A short story from my early blogging days. Probably around 2007-8. Examining my somewhat burgeoning kink. There is a different tone, a different voice there. Sometimes it is playfully poetic, but awkward. Sometimes it is just arrogant. Other times it is sweet.

In this new life, I have slipped into a variety of completely new relationships. I’ve always been the kind of person who has a small circle of close friends, and I tended to shy away from the masses of acquaintances people seemed to collect in this city. Now I seem to be joining an ever-growing group of interesting and open-minded people. This has led to months of fun, flirtation, and often fierce conversation. In some ways, these connections are almost better than all the sex and exploration. (Almost, but not quite.)

I hadn’t considered my sadistic side very much until about a year ago. If anything, I had often thought that I was squeamish about being too rough, in bed or otherwise. After a few lively scenes, I found that the little seed of a sadist in me was starting to bloom. The keys, I realized, were playing with masochists and talking about it first.

It’s funny how your personality changes in certain situations. I’ve noticed all these parts of myself that come out when I do certain things. The seducer: looking at sex as a challenge and an art form. The top: with his sarcasm and teasing. The daddy: who is overprotective while being dirty. The aspiring rigger: with his knitted brow and stern focus. The sadist: constantly wearing an evil grin and always thinking of the next form of torture.

Besides the cadre of smart and sexy friends I converse with, there are a few smart and sexy people that I beat up on a somewhat regular basis. It’s interesting because, in general, these are not exactly sexual relationships, though certainly, they all have sexual elements. Mostly, though, they are about administering pain.

For example, here is a tale of a girl, well, not really one person but sort of an amalgam of a few people I know. There are too many scenes in my head, and writing about the important parts of each would take too long. But basically, this is what I’m talking about.

We had been on a few dates. After-work drinks, talking and flirting, and exchanging the social currency of anecdote and background.

In this time, we used the complex mating language of eyes and subtext to explain our emotional availability. We danced around our proclivities. We ferreted out kinks and occasionally just came out and owned our desires.

Negotiation came later. By then, we had reached that plateau of reasonable trust and adequate acquaintance. The fourth date was to be at my apartment.

She was in her mid-twenties, bright, educated, good job, interesting life. The city seemed to either breed the complicated or pull them magnet-like from all points of the compass.

Dark hair with severe bangs and thick glasses. She had a wealth of interests which showed her curiosity, which to me was the most important virtue. She was cute, if not pretty, but her style brought her look to the next level. She knew how to wear clothes. She was an artist through and through, but more than that, she was an artist who could make a living which was certainly a precious thing in the city.

“I’m a masochist,” she said rather plainly. “I had a boyfriend who I finally convinced to spank me, but he never hit hard enough, and it always just left me unsatisfied.”

“‘I don’t want to hurt you, baby! I love you,’ is what he’d say.” she quoted in mocking a luggish tone.

I understood very well. Spanking was the gateway. It was still socially acceptable if a bit risqué by Cosmo standards. Still, it was a glimpse of that new world we wanted to explore a lot more thoroughly for many.

Back at my apartment, we had giddy grins and drinks. A conversation on the couch about work and the world, while both of us shifted closer and thought about how to start things. 

“So, you liked that last story I wrote, hm?” It was a way to gain a little control and bend the conversation toward where we both wanted to take it. 

“Yeah, you could say that. I think I came six times. I soaked my sheets.” I watched her eyes, there was some instinctual shame, but she actively fought it. She wanted to be bold, and she wanted to own it.

“Well, I guess you owe me,” I said, reaching over and caressing her breasts, finding the nipple, pinching it roughly as I watched her reaction. She bit her lip and then smiled.

It was silly, really, but nothing is better than a little ego-stroking to build one’s confidence. I moved in and kissed her, then my hand moved up to her hair and pulled her head back so I could drag my teeth across her naked neck.

I’ll skip the rest of the beginning. I’ve certainly told the tale of a girl being bent over the arm of my couch and spanked far too many times. While spanking her and getting her warmed up, I will say this: I did what I always do, progressed quickly at first to find that line, how much she can take. Pulling back and orbiting that line. Measuring everything else against it. 

I kept hitting her and measuring. Harder and harder I spanked, but she gritted her teeth and took it. The few times I leaned over her body and whispered my little check-up questions into her ear, she just nodded. She was fine. I should keep going, harder, more.

That’s when I knew I was going to get to cane someone for real. 

I only had one cane, though I was looking to remedy that. It was long and black and thin. Resin. Stingy and direct. I had never used it on another person, only on my own legs.

I forced myself to slow. I knew she still needed more warming up. I knew I had to be patient and calculating. I told her to lay down across my lap.

She was obedient and followed my every direction perfectly. Frankly, it was all really more sensation play than dominance—a casual beating, not a punishment. I didn’t want her to call me sir. I just wanted her to do what I said and take every stinging lash.

When I started, it was just a little bounce of the cane on her naked ass. Her skin was red from the spanking with a circle of light purple where I had hit her the hardest, but the cane made fresh and crisper red marks. Lines form, even from this light bouncing.

