How I Became A Simpering Sissy Slut

sexy posture with a corset

I had been a closet crossdresser for most of my life. Ever since the first time I had stolen a pair of my mother’s panties and jerked off with them I became obsessed with female clothing. I loved it all, panties, skirts, blouses, dresses, heels, the more girlie the better. Satin items were my favorite! I just loved the feeling the soft, silky material sliding across my skin. By the time I was 18, I had a whole chest filled with female frillies. I used to wait till late at night when both my sister and mother had gone to sleep, and then I would get all dressed up for a nice wanking session. I would put on stockings and my garter belt. Then I would slide a nice pair of sating panties up my legs after tucking my “package” away. Next would be a lacy padded bra to give me the illusion of some titties. A nice mini-skirt and satin blouse for that slutty secretary look, and then the outfit would get topped off with a nice pair of black heels.

Once I was all dressed I would hop on the internet and go cruising around various Crossdressing and Tranny websites until my clitty was so hard I couldn’t stand it. I would pull it out and jerk off furiously until I sprayed my cum into my other hand. For a while, I would just wipe it off my hand with a napkin or some toilet paper, but eventually, I started to lick my juices off my hand. Cum tasted so delicious to me that I even started to jerk off in the middle of the day without getting dressed just so I could have a tasty treat.


Strong women to keep you in line near

When I graduated from High School and moved on to College I decided to live off-campus so I wouldn’t have to deal with a pesky roommate, leaving me free to dress whenever I wanted. My first semester went well since I was living off my summer savings and didn’t have to work while enrolled, however by the time the second semester rolled around my savings was almost empty. So I started looking around town for a decent part-time job that would still allow me to focus on my studies.

After about 2 weeks of looking, I realized the flaw in my plan. Most of the part-time jobs had already been snatched up by other students during the first semester of the year. The only part-time job I had been able to find was an overnight clerk position at the only “Adult Bookstore” in town. I didn’t really want to take the job as it was the overnight shift meaning I would then have to stay awake to go to class and the find time to sleep after class but before my shift would start at 11:00 pm. That didn’t exactly leave me with a lot of time to get my school work done. Also not to mention that part of the overnight’s job was to clean up the video booths in the back. While I wasn’t opposed to doing it, it wasn’t exactly something I was chomping at the bit to do. However, since it was the only job I was able to find I took it. After two weeks I figured out that it didn’t get that busy between 3am-7am and I would be able to get some of my school work done during that time.

At first it wasn’t that big of a deal, sure I was tired during class, but I was able to keep my off-campus apartment and occasionally spend time in my girly clothes so I was happy. As the semester wore on though, the school work got more and more demanding, and I was having less and less time between getting my school work done and getting to my job to dress up. Soon I was not only worn out from all the work, but I was sexually frustrated on top of it, which was really defeating the whole point of having a job in the first place. That is when I got the brilliant idea to start bringing some of my clothes with me to work.

I would put on my stockings, garter, and panties while getting ready to go to work, but on top of that I would wear my “normal” clothes. In my backpack, I would stuff my blouse, skirt, panties, and heels. I would stay in my “normal” clothes until about 2:45 am that way the customers wouldn’t be freaked out by the new “girl” doing overnights. Then I would duck into one of the booths in back, throw on my blouse and skirt, slide my fuck me pumps onto my feet, and then teeter my way back to the counter to start nightly cleaning of the store.

I would teeter around on my heels dusting the displays and sweeping and mopping the floor. If anyone came in I would tell them that I was Candy, owner’s eldest daughter and that I was just covering for a week while the normal clerk was on vacation, not that it happened a lot.

Once the front end of the store had been cleaned I would go back into one of the booths for a little personal time with my clitty. Since I worked at the store not only did I have control of what was available to watch in the booths, but I also didn’t have to feed quarters into the machine, I could just set it to play on a loop. I would always find the nastiest tranny porn the store had, put it in the player, I would then select the option to have it play in all the booths at once (this was a testing function to make sure there were no problems with the feed in any of the booths without having to have multiple films in the machine.) I did this so that the moans of pleasure coming from the “gurls” would echo around the back room making me almost foam at the mouth with lust. I would let the sounds wash over me, fully enveloping me, so I would be transported to a fantasy land where I would take the place of the “gurl” that was on the screen. Through the waves of sound I would become her, so that in my head, it was me taking those yummy cocks into my mouth. It would be my ass getting pounded by a nice long, thick, dick. I would grab my rock hard clitty and start pumping like there was no tomorrow. Soon enough I would spray my load all over the floor to mix in with all the other “deposits” that had been left throughout the day. I would then drop to my knees and then lick up my deposit and any others my questing tongue would come across.

