My writings

She laid there sound asleep and naked, snuggled up under me speaking warmth. Her back was arched and her ass stuck out near my free hand. I reached down and rubbed her soft fluffy ass before placing a nice firm slap on her ass cheek, waking her from her rest. "Thank you Sir" she said as she open her eyes and looked at me. I continued to rub and slap her ass till it started to turn a dark pink. I massaged her now sore ass, reached down between her cheeks and felt the plug that was inserted in her ass a couple hours ago. "Did you have a good nap" I asked "Yes Sir" she replied. I rubbed my hand up her back and grabbed a fist full of hair and lifted her head off my chest. I pushed her down to my cock. I could feel as the tip of her tongue touched the tip of my cock before she accepted the head in her warm mouth. Using the fistful of hair, I pushed and pulled her head up and down as she cradled my cock with her mouth. After a couple strokes I pushed her head down while at the same time thrust my hips up and forced my cock deeper down her throat. I held her there till could feel as she started to gag and fight for air. I watched and kept her in place a little longer before releasing her head. She sucked in a big gulp of air before continuing to suck. I reached down and slapped her ass again and without releasing her hold on my cock, positioned herself so that I had a better view of her ass. "Spread them" I said firmly. She reached back and grabbed a check with each hand and separated her cheeks as wide as she could exposing the black jeweled plug I had inserted into her earlier. I reached reached down and pulled on it and observers her sphincter slowly release its tight grip on the plug. I love to watch as it spreads her asshole as I slowly pull it out, only to push it back in and then pull it out as I enjoy the process of it stretching her asshole open all over again. I pulled on it one final time and smiled at the sound it made as the fattest part squeezed it's way out. Her asshole was stretched open and I could see inside her. I stopped her from sucking and made her get the lube on the night stand. She knelt on the bed at my side with her ass cocked and while I spread her cheeks, she lubed up her asshole, then my hand. After whooping her hands she got back in position, mouth wrapped around my cock, ass spread and in position. I started with two fingers in here asshole and worked them back and forth. I work another finger in then another. With my four fingers working her asshole, I use my thumb to tease her wet pussy. She moans as she's sucking which causes a wonderful vibration sensation on my cock. I work my thumb in her asshole, she slows down on sucking as I now am trying to push my whole hand in her ass. As my knuckles reach her sphincter I can fee her pushing pack. Her attention now focused on letting my knuckles pasted he sphincter. I wiggle my fingers and wrist as I fight against her sphincter till it finally stretches enough and my fist goes completely in. She lets out a loud groan as my fist makes it all the way in. After taking another breath she resumes sucking. Her sucking intensity now increased as I fuck her ass with my fist. Her sphincter wraps around my wrist and her ass makes a wonderful sucking sound. I continue to fist her asshole faster and faster. She matched my fisting pace sucking me harder and harder. We continue to match pace as her asshole continues to make that great sucking sound. I can feel myself getting ready to cum. I use my free hand to hold her head I shoot a load of hot cum down her throat. She sucks it all down and continues to suck. I stop fisting her ass and start to pull my had out. Her asshole though worked over still has a grip on my fist as I hear her groan with my cock still in her mouth. Her sphincter stretched some more and I finals get my knuckles past. With my had out I admire her asshole all stretched out and red as she keeps her cheeks spread for me to view. I watch until it finally shrinks back to normal. I reach for the jeweled plug and slip it back in her ass. She gets up and I admire her ass as she walks to the bathroom and comes back with a wash rag and whips down my cock and then my hand. The jeweled plug just showing as she makes her way back to the bathroom. She comes back and snuggles up next to me almost in the same position as before. As she gets comfy, I wrap my arm around her and rub her back as I feel her slowly fall back to sleep. I think in my head "in a couple hours I'll wake you up and we'll do it all over again, after all this is asshole stretching weekend"

It was around 12:30am when my phone rang. I was waiting on the call to come, On the other end a soft voice said “I’m outside Sir”. I walked to the window and parted the curtain to see her car parked next to mine. I instructed her to turn on her overhead light so I can see her. “Did you bring your toy bag?” I asked, “Yes Sir” she replied. “Put it on the front seat” I told her. I watched as she reached to the back seat and lifted the bag over to the the front seat. “Remove your plug and put it on your dash”, she searched around the bag and placed a medium sized black anal plug on her dash. She looked back at me through her windshield awaiting my next command. “Strip” I commanded, she replied back “Sir?”. “I did not stutter did I”, “No Sir” she replied. She looked around the parking lot making sure there wasn’t anyone walking around, or open windows. She put the phone down on the dash and slowly removed her top, still nervously looking around. From her shifting around I can tell she was working her pants down over her large ass. She placed her pants down on the front seat, and started to pull the shoulder straps from her bra when she paused. I looked across and saw a light from one of the room doors as one of the other guests came out and walked towards their car. He removed something from the trunk and went back to the room. I looked back at her and could see the panic in her eyes, “Continue” I said as she proceeded to remove her bra. Her breasts hung just below the steering wheel and dash so I wasn’t able to see her nipples, but for a woman of her age and size she still had a full pair. Looking around she reached for the phone on the dash and put it to her ear and said “I’m done Sir”. “Very good” I replied, “Now the plug, go ahead and insert it”. “Yes Sir” she replied “Can I use some lube sir…..I’m a bit tight”, “Yes you may”. She dug around in the bag again an found the lube. The plug now glister in the light when she lubed it up. She then reached round and I could hear her grunting and see her face wincing as she worked the plug between her fat ass and the seat. She let out a slow long groan as I pictured the plug slowly working its way into her ass. As little squeal with a sigh of relief as the fattest part of the plug made it past her spinster and pulled securely in her asshole. “All done Sir” she said as she still wiggled around a little trying to get comfortable with the dildo in her ass. “Very well, pick up your bag and clothes and come to the door”, “Yes Sir” she replied. She looked around again making sure no one was around before she exited the car. Her pale white body glowed slightly as she closed her door and locked the car. Her full breasts rested on her stomach as her ass jiggled as she moved. The plug was clearly lost between her fat cheeks but you could still see where it stretched her cheeks, pulling at the insides of her ass cheeks. She paused between the cars and took one last look before making her way hurriedly and somewhat uncomfortably with the plug in her ass towards my room door. I let the curtain fall and slowly made my way to the door. I opened the door to see her nervously shaking and looking around, praying that no one opens their door to find her standing there naked. “Do you remember what you are to say” She nodded and started reciting her entrance statement. “Thank you Sir for allowing me to serve you over the next two days. I will do my best to make sure that your happiness is my priority. Should I fail to please you I understand that I will be punished as you see fit. Sir I’m now yours to use as you please” “Good girl, I see you memorized it well”. She smiled and nodded as I motioned for her to come in. I closed the door and watched her pale white ass jiggle as she made her way across the room. As she bent to put down her bag and clothes I caught a glimpse of the plug wedged up her ass and thought of the fun I was going to have over the weekend with her, and how I wanted to leave my mark on that fresh white canvas of an ass she had.