Painful Pleasures


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Painful Pleasure by Patrick Richard

Remember the song Sweet Dreams by the Eurythmics?  It went…  “Some of them want to use you, Some of them want to be used by you, Some of them want to abuse you, Some of them want to be abused….”

Well, Dylan MacGregor fit right into the lines of that song.  He wanted to be “used and abused” but not just by anyone.  He wanted a sadistic Mistress, dressed in sexy, black leather, carrying a big whip who would give him the discipline, pain and humiliation he desired.

He wasn’t born that way, but something triggered those thoughts and needs.  As far back as he could remember, he was intrigued with ropes and chains, especially if they were wrapped around him and secured extra tight.

Dylan spent hours and days during his youth, tying himself up and enjoying his self-inflicted bondage and pain.  He was a true masochist.  As the years went by, and he went through puberty, it became a total, sexual thing.  He didn’t want to hurt others.  It was the exact opposite.  He quickly found that his self-abuse and intense pain made his ejaculations far better than normal.

He explored numerous fetishes and constantly searched for a way to fulfil his dreams and desires.  Then the internet changed everything.  He was able to live his life vicariously through the bondage, discipline and pain of others.  He found story sites that fed his needs both physically and sexually, but they excited him far more than satisfying him.  He needed far more.  Deep inside, Dylan wished he could change places with the victims in those stories who were brutally tortured and abused for the pleasure of others.

Then one day his life changed dramatically.  Entirely by accident a woman came into his life who gave him everything he wanted.  They were so much alike except he wanted pain, and she liked to dish it out, making her victims scream.  It was an aphrodisiac for his new-found Mistress.  And that was just the beginning.

When his Mistress asked him what he wanted, he simply replied, “I want it all!”

Dylan found several people who would use him, and the rest is history.  Dylan got everything he ever wanted and far, far more.  Remember that line, “Be careful what you wish for, because you may get it all.”  There’s no doubt about it – he did.

Femdom, consensual, nonconsensual, blackmail, bondage, discipline, torture, pain, humiliation, chastity, crossdressing, feminization, cuckold, lesbian love, oral, anal and more.

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Weight .99 lbs
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Finally I got my head together and decided to go get some beer for tonight. I headed to a small convenience store just a few miles away. I bought a 30 pack of Miller Lite and headed back to my apartment. On the way, however, I passed an adult book store. As excited as I was from what happened earlier, I had to stop. It drew me in. I wandered around and looked at the various bondage equipment.

As I started to move on, I heard a voice, “Can I show you something?”

“I was just looking.”

“We just got in a new selection of hand cuffs and leg irons,” the woman explained. “The cuffs are wider and stronger, so they don’t cut into your skin when squeezed down tight. Maybe you’d like to try them. How about slipping into one of these hoods or strait jackets?”

“Not today, thanks anyway.”

“They come in both leather and canvas, but I prefer the leather. There’s something about the smell of hot sex and leather, don’t you think?”

“Yea, I like both and a mixture might be rather intoxicating.”

“Oh, trust me. It is.”

“Maybe another time,” I responded. “I have three women waiting for me to bring the beer to go along with their pizza.”

“Tell you what. Bring that beer to my house tonight, and we’ll play. I bet it will be a lot more fun than listening to three women gossip. And I get the feeling that you’d like to be wearing this tonight. You seem to be the submissive type. Imagine being buckled up tight in this strong leather jacket with no possibility of escape, so I can do what I want to you. I’d let you lick my pussy while I suck your long, hard cock. Or maybe you’d prefer a crop across your naked ass a couple dozen times. I’d do either. Nope, I’d do both. You’d like that, wouldn’t you?”

“Oh yea. Maybe another night. I’ll keep it in mind.”

She smiled and started to walk away, but suddenly turned,  “By the way, I’m Sally. I open this place every morning during the week and get off at four. Stop back soon.”

“I might just do that. Have a great night.”

“Wait,” she said, as she reached into her back pocket and pulled out a pen. On a scrap of paper, she wrote down her cell number. “Call me anytime if you want to play. It would be fun having you on your knees in front of me.”

“I’ll give it some thought.”

