tagTranssexuals & CrossdressersMy Shemale Stepmother

My Shemale Stepmother

bybritneyfan©

My parents split up when I was eighteen, I was a little distressed by it but we had never been as close as some. Still, I didn't really see what had driven them apart so quickly and so thoroughly that they never even spoke any more. I guessed maybe one of them must have had an affair and that was really all that I thought about it. I went off to college and life went on. That following summer, when I was nineteen, I moved in to live with my dad for the summer. He had bounced back quickly following the divorce and had already found someone new and I had to say, he had done pretty well for himself. Carla was a hot, curvaceous Brazilian model, tall and long legged with olive skin and sun kissed blonde hair. Everywhere she went, eyes turned to follow her ass she wiggled her ass in the tight skirts she loved to wear. There was just something about her, sure she was super sexy but there was something extra special that set her apart from other women, something in the way she carried herself and talked and laughed, so confident of her own allure and sexuality. Where, at first, I was impressed with my dad and how he'd managed to get himself such a woman, it wasn't long before I started to become jealous and began to fantasise about my hot latin stepmum.

Any son who catches a glimpse of their father having sex is inevitably going to be pretty massively effected by it, but for me this event had even greater significance, it was the day that pretty much changed my life for good. I couldn't stop thinking about Carla, she was on my mind constantly. Even at work in shelf stacking summer job, I was distracted all the time by my thoughts of what it would be like to stick my cock deep inside that hot Brazilian body where my dad had been before. I knew it was wrong to think that way about my stepmother but what could I do? I felt like I couldn't control my own mind any more, she was always there. Finally, I decided that no matter what the consequences, I just had to see Carla's naked body, it was the only thought that consumed me.

One day, I got home from my job early and the house seemed empty and deserted, but as I walked upstairs I began to hear moans coming from the bedroom and began to guess what that would mean. Carla would be there, exposed in all her naked beauty, having sex with my father. Before I really knew quite what I was doing, I knew that I had to see this and I quietly tiptoed up the stairs to the door of my dad's room which was slightly ajar and peered through the gap.

I don't know quite what it was that I expected to see but what I did see was certainly something very very different. The scene before me was something that I would never have expected to see in a million years. Sure, in the middle of the room was just what I had hoped to see, Carla's tall, toned body almost completely naked. I had a great view of the curve of her pert, round breasts, her flat stomach and long legs in thigh high leather stiletto boots that made her tower even taller over my father who knelt in front of her and, now this was the shocking bit, was sucking on her big, thick, hard cock, almost twice the length of mine! That's right, my gorgeous new stepmother wasn't a beautiful girl at all, she was a shemale! Clearly my dad didn't have any problem with it as he slobbered eagerly all over her thick manhood.

"Oh, baby, you sure know how to turn a girl like me on," Carla moaned in her thick Brazilian accent, "If you don't watch out I'm gonna cum right down your throat. You'd like that wouldn't you, you dirty little cocksucking sissy?"

"Yes mistress," my father, humiliated by this hot dominant shemale and loving it, replied, taking her cock from his mouth for a moment, "I want to make you cum, I want to drink all your juices as you fuck my throat with your big, hard cock."

I couldn't watch this any longer, it was just too weird. I turned away from the bedroom door and dashed away back to my own room. Well, you would think that seeing this little, or actually rather large, extra side to the woman of my fantasies would make me stop thinking of her like that and certainly, that was what I thought when I got back to my room. But it turned out that this was not the case at all. In fact, seeing how Carla was extra endowed only served to turn me on more. I didn't realise it until I was lying on the bed in my room, but the sight of my father orally servicing the beautiful shemale had given me a massive hardon even as I felt disgusted by it. I couldn't help but jerk my dick off while picturing the much larger and more impressive size of Carla's in think of it violating my throat as right now it was doing to my father.

