The Ultimatum, Part 2

Previously, on The Ultimatum, Part 1:

Her grasp on my wrist tightened, and she pinned it against my hip. I felt her leg cross over both of mine. The new restraints felt like a straight jacket. Now my humiliation of being bent over her lap in my white briefs, was worsened by a feeling of utter helplessness. I felt the cool wood of the paddle rest across my butt. 

“I have a feeling that you’re the crying type. Let’s find out, shall we?” 

I instantly realized that I had made the wrong decision

To be continued…

For a second I panicked. I tried to wiggle free from her, but my movements were swiftly constrained by her arm and leg. She was tall, and in excellent shape. But even considering that, she was stronger than she looked. 

“No no, young man…you agreed to receive a paddling, and that is exactly what will happen. You try to wiggle free like that again, and I will give it to you again later tomorrow.”

The paddle remained rested against my bottom. Seconds went by, and nothing happened. She was tormenting me…making me wait for the first stroke. It was an effective tactic, as my anxiety was growing stronger by the second. 

“Unless of course, you’d like to take the eviction option,” she continued, her voice piercing the silence.

Part of me wanted to take the out she was giving me. But somehow I couldn’t bring myself to do it. She had a strange power over me. I felt helpless, not only physically, but mentally as well. When she talked to me in that stern, maternal voice, I ceased to be a man. Instead, I was reduced to the state of a helpless, and naughty little boy.

“No? Well, ok then. You asked for it, sweetheart.”

Suddenly, the cool touch of the paddle disappeared. My body tightened in anticipation. I closed my eyes, and braced for the worst. I was not disappointed. The paddle smacked into my butt with enormous force. The sting took me completely off guard, as I jerked my head up and yelped in a high pitched voice, “Owwwwww!” I tried to kick my legs, but her hold on me was too firm.

Once again the paddle rested on my butt. She padded my bottom with it a few times as she spoke,”Did that feel good?” she taunted.

“No!” I shouted. As soon as the words left my mouth, I regretted them. It was purely a reflex from the pain. But that didn’t matter to her. 

“Excuse me, Cameron??” she said, sounding genuinely surprised. She leaned in, and whispered in my ear. “Don’t you ever fucking yell at me again. And when I ask you a question, you address me as Miss Kristen. Just for that…”

The paddle lifted off once again. She grabbed at the waistband of my briefs with the paddle still in hand, and yanked the back of them down to my thighs, just enough to expose my bottom.

“Oooohhhh…what a cute little but you have,” she said giddily. “I’m going to enjoy punishing you even more now that you have made this so much worse for yourself.”

I was still breathing heavily, and recovering from the initial swat over my underwear. I couldn’t comprehend how the pain could possibly get worse. 

“You have nine more swats coming, naughty boy. It would have been six over your underwear, but you had to raise your voice at me. I hope getting paddled on your bare little fanny will teach you to take your punishment more graciously next time.”

“Next time?” I thought to myself. “What did she mean by that?”

Before I had time to ponder the question I felt the next smack land mercilessly on my bare flesh. I yelped again, a little louder. Then the next one came, just as hard as the first two. I cried out again, but as I did my voice broke, and I felt my eyes well up with tears. Another swat landed, and then another. I broke completely, and I began to cry like a helpless little boy.

I felt the paddle rest on my cheeks again. My crying became louder, and I began to mutter the words “I’m sorry Miss Kristen,” again, and again under my breath.

The paddle began to move back and forth across my behind. It was soothing, but no longer cool to the touch. My cheeks were burning. She let me lie there for a few moments, as I continued to cry.

“Ohhhh, sounds like someone is becoming a very sorry young man. It’s not fun to have your bottom paddled is it now?”

“No miss Kristen,” I replied after a sniffle. My tears were beginning to fall to the gray carpet that lay only a couple of feet beneath me. 

“Awwww, are you crying sweetie?” she said in a taunting voice. “Don’t worry…you have five more coming, and then it will aaaaaall be over.”

The paddle was moving in circular motions now. She let me cry for a few minutes while she soothed my bottom. The sting on my cheeks was turning to a pleasant tingle. It was confusing, but for a moment I felt grateful for the discipline I was receiving. The hardest part was over, I thought. Now just five more spanks, and I’d be free.

“Are you ready for me to resume your spanking?” she asked.

She released my wrist, and I grabbed onto the chair for stability. Her fingers were now caressing my thighs, as the paddle traveled down my legs and rested on my calves. Her fingertips caused ticklish shivers to travel up my body, but they were heaven compared to the scourge of the paddle. I began to giggle slightly. Her hand moved to my inner thighs, and started to inch upwards.