Once my inner slut had been satisfied I would get the mop and bucket and clean out the rest of the stalls. Then usually around 6:30 I would change back into my “normal” clothes before the morning clerk would come in and relieve me.

Now we don’t “allow” sex in the back, but we don’t exactly discourage it either. I mean one of the booths had glory holes in both it’s walls. I had asked the owner about it when I first got hired. He had said that even if they don’t get used, the simple fact that they are there brings in more customers, on the off chance they might get to use it. He then went on to explain that while we don’t allow couples into the booths together, we do let customers use the glory holes as long as they don’t make too much noise. Wanna take a guess as to which booth I always took my “personal” break-in?

With all ten booths playing at once it is quite loud in back, which is probably why I hadn’t heard him enter that night. While I was wildly jerking off in fantasy fuck land, he must have entered the booth next to mine and heard me moaning. Just as I started to spray my load all over the floor I heard him start to clap. “That was amazingly sexy you slut. Watching you play with your sissy clitty got my cock nice and hard. Why don’t you get on your slut knees and help relieve the pressure YOU caused.” and with that, a 8 inch cock slid through the glory hole.

Part of me wanted to bolt out of the booth, but another part of me couldn’t help but stare at the wonderful piece of man meat. I had never seen another man’s dick in person, and I couldn’t help but salivate like one of Pavlov’s dogs while looking at it.

“What are you waiting for you cock tease? Don’t you want this nice hard cock in your sissy mouth? If you don’t hurry the fuck up I’m just gonna kick in the door and rape your slutty ass, get those cocksucking lips on my cock NOW!” he yelled to be heard over the sound of hardcore tranny sex.

I couldn’t help it, the way he was talking to me fully awakened my inner slut. I sank to my knees in front of the glory hole and began to lick his cock like it was the best tasting ice cream cone I had ever had in my life. I ran my tongue all the way from his piss hole to the base of his shaft and back again. As I was swirling my tongue around his beautiful cock head I felt my clitty start to harden again. “Oh my god” I thought “Sucking this stranger’s cock has got my clitty hard enough to spurt again. What is wrong with me? Why does this feel so fucking good?”

While I was still licking the head of his cock I heard him say “Tony was right you are a grade-A slut. That’s right sissy the owner told me about you. Bet you didn’t know that he could tape into the security camera’s from at home. He has known about your little kinky “hobby” for the last couple of weeks. At first, he was pissed, so pissed in fact that he was gonna fire your fucking faggot ass, but then he got to thinking. He figured if he could turn you full on faggot, he might be able to draw in some more late-night customers by locking your ass in this booth and making you service the punters that pay for the booths next to you. That is where I come in. You see I specialize it turning little fags into full on sissy cum sluts. When I’m done with you, you will be the best fucking cock slut on the planet. Now stop teasing me with that velvety tongue and fucking start sucking whore!”

I couldn’t help myself, the more and more he talked the more turned on I got. I was so fucking hot that I didn’t even care anymore, I just had to get off again. I slowly took his head into my mouth. As I worked my way down his shaft and back up again I felt even more blood flow into my clitty. It was so hard now it almost hurt.

I kept working his cock over with my mouth, gradually picking up my pace. “Oh that’s it you fucking faggot. Yeah suck that fucking cock. You love sliding my man meat in between those slutty lips. I bet that you little sissy clitty is hard from servicing a real cock isn’t it slut? Yeah bitch, make me shoot my fucking cum down your throat. You know you want it, don’t you, you little cum dump?” The more he degraded me the faster I bobbed up and down and his dick. Soon I looked like a piston slamming up and down on his rod. “Oh god slut get ready. I’m gonna cum down your fucking throat. You had better swallow it all, HERE IT COMES YOU FAG!”

His cock twitched inside my mouth and hot man juice began to flood my mouth. Spurt after spurt flowed into my mouth and down my throat. With each shot of his cum, my own pleasure increased until I screamed out in orgasm, letting his dick slide out of my mouth and sending his last few spurts all over my face. I slid down the wall and just laid there in a pool of my own cum. That had been the most intense orgasm I had ever had, and I hadn’t even touched myself.

As I laid there trying to recover from that mind bending orgasm, I saw him withdraw his cock from the hole. My mind was still floating in the post orgasm fog when about a minute later the door to my booth opened up and he stared down at me with a needle in his hand. Still panting I meekly tried to sit up and scurry away from him, but I my body was still bogged down in post orgasmic bliss, and I was too uncoordinated. He quickly stepped over me and stuck the needle into the meat of my arm. As he pressed the plunger down, he looked at me and smiled “When you wake up, you will be a completely different person, say goodbye to Rob the closet crossdresser, and say hello to Candy Cumdump.”

