Aileen Ch. 01

byTiffyKitty93©

~The following is just a fantasy. Any actual names or likenesses to real persons or events in entirely unintentional and coincidental.~




Rain. Oh how I hate the rain. Only bad things have ever happened to me in the rain. Two years ago, when I was sixteen, My parents argued and decided to get divorced in the middle of a rain storm. However what happened in the rain last year, was even worse. My mother left for work and was carjacked and killed. By my father. He then committed suicide shortly after, leaving me all alone. Our house was already paid off so fortunately; the state allowed me to stay in our house and sent men to check on me every so often. If I had been any younger, they probably wouldn't have let me stay.

Now fast forward to just 2 short months ago. I was having some problems with my girlfriend Eileen. The problems with her were typical seventeen year old relationship qualms but they just exacerbated a private issue I was dealing with. I had felt more like a girl than a boy for a very long time, and after my parents' death, I was left a house that still had a bedroom full of my mother's old things. I'm glad I didn't really grow much. Being only 5'5 and 130 pounds if I'm lucky, I was nearly the exact same size as my mother. We even had the same size feet, which made everything so much easier. When I was alone at home, I would fully dress up in everything my mom had left. For the time being, I never wanted to go farther than that though. I loved Eileen, so I couldn't like men. It wasn't until it rained again that night, and Eileen passed away from a drug overdose that things began to change forever. I knew she was using, but I couldn't do anything to stop her.

After her funeral, I decided to become a shut-in. I didn't have much company. Didn't want it. Anyone that got close to me met an untimely end. Before Eileen had let go and passed away, I had told her about myself and what things I was feeling. She left me all of her clothes and makeup and her savings account in her last will and testament, though it wasn't much as she had poured so much of it into drugs. It only totaled out to about $350 dollars, smaller than my average paycheck at my 32 hour a week job.

Two weeks later is where this story really begins. It was raining again. Today was our midterms at school so I had to go. I walked to school in my least favorite thing in the world, rain. Of course when I got to the building, Bill, this overbearing bully, decided to start cracking jokes and trying to bait me into doing something I or he might regret.

"Hey look guys! It's Allen the hermit. Awww did you decide to actually come out and play in the rain today?"

"Bill, please back off. I just want to get in here, get my tests done and go home. No one needs any trouble."

"Ah but that's where you wrong, little man. I thrive on trouble." He pushed me down into a puddle, laughing and hooting with his lackeys the whole way into the building. Just as I was about to pick myself up and go home, a hand reached out to help me up. It was Dillon. At one point, I would have considered him my best friend. However, I'm not sure a shut-in can have a best friend.

"You okay? Did he hurt you?"

"Just my pride. I should probably just go home and dry off. I'll take make up exams."

"Nah, it's okay. The nurse has a washer and dryer, and robes stuff like that. They can just bring your first exams into the office while you wait on your clothes."

"I guess so." Dillon walked with me to the nurse's office. I always felt so small around him. He was 6' tall and about 185 lbs of lean muscle. After he left me at the door, I felt a little strange. I wanted him to stay. For some reason, I felt safe with him there. I walked in the nurse's office and explained what happened. She had me go into the other room and strip. I put on a robe and waited for my clothes to dry. I had low testosterone levels so my body hair didn't grow much. I had it, but barely any. From a distance, I looked completely shaven standing there in the robe. I looked in the mirror and at first glance, thought there was someone else standing there in a robe. A girl. The nurse walked in and handed me my first two exams to get started on.

"Allen?" About two hours had passed. "I got your clothes dry but there was a problem with your boxers. They shrank. I didn't realize they were delicate. I'll go find you some new underwear."

"Okay."

"Here you go. I'm sorry about the um... style. It was all we had that would fit you and well I thought it would be better than nothing.. We keep a surplus of these in case girls get their periods unexpectedly." I gasped as she slid a pair of pink satin panties through the door. I really wanted to wear these panties. I picked them up and they felt so smooth. I pulled them u my legs carefully and tucked my small member in to smooth out the front. I redressed and headed out to finish my last few classes.

