The clock on the bedside table clicked loudly in the otherwise quiet room. A soft buzz of cicadas outside drifted in through the small gap in the raised window. The room seemed to glow with pink from the afternoon sun.
The room hadn't changed much since Rachel had begun her fashion phase in high school. Her closet (and the closet of the guest room) were stuffed with dresses and clothes she'd bought or designed herself. After getting her job with Limited Brands (home of Victoria's Secret and Pink), lingerie of all sorts found its way into her closets, drawers, and piles.
Aside from the old bed with the headboard and footboard made of metal tubes and painted pink, the room had a draftsman's table covered with her clothing sketches, a chest of drawers always hanging open and stuffed with her clothes, a small desk for her computer, and some shelves with mementos from childhood: stuffed animals, Barbie dolls wearing outfits she'd designed, photo collages of her with high school friends including the graduation shot from a year ago. It all made sense for a girl still living at home to save up money while she pursued her dream career. What didn't make sense was her brother, Len, lying down on her bed and in the condition he was in.
To start, Len was dressed in lingerie, specifically his sister's lingerie: satin string bikini panties, thigh high stockings, a tight satin corset with garters to the stockings, and a pink satin neck choker. The fact that the lingerie fit him perfectly was a blessing Len never stopped giving thanks for. In addition to the lingerie, he was wearing a pair of her "fuck me pumps" in patent leather with slender buckled ankle straps. He'd brought some of his own contributions to this play outfit. There was a large, cock-shaped butt plug more than filling his ass. Around each wrist and ankle was a strong pink leather strap with a D-ring. At the moment, sturdy metal chains ran from both ankle straps to the far edges of the footboard where they were securely padlocked to the metal. Another similar chain secured his left hand snug to one end of the head board with another closed padlock.
This is where Len had gotten several times before... softly fingering the last padlock for his right wrist. Of course, he couldn't close it and complete the trap he'd designed for himself. Even now if Rachel was to come home early, he would be in a desperate panic to unlock the other three and escape to his room to hide. That edge of panic had his breathing rapid and his heart racing even more than the deliciously tight and body-shaping corset. It was also what was giving his cock that extra, exquisite edge of erection that took simple masturbation to a whole other level.
He'd wondered if this was similar to what the people who partially choked themselves as they masturbated felt, some spike in excitement and pleasure with the danger and the risk. He was certainly addicted to this sensation and he enjoyed simply laying there, drinking every sight, every smell, every sensation into his mind, swelling his sexual hunger and desires. He'd wrapped himself in every feminine bit of Rachel, seeking to transform himself in his mind. Even her brand of lipstick was painted on his lips and he'd stolen a bit of her favorite clubbing perfume to dab around his body.
Wearing panties had started back when he first hit puberty and Rachel's drawers had provided him ample supply for his nightly fantasizing. For better or worse, the Internet had been the great educator, connecting Len to the world of panty-sluts, feminization, and most of all, sissies. Encouraged by similar fetishists around the world in their anonymous playgrounds, Len had learned and refined his play times. He'd even begun to shop for lingerie for himself in stores, terrified but also incredibly aroused at the risky process, wondering if the sales girls realized they were for him... slowly making his interactions more and more clear so there wasn't even a question and relishing in knowing that they knew what a sissy he was.
Now he was here on his sister's bed again, cock so hard it was aching as it lifted Rachel's panties into a tent he could see down. Precum was oozing out of his tip and pooling on his waist. He was completely shaved there and actually from the neck down. He'd joined the high school swim team just for the excuse to get to stay shaved and girly smooth and now after high school he kept it up "out of habit". Well that was his prepared excuse but the question had never come.
He shifted a little quickly listing all the sensations... the corset which was tight to give him a girlish hourglass body but kept his breathing deliciously shallow... the satin panties which slid around his bottom and hips like the caress of a lover... the exquisite pull of the garters on the stockings, tugging them up his legs... the enforced arch of the heels on his feet... the tightness of the pink satin choker... the pull and restraint of his bondage. He couldn't help but moan in his practiced soft high voice.
