoes. Once we went to San Onofre. The parking was just a stretch of roadside between the highway and the beach and each parking slot had a picnic table and shelter and we fucked on the picnic table in full view of cars and people alike. And then we went to the nude beach. She made me walk nude while she wore her bikini. I didn't know this was "submissive" then, I just liked her telling me what to do.

She loved being a woman too. She wore makeup, had a little ritual she followed and I became part of that. I would do her toes. I would bathe her. I didn't know this had a name, it just felt like we were both enjoying it.

I'll never forget, during our on-again, off-again relationship, near the end, the last time we were together, she invited me to come meet her and her friends at the bowling alley. I rushed to her. I'd thought I'd never hear from her again. I was masturbating. I was wearing panties. She called and asked me to come so I just threw on my clothes over my panties and showed up.

They were all leaving when I arrived and she asked me to drive her home. She was drunk. She never got drunk. She smoked, did pills, but she never drank.

In the car she was all over me. Whispering in my ear, she was calling me her sissy, and her panty boy. I had no idea what these terms were or that they were actual terms, I just thought she was drunk and saying things that were true. I was a sissy and a panty boy, but just for her, not because it was an actual thing. In the car, "I bet you're wearing panties right now aren't you sissy boy."

I was and that she knew was pure coincidence, I thought. She really knew me though. She knew I'd be wearing panties. Back at her apartment we fucked that night like wild animals. We scissored. I will never forget it and to this day, 30 years later, when I masturbate I think of that night. We scissored and fucked like lesbian whores and when it came my turn to orgasm she pushed me back onto my shoulder blades and jacked my cock off onto my face and mouth.

When Joan sent me her story, it had elements of dominant and submissiveness. These are terms I'd come to know and understand since dating Jacqueline. When I saw them in Joan's writing I knew she knew what these terms were too.

After I got her email, I responded right away. I knew the risk she'd taken sending me this story. She must have been terrified I'd reject her. I wanted to assuage that anxiety. I told her I loved it. I told her I masturbated reading it. I opened myself up to her and gave her something to hold on to so she wouldn't feel alone in her endeavor.

We began writing together on a shared doc. We'd write notes and comments, sometimes we'd be online at the same time and it made it feel like we were having sex.

I played it cool. I didn't want to scare her off. I had no idea that she knew about me already. I had no idea that she'd found my literotica stories.

I'd only find that out after the fact and when I look back on it, she was the one controlling everything. When I think back on that, I realize that Joan was the best lover I'd ever had and we never once had physical contact.