Josephine

Author's Note

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This story is part of a challenge I posed to myself to write a story for every Literotica category. I had originally thought that it would be more sexually charged, but as I worked on the character development in this story it turned into something unexpected. It became a story about a person's struggle with and eventual transition away from heteronormative expectations.

Thank you for taking the time to read it.

Joey

====

Ever since I was a young teen, I had been drawn to women's clothing.

Maybe it was because my older sister imprinted on me as a role model, or maybe I was just responding to the way she always seemed to smell like an animal in heat. Whatever it was, her clothing drew me.

My older sister was hot. Not in a super-model sort of way, but more in an attitude sort of way. She did have a nice body and an attractive face, but she was strong and kind of tom-boyish too. And she was most definitely oversexed.

I was a young, scrawny boy with no prospects for getting laid yet.

I don't remember how it started, and I knew it could get in me into a lot of trouble, but at some point I began pulling underwear out of her laundry to smell as I indulged in the vice of most partner-less, hormone driven males. At first it was just a sniff, but it was not long before I found myself burying my face in them. And if she had worn them after having sex, the musky smell would drive me insane.

Then my urges escalated and I started wearing them. I can't even remember when I started putting them on. I didn't think she'd notice. When no one else was home I would find a dirty pair of her stockings, panties and a bra to wear and look at myself in the mirror.

My sister started complaining about how her favorite stockings kept getting runs in them. Our mother took the opportunity to suggest that her clothing might last longer if she didn't pray like a whore.

Then one day I shaved my legs.

I wasn't even very hairy to begin with. Being blonde, my leg hair was very fine and pale. I told myself it wouldn't be noticeable and anyway. I thought it would grow back in just a couple of days. But once the euphoria of giving in to the urge passed, I realized how noticeable it was. And it took longer to grow back than I anticipated.

I was climbing up into the hay loft when I slipped. It wasn't a terrible fall, but I banged my shins pretty badly on the way down.

I was rolling on the ground holding my shins and spitting vulgarities when my sister ran in to see if I was alright. She saw blood soaking into a tear in my jeans and carefully rolled up the pant leg to see how bad it was.

I was in too much immediate pain to think about it. She was saying something about it being a really bad skinning but that it was probably nothing serious when she paused. She was holding my leg and I realized that she could see or maybe even feel they were stubbly.

I was in pain and horrified. Fear overcame pain. I froze. I felt her run her hand up across my skin intentionally. I felt the stubble move under her hand like only stubble moves. She blinked a couple of times.

And then she said that I should clean it up and walk it off so our mother wouldn't have to worry about it. She patted me on the side, got up and left.

In a moment of paranoia I thought that she had immediately understood everything and knew all of my sins. But whether this was true or not, she was right. I couldn't risk Mother examining the injury.

The realization of being caught frightened me. No one could know. If anyone found out there was no way that a pervert like me would get out of that little town alive. The fear was enough to make me give up my teen experiments with my sister's underwear.

Joe

===

I was a man. I was 22 years old, worked in a local plant, and had just gotten a degree in accounting from a nearby community college. I had even managed to have a few short term girlfriends.

I still didn't have many friends. I wasn't really into hunting or sports, and when I tried to fake interest it didn't really sell. Other than working, drinking and raising babies there really wasn't much else to do or talk about in that small, non-descript town.

The few women that had put out were husband hunting, I think. They figured that I had a degree so maybe I'd end up in management at the local plant and be a good provider. But in the end I always ended up being a little too nerdy or unmanly for them.

I was having a dry spell. Perhaps the last dry spell, I thought. There really weren't all that many available women in town. And the few available women in town had all given me a try and decided to move on.

The most recent of these departed women had left a few of her things at my apartment. She had stayed over on a number of occasions and had left a few changes of clothing. All of the women I had dated had done that. Sometimes I wonder if women do that on purpose as a way to mark territory.

