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Story Info

Posting Date 2006-07-10 19:28:40
Author tarnished
Title Pain and Ecstasy
Category tried Sado/Masochism
Where it happend My bedroom
Age then 17
Age now 23
Viewed 266
Story Length 2248

(9 votes / 89 points)

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Pain and Ecstasy


Let's see, where to start? When I was 17, I had a boyfriend who was 21. He was not my first lover, but he was the first who was substantially more experienced than me. I tried many new things with Mike, most significantly S&M. I can say he awoke my submissive side something fierce.

On this particular night, my parents were out of town and we were alone in my house. We both knew that a night of hot sex was in store. I had no idea how hot. After we ate, Mike produced a video tape. I was a little taken a back figuring we would head more or less immediately for my bed. He insisted, taking a stronger tone than usual. The tape, he explained, was the "Story of O." I had no idea what this was. He said it was about a woman who became a slave and was used by many men. Now, my boyfriend and I had tried a little spanking and one very short bout of restraining. But nothing like what I was to see O go through. As we watched the tape, Mike's hands roamed freely over my body. To be honest, I was incredibly focused on the tape. When O was initiated at Roissy, I nearly came myself. By the end of the tape, both from the visual images and Mike's hands, I had come 3 times.

After the tape, Mike took my hand and led me upstairs to my room. Once there, he told me to sit on the bed, using again that stronger tone. I was willing to do anything at that point that culminated in my being fucked! He reached into his backpack and pulled out a few things. He said that he wanted to try some of the things that O went through. My eyes went wide I was not sure I could take anything that had been done`to O. He showed me some of the items...Several scarves, a dildo (bigger than any I had!) and a belt. He told me that he wanted to tie me up, whip me and then fuck me. He said that he would not do any damage but that I would not have any option to resist once we started. I was so hot still from the video that I agreed.

He told me to stand and to strip while he watched. I quickly took my clothes off. He had me stand there while he examined my body. This attention was incredibly frustrating. He then had me kneel down while he stripped. When he was nude, he came to me and told me to suck him off. He said that when he did fuck me he wanted to be able to fuck me for a long time. I took his cock into my mouth and licked it thoroughly before sliding it down my throat. I gagged only briefly before my throat relaxed. I knew that he would not last too long though he surprised me by telling me to lower my hands. He took both sides of my head into his hands and really began to fuck my face. He only lasted a few seconds after this and he came hard down my throat. I swallowed as much as I could, some cum dribbling down my chin. When he was finished, he told me to clean my face with my fingers and then to suck them clean.

After a few seconds of catching his breath, he put two of my pillows in the center of the bed and threw the rest off. He told me to lie face down over them. I began to get a little nervous and begged him just to fuck me. He shook his head and said either I obeyed or he would leave. Some choice. I lay over the pillows and awaited my fate. He began by securing my hands to the bed posts. I tried pulling on them but I knew it was useless. He then tied my ankles similarly. I knew I must make quite the scene now, spread-eagled face down on the bed, my ass up in the air. He then took my panties and his last scarf and kneeled by my head. He pulled on my hair so he could look me in the eyes. He said that he was going to gag me now and that this was the last chance to wimp out. I told him to be Sir Stephen and use me as he wished. He smiled and then shoved my panties --clean thankfully, though slimy with my juices -- into my mouth and tied the scarf around my head.

I lay there for a few moments while he arranged things behind me. I couldn't really tell what he was doing. He then climbed back on the bed, between my legs. I wondered if he had changed his mind and was going to fuck me now. The first slap of his hand quickly made me realize he was on track. I flinched more from surprise than pain at the first slap. However, he began to rain slaps down on my ass with both hands very quickly. The pain began to build and I squirmed in the bonds. He went on for 3 or 4 minutes, my ass, I am sure, turning a deep red. I was moaning into my gag but had not screamed. I thought myself quite brave at handling the spanking. After he stopped, he remained on the bed between my legs and I again, hoped that he would forget about the belt and fuck me. Well, fuck me he did but with the dildo he had brought. It was 8 or 9 inches long, longer than Mike was but not as thick. It slid into my cunt very easily as I was still wet from the video. He fucked me with it, moving it quickly in and out, for awhile, pushing me to another orgasm. I think he wanted me to cum, knowing what he had in store for me. The dildo pounded deep inside me, making me gasp for air. It took only a minute or two and I came for the fourth time that night.

