Working as a tranny escort is my favorite way to earn money and get lots of cock, at the same time. I love to put on sexy panties and show off my body to men, so it is a job I enjoy doing the most. The fact that lots of men really like me and call me back again and again makes me feel wonderful, as well.
I have long hair that makes me look like a woman from behind and my breasts are big for a man's and they get played with and sucked on like a woman's. In fact, most of my clients tell me I'm more feminine than their wives, girlfriends and secretaries.
They say that clothes make the man and when those clothes are a sexy little pair of panties, a matching bra, stockings, garter belt or a g-string, the clothes make the man feel like a woman. And that is how I prepare for my dates as an escort, by slipping on sexy lingerie, doing my nails, hair, make-up, lipstick, eyeliner and shadow and putting on some perfume.
For this date, I also wore a skirt and blouse and high heels. The client wanted me to come to his office and pretend I was his sexy secretary and strip for him. The fact that he wanted me to sit on his desk while he sucked my cock good sounded very appealing to me.
It was late in the afternoon when I showed up. He had already sent his real secretary home for the day. He was seated behind his desk with a pornographic magazine on it open in front of him and his pants were down and his cock already hard. This would be easy, I figured. I could just strip for him and give him a good blowjob then let him blow me before getting my money and leaving.
My plans were changed when he opened a desk drawer containing lots of dildos and vibrators. It turned out that my client was an ass man
who wanted to use his dildos and vibrators on my ass. While I had nothing against using dildos and vibrators, I normally did not do it seated on a man's desk in his office while he blew me at the same time. But that was how my day was going to go.
Walking into the office to meet my client and seeing him reclining back in his big chair with a porno magazine on his desk and his boner in his hand was a first. Usually, I had to make the client hard by showing him my body. But with Greg, he had already been looking at the sexy female bodies in the nudie magazine to get turned on for me.
"Hi, I'm Courtney. You must be Greg."
"Yes, I'm Greg. But I want you to call me sir." said Greg.
I looked down behind his desk at his boner he was holding. "Is there something I can help you with, sir?"
"Yes," he said smiling. "I was just looking at this girly magazine and it doesn't show enough hot ass in it. I'm an ass man and I really need to see some sexy ass. I thought maybe you could sit on my desk and show me your ass and let me play with it."
I was certain he would have wanted a blowjob as hard as his cock was, but since he was an ass man I was ready for another type of experience. Ass men always want to end up fucking you after they are done playing with your ass. It is quite different than men who just want to exchange blow jobs after some hot foreplay.
I walked behind Greg's desk and was instantly turned on by his big boner. It was 10 inches long and nicely shaped with a big head on it. I stood with my back to Greg and pulled up my skirt, showing him my nice ass ckeeks hanging out of the black lace thong under my matching lace garter belt. The smile on his face told me he was truly an ass man and he especially loved it when I lowered my ass and rubbed it all over his big boner.
"Baby, you want to get fucked, don't you," said Greg.
"Well, you're the one with the big boner, sir," I said with a sweet girly voice. "I'm just following your lead."
He was looking at my hot ass and then down my legs at my black stockings.
"Baby, I think I'm going to love fucking you with my big boner. But not now. You're such a slutty secretary, I might have to give you a big bonus so you want to work for me some more."
"Anything to please you, sir," I said, as I unfastened my skirt and let it fall to the floor.
Next, I started unbuttoning my sexy white blouse. Normally, I would show off my black lace bra through it for a man. But since Greg was already turned on by the girls in the nudie magazine, I was letting him see my body sooner. I get turned on looking at men's big cocks, so already my little clitty dick was fully erect and starting to leak fluid like a little pussy.
When I finished unbuttoning my blouse, I picked up the porno magazine off Greg's desk and pointed at the picture of the girl's ass Greg had been jerking off to when I came in.
"Do you think her ass is nicer than mine?"
"No. I think your ass is nicer," he said.
He reached out and felt my ass cheek like a man petting a puppy.
"Then why are you wasting your time wanting to give your cum to girls like her when you can give it to me, your horny secretary who wants all the cock you can give her."
