When I was 19, I had my first moment of clarity. My first sexual expierences seemed to be lacking something. I gave it a few years, a few different partners, and still something was not right. They boys I slept with in high school were okay, but none really took me where I really wanted to go. I never really knew where I wanted to go until I got there. When I was 17 I started taking out personal ads trying to find an older man, thinking that maybe that was the answer. I had slept with a few older men, and still nothing. Nothing but the empty feeling. I had orgasms, but the emptiness still returned. The week before I turned 19 I had gone to the local coffee shop to meet a man who I had been talking to on the phone. He had called in response to an ad I had placed. I only lived a few blocks away, so I chose to walk to the coffee shop instead of driving. If there was one thing I had learned on this journey of self discovery, it was how to avoid being stalked. It was the middle of October, and it was starting to get cold. I checked myself in the hall mirror as I was walking out the door. I had chose faded jeans, a tank top, covered by a big wool sweater. I was trying not to look too easy. I figured if it didn't work out, at least I did not look that attractive. I shoved my keys and my pepper spray in my purse and took off. As I approached the coffee shop, I saw him. He was younger than I imagined, I would have put him at or around 36. He had told me previously that he was 42. I walked by and pretended not to notice him as I want in for a cup of tea. "Mike?" I asked as I walked by his table. "That would be me" he said in a slightly gravely voice. He handed me an envelope and got up and walked down to his car, got in and drove off. Nice I thought, didn't even get two words out before he took off. I was a little miffed, I mean I am almost 19 years old, what guy his age would not want to take me back to his place for a little play time? I sat down and opened the letter. There were directions to his house, his number and a time set up. The note stated to come by his house, pack enough things for a weekend in, and to park my car on the street. The time was for the following Friday evening. I knew in an instant that I would go. I thought about it all week. I had made a copy of the note, the personal ad, his number and the name he had given me. I locked it in my desk drawer, you never can tell these days. I once again, checked everything in the mirror before I left. I had packed a few of my favorite toys, some lingerie and my shower stuff. I was shaking when I pulled up in front of the house, I called the number, he just answered and said the key was under the mat, to come on in, and take the stairs down to the basement, he would be waiting. My heart was beating a mile a minute as I unlocked the door with shaking hands. I stepped inside, and went straight to the stairs. I thought my knees were going to buckle as I walked down the narrow steps. I reached the bottom step he was sitting in a chair reading a book. There was an opera playing in the background. "Hi" is all I said. He put his book down and took my bag. He put the bag on the chair and took my hand. He led me to a couch. He undid my sneakers, took them off slowly. He slowly took off my socks. He stood up, and then quite matter of factly removed my sweater, my t-shirt that was underneath, removed my bra. He did take a few minutes to admire my full breasts. He went next to my jeans and then my panties. I had chosen to wear a matching bra and lacy thong. After he completely undressed me, he took my hand and let me down a hallway to a bedroom. The room was near empty except for a bed, a dresser, a night stand and a chair. Nothing on the walls, and no windows. I was starting to get creeped out a little. "If you could just lay down on the bed for a minute, I'll be right back" he said with a sincere smile. The kind of smile adults only get when they are really excited about something fun. I laid down, made myself comfortable. The room was the perfect temperature, not too cold, not too warm. He returned completely nude. He laid on the bed next to me. "I know what you're going through with the feeling of emptiness. If you can just trust me, I think I can show you what you have been looking for." He spread my legs and knelt between them. He took a few of the pillows and put them beneath my butt to prop me up a little. He then got up and crossed the room to the dresser. He began collecting some things, I could hear some clanking. He then switched off the lamp. There was a little bit of light, just enough to see coming from the open door. I felt him spreading lube all over me. my pussy, my ass. "Do you trust me?" he asked. I didn't really, but if it led me to the expierience I had been chasing, it was going to be worth it. "As long as you stop when I say, then anything goes." I could not believe those words left my lips. He had some strange spell over me. I felt his hands starting to part my lips, I was instantly wet. His large