tagTranssexuals & CrossdressersMr. Wallace and Me Pt. 01-05

Mr. Wallace and Me Pt. 01-05


(The author welcomes comment via the CONTACT tab on his profile.)

My name is Bill. I'm just out of high school, and still living at home. I had decided to take a year off before I went to college. I was tired of studying, and being the best diver on our swimming team had been a lot of pressure. I hadn't had time for much dating, and I was looking forward to going off the diet that I've had to be on ever since I could remember and taking a scissors to that tight rubber cap I had to wear over my blond ponytail whenever I was in the pool.. I'm 5-6 and 130 pounds. The girls in high school ignored me and my sex life consisted of playing with myself while looking at Internet porn.

The only job I could find was as a night security guard at an old factory in my small hometown. The factory used to be humming 24 hours a day, but since the economy had tanked, there is only one shift, and I'm all by myself overnight. It's such a nothing job that if I had to do it for more than a year, I think I would go mad. My supervisor, Ted Wallace, has been there for about 30 years, and I never met a bigger loser in my life. He's a 63-year-old former Marine, but you'd never know it by looking at him now. His pockmarked face usually needs a shave, and it's almost always scowling. He's about 6-4 and he's got to be pushing 290 pounds. He's on duty every day when I come in, and he's a stickler for all the company rules. Most of those rules don't make a lot of sense to me. I mean, it's not like the Iranians are going to invade the factory any time soon. One of those rules was to stay away from the company computers and just do my rounds.

It took me only a few weeks before I found a computer in a corner of the third floor where I could pass hours looking at porn. This wasn't such a bad job after that.... until one evening when I came in to work, and there was Mr. Wallace's fat face smugly smiling at me.

"C'mere, kid," he said, motioning to his computer monitor with a pudgy hand. "I keep telling you how much you have to learn, and that includes where all of our security cameras are located."

My eyes grew wide as I leaned in over where he was sitting, smelling his sickly, pungent after-shave, which he must have had on him at least two days based on the stubble on his face.What I saw on the tape from last night almost made my heart stop.

There I was, sitting in front of the computer, my eyes half-open, my pants and underpants around my ankles, my necktie very loose and my uniform shirt unbuttoned. My left hand was pinching my right nipple, and my right was around my slim, 4-inch circumsized penis.

I turned away from the screen, started to stammer, and tears were forming in my eyes. I started to move away, but Mr. Wallace grabbed my wrist.

"No, Billy boy," the fat man said with a derisive laugh. "It's just getting to the best part."

I almost couldn't see the screen through my tears as my slender little penis erupted, my left hand preventing my cum from getting over the computer. Mr. Wallace let go of my wrist, and I stumbled back.

"Now," he said, smiling widely enough for me to notice he was missing a side tooth. I had never seen him smile before. "What should we do about this, Billy boy? I should certainly have you fired. I could probably have you arrested, too, for putting company equipment at risk. Of course, I'll have to see that your parents see this tape. I've got it on my home computer already. I'll almost certainly post it on Facebook."

I was literally shaking.

"Please, Ted ... Mr. Wallace, please ... not that. I'll never do it again. I'll work extra hours for no pay. Please ... don't. Why would you do this to me?"

He laughed again.

"Why, you little shit," he said, "do you think I'm stupid? I can tell every time you come in to work that you think you're better than me, that I'm a nothing guy in a nothing job."

My eyes almost shut as I tried to keep from crying, I slowly shook my head "no," even as I knew he was right.

"I ... I'm sorry, Mr. Wallace."

He looked me up and down and smirked.

"I'll tell you what, Billy boy," he said. "I'll keep this our secret ... at least for a while. We'll see how sorry you are. My house has been a mess ever since my wife divorced me ... what has it been, 16 years now? Well, from now on, every Saturday afternoon, you're gonna come over and clean my house."

I brightened just a bit.

"That's it? I've just got to clean your house ... and you won't let anyone else see the tape?"

"That's it," he said. "But I'm particular about how my house is cleaned. You'll have to follow all my instructions when you're there. If you don't, or if you miss one Saturday, the tape goes out to everyone."

He wrote his address on a piece of paper and told me to get there at 12:30 sharp before he picked up his things and left at the end of his shift.

The next two nights at work passed without more than a few words passing between us as we met on our shifts, except I called him Mr. Wallace instead of Ted, like I had been doing.

