A New Me...

This story is completely true. I hope you enjoy it because I have been dying to write it for almost 4 years now!

Hi, my name is Ashley. At the time of writing this story I am a 24 year old crossdresser living full time as a woman. It wasn't always like this however...so let me tell you about how it all began.

Chapter 1: The beginning, and going out.

Flash back 10 years when I had just turned 18 years old and had just been accepted into the University of Vermont. I was ecstatic because this was my reach school (I wasn't all that smart book wise) and it was the school that my sister Elizabeth (20, a junior) was already attending.

My sister and I were as close as you can get sibling wise. She was always there for me during high school and would always help me out when kids at school would pick on me. I wasn't the biggest kid...I was only 5' 5" and weighed about 135 pounds. I had also never really quite hit puberty and didn't grow much hair on my body, especially in my face. I was also into heavy grunge music and wanted to emulate some of that 90's look with kind of longish hair that fell to shoulder length. (brunette).

This caused me to become kind of introverted. I didn't really have many friends, and because of that, it caused my sister to take me under her wing so to speak. She was beautiful. She was the exact same size as me. Actually, her body looked a lot like mine except that she had size C breasts and blonde hair. She was a very popular girl when we were in high school. She had a lot of boyfriends and was a cheerleader in high school and at Vermont. She also has a killer butt, which we both share, as well as hips...(something that was always very awkward for me as a boy).

Being so close, we did a lot of things together. She also had really cool friends in high school which would always accept me into their hang outs at home and stuff. They would talk about all sorts of girly things...boys, shopping, school, and even sex. This had an affect on me throughout my entire life.

You see...my sister didn't know this, but when she would go out with her friends I would try on all sorts of her clothing. My favorite and first parts of her clothing were her underwear. From a very young age (12) I had put on her panties and would wear them under my clothes whenever I had the chance. When she got older she kept getting sexier and sexier undergarments, and I would keep evolving into wearing more and more of her clothing. Not just the underwear, but the bras, the shirts, the pants, the dresses, and the heels. I eventually would start wearing her make up too.

But back to the story! So I had just moved into U of V. I had gotten a single dorm like I had requested and had unpacked everything and set up my room. My parents had put everything away for me and helped set up my room and were now leaving. I had brought a special bag with just a few pairs of my sister's thongs that I tucked away under my bed without them noticing. When they left, we had some stupid meeting with our Resident Assistant in the hallway where we had to say our names and stuff.

After the meeting, my neighbor to the right of me came in and greeted me. His name was Paul. He was huge! He stood at about 6'4" and had muscles everywhere. He told me that he played for the hockey team and that he was actually 20 because he had gone to prep school for hockey but was also a freshman. I said hi to him and we talked for a bit but realized that we didn't have much in common so he left.

Finally! I thought to myself as I went under my bed to grab the bag of underwear I had stowed there. I was in such a rush that I had forgot to lock the door as I went into the bag and grabbed one of my favorite thongs. I had stolen so many of my sister's underwear by this time I had no clue how she had not noticed. It was a pink and black thong with ruffles along the top and a tie string in the back above the butt. The front had pink flowers and was made of a sort of stretchy mesh material that was see through. I pulled down my shorts and boxers and slid it up my legs. I was a heavy masterbater, and it made my balls very small...which went well with my penis size which was roughly a solid 4" when hard. Because of this I never tucked, and just kept my soft penis and balls in the encasing of the thong.

I looked back at myself in the full length mirror on the door and admired my ass. At this time in my life I had never considered my sexual orientation. I would masturbate to all sorts of pornography. Shemale, crossdresser, straight, gay, whichever i was feeling at the time. But I had no inclination towards any gender. I just liked looking like a girl, and would envy girls daily. I had shaved before leaving for school and was completely hairless except for my head and eyebrows. I was also a heavy pre-cummer, and some was already leaking into the thong just looking at my wonderful full bubble butt.

Just then, the door knob started turning and I was frozen with fear...Who could this be? Not an RA please! Not my parents! Not Paul!

It was neither...In the door frame stood my sister...holding a case of beer. For a second we just started at each other. My head turned over my shoulder at her, with my ass in clear view encased in her black and pink thong. Her standing there with the 30 rack in a skirt, black tights, tan boots, and a white sweatshirt.

