The Applicant

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Cross-dressing man gets job as female secretary.
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bunny3374
bunny3374
138 Followers

Chapter 1

I worked in an office as a secretary, and my friend Margaret worked there too. It was our job to interview new candidates for positions opening every few weeks. This week, we were to interview for another secretary position in our building. Margaret and I met in my office one afternoon to look over the potential applicants for the job, selecting two from the pile of 20 that applied. We interviewed the first person the next morning, but it turned out that she was not right for the job, so we called in the second person, a woman named Heather Smith.

Heather showed up at Margaret's office at nine sharp the next morning for her interview. I was in Margaret's office sipping at a cup of french vanilla cappuccino and Margaret was having a cup of coffee. Heather came in and introduced herself to us. She was wearing a very curly blonde wig that fell to the middle of her back, and she also had on a loose fitting white blouse, a knee length black skirt, white stockings and black five inch heels. Margaret directed Heather to sit in the chair by her desk, then asked me to step out into the hall with her for a moment. We excused ourselves and stepped out the door, closing it behind me.

Margaret said to me, "Heather is a guy dressed like a woman, Chrissy. I could see the shadow of a mustache and beard, and those shoes were too big to be for a true woman. I bet we could get him to do a lot of stuff for us. I'll ask him some questions and see what's going on, then we can test him for his faithfulness. Hahaha! What do you think? Wanna try it?" I smiled as I thought it over, then nodded my head with a sly smile on my face as we stepped back into the office. Heather hadn't moved, and was just sitting there fidgeting with a single plain gold bracelet on her wrist. She stood up as Margaret and I came into the office and Margaret told her to resume her seat for the interview.

I moved behind Margaret and leaned against the window sill, casually watching Heather as Margaret began asking the usual office related interview questions and employment history. Heather gave all the usual replies for the questions, but added one thing that caught my attention. Margaret asked, "What skills do you possess that would work for this position that you are applying for?"

Heather's reply was, "I can type 84 words per minute. I know how to use a typewriter and computer both, as well as a copier and fax machine. I make great coffee and can remember exactly the way every person in the office likes their coffee, and I'm willing do to whatever it takes to become a success at this position."

I arched my brow and said, "Anything at all to become successful?" Heather simply nodded her head yes. Margaret turned to look at me and smiled, knowing exactly what I was thinking, because she was thinking the same thing. Margaret made some notes on Heather's application, then sent Heather down to the second floor Personnel office to get the New Employees packet and the orientation information. After Heather left Margaret's office, I took a seat in the chair where Heather was sitting a few moments before.

Margaret smiled and I knew what she was thinking. "Heather's perfect for the job and everything else we have in mind, Chrissy." she said with a devilish grin.

"She, or should I say He, sure is! We'll have a lot of fun with him/her." I replied. Margaret opened the bottom drawer of her black file cabinet, and pulled out a black leather box. She took the key from her desk drawer and unlocked the small padlock then opened the box to reveal a collection of dildos, vibrators, condoms, handcuffs, blindfolds, anal plugs, silk scarves, lubricants, and a studded collar with a black leather dog leash attached to it. She looked at me and said, "Chrissy, I do believe your eyes are twinkling in anticipation! Your face is aglow with happiness!" I blushed and tried to control my rapid breathing. We both knew what I was looking forward to.

I said, "I wonder how big his sissy clitty is under those girly clothes."

Margaret said, "Well, we will find out tomorrow morning when 'Heather' shows up for work. We'll have 'her' come in here for a 'meeting' during her break so she's not missed at her desk in the outer office."

Right after Margaret said that, a knock sounded on the door. She quickly hid the black box under her desk. I stood and moved back to the window sill as Margaret went to the door and opened it to see Heather standing there with two large yellow envelopes in her hand. Margaret motioned Heather into the office and took the packets before sitting and having Heather sit. Margaret went over the paper work with Heather then told her to report to work at 8:30 am sharp the next day for her first day of work. We all shook hands then Heather left.

We watched out the window as 'Heather' emerged from the building's front door, three floors below us. She walked like a woman but Margaret and I both knew she was a man. We watched her get into a big blue Chevy pick-up truck and drive away then we turned back into the office to begin planning our fun for Heather. We planned for almost two hours before calling it a day and putting everything back in the leather box. Margaret put the box back in her file drawer after locking it back up, then closed and locked the file cabinet.

