Introduction:
Hi my name is Jason and I’m 19 years old. I was living with my parents and looking for a job and a place of my own. I did have a job but it was just a part time job at some restaurant, just to kill some time.
Anyways, one day my mum called me downstairs and said that Mrs. Fletcher from across the street was asking for me. I went downstairs and there she was waiting for me. Seeing me she said “Jason, hi, I’m going on a business trip for about two weeks and was wondering if you could look just check up on my son while I was gone.” Mrs. Fletcher was actually fairly good-looking with red hair and light blue eyes. She lived alone with her teenage son Sam. Sam was pretty much a quiet kid around 14.
“I just want you to check up on Sam after about every two days so I don’t have to worry about it. I can’t miss this trip and I can’t take Sam with me” she continued. “No problem Mrs. Fletcher” I replied “ill do that.” She looked reassured and said “well then ill get going, thanks again Jason.” I just smiled politely.
When she was gone, my mum came back and said “well well, look who’s getting responsible here.”
“Hey it’s not my problem that people find me responsible.” Actually I’m 6’2” and a little on the muscled side. I was pretty athletic so I’m in good shape.
By Tuesday I had almost forgotten about my commitment when all of a sudden I remembered that I hadn’t checked up on Sam. So after dinner I went up to his house and the lights were still on. I knocked and nobody answered. Since it was pretty early so he couldn’t be asleep and there were faint sounds coming, like people talking. I cautiously opened the door and went inside. The living room and ground floor was empty so I decided to check the bedrooms.
When I neared the stairs, the sounds I could hear were getting especially suspicious. Needless to say that I decided to investigate. The last bedroom on the landing was open and light was streaming out. The sounds were unmistakably of sex, moans and grunts. And there was the sound of a paddle being hit on bare skin.
“Take it slut; take it deep in that fucking mouth. I want it all slick when I push it deep into your poopchute.”
“oh shit!” I thought “this kid is in some serious trouble”
I inched closer, looked around the door and thank my lucky stars that I hadn’t called 911 then.
All those sounds were coming from a plasma screen that showed a man plowing his huge cock into the mouth of a girl. I almost laughed out loud but caught myself just in time. Sam was lying on the bed and luckily he didn’t hear it neither could he see me as he had his back to me.
But as soon as I focused I realized what he was wearing and I was shocked beyond measure. From the back I could see hair streaming down his back and the straps of a bra. As if on cue the man and the girl on the porn flick changed angles and I realized that it wasn’t a girl at all. It was a tranny.
I consider myself straight but I’ve always had a fascination with trannys. Maybe it’s the taboo part of it. With time this fascination grew and included transvestites. But the only problem was that I found only feminine transsexuals appealing. I just wasn’t attracted to a guy in a dress. She had to be really feminine.
Needless to say that I could feel my cock stirring in my boxers. And almost on its own accord I reached into my pocket and took several pictures of Sam from behind. I slowly moved back into the landing and took a deep breath. This was an opportunity that I couldn’t miss.
I took some heavy steps and moved into the room. When I entered, he was just turning off the plasma TV. I stopped dead in my tracks because Sam had actually make up on his face and he had done some damn good job. He lips looked plump and a succulent red and he had smoky eyes and a little blush. He was standing there with his mouth open and holding a dildo in his hand that look slickened.
“What the hell is going on here” I yelled. “Who the hell said you could come in asshole” Sam screamed at me. “Your mom” I replied almost calmly “guess she didn’t realize what a little tranny whore you are”
By now Sam was standing on the far end of the room and the gravity of the situation had started to sink in. He had tears in his eyes and was muttering “shit, shit, shit” under his breath. “You want to explain any of this?” he looked at me fearfully and said “please don’t tell anyone”
Feeling pretty much in control I moved into the room and said “that depends Sam. If you do as I tell you nobody will hear anything about this.” He looked pleadingly at me and said “please ill do anything.”
As I moved into the room I gave Sam a once over. He was wearing red glossy lipstick and a black wig, red bra and matching stocking. 3” black heels completed his look. By now my cock was fully engorged and blatantly on display as a huge bulge in my jeans. I sat down on the edge of the bed and motioned Sam towards me. “Sit” I said patting on my lap. He looked at me apprehensively and thought better of it and gingerly sat down on the edge of my lap.
