Kasey's Confession Ch. 01

My name is Kasey. This is the true story of my journey into a life of dressing as a woman, role-playing with men and eventually spending over a decade being sexually submissive to men and being passed around freely between them.

My journey began nearly twenty years ago and started at a different place than most crossdressers. I was obsessed with women's legs to the point where it became a fetish. One day a woman I was seeing, upon hearing me complain about her legs having stubble on them, told me I should try shaving my own legs if I thought it was so easy to keep them smooth all the time.

So I started shaving my legs. At first I just wanted to prove to her that I could do it, but I was amazed at how good my own legs looked after being shaved. When she dared me to keep shaving, she told me, "Just doing it once doesn't prove anything; keeping them that way is the hard part."

So, I kept shaving, and the more I did the more I wanted them to look good. I started shaving up to my waist and modeling for myself in front of the mirror. I bought a pair of short shorts and started showing off. Eventually I wanted to show my legs off in public and felt having a girlfriend would keep people from getting "the wrong idea" about me.

Eventually my girlfriend threw in the towel on me. She said she'd created a monster and couldn't deal with my obsession with showing off. Her departure started a period in my life where I became very nervous about going out in my shorts, but at the same time my desire to do so became greater.

Whenever I was out at the supermarket or gas station or just about anywhere I went in my short shorts I would notice men checking out my legs. Sometimes they looked confused or annoyed when they saw I was a guy, but every once and a while there would be a man who smiled or winked at me.

I was loathe to admit it, but I'd feel butterflies every time a man would check out my legs and smile or wink or otherwise indicate that he liked what he saw. Then one day I was in the supermarket in my newest shorts, a white pair so short I worried my balls might pop out the side if I turned too quickly. I noticed a man looking at my legs and following me around the store. At one point I glanced over and down at his crotch.

He had a huge bulge in his pants. My heart fluttered and a giggle burst out of me.

I rushed to get out of the store, feeling suddenly awkward and confused. The rush I got from having men check out my legs got so much more intense when I realized this man who was following me around had a raging hard-on.

I kept telling myself it was an anomaly. I was completely straight and of course I liked that I turned this man on. What did I expect from wanting men to appreciate my legs? Did I think they would write poetry about them?

At that point I started fantasizing all the time about men, about being dressed up like a woman in very sexy clothes that showed off my legs, and about being made to service the erections I gave them. I started shopping for high heeled shoes, short skirts, thigh high stockings and began posing in front of the mirror and liking what I saw.

The fantasies became more intense over time and as I started doing things like painting my toenails and wearing lace or thong panties all the time, even under my pants at work. My public appearances were more daring as well. I started tanning my legs, wearing shorts that could not be passed off as men's shorts or unisex, and would actually try, once or twice, walking around in short shorts with lace-topped ankle socks and women's sneakers.

I started meeting men online, at first just to talk and then to meet so I could show off my legs to guys who were interested in seeing them. I would meet them in parking lots at first, but it felt goofy and uncomfortable and so I started setting up to meet them casually at a bar near where I lived. It was a place where people stopped for a drink on the way home or met with friends for a few rounds. It had a laid back feel and the bartender I usually saw there, a young woman named Jen, was very friendly and always seemed glad to see me.

I got comfortable meeting men at the bar, and as I did my fantasies became more intense and outrageous. I started going out to men's cars with them and letting them touch and fondle my legs. Then I met a man who told me he really wanted to jerk off on my legs.

At first I said nothing. I was surprised by the request and the way in which he casually brought it up. I measured my insistence that I was completely straight and just wanted men to admire my legs against the intense sexual fantasies I was constantly having involving men. I decided it was not going to interfere with my "straight guy with great legs" persona and would be an even better way of showing off and having my legs appreciated.

It was awkward in the front seat of my new friend's car. He was trying to feel my thighs with his left hand while jerking off with his right. When he pulled out his hard cock, it was of very average size, maybe a bit smaller than most, he was furiously trying to get off.

"Look," I said, "I live just around the corner. Why don't we do this at my place?"

