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My New Boss
Working almost an hour from home is never ideal. Sure, being from a small town in the middle of nowhere makes that almost impossible, unless I wanted to try and retire from fast food. So, I have no other options than to hop in the car every morning to drive across the state to my office job. There is a plus side though, working in a larger area gave me much more opportunities to meet new people.
Growing up in a small town in Michigan was always bound to be hard for someone like me. I knew from a young age that I was different from the other boys in my class. When they were talking about seeing Pamela Anderson bounding down the beach, I was thinking about Brad Pitt flexing his abs in Fight Club. When boys would talk about what it might be like to finally grab a tit, I was thinking about how it would feel to wrap my hand around a cock other than my own. It was hard to play it cool when in a crowd of the other boys, but I made it through nonetheless. But the hardest part growing up like me was knowing that if I stayed in my hometown that I would never experience those things that I truly desired. When you are a straight young boy, a crush never means never, but when you are a young gay boy in a small town, it always means never. Depression always hit me hard so when I eventually graduated high school I knew that I needed to get out, no matter what it took.
College was always out of the question. My parents were always stuck in the small town living that slowly turns into a form of complacency that you learn to accept. Money was always tight because working in small town businesses only allowed you to make enough money to keep the heat on, then gas up the car to drive back to work. College was always preached to me as "unnecessary" and "luxury", which turned into, "whats wrong with working at the gas station? You can make $8/hr!". Thinking that statement is reasonable is the reason they will never leave, and why I had no choice but to at least try.
I applied for what seemed to be thousands of jobs on Craiglist that always seemed to go into one email inbox, then made it directly to the trash. Sure I knew that I was inexperienced, and I live nearly two hours away from any job I applied for, but I was ready, ambitious, desperate.
One day when I got home from part time job at the local convenience store, I opened my laptop to check my email, hoping that I got a response. Sure enough, there it was, one unopened message from a company called "Painter's Insurance Company". I don't remember applying for them, but the heading started with "Good afternoon Ryan,".
Couldn't have been a fluke, that was my name. Reading further into the description, it listed some of the responsibilities which included: receiving calls, taking notes for the agents during meetings, getting coffee when requested. Seemed like normal secretary work, or what I imagined secretary work. What caught my eye next was they pay. Starting out I would be making $18/hr! I jumped right to the reply button to show my interest. I typed a short response detailing some of the reasons that I would be a good employee, a little about my background, then attached my resume, then pressed the send button. I crossed my fingers, toes, everything! I leaned back in my chair and immediately began to daydream about what I could do with that kind of money. The feeling of finally getting away from this prison seemed to be getting closer with every breath.
The remainder of that night, and the next shift at work I could barely think about anything else. I wanted 3pm to get here so I could rush home, and hopefully see my answer. The time finally came. I jumped into my car, and sped across the two blocks to my home. I ran inside, kicking my shoes to the corner, and sprinted to my bedroom. I opened my laptop, and opened my email. Nothing. No new messages. My heart sank with disappointment. I figured that maybe my experience was just not enough. Maybe I showed too much excitement in my reply, and they figured that I was maybe just too immature. Either way, I wanted to cry. When something so great feels so close, only for it to speed away almost feels worse than ever having hope in the first place. But just as I was about to close my laptop, the "ding" of a new email sounded. I flipped it back open, and navigated back to my email. It was a reply from the insurance job! My heart went from sinking to pounding through my chest. I opened the email, and began to read.
Dear Ryan,
We are happy to hear that you are interested in working for Painter's Insurance Co. We are one of the fastest growing insurance agencies in Michigan, with more that 1000 new customers each month! As you saw in our job description, we are looking for a candidate that will mesh well with our very small team, and is not afraid to take chances. If the position does seem like it is an entry level, that's because it is! The entry to a career with a family owned business that plans to be around for many years! There are only a few things that we will need from you at this moment. First, we need all of your personal info so that we can set you up as an employee. Second, we will need a full body shot of you in a tight white t-shirt and nicely fitting black pants for your employee photo. Then finally, just a list of previous relationships you may have had with anybody (girlfriend, boyfriend, etc.). And that's it! We do look forward to hearing from you soon, and also look forward to working with you in the future.
Sincerely,
Bradley P.
I couldn't believe it. Were they just trying to hire me on the spot? My excitement was now going wild! I read through the list of things that he needed from me again, and they all started to seem kind of weird. Sure, the personal info seemed normal enough, but a full body picture of me in a tight white shirt? Also, why would they need to know my previous relationships? I considered all of these things, then realized that none of these things mattered if it meant that I was going to be making $18/hr!
