One Step Too Far

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.

"FUCK!" he yelled, eyes flying open. He yanked hard with his right wrist and then his left one. He strained to just pull out of it but had to stop, his breathing ragged. Why did he have to buy the cuffs with the steel band?!? Why did he have to make it so real? Well, that is what made it so compelling, so intensely erotic. And what made it his downfall.

How could he have done it? He KNEW he could never close all four of the locks. He had to clean up and put her room back like it was. He pulled again and again, arms and legs, hoping something would give. Even the bed was solidly constructed with metal and he wasn't strong enough to break it.

"Oh God Oh God Oh God Oh God," he moaned, struggling to find some way out. The more he struggled, the more he found himself getting erect again. "Oh shit, really?!?" He moaned and was right back into his sexual fantasy world, now fully restrained and bound as a slutty sissy. He struggled and squirmed, feeling all of the clothing again and felt his arousal coming back in full force.

"Oh fuck no please don't," he began begging to his invisible captor. What if she made him eat her pussy? What if he made him suck his cock? The more he struggled and had to admit he was completely bound and trapped the more excited he got. His body had recovered quicker than he could remember and his balls ached.

He lost track of time but worked himself up again until his cock erupted. Less than the original, but cum still splattered the corset and his skin. More caught against the waist of Rachel's panties, soaking them.

Finally, his sexual obsession seemed to let go of him. He stared around the room. He held up each of the chains in turn, looking at them logically for some flaw in his design, knowing already that there was none. Pretty simple to secure a wrist or ankle to something heavy.

He let his head drop back.

"Okay. Life will go on. I'll survive this. Someone will come home and find me. They will be shocked but they'll have to let me go eventually. I'll clean up and strip out of Rachel's clothes."

Just talking it through calmed him a little.

"There will be a reckoning. What's the worst case? Kicked out of the house? Disowned? Police? No, they'd never go to the police but I'll probably have to find another place to live except I have no money. I could be homeless within days. Fuck, what would I do? I've broken everyone's trust but they wouldn't turn me on to the street, would they? Maybe counseling. Yes, I need counseling. An addict's group maybe."

He realized he was babbling so quieted himself. He felt his cum cooling on his skin. Glancing down, his cock had softened and Rachel's satin panties had settled over it again, the waistband sitting in and dividing the pool of cum, his cock gone. For a moment he enjoyed looking at himself in panties unmarred by a raging erection, feeling extra feminine.

He listened to the sounds of the street through his sister's bedroom window. Who would get home first? Would they tell everyone? He lay there listening for the tell-tale grinding rubber of car tires on the driveway. Glancing on the bed side clock, he guessed he had two more hours.

A long time to wait for hell to pay. Well, just so long as he didn't fall asleep...

The dream was intense. He was shackled all sissy, trapped and he was getting so aroused. Except for something pushing on his foot. He struggled to rise through the layers of sleep but finally opened his eyes. His predicament came rushing back to him and only made his traitorous cock swell further, tenting the panties. He looked to the end of the bed.

Rachel was sitting in the chair from her computer desk. She had a cocktail and looked like she was still dressed in her work clothes. She was looking at him in all his glory.

"So. Who did this to you?" she asked with an effort at calm, and took another long drink. There was an empty cocktail glass already on the table.

"I'm so sorry, Rachel. Please don't hate me. I don't know what came over me. I... it was me." She didn't look surprised that her offered fig leaf of an antagonist wasn't needed. She just stared at him several moments, sipping her drink.

"What came over you? What came over you to put on my panties? Came over you to put on my corset? To use my makeup? To wear my heels?" she said her voice growing louder and louder. "To lie on my bed? To fucking chain your perv ass to my fucking bed?!?" She steeled herself and attempted calm.

"I'm not surprised. I'm really not. Did you really think you could wear my panties and jack off in them and I'd never catch on? That you could use my lipstick and I wouldn't notice? I just had no idea you were perving all over MY BED! And what the fuck is up with the chains? What could you be thinking?!?"

He felt crushed. Having Rachel so angry at him was devastating. He felt like he was going to start crying.

"Please, Rachel. Let me go. The key is in the top of the corset."

"You're pathetic. I told my girlfriends you were a total perv but they didn't believe me. If they could see..." and with that her voice trailed off.

She stepped over to pull the key out and promptly put it in her pocket. With that, she left the room. He froze and listened until it was clear that she was driving away. He began to weep. Now his parents would find him too and he was sure to be sent off.

