First story. Be kind. I love this site, it's great, and I wanted to be a part of it. Hope people like it. Any constructive criticism would be gladly appreciated.
-J

So, I had just graduated from College and not unlike everyone my age, I went looking for a job. I started with trying to find a job that I actually went to school for, but to no avail. I got home from my search and found a bill on my counter from my Student Loans. My roommate, Pete, was watching television and drinking a beer.

“Hey man,” he said over his shoulder.

“Hey.”

“Any luck finding a job?” he asked.

“Nope. Going to have to put in an application at McDonalds or something,” I quipped.

“Alex, that would suck. Keep looking, I’m sure you’ll find something.”

Unfortunately, for the next two weeks I found nothing. I stopped at every store and applied, but heard nothing back. I reluctantly stopped in a place called Patti’s and went up to the counter.

“Are you hiring?” I asked.

The girl behind the counter, a cute blond, just kind of stared at me.

“Uh…we only hire girls,” she said with a laugh. “Sorry.”

“Right. Yeah, I guess it was a stupid question,” I said and quickly walked out with my tail stuck between my legs.

I decided to pack it in and go home, because when all else fails nothing is better than getting completely shitfaced and forgetting your bad day.

I was on my fifth or eighth beer and crashed in the chair at my desk. I leaned back and downed the rest of my beer in a few gulps and closed my eyes. I let the chair carry me back to a sitting position and right in view of my large closet. I stood up and went inside the closet. It was pretty fucking big, but I used not even half of it. The other half was full of clothes that my ex-girlfriend left behind when she went overseas with some Limey bastard.

I drunkenly touched her clothes, they were soft, and I felt weird afterward, so I shut the light and left the closet.

I entered the bathroom connected to my room and drained the lizard, so to speak. I stood in front of the mirror, my hair had gotten long it fell down past my chin a bit — maybe that was the reason no one would hire me — I looked like a grunge-rocker. I ran my hand through my hair and let it fall. It briefly stayed up with a thick strand sliding around my face. Then it dawned on me… I could… No, that’s ridiculous, because I wasn't a-

I was in the closet looking at her clothes. She had a bunch of dresses, and some blouses, and some tops, and even a few pairs of pants.

“This is ridiculous, I can’t …” I said aloud, but grabbed a green dress from a hanger and went into my bedroom before I lost my nerve.

I quickly locked the door and undressed. I unzipped the dress and stepped into and pulled the short sleeves over my shoulders. It fit well, too well actually, and I zipped the back up. The only thing that was off was a bit of hair on my chest and my legs. I wasn’t all that hairy, I have a notoriously hard time growing any facial hair and not looking like a pedophile. I stood in front of the mirror and marveled at the sight. I wasn't beautiful, but I wasn't exactly ugly, I guess. I ran my hands through my hair and let it fall out a bit at the sides. It looked bad, but mainly because I hadn't washed it in two days, so… I went to the store.

I obviously didn't wear the dress to the store, because that would be ridiculous. I wore a pair of jeans my ex left in the closet, which fit extremely tight, but also not tight at the same time. I wore a gray sweatshirt and a pair of large -extremely so- sunglasses, brushed some hair into my eyes. I even went a little above and beyond with some lip gloss she left behind. It actually reminded me of her, but I pushed that thought out of my mind. I actually fit into her heels, but fuck, I couldn't walk in them to save my life, so I wore a pair of flip flops and left the apartment.

I went around the corner to the local Walgreen's and went straight to the wall of razors. I picked up a pink package of Gilette Venus razors and looked at them. A girl, wearing a ton of makeup, came up to me.

“Finding everything alright, sweetie?” she asked.

I nodded and tried out a higher voice. “Yes, thank you.”

I picked some shave gel and walked around the store a bit until I came to nail polish and makeup. I picked up some red nail polish, some remover, some false nails, some mascara, some different lip gloss, and forgot about one importing thing. I went to the other aisle and went to the shampoo. I wanted something that would give my hair …something other than flatness. I picked up a bottle of John Frieda Shampoo that said Luxurious Volume and a conditioner that went along with it. I turned around and there were blow driers and curling irons and straighteners. All of these things I had no idea about, but I bought them all.

I got home and immediately went on youtube, because I remembered Jocelyn, my ex, watching tutorial videos about how to do things to your hair and makeup and whatever else. I started watching things about curling your hair and immediately it was easy. These broads could teach, I stopped the videos, took a quick shower (with the new shampoo) and shaved my entire body. I blow dried my hair for the first time ever and it was a weird experience. My hair was fluffy and I followed the directions of the youtube video to straighten it and ultimately it came out pretty much the way it was suppose to.

After I straightened my hair with the help of youtube, I turned towards makeup which actually was pretty easy aside from poking myself in the eye half a dozen times. I mastered mascara and eyeliner and blush. I looked at my eyebrows, but deemed them similar to a lot of the videos I was watching so I left them alone.

