A Long Journey To My Brother

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A young woman with a penis learns who she truly wants.
17.3k words
4.58
42.5k
64

Part 1 of the 2 part series

Updated 06/10/2023
Created 08/04/2021
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You don't know how badly you need someone until you do. Or why. But you do. I needed my brother, more than I ever thought possible. He saved my life.

It wasn't easy being born with a dick. Not when otherwise you're a female, with female parts (save the defining one), female looks and a female mentality. And no, it's not a big dick. I'm being generous to myself if I say it's more than four and a half inches. But it works and feels like one. It certainly behaves like one.

I never knew a life without it. Growing up in a small western Michigan city, with no shortage of rednecks, I knew that a girl with a penis was not only unusual, but considered alien and even wrong. I learned early on to hide that detail for the sake of my safety and sanity. Nobody needed to know about it, and I kept people out of that part of my life. They weren't close to me, so there was no need for them to be aware of it. My family was another matter.

My father was happy to have a second boy. He considered them stronger. My mother was disappointed, but she didn't want another child once I came along. Two were enough.

Of course, seeing the second boy begin to develop female characteristics wasn't easily understood either. Higher voice, softer features, a much smaller body than my brother at the same age, they didn't make sense. The medical tests made even less, and when the doctors determined that my body was actually a female body, nothing made sense, at least to my parents. It was 1981, and even though I'd been named Taylor, both the pop star and the definition of trans were many years away, not to mention the concept. I was six, and my body only made me an abomination to others. My father began leaving the next year.

By the time I was eight, he was gone for good. It hurt like hell, and left me with plenty of additional neurosis, yet looking back, it was probably for the best. He wouldn't have been able to contain his rage, and I would have borne the brunt of it. Dealing with my mother was bad enough.

She tried to contain her anger, but it would periodically spit out in petty and destructive ways. When I was seven, she refused to buy me girl's clothes, a situation that would continue off and on for the next eleven years. At ten, our doctor had to step in when my mother insisted I take gym class, which fortunately had been excused from my life. I will always be thankful to him for sparing me that certain humiliation and degradation. And at twelve, Mom told me that since I wouldn't be having a period, bras needn't be on the shopping list through my teens. She said I could be an "in-between" for the rest of my life. It was around that point I first considered ending it all.

It began with trying to drink two large bottles of Mom's booze, of which she had stashed many around the house. All that did was make me violently ill. I soon graduated to self-harm, mostly cutting myself, leaving me with many scars and a habit of wearing long-sleeved shirts. At fifteen, I even acquired a snub-nosed pistol, ostensibly for "protection", though the only protection I really needed was from myself. Thank God I got it. My brother found the gun, sensed what it would be used for, and threw it away. Jacob knew how to protect me from my biggest dangers.

My older brother wasn't a shining star, nor was he everybody's favourite. Hell, there were many times when I wanted him on the other side of the planet. Silent, sullen, often cranky, Jacob was every bad teenage stereotype come to life. He had few friends and even fewer prospects. Our father's absence and mother's increasing alcoholism had left him with both a fatalistic outlook and the burden of being "the man of the house", a title and position Jacob wanted nothing to do with. Yet when the chips were down, I could count on him like nobody else.

When I was bullied on the playground for being a little different (though the other kids had no idea just how different), he would step in and protect me. When our mother was drunk and looking to lash out, he would goad her into some argument, allowing me to escape. When I was fourteen and had finally began to develop, he escorted me down to the department store, reluctantly introduced me to the sales associate in the young women's division, and then paid for the bras which I was both embarrassed by and thankful for. While usually grumpy at these instances, Jacob would come through without fail. He was my aggrieved anti-hero.

On Independence Day of 1990, Jacob shattered my world. He told my mother and I that he had signed up with the military and would start basic training the following month. Having turned eighteen a few months earlier and just finished high school, he'd been able to sign up without any parental involvement. In retrospect, it was obvious that Jacob felt this was his only way out of our depressed town, not to mention his depressing home situation. But all I could see was that he was abandoning me. I was fifteen, and the shit was going to rise.