“Not here, sweetheart” I said, grabbed him around the waist and lifted him plop onto the middle of my lap. “What do you want?” he whispered fearfully. “Well baby, I have two rules and if you follow those two without question you don’t have to worry about your secret, and if not, well the lets just say that school wont a pleasant place and of course how you’ll explain it to your mum.”
“The rules are
1. You will never say to no to me
2. You will always speak in a girlish voice”
I said while stroking the inside of his thigh.
“Okay” was all he could muster.
I stood up and grabbed him around the waist “well baby, from now on you are Samantha for me”
I stroked her back and felt Goosebumps all over her; I let my hand wander down and cupped a cheek of her ass. It was plump and full with a little bounce in it. Suddenly the need inside me seemed to double I pushed her against the wall and pinned her body between me and it. I could feel every contour of her body as I pressed against her. I could even feel her heart racing and her breath starting to quicken.
I grabbed both her hands in one of my own and put them behind her back. I cupped her flat chest and pinched a nipple through the bra. It hardened into a nub at my touch. I pinched it and rolled it between my thumb and forefinger, making her moan with the pleasure and pain. I took off her bra and flung it aside. Her small pinkish brown nipples hardened due to the cool air. I tipped her head back and pressed my lips against hers. Her lips were soft and tasted of cherry. Slowly she parted her lips and I forced my tongue into her mouth and soon our tongues were dueling with each other. I let go of her hands and grabbed her ass. While she put her hands around my neck to pull herself up to me. I pulled her to the bed and threw her onto it. I spied a stocking sticking out of the closet and pulled it out. I caught one of her legs and pulled her towards me. Pushing her face down on the bed I pulled her hands together behind her back and tied them with the stocking. She had been complaining the whole time so I gave her ass a hefty slap and said “remember the rules, bitch”
I slowly took of my clothes and when she saw my 7” cock spring out her eyes seemed to be glued to it. I lay down on the bed and told her to service my dick with her mouth. She was eager but a little clumsy. I couldn’t believe that this was the first time she was sucking cock because she didn’t seem a bit disgusted. Rather she seemed to be enjoying and I was definitely enjoying watching her plump lips go to work on my throbbing manmeat.
Picking up the bottle of lube from the nightstand, I straightened up and said “its time to take your cherry, baby”
I put a healthy amount on my dick and pulled her towards me. I parted her ass cheeks and there was the treasure. I squirted some lube up her poopchute and some onto the brown starfish. I slowly inserted my middle finger into her and met little resistance. Apparently she had had a little ‘practice’ before no doubt with the dildo. I easily worked two fingers into her and began reaming her out. By now her little 4” clit was fully erect and she was moaning deeply.
Took out my fingers and put her in doggystyle position and I mounted her. “All right bitch, I want you to relax and push your fucking asshole out.” There was a fair amount of resistance but after a mighty push I managed to push my cockhead inside her sphincter. Immediately the ring closed around me like a vice.
Slowly I managed to push all 7” inches into her and had my balls resting against hers. I slowly pulled out and pushed in home. The heat from the rectum was almost scalding and her ass was holding on to me so hard that some of her asshole would be pulled out when I pulled out my cock. Slowly we built a rhythm and even my little bitch started to get verbal.
“Fuck my ass. OH OH OH OH. Yesssssssssss GODDDDDDDD YESSSSSSSS OHHHHH FUCK”
I pushed down on every down stroke so that I hit her prostate and she would buck underneath me. I pulled her up so that we were both on our knees and started kissing and licking her earlobe making her moan. Turning her head I pushed my tongue into her hot mouth. I could feel her moan as I started twisting and pinching her nipples.
I grabbed her engorged clit and her ass tightened even more around me. Slowly I started jerking her little clitty. With my other hand I made a little noose with my thumb and forefinger and encircled her balls, pulling them away from her body and squeezing them. I could feel the tightening in my balls too and knew that I was about to cum.
I pulled away from her mouth and whispered in her ear “do you want to cum baby doll?” she replied in a small girlish voice “please make me come” I suckled her earlobe and put my tongue in her ear. As soon as I did that she started to shudder and I felt her ass squeezing my cock in spasms, which tipped me over the edge into orgasm oblivion.
Both of us fell onto the bed, I rolled over still embedded inside her and rolled her onto me. After catching my breath I realized that Samantha had fallen asleep over me so I reached for my cell in my jeans and called my mom to tell her that I wouldn’t be spending the night at home. Then I pulled the covers over both of us.
This fortnight looked really promising.

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