The Applicant

"Baby, that's so fucking hot! Can I come over to see you during your lunch break today? My cock is so hard and hurting from wanting you, baby." he said.

"Yes my love, come over around noon. I'll be in my office, and Amy-Lynn will be in the cafeteria having her lunch so she wont know you were here. I'll leave the door unlocked for you when I get back from my meeting with Margaret and her new secretary, Heather. I have to go now, lover, but I promise you will be a happy man when you get here! I love you, Jeff! See you soon!! Kisses!" I said, then he said good bye and I hung up the phone.

I did some work for a while, until it was time to go to Margaret's office. I put my computer in stand-by mode and left my office, locking it behind me. Amy-Lynn was still at her desk typing so I told her I'd be at Margaret's office if anyone came looking for me, then I left the outer office and walked down the hall. I went into Margaret's outer office and saw Heather there labeling some files and forms. I said, "Hi Heather, how's it going?"

She replied in a high pitched female voice, "Just fine, thank you. Margaret is in her office waiting for you. Go on in." I thanked her and knocked once on Margaret's door before opening it and going inside. She was sitting on the sofa sipping a coffee and flipping through the newest issue of Playgirl. She glanced up and smiled as I stepped into the office. She stood and we hugged, then she handed me the magazine.

"Look at the guy they chose for the centerfold this month, girl! He's to die for! Total babe and sex god! MMMMMM!!" she said, practically drooling all over my hand as she pointed him out to me. I looked at the pages and he was absolutely gorgeous! Long shoulder length black hair, broad muscular shoulders, powerful arms and legs, flat wash-board abs, and a huge cock that must have been at least 11 inches long and rock hard. My legs started to turn to jelly as I closed my eyes, imagining that stud servicing me in every way imaginable. I had to sit so I dropped onto the sofa beside Margaret. We chatted about the hunk in the magazine, then she put it away, in the drawer of her desk. I could tell by the look on her face that it was time to get down to business with 'Heather'.

"First of all, we have to find out Heather's real name, her boy name. In order for us to make him bow to our every demand, we need to know everything about him, especially what got him to start dressing like a woman and calling himself 'Heather.' " she said softly.

I suggested, "Let's bring Heather in here and see what exactly he would do to keep this job, Margaret. That's the only way we'll be able to know what's going on. I REALLY want to know what's under those skirts!!"

Chapter 4

Margaret smiled and said, "And you shall, in just a moment, my dear friend."

She pressed the button on the intercom and asked Heather to step into her office. Less than a minute later, Heather tapped lightly on the door and stepped inside, closing the door behind her. Margaret and I both greeted her and Margaret asked her to sit in the chair opposite the one I was in, in front of Margaret's desk. She sat and primly crossed her legs like a woman usually does. I glanced at her legs and noticed that there were no tell-tale lines from hair on them. 'He must shave them to feel more lady-like.' I thought to myself.

Margaret asked Heather, "When we interviewed you yesterday, you said you'd do anything to keep this job if you got it, is that correct?" Heather nodded, a confused look on his/her face. Margaret said, "Would you do whatever Chrissy or myself asked of you, and I do mean ANYTHING?" Heather nodded again, glanced toward the door and shifted his body in the chair nervously.

I said, "It's ok Heather, no one will bother us. We just want to know what kinds of things you would do to keep this job. May I ask, would you undress for Margaret and I, right here right now?" Heather looked surprised at that request. Margaret went to make sure the door was locked then turned back to Heather and I.

Margaret said, "Now Heather, remove your shirt and skirt, then sit on the couch." Margaret went back to her chair behind her desk and sat, then took out the key to the file cabinet as Heather began to unbutton her blouse. As the buttons opened, a smooth, hair-free chest emerged, covered by a white lacy bra. She took the shirt off and laid it on the chair. "Now the bra, Heather." Margaret said. Heather acted like she didn't want to remove the bra, but Margaret said, "Remove the bra now, or go home without a job, Heather." Heather slowly reached behind her back and unhooked the bra. It slid down her arms, carrying the artificial breasts with it and revealing a smoothly shaved man chest.

"Heather, Margaret and I both know you're a man, so there's no reason to be shy or embarrassed about it. I could tell when you came into the office yesterday for your interview that you were really a man. There's just some things that men can't do as well as women, mainly walking as smoothly and gracefully as a woman. That's how I knew the truth. Now, what I really want to know is, what is your REAL name and why do you dress as a woman?" I asked him.

