I AM NOT THE ORIGINAL AUTHOR! THIS IS ONLY A REPOST!


I finally got home to my apartment from school. Today was my last exam of the semester, marking the start of winter break. As I walked in, I saw my roommate John grabbing his duffle bag, ready to leave.
"I'm off, I'll see you later." was all he said as he went out the door.
He was likely leaving to stay with his parents for the break, but we don't talk much. Our other roommate Sam had finished his exams earlier left two days ago.
My name is Matt. I am 19, a freshman in college, and I just finished my first semester. I thought I had done well on my last exam and was feeling quite proud of myself. Having the apartment to myself, I pulled up a few of my favorite sites and decided to have my own personal celebration. Right as I was getting into it, I was startled by a sudden knock at the door. I was so surprised I jumped out of my seat nearly knocking my laptop off the desk. I pulled up my boxers and pants and steadied my breathing as I went to answer the door.
“I have got a delivery for a, uh ...” the delivery man paused as he looked at the sheet, “... for a Matthew Garner.” he said somewhat quizzically looking at a small box from a woman's clothing store.
I tried not to blush as I rushed a signature. He couldn't have known the clothes were mine, "surely he'd assume they are for a girlfriend and not mine" I told myself. I glanced behind me at my living room, it was obviously devoid of any female touch, littered with trash, cans, and old food. My face felt on fire and glowed red. I could see in his face that he knew they were mine, and that he thought it was completely disgusting. I hate to admit it, but through all the embarrassment I felt a little turned on. I took the box and quickly shut and locked the door. I looked at the package and realized how grateful this had not come an hour earlier when Sam would have been here. I concluded that ordering the clothes as I did was a foolish decision lacking foresight, and I was feeling especially lucky.
I grew up with three older sisters, and we were all very close in age. For a boy I had a skinny, almost feminine body. I also always had longer hair; I didn't mind long hair and money was tight so my parents never complained about not paying for haircuts. Naturally, when I was much younger, my sisters would play with me as a doll, they dressed me up in their old clothes and practiced applying make-up. I never resisted too much, and secretly enjoyed the games thinking I looked very pretty as a girl, sometimes prettier than my sisters.
I don't know how much my sisters had influenced me, but since I was young I always wished I was a girl. Aside from feeling pretty, my sisters clothes were soft, silky, or any number of other pleasant textures that felt so much better than boy clothes. Then there were all the accessories. Jewelry, purses, hair clips, shoes, there were so many things girls got to wear that boys could not. So after my sisters stopped dressing me up and I discovered masturbation, whenever I was home alone I would sneak into their rooms and dress myself up. Dressing up would make me horny and I would usually just jack off followed by a shower. But sometimes when I had a lot of time, I would get dressed up and lounge around the house pretending to be a girl for the day.
I enjoyed crossdressing, but I'm not gay. Sometimes when pretending to be a girl I would imagine what it would feel like to be fucked by a guy, but I was definitely attracted to women. I managed to get a couple girlfriends, but they never went very far or lasted too long. I was a quiet, scrawny, guy that the girls never seemed to notice. Dressed up, I could be incredibly hot. It would make me disappointed, how hard it was for me to get a girlfriend, but how easily I could get I boyfriend if I were a girl.
