Something New Ch. 24

Waking up with a single ray of dawn sun shining through the basement window was an eerie way to wake up. It wasn't as cold as I thought it would be but that might have to do more with the warm body of my wife curled up into me. The mattress was hard and barely padded against the cold hard cement floor but I can't remember the last time I was this comfortable cuddling my wife. I wrapped my arm around her to squeeze her tightly but gently so as not to wake her. She nuzzled her way into me and in a sleeping mumble I made out the words that changed my mood in an instant.

"Mmmm Jared." She moaned into me.

It felt like a betrayal but I guess it made sense right? She just had the most incredible night last night. For the first time in her life she was fucked in the ass by a huge black cock and squirted in a mind numbing orgasm. Of course she would still be dreaming about that man. It still stung to hear my wife moan another man's name in her sleep.

I stared around the room wondering what time it was. Is the door still locked? Surely Jared and Lauren wouldn't let me be late to work? I was Jared's sissy prostitute after all. I had to make that money for him. I can't believe I have sex with men for money! What has become of me? Even right now I am curled up on a hard mattress locked in my own basement still dressed in a girly outfit and a wig. Surrounding us is a studio of cameras ominously staring down at us as we sleep.

Now Jared and Lauren had a video of my wife getting ass fucked by Jared. What were they going to do with that? Should I tell my wife? Maybe now, the morning after, she might not be so comfortable with all of this? Maybe I can get her to ask her sister to put an end to this? Although I can't get her to stop my prostitution because she doesn't know about that? How did this get all pear shaped so fast?

I either dozed off or was just in a deep state of contemplation because I startled at the sound of the basement door unlocking and swinging open. The light let in from the door illuminated the whole dark basement. I didn't want to move and risk waking up my wife to see who walked down the stairs. Soon enough the looming face of Lauren, my sister in-law, peered over me, smiling.

"Aww so cute," she whispered, ringing her hands before gesturing to an imaginary wrist watch.

Carefully I detangled myself from my wife and slowly rolled off the mattress. I didn't realize how sore I was until I tried to stand. Two gangbangs in two days really has a way of making muscles sore that you didn't even know you had.

Lauren escorted me up the stairs and into the bright morning.

"How'd you sleep sweetie?" Lauren asked sweetly like she actually cared.

"Fine" I mumbled, still groggy.

"Well you better go get cleaned up. Your uniform is already in the bathroom. Can't have you being late. I hear Lawrence has a big day planned for you." Lauren seemed so excited for whatever it was she was keeping from me.

I looked to the basement and back to her.

"Don't worry I'll throw a blanket over her. She's going to need her rest. She's got a lot planned today as well."

I went to speak but she shushed me and ushered me to the bathroom. I obeyed, but mostly because I was still so tired. Once I got into the bathroom I saw my uniform. A polka dot bikini. I stared at it for a couple minutes before I got undressed and got the shower running. Once the warm water hit my naked skin I started to feel so much better.

When I got out of the shower I slipped on the bikini and looked at myself in the mirror. What have I become? I even looked feminine standing there in a polka dot bikini with a slight bulge from the chastity cage still firmly locked around my penis. Hanging my head in shame I left the bathroom to pick out a suit for work.

When I walked downstairs I was greeted by Jared, who was pressed up against Lauren's backside. I averted my eyes as Jared spoke.

"Good morning Jennifer. Ready to make daddy proud?"

"Daddy?" I questioned looking between them.

Lauren chuckled as Jared nuzzled her neck.

"Mmm I like the sound of that baby. I wonder if we can get my sister to call you Daddy next time you fuck her in the ass. Maybe we can shoot a little scene. Black daddy in law fucks slutty daughter in law in the ass."

Jared continued to nuzzle Lauren's neck causing her eyes to roll back. I'm sure imagining her production helped too.

I didn't know what I should say. I stammered and mumbled incoherently.

"Mmm, slow down baby. Save your energy you got 3 asses to tame in the house. That's a lot even for a bull like you."

Lauren was talking to her boyfriend but she was looking at me the whole time.

"You are right. I can't be selfish. Speaking of tame asses, shouldn't you be on your way to making me more money bitch?" Jared asked me.

