Freudian Transformation turteneckfan@hotmail.com Copyright 2007 All rights reserved
Katie was our new IT manager, and she was smoking hot. I had asked her out several times, but apparently my not-so-hot reputation with the other girls in the office got around to her first, and she consistently shot me down. Consequently, I was utterly shocked when she invited me to a party that she was hosting, and I accepted without hesitation. I could barely contain myself with the visions of what I wanted to do to her. To make it even better, the entire company was closed the following week for annual equipment maintenance, so thought of fucking her for an entire week dominated my thoughts.
I arrived at her house, and she ushered me in. She led me to her family room, where I was a bit shocked to see several other girls from my office Chrissy, Dawn, Heather, Julia, Sarah, and Tracy. My first impression was that it did not look like much of a party to me, as all six of them seemed to be looking at me with barely-contained hostility. My second impression was one of confusion, as I saw a few laptops set up, along with reams of paper that the girls were paging through.
Katie told me to sit down in the chair facing the girls, and feeling a bit uncomfortable and not knowing what else to do, I sat down. Katie then launched into the reason why I was to be the guest of honor tonight. She explained that, as part of her job, she was required to audit all PCs in our office for inappropriate material. As soon as she said that, my heart skipped a beat.
She continued on, describing in graphic detail all of the filth (her words, not mine) that she had found on my PC, ranging from straight pornography, bondage pictures, S&M pictures, and even worse. At first, she wanted to give me the benefit of the doubt, but she had started tracking my PC usage and web-browsing over the last three weeks, and she was able to confirm, without a doubt, that I was downloading tremendous amounts of pornography on my work PC during working hours.
I started to protest, but she suddenly got pissed and cut me off. She yelled at me to shut the fuck up, and if I wanted to save my career and my life savings, I had better keep quiet and listen. With my heart pounding so hard that it felt like it would burst from my chest, I shut my mouth.
Katie calmed down a bit and started again. She said that she took a closer look at my hard drive, and she found over one hundred word processing files that were password protected. Because these files were located in the same folder as the pornography, she had a hunch that they were not appropriate for the office, and one of her programs easily cracked the password. She said that she was utterly appalled at what was contained in these word processing files.
I of course knew what she was talking about, and the reams of paper that the girls were paging through, and their hostile looks, suddenly made sense. Not only did I have the habit of viewing and downloading porn, I also wrote my own stories. Over the years, I had written hundreds of explicit stories, most along the themes of bondage, sadism and masochism, humiliation, rape, etc. The kicker was, in all of these stories, I had primarily used the girls in my office as the victims, and me as the aggressor. On top of all that, I also doctored up some digital pictures from our company holiday party, superimposing the girl's heads on pictures of women being bound and fucked. They were all apparently reading those stories and perusing those photos as I arrived.
Katie said that, at first, she was simply going to turn me in to my boss and let her deal with me, but in all of her years managing IT systems, she had never run across such an appalling cache of porn, and she decided to leave my punishment up to the girls in the office whom I had written about. I was therefore invited to the party tonight to be their guest of honor, and I would be given the courtesy of picking my own punishment.
Katie laid out option number one for me I could leave the party now, and she would immediately report all of her findings to my boss. Not only would I be summarily fired, but I would also be sued for sexual harassment by each of the girls, almost guaranteeing my financial ruin.
I must have turned white as a ghost, and Katie quickly moved on to option number two. In lieu of reporting me to my boss and suing me for all I was worth, I could agree to an alternate punishment. This alternate punishment would simply teach me a lesson on the evils of objectifying and humiliating women, and I had to agree to follow every single command given to me by any of the girls.
I was then given 60 seconds to decide my punishment. It was honestly a fairly easy decision for me: I needed my job, and given my career, I simply would not be able to recover from a firing and multiple lawsuits. I readily agreed to the alternate punishment.
As soon as I had agreed, all of the girls flashed me wicked smiles. Katie seemed particularly pleased, and she gave me my first order I was to stand up and remove all of my clothes. With that statement, I started to feel like maybe this would not be so bad. After all, I rationalized, why would they have me get undressed unless they wanted to have sex? Although I did not smile, and I was in fact still reeling from what Katie had told me, I hopped up and stripped down. Katie ordered me to put all of my clothes in a garbage bag, and she took them away.
Upon her return, my perhaps irrational hopes of sex were immediately dashed.
Katie explained that, to understand the evils of objectifying and humiliating women, I would become a woman. I would be their object - their bitch - to do with as they pleased. They had decided that, to make the experience as psychologically mind-altering as they felt it needed to be, I would proceed through the five Freudian stages of life, but of course slightly modified to suit their purposes and to fit the experience into a short time. Katie then produced a camcorder and informed me that my Freudian transformation would be taped for posterity's sake.
My mind could not quite grasp what she had just told me, and although I had heard for Freud, I slept through most of my college classes, and I hadn't the foggiest idea what the five Freudian stages were. I was about to learn....
Oral Stage
Katie explained that Freud's first stage of development was the oral stage, usually occurring in infancy and predominated by an oral fixation. The first part of my punishment would be to successfully complete the oral stage, but first I had some preparation to go through.
I was marched into Katie's bathroom, where I was ordered to get in the shower. I was handed a bottle of hair removal cream, a razor and some dove soap, and told to remove all of the hair from my neck down and also the stubble from my face. Over the next 30 minutes, and as Katie caught everything on the camcorder, I proceeded to remove all of the hair from my body except for my eyebrows and the hair on top of my head.
I returned to the living room, still naked and now pink and hairless, and I cringed when I saw what was to be my outfit laid out: they were apparently going to dress me up like a little girl. Katie ordered me to put the outfit on, and I turned red with humiliation as the girls watched me dress. First I put on a cloth diaper, which I fastened with large pink safety pins. Then I put on a pair of white babydoll socks, complete with large pink ruffles, and a pair of pink mary-janes. Then I put on an enormous white petticoat, and I slipped what can only be described as a sissy dress over my head. The dress was made of sparkly pink satin, and it was adorned with puffy sleeves, white lace at the collar, shoulders, cuffs, and hem, with white bows down the front. I completed the outfit by attaching a sash adorned with a large white bow around my waist.
I was ordered to sit at a vanity that had been set up in the living room, and I was told to paint my fingernails pink and then apply pink blush to my cheeks. To complete my look, I had to put on glossy pink lipstick. Chrissy took over from there and proceeded to cut, curl and style my long blond hair, finishing off my new hairstyle with a large pink bow attached to the top of my head. I then had to attach pink heart-shaped clip-on earrings.
I was ordered to get up and model my new outfit for them. Dawn even taught me how to curtsey, and I had to place one foot behind me, daintily hold up the edges of my dress, and essential bow to them. I was further humiliated as they started to call me their darling little sissy boy, and after some debate, they decided that my new name should be Holly.
