Chapter 6: Jade

Sunday, September 17, 2023

“Don’t you think Mark is cute?” Opal asked me for the sixth time in the last twenty minutes.

I rolled my eyes even though she couldn’t see me because I was driving, and we were speaking through the Bluetooth connection in my car.

“Opal, what does it matter what I think? You’re the one who likes him. Not me!”

“But I want your approval. I’m thinking about, you know, giving him my virginity.”

“Whatever, Opal. He’s gorgeous. He’s so sexy I may steal him from you. Every time I see him, I have to change my panties because they get so wet.”

“Okay...” Opal said in an exasperated tone. “Enough sarcasm. Your opinion matters to me. You have way more experience with sex than me. I need some input, dammit!”

“Is that your way of calling me a slut?” I asked.

“No! But just one question: how many people did you sleep with in your freshman year?”

“Guys or girls?”

“See what I mean? Just answer my question. Should I do it with him or not?”

I took a deep breath and forced myself to focus. It was not an easy task, considering where I was headed. “Okay ... Is he nice to you?”

“Yeah. He’s not pushy or rude.”

“Does he give you butterflies in your tummy when he gets close to you?”

“Mhmm.”

“Do you think he’s cute?”

“I think he’s hot!” Opal declared. “I can’t believe he’s Marjorie’s nephew.”

“Then, if you feel it’s right, go for it.”

There was a brief pause on the phone before Opal said, “Okay, thank you! What are you doing right now? Do you want to hang out? Mark is busy with friends tonight. I think they’re drinking and watching Sunday Night Football. Is there a football team called the Dolphins?”

“Yes. Why don’t you hang out with him?”

“I don’t know anything about football. I’ll look dumb.”

“Ask him to teach you. He’d love that. I’m hanging out with my study group.”

“Fine...” Opal moaned. “Bye.”

“Love you.”

When the phone call ended, I quickly tried to think of anybody else I could call, but I was running out of time. Sir had said that being more than five minutes late more than once would result in having all my videos released to everybody I knew. I didn’t want to waste my one free absence.

It was 8:49 p.m., and I was already in the hotel parking lot. Sir had asked me to wear certain items of clothing that I did not own, so I purchased them earlier today before my shift at the library. I wore a tight black minidress with spaghetti straps, a simple red choker, and black pumps with nude stockings. Red lipstick matching the choker adorned my lips, along with simple makeup applied as Sir requested.

Just as I was about to get out of the car, my phone rang again. It was Fanny. I picked it up and cleared my throat.

“Hey, Fanny,” I said as brightly as I could.

“Hey, where are you?” she answered. “I’m at your apartment with pizza.”

“Oh, Fanny ... I said maybe. I’m on my way to my mom’s house. It was a spur-of-the-moment thing, and she needs me. You know how she’s doing right now with my dad and stuff.”

“Yeah ... I know,” Fanny said. I could practically hear her pout. “It feels like forever since we spent time together.”

“You spent the night at my house on Monday,” I reminded her. “We spent all night together.” I remembered this well because I had milked myself dry before she arrived so she wouldn’t discover I was lactating and start asking questions.

“And it was amazing,” Fanny said. “But that was like five days ago. And you seemed distracted for a big chunk of the time.”

Fanny was horny for me. She was always horny for me since she’d become my witness. Part of me was annoyed by her, but another part knew it was my fault she felt the way she did. I needed to be more understanding and accommodating. “Do you want to spend tomorrow with me? Like the whole day after class? I don’t work tomorrow.”

“Yeah,” Fanny said. “I would love that.”

“K, let’s do it. We’ll do whatever you want.”

Fanny giggled into the phone. “Don’t say that. I’ll drain you dry of all your fluids.”

“If that’s what you want,” I said. “I’ll fuck you senseless.”

“I’m holding you to it. I’ll see you tomorrow in class.”

“Love you,” I told her.

“I love you, too.”

