Shawna's First

this is the story of how lost my virginity and began my journey to be the goddess I am today!

I have always known, even as a small child, that I was unlike other boys. I started stealing my sister's clothing at the age of the eight. My parents caught me numerous times dressed as a girl, always telling me it was wrong and trying to discipline me. I enjoyed wearing her dresses, underwear and especially her shoes. My sister Kara was 18 at the time and rather promiscuous. She would dress very provocatively, wearing high heels, and very short tight skirts. The only thing I ever wanted to be was her. She was absolutely beautiful, with long straight light blond hair and piercing light blue eyes. Her body was unbelievable, perfectly proportioned for a woman of 5 ft. 5. I remember seeing all the boys she would bring home when my parents were working, and take up to her room. I could hear them having sex. It sounded like great fun, and I wanted to try. After they would leave, I would sneak into her room and try on her clothing, looking at myself in the mirror and thinking what a pretty young girl I was .

Fast forward 10 years, my parents are dead. I received a substantial sum of money from their life-insurance, but promised to stay with my sister through high school, so I'm living with her family. I am an 18 year-old virgin transsexual. My sister has some suspicions about my unique needs, but can't find a way to talk to me about them. As a boy I am unremarkable appearing, but as a girl I'm stunning. At 5 ft. 6 and 126 lbs., I have a similar build to my sister before she had her children. My hair is the same light blond and my eyes are the same light blue.

I have not had a haircut since my parents died three years ago, and it is now halfway down my back. I have very shapely legs that are topped off by a small tight ass. I have slender hips and a nice flat stomach. My shoulders are slight and my arms are thin and end in long thin fingers. Half of my closet is devoted to women's clothing. The tighter and shorter the better. I also have an extensive collection of stiletto heeled shoes and boots. And I want to get laid. I dress in my bedroom every night, practicing walking in my heels and talking in a baby doll voice, trying to make myself the perfect girl. I didn't have breasts yet, but I also looked five years younger than I was, so it didn't bother me. I fantasize about being taken the way my sister was when she was a teenager, jerking off constantly.

I decided that Memorial Day weekend I would lose my virginity. I would travel to the gay barin the town next to ours, the Homestead, and find a man to fuck me. I would go on Friday, when my sister and her family left for the weekend to go to the shore, that would leave me the weekend with my new lover. The week passed excruciatingly slowly, I began to plan out and fantasize about what was going to happen on Friday. I chose the perfect outfit, the perfect fuck me shoes and continued to work on my makeup. High-school was the last thing on my mind all week, as an honor roll student my graduating was all but guaranteed, but that didn't stop some of my teachers for making life miserable. Especially Mr. Booth the gym teacher.

He was a legend at our high school, Mr. All -State basketball and football who went off to college and would have gone pro but was injured. His playing days over, he returned home to begin teaching at his alma mater. It was as if he was put together by committee, picking the perfect parts for him. He was six-foot six, jet black hair and light brown eyes, perpetually tan and very well muscled, but not a body builder type. All of the girls lusted after him, and all the boys wanted to be him. He was friendly to the jocks, but enjoyed picking on the less athletic students in his classes. That included me, and at times I thought it was only me. I hated him.

Friday night finally arrived. My sister and her family left shortly after 3:30 which left me five hours to get ready for my big night out. I first took a shower and shaved my entire body so that I was silky smooth. Then I took a long hot bath with scented oil to give my body a lovely scent. I put on my sister's silk robe and went to do my makeup and hair. The makeup was easy, and the blush, mascara, eyeliner and lipstick went on quickly. I knew how I wanted my hair it was only a matter of getting it done. It took almost an hour but finally the single braid down the middle of my back was perfect, with a white bow tied at the end. Now it was time to get dressed.

There was a problem, I had a raging hard-on. Taking care of that did not take very long. I pulled on the smallest pair of black lace panties I had and tried to snuggle my still semi-hard cock down between my legs. A black leather micro mini skirt that sat nice and low on my hips was next, followed by a loose white silk blouse which I tied off halfway down to show off my flat mid-riff. I chose a black leather choker to adorn my neck, and large gold hoop earrings. When I thought I was ready I added the finishing touch, 5 in. black leather ankle boots. I looked at myself in the mirror and was amazed. I was now a beautiful young woman who any man would want to have. My cock was straining against my panties. I was ready.

