I was sitting in the living room, watching movies with hookers that were fucked in all imaginable ways, and I was slowly playing with my dick! My excitement was so big that I decided to make one of my wildest fantasies to come true: to spend a night as a hooker!
My dick went stiffer to the idea; my girlfriend was at her parent's house away for the weekend, so everything was ideal! I went to the bathroom, and shaved my legs, balls, ass and my whole upper body. I took special precaution shaving every last piece of hair so that I had a nice soft and smooth skin. I used a lotion that my wife used after shaving, and the results were fantastic. Nice soft skin and the smell completely feminine. I stuck my but on the tap, and managed to get some hot water inside, which I pushed out emptying my bowels and cleaning my ass completely. I slowly inserted my index finger inside my butt, and it felt like heaven! Clean, soft, so smooth and smelling so female, so nice!
I got out of the bath and went straight to my personal collection of panties and lingerie from my ex-girlfriends, which I keep well hidden in the garage. I usually sniff and even taste them getting the natural odor and taste of all my past girlfriends inside my mouth, while I masturbate with my dick. But this time it was so different. I chose the most soiled one's I had, a white laced g-string from a very juicy woman I was fucking for more than a year. I pulled it up until it disappeared inside my butt crack. My dick and balls were squeezed firmly against my belly. The laced string was rubbing against my asshole quite annoyingly as I tried to walk and frankly it felt pretty uncomfortable, but I didn't care at all.
I put on a pair of long black stockings with their garter belt, and above of these a black mini skirt from the laundry of my girlfriend I also took her higher heel shoes and put them on. I looked my ass in the mirror, and tried to imagine that it was a lady's ass. It looked very good, and I pulled the skirt up as far as I could, making sure that a glimpse of my white panties could be seen as I walked. My dick almost exploded while I was looking in the mirror my firm ass and panties, under the skirt! I have long legs, with a round firm butt, and the sight of my shaved ass-crack with the white lace protruding right in the middle of it made me horny as hell.
I put on a dark black wig, a bra, and I was ready to hit the road! My heart was beating like crazy from the anxiety, but I was determined to make it real this time! So I took the car and stopped at a famous street where men could find transsexual prostitutes. I parked my car near by, found a good spot and waited there, pretending to be speaking to my cell phone.
Soon enough a car approached, and a young boy inside asked me about the price. He was looking pretty embraced but he just wouldn't take his eyes off my thighs and skirt. I was flattered, and I responded that I wanted 100 bucks. Actually, I wasn't going for the money, but since I had to pretend that I was a prostitute for real, I played my role. He said ok, and pushed the door open. I got inside, and told him to drive to a hotel. I was sitting next to my first customer, full with excitement, and I decided to behave as the prostitute of my dreams!
I slightly opened my legs, and pushed my skirt up, revealing the garters and the upper part of my stockings, giving him a view of my panties. He was driving and looking between my legs, trying to get the best view he could of my panties. I was feeling so great, so desirable, so much in control! My dick was getting bigger and bigger, and I tried to think of something else than the situation, so that I could make this just perfect.
We arrived at the hotel, and got up to the room. I locked the door beside me, and ordered him to get undressed. He got all of his clothes of and he lied down in bed. He had a thin and rather small hairless dick, with good sized balls, and he was already semi erect. I approached him, and pulled my skirt up, turning around, giving him a good view of my string, buried deep inside my ass, just under my skirt.
"Is this what you want?" I said in a soft voice, as I slowly moved my fingers under the panties, caressing tenderly my ass.
His dick got hard, and I got even hornier with the sense of authority I had over this young boy. I got over him, as I was, completely dressed, with my ass above his head, and my head just above his dick, in a sixty nine position. I slowly opened my mouth and got his dick inside. I started moving my head up and down, while I was sucking his stiff dick with lust. My hand got over his balls, and I softly squeezed them as I deep throated his dick at the same time. I was giving him the blowjob of my life, when I decided to add a little spice to it.
I lowered my ass on his face, and with my hand I parted my panties, giving him access to my asshole. I moaned like a proper lady, and commanded him: "Lick me there, come on, I need to feel you there! Lick me boy, make me moist and ready for you! Suck my soft pussy!"
He stuck his tongue against my anus, and started to lick me, getting a good taste of my ass and my ex girlfriends pussy. His dick went rock hard as I stuck my middle finger deep inside his firm asshole. He was gladly accepting it more and more, and he suddenly exploded in my mouth, giving me a thick load of cum, which I immediately swallowed, while at the same time I was squeezing his prostate, milking him inside my mouth. I sucked him dry, and swallowed every last bit of his cum, just like my wife was doing with my own. I let go of his dick as it was now very small, and sat over his face, rubbing my ass up and down, back and front against his mouth, really enjoying the feeling of getting my asshole sucked.
I got up and removed my skirt and panties, revealing the full length of erect penis, hidden inside the lingerie, but I was still wearing my garter belt and stockings and my high heel shoes. I was going to be dressed like a lady for the rest of the night.
My ass was soft with his saliva, ready to be fucked, but his dick was still a limb. I tried to give him another blowjob, but with no success. His orgasm was so big, that it would take a lot of time before he could get it up again. I was very frustrated as I was urgently needed a good fuck back there and my dick was hurting me pretty badly.
"Let me help you with that" he said, to my amazement, grabbing my erect dick, and getting it in his open mouth. He was trying to give me a blow job, and I was starting to enjoy the feeling of his inexperienced mouth on my dick.
"You know, I want to become a little bit of a lady myself" he said. He got up, and got at all fours on the bed. "Please be gentle" he continued. "It's my first time, but I really liked the feeling of your finger inside my ass just a minute ago", he admitted.
I got beside him, and started to suck his virgin asshole. As soon as it was soft enough, I placed my dick against him, and gently pushed myself inside. He was completely relaxed, and I managed to get my fully erected thick dick, inside his hot ass, up to its full length. I started fucking him in mad lust, obviously hurting him, but he wouldn't move. He stood still, while his ass was on complete fire, and I was dominating him as if he was the cheap hooker.
He started to moan, and with his hand he reached for my balls. He started rubbing his balls against mine, and I became so horny, that my dick started shooting its load deep inside his busted asshole. I collapsed on top of him, and he sucked dry my dirty penis.
We lied down for half an hour or so, and then he got up, gave me 200 dollars for the extra care, and left the hotel. I got up and went straight for a hot shower. I was more than anxious to get my self cleaned up, and ready for my next client. The night had just begun and I was determined to make the most out of it!
Should I continue with this story? Please mail me with your comments. Thanx for reading! -Jim-