Then we both moved at once. I turned around and covered my self up while she hurried in and closed the door.

"I...I can explain!" I tried to get out.

"ALEX!" she screamed, then quietly "What the hell are you wearing! Are those my panties?!"

"Y...yes..." I started crying "I'm so...so sorry!" I put my head into my hands and cried.

"Little brother, don't be sorry. You honestly don't think that I didn't notice that every time I bought new underwear they were stretched in the crotch? That they would go missing for weeks at a time just to magically appear washed and in my dresser drawer again?"

"You mean...you've known this whole time?" I asked through sobs.

"Of course I have! I've been waiting ages for you to tell me! Are you gay? Do you like boys? Why do you do it?!"

So we started talking. I told her all about it. How I had the figure of a teenage girl. How I was always so envious of her life. How I was constantly picked on and just wanted to look just like her and hang out with her and her friends because my life sucked.

"You know what little bro, I think that I can help you out with something if you want to go along with it...."

"What do you mean?"

"Well...you see I haven't really told my friends that my sibling was coming to this school yet. You haven't always been really sociable with people, and I just didn't want to mess anything up with them. I had trouble making friends here, and I didn't want to show them my kid brother who doesn't like talking to anyone. But now that I know why you were like this...I want to help you out."

"How?"

"What do you say...you become my sister?"

"How would that work! I have to take classes as Alex! I got accepted here as a boy!"

"Oh I know, don't worry about that. You can take all of your classes as a boy, but when you come hang out with me, and my friends, you will be my sister. Ashley."

"I...I don't know, it seems kind of risky."

"Nonsense. Come to my apartment tonight. And wear those panties hehe."

*******

For the rest of the day I was extremely nervous/excited. I wasted time by watching TV and playing some video games in my dorm until the clock rolled around to 6pm and I made my way over to her apartment. I was wearing the black and pink thong like she requested underneath my jeans.

I rang the buzzer and she buzzed me in and told me to come up. I got up the stairs and knocked on her door. She let me in. Her apartment was a single like mine. It was a large studio type apartment. It had a kitchen and a living room and a bed all in the same big room. It also had a bathroom and a closet attached to it next to the bed.

"How's my little bro...sister!? Nervous?!"

"You have no idea..."

"Don't be, this is going to be a great night! We are going to go out to a party with some of my friends. It gets pretty wild here on the first night of the semester."

"Yipee..." I said unenthusiastically.

My sister was already dressed. She had a short purple dress on. It had ruffles at the hem of the dress, and was tight to her body. Her hair was up in a type of loose bun, and her make up and nails were also a light shade of purple. Her heels were black, and were huge. She liked to wear big heels. They were about 4" big with a 1" platform. She looked hot!

"Stop looking at me like that weirdo! You're creeping me out. You are going to look just like this...but hotter! All the boys are going to want to get with you tonight!" She laughed at me with a wink.

"I don't want that! I just want to have some fun for a few hours with you and your friends and sleep here and go home!"

"Ha! Not if I get lucky tonight you aren't sis...you will be going back to your room!"

"Ew!!! Please don't talk about your boyfriends in front of me."

"Come on sis, all girls talk about their boys. Even one night stands. Now come on, let's get you ready. Strip!"

I took off my pants and shirt and stood there in the black and pink thong...already leaking pre-cum in anticipation. I instinctively lowered my hands to cover my small bulge.

"No need sis, we will both be seeing each other getting ready from now on, so it's only a matter of time. Plus your small penis is cute...it's perfect for a girl...who has a penis," she laughed again.

I was beat red but did as she said. I stood there awkwardly with my hands to the side as my sister looked over my body.

"Well it looks like my sister knows how to shave herself...let's get to work on your nails and make up."

I showered and returned to her with a towel on my hair and the pink and black thong on. She had me sit down at the table and she got out some nail polish. She painted my fingernails first. A bright shade of pink. Than she went to my toenails. She did a french pedicure, and they looked sexy...precum was leaking into my panties once again....Next she moved to my face, where she went to work with all sorts of make up that I had no clue what was going on. She blow dried my hair and than straightened it and curled it into some wavy curls that hung by the side of my face.