Over the next few days, my obsession with Carla and her cock grew and grew until I just found myself staring longingly at her wherever she went, watching her feminine figure showed off by the tight dresses she wore and imagining that little piece of masculinity the skirts concealed. At night I would masturbate and these days all I could picture was Carla's cock. Try as I might, though, I couldn't get another glimpse of it for real or another sight of her taking my father. Not in reality anyway. But, what I did do was start to think how little I really knew about Carla, who she was, where she had come from. My dad had told me that she was a model and I had accepted this pretty readily, I mean she was the most beautiful creature I had ever laid eyes on so it wasn't hard for me to imagine her modelling. But now that I knew something more about the real her, I began to wonder just what kind of model she really was. When I was sure that I had the house to myself, I googled her, searching for "Carla Rodrigues" yielding thousands of hits. Why hadn't I thought of this before? My suspicions were confirmed when I had to go through a number of age confirmation pages to get to the sites that I was interested in. Sure enough, here were galleries of Carla the model, posing in sexy, revealing clothes and underwear, and stripping them off to reveal her monster cock. I was getting pretty hard myself just looking at these pictures and the video section was even more exciting. My cock was straining fit to burst against my tight jeans just at the clips of Carla stroking off her beautiful meat but it got better as the videos turned to Carla going down on guys, or more often, them sucking her cock, or them fucking each other.

One video in particular held my attention for many viewings. Carla was dressed in full dominatrix gear, a tight black leather corset and the thigh high stilettos I had seen her in the other day with matching black leather gloves up to her elbows. In her hand was a whip. The man that she was with was chained to a bed, his hands cuffed to the posts of the headboard and his legs tied up to his hands so they were wide open and his ass was pulled up into the air. His smallish cock was pulled up to allow Carla access to his ass, she knelt over him and was fucking him, thrusting her hard cock deep up into his ass. He was whimpering with the pain of his uncomfortable position, her tearing open his ass and her striking him with the whip but he was obviously enjoying it too.

"What do you want, slave?" Carla said in a hard edged voice, striking him with the whip.

"I want you to fuck me harder, mistress," came the reply, "Harder and faster."

Carla was only too happy to oblige, tearing into his ass with even greater vigour and excitement.

"You like that don't you sissy boy?" she taunted, "You just love having your ass fucked like a little girl, like a slutty bitch."

"Yes mistress," the man in the video moaned, "I love to be fucked by your big, throbbing cock, I want to be used as your sissy whore!"

This video turned me on so much that I couldn't help myself, I took out my cock and began to jerk it off. As Carla made the guy cum and from his position of his ass and cock raised up above him, his own cum dripped down into his mouth. I couldn't help but blow my load all over my chest. It was only as the camera zoomed in on a close up of the guy drinking down his own cum as Carla taunted "Wow slave, you even love cum like a slutty whore," that I realised that the man fucked and humiliated in this video was my own father. No wonder my mum had divorced him. Not only was my new stepmum a shemale pornstar but there was my dad up on the internet for anyone to see, begging to have his ass fucked harder by her. It was humiliating and yet I could only feel jealous that it was him and not me getting fucked by gorgeous Carla. Oh well, as it turned out, I would get my chance to star in my own Carla Rodrigues internet video, but we'll get to that later.

First, I need to tell you how I finally ended up fulfilling some of my fantasies and seeing what it would be like being with my hot pornstar shemale stepmother. It was my day off and I spent it, as I spent most of them, lazing around the house, watching TV and trying not to think too much about Carla, something that was as ever proving pretty difficult. She had gone shopping but would soon be back and then it would be just me and her in the house, this didn't really happen very often and this would be the first time since I caught a glimpse of the real her and had been gaining elicit pleasure from her website. I knew it would be awkward being around her alone, I wouldn't know where to look and would probably have to start hiding an erection pretty soon.

I heard the door and the sound of Carla's strongly accented voice calling "Hiya, I'm back." She came into the living room carrying a load of shopping bags looking as ever the very definition of drop dead gorgeous perfection in a tight little yellow mini-dress and four inch heeled sandals. She beamed a white smile at me.

"Oh, I am glad I caught you on your own, Richard," she said to me and I felt a thrill to be needed by such a beautiful woman, "I have bought some new things and I want your opinion on what your daddy will think of them."

