I was eighteen and in high school when it happened, my b*****r was twenty and still living at home. I had to borrow my b*****r’s computer one day to do some work for school and I guess maybe I let my curiosity get the better of me a little as I found myself instead of writing the essay I was supposed to be working on, looking through what files he had saved on his computer. I was pretty interested in particular by a very full folder hidden away in a place that you would not expect to find it. Now, I’d been a teenage boy for long enough to know that I had probably just stumbled across my b*****r’s stash of porn saved from online. Now, it’s perfectly natural in such a situation to check out what’s available, when there’s an opportunity to look at porn it’s not common for an eighteen year old guy to turn down that opportunity. And besides, I was finding myself slightly curious about just what my b*****r was into. We had never been that close, he was big, sporty and laddish and I was small and introverted, and didn’t really share things like other b*****rs might so I really didn’t know, did he prefer blondes or brunettes? Curvy or skinny girls? I really couldn’t tell you.
Whatever I might have assumed about my b*****r’s tastes, I could not have expected what greeted me when I started opening the files in that folder. Because what I found was a huge number of picture and movie files showing beautiful women of all kinds, white and black, fair haired and dark, busty and flat chested, but all sharing one very obvious feature, a very unfeminine cock between their legs. Yes, it turns out my b*****r had a little bit of a thing for girls that were a little more than they seemed. Well, more than a little bit of a thing, he was completely obsessed. There were images of gorgeous, convincing, feminine crossdressers and shemales posing in sexy lingerie, getting their cocks out and stroking them and then more hardcore stuff, shemales sucking off guys or being sucked off, getting fucked and fucking. It was an amazing collection and it showed that this wasn’t a passing fancy for Darren, this was something he had invested a lot of his time in exploring, I wondered which were his favourites and how many times he had sat there in front of his computer wanking himself to these images.
After my initial reaction of shock and surprise, I didn’t know quite what to think about this discovery about my macho b*****r. It seemed so weird and disturbing to get a window into the kinky things that turned him on and it was certainly something that I had never really thought about too much before, these men who could pass successfully as hot and sexy women yet beneath their skirts still held onto that one strong aspect of masculinity. Although it started out just seeming weird, I was finding I couldn’t stop looking at this stuff, I kept opening the files, playing the videos, I was engrossed, completely fascinated by these strange but beautiful creatures. It began to be an incredible turn on for me watching a hot girl fucked hard in her tight arse while she stroked her own hard cock.
I was beginning to see what Darren saw in these shemales, they were something special and watching them I began to wonder what had made them want to become like women in the first place, what had attracted them to cladding their bodies in those soft and sexy clothes and acting like dirty sluts, giving it up to anyone who wanted it. By now, what had seemed weird and unnatural was starting to sound exciting and alluring and I realised I wasn’t just fantasising about these beautiful heshe girls on the screen but fantasising about what it would be like to be like them, to be a hot slut chick with a dick dressed in sexy lace lingerie.
I knew I had to find out and I knew just how, after all there was someone very close to me who I was pretty sure shared some of my new fantasies and could probably be persuaded to explore them with me. I wondered whether Darren had ever been with a real tranny girl before, I mean he was pretty popular and especially with the girls, he was tall, muscular and handsome, but I couldn’t imagine where he would meet a girl who could show him just what he wanted and anyway he had a reputation to keep up, he couldn’t let people know just the kind of women he really would go for or that reputation would be ruined. I kind of hoped he hadn’t lived out his internet fantasy in real life, it would make it a lot easier for me to seduce him. Yes, that was my plan, to give my b*****r a taste of what he longed for and get to fuck a girl who wasn’t quite all woman and to let me try out a bit more of my feminine side, I decided to seduce him. I knew it was going to be tough, even though he lusted after transvestite and transsexual girls would he be able to get over his macho exterior and actually let himself fuck one? And not only that but I was his b*****r and that would be a pretty big hurdle to get over for anyone. Still, I was pretty confident that as long as I could transform myself into a sexy and convincing enough woman then he couldn’t help but give in to his lustful side and given an effective enough transformation then I could almost become like a separate person, I hoped he would stop seeing me as his geeky younger b*****r and instead just fall head over heels in lust with the sexy Cynthia, that was the girly name I had picked for the person I was to become.