I watched him swallow a few times, then clear his throat. In a deep manly voice, he said, "My real name is Jack, and I would do ANYTHING to keep this job. My wife divorced me and took the kids, then I discovered some of her old clothes that she left when she moved herself and the kids out of my house. I was depressed that she left me, but curious about what it was like to dress as a woman, so I kind of played around with the idea for a few days before starting with putting on just a pair of her panties. I found that I loved the feel of the cool silk against my skin, so I would wear them under my jeans or sweat pants when I went to work or the gym. When I was home alone, I'd wear some of her old make-up, usually just a little lipstick or eye shadow. Then one day, I decided to put on one of her bras, stuffed with a couple of small towels to fill the cups, then one of her old maternity dresses. I admit that I liked the way I looked and felt in those clothes. So, I decided to go all the way and I purchased these breasts and more clothes and make-up, and a couple of wigs until my real hair grew long enough to pass as a woman."

I was speechless, and Margaret looked at me with a twinkle in her eyes and a knowing smile on her face, then she turned to Jack and said, "So Jack, do you tend to be more dominant or submissive, sexually?"

He blushed, and then said, "I guess I'd have to say that I am somewhat submissive, although sometimes I like being in control in the bedroom, when I'm in what I call my 'man mood' and wanting to get some release fast."

I said, "Jack, would you take off that skirt now? I want to see what's under it." He blushed a deeper pink then slid his hands down to the waist band and unhooked the little hooks before sliding it down over his hips and ass, and letting it fall to the floor. He was wearing a pair of white women's briefs under a white garter belt holding up the white thigh-high stockings. I looked closely and could see the outline of his flaccid penis and his testicles, and I unconsciously licked my lips as I saw his shaft begin to grow under my gaze. I felt the moisture gather in my own panties, and couldn't resist reaching my hand into my pocket discreetly and switching on the remote to the vibrating 'egg' that I still had in my pussy.

I heard Margaret tell Jack to take off those panties and lay on the couch, which he did, fully exposing his semi-hard cock to both of us. I walked over to the couch, switching off the remote on my way, and I knelt between his legs, taking his cock in my hand and stroking it slowly as Margaret hiked up her skirt, slid off her panties, and straddled his chest. She said, "Lick my cunt, you naughty secretary." I looked up at her and smiled as I began licking Jack's cock, savoring the texture of his flesh on my tongue. Margaret moaned as his tongue hesitantly flicked at her wet flesh. I watched them as I continued to lick his cock, and I saw him bury his face in her cunt, making long strokes with his tongue, burying it deep in her wet pussy. She was grinding her pelvis against his face, and I could tell by her breathing that she was getting close to an orgasm already.

I began to suck his cock hard and stroke it fast, wanting him to climax as well. My right hand crept down to my pocket, switched on the remote again, then I moved my hand down to rub my clit. He was rock hard beneath my lips, and I guessed that he was about 8 inches long and close to a couple inches thick. I closed my eyes as I sucked him off, and wanted so bad to feel this glorious shaft deep inside me. I made up my mind then to remove the vibe from my sopping wet cunt and turn it off, then I stopped sucking him, and stood to remove my panties and pull up my skirt so I could straddle his lap. Margaret turned around to face me, and Jack continued to eat her pussy, occasionally sliding his tongue over and into her ass. I straddled Jack's lap and wrapped my hand around his cock to guide it into my wet pussy, slowly lowering myself on him and feeling him stretch my tight hole.

Margaret smiled at me as she wrapped her arms around me as we both got pleasured from this sub male. We were like that for a few minutes, before Margaret said, "Time for Chrissy and I to trade places! Stop eating for a minute, Jack." as she got off of his face and helped me to turn around and sit on his face before she climbed onto his lap and impaled herself with his rock hard love stick. I was enjoying his talented tongue work and within moments, I felt my juices flowing out of my pussy and into his mouth, which he greedily lapped up. I looked at Margaret, and she was riding him hard and fast, her breasts bouncing with each thrust. I felt and heard Jack groaning that he was about to cum, and she rode him faster and harder, making him work hard to control himself.