I was putting her things into a bag so that when she inevitably stopped by to pick up them up we could minimize the awkwardness of breaking up. I was holding a pair of frilly panties in my hand and thinking that she was the last woman in town and that this could be an awfully long dry spell.

I lifted them to my nose to smell her pussy one last time. The urge snuck back into my mind. My cock grew hard and I figured, "What the fuck. I may as well."

Before she picked them up, I washed all of her things to make sure there weren't any cum stains. She said that I was considerate and so on and so on. And left just like the others had.

But the urge, that perverted thrill, was back. It was a casual thought. I didn't have access to any women's clothing. But as the dry spell wore on my mind started trying to find ways to make jerking off more thrilling.

I stopped by Mother's house after church on Sunday, like I always did, to have lunch and listen to her lovingly tell me I needed to find a good woman to mother my children and how she wasn't getting any younger and wanted to be a grandmother.

Mother was all of 45 years old and already trying to lay mortality guilt on me like it was the middle ages and she could die of old age at any moment. But it would be alright and she could pass into heaven joyfully knowing that I had given her good, strong grandchildren to carry on my father's name.

My sister had moved to a big city and hadn't visited in a while. Mother wanted me to send her a few things that were in her old room. Trying to be a good son, I went and packed up some of my sister's winter clothes "so she wouldn't catch her death". And, of course, the crucifix that my sister had absent mindedly left hanging over her bed instead of taking with her.

I was looking into her underclothes drawer to get some warm socks like Mother had asked when I became momentarily transfixed. My fingers brushed lightly across her carefully folded tights. She had even left some of her panties and a bra behind.

I could feel my heartbeat pulsing in my temples.

And I casually packed those things as well. But they never made it into the box that I mailed the next day.

The next night they sat carefully laid out on my little coffee table while I sipped beer. My mind was racing between desire and fearful shame.

She had left behind older items. The underwear had a few small holes around the waistband. The bra's elastic was worn out. And the tights and stockings had runs. But they were soft and they felt good n my fingers. Her scent had been washed clean from them, but I could feel my cock throbbing against the containment of my jeans.

I couldn't resist.

Every night after I thought everyone in this tiny town had gone to bed I would slip into my sister's old undergarments. At first it was just to sexual gratify myself like I used to. But soon I found myself falling asleep in her old panties. I loved waking up in the morning with my morning wood straining against the fabric of the snug panties.

I began to be bold. I started wearing the panties under my boxers when I was out around town. It stopped even being a constant sexual thrill. I simply loved the way they felt. And I loved the way that they made me feel.

Sudden Migration

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My sister was waiting for me when I got home from work. It was a small town. Everyone knew everyone. My landlord had let her. We were siblings after all, right?

But I was surprised. I had no idea that she was coming to visit. And it was the middle of the week. She had a regular day job. And she had spent hours driving.

We made family-style small talk, but I could tell that something was wrong. Even if her behavior hadn't tipped me off, the whole situation was alarming. Something was wrong and she was trying to find a way to get to it.

She talked about how I'd love the city she lived in. How great it was. She went on and on and then said that I should come live there. I could even stay with her until I got myself set up.

It was rushed and pushy. Finally she got right to it.

"Joey ...," she said. She had always called me Joey when she was slipping into protective older sister mode.

"Joey", she said, "you need to come with me. Tonight. Now. Pack up what you need. We'll figure out the rest later."

She was dead serious. And she was pale. She produced the plain brown paper bag that I kept my girly underclothes in. I didn't even think of them as hers anymore. They were mine.

She didn't even open the bag. We both knew what was inside. We just looked at each other. I didn't even ask how she found out, or how she had found the bag. I tried to stammer out an explanation.

"Stop," she said. "I don't care about what's in this bag. And I don't care about what you do. You're my little brother and I love you. No matter who or what you are. But someone else knows."

My head grew light and I could hear the panic and blood rushing in my ears.

