Brittany's Strapon Hell Week 02

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Day two finds Brad in more precarious situations.
2.7k words
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Part 2 of the 5 part series

Updated 11/01/2022
Created 05/03/2006
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Brittany's Strapon Hell Week 2: "Humiliation with Codi and Courtney"

I am attempting to make these stories stand-alone as well as make sense in a series. If you like this, make sure to read my other stories. Think of your votes and comments as your contribution to my stories! Thanks!

After my ordeal of being made up to look like submissive Asian porn star Ava Devine and gang banged and covered in cum by Mistress Brittany's strapon class, I had passed out in the hotel room. I awoke to find myself back to my old, blonde, Caucasian self, but I was also tied to a bed in doggy position, wearing my chain mail bra and thong. My legs were spread by a spreader bar, my hands were tied together in front of me, and a rope around my waist secured me to the two head posts of the bed.

No sooner had I realized this, than there was a rustle at the door, and in walked Codi Milo and Courtney Cummz. Both of these girls were rather new to the porn scene, and looked like they could be average college girls. Codi was a beautiful blonde with very large tits and a great ass. Courtney, on the other hand, was a striking brunette, with her nose, nipples, navel and clit pierced, and a sexy tattoo on her lower back. She was very beautiful and very dirty.

"Just how we left her," laughed Courtney. "Let me explain how this works, slave. We go to class for most of the morning, and each day you are assigned to two of us. Each day there is a different theme, and at the end of the day, you have to guess what that theme is. If you are correct, we pass that day, and you get to move on to another pair of mistresses. If you are wrong, you spend the next day with that pair, until you get it right. As you can see, this could last for as little as just this week, or as long as it needs to. Now, let's get started."

With that, Courtney shoved something small into my ear, and then walked across the room and spoke into a tiny microphone. It fed her speech right into my ear. At the same time, Codi was busy spreading some sort of cream on my ass and working it in with her finger. She also mounted a suction cup dildo to the head of the bed that was easily within my reach. All of a sudden, I felt an intense itching in my ass, and I backed up on the dildo. The girls started to laugh, and went and hid in the closet.

I had never felt such an intense itching in my life, and I began to violently ram myself deeply with the dildo in an attempt to make it stop. They had cleverly placed the dildo so that despite my best efforts, I could not quite get it all way up my ass. I was so busy ramming my ass against the headboard, that I did not hear the door open. "Oh my goodness," I heard a woman exclaim. I looked up to see about a dozen college-aged girls in cheerleader outfits, surrounding the bed. "There must have been a mix up in the rooms," she said.

I heard Courtney's voice in my ear, and I repeated what she said. "My mistresses request that you stay. I am really horny right now. I have an itch that I can't quite scratch. Please fuck my ass with that dildo," I said. "I really like rough sex, please abuse me, I'm a whore," I continued, my face burning red.

Soon, shock turned to laughter. One of the girls got behind me and removed the dildo from the headboard, and shoved it all the way into my ass. She leaned back and began to work the dildo with her foot, while one of her friends stuck her ass in my face. I carefully removed her thong with my teeth, and began licking her asshole, as she ground herself against me. Others began slapping me and spitting on me. One of the girls got out the camcorder and began recording the scene. Again, I repeated Courtney's words, "Please keep fucking me in the ass. I need something bigger. Pull it out and let me taste my ass. I need something bigger back there." The girls laughed and stuffed my ass dildo into my mouth, and scurried around for something to replace it.

I looked back to see a curling iron poised at the tip of my asshole. The girl welding it, unceremoniously jammed it in all the way to the base, simultaneously scratching the itch, but forcing me to scream into my cock gag, and orgasm, staining the pillow I was propped up on. "Oh dear, I'm such a slut," I repeated as I wiped the cum onto my face, "I'll go get another one." With that I was unbound and helped to my feet. Courtney told me that there was a dress for me under the bed, so I lifted it out and put it on. It was a royal blue mini dress that was a stripper's costume. It was very short, barely covered my tits, my pussy or my ass, and it was slit to the hip on both sides.