Well, it wasn’t long before I got my chance, although it seemed an age with almost every waking minute cementing my desire to transform myself into a naughty girly slut making me unable to concentrate on anything but my fantasies. One evening, my parents were gone away for the weekend, leaving just me and Darren in the house. Darren had gone to a friend’s house where they would probably drink beer and watch TV. Hopefully, when he got back a little d***k his inhibitions would be loosened up and he’d be more receptive to Cynthia.
With the house to myself, I ran a bath to get myself totally clean and shaved off all my body hair with my mother’s leg razor, giving me silky smooth legs. Already I was starting to feel more feminine and loved the feel of running my hands up the soft smoothness of my hairless legs. I dried myself off and sprayed a little of my mother’s perfume on to give me an alluringly sexy, womanly scent. Then it was time to raid my mum’s closet for suitable seduction outfits.
Fortunately, my mum had been a pretty attractive woman in her day and remained so even now, I guess she’s where I got my slight frame and long legs from, so she still had a pretty sexy wardrobe. I decided to keep it fairly simple so went for a dark suede knee length skirt and a white blouse with short puffy sleeves that was so thin it was basically see through. Now for the exciting part, the underwear. My mum had something of a treasure trove of sexy lingerie and I ended up opting for a pair of lacy bikini cut briefs and a matching bra. Stuffing the bra with tissues gave me what approximated my mum’s C-cup and then sliding the panties up my newly smooth legs was something of an erotic feeling. In the underwear I felt totally girly and the soft feel of the lace on my cock and arse was delightful. I slid the skirt up my thighs and zipped it up, being taller than my mother it came to a little above my knees and showed off an impressive amount of my long bare legs (I hoped Darren was a leg man as mine were definitely my best feature as Cynthia, something that would be the envy of many real girls).
I was pleased to note on doing up the blouse that the outline and colour of my naughty red bra was clearly visible through the thin fabric but as I was using tonight to try and get off with a macho lad I decided to reveal a little more, leaving a couple of buttons undone so the scarlet lace around where my cleavage would be was well visible. I topped the outfit off with sexy shoes, red with four inch heels that were at first difficult to walk in but, after a little practice, gaving me a sexy sway to my walk and did not end of good to the curve of my calves and the sight of my pert little arse in the suede skirt.
All I needed now was hair and make up, I thanked my luck that I had recently been growing my brown hair long and it didn’t take too much time with my mother’s styling products to make some gorgeously feminine waves that fell over my shoulders and instantly made my face look more womanly. A little make up further enhanced that with blush to bring out my cheekbones, dark eyeshadow and scarlet lipstick the same colour as my bra and shoes. Looking in the mirror, I could tell that I would do pretty well. I had never considered quite how good a girl I would make even when planning this but the clothes, hair and make up completely transformed me. I was Cynthia, long legged beauty with the kind of slutty make up job that a guy like my b*****r was sure to go for. Now, all I had to do was wait.
After a drink to calm my nerves, I sat on the sofa and waited for my b*****r to return, all sorts of thoughts running through my head. If he doesn’t go for it then what will he tell mum and dad? If he does then I’ll not only be getting fucked for the first time but by my own b*****r. I just hoped I was ready to handle that. Well, I guess there was nothing for it, nothing I could do now as I heard the front door opening and my b*****r’s footstep stumbling a little on the threshold. As I heard the door slam behind him I steeled myself for whatever was to come and went out into the hallway to meet him.
“What the fuck?” said a visibly slightly d***k Darren as he watched a hot girl saunter towards him in a short skirt and heels, only realising it was me when I was right beside him.
“Welcome home, big boy,” I said in my best husky feminine tones, reaching up and running my hand along his arm, caressing his impressive bicep.
“Steve, what are you doing? Why are you dressed like that?” he sounded more confused than angry.
“Tonight it’s Cynthia,” I said, still rubbing his arm but now leaning to whisper in his ear, “And tonight I’m all for you.”
“Come on Steve, what’s going on?” he said, pushing me away.
“I know what you want,” I continued in Cynthia’s sexy accent, licking my scarlet lips saucily just in front of him, “You want a girl like me and tonight you can have her.”
“I don’t know what you’re talking about Steve,” my b*****r said as he let himself be taken by the hand and led into the living room, sitting on the sofa beside me, “I’m not into that shit, I’m not gay and you’re my fucking b*****r, man.”
“You don’t have to lie to me, honey,” I reached over and began to rub his crotch, “I know all about your little kinks and fantasies and I want to help you with them. Don’t you want me to help you?” I pouted my scarlet lips.
