I caught up with a old friend, and this is what happened.
It was a sunny summers day and I did not know what to do with myself. Eventually, after much deliberation, I decided to go for a walk down to the shops. I did not need anything but at least it was something to occupy myself. As soon as I arrived I walked into the doors of the centre our eyes met. It had been so long since I had seen her, but my feelings remained. I had a crush on Jenn since we were in school together. She had always been a bigger girl, tall with sexy curves encasing her body. Her breasts were large as well, at least a cup size F, and bounced subtly as she walked toward me. Her hair was cut short and styled perfectly atop her head, coloured a light blonde. Her skin was lightly tanned from all the time she spent outdoors, at the beach or in the park on weekends. All the way down to her fingers she was perfectly groomed, a product of her part time employment. By day she worked at a technology retailer as the manager of the establishment. In her spare time she ran her own business selling manicures and pedicures from home, which accounted for her perfectly styled nails, both on her fingers and her toes. She did take good care of herself, that was for certain. As she approached me my head was filled by the vulgar fantasies that I had dreamt of her over the years. I was of a short, slim build, quite frankly her polar opposite. My imagination ran wild with fantasies of me being punished by her, bending to her every whim and desire. I almost got a hard on in the middle of the store just looking at her in those open toe fuck me heels. I tried desperately to snap out of it as she stood before me. She towered above with a smile plastered across her face. “Fancy seeing you here,” She greeted me. I nodded in agreement. Soon we got to chatting and she eventually asked me to her house the following day. “It would be so nice to catch up, it's been so long since we had a real conversation,” She commented. We arranged to meet at around 3 o'clock in the afternoon, for a coffee at her place. I eagerly agreed. Just being near her made me want to wank almost immediately. But of course, being in such a public place, I refrained. The next day could not arrive soon enough. That night my sleep was restless just thinking about what could possibly take place the following day. My imagination ran wild with sexual encounters involving Jenn in her beautiful home. The possibilities were endless. I found myself wanking over and over again at the thought of her stunning pedicured toes, big tits and fat ass. Her soft curves and warm face. Finally, I was able to get a few hours sleep before I was awoken by the sunlight seeping through the curtains of my bedroom window. I was ecstatic to be awake that morning, dreaming of what was to come when I caught up with Jenn. The day progressed slowly with the anticipation of what was looming that afternoon. I was ready hours ahead of time and sat nervously on the couch checking the time every minute. Finally, it was 2.45 pm and time to make my move. As I drove up the long driveway my heart began to race. I wondered how the evening would play out. Was she more interested in me than I originally thought? There was only one way to find out. I nervous evacuated the car and took a deep breath in. Her house was the perfect representation of her. I could see the cross fit dead centre in the front window, she loved to stay in shape using that thing. Everything was delicate and feminine. I arrived at the front door and rang the bell cautiously. Jenn greeted me almost instantly with open arms. She smiled at me with those sexy lips of hers and welcomed me inside. “It's so good to see you!” She said ecstatically. I nodded in agreement. At once I felt relaxed again. She made me feel at home straight away. Minutes later we were already seated in her lounge room having a mug of piping hot coffee. I sipped on the boiling beverage and listened intently to what she had to say. I hung on her every word. I took in the scent of her home, I got a whiff of the chemicals she must use in her own business. It smelled like the nail salons that I passed in the mall infrequently. I asked her how work was going, “Absolutely brilliant!” She replied. I was happy for her. It seemed that everything was going her way since we last spoke. After that I barely heard a word. It was like a switch flipped in my brain and all I could think about was her in a sexual tone. Her breasts heaved as she spoke in her deep, feminine voice. Her fingers fiddled with the handle of the mug and the sugar bowl on the table. She could not keep her perfectly manicured fingers still. She flipped her hair subtly every so often as the short strands fell in front of her eyes while she talked to me. I felt the boner growing inside of my pants as her body did things to me. My imagination went rogue again, just as it had in my dreams the night before. I wanted her to own me, to have her way with me. To be a slave to her every whim. I wondered endlessly what she would be like as a mistress. Little did I know I would not have to wonder for long... “Hello?” Oh no, I had snapped out of reality for a little too long. Jenn looked at me puzzled as I politely urged her to repeat the question she had just asked. I could not hear a single word as my erection pressed harder against my pants. I could not take this a second longer, what if she saw? Would she think I was a freak? I needed to relieve myself, and fast. “Excuse me, Jenn. I just need to go to the bathroom,” I stuttered. She nodded and seconds later I was rushing down the hallway. What options did I have? I had to think fast. On my way to the bathroom I found the answer. Her bedroom door was slightly open and as I peered inside I could see a beautiful pair of strapped, black heels laying carelessly on the carpet from their previous wear. My boner pressed harder still against my boxer shorts and, in my desperation, I entered her private bedroom and picked the left shoe off the floor. I undid my pants and allowed my erection to stand at its full length as I breathed a sigh