8 comments/ 52679 views/ 20 favorites My Brother's Love By: chocolatecookie3 Thomas was my brother. My parents adopted him when we were kids, so I had always thought of him that way. By high school I had started to have confusing feelings for him, but I thought college would make those go away. I wasn't prepared for the rush of emotions I felt when I saw him on my first break home from school. "Sis! I hardly recognized you!" he said when I walked in the door. Before I could react, he grabbed me into a hug. "Thomas, I missed you," I managed to squeak. He had big square shoulders, and I always thought of him as a typical jock. Now his arms felt strong and safe. I pulled away, embarrassed but warm. I saw him look me up and down. I had also filled out some; the freshman fifteen had gone to my hips and exercise had expanded my chest. "Wow, Caroline, you look great," he said. "Don't just stand there," Mom said, pushing by to get a hug. "Go get her bags." I was relieved for the interruption. I had messed around with a few guys at school, but none of them made me feel like my brother. Stop that, I thought to myself. He's my brother, not a potential boyfriend. I went to my old room, and I didn't have any time to compose myself before Thomas came in with my bags. He dropped them on the dresser and jumped on my bed. "So what's college like?" he asked, lying on his stomach and propping up his head with his arms. "You should I know, you went." I said, unpacking my suitcase. "Yeah, but I didn't get to go to big ole State U. Are there a ton of hot girls? Besides you, of course." "Thomas!" I blushed. "There are a lot of fraternity girls in my dorm. I don't go to a lot of parties, though. Not my thing." "No, I'm sure you are the perfect student. Always straight As in high school." He sighed. "Did you have a little fun at least? Looks like you've been working out." "I joined the colorguard. Who knew flag twirling could build muscle?" The days outside had also darkened my skin. Back in high school, people had always assumed we were related because we had the same skin tone, the color of dark wood. I held my arm against his. "I got a tan," I said. He laughed. "You got some muscles, too." He ran his hand up to my shoulder. They were still big and rough. He played football in high school. I shook myself away. I had goosebumps. "What are you doing here?" I asked, trying to sound casual. "I quit the job and came back. I'm crashing until I find a new one." He only went to school two years before going into a trade, something to do with electricity. "Mom still has both our rooms the same." "I noticed," I said, looking around. Had I really outgrown the pop stars and princesses in one semester? "It feels good to be home." "I know what you mean," he said, staring at me. I turned away quickly, wondering why I felt like blushing again. He's only your brother, I thought to myself. I remembered seeing him in the bathroom one weekend when he came home to visit. It was just after my 18th birthday, a few months before I graduated high school. I never thought much of banging on the bathroom door to get him out, but this time I noticed the door wasn't all the way closed. When I looked in, he was undressing to get in the shower, facing the doorway but looking down. I saw the toned muscles rippling under his dark brown skin. His arms and legs were slim and round—they gave him a lot of speed on the football field. His wrinkly cock was swinging between his legs. It looked long even while flaccid, and I wondered what it would look like hard. Thomas never brought many girls home, but I'd overheard him tell his friends how they liked to suck it. That day I thought about what it would be like to taste him. I was ashamed of my thoughts, but it still made me wet. I had slipped away without disturbing him. Mom made all of my favorites for dinner. She was humming and pecking like a hen. I think she missed me more than I missed her. Dad was the same as usual, watching TV and checking his phone. Thomas kept watching me, teasing and asking questions about college life. We had not kept in touch, so it was good to be with him again. I just wished I could stop thinking about how handsome he was. Before bed, I decided to read my book. It was a trashy romance novel, but I loved the sex scenes. I was wearing just a t-shirt and panties for easy access. Just as it was getting to a good part, my door swung open and Thomas bounded in. "What are you doing?" he asked as I shoved the book under the covers. "What are you reading?" He pulled down the covers and grabbed the book. "Oh, sis! Look who's being naughty!" "Stop it," I whined, trying to grab it back. "I'm an adult. I can read whatever I want." Thomas flipped open to a page. "'He rubbed his quivering manhood over her flooded lips...' Does that get you hot, sis?" I crossed my arms and didn't answer. He grinned at me mischievously. "So how about it, you getting any in college? Not just reading about it, I hope." I shrugged. "I've been out with a few guys." "Yeah? And?" I squirmed. "Why do you want to know?" "I just want to make sure you're having fun," he said, flipping through the book. "God knows you couldn't get in any trouble in this house." Our parents had been kind of strict. "I've done...a couple of things." "Like what?" "Thomas! I