I gave Margaret a hug and told her I'd see her tomorrow, then left to return to my own office to get my purse and jacket. I grabbed my car keys from my desk drawer and locked my office behind me. I walked to the elevator, passing Margaret's office on my way. I heard moaning coming from her office, and noticed her door was open a little bit, so I took a peek inside to see what was going on. I saw her laying on the couch in her office, naked as a baby, eyes closed tight as she pushed a huge dildo into her pussy. I could see her fluids coating it and her moaning got louder as she approached her climax, suddenly screaming out Heather's name. I felt moisture gather in my own pussy and couldn't wait to get home to use my shower massage head to get my own release, especially after watching Margaret masturbate that way.

I quietly left her doorway and returned to the elevator, stepping inside. Luckily, I was the only one in there so I did a quick rub-off of my own, just enough to hold me until I got to my car and on my way home.

Chapter 2

Five minutes later, I was at my car, unlocking the door and getting in. I buckled my seatbelt and started the car. I pulled out of the parking lot and went home, anxious to get to my shower and my toys to ease the itch between my legs. My right hand went beneath the hem of my skirt and into my panties to caress my swollen pussy lips while I kept my left hand on the steering wheel. I brushed my fingertips over my clit and moaned softly to myself.

I said out loud, "I really need to get a vibe to keep in the glove box of my car for times like this." and vowed to go to the sex shop before going home. I turned left onto Brigham Street and went to the sex shop. I parked the car and went inside, going right to the section of the store where the vibrators were. I selected a large, thick 8-inch fleshy vibrating dildo, a smaller six-inch slim vibe, a fingertip vibe, and a vibrating vaginal 'egg' with a remote control. I paid for my purchases and left the store, a red shopping bag in my hand. I got back in my car and left the parking area, driving back toward home. Fifteen minutes later, I turned into my driveway and pulled the car into the garage. I grabbed my purse and the shopping bag, and hurried inside, shedding my jacket and shoes in the kitchen and dropping my purse on the table. I went down the hall to my bedroom and quickly undressed, down to my bra and panties, which were soaking wet from the orgasms I had in the elevator and car.

I removed the vibes from the bag and opened their packages, laying them out on the bed. I read the instructions on the packages for using and cleaning them, then sat on the bed. I opened the top drawer of my night stand and took out my bottle of warming lubricant, laying it on the bed by the toys. The first one I wanted to try was the 'egg', so I took it in my hand and dripped some lube on it, smearing it around with my hands. I wiped my hand off with a tissue, then removed my panties with my empty hand. I laid back on the bed and raised my knees up, spreading my legs wide. I fingered my pussy to get it wet, then slowly slid the 'egg' into my vagina, pushing it in deep with my fingers so only the cord for it was hanging out of me. I closed my legs together to keep it from coming out, and pressed the power button on the remote.

The first sensations were exquisite as the vibrator hummed in a low setting. I moaned softly, but wanted more. I turned the speed up to medium, and my hips rose to meet the imaginary thrusts of a lover's cock as the vibrator caressed my love tunnel. I closed my eyes and began squeezing my breasts and pinching my nipples hard. I could feel my pussy getting wetter, so I picked up the fingertip vibe and slid it onto my middle finger of my right hand, then turned it on and put it on my clit lightly, reveling in the awesome sensations shooting through my groin. I could feel my orgasm getting closer and closer with each second that ticked by. I couldn't hold it back any longer so I turned both the 'egg' and finger vibes up to the high settings, and began rubbing my clit hard with the finger vibe as the 'egg' was making love to my hole.

Within seconds, my legs were squeezing tightly together and I was holding the finger vibe on my clit as my tunnel contracted around the egg vibe. I felt the fluids leaking out and running down the crack of my ass, but I wanted more. I turned off the vibes and removed the dripping wet egg vibe from my pussy with a gentle tug on the cord for it, a rush of warm liquid oozing out behind it.