Three years of high school is a long time to be lonely, not to mention agonized. None of it got better. Mom got worse, school was just there and I had few friends. Worst of all, the best part of my life was actually on the other side of the planet. And considering his communication skills, we were lucky to get a letter from Jacob every few months. Oftentimes, the only way we knew he was alive was that his employer didn't send anyone to our door.

Jacob's timing had been pretty shitty. A month after he enlisted, the Iraqi army invaded Kuwait, leading to America and a number of other countries returning the favour several months later. Our country, and military, was suddenly at war a world away from western Michigan. It would have been little more than news hour TV for us except for one important thing. Jacob was there.

Although he wasn't in direct combat, we knew that my brother was involved in some fashion. His few letters came from the Middle East, and in his usual restrained way, Jacob told us that he had a particular assignment without providing specifics. Even when the brief war ended, he remained in Iraq and continued with his duties. I wanted to know and I didn't. Mostly, I wanted him home.

Our mother didn't deal with it very well. Her drinking increased, as did her outbursts directed my way. I couldn't be bullied in quite the same way as when younger, but it didn't make my days a vacation in paradise.

"Don't you have a boyfriend yet? Or a girlfriend? Or some sort of friend? What's wrong with you?"

Like many unhappy parents, my mother knew how to strike a nerve. I was late in my second year of high school, yet nowhere close to having a date for the sophomore dance. It shouldn't have been a surprise, as the thought of having any sort of relationship was strictly fantasy. I was growing into a scruffy, scraggly young lady, not horrible to look at, but quite rough around the edges, and my self-esteem was more fragile than cheaply made crystal. Worse yet, I found that I was more attracted to boys than girls, which could be very dangerous. If I ever got intimate with a male and he flipped out, got violent and then spread the word about what I had between my legs, life would never be safe.

Girls could have been almost as hazardous, largely due to the fact that I knew this was one secret they would not keep. Word would quickly get around and life would be a living hell. I knew I needed to keep my distance from people.

There was only one person who could keep my secret, not out of guilt and anger but due to consideration, and he was thousands of miles away.

Jacob returned in the fall of '91. He wasn't discharged but had managed to get a month's furlough, allowing my brother to come home and for me to breathe a little easier. Mom cried and doted over him for a few days before returning to her accustomed manner and habits. Our small, rented house slipped back to its usual air of strung tension.

"So what were you doing over there?"

Our mother was passed out, probably for the night, a true relief to be sure. It enabled Jacob to be a little more willing to open up, at least by his standards.

"M.A."

He honestly thought that said everything.

"Huh?"

"M.A." Eventually he noticed the confusion on my face. "Mortuary Affairs. Used to be known as Graves Registration. Means scooping up the dead bodies, figurin' out who they were, and gettin' them ready to be returned." I had thought I was ready to hear anything. I'd been wrong.

"How did you get that job?"

"They said who's willing to work for M.A.? I thought it was something to do with Military Affairs. Gettin' some general's coffee or somethin'. Didn't know they'd changed the name."

I was horrified. My brother had been stuck with the worst job imaginable. Thinking about it for long would have been too much, so I decided to move the conversation forward.

"You don't have to go back to that, right? I mean, the war's over."

"No. I'm not going back to the army."

"You're leaving the military?"

"Sort of. I'm making a transfer, kinda." Once again, Jacob was confusing me. Nobody did it better.

"I don't understand."

"I've signed up with the U.N. They have a unit, a program, to settle hot spots before they become wars. They call it Peacekeeping."

"What does that mean?"

"Means I'll be travelling around to different places, negotiating to stop wars before they start."

The thought of my brother negotiating anything was funny, and I saw a chance for levity.

"Geez, ya coulda gone to law school for that. Is that what you're gonna do? Sit around a conference table and talk about stopping fights? You going to wear a dapper suit? Or maybe they'll just give you something to calm them down. How does a baby blue helmet sound?" I thought it was hilarious. Little did I know. My brother scoffed.

"Hey, I'll still be a soldier. Just won't have to fight everything that moves. From the sounds of it, I won't have to fight much at all. Just wave my magic wand and watch them do their thing. Be nice and easy."

Little did Jacob know what it would entail. His move would result in the worst horror film he could have possibly seen.