Dillon met me at the door for our last class of the day. We both had the same teacher for Business Math and he always sat near me.

"So how'd your day go?"

"Terrible. Same as usual." I walked into the room, unaware Dillon was looking down at something behind me. I felt so comfortable in these panties that when I got home that day, I decided I was going to wear only panties from now on. Hell, I wanted to dress like a girl anyway, so why not?

Flash forward to present day. My 18th birthday to be exact. For the past two weeks, I had been wearing panties instead of boxers. In fact, I threw all of my old boxers away. I replaced the underwear drawer in my room with a mix of the cutest panties from Eileen's and my mother's old wardrobes. In addition to that, I had started shaving my entire body. And the strangest part was, they had been the best two weeks of my life. My luck had seemed to turn around. Bill stopped bullying me, everyone started talking to me, initiating conversations mind you, and i began to come out of my shell. I became friends with the preppier girls, who actually turned out to be pretty nice. They kind of let me in to their inner circle, and before I knew it I was hearing stories about their boyfriends, listening to make-up tricks, and even heard conversations about sex moves they were using that made them and their boyfriend's orgasm uncontrollably. My life had turned around so much that, I even decided to start hanging out with people again. I wasn't going to spend my 18th alone, so I decided to walk home with Dillon today and stay at his place tonight.

It had rained last night and the ground was still soaking wet. There were puddles everywhere. When we were almost to Dillon's house, it happened. I slipped and fell into a mud puddle. I was drenched. Dillon helped me to my feet and nearly carried me back to his house. Once we got inside, I ran to his bathroom and stripped.

"Allen. I'm going to see if I have any clothes that fit you. Go ahead and shower, clean yourself up." When I got out of the shower and toweled off, I noticed the clothes Dillon had left out for me. There was a note on top that said,

"Sorry, these are my ex-gf's. It's all I had that would fit you. I put her underwear in here too so it might make you a bit more comfortable and complete the look. Ran out to the store. BRB. - Dillon."

I kind of laughed to myself. But thought, what the hell. This is what I wanted to do anyway. If Dillon left his ex-girlfriend's clothes out for me, he must not have a problem with it anyway. Maybe I'd even tell him I've been secretly crossdressing for a couple of years now. I pulled the panties up my legs, purple with pink skulls and satin like the first pair I wore. The matching bra looked to be about a b-cup. I tightened the straps the best I could, giving myself a little bit of cleavage. I grabbed the skirt next, a blue denim one, pleated at the bottom. After fastening the buttons on the skirt, I grabbed the pink bejeweled camisole that read "princess" across the bust. Now my black hair wasn't long, about only to my chin, but I spent about 20 minutes fiddling with it and his mom's straightener. I had given myself a nice little feminine looking style that framed my face nicely.

Luckily, his parents were going to be gone for the whole weekend so we were alone. I decided, since the nearest store was about 45 minutes away by car (we walk to school because it's closer to our houses), that I had time to play with his mom's make-up. I remembered little things the girls had talked about while applying eyeliner, mascara, light purple eye-shadow, and a little coat of lip gloss. I added a little bit of foundation just to smooth out the look. I looked into the mirror and almost couldn't breathe. I looked as good, if not better than some of the girls at school. My petite stature made this look seamless. I looked and felt like an 18 year-old girl. Since I Still had some time, I quickly painted my toenails and fingernails with some borrowed nail polish from his mom. It was purple with pink sparkles. Perfect match to my underwear.

Since I was already in his mom's things, I decided to look for a pair of shoes. Our mom's used to share shoes so I knew they'd fit me. I lucked out and found a pair of black heels that complemented my hair perfectly. I also found a cute black bracelet and a diamond heart necklace. With everything done, I decided to turn on the T.V and wait for Dillon to get home. When I did, I saw something I guess Dillon had been watching. It was a porn scene. This taller kind of buff guy was just manhandling this petite little girl. He was just pumping himself in and out of her and she was moaning with pleasure. When he laid her down on the bed, she splayed out like a rag doll. She was so tiny. The only thing on her that had any weight to it was her breasts. The second biggest thing on her was her... cock? She had a penis that was near rock hard flopping around as her boobs bounced up and down with each thrust her partner gave into her ass. I was so entranced by the video that I jumped when I heard Dillon behind me.