I looked to the basement wondering if I should try to say goodbye. While also wondering how I would do that knowing I was going to be a sissy hooker more than an office jockey. I looked to the floor feeling ashamed.

"Don't look so glum. I'll take good care of your wife. In fact we plan on going to the water park again." Jared spanked Lauren's ass as he walked around the counter toward me.

I shuffled my feet as he approached. When he was inches from me he just stood there until I worked up the courage to look him in the face. He smiled at me and brought his hands up to straighten my tie. I jumped a little at his movements.

"Why so jumpy Jennifer? I wouldn't hurt my little cash cow." He patted my chest and walked back to the counter to pour himself a cup of coffee.

"I uh I should get going." I stammered not knowing what else to do. "um have fun at the park again?"

"Oh we plan to." Lauren said in a tone that did not put me to ease.

When I got into work I was surprised to find my desk so clean and organized. Jessica and Amber must've been by again to take my work for me. I sat down at my desk and just zoned out. I finally had a second to myself. I let out a deep relaxing sigh. Then my phone buzzed. It was Lawrence.

"Heard you got in. Congratulations, I have arranged a little road trip today."

My heart sank as I read the text. Was this it? Was I going to the Pit? How many guys were going to gangbang me?

All I texted back was, "road trip?"

"There is an exclusive gloryhole that features special events and I got you into the short list of sissy talents."

"So these will be complete strangers? Not your clients? Will there be other sissy's there?" I texted back. I was nervous. I was going to go to my first real glory hole.

"Yes on all counts. This is a very exclusive event. Only a couple of girls make it every month. The guys are premium members so don't worry about that. I will be there to pick you up in a little bit. This will take most of the day."

"Oh okay, what will everyone else think when I'm gone all day?"

"The official cover is a convention for prospective clients. It's vague enough no one asks much more. See you in a bit babe."

I didn't respond, I just set my phone down and tried to come to grips about the fact I was going to a gloryhole. Was I excited? Why was I excited?

Before I could go down that rabbit hole there was a knock on the door. I wondered if Lawrence would bother texting me if he was going to be mere seconds, but I was surprised to find a familiar redhead poking her head around the corner.

"Is this a bad time?"

"No no of course not. Come in. What can I do for you?" I stood up motioning for the intern to come in.

"I came to see if you had time to talk about presenting and managing a crowd." She looked around the room subtly like she was looking for something.

"Um, I have a few minutes before I leave."

"Leave?" She asked as she sat down at a chair in front of my desk.

"Yeah I have a... uh convention to go to." I almost forgot what Lawrence had called it.

"Oh that is cool. I don't suppose I could come and see you in action? I've really admired your work."

I blinked dumbfounded.

"Uh well it's kind of an exclusive event. Maybe another time."

"Oh right of course. I just know that there is a lot you can teach me and I am willing to do anything to get ahead."

She shot me a little wink that made me realize that she was hitting on me. This was a new thing even before all of this sissy stuff.

"Uh well that's a uh good attitude to have. Ambition will take you far. I do have one question?"

"What's that?"

"You're an intern right? Have you heard any rumors about some inappropriate behavior here?"

"Um I'm not sure what you mean." She looked away clearly knowing exactly what I meant.

"It's okay I'm just out of the information chain and I like knowing what's going around the water cooler. I'm not going to narc on anyone."

"Well there is one thing. There is this rumor going around about a woman entertaining a lot of men but no one has met her. There have just been a lot of men coming and going. Some woman named Jennifer."

My heart fluttered as she said my secret identity.

"oh really is that so? That's juicy. "

Motivated by this she leaned forward and continued.

" People say she's even charging them for her time. Like a prostitute. But no one knows a Jennifer that works here. Least not one who could entertain all these men. Oh oh and rumor has it it's exclusively black men. "

" That's um crazy. " I said, trying to hold back anything that might give me away.

"I know right. I mean I can understand sleeping with your supervisor or a supervisor sleeping with an intern... " she stopped realizing what she just said. "I mean you hear that stuff all the time."

The room fell into an uncomfortable silence for a beat.

"I'm sorry I don't think I caught your name."

" Oh I'm sorry I'm Kayla. I'm an intern... "

After her last comment 'intern' seemed to have a different ring to it. I figured I should go for a joke to lighten the mood.