It was the first time I brought a man back to my apartment for any reason relating to my legs or my crossdressing. Alan was a very non-threatening kind of guy and he was incredibly turned on by my legs and how freely I let him run his hands all over them. The least I could do was make it comfortable for him to get off on them.

The first thing Alan asked after we were in my apartment was if I'd put on a pair of high heels for him. We'd talked about the outfits I wore at home online, and now that we were back at my place and safe from prying eyes, it seemed a logical step.

I brought out one of the two pairs of heels I had at that time and sat down at the kitchen table next to Alan. As I started to take off my sneakers, he excitedly grabbed my leg and pulled it up on his lap.

"Let me do it," he said, breathing very fast and deep. He untied my left sneaker and quickly yanked it off, throwing it absently across the room before pulling off my sock and dropping it on the floor.

One of the things that always bothered me most when I dressed was my large feet, which required a size twelve in women's shoes. I was self-conscious of this whenever I wore heels and had not yet worn them in front of a man.

"I love your toenail polish," Alan said as he continued breathing heavy while pulling my foot up to his face for a closer look. "You have very beautiful feet."

Those words gave me butterflies and I smiled. My own erection was straining against the material of my shorts and I popped it out the bottom of the leg of my shorts where I started absently stroking it while Alan kissed my feet and along my leg while furiously jerking his own cock.

It wasn't long before his body jerked back and he yelled out "You bitch!" while his semen shot out of his cock. Most of his load landed on my legs but one stray stream caught me across the cheek and landed in my hair.

Once Alan caught his breath, he quickly gathered up his clothes, pulled his pants back on and slipped into his shoes. He muttered and quick thanks and headed out the door without saying another word.

Sitting there, still hard as a rock, I looked at my cum-covered leg and started jerking off while kissing and licking my own legs. When my tongue wandered over to where Alan's cum was dripping I paused for a moment and lapped at it. When I realized how good it tasted I began jerking myself off relentlessly as I devoured the present Alan had left me with.

After I finally came, all I could think about was feeling disgusted about having eaten another man's semen and how weird it felt to have him jerking off on my legs.

Even though it had been an incredible experience, I felt sick afterwards. I stood in the bathroom looking at myself in my tight little shorts. What was I doing?

I stepped back, wrestling with the conflicting thoughts and emotions running through my head, and one single thought came blasting to the surface.

"A man got off while kissing my beautiful legs."

With that thought I fought off my misgivings and fears and told myself I didn't need to stop showing off my legs. I didn't need to stop meeting men.

I wanted to meet more men. I wanted to show off my legs more often. I NEEDED the attention and the reinforcement of my belief that I had gorgeous female legs.

Instead of backing away I started going out to places like the supermarket and gas station all the time with my short shorts on. I would get some stares, the occasional nasty hateful remark, and sometimes the long lusty looks that gave me butterflies.

Although I never wore anything other than a t-shirt, shorts and sneakers to the bar, and I never hooked up directly with any of the guys I met there, the frequency of my meetings would attract the interest of Jen, the bartender who usually worked during the afternoons I met men there. One afternoon when my "date" didn't bother to show up on time, I found myself sitting at the bar talking to Jen while I waited.

At one point she leaned across the bar and whispered, "I bet you give GREAT head."

"What?" I was caught completely off-guard.

"Oh come on, all those guys you meet here?"

"You've really got me figured all wrong," I told her. "Those are just guys I work with. Sometimes we meet up for a beer."

"Whatever," she said and slid me another beer. "That one's on me. I didn't mean to offend you."

"Thanks," I said sheepishly. "You didn't offend me, it's just that, you know..."

"Sweetie," she said while gently placing her hand on mine, "you come in here three or four times a week and always meet a different guy. I can tell you've never met before. They stare at those legs of yours and you stare at the bulge in their pants. It doesn't take a rocket scientist, you know?"

I looked down silently at my beer, glad that the bar was empty except for Jen and me. Then the guy I was meeting walked in.

"Kasey?"

Mike was different than the other men I had met. On the whole, most of the guys I met were timid and let me direct the conversation. Mike was a more dominant personality and I knew that before I agreed to meet him.

