tagTransgender & CrossdressersBrotherly Love, Sisterly Love Ch. 01

Brotherly Love, Sisterly Love Ch. 01



My brother and I were especially close, as twins often are. We shared everything, including all our thoughts, feelings, experiences and desires. Even though we were eighteen, we still shared a bedroom too. It wasn't like there were things that we kept private from each other, it was the two of us wanting privacy from the rest of the world. This closeness and togetherness was often particularly valuable to us as neither of us had many friends apart from each other. Some people might suggest that that was because we were so close to each other that it shut other people out. Anyway, whatever the reason, we were always glad of each other's company.

Inevitably, our sexual awakening came together, as we would discuss our image of our ultimate fantasy girl and what we could do together and we would both lay back on our beds and masturbate, often reaching a climax almost simultaneously. However, these fantasies were to remain no more than teenage boys' fevered imaginations. Neither of us ever enjoyed much success with girls and by now, aged eighteen, we both remained painfully inexperienced, both virgins. While all the other guys in school were bragging about their sexual exploits and conquests, we felt ever more and more left out and more and more curious about what it would be like to be with a woman.

It's hardly as though our house was free of any kind of sexual activity, though. Whenever she was home, our twenty-one year old sister Charlotte would bring men back to her room and we would hear through the thin walls between our bedroom and hers the screams and moans and we would imagine the kinds of sexy situations we could see if only the wall wasn't there. Now, don't go thinking we were obsessed with incestuous lust for our sister, but understand that it was hard for us sexually frustrated teenagers living in the same house as a promiscuous woman in the years of her blossoming sexuality.

Even though she was our sister, both me and Robert had to admit she was absolutely gorgeous. While the men in our family were all short, unremarkable and unassuming in appearance, the women were distinguished by being tall and slender with striking good looks and Charlotte was the sexiest of the lot. She had cascades of shiny, dark, wavy hair falling over a face whose beautiful, soft features were offset by a wickedly naughty grin. Her breasts were pert and round and just big enough to draw the gaze of any passing guy. That was if their attention wasn't instead drawn to her long legs which she delighted in showing off in the shortest of skirts. Yes, not only was Charlotte blessed with natural beauty, she also did everything she could to draw attention to it by dressing as sexy as she could, until no man she walked passed could resist staring and drooling. I guess she got that from our mother, who was something of an object of desire in her own day and who still turned heads of younger men (and even some of Charlotte's boyfriends) despite being well into her forties.

Anyway, that's Charlotte and this story isn't really about her, at least not yet, so none of this is especially relevant, except for the fact that, even when she was living away at college, she had a wardrobe full of sexy, exciting clothes in our house. These clothes do play something of a vital part in our story.


Richard and me used to sneak into Charlotte's room and take things. At first it was her lingerie catalogues. We didn't have any porno magazines and so this was the closest we could get. Not that we minded too much, Charlotte loved for even her underwear to be as sexy as possible so we had pages of great looking girls wearing the sexiest underwear to jerk off over. At first, we thought it was mostly the hot models that were turning us on so much but increasingly, we realised that it was the super sexy underwear on show that we really liked. When we did get our hands on an actual porno magazine, we looked on the naked girls with a little disappointment, not seeing their curves covered in silk, satin and lace.

After this discovery, we went looking in Charlotte's room for more than just pictures, we wanted the real thing. Fortunately, the drawers in her bedroom were still filled with her gorgeous underwear, even with her having taken much of her stuff back to college. We grabbed some of her panties and rushed back to our bedroom. Our cocks were already semi-erect from the excitement. We dropped ourselves down onto our beds side by side and pulled out our cocks, beginning to stroke them while admiring and sniffing our sister's panties. Richard had taken a pair of frilly black lacy french cut panties while I had a pink silk thong. Richard began to rub the panties against his shaft and moaned with pleasure.

"Man," he groaned, "You should try this."

I took the pink thong and wrapped it round my cock as I stroked it. It felt so soft and sensual and erotic against my skin, I could really see why Charlotte wanted to wear things like this all the time, although I did come to wonder how she managed to go about her normal business without just being permanently aroused.

"Oh yeah," I said, rubbing my cock with the panties, "That feels soooo good."

