Amelia Jones Ch. 01

This is a work of fiction. Names, characters, businesses, places, merchandise, companies, events and incidents are either the products of the author's imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters in sexual situations are 18 years or older.

For Todd. I hope someday to address you as Amelia Jones. Until then ...

Prologue

I'm a woman trapped in a man's body. I've known it for years, and yet only recently have admitted it to myself.

I grew up in a small town in Ohio. You wouldn't recognize the name even if I told it to you. It's about 60 miles from Dayton and about a million miles away from where I really wanted to be. White bread suburbia. The family car parked in the driveway. Screen doors to keep out the bugs. It didn't occur to anyone to lock their doors. Everybody knew everything about everybody else. Not exactly the best place to keep this kind of secret.

I suspected something was amiss as early as the age of eighteen, when I went into my older sister's room and started trying on some of her clothes. A bra (she was still relatively flat chested as far as I could tell), a frilly skirt, her patent leather shoes. It made me feel good and I didn't know why.

The other boys that I hung out with were already talking about girls (as if they knew what they were talking about). I kept my mouth shut because I didn't want to fuck those girls -- I wanted to be them.

Every now and again I would go through my sister's dresser drawers, trying on her clothes and even sniffing the panties she threw in the hamper. This continued for a few months, until one day she unexpectedly came home early from her junior college and caught me in her room wearing her bra and panties.

"What the fuck Todd? What are you doing in my stuff?" As my older sister, she told me repeatedly that I was on the Earth simply to annoy her. This was a major transgression (no pun intended). She ripped the bra and panties off me, leaving me naked and ashamed.

"What are you? Some kind of pervert?" She picked up my clothes off the floor and threw them out of room and then shoved me out, slamming the door behind me. I grabbed my clothes and dashed to my room before my mother saw me. I shut my bedroom door behind me, leaning against it panting and embarrassed. I also had a raging erection. I threw myself on my bed and masturbated, praying my mother wouldn't interrupt me. Something about wearing her clothes stirred a desire deep inside me, a desire I couldn't suppress, even to this day.

After my awful experience with my sister, I started experimenting with my mother's things. Every Wednesday she played bridge with her friends and when I got home from school at 3, I had two full hours by myself at home.

I started by going through her underwear drawer. Her bras were considerably larger -- the tag inside them said "34D." I stuffed her pantyhose in them and admired myself in the full length mirror in her closet. I would take a pair of her used panties out of the hamper and put the gusset over my nose while I beat off in their walk-in closet. It was heaven to inhale her rich, musky smell as my hand glided over my turgid penis. I would use her panties to wipe up the mess and then sniff the combination of her sex and my cum. I kept the cum stained panties under my mattress and would use them several times before I washed them in my sink and returned them to the hamper.

Dress up advanced to her dresses and high heel pumps. By this time, I was fourteen, and only about two inches shorter than her. I loved her wispy sundresses and stiletto pumps. I tried walking in them, shuffling my feet on the floor and trying to feel glamorous. I always ended up masturbating on my parent's bed, usually with a freshly used set of panties.

I started noticing my mother more, looking more intently at her large, rounded breasts. I might catch a glimpse of her naked, after taking a shower. Or maybe bending over and allowing me a view of the deep valley between her snow white breasts. I wished I had breasts like hers.

One day my mother was cleaning my room and decided to flip the mattress. She found a pair of her panties wedged between the mattress and box spring. She recognized them as hers. She waited at the kitchen table till I came home from school. I came in the side door to the kitchen, and my heart sank when I saw the panties sitting on the table in front of her. I knew they were caked with my semen.

"What's this?" she asked me. She held up the panties with two fingers, as if she was holding a dead mouse by the tail.

I fumbled for an answer but nothing came out.

"It's disgusting." She got up and went over to the stainless steel trash can. She stepped on the foot pedal and lid popped open. She made a show of dropping the heavily soiled panties inside it.

"You'll stay out of my room from now on. Do you hear me?"

I nodded.

