My First Time

I grew up in San Francisco where sexuality was always on display. I explored pornography and sexuality at a young age and have always had an adventurous soul. When I was about 14 or 15 years old I began to see pictures and ads from she-male escorts and felt a curiously strong draw towards these fabulous creatures...the best of both worlds as the saying goes.

At 18 I was preparing to leave for college. I spent the summer working outdoors which made me tan and fit...my blonde hair becoming bleached by the sun. So here I was, 18 years old, tall and lean, and growing impatient to fulfill my fantasy of meeting a she-male. Whenever I could I poured through the papers in the news racks and finally saw an article on the transgender scene that pointed out all the clubs and bars in town where the scene came to life. This was my chance.

I went down late on a Friday night...nearly midnight as I recall. There was no one at the door, lucky me, so I slipped inside and found a table in the back by the dance floor. I sat and watched in wonder as my fantasy moved all about me...beautiful and mysterious 'women' filled the room.

I had been there only a little while when a beautiful black she-male pulled up a chair and sat down. She was tall and thin, dark-complexion, high-cheekbones and dressed in a sheer black outfit. I stammered as I said hello.

She introduced herself as Rhonda and asked me my name. I told her and she smiled...I was certain she knew I was underage and she had simply sat down to toy with me. Later I would learn that I was half right.

We talked a bit and then she asked me if I knew what kind of 'lady' she was. I told her she was a beautiful one but she didn't let it go at that. She said she was a lady with a big cock and that she thought I had somehow ended up in the wrong place. Feely bold I told her that I knew she had a cock but that if it was bigger than mine I would drop to my knees and suck it for her. In an instant her face broke into a smile and she told me I had just made a big mistake. She finished her drink and told me we were leaving...I obediently followed her out the front door.

When we arrived at her apartment, off the alley and up the green flight of stairs, she told me to undress so I could prove that I was big...she sat on the couch and watched as I took off my shoes, my shirt and then dropped my pants. She had me turn around on her command so she could survey my ass and told me I was about to lose this little contest I had started. I was standing there in the middle of the room...my hard 8" standing tall...and I gasped when she pulled up her dress. I collapsed to my knees and knelt there is wonder as she began to stroke her un-cut cock...it just grew and grew until it stood a full, thick 10"...just a few inches from my face.

I had never been happier about losing and I just couldn't resist. I wrapped both of my hands around her cock and jammed the head into my mouth...so hungry for her cock and so eager to please. I listened to her instructions as I bobbed and stroked...and realized she was training me to suck my very first cock. She was so huge that I couldn't fit her all the way down but I tried my best...filling my mouth, working my hands and trying to open my throat the way I had seen girls do on me and in the movies. I wanted so bad to please her and get her to shoot a load from that big, black cock.

I must have been there on my knees for half an hour before she pulled me up by my hair...she knew I would do anything to earn her praise. She took me to the bedroom and put me on the bed...hands and knees...doggy style. She could tell I was excited and scared as she lubed me up...sliding that massive cock back and forth in the crack of my ass before finally starting in on me. She never needed to ask if I was a virgin...that was obvious when she slipped the head of her cock into me. I wailed out and she grabbed my hips...holding me still and resisting my attempt to pull off of her throbbing cock. She held me still for a moment or two and then began to rock just slightly...back and forth just and inch as my ass unclenched and she could feel my desire take over and welcome her in. I looked back and she grinned...working me deeper, inch by inch until I had it all and I could feel her balls touching mine. I felt a strange surge of pride as she smiled down on me, now I knew she was pleased with me.

She rode me slow...quickening at times and eventually filled me with cum. I fell forward onto the bed, amazed with this new feeling, and the fabulous sight of her spent cock shrinking from its hardness, and the excitement it had delivered into my body. When I went to leave...she walked me to the door...kissed me and said "now don't be a stranger". I was sure I would be back...but that is a story for another time.

So that is how it began...I still crave she-male cock, big and black is my favorite...and I have been at it for 20 years since.