They unanimously decided that there was one problem with my new look, and I was told to sit back down as Tracy mercilessly plucked my eyebrows. By the time she finished, my eyebrows were thin and had quite the feminine arch.
Finally satisfied with my new look, I was told to kneel at the coffee table, where a large dildo, complete with realistic veins and balls, was placed before me. Katie informed me that my oral training was to start now, and I was instructed to pick up the dildo. Over the course of the next hour, I was essentially taught how to give a blow job, and I kissed, licked and sucked on the dildo until my jaw ached. The hardest part was when they taught me how to deep throat. I gagged repeatedly as I forced the dildo deeper and deeper into my mouth, but I finally learned how to relax my throat, suppress my gag reflex, and take the entire length of the dildo into my mouth. The girls really got into this and gave me pointers, suggestions and commands to improve my cocksucking skills.
After my initial training, I had to keep the dildo firmly in my mouth as I served the girls drinks and snacks. Whenever I had nothing to do for them, I had to kneel at the coffee table and practice my newfound cocksucking skills on the dildo. At one point, Julia popped in some gay porn, and I was forced to watch guys suck each other off and mimic their actions on the dildo. Then, over the course of the rest of the night, each of the girls strapped on a dildo, and I had to pretend to suck each of them off to their satisfaction. I was not allowed to close my eyes during these sessions; rather, I had to look directly into each girl's eyes and voice my pleasure at being permitted to suck on their cock.
By the time the girls started to tire out, my lips and jaw were practically numb from all of the sucking I had done. The dildo in my mouth was replaced by a penis-shaped gag with a long, thin tube emanating from it, and the gag was tightly locked around my head. A collar was locked around my neck, my hands were cuffed and locked behind my back, and my ankles were cuffed and locked together with a very short chain, effectively hobbling me. I was led to a corner of the living room that had a small piece of plastic on the floor and a chain that hung from an eye-bolt in the ceiling.
The chain was locked to my collar, and it was adjusted so that I had to stand up. Then Katie attached a funnel to the tube in my penis gag and informed me that a growing little sissy boy needs lots of milk to grow into a healthy woman. The girls then proceeded to pour glass after class into the funnel. I was unable to stop the flow of milk into my mouth, and the penis gag was so tight, none could even leak out of my mouth, so I was forced to swallow as much as they poured in. By the time they finished, I must have had eight full glasses of milk, and my stomach felt bloated.
Katie told me that they had one last treat for me for the night. The funnel was removed from the tube, and a vinyl sheath was attached in its place. Katie then pulled up my dress and petticoat, pulled down my diaper, squirted some KY jelly in her hand, and started to fondle my hairless balls and cock. Even though I was utterly humiliated, standing there in a sissy dress, bound and with a penis gag in my mouth, her touch was like an electric jolt, and my cock immediately reacted. In no time, I was fully erect.
Katie then slid the sheath over my engorged cock, and it suddenly became horrifyingly clear what the sheath was for: she had essentially connected my cock to my own mouth! Smiling wickedly, Katie proceeded to jerk me off. I was powerless to stop her, and I felt my own orgasm inexorably building. I shook my head no, but she was relentless, and in a matter of minutes, I could not hold back any longer and I shot an enormous load into the sheath. When I finished, cum filled up the lower portion of the tube. Katie then pinched the tube at the end of the sheath and began to slowly work her way up the tube. My eyes grew wide as I watched my semen work its way up the tube and towards the gag in my mouth. Katie stopped just as my semen reached my gag and asked me if I was ready for my treat. I let out an anguished grunt through my gag, and laughing, Katie quickly moved her pinched fingers all the way up to the gag.
Semen poured into my mouth, and I had to swallow or choke. It coated my tongue and throat, and I tasted cum for the very first time. Katie pinched my cheek and told me that there would be much more of that yummy treat. She then removed the sheath from my cock and wiped up the tiny amount of semen left in it. She then spread that over my lips. She pulled up my diaper, lowered my petticoat and skirt, and loosened the slack on the chain to the ceiling so I could lie down. With that, all of the girls left the room, and before she turned off the lights, Katie told me to have a lovely night, and she hoped I could make it through the night like a big girl and not have an accident.
I struggled to get free, but to no avail. The ramifications of Katie's parting words to me, along with the diaper and the plastic sheet under me, became apparent: the eight glasses of milk they had fed me (not to mention my own semen) was working its way through me, and I suddenly had to pee. I squirmed and wriggled and tried to call our for someone, but if they heard my muffled pleas, the girls did not respond. I started to cry as the urge to urinate became unbearable, and I eventually had no choice but to pee in my diaper. I spent a restless night in a pee-soaked diaper, tied up with a penis gag and the aftertaste of semen in my mouth.
I don't think that I really slept at all, and the night seemed to stretch on forever. Daylight finally started to creep through the windows, and I heard stirring in other parts of the house. Finally, Katie and the girls appeared, and I was immediately chastised for being such a bad little sissy and peeing on myself. My ankles and wrists were uncuffed, and the collar was unlocked from around my neck, but the penis gag was left securely locked in my mouth. I was ordered to clean my mess up, and I had to hand-wash my urine-soaked diaper and dress. Only after I had cleaned everything up to their satisfaction was I permitted to get in the shower and clean myself up, but I still had the penis gag locked in my mouth. While in the shower, I had to shave by entire body again to ensure smooth, hairless skin.
When I emerged from the shower, the girls debated whether or not I had successfully completed the oral stage. They all agreed that I was able to suck cock like a pro, and they decided I could move on to the next stage in my transformation.
Anal Stage
Katie explained that Freud's next stage of development was the anal stage, and I would be permitted to work my way through that now. Katie removed the penis gag from my mouth, and I was then immediately ordered onto my knees, with my head resting on the floor. My ass was completely exposed, and Katie produced a large enema bag. She unceremoniously inserted the nozzle into my rectum and released the contents of the enema into my bowels.
After she had emptied the entire contents into me, I was ordered to remain in that position for several minutes. I was cramping up by the time I was permitted to rush to the bathroom and relieve myself. I returned only to have the same process done two more times. I had to hop in the shower one more time to make sure I was completely clean, and by the time I was finished, I was completely cleaned out and my legs felt like jelly.
I was then ordered to put on my next outfit. This time around, they had me dress up like a schoolgirl. First I put on a pair of crotchless white panties adorned with red hearts (crotchless to apparently allow easy access to my ass), and then I put on a white turtleneck with red ruffles at the collar and cuffs. I slipped a pleated plaid jumper over my head, and I pulled on a pair of red cable knit knee socks. Then I put on a pair of black and white saddle shoes.
