5/5 Sissy Castration Stories – YOU KNEW

You had willingly searched and jerked off to sissy porn for years. You regularly read Literotica fiction and would love to stroke yourself for hours. It was not uncommon for you to chat or flirt with other bloggers or online friends. You sought out a deeper role. The hypnosis of online flirts and short sissy skirts led to cravings, stronger and stronger with each passing week. You knew that this was a slippery slope; you knew you wanted more.

As a grown man, now 30, you loved your guilty secret of pining over females and their magnetic power. You paid unusually close attention to women’s fashion styling and was rewarded with a heightened sense of sexuality. You lusted over gym barbies, cocktail waitresses, beach babes, and young hot moms, always looking so put together and fuckable.

You loved to come home from work and pretend to be a chick. Occasionally you got poppered up and would dizzily finger your ass. There was nothing like cumming with something up your ass. You explored your hole and enjoyed taking on a penetrated role.

You began to have feminine thoughts and to try to empathize on how women must feel during sex and relationships. You always loved their delicate style and the soft luxury of feminine clothing materials.

It wasn’t until about a month ago that you got drunk enough to order some toys and lingerie on Amazon. A simple series of 3 butt plugs, each graduated in size, a short red plain school girl skirt, pink thong with white lace adornments, and white thigh high stockings that did not require a garter. You felt this was a good basic start to living out your fantasies at home, in private.

The clothes arrived on Friday. When you got home from work you jumped at the opportunity to dress up and goon out. You showered, shaved your sissy balls and cock, shaved your thighs and ass, and trimmed your lower leg hair as best as you could.

Lotioning and perfuming yourself before getting dressed the first time was a rushed and sweaty-nervous experience. You used some coconut oil lotion and a sample of ladies perfume that an ex-girlfriend had left at your place. As you sprayed the bottle on your neck, you were so eager to feel like a bitch. You remember your shortened breath and excitement.

You slid up the stockings first, and you remember it being easier than you thought it would be. Girls always made such a fuss. Once you had both stockings rolled all the way up your shaved and groomed legs, you evened them out in the mirror and felt just how good it felt to rub your legs together. The sound, the sensation, the nylon pantyhose was cooling and so shockingly soft on your skin.

You gasped at the simple pleasure of your legs and feet teasing yourself. You wanted to roll around and jerk already. But you continued, and slid the pink panties up your legs and tucked in your smooth cock and balls. Somehow it seemed they knew it was time to be feminine, and your balls had risen up toward your tummy and cock was limp as it could be.

You felt such a yearning in your stomach and backside. You felt hornier than usual, and sexier than usual. You wondered if there was a correlation.

You remembered the butt plugs and somehow had a faint whiff of poppers cross through your olfactory memory. You grabbed the small brown bottle from your nightstand and took a short draw. You held in your breath and attempted to relax, before a rush of warmth and radiant passion took over your body.

Your hole clenched. You relished in the anticipation. You pulled your panties to the size and bent over your bed. You lubed up a Medium sized butt plug and slid it in slowly, teasing your hole, as you had liked to do with your fingers. You went in and out, gently but forcefully stretching out your little hole. You wanted to be good.

Fitting in past the large bulbed end of the plug, you sighed deeply as the penetrator slid into place and nuzzled up to your prostate. You seized the opportunity to clench your anus around the plug and acknowledge its invasive presence. You felt like such a bitch, as you pulled your pink thong back into place. It was tight and stretchy, holding your plug in place, not letting you push it out from your eager hole.

You were almost finished getting ready. You pulled the skirt up your nylon-clad legs, wondering how pink pantyhose or black fishnets might look. You thought about what a full nylon bodysuit might do for your arousal.

You knew how to zip the skirt in front then slide it around back. You had watched your sisters and her friends do it all the time. You loved the voyeurism of watching ladies undress or dress. This was all part of your arousal. You wanted to be one of them. As you pulled the skirt around and flattened the pleats, you sighed again and this time felt your cock begin to stiffen. Your ass squeezed the plug and you moaned with a pouty lip, wishing you had some lip gloss on to complete the look.

