Putting the ad in the paper was simply out of a need for money.
It simply read:
Shemale Escort For Hire
Fees vary depending on your needs and the length of time services are required. By Appointment only.
And was followed by my phone number.
To my surprise my phones started ringing almost as soon as the ad came out.
It has been almost two weeks now and I have had some very interesting calls followed by some very interesting evenings but last night was the best so far.
I followed his instructions to the letter. At exactly 7pm I was unlocking the door of the pent house that he had reserved. Once inside I found a note on the kitchen counter instructing me to make two drinks, one of my choosing for me and the other a whiskey sour for him. I was then to put on the clothes laid out for me on the bed and then sit in the brown chair facing the window and wait. When I heard the door I was not to get up or turn around. If I did not follow instructions to the letter, I would have to refund his money, and he had paid a pretty penny.
Sitting there waiting for him my dick was rock hard from anticipation. I didn’t wait long and the door was opening.
I heard him walk to the kitchen and pick up his drink. As his footsteps got closer, the smell of his cologne filled the room.
He stepped into view and got on his knees in front of me. Without a word he took my hard cock into his mouth and began sucking it like his life depended on it.
Just when I was about to cum he stood up, took off his pants and boxers and straddled me, sliding my dick into his tight and already lubricated ass.
He went achingly slow and I could tell that this was the first time anything had entered him.
Finally, after what seemed like ten minutes at least I was balls deep inside him.
He didn’t move at all but leaned over and kissed me full and deep on the mouth before grinding in small circles on my cock and making me explode inside of him while he exploded in between our bodies.
Without a word he got up and put his boxers and pants back on. He handed me an envelope and walked out of the door.
In the envelope I found a note saying he would be in touch, and to enjoy the room for the rest of the evening, along with five hundred dollars for dinner.
Tag Archive: suck my tranny dick
Shemale Escort For Hire
A Brand New Sissy
A brand new sissy has arrived. She came to me on Christmas with her Christmas wish to serve a sexy shemale as a bottom loving, dick sucking, submissive sissy. She sat, hands folded on her lap as she told me how miserable it was to live as a man when inside all she wanted to do was wear pretty clothes and serve a beautiful shemale. She begged me to take her as my own. How could I refuse? New Year’s Eve will be her coming out. Until then we have a week of hard core sissy training to prepare her.
Suck my Dirty Dick
Suck this big cock. Smells like leftover pussy, doesn’t it? That’s because my BBC lover allowed me to fuck his fine, firm ass. I pulled my fuckstick from his cummy asshole and didn’t even wash it. I wanted it to be nice and ripe for your first training session. Since you are such a sissy little cocksucker, I knew you would love to be forced to suck the slime from my big shemale cock. You are one dirty little faggot but you are so obedient. Last time I made you slurp the dirty cum from my pussy and then allowed you to fuck my well used cum pit. You whimpered and whined as you ate that ass but you were so turned on that you went balls-deep into my turd tunnel. Humiliating you just makes you so damn hard. You know you can’t resist the lure of a dominant shemale, the taste of my cock, and the way that I own your fairy ass. On your knees, slut, cause it’s time for the lesson to begin.
Coming Out Party
My nephew has wanted to come out for some time now but we live in a small town and people talk. Now that high school is over and college is in a big city he is finally ready to live as the woman that he has always wanted to be. He has started taking hormones and breasts are beginning to develop, facial hair is disappearing and the transformation is not something he can hide anymore. Tonight is the big night and Cookie is making her debut. We are having a huge party at my house and I have invited several of my tranny loving friends so that Cookie can get her cherry popped as the woman that she is. It is going to be so exciting and I may even get a piece if her myself!
Santa HO cums tonight.