Barely covered, face streaked with cum, I made my way down to the front desk, curling iron still lodged in my ass. The poor little blonde 16 year old receptionist didn't know how to react. I handed her the pillow and explained that I needed a new one. She asked my name and room number. I looked to see the girls, as well as Codi and Courtney standing on the balcony yelling down to her my name and room number. "You don't look like a 'Brad' to me," the receptionist said.

"Oh he sure is," Codi yelled down. "Show her, slut," she commanded. Humiliated, I jumped up on the desk, got on my hands and knees, flipped the mini skirt up, and showed her my tiny cock and what was lodged in my ass. She gasped, and there was a roar of laughter from the balcony. As the receptionist came back with the new pillow, I looked up to see Codi wielding a large dildo in her hands. "Hey doggy, go fetch the bone," she yelled as she tossed the monster down toward me. I tried to catch it, but it slapped me in the face, to the great amusement of the cheerleaders and the receptionist. I got down on my hands and knees and retrieved the cock with my mouth. "Slave, you better keep that cock in your mouth and you better not drop that pillow," Codi hollered.

Defeated, I crawled over to the girl, who placed the pillow on my back. "Please ride me like the animal I am," I mumbled with a mouth full of cock. After a moment's hesitation, she jumped on my back, dug her heels into my sides, and commanded me to move. We made our way to the all glass elevator and she had me back up to the back, so that my ass was resting on the back wall. I looked down as we started to climb and noticed we had assembled quite a crowd. Loving the attention, she began to grab my hair and lean back, slamming my ass against the glass wall and jamming the curling iron further into my ass.

As we approached the room, she dismounted and began chatting and laughing with the girls. We got back inside and she was carrying a good sized wad of money. "This is the easiest money I've ever made," she laughed. With that, she jerked the curling iron out to the base, and then violently shoved it back up my ass, all the way to the handle. It was more than I could handle, and I again blew my load, this time all over her shoes. She grabbed my head and forced me to lick it up, to the laughter and encouragement of the rest of the girls there. I was then tossed to the ground. As she walked away, she threw two dollar bills on me," You were pretty good sweetheart, thanks," she laughed, as she walked away.

"Well, I think it's time for us to go," Courtney announced. "Slut here has a long day ahead of her." Courtney and Codi left the room, with me crawling behind them. Right as I was about to exit, one of the girls stopped grabbed me by the ankle and pulled me back into the room. Apparently she wanted her curling iron back, and she jerked it from my ass, which sent the room into laughter yet again.

We finally got back to the room, and I was commanded to clean up and get dressed. I got out of the shower and put on a sexy yellow summer dress, that even in my heels, touched the floor. Courtney and Codi both entered the room, wearing sexy, yet not as long, summer dresses. "Baby, I have a feeling you are going to need more clothes by the end of the week, so we are taking you shopping," Codi informed me.

Fifteen minutes later, we were entering a local Florida shopping mall. We walked into the first department store, and discovered that the juniors section was on the second floor, so we got on the escalator. Right as we neared the top, Codi stopped in front of me. All of a sudden I felt a tug, and heard a rip. My dress was stuck in the escalator!!! Slowly my dress began to get sucked into the machine, exposing more and more of my naked body. Unfortunately, the waist did not tear; it only caught so that I was effectively naked and trapped in place all at the same time. I covered my little cock with my hands, as the girls began to mock me. "You stupid slut, what were you thinking?" she yelled. "You've gone and ruined your dress too!"

I was gathering quite a crowd by this time, and people were pointing and laughing. "I hope you are enjoying the show," I repeated from the earpiece. "Does anyone have a cock for my ass?" I couldn't believe I said that! Finally a security guard cut me loose, and my mistresses and I walked back to the juniors section. I was told to stand out in the aisle while they picked out clothes for me. A dressing room was out of the question, I was going to try everything on right here. I was tossed a micro mini skirt, which couldn't have been more than nine inches long, and I quickly slid it around my hips. It barely covered my ass.

There were no shirts that would remotely cover my tits, so we walked to the other end of the store, getting many looks from passersby, as I was still completely topless. Finally Codi tossed me a tiny white tank top, which I gratefully pulled over my tits. "Oh my goodness, we don't have any money!" she exclaimed.