I was told to sit back down at the vanity, and I removed the remnants of the blush and lipstick from the day before. I also removed the pink polish from my fingernails, only to replace it with red polish. I reapplied blush and put on some light red lipstick, and this time, I had to put on a little bit of eyeshadow. Katie explained that I was still a young girl, so too much make-up would be a no-no. I clipped on a pair of red heart-shaped earrings, and Chrissy again did my hair, this time giving me two braids that were tied off by red ribbons.
They had me model my new outfit again, and once satisfied, I was presented with a string of ben- wa balls and some KY jelly. I was ordered to get on all fours, lift my skirt, lower my panties, and pleasure myself with the balls. I spent the next 30 minutes or so working the balls in and out of my ass. Then I was handed a small butt-plug, and I had to work that in and out of my ass. At one point, I had to place it on a chair and essentially ride up and down on it. Over the course of the next several hours, I had to insert progressively larger and larger dildos into my ass and basically fuck myself with them.
My ass ached from the constant fucking I was giving myself, and the girls had me switch positions to teach me the best ways to provide free access to my sissy ass-hole. The entire ordeal was humiliating, but perhaps the most humiliating position was when I had to get on my back, spread my legs, and fuck myself while being ordered to moan in pleasure, all the while watching myself in a mirror.
After a while, and as the girls chatted among themselves, I had to ride what can only be called a fucking ball. It was a large inflated ball with a dildo attached to it, and I had to sit on the dildo and bounce up and down. The dildo slammed in and out of my ass, and it really, really hurt. Finally, they tired of this, and they handed me the biggest dildo yet: it was apparently taken from a casting of a porn star, and it was at least ten inches long and incredibly thick. I had to slowly work it into my ass. I literally thought that I would split in two, and tears welled up in my eyes as I worked the huge cock into my ass. After I finally managed to insert it all the way in, Katie fastened it to a harness that was locked around my waist. She pulled another attached strap between my legs, slipped my cock and balls through a small O-ring, and locked that strap to the one around my waist. This effectively locked the dildo up my ass.
To make matters worse, Katie pushed a button on a tiny remote control, and the dildo started to vibrate in my ass. The vibrations stimulated my prostrate, and much to my horror and dismay, my cock sprang to life. In less than a minute, my cock was fully erect, and because I had crotchless panties on, it caused the skirt on my jumper to tent outward. The girls immediately noticed this, and I was even further humiliated as they made comments how much I obviously enjoyed having a nice, big cock up my ass. They even made me lift my skirt up to show off my erection for the camera.
I spent the next several hours serving the girls, and they made fun of the way I was walking, telling me that I walked like I had something up my ass. Then they would giggle and "remember" that I did, in fact, have something up my ass - an enormous vibrating dildo.
Towards the end of the night, Katie unlocked the harness and removed the dildo, only to attach the harness around her own waist with the dildo sticking straight out. I then had to get down on all fours, face the camcorder, and plead with Katie to fuck me like a woman.
I had to describe in graphic detail why I wanted to be fucked up the ass so much. Katie finally accepted my pleas, placed the tip of the dildo at my sphincter, grabbed my hips, and thrust forward. Although my ass was already stretched from the full day of having something up my ass at virtually all times, Katie's abrupt penetration hurt badly, and I squealed in pain. She spent the next 15 minutes or so fucking my ass hard while I was ordered to encourage her to fuck me even harder and faster, and I had to moan in ecstacy. When Katie finished, Dawn replaced her and fucked me hard again. This went on for hours until each of the girls had the opportunity to fuck my ass. I think that Sarah humiliated me the most when she flipped me on my back and fucked my ass from the front. I had to look into her eyes and thank her for making me feel so good.
After they had all finished with me, the dildo was left vibrating in my ass, and the harness was once again locked in place. My ankles were locked together, and my wrists cuffed behind my back. The collar was locked around my neck and attached to the chain hanging from the ceiling, again forcing me to stand. Then, Katie said that she thought I should get a jump on the next stage, and the penis gag was shoved into my mouth and locked in place.
In a repeat performance of the night before, Katie fondled me until I was hard, and the sheath attached to the tube in my gag was placed over my cock. She jerked me off and quickly forced the semen up to my gag, where it once again flooded into my mouth. She removed the sheath, wiped up the excess semen, but this time smeared it just under my nose so I could inhale the scent of semen the entire night. The chain was then loosened so I could lie down, and they left the room.
I was so exhausted from the previous sleepless night that, even with the penis in my mouth and the vibrating dildo in my ass, I did manage to get some sleep. They mercifully did not fill me up with liquids, so at least it was an accident-free night. They actually had to wake me up the next morning.
Phallic Stage
Katie informed me that I had successfully completed the anal stage, and today I would move on to the phallic stage. I was unlocked, and the gag in my mouth and the dildo up my ass was removed. I got in the shower and again shaved my body.
My next outfit was laid out for me, and this time I would have to dress up more like a younger teenage girl. I pulled on a pair of crotchless white panties, and then I put on a white bra. Katie handed me a pair of silicone breast enhancers, which gave me the appearance of having probably A-cup breasts.
Before I was permitted to put the rest of my outfit on, I had to wipe the remnants of the make-up from my face, and I had to remove my nail polish. I had to then paint my toenails a deep red color, and I painted my fingernails with the same polish.
After my nails dried, I pulled on a short pleated denim miniskirt with white lace detail at the hem, a white turtleneck with red hearts printed on it, and a red v-neck cardigan with ruffles on the sleeves. To finish the outfit off, I put on a pair of red cable knit legwarmers and a pair of red mary-janes. Chrissy once again did my hair, affixing a large white bow with red hearts to the crown of my head.
Katie then announced that she thought I was old enough for pierced ears, and she proceeded to pierce both of my ears, but instead of keeping the starter studs in place, she inserted diamond studs. With my ears still stinging from the piercing, I was then taught how to apply full make-up. I started with foundation, and I was taught how to blend it in. Then I put on blush, red lip liner and glossy red lipstick. The eyes were the hardest part, and it took me several attempts to apply my eyeliner. I used a little bit of mascara and then finished my eyes with blue eyeshadow. I finished off the entire look with a light application of powder.
Yet again, I had to model my outfit for them, and once satisfied, I was permitted to move to the next stage of my transformation. Katie explained that today would be all things phallic for me, and I would learn how to accommodate a cock in my ass and in my mouth at the same time, all the while stroking a cock in each hand.
They started me off by handing me two dildos, and I had to insert one up my ass and fuck myself while I sucked on the other one. After they were satisfied with that performance, I had to ride the bouncy ball with the dildo while holding the other dildo in my mouth. For the rest of the day, it was like a combination of day one and day two I had a cock in my mouth and a cock up my ass the entire time. Towards the evening, all of the girls strapped on dildos, and they rotated around me - I would suck on one while another fucked my ass, and at the same time, I would stroke a dildo in each hand. They periodically had me switch positions so I could practice in all of the angles.