Finally, it was Saturday afternoon, and I told my parents I was spending the day with friends. I found his double-wide trailer house in a lower middle class neighborhood. Dressed in jeans, a T-shirt and sneakers, I rang the bell. He opened the door in a bathrobe that was probably older than I am. Somehow, he looked even bigger than he did at work, where he was mostly sitting on his fat butt. The place reeked of cigar smoke, and there were clothes and magazines and fast-food bags strewn around. There was a sink full of dishes that probably weren't washed for weeks.

"Come in, Billy boy," he said expansively. "Five minutes early, I like that."

He put his fat hand on the small of my back and led me to the bedroom door.

"Go in there and change," he said matter-of-factly.

"Change?" I asked, confused.

"Yeah," he said, his hand on my back urging me into the bedroom. "When you clean my house, you're going to dress the way I want you to."

The bedroom was a dissheveled mess, but on the rumpled bed was a crisp, blue house dress.

"You ... you can't be serious," I said.

Mr. Wallace sauntered, if a man that big and fat can saunter, over to his bedroom computer, punched a few keys, and there I was on the screen showing me beating off at work. His eyes were steely and mean.

"Oh, I'm serious, Billy boy," he said. "I'm dead serious. Now, you get out of your clothes and put that dress on. No underwear, you understand? You can go barefoot today. I'll be waiting in the living room. Snap it up. You've got a lot of work to do."

After he left the room, my mind was in a haze. It's bad enough I have to clean this fat, old man's pigsty, but in a dress? There wasn't anything I could do about it, though, and I looked at myself in the bedroom's full-length mirror as I took off my clothes. I don't have much body hair to start with, and that I had I shaved because I was on the swimming and diving team. Was this Mr. Wallace's method of humiliating me for my attitude at work?

I pulled the dress over my head, and it eased down over my body, coming down to a few inches above my knees. The built-in belt was snug but not too snug on my concave waist. The elastic top of the dress had puffy sleeves that just did cover my shoulders, and the scoop neck revealed a good deal of my chest and my upper back, on which rested my blond ponytail. Swimming and diving had given me a taut body and breasts that jutted out just a little, giving me a hint of cleavage in the dress.

I looked in the mirror and had to admit that I looked pretty nice, but I felt ridiculous. I walked out into the living room. Mr. Wallace was sprawled on the couch in that ratty robe while watching football.

"Ah," he said. "you look very pretty."

I didn't say anything. I just stood there, mortified.

"You can start on the dishes, Billy," he said. "But first, fetch me a beer, will you, honey?"

"Honey?" I thought. "Did he just call me 'honey?'"

I walked to the refrigerator and opened it. It smelled like something had died in there. I took out a can of beer and brought it to him, humiliated with each step I took in that dress. He looked up at me, then turned his attention to the game. I was being dismissed to do my housework, reinforcing my feminine role while the man of the house watched football.

I started on the huge pile of dishes, my mind in a whirl in the dress. In about 10 minutes, Mr. Wallace called to me.

"Hey, Billy, he said, "fetch me another beer."

I stopped what I was doing, dried my hands on a towel and obediently brought him another beer. He smiled that missing tooth grin at me, handed me his empty beer can and said, "Thanks, hon."

A chill went through me. Something in me was pleased that I had pleased him, and that bothered me.Walking back, I felt and heard the skirt of my dress swishing. It made an interesting sound.

After I got through with the dishes, he told me to tidy up the living room but not block his view of the game.

"Oh, and one other thing," he said, "every five minutes, I want you to go into the bedroom and look at yourself in the mirror."

I could see what the bastard was up to. He wanted to keep reinforcing my mental image of myself dressed as a girl. I was already arching my back femininely and bending my knees rather than leaning over as I picked up things around the couch so as not to block his view of the TV. When I wasn't stopping what I'm doing to fetch him another beer, I was going into the bedroom to look at myself in the mirror. For some reason, when I looked in the mirror, I would adjust the dress or move a stray hair off my forehead or some other little thing that would help me look a bit better. When I walked back to the living room, for some reason my palms faced forward and my shoulders were back

The living room needed vacuuming, but when I asked Mr. Wallace, he said he didn't want the noise. He said I should go make the bed and pick up the clothes in the bedroom, and not to forget about looking in the mirror every few minutes.

I couldn't help moving differently in the dress than in my male clothes. When I looked in the mirror, I had to admit that ... well ... I was pretty. About a half hour later, the bed was made, the room was a bit neater, and I was looking at myself in the full-length mirror when I heard Mr. Wallace walk in behind me. I saw the fat slob in the mirror.

