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Pillow Stories

This Hurts Me More Than It Hurts You

by Stephanie Schaeffer
(11/19/03)

I was in college the first time a man asked me to spank him. It was in the dorms at Columbia. I was fooling around with a sophomore after consuming quite a bit of alcohol, and as soon as we got naked he handed me an ordinary leather belt and told me to hit him across the butt with it.

"Really?" I asked him. "Are you serious?"

"Please," he said. He rolled over and presented his ass.

I was coming down. I had a headache and needed to pee. "I can't do this," I told him. I got up, used the toilet and washed my face and when I returned he was passed out on his roommate's futon.

But oddly enough, even though the initial thought of it had repulsed me, over the years it became the thing I fantasized about the most. Spanking. Not being spanked, but being the spanker. I liked to fantasize about spanking men.

With each rotation of my hips, I'd visualize applying an enthusiastic hand to the eager behind of some deserving date. Tantalizing my swollen clit with a lubed finger, I'd picture different implements -- the back of a hairbrush, a leather paddle, a thin birch rod -- until I settled on the one that was most stimulating. I'd also imagine various guys; my last e-date, some hot movie celebrity. That sophomore in college and how differently things could have gone if I'd just smacked him with his belt like he'd asked. Now, envisioning some beau's blushing cheeks never failed to bring me to climax.

An ex-boyfriend of mine, Elliot, started making a regular appearance in my spanking fantasies of late. A typical Elliot fantasy progressed as follows: while rubbing myself tentatively through my thin cotton panties, I visualized the faces Elliot used to make when fucking, only in my imagination he was making them while I spanked him. Then, I'd plunk his sore ass down in a chair and suck his dick. At this point my underwear was down around my knees, thumb circling my clit with fervor. As my fantasy self straddled him and fucked him until he came screaming, my thighs would be pressed around my hand, urgently squeezing the finger up my pussy as I came along with him.

I hadn't thought about Elliot in a sexual way since before we broke up last year. It was that old cliché of us being at different points in our lives. I was in my mid-twenties and had just started graduate school. Elliot, at 31, had recently co-founded a small computer consulting start-up. He was putting in long hours at the company. It was his baby, his anchor, his sweat and blood, and his availability was limited. Our courtship consisted of 15 minute coffee dates at odd hours of the day whenever he could fit them into his agenda. He was a proficient lover, particularly adept at oral sex, but only when he could find the time, which was scarcely once a week.

We’d had an amicable split. By the time he mustered up the courage to feed me the "I don't have the time for a relationship right now" line, I'd already gotten involved with a fellow graduate student at the university who had more time on his hands and shared my interest in Kierkegaard.

I still ran into Elliot quite often at my favorite study spot, The Local Mocha. His office was nearby, and he stopped there morning and night for his caffeine fix. We'd become friends, of sorts, having a coffee together from time to time. I'd taken up with the on-line dating scene after Rolf, the grad student, had moved to Minnesota to pursue a community college teaching opportunity, and Elliot always liked hearing about my most recent romantic escapades. He laughed at my stories of stand-ups, one-night stands, and threesomes gone awry. I thought it was his way of living vicariously.

Elliot hadn't dated anyone for a while, but recently he'd begun seeing Kara, an emaciated, elongated 19 year-old with fuchsia hair and modeling aspirations. I was surprised by his choice but didn't say anything. Our conversations mostly centered on his work and my bad dates.

Now Elliot had started showing up in my fantasies and all this masturbation was getting in the way of my school work. It was a Monday night. The lit review I had procrastinated on all weekend and just barely finished was due at 8:30 a.m. the next morning. My printer, I had just discovered, was all out of ink.

With a frustrated sigh, I popped the disc out of the drive and headed off on foot to the copy place near The Local Mocha. When I got there, the storefront was dark. I glanced at the posted hours. 9am -- 9pm.

"Fuck," I said, aloud.

"Problem?" It was Elliot. I wondered momentarily what he was doing there until I remembered he’d told me his office space was on the block. He had a Local Mocha to-go cup in his hand, probably his usual double espresso.