Ready for a little ho-ho-ho in your life? Or would you rather be my HO? I love training new faggot-sluts to accept what they really want for Christmas. Come sit on shemale Santa’s lap and tell me you’ve been a good little sissy. Good boys get a special candy cane from Santa. Bad boys get to suck Santa’s asshole. This Santa has a whole lotta goodness in his sack. How about a taste? Christmas is my favorite holiday, bouncing little boys on my lap and it looks perfectly normal. My favorite is dressing like Ms. Clause in a sexy Santa suit. Red velvet and patent leather belt and heels. White fur trim and a red lace thong. When a bad boy dares slide his hand under my skirt, he gets a great big candy cane surprise. Let’s do a call and make Christmas cum early.
Santa’s Helper
Extra money is always a plus so when i saw the ad for Santa’s helper at the mall I jumped at the chance. The first day on the job was long but Santa was more then jolly. Underneath that cotton beard was a sexy ass man that had my helper cock hard all day long. All I wanted to do was sit on his lap and show him a shemale surprise. I wanted to give him a gift of my own, my dick in a box all gift wrapped and ready to be opened.
After our shift I couldn’t help sneaking a peek at him changing out of his red suit and into his street clothes. His rippling muscles were to much to resist.
Throwing caution to the wind, I walked up behind him and started rubbing his shoulders.
He leaned back into me with a moan and I know he felt my hard dick on his back, but he didn’t seem to be phased by it.
Suddenly he turned his head and put his mouth on my hard dick threw my skirt and his hand reached back and cupped my tit.
Merry Fuckmas to me!
A special gift to open.
Did you wake up hard dreaming about sucking a teenage tranny cock again? Maybe it’s time that we get together and I show you what it really feels like to sink your cock into a tight young school girl ass, especially when it has an 8 inch meatstick attached. Yes, I look like your average hot teen, complete with braces, but when you pull up my skirt, you discover my dirty secret. A throbbing cock that needs some virgin ass-pussy to penetrate. I can fuck for hours and I will fill your new boy-pussy up with loads of cum. I wanna see strands of cum hanging off your chin, and you, on your knees, begging for more.
So stop the fantasy shit and come talk to the real deal. I’m a switch hitter so I can play top or bottom. Gentle or rough. You make the call and I will whisper my naughty secrets into your ear. Let’s jerk off together.
Tranny Phone Sex
Tranny phone sex on your mind? Does my body turn you on? My big fake tits and my big dripping cock makes your cock hard. I am a sexy woman but I also have a cock like a man. You love getting your dick sucked and you love fucking a whore in the ass. So why don’t you get on your knees and rub my cock around your lips. Give the head of my cock light kisses. Take get the fat mushroom tip into your big dick sucking lips. Run your tongue around the rib of my dick head. Flick my piss hole with your tongue. Slowly take my cock deeper in your mouth. Rub your dick as you suck my cock. Take it slow and enjoy your first time sucking a cock. I can’t wait to fuck your tight virgin ass.
Silly Sissy
Being a gorgeous transvestite shemale that surrounds herself with other equally fabulous and superior females means we have standards. So when a cross dressing sissy walks into the club, trying to look marvelous but falling so short, I can’t help but feel sorry for her. Some of the girls tease and humiliate her. They laugh and joke about how she looks like a wanna be queen. I felt so sorry for the poor dear that I took her home with me to give her a make over and some tips on how to be a true woman, even if she didn’t have tits yet. When I saw the transformation that I created, my dick got so hard that the pre-cum was oozing out of it before it was touched. She looked in the mirror and twirled smiling from her lips to her mouth before dropping to the ground and giving me the best fucking blowjob I have ever had! I fucked her deep into the night and found that she was still beautiful, even with her mascara running and her lipstick smeared.
Let me break that ass.
I spread your ass cheeks to look at your puckered boy pussy. It is tight and I know that you are an anal virgin. There is nothing I like better than breaking in a new slut. Especially a straight guy who says he doesn’t want cock. You KNOW you want it, think about it, crave it. You can’t wait to taste my cum. You beg me to break you in, fuck you, use you. All of you newbies say this. You can pretend, but the way you look when you first see my ladyboy cock tells me differently. You mouth opens eagerly as your own boner throbs. Suck my big cock, sissy boy. One taste of cum and you’ll never be the same.