She then got out some tweezers and worked on my eyebrows. I knew now that everything that she had just done could be reversed, but shaping my eyebrows was permanent. I was really in for the long haul...

When that was all done she had me get up and go over to her closet. She got out a black bra that had lace on the cups. From there she opened up a box of breast forms ("Bought these for this occasion today hehe") and put them in the cups, giving me a real feel on my chest.

Next she pulled out a black dress. Much like her own in that it was short. I pulled it over my head. It came down to about mid thigh, barely covering my butt. It had ruffles on the sleeves, and a very revealing bust line.

Than she pulled out a pair of pink heels. They were 4" with a 1" platform, just like her own, and had a bow in the back, just above the heel.

"Holy shit sis!" Liz squeeled, "You look hotter than all of my friends!"

She turned me around and faced me to the full length mirror on her bathroom door. What I saw completely shocked me. It wasn't me anymore...it was a hot freshman college girl, standing there looking completely shocked. My make up and freckles were perfect. I had a light shade of pink that matched my nails and heels. My lips were painted with a bright pink lip gloss.

I twirled around. My ass was amazing. Like super-model amazing. The heels had pushed it back and up, and it was framed perfectly by the dress. I was getting hard, and precum was leaking, no, flowing into my panties now as I became rock hard.

"I...I don't know what to say...thanks Liz..." I said in astonishment.

"Don't thank me, you look amazing! Now let's practice some walking, and work on that voice of yours!"

So I started walking around the room working on practicing to move my hips and my voice to become slightly higher pitched.

I got it down in no time, and we were ready to go! We walked into the cool autumn air, and were heading to pick up 3 of Liz's friends and head to the party.

"So where are we going tonight?" I asked in my new girlish voice nervously.

"To the hockey house of course, that is where the biggest and best parties are thrown here at UVM. They have the hottest guys there too...you're going to LOVE it!"

"Liz, I told you I don't want to get with guys! I am straight, I just like the clothes girls wear..."

"Ok sis, suit yourself, but good luck fending off the guys tonight!"

So we got to my sister's friend's apartment and went upstairs to get the other 3 girls. Amanda, Kristen, and Sara were their names, and they looked just about as hot as we did. They were all wearing the same sorts of clothes we were, with slutty heels, and short dressed. We exchanged hellos, and I was very nervous saying hi and getting introduced as my sister's sister. It was weird...

We started to take some shots to "pregame" the party and I started to get more and more buzzed. This was my first time drinking, and I was loving the feeling. All my anti-social behavior that I was used to was going away, and I was talking and acting as girlish as possible. I was doing a good job too, because her friends were loving me. They kept saying how they were so excited to have a new friend come to the parties with us and loved that I was so fun.

So after we took about 4 shots each we all got ready and started to walk to the hockey house. My feet were killing me, being the first time I was ever wearing heels, let alone monstrous ones like these.

We approached the house, and from the outside I could already tell this was the place to be. It was so loud from the outside and there were a bunch of people already outside and noticeably drunk. People were playing dizzy bat and beer pong, and most of them were older, looking like Juniors and Seniors.

My nerves started to come back to me, and I was extremely nervous that someone would notice that I was a guy. But that quickly went away as we entered the house and 3 guys migrated towards us and started some conversation.

My sister deflected their comments and moved us deeper into the house.

"Hey Ryan!" Liz shouted over the music to a guy about 6'1" With huge muscles and black hair.

"Liz! I'm so glad you came! And who is this?!" The guy said as he tilted his head towards me.

"This is my sister, Ashley! She is a freshmen, and this is her first time out, and first time drunk too hehe."

"Well Ashley, nice to meet you...I hope you have fun tonight. There are some freshmen kids here on our team. They are already pretty trashed though considering we had our hockey initiation tonight."

Just then to my left a hulking guy came over and through his arm around me and my sister. I looked up and then my face went white with terror. There stood Paul, one arm around my neck, the other around my sister's.

"What up Paul," said Ryan "looks like we have a new girl for you to meet...Paul meet Ashley. Ashley, Paul.

"Hey sexy," he breathed on me with an intense smell of alcohol, while also pinching my ass.