As I was going through youtube I typed in cross-dressing, because that was technically what I was doing. A video had the word “tuck” in the title and almost immediately I got a pit in my stomach. I couldn't have forgotten about my dick and yet, I did. I looked at myself in the mirror and was stunned at what I saw…a pretty girl with a bulge in her shorts.

The tuck video was pretty self explanatory…take a sock and cut off the ends, then loop a headband through it and put your legs through the holes and pull it up. I did this and it was weird. I wore it for a while under my shorts to get used to it, but eventually took it off. I also realized that I needed the female undergarments, because I wasn't going to be able to wear boxer briefs under a dress or in skinny jeans. I had just done so previously, because I was wearing the baggy sweatshirt, but I certainly couldn't wear that out all the time.

I left the house again, this time wearing the green dress and a pair of lone tighty-whiteys I still had lying around whereas it would be easy to utilize the tuck rule.

I went to Walmart, because at the very least I can buy things in the self-check, so I went inside and immediately went to the women’s section and stood in the double aisle with the underwear. I found a couple of different kinds in the same size — roughly estimating what would fit by opening a package and holding them against me — and bought them.

I returned home, went into my room, and locked the door. Then I pulled on a pair of cotton boy-shorts over the homemade tuck device and lifted up the skirt. I was flat.

The next morning I waited for Pete to go to work, got up and redid all my makeup, did my hair with the straightener again — I was really getting the hang of it — and pulled on a maroon dress from the closet. I always liked Jocelyn in this dress and I was hoping it fit. It did, I stepped into it, zipped up and rooted around in the closet for a pair of flat shoes. I couldn't find any, but I found a pair of maroon colored wedge-like heels. I pulled them on and quickly tried teaching myself how to walk.

It was ultimately a success and I was able to make it to the elevator of the building without killing myself.
At the mall, I went to Patti’s and forced myself to go inside. I went up to the counter and stood there for a moment in line behind their shoppers. Finally at the front counter.

“Can I help you, Miss?” the same girl asked.

“I was wondering if you’re hiring?”

“Of course, let me get you an application!” she reached under the desk and handed it over. “If you fill it out now, you might be able to get an interview today. My boss isn't too busy.”

“Great, thank you so much.”

I went to the side and looked at the application — I didn't know what name to put, but soon realized that my name was kind of ambiguous. I wrote Alex.

Two months passed by with me working at Patti’s I was actually doing really well there and had even gotten a raise. My closet, which used to be guy clothes was quickly filling with girls clothes and I was learning how to be a girl more every day. My hair, which was longish to begin with, was down to my shoulders and I kept it in loose curls.

Pete left before I left for work and was in bed before I got home, so the situation never had to be explained until today when I got home from work.

I walked in the front door and directly into the kitchen, to grab a glass of red from the fridge and nearly had a heart attack with Pete standing at the stove heating something in a pot. He turned, looked at me, and went back to his pot.

Then he realized and turned back toward me.

"ALEX? What the fuck!?”

I nearly fainted. I was horrified. I never wanted anyone to find out.

“Alright! Here’s the story. I couldn't find a job and I started dressing like a girl so I could get a job at a clothing store in the mall. It’s been going on for 2 months,” I started. “I can’t stop. I like the job and I make really good money.”

“Jesus Christ, you’re a pretty hot chick,” Pete said.

My face glowed red, no doubt, “Thanks, I guess.”

“Go get changed, I made some dinner. I’ll share.”

I ran into the bedroom and I was shaking. I pulled on a pair of sweatpants that had Juicy on the butt — they were super fucking comfortable — and a loose t-shirt. I put my hair up in a pony tail and went back to the living room where Pete had a bowl set up for me.

“Christ,” he muttered.

“I can go back…” I started.

“No, it’s fine.”

After dinner, we sat there talking, it was weird, I was drinking red wine, and he was drinking beer. We were both drunk and laughing. Pete leaned in forward and pushed a strand of hair out of my face.

“Pete…”

“God damn it, you’re…”

He never finished the sentence, because instead he put his mouth on mine and we started kissing. It was good. I never thought I’d say that, but it was good. We stretched out on the couch and heavy petting commenced.

“Pete, stop…”

I pushed him up a bit.

“We’re both going to regret this, you know…”

He abruptly stopped my words by kissing me on the mouth and before I knew it he picked me up, my legs wrapped around his torso, and carrying me to his room. We fell on his bed, and continued kissing and Pete pulled off his shirt, and then pulled off my shirt revealing a very unfilled bra and he kissed my neck...

“I want to fuck you…” he whispered, his hot breath on my neck. “I want to fuck you, so bad.”

I bit his bottom lip, my body taking control, fighting against the tucking device.

“So? Do it…” I whispered.