"You know, Billy, you really are pretty," he said as his fat hands went around my tiny waist, "and you're a much better housemaid than you are a security guard."

I wanted his hands off me, but then there was that tape.

I could feel his thick fingers fiddle with the rubber band holding my ponytail, and then I felt it break and saw in the mirror as my blond hair spread out over my shoulders and back. I heard Mr. Wallace's hard breathing and felt his breath on my neck. His hands moved up from my waist to my puffy sleeves, which he ever-so-slowly pulled just off my slender shoulders. I started to tremble and breathe hard as I looked at this giant in the mirror behind a sweet-looking ... yes ... girl.

My mind fought against this image. I'm a man, after all, and determined not to react to the touch of this fat, ugly old man who is blackmailing me, no matter what. But something about my shoulders being exposed made me feel so vulnerable ... so feminine.

Mr. Wallace's robe came open. I could see a thick penis emerging from a gray and black bush of pubic hair. Then he kissed my right shoulder ... just once, and a chill went through me.

"N----no," I said weakly.

Mr. Wallace's hands went to my bare shoulders as his mouth began kissing and licking and nibbling my neck. I stood straight up, impassively, even as my little penis got stiff in my dress. I hoped he didn't notice.

"Mr. Wallace ... please ... I ... I'm ... not interested."

Mr. Wallace just kept on his caressing my sensitive shoulders, licking, kissing and nibbling my neck as I stood there hoping he would get frustrated and give up.

But, he didn't stop.

"It's all right, Billy," he said as his pockmarked, stubby, fat face moved my hair out of the way of his gentle assault. "We have the entire afternoon."

I stood there, looking in the mirror as my old, fat supervisor just kept kissing and nibbling my neck. I never knew my shoulders were so sensitive until I felt his hands alternate between feathery touches and powerful grasps. The seconds turned to minutes ... and the minutes dragged on. I didn't realize it, but my shoulders began to shimmy just a bit, his gamey after-shave making me a little dizzy as he kept up his assault on my neck.

I ... couldn't ... help ... it. His fat lips were giving me the chills. His hands caressing my shoulders made me feel so ... so desired and ... yes, feminine. I closed my eyes and tilted my head to give him more access to my neck.

That little movement was apparently what he was waiting for. His robe fell away, revealing his disgusting, hairy body. He intensified his assault, pulling my hair back and biting my neck. His tongue traced my collar bone as he twisted my body from behind. I cried out as he bent me back, my hands reaching for his shoulders to keep myself from falling. His lips searched for mine. I kept my lips shut tight, but he was insistent. My body went limp in his grasp, and his thick lips moved on mine. Then, for the first time in my life, there was a tongue in my mouth that wasn't mine.

I never felt like this before. In my mind, I was a pretty young girl being despoiled by a fat, ugly, old brute.We kissed for minutes ... or maybe it was hours. All I knew was that I was surrendering to the overwhelming girth and power of my worthless boss in my nothing job. I was making little girly noises as we kissed and I clung to Mr. Wallace's putrid body.

The look of utter triumph on his face made me ashamed, but still, I yearned for his kiss, his hands on my chest and shoulders, my dress remaining on my quivering body.

As his lips pressed against mine, he lifted me up, one thick arm under my legs, the other behind my back. He lay me gently on the bed and raised my arms to either side of my head, my palms femininely outward, my slender bare shoulders shimmying slightly and revealing my desire.

Mr. Wallace stood diagonally over me, his fat, disgusting belly hanging over his thick cock. I looked up at him, breathing hard, feeling like a pretty, young girl in the clutches of an ugly, old monster. My mouth silently mouthed one word of desire.

"Please ....?"

Mr. Wallace smiled much too confidently, bent over and lifted the skirt of my dress, revealing my slender, erect, little penis.

"Damn, Billy," he said, "with that little excuse for a dick, you're better off as a girl."

My face turned red, my wrists on either side of my head as he lowered his face to my penis, My eyes grew wide as his thick lips encompassed my penis.

I groaned out loud. Then my body began to undulate.

He started sucking rapidly, and I hardly noticed as his middle finger maneuvered its way slightly into my rectum. I was going to shoot any second, but he lifted his sweaty face and smiled at me triumphantly.

"Want me to stop, Billy?"

I was lying there in this pretty dress. I had surrendered myself to this awful man I despised. I was so ashamed, but I had to cum. I just had to cum.