"You know, with you looking like that, I almost kind of want to join them." I turned around and saw him looking me up and down. From my painted toes sticking out of my heels to the black bob framing my dolled up face. His eyes darted to my cleavage through the top of my cami, and to the flat front of my skirt. My legs caught his attention next. "You shave them?"

"Yeah. I... well... this isn't my first time crossdressing."

"I know. I saw the panties you've been wearing for the past couple of weeks. I didn't know you were shaving your legs though. That's awesome."

"I shave everything. It makes me look more girlish."

"I can see that. What about that make-up? A pro couldn't have done better."

"I picked up some tips from the girls at school. They talk about it a lot."

"Awesome. Here why don't we just sit down and have a drink? I got some sodas and some tea."

"Tea is fine." He came back and sat down next to me on the couch. He put a glass of tea on the table in front of me as we both watched this guy fucking this tiny little shemale. The more I watched it, the more turned on I was getting. I say turned on because it was... different. I wasn't getting hard all the way. My cock was stiffening but the real turn-on spot was my ass. It was tingling with this strange sensation I hadn't felt before. Like it was almost craving something. By this point, Dillon had put his arm around me without me noticing. Without realizing it, I had snuggled closer to him. In fact, I was inches from being on his lap. My head was resting on his chest until, it happened. I suddenly felt adventurous.

I looked up into his big brown eyes, and then I kissed him. Or he kissed me. I wasn't sure which. It had happened so fast. I swung my leg over until I was straddling his lap. We were exploring each other's mouths with our tongues as I was stroking his chest through his shirt. He reached up and grabbed my breasts, squeezing them a little. I gasped with a pleasure I had never experienced before. My ass was grinding on his jeans and I could feel his growing erection through them and my panties.

I suddenly felt the urge to do something about that growing rod in his pants. I slinked down onto the floor and helped him unzip his pants. From my knees, I looked up at him an mouthed, "please?". He nodded and I grabbed his still hardening cock. It had to be close to 9 inches.I stroked it a few times moving my hand up and down from head to balls before giving it a little lick. He jumped at this, but it seemed to be out of surprise rather than disgust.

"Go ahead, baby girl. Suck it." I obliged his request. My glossed lips kissed the head of his now fully erect, 10 inch penis. I opened my lips and let him slowly push it into my waiting mouth. I almost gagged at first as he slowly pushed it towards the back of my throat. I loved the feeling of it as it slid in. I still remember that taste. The tip hit the back of my throat as I stopped myself from gagging. He continued to push in and out as I bobbed my head and rhythm to the throat fucking action. I deep-throated him a few more times before the tingling in my ass became far more intense. My ass involuntarily wiggled in response, and Dillon saw it.

"Do you want me to put my cock in there?" It wiggled again and I nodded in response, cock still in my mouth. He pulled it out and I instantly wanted it back in. I felt like a baby who had dropped her favorite binkie. The tingling in my ass became far more intense when I thought the word 'her' and it was almost like an itch that I knew only one thing in this room can scratch. Dillon leaned over and grabbed two things from a bag. One I recognized as a condom, and the other was a tube of something. I suddenly felt a finger push through my hole. It had something cold on it and I realized the tube must have been lube. I was on all fours waiting as I felt two fingers enter this time. I brought a hand to my chest and squeezed my breast the way he had earlier. The touch sent a shock wave throughout my body that caused the itching tingle in my ass to get worse. Three fingers in. Four. Finally I felt his fifth finger enter my ass. He was spreading my hole, trying to stretch it and he succeeded. As soon as he removed his hand, I instantly wanted it back in there. The emptiness was short-lived as I finally got what i had been waiting for.