After my orgasm, he slid the dildo out and got off the bed. I heard him pick up something and I suspected it was his belt. I could hear swishing it through the air and my heart skipped a beat or two. I did not know if I could handle this pain. I also knew that I had no choice...I was going to be whipped. He draped the belt over my ass and told me to be brave. I screamed at the first stroke. The pain laced deep into my butt, unlike anything I had ever felt before. I regained a little bit of control through the next few strokes though the pain was incredible. I flinched trying to anticipate the strokes, hoping my muscles would minimize the pain. I really had no clue. After 6 or 7 strokes, I went limp and the strokes really cut into me. I began screaming at each stroke, begging him to stop. I doubt he heard or understood me anyway and he continued to whip my ass. As the tears flowed down my face, my voice became hoarse from screaming. His strokes slowed down, so I hoped he was nearly through. He paused for a second and then said I would get five more as a punishment for not swallowing all of his cum earlier. I was sobbing on the bed and tried again to hold my ass muscles tight. But it was useless, the belt cut deep into the soft tissue, wrenching more sobs from me. The last blow nearly made me pass out.

I must have sobbed for 5 minutes on the bed before I began to realize the whipping was over. My ass was on fire. I thought for sure I must be bleeding and that my ass would be scarred for the rest of my life. Part of me was furious at Mike but I was mostly too exhausted from the whipping. Mike got on the bed again and this time moved his cock into my cunt. He fucked down deeply into me, my body shuddering from the penetration. I moaned again as his thighs pushed into my brusied ass. He fucked me steadily for a few minutes, my cunt starting to heat up again. He paused for a moment and grabbed something behind him. As his cock lay just inside my cunt, I felt his finger push into my asshole. He had done this before during sex but something seemed different. Eventually I figured out that his finger was coated with some sort of lubricant. I had always refused his inquiries about anal sex. I was still an anal virgin at that point, not even my dildo pushing into that hole. My mind raced as he continued to fuck me with his cock, now pushing two fingers into my tight rear hole.

Mike withdrew his fingers and laid his body completely over mine, his cock deep inside me. He whispered into my ear that he wanted to fuck my ass but that I could say no. My ass was really in pain as he laid his body weight on it. I knew what he was asking but my mind was really too dazed to think about it. For some reason, I kept thinking back to the video. O had been fucked in the ass by several of the men who used her. I knew that a slave could not refuse such a request. I weakily shook my head yes. Mike lifted himself up and slid his cock out of my cunt. I knew what was coming and knew that it would hurt, almost as much as the whipping. Maybe the pain from the whipping would dull this pain...Or so I hoped. Mike began to push his cock at my asshole. I whimpered and reflexively tightened my ass. He spanked my ass hard with his hand and told me I had to relax. Yeah right.

With willpower I did not know I had, I relaxed my asshole as best as I could and waited to lose my last cherry. I nearly screamed when his cock finally pushed into my ass. I could not believe something that big was trying to force its way in. His pressure was relentless and inch after inch slid in. I was in near shock as my asshole was forced open so wide. I moaned and writhed a bit until he slapped me again and told me to lie still. I gasped again in pain when I felt him push the final bit of his cock in my ass. My entire ass, inside and out, was in great pain. He paused there for a moment before he began to pull out. I thought somehow that would feel better, but the tissue in my rectum was so sore that it felt worse. Even with the lubricant, my ass was stretched painfully wide. Once his cock was nearly out of my ass he slammed back into me hard. I screamed but it did not stop him. He began to fuck my ass every bit as hard as he had been my cunt. I could not believe this was happening, what felt like a telephone pole was fucking my asshole. He fucked my ass for what seemed like 10 minutes before pausing. He reached behind him and grabbed the dildo again. While still deep in my ass, he shoved the dildo back in my cunt. My mind began to swim in overwhelming sensation. My ass was on fire, it felt like it had a bat shoved in it and now my cunt was filled. He resumed fucking my ass, his movements causing the didlo to move in my cunt. The heat from the ass and the presence of the dildo caused an orgasm to build quickly. I came for the fifth time that night as I felt Mike cum in my ass. The sensation of cum drenching my bowels for the first time is one I will never forget.

After he came, he untied me. He held me in his arms as he tried to quiet my mind and body. Eventually he asked what I had thought of it. I told him I was not sure. The condition of my ass finally made me get out of bed and totter over to the mirror. I was surprised that the ass, while very red and with lots of whip marks across it, did not look all that damaged. It sure felt different. I went back to the bed, to his arms, and slept the night away.

Since that wonderful first night, I have had other lovers and a few Masters. I have come close to what O experienced in her tale. I am still seeking Roissy however. I am a slave, I know that. My night with Mike was my first real taste of it.

I am curious as to what people think of this story. This is my first attempt at writing down any of my experiences. Please let me know what you think (or if you know where I can find Roissy!) and email me at I look forward to hearing from you.


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