When I woke up I was in a large 4-post bed covered by luxurious pink satin sheets. My head was pounding so hard it felt like it had been through a rock tumbler. I opened my eyes and immediately regretted that decision as the bright sun pierced right through my skull and made the pounding much worse. I reflexively slammed my eyelids shut again and tried to curl up into the fetal position, which is when I made my next discovery.

I was tightly bound spread eagle to the posts of the bed with silk ropes! Furthermore the satin sheet appeared to be tucked so into the bed so tightly that I could barely wiggle around, let alone curl up into the tight ball like I had reflexively tried to do. I was bound within a satin prison! The more I tried to struggle against my bonds and the sheets the more the satin caressed my body, which in turn sent blood rushing to my clitty.

I was still struggling against my bonds, when all of a sudden I felt my growing hard-on press into the plastic walls of what I assumed could only be a cock-cage. This really sent me into a panic. However the more I freaked out and tried to escape the more turned on I got from the satin, which just added to my frustration and panic. What a vicious circle I was trapped in.

Eventually the frustration just outright replaced the panic. The combination of my satin prison and my inability to get hard was driving me insane. Soon I didn’t even care about escaping from the satin, I just needed to get off.

After what seemed like hours I finally heard something other than the sounds of my own struggling. I slowly opened my eyes expecting to see my captor looking at me, which was, and wasn’t the case. What I had apparently heard was the monitor directly above my head turning on. Since it was the only other stimulation I had been exposed to besides my satin pleasure prison I couldn’t help but stare at it, and on the screen was the man from the porn shop.

“I hope you have been enjoying my little sissy mind breaking prison. It’s time to step up to the next level of your training.”

I felt something begin to push it’s way into my ass. It kept firmly pressing against my sphincter until it began to slid in. My eyes bulged out as it finally pushed itself all the way into what until moments ago had been my virgin ass. Once it was fully seated inside me I felt it start to pump some sort of liquid into me.

With the liquid came a warm rush of chemicals that spread throughout my body, and suddenly all my physical sensations seemed to get amplified by a hundred. I couldn’t help but wiggle around even more as the feeling of the satin sliding across my body became truly unresistant torture.

“Ah it looks like that enema filled with Mdma is doing it’s job. You see slut I like my trainee’s completely mind broken before I even start their actual training. Between the frustration of not being able to get hard and the amplified body sensations from the Ecstasy it usually doesn’t take long, maybe a week at most before their minds shatter. A week is too long it seems for your former boss though, so I will be speeding up the process by adding in a constant stream of porn on the monitor here. Subliminals have been added to the sound from the porn to further speed up the mind breaking. You probably won’t make it more than 10 hours before your a drooling idiot just begging to be allowed to cum. Just to be on the safe side though I’m gonna leave you in there for the next two days. Have fun and say goodbye to the bright college kid you used to be.”

With that, his image was gone from the screen and in place was hot bitch in latex. She was wearing a black latex catsuit that looked like it had been painted on. Her make up was super trashy with lots of eyeshadow, and big red cocksucking lips. Her tits where so massive they looked like they might cause the catsuit to have a blowout. Completing the outfit was a pair of gorgeous six in fuck-me pumps. She began to dance and caress her body to the background techno beat.

After a few moments, the camera panned backward to reveal two men sitting on a leather couch watching the stunning bimbo rub herself all over. As they came on to the screen she strutted her way over to the couch and sank to her knees.

Using both hands she freed their cocks from their cotton prisons and began to jerk both of the men off. Once she had them nice and hard she began to give them alternating blow jobs. Their cocks were huge! The one on the right guy had to be a good 10 inches. The guy on the left was the smaller of the two at about 8 inches but he clearly had WAY more girth than the guy on the right.

After a few minutes of her sliding down one cock and then the other the man with the fat cock ordered the bitch to stand up and spread her legs. Once she had assumed the position he motioned the other man to go stand behind her. She leaned back into him as he began to maul her huge rack with his powerful hands, and her hands reached behind her back to continue to fondle his cock.

At this point, the other man reached for the crotch zipper in the catsuit and began to unzip it. Instead of revealing a sopping wet pussy, a small little cockette flopped out. It paled in comparison to the pieces of man meat on the guys, but was sexy in it’s own kinda way. He keeps undoing the zipper until it was completely unzipped and her cock and ass were totally exposed.

