Sissy Awakening Ch. 04

- Sissy Goes to Work -

The morning had arrived and I had to get dressed for work. I wasn't sure what to wear though. I didn't know what Doug want going to have me do now that I was changing to an office position.

I took the breast forms, glued them in place onto my chest and found a matching bra and panty set that was simple black bra with a cheeky panty. I pulled a blue dress off the hanger and pulled it up over my hips. Looking in the mirror I could see a bump where my balls protruded from the cage slightly, and the top of the breast forms were visible. I'd need a sweater. I ditched the dress in a pile. I grabbed my red tartan skirt that let the tops of my knees poke out and paired it with a nice pink blouse. I felt I looked too little girlish for an actual job. That too was ditched into the pile of rejects.

Sarah finally came in to help me. I didn't have much time left to mess around, so she sat me down and did my makeup for me. That calmed me down a bit and I started relaxing. I needed to think simple. Once Sarah did my makeup I looked quite wonderful really. She was so good to me even though all the issues we were going through. I pulled a simple black skirt from the pile on the floor and buttoned up a white 3/4 sleeve blouse and topped with a nice red jacket. I looked nice and professional at the same time. When I walked in the 3" pumps, I could feel the air caress my legs nicely.

I said goodbye to Sarah and hugged her tightly. She held onto me a moment longer than normal and kissed me on the forehead. I was already going to be late.

I pulled into the yard so nervous. Parked my work truck and stepped into the office. I walked right into Doug's office first. He looked up from his desk.

"Can I help you ma'am?" He said to me.

I was surprised that he didn't recognize me right off the bat, and he called me ma'am. That meant I was at least passing for the first couple moments. That made me happy, and I smiled at him.

"It's me... Samantha!" I said to him with a big smile on my face. It didn't initially register, so I said "Sam?!!"

Realization hit him and he sat back in his chair. I wide smile played across his face.

"Jesus Christ! Come over here and turn around for me!" He said excitedly.

I walked over just out of arms reach and threw my hands out to my side and spun around slowly letting him drink in the view.

"Lift that skirt, lemme get a look at that fine ass of yours!" He demanded.

I just looked at him. It felt good to be desired, and wanted. I liked how he wanted to see my body, but I was conflicted. I didn't want to just come here and fuck the boss... but that wouldn't really be the worst thing in the world. So I lifted the skirt up over my hips and thrust my ass cheeks out as I turned my ass toward my boss. I bent at the waist and shook my ass making my cheeks jiggle. Next thing I knew, his face was buried in my ass crack. He was sniffing in deeply, smelling my ass. His hands were clutching wildly at my hips and I shook my ass on his face.

He broke free as I stood and let the skirt fall back below my waist, and turned around. He was still on his knees when I walked past him to his side of the desk. I sat in his chair and leaned forward. He walked up to me and stood with his crotch at my face. I knew he wanted to fuck my ass but I only had one pad in my purse and I didn't want to use it first thing in the morning.

He pulled his cock free and brought it up to my mouth. It was hardening in his hand as I reached out with my tongue and licked the tip. Almost in one motion, he let go of his dick and I engulfed it into my mouth. I sucked and bobbed on his cock while playing with his balls. I wanted his cum in my mouth as soon as possible. I could feel he was close, and he started pulling away from me. I clapped my mouth around his dick and let go. Holding his ass cheeks I pulled him into me and forced him to cum in my mouth. I felt his knees tremble as he unloaded his hot sticky seed into my throat.

He stood there with his softening cock in my mouth and his hands at the back of my head as I continued rolling his cock head around my mouth. His hips were still bucking when he finally broke free from my grasp.

"Where the fuck did you learn to suck a dick like that!" He worded breathlessly.

I opened my mouth to show him his cum. I rolled it around my mouth with my tongue before I closed my mouth and swallowed the whole load. Then I opened my mouth and showed him it was gone.

"Yummy!" I said.

I felt like such a dirty whore swallowing his cum like that, but at least I wouldn't be leaking his cum out my ass pussy all day! I stood and swapped positions with my boss. He sat and smiled as he watched me move around to the other side of his desk.

"God, what am I going to do with you?" He asked rhetorically.