I hung up again and checked the time—8:56 p.m. “Damn,” I muttered as I hurried into the hotel. I ignored Carol, the night clerk, who was probably used to seeing me dressed like a slut by now. I didn’t even glance at the check-in desk.

My stomach flip-flopped up the elevator, and I knocked on the door four times before my phone’s clock changed to 9:01 p.m. I entered the room to see Sir wearing a different outfit and mask today. Per the norm, several cameras were aimed from different angles, all pointing to the living room area where we would spend part of our time “playing.”

I knelt before my blackmailer and said, “Your servant is here to please you, Sir.”

Sir looked down on me wearing a kabuki mask, except it also glowed neon purple eyes, green lines as eyebrows and cheek lines, and blue lips that formed a deep frown. Instead of an androgynous business suit like our first two sessions, today Sir wore plain black spandex. Still, the lighting prevented me from seeing enough detail to discern any curves or bulges.

“This will be our last meeting at this hotel, Jade,” the deep, modified voice informed me. “Your next session will be at a new location. From now on, you will picked up by a car and taken to one of my studios.”

“Yes, Sir.” I bowed my head a little lower.

“Remove all of your clothing and place it on the chair.”

I stood and undressed, folding my clothes and laying them on one of the sitting chairs in the penthouse suite’s living room. My breasts were stiff and swollen again, just as sensitive as the week before due to the overabundance of fluid stored in them. Though I would never admit it, I looked forward to having them milked simply for the relief it would bring. Sir reached out a gloved hand and touched my right boob. I winced at the slightest pressure. Usually, I was allowed to milk myself every night before bed, but I received a text from Sir on Friday morning informing me that I was forbidden to milk myself on Friday, Saturday, and Sunday. I’d cried after reading it because I knew how sore my breasts were going to be. Even at the end of one day, they were very tender. Three days was downright agony.

“Good,” Sir mused. “My little cow wants to be milked again, doesn’t she?”

“Yes, Sir.”

“Perhaps a little pain to make the relief that much sweeter?”

Sir went to the coffee table, where several toys formed a neat row. Two toys were chosen: a riding crop and a pair of arm cuffs with a locking mechanism. Sir slipped the cuffs on my arms and folded them behind me before locking the mechanism so I couldn’t move my arms.

“Count each time you feel the sting of my crop. If you can get to twenty lashes without a tear falling from your eye, I will milk you. If not, we will try something else.”

“Yes, Sir,” I whispered.

Sir had warned me more than once that pleasure and pain would be intermingled heavily in our sessions, but his focus the first two weeks had primarily been pleasure, which I didn’t mind so much, all things considered. Now, I braced myself for the worst.

With riding crop in hand, Sir circled me slowly, smacking the end of the crop against a gloved palm. “Where to start? Your body is positively delicious. How about ... here?”

THWACK!

The crop stung into my ribs just below my left boob. I jumped, but the only sound I made was “One.” That hadn’t been so bad.

“Very good,” Sir said. “Let’s try again.”

THWACK!

“Two!” I gasped as the crop bit my thigh.

THWACK!

“Three!” My other thigh.

Twin scarlet lines blossomed on my thighs. Heat radiated from all three spots where Sir had swatted me. Sir watched me through the mask, which betrayed no emotion, just a constantly scowling kabuki face.

THWACK! THWACK! THWACK!

I screamed as the next three smacks all landed on my breasts and nipples. I hadn’t prepared myself for those areas. My eyes watered, and I bent all my focus to stopping my tears. I breathed deeply through my nose, pushing through the pain and trying to think about something else—anything else—but all I could think of was how badly my breasts now ached and stung.

“Four five six!” I finally said.

Sir watched my face for several seconds before beginning to circle me again. “Excellent, Jade. You have phenomenal self-control. You make for such a nice toy.”

The compliment boosted my spirits enough to help me regain my composure.

“Lean forward with your face on the ground.”

“Yes, Sir.”

