Painful Pleasures

Chapter One-3

“This excites you, doesn’t it?”

“Oh God, yes, Mistress!”

“Well, these will have to go. Either step out of them, or I’ll have to cut them off.”

She pulled my briefs down, leaving me totally exposed. Yea, it stuck up tall and straight.

A thick strap was pulled down over my arms, pushed through a keeper, crossed below my balls and tightened through a buckle in the back on the other side. She did the same with the other leather strap, holding the i***t-style jacket perfectly in place. As I stood there with her totally in control, I wondered what she had in mind.

Then she grabbed my erection, using it as a handle and pulled me into her bedroom.

“Get on the bed and spread your legs.”

I did with no response.

She put leather cuffs around each ankle and spread them wider, hooking them to straps that came from the lower corners of the bed.

“Comfy, slave?”

“Yes, Mistress.”

She just smiled, put a collar around my neck and fastened it to a strap connected to the headboard.

“I’ll be back. Don’t go anyplace. Okay?”

She disappeared for a few minutes, but finally reappeared wearing a bra that left her n*****s exposed and a garter belt that held up black lace stockings. Seeing her dresses that way brought my c**k to full attention once more.

“I guess you like my outfit,” she said, as she climbed up on the bed. Before I could answer, she straddled my head and lowered her p***y to my mouth. “You know what to do.”

She lowered herself down and I dove right in, licking her hot t**t, making her moan with unbridled pleasure. Then she leaned over and took my c**k in her mouth.

“Don’t hurry, slave. We have all night.”

Over the next hour I rocked her clear to her soul several times, but she never let me blow. She had me close before biting my c**k or chewing on my balls. I was denied any pleasure. I realized that as a slave, she was the only one that mattered. It was my duty to please her and expect nothing in return.

Finally she climbed off and headed to the bathroom. She returned after a while, adding a small thong to her outfit.

“What did I tell you we would do after I had my pleasure?”

“Ah, I don’t remember.”

“Oh, I bet you do. Think hard if you know what’s good for you.”

“You said you’d whip my ass with a crop.”

She released my ankles and the collar, making me get up and move to the end of her bed. My feet were spread wide and refastened to the legs of the bed. Another strap was hooked to my collar and pulled tight, forcing me to bend over, exposing my ass to her. Before going any further, she loosened the straps that came up between my legs so there was nothing in her way - just a bare ass fully exposed and waiting for her whip.

Then she started. Her hands softly rubbed my ass cheeks and then found my c**k and balls. She took several minutes to get me hard once more, but she continued bringing me right to a stroke before blowing. At that moment, her crop struck my ass, leaving a line of fire and pain from one side to the other.

“Ah – h – h…!”

“That’s what you wanted, isn’t it?”

“Yes, Mistress.”

“Many guys think they want a whipping until after the first stroke of my whip. Then they start begging me to release them, screaming that it hurts too much. But you didn’t.”

Mistress Sally reached between my legs and felt my throbbing c**k. She stroked it a couple more times before picking up her whip again.

“Please don’t stop,” I begged.

“Which one – your c**k or the whip?”

“Both, Mistress.”

Moments later I heard the slight sound of the whip cutting through the air. When it hit me and left a dark red mark, I remained silent. She struck me again even harder, before working her hand up and down my hard pole.

And that’s how it went. She kept me right on the precipice of pleasure before striking me with her whip. Over and over, never letting me blow, then raising another dark purple welt on my ass.

Sure I moaned and yelled, but I never asked her to stop. It got to the point that I wanted the whip, knowing it was the only way that I could blow. I wanted her to hurt me. I screamed in pain, yet begged for more, and she gave it to me, always denying me my pleasure.

Finally she tired of the game and released me, but my night was far from over. I knelt on my knees, as she draped her legs over my shoulders. Her fingers twisted in my hair and pulled me tighter between her legs. Her p***y was dripping wet with her juice. Whipping me had really excited her. She moved the crotch of her panties out of the way, and I brought her to another very-vocal, multiple orgasm.

When she finally pushed me away, I made the mistake of asking for my own pleasure. After all, my balls were so full and ached from the buildup of c*m after tonight’s ordeal.

“Oh slave. You came here tonight to give me pleasure. Yours doesn’t matter. After all, you are just a worthless slave, destined to serve a superior woman – your Mistress.”

“But….”

She laughed and made me lay down on the bed with my legs spread.

“I’ll be right back in a minute to take care of your little problem.”

I wondered if she was going to let me c*m, but down deep I knew it was not going to happen. That’s not how it works. A slave never gets that pleasure in the presence of his Mistress. I figured I could get some satisfaction when I got home.

A few minutes later she did return, and I immediately knew I was f****d. She had a bag of ice and a stainless steel chastity device in her hands.

“This one might be a little bit too small, but it won’t make any difference. After all, it’s your c**k and balls that will be locked inside it.”

“Please Mistress. Don’t do this to me. I’m so horny. I need to cum.”

“No, slave… you only think you do. I don’t want you going home and jerking off. I want you to go home and have just one thing on your mind – me, your Mistress. Besides that, I really think that down deep you want me to lock you up and keep you in chastity. You want someone to control you. And you know as well as I do, that once you jerk off the excitement is gone. Then you’ll wonder if what we did here tonight was worth it.”

“No, Mistress, this is what I’ve dreamed about for years.”

She just laughed, and I realized that none of this was my choice. I was the one in the strait jacket. She had all the control.

The ice was put on my privates and lay there while she leaned over and passionately kissed me. Finally she closed the main metal band around my entire package. It had an oval shape and was rather snug when she snapped it shut. After aligning a urethral tube with my piss hole, my pecker was pushed and forced into the small, curved cage. Even as soft as I was, it was difficult for her to squeeze my c**k in and click the lock shut.

“Please, Mistress. It’s way too tight. How can I possibly wear this?”

“I guess at this point, slave, you don’t have a choice. You can stop by the store next Tuesday, and we’ll discuss it.”

“But that’s five days.”

“Do you want me to make it longer?”

“No, please. Don’t do this to me.”

“Instead of complaining, you should be thanking me for taking control of your worthless little pecker and locking it up so tight. So let’s make it next Friday. Be in the store at nine, and we’ll see if your attitude changes.”

I never said another word. She released me and sent me on my way.

“Don’t forget… a week from tomorrow at nine.”

“Yes, Mistress, I’ll be there.”

“Oh… I bet you will,” she laughed.

When I got to my car, I realized what I had endured tonight. It was difficult to sit after the whipping, but it felt so good. Just thinking about it made my c**k try to get hard.

I left and drove home, wondering how I could ever make it until then. But I realized that I had no choice. Besides that, it was another one of my dreams that had come true.

It was only about twenty miles but sitting for that long was rather difficult. In spite of it all I finally made it home. Luckily, Marti’s lights were off, so I made it inside without seeing her.

I headed right to the bathroom and undressed. As I stood in front of the full-length mirror, my eyes were fixed on the stainless steel cage that confined my pride and joy. I closely examined it, knowing there was no escape. But then I turned around. My ass was a mass of black and blue with numerous darker welts crisscrossing both cheeks. I couldn’t believe what she did to me, but more importantly, I couldn’t believe I took it.

I rubbed a generous amount of aloe lotion on my ass, slipped into some clean shorts and headed for bed. I would deal with my problems in the morning, knowing the true color of my ass would definitely show.