can't tell you what." "Yes, you can." He pushed up to sit beside me. "Mom and Dad are out at dinner, remember? Look, you can whisper it to me." He dramatically looked around the room, and then cocked his ear toward me. I felt warm all over. "Well, I gave this guy a blow job." I wasn't a virgin, but until college it had all been one guy. "Bravo, a blow job." He politely clapped. "Did he return the favor?" When I shook my head, he said, "He didn't? Did he even finger you?" "It's only been one semester," I joked. It wasn't enough to divert the look in his eyes. I tried to tamp down the tingle in my crotch. "It's no big deal." "Do you like to masturbate, sis?" he asked in a low voice. I couldn't help but look down his pajama bottoms. Was there a bulge there? "Why?" "I mean, you're reading a trashy sex novel, what if you get horny?" I was already horny. "Then I'd...do something. After my brother left the room," I said, trying to at least pretend to fight. He looked around again, smiling wickedly. "I don't see any brothers. No parents, either." I just stared at him, hardly able to breathe. "Look Caroline, I know I'm technically your brother, but I've always thought you were pretty hot. Especially when you came home the other day. Doesn't that make me a terrible brother?" "Yes," I said, my voice shaking. "Adopted brother." He put the book down and reached down into my pants. His fingers quickly found my wetness. "Are you horny, Caroline?" he asked, lightly stroking my clit. "Want me to help you 'do something?'" I closed my eyes, trying to imagine anyone but my brother doing this. I couldn't. I didn't want anyone but my brother doing this. He circled my clit with his thumb while his fingers dove in and out of my pussy. It felt so good. I leaned my head back and massaged my breasts with my hands. He rubbed until the tingle became a flood. I pumped against his palm as the wave hit me, moaning as my juices covered his hand. He pulled away and sucked on his fingers. "Mmm," he said. I felt faint watching him. My brother. "God, that was hot. I think I have my own problem to take care of now." I didn't need any other prompting. I leaned over and pulled on his pajama pants. His cock popped out, stiff and thick. Anxiously I looked toward the door. What if mom and dad came home? "It's ok, sis," Thomas whispered. Taking a deep breath, I placed my hand on his cock. I rubbed it gently, eliciting a groan from him. I looked back. He had closed his eyes and rolled his head back. "Put it in your mouth," he whispered. "Please." I bent down and licked the head of his cock. It bounced away, and when it came back, I caught it in my mouth. He groaned louder as I pulled the shaft in past my lips and down my throat. I couldn't get past my gag reflex, but I knew how to use my tongue and hand. He rubbed my back while I worked. Suddenly he lifted his hips. "Oh fuck, Caroline, I'm going to come!" As soon as he said it, his cock shuddered and streams of cum started to hit the roof of my mouth. I tried to swallow as much as I could, but the rest seeped into my hand onto his crotch. He exhaled loudly and grinned. I blushed. "How was that?" he asked. "Better than your dates?" I nodded. "You going to let me eat you out?" "Maybe tomorrow," I said. "We can't get caught." He put a finger on his lips. "It's our secret." He was gone most of the next day. I spent the whole time wondering if I should tell Mom and Dad what happened. I relived every moment, bouncing between guilt and happiness. He wouldn't meet my eyes when he came home. I took that to mean he regretted it, so I kept quiet. He was still cheerful at dinner, but he didn't tease me as much. When I tried to catch his eye, he looked away. Soon a friend called, and he was out the door again. I went to bed confused—relieved that we didn't have to talk about it, sad that he hadn't enjoyed himself. I thought about him all night. His hands, his cock, his mouth. What would it be like to kiss him? Would it feel weird? I thought I was dreaming when I felt him slip in bed behind me. His hands reached around to cover my breasts, and he kissed my neck. I leaned back and could feel his cock pressing against me. He was naked. Shocked, I turned over and looked at him. "What are you doing?" I asked in a whisper. "I'm coming back for seconds." I could hear the smile in his voice. "You hardly talked to me all day," I complained. "I know. I just didn't want it to be weird. But I had fun, Caroline. I liked it." He leaned down blindly and kissed my cheek. "A lot." The next kiss was more accurate, capturing my mouth. I kissed him back and felt my body rising to meet his. He pulled me close and pushed his tongue deep inside me. When he pulled away, we were both breathing fast. "What if Mom or Dad wakes up?" I asked. "I closed the door this time." He reached under my shirt, and I helped him pull it off. He held on to one breast while he licked the other, and then he switched. I shivered. He kissed down my belly, and when he reached my panties he pulled them off. He drew his finger down across my slit. He traced the outside and then the inside lips. Finally, he knelt down and followed the same path with his tongue. I shivered again, happy that I always kept that area shaved. Now my brother was enjoying it. He reached his tongue inside me, tasting