Painful Pleaures by Patrick Richards

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Painful Pleaures

(Patrick Richards)


Painful Pleasures

Chapter One

 

"I know what you want and need, slave boy. I can't wait for us to play. I'll see you soon."

That strange, yet very intriguing message appeared on my laptop screen when I opened it up this morning. I know it had been a rough night of drinking, but I wasn't that drunk, was I? I rubbed my eyes and read it again, but the words hadn't changed a bit.

"Holy fuck!" I wondered. "Who wrote this? How does anyone know the things that excite me?"

I reread it several times and felt something stirring deep within me, clear to my soul. By the fourth or fifth reading of the post, my cock had swelled to its maximum proportions and pre-cum dripped from the very tip.

Yea, I'm into some kinky shit. I am intrigued with bondage. It has been a game I've played for as long as I can remember, but no one else knows about my secret fetish. I've never told anyone, and no one ever caught me when I was all tied up. Self-bondage became a regular way of self-gratification and entertainment. It had been my own little fantasy game since I was just a kid. By the time I hit puberty, it became totally sexual. It wasn't that I wanted to tie up my friends and have my way with them. No, I wanted to be their victim - tied up and helpless - the damsel in distress so to speak. But it never happened. We never played those games. It was just me, exploring my sexuality in an entirely different way. Many times I had amazing orgasms, as I struggled for release. Bondage became the trigger.

My need to be bound and helpless never died. It was just the opposite. It lived. It grew within me. It dominated my thoughts and actions every day of my life. And with the internet it got more intense. My desires were fueled by the many stories and porn sites available. I was able to live my fantasies through the domination, struggles and pain of others. I spent many hours in self-bondage, often very painful at times. Over the years I put together a collection of "toys" to enhance my sessions. Telling anyone would have been too embarrassing. Besides, most of it is just a dream. Hell, who am I kidding. It became a way of life.

The truth is, I like porn. No, I love it. It's a definite part of me. I especially like stories, videos and pictures of Femdom games. It excites me when I see or read about a guy being put in strict, tight bondage and forced to serve his cruel and demanding Mistress. I always wondered what it would be like to be helplessly shackled on my knees in front of a sadistic woman dressed in sexy black leather with a vicious whip in her hand. Nipple showing bras, tiny pussy-covering thongs, garter belts holding up fishnet stockings and knee high boots with tall stiletto heels completed my fantasy. I'd get an erection just imagining what painful things she would do to me, but it wasn't real.

As I stood there nearly naked in front of my computer, my cock tented the front of my underwear. It didn't surprise me that the message and my related thoughts excited me that way. I was as hard as steel. Unconsciously my hand slipped down inside my snug boxer briefs. I grasped my throbbing cock and rubbed it, as I read the message once more.

"I know what you want and need," I read aloud, so I could actually hear it. "I can't wait for us to play."

I wondered what she wanted to do to me. Was she into bondage and discipline? Would she...?

"Oh fuck!" I whispered. "I don't even know if the person who left this message is a woman. After all, I'm not gay. I'm not attracted to men at all. I'm just assuming and hoping it's a woman since it's my desire to serve a Mistress rather than a Master."

The thoughts that raced through my mind had caused a rock hard, full-blown erection. My hand released my stiff, seven and a half inch cock from within the silky fabric that held it.

As I headed for the bathroom to jerk off, someone knocked at my door.

"Dylan, are you up?" she yelled. "You said you wanted to go for a run."

"Ye - yea, I'm up." I was really up. "Give me a couple of minutes."

"Come on, just let me in."

"I'm not dressed. I'll be right there," I responded.

"Oh, come on. When have you ever been so fuckin' bashful?"

I walked slowly to the door and turned my back to it, as I twisted the dead bolt.

"Come on in. I'll be right out," I told her, making sure she couldn't see the overly large bulge in my underwear.

As I made my way to the bedroom, I heard her quietly comment, "Nice butt."

I smiled and quickly slipped into a pair of shorts and a tank top. With a pair of socks and my running shoes I headed back into the living room. I wondered if she was anywhere near my computer. I think I left the message showing. She wasn't. Marti stood next to the door waiting for me.

The tall, sexy, long-legged blond - yea, I fucked her a few times, go back a couple of years. When I moved into this condo, she already lived across the hall. We dated a few times, but just became good friends. Neither of us wanted a serious relationship.

Let me explain, so you are up to date. I took a position at the nearby university as an English professor teaching American Literature. Marti is the Assistant Director of Admissions. It's much easier just being friends and neighbors. Sure we had sex a few times, but working somewhat together may have caused some problems in the future.