Eventually I made it through high school and moved to college. My sisters being older than I had all already moved out, so I was left with a small cache of clothes and cosmetics I stole over the years. Unfortunately my parents got sentimental about their youngest child moving out and wanted to help me pack. I managed to hide the clothes from my parents and save myself from being caught, but I was forced to leave them all behind.
Throughout the semester I would reminisce of dancing around in a cute sun dress or the feel of lace gliding along my body. Fast forward to one week ago. I would occasionally go out to parties, and I was introduced to alcohol and weed. I wanted to take my mind of studying for a bit, and have a small stash of weed, I decided to smoke some to relax and clear my head. After smoking a joint, I found myself horny and browsing image boards for porn. Then I stumbled into a thread of crossdressers thinking they were girls before I looked closer. It may have been because I was high, but those pictures were hot and I really missed getting dressed up. In the spur of the moment I used up the last of my birthday money ordering an outfit.
I brought the box to my room where I eagerly opened it. I pulled out my new outfit and laid it out in front of me on the bed. A snug, simple, blue and brown sweater with a slender black skirt. Under that was a matching, silk, red and pink panty and bra set. And then there was a small make-up kit. A smoked a joint before putting on my ensemble. Once the skirt was on, my leg hair was glaringly obvious. I stripped and drew myself a bath. I found my razor and got to work making myself smooth. Since it was winter I figured I could get by for a month or two all covered up while my body hair regrew.
The silk panties sliding up my bare legs made me fully erect. I ignored my wood and tucked it away as best I could while I finished getting dressed. With my legs shaved, hair braided, bra stuffed, and make-up done I looked into the mirror. The girl looking back at me was drop-dead gorgeous; well except for the awkward tent in the skirt.
I spread out on my bed, imagining myself to be a girl. I slid my hand up my smooth leg pretending to be caressed by my boyfriend. By now my penis was throbbing at full attention, begging for release. I stroked myself, bursting almost immediately. All that pent up desire from over the semester just released itself all over myself and my new clothes. I just lay there in bed panting, trying to catch my breath, and I eventually drifted into a nap.
I woke up dressed as a girl and covered in my own cum about an hour later. I put the skirt and sweater in the washing machine and hopped in the shower. I couldn't stop thinking about be dressed up, being a girl, and being with a boyfriend. As I stood in the shower I began rubbing myself between my legs, pretending I had a pussy, massaging my prostate. I never knew how good that could feel, and how hard it could make me. I was erect once again. I grabbed my shaft and started pumping furiously. I was thinking about how hot I had looked with my cute glasses, braided hair, and b-cups. As I thought about this, about me as a girl being felt up, I just got harder. I was pumping as fast as I could now, imagining fucking that girl, while wondering what it felt like to be fucked as that girl. With a violent shudder I came. Once I caught my breath, I finished washing up and got out of the shower.
As I was still alone, and still hairless, I slipped into the bra and panties while I fixed a bowl of cereal and turned on the TV.