my wetness. I moaned and lifted my hips to meet him. He licked upward and found my clit. He played with me for a long time, bringing me agonizingly close to an orgasm. He pulled up my ear and whispered, "Are you going to let me fuck you, sis?" I nodded, but knowing if he could see it, I whispered, "Yes." I had never wanted anything so badly as my brother's cock. He positioned himself over me and easily slid in. It felt like a perfect fit. I squeezed my pelvic muscles and he groaned. He made quick thrusts into me, and I wrapped my arms around his wide shoulders. My orgasm thundered through me. As I shook underneath him, I heard him saying, "Oh fuck, Caroline!" He repeated my name as he released himself inside me, and then he was still. I held him on top of me until I felt him getting soft. Neither of us seemed to want to move. Finally, he rolled out of my arms onto his side. I couldn't see his face, but I heard him sigh. "You better not have any STDs," he said, back to his joking self. "Thomas!" I hit him, and he laughed. He was still my brother. "What do we do now?" I felt him shrug. "We just have to pretend like everything's normal. It's not like we can tell Mom and Dad. I'm going to come visit you at college, though." "You will?" I asked, excited. "As long you pretend I'm your boyfriend." He traced his fingers over my face. "How will they know?" "We look alike." I giggled. "All black people look alike!" We both laughed out loud, but then I shushed him. I didn't want to wake up Mom and Dad. "Do you think we'll get away with it?" "I don't care if we do or not. I just know that I love you, in that way." He kissed me, and my stomach tingled. I'd never felt happier. My Brother's Lover I was eighteen and in high school when it happened, my brother was twenty and still living at home. I had to borrow my brother'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 brother'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 brother 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 brothers 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 brother'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 brother 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 brother. 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 brother 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 brother 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 brother 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 drunk 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 brother 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 brother 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 brother. 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 brother'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 drunk 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 brother 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 brother, 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, brother." "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 brother'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 brother grunted as I licked all around his shaft, "Who would have thought my little brother 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 brother, 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 brother'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 brother'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 brother's beast. 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 sister 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 brother." As I slurped on the pre-cum leaking from my brother'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 brother's personal crossdressing slut, I needed to get fucked and the more I sucked on my brother'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 brother 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 brother'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 sister," I waved my hard cock at him, "This really turns you on doesn't it, the sight of your slut of a sister 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 blood 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 brother'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. My Brother's Lover I was washing my hair, bent over the bath as I felt a pair of arms slide around my waist and lift me a few centimetres off the floor. "Oh!" I gasped, wriggling in the arms of my boyfriend and throwing the handful of soapy water in my hands at his grasp, "you do pick your times, don't you?!" He laughed, the low growling timbre of his voice hot against my neck as he loosened his hold to let me down to floor-level whilst keeping his arms loosely hooked around my body. "I don't know, there's something very cute about you with bubbly hair," he whispered in my ear, before giving me a playful swat on my ass and letting me go. I was staying at his for the first time in our short relationship so far and was enjoying it enormously - the only fly in the ointment was the fact that, like him enormously as I did, I was beginning to realise that that was it - I liked him. I wasn't about to fall in love with him and I very much doubted I could, lovely as he was, he just didn't have the -pow- factor that I needed to get me to fall head over heels for someone. I sighed, and continued to