Finally I was ready, and we headed out. We try to run five or six miles every other day. She was wearing black, skin tight capris and a purple sports bra. God, she looked hot. She has a beautiful ass and a nice set of boobs. They're not too big. Actually they were just right for me. But, as I said - we're just good friends and live next door to each other.

We ran up the county road, heading towards the campus. It was our normal route since there was far less traffic. I enjoyed running behind her and watching her tight butt. I'm sure she knew why I wanted her to lead.

As we ran, I thought about this morning's message. I wondered if she was the one who left it. She probably knows me better than anyone in the area, but I never brought it up to her. Besides, she didn't look the type. But then I thought, what's the type. What distinguishes her from a dominatrix?" What normal woman would want to play BDSM games anyway?

I remembered the times we spent together. She never appeared to be a dominate person, but she wasn't submissive either. Marti was a strong woman who knew what she wanted. But, who else knows me as well as she does?

We continued along and finally headed down the home stretch. When we got back to our condo building, she asked, "Erica and Jenny are coming over for pizza tonight. Do you want to join us?"

"Sure... want me to bring the beer?"

"Great. Be at my place by 7:00. It was a good run today. See you later, buddy."

Once inside I opened my laptop to see if there were any more messages. On one hand I hoped there was, but on the other hand maybe it was better that there wasn't. So I headed to the shower.

I let the hot water cascade down over me and dreamed of serving a Mistress. Immediately I got hard, so I took advantage of the situation. I jerked off and shot a tremendous load of jism against the shower wall. Having thoughts about possible bondage and servitude all day made me really horny and even the satisfaction of a hand job wasn't enough. I needed more. After slipping into a pair of sweats I headed back to my laptop and logged into my favorite sites. I clicked on the bondage story site I like and read a recently posted tale entitled, "Paddled and Pegged."

The story was about a guy who was locked over a heavy bondage horse, waiting to have his ass blistered. He struggled against the thick leather cuffs that held him in the perfect position, knowing what was going to happen. His Mistress started with a thick Spencer paddle. It was about a foot long and six inches wide. The numerous holes in its wooden surfaces allowed her to swing her arm faster, striking his tender buttocks even harder, causing him excruciating pain.

My cock instantly got hard, knowing he howled through his gag, as the first stroke of the paddle smashed across both ass cheeks, leaving a wide, dark red swath of agony. I imagined hearing he loud crack from its impact echoing from the walls of her chamber. His screams and muffled howls were nearly silenced by the over-sized gag. Her slave bucked and fought with all his might to escape, but just had to lay there and take all two dozen powerful strokes of the hideous paddle.

"Holy fuck!" I wanted it so badly.

I had to stop reading the story in order to adjust my cock. It had immediately come to full attention, filling with hot, sex-charged blood. The description of the brutal beating turned me on so much. My heart was pounding, and my breathing increased. I wished there were a video so I could actually see the action. I pushed the elastic waistband of my sweats down and pulled out my cock and balls. With my left hand I fondled my nuts while slowly stroking my hard cock with the other. My balls tingled and the excitement grew, so I read on.

When she finished the brutal beating, his Mistress stood before him wearing an enormous strap-on dong. She removed his gag before twisting her fingers in his hair. Then she yanked his head up, so he could see her evil weapon. It was nearly a foot long while her thumb and fingers couldn't even reach around it. Fear engulfed him, as he realized where she was going to put her fake dick.

"Kiss it, slave. Suck my huge cock, so I can fuck you," she demanded.

Reluctantly he opened his mouth and licked the head of her dong. Slowly she pushed it beyond his lips a couple of inches.

"Just think how it will feel when I fuck you with this monster."

Unintentionally I felt my ass muscles tighten.

He shook his head back and forth and tried to mumble, "N - o - o - o...!"

She just laughed and walked around behind him. A tiny bit of lube was added to the head of her dick and even less was rubbed on the outside of his small, tight rectal hole. Normally a couple of fingers and lots of that slick stuff would help, but this was not the case. She wanted to destroy his poor hole and cause him the most pain possible.

"When I'm through reaming out your ass, you'll never be the same."

"Please, Mistress," he begged incoherently, as she put the head of her fake cock against his ass bud. There was no foreplay or finger stretching of his anal cavity. She wanted to hurt her slave. She enjoyed making him suffer.

Her fingers dug into the sides of his hips for leverage. Then she pushed, as he screamed in agony. He tried to squeeze his ass muscles shut, but there was no stopping her.

"No, Mistress! No - o - o - o...!" he screamed. "It's way too big!"

My heart was pounding and my breathing increased as I read on.