"Hi," I said as I turned to him while trying to keep an eye on Jen. "You must be Mike."

"Yeah," he said and sat down on the stool next to me.

"I thought we could get a table near the back—"

"This is fine," he said. "Sit with your legs crossed like a good girl."

Jen heard everything, and came over with a big smile. "What can I get you to drink, Mike?"

I had crossed my legs and looked away as Mike ordered a beer and told Jen to bring a shot of tequila for me. I kept looking away from Jen while trying not to ignore Mike, cringing at the idea of them talking.

"Where do you and Kasey know each other from?" Jen asked Mike.

"From online," Mike said.

"One of those dating sites?" Jen asked, causing me to visibly cringe.

Mike took his beer in hand and put the shot of tequila in mine. "Not exactly," Mike told her.

I drained the tequila shot and got up from the bar. "I have to go," I told Jen. "How much do I owe you?"

"I've got it," Mike told me.

"Thanks," I muttered and rushed out of the bar. I had just gotten to my car when I heard Mike's voice from behind me.

"Do you always rush off like this?" he asked. "You are a terrible tease."

"I don't know what I'm doing," I told him as I opened my car door. "I'm sorry."

"Relax," he told me. "You are very confused right now because you want something your brain keeps telling you is wrong. And you don't know whether you can do it or not and you're scared."

"I don't want to do anything. I just want to go home."

"You want to start sucking cock."

"Oh gosh, no," I said and made a face. "I'm sorry if you thought—"

"You told me online you fantasize about it all the time."

"Yeah, sure, but that is just fantasy."

"And you go out all the time in those tight little shorts meeting men. You fantasize constantly about being on your knees sucking cock. You are a very confused wannabe sissy."

"I'm sorry, I don't know, I just—"

"Why don't you go back to your apartment and get all dressed up in one of those miniskirts and some high heels like you talked about online. I will call you in an hour. If you want me to come over and teach you how to suck cock, just answer and let me know your address and I'll be over. If not, don't answer the phone and I won't bother you ever again."

"I'm really sorry, I think I gave you the wrong idea."

"No problem. You just go on home and decide what you want. If I come over, I WILL make you suck my cock and you WILL love it. Otherwise, you can keep fooling around playing games with men, but after a while they'll start getting real bored with you."

I jumped into my car and drove home.

At first I was determined to put an immediate end to what I had started calling my "hobby." Things had gotten out of hand, I told myself. All I wanted was to show off my legs and have men appreciate them. I wasn't about to start sucking cock, even though I fantasized about it constantly. I was just going to stop and go back to being "normal."

Then I opened my closet and looked at the pair of high heels I had recently purchased, six-inch platforms, and the miniskirts and panties I had been collecting. I had tears in my eyes as I pulled my girl clothes out of the closet and started trying on different combinations. By the time I found a combination of clothes that made me look like a sexy stripper, my phone was ringing.

I paused, staring at the phone as it rang. I knew the answering machine would pick up after four rings, so as the third ring came and went I made a decision and picked up the phone.

"Hello?" I asked in a feminine voice.

"Is this Kasey?"

"Yes." I could hear my heart pounding.

"This is Mike. Give me your address."

I paused, struggling to speak, my heart pounding louder and my hands shaking as I looked down at myself in a miniskirt, high heels and pink ankle socks with lace tops.

"Don't be afraid, Kasey," Mike said. "You want to suck cock, don't you?"

"Yes," I sighed after another pause.

"Give me your address."

I gave it to him, stuttering and crying as I did. After I hung up, I found myself curled up in a ball on the floor hugging my knees and rocking myself. There was no turning back. Mike was going to come over and I was going to become a cocksucker.

When the doorbell rang I struggled to get to my feet. Standing up in six-inch platform heels wasn't easy, given the fact that I was shaking and both nervous and excited at the same time. I tried to walk gracefully to the front door of my studio apartment, stumbling several times, but finally able to reach the door. I opened it slowly, and once I saw Mike standing there and smiling, I quickly opened it the rest of the way and welcomed him into my home.

"I know it is a difficult step," Mike said as he looked at my tear-stained face. "It isn't easy for someone who has been pretending to be a man for so long to accept that what he really wants is to be on his knees in front of men being submissive to their needs."