warm hands carressed my shaved lips. He began to gently tug at my clit. "Okay, hold still." He said. Spreading my lips wide with one hand, he reached for something that was on the night stand. "Ready?" he asked me. I just moaned. I was so turned on I could not even speak. I had no idea what was in his hand. I was caught up in being so turned on, I started to panic a little. That just made me more turned on, and wetter. I felt him spread my lips very far apart, He had on hand spreading my lips apart so far that I could feel the heat from his hands on my clit. I Felt a sharp, not entirely unpleasant pain on my clit. "Ooooh, what is that?" I asked him. I was loving the pain. "It is an alligator clip. Like a clothespin with teeth." He said gently. "Is that okay?" All I could do was moan with pleasure. It felt like a permanent bite. I have had men bite my clit before, but this picked up where they had left off. It was heavenly. It hurt, it stung, and it felt good. I felt my pussy aching for him. I wanted to fuck so bad I thought I was going to pass out. I arched my hips towards him. "Not just yet, we have only gotten started." He told me with a chuckle. I started to pull my lips again. I felt another duller version of the clip that he had placed on my clit. I started to realize that he was placing tiny little clips down both sides of my lips. It felt like close to 5 on each side. They felt small, like little pinches. I thought I was going to cum on the spot. "Not Yet" was all he kept saying. He kept asking me if I wanted him to continue. I just kept moaning and arching my hips up to him. He sat back to admire his handywork. I felt him tugging on the clips a little. I had no idea what he was doing. "Do you want me to bring a mirror for you to see?" I just kept moaning and nodding my head yes. He went down the hall and returned carrying a full size mirror. I placed in at the foot of the bed and adjusted it so I could see. What I saw turned me on so much. He had attached tiny little clips to my pussy lips and then strung them all together with a piece of red thread. My pussy almost looked like it was smiling. He had placed the clips up higher, so he still had access to my pussy and my ass. IT was beautifull. He had tied it neatly with a little red bow. I just wanted to look at it forever. It felt like heaven and looked like a piece of art. "I love it!" I blurted out. "Do you want to keep going?" He asked gently. "Want to take a break?" he asked. I just shook my head. He knelt down between my open thighs. All I could see in the mirror was his back. And a towel on the bed. I felt him apply more lube. This type of lube stung for just a minute, and then a very subtle numbing sensation. I felt him caressing my urethrea. He was trying to get his pinky inside. It was stinging like mad. I concentrated on the feeling of the clips, and remembered how beautifull they looked clamped to my pussy lips and tied together with the red string. "Okay, this is going to sting for a minute, so take three deep breaths and exhale through your mouth, okay?" I heard more clanking. I felt him spreading my lips wide, really wide. I took my first deep breath. I felt something cold and hard against my urethra. As I started to exhale out of my mouth, I felt that cold and hard thing pressing a little harder against my hole. I felt a little more stinging lube, and then took another deep breath. This time as I started to exhale I felt the cold hard thing forcing it's way into my pee hole. It was forcing and stinging. It hurt, it was heaven , it was hell, but it was good. As I continued to exhale I felt it go farther into me. It was spreading me apart. I knew it was little, but it hurt so bad. I had never had anything in my urethra before. I was a totally new expiereince for me. I drew in another breath sharply. "Hold your breath." he stated. "Count to 5, then exhale." I felt him twisting the metal around and around. It stung so bad. I had counted to 5 and was starting to exhale. I felt the metal go into me as far as it could. I felt something heavy around the opening of my hole. It must be something to keep it from going too far. I was panting at this point. It was more pain than I had ever felt. Though I was beginning to feel a little better. The pain was slowly subsiding into a dull ache. It felt so foreign, but felt so good. I was still breathing hard when I felt him touch the long piece of metal. He had tapped it with something and it vibrated inside of me. I almost lost it then. "One more time?" He asked me as he tapped on the metal. I nodded my head. "This time six deep breaths, exhale through your mouth. On the last three, hold your breath to the count of five." He instructed. I loved that. I loved how he left me no choice but to follow his instructions. I took my first deep breath. I felt him taking the metal piece between his thumb and finger. As I exhaled I felt him taking it out of me. As he slowly drew it out, I did not feel any pain, just the pleasure of the new experience. I took another