While he hesitated for a moment, I decided to press home my advantage, leaning across and taking his head in my hands I pulled him to me, kissing him on the lips, letting my tongue slip into his mouth. He tried to push me away with his hands but his mouth opened and his tongue began to stroke mine even as the kiss broke. I had never even wanted to kiss a guy before, I didn’t feel gay doing this, just like I was a woman being with a man, but it felt great to do it, he tasted strong and musky and I longed for more. A little of my red lipstick was left smeared on his mouth.
“Steve…?” he said in an almost pleading tone, begging me to stop but urging me on at the same time.
“Call me Cynthia, baby,” I said, returning my hand to his crotch where I could now feel a little hardness, it gave me a rush of excitement to realise I was the one giving him that.
“Cynthia,” he said, and I had already won a small victory by getting him to use that name for me, “I don’t want this, what are you doing?”
“Come on, we both know this is just what you want,” I said as I unzipped his trousers and freed his cock, long, thick and growing in hardness all the time as my hand touched its nakedness, “Just look what it is that I do to you, and you do the same to me honey, just look at that.” I lifted my suede skirt around my waist and pulled aside my panties to show him my own cock, considerably smaller than his but just as excited.
At the sight of my cock sticking out from under my skirt and panties, his eyes began to widen and stare with ill disguised lust. I could tell that I was just the kind of girl for him, feminine in body and dress but with a nice hard cock at the same time. I wrapped my fingers around his cock, it was so thick they barely went all around it, and began to masturbate him while the other hand did the same with my own member.
“Oh, uh,” groaned Darren, “Steve, uh, Cynthia, please don’t. This is really not right.”
He told me to stop but he did nothing with his body but let me stroke his big cock and hungrily eye up my feminine appearance and my own little dick. I took this as a good sign, especially as, when I squeezed my hand around his shaft and began to wank him harder he groaned and his cock grew even firmer. I leant over and said to him in a slightly taunting tone.
“Come on babe, just admit you want me. We both know you’d just love for a hot girl like me to get her lips round your cock even as she jerks off a cock of her own. If you just admit to what you want it’ll be a lot easier.”
“Mmmm, Cynthia,” he moaned.
“Yes,” I giggled, seeing him used to saying my feminine name.
“I do want you,” he sighed, even I was surprised to hear him say it, he must really want it bad for his willpower to break down so quickly, “I’ve always fantasised about being with a gorgeous tranny girl like you, Cynthia, just like you kinky slut wanting so bad to suck off a big, studly guy like me.”
“Oh yes,” I gasped, not wanting to let this moment go, “I am a naughty slut and it’s your cock I want inside me, b*****r.”
“Come on then, bitch,” he said, “suck it.”
I loved it that now he seemed willing to just go with the situation and act out his fantasy, he wanted to take control. I loved the feel of Cynthia becoming his bitch, his slut, of putting my feminine self completely in the power of a strong, masculine man. I slid to the floor and got on my knees between my b*****r’s open legs where he remained sat on the sofa. Close up, his monster cock looked even bigger, thick, throbbing and veiny and just waiting for me to take it inside me.
“It’s sooo big,” I sighed with my lips up close, “I don’t know if I can handle it.”
I wasn’t just teasing him, I was seriously worried, having gone from never taking a cock in my mouth before straight to something this big was going to take a big effort. I still held it in my hand, stroking the shaft as I licked my tongue along it, my other hand under my skirt jerked off my own little cock.
“Uh, yeah, that’s it, you’re a natural,” my b*****r grunted as I licked all around his shaft, “Who would have thought my little b*****r would make such a hot cock hungry slut?”
I couldn’t believe how much it was turning him on that the crossdressing slut licking his cock was his own b*****r, I thought that the Cynthia persona would be necessary to let him get beyond that fact but instead it was part of what was making his cock so hard in my hand. And the fact that I was turning him on so much acted as something of a greater turn on to me, stroking my own cock. I kissed the swollen head of Darren’s dick and then opened up my painted lips and let it slip inside, circling my tongue around his foreskin and tasting a little salty pre-cum. It was a taste that spurred me on to desire more and I loved the feel of my b*****r’s warm, hard member filling my mouth. I couldn’t really fit more than the head in but even this was pretty amazing as a moved my mouth around it, all the while still stroking my hand along the base of his shaft. This wasn’t enough for Darren, however, and he took his hand and held me by the back of my head, locking his fingers in the dark feminine waves of my hair and pushing me down onto his cock.