of relief while it flopped out in front of me. I brought the shoe up to my face and took a deep breath in. I could smell the sweet scent of her pedicured feet and it was overwhelming. Her shoes were far bigger than mine, size ten and a half fitting in with her larger frame and curvaceous body. I began rubbing my cock up and down, picturing her playing with her big feet in front of me. A few minutes passed and I was getting closer and closer to orgasm. I completely forgot where I was, that was until I heard the door creak open behind me. “What are you doing?” Jenn squealed as I turned around, dick still clutched in my hand. I dropped the shoe on the floor as I spun to face her. What should I do? She caught me in the most compromising situation. I wondered what would happen from here. I need not have wondered for long. To my surprise, a smile appeared on her face as I stood pants less in the middle of her bedroom. “Uhhh,” I could not find the words to answer her. There was nothing I could say, it was obvious what was going on in here. She took a few steps toward me and I watched her, frozen, with my cock still hard. “You have a foot fetish, do you? Well, I must admit I am flattered,” She cooed. Then she was just inches from me. I could smell her perfume piercing my nostrils as she stood above me. She grasped my cock in her hand and squeezed it, hard. I winced at the pain of her grip on my erect penis below. She pulled me closer and reached around to spank my ass with her big hands. It stung in the most exhilarating way. I moaned as she spanked me again, harder this time. Without a word, she spun me around so that my back was facing her. She pushed my back down so that I was bent over in front of her. I braced myself for the inevitable punishment I was about to receive. It was like my dreams were coming to fruition. I was both shocked and turned on by the events that were unfolding on what started out as a normal evening. I cried out as her blows came down upon me. On one cheek and then the other. “You have been such a bad boy,” She told me as she spanked me harder and harder. She was right. “What gives you the right to come into MY room and wank over MY shoes? Now you can take your punishment like the dirty little whore you are!” She told me. That was fine with me. I wondered what punishment I was about to get for my bad behaviour. She stopped for a moment. I could feel that my ass was beginning to turn red. It hurt just a little, in comparison to how much I was loving it. She walked over to her night stand, with me still bent over in the middle of the room, pants around my ankles. I looked up at her as she took what looked like a bottle of lube out of the draw. She walked back toward me and leaned down to whisper in my ear. “Now I am going to have some fun with you,” She said seductively. My cock was throbbing by this point. She reached up beneath me and pulled on my cock a few times before slapping it hard. I moaned in slight pain. She made her way back behind me and forced my head down so that I could not see what was going on. It made it all the more hot. Moments later I felt the lube sliding down my ass. It crept between my cheeks and she rubbed it in. That was when Jenn slid a finger right up my asshole. I had never had anything inside my ass before and it was slightly painful. But this pain, mixed with the immense pleasure I was feeling from her touch. “You are really tight. I'll need to work on this a little if I am gonna fuck you later,” She warned me. Then I felt another finger push inside. I could feel my asshole stretching around her fingers. I moaned as another and then another pushed inside. Soon I had four of her long fingers sliding in and out of me. She squirted another portion of lube around my ass to make the fingering a little easier. Suddenly, she removed them all and reached down to the floor to pick up a pair of discarded stockings. She grabbed my arms and pulled them behind my back. I felt her tie them tightly together. I was trapped by this beautiful woman and I could not control myself. “Now, it's time you do something for me,” She told me. A hand found its way to my shoulder and she pushed me to a kneeling position on the carpeted floor. My heart raced as she removed the heels that she had adorned for our meeting. She sat in front of me on the bed as she slowly took them off one at a time. They fell to the floor next to the other pair I had been admiring earlier. She dangled both of her feet in front of my face as I kneeled helplessly on the ground. She moved my hair out of my face with her toes as she toyed with my slim frame on the floor. They got closer and closer to my face as she giggled on the bed. “You are gonna suck on my toes and lick my feet, you dirty slut,” She told me. I nodded my response. I would do anything for her. Jenn's big feet were just inches from my mouth. “Open,” She instructed. I did as I was told, like a good slave. Her toes found their way into my mouth and I sucked tenderly on each one. She leaned back and moaned her approval. I sucked harder. I wanted to please her so badly. She pushed more of her toes in at once. Before I knew it I had her whole big foot in my mouth, all of her toes. My tongue wrapped around each toe individually inside of my mouth. She took her foot out and raised the other. “Lick it, my little whore,” She told me. I obeyed. I did as I was told. I closed my eyes and licked her foot up and down, as best I could, having never done anything like this before. I was loving it. I loved her degrading me and making me her little bitch. I wondered where all of this would lead from here. I wanted her to do whatever she wanted to me. I was entirely at her disposal. She pulled her foot away and smiled at me. “That was a good boy,” She complimented as she rose from her seated position and began to get undressed. I marvelled at her naked body standing right in front of me. It really was a dream come true. “Now, it's time for you to lick my asshole. I know you will do a good job for me, you dirty slut,” She berated me. My jaw dropped. Before I knew it her huge ass was right