wash my hair, rinsing the shampoo out and sliding conditioner through the strands as I became conscious of someone standing behind me. Assuming it was Greg, I smiled into the bath and held out my hand to take his. Feeling fingers sliding around my proffered hand, I continued to wash my hair clean before a very different, yet strangely familiar, voice to his began to say in a wryly amused voice; "well, it's not often I find strange women washing their hair in my parents house, that's for sure...". I whipped my hand away and flicked my hair out of my face in surprise, inadvertently splattering both me and the strange man, who - oh, SHIT - it appeared was Greg's brother. "Oh, God - I didn't think anyone else was here - " I began, only realising as I spoke that if he didn't know who I was, this would just incriminate me further... "I mean... I'm here with Greg, I take it you're his brother?" Much better. His brows raised, and he looked me up and down, only now did it cross my mind that we were standing much too close and the realisation sent a flutter of awareness down my spine as his lip quirked and he opened his mouth to speak. "You don't really look like my brother's type, that's for sure..." he said to me, his hands on his hips. "Oh really? And what type is that, exactly..?" I responded, realising too late that the flirtatious tone in my voice was blatantly obvious to the most thick skinned of people, and this man did not strike me as particularly obtuse. His brows raised, but he didn't seem particularly put out, as he suddenly grabbed my hips and lowered his head to meet mine. The shock of the kiss sent shivers through my bones as I arched my back towards him and looped my arms around his neck before I realised what I was doing and pulled away, barely five seconds after the kiss started but out of breath and red cheeked. He was looking at me with a smile on his face, his hands still on my hips as we stared at each-other. "Well," he said softly, "my brother doesn't normally go for my type, so I don't get the urge to kiss them quite like that..." His words reminded me forcefully of the situation we'd created, and I pulled away from him, running my fingers through my wet hair as I turned my back on him and switched the water off. "That didn't happen, okay?" I said with my back still turned away from him and I could feel him moving closer towards me with every cell in my body - God help me, but I wanted to feel his lips on mine again. I was so close to turning around and taking away any credibility to my words when I heard Greg in the doorway. "Oh, hey, James..." he said, surprised. "I didn't realise you were staying here tonight as well," he continued, his voice trailing off slightly as he noted how closely we were standing. "I see you've met Fran, then..." "Yes," James replied, and as I turned around from the bath, he was walking out the door. "I'd say we're quite well acquainted now, wouldn't you?" he directed at me, throwing a wink over Greg's shoulder. I glared at him and then focussed my attention on my boyfriend, his brother! Oh, my God - what was I even thinking of? I couldn't do this to Greg, and honestly, I shouldn't even have come tonight, knowing as I did that the relationship was doomed to failure. I closed my eyes against his face, lined with confusion at the situation I'd put him in. "Greg, listen - we need to talk." -x- Unfortunately, having broken up with him, he was my ride home so as I packed my belongings to return to the city, I was preparing mentally for an incredibly awkward journey as I became aware of someone standing in the doorway behind me. Knowing from earlier that the one person who could make me so aware of their movements was not the man I had just dumped, I stiffened before he even said anything. "Yes?" I snapped, as I sensed him moving closer towards me, and jumped out of my skin as he placed his hands on my hips. "Just what do you think you're doing?" "You didn't need to break up with him, you know - but I take it I was a big motivator in that decision, right?" James said, letting go of my hips and standing back a little. I crossed my arms over my chest and turned around. "Well, you don't say? I don't normally go around letting my boyfriend's brothers kiss me," I told him, trying to inject a little bit of sternness into my tone but failing miserably. I guess it was a testament to the sizzling atmosphere between us that it somehow managed to come out flirtatiously - I closed my eyes and shook my head, giving up on any kind of moral high ground attempt. "Honestly, it wasn't you - I just knew things weren't right and what happened just proved it." He shook his head and took a step closer to me again, "Fran." "What?" "I know I must seem a total ass for kissing you, but honestly, I'd do it again. I don't normally go around kissing girls my brother's dating, you know..." he shook his head, and ran his fingers through his hair, closing his eyes for a second, "but I guess you don't believe that." I considered for a moment. I mean, yeah - the guy was obviously a bit of a jerk if he was still trying to come on to me but really - I couldn't be imagining the electric heat between us, and if he was a jerk... what did that make me? Honestly - he didn't strike me as a bad guy, if you ignored the fact that he was