I first typed out my response, filling in my personal info, then letting them know that I was never in a relationship before, which felt kind of awkward. I then was tasked with finding a tight fitting white shirt, and tight fitting black pants. All of my personal clothes were what I would call, raggy, outdated? Nothing I owned was particularly nice. I dug and dug through my clothes, but all I could come up with was just some torn jeans, and black band shirts. Shit. I began to think where I could find a outfit that he had described, and all that I could come up with were some of my sister's black leggings, and maybe a shirt that she may have?
I was never a big guy. My frame was what you would consider small. I was barely 5' 8" and on a good day I would weight 120lb. I was a shrimp my entire life. My older sister Sarah would always pick on me because I never grew past her, we were always close to the same size, heck, we even looked the same. It was always embarrassing when we would go to Christmas at our grandparents and grandma would always call me Sarah.
That is when it clicked in my head, Sarah would have to have something. I figured that if I did find something, all I would have to do is make sure that the camera didn't make it obvious that I was wearing my sister's clothes. I crept down the hall to her room which was situated across from my parents'. I cracked the door to make sure that she was still at her boyfriend's house, and noticed that her room was empty. I pushed the door a little further, then stepped in, clicking the door behind me. I walked over to Sarah's closet and slid it open. She had a small dresser in the middle of the hanging dresses, jeans, and everything else a girl could not fit in three drawers. I opened the second one down, knowing that the top probably contained a pile of panties. Jackpot. The drawer was full of leggings. Black, pink, tan, red, every color imaginable. I pulled out the first black ones that I saw, then closed the drawer. I held them in front of me, and realized then that the material was amazingly soft and stretchy. I pulled the waist band, then let it go, not knowing how wide they could actually go. I threw them over my shoulder, then started the search for a simple white shirt. The drawers past the second were a no go. They only had more jeans, sweatpants, and a couple long sleeved shirts. That was when I decided that I would have to take the chance, and open the first drawer. Sure enough, it was the panty drawer. It was overflowing with colorful underwear. I tried to search through and luckily, I found what I was looking for. She had a small pile of nearly see through white shirts that were pile to the left of the drawer. Again, I grabbed the first one on top, then shut the drawer. I took my bounty, and made my escape.
Once back to my room, I figured that this would be as good of a time as ever to get it done. I dropped the jeans that I had been wearing to the floor, then pulled my work shirt over my head. I was standing at the foot of my bed looking at the women's clothes that sat before me. I decided to go with the shirt first, knowing that it was probably going to be just a shirt. I pulled it over my head, and let it fall down my torso. The fabric felt amazingly soft, almost luxurious, and this was just a shirt, what was everything else like. I grabbed the leggings, and stepped into each leg, then pulled them over my hips, and onto my waist line. The fabric felt even better. The tightness that the pants had on every curve of my legs felt amazing. I walked over to my full sized mirror on the back of my door to take a look. What I saw made my jaw drop. My grandma wasn't far off when she mistook me for Sarah. I really did look like her aside from the hair. Sarah always had hair that went down her back, where I always kept mine somewhat long for a guy, about jaw length. Everything else though was just so close.
I shook my head to get out of the trance I was in, and remembered that I had a job to do. I set my phone on my desk, set the timer, then backed away so that I could get my entire body in frame. The flash went off, and I grabbed my phone to check. Looked good to me but what I did notice was that you could clearly see that my boxers were bunched up under the leggings. I figured that it was just for an employee pictures so I attached it to the email anyways. I sent the message, and waited for the response on what to do next. I got up from my chair, and dressed back in my clothes, almost missing the feeling of the foreign materiel on me, but I knew that Sarah would be home any moment and she would kill me if she knew that I was parading around in her clothes.
I clicked Sarah's door behind me closed, then made my way back to my room. Once I opened the door I could see that I already had an unread message. I checked, and it was a reply from the message that I had just sent. I quickly opened it and started to read.
Dear Ryan,
I was please to receive your info and pictures! They look great! Exactly who we are looking for! One issues that we can see though. Under you black pants, we can see what we think is the outline of your undergarments. Here at our agency, that will be unacceptable. When you come in for your first day, be sure to not have anything that can be seen through your pants, but please where those exact style pants. Other than that, they look great! We are pleased here at Painter's to off you a position as secretary! If you are to accept this position, your first day will be scheduled for next Monday at 6am sharp! We look forward to you joining our team!
Yours,
Bradley P.