You couldn’t get over how sexy your legs looked. From the waist down, it amazed you how passable you thought you were. Your slender and muscular legs presented themselves well in the hosiery and skirt, but you knew there were some things that would complete the look.

Painted toenails. Belly button ring. You cringed at what a girly and crazy thought that was. Your cock stiffened, imagining dangling jewelry and a diamond stud pierced into your tummy. It turned you on to consider the sex appeal it gave for women. You knew you wouldn’t go that far, you thought. But you figured nailpolish would up the ante for next time.

Next time was inevitable. You knew this wouldn’t be your last time feeling this sexy. You knew you could definitely wear and conceal toe nail polish, as part of your naughty secret at work and in public. You thought about how you could wear the thigh highs and panties under your slacks or jeans too. Of course, you had thought about all this before. But now it was real.

Your wanton desire for feminine touches was becoming overwhelming. You took a breath and decided to smoke a joint. It relaxed you, and you smoked like a girl.

You got high there on the floor, laying down and rolling around, rubbing your legs together and posing in the mirror, bent over in your skirt. You loved the sensation of it all and wanted to go deeper. You knew your first time should be memorable.

You knew that going online like this would arouse you wildly. You quickly found one of the men you regularly exchanged messages with online, and you were pleased to see his green indicator bubble as Online Now. His location was 5.9 miles away, as it always had been – this particular man was one you had seriously considered hooking up with due to his proximity and assertive way of writing.

You had never seen his face, but you loved his chats. You loved re-reading and edging to your own convo with him. You had teased this man for a few months, sending him pics of yourself naked and a full face shot as well over time. You had said you wanted to meet up with him, but you knew you would always flake out.

You knew this time could be different. You knew it was a Friday night and there were no plans. You quickly shot him a note that seemed to fly out from your fingers. “I’m ready.” The period on the sentence made you feel like it was so official.

There was a flash of hot passion that ran through your spine and down into your ass and prostate. Your balls tingled and rose up in your panties. Your cock throbbed and your hole clenched in sync.

You knew this man was serious. You could see him typing in the chat bubble, as you had seen many times before. His message was what you had hoped for in your lust-fueled and stoned horny state of mind, but it contained the stark ultimatum that you feared was on its way:

“Good, boy. At last. Come to my place within the next hour, or I will block and remove your profile. Enough teasing, from you. 565 Edgewood Lane. Knock hard twice. Clock begins NOW.”

You squirmed with arousal and squeaked with nervousness. You hated and loved the now-or-never mentality. You felt like you were being forced. You knew that force turned you on.

You were glad to hear that the man seemed to be expecting your message. You didn’t even know his name, just his online username, DominantDaddy. You loved this name and his private way of coaxing you in from afar. He sounded serious and experienced. You knew that deciding to go there would be a risky and exciting endeavor. You chose to get ready.

You knew your ass would be in play. You removed the plug, cleaned up a bit, and went ahead to push in the 3rd and largest sized butt toy. Your ass was successful in swallowing it, as you had committed to your role as a receptacle. It was always in your head to be objectified and lusted over.

This was now your chance. This man had wanted you, you reasoned. This man had known you would come around, again. He knew you needed some reigning in and support. You knew you wanted to make sure it went well. You pulled your panties back up and checked to ensure your stockings were held up evenly and that you looked the sexiest you could.

You couldn’t wear the skirt over there. That would be too far. You didn’t want to be seen in public crossdressing. You slowly, and in genuine strip-tease fashion, seduced yourself in the mirror by slinking out of the plaid schoolgirl pleated fabric.

As it fell to the ground, you made another pouty lip and mouthed “I’m baaaad” to yourself in a sultry, poorly-done-slutty, voice. You were convincing yourself that you were indeed bad, and headed down a road that you knew would be dangerous. This scene was playing out like a movie fantasy in your head.

You pulled up your sweats and threw on a hoodie. You slipped into some sneakers and noticed how funny the nylon felt inside your shoes. Your toes felt naked and yet still somehow slippery and smoother than ever. It was sensational. Your cock felt great in the panties under your sweats.

You knew you could hang out in this sort of thong anytime. Your dick danced and twitched as you walked to grab your phone and keys before heading out the door. You thought about leaving your wallet on the table by the door.

