My Dominant Sissy

With the news that one of our largest customers, a clothing company that specialized in apparel for the black urban hip hop scene, was considering going with a marketing firm that was more in touch with there target market, Anthony and I were chosen to go and try to save the account. I had worked my way up the ladder (Director of Marketing) with the company over the last couple of years, while Anthony was a relatively new to the company. Anthony was hired for his uncanny since of style and had really impressed the company with his work with the ladies product line clients that we provided PR and marketing for. Anthony seemed to “really” be in touch with his feminine side and while no one knew of his personal life, the 5’5 chubby clean-shaven 26 year old never intimidated anyone with his since of masculinity.

The trip started all right as our plane took off on time and during the flight we reviewed some of the clients past marketing pieces and Anthony began to offer his visions of what would really work for this client. As usual his ideas were right on target. He even brought along some test photo shots that he and his photographer had put together. The ads were past sexy!! All of the ads featured sexy black women of all shapes and sizes in extreme high heels scantily clad with wild colored makeup schemes. I got a little warm looking at them. I then commented, that I a sexy sista in open toed high heels with juicy lips make me weak in the knees and Anthony commented that he was also really turned on by the same. Maybe Anthony wasn’t as feminine as I thought…

We landed in New Orleans, grabbed our luggage and caught a cab to the hotel. Upon checking in we were told of a mix up and that only one room was currently ready and that the other “should” be ready within the next couple of hours. It was only 2pm so I didn’t think that it would be a problem so we took our things up to the available room. Anthony had some work to do for one of his other clients so he decided to stay I the room as I took a little stroll through New Orleans. After several stops and drinks I returned to the hotel at about 6pm. I stopped at the desk to see if my room was ready. Not a chance, it wouldn’t be available until tomorrow…at least the one room had two beds. I made my way back to the room. Anthony was in the bathroom and after 2 minutes or so; I heard the shower come on. I laid down on one of the beds and started to dose off. I was awakened by Anthony’s voice… “So what do you think of this?” I sleepily rolled over to see a sexy full figured sista in the sexiest outfit I had ever seen. Whoa! “So I take it you like the look” the voice of Anthony spoke again.

Anthony!!! Is that you? You look just like a sexy woman. Call me Toni, and hell yeah; it is all me and tonight I am going to be more than a woman. I then noticed the very long but slim black dick hanging out the leg of “Toni’s” thong. As Toni started to walk toward me I started to sit up. Don’t get up!!! Toni said in a very assertive voice. Somehow the strength in his voice and the swinging of his black dick memorized me and I didn’t move. Toni sashayed over to me and lowered his face down beside mine and said I am going to show you what sexy “really” is. Without warning Toni cupped my balls through my pants and gave a firm squeeze. When I went to let out a gasp, my lips were met by Toni’s and then his/her tongue was searching for mine. I found myself kissing her back…. I then tried to break away…Toni, with a stern look said don’t stop momma from having fun. With that she shoved her tongue back in my mouth and roughly kissed me. My mind wanted to run but my dick suddenly went rigid. Toni backed off and “ordered” me to take off my clothes, pants first. I didn’t move fast enough so Toni firmly squeezed my now sensitive balls. Hurry Up!!! I quickly removed my pants and started on my shirt. My reward for working faster was the full thick lipstick covered lips of Toni, engulfing my dick. What a feeling, I was on my tippy toes as she brought me right to the edge and stopped. Toni backed off my dick and I tried to force her head back on me when she violently slapped my ass. “I control this dick, you will cum when I “let” you cum. Now turn around, mamma wants to see her new pussy!

Wait a minute!! I said before her hand crashed down on my ass once again. Didn’t I say momma was in control of this? I turned around quickly; mamma then proceeded to spread my ass cheeks. I felt here hot breath and then the most unbelievable feeling I had ever felt as her tongue started licking my hole. My knees buckled and I almost fell over. Toni held my hips tightly as she began to work her tongue into my ass. She worked my ass until I was bucking back at her like a bitch in heat. She suddenly stopped and pushed me onto my side on the bed. I was still shaking with excitement when Toni, shoved her 9 in long but thin dick in my mouth. It was already rock hard. Toni said you had better make it wet so I don’t do damage when I put it in my new pussy. She must have noticed the look of horror in my face as she said don’t worry, mamma loves to make a pussy purr. You will be begging for it before the night ends. With that she rolled me on my back and pulled my legs up over her shoulders. “ I want to see your face when you start falling in love with my dick”. She grabbed a tube of lube and oiled me up good. She put her dick at the entrance of my ass and started applying constant pressure. I didn’t think it would go in until my ass suddenly opened up and let the head in. I was experiencing some pain but Toni eased the pressure until I was breathing easily again. She slowly eased more and more of her dick into me. She told me she loves masculine men cause they can take the pain long enough to let it feel good. When I got comfortable with her size she started gentle fucking motions. Her efforts got stronger and stronger until she was fucking me with unbelievable force. I began my bucking again as I felt my cum building in my balls. Toni started playing with my nipples and that was it…I shot cum all over my own face. When Toni saw the cum shooting she pulled out and added here own load. Mamma cleaned me up and I dozed off. I was awakened by Toni’s ragging hard-on at the crack of my ass. I rolled to my side and let her enter me. Toni forcefully fucked me 3 more times that night and I loved ever inch of it. Toni decided that she should meet our customer while in drag the next day and even though I was not sure it was a good idea, I had to admit that she passed so well that no one would know. We went to the meeting and the exotic looking beauty that I brought along more than intrigued our client. Needless to say, Toni saved the account as all I could do in the meeting is look at her sexy painted toe nails in here open toe high heeled shoes during the meeting. We stopped at a restaurant after the meeting for a bit to eat and after the waiter took our order I turned to Toni and passionately kissed her. After the kiss Toni looked right into my eyes and said, now that’s mammas baby. 

Anthony was the most talented designer we had at the firm and after a year of success with our firm he became Toni full time. Our clients only know him as a sexy full figured woman and the rest of our employees see him as a feminine gay transgendered boy, but when Toni comes into the office in sexy open toed high heels, I know I am going to get fucked by my pretty but dominant girlfriend.