Beautiful Bottom by Dalia

Beautiful Bottom.

Tom was an architect.

We first met at a munch on Queen Street in Toronto.  He was a regular in the scene, though not one of my immediate friends.  He loved to dress in leathers.  Lean, well toned, he looked good in anything he wore and he knew it.

He was youngish, late twenties or early thirties and considered himself a serious player.  I had seen him worked over in play and could vouch for his pain tolerance being high.  He also had a rep for being a total slut.

That one night he wore just leather pants to a public party.  After chatting me up for a while he told me he liked it rough.

I raised an eyebrow and waited in silence.

“I mean really rough” he said with a challenging gleam in his eye and a slight smirk playing on his lips.  “No one has ever made me cry.”

I smiled. “Why don’t you come back with us to K’s place”  I gave him the location of the home.

Later that night all were all settled comfortably, chatting in the living room of K’s home, me behind the sofa, sitting off it’s edge, behind Tom, my hands playing with his thick dark hair.  He looked up and smiled.  I walked to the stairs and looked back at him, then descended.

I could hear the living room go silent and then laughter, as he arose to follow.  Calls of “Have fun” and “Good luck” accompanied his departure.

K had a dungeon in her basement.

I took a set of cuffs and stood in the centre of the room.  He came towards me, that smarmy smile still playing on his face.

“You think you can make me cry?” he taunted.

“Is crying important to you?” I asked, my chin raised, head tilted just slightly to the side.

He looked a little startled at the question and took a moment to respond, “Yah, I guess it is”  The smile left his face.

“Once these cuffs go on, you will not be released till you cry ‘uncle’.  Uncle is your only safeword.”

He laughed in my face and held out his hands.

I placed the cuffs on both wrists, took one hand in mine, smiled and walked around back of him, reached around, stroking his cock through his leather pants.  He arched back against me, and I grabbed the other wrist, securing them together behind him.

I walked to the wall and lowered a rope on a pulley so that when attached his wrists would stay at approximately the same height and re-secured it.  I snapped the latch at the end of the rope in place.

I walked up to him and teased his cock some more then opened his pants and removed them.

I grabbed a high-backed stool from the side from the room and sat before him.  Left leg went up, pointed stiletto boot resting on his shoulder, the other between his legs, playing with his balls.

“Kiss the boot”

“That’s not really my thing”  he said, as my right leg dropped a bit and came back hard.

“Kiss it” I said as he groaned and his eyes watered, knees buckling a bit.

He turned his head and began kissing the tops.  I moved my foot to give him the dirty sole.  He moved back a bit but not far as the pointy tip rested at the base of his balls.

Our eyes met and he kissed it.  “Lick” I said as the rough edge of the right boot scrapped over his balls.  A choked groan escaped him and his mouth remained shut.  I kicked again this time hitting more between the ass cheeks and he gasped, the toe of my boot entering his mouth.  “Suck then”  And he complied.  Even more eagerly this time.

I let him lick clean both my boots.  He paid particular attention to sucking off the stiletto heels, suggestively, his eyes telling me he found this hawt.

“You are such a slut” He smiled while sucking even harder.  I removed my foot.

I lowered the rope length more; raised my leather mini dress up a little and secured a strap on to myself as he watched.  I grabbed his hair and forced it his head down and watched as his wrists raised a bit behind him.

“Since you are so good at sucking… “I trailed off and rubbed the tip around his mouth and he laughed and said “Oh yah!”

I lifted his head by the hair again and slapped him hard, leaving a red mark on his face.

“When I want to hear from you cunt I will let you know.”  I immediately pushed his head back down and forced the dildo between not so happy lips.

But being the slut he is, he began respond, to get into the groove and as soon as he relaxed I took over, pumping, making him gag and gasp.  Tears welled in his eyes and fell down his cheeks.

I released him red faced and pulled out an old fashioned hand mirror.  “Not so pretty now.”

He spluttered.  “This isn’t crying”

I rolled a spanking horse over and locked it in place.  He bent over it, his breath coming just a little faster.  I secured the waist belt and released him from the pulley, though his wrists were still bound.

I brought out my cane and began disciplining him.  “I told you when I wanted to hear from you I’d let you know.”

“Yes, Ma’am.  Sorry, Ma’am” he gasped from his beautifully engorged lips.

“I will leave my mark on you, because for all your challenge and talk, you can do squat about it bitch.”

His not warmed skin began to mark quickly.

“Yes Ma’am.  Thank you, Ma’am”

I pull down the cane, and rubbed my hand over his ass, cupping his balls and pulled downward while his cock strained against the wooden horse.

“Thank you, Ma’am” he groaned.

I spread his butt cheeks painfully wide and spit.

“Dirty cunt.  You don’t want it rough, you just want to be used”

“No… “ he began and my finger slipped into his ass and started roughly moving in it, “yes…”

I laughed and removed my finger.

“Seems like my little slut is actually a dog in heat”

I grabbed a collar and leash and put it on him.

“There we go.”

I released him from the horse, pulled him by the neck, by the lead, making him stumble back towards me and then pressed against the back of his knees, forcing him to kneel.

“Kiss the boots doggy”  He bent to kiss them and as he became prone, I moved away forcing him to scramble on his knees to follow, unable to get upright.

“Let’s go for a walk”

“Fuck”  He exclaimed and I brought my boot up to his neck and pressed down.  His face crushed to the floor, spitting angry.

“I thought you liked rough?  You’re just a fucking pussy though, aren’t you?”

“No!”  he exclaimed and I raised my foot and brought it back down on his pretty face.  Tears welled in his eyes again.  Tears of frustration.

“Pussy, did you have something to say?”

“No Ma’am” He said through gritted teeth.

I removed my foot and dragged him a few more feet.

I picked up some lipstick and put it on him, his head twisting to avoid it, smearing it all over his face.  “Pretty slut” and I slapped him again.

I yanked up is collar and he struggled to find a crouch.  “Get up you stupid slut”

He opened his mouth to complain and shut it again.

“Slut is learning”

I grabbed some lube and a wooden chair this time, bending him over the back of it.  He relaxed a bit.  I prepped myself but not him.

“Wouldn’t want to be too gentle with my man-pussy” I said and he tensed as I placed the strap on to the entrance of his ass.  “Tell me you want it”

He laughed.

I grabbed his balls and squeezed hard.  “Arrrrgh!”

“Tell me”

“I want it”
“Beg for it”

“I don’t fucking BEG”

I reached around and slapped his cock peeking through the back of the chair.

“AAAAH”

I squeezed his balls and did not release.

“Please- give- it- to- me----”

“Why?”

“because I’m a dirty little whore Ma’am”

“Why?

“Because I thought I could take it and I can’t and you win, please just do it”

I released his balls and started fucking his ass, easing into it, gaining momentum.  I reached from behind to stroke his cock.  He didn’t take long to cum and still I stroked and rocked his ass. I milked and milked, and he began to cry.

“What do you say slut?”

“No.”

“What do you say?”

And on and on it went, his pride warring with his pain until he called it; gasping, slobbering, sobbing.

“Uncle.”