"Do you want me to tell your father about this?" I shook my head. My father was the coach of the Pee Wee football team that I was on. He wouldn't take too kindly to knowing I liked to wear my mother's clothes and beat off in her underwear.

"If I find out that you've done this again, I'm going to tell him."

I cowered in front of her.

"Go to your room. You make me sick when I look at you."

I slunk to my room, embarrassed again, but not before sneaking one last look at her heaving breasts. I had an erection in my pants that needed immediate attention.

My last memorable moment was something that both shamed me and defined me. It was sometime after my eighteenth birthday, after high school graduation but before I went to college. My mom and dad had gotten divorced a few years back and my mom had already had a handful of boyfriends. Her then current boyfriend Morgan was probably five years younger and was a carpenter with a local residential contractor. My bedroom was down the hall from hers, and I could often hear them going at it while I masturbated, picturing his buffed body, glistening with sweat, fondling my mom's hanging tits while he fucked her from behind.

On that particular day I heard them having sex, then showering and leaving for dinner. My mom told me not to wait up for them. When I heard the door slam shut that was my cue to go into her bedroom. I went for my/her favorite black lace bra and panty set. I laid in the bed in the spot usually occupied by my mother, imagining that Morgan was fucking me instead of her. I leaned over to the side, and could smell the distinctive odor of sex emanating from the bedside wastebasket. I moved aside a few sticky tissues and uncovered a used condom with a knot tied in it. The cum in it was still warm.

I held it with two fingers and watched the cum in it pool into the reservoir tip, filling it. I looked at the milky white splooge and wondered what it would taste like. I'd tasted my own many times. I found a safety pin in the nightstand drawer and pricking the tip as it hung over my open mouth. I watched the thick splooge drip onto my tongue. I was revolted by its tart taste and slimy texture as it pooled on my tongue. But it didn't stop me from sucking hard on the tip, tasting both the cum and the lubricant on the condom, using my fingers to squeeze every drop of the ejaculate into my mouth, tasting it, and swallowing it.

I knew it was a dirty, wicked thing to do -- to intrude on my mother's most intimate moment. But to taste another man's cum -- it became a lifelong obsession of mine.

I was stroking myself, still tasting a residual saltiness, when I heard my mother's voice from downstairs.

"My purse is upstairs."

I heard the clunking of Morgan's shoes on the stairs, and then the bedroom door opening.

"What the fuck!" Morgan was looking at me, prone on the bed in my mother's bra and panties (the panties were actually down around my ankles), my cock was bobbing in the air, and I was holding his recently used condom in my hand.

"What is it?" my mom cried from downstairs.

"Nothing," Morgan called out. "I just stubbed my toe. I'll be down in a minute." He shut the bedroom door and stood at the foot of the bed.

He loomed over the bed, watching me shiver, even though it was warm in the room.

"You fucking queer. What the fuck are you doing?"

"I ... I ... I don't know," I stuttered. I pulled up the covers to my chin.

He came around to the side of the bed and pulled the covers back down, exposing me and my shame.

"Should I call your mother up here?"

"No ... no ... please." Anything but that. She would absolutely kill me.

"You're going to be my little sissy boy," he declared, his eyes almost glowing. He threw the sheets back over me.

"Wwwhat do you mean?" I had an inkling what he meant. I was afraid ... and excited.

"You'll find out." He grabbed my mom's purse and left. Once I heard the front door shut I tried to put everything back where it was and went into my bedroom, shaking and in fear. I was discovered.

Morgan was a hunk of a man, and after that incident he tended to glower at me as if I was a disgusting piece of shit. I kept my distance from him, not knowing what was going through his mind. One night I heard noises from my mom's bedroom, then her door opening. I had no doubt they had just finished having sex.

" ... back in a minute. Just going to grab a beer and some leftover pizza," I heard him say.

He padded down the hallway in his bare feet and opened my door. He was naked, but for a towel wrapped around his waist. His arms, legs and chest were covered in a generous amount of curly, dark hair. He had a two day growth of beard. There was sweat still beaded on his forehead. He shut the door behind him, dropping the towel to the floor so I could see his flaccid cock. It was longer and thicker than mine was, even when erect.

