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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 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” . 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 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.

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Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

1 year ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

1 year ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
2 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

1 year ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

2 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

3 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

2 years ago
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Cum Craved Sissy

Taking a quick look at the clock, I noticed that the delivery had run late, and I was immediately stressed at the fact that Mistress would be home shortly. I knew I didn't have time to shower, and there was certainly no time for much cleanup either. I just pealed the skin-tight jeans down, crumpled them up and buried them at the bottom of the hamper.I carefully pulled the bright yellow panties down my legs, trying not to make any more mess. I washed the creamy jism away in the sink, squeezed...

2 years ago
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Born a Sissy

Born a Sissy This is the story told by me "grandmother" and my grandson Timmy. Most of it is true and only some parts have been modified. It all started back in 1979 when Timmy was only 9 years old. He was a beautiful child that I loved dearly. Timmy's mother, my daughter, had him at the young age of 17. Being so young she was not quite ready to be a full time mother. She was just like any other teenage girl who had social obligations to meet. She was a good mother but I understood...

2 years ago
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sissy

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you!After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in place of course, and returned to the store. Not sure what to expect I walked slowly through the door.The salesladies smiled and said, "Look...

2 years ago
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From manager to sub sissy

Cindy was a co-worker; well actually I was Her manager. Even though I was Her manger, W/we were very close friends. As a matter of fact I still consider Her my best friend. Everyone in the office was sure that we were having an affair, but we were just friends. I must admit that I would have loved to have an ongoing affair with Her. I know that I am not near man enough for Her and I have always know that from the first time I saw Her. Eventually after being friends for many years, I...

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