As the show flashed on in front of me, I could not focus on it at all. My mind kept going back to crossdressing. After being found out by the delivery man, and then my afternoon masturbating, I couldn't stop thinking about being dressed up as a girl, and how hot it had made me. The more I thought about the delivery man, the hornier I became. I wasn't thinking about the guy himself, but how humiliated I was when I was found out, and how much that turned me on. I looked in the mirror at myself in my bra and panties and make-up. I looked good, and I had a sudden urge to go out.
As much as I wanted to, the more I thought about it, the worse of an idea it became. Where would I go, how would I talk to people, what would I do if I was found out. Going out as a girl was a bad idea, and as good as I looked I was too afraid of being caught.
I knew it was a bad idea, but my mind kept racing back to the humiliation, the excitement I felt. An idea popped in my head. I have always been an avid runner, running a few mile every day, which kept me slim and toned. I thought of my winter running clothes that I never use. I had a set of black running tights, a skin tight, long sleeve, black running shirt, and some small neon green running shorts that I pulled out.
I have made a habit of smoking weed before I go running; I found it allows me to relax, get in a good groove, and just lose myself while I run. I loaded my pipe as I contemplated the idea. My running clothes were technically unisex, and would work on a girl just as well as on a guy. If I waited until dark to go, people would only see my hair and breasts and assume I was a girl. If I just kept my head down and ran like usual, nobody would be able to tell I was a guy.
I finished smoking the bowl I loaded. I pulled the tights up over my cute red panties. The bra was completely unfit for sports, but it was all I had and I pulled the stretchy shirt on trying no to mess up my hair. I walked in front of the mirror, and was shocked at how good the outfit looked. The tights and shirt clung to my body, leaving almost nothing to the imagination. I tucked my penis between my legs making the bulge in the tights go away. I then slipped on the shorts which turned out to be a cute way to top off my running outfit. I was too hot, for sure, to be mistaken for a guy.
In the course of a single day I was becoming more obsessed with crossdressing than I ever had before. I was sitting at my desk dressed for running, trying to pass the time until it became dark outside. I didn't have to wait much more than an hour. Being dressed up all day, I began to adopt a more feminine demeanor. I passed by smoking and playing with my hair and make-up.
It was 8:07 and dark outside. As I got up to leave I was feeling eager and nervous. I've dressed up plenty of times before, but this was my first time going out in public. I was beginning to feel a little horny as well. As I was opening my front door, I heard voices outside, and I froze. I looked through the peephole and saw my neighbors talking out near the parking lot. A strange wouldn't think twice after seeing me, but these guys know my face and they know no girls (let alone one as hot as I looked) would come near my apartment. They would see through me the second I stepped out.
I wracked my brain for a way to get by them unnoticed. Maybe I could cover myself up and get by them. I put on my thick hooded jacket, and I pulled some sweatpants over the tights. I looked mostly normal, except that I was covered in make-up. I walked out past my neighbors towards my car. I was hunched over looking at my cellphone, my face hidden from view. I got in my car and drove while thinking only of putting distance between me and my neighbors. I drove down to a nearby park I often run at. I stripped off my jacket and sweats, and I looked myself over in the visor mirror. Feeling more anxious than ever, I got out of the car and began jogging down a trail.
As a car drove down the road I saw the driver turn his head to follow me. I wasn't sure if he liked what he saw, or if he saw through it and was just shocked. I put it out of my head and kept running. Down the path, my heart began thudding as I approached two younger guys skateboarding. The first one spotted me and I could see him looking me up and down. He nodded towards me to his friend. Its amazing how stupidly obvious boys can be. As I passed, the second kid tried to impress me with kickflip, but he failed the landing and almost hit me with his board. I shot him the best glare I could manage as I jogged passed him. Truth be told, I was exhilarated. Their stares, undressing me with their eyes, felt as validating as it did violating. I had passed the first test.
As I continued, I was thinking about myself all dressed up and running. My hot, sweaty, sexy body wrapped in the skintight black, being watched by all kinds of guys as I ran along. My back started to ache, and I realized it was from wearing a bra all day. I suddenly sympathized with the 60's bra burners. Next, my sides began to cramp up. It then dawned on me that I hadn't eaten anything all day and I was absolutely starving. Between my back and the cramps I had to stop and rest. I was near a playground so I walked over and sat in one of the swings. That was when I heard some movement behind the slides. A small group a large guys step out and walked towards me. I recognized one of them from school. He was in my history class, and before and after he would always be lifting weights in the gym. I never realized how big these guys were compared to me. As they got closer, I felt smaller and smaller.