"Hey," I said in my quietest girlish voice...

But that pinch did something to me. Maybe it was the alcohol. Maybe it was just my own feelings towards guys...but I got rock hard in my panties. It was like a turning point in my own head...something just...went off.

My sister looked down and noticed the tiny bulge, instantly grabbed me and pulled me to the side.

"Sis, relax. Looks like someone does want to be hit on boys tonight! Ryan is this kid I had been with last year. We were kind of...fuck buddies. All the hockey kids are extremely built, and the best lays on campus...but are really rough. I don't want you to do something you don't want to get messed up in, or hurt."

"Liz, I'll be fine!" I giggled at her, "I just want to have some fun!"

"Ok...but be careful," She said worried.

With that I sexily walked over to Paul, and grabbed his hand.

"Do you have some more alcohol?" I asked sheepishly.

"Yes...yes I do, come up to Ryan's room, that is where my beers are," he slurred back to me.

So he took me by the hand and led me upstairs, with the sounds of woooo coming from his friends. He led me up into Ryan's room and shut the door behind him. He went behind his desk and grabbed 4 beers, and a funnel.

"You ever done this before?" He asked me.

"No, never!"

"Well come on, it's easy."

He poured 2 beers into the funnel and stopped it at the nozzle. When all the foam was cleared away he said, "Get on your knees, and put this end in your mouth."

So I knelt down on the floor, my sexy bubble butt resting against the spiked heels and put the nozzle in my mouth. The beer came flooding into my mouth and I managed to swallow it all.

"Mmmm, that looked hot," Said Paul.

"What?" I said taken aback.

"You just looked hot...sucking on that hose..." Paul said, stroking the unmistakable outline of a giant penis in his jeans.

I don't know what came over me, I was extremely hard and leaking precum again, as I moved towards Paul, looked up and kissed him on the lips! The strong smell of beer and other alcohol invaded my mouth as well as his tongue. I had never been kissed before, and it was so weird that it was a guy! He was rough, and sloppy. I was just letting him force his way into my mouth as much as he could get to.

As we were making out, he was moving his hands down to my ass and rubbing and grabbing it. Pulling my cheeks apart and smacking it from time to time. I was so horny, but staying far enough away from him that my own penis would not rub his gigantic one. I started to move my hand over it. It must of been at least 8" and very thick...then he broke our make out session.

"I'm very drunk Ashley...I don't want to do something you don't want to do, I can't risk being kicked off the hockey team if you thought I was raping you or anything."

"Shhh, just keep going, you're not doing anything wrong...I'm so wet..."

And I was...i was leaking precum so much into my panties it had to be leaking onto the floor by now...

"Ok cool, then bend over." he said abruptly.

I was so nervous now...he couldn't know my secret! Thinking fast the first thing I said was "I'm on my period!"

"Oh thats cool, we will do it in the ass then...are you cool with that?"

"Do I have a choice?" I winked at him. "It will be my first time though..."

"Mine too...but don't tell the guys, they think I'm a ladies man haha"

With that I spun around, walked over to the couch moving my hips seductively, and laid over the couch arm with my ass in the air, making sure to squish my bulge into the arm to not let it be seen.

Paul moved behind me, already taking off his pants and lining up his cock with my waiting hole. He hooked his finger into my thong, and pulled it over to the side. "Mmmm you have such a tight little hole and a great ass Ashley."

"Thanks hehe! Hurry up I'm so horny! But go slow!" I said not really making sense in lust and drunkedness.

Paul put his finger into his mouth and sucked on it. He added one finger to my hole, and then a second quickly followed. It hurt at first, but he was slow and gentle, moving eventually three fingers into my waiting hole and pumping in and out slowly. Girly little moans escaped my mouth as his fingers fucked my virgin boy pussy.

"Are you ready Ashley?"

"Yes...sexy," I said in between moans.

Paul pulled his fingers from my hole and moved his huge penis head to my waiting now slightly loosened hole. He then pushed a tiny bit and I felt what felt like fire on the entrance to my ass. It felt like a mack truck was trying to enter my body, but slowly, inch by inch he worked his way in. Stopping every other inch and letting it rest there before all 8 huge inches was filling my insides.