The drive to the bar took about 25 minutes, but it felt like two hours. As I pulled into the parking lot of the Homestead, the butterflies in my stomach nearly made me turn around and go home, but my lust and need for a man gave me the courage to go inside. It was like walking into a candy shop, about 80 men of all ages and sizes milling about a dimly lit room. The small dance floor in the middle of the bar was crowded with shirtless men gyrating to the disco beat. The smell of leather, denim, sweat, smoke and cologne filled the air. I could feel a hundred eyes watching me as I moved across the room. The butterflies returned, so instead of going to the bar I went to the ladies room. I ran into the third stall and sat on the toilet, my mind racing. What was I doing here?

Was I really ready to go through with my fantasies and lose my virginity? I looked around the stall, seeing the graffiti written on the tan walls all offering a good time if I would simply call this number. And I noted a hole about 3 in. wide in both the door and wall, next to the toilet paper dispenser. Glory holes, I had read about these in the magazine's I'd bought . I had been in there for about five minutes staring at my well manicured hands, trying to drum up the courage to step out and live my fantasy when something caught my eye. Someone entered the stall next to me and had put their cock through the glory hole. I was mortified, with feelings of lust and revulsion fighting in my body. A voice from the other stall prodded me into action.

" Why don't you just stroked it little girl. It won't bite. " it said.

I reached a tentative hand out and touched another's cock for the first time. It felt hard and soft at the same time and it was incredibly hot. It wasn't any longer than my own 7 in. member, but it was thicker than mine. I wrapped my fingers around the shaft and slowly started to jerk off my visitor. I heard a groan and then the voice returned.

" Your doing beautifully, that feels fantastic. Why don't you kiss it?"

He was prodding me into giving him a blow job. I didn't know what to do, but lust was beginning to take hold of my body. I knelt on the dirty bathroom floor and stared at the cock in front of me. I brought my lips to its head and gave it a light kiss. Another groan empowered me. I was in control of giving this man pleasure. My lips parted and I started taking his cock into my mouth. Having never given a blow job before, I didn't really know what I was doing. I alternated sucking as much of him into me as I could with concentrating solely on his head and jerking him off with my hand. My other hand was under my skirt and inside my panties tugging my own cock. I came quickly, shooting cum all over my thighs. All the while I continued to blow my anonymous visitor. I was in heaven and my excitement and joy only increased when he screamed.

"I'm cumming!!!!"I wanted to watch this happen, so I pulled his cock from my mouth and jerked him off furiously. With my face only inches away the first blast of cum hit me right on the cheek. It was quickly followed by four more from the bucking , spasming cock in my hand. They all hit my face. I let go and reached for some toilet paper to wipe the cum from my face, and licked my lips tasting some of his seed. It was delicious, and I knew I had to have more.

" Thank you sweetheart, that was incredible. When you decide to come out to the bar I'll buy you a drink . " and with that my visitor left.

I finished wiping the cum from my face and legs and stood up. As I picked up my hand bag another cock, smaller than the first, appeared in the glory hole. I reached out and gave it a quick tug saying in my sweetest voice

" The lady needs to have a drink, but thank you for the offer lover. "

And with that I stepped out of the stall and went to the mirror. My makeup was a mess. A handsome middle-aged man, obviously the owner of the second cock, stepped out of the stall and smiled gently as he walked out the door. It took about five minutes to fix my makeup and clean the dirt off of my knees. Finally I stepped out of the ladies' room and went to the bar.

I found a seat near the end of the bar and waited for the bartender, an older woman, to arrive. She was talking to a heavyset man at the other end of the bar when I caught her eye. She came with a warm smile and a glass of white wine and introduced herself as Meg, telling me the gentleman at the far end of the bar had bought me the drink.

"That's some way to introduce yourself to the regulars. " Meg said.

"What do you mean?"

"Blowing the first man you meet 10 minutes after arriving here." she smiled.

I was shocked at what she was saying, and it was obviously showing on my face.

