Painful Pleasures

Chapter One-1

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 f**k!” 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 c**k had swelled to its maximum proportions and pre-c*m dripped from the very tip.

Yea, I’m into some kinky s**t. 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 s****l. 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. n****e showing bras, tiny p***y-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 c**k 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 c**k 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 f**k!” 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 c**k 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 f****d 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 s*x 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 b**m 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 c**k 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 f**k!” I wanted it so badly.

I had to stop reading the story in order to adjust my c**k. It had immediately come to full attention, filling with hot, s*x-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 c**k and balls. With my left hand I fondled my nuts while slowly stroking my hard c**k 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 d**k.

“Kiss it, slave. Suck my huge c**k, so I can f**k 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 f**k 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 d**k 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 c**k 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 c**k 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, f*****g rhythm. Her slave cried and wailed from the violent rape.

My hand rubbed my c**k 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 f****d him again even harder, slamming her hard c**k in even deeper. His screams had diminished to soft babbles and cries. Her slave had given up. There was no fight left in him.