Now that I am older, a young man now, I can work to support myself and even treat myself to a session with a Mistress. I moved to NYC. I knew from reading dominant newspapers that many Mistresses worked there. I have always loved dark haired dominant women. I wanted to have a session with a Mistress with dark hair. I also looked for a Mistress that was taller than me, and bigger that me. After all, I'm just a small guy.

I found an ad for Mistress Destiny. She was perfect! My dream Mistress! She has dark hair, straight, long and smooth. Her hair is very fragrant. She is tall, 5 foot 10 inches barefoot. When I met her she wore 8 inch heels. She was very tall! Her skin is fair, and, to make her look even more dominant, she has many tattoos on her arms. Her body is very womanly. She has firm, full breasts, and a small waist. Her thighs are full and lush. Her hips are full, too. Her long legs go on forever. She is my dream come true!

When I met her for the first time, I could not believe how beautiful she looked. I had seen many photographs of her, both from her ads and on her website, http://punishmentsquare.com/destiny/index.html. But I was not prepared for the beauty she possessed when I FINALLY laid my eyes on her in person. She asked me what I would like to do in session, and really listened to what my interests were. I told her I wanted to give myself up to her completely. But how? Could I possibly be kept by her? Was I interesting enough to amuse her?

She did indeed give me some of her ideas about what to do in session. She told me to get undressed and to put a rubber hood on my head to cover my face except for my eyes. I did, and waited on the floor on my hands and knees. The floor was carpeted and warm, and I felt like I belonged there, in my submissive position.

After a few minutes that seemed like an hour, Mistress Destiny came into the room. She wore a black bustier made out of lace that cupped her beautiful breasts. She had on a leather garter belt that laced up the front. She wore tight, girdle like panties. She wore flesh colored nylon stockings. These stockings were the older kind, the kind that are very shiny and smooth. She wore 8 inch high heels that had straps around the ankles. She wore a very dominant collar around her long neck. Her skin was fair and flawless and her tattoos were colorful and very high quality. She went over to a suitcase that contained a large assortment of S & M equipment and proceeded to buckle a strap-on harness with a dildo affixed to it onto herself. I asked her what the strap-on dildo was for.

"You'll see," she purred to me.

She instructed me to get on my hands and raise my butt high in to the air. She then put a rubber glove on her hand and squeezed some k-y lubricant on her hand. By now I knew she was going to explore my virgin asshole! I am so scared, this is too much!

The next thing I knew, I felt her middle finger gently running around the rim of my asshole, warming the k-y lubricant. Ok, this wasn't so bad, so far! Next, ever so gently, I could feel her probing finger inside my asshole. I was surprised how easily she could slip her finger in and out of me. First, she used one finger, then two fingers. She rubbed my prostate, and Boy, did that feel good! I wasn't scared anymore, and started to relax.

"You are going to give yourself to me completely!" Destiny said.

And with that, she slowly inserted the dildo in my ass. I was ready for it, and it slid right in. At first she fucked my asshole very slowly. She started to fuck me harder and deeper.

"You're not a virgin anymore, slave!" Destiny said.

I wanted all of her dildo, so I begged her to fuck me as deep as possible. And she did! The dildo disappeared in my ass with every stroke!

She withdrew from my ass, changed the condom that was on it, put a new one on it, and rubbed the dildo on my face. I would have sucked it, But there wasn't a hole in the mask for my mouth. I begged her to put it back in my asshole. She told me to get back into my slave position, and she rammed it in so hard and fucked me so fast that I almost came! I begged her to let me masturbate, and she just laughed. Her laugh was cruel. She just laughed and laughed. The more she laughed, the closer I came to coming. By now I was over the edge, I was going to come without even masturbating! Mistress Destiny was fucking my asshole and my come was shooting out of my cock!