First Day on the Job Ch. 02

This is a continuation of chapter 1. All characters are over 18 and are consenting adults.

I laid there gathering myself. Thinking through everything that just happened. The last 24 hours had been a whirlwind.

Derrick was standing up talking to Tyrell. I watched intently as his big black cock, now soft, still immense, swung beneath him.

I reached down and traced my still gaping ass. I would never be the same. There is no going back to a normal, straight, life after getting completely annihilated by a big black cock like his.

"Why don't you go get cleaned up, baby. You are absolutely covered in your own cum," he said with a touch of arrogance.

I blushed. He had every right to be arrogant. He successfully made me his. He successfully made me cum so many times that by my last orgasm my little penis was firing blanks and trembling in pleasure. And he knew the power he held over me.

Many women and sissies never get to experience a real cock. But I was lucky enough to only know a real cock. And there was no going back. I was completely hooked on big black cock.

I stood up to head to the bathroom and clean up. Derrick smiled upon seeing how my little penis was once again, fully hard.

He grabbed his big black cock and lewdly shook it at me, winking and smiling.

"Oh my god, stop Derrick!" I laughed in embarrassment as I scurried to the bathroom, still in my wedge sandals.

I closed the door behind me and looked at myself in the mirror. I looked exactly as I felt, like a freshly fucked sissy. My own sissy cum was caked to my stomach and bra. My little penis stood at attention, unable to shake the images of Derrick's big black cock. My hair disheveled from being dominated. My cheeks flush with embarrassment and pleasure.

But despite all of it, I felt good. I felt fucking great actually!

I took my bra off and hopped in the shower, scrubbing myself. I was lucky that my body was naturally hairless below my eyebrows, shaving would be a challenge.

I turned off the shower and went to my closet and dresser, not knowing what to wear.

Start with the basics, I thought, going to my lingerie drawer. I quickly found a lacy lavender thing that I loved.

While my penis had softened in the shower, it twitched back to life as soon as I stepped into the thong. I moaned as the back of the thong pressed against my very sore asshole.

However, the soreness almost hurt in a good way. In a way that triggered all the memories of being truly dominated by a big black cock. Images, now seared into my brain, flashed before me as I closed my eyes and bit my lip.

I covered my mouth with one hand and reached down to rub my hard little penis from the outside of my thong with the palm of my other hand.

I moaned.

"Jess, what are doing?" Derrick said.

I was so caught up in my own world that I didn't hear him open the door.

"Oh, sorry, Sir, I was..." I apologized, trying to explain myself.

"Jess, we talked about this earlier, but I do recognize it was when I was fucking you with my big black cock, so I'll give you a pass this time. But you are not to touch yourself like that. If you are having a hard time restraining yourself, we will figure out alternative measures. Do you understand?" He said.

I quickly moved my hands to side and looked down the floor submissively. I nodded to demonstrate my understanding. He wasn't being mean, just firm. I appreciated his consistency with rules and expectations of me.

I wanted to show him that I was eager to follow his lead, that I could obey him.

I lifted my head, he had his clothes back on. I was disappointed that I couldn't sneak a glimpse of his big black cock. I looked him in the eyes.

"Do you have any other expectations for me, Sir? I don't want to disappoint you," I asked.

"That's a good sissy, very respectful. That's actually why I came in here. There are a few expectations that I wanted to be clear on," he said kindly.

"Thank you, Sir," I said, looking up at him with big doe eyes.

He held up a bag.

"First order of business. Bend over the bed," he instructed.

Obediently, I turned around and bent over. Still standing, but with my hands on the bed.

"Unless instructed, you will be plugged 24:7. If my big black cock isn't deep inside of you, this will keep you company," he said as he held a giant black butt plug in front of my eyes.

I almost went cross eyed staring at it. My knees felt weak.

He continued, "sissies are easily distracted and absent minded, a constant reminder such as this will help you focus on being the best sissy you can be."

I moaned loudly and fell forward onto the bed as he shoved it inside of me in one push.

"Good job baby, now stand up and put these heels on. I expect you to always be in heels unless at the gym," he said, handing me a pair of black stilettos.