While the first man keeps manhandling her gorgeous tits, the other took her sweet little cockette into his mouth and began to suck her off. As he did this the satin sheet seemed to tighten down even harder against my body, and then it began to move from side to side on my body. It must have been attached to some sort of motor underneath the bed, because it was now liberally sliding back and forth about a foot and a half across my body all while keeping up what felt like a bone crushing amount of pressure. It was a much more intense sensation than my meek struggles had caused. Combined with the Ecstasy coursing through my system it would have made me cum on the spot, but that infernal cock-cage refused to let me even get hard.

Also when the sheet started to move I started to hear voices whispering in my ears. They kept whispering about wanting to be the “Gurl” in the movie. How nice it would be to have man catching tits like her’s. To have her soft full cocksucking lips, her padded bottom, her amazingly silky hair. It would be amazing to be a beautiful bimbo like her, not having to worry about anything other than attracting more cocks. That makeup is perfect for attracting cocks to suck on. To be free of inhibitions like her. To let men grope and fondle your body like her’s. It must feel amazing to be so obedient. To surrender all thoughts to the pleasure of your body. Letting go and becoming a creature of sexual pleasure.

Between the porn, the moving satin sheet, the drugs and every present voice I really was starting to lose my mind. I kept trying to form coherent thoughts, but every time the all out assualt on my sense knocked them loose. I was starting to experience sensory overload.

Suddenly the man on the screen stopped sucking her coquette and stood up. When he did that the sheet stopped moving. You would think that I would have been happy, but I was already so far gone that I started to cry in frustration.

I yelled out “Please god don’t stop! I need to cum! Just let me fucking cum and I will do whatever you want!” I was so caught up in my desperate need to cum that I didn’t notice what had been happening on the screen.

The man with the fat cock had stood up and grabbed what looked like a padded bar stool with cuffs attached to one set of its legs. He and the other man had bent the beautiful gurl over the stool and locked her hands into the cuffs. They then put a heavy rubber training collar around her neck that forced her to keep her head in such a position that her mouth was easily accessible. In fact, both of her holes were now easily accessible.

Once both men had resumed their respective positions the whispering voices drew my attention back to the screen. The man behind the gurl shoved all of his nice cock into her boipussy, and the man in front pushed his cock into her mouth. At the same time not only did the sheet start its assault but the plugin my ass that I had forgotten about started to pump in and out of my own boipussy.

“OH GOD! YES! FUCK ME! FUCK ME! FUCK ME!” I screamed out. Wave after wave of undeniable pleasure washed through me. My nerve endings were on fire. I felt my mind begin to crack into little pieces from the combined sensations of pleasure and the constant frustration of not being able to cum. So much cum had built up during the last 4 or 5 hours that it was just leaking out of my cock now. I was trapped in that satin prison with no escape, my boipussy was being rammed like there wasn’t going to be a tomorrow, all while being forced to watch this incredibly hot porno flick.

This is when the whispering voices pulled out all the stops. They stopped being generic statements and started to directly address me

“Candy likes to feel sexy. Candy wants to be the gurl on the screen. Candy loves to suck and fuck. Candy is an obedient sissy slut. Candy needs cum every day. Candy lives to please men. Pleasing men gives Candy pleasure. Candy loves making cocks hard. Candy needs cocks to be hard. Without hard cocks, Candy doesn’t get any cum. When Candy is an obedient slut she makes cocks hard. Cocks like a slut who follows commands. Candy wants to be the best slut ever.”

“Candy wants big fake tits. Big fake tits make cocks hard. Without hard cocks, Candy doesn’t get any cum. Candy needs cum every day. Candy loves to suck and fuck. Candy only cares about things that make cocks hard. Clothes, Make Up, and High Heels make cocks hard. Candy only cares about Clothes, Makeup, and High Heels. Clothes, Make Up, and High Heels make Candy feel sexy. Candy loves to feel sexy. Sexy sluts make cocks hard. Candy is a sexy slut. Sexy Sluts obey. Candy is a sexy slut”

On and on it went. Never stopping, just ramming these thoughts into my head. I couldn’t take it anymore. My mind shattered into a million little pieces and Rob disappeared forever. Desperate to fill the void my mind latched onto those voices. Slowly but surely they rebuilt my destroyed sense of self. The more and more they droned on the more and more I could visualize this sexy sissy. I could see her outline, her shape that classic hourglass figure. With each passing moment, she became clearer and clearer. Finally, as all three actors in the porno began to climax, the voices all simultaneously shouted out.

“YOU ARE CANDY CUMDUMP! YOU ARE THE BEST FUCKING SISSY SLUT ON THE PLANET!” and with that final statement echoing around in my skull as I passed out from sheer sensory overload, Candy Cumdump was born.

Last Updated on 8 months by pseudonymous