Much quicker than usual, we soon found ourselves both blowing our loads all over into our sister's sexy panties and this was just the beginning. From then on, jerking off with Charlotte's panties became a regular occurrence between the two of us, and one that would lead to much, much more.


Of course, the time we spent jerking off into sexy panties in part just served to make us want even more to enjoy some kind of real sexual intimacy with a girl and feel her body in such pretty lingerie pressed against us. One day, we were lying back side by side across my bed and I mentioned this to my brother.

"This is all very well," I said, a pair of pale blue bikini cut panties covering my semi-erect cock, "But it's not the real touch of a woman, no is it?"

That's when Robert reached across and did something totally unexpected. He put his hand over the pale blue satin and wrapped his fingers around my shaft, beginning to rub it.

"What are you doing man?" I said, turning, shocked, to face him.

"I thought you'd want to feel what it would be like for it to be someone else getting you off for a change."

"Yeah," I said, as if stating the obvious, "A girl, not you."

"Don't worry," he said, "I know just the thing, wait right here." He grabbed the sky blue panties that lay across my crotch, "I'm gonna need these."

With that, he left the room and I sat there on the bed waiting, with my pants around my ankles and my cock exposed. I wondered what he was up to. We were normally so knowledgeable about each other's secrets but I had no idea what was happening now. I had to admit that when he had put his hand on my cock, my body had sung with a little thrill of excitement, but it was just too strange, he was a man, and my brother, after all. Now, after waiting for quite a while, I was no longer aroused or curious but becoming a little bored. I had just bent over to pull my pants back up when I heard footsteps and an unfamiliar voice in the doorway.

"You wanted a girl, well, how about me?"

I looked up, startled, I didn't think there was anybody in the house, and there was Robert standing in the doorway. Or rather, not quite the usual Robert. At first glance, it was indeed a pretty teenage girl, albeit a short haired, flat chested one. Only after a second was it apparent that it was my twin brother dressed up. He was wearing some of Charlotte's sexy clothes, his legs were bare except for a tiny, short denim mini-skirt of hers and three inch wedge sandals on his feet. Fortunately, his legs like mine were largely hairless and it was now pretty clear that Charlotte wasn't the only one to have inherited our mother's long, elegant, feminine legs. On top of that, the girl, or rather Robert, was wearing a pale blue satin camisole that we had seen in Charlotte's catalogue paired with the panties I had had earlier. Sure enough, Robert lifted his skirt to give me a little flash of underneath to show me he was now wearing the same panties. The cami was made of satin thin enough to show Robert's skin beneath and was decorated with white and turquoise green flowers, much like the panties. I could see that he was also wearing shimmering pink lipgloss.

"Robert? What the....?!" I began to say, but he interrupted.

"Call me Rebecca," he said in the same soft, high pitched feminine voice he had used earlier, as he tottered over his higher than usual footwear, swaying his hips in an alluringly womanly way.

I stared open mouthed at the transformation in the twin I thought I knew so well as he/she knelt on the ground by my bed. Finally, I opened my mouth to speak but he/she put a finger to my lips and I noticed that he/she had painted his/her nails in a similar shiny pink to his/her lips.

"Shhh," came Rebecca's voice, "Don't talk, just let me show you what a girl can do for you."

With that, "she" leaned over and wrapped her fingers around my cock for the second time that afternoon and began to stroke until, very soon, it was rock hard. Close up, looking at "her" face, it was pretty clear that "she" was really my twin brother but she still looked pretty good as a girl and the look and feel of her hands with their pink painted nails, as they ran all over my cock and balls in just the way we liked to do for ourselves, was truly arousing.

"Rebecca" shifted position so she was sitting up beside me on the bed. Still stroking my cock, she leaned over and played with my ear with her lips and tongue as she whispered in the soft and sensual voice she was perfecting even as she used it.

"See how hot this can be when there's a girl involved," she whispered, "And look how wet you're making me."

She pulled away and lifted her skirt where there was now an obvious reminder of her masculinity. The blue satin bikini briefs were now straining to contain Robert's hard cock, the swollen head of which poked out from above the elastic waistband. Sure enough, as she had promised, the satin was soaked to being transparent with pre-cum. Still rubbing my cock with one hand, Rebecca reached over and took my had in her free one and guided it onto her panty covered meat.