"Please don't stop, Mr. Wallace."

He smiled again, actually more of a triumphant leer, his right hand digging more into my bottom, his left slowly tracing over my chest, moving from one bare shoulder to another, only touching what the dress made bare, ignoring my nipples. His mouth, a minute ago on my penis, now covered my lips, his tongue owning my pliant mouth.

He whispered.

"Are you a pretty girl, Billy boy?"

His finger now completely inside me, I nodded.

"Say it, Billy boy."

Mr. Wallace's finger pumped in and out of me. It felt like a baseball bat.

"I ... I'm ... I'm a ... pretty ... girl, Mr. Wallace."

Another leer, and the fat man was under my skirt again, my penis entirely in his mouth, his finger pumping my bottom. Ten seconds later, my mind dizzy, I cried out loudly as I exploded into Mr. Wallace's mouth. I didn't feel like a boy. I felt like a girl ... a woman ... achieving the best orgasm of my life. His finger pounding away at my rectum, I finally eased back ... limp, moaning contentedly, luxuriously, slowly shimmying my bare shoulders. Mr. Wallace removed his finger. His enormous body covered mine as his hands gripped my shoulders. His mouth covered mine, his mouth maneuvering mine open. I was too weak to resist. To my horror, I felt my own cum sliding into my mouth. The bastard had saved it to feed to me. I tried to struggle, but his weight on me and his thick hands on my shoulders made it impossible.

He kissed me, rubbing his cum-covered tongue over mine for several minutes before collapsing atop me. Long minutes passed until he woke up. Was he going to fuck me? The big man rolled off me, breathing hard.

"Go get dressed, Billy," he said.

I slowly removed my gown and dressed in my male clothes. It felt a little weird. I kinda missed the dress.

"Y'know," I said, "I don't mind staying and tidying the place up some more."

The big, old man got up and pulled my hair sharply, walking me rapidly to the door. He bit my neck one last time, then opened the door and shoved me out.

"I'll see you at work Monday,: he snarled. "And next Saturday, Billy, Don't even think about being late coming over here."

(To be continued.)

Mr. Wallace and Me (Part 2)

By Robin O.

(The author welcomes comment at oberon_52@hotmail.com)

The cool air hit me outside Mr. Wallace's doublewide trailer as I staggered to the car I had borrowed from my mom. My body was shaking and I was having trouble catching my breath. I don't even remember starting up the engine and driving away. I couldn't make my mind believe what had just happened to me. Fat, disgusting, old Mr. Wallace I always thought was such a loser, had turned me into ... into ... my eyes started to mist up.

I looked in the rear view mirror and turned my head a little. There was the red mark where Mr. Wallace had taken that last bite of my neck. I had let him kiss me ... and I kissed him back as his big, fat hands had held me and caressed me like I was some girl. He was in total charge of me. He didn't even have to play with my tits to get me all pliant and girly. He had put his stubby finger up my bottom. He made me beg for him to let me cum. My mind went back to seeing his thick, old cock hanging there flacid. My heart started beating faster. What if he ... what if he had told me to suck it? Would I have? The answer came over me along with a wave of incredible nausea.

I pulled the car over, kinda screaching the brakes. I opened the car door and lunged out, certain I was about to throw up. There I was, hanging half out of the door, and trying to keep from vomiting in my mom's car. I had been too nervous to eat breakfast, and I was in Mr. Wallace's house for hours without eating anything, and instead of actually throwing up, I had the dry heaves. It felt awful, almost as awful as realizing that I would have sucked that fat prick's prick if he had wanted me to.

It took me about 10 minutes before the nausea let up enough for me to resume driving. As I drove, I got more and more angry, more determined that no one -- least of all that fat bastard Mr. Wallace -- would ever make me feel like anything other than a man again. When I got home, I said hello to Mom and Dad, then I took a hot, cleansing shower, determined to scald off any vestige of the humiliation I had been feeling.

I dried myself off, then put on my white terrycloth bathrobe, tying the belt snug around my narrow waist. I started brushing out my blond hair in front of the mirror as the fog on it slowly dissipated. I am a man, dammit. I looked at my thick hair in the mirror, remembering, despite trying to forget, how it had fallen over my shoulders and neck after Mr. Wallace had snapped the rubber band holding my ponytail. Almost hypnotically, I moved the top of my robe just off my shoulders, revealing them, in addition to my chest, baring it in a triangle to the start of my small, firm swimmer's breasts.

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