You paused and reasoned you would want to have ID and some cash while driving. No credit cards. But you took $20 and your drivers license in case of emergency. You didn’t know this man you were meeting. But you wanted to take at least some precaution.

You buckled up and started the engine. You knew the way to the man’s house after looking it up. The 10 minute drive would feel like an eternity, considering what the man might have you do, for his amusement and entertainment.

You remembered he had called you an “ultra sub slut boy” several times during your chats. You recalled he referenced something called “slut duty” and how he once had seemingly joked about “whoring, pimping, and using” you in a “safe and sane, discrete setting”. You knew that being pimped and whored was seldom safe and far from discrete.

Your cock felt insignificant when compared to the throbbing in your ass as you drove. You tried to avoid bumps. You kept your white-knuckles on the wheel and considered turning back.

You knew your ass was likely to take more action than just this silicone plug. You weren’t sure if you were ready, but you knew you had come this far. You knew you had to give it a try.

Pulling up to the address on Edgewood was a relief. You saw his house with a light on the porch. It was normal and unassuming in a good part of town.

The clock showed 7:28pm. You had a couple deep breaths and turned off your phone. You put it in the center console along with your license and money.

After a sip of water and adjusting your plug and panties as best you could, you got out of the car, locked it, and proceeded towards the front door. You knew his directions were clear as day.

As if possessed by your own lust, you did not pause once you got to the door. Two loud knocks rang out, as if somebody else’s hand had done it. You had made it here. You knew you did not want to turn around now.

Anticipation boiled inside you over the next 12 seconds. At first there was a long dropping pause of silence and your stomach churned. Then you could hear the man inside moving around. You sensed his energy coming to the door.

You felt you could see him inspecting you through the eyehole. As before, he got to see you long before you got to see him. He paused on the other side of the door intentionally, letting tension mount, before you heard the handle turn and click.

The door swung open and you were greeted with a tall and sturdy Sir, at least 6’3″ and 240 lbs. He wore dark jeans and a dark grey t-shirt, showing off worked out arms and broad shoulders. His brown hair was greying in places and his stubble eluded to a hard week’s work. He held a drink in his hand. You could smell his musk and the burning of candles inside.

“Come in, boy. Welcome,” The man said, and smiled at you charmingly. You stepped up and into his home. It was well appointed with leather couches and hardwood floors.

You saw that he had the lights set down a bit low and that was clearly intrigued to seduce you.

“Hello Sir. Thank You.” All you knew how to do from here was follow his direction. You did not want to say the wrong thing. Greeting him and thanking him seemed to flow naturally from your lips. He seemed to like your polite behavior.

“Strip, please.”

You heard his words and understood that this was the next natural step. He was in control now and you had felt you were ready for this sort of play. You were eager to submit and assume your position. Your sweatshirt came off swiftly and you hung it on a hook.

Your sweats were hiding a secret passion that the man had only heard you talk about. You had only gotten the panties, stockings and plug in the mail that day. With maintained eye contact and the brief moment of pause before pulling your pants down, it was somehow communicated that you had a surprise for Sir.

Your innocent eyebrow raise and flirty way of playing with the waistband was exactly the kind of femme behavior that the man wanted to see, and that you were beginning to feel natural providing.

Your sweats hit the floor and you felt the cool air return to your stocking-clad legs. Your cock was growing now as you exposed your sissy secrets to another man in the flesh.

The power exchange was well on its way. You knew that stepping out of your shoes without untying them and kicking your pants to the side was not very ladylike, but you were so flustered and nervous by the situation that you simply wanted to obey the man.

He watched you like a hawk on prey. His eyes studied your trembling hands and the obviously feigned confidence in your eyes. Despite your nerves, he licked his lips at your obedience.

You could feel his gaze checking out your pink panties and white stockings, not saying a word. It seemed like he noticed your unpainted toenails and that he was displeased with the hair across your upper chest. Hoping to please him, you began to pose and rub your knees together, as if like a young and inexperienced little girl.

“Cute,” the man commented. “You’re really a catch.”

