This is a true story that began when I was about 5. This is my first story, so please, any feedback would be great.
When I was about 5 yrs old I somehow discovered that I enjoyed women's clothing, especially wearing them. It started off rather innocently, wearing my moms or sisters dress along with heels. I used to put 2 stuffed bears as boobs. As I got a little older I seemed to have forgotten all about this for a few years.
Let me describe myself a little before we go any further. At age 15, I was about 5' 4" maybe 120 lbs, longish brown hair, green eyes and a very fem ass.
When I turned 15 or 16, I was able to get a paper route early in the morning. I would get up about 5, load up the papers in the bag on the front of my bike and get to work. As the months passed I was enjoying making some money of my own and really liked be up and out of the house before dawn, Once summer came around, I really learned to love getting up early, Mostly because people would hang their laundry out to dry the night before and go out and get it once they woke up. My old desires to wear women's clothes came rushing back to me, and I often found myself between houses staring at cotton panties and lace bras. It wasn't too long before I got a little more daring, jumping fences to feel the feminem intimates against my face...
Before too long I was taking these gorgeous pieces of clothing home with me and trying them on when no one was around, Then one day I came across some black spandex short shorts, a sexy nylon pair of panties (thongs) and a yellow nylony top. I couldn't wait to get home and try them on. I think I was 12 when I had my first orgasm, wearing these beautiful clothes. Towards the end of that summer I got even more daring and would wear these clothes outside while delivering the papers, actually hoping a man would see me and make me do things with him.. I could imagine him pulling me close to him, kissing me roughly, taking my small girlish hand and making me stroke his hard cock through his jeans. Once he was all hot and bothered, he would push me down to my knees and tell me to look into his eyes while I unbutton his pants and slowly pull them down til his hard cock slapped me in my face. Then he would tease that big cock against my lips, slowly parting them. I would slowly open my mouth and allow his cock to enter between my lips. Taking as much as I could before I choked. He would pull that cock out of my mouth and lean down to kiss me before roughly grabbing me by the back of my head and forcing all his cock down the back of my throat, making my eyes tear and fuel this passion I have to pleasure this man as best I could. I would get into a nice rhythm of licking and sucking the head, then forcing my way down to the root, his pubes tickling my nose, stroking him slow then fast, making him moan, all the while staring up at him. Before I knew it my fantasy suck was over as he blasted a thick creamy load in my mouth. He wanted me to show him his load in my mouth before I swallowed it all....
The days started growing colder and I still wore my sexy clothes underneathe my boy clothes while delivering papers. A few times a car or truck would pass me and I would flash them a little bit of what I had on close to my skin. A few stopped then kept going, I wasn't sure how, but I was determined to make my fantasy a reality. I was really enjoying dressing up as a woman and collected quite a large amount to pretty much fit any mood. But my favorites were still the spandex short shorts, hiked up a little into the crack of my ass. I would wear the yellow nylon top tied up as a belly shirt. I could make myself look very passable without any make-up.
When I was 16, I was masterbating several times a day, sometimes playing with my ass till I came hard. Once, I had the idea to get a carrot and try to fuck myself with it. It felt soo good I had to have more. This became a regular thing, gradually using bigger objects until I could get a Mag-lite in my "gurl" parts.
One morning, a surprisingly warm winter morning I had a chance to fulfill one of my fantasies. I was about half-way through my route and I had to pee real bad, I decided to go into the alley that seperated houses to relieve myself. While pulling my pants and panties down I noticed someone looking out their back door and right at me. My heart skipped a beat as this tall, well built man opened the door and started walking towards me. He also pulled his pants down and pulled his semi- erect cock out and started pissing. He started mumbling something about being locked out of his house and he was soo drunk he couldn't find his key. I realized this guy was talking to himself and I don't think he even seen me. I watched this guy shake off the last few drops and looked up right into my eyes. I had finished my business and tucked myself into my panties. I turned around so my back was towards him and started shaking my ass a little, biting my lip, I turned my upper body to look at him. This guy was stroking his cock and staring at my ass. I was so turned on... I started sucking my finger, hoping he'll get the idea, but he didn't, he just stood there jerking off staring at my ass. So I decided I would do something about this. I slowly walked over to him, took his hand off his cock and replaced it with mine. My first cock in my hand other than my own. I loved it... Anyway I started stroking this nice 6" penis with a large helmet looking head. I reached down and cupped his hairy balls, feeling the weight in my hand. I sped up then slowed down my stroking, just really enjoying the moment and power I seemed to have with a cock in my hand. He started moaning and reached for my ass. I loved the way he was massaging my ass while I stroked his hard cock, I started asking him if he liked my ass, what do you want to do with my ass, want to feel my ass sliding up and down your fat cock?? Mmmm baby, I want you to fuck my ass so slow. C'mon baby put that cock in my ass, make me a real woman... mmm baby please, don't make me beg.... I was soo turned on. This guy was leaking pre-cum all over my hand. I should have stopped stroking him, cause I really did want him in my ass, but I didn't and before I knew it he pumped a huge amount of cum on my legs and panties. Alot went on my hand and even some on my shoes. As soon as he was done he zipped up and went back inside.. How rude!!! He didn't even let me clean his cock off or watch me lick his jizz off my hand or rub his cum all over my panty encased cock. But I found out I LOVED the taste of cum. Couldn't wait for another experience and taste it straight from the source. MMM.
Hope you enjoyed!!! Im looking forward to hearing what you think... More to cum if you like this soo far. <3