deep breath, as I exhaled I felt the metal completely leave my body. I felt my hole gaping and mourning its removal. With my next breath, I felt more stinging lube, heard more clanking. I was sure he was going to do it over again. I waited in anticipation. "Don't forget to count to five." he warned. I slowly drew in my next breath. Before I even counted to two, I felt another hard piece of metal at my small opening. This was different though. It felt huge compared to the last one. I had counted to five, and began to exhale. I felt it then. It was so sharp and painfull that I stopped exhaling. "Keep breathing." He said. Oh my God, what the hell is happening to me? I felt the familiar pain, the stinging, but there was a new edge to it this time. I drew in another breath, this time as I was holding my breath and counting, I felt it go in. He was really shoving it hard this time. As I started to exhale He shoved it in all the way to the hilt. I was too stunned to stop breathing. The pain and the pleasure were paralizing. I drew in another breath, he pulled the metal almost all the way out. As I exhaled he slowly eased it back in. When it was in all the way, I drew in another breath and exhaled. "You are doing so good. I am so happy for you." He said with a beaming smile. " I am just going to leave you like that for a second, while I go and get something." With that, he left the room, went down the hall. I was still breathing and looking in the mirror at myslef. I loved the way I looked just then. I had started to sweat, and my hair was just a little damp around the edges of my face. In addition to the clips adn thread, there was something else. I could see now that metal piece was about the size of my index finger. There were a few little drops of blood on the sheet. It was okay, Iloved it. The pain made me feel right. I took my finder and slipped it into my pussy to see what it would feel like with the metal still in my urethra. It was amazing. I heard footsteps coming, I quickly took my finger out and placed both my hands behind head. He came in carrying a box of condoms. "Is this okay with you?" He asked. "Oh God yes, I can't wait." "I am only going to penetrate you for a moment, I want to stretch you out for something a little bigger if you don't mind." He stated. I spread my legs a little wider, inviting him to fuck my pussy. He knelt on the bed and then placed his hands on my hips. He flipped me over easily. He then placed a smaller mirror under us. I was on my hands and knees so that I could see everything on the mirror he had placed on the bed underneath us. I feel him spreading fresh lube all over my ass. I love anal, so I can't wait for him to start. I feel the head of his cock pressing against my hole. I push myself back against him, and I feel the head of his cock penetrate me. I did not get a good look at him before, but he feels pretty big. I feel a familiar dull sting. My hole contracts on him a few times before loosening up a little so he can slide the rest of the way in. He feels magnificent. I feel the clamps on my lips, the metal in my pee hole. He reaches around and holds the metal so it will stay in place. I start arching my hips and fucking his cock with my ass. "Hey, don't get too carried away, I am only trying to stretch you out a little." He says a little too sternly. I stop immediately. I can't figure out if he is enjoying this, or what. He does not seem to want to fuck, so I am taken aback. Oh well, If he didn't liek what he was doing he could stop anytime. I looked down at the mirror to see his tight sac bumping my wet pussy gently as he thrust himself into my ass. Amazing. I had never seen my pussy look so beautifull. The red thread was dripping with my juices. It was so hard not to cum. I knew that he did not want me cumming just yet, so I looked up at the wall instead. He stopped thrusting and gently pulled out. "Ready?" he asked. I nodded again. He flipped my back over, so that I was facing him again. He propped my ass back up on some pillows. "Okay, remember the breathing thing we did a while ago? Do it again okay?" He purred in a low and soft voice. I knew he was extremely turned on by what he was doing to me. I felt more lube, this time he stuck two fingers inside of my ass and spread the lube. I heard more clanking around. I looked in the mirror, but could only see his back. With is fingers still inside of me, twirling around, spreading me out, I placed another cold metal thing against me. He took his fingers out of me a little, spreading his fingers wide, opening me up, I felt the metal penetrating me. He took his fingers out and there was only the metal. I felt him slide it up farther in side of me. It was cold and it had rounded edges. It was an entirely new feeling. When he had gotten it in all the way, I felt more lube. "Just keep breathing and hold still." He said. I started on my breathing and I felt myself being spread, farther and farther. It should have been uncomfortable, any sane person would not like this. I love