He started growling, and we both knew he was going to explode, so she quickly got off of his lap and I got off his face, and she started stroking him fast. Seconds later, the first jet of thick sticky hot cum shot out of his pee-hole and landed in a puddle on the floor. It was followed by several more streams, which landed on Margaret's face and chest, and even on my tits and leg since I was on my knees by Margaret, fondling Jack's balls as she jerked him off. When the cum was just a little trickle from the head of his cock, we all collapsed on the sofa and snuggled, still touching each other intimately. I sighed contentedly as Jack kissed first Margaret, then myself in a deep passionate tongue-dueling kiss. After about ten minutes, we got up and fixed our clothing, and Jack resumed his female persona, putting the breasts, bra, panties, skirt and blouse back on.

Margaret said, "Jack, how would you like to be my and Chrissy's sexual slave a few times a week? There would be some tasks that we would have you do without question, if you accept."

He thought it over for a few moments, then said, "I'd be glad to, Margaret. Since my divorce, I haven't been very interested in the whole dating scene, and have resorted to porn videos, internet porn and magazines to relieve myself every couple days, but if I could make you and Chrissy happy sexually, I will try my best to be a good sex slave for you both. What did you have in mind for the tasks, anyhow?"

"Well, you could start by sending both Chrissy and I two erotic emails every day, complete with pictures and you must type your own description for each photo. Then this weekend, when you are alone, we want you to go to The Pleasure Palace and purchase a few items. I will give you a list later today before you leave to go home. On Monday, you have to bring in the items to me and Chrissy, and you have to use them in front of us on yourself, and use them on us as well. Do you think you can do that, Jack?" she asked. He thought a moment then nodded in agreement. Margaret sent him out to clean up in the bathroom, then she and I cleaned up the cum mess in her office as we talked about that wonderful new experience, both of us agreeing that the fun was only just beginning for all three of us.

After she and I cleaned up the mess, and ourselves, we sat at her desk, writing down a list of items for Jack to buy at the sex store: 2 pair of vibrating nipple clamps, two nine inch dildos, four porn videos, an assortment of flavored lubricants, two "Make Your Own Dildo" kits, and a pink butt plug, which Margaret said she would make Jack use at work.

Chapter 5

Margaret made a note to purchase a portable DVD player and a good supply of paper towels to keep in her office closet, along with several clothing items: sexy silk lingerie with bras, panties, stockings, and garter belts; shoes and slippers, a bathrobe, and a few sexy dresses. She took the black box out of the file drawer and inventoried the contents to see what she would need to add to it. She currently had 4 dildos of different lengths and thicknesses, 2 vibrators - an 8 inch and a 4 inch one, a pair of gold plated metal handcuffs, a pair of black leather cuffs, a fuzzy pink pair of cuffs, 2 black blindfolds, 5 silk scarves in black, red, white, blue and pink, a twelve pack of colored condoms, and two bottles of lubricant, one unflavored, one strawberry.

She looked up at me and said, "I think I just need to get more lubricants, maybe cinnamon and cherry and orange flavors. Oh, and a bottle of the kind that heats up as you use it. I bet we could get Heather squirming with that stuff on her." We both laughed at the thought of Heather having that lube spread all over his rod as it heats up and he starts to move around and groan. I looked at Margaret and she said, "Girl, you got a twinkle in your eyes! I know what you're thinking! We'll do that on Monday!"

She closed up the box and put it back in the file drawer, locked it up good, and re-wrote the list to give to Heather for her weekend shopping adventure. She tucked the other lists into her purse before pressing the intercom button on her phone and calling Heather into the office. A moment later, Heather knocked on the door and stepped inside. We both said hello to her and Margaret asked, "Were you working on your 'tasks' already, Heather?" She nodded and stepped over to stand in front of Margaret's desk. Margaret handed Heather the list and said, "You are to get these items this weekend at The Pleasure Palace, and you are to go there dressed like you are now, as a woman. If the salesperson asks, you are to say that you are getting the items to surprise your husband with a romantic night alone. After you pay for them, lay them out on the seat of your car and take a picture as proof that you bought them. Email the pictures to me and to Chrissy. Then make the 'kits' and bring the finished product to work with you on Monday along with the other items so we can see what you got and how you would use them for us. Any questions?"

Heather looked over the list and said, "This list seems pretty easy to finish. I don't have any questions right now, except that I was wondering, wouldn't you want me to make the kits here with you both watching and helping me do it?"