"See how swollen you make my little clitty," she giggled.

Instinctively, I ran my fingers along and around her cock through the thin material of our sister's panties. It was just like stroking my own (despite the way she was dressed, "Rebecca" was, after all, my identical twin), except rubbing this hard shaft elicited a hot, sexual and distinctly feminine moan from my companion. What with the sounds and looks of Robert playing the hot girl Rebecca to perfection and her expert hand job, it wasn't long before my cock spurted forth all over her hand and she filled her panties with similar creamy white juices.

"Fuck, honey," she moaned, "You sure know how to excite a girl."

I collapsed back on the bed and watched Robert strip out of Charlotte's clothes (or, rather, what I had come to think of as Rachel's clothes) and transform back into himself. Sitting back beside me, he turned and grinned.

"So, Richard," he said, "How was it, being with a woman?"

"Pretty awesome," I grinned back, and it had been, I was dying to see what more Rebecca could for me and to do what I could to thank Robert, "I hope you can get an experience like that some day soon."

"It might be sooner than you think," he replied slyly, "That girl, Rebecca, has a twin sister and I'm hoping she can show me a good time," and then reverting to speaking in Rebecca's womanly tones, he added, "So, how about it, Rachel?"


It was a week after I had dressed as Rebecca and given my brother a hand job and once more we had the house to ourselves for the weekend. I found myself in Charlotte's room looking through her wardrobe for suitable outfits while Richard was in the shower, shaving off all his body hair. Like me, he didn't have too much hair anyway, but we had the whole day and without the hurry that I had been in to reveal Rebecca to him, we were going to be able to really have a go at a proper transformation for Rachel.

Richard hadn't needed too much persuading to try things out the other way around and to become "Rachel". He had acted a little coy and unsure at first but I could see he longed to further explore our sexuality as I did.

"You think it feels good just touching the panties, imagine how sexy and turned on I felt wearing them," I coaxed him, "And it's not just panties, there's all those different kinds of lingerie we coveted in those catalogues."

I didn't tell him quite how sexy and aroused I felt in playing the role of the seductive girl. Just for those few minutes, the persona of Rebecca and her sensual clothing had made me happier and more excited than I had been in years. I actually felt quite jealous of my brother getting to play the woman today while I had to be boring old me in my ordinary male clothes. As I said, I didn't tell Richard all this, but we're twins and we can often tell what the other was thinking, that was when we weren't already thinking alike anyway. It could well be that he would love playing Rachel as much as I had Rebecca.

I'd been thinking about it ever since we'd first masturbated into Charlotte's panties, what would it be like to wear them? To wear other sexy lingerie? To dress and act like a hot girl like Charlotte? And, when my brother had wanted to feel the touch of a woman then I saw my chance to explore these questions and feelings. After all, we had always shared everything, hadn't we?

Back to today, and I could hear the shower stopping and Richard getting out and padding into the room wrapped in a towel. I turned my thoughts back to consider today's dress up session. Richard had said that he was most impressed by Rebecca's long, beautiful legs, every bit as sexy as Charlotte's, Richard had said. As Rebecca's twin, Rachel should have similarly excellent legs, a feature I was determined to bring to the fore. I was thinking stockings, heels and very short skirts, and had found in Charlotte's closet clothes that would suit my purposes well.

I had found a tight, short, little navy blue dress that Charlotte had worn to summer parties when she was out age. The skirt of the chiffon dress was barely even knee length and the plunging v-neckline contrived to show off her blossoming cleavage. Fortunately, in my searching through her things, I had found some silicone breast forms she had used before she developed enough and wanted to look sexier and older than she really was. So, at least Rachel would have bigger, better breasts than Rebecca. Also, I had picked the dress because it had a pale blue ribbon waist cincher that tied in a bow at the back, which Charlotte had used to give her a more curvy figure. It would force Rachel's waist in and her chest out and create a more feminine hour-glass figure for her.

Richard was now standing, surveying all that I had found for him to turn him into Rachel. He seemed a little unnerved by how far I was taking the transformation but didn't turn away at all.