I grabbed my cell phone from the night stand and dialed my boyfriend Jeff's phone number, letting it ring 4 times. He didn't answer but I knew he would call back if he could. I waited 5 minutes. He didn't call, so I figured he was busy. I put the phone back and picked up the 8-inch vibrating dildo and the slim-vibe. I lubed both well, and slid the slim one slowly into my ass after turning it on to the low setting. I pressed down with my hips to hold it in there while I slipped the big one into my hot wet pussy, all the way in on one thrust. I picked up the finger vibe again and rubbed it over my clit with my left hand while the 8-inch vibe was throbbing in my pussy as I moved it in and out with my right hand.

The feelings I was experiencing were so intense that it didn't take long for me to climax again. My whole body was tingling and I felt as if I might pass out with pleasure. It was incredible!! This was definitely something that Jeff had never made me feel before, and I was going to have to email him all about it after my shower. I would also have to email or call Margaret to tell her about it too. I just know they both would enjoy hearing about how I pleasured myself with these new toys. I screamed out my orgasm within moments, and lay on the bed panting and dizzy. I put all the toys on the night stand, then tried sitting up, but got dizzy again, so I laid back down for a few more minutes.

After about ten minutes, I was able to sit up without getting dizzy, so I picked up the toys and carried them to the bathroom so I could clean them off before my shower. I washed them all well and laid them out on a towel on the counter to dry, then I turned to start the water in the shower. I stepped in and let the warm water caress my flushed skin. I washed my long brown hair and shaved my legs and underarms, then washed my body with rose-scented body wash, being sure to wash my pussy and ass well, then rinsed off and stepped out, wrapping a large purple towel around my lush body. I grabbed another towel and dried my hair with it, then went back to the bedroom to slide on some underwear and a nightshirt. I slid my feet into my pink fuzzy slippers and went to the kitchen to make some dinner.

As I was putting some leftover chicken and potatoes and broccoli into the microwave, the phone rang. I went to answer it and found out it was Jeff, returning my call. We chatted for a few minutes, then I told him about my toy fun. I could hear him breathing heavy and he told me he was rubbing his cock through his jeans. I sat on the couch and began telling him everything I did with the new vibrators. I closed my eyes and I could hear a loud 'slap, slap, slap' as he stroked his cock quickly, then a loud growl-ish groan as he exploded his cum all over his stomach. I could tell that he had a big load from the way he was grunting, and I licked my lips, wishing I was sucking his cock and licking his cum from his tummy. I smiled as he thanked me for the great cum, and I told him I'd be glad to show him in person after work the next day. He readily agreed to be here waiting for me, since he had his own key to my house. We said goodbye and told each other, "I love you," then hung up the phones.

I went back to the kitchen and took my dinner from the microwave, grabbed a diet cola from the fridge and went to the couch. I put my plate on the coffee table and grabbed the remote control for the TV, putting it on my favorite movie that was on that night. I watched my movie and ate my dinner. My cat, Boots, came up and curled up beside me on the couch and I idly stroked his long soft fur as he purred loudly. When the movie was done, I looked at the clock. It said 9:45 pm. I stood, trying not to disturb the sleeping Boots, and picked up my plate and soda can, taking them to the kitchen. I yawned, then made sure the doors and windows were locked before I went to my bathroom to pee and brush my teeth. I grabbed my toys from the counter and put all but the 'egg' in my night stand drawer. I put that in my purse to take to work with me. I made sure my alarm clock was set for 7:00 am and I went to bed, snuggling under my blankets, falling asleep almost as soon as my head hit my pillow.

The next morning, my alarm went off at seven sharp. I got up and took a quick shower, then dressed in my black bra and thong panties, a red garter belt with black stocking straps, and black silk stockings. I pulled a short denim mini-skirt, a tight white blouse with short sleeves, and my red 4-inch heels from the closet and put them on. I fixed up my hair so it was pulled back out of my face with a pair of barrettes, did my make-up, then went to the kitchen. I poured some coffee into my travel mug and grabbed a packet of PopTarts from the cupboard for breakfast. I grabbed my jacket and purse and car keys, locked up the house behind me and went to the car in the garage to leave for work.

Twenty minutes later, I pulled my red Corvette into my parking space at work, right next to Margaret's black BMW. I went inside to the elevator to find Margaret there with Heather, who was early. They were talking and both greeted me warmly when I approached. I said to Margaret, "I have to something to talk to you about later, Margaret. It's about what I did after work yesterday, hahaha."