Unfortunately, the day came when Jacob left once more. We saw him off at the train station where he caught the Amtrak to Chicago before flying to New York. Our mother had honoured the occasion by downing a fifth of bourbon before passing out in the bleak station lobby. Jacob gave me a wordless hug before shouldering his bag and climbing into the second-class car. I refused to cry at that point. The tears would come later.

My high school graduation came in '93, and with it a relief that I had managed my school years without "the big reveal". To my knowledge, nobody outside of my family knew about my penis and I intended to keep it that way. Having turned eighteen a couple of months earlier, I was now an adult and knew that my privacy could be easier kept but my safety would be at greater risk. As long as I kept it in my pants (or occasional long, loose skirt), there shouldn't have been any reason for compromise. Unfortunately, that left one problem. I didn't always want to keep it in my pants.

I'm human. I have a body, a body with moving parts and raging hormones (probably quite the mix of estrogen and testosterone), with needs, desires and urges flowing through it. I would get horny, just like other people, and wanted to find ways to relieve that horniness. Naturally masturbation was a staple, as having one hand on my cock and the other on my tits was a pretty common occurrence. Sometimes a finger would get inserted into my back door since I didn't have a pussy to fill. I even graduated to a butt plug for especially randy moments. But that could only go so far, as what I really wanted was to fuck and get fucked.

It wasn't easy. I was more attracted to men than women, though I could appreciate a woman's allure and might even be willing to sleep with one given the right circumstances. But it was mainly men who turned my crank. Unfortunately, I knew that my dick would not only be a turn-off for most of them, but a sizable number of those men could become treacherous if they knew my complete physical resources. Particularly in my hometown. I needed to be cautious, which meant I had to be smart and selective.

My looks were only a mild asset. The scraggly, unkempt look which had been my adolescent companion never really left, with my dirty blond hair resisting effective hairstyling and lips that were the opposite of pouty. In addition, my curves were limited as my hips were slim and my tits, though fronted by pointy nipples aching to be licked and sucked, never went beyond a B cup and weren't terribly perky either. To top it off, my legs were skinny and lacked shape. I often gave the appearance of someone who hadn't filled into her body.

Fortunately, I did have a couple of things going for me. My face was not unattractive, if one could get past my lack of makeup and moisturized skin, and those slim hips gave me a small tight backside which could hold a dollar bill between its cheeks, not to mention a plug in my hole. I suspected a couple of fellows had held dirty thoughts about my body. I simply didn't have the confidence to find out.

My day to day life wouldn't have been much incentive either. Knowing I would need some sort of income to realize any future plans (whatever they might be), as well as to keep my mother at bay, I looked around town for a decent job. Like Jacob, I didn't have a whole lot of connections to give me a leg up. Fortunately, a diner on the outskirts of town were in dire need of a new waitress. Between plenty of shifts, a reasonable amount of tips, and a dress code that did not require short skirts or tight pants, it was a moderate salvation that gave me some slight independence. It also allowed me to learn the flirting habits of various men, most of them older, which enabled me a couple of discreet encounters. Sadly, they would be less than ideal introductions to sex and relationships.

The first time was on a rainy night in a pickup truck. In the cab, not the bed. He was twice my age, pot-bellied, and stunk of cigarettes. He also didn't mind that I had a cock, just so long as I had tits for mauling and a hole for thrusting. His cock was only average length but rather thick, as I learned when he shoved it up my virgin hole without any sort of lube. The pain was so stunning that I couldn't scream, I couldn't gasp, I couldn't make any sort of noise. He just slammed into me, over and over, grunting like a grizzly bear as I wondered if this was what sex really was. My own cock was completely soft, so I just assumed that I wasn't aroused enough and maybe the next time would be better. I thought of the diner's yellow tablecloths while I waited for him to finish. Once he did, shooting his cum directly into my ass (what a desperate idiot I was not to insist on a condom), he slowed down, breathing heavily, before stating in a flat voice, "Sorry I can't give you a ride home. Think there's a bus stop down the road." Whatever the ideal first time was, this had been miles away.

Six months, two blood tests, and endless contemplation later, I took another chance on sex. Once again it was an older man, but this time we had a motel room, he used lube, and I was turned on. I came, my hole felt better, and I felt better. If not romantic, it was at least a good experience. That was until he spoke while rising from the bed.