I was now feeling a little unsure of myself, seeing Charlotte's clothes all laid our for me by my brother. It wasn't that I didn't want to do this. No, my brother had done enough to convince me of the pleasure that could be gained from such an erotic game of dress up, not so much in what he said but just the sense he gave. Twins can tell, you see. It was more just nerves. I mean, it's one thing to get turned on looking in a lingerie catalogue, but it's a big step from that to dressing up in your own lingerie, not to mention what it could lead to, what I wanted it to lead to. I felt scared, but it was a mixture of being scared and excited about what was to come. In the shower, with my body hair washing down the drain, feeling my newly soft and smooth body, I was already beginning to feel more like Rachel, wanting to be more like her.

I dropped my towel to the floor, my body dry but still soft. Robert handed me a pair of panties, white lace with little bows around the waistband. I knew them well, I had told Robert a couple of weeks earlier that they were my favourites in Charlotte's wardrobe. I smiled now at the recognition and his memory. I stepped into the panties and slid them up my legs. Robert was right, this was way better wearing them than feeling them. My cock and ass were snugly enveloped in soft, sensual lace. Robert helped me into a matching lacy white bra and filled the cups with Charlotte's breasts forms, giving me a quite convincing B-cup.

I was already feeling girlier. I needed Robert's help again to clip on the white lace garter belt, but then when he passed me the white silk stockings, my heart skipped a beat. They were so sexy, I was shocked Charlotte would leave things like this behind at home, and I was dying to put them on. I was not disappointed, an electric thrill ran through my body as I rolled the sensual silk up my newly smooth, shaved legs. Robert helped pull the gorgeous, dark blue dress over my head, it fell tightly into place around my body with the skirt flaring out a little from the waist but barely long enough to cover my stocking tops. Robert tied the pale blue ribbon tight around my waist, forcing my figure into a more feminine shape. Then it was just shoes and make-up and my transformation from Richard to Rachel was complete.

The shoes were pale blue with six inch stiletto heels that were almost impossible to walk in but made my calves and legs look even better, enhancing both the curve and length of them. For my make-up, I left Robert to apply it all, he was really no more experienced than me but he seemed already quite a bit more confident. He particularly gave me very dramatic eyes with long lashes, dark eyeliner and pale blue eyeshadow. My lips were painted a pinkish shade of red and, as with Rebecca, my hands were made more feminine with painted nails, in my case a glittery blue.

Admiring myself in the mirror, I couldn't see anything of Richard, she was all Rachel, I was all Rachel. And Rachel was hot. I couldn't believe it, I looked in the mirror and I was gorgeous with my long sexy legs in their short skirt, stockings and heels. My breasts jutted forwards convincingly and, with the make-up on, my face was not only feminine, but attractively so. As guys, me and Robert had always faded into the background and now I understood why. Our slight figures and soft complexions were those of beautiful young girls not masculine men.

But, it wasn't just the look that had transformed me to Rachel. The feel of the clothes was staring to change my outlook too. I loved the feel of the girlie panties on my cock, and the sensual silk stockings that rubbed together with every move I made. I loved how the dress clung so tight to my waist and then rustled loosely around my thighs, it felt exciting and free and new. Just at that moment, I wished I could always remain that way.

Robert turned me to face him and smiled at his work, "Wow, Rachel, you're even sexier than your sister," he said, his impressed voice sounding pretty genuine, "Let's see if you can do everything she can."

I no longer felt any nerves, I was feeling just as Rachel would be right nor, a nice girl about to turn naughty. I knew just what Robert wanted from me and I gave him a lascivious grin and pushed him back onto Charlotte's bed and pretty quickly I had unbuttoned his pants and pulled out his cock. It was already quite hard and I gave a little giggle and looked up at him.

"Ooooh, did I do that to you, honey?" I said, my Rachel voice girlier and higher pitched than Rebecca's sensual, womanly tones.

It gave me a thrill to know that just looking at Rachel had already given my brother a semi hard-on. I was determined to turn him on even further. I knelt on all fours in front of the bed, my ass in the air, giving him a good view of my skirt riding up and my white stockinged legs, leaning forward to show off my fake cleavage which he was looking straight down. I licked my pink lips lustfully and began to stroke my hand up and down his cock, which I could already feel grown harder and thicker in my hand.

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bysexy_jessie© 8 comments/ 167907 views/ 122 favorites

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