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As it begins to pour I decide to seek shelter in a quiet bar. Apparently it was supposed to be 'happy hour'. Not many were around. A lonesome old man in a double breasted business suit had his face down on a table clutching a nearly empty bear mug. As I peer to my right a rather young couple decide on a song to be played on the jukebox. It was the usual night at Cappy's Bar and Grill. I grab a seat at the table in the back. I tried to stay isolated as possible. I was not surprised to see old Cappy was nowhere to be seen. I had just escaped from the office after doing three hours of overtime. Luckily I had no wife and kids to go to. My last girlfriend was very dependent on me. Always asking me for money or transportation. But that was a month ago. I haven't seen her since. I take off my raincoat and set it on the chair beside me. Finally one of Cappy's waitresses comes over. Shirley had worked here for many years. Her sagging eyes didn't seemed to convey a sense of unhappiness. I ordered myself a Rolling Rock. It was after an hour I noticed something out of the ordinary appear in the bar. The long slender legs of a fine brunette walked through the main entrance. She seemed to capture everyone's attention including the old drunken bastard who suddenly awoke to the sound of her clattering high heels. She sat on a bar stool turning the seat left and right showing her legs and her heels. She had on one the most beautiful pairs of black patent shoes I had ever seen. The pumps had a gold buckle around the front and a golden spiked heel arching upwards at an erotic height of 7 inches. I was wonderfully aroused at the sight of her stilleto heels. She also saw my arousement. My pants began to bulge. I grabbed the bottle of beer and tried to calm myself down. I have never seen such high heels on such a pretty woman. My last girlfriend always complained about the pain of wearing such high heels. The highest heel she has ever worn was about 2 inches. I kept asking myself if I should go over and chat with her. While I was wondering I stared at her lucious legs and heels. She was also wearing a raincoat; a long black shiny slicker, but she did not take it off. All you could see was her hair, coat, legs and heels. I noticed that her shoes were wet from the water trickling down her raincoat. It was dripping onto her shoes and all the way down her spiked heels, finally creating a large puddle below her. After a minute I could not take it any longer. I walked over to her and asked her how a pretty lady like her ended up in such an awful place. She replied by asking how such a handsome man as I would ended up here too. I whispered into her ear that it was destiny. She giggled. I was captivated at how gorgeous she was! She was like a brunette version of a Nikki Taylor. Cute, yet very sexy. I asked her where she worked and to my amazement it turned out she was working on the floor below me in the office building. She was also kept after work to do overtime. Her name was Bridget. For half an hour we got to know each other. I looked at my watch and it was time for me to go. I offered to walk her home and did so. We walked up the stairs in the apartment building. It seemed very run down. There was musty odor that made me almost nauseous. At last we made it to her apartment. I let her walk in front of me. Again my manhood began to bulge, as I could not resist the sight of her high heels. When we got to her door. She asked me to stay. I wasn't sure. After all we had just met. But, of course, I entered her well furnished home. She locked the door after me. I didn't expect to be here for much longer. Before I could turn around and comment on her beautiful apartment, she grabbed me by my shirt and thrust her mouth to mine. I tried to undress myself while we kissed passionately. Her hands were working me from head to toe. She pulled away and walked into her bedroom telling me to get comfortable. I sat on her sofa noticing that her shoes were on the carpet. I handled one shoe and smelled her wonderful scent. My cock began to get even harder, but this time I could not control myself. I grasped her right shoe and shoved it into my crotch. My long penis fit well in her size nine shoe. I came all over the inside. I was relieved, but a little embarassed. When I turned around, she was standing there dressed in sexy black, lacy lingerie. She waved her finger at me and told me how naughty I was. She then struck me with a whip that was in her hand,almost knocking me unconcious. Before I could get up she had already began tying me up. I was too dizzy to know what was going on. So I let it be. I was on my knees, my arms and wrists were tied behind me, and my ankles were bound. I begged her to release me. She was angry at me for jizzing in her shoe. But then she licked all the cum out. Next she shoved the same shoe into my mouth so the 7 inch heel was scratching at the back of my throat and I felt like choking. She tied that around my head like a patent leather gag. Next she went to my crotch and tied the left shoe to me with my cock inside. She told me to start humping into the shoe or she would strike me again. I did so with no hesitation. She walked back into her room and returned wearing a pair of platform shoes with a 12 inch heel. I was afraid that she would start kicking me. She told me not to stop. I came until it was dripping out of her shoe and onto the carpet. After the euphoria of orgasm started to wear off, I started to get frightened. What was next? The heels she wore were the highest I had ever seen. The width of the heel was about 1 1/2 inches but increased in width going up to the heel. I was afraid. She pushed me forward until my head and my knees touched the floor. I felt a lengthy object enter my anus! She shouted out how much of the heel I was taking in. One...two...three...six inches! I was in so much pain. Finally after a few seconds of her long heels probing my rectum, I began to cry out around the heel in my mouth. But she continued. 12 inches. She had inserted the whole high heel into my anus and began fucking me with it. As she thrust the heel in and out of me I seemed to get used to the pain and began to feel how erotic this was becoming. My erected penis continued to shoot off cum. I was in a moment of ecstacy. Now she began a different pace. More slowly. Smoothly she pumped the heel in and out of me. When she was done she took off her shoe and kept the heel firmly planted in me. My anus was so sore now. Then she dragged me into a cage in a seperate room. She wipped me several times and put nipple clamps on me. She was getting aroused through all this, seeing two of her heels piercing my body,one in my mouth and one in my ass, and another one protecting my manhood. I suddenly fainted from all the pain and was sure I would never awaken. But it had been worth it to enjoy my most erotic adventure ever.