One of her friends had called her to let her know that people were talking. There were some good old boys at the plant that had been drinking the night before and talking about how they should do something about that sissy-boy faggot. Me. They were talking about me. My sister's friend knew what that meant. My sister knew what that meant. And I knew what that meant.

In a town like ours it meant that my life was in danger. It had happened before. And I wasn't even gay! I just liked to wear women's underwear!

I was a zombie. My sister helped me grab a few things and shuffled me down the stairs and into her car and before I even realized what was happening I was on the state road heading out of town.

My sister's friend called her back the next day to find out if I was alright. The very same night that my sister had come for me someone had kicked in the door to my apartment not too long after the local bar had closed and trashed the place. If I had still been there I would have likely been beaten to death in my own bed.

I never did see my mother again.

Adaptation

==========

Once the initial fog of my sudden move wore off I did my best to tie up loose ends "back home".

Mother wouldn't accept my calls. When she heard my voice she would hang up.

My former employer seemed happy to be rid of me and had no problem forwarding my last paycheck to my mother. "It was the least I could do for all the pain I had caused her."

My former landlord was furious about the apartment and wanted to send me a bill for damages. He even threatened to have the police chief hunt me down to bring me back and account for the damage done.

I gave no one any indication of where I had gone. I was actually a little afraid that someone would hunt me down to finish the job.

But my sister had been earnest about letting me live with her. Space was tight, but we had grown up in a small house and were used to living with each other in this way.

It took me a long time to get back on my feet from the shock of knowing that whoever had just tried to kill me was someone I had probably gone to church with every Sunday for my entire life.

But my sister helped me adapt to my new life. After a few months I had managed to pick up a pretty good job using my degree and between us we had enough money to move to a slightly larger space.

The fear had a strange impact on me. I did my best to be a good, manly man. I was in pretty good shape, but I started working out intentionally. I began to dress in a more conservatively masculine manner. And I threw away the brown paper bag full of women's undergarments and shame.

I did my best to purge it from myself. Giving in to those perverted urges had very nearly gotten me killed. And as far as my Mother was concerned, I was dead.

It was difficult to sleep at first. The noise was almost unbearable. Every corner of the city seemed to reek of urine and rotting food.

I cried myself to sleep some nights. I cried for how foolish I had been. I prayed for forgiveness. I swore to be the man Mother wanted me to be, and Father would have wanted me to be, even if she would never see me again. Because, I thought, that's what men do.

But I found it easier to make friends in the city. There were all kinds of people there. If I didn't want to talk about sports, I could find people to talk about books. The library system and the museums were a delight to me. For the first time in my life I felt like I didn't have to completely suppress myself just to fit in. And this joy got me through the worst of it.

I adapted. I grew. And I swore that my foolish perversion was behind me. Because, I thought, "That's what men do."

Comfort and Submission

======================

My sister was still an oversexed minx, but our new apartment was large enough to ignore her having loud sex every other night. She seemed to have a three or four men that would visit her in a sort of rotation. I figured that it was a "city" thing. The guys all seemed to know each other and the sex seemed pretty casual.

Eventually some of her girlfriends began to inquire about me, and I went on a few dates. I did my best to mimic my older sister's casual demeanor about sex. It turns out that most women weren't actually cool with that. But some were.

One night one of my lovers tried to get me to put her panties on. She said that she was turned on by the idea of me wearing her panties.

I was shocked, and suddenly scared. Had my sister said something? I think my resistance must have been anticipated, perhaps even happily so. She probably assumed it was the same resistance that most apparently "straight" man would offer.

My lover seemed to enjoy the process of persuading me. She took control and I found myself yielding to her wishes.

I had never shared this with anyone before. I had always done my best to hide it. And I hadn't indulged in this since fleeing to the city.

The experience was amazing. She was gentle, but firm with her commands. And there was no doubt that she was giving commands, no matter how persuasively they were couched.