“Come on you dirty whore, suck my big fat cock,” he said as I took a whole couple of inches of its length into my mouth. I could only hum and gargle with my mouth completely full but it didn’t matter to him, he was going to get what he wanted, “You just love sucking on your b*****r’s hard cock don’t you you little slut?”
“Mmmm, agrh” I could only gargle and mumble with my mouth full as I began to gag on my b*****r’s b**st.
Fortunately, he released the pressure on the back of my head a little, allowing me to let it slip back out of my mouth, letting me gasp for air for a second. As soon as his cock was gone from my mouth, I wanted it back in and was soon slobbering back all over it, bobbing my head back and forth as Darren held me down, all the time trying to relax my throat and trying to take that little bit more in.
“Fuck yes, Cynthia, my slutty tranny s****r you suck cock like a pro,” Darren was turning me on even more with his dirty talk as I opened my throat for his massive cock, “A filthy whore in lingerie with a nice firm cock of her own. Just the kind of bitch I like, my own sissy b*****r.”
As I slurped on the pre-cum leaking from my b*****r’s cock I felt my own wetness staining my mother’s red lace panties that I still wore, I knew that much more of this and my own cock was going to explode. But there was one thing that I was yet to experience in my night as my b*****r’s personal crossdressing slut, I needed to get fucked and the more I sucked on my b*****r’s hard cock the more I needed it bad. I was desperate to feel myself completely used like a real whore of a girl, to feel that massive cock violating my little arse. Fortunately for me, my kinky older b*****r seemed to be having the exact same thoughts.
“Alright bitch, now how about I have a go at that sweet little tranny arse of yours,” he said lasciviously, “Sissy sluts like you need a really good fucking.”
I took my lips from around my b*****r’s meat, pleased to see my scarlet lipstick streaked across his long thick shaft, and got up. He told me to lie back on the sofa and open my legs. I pouted and licked my lips with a naughty come hither look and said in my husky Cynthia voice.
“Come on then, baby, I want to feel your big cock up inside me,” I sighed slightly, “And I know you just can’t wait to fuck your sissy s****r,” I waved my hard cock at him, “This really turns you on doesn’t it, the sight of your slut of a s****r with her skirt pulled up, legs wide open and a big cock all hard just for you?”
“Fuck, you’re one hot little bitch and it’s going to be my pleasure to take your cherry as I fuck your sissy bitch arse.”
He positioned himself between my legs and held the heels of my slutty red shoes, pulling my legs wide open and bringing my arse up so my knees were almost up around his shoulders. He pulled my scarlet lace panties further aside and pulled my hard cock up to reveal the tight, puckered entrance of my never yet entered arse. He spat on his hand and stuck his finger inside me to give my arse hole a bit of lubrication but I felt that it wasn’t going to be enough for his nine inch monster. His cock was already slick and wet with a combination of my saliva and his own pre-cum.
He pushed the head up inside me and I tried my hardest to relax but it was incredibly painful and this was only the first inch. Gradually, as my arse adjusted to the pain of it, he pushed more and more up inside me, until at about six inches he stopped. I felt completely impaled on his huge pole and completely under his control, unable to barely move. He withdrew most of it and then rammed it straight back in.
“Oh God,” I screamed almost blacking out as the bl**d rushed to my head.
“How do you like that, slut?” Darren said as he stood commandingly over me, “You’re my little bitch now, Cynthia.”
As he said that, he pulled out and rammed his cock back in, even deeper this time as I swooned once more with the pain and let out a girly little yelp. Before too long, he began to thrust regularly in and out of my tight, little virgin arse and I was shocked to find the whole of his nine inches buried deep inside me, no wonder I felt impaled and filled by him. Even though it still hurt like hell, I was beginning to feel incredibly stimulated in places deep up inside me that I never knew could feel this great. I started to get into it, with my b*****r’s hands on my waist, holding up my suede skirt, he levered himself to thrust harder and deeper, his balls now slapping against my arse, meanwhile I began to rock my hips so I rode to meet his thrusts.
“Uh, ah, mmmm, yes, fuck, b*****r, fuck me, use me like your dirty bitch, oh God yes!” I began to moan and scream, “Fuck my virgin arse, b*****r, take your slutty sissy s****r’s cherry! Make me a woman, make me your bitch!”
