This is my first attempt starting a story. Let me know what you think and if you like it I can continue.

[Part 1](https://www.reddit.com/r/Femdomstories/comments/g24dwe/my_college_adventure/)

[Part 7](https://www.reddit.com/r/Femdomstories/comments/g9umz5/my_college_adventure_part_7/)

My College Adventure Part 8  

I arrived the next morning to find Shelby waiting on the front porch. I said hi and she replied pleasantly. As we were saying hi Steph opened the doorway and ordered us inside and to strip. When the two of us were naked she had us spread our legs and bend over. The next thing I felt was the plug being pulled from my asshole. “Let’s hope these did the trick” Steph said.  She had us follow her into the living room. We were both shocked at what we saw. In front of us were two wooden benches. Each one had a row of 5 dildos attached to it. Starting from small and increasing in size up to the last largest one. Steph smiled, “Today, you will be competing to see who can ride the bench the fastest. You will start at the small dildo, lower your asshole onto it until you’re fully seated on the bench. You will then lift off and repeat the process 5 times. When you have completed the fifth time you will step forward and repeat the task with the next dildo. So on and forth until the last dildo. The one that completes this first will receive a prize while the loser will receive a punishment. Should you fail the task any point the punishment will be extremely unpleasant. So I suggest you try your hardest.” 

With that we both took our place at the start of the bench. I was worried that I was not going to do well. We both applied a generous amount of lube to our assholes and got ready. “Begin” shouted Steph. I closed my eyes and lowered myself to the dildo. As I felt the tip of the fake cock touch my asshole I looked down. I wondered how I had gotten here. Naked, a cage on my cock and about to rape my own ass. I paused. Looked over at Shelby. She had slid down onto the first dildo with ease and was starting her trip up. I took a deep breath and let all of my weight down onto the fake cock. I felt it invade my hole. Feeling like it was never ending. Finally, I sat onto the bench. I gasped at the feeling of this foreign object deep inside me. I pushed any thought of normalcy out of my mind and quickly stood up and brought myself back down onto it. As I made my way down the fifth time, I noticed Shelby had moved to the second dildo. She seemed to slide down onto it just as easily as the first.

I moved toward my next target. Sitting down I felt myself stretch even more around it. Feeling pain with every inch, I forced the dildo inside me. It wasn’t much harder than the first, but it was a noticeable difference. Halfway through, Shelby had made her way to the third dildo. I pushed hard and slammed myself down onto the second as fast as I could to try and catch up. I heard her moan as she slid onto the third. She had started to slow a bit. I made my way to the third and immediately understood the moan. In my haste to catch up I hadn’t thought of the difference in size. This one was a much bigger difference than the first to the second. I had wasted no time and slammed myself onto it. I was now sitting on the bench screaming in pain with my newest rapist deep in my ass. I watched in horror as Shelby slowly lowered and raised herself onto the dildo and stepped toward the fourth. I knew there that I was going to lose. I sat for another moment and then slowly continued my task. As I finished and made my way to the fourth, I saw Shelby. Slowly lowering herself down and wincing, onto the final dildo. It looked massive. I cried through the entire fourth dildo and as I moved to the fifth, I saw Shelby’s ass bottom out on the fifth and Steph yell, “We have a winner”. She then turned to me and waited for me to finish. It took me 15 more minutes to get through the agonizing task of dildo number 5. As I finished, she spoke. “Congrats to Shelby on your victory. As a reward you will be getting your long overdue orgasm. You will receive it from Brian’s mouth. Brian, as punishment for losing you will first be providing Shelby her orgasm, then you will be cleaning each dildo with your mouth, and you will be forfeiting your next orgasm, whenever you finally earn it.” I was dejected. Steph continued, “This is an important task for the two of you to practice. I have a group of friends that I get together with every month where we hold these races for our slaves. You two will be representing me at the next one. The punishment for losing at those races involves quite a bit more pain. So, I suggest you start practicing.” She looked directly at me. Now Shelby come relax on the couch and Brian take your place between her legs.

As I knelt in front of Shelby’s pussy, I could see how needy she really was. She was soaking wet; I could smell her weeks of denial. I brought my tongue to her clit and she writhed in pleasure. I lapped up every bit of her juices and it seemed they were immediately replaced with more. It didn’t take long. Darting my tongue around her pussy she started to buck. She grabbed my head and thrust her mound into my mouth as she erupted in a ferocious orgasm. As soon as it struck it felt like it was over. Shelby released my head and slumped into the couch. Steph looked and me and pointed to the benches. I slowly crawled to them and began to deep throat each one. They had an interesting flavor. My own ass and Shelby’s ass mixed with lube. As I finished the last one, I was told to get dressed and go home. As I left, I saw Shelby still laying on the couch basking in post orgasmic bliss and have never felt more jealous.