The guy's name came to mind; it was Charles. He was in the center and approached me while the other walked around surrounding me. This was a small, uneventful, college town, nothing bad would happen to me here, yet Charles gaze left me feeling totally vulnerable.
“Isn't it a little late for a cute girl to be out running?” he asked.
I broke the gaze and looked down. I couldn't answer, I looked the part, but I was terrified my voice would give me away if I spoke. So I just looked down in silence, hoping he would go away if I just ignored him.
When it was clear I wasn't going to answer, he casually took a step forward. “Hey, no reason for the silent treatment here, I just wanted to talk, what's you name?”
I couldn't think of anything to do, and he was getting closer.
“Look you could at least say something, its really damn rude to just ignore someone.” He was sounding a little angry.
Ignoring him was not working. I looked up and saw he was a couple paces in front of me. Without thinking, I stood up and ran. I tried to get by him, but he was too quick and caught me in his arms.
“Whoa now, a little startled?” he laughed, “no need to go running.”
I was struggling to get free but his arms held me there like a vice. Panicking, I kicked out connecting with his shin. He yelped and I pulled free turning to run, but I turned right into the arms of his friend, who shoved me to the ground. I found myself utterly helpless and scared, looking around.
The town I live in is pretty religious, and they are not tolerant of anything deviant like crossdressing. I had no idea what would happen if they found out I was actually a guy.
“Sorry, I'm Britney.” I said in a soft voice as best I could.
“That's better Britney,” Charles said holding his shin, “but I'm afraid you hurt my shin.”
“I'm sorry” I said softly again.
“Oh sorry's not going to cut it, especially when you can even look at me when you say.” He said with a dominating tone. “How are you going to make my shin feel better?”
He was standing in front of me now, and I could see a bulge building in his pants. It dawned on me how he was expecting me to make his shin feel better. I couldn't risk him touching or grabbing at me. I looked around frantically and just saw five faces circling me, I was trapped and had nowhere to run. I had no choice and resigned myself to my fate. I thought that maybe I could please him and get away mostly unharmed.
I pulled myself up on my knees and looked I Charles. I reach forward and unzipped his jeans bringing a smile to his face. I reached in and pulled out his hard cock. It was huge, all I could really compare it to was mine, which it dwarfed. It would be hard to get that in my mouth.
With that thought, the reality of what I was doing hit me. I fell into such a female role that it almost seemed normal, but I was about to suck another guy's dick. I closed my eye and began slowly stroking. Charles subtly swayed his hips with my stroke, anticipation in his eyes. He inched closer to me, and his hot cock was right in my face. I leaned forward and kissed it. Then again, and again. I was kissing and licking up and down his shaft while massaging his balls. While I have never done this, or even imagined doing this, I could only think of doing what would have made me feel good.
I closed my eyes and I was Britney. I was no longer Matt being raped by Charles. I was Britney pleasuring my boyfriend. I kissed his tip again and slowly licked my lips, parted them and began sucking on his head. This must have been too much for him. He groaned and thrust forward, filling my mouth. I pulled back, and he reached down slamming my head forward, gagging me on his dick. He held me there while I choked. He held me until my throat relaxed and I stopped struggling. Then he held my head in place and began thrusting, fucking my mouth. Tears were pouring out of my eyes, but my crying and screaming were muffled by his cock.
Charles was still holding my head still thrusting in out, bucking with pleasure. His cock was swelling and I knew he would cum soon, but I wasn't expecting any warning. Charles finally slammed forward hard, ramming his dick down my throat. Before I could start gagging from that, he came pumping loads right down my throat. He pulled out and dropped my head. I let it hang there, coughing and choking, trying to breathe and clear my throat, lying in a heap on the ground.
I was disoriented and felt like I was spinning, then I figured out that I wasn't spinning, I was being picked up. The guy behind me picked up my legs, and I knew he was about to tear off my tights. I panicked and began flailing. Two other guys held me down laughing, as I felt fingers wrap around the waste band. He yanked my tights and panties down, and his eyes went straight to my dick.
“What the fuck!?” He yelled as he threw my legs to the ground, followed by a swift kick to my side. I screamed out and curled up. These guys are going to beat me to death, I am going to die here kept looping through my head. I felt a couple more kicks and a hit to my partially covered face.
Then it was over, the pain was still there, but the beating had stopped before it really got started. I was confused but grateful. I looked up and saw some headlights approaching, then I was blinded. A spot light was flipped on me as lights begin to flash. I pulled my tights up, hoping the officer didn't spot my package, then I just laid there curled up and crying.