He laid there, miserable, until he heard Rachel's car return. He heard voices. Voices! Girls and guys! Rachel was laughing. His face burned red at the thought of the humiliation. He pretended that he couldn't recognize the voices of his sister's friends and just closed his eyes.

"Didn't I tell you? I told you he was a perv!" accused Rachel from inside the room. His eyes opened and saw Jeremy, Lisa, and Beth standing there as well. Rachel was still angry but the others were grinning and then laughing. What made Len sink even lower was that the humiliation was getting his cock hard again. He was a pathetic sissy slut!

"He's gone tonight! I shouldn't have to live with some sex maniac sissy pervert!" complained Rachel.

"Wait, wait," interrupted Beth. Beth was a beautiful African-American plus size model Rachel had befriended at the Limited. Len had drooled over her lingerie pictures online plenty of times. "This is actually perfect. Haven't you ever wanted to make your brother do anything you wanted?"

"He's already pathetic, doing laundry, cleaning, and cooking around here."

"Well, I can think of a lot more interesting things he can do. Think of every time you've been so horny and Jeremy here is no help." Jeremy shrugged his shoulders in acknowledgement. Beth leaned over and pulled the panties down to spring Len's cock free. "I mean, hello, he's what 7? 8 inches? I could use some of that at my beck and call!" Jeremy whistled and gave Len a wink. Len knew Jeremy was gay and also a model for the Limited.

"Jeez, Beth, he's my brother for Chrissakes," complained Rachel although her response was softer than Len had expected.

"Oh if you don't like that, I'm sure he eats good pussy. Wussy men love eating pussy and it looks like he wants to be a lesbian anyway."

"Lisa, tell her that's all crazy talk," pleaded Rachel, unwilling to surrender her moral high ground for the promise of blackmailed sexual favors.

"Well, I get you not wanting to think of your brother that way, but he's hardly your brother any more, right?" added Lisa with a thoughtful air. "He's... she's a little slut. A slutty little sister. I bet he'd do anything to be your sissy doll. I bet he'd suck cock."

Lisa's choices of words shocked Len. It was like she was reading it from one of the sissy forums Len hung around online. Rachel looked from one to the other and then back to Len.

"Alright, Sis, let's have it. Are they right? Are you a pathetic sissy fuck doll I should be using any way I please? You'll do anything to be my little dress-up girlfriend?"

Len could hardly breathe but he nodded vigorously and then blurted "Yes, Rachel, yes I want to be your sissy girl sex toy!"

The group laughed at Len's eager response which just made his cock throb. Even Rachel seemed to lose her anger a bit.

"I think we need to test him," offered Jeremy. "Do you know if he's gay?"

"The way he's always ogling me, I don't think so. Maybe bi but I never saw him looking at other guys."

"Well, I know just the test." With that, Jeremy, Rachel's gay friend, unzipped his jeans and pulled out a quickly stiffening cock.

"Oh God Jeremy," laughed Beth. "You've wanted to show us your cock forever!"

"Oh hush, you wouldn't know what to do with it," teased Jeremy as he moved to the side of the bed. "I'm betting sissy slut here knows!" He began to stroke his cock, getting it full and stiff, a little pre-cum on the tip. He leaned over the side of the bed, bringing the tip of his cock to a couple inches from Len's face. Len looked at Rachel.

"If I'm going to keep your secret, you better show me you're ready to do ANYTHING we say, perv," muttered Rachel.

Len nodded, meeting her eyes. There would be more discussed later but the deal was struck.

A flash caught Len's attention. Lisa was taking pictures and video with her phone. "Always have insurance, Rach," she added.

Len turned toward Jeremy's cock and opened his mouth. He covered his teeth with his lips and strained forward to slide the head in his mouth. He locked his lips around the head and began to lick with his tongue.

"Oh fuck!" blurted Beth. "She's a sissy cocksucker!"

Len thrilled to the words and became more eager, as far as his bondage allowed. Jeremy soon began thrusting and Len felt the man's big cock fill his mouth back to his throat.

"Mmmm he's got a nice, tight mouth," grunted Jeremy bracing himself with a hand on the head board.

"Suck that cock, sissy," cooed Beth. "What a slut you are! Taste his cum!" Len started moaning in pleasure, thrilling to have a cock in his mouth as he'd fantasized about countless nights. He even tried to deep throat the cock but coughed and couldn't keep it down very long.