At the end of the night, I was again chained in the corner with my ankles locked together, but this time my hands remained free. I had to insert the penis gag and lock it in place, and Katie ordered me to bring myself to an erection. As soon as I was hard, Katie ordered me to place the sheath over my cock and ordered me to insert the vibrating dildo into my ass. I then had to fuck myself with the dildo while I jerked myself off. With each thrust of the dildo into my ass, I had to pump my own erection. Katie told me I would need to keep this up until I came.
After 10 minutes of fucking myself and jerking off, I shot an unbelievable load of semen into the tube attached to the sheath. My orgasm was intensified by the vibrations of the dildo up my ass, and I involuntarily let out a true moan of pleasure as I came. As soon as I finished cumming, I had to place the vibrating dildo into the harness and lock it up my ass. Then Katie ordered me to do the honors and move the semen up the tube into my mouth. I decided to make it quick, and for the third time in as many days, semen flooded into my mouth.
I was then permitted to remove the sheath, and I had to wipe up any excess semen and spread it under my nose. Tracy then handed me a dildo for each hand, and I was told that I had best be holding them both when they returned in the morning. They turned the lights out, and I fell asleep with the vibrating dildo up my ass and penis gag in my mouth, all the while clutching a dildo in each hand.
Latent Stage
The next morning, I was miraculously still clutching both dildos. I was unlocked, and I was permitted to release my hold on the dildos in my hand, allowed to remove the still-vibrating cock from my ass, and allowed to remove the penis gag from my mouth. Katie announced that I had successfully completed the phallic stage, and today I would move into the Latent stage. Here I would learn how to be a girl, and I had quite the busy day planned for me.
After hopping in the shower and shaving, I cringed when I saw my next outfit: a cheerleading uniform. I put on a pair of pink satin panties and a matching bra, which I stuffed with two silicone enhancers on each side to give me a B-cup. Then I slipped on a white turtleneck bodysuit, cheerleading skirt and sleeveless vest, along with anklets and white cheerleading shoes. I sat down and touched up my fingernails and applied full make-up. Chrissy once again fixed my hair, but this time clipping a hair bow in place that matched my cheerleading uniform.
Satisfied with my appearance, I was then taught how to be a cheerleader. They had me jump, twirl, kick my legs up, and sing chants, all for the benefit of the camcorder. Out of the blue, Katie suddenly shouted out "Regression!", and I was handed two dildos. Apparently Katie decided that I needed to backslide for a bit into the phallic stage, and in full cheerleading regalia, I had to fuck myself with one dildo while I sucked on the other one. I fixed them all lunch with the vibrating dildo still up my ass and the dildo firmly in my mouth.
After lunch, Katie decided that my regression was over with, and I was told to strip out of my cheerleading uniform. I kept my panties and bra on, and Katie inserted yet another breast enhancer into my bra, making me a C-cup. I carefully slipped a pink angora turtleneck sweaterdress over my head so as not to mess up my make-up, and I put on a pair of pink pumps. I re-did my hair, only this time without any accessories. Katie then handed me a purse and, before I could really comprehend what was happening, I was ushered out to her car.
Katie drove to a nearby mall, and I was told that I had several appointments scheduled. She handed me a list of my appointments, along with specific instructions for each. I was mortified when she ordered me out of the car. She warned me that I had best follow all instructions on her list, or suffer the consequences, and she would meet me in the women's restroom after my last appointment. She added that she or one of the other girls may check up on me, so I had best be a good girl. She then drove away.
Not knowing what else to do, I headed into the mall. I was utterly self-conscious as my heels clicked on floor, and I could swear that everyone could see right through me and know that I was a guy in a dress and make-up. I tried to keep my eyes focused straight ahead of me, and I walked as quickly as I could to my first appointment, which was at a nail shop near the middle of the mall.
It seemed like the walk to the nail shop took forever, and pursuant to Katie's instructions, I went up to the counter and told the receptionist that "Holly" was here for a pedicure and manicure appointment. The girl looked up at me, giggled, and commented that I was the first cross-dresser that they had ever worked on. I was utterly humiliated and speechless, and I tried to stammer out some response as I was led to a table. The girl giggled again and reassured me that they were ok with giving a cross-dresser a pedicure and manicure.
I was placed at a table immediately in front of the window out into the mall, so everyone that passed by could see me. I was frankly too embarrassed and tongue-tied to even protest. A teenage girl sat down to do my pedicure, and as she worked on my toes, she bombarded me with questions about cross-dressing. Katie had covered this in her instructions, and she written that if someone were to ask me if I was a cross-dresser, I was to freely admit it and embellish as needed. So, I had to explain to this giggling teenager my (fictional) life history as a cross-dresser.
The girl finally finished working on my toenails, and she asked me what color I wanted to use on them. Again, Katie's instructions covered this, and I picked out a pearly pink color. As soon as the girl finished painting my toenails, she inserted cotton spacers between my toes, and looking at my pink pumps, she gave me a pair of disposable flip-flops to wear until my toenails dried.
Another girl then took her place and started to work on my fingernails. I was bombarded by another round of questions about being a cross-dresser as she attached long extensions to each of my fingernails. She finished them off with several coats of the same pearly pink polish and a topcoat. As I went to pay, it struck me that I had no idea if I had any money on me, and I carefully opened the purse that Katie had handed me before we left. After digging through make- up, I found a little change purse. I opened it up, and there was no cash - only my driver's license and my credit card. I went ahead and charged it to my account.
I headed out for my next appointment, carrying my pink pumps in my hand and wearing the flip- flops and the cotton spacers between my toes. I walked to the far end of the mall to a hair salon, and I again told the receptionist that "Holly" was here for a hair appointment. Although this receptionist did not make a direct comment about cross-dressing, I could tell by the way she was looking at me that she knew I was a guy.
I was ushered back to a chair, and a perky girl approached me. She introduced herself as a personal friend of Katie's and confirmed that I was there for "the works". Katie's only instructions regarding the haircut were to simply agree to whatever the hairstylist recommended and then act like I absolutely loved whatever was done to me, so I meekly agreed with the girl that I was here for the "works", whatever that was. She washed my hair, toweled it dry, and proceeded to apply some type of cream to my hair, using a lot of foil. After letting that sit, she rinsed my hair and gave me a trim. After trimming up my hair, she applied some kind of solution to my hair and put it in curlers. I never faced a mirror, so I could not tell what was happening. I was then parked under a dryer and given the latest ladies magazines to read.
After my hair finished setting (or whatever it was doing), I was led back to the chair where my hair was finished off. The hairstylist swung me around, and I was utterly blown away. First off, my blond hair had been lightened, but with dramatic highlights throughout. I had also apparently been given a perm because my hair cascaded down in gentle curls. I was utterly speechless, and when the hairstylist asked me what I thought, all remember Katie's instructions to act like I loved it, so I did.