"I have to print out this paper for class tomorrow, I'm all out of ink and this place is closed," I said.

"You can use the printer in my office," he offered.

His office, it turned out, was in a building just two doors down on the third floor. I waited as he rummaged through his pockets for the keys. He unlocked the door and ushered me inside. We were alone. His partner, clearly the one with a greater sense of the concept of work/life balance, had already gone home. The office had that distinct buzz that offices always seem to have.

I followed Elliot to his computer station and handed him my disc. As he fiddled with the computer, I surveyed his workspace. There was a snapshot of him and Kara on the desk amidst some papers. It looked like it had been taken at an office party or similar function. Little bitch looks like she just swallowed a lemon, I thought.

"How's Kara?" I asked.

"Fine," he said.

He bent over the desk to turn on the printer. His gray wool pants stretched tight over his ass. I could tell there was a nickel in his back pocket, and something that looked like it could be a gum wrapper. I traced the curves of his butt with my eyes. It was all I could do to prevent myself from reaching out and swatting those cheeks.

"What is it?" he asked, catching me looking at him and straightening up.

"I'm just looking at your ass," I told him.

He stared at me, expressionless.

"It's nice," I said.

This time he looked amused.

"So is that," I added, looking pointedly at his crotch.

Now he was more than amused. "It's pitching a tent," I told him.

"That it is," he said. We both admired his hard-on.

"Bend over the desk again." I told him.

"Why?"

"So I can see your ass."

He bent over as I asked, playing along.

"I'm going to spank you," I said.

"What?"

"I'm going to spank you."

He didn't object. I took this to be an assent. I smacked his butt. He didn't flinch. I slapped his ass again, harder. And again.

"Take off your pants." I wanted to feel his bare skin, to see my handprint vividly branded across his fine expanse of ass, but he took my order to mean punishment was over.

He turned around and embraced me. His dick was as hard as a board. We fucked right there on the desk. I left a sweaty butt print on the cheap veneer finish.

I didn't see Elliot around the next couple of days. He didn't call either. I don't know why I expected him to. I didn't even know if he still had my telephone number. Still, it bothered me a little.

Feeling restless late one night, I did an Internet search, typing in "spanking." All I found were a bunch of sites containing photos of barely legal women dressed ridiculously as Catholic schoolgirls, sprawled over the laps of some pervy looking older men, tears running down their faces as their fannies got slapped silly. Not what I was looking for.

On Friday of that same week I went to Chez Arlene to hear my friend Scott's band play. I was chatting with Scott on the smoking patio between sets when Elliot came in with Kara. He didn't acknowledge me. Kara had on a pink halter top and stretch jeans and looked like she hadn't eaten for months. She was chattering on about something -- I couldn't decipher what -- and Elliot placed his hand patronizingly on the small of her back as if to encourage her along inside, away from my vicinity.

We didn't speak to each other throughout the course of the evening. I drank a beer and left after Scott's last set, furious. I thought about the stripes I would leave on Elliot's ass the next time I saw him. I contemplated making him count after each stroke.

Over the weekend, I scheduled a meeting with another e-date. I thought I might as well since it didn't look like things between me and Elliot would go any further. Mitch was a lawyer, mid-thirties, new in town, never married, no kids. We agreed to meet at 2 p.m. on Sunday at The Local Mocha.

My date looked pleased to see me, but his straight-laced hunter green polo shirt and white shorts made me cringe. After exchanging pleasantries we ordered two coffees and sat down at a table near the window. "So you went to Georgetown?" I asked Mitch, making conversation. "What was living in D.C. like?"

Elliot came in and ordered a double espresso. I saw him do a double take at me and my date. Mitch was answering my question, but I wasn't paying attention. Elliot got his coffee to go and left. Through the window, I watched his ass as he walked across the street. He was wearing corduroys, and the fabric was worn a little on the seat.

Mitch and I continued with the small talk. Over refills, the subject of S & M came up.