I sat across from him and crossed my legs. I could still taste his cum in my mouth. I liked the taste of his cum and was getting used to the idea of being his personal work toy.

"Well... Walt, the purchasing guy just retired a few months ago. I've been doing his job. I guess you could help with that for the time being. You'll have an office down in the basement. Get with Pam. She can help you get set up down there." He said.

"Oh, like I have an actual job?" I said somewhat surprised.

"You didn't really think I was ONLY going to be fucking your mouth and ass did you?" He asked rhetorically.

"No, you'll have to actually do some work too. But there're some benefits to being my special girl!" He added with a wink.

"Hmm, I like the sound of that!" I said.

"Go get settled in and I'll come help you get started." He replied before returning to his work.

I spun on my heels and walked out the door to find Pam. She had been sitting at her desk right outside Doug's office. It was clear she could hear everything that had happened because of her disdainful look.

"Come on then, let's go to the basement." She said irritated.

We walked down the stairs, and I couldn't help but notice her perfume. It smelled really nice. I had to get some for myself too!

"Your perfume smells wonderful, what is it?" I asked.

"It's not for whores!" She snapped back.

Well okay then! I'll have to remember not to fuck with Pam! She is a BITCH!

I remained quiet the rest of the trip to the basement and once there, she just pointed to the desk, and walked away. I spent the morning setting up my desk alone. Around lunchtime I snuck up to the break room to see what was going on. It seemed that Pam had already turned half of the office staff against me. Figures... I'd just eat alone.

About an hour after lunch, I was just sitting at my desk looking over accounts when the yard manager came down to see me. Usually an email would do the job when someone needed something, but he had to see if the rumors were true.

Daniel walked in and peeked around the corner to look at me without being seen. It didn't work though. He was a good-looking guy with his short hair and scruffy beard. He'd always been a skinny guy but in the last couple years he packed on some weight in muscle. He'd been through a divorce and was back on the market.

"What can I do for you Daniel?" I said to him as he peeked around the corner.

"I wanted to see if it was true!" He said rounding the corner.

"Jesus man, you're fuckin' hot!" He added.

"Um, thanks." I said.

He had crossed the room and was standing right next to me. I could see his bulge sticking out right at eye level.

"Do you maybe need some help with something?" I said still staring at his bulge.

He didn't say a word. He just pulled his pecker out a couple inches from my face. It was already hard, and smelled like musty ball sweat. His cock pulsated as it started at me. I grabbed his dick, it was so smooth and warm. I rubbed down its 6" length. The length may have been average but I had to stretch my mouth all the way open to fit it in my mouth. I wondered how it would feel in my ass.

I stood up, still sucking on his cock, I pushed him away from my desk, and reached up under my skirt. He was fucking my face as I dropped my panties around my ankles.

I flipped my skirt up over my hips and turned around, offering him my ass. Daniel didn't seem to care what hole he was using and he placed his swollen dick head right at the entrance to my sex hole. He grabbed the material of the skirt into his fist and pulled himself into me.

His balls started slapping my own and my clitty was hard as a rock inside its stainless steel prison. I so desperately wanted to tug on my cock right then but I knew it was only a matter of time before it was spurting without any stimulation at all.

Moments later I looked down to see the first strings of cum forming at the tip of my cage. The waves of pleasure seemed to wash through my insides and right out the tip of my cage. Daniel was pounding my ass. Noisy slapping and grinding sounds had to be pouring up the stairs to the rest of the offices. I felt so sexy thinking other people could hear me having sex!

Daniel grunted loudly and pulled on my hips. I could feel the wads of cum being shot into my fuck hole. My ass pussy was still quivering from the aftershocks of my own orgasm. We both stood there, I bent over and Daniel softening in my ass, trying to catch our breath.

Out of the corner of my eye, I could see two women watching us. I didn't know how long they had been there or what they had actually seen but they watched as Daniels cock softened and fell out of my ass pussy. They watched him walk right past them and then they watched me grab the pad from my purse and put it in the crotch of my panties to catch the cum that was no doubt going to start leaking from my hole at any moment.

I pulled my panties back up, straightened my skirt and sat back down.

"Does either of you need help with something?" I asked the two women.

