Bottoming to a Man

He was a somewhat famous and remarkably talented artist and educator. Ten years older than me, or so. He was taller and broader than me, with a large thick beard. We had met and spoken a few times, but he saw me walking around at an event with my pant legs folded up with purple socks and sock garters and he complimented me on my calves. He later approached me and said he would love to cane my calves. I accepted, nervously.

There was something very different about the way he grabbed me by the scruff of my neck and pushed me against a wall. He asked if I would be a good boy for him. I nodded, “yessir,” my head going into a very different space that I was used to.

Then he started hitting me, reasonably hard, on the calves with various thickness of canes. Most of the time he held me by the back of my neck of pit his large hand on my back to steady me. It’s something I started doing in scenes, maintaining a physical connection and a reminder of control.

As usual, I became pretty stoic, just my hands on the wall, my jaw tight, taking every strike silently. He wasn’t having that though, he roughed me up, pull me out of my trance.

The scene went on and finally he asked if I could take “five of his best.”

I eagerly agree. My head and body had transitioned to a place where I could take a lot of pain and transform it into something else. Pleasure? Power? Something. I was greedy for more and getting cocky.

He pulled back with a thick rattan cane and thwack. Then again. Then he leaned in and asked “aren’t you going to count for me?”

I smiled up at him.

“Oh, did you start?” I bratted.

His smile became huge. “Oh, thank you for saying that,” he said, going to his back and getting a much meaner resin cane.

Cocky bratty Jack lasted one one or two hits. Then my knees buckled and I could stand up.

The Valet

The dry cleaner (a lovely woman from Belarus, I believe) had my order hanging near the cash register, waiting for me. She tried to brush away my tip, but as always she eventually conceded with a smile and daintily shoved the few extra dollars (as daintily as someone can shove something) into her vast brassiere.

Usually by 8:30, which my pocketwatch told me it had just struck, I’d be making coffee, but since my employer was “with guest” and the various grinding of beans and screaming of espresso making apparati would, I’m sure, be a less than ideal wake up call, I was out running the errands which I usually saved for later in the day.

The mornings when my employer had an overnight guest (or guests, as sometimes happens) were some of the most challenging in my professional life, I assure you. Still, in their own way, they were some of the most rewarding.

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Print Anthology


Writing Dirty: Erotic Stories by Jack Stratton, now in print!


Available on Amazon and CreateSpace

Here’s what people are saying about Writing Dirty:

“Jack Stratton’s erotica is deep, dirty, and thoughtful… he often writes from the dominant’s perspective, which is more rare in erotica than you would think, and his explorations of sadism are insightful and transformative. I often see my own play differently after reading his work. And of course they’re just plain sexy, turning me on and inspiring my desire.”
Sinclair Sexsmith, author of Sweet & Rough: Queer Kink Erotica

“This book proves that you can write sexy BDSM that includes condoms, consent, and communication. And really great sex scenes with as much
tension as anything I’ve read in a long time.”
Guy New York, author of Brorotica

“This story worked as my introduction to the possibility of negotiation in the context of SM relationships and how regular people might do it. But of course the story is very hot, which makes everything to do with it seem appealing. Our hero is likable, self-depracating and sometimes confused… Did I mention this story is hot?”

“Pretty much anything by Jack Stratton is worth reading.”

“Kindle’s King of Taboo Titillation, Jack Stratton, scores five points from my “judges” with this coming, of-age sexual awakening and deep, satisfying life experiences.”
– Amazon Reviews

Girls’ Night In

Friday night was for going out. Saturdays were for brunch and adventures. Sunday though, Sunday was girls’ night in.

Well, theoretically. I actually didn’t go out much on Fridays or Saturdays, but my roommate did. She took pity on me though and would watch dumb tv shows and silly movies with me on Sunday.

“Becca, popcorn?” my roommate Cassie shouted from the kitchen.

“Yes, duh!” I replied.

She laughed and ran into the living room holding two jars. “Cinnamon Kettle Corn or Mexican Spice?”

“Surprise me,” I said with my usual crooked smile.

As per usual, Cassie’s outfit was shocking. Little black panties, gray thigh high socks, and no top or bra.

“A bowl of each!” she proclaimed.