Still reeling from my new hairstyle and color, I paid an obscene amount of money to the cashier. I then discarded my flip-flops, put my pink pumps back on, and headed down the mall to my next destination - an earring shop. There I had my ears pierced yet again, and after bribing the technician, I left the shop wearing new silver hoops in my existing piercings and, instead of the starter studs, I wore my diamond studs in each of my new upper piercings.
I headed off to my fourth stop, which was a shoe store. Katie instructed me to purchase a pair of black leather boots with at least three-inch heels. I again paid an obscene amount for my purchase, and I headed out to my next stop, which was a lingerie store. Forking out even more money, I purchased several bra and panty sets (I was allowed to choose my own styles, but they had to be hyper feminine), a pink satin corset, and several pairs of stockings. The clerk at the lingerie store also knew I was a guy because, on my way out, she said "Enjoy your purchases, sir!"
Completely humiliated by that comment, I headed down to my last stop - one of the main department stores. I first headed to a make-up counter specified in Katie's note, and the woman behind the counter was apparently expecting me. Mentioning that she was a friend of Katie's, she sat me down, removed the make-up that I had on, and gave me a full make-over. By the time she finished, you could barely even tell I was a guy.
With my make-over finished, and after buying a ton of make-up, I headed to my last destination in the department store, which was women's clothes. There, Katie instructed me to pick out and buy a skirt and sweater set, with the instructions that it had to be hyper-feminine and the sweater had to be a turtleneck to hide my adams' apple. She noted that I should try my clothes on first because if they did not fit, she would be very, very angry.
I picked out a pleated grey skirt and a pink cable knit turtleneck sweater, grabbing multiples of each because I was guessing on the sizes, and I headed to a dressing room. As I was already in a dress and made up completely like a woman, I did not give a second thought to going in the women's changing room and, luckily, there was no one there. I first tried on the skirt, and it took me several attempts to get the right size, which ended up being a 10. The turtleneck was easier, and I settled on a large. I gathered the skirt and sweater and headed off to pay for them.
The last instruction on Katie's note was to wait for her in the women's restroom near the middle of the mall. She warned me that I had best be waiting in the restroom for her, and I was not permitted to hide in a stall I should simply stare into the mirror and act like I was fixing my make-up if anyone came in.
I reached the restroom, praying that Katie would already be there, but no one was in the hallway, and I entered the women's restroom with trepidation. I was relieved when I saw that no one was in the restroom, but that relief was short-lived when a woman in her 20s came in. I tried to act like I was busy primping my hair, but the woman wanted to make small talk. I could not really ignore her, so I mumbled some response. The woman shot me a strange look and she quickly left. At least I had the bathroom to myself again.
About five minutes later, I almost jumped out of my skin when someone started to knock loudly on the bathroom door. I thought I would have a heart attack when the person knocking announced themselves as "security" as ordered me to come out of the bathroom. I gathered my purchases and, shaking, walked out of the bathroom. The woman who had just been in the bathroom was there, and she identified me to the two security guards as the pervert she had just encountered, adding that it freaked her out to find a guy dressed like a girl hanging out in the women's restroom. The first security guard shot me a nasty look and informed that I would have to come with him. I tried to protest, pointing out how I was dressed and that I didn't even think about it, but the guard cut me off, telling me that I would need to come with them to the security office, and I could explain everything to the police when they arrived.
I was horrified as they actually cuffed my hands behind my back. If people were not looking at me before, they were certainly looking at me now as I was led, hands cuffed behind my back, down the center of the mall to the security office.
The security guards led me to a holding cell containing only a table and chair, and surrounded by one-way glass. I began to plead with them not to call the cops. I told them that I couldn't be arrested dressed as I was, and I begged them to let me go. I promised that I would never return to the mall, and I would do absolutely anything if they would let me go. The first guard looked at me funny, paused for a second, seemed to think about something, and then had a whispered conversation with the second guard. They seemed to agree on something, and the first guard leaned against the table. What he said next stunned me.
"Tell you what. We'll let you go on one condition, and you have until the count of ten to decide. Either the cops come and arrest you, or you drop to your knees right now and suck us both off. Ten. Nine. Eight...."
It took me until he was at the count of five to comprehend what he had said, and my mind raced over the trauma that was to ensue if I was arrested dressed like I was. Feeling utterly trapped and helpless, I sank to my knees by the time he reached the number two.
Flashing a wicked smile, the first guard stepped up to me, unzipped his pants and pulled out his soft but large cock. He then told me to lick him. My hands were still cuffed behind my back, making it difficult, but I leaned forward and started to lick his penis, tasting another man's cock for the very first time. He lifted his cock up and I ran my tongue up and down the sensitive underside of his shaft, making it glisten with my saliva. His cock grew larger as I licked every part of his manhood, and he even had me suck on his large balls for a while.
The musky scent of his manhood filled my nostrils as I continued to lavish my tongue up and down and all around his cock.
Soon, his cock was fully erect and throbbing, and pre-cum glistened at the tip of his engorged purple cock-head. He ordered me to pucker up for a kiss, and he wiped the oozing pre-cum from his cock onto my pink lips. He then told me to lick my lips seductively. As I licked his pre-cum from my lips, I tasted another man's semen for the first time, and unlike my own (which I had tasted three times over the last few days), his was slightly salty.
He then ordered me to blow him. I opened my mouth and wrapped my pink lips around his shaft. I wanted to get this over with as soon as possible, and remembering the pointers that the girls had given me, I started to work his cock in and out of my mouth. Using my tongue and lower lip, I worked on the sensitive underside of his shaft, occasionally focusing solely on his head of his cock. I was mortified and the slurping and sucking sounds that I was involuntarily making as I worked his cock deeper and deeper into my mouth, and soon, I was deep-throating him. At one point, he grabbed my head with his hands and basically started to fuck my mouth. I felt his cock twitch in my mouth, and at the same time, I heard him moan. Suddenly, cum started to flood into my mouth. He still had a firm grip on my head, preventing me from pulling back, and I had to either swallow or choke, so I swallowed what I could. He shot an enormous load into my mouth, and I could not swallow it all, and his semen leaked out of the corners of my mouth and dribbled down my chin. After he finished, he had me lick his cock clean.
As soon as I had finished blowing the first guard, the second guard took his place. Apparently my performance on the first guard had aroused the second guard because he was already fully- erect. The second guard was a large black man, and at least in this case, the stereotype that black me have enormous cocks was dead-on. His cock was simply massive - probably ten or eleven inches long and so thick, I would not have been able to wrap my hand around his shaft and have my thumb and forefinger touch.
I stared at his cock in disbelief, but I snapped out of it when he said "Lick it, Bitch!". I ran my tongue up and down his enormous black cock until he ordered me to suck. I opened my mouth as wide as I could, but I could only take less than half of him into my mouth. This apparently pissed him off, and he grabbed my head and tried to force more of his manhood into my mouth. Although I had learned how to control my gag reflex, he was simply too much for me to handle, and I started to uncontrollably choke.