I jumped at the email, pumping my fist in the air with triumph! I had finally found my way out of this small town! I quickly sent a reply saying that I was interested, and looking forward to working with them. But when I sat there and considered, he had seen my boxers through my pants, and they still wanted me to wear those exact pants? Did he notice that I was wearing leggings and not just some formal black pants? I did not want to try my luck so I knew that I would have to just wear some black leggings. But where would I get some from? I didn't have the balls to go and buy some from the local Walmart! Maybe if I were just able to borrow Sarah's, she wouldn't even notice? I mean, she does have like thirty pairs in her drawers. But I also had another dilemma. I didn't have anything to wear underneath them, I mean, nothing that wouldn't be able to be seen. All I own are boxers. Maybe I could go commando, that way I have zero chance for my undies to be seen. I decided then that I would have to just suck it up, and grab the leggings back from Sarah.
I crept back into Sarah's room, and made my way back to her dresser. I opened the drawer to the leggings, and grabbed the ones I had before. I threw them over my shoulder, and decided also that I should probably grab a white shirt from her as well, just until I could go buy my own at the store. I opened her top drawer, and grabbed the white shirt from where I left it. My eye then was drawn to the pile of panties that were laying there. I thought to myself then that I would never be able to just go to work with no underwear on. That would be insane. But I also knew that I had no other options in my own wardrobe. I sifted through her pile of panties and found a nice, black, simple thong that might just work. I grabbed my haul, and made my way to back to my room.
Once back in my room, I looked at the pile of women's clothes and started to think that I may be over my head. Sure, I had just worn the top and bottoms, but I had never worn a thong! The thought first scared me, but then, it started to thrill me. I could feel a warmth all throughout my body at the thought of pulling on some women's panties. With a flash, I pulled down my manly pants and underwear, then stepped both legs into the black thong. I pulled them up to my hip, then spread my cheeks so that the string would set snugly in my crack. The tightness that they gave me around my pitiful package felt wonderful. I walked around my room, exaggerating each step so that I could clearly feel the fabric tickle my asshole. The fabric that was now cupping my small cock, and balls was nearly making it look like I didn't have any to begin with. I was in love at that moment. My heart was racing. The new experience of having another gender's underwear on was nearly overwhelming. I decided then that I would give these a real try by wearing them under my manly pants for a but, just to see if I could do a whole day in them. I pulled on my jeans, stuffed the rest of the clothes in a safe spot for Monday morning. Then I chose to go for a walk around the neighborhood. My secret keep safely behind my men's pants.
Over the weekend, I didn't just wear them on that walk. I wore them the entire weekend! I loved the way they made me feel. The soft satin fabric, the way they sat high on my hips, the way the string would every once in a while rub my puckered hole, the way that they almost made my cock disappear. Everything. And when Sarah got home that night, she was none the wiser. She went the entire weekend without even saying a word. Maybe it was because she already had a mountain of clothes so she would never notice anything missing.
Monday finally arrived, and I could not sleep the night before. I was up ten minutes before my alarm and started to get ready. I took a shower, but that didn't go as planned either. My body wash that I had normally used was out, so I had to reluctantly use Sarah's. But to my surprise, I absolutely loved the smell. The scent of lavender filled the steamy bathroom, and I knew that I was in love at that moment! Even after I got out, I would still smell my arms, getting whiffs of the girly scent that was now intoxicating. When back at my room, I pulled on the black thong that I had washed three times over the weekend, just because I couldn't keep out of it. I pulled over the tight, white shirt, then pulled up the leggings to my hips, feeling the tight, elastic material hug all of my curves. I stepped over to the mirror to take a look, and who was looking back at me was not Ryan. I looked myself up and down, noticing the good choice to go with a thong. I spun around to check out my ass, and noticed that the leggings were slightly riding up my crack, defining both cheeks very well. I almost pulled them out, but decided against it, my ass looked great! I looked around for some shoes that would work with the outfit, and the only ones that I could find were some low top Converse that went extremely well with the outfit. Before stepping out of my bedroom I got one more good look at myself in the mirror, then stepped out to my first day on the job.
The drive to the office was not nearly as bad as I thought it was going to be. Yes, it was almost an hour long, but I was also able to catch up on some of my podcasts that I had been missing out on. I pulled up to the building of Painter's Insurance Co. It was a single layer brick building that had a double door in the center, and windows to either side. I walked through the double doors, and was greeted by a young women that was sitting at the front desk. She was on the phone when I walked up, so I sat next to the chest high counter to wait for her to finish up.
