HOW IT STARTED FOR CHERRY

Some things you can’t forget. They follow you into the alleyways of your dreams and reveal themselves over and over in the moments you are most vulnerable. For the person who would become Cherry, it was in the first moments of wakefulness or in dreams.

Cherry is naturally 5’8” and has long, full copper hair, deep blue eyes, and fair, milky skin. Cherry had a different name back then—but it’s almost forgotten now. An athlete from an early age, Cherry prioritized fitness and was happy with how life was going. Cherry loved sex, loved women, and had lots of friends and connections. Back then, Cherry was not “Cherry”. This is the story of what made her—Cherry.

Sometimes, I wake up remembering Suzanne. It all started there. I was 28. She was 30, blonde, divorced, and the mother of a 12-year-old bitchy daughter. She was also a therapist, hedonist, and sexual adventuress who rode a laid-back 900 cc Japanese boulevard bike. It was Halloween, and we decided to go out in Denver to a club in costume to dance. Under pressure from her, I agreed to cross-dress. She had a friend who had transitioned and loaned me footwear, but Suzanne bought me the clothes I wore and did my makeup. It was all for a laugh and a riot. Nothing profound to come, or so I thought.

That night would burn itself into my brain. The strange free feeling of walking out of her Boulder apartment dressed in spike-heeled ankle boots, black tights, a tight red pleather miniskirt hugging my fat round ass, and the sheer top barely disguising the fake tits all under a black leather jacket. The image is ever at the edge of my waking life. I could, at times, still almost feel the tight panties and tape holding my largish dick tucked in and the wind against my thighs, blowing between my legs; her hand occasionally on my thigh or teasing my squashed cock; and my long hair, braided, flowing out from under the helmet behind us as she gunned the bike down the highway and into the city. She wore lady-biker boots, tight black leather pants, and a vest that pushed her full tits together. A heavily chained leather jacket, zipped tight, completed the outfit, and a hooded cat mask was in her shoulder bag, along with who knew what. Her long hair spilled out wildly from under her black, full-faced helmet. Saddlebags hung under my tight-clad thighs, the fringe tickling me and streaming in the cool night air. I felt as free as a wave on the sea.

In the club, she wanted me to dance with boys, but I refused. We had drinks, and she wanted me to flirt with the metrosexuals at the next table. She teased me incessantly, and the tightness in my belly and light-headedness almost convinced me, but I still denied it even though the strange titillations coursing through my body were sending other messages and I found myself imagining and wondering - “What if…?” She did a surprise for me that I discovered soon enough.

We left the club and walked through the streets of Denver as people caroused in uninhibited costumes. She spanked my ass repeatedly as we walked and stopped me at the bus stop bench just outside of the parking garage where her 900cc bike was parked.

She pulled me in closely and kissed me hungrily, shoving her breasts into my ribs while her tongue probed deep into my mouth.

“Grab hold of the bench and bend over, honey!” she crooned

I hesitated, but she moved me into position and began spanking me lightly. After the initial shock, I realized how much I liked it and arched my back, pushing my ass up into it.

Her voice was suddenly loud. “Anyone want to help me spank this slut?!”

She forcefully held my neck down and stood beside me, her leather pants tight against her strong legs. I only struggled a little, and she laughed. I could sense other people gathering around and heard some laugh some more. A few people took her up on the offer and spanked me while she encouraged them:

“It’s her first night out in Denver, and she wants to remember it! Keep going—don't worry, she loves it all! Who knows what she’ll do if you get her hot enough!”

Suzanne kept pushing her thighs against my face while she humiliated me verbally and offered up my ass for people to abuse. Gradually I became aware of a bulge in her pants that hadn’t been there when we left the house.

After some time, my head now entirely spinning and me completely disoriented, hot, and bothered, she stopped the spanking line to moans of disappointment and laughter.

“I have to take her out of here now! But you can walk us to the garage where we’re parked.”

She took my hand with a strange look, and in a daze, I let her lead me into the dull light of the garage. We got to the bike, and she turned around.

“Watch this!” she said and straddled the bike, unzipped her pants, and pulled out a fat fake cock. Its textured veins bulged, and her laughter echoed as the dozen or so costumed spectators gathered around.

“Suck it, BITCH," she commanded. Everything went still and quiet as I watched her suggestively thrusting her hips up and down while she pinched her nipple and stroked her breast.

“SUCK IT! I said—you know you want it.”