Margaret looked at me and asked,"Well Chrissy, what do you think? Should our little slave here make the kits in front of us, or all alone at home?"

I didn't need any time to think that over, and I immediately said, "Make them here with us, of course! You might need help keeping your cock hard, and I know just how to do it! Mmmmm!!" Margaret saw the gleam in my eyes and smiled, knowing what I had in mind.

She said, "Okay Heather, we'll see you here at nine o'clock sharp Monday morning for a special 'meeting' and we will not be disturbed for a few hours. Take your list and go home, then do the shopping first thing tomorrow morning. Don't forget to email the photos to us as soon as you get home. Have a good weekend Heather, see you Monday!" With that, Heather turned and left the office to return to her desk and finish the first task of emailing the sexy erotic photos to me and Margaret.

Margaret and I said goodbye to each other with a hug, and then I left her office. Heather was at her desk working on the computer, and I said goodbye to her on my way out. I went down the hall and into my office, where Amy-Lynn was just turning off her computer to go on her lunch break. I knew she would be gone at least an hour, so I hurried into my office and quickly dialed Jeff's phone. He answered immediately and I asked where he was. He said, "Baby, I'm in the elevator about to step into the hall outside your office."

My pussy was already soaked, and I said, "Amy-Lynn is just leaving for lunch, so come on in, lover! I'll be waiting for you." We hung up at the same time and I quickly removed my panties from under my skirt, tossing them into the drawer of my desk. I still had the 'egg' in my pussy, but I pulled it out and cleaned up a bit using the baby wipes that I keep handy in the top drawer. I wiped the 'egg' off and then laid it on my desk as the door opened, revealing my handsome boyfriend Jeff. He was dressed in a tight black sleeveless muscle shirt, black jeans, his black sneakers and his skull biker cap. He had trimmed his beard and mustache down to just a goatee, and he looked sooo gorgeous! My pussy muscles tightened in anticipation of his loving tongue and cock, which I could see pressing against the buttons of his jeans.

He came in and closed the door, locking it behind him, then I ran to him and threw my arms around him in a big bear hug as he plundered my mouth with his lips and tongue in a passionate kiss. I felt his hand slide under my skirt and cup my bare ass and he growled as his fingers slid between my ass cheeks. His hand then slid down behind my thigh and lifted my leg so he could plunge his fingers into my hot wet pussy. He fingered me quickly and brought me to an orgasm almost immediately. My legs were weak so he picked me up and carried me to the couch, laying me on my back and spreading my legs wide. He buried his face in my cunt, licking and sucking my juices, nibbling gently on my clit and making me moan loudly. I wanted to feel his cock so badly that I reached down and began unbuttoning his jeans, then shoving my hand inside and grabbing his rock hard cock.

I stroked him slowly, my thumb caressing his head and spreading the pre-cum around on it. He let me up enough so I could turn around and take him into my mouth as far as I could without gagging. I sucked and licked and stroked him til I sensed he was close to cumming, then I stopped and turned around, got on my knees on the couch and he spread open my pussy lips with one hand as he guided his cock into my cunt with his other hand. He was fully encased in my wetness within a couple seconds, and started pounding my cunt hard and fast, his balls slapping my clit with each thrust. I was moaning and panting, and my tits were slapping against each other since I had freed them from my bra and shirt while Jeff was eating my pussy. He put his hands on my shoulders and pulled me upright, wrapping his left arm around me, beneath my tits. His right hand cupped my left tit and was gently pinching my nipple, sending shockwaves through me, from my nipple to my pussy.

Chapter 6

He whispered in my ear, "Baby, I felt your cunt tighten when I pinched your nipple, and I loved it! It feels incredible baby! You're so tight and hot! Cum for me baby! Soak my cock with your juices!" I closed my eyes and focused on his pounding thrusts, ramming his cock into me hard and fast and deep, wanting him filling me completely. I could feel wetness seeping down my thighs as my fluids flooded his cock when I orgasmed on him. He didn't stop, just kept ramming and thrusting within me until he was close to his own release. He growled and suddenly pulled out, frantically stroking his cock over my ass. His hot wet cum shot out onto my ass cheeks in several long white strands. I felt some of it leaking down my ass crack as he rubbed the head of his cock over my ass.