"Yes, Mr. Painter will be glad to see you this after noon. Yes, he will be here this time."
The tone of the women's voice through me off for a second. She almost sounded like her voice was deeper than it should be.
"Thank you Mr. Peterson, we look forward to seeing you this afternoon. Bye bye." she hung up the phone, then swiveled her chair in my direction. "Hi, how can I help you?" s
"I'm Ryan, I'm actually here for my first day."
"Oh right, I remember seeing your face. Bradley is on a call right now, is there anything I can get you while you wait?" the nice women said.
"Nope, I should be fine, but thank you."
"I'm sorry, where are my manners. I'm Seth."
This caught me off guard, Seth?
"Nice to meet you Seth." and I shook her hand.
"If you want to just have a seat over there, I will let him know that you are here." Seth said. Pointing to the banks of chairs in the corner.
"Thank you" then I turned towards the chairs.
My mind was now in a million different directions. Was Seth a women? Was he trans? I was not sure what to even think, but I had no further time because just as my ass hit the seat, the large wooden door on the wall behind where Seth was sitting opened.
"Ryan?" Bradley stood in the doorway to his office. I stood up and walked towards him with a smile. "Ryan, I presume?" he said, extending a hand towards me.
"Yup, I'm Ryan. Nice to me you." I said, returning my hand to meet his.
"I'm glad to see you, come in, please." he turned towards his giant office, an I followed him in.
Once in he made his way behind his desk, and sat down in his large, leather chair.
"Please, have a seat. Is there anything that I can get for you?"
"I think I should be fine for now, but thank you." I said, pulling out a chair from his massive oak desk, then taking a seat across from him.
"So, how do you like the building so far?" he said, clasping his fingers together, and focusing his eyes on me.
"It is exactly what I'm looking for!" I responded
"That's great to hear!"
"But I do have a few questions though. I guess I was just a little confused because I thought that the job description said that I was going to be a secretary? Wouldn't that be what Seth is out there?"
"Wow, getting right to business I see. I like that." he smiled. "You and Seth will be splitting the duties of secretary. While one of you is busy with a client, the other will be running the front desk. Kind of like a secretary team, if you get my drift?"
I nodded, giving him the impression that I did, but truly, I didn't. "See, here at Painter's, we like to treat out guests with the best service in the business. The majority of our customers here have a particular taste in women, and normally, they are afraid to explore these interests. We give these gentleman a chance to explore those desires in a setting that is both private, and confidential."
"So you run a brothel?" I said, trying to understand but failing.
"No no no. We just offer them the chance to act on those desires, but also buy insurance from us, just so the people they don't want to know are non the wiser."
I nodded, still trying to see where he was going. "But, when you say women, I'm not a woman though?"
"I know, but you can pass as a woman easily though. And I guess that I used the term woman incorrectly. These men are looking for sissy little men that will treat them right. You kind of see what I'm getting at now?"
"I guess I do. But, does that mean that I will have to sleep with some men?" I asked, my curiosity now becoming excitement.
"I'm not going to say exactly what you will have to do because it is different with every client, but yes, some of them prefer to get a little frisky from time to time."
"Oh, wow. I guess, how did you know that I would be the right candidate for this role?"
"We really didn't usually we just scout through people's social media pages, looking for the right fit. Seth out there came across your Facebook, and noticed that you had the right body for what we are looking for. Further into your page, we notice that you weren't outwardly gay, but we could tell that you were interested in men."
My cheeks flushed at that statement, maybe I wasn't being that careful.
"So that I why you needed me to dress in something a little tighter? See if I could come across as a women?"
"You got it. So, do you think that you are ready to see you first client?" Brad said, standing from his desk, and walking towards his large wooden door.
"Well, sure, I guess." I said, standing from my chair, and pushing it back into place.
"Great! Because I believe we have one of our most loyal customers here right now. Jim! How are ya." Bradley said, extending his had to a large man next to the desk where Seth was sitting.
"Great Brad! So I hear you have a new secretary starting today?" Jim said, looking over in my direction.
"We sure do, this is Jenny. Jenny this is Jim. He has been with us for years."
Jenny? Did he just introduce me as Jenny?
"Nice to meet you dear." he shook my hand lightly.
"Now why don't you both go ahead to room one over there." Brad pointed to a door in the lobby that had a large, red one attached to the front. "Remember Jim, you only have twenty minutes this time."
"Yeah I know, I wont go over this time." Jim said, grabbing my hand again. "Why don't you follow me sweety." He guided me towards room one.
