So let's recap shall we.
I'm a 38 year-old transsexual hooker. A 23 year-old military boy is standing at full attention, shirtless in front of me. He wants to pay to have his first sexual experience with a man. He picked me.
I pinched myself. Nope, not dreaming.
What the hell is going on here?
Ok, I can admit, I have had a few young ones in my career, but they either want a girlfriend with a dick or a mama with a bank roll. Both of which I am neither. This kid is totally legit. He had the money upfront, even paid more, and was ready for business. Chris knows more then he is letting on. Not to say that I am not going to enjoy this for a change, but mama needs a new dress.
Chris was still standing at attention awaiting his next order. The water had left a trail on his chest. The top of his pants absorbed the remaining liquid. Each of his muscles were taught able to react in a split second. He was not a Muscle- Mary, but lean and well defined nonetheless. I could just start to see the goose bumps start to form on his arms. I stood up from the love seat with a quick snap. He didn't even flinch. I walked around Chris inspecting every inch of his body. As I reached his back, I took my hand and placed it less then a millimetre from his skin but did not touch him. I felt the heat from his body travel through the thin strip of air to my hand. The goose bumps got bigger as I moved my hand slowly over his back, not allowing my hand to touch him. Not allowing Chris to touch me either. This was my game. His breathing quickened and his shoulders quivered slightly, held back by the restraint of his training. I had a feeling that he wanted to forgo his training. I looked down at the olive military jacket and hat. Let's take this game up a level.
“Soldier; Stay here while I get comfortable.”
“Yes Ma'am.” He respectfully snapped.
I scooped up the jacket and hat and headed to the bathroom. From my vantage point, if I opened the door slightly, and angled the medicine cabinet mirror, I could see Chris' standing profile. I had to keep an eye on him; I didn't trust him that much.
I began to undress. Removing my black dress shirt carefully, hanging it on the back of the door and clinking the diamond cufflinks in to the dish on the back of the toilet. I shimmed out of my black skirt and nylons and let them fall to the floor. Thank god I shaved today. I peered up at the reflection of the young man in my mirror. It was like a still-life portrait. He was perfectly still. I figured as much. Chris, in his own mind, did not want to piss me off. That was evident. I checked my tuck and made sure I was as presentable as I could be in my body slimmer and panties. I slipped the jacket on and looked at myself in the mirror on the back of the door. It fit perfectly and it sat just below my mid thigh. It covered just enough. I quickly flipped my wig from a pony-tail to a tight bun. As I adorned my wigged head with the hat, I felt like an air of authority was being passed on to me through the generations of women (and men) before me. That's much better, I thought. I looked myself over once more in the mirror and though this outfit would be fabulous for the Miss Gay Canada pageant and Bette Midler's boogie-woogie bugle boy!! I flipped on my heels and headed back to the living room. We'll save that for later, back to my guest.
“Well Soldier, how do I look?” I coyly questioned Chris, fully knowing the answer.
“Amazing Ma'am!” His eyes were as big as hubcaps on a brand new Jag.
“ Thank you, Soldier.” As I spoke I caressed every part of his body was my eyes. The front of his water stained pants grew tighter as he stood in my shadow.
I finally touched him and he quietly gasped. I continued my circle drawing my hand around the front of him. I used the back of my hand and gently caressed his shoulder. I drew my hands down his chest avoiding his nipple seductively and brushed down to his firm stomach. I held my hand there and felt him breathe for a moment. I lifted my head and looked him square in the eyes. He looked back .
“ Thank you ma'am ” he quipped quietly.
I stepped back from him and admired his youth and maturity in one descending gaze. I thought of a plan of action, smiled, and made my move.
“ Ready to play soldier ?”
“ Yes ma'am ready if you are ma'am ”
“Are you talking back to me soldier ?” I snapped.
“I wouldn't have asked you if I wasn't!” This is starting to be fun, I thought. A chance to be bitchy and get paid for it. Life is good
“ Sorry ma'am I didn't mean to offend to ma'am. It won ' t happen again ma'am”
Chris stood even more rigid than before. It was as if he had a poll running up the length of his body, inserted somewhere inconspicuous. How did that get there? I pondered as I chuckled in my head, O.K. It is time to get back to business.
“G o get me a stool from kitchen soldier” I stoically stated.
“ yes ma'am ! ”
Chris broke from his stance and scurried to the kitchen. He grabbed the stool from the breakfast nook at the other end of the kitchen and hustled back to me. Wow , I wish you with your all the time , I thought. He stood ridged once again in front of me holding the stool in mid-air.
“P lace It' s over there soldier ” . I ordered and pointed to the front of the loveseat. I spoke with an annoyed tone.
