A Fan of Amy Pt. 01

To say I was a late bloomer is to put things nicely. Until I left my parents' house for college I had never seen porn before, but boy did I catch up fast. As I started to understand how much fun jacking off was I started to appreciate more and more the cloths those sexy porn stars would wear, I would even find myself going back to the start of the videos just to look closer at their cloths. Be they strapless, push up, laced, trimmed, or woven bras with matching panties with a wide range of colors; a nice garter attached to fish net stocks, leggings, knee length socks with nice red bows on top; a sexy gray school girl sweater covering a oh so small white blouse that exposed the chest; and so much more.

Beyond the porn I felt being out of the house and being an 18 year old college student made me a man! But not so much a man as I'm 5'4", slim build, baby face, with bright hazel eyes and deep chestnut colored hair. In fact, more than a couple of time while working at my local Walmart I had customers call me miss, which kept planting more and more ideas into my head.

After a couple of months of admiring the sexy clothes of all the actresses I was enjoying so much, I took the leap, I bought for the first time my own lingerie a pair of matching hot pink lace push-up bra and lace strappy thong. The whole week I was stressed waiting for my package to arrive hoping my roommate didn't see the package. When the fateful day arrived, and I got home I couldn't have jumped any higher as I saw the package in front of my door. I scrambled into my apartment and locked the door behind me, my heart racing. I went into my room and closed the door. Slowly opening the box my heart started to race, I will never forget that moment holding my first pair of bra and panties.

Suffice to say my dick was rock hard in an instant. I stripped down and double checked that my door was locked, I slowly put on the panties enjoying the feeling of the running against my skin. My cock pressed against the snug fabric as I carefully put on the bra. I turned around and faced the half mirror in my room and I was shocked at what I saw. "Damn I really could be girl" I thought to myself, my smooth face, which was never able to grow facial hair; long natural eye lashes, accentuating my eyes; my shoulder length chestnut hair shining softly in the light; and my smooth skin which I painfully shave almost every day. "Fuck! I'm hot!" I thought to myself as my cock twitched with excitement.

As I reached down to touch my twitching and now leaking member, I heard my roommate come in. "Will you home?" John shouted. I quickly grabbed a pair of sweatpants and t-shirt to throw over the cloths but the friction on my body was too much and my body betrayed me as I started to cum. While convulsing in pleasure and moaning a little I heard knocking at my door, "Dude you ok?"

"Y-y-esssss, I'm fine" I say while panting and trying not to betray my ruined orgasm.

"You want a pizza?"

"Fuck that's what he had to ask to ruin me cumming!" I thought to myself. "No, I'm good" I said as I look down and my own cum covered chest and dirty panties.

"Ok suit yourself." As John I heard walk away, I was finally able to relax a little.

Since that first time I started to get a thirst for wearing women's cloths not just lingerie. It started off small, a pencil skirt and tight button-down shirt my sister had never really worn I brought them back to my apartment after visiting home one-time. And then I slowly bought more and more so much so that I ended up needing to buy a dresser just for the women's cloths.

I felt that John was getting more and more suspicious of my activities as the packages kept on coming in, along with finding every so often a pair of panties, a women's shirt or some other piece of women's clothing strewn about the apartment. I always shrugged it off saying it was a friend of mine's who stayed the night.

Now by this point I knew I was becoming a sissy, but very much in the closet. Almost every time I wanted to do one of my crossdressing adventures, as I liked to think of them, I checked 5 times to make sure my roommate wasn't going to be home and I could head out in my sexy clothes and makeup. I had gotten into the routine, John heading home for the weekend and me waiting 15 minutes to start my transformation into "Amy".

This weekend was no different, "See you on Sunday dude!" I heard John yell as he closed the door behind him. I looked out the window making sure he had headed towards the bus before I started my transformation into Amy. After an hour I stepped away from my mirror and admired my work once again. I was wearing my Britney Spears "Hit me baby" outfit, a white crop top tied under my chest, with a grey knit arm warmer, a plaid red and black skirt, black lace stockings, with black 4 inch heels and underneath my slutty red lace garter, crotchless red panties, and half cup bra covering my "budding" breasts. Checking to make sure my mascara, lipstick and eye shadow didn't smudge and that my nearly constant hard on wasn't visible; I headed over to my Amy dresser and pulled open the bottom drawer, the toy drawer. After musing over the array of different sized dildos, anal beads, and vibrating eggs I settled on a crimson red 3" wide butt plug. I had gotten already use to relaxing myself and soon the toy was lodge deep inside of me, making my little cock leak a little bit of cum. I was always astounded how the butt plug made me sway my hips more and more like a proper slutty girl. With me all gussied up, I headed out the door.

I took my usual walk around my neighborhood making sure to take note of all the men who turn to look at me. I finally got to my favorite spot, a secluded bench at our local part "hidden" mostly under a tree.

I then spent the next 20 minutes taking selfy after selfy making sure I got the perfect angle to show off my chest and slim sexy figure, and "O" face as the butt plug was doing its job. After I finally found the perfect one, I opened Amy's social media and uploaded the photo. Not more than a minute passed before I heard my phone beep telling me I got a new message. I smiled from ear to ear as it was from my favorite follower JohnnySinner432, "You look sexy as usual Amy! Love the outfit!" A few seconds later another messaged popped up from him, one that too this day is burned into my brain, a picture of his rather large erect cock. Now I admit I've gotten more than a few dick picks since opening the account, but none like his. Too say this cock was perfect would be an understatement. Before I could even respond he deleted the message.