She just laughed and increased the force, pushing harder and harder with her hips. Suddenly the massive mushroom-shaped head disappeared in his ass, ripping and stretching his poor hole. Howls and shrieks marked his attempt to tear himself from the horse. His Mistress grabbed his hips even harder, digging in her nails. She drove the dildo another six inches into his bowels. His cries and wails continued, as she pulled it back a couple of inches, giving him a slight reprieve. Then with a sadistic chuckle, she drove the entire hard rubber cock in clear to the hilt. Her thighs slapped against his pain-stricken, black and blue ass cheeks. After grinding it in as deep as possible, his Mistress built up a hard, steady, fucking rhythm. Her slave cried and wailed from the violent rape.

My hand rubbed my cock up and down. I was getting closer to blowing.

It took her several long, agonizing minutes to finally get herself off. Her moans and howls of lustful pleasure filled the chamber, as she had her first orgasm, but she needed more. After a brief rest, she fucked him again even harder, slamming her hard cock in even deeper. His screams had diminished to soft babbles and cries. Her slave had given up. There was no fight left in him.

I did it even harder, stroking it up and down.

But she wasn't finished. She pulled it out and made him lick her dick clean before going to her cupboard. When she returned, she lubed up an even bigger butt plug and forced it in his ass, stretching him even further.

I continued beating my meat. I was nearly there.

"I'll see you in the morning, slave. It sure has been fun," she said, as the lights went out and the dungeon door was locked.

The story may have ended, but I wasn't done. My cock was as hard as a metal poker. Pre-cum dripped down onto my hand. I stroked it harder, having been totally turned on by the author's details. Moments later I felt that wonderful tingling in my cock and balls. Long strings of cream-colored cum shot from my dick, creating a mess in my sweats, but I didn't care. That whole episode excited me. I wished I had been the guy locked over the horse.

Finally, I shut down the story site and headed into the bathroom to clean up. When I returned there was a note on the screen.

"Naughty, naughty, naughty.... You got yourself off on that other guy's misery. I can't wait to make you my slave. I'll paddle your ass and fuck you like that poor guy in the story if you want. After all, you'd willingly change places with him, wouldn't you?"

Sheepishly, I responded by nodding my head up and down and writing, "Yes, Mistress."

I quickly came to my senses and typed a response, "How do you know about the story I just read?"

"It's simple. I hacked into your computer months ago. I've been monitoring your activities ever since you placed your ad on FetLife looking for a Mistress. I like to know who I'm dealing with before getting involved. It's funny... turns out I actually live just a short distance from you. I know everything about you - where you work, who you see and what actually excites you."

"So what do you want?"

"Isn't it obvious? I want you groveling at my feet, begging to serve me, and even though you don't realize it yet, you want me. We have so much in common. Our interests are nearly identical except that I'm the sadist and you're the masochist - both liking sex, pain and bondage. So, you asked what I want? I want to own you, abuse you and make you my slave."

"Your slave?"

"Yes, my slave. I want you locked up in my shackles, willing to satisfy my every need and crave the pain I offer. You went trolling the internet looking for a Mistress, didn't you?"

"Yes."

"Well, she found you, and you seem to fit all her needs."

"But I don't even know you."

"You're wrong, dear friend. We've actually run into each other a few times since you moved here."

"So, who are you?"

"I'm your Mistress. That's all you need to know for now. Give some thought to what you have become and what you really want. I just might give it to you. I'll contact you again soon."

"But...."

There was no response. I just sat there and stared at the screen, but quickly noticed. I had another hard-on. My sex juice had already dripped from the end of my throbbing cock, leaving a large wet spot in my sweats.

I ran our conversation over and over again in my head. She was right. Being a slave would be a dream come true. It's what I've always wanted, but what if she isn't my type. I realize that once I agree and submit to her, I'm committed until she has no more use for me. My God! We never discussed limits or safe words. Panic instantly washed over me. There's no way I could take the paddling the guy in the story endured. Sure it was only twenty-four strokes with her paddle, but the force would have been far beyond my limits. Hell, I don't know my limits. And then there was the rape. Sure I've played with butt plugs, but mine are far smaller than the rubber cock she used on him.

There's an old saying that comes to mind. "Don't bite off more than you can chew." Am I going to get in too deep, because once I allow someone to tie me up or lock me in cuffs, it's too late. She can do whatever she wants, and I won't be able to stop her. I will have given up all control. But that's what makes it so exciting. Somewhere I read it was all about trust and an exchange of power. I would need to submit to her completely. I guess that's where it all starts. I'll take it slow and see where it goes.

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.