I stepped into them and gathered my balance. The heels seemed to accentuate my legs and ass, making my new plug hit even more sensitive areas.

I moaned and anxiously wiggled my hips. I looked down at a dark spot of pre-cum leaking through my lavender thong.

It took everything I had not to reach out and rub it. I could have cum so quickly if I was allowed to.

I bit my lip to help take my mind off of it.

"I think it's really cute when you bite your lip to try not to cum," he said as he grabbed my wrist and pulled me into him.

In my new heels, I stumbled forward into his chest.

He placed his other hand on my ass, before leaning down to kiss me. I moaned into his mouth as he tapped the base of my butt plug, sending a warm vibration through me. Being so much shorter than him, I felt his big black cock against my stomach. I placed my hand on it, over his jeans, a gave it a squeeze.

"There will be time for that later, Sissy," he said breaking off the kiss.

"I'm looking forward to it, Sir," I said, taking a step back.

He looked at the growing wet spot on my thong and smiled.

"Ok so for your expectations, what have we gone over so far?" He asked.

I looked up at him and spoke clearly to show I understood.

"I will always wear heels, except for the gym. I will always have a butt plug inside of me unless you are fucking me with your big black cock or instructed otherwise, and I will not touch my little white penis to pleasure myself," I responded confidently.

"Very good. Next, I expect you to always wear a bra. You can decide what else to wear, but you should consider a thong, bra, and heels your uniform," he said.

"Yes, Sir," I said as I turned around and walked to the dresser.

I rifled through all the sexy lingerie that I would be wearing for Derrick until I found the matching lavender one. I clasped it on and put my arms through it before walking back to him, as if I was undergoing an inspection.

"Finally, I will require a few alterations which you will undergo over the next few days. Ears pierced, belly button pierced, hair dyed to be more blonde, and you will also wear mascara and lip stick. However, you will also wear this," he said, holding up a small pink cuff.

"What's that, Sir?" I asked.

He took a step forward and pulled the front of my thong aside, freeing my hard little boner which pointed out directly to him.

I shuddered in pleasure as he grabbed my aching penis.

"I like jewelry on my sissy. This is just a reminder for you," he said.

I looked down as he slid the pink, elastic cuff over the head of my penis.

I bit my lip as cum leaked out from his touch.

"Easy baby, you are always on edge aren't you?" He asked.

I nodded, trying my best not to shoot whatever had built back up in my tiny balls onto him or the floor.

Eventually, he got the cuff down to my base and let go as it constricted against my hard penis.

In looked down to see 2 diamonds embedded into it, with "Derrick's Sissy" inscribed in between them.

I bit my lip harder as he tucked me back into my panties.

"Thank you, Sir. I look forward to any other alterations that you see fit," I said.

"Want to see something fun?" he asked.

Confused, I nodded my head.

I watched intently as he pulled out a small remote and pushed a button.

BUZZ!!!!!

"Oh my goddddddddd!!!" I moaned, immediately reaching back to grab hold of the butt plug that was vibrating inside of me.

My knees clicked together as I struggled to stand. I bit my lip.

Derrick laughed as he watched me struggle.

I tried to speak, "I... I... I can't fight it, Sir. I think I'm going to..."

Derrick looked down at the growing dark purple spot in my lavender panties and pressed another button.

BUZZ!!!

I moved one hand off my plug to my penis as my cuff started to vibrate.

"Now now now, no touching," he said.

He grabbed both of my wrists and pulled them above me.

I tried my best to keep my balance in my heels as my body shook. The vibrations coursed through my body. Derrick laughed as I struggled to keep my composure.

I moaned loudly and bit my lip.

"Sir... Sir... I don't... I don't think I can hold it back any further. Please... please stop them," I said.

Derrick laughed again and lifted me up in the air by my wrists above my head until I was face to face with him. My feet were a foot off the ground.

He leaned forward and pressed his lips up against my ear.

"Are you my sissy?" He said in a low, manly whisper.

"Mmmhmm," I nodded as my body flailed under his control, "I'm your Sissy, Sir."

"Do not cum yet then, Sissy," he said.

I squeezed my eyes shut and bit my lip. I felt sweat start to form on my forehead. I focused with all my sissy willpower not to cum. I tried to do math in my head, anything.