This was not easy with my arms restrained behind my back. I had to use my abs to slowly lower my upper half without crashing my face into the carpet. I finally did so with my head turned, but the carpet fibers on my hypersensitive nipples threatened to drive me mad.

THWACK! THWACK!

The hardest swats yet seared across both of my asscheeks.

“Seven! Eight!” I hissed into the carpet.

THWACK!

“Nine!”

THWACK! Right against my labia.

“Ten!” I grunted.

THWACK! In between my ass cheeks. My entire backside throbbed badly.

“Eleven!”

THWACK! THWACK! THWACK! THWACK! Four hard shots starting just under my butt and traveling down the back of my thighs.

“Twelve, thirteen, fourteen, fifteen!” I cried out with a definite note of desperation in my voice. I closed my eyes tightly to keep any tears from falling.

“Back to a kneeling position!” Sir barked.

Getting back up was even more challenging to do than bending over. I’d been holding my breath, and tears nearly came out, but I forced myself to exhale as I got up. This helped stem the flow.

Another THWACK! before I was ready. Sharp pain seared across my abs. I yelped and gasped. That one had not only caught me off-guard, but it had taken my breath away.

“Sixteen!” I said through gritted teeth. I told myself silently not to cry. No matter what happened next, I could not weep. Sir stood and watched me again.

“You’re very close, Jade. Are you going to be able to take these last four, or are you going to break?”

THWACK!

My upper arm. This was the easiest of all of the blows so far. I relaxed a little. Sir was going to take it easy on me.

“Seventeen!”

THWACK!

I screamed. My left breast exploded with pure agony. “EIGHTEEN!” I shrieked as I ground my teeth together to prevent my eyes from leaking. The pain was too much to—

THWACK!

I crumpled to the floor as my right breast erupted with matching agony. “NINETEEN!” I needed to empty my breasts immediately.

“Get up, Jade!” Sir barked.

I forced myself back to my knees, unable to tell if any tears had leaked from my eyes. Sir inspected my face closely, then nodded with satisfaction. “I should punish you severely for losing your composure, but I won’t.”

“Yes, Sir.”

“This last one will be across both of your breasts. That will be punishment enough. Brace yourself.”

I stiffened every muscle in my body and held my breath. If I just could get through this, I would find relief. I could do that. I had no doubt.

The crop came down with a high-pitched whooooosh through the air and caught me at the front of my breasts just above my nipples. I bit my lip so hard I tasted blood. But I did not cry.

Sir seemed impressed as the tools were placed back onto the coffee table along with the restraints on my arms. I stretched myself out and observed thin red welts on my chest, stomach, thighs, rib, and arm, with more unseen on my back, ass, and thighs.

“Beautiful,” Sir said, observing my body. “Let’s go to the bedroom.”

“Yes, Sir.”

Sir had me sit in a chair, legs splayed to show off my pussy. Then Sir rolled in a fucking machine, adjusted it to the height of my vagina, then applied copious amounts of lubricant to the dildo. After readying the machine, Sir attached suction cups to my breasts. My body tingled with the anticipation of being milked.

The suction began, and I sagged into the chair, my head rolling back in pleasure. Then the machine pistoned into my cunt, filling me nicely. The residual pain of my welts faded as gush after gush of fresh milk pumped from my nipples. I couldn’t say which part of the ecstasy pushed me over the edge: the rushing fluids from my tits or the steady pounding in my pussy, but the orgasm took me hard and swept me away from the hotel and from Sir for a good half minute. I screamed yet again, but this time in pure ecstasy, and rode out the climax into a second one as the machine pummeled my poor pussy.

By the time Sir removed the suction cups from my nipples, I had cum three times and filled up two bottles of warm milk. My body tingled incredibly. Every nerve pulsed and hummed with brilliant awareness. I could not remember ever feeling more alive than I did then.

“You’re beginning to understand what I once learned,” Sir commented. “The combination of pleasure and pain is transcendent and equally important to achieve a higher plane of consciousness. The experience you are having now ... I will take you to higher heights and lower depths before our year ends. You will understand what it means to truly live before I am finished with you, Jade.”