“Oh my, are we ticklish dear?” she said. I could hear the smile in her voice, but I didn’t respond. Her fingers danced hurriedly on my skin, and my crying turned to uncontrollable laughter. 

“Ohhhh, you are ticklish. A naughty, ticklish boy who cries when he’s getting spanked. What more could I ask for?” she said with a girlish giggle.

And just as she said it, I felt her fingertips on my balls, which were still covered by my briefs. She caressed them for a moment or two, and then began to massage them, rolling them around in her hand. I had no idea how to respond. This woman was clearly abusing me, but I couldn’t bring myself to protest. Feeling her greedy hands on my body only increased my feeling of helplessness, which I inexplicably found gratifying. At least the guilt I felt over my late rent was becoming a distant memory.  Maybe this was how I repay her, I thought.

It wasn’t long before my manhood started to swell. Kristen massaged my balls a little longer until I was rock hard, up against her right leg. I heard her giggle in amusement.

“Ohhhh, you are a very naughty, naughty boy, Cameron. Here I was trying to humiliate you as part of your punishment, and you are sexualizing it! I have no choice but to paddle you even harder.”

The next thing I remember, she removed her hand from between my legs, and the paddle returned to my butt, only to lift off for the third time. It quickly came back down harder than before, beginning what I can only describe as the most painful moment of my life. I gasped at the crack of the paddle, unable to utter a sound, as the tears filled my eyes again. The paddle rested on my bottom for about a second, and was then followed by another ferocious smack. Another came quickly after. I began to whimper. The spanks were no longer as shocking as the first ones, but they were even more painful. I jerked, and cried softly with each wack, as Kristen laid down the remainder of my paddling.

The spanks continued longer than she had promised. Later I would find out that she decided she would paddle me until my erection was gone. When the last smack finally landed, I jerked so hard that I felt her struggle to keep me in position. I felt something roll down my right leg. I looked down, and could see a puddle of my own tears on the carpet.

“Well, young man…congratulations, you managed to break my paddle. At least I know I didn’t go easy on you. You’re gonna buy me a new one. And you’re gonna buy it in person at the store while I supervise you…is that understood?”

I was overcome with humiliation. But I didn’t dare defy her. “Yes miss Kristen,” I replied as I continued to cry softly.

“Good boy,” she said gently.

Her finger tips returned to my thighs, caressing up and down. Before long she resumed playing with my balls which was a welcome distraction from the burning on my backside. It became clear to me that as long as I lived under her roof, I would not be allowed the dignity of manhood. I was her boyish plaything – there to be spanked, fondled, and used whenever she wished. I wasn’t sure how I felt about getting spanked again, but if she allowed me to stay in my room at such a steep discount, and she touched me like this, maybe it was a price worth paying, I thought to myself.

“Cameron, you took your spanking like a good boy, and I’m very proud of you for doing so. Now what I want you to do is stand up, and march yourself to the corner. You may not pull your pants up, and you may not touch, or rub your bottom. You may not cover yourself in any way”

She lifted her leg, and released me from her grasp. I hesitated to stand up since my I was almost completely erect again. I lay there still over her lap, afraid to move.

“Young man, get up and do as I told you or I am going to take your belt off and whip your ass with it!” she commanded firmly.

Her threat jolted me into action. I stood up quickly, and performed the awful walk of shame over to the corner: hands at my sides, my pants around my ankles, my red butt, and erect penis on full display. I picked the corner just left to the window over looking the street. I was pretty sure no one would be able to see me from there. I was happy to be able to hide the worst of my nudity in the corner as I stuck my nose into the drywall. 

“That’s better,” she said. “Now I will be back in 10 minutes to check on you, and then we will finish up.”

“Yes, miss Kristen,” I replied.

She left the room, and I was finally alone to take in the strange events that had just transpired. I had no idea idea what she meant by “finish up” but at least I knew there was an end in sight. 

The minutes felt like hours as the last of my tears from my face, and I breathed in the dull scent of drywall again, and again. My bottom tingled with warmth, and my dick hung loosely. After a while it was no longer erect, but it was thick, and ready.

I heard Kristen’s footsteps as she re-entered the room. 

“Good boy,” she said. “Now let’s see how badly you want to keep your room, shall we?” she said with a devilish chuckle.