Satisfied with my pathetic attempt, he whispered one more time, "you can cum now."

Finally having his permission, the dam broke. I let out a loud moan and cum flooded into my lavender thong. My hips bucked like a fish in the air as he held me from my wrists.

Eventually my orgasm subsided, and he turned the vibrations off, setting me back on the ground.

"Looks like you might need a dry thong. why don't you change and meet us in the kitchen," he said, walking out.

I tried to catch my breath after that display of ownership. My knees were weak and I collapsed backwards onto the bed. Forgetting about my plug, I moaned loudly as the now dormant plug was pushed deeper into my ass.

I laid back, easing the pressure from my plug. After a couple of minutes, I regrouped and stood back up, walking over to find a dry thong.

Less than 24 hours into this, and I had already soaked 4 thongs with my own cum. I shook my head and smiled, looking for my next victim.

I quickly decided to go with a white thong with a pink bow on each hip. I found the matching bra which had a similar pink bow in the middle of the chest.

I looked at myself in the mirror and admired how I looked. I loved how my penis was so small that it could fit neatly in my thong. I loved how even my boner was feminine and couldn't break free from the thin material of a thong. And I loved how I could see the outline of my penis cuff, detailing who I was now.

I opened the closet to look for what else to wear. I was quickly drawn to a white flimsy skirt. I stepped into it. It sat low on my hips and barely covered my ass. I turned quickly and watched in the mirror how the sudden movement exposed my ass for a second.

I walked over to my dresser and found a pink tank top. I put it on and adjusted my bra under it.

The tank top turned out to be more of a crop top, ending on my rips. I smiled at myself in the mirror as I put my hair back up in a ponytail.

I looked HOT!

Full of new found sissy confidence, I walked back out to greet everyone in the kitchen.

Derrick and Tyrell were sitting at the hi top kitchen table with two of the other crew members, both hot white females.

"There she is!" Derrick said.

I walked up to Derrick and squeezed next to him since there weren't any other chairs.

"Get up here," he said, lifting me up and setting my down on his lap.

I moaned and bit my lip.

"There's that little lip bite. Did you almost cum there?" Derrick asked.

I blushed and sat in silence, hoping it was a rhetorical question.

"Did you not hear me?" He said again.

Trying not to make eye contact with the table, I answered him, "Oh sorry, Sir. Yes. I... ummm.. when you set me down your big black black cock pushed my butt plug in a bit further. It felt so good."

I wiggled my ass on his big black cock.

The girls both giggled.

I blushed.

Tyrell spoke up, "alright let's make this official. So Jess, I know we had already agreed upon an unpaid internship, but I feel like your scope has changed and we want you to be a part of product. That being said, what do you think about 5%? Which is standard for a newbie in the industry. But this way, if we make $100k, you get $5k."

I thought for a second, then about Derrick's big black cock under me, and the sexy clothes I was wearing.

"And all these clothes are mine? And kitchen will be stocked as we initially discusses?" I said.

"Absolutely," Tyrell said, handing me a pen and sliding a piece of paper over.

This deal was too good to be true. Quickly, I signed it.

"Amazing, let's celebrate!" Tyrell said.

"Why don't you be a good sissy and go get that tray over there?" Derrick said.

He set me on the floor and I walked over to get the tray of champaign that was already poured.

I picked it up and turned to walk back towards them.

"You were right Tyrell, that butt plug really makes her hips sway," Derrick said.

I blushed, trying to ignore the conversation about my butt plug before setting the tray on the table.

We all grabbed a glass.

"To our new venture, I'm thinking we should name it, 'Sissy Jess: Big Black Cock Summer' Tyrell said.

"I like it, get's right the point," Derrick said.

"It will market well," said one of the other girls.

"What are we thinking for business model? Subscription? Pay by time spent on stream?" Said the other.

They discussed the logistics while I tried to keep up. But no one asked for my opinion.

By the end it was decided that people could tap into the live stream 24:7. They would be charged $10 an hour. Or they could get a summer pass for $250.

I would also do live chats, exclusive to members twice a week.