The head of his cock poked my hole and I felt it slowly slide in. He must have put some lube on the condom too because it slid in easier than I thought it would. I felt a twinge of pain at first. I screamed out a little in a mix of pain and pleasure. It was the most feminine sound I had ever heard myself make. In fact, I sounded just like the girl in the video. At this, the pain began to stop as Dillon kept slowly pulling and pushing in and out of my ass. He kept up this pace until the pain was completely gone. I started pushing back in tandem with his thrusts and he took the hint. He began to speed up. I moaned in pleasure as he continued doggy-style fucking me. He was pumping my ass faster and faster, his cock going all the way in my rectum. I felt his balls slapping up against me. He got faster and faster and I was just loving every second.

"I wanna try something." I breathed through moans. I saw this in the video and wanted to do it. "Sit on the couch." At this I think he knew where I was going. I straddled his lap again and grabbed his cock. I held it steady as I slowly lowered myself on to it. He then grabbed my waist and helped me out. Suddenly, I was sitting on his lap, cock all the way in my ass. He lifted me up until it was almost out and then I put myself back down. Then we got into rhythm. He Began just bouncing me up and down on him, me moaning and screaming which the occasional 'fuck' or 'yeah' thrown in. The sounds of flesh meeting flesh as I bounced my ass off of his lap were turning me on even more. This continued for almost 30 minutes before he stopped me. We had been going at each other for over an hour in the living room but he wanted to move it.

He picked me up and walked, cock never leaving my ass, into his bedroom. He put me down on the bed and I splayed myself out like the girl in the video did. I wrapped my legs around his back as he pushed himself back into my ass. I felt his cock start to twinge and remembered something one of the girls had said.

Even though I didn't have a pussy, I thought the the same logic should apply and it did. When Dillon pushed all the way in I held him there with my legs. I then started grinding my ass on him, twisting it in a circle, and I yelled from the pleasure of his cock twirling around in my ass, hitting every crevice. My body began to shake uncontrollably as did his. I then felt the tip of his cock poke through the condom right before jet after jet of his cum leaked into my ass. I held him there and let him unload into me, loving this strange new feeling of cum filling me up. When he was done, he pulled out and flopped over onto the bed.

"Wow. That was..."

"Amazing." I finished for him.

"You know, we definitely have to do this more often."

"Oh yeah, Dillon." I said looking over at him promiscuously. I wiggled my ass a little and winked.

"Haha. If we're going to make this a thing... well I just can't keep calling you Allen."

"I like Aileen. You know with an A instead of an E. It makes me feel like I'm kind of... living the life Eileen should have."

"Okay, Aileen. But first I have to tell you something. I kind of knocked you into the puddle on purpose. And well, there was a little bit of ecstasy in your tea. I thought you needed a little encouragement."

"well you were right. But not anymore. I'm all yours, Dillon." I giggled and kissed him before I laid my head on his chest and we both passed out.

I had the weirdest dream that night. I saw two little 8 year old boys playing in a yard. Then the two were in a room. One of the boys was playing with a dress.

:"Maybe you should put it on, bzzt? Let's see what it looks like!"

"I don't know, bzzt. Dresses are for girls right?"

"well you're kind of like a girl anyways. I mean you're smaller and you like flowers and dolls and not sports and boy stuff. You like, you know, girl stuff."

"You're right. Maybe I was supposed to be a girl. Okay! I'll put it on!"

The little boy put the dress on and then motioned to the other boy to come back into the room.

"Well, bzzt. What do you think?" He twirled around in his dress as the other boy stood there open mouthed.

"Wow, bzzt! You look just like a girl! Let's play house. I'll be the daddy if you want to be the mommy?"

"Okay! So I guess as the daddy, you have to go to work right?"

"Yep. And then I come home and give the mommy a hello kiss haha!"

The boy went out of the room with a toy briefcase. he came back in and as he said, gave the little boy in the dress a peck on the cheek.

"I'm home, honey!" And she blushed as her pretend husband gave her a hug and asked what they were having for dinner.:

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by Anonymous11/10/13

More Please!

I really enjoyed your tale and hope you continue with more chapters soon!

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