That first real hit, that whoosh through the air, made her back arch. She took it, but it was a lot for her. She had only ever been spanked with a hand. I hit her again, once on each cheek and then once across both. Her hands didn’t come up to protect her tender flesh, but she is suddenly still. I let the pain reverberate. 

I let her feel it and process it. I put my hand on her back and steadied her, letting her know I understood that it hurt and I was letting her deal with it.

Each hit left three lines; red, then white, then red again. As I bounced the cane on her skin again, I saw that the four hard hits had started to bruise. It made me hard. It made me giddy. I wanted to ruin her. I wanted to mark her. I wanted her to feel the marks all week and get wet every time she sat down and winced.

I got to work on her, bouncing the cane harder, making little syncopated rhythms that I remembered my drummer had friend taught me. I waited until the skin was red and hungry, and then I hit her hard a few more times, relishing each sound. I hit her harder, pulling my arm back farther and taking full swings that turn purple immediately.

She finally broke a little and let out a loud “no, please!” She didn’t block me, though. She just slumped forward a little. I soothed her. I left her breath. After a few minutes, I tried to pull her up, to stand.

When I pulled her up, her legs didn’t work properly, and suddenly, I was holding her. I laugh and spun her around. I push her against the wall. She gasped and smiled. I knew my clean white wall was hard and cold against her bare ass.

My hand moved down her body and slipped between her thighs. She was so wet her thighs were slick. She buried her head in my shoulder as the pleasure overtook her for a moment. I pulled my hand away. It wasn’t cuddling time. It wasn’t time for pleasure. Those would come.

I moved my hand back up and cupped her breast. She sighed happily. I pulled back and slapped her breast hard. Her eyes flashed open. I cupped each one and slapped it down again. She looked unsure how to take it. She was squirming.

“Do you like that?” She nodded quickly, eagerly. 

“Has anyone done this before?” She shook her head. It was hard for her to talk when she got into that space. I slap her harder, focusing on her nipples. Slap, slap, waiting for her wince, measuring out the limits of this new activity.

“Why do you like it?”

“It hurts,” she said with that sort of look in her eyes that told me that it was once something she was ashamed of, but now she was proud, or at least comfortable with. Her tongue was thick in her mouth, and it was hard for her to create sentences, but she tried to continue.

“I like it because I can see it. Usually, it’s my ass, and I can’t see it happen.”

I devoured the flush in her cheeks when she said that. It was useful information, and information meant I could hurt her in more complicated ways.

I hit her breasts a few more times and relished her yelps and moans. She was so tough when I was spanking her, but her breasts were a lot more sensitive, and she wasn’t used to the sensations.

This whole time I was fully dressed. That was part of the scene, though I didn’t realize that for a while. She was a plaything, being stripped and used and hurt.

I sat her on the couch and went to get some other toys, ones I keep fresh in ziplock bags, sterile and ready. She watched me with wide eyes.

I plugged into the wall my favorite vibrating implement and shoved it between her half-closed legs. I pushed her back a bit, manhandling her, and got the head of the condom-covered toy against her clit. I closed her legs against it, letting her thighs hold it in position. As I turned it on, I struck the tops of her thighs with my hand.

She bit her lip and ground against the vibrator. I got out the cane, letting her see it. Her eyes were wide, but she said nothing. I rose it up and she closed her eyes. I hit her one time across her thighs and she held her breath. When she opened her eyes, I knew she had enough of that.

I switched to the riding crop, taking it to her breasts. I hit the tender bottoms of each breast, then the sides, the quick snaps on the nipples that made her cry out.

When I flipped her around, her knees on my couch and her arms and head hanging over the arm. She let me move her like a limp doll.

I let loose with the crop a few times. The marks I had left before were sharp violet. When she squirmed away from the pain, I went to work on her with the vibrator again. 

The cycle started once more, cries and yelps followed by moans and whimpers. The crop and then the vibrator until she whined every time I pulled the vibrator away. I hit her a few more times and then held her down and pressed the vibrator on high against her sopping sex.

She mewed and tensed and came hard against me, pulling at my arm. When she was done pulled the vibrator away, and just as she sighed in relief, I pushed it back against her now over-sensitive clit.

She fought against the over-stimulation, but I held it to her. I let her ride it out until her hips were bucking again, and she came hard again.

When she came down, I sank into the couch next to her and helped her as she gasped for air and shivered. I petted her hair and smiled at her, and soothed her, careful not to touch her still hot and stinging ass.

When we finally got up, I saw something spectacular. It was my first real masterpiece. Her ass was almost uniformly purple with lines of wine red and angry pink and speckles of her pale skin showing through. I spun her around and marveled at it. Her thighs had a few scattered lines but nothing like her ass. 

It was perfect. She stood in front of my mirror and kept touching the raised marks and smiling at her little prize. She was just as happy as I was because it was the first time she had gone that far and gotten what she had been fantasizing about.

Through that next week, I emailed her, checking in on the progress. The bruises lasted weeks. Those first few days, she could hardly sit, and she had to go to the bathroom of her office and finger herself because the pain was so intense and the memories so inescapable.