I could just about stammer OK and then she thanked me with a kiss on the cheek which made me blush bright red before turning and taking her shopping bags upstairs. A few minutes later she returned, looking even more stunning in a green halter top that exposed both her fine cleavage and her midriff above a tiny denim mini-skirt. I muttered a few words to the effect of how she looked fine and my dad would probably like it, where what I was really thinking was that she looked unbelievably stunning and that I didn't care about my dad, I wanted to fuck her myself right there. What followed was a strange combination of agony and ecstasy as my hot stepmum paraded before me in a succession of revealing outfits she had bought to impress my dad but that were totally turning me on.

"Now, I have something extra special to show you," Carla said as she left the room one last time.

I had almost got my erection under control and back to its normal size, thinking about the least sexy things I could possibly come up with, when Carla sashayed back into the room and ruined all my hard work with just one look at her. She was now dressed in some of the sexiest underwear available. If before it had been strange and arousing seeing my stepmum in ordinary sexy outfits, the sight of her in a sexy lingerie was just about ready to send me over the edge.

She was dressed in a black bra and panty set with red lace around the top of her bra cups drawing the eye into her seductive cleavage and further red lace around the waist band of her panties. Her gorgeous long legs were covered by black fishnet stockings held up by black and red lace suspenders. The beautiful length and arch of her legs were completed by a pair of six inch heeled black shoes.

"So, what do you think, honey?" she purred seductively, "You think your daddy will like me in these."

I couldn't speak, I just sat there, mouth agape, looking at her beautiful brown body in her black and red lingerie. I looked down at her pretty panties and could see the outline of her cock inside them and that just served to turn me on even more. I was awkwardly trying to cross my legs to disguise my growing hardon when Carla came and sat down next to me on the sofa.

"Or maybe you like me too in this lingerie?" she said, looking at me with her wide hazel eyes. "It's OK baby, I see the way you look at me," she said reaching her hand over to stroke it across my crotch, "I know you think I'm sexy, baby, and I think you a sexy boy too." I was dumbstruck and mesmerised as she unzipped my fly and pulled out my fully erect cock. "That's a nice, sweet little cock you have there, just like your daddy's," she smiled, leaning over, she began to stroke it with her hand and placed a little kiss on the tip of it before looking up into my eyes, "You want me to suck your pretty little cock?" she asked, God I wanted that more than anything but I was too dumbstruck by the whole situation to respond. Thinking perhaps that I was unsure of myself, she sat up again beside me, "Or maybe you prefer it like your daddy does," she said, pulling down the waistband of her black panties to pull out her cock, even only a tiny bit erect, it already dwarfed mine completely, "Maybe you rather suck me off?"

I stared at her cock, I'd never seen another one up this close and never seen one at all half as impressive as Carla's, it was even more so when it came out of such a beautiful, curvy, womanly body. It was at least eight inches long, uncut and totally hairless except for a tiny heart shaved into her pubic hair just above it. Carla took my hand in hers and wrapped it around her cock which was already becoming harder, longer and thicker, I offered no resistance to this. I could feel the warmth of it in my hand which could barely reach around the whole thickness of it. I didn't know what to do.

"Don't be scared honey," Carla said, "I know you want this, I've seen you watching me and your daddy, I know you wanna be in his place. You wanna go down on a big hard cock."

Not totally feeling in control of my actions I found myself stroking her dick, feeling it grow stronger and harder in my hand. She pulled me over and kissed me on the lips, rubbing her tongue against mine, I couldn't help but start pulling harder on her cock. She pulled one of her breasts out of her bra and pushed me down from her lips to her tits until I was suckling on her nipple.

"Oh honey, that feels good," she moaned, "You like your new mummy's breasts much better than your old mummy's now don't you?"

At this reminder that the woman whose breasts I was enjoying was my stepmother, that my father had been here before me, I felt my cock grow even harder and more excited. I couldn't believe the thought of doing this to my father's choice of woman would be such a turn on. Her cock was now fully erect in my hand and stuck up from her little womanly body in such a strange, new and exciting way.

"Oh, baby, your lips are so great on mummy's tits but how about you get a taste of her cock."