"We better get going. I gotta be home before my wife gets back."

Fuck. He was married. I was an idiot. He'd never said anything, but I'd talked to enough husbands at the diner to know the signs. I should have seen it, but my cock was thinking something else. I was now "the other woman", if only one time, and I felt like a cheap whore. Not exactly what I hoped to be doing with my life.

They say a cock has no conscience. Well, I can tell you it has no self-respect either. When the guy called a week later, whispering sweet nothings and sour everythings, I remembered the feelings. The feeling of his mouth on my breasts, the feeling of his hand on my hard cock, the feeling of his long, slim dick thrusting into my asshole. Slut, whore, harlot, I called myself all of these names and more. I couldn't look myself in the mirror.

We met at the motel.

I saw him three more times. Not only did he bugger me good each time, but on the last occasion, he even sucked me off and let me thrust into his butt. Taking it was getting easier and better each time, but giving it to someone else, slidiing my dick in and out of their ass, that was incredible. No wonder guys were so stupid. Most of their thinking must have been pointed towards a hole. It was addictive. No matter how shitty I felt about myself, it was more than covered by the feeling of fucking someone with my cock.

That was the last time we met, and neither of us had much choice in the matter. His wife discovered his wanderings, the person he was wandering to, and somehow, she learned all about me. Everything. In short order, she served him with divorce papers and said if she didn't get the house, the kids and their investment portfolio, she would reveal his love for dick and laugh while he slit his throat. He was soon gone, from my life, from our town, and for all I knew, perhaps from existence.

By comparison, I got off easy. His wife made a visit to the diner (thank God at the back door) and proceeded to let me know, in a cold monotone, that I was a slut, a cheap whore, a homewrecker, and above all else, an inhuman freak who should have been strangled at birth. My eyes were down, my head was down, and I was down. What could I have said? I had fucked up, and my tears gave her pleasure. She slapped me, kneed me in the groin and left me laying as she got in her new Lexus and sped off. The rain began to fall.

I was nineteen and learning the hard way.

Periodically, my brother would write me. We had learned that he should send me the mail and I would deal with Mom. She barely cared, why should she know? After a brief return to Iraq, Jacob would go to the fracturing Yugoslavia for two years, followed by a year in Africa before returning to Bosnia in '95. He didn't tell me many details, though he often raged at the fact that he couldn't do anything if the combatants decided to keep fighting. At that point, he was little more than an observer. It sounded like it sucked, but I had no idea just how much. Besides, I had my own shit to overcome.

It had become obvious that I was in a dead-end job, in a dead-end town, and my life would be a dead-end if I didn't get the hell out. But I also knew that I'd never get towards anything good if I just looked to get away. I had to be going in a direction. To that end, education was an obvious target.

During my school days, I hadn't quite been a scholar, but I did okay. However, I knew that being better than okay would help, so to that end, I took a couple of correspondence courses to shore up some weaknesses and discover some strengths. I also began to look around for colleges and universities that might be a good fit. Needless to say, none of them were anywhere in Michigan.

I also began to travel in order to expand my horizons, not to mention scope out some potential schools. It was on one such trip, in Chicago, that I had my first sexual encounter with a woman.

Her English wasn't great, nor was her waistline, but she had a twinkle in her eye and we quickly connected. I soon found myself on her bed, on her body, losing clothes and gaining confidence. Amazingly, she didn't mind my cock, she simply said that she knew where to put it. I was elated. Though I preferred the musky aura of a man, her soft lips and big tits were enough to make me rise up and plunge forward. It was going to be a thrill.

It was weird. As soon as I sank into her pussy and began thrusting, I sensed that something was amiss. She had the right parts and we were fitting tab A into slot B, but it just felt a little off. The connection we'd found seemed to have slipped away. It wasn't so glaring that I couldn't finish the job, either for me or for her (I went down on her after I'd cum into the condom), but it all felt a little surreal, almost out-of-bodyish, and I wondered if I was in the wrong place. In a sense, I was. It wasn't a bad place, just not where I felt the most comfortable. I'm sure she sensed it as well.