Pain and Pleasure

“I want you to call into the chatline Saturday night and get five men off,” Sir demanded when we spoke Friday night.

“Yes, Sir.”

“I want the huge dildo in your pussy. Just the head, at first. After each man comes, I want you to insert the dildo another inch. You may come with the last man.”

“Yes, Sir.” I nodded, though he couldn’t see me, let my eyes drift shut, and bit back a whimper.

“Do you understand your assignment, bitch?”

“Yes, Sir.”

He hung up.

Saturday night my senses were on high alert because of Sir’s control. The bedroom lights were brighter. The thud of the closing door, the click of the latch, louder. Darkness was a curtain enfolding me in my sanctuary.

I piled three pillows behind me and leaned back, buckled on my collar, planted my feet on the mattress, inserted the head of the lubed dildo, and dialed the chatline.

Phone in one hand, my thumb of the other circled and caressed my clit. I made a black man come, then a white guy.

Some men talk and I listen. Some I answer their questions. Others role play and we participate together. The third man, an older black guy who “loves white pussy,” recited it like a mantra as he jacked off and came.

Each time, I pushed the dildo in as Sir instructed. The third time, pain shot through me. A jolt so shocking I couldn’t breathe. I dropped the phone. The operator droned her spiel. Her voice aggravating the ache between my thighs. I fumbled for the instrument and hung up.

The dildo had hit my pelvic bone, though I’ve taken at least seven and half inches of this monster phallus before, it refused to push past it.

I scooted down in the bed, pressed my feet into the mattress, and lifted my ass just off the surface. I kept pressure on the fake balls and breathed through the sharp pain. After five or six minutes it didn’t lessen, so I called the chatline again, hoping to get through the last two, resigning that I wouldn’t be able to come, though Sir allowed it.

I half-listened to the men’s greetings. Soon I made myself focus on them and push away the ache. As I did pleasure blossomed in my cunt.

I spoke with a white guy who loved that I’m a white woman owned by a black man. I was so turned on by the time he finished my pussy clenched the dildo. It was time to push it in another inch. I tensed. Agony seared my insides. I couldn’t take deep breaths. My voice came out on a whisper.

Sir asked me one time had I ever been taken to a place where pain bordered pleasure. I’ve been caned. My leash used as a whip, spanked with a paddle, belt, hand, and crop. I’ve been flogged. My partners have given me dull pain. I’ve always stood on the edge, felt a longing, knowing if I just had more I’d find what was missing.

Saturday night it happened. Pleasure blossomed and hovered just out of reach.

I weeded out five or six men to get to the final guy. A black man. He used me. I opened my mouth like I sucked him, gagging on his BBC as he shoved it down my throat. I panted and moaned, incapable of coherent speech.

I pushed. The dildo would not move. I pulled that fucker out, smeared my juices up and down the shaft, and shoved it back in hoping to get that last inch for Sir. Stinging stabbed my cunt.

He came.

I disconnected the call and the clash of pain and pleasure that had warred the last forty-five minutes ended. Pleasure took the upper hand and I felt the walls of my pussy flutter around the dildo.

Miniscule contractions. Excitement bubbled in my chest. It was there. I hung on the verge of a new, exciting experience. I opened my mind and body to both the pain and pleasure, tasting, savoring it. Pleasure never outweighed the pain, but the pain didn’t stomp out my orgasm.

I eased the dildo out and lay back on the bed enjoying the aftershocks.

Fast forward to Wednesday night. Sir texted around eleven thirty. He instructed me to put the big dildo in and get on the chatline.

Contact me for permission to cum. All black men. Push it in deeper each time.

Yes, Sir.

Sir texted three times while I got the men off.

Put it in, whore. Turn pain into pleasure. Deeper, whore.

I got five men off and inched in the dildo each time. I hung up.

Stuffed, my pussy smarting, I texted, Sir, may I come?


Yes, Sir?


Yes, Sir.

On that line between pain and pleasure?

Yes, Sir.

Push it in another inch, go all out.

Yes, Sir. It took several minutes. And I gripped it between my thighs to keep my pussy from pushing it back out.

Call me.

My mind awash in pain, I didn’t realize Sir had answered. Normally, I can recite every word of our conversation. I cannot recall half of it.

“Come,” he said.

The sound of his voice and the word was all I needed to hear. The walls of my cunt squeezed that dildo, pleasure numbed my brain where moments ago it throbbed and ached.

He asked me again if I hurt. Did it feel good? Shuffling ensued on Sir’s end of the phone. Blood roared in my ears, I thought he might have spoken. I asked what he’d said, but he didn’t reply.

He let me come again.

Experiencing pain and pleasure by Sir’s commands was like touching something so cold it’s hot. Mixed signals tricking the brain.

Muffled voices crowded out coherent thought. His breath labored and mine sped up matching his. Blood buzzed through my head.

Sir was training. Surely not this late or rather so early Thursday morning. I thought he’d finished. Obviously not. I imagined a new submissive kneeled between Sir’s thighs, his thick, long, hard black dick stuffed between her rosy lips. Mascara bleeding black tears onto her pink cheeks. Soon she’d gag for air, choke on his seed. Those scattered uncertain thoughts combined with the agony and ecstasy inside me, and my need rocketed.

“Who owns you?”

“You do, Sir.”

“Who else owns you?”

I said the young black man’s name Sir began sharing me with last fall.

“Say it,” Sir commanded, once, then again.

I did both times.

“Say it.”

“Sir…” I really wasn’t happy he continued to make me. but I obeyed.

“Keeping saying his name.”

I repeated it over and over.


I screamed my release.

The line went dead.

I lay there in a stupor, harsh breaths pushed past my lips, pleasure overtook the excruciating convulsions. I wanted to lie there revel in the orgasm for hours.

Sir used me, the woman kneeling at his feet. Had he let her come? Did she want to or did she prefer being denied? He controlled us both, yet our obedience gave him his release. I couldn’t say which of the three of us was the luckiest.

I reached for the phone, toying with the idea of calling Sir and begging for more. His ringtone interrupted my ecstasy.

Now, get back on the chatline and get two more men off, whore. You are not allowed to cum again.

So many horny men that night.

Ten minutes later I texted Sir. Finished, Sir.


Another sweet release gripped my body and mind.

Take a picture and send it to my phone of what’s sticking out of your cunt and then take it out.

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