I just froze up, and before I had any time to think there was an officer over me with a blanket asking if I was hurt.
I shook my head no and started sit up. As I was pushing myself up he wrapped the small blanket around me.
"I am officer Hosler, what is your name miss?" he asked gently while helping me sit up on the curb.
I was terrified to speak but I had to say something. I said as soft I could, "Brittney," while looking down.
"You safe now Brittney, everything will be OK" he reassured me as he squat infront of me so he was close to eye-level.
Officer Hosler didn't look like a cop. His face was slender, shaved but with a day's worth of stubble. He was handsome, almost pretty, with a smile and eyes that girls must have loved to stare at. The way he was looking at me, that strong gaze just a foot from my face and his hand lightly rubbing my shoulder. I don't how long I sat there staring into his eyes like some helpless lovestruck teenager.
I snapped out of it when he spoke, "Can you tell me what happened?"
"They hit me and took my ipod," I lied.
He didn't say anything, just returned my stare and brushed my cheek with his finger. Doing that me off. After spending the day as a girl, the taste in my mouth, thinking about how Officer Hosler was looking at me, I couldn't help but grow hard. I immidiately looked down to see if it was showing. When I looked up I saw he was following my gaze and looking at my very noticeable erection.
"You're safe now Brittney," he said again. He lifted my chin and leaned in to kiss me. It was a deep and long kiss. I kew I should have been terrified about what would happen next, and that I should have feared the worst with how my night was progressing. But, strangely being embraced by officer Hosler did make me feel safe. I kissed him back, hard.
Slowly, the kiss broke, and he helped me to my feet. He was looking past me and I turned around and saw he was looking at the playground hidden in shadow. I had a feeling I knew what he was thinking.
"Why don't we go have a look around, maybe they dropped your ipod as they ran away." He took me by the hand and led me towards some trees.
Under the shade of the trees it was almost too dark to see, but for some moonlight. My heart was pounding. I knew something was going to happen, and I was eager. He stopped and turned towards me, pushing me gently agains the trunk of a tree.
"God, you are truly beautiful Brittney" he said scincerely. The events from before slipped from my mind and I'm sure my face lit up as I blushed.
"Thank you for saving me Officer Hosler," I said meekly.
"Call me Rick." He leaned in to find me welcoming of another kiss.
His hands wandered down and cupped my stuffed bra. Playing along, I broke the kiss only long enough to let out an encouraging moan.
One hand continued playing with my tits while the other slid further, resting on my ass. I reached out, my hand a little shaky, and I brushed his bulging cock through his pants. This brought a squeeze to my ass. I continued to rub him, and then I took him by surprise by biting his lip. I was incredibly horney and falling more and more into character. I wanted his cock, and unzipped his pants. I reached in and found his penis. Grabbing it with my cold hands was enough to break the kiss. I pulled him out and stroked slowly. I looked him in the eyes and gave him a peck on the lips before lowering myself to my knees.
I sat there stroking him watching the pleasure on his face intently. I leaned in and kissed him a few times before taking him completely in my mouth. I got lost in the repition of the blow job I was giving. He began to pull back, but I wasn't done yet and kept leaning in. He finally stopped me and pulled me back to my feet with a huge smile across his face. Without speaking his cut off my quizzical look with another kiss. Then to my surprise, he reached down and began stroking my dick. All he said was "You don't know how hot you are right now."
He pulled down my shorts and tights to expose my red panties. He smiled before pulling those down to. Before I knew what he was doing, he was in from of me, sucking my cock! And, it felt amazing.
"Moan for me Brittney you sexy whore." He stopped long enough to say.
I began mimicing the girls I had seen in porn, panting and moaning as feminine as I could. And then he stopped.
Rick layed on his back. He reached up and grabbed my member, pulling it to his opened mouth. I realized what he wanted. I got into position and we began sucking each other.
Before long, I began to taste a his precum, and I blew my load before I could warn him. As I did I took him deeply while he filled my mouth too.
After sucking everything I could, I crawled around to face him again.
"Thank you Rick, that was wonderful" and I dropped on to cuddle him a little.
"Thank you Brittney, I've never been with a more beatuiful woman." He knew how to get to me.
We lay there for a minute before we heard the dispatcher on his radio.
Rick hopped up and answered the call, sounding as if nothing had happened.
When he was done, he turned back to me and said "Let me take you home Brittney."