"My ex-fiancée liked to get spanked," my date said, lowering his voice and leaning forward, preparing to evaluate my reaction. "Do you?"

"I like to do the spanking," I said.

"Oh," he said, surprised, disappointed. "But quite frankly what you really want is some dashing gentleman to take you over his knee and--"

"No," I said, "Not really."

Mitch cleared his throat and fiddled with his coffee stirrer. Our date ended shortly after that.

At home later that night, I tried to read, but I couldn't concentrate. I felt bored and lonely. I checked my email and I had some responses from interested e-dates, but the experience with Mitch had left me feeling drained. I didn't have the energy for more "getting to know you" chitchat.

I was preparing for bed when the doorbell rang. I looked through the peephole. It was Elliot.

I opened the door and he stood there looking at me with a coy smile on his face. "I've been bad," he said.

I closed the door and followed him into the bedroom. He was already in position, bent over the bed. I lowered his trousers and boxers, exposing his ripe peach ass. Removing the belt from his pants, I set it aside for later. Elliot waited in anticipation.

I smacked his bare butt with my palm open and fingers spread, not too hard at first. I was just warming up. He braced himself, wanting more. I reached for the belt, holding the buckle away at a safe distance and gripping the strap in the middle for tighter control.

It came down across his bottom with a satisfying snap. I admonished him as the leather tongue licked his behind.

"You've--" snap! "been--" snap! "a really--" snap! "bad--" snap! "boyfriend!" Snap!

Elliot clenched his stinging buttocks, pressing himself against the mattress in attempt to alleviate the agony of his stiff cock.

His ass was glowing red. I let him cool off for a minute before searing his butt with another succession of lashes.

I lay the belt down. Gently I ran my fingertips over his tingling skin. He quivered.

I picked up a hairbrush and softly rubbed the smooth wooden side over his bottom in a circular motion. Elliot sighed and relaxed a bit. Swiftly, I dealt two sound whacks to the center of each rosy cheek. Elliot yelped. He clutched at the bedsheets as I paddled away. His ass was now scarlet. Just looking at it made my own cheeks flush in empathy. I stopped to finger myself. My pussy was hot to the touch.

I caught Elliot looking at me expectantly so I went for the belt again, crisscrossing his backside with the leather strap. I could tell it stung, but he took it like a man.

I leaned back against the wall, eyes closed, rubbing the leather belt tip underneath my panties, against my clit. I came almost immediately, like warm butter melting down my thighs. I opened my eyes. Elliot hadn't strayed from position.

The spanking had left marks. Not severe, but marks nonetheless. I went to the kitchen for ice. I returned and Elliot was still face down on the bed. I could practically see his ass throbbing. He raised his head up and watched me as I went over to him, cup in hand. I put an ice cube in my mouth and ran my chilled tongue over his hot tender skin. He murmured. Gently spreading his cheeks, I lapped leisurely around the circumference of his asshole.

I turned him over, cushioning his sore bottom with a pillow. His dick bobbed in the air. Transferring the melting ice to the inside of my cheek, I took the head of his penis into my mouth and sucked. Elliot moaned. Soon he pulled out of my mouth and came, splattering my chest and throat.

"Thanks for the pearls," I told him, and he laughed.

He didn't stay long. It wasn't even half past ten when he got up and reached for his clothes.

"I gotta go," he said. "Early meeting."

I watched him dress, his back to me. Across his butt was belted out a constellation of little red stars.

I was at The Local Mocha the next morning when Elliot came in with Kara. His walk seemed a bit stiffer than usual. Some friends invited them to sit down at their table, but Elliot said he preferred to stand. "I have a meeting at the office in ten minutes," he explained.

Elliot stood in line waiting for his double espresso. While Kara was in the ladies room, I walked up to him to say hello. I knew she'd be in there for at least twenty minutes, checking her make-up.

I pinched his butt and he winced. "Nice ass," I told him.

He smiled. "I'll call you tomorrow," he said.

©2003 by Stephanie Schaeffer

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