it. "More" I moaned. It spread me farther. It was getting to be quite painful, but the pleasure was on the heels of the pain. It felt like I was spread enough for him to get his fist into me. I heard a click, and the spreading stopped. I felt more lube inside my ass. I was open so far, that I could feel the air. I heard him rummaging through a drawer somewhere. I was in a half awake, half dream state. I could not even open my eyes. I felt him kneel back on the bed. I felt the metal being removed. It was not closing at all, only being pulled out. I felt even more lube. When the metal was out, I felt something else. It was warmer, definately not metal, not human flesh either. It almost felt like wood. I opened one of my eyes and say a very thick and smooth piece of carved wood. He looked at me and winked, I closed my eye and I moaned even louder. The piece of wood looked almost like a carved butt plug, only bigger. I heard him lubing up the wood. I felt it again at my hole, it had not penetrated yet. He was pressing it against me. I automatically started my breathing again. I knew the routine by now. As I inhaled the first time, I felt a very painful dull pressing. As I exhaled I tensed my stomach muscles so that I could open up my ass a little more. I felt a stab of excruciating pain, and I instantly knew it was in . My hole was contracting and aching and stinging. It was all too much. My urethra, my ass, both were stinging and hurting and contracting. "Be a good sport now." He said. I could hear his smile. I took another deep breath and bore down like I was trying to push the object out. "That is good, keep doing that. Just a little more to go.' He was encouraging me. I loved that. I pressed against it again, this time in went all the in to the hilt. I moaned so loud and so deep that I almost came. "Just hang on, just a minute or two more." he persisted. I felt him touching the metal that was inside of my pee hole, he was taking it out, very gently. He moved to the side so that I could see. I was speechless. My ass was stretched so far around the wood, that it had torn just a little. The metal he was pulling out of my hole had streaks of pink blood on it. When he had completely removed it, my hole gaped and contracted. I instantly missed the feeling of that metal. The red string was now soaked and dripping with my juice. My pussy ached so bad for him. Somehow during this I had fallen, and fallen hard. I had never felt anything close to what he had made me feel over the last couple of hours. I was gasping for breath, I was arching my hips towards him. He got to his knees, and put his hands under my ass. He lifted me up and shoved his cock into my pussy. In one smooth motion he was all the way in. He held me onto him and reached around with one of his hands and gently started tugging on the piece of wood that was in my ass. He thrust his cock into me and started fucking my ass with the wood all at the same time. I was in heaven. It didn't even hurt, I am sure it did, but in my fucked up little mind it was pure pleasure. I came instantly. I came so hard I passed out for a moment. I had never had that kind of orgasm. It just would not stop. I was cumming so hard. I was talking to him, I have no idea what I was saying. He kept on fucking me, increasing his speed. He kept fucking my ass as well. It felt so good. I felt him stiffen. I finished off with three really good, hard and deep thrusts. He opened his eyes and looked down at me, adoringly. "You have no idea how long I have waited for someone to share this with." he said gasping. " I have a lot more I'd like to do to you." He confessed. He pulled out of me, removed his condom. "This is going to be a bit more uncomfortable when I take this out." He warned as he tugged at the wood that was still in my ass. He flipped me back over onto my hands and knees. I felt him pulling and I started pushing against the wood. It was slowly starting to come out. With one last push it came out. He showed it to me and it also had streaks of pink blood running up and down it. He slipped me back over, and let me look at myself in the mirror. There was pink blood beginning to drip from my ass, and there was a little more coming out of my urethra. It looked awesome and felt even better. He knelt between my thighs and started to undo the string. I felt the rush of blood to my pussy lips where he was taking the clips off. It was a painful warm throb, but it felt so good. When he was finished, I looked at my lips and saw the indents from the clips. Beautifull. I had never felt so clear, and whole as I did laying on that bed. I know it may sound sick to a lot of you, but it was one of the best times I have had in my life. I got up and he showed me to the bathroom so I could get cleaned up. When I returned to the room, he had put on some pajama pants and was laying down. I put on a pair of clean underwear and laid down next to him. I drifted off to sleep recounting the night in my head.
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