"Oh, I want to fuck you so bad," he said.
"Baby, every man does," I replied. "I think you're really going to like me as your new secretary, sir. I'm a cum-loving little slut who can't get enough cock in her ass."
"Oh, I can see you like to suck some cock. You have the right clothes on for it. But first I want to suck yours while I play with this nice ass. Sit up on my desk and spread your legs for me, Courtney."
Part of the fun of being a crossdressing callboy escort is getting to act out my clients' fantasies. And when their fantasies involve sucking my dick while they put a vibrator in my ass, I love it. I gladly did as my "boss" told me and sat on his desk, putting my ass and shaved cock poking through my tight panties right in front of him.
Greg opened the top desk drawer and it was filled with dildos, vibrators and butt plugs all shapes and sizes. There was a six inch vibrator and a big flesh-colored ten inch dildo. I picked up the silver eight inch vibrator called The Silver Knight. It reminded me of the first vibrator I bought when I was 17 and wanted to feel like a girl with a big cock inside her. I would lie in my bed at night and put it in me with Vasaline and love feeling like I was being fucked by a man. Now, I had those same feelings knowing I was about to be fucked by Greg.
"This one will get me ready for you, sir" I said.
Greg smiled as he took the cock-shaped vibrator from me and reached for my sexy little blck panties to pull them down. My shaved dick was already hard for him ever since I saw his big ten inch cock.
"You probably think I'm a slut because I got turned on when I saw your hard cock."
"I've always wanted my secretary to be a slut," said Greg. "I'm glad you are a slut"
"That vibrator looks good and I'm sure it will get me ready for your big cock, sir. I'm going to enjoy being your secretary."
When Greg pulled my little panties down and saw my shaved dick, he immediately licked his lips. He undid my garter snaps so he could pull my panties all the way down to my ankles. It felt so girlish having a man preparing me to be fucked.
I looked down at my new lover/boss' ten inch cock and saw it was still rock hard. Oh, it was going to feel so good, I thought. First, a nice eight inch vibrator in me and then a big hard ten inch cock. This man was truly an ass aficionado and I felt like a lucky girl.
"I love getting a fresh ass," said Greg.
"Baby, I like giving at the office. I'm gonna love being your secretary."
It was true. As a callboy, I sometimes had clients have me come to their office. These were usually handsome, married men with really big ones. Being a sexy slut who loves big ones, I was always happy to go to a man's office for the purpose of pleasing him. Now, here I was with a handsome man with a ten inch boner who couldn't wait to get me ready to put it in me. The pleasure of my profession was occuring to me.
The thing with these office romances, the men were so handsome, well-hung and successful, they often made me wish I was their sexy little wife waiting at home in her sexiest lingerie for him to spend the night with, every day. I could think of my fantasies, too.
Sitting back on his desk with my legs spread for Greg, I watched as he put Vasaline on the tip of The Silver Knight, an 8 inch vibrator and put it up to my ass. I braced myself for impact as the big, silver, cock-looking device entered my tight little ass.
"Ohh, yeah," I said. "That feels good, sir."
Greg smiled as he worked the full 8 inches of the vibrator inside me. "Tell me if this feels good,' he said.
He leaned forward and took my entire clitty dick into his mouth and started sucking me while he worked the vibrator around in my ass.
"Ohh, yeah, honey," I said. "I love it."
Here I was getting paid to get my ass reamed by a big vibrator and my dick sucked by my handsome "boss" and I was the one getting paid. I really do have a wonderful job, I thought. And the best part was that I was going to have Greg bend me over his desk and thrust his big 10 inch cock inside my tight little ass very soon.
This was so sexy on so many levels. There was the fantasy about being a sexy secretary having sex with her boss, there was the thrill of being paid to be a call girl with her client, and there was my own sexy fantasy that I was Greg's hot wife who got his cock every night. Oh, I couldn't wait to feel his cock inside me.
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<a href="https://www.lushstories.com/stories/crossdressing/the-sexy-secretary-gives-at-the-office.aspx">The Sexy Secretary Gives at the Office</a>