"Was that by accident?" I thought to myself as my own member twitched a bit in excitement. A little flush in the face and getting a little worried I stayed to long in my secret spot I headed back to my apartment. "What if it wasn't by accident? Should I message him about it?" so many questions were running in my mind as I opened the door to my apartment.

"Will? Is that you?"

"FUCK!" I thought as I John's question rang through the apartment. "He wasn't supposed to be home for the weekend!" Not wanting to have him thinking it was a someone trying to steal from us I let out a quick squeak as I tried not to make too much noise in my heels as I practically ran into my room, "Ya, it's me."

Just as I opened the door to my room, I hear the door to John's room open, "What's all that loud clicking noise, you bring a girl home?" And then the sound I dreaded for the past two years, a gasp from him. I slammed the door shut and lock the door, my heart racing. John comes practically banging down my door, "Dude was that you?"

"Fuck he saw me, Fuck fuck fuck fuck!" I thought to myself. "I don't have time to change, he caught me!"

"John leave me alone!" I shout. I hear him retreat a little and start to breath a little bit, before my phone rings and I see a message from my favorite follower, "Will?"

My face couldn't have turned a brighter shade of red, "JohnnySinner432 is my roommate?!" I thought in shock. Unable to respond I heard John whisper by the door, "Amy?"

I would be lying if I didn't say my cock twitched after hearing him say my sissy name. My breath caught, but after what seem to be hours I responded, "Yes-s-s-s"

"Let me in please."

I slowly rose from the floor straightened up how I looked and slowly opened the door to see my roommate's shocked face, "Amy? I mean Will? I mean what the fuck dude!" I try not to break down right then and there.

"Explain everything!" John pushed himself into my room and took a seat on my bed. Still in shock I walk over to my chair and sit cross legged feeling my butt plug nestle further into me. "This is me," I say after nearly two minutes of silence.

"What's that supposed to me? You're telling me you're the girl I've been fantasizing about for the better part of half a year? You're the girl that I've been practically sexting with for the past couple of months?! You're the reason I broke up with my girlfriend?"

I was taken aback and mostly flattered by what John said, even more so as I saw what seemed to be a growth in his shorts. "Yes? I guess?" I said still trying to process all of what he said.

"When did this start?" John said noticing my gaze at his crotch and deciding not to cover but rather accentuate his growing member.

Feeling my body react to see his tent I look for the first time really at my roommate. John was also of similar height to me, maybe two inches taller; toned body thanks to his running, honey colored eyes, and strawberry blonde hair. "He actually looks somewhat cute," I thought biting my lower lip. "Well I've always loved women's cloths," I said as I uncrossed my legs and moving my chair closer to my bed. "And then about two years ago I started to buy my own. Which eventually lead me into the persona of Amy" I said in a rather feminine voice. John's eyes went wide, and his now fully erect dick twitched a little.

Before I could get another word out, I felt his lips press against mine, probing me with is soft lips and tongue. After a moment of confusion, I start to kiss him back more fiercely throwing us onto my bed. He laid back and I straddled myself over him pressing my bubble butt against his shorts.

"Fuck Amy!" I heard him groan as we continued to kiss ever so softly but hungrily. John pulled me close, flipped me over onto my back and lifted my skirt. "How is it this site is probably the sexiest thing I've seen." I hear John said along with a click of a photo from his phone. "For me for later," he laughed as he pulled down his shorts revealing the most amazing cock ever, the "accidental" dick pick from before did it no justice. His cock had to have been 9" long, 2" thick, perfect olive tan color, a pulsating vein, with a pink head leaking precum, and no hair anywhere.

"Your cock is the most amazing thing I have ever seen," I said shock at that the words left my mouth.

"Well you're the sexiest thing I've ever seen," he said back, grabbing the base of the plug and pulling ever so slowly. The feeling was incredible, and I nearly came, but after the toy was out of me, I felt empty. Not being able to hold his excitement I felt his cock press against my pulsating boi-pussy. Letting out a little moan feeling his cock run over my g-spot I murmur, "A little slower big boy."

He chuckles a little and slows down the pace, "Sorry Amy your body was just so inviting." I slowly feel him filling my waiting body and gasp in pleasure as I feel his balls hit ass, making my whole-body quiver with pleasure and nearly cum.

He started to rock back and forth my ass hungrily holding onto his monster cock. "Oh Johnny fuck me! Turn me into your cock slut!" I say in a trance feeling for the first time a real cock inside me. As though I flipped a switch in his mind John start to move faster and reaching into my half open blouse and began to roll my nipples in his soft fingers. The feeling of his soft fingers on my chest pushed me over the edge, "I'm cumming!" I shouted as my body arched and rope after rope of cum shot against my skirt and his shirt.

"Fuck!' John said as he grabbed my legs and pressed deep inside me and started to fill my body with his warm sweet cum. Exhausted John fell onto my chest, cock still buried deep inside me. "I think I could get use to that Amy" he whispered in my ear and I felt a wave of pure joy fall over me.