He finally relented and pulled out in disgust. What he did next almost made me cry - he ordered me to get up off my knees and he led me over to the desk. He spun me around so that I faced the desk, lifted my sweaterdress to my waist, and he bent me over so that my torso rested on the top of the desk. He ordered me to spread my legs and he lowered my panties just enough to expose my ass. I could see myself in the reflection of the one-way glass, bent over the desk, fully made- up like a woman with semen still glistening on my lips and chin, and I watched as he spit into his hands, rubbed it on gigantic cock to lube himself up, and positioned himself between the cheeks of my ass. He then ordered me to beg and plead with him to fuck my ass. I was utterly humiliated as the first guard whom I had just sucked off chuckled as I proceeded to beg the second guard to fuck my sissy white ass with his big, black cock. I even had to tell him how bad I wanted his cock up my ass, and how I just loved to get fucked by a real man.
I guess he finally grew weary of my begging, and he suddenly shoved his cock into my ass. I squealed in shock and pain, but I guess it could have been worse - at least my asshole had been stretched a bit by the girls fucking me with the dildos. He then proceeded to fuck my ass hard, and I could feel his gigantic balls slapping against my ass as he repeatedly thrust his enormous cock deep inside of me.
When he had bent me over the desk, my own cock had become trapped underneath me. To my complete horror and dismay, the movement of my own cock, trapped between my body and my silk panties - and the stimulation of my own prostrate - as the guard pounded my ass caused my cock to betray me and spring to life. My cock was soon fully erect beneath me, and the repeated thrusting of the cock up my ass, and the movement of my body against my own cock trapped beneath me, was having the same effect as jerking me off. Even though I was essentially being raped, and even though I was humiliated beyond all imagination, I could feel myself inexorably approaching orgasm.
I tried to stop myself, but I soon reached the point of no return. As I always involuntarily do when I reach orgasm, I let out loud moans of ecstacy as I started to cum. Either my moans got to the guard fucking my ass, or the involuntary constrictions of my sphincter around his cock got to him, as I heard him start to moan. Although I could not actually feel him cum inside of me, I could feel his semen leaking out of my asshole and run down the crack of my ass to my shaved balls.
Sated, the second guard pulled his cock out of my ass, and as he withdrew, I could feel a lot more semen run down my ass. He wiped his cock off on my panties, pulled them back up, and patted my ass, complimenting me on the fine fuck. Both guards got quite a kick out of the fact that I had had an orgasm myself, and they both commented how much I must have enjoyed getting fucked to have actually reached orgasm without even touching myself.
The guards unlocked my handcuffs and allowed me to stand up and lower my sweaterdress. My panties were a sticky mess, and my own semen mixed with the second guard's semen as it continued to leak out of my ass. They told me I had ten seconds to gather my purchased and get out. I didn't even have time to wipe the semen from my mouth as I rushed out of the security office into the mall, where I immediately encountered Katie, who was talking and laughing with the woman who had originally called security on me.
I was momentarily dumbfounded, and then Katie spotted me. Both women walked up to me and burst out laughing. Katie, almost doubled over with laughter, handed me a tissue and, between fits of laughter, told me that I should probably wipe the man-juice from my lips and chin. She then introduced me to her friend Erika, who had apparently conspired with Katie to set me up.
Then both security guards walked out, and each gave Katie a hug and a kiss. They had apparently been in on it, too. The first guard told Katie that I was quite the cocksucker, and the second guard grinned as he told Katie that I had quite a nice little sissy ass to fuck. Then they both had to chime in about how I had reached orgasm myself. Katie's eyes grew wide at this revelation, and winking at me, she told me that she always had a hunch that I was a true sissy, and this just confirmed her hunch. By this time, I was beet red with humiliation, and to add insult to injury, the first security guard handed Katie a videotape and told her that all had been filmed, and from multiple angles. He noted that the best shot by far was the look of pure pleasure on my face as I got fucked up the ass and reached my own orgasm.
Katie thanked all parties involved and ushered me out of the mall. I was on the verge of tears, and it did not help much when she noted that I was walking a bit funny. I gingerly sat in the car, and I squirmed from the sticky mess in my panties. We did not head straight back to her place, though, and my heart sank as she pulled into the parking lot for an adult porn shop. She gave me a list and told me to go in and make my purchases.
The shop apparently catered to the fetish and S&M crowd, and I scanned the store for the items on the list. First I selected a pair of D-size silicone breasts, complete with realistic nipples. Then I picked out a very specific maids dress, complete with a huge crinoline petticoat, and a pair of four-inch bondage heels, complete with tiny padlocks that would secure the shoes around my ankles. I blanched as the bored-looking clerk rang up my purchases, and I worried about maxing out my credit card as the total came to well over a thousand dollars.
I hauled out my purchases to Katie's car, and I again turned beet red when she commented that I had a large wet spot on the back of my sweaterdress, apparently where the semen had leaked out or through my panties. We then finally drove back to her place.
The girls were waiting for us, and they oohed and aahed over by make-over. Katie, grinning like the cheshire cat, told them that she had quite a story about my adventures today, but first I needed to be put in my place. Katie ordered me to take off my still-soaked panties and put them aside. The other girls gave Katie questioning looks, and it readily became apparent that they were not in on Katie's set-up with the guards at the mall.
Katie had me kneel down and lock my ankles together, and then she had me lock my wrists behind my back and lock my handcuffs to the chain on the cuffs attached to my ankles, preventing me from getting up. She then told me to open wide, and she stuffed the semen-soaked panties into my mouth. She then launched into telling the other girls that I apparently could not wait for the official start of my adult stage, and I had taken matters into my own hands at the mall. Katie then produced the videotape, popped it into the VCR and hit play.
I was forced to watch myself give the first guard a blowjob from several angles as the other girls looked on in utter dismay and delight. They positively squealed with excitement when he came in my mouth, and they got even more excited when they saw the size of the black guard's cock. They were astonished that I could fit as much of his cock in my mouth as I did, and then, when he bent me over the desk, they all shook their head in disbelief. My pleas to be fucked up the ass were quite audible, and the girls actually applauded when the guard rammed his cock up my ass. Katie hushed the girls and told them the best part was yet to come, and she told them to focus on the look of my face. Katie then noticed that I was looking down at the ground, and she ordered me to watch what I knew was coming.
The shot was straight on and clearly showed both my face and the guard fucking my ass. Then I started to moan, and even though I don't remember saying it, the words "oh yes" clearly escaped my lips and my orgasm overtook me. I was clearly bucking and shaking with the intensity of my orgasm, and as the guard shot his load deep inside my ass, a look of pure pleasure was, without question, on my face. The girls roared and erupted in applause. At that point, every shred of masculinity that may have been left in my psyche was completely eradicated.