"Come here sissy boy."

I was laying on my bed. My eyes were as big as saucers. I couldn't take my eyes off his big cock, shiny with a combination of his cum and my mom's pussy juice. My cock was pressing against the zipper of my jeans. I stood next to the bed.

"Over here, and on your knees." His voice was deep and commanding.

I got on my knees in front of him, about to worship his cock. He lifted up the bulbous head and rubbed it against my lips.

"Open."

I did.

He slid his cock into my mouth, stuffing it full. I could taste him. I could taste my mother. He knew what I wanted to do.

"Go ahead sissy boy. Beat your meat while you suck me off."

With his cock in my mouth, I managed to unfasten my pants and pull out my erect penis, using my right hand to pump it and my left hand to encircle the girth of his manhood. He used his hands to push my head towards him, driving his cock to the back of my throat. With saliva dripping off my chin, his tool started jetting hot cum into my mouth. He grunted, ejaculating more, until his cum started to drip out of my mouth as well.

"Morgan, you coming back?" I heard my mom call from her room.

"In a minute," he bellowed. Then in a gruff voice he said, "Clean my cock, sissy boy."

I did. It was the best day of my life.

Chapter One

That was my earliest experiences with my transsexual urges. It portended a future of guilt, suppression, frustration ... and occasionally elation. So here I was, a married man at age 45. My wife Muriel bore two wonderful children, and both were in college. With the kids away from home, I finally summoned the courage two months ago to tell my wife about my secret urges. I just couldn't hold it inside me anymore, and if there was anyone who would understand, it would be her.

I was wrong.

I thought I knew her. I thought she confessed all of her innermost secrets to me. I'd explored every inch of her body. Like my mother, she had large breasts, even larger than my mother, and I could spend hours sucking, fondling and licking them. I also took great pride in bringing her off with my tongue. I would spend hours licking her pussy and asshole, knowing when and where to touch her to bring about the most intense orgasms. I never confessed this to her, even when I told her I was a closet transsexual, but I often thought about ourselves as lesbian lovers. Even though we had intercourse, it was an afterthought for me.

Two Months Earlier

I remember the day I told her. It was my 45^th birthday. We always had sex on my birthday, and sometimes I would ask for something "special" and oftentimes she would grant my one-time request. I think it was my 30^th birthday when we had anal intercourse. That was not to be repeated. On my 40^th birthday she let me come in her mouth. That was not to be repeated. I was hoping that the third time would be the charm.

We finished the birthday dinner Muriel prepared and she was finishing taking a shower. She walked in naked, but for a towel wrapped around her wet hair. I was in the bed sitting up, with my pajamas on, watching her tits bounce as she walked in.

"You've got that look on your face," she said, unwrapping the towel and drying her hair again.

"What?" I asked, again showing my ignorance, but not taking my eyes off her pendulous breasts.

"You want something from me." She said it in a way that made me not want to ask her.

"Never mind," I said. I wanted her to feel a bit bad because she made me feel guilty about asking for something special on my birthday.

She realized she was being a bit of an ass. "Let's start over. Happy birthday! Is there something special you want to do today? She dropped the towel down on the ground. Even though I have strong transsexual urges, her body still made me hard. I wanted to fondle her tits, lick her pussy, eat out her asshole. The primal urge started to rise inside me.

She could see I had that look in my eye. It made her feel good that I still wanted her. "So what is it?" This time she asked nicer. I was still trying to decide if I should ask her. I'd been thinking about it on and off for several months. A baby step. That's all I wanted.

I steeled myself and then just spit it out. "I was hoping I could wear a pair of your panties and have you suck me off while I'm wearing them."

"My panties don't have a hole in them."

"No ... no ... you would hold the elastic waistband down, you know, while you're licking me."

There was a long pause. Her wheels were turning. "What's going on Todd?"

"What do you mean?" I knew exactly what she meant. I was just buying time to slow my mind down.

