Hello Cassie

Hi. My name is Cassie. This is my story. I hope you find it entertaining, but if you don’t, well, it is what it is. I didn’t plan it, never could have predicted it, and though some of the events that changed me and allowed me to be who I have become were difficult, I will always be grateful for the realizations and change they ultimately brought to me. They freed me. Like a cat who fights you every step of the way through a bath, and then is so pleased how good she feels.

At the time, I had just moved out of my parents house for the first time, and moved in with my best friend, Micky. Had I wanted, my parents had provided me with a free ride to an enjoyable life, with ivy league schools and a fast track in a major defense company. But, I preferred skipping school, surfing, and getting high. I was expelled from 10th grade 4 times. To say I was a disappointment to them would be an understatement. I was good at tennis and running, but not contact sports. I was slight, maybe 135 at 5’9”, and not muscled, definitely not confident, couldn’t handle myself in a fight. I would have told you I was all about girls, but I was pretty screwed up with anxieties and insecurities. Although I’d had a few girlfriends, and made out, I had yet to actually have intercourse. This kept me ‘messed up,’ wondering what was wrong and if I was gay. I had several humiliating incidents where the girl was ready and I chickened out. I desperately wished to be normal. I had had a few blowjobs from prostitutes, but also was (sort of, maybe) molested twice by male strangers. So, add and subtract, and I was a mess sexually. I’m sure the **** I was doing didn’t help.

I was living in a run down hippie house with my best friend, and going to the beach, surfing, and getting drunk and high were my main pursuits. We sold pot and sometimes coke for spending money and to have leisure ****, beer, and cigarettes. Oh yeah, and food. I would have told you I was happy, living the good life. Until Buck showed up and took residence on the couch in the living room.

I have to admit it: I was more than a little pissed at Micky for bringing Buck Buchanon into my life. For good reason: Buck was a seriously scary dude. A true badass, I’d seen him destroy men 3 times his size, and he wasn’t small. I guess he’d been away in prison doing time for killing his wife, manslaughter. I heard he’d done 2 other bids for ****. He’d told me once that he didn’t mind prison at all. He would beat up the baddest dude in each gang, take whoever he wanted to be his bitch, run contraband, bribe the guards, and live large in the pen. I especially didn’t like the part about taking a bitch, and the way he looked at me when he said it. Also, it seemed he knew something about me, something I couldn’t admit to myself, much less anybody else. And there was this other thing…At around age 11 when I had a crush on my sitter (I had a younger sister and my folks both worked,) I had taken her swimsuit and jerked off while sniffing the crotch. Since then my father had busted me several times in my mother’s bra, and/or fucking myself with a cucumber or anything cylindrical. My father never spoke of it other than to yell at me when he caught me. Mickey had caught me too, suddenly appearing at my window, and I never knew how much he saw. We never spoke of it. But I wondered if he told Buck, because it seemed like Buck knew. Something.

There were some comments Buck made: how tight my jeans were, how I had a nice ass for a boy. I just didn’t reply and got away from him as fast as I could, burning with shame. But one night I overheard him and Micky talking about me, and though I couldn’t hear all the details, I could surmise that he was taking about fucking me, whether I wanted to or not, and that Micky convinced him not to. I remember being terrified and sleepless all night. Mind you, I pretty much knew that if Buck ‘owned’ you, you got beat up a lot too.

Things remained like that. For a while. Then The Event happened. Around 3 am, in my bed, after passing out from too much beer and whiskey, I came awake to find my underwear already down to my knees, and strong hands pressing me firmly face down into my mattress. I was shocked, I guess I’d been dreaming about a girl at the bar that I almost got to come home with, but I was too drunk and she got off the hook. Whatever, I had a hardon when I came to.