The video from my first 24 hours, would be cut down into a marketing preview and posted to porn sites and social. The preview, however, would end right before right before Derrick entered me.

The entire video would only be available to people who sign up for the entire summer.

I would also create a social handle for myself, under the name "SissyJess4BBC" to promote the content.

I went along with it all and stood at the table quietly while they hashed it out. They were the pros. Getting 5% had me invested. Well that and craving Derrick's big black cock.

Through the conversation, I picked up that the one girl was named Becky, and the other was Lisa.

"Wait, was Becky even real from the original project?" I asked.

They all laughed, then Becky answered, "no, we just used my name. Derrick is much too big for me, no offense Derrick."

"None, taken. I think Jess here is happy you turned me down," he said, patting me on the ass.

I took a sip of champagne.

Becky rummaged through her bag, "here is your phone that we have all set up for you."

She handed me brand new phone with a pink case that said 'Sissy Jess' on it.

"I have you all set up on social media. Why don't you make your first post?" Becky encouraged.

"What do I say?" I asked.

"Whatever you want! Be natural, promote the content," she said.

Nervously, I started recording.

"Hi everyone! I'm... I'm... I'm Sissy Jess. Up until yesterday, I was just Jess. But in the last 24 hours I have become Sissy Jess. What else do you need to know about me? Well... as of a few hours ago, I'm hopelessly addicted to big black cock! And my master is Derrick and he's right here with me. We are going to be living together this summer here in LA and will be live streaming 24:7. Go online if you want to follow along. Maybe we can even do a drawing. If you sign up in the first 2 days, you'll be entered to win the pink thong that his big black cock made me cum all over earlier this morning. I can't wait for you all to be on this journey with me this summer!"

"Whoa, she's good," Becky said.

"How do I get people to see this?" I said.

"Just tag Turned Out Studios, and we'll repost from there," Becky said.

"Ok, done!" I said.

"How many followers does the studio have?" I asked.

Becky re-posted my video and then turned to me, "2.1 million," she said.

I turned red. 2.1 million people would see my little video. Surely someone would recognize me. My mind raced.

"Since we have time, do you want me to just go ahead with piercings, hair, and make-up?" Lisa asked Derrick, breaking the silence.

Not looking for my opinion, Derrick spoke up, "yea let's do it. Jess why don't you take my seat."

Derrick stood up and lifted me up onto the stool. Before I knew it, Lisa had a plastic case on the table and was preparing her piercing gun.

"Oh wait, let's get this for social," Becky said, picking up my phone.

It hurt for a minute, but pretty soon I had two diamond studs in my ears.

"Pretty soon, we'll replace those little studs with big hoops," Derrick said.

Next, Derrick picked me up and laid me on the table so Lisa could pierce my belly button. When it was done I looked down at a small spade charm that hung from a thin chain.

"What's this?" I asked, playing with it.

"A spade is a symbol for loyalty to big black cock. Derrick picked it out for you," Lisa said.

I turned my head to look at him, "thank you sir, I love it."

"Did you decide on her penis, Derrick? Do you want it pierced too?" Lisa asked.

"Let's pass on that for now. I'm concerned that she is going to need to be locked up, so I don't want a piercing to get in the way of her training," Derrick responded.

I blushed as they had this conversation over me, but I wasn't allowed to answer.

"Let's go ahead and do hair too though," Derrick said as he helped me off the table.

Lisa took my hand and led me to the bathroom where over the next hour, she worked on dying my hair.

While my hair set, she showed me how to do mascara, eye liner, lipstick, and nail polish.

When it was all said and done, I looked completely transformed and Becky had caught it all on camera. Gone was any trace of masculinity. Sissy Jess had arrived.

"Let's go show your man!" Lisa said.

She took me by the hand and I walked behind here.

"May I introduce you to the new, improved, Sissy Jess!" Lisa shouted.

I blushed and looked down from the attention as Derrick's jaw hit the floor. My new, blonde curls laid against my crop top. I swayed back and forth.

He stood up and walked over to me before leaning down to pick me up. I wrapped my legs around him as he pressed his forehead against mine.

"I knew you had potential, but damn. I wasn't expecting this," he said, before kissing me.