“Yes, Sir.”

“Did you prepare your bowels as I directed?”

“Yes, Sir.”

Along with my instructions not to milk myself Friday, Saturday, and Sunday, I had also been ordered to eat only a light dinner on Saturday and drink only fluids on Sunday. No food anymore if I was to meet Sir that day. Furthermore, I was to give myself two enemas: one at midday and one in the evening just before our sessions. I had followed Sir’s instructions, meaning I was pretty hungry. After three orgasms and the lashing session, my body was wiped.

Sir poured one of the bottles containing my milk into a champagne glass. Then it was handed to me.

“You look exhausted. You aren’t used to longer play sessions yet. Drink.”

Drink my own milk? The idea repulsed me. But it wasn’t an offer. It was an order.

I put the glass to my lips and sipped it. Other than being warm, the milk wasn’t bad at all. It reminded me of sweetened almond milk, which Marcy’s moms often drank. The smell of it reminded me of a baby’s scent. I drained the glass and almost instantly had more energy.

“On the floor, Jade.”

“Yes, Sir.”

I was placed in restraints again. This time, I was put into a rectangular metal frame with cuffs at the four corners. Sir adjusted the long ends of the frame to match my height. Then my ankles were cuffed at one end of the frame, my wrists at the other. After securing me, Sir rotated the frame until I was face down, ass up, my knees and elbows against the ground. My mouth was gagged, but my eyes were left uncovered.

Sir used a speculum to open my anus. I expected lube to be poured inside, but instead, something else went into my colon. My milk. It was the strangest sensation I’d ever felt, my bowels filling with warm, fresh milk. Then, Sir placed a plug into me and removed the speculum. The fucking machine was wheeled behind me and adjusted again to line up with my butthole.

I didn’t need to ask what was about to happen. Sir was going to use the machine to fuck my ass using my milk as lubricant. Before starting the machine, Sir placed a vibrating egg against my crotch and locked it into place with a buckling leather strap.

“Prepare yourself,” Sir said.

The plug was removed from my nether hole, and the machine began pistoning in and out of my ass at the same time the vibrator started buzzing against my clit. So many things hit me at once, and I experienced another of those mind-shattering moments where the massive stimulation overwhelmed me: the deep thrum of the vibrator, the squelching noise of the dildo ramming my asshole and splattering my milk across my buttcheeks, back, and pussy; the taste of my lactation still lingering on my tongue; the sheer fatigue of my body surrendering to Sir’s will.

And the pleasure. The overwhelming pleasure of it all. The way I was forced to kneel and take it even after cumming. I couldn’t let my arms or legs buckle. Even after I came the fourth time and my clit was so sensitive I wanted to scream, I couldn’t do anything about it.

This went on for over thirty minutes. I orgasmed three more times. When the gag was removed from my mouth, drool pooled on the floor below my face. I was in a haze from that point on, the fog of a broken mind where I didn’t really know where my body began and ended. I became a vessel of pain and pleasure. I knew I was suspended in a harness, legs, and arms spread. I was gagged, blindfolded, and had nipple clamps placed. My nipples were still incredibly sensitive, and this was the most unpleasant part of the final act of the night. Milk steadily dripped from my breasts onto the floor. Sir stood behind me and ate my pussy for quite some time, commenting on my pleasant flavor. Then Sir lowered me and directed me to manipulate my body to grow my cock. I did so in a daze. Then Sir resuspended me, then sucked my cock until my cum spurted in a ruined orgasm.

I heard the cum splatter. Soon after, I was released. I dressed mindlessly. Sir said some words to me, but I didn’t hear them. I made it back to my car, still in a trance-like state. I had no memory of my drive back. I ended up not at my apartment but at Velma’s. I knocked on the door, but she didn’t answer. It was after midnight when the haze started to lift from my mind. I was still sitting in front of Velma’s door, so I got up and went home.