"Don't worry sweetheart." Meg rested a hand on mine" It was just an unusual thing for a first timer to do. Usually they just stand in the corner looking like a deer caught in headlights. And Scott down there always tries to get to them early. What's your name honey?"

" Shawna" I answered in an wavering voice.

" Well Shawna, welcome to my second home. I know your young, probably too young to be drinking in my bar, but you look like a sweet little thing, I like you and you obviously have big balls to do what you did. "she winked at me. I blushed." So consider me your guardian angel for tonight." Meg gave me an easy smile"I'll keep an eye on you and give you the skinny on any one you'd like to know about. "

Taking a drink of wine to steady my voice I said" Thank you Meg, I really appreciate it." and with that she left to help some other customers. I looked in the mirror behind the bar and scanned the crowd looking for the middle-aged man from the bathroom. That was when I saw him. Mr. Booth, my sadistic gym teacher. He was standing in the middle of the dance floor, taller than everyone else in the room, wearing a skintight white T-shirt that showed off his beautiful chest and large arms. My mind began to race, did he see me? If he did would he recognize me? What would happen if he did? With my mind occupied with these questions, I reached into my hand bag and retrieved my cigarettes. With a shaky hand I pulled one out and went back again to look for my lighter. And that was when it happened.

" Tom Shaw" the voice said quietly into my right ear"fancy meeting you here."

I looked into the mirror to see Mr. Booth standing directly behind me with an evil grin on his face. I was horrified and didn't know what to do when I was rescued, at least momentarily, by Meg.

" Michael" she said" I want you to leave this little girl alone. Shawna, are you okay honey?"

Before I could answer, Mr. Booth answered for me.

"Shawna's fine Meg, we've known each other for almost four years. "he said as he rested a large hand on my shoulder. "I was just surprised to see her here."

Meg gave us a very hard look before turning to leave, and said"Honey, you just let me know if you need my help, okay?"

I nodded dumbly, too shocked to answer. Mr. Booth slid into the empty seat next to me and fixed a with his gaze.

"So you call yourself Shawna do you Mr. Shaw?" it sounded more like a hiss then a voice. " I've always thought you were a little to effeminate, but I never thought you wanted to be a girl. " He took my lighter from my hand and lit my cigarette for me. "If you want to be a girl, why don't you let me treat you like one." he said and put a hand on my thigh, just below the hem of my skirt.

"Mr. Booth" I stammered"please. If anyone found out about this I'd be ruined."

"I know Shawna, that's the beauty of the situation I find myself in. I have a male student who wants to be a girl, and is blowing men in the bathroom of the local gay bar." How did he know that? "I think that you and I should get better acquainted. " he smiled and I saw how beautiful his face really was. I could feel how hard my cock was underneath my skirt with his hand only inches away.

"Okay" I said numbly, transfixed by the rampaging lust I was feeling for him.

"So," he said" should we stay and have a drink together, or should we go someplace a little more intimate and get to know each other much better?" his eyes were positively afire.

Again I could only answer weakly "okay" and with that he stood. My eyes were at his crotch level and I saw a very large bulge in his tight jeans. I wanted to reach out and grab it, but Mr. Booth took my hand and began to gently pull me off my bar stool. I stubbed out my cigarette, picked up my hand bag, allowing Mr. Booth to direct me towards the door. He walked behind me, and slid his large hands down to rest on to my slender hips. More than once I felt that large cock of his brush my ass. Again I felt the eyes of the men in the bar on me, but I was more worried by my high-school teacher, who knew my secret, directing me out into the parking lot.

The night air was warm and smelled of blooms when we reached the parking lot. Mr. Booth informed me that we would be taking my car back to his house. He opened the passenger's door and told me to get in, then walked around and climbed in the driver's side. If I thought the ride to the bar was long, the ride to Mr. Booth's house seemed an eternity. He lived only a few blocks from my sisters', but it felt like we drove for hours. The entire ride was silent except for the radio.

As we pulled into his driveway Mr. Booth looked directly at me and said " Mr. Shaw, from now on you are my whore. I will call you Shawna, and you will service me whenever I want. In return I will protect your secret, understood?"

