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Mrs. Willows is enjoyed by the school principal.

I cringed and leaned forward in pain.

"EXCUSE ME? What did you just say? You failed to address me AND you failed to compliment my cooking. You don't want to make me angry, slave." She said, still pressing her fingernail against my cock.

"Please Miss Sarah I apologize! The food tastes amazing. You added just the perfect touch of thyme and rosemary. Please. I did not mean to insult you Miss Sarah!" I begged her for mercy.

She loosened her grip, and leaned in to kiss my cheek. "Nice recovery there slave, I might still let you cum today. Think before you speak though. Open your mouth." She said, giving me another bite of the stew. She fed me until I was full, periodically stroking my cock to keep me hard and on edge.

She took my blindfold off and led me to the bathroom. I'm not sure where my mistress was at this point, but Miss Sarah was keeping me on edge enough to not have much time to think about it too much. She gave me an enema and repeated the process until my insides were completely cleaned out, then filled me up and pushed a butt plug inside of me. Afterwards she led me outside to where my mistress was waiting. It was a beautiful day out, perfect temperature. I was completely naked still, and it was only a bit chilly when the wind blew. My mistress unbound my hands and ordered me to serve them tea from time to time, otherwise I stood nearby and waited patiently for my next orders.

"Take that plug out why don't you, let's see how long you can hold that enema in pet." Miss Sarah said to me, and I felt a bit worried. I had nearly 2 liters of water inside of me, I wasn't sure how long I could hold it in. I pulled the plug out of my ass and sprayed a bit of water onto the lawn.

Miss Sarah laughed at me, "Haha! You really have quite an entertaining submissive you know, he looks so embarrassed. It's kinda cute." she mocked me, then poured her tea out onto the yard. "Oh no dear slave, I seem to have spilled my tea. Care to run inside and make me some more?" she ordered me inside, knowing that I was likely to spill the enema all over the house and be punished for it. I obeyed.

A few minutes later I returned outside, walking very slowly. I had not managed to spill any inside, but it was quite a challenge. "Oh, welcome back dear, how do you feel now? Thanks for the tea!" Miss Sarah held her tea cup out to me.

"I can't hold it in much longer... please let me release it now Miss Sarah. Mistress? Please." I begged.

"Squat down," my mistress said, "if you can hold it in for another 10 seconds you can fuck both of us in the ass and cum inside whichever one of us you prefer. Deal?" I squatted down, my mistress watched the clock, "10... 9... 8..."

She barely got to 7 before I cried out and released the enema all over the grass below me. I was humiliated. Miss Sarah laughed at me, "I'm surprised he even made it that long. Just 7 more seconds and he would've been such a happy boy. Maybe we can still make him happy, though?" She reached into her bag and pulled out a medium-sized strapon.

My mistress nodded, "Oh yes Sarah, this one loves to be fucked in the ass by women he finds attractive, and I think he's quite fond of your looks."

Miss Sarah rubbed lube up and down the shaft of her strapon and beckoned me over. "Come slave, come sit on this hard cock of mine and show me. I followed her command, and straddled her in the oversized lawn chair. Before I could take it inside of me, my mistress stepped behind me and rubbed some lube against my tight hole. My mistress grabbed me by the waist pressed her own strapon against me, biting my ear and whispering to me, "Pet, we are going to push your limits today alright? You're going to take both of our cocks at the same time. We're going to double penetrate that tight little ass of yours."

"Y-yes ma'am... if you insist." I lowered myself onto Miss Sarah's strapon, pushing it inside of me slowly, while my mistress poked the tip of her strapon at my entrance.

"Don't worry, we can go slow at f

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