I went over to the lovely sales clerk and repeated, "I'm sorry, I don't have any money. I was wondering if you could take an alternate form of payment," I blushed, as I lifted the skirt over my ass and presented it to her.

I'm sure we can find something to do with a hot little piece of ass such as you," she stated. Before I knew it, I was over her knee, getting the spanking of a lifetime. I began to cry as more people gathered around. After what seemed like an hour, she stood me back up, and flipped my skirt down. "Do come back and visit us soon," she laughed.

With that we left the store. Courtney and Codi were on either side of me as we walked, and they joined hands behind my back. I was aware of a cool breeze on my red ass, and I realized they were holding my skirt up, as we walked through the mall. "Mommy, I can see her butt," I heard a little girl say. "It looks like she was a bad girl, mommy; it looks like she got a spanking." Again, my face burned, and we kept walking.

We stepped out of the mall and into a pedestrian mall on a college campus. Being spring, there were students everywhere, and the three of us looked like your average sexy coeds. Codi took her leave of us, and Courtney led me over to a bench. As we approached the bench, she grabbed me by the hair and threw me over the back of it. My tank top was quickly removed, and my hands were spread and secured to the arm rests. She tossed my shirt to the ground below me. Now I was effectively bent in half and I felt her writing something on my back in permanent marker. I felt her draw an arrow pointing down, as well as two arrows over my shoulders, which pointed to each of my large, swaying tits.

"Can I have your attention, please," Courtney shouted. "Our little slave here is pledging our sorority, and she needs to be punished. Don't be shy, step right up. Look how she's dressed, you know she wants this," she said, as she flipped up my skirt and started spanking me herself. I looked up to see Codi standing in front of me with two, strong, tan, muscular guys.

"I hope you came here to rough me up," I repeated. "I've been such a bad girl." One of the guys took Courtney's place at my ass, while the other one stayed in front and started slapping my tits. My mistresses stood to one side, arms crossed, laughing, encouraging and monitoring my assault. I closed my eyes and gritted my teeth, trying to fight back tears. I was afforded a brief respite, only to have the assault continue, with smaller, more feminine hands. I looked back to see a whole line of girls waiting to take their turn, my tits and ass already on fire. At this point, I had been tied for awhile and I really needed to go to the bathroom. "Mistress," I whined, "I really need to go potty."

"Slave you have two choices. You can either hold it, or go where you stand, like the animal you are," Mistress Courtney informed me, as she dumped water over me to momentarily cool the burning. Suddenly, three girls began spanking me in earnest, one began pinching my nipples, as the audience began to laugh again, and it became too much for me to bear. I began to pee in front of everyone, right on to my tank top on the ground. The laughter reached new levels, my face burned to rival my ass, as I began to cry. More water was dumped on me to clean me off, and my assault continued. By entire body was burning, my legs were sore from the heels, and I was a mess. Finally, Mistress Courtney flipped my skirt back down and untied me.

"I would like to thank you all for helping us out. I do have a confession to make though. We're not really in a sorority, and she's not really a woman," she said as she stood me up and lifted my skirt in the front. She is our sex slave, and we are her mistresses. We are taking her back to our dungeon now where we can give her a proper ass fucking." With that, I put on my now see though piss soaked tank top, and hobbled after my Mistresses to the laughter of the crowd.

As we entered the hotel room, I saw all the Mistresses assembled. Mistress Brittany stepped forward. "Well, ladies, this is the moment of truth," she said as she looked at Codi and Courtney. "By the looks of it, you ladies did a very fine job. So, slave, what do you think today's lesson was in?"

I looked at her from behind my red eyes and tear-stained face, "Humiliation, Mistress," I answered.

"Very good, slave," Brittany exclaimed. "Courtney and Codi, fine job ladies, you pass today's lesson. Slave, as your reward, you will get to spend tomorrow with Mistresses Jenna Jameson and Vanessa Blue."

"Oh, he in big trouble now, ain't that right girl," Vanessa said, as she high-fived Jenna. I stripped naked, and hobbled to the shower to clean up from today's abuse and ready myself for a long day tomorrow.

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