She said, "Ohhh, really?? I cant wait to hear about it. Come to my office around ten for a cup of coffee and we'll talk." I agreed to the meeting and we all stepped into the elevator, Heather between Margaret and myself. I couldn't help looking down at 'her' lap, wondering what was under that brown skirt and those beige stockings. I glanced up to see Margaret smiling at me, as if she knew what I was thinking, and I'm pretty sure she did know.

Chapter 3

A few minutes later, we emerged from the elevator and I went to my office to check my messages, telling Margaret and Heather, "I'll be at your office at 10:30 for that meeting, Margaret. See ya soon!" They waved to me as I walked down the hall. I smiled as I patted the side of my purse where I had that vibrating egg toy, and I couldn't get to my office fast enough! I went into the outer office where my secretary, Amy-Lynn was busily typing away on the computer. We exchanged our good mornings and I told her that I was not to be disturbed for any reason, unless Margaret or Heather wanted me for anything. I went into my office, locking the door behind me.

I went to my desk and flipped on the power switch for my computer. While that was booting up, I hung up my jacket and removed the 'egg' from my purse. I sat on my couch and slid down my panties and stockings, and raised my skirt. I slid the 'egg' into my hot, wet, waiting pussy then slid the remote up under the waistband of my skirt so I could put it in my pocket discreetly. I pulled my panties and stockings back up, then readjusted my skirt. I tucked the remote into my pocket and turned it on the low setting, feeling the steady vibrations deep inside my pussy as I tested it out. Oh my God, it felt sooo good to be so naughty in my office. I turned off the vibrator and went to my desk to check my messages on my computer.

I was scrolling down my list of messages when I came across one that Margaret had sent me. It was a link to a porn site that she wanted me to check out when I had some time. I looked at the clock and realized I still had an hour and 45 minutes before I had to be in her office for that meeting with her and Heather, so I clicked on the link. A few seconds later, the site popped up on my screen, revealing pictures of busty women being fucked by handsome, well-hung men, and some women being fucked by other women using dildo's, vibrators, and even some carrots and cucumbers. I was getting excited just from looking at the pictures, so I clicked on one showing a pair of ladies using cucumbers on each other.

The video began with the ladies kissing and touching each other's naked bodies, and licking each others pussy until they were glistening with saliva and love juices. They picked up the two large thick cucumbers and rubbed each other's wet cunts with them, then slowly began pushing them in and fucking each other with the vegetable. I had to admit, I was getting really turned on and I couldn't resist sliding my hand into my pocket and turning on the 'egg' vibe to the high setting immediately. My other hand slid beneath my skirt and fingered my clit as I watched the ladies fuck each other silly with a pair of 9 inch long cucumbers. Within moments, I felt my orgasm closing in and reached into the drawer of my desk for some tissues to clean up with afterward.

I fingered my pussy faster and harder as the 'egg' continued to vibrate deep in my cunt, closing my eyes tight as my climax hit me hard. I felt my juices leak out of my pussy and soak the crotch of my panties. I just sat there for a few minutes, after turning off the vibrator egg, letting my breathing get back to normal and for my body to stop tingling. I looked in my desk drawer hoping to find another pair of panties in there, but no such luck. So I just used the tissues to dry them as best as I could when I wiped my wet pussy. I tossed the tissues into my wastebasket and went back to reading my emails after saving that porn site on my favorites list. I thought of sending Margaret a Thank you email, but decided to just tell her when I saw her at the meeting.

Ten minutes later, my emails read and replied to, I glanced through the phone messages that waited on my desk. There were a couple from Jeff, and a few from some clients, which could wait until after lunch. I picked up my phone and dialed Jeff's cell phone. He picked up on the first ring. "Hi beautiful! How's my girl this morning?" he asked.

"I'm fine babe, just sitting here in my office looking at some porn and thinking how nice it would be to have your hard sexy cock thrusting deep in me as we both watch it together. But since you aren't here, lover, I had to settle for using my new vibrating 'egg' toy that I bought yesterday at The Pleasure Palace." I replied. I heard him moan as he thought about me using the toy.

bunny3374
bunny3374
138 Followers