I swirled my tongue around his as he kissed me deeper and deeper.

I couldn't tell where he was leading me, until he sat down onto the couch that he had took my virginity on just a few hours ago.

He leaned back as I once again straddled him.

Not wanting to break the kiss, I reached down and fumbled with his jeans, unbuttoning them

and tugging them down.

He lifted up his ass and took his jeans and boxer briefs off the rest of the way. Realizing I now had access to his big black cock, I quickly reached down and grabbed it with both hands.

"I want you inside of me so fucking bad," I moaned into his neck while I slowly jerked him off with both hands.

"Be my guest, Sissy," he said.

He sat up quickly to take his shirt off before leaning back against the couch.

"My plug, Sir," I whispered to him.

"Let me help you with that," he said reaching behind me.

With one hand, he moved my thong to the side. With the other he gripped the base of the big plug and pulled it out with a slight spin.

There was an audible suction pop and I moaned as cold air hit the inside of gaping ass.

"Oh my god, I need you back inside of me so bad. I hate the feeling of being empty," I moaned.

I reluctantly let go of his big black cock and moved forward so that his big black cock was now behind me.

I leaned forward and grabbed ahold of him once again, positioning him against my ass.

I moaned as I felt his tip against my asshole.

I leaned back slightly and bit my lip as he entered me.

Gone was the reluctant barrier that my ass had last time. My ass was now hungry for him. It craved every ounce of pleasure that it knew his big black cock could provide.

I kept leaning back, further and further as his big black cock snaked back into my well broken in ass.

"Damn baby, you are so tight," he said.

"You are so fucking big, Sir. I want every inch of you," I said, moaning louder.

I leaned back and grabbed his knees to steady myself as I made my final move to bury his entire big black cock inside of me.

I stayed there for a second and caught my breath. But pretty soon, I started moving my hips clockwise, expertly spiraling my way up and down his shaft.

He felt so good.

Once I got to his head, I pushed all the way back down in one fluid motion.

"Oh my godddd," I yelled, as I bit my lip.

I moved my hands to his shoulders and balanced myself as I started bouncing on his big black cock.

I tried different moved, but quickly found my spot, which was deep. Once he was fully inside of me, I would work my way up in chunks. 4 inches up, 3 down, 4 up, 3 down, until I had just his head in me and I could feel my asshole grabbing onto his ridges. Then I would slide all the way back down.

It felt amazing. It felt perfect. A sense of pleasure that was void from my life until earlier today.

"There you go baby," he said, encouraging me and putting his hands on my hips.

I worked my way back up in the same, perfect pattern. I loved how I could feel different parts of his cock and knew exactly where I was on it.

I got to my final position before I slid back down his big black cock, but before I could, he lifted me up off of him.

I moaned in a feeling of empty frustration. My body shook.

"Please, please, I need your big black cock," I started to beg.

I lifted my hands up to my new blonde curly hair and looked down at him as he held me above his magnificent cock.

He smiled, positioned me just above his big black cock and let go.

I wasn't prepared to catch myself as I was playing with my new hair.

I screamed in pleasure as my weight forced me to slide all the way down. My body convulsed and I bit my lip, but it was no use. I was overcome by another mind bending orgasm.

I curled into a little ball on his chest my orgasm flooded my thong. I moaned uncontrollably and drooled on his chest.

Then, he started fucking me hard. He held my hips and fucked me harder and harder with the full length of his big black cock.

I moaned and moaned as the onslaught continued. My asshole had gone numb. I was his for the taking.

Eventually, he squeezed my ass hard and shot what felt like another enormous load inside me.

After standing up and lifting me up, he laid me back down before withdrawing his big black cock. I moaned once again from the emptiness, before he easily jammed the butt plug back into me.

"Looks like you ruined another thong,"

He said to me.

I looked down, my white skirt had a large see thru spot from where my cum had leaked through.

"Thank you for that, Sir," I said with honest gratitude.

"Guys we already have 5,000 members, and they all watched that!" Becky yelled.

I blushed once again, but I didn't care. My afterglow was too strong.

Leave comments if you want more. Direct message me if you have ideas of things you want to read about in future chapters!