Katie patted me on the head and told me not to worry - there would be plenty more sucking and fucking in my future, but first, I needed to complete my Latent Stage, and then I could move on to the stuff that I so clearly enjoyed.
Katie removed the cum-soaked panties from my mouth, unlocked my wrists and ankles, and told me to strip all the way down. She produced some spray adhesive and coated the undersides of the silicone breasts that I had bought. She first attached the breasts to my chest, twisting them to ensure an even distribution of the adhesive, and she had me hold them in place while the adhesive set.
They made me look at myself in the mirror, and the transformation was stunning. From several feet away, the breasts looked like they were part of me, and with the exception of my hairless cock, you could not tell that I was a guy, particularly with my make-up and earrings on and my hair cut, colored and styled.
Dawn then retrieved my new pink satin corset, and she placed it around my waist. She mercilessly tightened it, reducing my waist by a good three or four inches. Then I had to put black fishnet stocking on and the new bondage heels, and I fastened the padlocks to my shoes, effectively locking them onto my feet. I then put on the petticoat and the maids uniform, and Katie ordered me to clean her entire house to prepare for the party this evening.
I spent the next several hours hobbling around in the bondage heels, cleaning everything in the house. After the girls were satisfied, I was ordered to wait by the door and let the guests in as they arrived. Katie informed me that the party would mark the beginning of the final stage of my transformation.
Adult Stage
The doorbell rang, and I opened the door with trepidation. The first two guests were the security guards from the mall, and the black guard patted me on the ass as he walked in. Over the next hour, about ten other guys showed up, and I had to serve them all drinks and dinner. After I had cleaned up from dinner, Katie announced it was time to officially start my adult stage.
I cringed as Katie explained to all of the guests that I had actually started my adult stage a bit early, and she thought that I should recreate for all of them my first encounter with real men. Katie then ordered me to get on my knees, and the first security guard stepped up to me. Katie then told me to go for it.
Feeling all eyes intently on me, I reached up, unzipped his pants, and carefully pulled out his cock from his underpants. Katie whispered in my ear that I had best take my time and give it my all, and I started to lick his cock. It was a bit easier this time because at least my hands were not cuffed behind my back, and I was able to stroke and caress his cock with my hands to get him fully erect. I then opened my mouth and wrapped my red lips around his shaft, slowly working my tongue and mouth up and down his throbbing manhood. Katie warned me several times to slow down and enjoy it, and I ended up sucking on his cock for a good twenty minutes as all of the party guests watched and shouted out suggestions. Katie then told me to show everyone my deep-throat skills, and I proceeded to take his entire shaft into my mouth, with my lower lip just touching his balls. With his cock buried all the way in my mouth, Katie had everyone take a nice, close look at my ability to deep-throat a real man.
Katie then told everyone that I was probably craving the taste of cum by now, and she told me to go ahead and finish him off for my yummy reward. I started to suck him off in earnest. I started by licking his balls and running my tongue up his shaft, at which point I would take his entire cock into my mouth for a deep suck. I did this several times and then simply started to slide his cock in an out of my mouth as quick as I could. He started to moan, and without much warning, his cum started to flood into my mouth. I again swallowed what I could, but some still dribbled out of the corners of my mouth and down my chin. After he finally finished shooting his load into my mouth, I licked his cock completely clean.
There was much applause, and several people commented on my superior cocksucking skills. Katie then told them that not only did I love sucking cock and tasting cum, but I also loved getting fucked up the ass. She then ordered me to demonstrate my love of getting fucked like a sissy.
The black guard stepped up, and Katie ordered me to get him ready. I unzipped his pants and pulled out his cock. Even though his cock was soft and flaccid, his manhood was still probably bigger than my own cock when it was fully erect. Using both of my hands and my tongue and mouth, I licked and massaged his penis until it was rock hard. He was simply awesome in size.
Katie handed me a tube of KY jelly and she had me lube him up. The then ordered me to spread my legs, bend over, lift my skirt and petticoat, and spread my cheeks apart for him. I had to beg him to fuck my sissy ass with his huge, black cock, and he stood behind me, placed the engorged head of his cock against my sphincter, and he grabbed my hips. Katie then ordered me to do the rest, but she warned me to take my time so I could savor the feeling of having such an incredible man enter me.
I slowly started to push back against his cock. I whimpered a bit as I worked the head of his cock into my ass, but the pain lessened a bit as I slowly worked the slightly narrower shaft of his cock into me. After what seemed like hours, I had worked his entire cock into my ass, and I felt his balls resting against the cheeks of my ass. Katie then told me that I should do most of the work, and to be sure to voice my pleasure of the sheer honor of having such a magnificent cock in my ass. With very little help from the black guard, I started to slowly work his cock in and out of my ass, moaning as I did so. After about ten minutes, I guess the guard got impatient, and he took over, and he started to fuck my ass hard. This time I think I did feel him cum inside of me, and just to make things a bit messier, he pulled out before he was finished and shot his remaining load in the crack of my ass.
Another round of applause followed, but Katie said that I had more to demonstrate. She asked for two volunteers, and two guys stepped up. I had to stroke them both to full erection, and then one took up position behind me while the other took up position in front of me. Then, as all of the guests watched, I was double-teamed. The guy fucking my ass came first, and instead of cumming inside of me, he pulled out at the last minute and came all over my bottom. Seconds later, the guy I was blowing pulled out, too, and I had to keep my mouth open as he shot his load into my mouth and onto my face.
Katie then asked for four volunteers, and I had to bring all four of them to erection. Then, as one of them fucked my ass and another fucked my mouth, I had to stroke the other two with my hands. Once again, the one fucking my ass came first (this time inside of me), and soon thereafter, the one fucking my mouth came deep in my throat. I then continued to jerk the other two guys off into my open mouth and swallow it all. Meanwhile, the girls had prepped the remaining guys, and I was then subjected to a circle jerk, with each of the remaining guys jerking off on my face and into my open mouth.
By the time they had all finished, cum was splattered all over my face, and a stead stream seamed to leak out of my ass. Katie did not allow me to clean myself up, though; rather, she had me pull my panties back up, get up off the ground, and personally thank each guy for the wonderful experience. Katie then ordered me to pull up my skirt and petticoat and fondle my sissy cock. This time, my cock did not betray me, and it did not get hard. Katie was not too happy about this, and she commented that I apparently needed some help getting myself aroused, and a nice, big vibrating dildo up my ass should do the trick. She produced the large vibrating dildo, and she ordered me to fuck myself with it as I stroked myself. The vibrations of the dildo against my prostrate apparently did the job, and soon I was hard. With cum all over my face, cum still leaking out of my ass, and as I fucked myself with the dildo, I jerked myself off. I involuntarily started to moan as my orgasm approached, and Katie placed a small bowl just under cock and ordered me to shoot my load into the bowl. Waves of pure pleasure, intensified by the vibrations of the dildo up my ass, washed over me as I shot an huge load of semen into the bowl, and by the time I finished, I was shaking and panting. Katie then had me get on all fours and lick my semen out of the bowl like a dog.