even making me think about this, but insane as it might sound... I believed him. I didn't think he did this regularly. My body relaxed slightly and I took a deep breath in, closing my eyes as I opened my mouth to talk before being interrupted. "Greg's gone, by the way," he told me. My eyes snapped open in shock, "what?!" I asked sharply. "He can't have, he's my ride!" "He asked me to take you back tomorrow - incidentally, he guessed what had happened," James said, a note of wry amusement in his voice, which was somewhat at odds with the guilt that I could see in his eyes. "He was a bit pissed, I think it's fair to say..." "Oh, God - that's awful," I muttered, before something else he'd said sunk into my brain. "You mean - we're spending the night here, together?" "Yeah," he replied, then understanding lightened his gaze. "Not together as in, together - but you know..." his hands moved to my hips again and he kept looking in my eyes, moving slowly as if waiting for me to say stop - but, God help me, although I knew I should halt him... I didn't. I let his hands move over my hips and his body slowly get closer to mine until our hips were touching and if I leant forward just a bit our lips would meet and we'd be kissing. Our eyes were glued together and I knew how easy it would be to succumb to the heat burning me up and lower my eyelashes and let our mouths join, but I shouldn't - I really shouldn't, but, oh - my eyelashes closed and his mouth brushed my lips gently, so gently that I let out a soft sigh and his mouth attacked mine passionately, our tongues fitting sensuously together and his hands holding my hips against his, no sound in the room apart from the soft kisses that he moved down my neck as his hand quickly unzipped the shift dress I was wearing. The metallic clinks made me pause for a second and brought reality home but, oh God, as his mouth moved over my neck and over the hollow in my shoulder I moved even closer to him and let the dress slide over my body and land in a heap of fluid material on the floor. I didn't know how it had reached this point so quickly, but I knew that we only had tonight and we had to make the most of it - this was wrong, so wrong, but it felt so right that as I pulled his t-shirt over his head and brought his bare torso to mine, skin against skin, all I wanted was to feel him inside me and I didn't care whose brother he was, much less that Greg probably knew exactly what we were doing right now. His body was hot against my skin, his jeans already halfway down his legs and his heavy shaft poking a tent inside his black boxers, as I pulled him backwards onto the bed and we toppled down, him on me and my legs open as the shape of his erection nudged between my legs and I wanted him deeper, much deeper. His mouth was wet on my neck and I opened my eyes, the white ceiling feeling so alien as we writhed on the bed, his hands pulling off my panties as he freed his erection from the fabric and the tip of his cock was pressed against my wet pussy, beginning to slip inside as he groaned and thrust his hips forward. He leant back and took hold of my legs and bent them back, my spine bending to open my hips totally to allow him access. He slid totally inside me, slowly now, the fiery rush we'd burnt up to get to this point forgotten for the moment - just me and him, his cock stretching me wide open as i felt it throbbing inside me. He looked down over my body, his eyes devouring my skin before they reached the sight of him deep inside me, our hips meeting as our bodies merged into one. He let out a soft moan and slid out of me almost completely before slamming inside me, fast and hard as the fire burnt me up again and I let out a cry, "James, please," as he fucked me now, holding my legs back as his hips jackhammered into mine and the sound was loud in the quiet room. Sounds were tearing out of his throat as I moaned loudly, so close now to orgasm but not quite able to slip over the edge until he lowered his hand to my clit and began to massage it, hard and quickly as his thumb beat a pattern into my brain as I shook and screamed out his name as I came hard, my pussy contracting around his cock as he thrust one last, hard time and groaned loudly and harshly into my ear as he came, the condom ballooning inside me as his body shuddered in the aftermath. I think this is going to be a good first visit home, don't you? My Brother's Lover "Uh, ah, mmmm, yes, fuck, brother, fuck me, use me like your dirty bitch, oh God yes!" I began to moan and scream, "Fuck my virgin arse, brother, take your slutty sissy sister'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, brother, 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 brother. "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 sister." I knew that with the extra attention of my brother 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, brother, 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 brother'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 brother'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 brother'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 brotherly 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 brothers but it did seem to have given me a new family role, Cynthia, my brother's slutty tranny lover.