He set up his pancakes, keeping the pat of butter in between the two for an even distribution, careful with the bottle of syrup as to not let it drip down the side. His long, slender finger tracing the edge of the spout, cleaning off the excess before popping it into his mouth and licking the tip clean. My little brother has always been a meticulous, neat person. He’s been staying with me and my boyfriend for the summer, just crashing on our couch because my apartment is closer to the campus where his classes are being held. It’s been years since we’ve lived under the same roof, and truth be told, there are a lot of times that I wished we still did. We had a lot of fun growing up together; what with him being several years my junior, it was easy to always get him to do what I wanted.
I usually got to pick how we spent our lazy summer days while our parents were at work. It started out innocently enough, every girl likes playing with dolls and what better to dress up and play with than a willing, malleable participant. We got older and grew out of the make believe tea parties and balls, but every now and then I still liked to dress him up, practice my makeup application skills, and see how pretty I could make him. It never crossed my mind that it was odd that he was never reluctant nor did he ever refuse.
We settled in on the couch after cleaning up after breakfast and had the tv on in the background while we each did our own things, me on my laptop, him on his phone. "My boyfriend is coming home in about an hour or two," I casually mention, "are you going to be out at all today?" My brother shrugged, "No, not really, did you want me to leave?" "You don't have to, if you don't think it'll be awkward hearing me with him." He kind of makes a face, but it's pretty obvious that it's not something that would bother him. "You little pervert," I tease, "come on, we have a bit of time, let's both go get dressed."
He sat down on my bed while I rummaged through my closet, trying to see what would catch my eye. A pair of thigh high stockings in white, a red and white cotton lacie panties and the matching bralette, all to be hidden beneath a plaid pleated skirt and a short sleeved button up. If we are going to dress up, I really don't see why we wouldn't go completely over the top with it all. I have all of the items picked out and lay them down on the bed next to where he's sitting. He removed his shirt and jeans and laid them down on the floor before taking his spot back on the bed. I nod at him to scoot back and take a seat between his spread legs. I pick up his legs one at a time and put a stocking over each foot, pulling it up, gentle as to not stretch it out too much, slowly so that he feels the nylon enveloping his calves and then his thighs.
The panties were a little trickier, as there were still some lines we never crossed. I had seen his penis plenty of times, but never had any kind of urge to touch it. He removed his underwear himself and I held the panties open at his feet for him to step into them. Usually, he'd pull them up himself, but I did it today, careful to avoid accidentally brushing my hand against his dick. It would have been easier to avoid if he weren't already nursing an erection, precum already creeping out. "Don't get my stuff dirty," I squint at him just as I let go of the panties, allowing the elastic waist to snap against his skin.
Everything else went on, piece by piece to complete the outfit. I took the time to admire this slow transformation, each item making him more and more feminine, each item changing his demeanor and stance ever so slightly. He stood up straighter, stuck out his cute little ass, and found it increasingly difficult to hide his delight in how sexy it all looked as an outfit. The skirt was shorter on him than it ever was on me because his legs were significantly longer, the bottom of the button up shirt also just barely touched the top of the skirt. "How do I look, sis?" He pulls at the hem of the shirt, it’s not quite opaque enough to hide the bright red bra from showing through, eagerly awaiting my approval. "Like the naughtiest of the sluttiest school girls," I tell him, half giggling because I knew that's exactly what he'd want to hear about himself.
I was putting the finishing touches on his make up, matching the lip gloss to the shimmery blush dusted across his cheeks, darkening his lips, staining them with a rouge, when we heard the lock on the door turn. "Shit!" we both shot each other a panicked look, "my boyfriend is home." I wasn't expecting him to be so early, but there wasn't much we could do at this point. Before we could even think to start taking anything off to hide what we were doing, my boyfriend was already halfway to my room. “Hey guys, what’re you up to?” he says from the hallway before stepping into the doorway and losing all train of thought when he lays his eyes on my little brother and me. A pin drop could be heard in the 5 seconds everyone just stared at each other.
My mouth couldn't hold it anymore as it widened, corners turning up and out, I burst out laughing at the ridiculousness of the situation. My bf joined me while my brother stood there blushing, beet red nearly head to toe, his posture shrunk back, hunched, and avoiding eye contact. Lipstick still in hand, I put some on and went over to kiss my bf hello. "So, this is what we used to do when we were younger and bored." My bf shook his head, still fairly amused. He didn't have any sisters so he didn't have much idea about what interactions were in the realm of normal.
