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Anna and I made it to the elevator and started making out as soon as the doors closed. The smell of her perfume, the taste of her lipstick driving me wild. My room was on the top floor, so we had 12 floors to make out on the elevator.
When the doors opened on the 12th floor, I told Anna to stay put. I looked out in the hall and saw no one was there. I went back in the elevator, unzipped and slipped my hard cock out of my pants. I picked Anna up and slid her down on my cock. Her pussy swallowed my cock completely and I headed out into the hallway, carrying her with my cock inside her.
As I stumbled slowly down the hall, fucking Anna's amazing pussy, I asked her what the deal was with Cheryl. Anna told me that Cheryl was the meanest girl in her high school. She teased Anna about her height and weight and her red hair. She was merciless and said she'd never find a man. Cheryl ended up marrying a total loser and was already divorced. As soon as Anna recognized our waitress was Cheryl, she wanted to really show her up.
I fucked Anna up against the door to my suite while I struggled to find my room key. Anna went on to tell me she wanted Cheryl to see that she had a man with an enormous cock and was getting kinky sex that Cheryl likely never did or ever would. This was a side of Anna I had never seen and it turned me on.
Even though I could have fucked Anna all night in the hallway, even if a crowd gathered to watch, we finally got it into the room. I laid Anna down on the bed and never let my cock leave her pussy. She begged me to fuck her hard, so I started pounding in and out of her wildly. She kicked her heels off and put her sweaty feet on my face as I fucked her deep and hard. A few minutes of hard pounding and she wrapped her nylon covered legs around me and held me in deep as her orgasm hit. That's when I felt that sensation I'd been longing for, her cervix opened slightly and grabbed the head of my cock. Anna whispered "I'm on birth control, so you can cum inside me Mike." My orgasm was ridiculous. I shot what felt like a hundred spurts of cum inside Anna's awesome pussy as she continued to milk my cock.
In those moments of mind bending intense orgasm, I decided I was going to hang onto Anna. I didn't know how that would work but I needed her as much as I needed my wife. Maybe she would be my apprentice and come live with my wife and I. My wife would agree to that, right? My wife would even want to make love to her too, right? It all sounded sane to me in my orgasm fogged brain.
I told Anna I needed to pop a Cialis as I wanted to make love to her until the sun came up. I slipped my cock out of her totally cum filled pussy and went to head to the bathroom when Anna stopped me. She wanted to suck my cock. She moved to the edge of the bed and took eight inches of my soft cock down her throat until I could feel her tongue darting out against my balls. This young woman kept amazing me.
When Anna was finished hungrily devouring my cum and her own juices off my cock, she slapped me on the ass and told me to get ready. I went to the bathroom and popped a pill. I wanted to fuck Anna all night long and, when the thought of my wife entered my mind, I only wished she was here to join in.
When I returned to the bed, Anna had removed her beautiful dress and was lying there with only her white nylons and heels on. Either the Cialis was kicking in or this visual was making my cock start to rise. Anna asked me a strange question and I felt a twinge of fear, even. She asked me if I had ever tried fisting. I told her that I hadn't and wondered, nervously, where she going with this. She told me that she had only ever been with women and she had been fisted many times. She said she craved the fullness and a woman's hand is perfect for satisfying that need. Anna also said she was ecstatic when she discovered that my cock could give her that kind of satisfaction too.
In that moment, I craved Anna more than air to breathe. I was the first man this hot, young woman had ever been with and I was humbled that she picked me. Anna then asked "Will you eat my pussy, please?". Even though her gaping pussy was oozing out a mix of her juices and my cum, I had to do it. I put her legs over my shoulders and dove my tongue deep into her. I slipped off one of her heels and rubbed her clit hard with the pointed toe as I lapped away at her perfect pussy.
The mix of my salty cum and her sweet juices wasn't all that bad. I stayed between Anna's legs, devouring her pussy for almost an hour. Once I finished gobbling up my cum and her orgasms flushed out her pussy, I started to really get to taste the essence of this woman. Her pussy tasted sweet and her juices were hot as they squirted out into my mouth. I brought her to so many orgasms, I was surprised she just kept wanting more. She must have had some amazing female lovers to condition her to endure countless orgasms.
When my tongue was worn out from devouring Anna's sweet pussy, I started to push her well worn high heel into her body. As much as she was loving that, she asked if I could try fisting her. I told her that my hands were probably much larger than any of her female lovers' hands. She said sweetly, "Oh Mike, I know that. I want to know if I can take more. I want my pussy stimulated as much as humanly possible." Who was I to argue?