I yelled “NO’ when I realized what was going on, but received a slap to the head that left me completely dazed, with my ear literally ringing. Defeated, I barely struggled as my legs were moved over the edge of the bed, and **** apart. I think I was in shock. I thought I knew what was going to happen, but my brain could not produce a coherent thought. The mental concept of what this might be like did not match the physical reality at all. I heard him spit, and he rubbed my asshole while I struggled and pleaded “no, no, no.” No one had ever touched my asshole in this manner, much less any manner, in my entire life. I felt completely violated, completely helpless. Then a freight train roared up my ass and it hurt!. I screamed like a little girl. But he just pulled it out and slammed it in again, and he would not stop. It went on forever and my rectum tore and bled and I sobbed into my sheets. I know now that, yes, I was ****, but he could have hurt me a lot worse. He was just drunk and fucking me, and he didn’t care one way or the other how I felt about it. And he had a really big cock. Each thrust hurt all the way to my stomach. Eventually he swelled even bigger, and shot at least three huge loads of cum deep into me. All I could think was "take it out, take it out." But instead he lay on top of me with his dick still up inside for a long while before pulling out and wiping himself on my buns. He put his hand inside my butt cheeks, got a bunch of scum, and wiped his hand across my face, smearing ass juice and cum all over my face and forcing it into my mouth and nose. Next he threw me back up onto my bed, climbed in with me, holding me spooned firmly with one large arm. I could feel that fearsome cock still throbbing and hot upon my skin, right in my ass crack, touching my anus. Then he began to snore.

I was completely sober now. I knew I was hurt, but not how badly, though I was sure I could not walk or run away, even if I had the chance. A couple times I tried to gently slip away, but he grasped me tighter, and I felt that cock twitch and begin to swell against my destroyed anus. I went stock still at those times, praying he would stay asleep. Maybe when he woke up he would not remember **** me, and he would just go away and we would never speak of it. I lay there, wide awake and still in shock. I could feel cum and juice all over my ass and face, and my asshole throbbed and ached. I could smell and taste only cum, ass juice, and Buck Buchanon, reeking of ****, cigarettes, and body odor. Hours passed, eventually he responded to some internal clock, and began to stir. He did not move his arm.

He said “good morning bitch,’ and reached over my leg to grasp my penis, stroking it a couple times. “What do you even do with this little thing?” I burned with shame. Now he grabbed my nuts and squeezed them cruelly, and **** me onto my back with my legs spread and over to the edge of the bed as my testicles screamed in outrage. “How do you say good morning to your new daddy today bitch?”

I once saw a video where a pride of lions was eating a gazelle, still alive. It didn’t move, seemingly not feeling them rip it’s body apart. It just stared at them, looking insulted and outraged. That is exactly how I felt. Buck spit on his hand and pressed it to my anus. I began to struggle, my ass was so hurt and no way I could bear even the thought of that cock going in again, but he raised his hand to slap me again, and I stilled while he bounced his cock against my asshole. Then he pressed it to my anus and plunged into me, thrusting savagely back and forth, plowing me relentlessly deep inside. He took me like a girl, on my back, legs spread over his arms, firmly holding my wrists with my feet up in the air. I could not move even an inch out of the way, he held me so effortlessly. He was unbelievably strong, probably from working construction all his life, and lifting weights in jail. In spite of myself, I sobbed and blubbered, even despite knowing my roommates were probably listening to all of it, every slap and stroke, every cry and sob. Hell, everyone in the house, the apartment above, and 2 houses either side of ours must have heard that! The humiliation was as painful as the ****. Almost. No, not really, not even close. I was absolutely mortified, but the physical pain was unbelievable.

After a while, he pulled out, and tossed me up onto my bed. I was a rag doll, I could not lift my legs at all. He climbed in, hoisted my ankles over my head again, and lowered himself on top of me, crushing and grinding my testicles between us.

Buck ordered: "Open your mouth bitch, give daddy some tongue.” I began to shake my head, but all he had to do was raise his hand, and I complied, sobbing. He probed deeply with his tongue, engaging mine in despite my revulsion. And he had me, completely. Not an ounce of resistance left. I couldn’t move at all, he had me pinned, and my asshole was completely open as he thrust against my stomach, deep in the recesses of my body. His tongue took away the last bit of resistance in me. He lifted my legs again and roared back into my asshole. He fucked me like that for a long time, alternately slowing down and speeding up again. Every other thrust my balls got pinned painfully between us, but he never cared about that. In fact, he seemed to enjoy it, making sure to crush them often. He kept sticking his tongue down my throat, and when he finally sped up, swelled and ejaculated a quart of hot sticky cum deep into me, I almost expected it to come up into my throat, and for him to taste it. He lay there upon me for a while, our breathing returning to somewhat normal. He made me open my mouth again, and tongue **** my mouth for a long time. I was so utterly defeated: mouth open and invaded, legs spread, anus gaping open with cum and whatever leaking out as it pleased.