As I threw back my long, wavy hair and groaned, I pushed out my chest, tearing open my white blouse (and hoping my mother didn’t still ever wear it) to reveal the lacy stuffed red bra beneath it. Really getting into the role of slutty Cynthia, I now almost imagined myself as a real girl and began to cup and play with my tissue breasts through the bra as if they were real as I arched my back and continued to meet Darren’s thrusts.
“God bitch, you’re tight, it’s incredible, the feel of your tiny arse on my cock, I feel I could cum any minute!” Darren groaned as he violated my tight arse.
Looking down, I could see what he meant. Frankly, it looked like one of the tranny porn films that Darren had on his computer, my little, slight body, with a blouse torn open and a filled red lace bra, a suede skirt hanging around my waist, my own hard cock showing out of the lacy panties that had been pulled aside, flopping around as my little pert arse and tiny arse hole was repeatedly violated by Darren ramming his massive meet between my little arse cheeks, my sexy, long bare womanly legs were wrapped around his back. He moved his hand from its place on my waist and wrapped it around my warm, hard cock, beginning to stroke it off even as he continued to fuck my arse, stimulating me both deep inside and on my cock.
“Oooo, ah, yes, b*****r, that feels amazing, keep doing that, I’m fucking loving it,” I screamed, and truly I was loving having my virginity violated by my own b*****r.
“God Cynthia, you’re quite a girl, tight arse, big tits and this lovely hard cock,” he groaned, “You’re everything a guy could want, my fucking sissy slut of a s****r.”
I knew that with the extra attention of my b*****r wanking my cock even as he fucked me it wouldn’t be long before I went right over the edge.
“Oh, oh, ooo, God, baby, keep jerking me, your going to make my little girly cock cum,” I yelled out.
“Fuck, slut, that’s it, cum for me,” he said, “I want to see you cover your girly lingerie in all your thick white cum.”
“Ah, aah, oooh, oh God, Fuck, OH!” I screamed as my body shook all the way through with an incredible orgasm, “Fuck, b*****r, I’m cumming!”
A stream of warm cum shot out of my cock and hit me on the chest, staining my mother’s sexy brown suede skirt. Darren continued to plough into my arse and pump his hand up and down my cock, milking my cum as it shot out in spurts, covering his hand and my thighs, skirt and chest. Some of it even shot up over my red lace bra and one stray drop hit me in the chin.. I stuck out my tongue and licked it up, almost instinctively, acting as I was like a dirty tranny porn star, I was just imitating them. But I loved the warm salty taste and the way it made me feel naughty for drinking my own juices. I knew I wanted more and was going to get some pretty soon from the looks of it.
“Fuck Cynthia, you naughty bitch, like the taste of cum do you, slut?” Darren was saying, “I’m gonna cum for you soon bitch and I’m gonna cum all over your slutty girl face.”
He pulled out of my arse and came around to where I was lying back on the sofa and stuck his cock in my face, jerking it off. Even though it had just come from my own stretched out arse, I put my lips around the head and sucked on it as the first of his cum shot out and hit the back of my throat. Warm and salty, it tasted great and I drank it down. More kept coming, much faster than I could swallow and I had to let my b*****r’s cock fall from between my lips as bubbles of cum leaked from the sides of my mouth. Darren continued to jerk off as he covered my face and hair with his cum.
“God, you really look like a dirty tranny porn star now, Cynthia, all covered in my cum, licking it up from your lips,” he laughed, as he finished cumming and put his cock away, leaving me collapsed on the sofa in my mother’s torn and cum soaked clothes and undies, covered in both my own and my b*****r’s cum. A little grin came to my sticky lips, my plan had come off better than I had ever expected, I had got to see just what it was like to be one of those crossdressing sluts on my b*****r’s porn films, dressing up, sucking cock and getting fucked like a real woman. It had been quite an evening.
Later, after I had cleaned myself up, hidden my mother’s ruined clothes and reverted to my male self, Darren came up to me and took me aside.
“Listen, man,” he said, being more b*****rly with me than usual, “You know that if what happened gets out then my reputation will be ruined, so just keep things to yourself, ok.” Well, I’d expected that, frankly, but I’d hoped he might mention thanks or something, tell me how much he enjoyed our evening together. And then, as he turned to go out, he just added, “Oh, and if Cynthia is around this evening, tell that dirty slut that I want to see her in my bedroom and maybe she can get her little arse fucked again.” He grinned and walked out and that was it between us. Well, the whole incident hadn’t made us any closer as b*****rs but it did seem to have given me a new f****y role, Cynthia, my b*****r’s slutty tranny lover.