"Yes" I said weakly" thank you Mr. Booth. "

"Don't thank me yet" he said as he stepped out of the car. I started to open my door when Mr. Booth opened it completely and offered me his hand. I took it, was helped out of the car and led to his house. It was small but nicely appointed. I was directed to the living room where Mr. Booth motioned to me to sit on the couch. I sat down and crossed my legs still feeling confused and mortified by what was going on. I didn't know what to do, but I also knew that my cock was rock hard and had been from the moment he put his hand on my thigh. He left the room and I could hear some shuffling from the kitchen. I went into my hand bag and pulled out a cigarette and lit it. He returned with a glass of wine and a beer and sat down next to me. He handed me the wine and his now his empty hand came to rest on my thigh again.

"How long have you been dressing Shawna?" he asked.

"For about four years" I said" but I've always wanted to be a girl. For as long as I can remember"

He took a drink of his beer and looked at my legs before asking " And how long have you been sexually active?"

What could I say? I didn't think, I just answered" Today was the first time I've ever been with anyone. "I took a large drink of wine

"Really! You are a virgin? So you've never been with anyone before you blew Scott tonight? Excellent. You and I are going to have so much fun together. When I'm done with you, you're not going to want to fuck anyone else. " and with that he stood up. He stripped off his shirt, turned to face me, and stepped right up to me. He put his hands behind my head and pulled me to his smooth chest.

"Ready to begin?" he said.

A wave of lust swept over me as I smelled him, my lips surrounded one of his nipples and I let my tongue flick back and forth over it. My hands stroked his back and slid down to cup his ass. He simply stood with his hands on the sides of my head and let me play. I could feel his cock, its heat and size against my stomach, growing. I reached for his zipper and found buttons. With my hands undoing the buttons of his fly, I began to kiss lightly down his stomach. My right hand went into his pants while my left pulled them down. I grabbed his cock as his pants slid by it. It was massive and it wasn't even fully erect. 10 in. long and too wide for my fingers to encircle it completely . His balls were large and hanging loosely below his huge dick. It was beautiful.

"Little girl, I want you to meet my friend." M. Booth said. "He may hurt you a little, but it's a pain you will love. "

What a smile crossed his face. I had both hands wrapped around his dick and a slowly stroking it. It was incredibly hot and even more heat was coming out of its head.

" Teach me how to suck your cock Mr. Booth." I said as I went to my knees.

" Open your sweet little mouth Shawna," he moved a hand to the side of my face and lightly pulled me forward " and let him in. "

I felt the huge head press against my lips, and I opened them. His cock head almost filled my mouth completely. Then he pushed in more until my mouth was completely full of cock.

"Relax your jaw little bit sweetheart, and this will be easier for both of us. " he instructed.

I tried to loosen my jaw, to free up space in my mouth for him. I still had both of my hands wrapped around the shaft and was slowly pumping him. He was rocking his hips back and forth and I began to match his rhythm. I was a learning quickly because more and more of that gorgeous cock was sliding over my lips and into my mouth. Mr. Booth reached over the top of my head to grab my braid, using it to push my mouth further down his fuck pole. I looked up at his face and saw he was staring intently at me taking his member.

"Your doing wonderfully Shawna, try using more tongue. " he smiled.

The tempo of my blow job was increasing. Mr. Booth was pushing my head down more quickly to meet his hip thrusts. I stroked with both hands and let my tongue tease the head of his cock every time he let it come to my lips. I was in ecstasy, my cock was rock hard under my skirt and I started to cum. Mr. Booth was not far behind me. His pace was increasing and I felt the second hand grab the side of my head. He was holding me tightly and began to pump his cock in and out of my mouth. I gagged a few times, but that didn't slow him down, in fact his speed seemed to increase. He was fucking my face and I loved it. The speed, the power, the heat and the raw pleasure of the length man meat going in and out of my mouth was more than my mind could take. I reached around, grabbed his powerful thighs and pulled him into me. I needed more of that cock in my mouth. I needed it all, I needed it down my throat, I needed to feel his balls against my chin, I needed to feel his pubic hair on my nose. Most of all I needed to feel his cum in my mouth, I needed to taste him. He obliged, pulling his cock out of my mouth and while still holding my braid, jerking off in my face.

"Open that pretty little mouth of yours wide baby, I want you to drink my load. "