They didn't respond, they only giggled and left. I recognized the one but couldn't remember her name. I always liked looking at her hot little body. I'd love to have a body like her's. I could do so much more with it than I could my own. Little flutters raced through my chest as I thought about having sex with some hot young stud in her ripe young body.

I must have daydreamed the rest of the day because when I finally noticed, it was already time to go home.

When I stood up, I noticed how wet my butt was from the cum that had leaked out of my ass. I thought back to when Daniel deposited his seed there and smiled to myself.

I sat on the toilet trying to expel the remaining cum from my hole when I heard three women enter the bathroom.

"Jen said they were having sex when she went down there with Pam and Jill!" The woman said stifling a laugh.

"Really, Daniel and Sam!" Another woman said disbelieving.

"She apparently goes by Samantha now!" The first woman added.

"I think she is really pretty." The third woman said.

The other two women laughed and called her a lesbian as they walked back out of the bathroom.

"You really are pretty... some people have no idea the struggles we go through Samantha." The third woman said.

I had finished my business quietly and dropped my skirt back around my legs. I cracked the door open to see the adorable sexy girl I had recognized earlier. I still couldn't place her name.

"That was really nice of you to stick up for me like that." I said to her.

"Would you like to go have some coffee with me tonight?" She said.

I weighed my options. Sarah was likely with Jake and she probably wasn't expecting me anytime soon anyway. Yeah... I could probably spare some time.

"I'm sorry, I can't remember your name. It's been a while." I said sheepishly.

She looked genuinely hurt that I'd forgotten her name, then she laughed quietly.

"Trinity, it's Trinity." She said.

"No, I knew that. What was your last name?" I added.

"Oh, Stevens, it's Trinity Stevens!" She said smiling at me.

"Sure, where do you want to go Trinity?" I said.

"Well there's a coffee shop right around the corner from my house, they make a great latte!" She said.

I gave her my phone number and she sent me a pin to the coffee shop. We both walked out together and drove to the coffee shop. She ended up living about four blocks away from me is all. I'd seen the coffee shop before but never thought to stop by. It was very trendy and there was a large LGBT presence there. I didn't realize it, but we both had to have lived in the progressive area of town.

We sat and drank our coffees while listening to various different people play their songs at the open mic night. We talked about how I had hired her 8 years ago for the payroll position when the office was much smaller. How it was working in the company and what she thought when she saw the changes I'd gone through over the last few days.

I was really enjoying my time with her, so much so that it had gotten dark by the time I'd realized it.

"Would you like to see my place?" She asked.

"I'd love to!" I said without thinking.

"I can't stay super late though, I've still got housework to do tonight." I added.

She gave me her address and we met at her place. She lived alone in a two story rambler that she inherited when her parents died. She had to buy her sister out but the rest of her inheritance covered that. She just worked to pay her monthly bills at that point.

She gave me a tour of her house that ended in her kitchen with a glass of wine. I wasn't much of a wine person but I obliged and had a glass with her that turned into two then five then I lost count.

"Hey, what's behind that door?" I asked her.

"That's my sex dungeon!" She said with a smirk.

"It's fine, you don't have to tell me if you don't want." I replied.

"Do you want to see it?" She said getting up and pulling a key from her pocket.

She opened the door and walked down the stairs. I followed a few feet behind her so I could look at her ass. I almost expected to see a game room or something but once I hit the bottom landing, I immediately recognized the St. Andrew's Cross and an entire wall of whips, straps, and various different bondage implements.

My clitty hardened inside its cage at the sight of all the wonderful things she had.

"I thought you were kidding, this is unlike anything I've ever seen Trinity!" I said.

"Down here, it's Mistress Trinity, up there it's just Trinity." She said.

"Oh, my apologies Mistress Trinity." I said while bowing my head to her.

I walked around touching the various pieces of furniture. I imagined myself bound to each one and end mounted the spanking bench. I noticed the straps that would go in each arm and leg. There was even a strap that looked like it might strap the bottoms cock and balls to the fence further immobilizing them. I imagined Mistress Trinity swatting my ass while I was bound to the bench.

She was smiling the whole time I was playing. I stopped at the stocks and she raised her eyebrows as I lowered my head into the largest hole and my arms into the smaller holes.