Mike took my right hand and placed it on his crotch. As I felt his bulge I shuddered, "Oh my goodness, you are so... hard."

He opened his pants and his fly enough to push his hard cock out and then put my hand on it. My eyes shot open wide and I couldn't help but smile.

As I stroked it gently with my fingertips I giggled. "I want to suck it," I confessed.

"You want to suck what?"

"I want to suck your cock," I replied quietly.

"I can't hear you. What do you want, sissy?"

Looking down at his hard, nine inch thick cock, unable to take my eyes off it and unable to stop thinking it was the most beautiful thing I'd ever seen, I loudly said, "I want to suck your cock!"

I found myself dropping to my knees without any coaxing, wanting to see his big hard cock closer, wanting to know what it would taste like and how it would feel sliding into my mouth. I kept stroking it, leaning in closer to smell him, and looking up hoping he approved. I leaned even closer after seeing him smiling down at me, and lightly kissed the head of his cock.

The first kiss felt so good I kissed it again and again. My kisses became more frequent, more passionate and I couldn't stop. Soon I was sliding the head of his cock into my mouth and licking it up and down the shaft while gasping and moaning.

"That's it, baby," Mike said, "let it all out. You've needed this for so long."

I was sliding more of his cock in and out of my mouth, then letting it slide out while kissing and licking his cock up and down to the balls, where I suddenly found myself burying my face while kissing them. Then I kissed my way up to the head of his cock and once again slid the head in past my lips and started sucking him the way I'd seen so many women do in porno movies.

I was so happy when he finally moaned, so glad I had given him pleasure, and he grabbed my hair and pulled my head away from him.

"I have got to sit down," he said, gasping. "You are one HUNGRY bitch."

I was eager to continue, but Mike told me to bring him a beer. Then he looked at the big mirror that sat on top of my dresser and asked if it came off.

"It was part of the dresser, but the back broke when I moved so it just kind of sits there." It was a big, full length mirror I had often taken down off the dresser to admire my legs when I dressed up by myself. Once Mike saw that it came down, he assisted me in taking it down and resting it against the wall alongside the chair he decided to sit on.

"I want you to watch yourself give me head," he said once he sat back down.

I looked over at myself in the mirror, standing in front of a man in heels and a miniskirt, my legs looking more beautiful than they ever had before even though my knees were shaking and I was very unsteady in my heels. It felt natural, and right, as I got back down on my knees in front of Mike.

He removed his shoes and his pants. Once I took his hard cock in my hand he told me to look in the mirror. I turned my head to see my tear-stained face just above Mike's cock, which my hand was gently stroking.

Through the tears was a look of happiness. My eyes were bright and I was smiling, but I had never seen myself looking so full of joy.

"Now you finally know what you are," Mike said. I slid my mouth back over the head of his cock as he told me, "Kasey, you are a natural born cocksucker."

I stopped for a moment, taking in the sledgehammer of the words Mike had just hit me with. I closed my eyes and thought about how many nights I had fantasized about this. I opened them again and looked at the mirror, my beautiful legs on display in a short skirt and high heels. My back was arched and my ass was in the air as I watched myself slowly descend back down the full length of his cock until it hit the back of my throat.

I gagged and pulled back slightly, then realized I was drooling all over his cock and balls. "Keep it nice and lubricated, sissy, it will slide up and down so much easier."

I nodded and kept sucking, sliding my mouth up and down the shaft of his cock, which seemed even harder now than it had before. I paused to run my tongue around the head of his cock, lavish his balls with my tongue and plant kisses all along the length of his gorgeous cock.

"I wish I had gotten prettier for you," I said, looking in the mirror and wishing I had a more girlish top and that I was wearing makeup and had long girlish hair.

"You can do that tomorrow," he said as he moaned and grabbed his cock with his right hand while pushing my head down on it with his left.

I felt a sense of panic as he tensed up, my head pulled down on his cock as he jerked it and then released his cock and pulled my head down hard on it. "Oh hell yeah!" he exclaimed as he came hard into my throat.