Once inside room one, I noticed that it was decorated nicely. It had simple paintings that looked like they were picked up from Ikea. The bed towards the back of the room was a queen sized that had a deep red comforter that was spread across it. The only light that was in the room was from a side table lamp that was on next to the bed, but it was incredibly dim.
"Why don't you go ahead and sit over there while I get ready." Jim said, pointing to a chair that was against the wall. I did as he told, and walked over to the chair, sat down, and crossed my legs like I had seen so many women do. Jim began to undress. He unbuttoned his pattern shirt, revealing a relatively large dad belly. He pulled the shirt from his shoulders, and I noticed that he had a good blanket of white hair across his torso. He locked eyes with me, then started to unbutton his pants. His pants fell to the ground, and he was not wearing underwear. The blanket of white hair did not stop at just his torso because he also had it surrounding his chubby, uncut cock.
"You like what you see huh?" he said, grabbing the thick, wad of flesh that was sitting on top of a massive bag of balls. I nodded back to him. "They why don't you come over here and see what you are missing." he was now stroking his cock, which seemed to grow fatter and fatter by the second. I walked over to him so that I was standing directly in front of him, my eyes level with his chest. I sat the palm of my hand on his chest, and started to rub his hairy chest, slowly working my way south over his cute belly , then taking over the stroking on his fat cock. His head tilted back as my hand grasped his member.
"Yes baby, you know what to do."
Truth be told, I didn't. This was the first time with another man's cock in my hand. I stroked harder and harder, but then I started to kneel down so that his cock was now eye level with my face. The smell of man cock wafted across my nose, and I knew then that this is exactly what I wanted. I pumped his cock a few more times before I opened my mouth wide, then sat the head of his cock on my lips. I danced my tongue across the tip of his cock, stopping only to teasing his piss hole.
"Yes baby, you know how daddy like it." I look up at him and he was now twisting his own nipples vigorously. I opened further, and started to push his cock further into my mouth, my tongue dragging across the under side of his shaft. Before I knew it, my nose was now sitting in his large white bush, his cock was now at the back of my throat. I let it sit there for a moment until my gag reflex took over. I pulled it from my mouth, along with a big string of slobber. I immediately slammed it back in, then aggressively started my mouth assault on his cock, pumping harder and harder on this old man's fat cock.
"Oh fuck baby, you better slow down, daddy wants a chance at that ass!" I did not listen, I wanted to taste everything that this man had to offer.
"Oh fuck baby, shit, I'm going to cum." I grabbed his ass from behind, and pulled him all the way into my mouth. His cock began to swell, then spurt fountains of cum directly down my throat. I slid my mouth away from his so the tip of his cock was now resting on my tongue, cock still pumping a lake of cum onto my tongue. I loved the taste of this old man's cum, I knew that I would.
"Holy shit baby girl, I knew you were going to be great, but no one here has ever sucked the cum out of me." I pulled his now shrinking cock from my mouth, then looked up at him with a slimy smile. I was still gulping his cum down. He walked over to his pants, then pulled them over his wet cock, being careful with his zipper. I stood up, and walked over to the door to the lobby, and waited for him to dress. Once he was dressed we walked out to the lobby where Seth was back on the phone with somebody, and Bradley was sitting there with another customer. He looked over to see me exiting the room.
"Jenny! Jim! That was not nearly twenty minutes!"
"I tell you what Brad, you got something special here." Jim said, gripping my shoulder.
"Well that is great to hear, I knew Jenny was going to fit in nicely here."
"Well thank you little lady, and thank you Brad but I have to get going." Jim turned, and walked to the doors.
"Well Jenny, since that took a little less time than I had thought, we have another client here that is ready to see you."
A tall man stood from the chair next to Bradley, and extended his hand. I shook it. The taste of Jim was still heavy on my tongue.
"This is Chris, he is another great client of ours, he has requested an hour with you today." Go ahead and use room two this time."
Two hours? What could happen in two hours?
"Come on honey, why don't you follow me?" Chris said, grabbing a handful of my ass, then pushing me towards room 2.
I was realizing that maybe I could learn to like being Jenny.
Thank you for reading! I plan on making this my first Sissy series. I love where Ryan is going, becoming Jenny, and also realizing how much he does like to wear women's clothes!
If you like this story, feel free to check out my Patreon at patreon.com/TedDavidson_Writer and also don't forget about my book that is on Amazon. It is titled "Snowed In With My Best Friend" by Ted Davidson.
Thank you for reading!