"Had there been any rumors about any redheaded interns?" I chuckled.

She chuckled, "oh no definitely not. But I have heard a talk about you sir."

The sir caught me off guard but I liked it, strangely.

"Uh me? What's being said about me?"

"Well besides the fact that you are a rock star when it comes to presentations. There is a rumor that maybe your marriage is not quite, I don't know, stable." It was a statement but she trailed off making it sound like a question.

I just stared at her speechless.

"It's none of my business, it's just a rumor." She quickly tried to back track.

"No no don't worry about it. We, uh, have a complicated relationship for sure."

"Is that a fact?" she gave me a look that made me blink in surprise. "Well if you ever need something simple I am more than willing to do my part. You know for the company of course."

She uncrossed her legs and I could see right up her skirt. She wasn't wearing panties and it was very bare. My restrained penis strained against the chastity cage.

"Kayla what are you..." before I could finish she stood up and walked around the desk.

"I would do anything to get a head in this company. I know the reputation this company has."

"What uh, what reputation would that be." I stammered as she sank to her knees in front of me and she ran her hands up my pant legs.

"To get a head you have to give it. Nothing cums for free." her voice was so sultry and soft it made me shutter just listening to it.

When her hand reached my crotch she felt the hard shell of the cage and she stopped confused.

"What is this?" she felt around and squeezed the hard shell.

I fumbled standing up and looked down at the sultry redhead intern on her knees before me.

"It's nothing. It's just... this isn't a good idea. You should probably..."

She stood up and stepped even closer to me. Her perfume was so sweet and her warm breath made me quiver.

"I'm very devoted to this company. I'll be around sir. Anytime you need to uncomplicate your life." At that she rose up and kissed me right on the lips.

When she pulled away I was still standing there like an idiot as she walked away.

"Just so you know. Whatever side piece you got around here, I can do better. I'd never miss a drop." she winked at me and glanced to the floor.

I stared at her perplexed for a minute before it hit me. She found cum on the floor after that first gangbang. She thought that it was my cum. She thought that I was hooking up with another girl here.

When she closed the door behind her it felt like I could breathe again. If I wasn't caged up right now the things that would have happened just now. I shook my head to clear the thoughts out as I sat back down. I looked at my phone and saw a message from my wife.

It was a selfie of her in a bikini like mine.

"I am so sore from last night's baby. I am walking funny today. Lauren said we are going to the water park again today. You sure you don't want to cum? *winky face"

"You look great honey. I'm sorry I can't come today. I have a convention today."

"That's great! Good luck today! I'll be sure to send you pictures of all the fun we have!"

She sent another picture of the three of them. Lauren had her hands wrapped around my wife, squeezing her full breasts and Jared was naked and my wife's hand was on his hard cock.

Before I could reply back there was another knock on the door. When I looked up I saw Lawrence poke his head around the door.

"Are you ready to go?"

"Yeah yeah how far away is it?" I stood up and frantically tried to straighten myself up. I was so nervous I felt like I was going to a presentation that I was unprepared for.

"It's not far but we will be gone for the day so don't bother leaving anything here."

"Right right of course."

He escorted me out of the room and as we walked around the building I kept finding eyes staring at me. I was so self conscious every look was suspicious. I saw some faces that were familiar. I got winks and kisses and lustful looks from some of the guys I have already serviced. We got to the parking garage and waiting for us was a black suburban with the engine running. I climbed in and Lawrence climbed in next to me.

He was right it wasn't far away but as fast as my heart was beating, every light felt like an eternity. When we pulled into a parking lot to an adult video store I looked at Lawrence who was opening a duffle bag. He pulled out a trench coat and handed it to me.

"I'm going to go in and make sure we are all ready. Take off your clothes and put this on. When we are ready, come in and I'll escort you to a booth. Take your time. There is no rush."

He didn't wait for me to respond. He just opened the door and left and walked inside. I looked at the trench coat and took some deep breaths. I took off my suit clothes and debated taking the bikini off but it was my uniform so I left it on. I put on the trench coat and tied it closed. Before I could open the door I looked at my phone and saw a message from my wife.

She was on her knees sucking Jared's big black cock while Lauren groped her from behind. Jared was holding the phone.