"C'mon, you know what I mean. Why would you want to wear my panties? Are you gay or something? Is there something you want to tell me?" There was an accusatory tone to her voice. I didn't like it. I had clearly misread her. She had already gone off the rails and we hadn't even done anything.

"No, I'm not gay." I didn't want to tell her that I really wanted to be a woman. What was my exit strategy?

"I don't think normal guys would ask for something like that. I could at least understand why you wanted to fuck my ass." We rarely spoke to each other in such graphic terms, and Muriel rarely said "fuck," even in private.

"Maybe I'm not a normal guy."

"Well, you fooled me. We've been married for twenty years."

"Well, I guess I'm not." Then I decided to be more upfront. "Sometimes I have fantasies about wearing your clothes."

"And do you?"

"Do I what?" I was being intentionally stupid.

"Wear my clothes," she said in exasperation.

"Of course not. It's just a fantasy." It was such a big fucking lie. Ever since we were married I secretly wore her clothes. Sometimes I would wear her panties under my suit when I went to work. On those days I'd masturbate in the men's room at lunch time and cum on her panties. If I was really horny I'd lick the cum off them. I probably had worn at one time or another everything she had in the closet. I loved wearing her 34DDD bras. I coveted her big tits.

"Just a fantasy?" She said it as if she didn't believe me. And having rifled through her closet for twenty years, I must have slipped up one of those times, maybe putting something back in the wrong place and her noticing it. I waited for the other shoe to drop, despite my weak denial. It did.

"I've known you've been wearing my clothes for quite some time."

Oh fuck. I knew it. Here it comes.

"Sometimes my clothes were moved. Sometimes I couldn't find my favorite bra or my favorite pair of panties. I really didn't know for sure until I found a pair of my panties in your underwear drawer. I knew I didn't put them there because they weren't clean. I could see your dried cum on them."

Fuck. Busted. "Why didn't you say anything?"

"What did you want me to say? Hey Todd, are you gay? Are you a transvestite? Or something worse? Do I need to see a divorce attorney?"

Oh fuck, this was spiraling out of control. I had to get this conversation re-centered. "Forget about what I asked. Let me ask you ... do you love me?"

"Well of course I love you. We've had two kids together. We've been married twenty years."

"That's not what I meant and you know it. Do you?"

She was a bit more thoughtful this time. "Yes, Todd, I do."

"I'm just trying to be honest with you. That's what people do when they're in love."

Her body language softened. "You're right. Maybe I'm being a bit harsh. But Todd, my underwear?"

I decided that honesty was not only the best policy, it was the only choice in this situation. "Yes, your underwear."

Muriel looked like she was going to give ground. It really wasn't the craziest request in the world, and it certainly wouldn't hurt anyone. "Well I guess I'll do it. Which pair did you want?"

Since she already called me out, I went to her underwear drawer and pulled out a pair of cream colored French cut panties with a frilly waistband. Maybe she knew this, but I probably beat off into those underwear more than any of the others.

"Those?" She laughed. "They're my favorites. At least you've got good taste."

I took off my pajamas and slipped them on. I stood in front of her. My cock was rock hard. The thin material of the panties was almost painful to me. She knelt in front of me and lowered the waistband with her thumb so my cock could pop out. I could feel the lace pressing against my balls. I was afraid I was going to cum without her touching me. I reached down and cupped her tits while she gripped the base of my cock with her hand and starting pumping while she used her lips to form an "O" and let me fuck her face.

"Oh God ... ," I moaned. "Muriel ... it feels so ... oh God ...".

I started to cum. It was too fast, but there was nothing I could do about it. White, sticky cum started flowing over her lips and dripping off her chin. I never wanted it to stop. I squeezed her tits while she continued to suck me off, even after I had come. The feeling was so intense I had to stop her.

"Please stop ... Muriel ... thank you ... thank you ...". I was breathless.

She wiped the cum off her chin with her finger. She got a box of tissues and wiped off her face, and then her hand.

"I didn't know that you'd enjoy this so much. Maybe there's a lot I don't know about you."

Now the cat was out of the bag. There was no turning back now.

End of Chapter One