“Looks to me like you have,” she said with a big smile, as she noticed a bulge growing in my pants.”

As I drove home, I smiled. “Holy shit! I’ve been propositioned twice today.”

When I got back to the condos, I saw that Erica and Jenny were already there, so I knocked on Marti’s door.

“Come on in. Why in hell are you knocking? You know if your door wasn’t locked, I’d walk right in. Never know what I might find you doing. Open us each a beer and sit down.”

“I’ve got to go across the hall for a couple of minutes. I’ll be right back.”

“You can use my toilet, after all, I do have running water.”

“That’s okay. I’ll be right back. I’ve got to check on something.”

When I got into my living room, I went right to my laptop and open it. I was disappointed. There was no message, but it was what I expected. I used my toilet and went back across the hall. I sat there listening to their chatter about who was seeing whom and who was sneaking around on their mate. Sally was right. It probably would have been more fun at her house.

Finally the pizza arrived. We ate and joked, but the conversation soon turned to me. Erica was wondering if I was seeing anyone. I told her I wasn’t, but I date every once in a while.

“Anyone we know?”

“Probably not. Besides, none are serious. They’re mostly dinner and drinks, sometimes with colleagues or friends. It’s something to do. Hell, I even took Marti out the other night. I wanted to try that new bar-b-que place out on Route 50. It was good, wasn’t it?”

“Yea,” Marti responded. “Their brisket was fantastic. I’d definitely go back there again.”

“So you had a few too many last night?”

“I guess. A couple of my old frat buddies were in town, so we met at Jake’s. I knew it wasn’t going to be good when Russ started buying shots.”

Finally Jenny said, “Hey, we’re going to the movies for the nine o’clock show. Wanna join us?”

“Thanks, but I have other plans.”

“Oh, got a date?”

“No, Bob and Russ are still in town. We’re getting together before they head home. Thanks anyway.”

I left them the beer and headed back across the hall. Again I opened my computer and hoped for a message, but there was nothing. So there I sat, wondering what to do. I opened the story site I liked and looked for something interesting. I tried a couple of stories, but for some reason they were totally boring. So I got up to relieve myself when I remembered the phone number that she left me earlier. I called.

“Hi, this is Sally. Leave me a message. I’ll either get back to you or I won’t!”

“Ah… this is the guy that you showed the jacket to earlier. I was wondering if you’d like me to bring over that beer and try on that leather outfit.”

Immediately she picked up. “I like Corona and lime. You can deliver it to 3545 Mountain Crest Drive.”

“I’ll be there shortly,” I said, but she had already hung up.

I immediately headed back to the convenience store, got a case of beer and two limes. I asked the attendant for directions and drove on. A few minutes later I was sitting in her driveway, wondering what I was doing there. I remembered what she said she wanted to do to me. Actually, I was scared to death. Was I really ready for this?

After taking a deep breath, I rang her door bell and was greeted with a smile. We made small talk while drinking a beer.

“Ready to try on that jacket?” she asked with a sadistic grin.

I knew that once I agreed, there was no turning back, but I finally told her that there was no time like the present. Moments later I was standing in her playroom wearing nothing but my underwear. She held out the jacket. I noticed the extra-long sleeves and the numerous straps and buckles that would secure it.

There was a bit of trepidation, as I held out my arms. They slid in deep, as she pulled it up over my shoulders.

“Turn around and surrender to me, slave.”

I did, as she requested. Moments later the straps in the back were buckled tight, and my arms were crossed to be secured tightly in the back as well. I knew there was no escape. I was hers to do with as she pleased. She reached around to draw one of the groin straps between my legs and felt my cock getting ever harder.

“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 idiot-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 nipples exposed and a garter belt that held up black lace stockings. Seeing her dressed that way brought my cock 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 pussy to my mouth. “You know what to do.”

She lowered herself down and I dove right in, licking her hot twat, making her moan with unbridled pleasure. Then she leaned over and took my cock 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 cock 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 cock 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 cock. She stroked it a couple more times before picking up her whip again.

“Please don’t stop,” I begged.

“Which one – your cock 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 pussy 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 cum 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.”


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 cum, 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 fucked. 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 cock 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 cock 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 cock 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.


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