The party broke up shortly thereafter, and after cleaning up, I was once again bound and locked in the corner. I was not permitted to clean myself up, and exhausted from the events of the day, I passed out.
The next morning, I was finally permitted to clean myself up, but I again had to put on the maids uniform. I reapplied my make-up and fixed my hair, and the vibrating dildo was once again locked into my ass. For the rest of the day, I had to go to each of the girl's houses and clean them to their satisfaction, all the while holding a dildo in my mouth with my ankles locked together with hobbling cuffs and my hands cuffed in front of me. When I finished, I had to prepare dinner at Katie's place, and I had to serve dinner to the girls and several male guests. For dessert, I had to crawl under the table, and as they had coffee and chatted, I had to blow each of the men at the table. I of course had to thank them for the treat.
The next day, I put on the outfit I had bought at the mall - black boots, grey pleated skirt, and pink cable turtleneck - and I went with the girls back to the mall. Because my own credit card was close to being maxed out, Katie made me sign up for a department store credit card, and I was forced to by an entire wardrobe of women's clothes for myself. I had to try on everything and model it for the girls, and by the time we finished, I had purchased thousands of dollars worth of shoes, skirts, dresses, sweaters, blouses, and accessories. On our way out, I had to stop in and see the two guards.
The black guard, whose name was Jake, seemed genuinely thrilled to see me, and he gave me a huge bear-hug, grinding his crotch into me as he did. Katie told me not to be shy and give my boyfriend a kiss. Before I could react, Jake grabbed the back of my head and gave me a long, passionate kiss. His tongue darted into my mouth, and I could feel him getting quite hard. His hand ventured under my skirt and fondled my ass, and as all the girls watched, he proceeded to twirl me around, bend me over, and fuck my ass. As Jake fucked me, Katie told Gary, the first guard, that I would probably be more than happy to suck him off, so I was double-teamed once again.
After the boys finished fucking me, we headed back to Katie's house where I put on a full fashion show for them (and the camera). The girls gave me pointers on how to walk like a woman, and by the time I was finished, I had gotten quite good at walking in heels.
I served the girls the entire week, and each day, I sucked at least three guys off and was fucked up the ass multiple times. At the end of each day, I had to fuck myself with the dildo while I jerked myself off, and I always had to lick up my own cum.
Saturday arrived, and Katie announced that tonight would be my big night. The girls argued a bit over my outfit for the evening, and they settled on fuzzy red angora turtleneck that had an enormous collar (probably six or seven inches folded over), with ruffled details and the collar and cuffs. I did not wear a bra, so the nipples from my breasts jutted out obscenely from the fuzzy fabric of the turtleneck. I then put on a pair of red satin panties, an incredibly short black leather miniskirt, sheer black stockings, and a pair of black stiletto "fuck-me" heels.
I made sure my make-up and nails were good, and Katie led me into the family room, where I was ordered to my knees. Katie explained that, to reach the pinnacle of my adult stage, I would be the guest of honor at the party tonight, and it would be a bukkake party thrown in my honor. I knew what bukkake parties were, and I felt sick with dread as Katie explained the rules of the evening. I was handed a large glass bowl, and over the course of the evening, each guest would jerk off into my mouth. I would not be permitted to swallow; rather, I was to deposit each "gift" into the bowl and then thank the man giving me the gift. This would continue over the course of the night, and after all "gifts" had been delivered, I would have the honor of drinking it all down.
Soon thereafter, the guests started arriving. Katie and the girls basically started a production line, fluffing each guy until they were just on the verge of cumming. The guy would then step up to me, I would open my mouth, and he would shoot his load into my open mouth. When he finished, I would let it dribble out of my mouth and into the bowl and then thank him. Over the next several hours, over fifty guys had jerked off into my mouth, some of them more than once, and the bowl slowly filled with semen. After all of the men had finished, Katie handed me the vibrating dildo and ordered me to fuck myself and jerk off into the bowl, too. When I had shot my load, Katie ordered me to lift the bowl to my lips and drink it all down.
It was a cold, slimy and congealed mess, but Katie warned me not to spill a precious drop, and I placed the bowl to my lips, tilted my head back, and slowly poured the contents of the bowl into my mouth. Katie ordered me to drink it all down at once, and I gulped down mouthful after mouthful of semen. By the time I finished, I must have swallowed almost half a gallon of semen, and Katie made me lick the bowl clean.
On Sunday, I simply watched as Katie and the girls spliced all of the footage of me over the last week together to create and entire documentary of my transformation. When they had finished, Katie told me she had one more surprise for me, and it was related to our return to work on the next day, but someone else wanted to fill me in on the surprise.
With that, at to my horror, Karen, my boss, walked in. Karen proceeded to explain how my entire transformation had been her idea, as Katie had done what she was supposed to do as IT Manager and had reported my porn stash to her immediately. Karen went on to explain that I could no longer serve in a management position, but I would be permitted to serve as her personal secretary. From this day forward, I would live and dress at all times like a woman, and I would basically become her obedient little sissy slave. The only other option I had would be to forfeit my career and my life savings to them in the ensuing lawsuits.
I was totally broken by then, and I simply broke down and cried. Karen paid little attention to my tears, and told me to report to work at 6:30 a.m. sharp wearing an appropriate skirt, sweater, and heels. A company meeting would be held at 8:30 a.m. to re-introduce me to the staff, and I would be expected to explain how I was going to proceed with gender reassignment surgery, but as part of that process, I had to live as a woman for a year. Karen would then explain my new secretarial role.
Epilogue
Thus began my life as Holly, a sissy slave to my boss and co-workers. Over the course of the next year, my feminization continued. I was put on a strict diet and exercise plan, and I dropped down to 125 pounds and a size 6 dress. I went through round after round of laser hair removal, and I had permanent eyeliner tattooed on my eyelids. Karen started me on female hormone therapy, and my testicles shrank down to tiny nubs. I had breast augmentation surgery, and I now have D-sized breasts. Karen also had my scrotum removed, but she did allow me to keep my largely non-functional penis. Finally, I had facial feminization surgery, where I had a nose job, cheek implants, a chin implant, fat injections in my lips, and my brow was shaved down and lifted. Finally, my adams' apple was shave down, and my vocal cords were shaved to raise the pitch of my voice. By the time all was said and done, and with the exception of my still-intact penis, I had been transformed into a complete woman. Katie and the girls ended up selling the video of my transformation on-line, and they made quite a profit. All of my possessions were sold, and I now live at Karen's house as her sissy maid, and I serve as her sissy secretary during the day at work.