"Let me show you what a good job I've done!" I walk over to my brother and start pointing out the different parts of the outfit. I show off how the skirt fits him, even flipping it up to show off the ass hugging panties, how the button up perfectly accentuates his thin waist and creates a bit of hip and really feminizes his body. There was just one last piece, I went into my closet and pulled out a wig I had for a costume one year. We were already caught and too far in to turn back now, my brother continued to comply. Embarrassed, but it was clear that my bf wasn't going to be mean about it. I adjusted the wig and brushed the stray hairs out of his pretty little face.
"Doesn't he look like a real girl?" He still hasn't said anything, but while turning him, I noticed his bulge has not subsided. I stand up next to him and ask my bf, "So whose ass looks better in my panties?" I hop up on my tip toes a little to lengthen my legs, but also just to jiggle playfully. He walks over to us and pretends to inspect us fairly, grabbing my familiar cheek and reaching between my legs to get a firm squeeze. I can see him hesitate for half a second, but then he reaches out to do the same to my brother. A smirk forms on his face as he says it's a tough call, maybe we should test it a little more, not only who has the better ass, but who the better girl is. “Who’s going to be the bigger cockslut tonight?” he teased. I looked down at my bf’s crotch and noticed that he, too, had quite the bulge pressing against the zipper on his jeans.
Before I knew it, I was on my knees in front of him, unbuckling his belt, unzipping his pants, and unleashing him. I felt my brother kneel down next to me. It looked even bigger from that angle because of the way it hung from his body, gravity pulling the weight of it down, perpendicular to his pelvis. My gaze direct, instead of looking up or down at it. Bouncing on each throb, slightly swinging between my eyes and hypnotizing me into a cockdrunk haze. My fingers make their way around the base as I opened my mouth with an outreached tongue, pressing his cock down onto it and guiding it straight to the back of my throat. I wrapped my tongue around the underside, swaying it side to side, and kept my lips sealed as I pulled my head away. I licked and teased his rod, kissing it up and down, getting every surface of it wet, tantalizing him with the view of my mouth worshiping his perfect cock.
I could feel my brother’s eyes glued to the scene, the raw tension in the room, the aching yearning in his thoughts. I pointed it towards my brother. “What did I tell you about keeping my panties clean?” There’s a notable wet spot built up along the outline of his dick. “It’s your turn,” I tell him, “don’t worry, I’ll help you.” I’m still holding my bf’s cock, my other hand now on the back of my brother’s head, easing the two closer together. He’s not showing any signs of resistance, his mouth opens as he licks his bottom lip, anticipating the moment their skin will meet. His chest heaving, accommodating his racing heart, and with a sharp inhale and a sigh of release, my little brother tasted his first cock. Any residual shyness left him and he downed it like it was the first real meal of his life. My teasing style was not imitated in any way.
Soft moans heard from both guys, I loved it even more than I thought I would. He picked up the pace and started sucking down the cock, my hand was still on the back of his head, but I wasn’t even doing much pushing. He forced himself down the length of my bf’s thick cock, came back up and licked, slobbered, and drooled all over it, gagging himself, continuing despite the discomfort. My hand was merely an excuse. I was “forcing him,” but we knew the truth. He was the hungrier one, the more driven between the two of us, the perfect sissyslut, out-performing his big sister.
The result was undeniable. My bf was lost in the pleasure of having his dick throated by an eager cockwhore, one who knew exactly how it should be done. His hips bucked, thrusting forward, pushing deeper down the willing hole. His balls began tightening and pulling closer into his body. “Make him cum, sweetie,” I start stroking my brother’s hair, “You’re doing such a good job.” The slick saliva coating every surface of my bf’s sensitive cock, combined with my brother’s impeccable tongue work and his unrelenting will to have no limit on how deep he could take the entirety of the member he was servicing had my bf emptying his load in no time. He started spurting on an upstroke, some of the cum splattered to the side of my brother’s face; the rest of it deposited directly on his tongue. He swallowed and then wiped off his cheek with one of his fingers, cleaning off the excess before popping it into his mouth and licking the tip clean. I leaned over and kissed him lovingly on the forehead, “you are such a good girl.”
Source: reddit.com/r/sexystories/comments/306d55/lets_both_get_dressed_sissycdinc
your stories always get me so effing hot.
Awesome!