She pushed my head further down until I was leaning over her lap with my face barely an inch away from her cock. Close up, it looked even more intimidatingly huge and I could see all the thick veins running through it, I wondered how on earth my dad managed to get it all in his mouth, let alone up his ass. Still, I yearned to get a taste of it and that's just what I did. I stuck out my tongue and licked up and down and around the shaft like it was the biggest, tastiest lollipop ever. Reaching the head, I found it glistening with precum, I liked the slightly salty taste on my lips and decided to go for more. I opened my lips and let the head slip inside my mouth, teasing the opening with my tongue.

"Oh yes, baby, that's it," Carla moaned, pushing my head further and further down her shaft until I found myself gagging on it only about half way down, "You're a natural honey, you'll soon get the hang of it. You suck cock just like your daddy does."

Trying to remember how my dad and the other guys in those videos had looked sucking on her cock, I slurped and bobbed up and down her thick hard beast, my mouth open as wide as it could go to fit something that thick inside it, gradually managing to take more and more inside me. With one hand I cupped and played with her bare breast while the other stroked what was still outside my mouth of her cock and balls. Soon, however, I found the hand on her breast straying and jerking off my own cock which was almost fit to explode. It seemed like Carla was too.

"Baby, if you keep this up you're gonna make me cum pretty soon. Oh, oh oooo, fuck, open up your throat honey because you're about to get a taste of my hot cum! Oh fuck yes," she groaned as she grabbed the side of my head and thrust her cock right down my throat before shooting her load inside me.

It was thick and warm and salty and tasted just delicious and I couldn't get enough of it, desperately trying to swallow down as much as possible but I couldn't swallow it as fast as it came spurting from my shemale stepmum's monster cock and soon she was spurting all over my face. I barely even noticed that I was still stroking my own cock until Carla leaned over and said, "Let me give you a hand there, baby."

It only took the briefest of touches of her hand to make my cock explode and shoot a load far further and greater than ever before. Loving the taste so much, I eagerly licked Carla's cum from my face and my own from my hand while she watched and laughed.

"Wow, baby, you really are your father's son, just a cumslut like him."

Sucking on my stepmum's cock was all that I could think about for days, but fortunately it wasn't too long until I got another opportunity to do just that. One evening, after work, my dad went out for a while. I was lying around in my room, as usual imagining myself going down on my stepmum's beautiful cock, when she came into the room.

"Hey honey," she said, "Your daddy's gone out for a while. How about you and me have a little fun?"

I sprang up like a shot and rushed eagerly into dad and Carla's bedroom. On one side of the room, Carla had set up a camera and tripod which she was just fiddling with. "Take your clothes off honey, you're going to be the star of my new video."

Well, I didn't know quite what I thought of the world getting to see my exploits with Carla, but if that was the price I had to pay for what I wanted to do with her then I guess I was willing to do it. After all, I was pretty much completely stripped out of my clothes by the time these thoughts had crossed my mind. Carla turned to me, she was dressed once more in her dominatrix boots and fishnet stockings with the same elbow high leather gloves, her breasts and cock were both exposed.

"Listen, you're my slave, OK," she said, sternly, "And you will call me mistress, you do exactly what I ask of you, OK?"

"Yes mistress," I said sheepishly, as she turned on the camera, wondering quite what I'd let myself in for while at the same time feeling my erection growing already.

"What a pathetic little cock you've got there, slave, far too small to be good for anything. You want to see what a real cock looks like, bitch," she waved her eight inch monster at me, beginning to jerk it off with a lascivious smirk at both me and the camera. "Does it bother you that a little girl like me has a much bigger cock than you, slave? Or do you just want to get your lips around it, be a little cocksucking slut whore like your daddy? That's all you little cocked sissy boys are good for."

"Yes mistress," I responded, hearing my whiny, lust filled voice and knowing I was beginning to sound like the cock lusting sissy boy she was calling me, "I want your beautiful cock, it's sooo much bigger and stronger than mine, I want it inside me."

"Get on your knees, bitch," she commanded, and, when I was slow to reply, she kicked me in the groin with her leather boot, I doubled over in pain and she put her foot on my shoulder and forced me to my knees, "Listen, slave, when I tell you to do something, you do it, quickly. Understand?"

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bybritneyfan© 34 comments/ 408490 views/ 136 favorites

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