I heard a light “pop” sound, followed by the squeeze of liquid from a plastic bottle. I felt her move closer to me until she reached around and grabbed my dick. Her hand was soaked in soothing, warm jelly. She began to stroke me slowly, as my manhood became erect once more, now throbbing with each stroke of her firm, yet dainty hand. I looked down in delight to see her painted pink nails, slick with KY jelly, moving back and forth along my Johnson, which was reaching a size I had never seen before. I began to breathe a deep sigh of relief, and I smiled, moving my hips in sync with her wrist.

She pressed her body against mine, pushing me deeper into the corner. I felt her bra up against my shirt, and her bare skin, and panties against my hips. She had undressed herself for this part, I realized. Her hair was wet. Her body smelled of shampoo, and coconut lotion. I realized that the spanking indeed was a small price to pay for the benefits of my new living arrangement. I decided to egg her on little.

“I’m sorry for being a bad boy miss Kristen. Please don’t spank me again,” I said in a small, pleading tone of voice.

A moment passed, and the stroking was punctuated with sharp smacks of her hand against my tender moon. 

“Ohh, I’l spank you as much as I want Cameron. You just keep your little mouth shut, and do as I say. Is that understood?” she said as she landed three more smacks on my left cheek.

“Owwww…yes miss Kristen!” I cried out. The smacks were stingy and biting. Her stroking was picking up speed, and her grip tightened. I was losing my breath. I could feel a shiver in my lower back as my body began to tremble with pleasure.

“Good boy!” she said excitedly. Three more smacks landed on my right cheek. I stuck my butt out to meet them. I could feel my heart pounding now, and I closed my eyes. The stoking, and spanking both intensified.

“Ohhhh Cameron, you are enjoying this waaaaayy too much,” she said with another smack. Her voice was breathy. She began to smack with almost every word, alternating my cheeks, as she scolded me. “If you…. make… a mess… on my wall… you are going… to… clean it up, and go straight …to bed…. without…dinner!!”

Her firm scolding then crescendoed into yelling. “You… are… such… a… naughty…. little… boy!”

“I don’t want to Kristen, please don’t make me. Let me cum on you please!” I begged her in desperation.

She removed her hand, and stopped spanking.  “Turn around!” she commanded.

I obeyed, only to find her on her knees in front front of me, wearing a pair of white cotton panties, and a bra of the same color. Her skin looked exquisitely soft, and I had the most incredible view of her cleavage. As I took it in, she returned her hand to my dick. Three strokes was all it took.

“Ahhhhhhh, Krist’!” I yelled out in a high pitched voice. I couldn’t finish my sentence before I felt my body swept up in a tsunami-like wave of orgasmic ecstasy. I closed my eyes and felt what seemed like a fire hose of semen pour out from my erection. It came out in several spurts – more than ever before. I felt my hips tremble, and I dropped to my knees. As I landed on the carpet, I felt the last spurt. I opened my eyes.

Kristen and I were now at eye level. She was smiling, with her hand still on my dick, rubbing gently with her fingers. I was completely out of breath, but as I recovered, I surveyed the damaged. A little bit of my cum had fallen on her lips, and was dripping down her chin. The rest was spread around her breasts in small puddles, with the exception of one large spurt that seemed to have landed inside of her cleavage, and another that was now dripping down her right thigh. Somehow her bra was intact. I put my hands on her shoulders to brace myself.

She wiped her mouth and dried it on her hip before kissing my forehead. “Well, it looks like you and I are gonna have a lot of fun together,” she said with a light chuckle.

“That was the strangest, and also one of the funnest things I’ve ever done,” I said as I finally caught my breath enough to put a sentence together.

“I’m glad you think so. But you notice that only one of us came right?”

“I’m sorry…can I fix that once I come back down to earth?” I replied as I laughed.

“How about we get you in the shower, and talk about it over dinner?”

“That sounds wonderful, Kris’…I mean, Miss Kristen.”

She stood up, and extended her hand to me. I took it, and got up off of my knees. She stepped closer, put her arms around me, and gave me a long, passionate french kiss. I could feel my juices dripping on her body, but I didn’t mind. Her warm, loving embrace contrasted deliciously with the stern, and domineering presence that had taken me captive only moments earlier. 

“I’ll make pasta tonight. You can have peach pie for dessert,” she said with a wink.

I laughed. “Anything for you,” I said.

“Good boy Cameron. Now go take a shower!” She smacked my naked bottom one last time. I waddled out of the room with my pants around my ankles.

As I showered, I replayed the whole scene in my mind. It was, by far, the most incredibly erotic experience of my life. Even the soreness on my backside was a bittersweet reminder that I was now in the care, and protection of a strict, yet irresistible woman. It’s not the kind of arrangement I would have dreamed up for myself. But I was elated to know that it was now mine for the keeping.