Pete stood up and pulled off his pants and then pulled off mine. He reached into a drawer in his nightstand and found what he was looking for: lube. He flipped me over onto my belly and lifted me to an all fours position and rubbed his dick against my asshole while lathering it up then with one fluid motion he was fucking me.

One hand on my left shoulder while he penetrated me with hard painful thrusts, the other moved my hair over my left shoulder and he leaned down and kissed my neck. He went for a few minutes before he came inside me and collapsed next to me on the bed.
I woke up the next morning in a world of hurt and Pete was gone. I got up, took a shower, and got ready for work. I wore a dress, because putting on pants was a painful idea at best and left.

At work, a co-worker Molly noticed I was walking a bit funny, and started laughing.

“Damn girl, you’re walking funny. You must’ve had sex last night.”

My face went flush.

“Oh my God, you did! Who is he?” she asked.

“My roommate,” I whispered and then I looked up and saw Pete walking into the store. “Who is walking into the store, right now!? Oh God.”

Molly laughed out loud and Pete spotted us. Molly ran off as he came over and looked me up and down.

“Sweet Christ,” he whistled.

“Stop it.”

“I mean, really, Alex, you look stunning.”

“Pete…”

“Listen, about last night, I…” he stopped. “I’m not gay.”

“Either am I!” I said in a hushed tone.

“Funny way of showing it, Alex, but let me finish… I’m not gay, but I’m so incredibly attracted to you. I’d be lying if I said I didn’t want to do it again.”

“Do you know how much pain I’m in?”

Pete kissed me full on the lips, abruptly, and then pulled away.

“I have to go; I’ll see you at home.”

I stood there stunned as Pete left the store; Molly was at the register laughing, “God, he’s cute!”
I just shook my head.

I got home a few hours later and Pete was in the kitchen making something in a pot.

“Hey hot stuff,” he called over his shoulder.

“Pete, last night was a onetime thing,” I said. “I mean…”

“Alex, stop it. You’re dressing like a girl… apparently all the time by the looks of it. You don’t even look like a guy in the least. If it wasn't me it would've been someone else.”

“You’re saying I would've let another guy screw me?” I asked.

“I don’t know, Alex. Sure we were a little drunk, but we had our wits about us,” Pete said. “You said something about regretting it, but I don’t regret it.”

“I don’t either, damn it,” I said, softly.

Pete grinned, walked over, and put his hands on my waist.

“Then let’s do it, huh?” he asked. “Let’s try and have a relationship.”

“A what?!”

“A relationship, I mean, we already live together, why not be together?”

“That’s crazy, Pete. You want to be my boyfriend?” I asked.

“I want to be your boyfriend,” he said, then kissed me on the cheek.

After dinner we were sitting on the couch, having some drinks, and watching some television. Pete leaned over and kissed me on neck, then the shoulder, then my arm, and hand and…I turned to him and pounced.

It was uncharacteristic, but someone giving me this time of attention, I was incredibly turned on. We started kissing and heavy petting ensued and I could feel his hands sliding down the back of my sweats.

“Not tonight, alright?” I whispered.

“Sure,” Pete said and kissed me lips.

That’s when I decided to go all in, to be in a relationship with my best friend, a guy …and I slowly moved down his body, and pulled at the waistband of his shorts. I pulled them down and his penis sprang to life. He was well endowed, which wasn’t surprising, he had his fair share of girlfriends and almost got engaged, but it was large. He could have any woman he wanted, probably, and he wanted me.

Having seen a multitude of porn in my lifetime, I had a kind of idea of what to do. So, I licked the tip of his penis and he groaned loudly and then took him in my mouth and commenced giving my first blowjob ever.
I went up and down, I licked, I sucked, I used a bit of teeth — all the things I’ve had done to me — and when Pete came, he came directly in my mouth; and I swallowed.

Afterward we lay there, post-blowjob, I sighed.

“You didn't have to do that, Alex, I…” Pete started.

“I don’t know what came over me, honestly. I thought about you actually wanting me, and I wanted you in return,” I whispered. “I never thought I’d be with a guy.”

“Either did I,” Pete laughed.

I smacked his shoulder and buried my face in his chest.

“You know we’re not making out tonight, right?” he said, with a grin.

“I hate you,” I said.

Five years later, Pete and I, are still together, still going strong in all ways. I got a job managing an upscale boutique and actually made enough money to get breast implants, but decided against them. Pete said they didn't matter to him and I decided they didn't matter to me, yet.

Pete wound up being a great guy, I thought, as we started this “relationship” that he would ultimately leave me for a real woman, but it never happened. He never strayed and that is something that will always make me love him.

On a Wednesday, in October, Pete and I were having dinner at a little Italian restaurant and over a bottle of red wine, he asked me to marry him, and I said yes.

Life works in mysterious ways.