I smiled and tucked the phone into my trench coat and stepped out of the car and marched to the front door. I kept looking around the parking lot to see if anyone could see me but luckily it was completely empty.

As I entered the store I saw the usual rows of porn, stands of lingerie, and wall of sex toys. I scanned around to look for Lawrence but didn't see him. I did, however, see nearly a dozen black men just milling about the store. So not to draw attention to myself I milled about as well.

I saw the sign for booths and walked to the back of the store. I stepped through the curtain and saw a dark hallway and Lawrence talking with another man and money exchanged hands. I stepped up to Lawrence's side and held my head down in supplication.

"Oh yes! That is a pretty one for sure! She will do nicely!" the man said, looking me up and down before leaving me and Lawrence in the dark hallway.

Lawrence turned to me and escorted me into a booth in the middle. I've never been to a video booth before so I took in the sight. On the wall was a small screen that sprang to life when Lawrence fed it some money. The video that popped up was interracial, of course, specifically a petite white woman surrounded by big, haulking, half naked, black men. There was a stool in the corner that Lawrence pulled out for me and motioned me to sit. The stool was really short and it put me more into a squatting position than a sitting one. At this vantage point I noticed the reason for the short stool. I was now eye level with the four holes in the walls, two on either side.

"Okay we have this booth for a couple of hours. I will lock the door behind me so that no one else can come in. If at any point you want to come out, knock three times on the door. Understand?"

I looked up at him and nodded my head. I was way too nervous to form words right now.

"Good! And relax, it's nothing that you haven't done before. Are you ready?"

I nodded my head like a scared little puppy, still unable to speak. Lawrence turned and walked out of the room and I heard the lock set. I was practically shaking, mostly from nerves but also it was cold in the booth. I still had my coat on.

"I love big black cocks!" a female voice filled the silence, "so much better than my pathetic white husband."

It was the woman on the screen, now on her knees surrounded by half a dozen big black cocks. I stared at the screen, transfixed.

"My husband would be so upset if he knew what I was doing right now." the pornstar confessed.

I have to admit I was really turned on right now. My caged penis was straining to get out.

I was startled by a knock on the wall and when I turned I was surprised to see a big black cock jutting from the wall. Steeling myself I stood up and removed my coat and I felt the chill of the cold air hit my pale skin. The only clothing I had on now was my polka dot bikini.

I knelt down at the wall and wrapped my fingers around the hard cock. It shrank away at my touch, startling me. I guess my hands were cold too. I started to stroke this meaty, anonymous, cock. I felt it grow even harder in my hand. I could hear moaning through the wall.

"Suck it bitch." came a muffled deep voice.

I licked my lips and brought my head to the bulbous cock before me. When I wrapped my lips around it I heard satisfying moans through the wall. I took up my duty and began to suck him deep and slow. The cock was so warm in my mouth it sent shivers down my spine. This stranger's cock was the only source of warmth in the tiny room. I quickly got hungry for all the warmth I could get. I began to suck faster and faster. I nearly smacked my face into the wall trying to take his whole cock into my mouth.

There was repeated tapping on the wall that I didn't understand what it was. Until I felt the familiar pulsing of this cock in my mouth and it exploded in a torrent of warm, gooey, liquid into my mouth. After he finished pulsing and pumped the last drop of his cum in my mouth he pulled back and I was left at an empty dark hole in the wall.

"I'm sorry baby, I just love big black cocks!" the pornstar on the screen said.

I turned to look at the tv and the woman was on her phone, apparently, talking to her husband as she sucked the men around her.

There was a heavy handed knock on the opposite wall. I turned to look and found another big black cock jutting out of the wall. This one was standing straight up. It was bouncing in the air like it was beckoning me closer. I crawled over to the opposite wall and began sucking this cock now as well. It felt even warmer than the last one. I moaned as I took the warm cock into my mouth. I didn't waste any time on this one and immediately sucked this cock hard and fast.

There were two knocks back on that other wall now. Not wanting to just stop, I began stroking this cock and turned my head to look and I saw now two hard black cocks sticking out of the wall. The booth was small enough I could grab a cock on opposite walls. I turned back to the cock at hand but the moment I turned my head back I was hit in the face with a blast of cum.