"Would you like to feel how restrictive that can be?" She asked.

My heart raced, I loved the idea of bondage but wasn't sure if I would actually like it or not.

"Sure... sorry, yes Mistress Trinity." I said.

She cranked on a large handle that lowered the head and arms down to where I was bent over at the waist. Then she pushed a thin table under my torso. Trinity dropped the top off the clamshell down over my arms and neck, then strapped my waist and legs to the table under my belly. I felt wonderfully immobilized. I felt a sharp pain in my arms and neck when I tested their hold and couldn't check my legs at all, they were completely immovable.

"How does that feel Sam?" She asked.

"Wonderful, Mistress Trinity!" I said.

"You know, I could do anything I wanted to you right now don't you?" She said playfully.

"Mmm... Yes Mistress Trinity, anything you want!" I said trying to say it with double meaning.

"What would you say if I told you that I was actually born with a penis Sam?" She asked.

"I don't think that would ever be an issue Mistress Trinity." I said.

"What would you say if I told you that I haven't touched my penis in almost a week Mistress Trinity?" I asked jokingly.

"Id say that we should see how long you really can go Sam!" She replied

"Are you sure you really want me to do anything I want to you?" She asked.

I felt so vulnerable strapped to that piece of furniture. I could feel my cage bump into the table below me. I could turn my head from side to side but it was very limited. My hands could only grasp at the air in front of them. Yes... she could have done whatever she wanted to me. I almost wanted her to do something, anything to me!

"I'd like to think that I'd like it. I'd hope that I liked it as much as you Mistress Trinity." I said.

"I would so love to play with you, explore your physical boundaries and the boundaries in your mind!" She whispered from behind me somewhere.

"You need to figure some things out with Sarah first." She said as she swatted my ass with what I assumed was a riding crop.

"Mmm... thank you Mistress Trinity!" I said.

Trinity removed the straps holding my legs to the table and lifted the top half of the stocks, allowing me to stand up. I could feel my clitty straining at its cage. She had only hit me once and I was hard. She made me so fucking horny, it was like I was 23 again! If only Sarah would be willing to do something like this with me, I thought.

We returned to the kitchen and she locked the door behind us. She pulled me into a hug and I could feel her breasts pressing into my ribs. She was somewhat short with nice smelling red hair and emerald green eyes. She was much thinner than I'd realized, when I wrapped my arms around her I could feel her ribs. I thought for a moment that I could feel something else pressing into the top of my leg. It had to be her stiff girl cock. I imagined what she might do with it if she had the chance. I imagined what I might do with it if I had the chance!

She walked me outside and stood at her side door as I headed to my truck. I had really over done it with the wine and thought better than to drive. I should probably walk home. Besides it was only 4 blocks away, I walked further from the Miller's the day before when Sarah forgot to pick me up.

"Is my truck okay here until morning? I've drank too much and should probably walk home." I asked.

"Sure, give me your keys and I'll just pick you up in the morning." She suggested.

I tossed her my keys thinking that'd be a great idea and spun on the balls of my feet in a great mood to start walking home. The night was cool and I enjoyed the feeling of the air in my bare legs. My skirt swished side to side with my hips and the fabric gently brushed the outside of my legs. I could feel my fake breasts bouncing with each step and I tried to imagine what it would be like if they were real.

- You win some, You lose some -

I got home and the lights were all out. I had given Trinity my keys, so I couldn't get inside. Sarah's car was gone so I knew she wasn't home either. I checked the garage door, and side door, then the back door too. They were all locked. My next hope was my bedroom windows. I couldn't remember if I left one open or not.

My windows happened to be open so I could crawl through there. It would have been hard enough in pants and boots but in pumps and a skirt, it was ten times harder. I fell inside with a loud thunk. It was pitch black, and I couldn't see a thing. I flipped the light on, and wandered through the house looking for Sarah. I found a note on the kitchen counter that was addressed to Sam.

(Dear Sam,

I left and I'm not coming back. I don't love you anymore. I can't offer you what you need. I thought I could incorporate your new desires into my life but I realized when you left for work this morning that I need a man, not a sissy and not a woman. I don't want to talk about this, you'll only mess with my mind. If you ever loved me, let me go.