You remember the compliment meaning the world to you, and feeling flushed that he liked your little outfit. You had always wanted to be referred to as a catch, a hottie, a babe. “Thanks Sir,” you shyly replied.

“Wait here. I have just the thing.”

You stood almost naked in his foyeur as he left around the corner. You began to relax. You felt a good connection based on the first few moments of your acquaintance. You took a breath and heard a closet door open in the other room.

Now that he was already doing something for you, to help begin the meeting, you felt an olive branch of trust coming.

He returned with a pair of white strappy high heels with platform bottoms. You became flushed with excited emotion. You had not been sure if the man liked sissy play or pantied boys or crossdressing in general. But now you knew he kept heels on hand. You wondered what else was in his closet.

You noticed that the heel was not too pointy, and that you would at least be somewhat stable. You also noticed locking mechanisms fastened to the straps. You knew these were not coming off for a while once you put them on. He put the shoes on the ground near your feet.

“Well? These look like your size. I also noticed you don’t have any nailpolish on.”

“Errr. ummm. I didn’t have any? Sir? Sorry Sir.” You blurted out, not sure what to do.

“That’s fine. Also, I wasn’t asking. My gurls don’t speak unless asked a question. Ok Pumpkin?” The man’s tone was so condescending but also sweet and authentic.

His sincerity won your silence quite easily. You mentally noted to pick out some nice nail polish or to consider driving to another nearby town to get a pedicure sometime, before seeing him again.

You knew that this would not be your last meeting with the man, already. Something in your gut told you so. It turned you on that you realized you were planning getting ready for a man on a future date. You returned to the moment at hand and bent down to put on the heels.

With only minor difficulty, you slipped your feet into the strappy heels. You figured they were at least 4″. Even with the additional height, as you stood up you realized that the man was still taller than you. He smiled at you and did a once-over of approval before bending down to secure locks to each of your ankles. The heels each clicked and your fate was continuing to take shape.

“Voilà!” the man announced. “Ok, now, follow me!” With the sexy heels now locked in place, the man seemed to have even more pep in his step. You could tell he was getting excited. Your steps forward were small at first, but you realized quite quickly that you were a natural walking in heels.

You felt like the panties and stockings made it easier for some reason, both that your legs and ass looked sexier than a man typically does, plus the notion that your strutting was all for the satisfaction of another man.

The power exuded from the man ratcheted up a notch when they got to a double doorway. The door was open and lights were low. As you approached, you saw a sturdy leather swing hanging from the center of the room. A dim spotlight hung over the sling dramatically.

The man looked at you and cocked an eyebrow, smirking, as he saw the stunned look of pleasure and terror on your face. You were amazed at how the empty sling made you feel. You suddenly longed to occupy the seat.

In a mind’s flash, you saw yourself up there, fastened tightly to the chains and dripping wet with cum, spit, and piss. You noticed the drain on the floor and the hose in the corner.

As you began studying the walls you saw various BDSM toys and leather & steel restraints. The man’s bondage room was professionally equipped and fully operable for fantasies to come true. Your jaw was dropped.

“Go ahead, hop up.” The man gestured towards the chair and was commanding you to comply. You did not have much choice and you did not show much restraint.

Nervously biting your thumbnail, you clacked forward in your heels towards the sling. Next to the strong black leather, your white nylons and pink lace set a bold contrast.

You turned around and knew that you wouldn’t be able to get up there without his help. You tried to think. You couldn’t jump in the heels and you didn’t want to fall and make a fool of yourself. You knew what he wanted you to say.

“Um. Sir. Can you… help?”

“What’s that, boy?”

“Can you please help me Sir? The swing is too high. Um.”

The man was coming toward you, grinning. “Well sure, boy. Let a man help this pretty boy up.”

His big arms and hands came around you. You felt so small and pliable in his hands as he lifted you right up off the ground and set your butt down in the soft pocked of the sling. You leaned back into the saddle and let out a sigh, dizzied by the strength that the man had displayed.

You knew this was a real force of a man and a very enticing situation you had gotten yourself into. Only hours ago you had been at home, edging to the standard old gooner pics and videos. Now, the man was working to secure your wrists and ankles to a heavy duty sex sling.

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