I couldn't believe the night still wasn't over yet, but I slowly nodded and felt Will direct me towards the bed. Will laid himself on the bed on his back and instructed me to straddle him. I did and I felt Sir come up behind me.
"Be gentle at first, Will, let her get used to it. She's never done it before," I heard Sir tell Will.
Will replied, "Oh I'll go slow," and winked at me. That wink scared me but I was glad that Sir was behind me and I was on top of Will; how much harm could Will possibly instill upon me when I was on top of him?
"I'm going to walk you through this, love," Sir said to me. I nodded. "Do exactly as I say, when I say it, okay baby?" I nodded again in response. "Good girl. Now slowly lower yourself onto Will's cock; let it go into that wonderful cunt of yours."
I nodded again and slowly lowered myself onto Will's semi-hard cock. I felt it stiffen inside me as I lowered myself more, letting his cock finally go all the way into willing pussy.
"Very good, now ride his cock, love. Ride his cock slow at first, and when I tell you to speed up, you will speed up, understand?"
I nodded and raised myself up, letting almost all of his cock expel from my pussy. I lowered myself down again and felt Will's hands reach up to grasp my hips.
"Not yet, Will. Let me do this for a little while, then you can have your way with her," Sir said to Will.
"Okay, okay," Will replied.
"Keep going, baby. Ignore him," Sir said gently to me. I nodded and started to lift myself up and down, creating a slow rhythm. I felt Sir's hands reach around me and fondle my nipples, making me wetter than before.
"Go faster now, love," Sir whispered into my ear as he began to lick my earlobe and neck. I complied, and sped up my thrusting. I had to admit, I really liked this so far. Up, down, up, down, I bounced off of Will's cock. I felt Sir's cock suddenly rubbing against my ass; just very gently reminding me of its' presence. I started to get nervous, but Sir calmed me when he said, "Relax baby. I'm going to make this pleasurable for all of us, I promise." I smiled and kept my steady rhythm.
When I had started to feel another fire kindle inside my loins, Sir whispered into my ear, "I think it's time for you to feel my cock inside you as well, don't you?" as he licked up my ear.
I moaned and responded, "Yes, Sir. I think I'm ready," even though I knew I wasn't really ready. I was surprised that Will had remained almost silent underneath me; besides a few moans every now and then he hadn't said a word to me, and that was how I liked it. I felt Sir's cock head press against my asshole.
"Lean forward, love," Sir said to me. "Help my cock get inside your wonderful asshole again." I leaned forward slightly and put my hands on Will's chest. I looked into Will's eyes and prepared myself for Sir's cock once more. He tried to push into my asshole, but couldn't get his head inside. He leaned down and spat on my asshole, that being the only kind of lubrication handy. "Help me, love. Push out for me like you did the first time," he said.
I pushed my asshole out as he pressed his head against my asshole. I bit my bottom lip and clasped my eyes shut to try and hide the intense pain this was causing. His cock head popped in past my sphincter and I couldn't help but lean forward and almost make his cock exit. I let out a whimper of discomfort and pain as Sir started pushing forward more. He had his hands on my hips and was pulling me back to him.
"Ahh! Sir, please, take your cock out! I can't take two! I just can't!" I screamed at him.
"Shh, hush now little one," he replied.
"No! I can't take two, Sir!" I said as I pulled myself forward and forced his cock to exit my burning asshole.
"Come here, cunt!" Sir screamed at me as he pulled my hips back towards him. He pushed his cock into my asshole once more and I again pulled myself forward enough to make it exit yet again. I felt his hand slap my ass and he said, "Alright, I was trying to be gentle with you, but now Will is going to punish you. Get up and stand beside the bed while we decide your punishment." I let a tear fall down my cheek as I got up after he did. Will got up and stood next to Sir. They began talking quietly, but I couldn't distinguish anything they were saying. I was very scared now; Sir had said that Will was to punish me. Sir had already punished me once and it was horrible; I didn't want to know what Will's punishments felt like.
I saw Will nod and I heard him say, "Move in front of your bed, facing me," Will said. I did as I was told. "Now, spread your arms up high and your legs far apart, like you're doing jumping jacks."
I complied and I felt him tie all four of my limbs to two of my posts. I began to cry silently as I saw Sir pull out a riding crop from a bag I hadn't noticed earlier. "Now, I'm going to hit you 100 times with this, anywhere I wish. After each hit, you are to say, ‘I will not disobey!'. You will not struggle and you will not scream. Do you understand?" I nodded and heaved a breath. My whole body was trembling with fear. I swore to myself I would not resist either of them again tonight.
I saw him crack the crop in the air a few times; my whole body wincing with each crack, anticipating each blow onto my soft body. Will walked over towards me and I saw an evil lust in his eyes. He loved it that I had disobeyed and that he got to punish me. I closed my eyes tightly and bit my bottom lip. I wasn't allowed to scream and I didn't want to get a more severe punishment for doing so. I anticipated the first blow, and felt it land on and scratch my left breast.
"Ohh!" I whimpered out in pain. Will waited a few minutes before he cracked the whip down on me again, this time landing on my right breast. I resisted the urge to scream at the top of my lungs as the third one hit my gaping cunt. The fourth came down twice as hard as the third had, and on the same place.
"AHH!" I screamed out; I couldn't help it.
I was prepared to hear Will or Sir verbally punish me, but Will only said, "That's it. Scream for me baby. And you're not saying what I asked you to. You'd better start saying it."
I nodded and from that point on I always said "I will not disobey!" after every hit. He hit me over and over again, not only on my breasts and my soaking cunt, but also on my thighs, shins and stomach. I hurt all over by the time he got to 50 and he untied me and turned me around. I almost didn't comply; I was in so much pain that I could hardly move. I reluctantly turned around and let him tie me in the same position. My ass got abused for the second time of the night.
When he had finally reached 100, my whole body was trembling with pain and I was barely whispering "I will not disobey" to Will. I had no more energy. It seemed like all of my energy had just been beaten out of me, and against my will at that. Will untied me and pushed me onto the bed. I curled myself up, trying to fall asleep I think, when Sir came over and gave me something to drink.
"Drink this. It will give you your energy back. We're not done yet, love," he said as he pressed a straw to my mouth. I drank all of the drink and he was right; within a few minutes I had all of my energy back. I was still in severe pain, but I was energized at least.
"Now, time to try again baby," Sir said. I nodded and we all three got situated. "We're starting over, little one, so remember, lower yourself onto his cock and slowly ride him until I say otherwise. Do not struggle this time when I try to put my cock into your asshole. Trust me, love, you'll love it after the pain goes away." I nodded again in response.