And I did. I did want it, though I had never thought about it before. It seemed like slow motion as I bent forwards and wrapped my lips around it. The strange silicon taste of it, her hand wrapped through my hair and her laughter and panting filling my ears. Somehow my hand found her cunt. Fingers slid in easily. She pumped my mouth but pulled my hand out of her dripping snatch, and grabbing my hair tightly, pulled my mouth off her fake dick to look into her lust-crazed eyes.

“You want it, don’t you? You really want it. You want to be bitched-out—fucked right now.”

I can remember hearing but not understanding and a blank space, then being face down on the hood of a car and her pushing into me painfully, but I wanted it, and it soon turned to pleasure. Sparks flew around my head, and people shouted encouragement and laughed and danced on the edge of my vision. I remember she came fucking my ass in that parking lot, then pushed her dildo back into her pants, climbed on the bike, started it up, and patted the seat behind her.

I pulled myself up off the car hood, wondering in the back of my head that there had been no alarm, pulled my skirt down and climbed on behind her, wrapped my arms around her waist and leaned into her back as she scooted into me.

Back in her apartment, I discovered that she wasn’t done with me.

“You are such a bitch but a good slut, so I am going to reward you,” she said.

“Get on your back and spread your legs.”

I was still dazed and out of my body, hovering in some light, airy place, so I lay down, put my heels on the mattress, and spread my legs as wide as possible.

“One day, I think you are going to be a real whore," she said, laughing a bit nastily. She had a tube of lube in her hand. Using her free hand, she released my cock, which sprang instantly to full, then squirted out a large amount of lube, and slathered it on my cock and down my ass crack to my hole.

“I’m going to help you get there, starting right now. Does that make you happy?’

Having no idea what she was getting at and suddenly desperate to cum, I nodded and said softly, “Yes, ma’am.”

“That’s 'Mistress', bitch. Say it!"

“Yes, Mistress,” I replied, and I felt her begin to work my cock slowly with one hand and tease my ass with the other.

“You want to get fucked again? You sure seemed to like it. All those people watching you? You are a little bit of an exhibitionist slut, aren’t you? You liked it. I know you did, but you didn’t cum. I’m going to make you cum now. I’m going to use my hands and make you cum. It’s going to change you. But don’t worry, I will be here to take care of you.”

I could feel her fingers at the entrance of my hole as she stroked me up and down,  slowly tightening and loosening her grip. Her eyes bored into mine, and I felt her adding fingers to the small thrusts of her hand. She started pumping my cock harder, and her hand pushed further.

“I’ve almost got my whole hand in your ass now, bitch. How do you like it?”

I could only mumble a response as something gave way, and she shouted a laugh.

"Good fucking whore- you took it all! You are going to be such a fucking slut. You have my whole fist in your ass now!”

I could tell in some way that I was humping her fist but couldn’t really believe it, and as she continued to pump my cock my brain went blank but still registered her verbal abuse and encouragement, which turned me on intensely.

When I came, I knew I was weeping with pleasure and shaking like nothing I had ever imagined. She held me close and kept her hand in me while she whispered in my ear what a good whore I was and how well I took cock and didn’t want a real one. After a time, she fed me the cum on her hand and smiled, saying:

“Now we know- you will always know what you really are…”

We dated for another year or so before she moved on to another lover, and I left for foreign places, but we never repeated that night, and it came to haunt me. But I would find other lovers to take me to where I now am… and this is the story of my conversion.

Although Suzanne and I dated semi-exclusively for several years, we never repeated the scene from that Halloween. There were many days and nights when she’d put some clothing and makeup out for me, and I would dress up like a prom queen or a leather slut and ride around behind her on her motorcycle, then go home, and she’d fuck me with a big two-way strap-on until she came. I loved knowing she was really getting off by fucking me, and it made me feel so tender towards her. After she came from pounding me, I’d fuck her dressed in girls' clothes and cum in her mouth or pussy. She liked it too. We’d sleep dressed in our play clothes and wake up laughing. But we never went full-on role-playing in public again. I was pretty happy to let that slide. It was a relief to know it wasn’t a full-time thing for me. Or so I thought.

Suzanne and I eventually broke up, and I moved to Hawaii, a place of endless sun, surf, exposed skin, hot nights, and sultry sunsets. I worked at a gym, taught fitness and vinyasa yoga classes, surfed, and swam daily. I was lean and ripped. And that is where I met the woman who would truly set me free.