I gave her a thumbs up, trying not to let her see that I was blushing.

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The Sexy Cats of Halloween

I’m not sure how or why, but one Halloween I decided to collect stray cats.

It started on the L train. Her name was Bianca, she was in college. She seemed a little self conscious about how low cut her dress was and how the tops of her thigh highs were visible when she walked because her dress was so short.

Her costume was just a black dress, black thigh high stockings held up with a pretty garter belt, cat ears, and whiskers drawn on her cheeks.

Her eyes were very wide and thickly rimmed with black eyeliner, a sharp wing at the edges of each eye. She was pretty and chubby and blushed when I complimented her dark red lipstick.

She was shy at first, but I was charming. She had left a party her friend threw early. She didn’t like the vibe. I told her I was collecting cats and we would make our own party. She thought it was a good idea.

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Getting Off

In her eyes, forever, there was a Midwest kindness. But New York City had let her down and most of the time she was sad under those thick black bangs.

It wasn’t exactly shame that shown in her face when she climbed the stairs to my apartment, but burden. Her kinks were a hassle and she wished she could come some other way, but she was stuck with her desires.

It concerned me, to a point, but there came a time when I had to trust in her ability to make up her own mind.

And after a few drinks her frown melted and the easy smile she fought against came out.

She was a good kid. Tall and strong, corn fed with a big ass. Tattooed arms and a too tight tee shirt.

Walking around my place naked when I had the curtains open made her nervous. She liked that.

What she hated, were the pigtails.

But in the end serving is what got her off. Embarrassment too. The way I made her ask for it. The way I spanked her until she was panting and begging. The way I laughed at how wet she got.

When she was getting fucked hard was the only time she stopped overthinking the world. I could see it in her eyes, a blank animal state, pure want and stupid lust.

Sometimes I felt guilty because I knew my belt was her drug of choice.

Usually I didn’t care.


In the beginning it was just a simple rule. Stay put. It made her nervous and excited. It made her happy because it was an easy rule to follow. It made her pout because it was too easy, she wanted to show him that she could do more. She could be a good girl. She could be useful in all sorts of ways.

The place she was asked to stay was his lap, which was sweet. She tried to be still as he typed on his computer. Occasionally he got up, but she was to stay in the living room, waiting for him to return.

He brought her tea and petted her hair and she tried to be patient and unobtrusive while he worked.

The reality crept up after the second hour.

“Sir, can I-”

“Shh,” he said, putting a finger over her lips.

She quieted down. There was a pressure building between her legs. Too much tea. It made her jittery and have to pee. She wasn’t sure how to ask without braking her silence.

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Show Me

My first love was a cruel hearted girl, but that’s a story for another time.

My second was a soft and sweet thing whose heart I broke accidentally, like knocking a China cup off a table.

Her name was Sophia and she was always smiling, which was alien to my angry teenage heart. She was the first person who showed me that love could be playful and silly.

She was both shy and adventurous all at once. Constantly daring me to make moves and then getting cold feet.

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Reading on Nov 6, 2015

Come join Sinclair Sexsmith, Kathleen Warnock, Carol Rosenfeld, Jack Stratton, Felice Shays, Guy New York, Marissa Quenqua & Kelli Dunham for a night of reading dirty stories at everyone’s favorite bookstore, cafe, & activist center, Bluestockings!

Celebrate the paperback release of Sinclair’s full-length kinky queer erotica short story collection, Sweet & Rough.

Bluestockings Bookstore, Café, & Activist Center
172 Allen St, New York, New York 10002
Friday, November 6 at 7:00pm

$5 donation suggested, NOTAFLOF
RSVP on Facebook

Greedy Queen

In celebration of putting some of my old ebooks back on Amazon and setting up a new reading and various other new ideas, here is the last ebook I published, if your amusement. It’s a light, sexy tale of facesitting and fun.

Henry got Marisol’s text message just as his lunch meeting started.

On the little screen of his phone was a picture of her thick thighs, just barely covered by a pretty summer dress.

“Just got out of the spa. Waxed completely bare,” she wrote.

He went to reply so quickly he almost dropped his phone.

“You should come over. I’m not busy, I can leave the office in a half an hour,” he typed.

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