He let his mind dance through snippets of his favorite fantasies... bound and waiting to be used by pretty girls... bound and waiting to be force fed a guy's cock... multiple cocks... His ass twitched with special desire around the butt plug. Bound and waiting to be used... by Rachel.
He quickly pushed the thought away even though it gave him an even deeper jolt of desire. Surely his lingerie and bondage games were taboo but not in a way that thinking about his sister that way was. Still, wearing her lingerie made thinking about her sexually easier and those thoughts would not go away.
Unbidden, the image of Rachel out of the shower that he'd 'accidentally' seen six months earlier returned, searing and fresh in his mind's eye. He saw the curve of her full breasts, her round bottom and the little strip of hair she kept over her pussy. He saw how her blonde hair looked darker all wet and it laid wet on her shoulders and neck.
There were other images... times they'd gone to the pool together and he'd watched her sunning in her skimpy bikinis... glimpses of what panties she was wearing. He'd stolen enough glances that she already called him "perv". If only she knew.
He moaned and shifted again, the delicious ache of his rigid cock begging him to hurry with his play time, to edge higher and higher until the intensity of his need, the tightness of his balls almost made him pass out. He tried to draw it out further.
Which panties was Rachel wearing today? Wednesdays were usually a thong and a short skirt as she always went out after work with the other designers to celebrate 'hump day'. Satin, of course, as most of her panties were. Len was very familiar with the house laundry and tracked her habits. After his own graduation from high school as part of the deal of still living at home, he'd volunteered to do all the family's laundry. Rachel still washed her special pieces (like the corset) by hand but he got to appreciate all of her normal underwear and had become very proficient at avoiding the cleaning gotchas of different kinds of clothes.
Their parents had also engaged him to help with house cleaning and preparing meals after his job had fallen through and he hadn't found another one yet. Rachel didn't have to as she was able to pay rent though at their parent's forgiving prices. It just gave her time to relax while he always seemed to be taking care of something around the house.
He smiled thinking back to an off-hand remark she'd made a few weeks ago that never ceased to thrill him. He'd been carrying up a basket of clean laundry headed to the bedrooms when she passed him, some trashy novel in her hand as she headed to the back yard to sun herself. "Keep this up and we'll have to get you a little french maid's outfit!" The moment had gotten his cock hard many times as he imagined slipping into such a satiny, femme confection and letting her catch him.
His cock ached again, even more insistent that he bring this fantasy time to a close. He eagerly relented slightly and began to squirm on the bed, flooding his mind with the sensations of the tight and slippery lingerie, the way each piece pulled softly on his skin, pulled in ways no male clothing could heightening his awareness of what a complete sissy he was.
He was so close, his cock throbbing... fingering the open padlock around his right wrist... so close to being completely trapped and at the mercy of whoever found him all sissied-up... he was moaning louder now, the feminine timber he practiced daily... squirming more, trapped and desperate, every inch of his body an organ of arousal, every sensation, every idea... he wanted more... deeper... he wanted that flood of pleasure that every new line crossed gave him... he wanted to erupt as a sissy... squirming, writhing on Rachel's bed... in Rachel's underwear... doors all open... almost caught... almost discovered like this... he was panting now... whining... begging... he can't but he wants it... all that matters is an orgasm bigger than he'd ever felt before... its insane to even think about it but he can't help it now, lost in his sexual desires... he won't trap himself... but if he did...
click.
The final padlock clicked shut sounding like a gunshot in Len's ears. He was completely trapped now and he screamed as his cock and balls clenched tight, the erotic tension searing over his body as he arched his back and then came! Rope after rope of thick white cum shot from his cock all over the corset, then his belly, then pooling under the panties...
He passed out.
Slowly he drifted back to consciousness. The haze of erotic rapture had almost completely faded but he was still floating in the memory of the pleasure. Must not have been out more than a few moments. He'd never felt that good before. Maybe this is what heroin feels like? God he could kill for that pleasure.
Shifting, he pulled his right hand to start to free himself and felt the chain pull tight.