in my face. She grabbed each of her ass cheeks and spread them wide so that her pink, pouting asshole was right in front of my lips. She leaned back and pressed it against my face. I could barely breathe as I licked around the outside of her hole. She moaned and convulsed as I worked away as best I could. I gently ran my tongue around and around. I wanted desperately to please her. I wanted to be her dirty little slut forever. “That is a good whore,” She moaned from above. I nodded in agreement as I just continued to lick her dirty asshole. My cock throbbed as I rimmed her relentlessly. I could tell she was enjoying herself. “I think its almost time for you to get a good fucking, slut,” She said breathily. I was scared but excited at the same time. She leaned forward ever so slightly so that I was no longer being smothered by her big ass cheeks. I panted as she stood up and made her way back to the night stand. She opened the draw again and pulled out a big, black strap on dildo. I was horrified that I would be taking that inside my ass. I was not sure it would fit, even with the entire bottle of lube. It was all foreign to me. But still, I was looking forward to it, all of it. Especially at the hands of Jenn. I watched tentatively as she pulled it on her chubby body. I watched as her curves strapped into the harness and she was standing in front of me with the big dick pointed directly at my face. It was bigger than mine, bigger than any I had ever seen. I was worried beyond belief. “Are you ready for this?” She said, rubbing the strap on as she spoke. I nodded, although I was not sure that I really was ready for it. I just felt the need to please her so badly. She laughed, villainously, “Well, you can't have it yet, you little whore,” She told me. Then she strode back toward me and positioned herself above. She looked down at me, and I up at her, as she spat on my face. I felt the saliva run down my face as I closed my eyes. She spat on me again. Then, without a word spoken between us, she grabbed my chin and shoved the strap on deep inside my mouth. I gagged as it hit the back of my throat. She laughed at my struggle. “I love watching you sucking on my big cock,” She assured me as she pulled back and then back in. Finally, I knew what it felt like. The hard rubber moved in and out of my mouth with ease. She spat on my face again as she fucked my throat hard. I tried my best to take it but it was too much. My eyes began to water, my tears combining with the spit covering my face as she forced the strap on deeper down my throat. She moaned at the pleasure she was feeling from fucking my mouth as hard as she could. I loved watching what I was doing to her, and what she was subsequently doing to me. “You like that, don't you, filthy slut?” She cried. I tried to respond but all that came out was a muffled moan. I could not even nod my head. I wanted to know what it would feel like to have her big cock inside my ass too. I would not have to wait long. It was almost time for her to fuck me as hard as she was fucking my mouth. “I think you're ready, you have been sucking this dick good,” She pulled it quickly from my mouth and walked behind me. She pushed my face into the carpet as she spat on my waiting asshole and rubbed the head of her dildo against it. I felt ready, I hoped that I was. I did not have much time to wonder though as her shoved it inside me as hard as she could. I screamed at the pain I felt while she moved in and out of me. “This is what you get for what you did, you little fucking slut,” She scolded me as she fucked my asshole hard. I could feel myself tightening around the cock as she moved. I could sense her getting closer and closer to orgasm with her strap on rubbing against her clit. She grabbed my ass hard as she fucked me even harder. She spanked me again as she came closer and closer to finishing. “You are a good whore, you are gonna make me cum,” She moaned. I pressed my face against the carpet as I tried desperately to please her. I wanted her to cum, I needed her to cum while she was fucking my virgin asshole. Seconds later it happened. She pulled me close as I heard her come to her sweet release. She screamed her pleasure as she held the cock inside me, rubbing her body against my ass as she came hard. “Oh yeah! That was good, you dirty little whore,” She complimented me. She pulled her dildo out of me and allowed me to collapse on the floor. I felt my asshole gaping after the hard fucking I had received. But it was not over yet. My cock was still hard and throbbing beneath me. She rolled me over and looked down at my hard dick. “I guess we should finally do something about that, shouldn't we?” She said, seductively. Then she instructed me exactly how she wanted me to finish. “Now, take your cock in your hands again, just like when I walked in the room before. You know what I mean, don't you whore?” She told me, and I did exactly as she commanded. I held my cock in my hand and began to stroke it. I would not last much longer either. I was close before but as I held my cock in my hand I could feel it welling up. “You are going to cum all over your face. I know you can shoot your load that far. I want you to cover your face in your own cum,” She said sternly. It was happening all too soon. I moaned deep and long as I shot my cum all over my own face. It dripped down my cheeks and chin, onto my chest below as I laid there, stunned at what had transpired between us that evening. It was not what I had been expecting, that was for sure.
Caught and punished by Jenn and you won't believe what happened with pictures
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daughtersfeet
- Posts: 248
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Caught and punished by Jenn and you won't believe what happened with pictures
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Newfootlover
- Posts: 2558
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Re: Caught and punished by Jenn and you won't believe what happened with pictures
What an incredible story, she's looks and sounds amazing!! You're a lucky guy!!