The ride back was quiet and uneventful. I showed him where my car was and he pulled next to it. I gave him a quick kiss on the cheek, said "Thank you for everything Rick", then got out. He watched me as I got into my car and drove off. Through my rear-view mirror I watched him pull out and drive off in the other direction.

I drove home, parked, and put back on my sweats and jacket. As I got closer to my apartment, I noticed someone at the steps. As I got clsoer, I saw that it was a girl, but I couldn't place her as one of my neighbors. With my head down, I just walked past her showing not attention.
"Matt?"

What the fuck is my sister doing here?

It was my sister Rachel. She was a year older than me and going to college just out of state. She had just finished her finals and was passing through on her way home. She said she may stop by, but I didn't expect her without at least calling first.

I simply walked past her towards my door and she followed.
"Where were you?"
I opened my door and she followed me inside. I stood there with my back to her. I was now freaking out. All the emotions and hormones were pumping through me. I couldn't think of anything to do or say. I just stood there in my apartment, silent.
"Are you alright?" she said cautiously as she shut the door. She walked around to face me and I just stood there, eyes cast on the ground.
"What are you wearing? Is that make... Is your hair braid... What is going on?"

I was cornered with nowhere to go, so I unzipped my jacket and dropped my sweats.
After a moment she burst into laughter.

I was overwhelmed and just slumped to my knees and began sobbing.
"Oh honey!" she said instinctively, "Matt, Matt, its OK, stop crying."
After a minute of comforting me she helped me up and wrapped me in a tight loving hug.
"You know I'll always love you, you're my brother. I'm just a little surprised by all of this."
She held me out at arms length looking me over "now lets get a look at you, you know I was always a little suspiscious of you over disappearing clothes."
I'm sure my face was as bright as it could be. "Please don't tell anyone."
"Is that all you're worried about, me telling someone? Please, no you should be worrying about your eyeliner honey." she laughed.
"I'll do anything, just don't tell mom and dad."
"Look, this will be our little secret, besides if you knew some of the things I've done..." she trailed off with a wink.

"This isn't what I was expecting, but let's take a good look at you, come into the light" She pulled me into the living room.
"Hmmm... not bad, you have some potential."

"Now this isn't going to be some sort of freebie mind you Matt," Rachel said, "remember that time you told on me when you caught me with Chris? Or the time you told on me for smoking weed, by the way don't think I can't smell that. Oh no, we're going to have some fun, but I would never do something like tell on you."
"What... What do you want me to do?"
"Well you can start by bring my suitcase in, and then loading a bowl. I need to smoke to deal with this." she said.

I did as she asked, then we were in the living room passing the pipe, and drinking beer.
Then we just sat around smoking and talking. We caught up on how each other's semester went, and before I knew it she was talking about guy trouble and I was nodding along. We were getting to just girl talk now, and she turned to me and said "If you're going to be dressed like this, you need another name."
"Brittney"
"Ooh, that's a fitting name, you do make a goo Brittney. So Brittney, are there any guys in your life."
Rick came to mind, but I was hesitant to be that open with my sister. "No." I lied "I like dressing up, and I might be a little curious, but I'm still attracted to girls." It was mostly true.

"Tonight!" She exclaimed, "You will have your first proper girls' sleepover." She wanted me to change into a spare set of her pajamas. When I took off my running outfit I was standing there in my panties and bra. "You're legs look sexy all smooth like that" She said sliding her hand along one. "But' you're still too hairy." She said looking at my chest and armpits.

By this point we were both high and drunk. And then we were in the bathroom with shaving cream and a razor. She had me take off my bra and I was standing in just panties, running some bath water. Then Rachel just reached up and pulled her shit over her head and dropped her skirt. "Now drop those panties and get in, we can't have a hairy Brittney running around." She commanded.
If I were sober, I would have questioned what was going on. Instead I looked at my sister standing, grinning at me in a lace bra and panties. Maybe I was inebriated, but she was absolutely gorgeous.
My dick stood up hard as I pulled the silk down my legs.