And when we were both exhausted she "made me" wear them to sleep.

The next morning I awoke with a morning hard-on like I had never experienced before. I looked down to see her lips playing along the head of my cock sticking up over the top of the panties.

When she saw that I was awake, she straddled one of my thighs and began stroking the head of my cock with her fingers.

When I tried to raise my arms to grab her, she pushed my arms down and told me to lie very still. She playfully kept me on the edge of cumming for what seemed like forever while she ground her wet pussy onto my thigh.

She whispered and moaned how my obedience got her off and how she loved the way I looked in her panties. She persuaded my agreement and refused to allow me to cum until I admitted to enjoying submission and to wearing her panties.

My orgasm was intense, and unusually loud. When I finished spurting into her hand and onto my own stomach, she leaned down and ran her cum covered fingers through my hair and down the side of my face. Leaning in, she kissed me deeply while grinding herself over the edge of orgasm against my thigh.

When she left I was still wearing her panties and had my own cum drying in my hair and on my cheek.

I pulled a robe on to take a piss and get some coffee. My sister smirked at me over her oatmeal before I rubbed my cheek and realized why.

Exploration

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Once I realized that there were other people that enjoyed indulging in the same kinks that I enjoyed, my life began to change for the better.

My lovers became more adventurous and I started seeing overlapping themes. It almost seemed like a conspiracy. And it wasn't long before I had yielded completely, confident that these city people were more enlightened than the small town folk that had sought to do violence to my person.

To be playful, I would show up to a date already wearing the panties that the woman had left behind the last time. I figured that if anyone caught me I would simply explain that I was on my way to fuck a beautiful woman who was turned on by seeing me in her panties.

I went to parties where people flirted and openly discussed their kinks. Knowing that I didn't have to conceal my kinks as tightly, they actually controlled my thoughts less. Wearing women's clothing just became a casual "sometimes" game to play in the bedroom. And I discovered that while I sometimes enjoyed being dominated, once the initial thrill wore off it really was just a "sometimes" thing with the right people.

Even my sister, I discovered, was privy to this talk. She was comfortable and seemed to be completely non-judgmental about my sexual deviancy. It was a tremendous relief.

But over time I began to notice my own attitude changing. Even outside of the context of sexual games, I began to find myself wondering why I shouldn't wear whatever clothing I wanted to. I found myself beginning to find women's clothing more generally attractive.

One of my lovers convinced me to shave my legs. Another lover helped me pick out stockings and a garter belt. But it was still all a part of having sex.

One night when my sister was out, two of my lovers came over together and they spent the evening dolling me up in full drag and then pretending I was a straight woman so that they could seduce me into having a lesbian threesome.

It was dark and they wanted to go out to a certain bar that they knew, but I drew the line and we stayed in. But the next day I found myself wondering where they thought that we could go and no one would mind that I was a man in drag.

I asked my sister about it and she said that she had been there, and that it was not unusual for people to go there to publicly cross dress but that even in a fairly liberal city you still had to watch out for gay bashers who would sometimes prowl around known gay bars and drag clubs looking for people to beat up.

It was a conversation that I tried to start as a nonchalant question but ended up being longer and more confessional than I imagined it could be. It turns out that my sister already knew most of it and suspected the rest. She was actually every bit as kinky as me, and perhaps even more so.

She did warn me that women were probably going to try to push me to see how far I'd go, and that I should be careful to not do anything I was uncomfortable with.

In terms of lifestyle, she said that she had no problem with me wearing women's clothing around the house if that's what I wanted to do. But that if I did so when anyone else was around then I had better be prepared for her bisexual male friends to hit on me, if they weren't already.

Oh – and that it wasn't cool to borrow her clothes without asking. We were both grown-ups now and I could buy my own lingerie.

We both laughed a little. It had started off awkward, become confessional and ended with me so incredibly happy to know that I didn't have to hide anything from my sister anymore.