I pulled Anna's heel out of her sopping pussy, and jammed my raging boner inside her shoe. I had to really stretch her shoe to get my cock deep in the toe box and my balls in the heel cup. Once I did, her heel was locked on my cock. My cock was throbbing hard inside Anna's leather heel. Anna's pussy was so wet and ready, I started by easily pushing three fingers inside her. She moaned as I added a fourth finger. I fucked her with four fingers and occasionally buried my fingers to the knuckles and ground my thumb into her clit.
Anna begged me to add my thumb, so I pulled my fingers out enough to add my thumb in a duckbill shape. I started to push my hand inside her and she bucked her hips wildly trying to get her pussy to swallow more. I didn't know then but I came to realize later this sweet girl was a size queen. She was genetically gifted with an amazing pussy and she wanted to use it for her utmost pleasure.
Once I reached the widest part of my hand, her pussy could take no more. She screamed at me to push harder but, despite trying to force her open with as much effort as I could push with, this just wasn't going to happen now. I held most of my weight down on my arm and her pussy contracted and pulsed wildly trying to swallow my fist. After her stretched hole released an orgasm, I slowly withdrew my hand from Anna.
As soon as Anna looked down and saw my cock throbbing inside her high heel and stretching the leather vamp, she pulled it towards her pussy. Her heel was so locked on my cock, it was like it had become part of me. She guided the pointed toe into the entrance of her gaping hole. I knew she could take the heel in her pussy but I didn't know if the extra girth of my cock would fit along with the shoe.
As I began to slide into Anna's pussy, she wrapped her nylon covered legs around me and pulled me in. Once my cock and her heel were at the widest part, it seemed like it was going no deeper. Anna gyrated her hips wildly and kept pulling me in with her legs. I encouraged her to take it all. I complimented Anna on her amazing pussy and how much I loved her and how she needed to feel her heel deep inside her body.
As I continued, Anna's body erupted in a massive orgasm and, between the slickness of her flowing juices and her pussy convulsions, my cock and her size 10 heel popped in past the widest part and sank home to the heel. I looked down and could see my pelvis touching hers, our bodies interlocked with her worn and dirty shoe.
As much as I loved how forbidden it was for my married cock to be inside both this young woman's high heel and her pussy, any guilt I felt was overridden by how much I craved feeling Anna's cervix gripping the head of my cock. I also realized that Anna was experiencing the deepest pleasure she ever had, since the toe of her shoe was in about two inches deeper than my cock had ever touched. I wondered if the narrower toe had entered the deepest, most sacred place in her womb.
Without moving my cock, Anna's cries of ecstasy and the gush of her juices soaking her own shoe and my cock answered my question. Her orgasm started from deep within and, once it finished, I began sliding in and out of her pussy. Her filthy heel was like a condom hugging my raging boner and I was able to start fucking her really hard without my cock coming out of her shoe. My cock and her shoe were one. I alternated between fucking her fast and hard to sliding all the way out and all the way in as deep as I could thrust. Every time I hit bottom, Anna cried out in pleasure.
With her shoe dulling the intensity of Anna's pussy and only part of the top of my cock feeling anything, I was able to fuck Anna for almost an hour before I felt my orgasm boiling inside me. After fucking Anna for so long and her pussy releasing innumerable orgasms, the warmth of our bodies and the complete soaking her heel had been taking, my cock started to permanently deform and stretch her shoe to the point where my cock was starting to move around inside her shoe. When I'd pull out, her shoe started to stay buried and I was now fucking her shoe inside her pussy. The feeling on my cock head as it plunged into the soaked toe box of her heel made my orgasm start. I stroked in and out a couple more times and, on my last stroke to full depth, my cock slipped over the vamp into a space that almost crushed the head of my cock. Anna screamed "Oh my god Mike, you're fucking my cervix. Cum in my womb. Blow your load into my soul."
Anna's cries put me over the top. I shot what felt like another hundred spurts of cum directly into Anna's womb. As soon as my cock finished raging an orgasm out, I felt Anna's cervix push me and her destroyed heel out. I slid my still hard cock out of Anna and then her heel out. It was completely destroyed and full of cum and pussy juice. Anna grabbed the shoe from me and licked a bunch of the wetness from it and then slipped it back onto her foot. She then licked my cock completely clean, pulled off her other heel and jammed it onto my cock. She told me her shoes need to match and she needed to be fucked deeply again.
I fucked Anna really hard again with her other well worn heel on my cock until penetrating her cervix had become easier. After about half an hour of fucking Anna, I pulled out and put her heel back on her foot. I plunged my cock back in deep and thrust as hard as I could. Instead of her cervix squeezing the head of my cock to keep it out, I felt her body open up for me and allow a couple of inches of my cock to penetrate the deepest part of her womb. I released another load deep inside Anna's womb and she cried out for me to fuck her hard.
"Oh Mike, I've never been touched so deep. I've never felt so full, so complete. It's like you're fucking my very soul. I need you Mike. I want to be your apprentice and have you take me with you, wherever you go next."
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