“ Yes ma'am ”
Once again, he sprang into action like a deer bounding through and open field. He gently, but quickly, placed it down where I had instructed and ran back to his starting point as before, in perfect military stance.
“Thank you Soldier” and before I could finish allowing the words to escape my mouth, he snapped out his response. “Your Welcome Ma'am”
“OK Soldier, ENOUGH!” I commanded. Chris' eyes fluttered as if startled. I walked over to the stool, which rose tall against my side, and sat upon it. I was above Chris towering and maintained my air of superiority.
“Take off my shoes soldier!”
“Yes Ma'am!” exploded from his mouth as he collapsed to the floor, crouching at my feet and clumsily tried to unbuckle my heels.
“Slowly Soldier, I want to enjoy this”.
“Yes Ma'am, Sorry Ma'am”.
“Don't apologize…just do it”
“Yes Ma'am”
I rolled my eyes at the utterance of that word. Was He going to do that ALL NIGHT?? Let's make this more interesting then.
“Use your teeth soldier...no marks on the shoes… do you know how much I paid for these... Can you do that solider?”
“Yes Ma'am”
UGGGGGGGHHHHH
Chris knelt down and placed his mouth near the tiny black buckle of my curved stiletto. To my amazement, he adeptly flicked his tongue and released my foot from its prison. He looked up at me for approval, smirk and all. I winked at him nonchalantly and motioned for the other foot. Within seconds, the other was free at last. Hmmm where did he learn that? I thanked him by rubbing his hard crotch with my free foot. By the look in his eyes, he could have came that instant.
He softly moaned as I moved my foot gently up and down on his shaft. I could feel it softly pulse, as he closed his eyes and enjoyed the moment.
“Easy now, we have only just begun.” Immediately Karen Carpenter sprang into my head and began to sing. I shook the thought hard from my mind and gave Chris my full attention. I defiantly want him to come back. I abruptly moved my foot away and in a knee-jerk response, his eyes flicked open as if to say ‘What the fuck?'
“Problem Solider?” I sarcastically asked.
“Ug…No Ma'am…I just thought…”
“No, solider, DON'T THINK…” I pushed him over with my heel planted on his chest. He stared at me doe-eye.
“JUST DO! Do I make myself clear?” I quietly commanded.
“Yes Ma'am.”
“Your job solider is to please me. I will instruct you. Do you understand me solider?”
“Yes Ma'am.” He reeled back from the sting of my words. He crept to his knees and slowly began to rub my feet.
“That better Solider. Very good.”
He scampered up to my calves kneading them like bread dough. Oh JEESH!! Here we go, straight for the crotch. Are they ever going to learn? His hands, as predicted, scurried up my thigh and he pounced on what he thought was my crotch. I spun around on the stool once again shoving him to the side.
“Do I have to show you everything? Stand Up Solider.”
He looked at me sheepishly, knowing that he did something wrong before I even spoke. He slowly rose to his feet and assumed his position. I slid off the stool, now considerably shorter without my heels, and stood directly in front of him. I was mere inches from his body. DAMN! He smells good . I took my hand and placed it on his chest. I felt his heart pound in his chest. I began to caress him gently as before, avoiding his nipple, and moving across his hard stomach. I grabbed the top of his pants and pulled him towards me roughly.
“We need to get rid of these pants soldier. I think you have a concealed weapon.”
“Yes Ma'am.” He quickly reached for his belt and attempted to remove it with hands that had suddenly become all thumbs.
“Allow me.” I cooed knowing full well of what I was about to do could make or finish this date early.
I placed Chris' hands behind his back and moved my hands back around to his hard stomach. I kept my hands in place and lowered to my knees. The prize was directly in front of me. Using my teeth, and trying not to get make-up on the front of his pants, I gently pulled on the loose end of his belt. I pushed it through the buckle and bit the soft leather. I pulled hard on his belt and Chris almost with it. The buckle popped over as the catch loosened and fell forward. I then commandeered the buckle and slipped the end out of it. I looked up at Chris who eyes were so big and glossy they looked as if they were going to pop. I bit the top of his pants and yanked the fabric off of the button in a quick jolt. The only thing left was the zipper, my favourite. I looked up again at the very impressed Chris and winked. I flicked the zipper tab with my tongue and clenched it between my teeth. Following its path, I pulled it lower and the filling behind it pushed forward. I lower my hands and grabbed the top edge of his pants and pulled them down to free his now full erection
“I was right; you do have a concealed weapon. I am going to have to inspect that Chris.”
“Yes Ma'am” he whispered.
I helped him out of his pants and socks and led him towards the bedroom. I still can't believe I am working right now. Hell I would do this one for free…
That statement scared me, only because it was true.
