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.
