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Dianne walked towards me with a maniacal smile and a dildo in her hand. I was afraid and didn’t know what she was going to do with me. It didn't feel right. Why would a woman with a family want a shrunken 16 year old boy? My thoughts were all over the place. I also caught myself thinking about how beautiful she was.

Dianne reached down, picked me up, and then brought me close to her face, "I'll make you a deal. Since I caught you exploring my body and being a little perverted boy, you must pleasure me and if you're good, I'll give you back to your sister."

My thoughts of the last boy all disappeared and the only thing my brain focused on was 'pleasure me'.

"Well I'm not exactly sure what you mean but how could I ever turn down such a magnificent woman like yourself." I replied gulping and still a little unsure of everything, but at the same time excited.

Dianne didn't say anything else, she just smiled and then pushed me into the slit so that my head was sticking out of the end of the dildo. Then she got onto her bed, laid down on her back, and brought the dildo up to her stomach. She slowing ran the dildo up and down in between her breasts and moaned slightly. Then she rubbed the head of the dildo back and forth across her nipple making it rock hard. She moaned a little louder. She could feel the bump at the end of the dildo and it doubled the pleasure she would normally get. She lowered the dildo to her lips where she only just pushed against it without entering. Her pussy was really wet and craved more; however, Dianne resisted her urges to penetrate, and then moved the dildo head to her clit. She could feel the tiny hands working magic on her as she exploded with pleasure. Her back arched and she moaned in heavy breathes. She grabbed the bed sheets underneath her free hand and her body tightened.

"Ohh Max, I'm gonna cum" Dianne screamed.

Once Dianne put me into the slit, I felt almost like I was in the 'cockpit' of an airplane. I laughed to myself at the immature joke. The walls that held me in place were squishy and slightly sticky. It was decently comfortable. Dianne flew me around until I crash landed onto her stomach with a jiggle. I looked up Dianne's chest and could see to two giant mountains of boobs. She had squished them together with her arms and they were spectacular. The dildo was then moved forward penetrating her mountains. I had a first-person view and it was amazing, I was so turned on. Once I got through, I saw a glimpse of Dianne's face as she laid there with her eyes looking down towards me. She was so confident and sexy, I never thought I'd be so in love with a middle aged woman. The dildo retreated back the way it came, and then pushed forward again. This repeated several times and Dianne started moaning. The moan was more of a throat moan, so it vibrated her chest and sounded louder for me. Next she positioned me so that I could kiss her hard nipple and also rub me into them. It was bigger than my sister's or Steph's and had more small bumps positioned around the tip. I wished I was bigger so I could have sucked on it. Dianne then lowered me down so I was face to face with her pussy. Her hungry lips opened as I was slowly pushed through but not yet inside. Her familiar smell consumed my nose and then my hormones. I could see her pussy ready to swallow me whole, but she didn't let it, at least not yet I figured. I liked how Dianne was more experienced than the girls, she took more time with everything and eased her way to the ultimate orgasm. I was going to make it ultimate. Once I was brought up to her clit, I pulled my arms out of the slit. My hands grabbed her already hard clit and I worked my magic. I could feel Dianne's reaction as she clenched her lips tighter and I heard her moans get a lot louder. I was so turned on by it all that I began humping the inside of the dildo and I was rubbing her clit really hard. Once Dianne said she was going to cum, I turned into an animal. In return, her body arched and shook in pleasure. She pushed the dildo hard into her clit squishing my face into it but I didn't care. We both cam at the same time. 

Dianne's breathe was really heavy and she twitched from the aftershock of pleasure.

"Mhmmmm, Max, that was even better than what I remember it being. You're such a good little toy aren't you" She said with an exhausted breathe. 

I was too exhausted to reply, plus my face was still down by her pussy. I had maybe a minute to rest and then the dildo started moving again. 

Dianne's clit was too sensitive to go again but she still desired more pleasure. She lowered the dildo sliding it in between her lips to her awaiting hole. Her pussy was already dripping wet so with just a little pressure, the dildo slid inside. She gasped as it spread her pussy open. Moving it slowly, she moved it in and out. Dianne moaned in pleasure as she continued. Then she repositioned it so it was driving up into her G spot. Her speed picked up and she squeezed the dildo hard in her hand. She felt something small fly out and land on her G spot which made her bite her lip in immense pleasure. She thrusted the dildo harder and could feel her juices fill her pussy. She was ready to finish. Pleasure consumed her body as she pushed the dildo harder and deeper inside. In fear of screaming too loud she bite her pillow. Her body shook again but more intense and she started squirting juices out onto her bed. Dianne had never felt pleasure to this extent before, she was experiencing a tidal wave of numb tingling feelings all over her body. She gave one last giant thrust with the dildo and then sprayed cum all over her sheets. Once her body relaxed, she felt like she was floating on a cloud and she just laid there taking it all in. After 10 minutes she remembered about Max. She could slightly feel something still moving around deep inside her.

I thought Dianne was satisfied after the first orgasm but apparently she wanted more. She lowered me, sliding my face along her pussy until I reached her hole. Then almost like a rollercoaster starting up, I slowly made my way inside. It was dark, wet, and well pretty much the same as Steph's. I was covered by her juices as she moved me in and out. Her insides expanded and then contracted, repeating over and over. I was enjoying being Dianne's little fuck toy, at least until she changed the angle. I had watched enough porn to know roughly where the G spot was, and now I was literally smashing my face into it. I could tell by her movements and speed that she was enjoying it; however, I had stopped having fun. For me, it became more of a survival thing. Using my arms to shield from the force of smashing into her pussy walls, and trying to not get sick from the repetitive motions. Then without any warning, I shot out of the dildo and landed on her G spot. The dildo then became a battering ram and it pounded on my back. Luckily Dianne's pussy filled with juices and I was washed out of the way. I swam in her juices for only a few seconds before the dildo came back and pinned me to the back wall of her pussy. I could tell that Dianne was going to cum soon. Her body shook and I could hear muffled moaning getting louder. If I wasn't so beat up I probably would have started jacking off. The dildo gave one last hard punch and my head went into the hole leading to her cervix. I was stuck unable to free myself as Dianne had a massive orgasm. I could barely breathe in there but once Dianne relaxed, I was able to turn my head and get some air. For what seemed like forever, I just squirmed around helplessly. Finally a finger found me and forcefully pushed me to the side allowing me to escape. Then it scooped me up and pulled me back out to freedom. I had never thought something I loved so much could have nearly been the death of me. At least now I'll be able to go back to my sister.

 

Chapter End Notes:

 

* Will Dianne let Max go back to his sister? Or will she keep him all to herself?

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