Eventually he grinned at me and said: “say it.” I looked at him, confused, and he said: “say good morning Daddy. And look me in my eyes and make me feel it.”

And, God help me, I looked into his cold pale blue eyes, mustered something for a smile, and said: “Good morning Daddy.” Anything at all to make him leave.

“Perfect. Ok bitch, that was one sweet ass, I knew it would be. Don’t worry about not being able to walk, none of my new bitches can walk for the first couple days. Say Bye Daddy, have a great day.”

And I said: “Bye Daddy, have a great day!”

He left the bedroom. I heard conversation in the living room, mostly muted, some laughing, and I did make out: “can’t walk right now,” and more laughter. I literally burned with shame. I was so mortified. There were breakfast smells and noises, and finally, the front door, a car leaving the yard. Somehow I rolled a bit onto my arm, and watched as he left, my bed being almost even with my window, and it seemed to me that he was smirking at me as he left. I fell back into my sheets, overcome by the ravages perpetrated upon my body. I lay there for 3 or 4 hours perhaps. I knew I must need to pee but even my bladder was too beaten to function. I lay there with wet spots in the sheets. About an hour after Buck left, with no warning, not that I could have done anything about it anyway, I had a large cum and anal juice discharge spontaneously from somewhere deep inside my defeated anus, which I had **** but to just lay in. I could not move my legs at all. Later, there was a soft knocking at my door, and my best friend Micky and his girlfriend Janice entered tentatively. Now it seemed, my mortification was complete.

Let me tell you about Janice. About 6 months prior, she had overdone the **** and Micky asked to leave her with me, in my bedroom. The idea of all that beautiful, sexy redheaded woman lying helpless on my floor was too much for me. I had a raging hardon. I crept over to her in the dark, and groped her breasts a bit, but when I tried to get her pants off, she seemed aware enough to block me, like she was just pretending to be asleep. So I jerked off into a towel while sniffing her panties, and I swear I heard her laugh at me when I came. Ashamed, I crept back to my bed and went to sleep, trying to forget it. Let me describe her, because she is something, and I defy any man to not be overcome with lust if she was passed out so accessible on your bedroom floor. She was really tall, close to 6 feet, maybe 5’11”, a good match for Micky's 6’2”. She had long red hair, green eyes, and an amazing figure. She was blessed with a couple of the most beautiful breasts I have ever seen: large, proportionate for a big girl, not sloppy or fat like a lot of big breasts, but big, full, and firm, no sag or droop at all. She had this sexy turn to her mouth that made me want to get in there, and beautiful big white teeth. In short, a total hottie. And she worked out, lifting weights at the gym with Micky. Although she never let it take her sexiness away, she was always more jacked than me. If I hadn’t been a bit drunk and stoned, and she hadn't been apparently ****, I never would have had the courage to creep over and feel her up that night.

So now, here she was looking upon me, and I'm completely naked, obviously having been thoroughly **** like a girl, legs up and spread akimbo and my pathetic penis and asshole completely on display, obviously savaged. I tried, but I could not even close my legs or cover myself.

Micky shook his head and said “so sorry dude, I wasn’t here…” Janice said nothing, but the look of pity on her face was worse than anything she might have said. I couldn’t walk at all, even with help, so they brought me a milk jug to pee in, and helped me to the edge of the bed for that. Janice put towels down on the wet spots which they laid me back down on, and after some unspoken agreement, Janice returned with a couple buckets and wash rags and gave me a bed bath, first washing and drying my crotch, and then rolling me on my side to clean my ass. I felt a strange mixture of humiliation and gratitude.

Roommate Old Bill stuck his head into my room, further escalating my shame, and asked “is he ok,” to which Micky replied “he will be, in a day or so, just needs to rest.” Nothing else happened that day except they brought me some water, and aspirin, and I peed in the jug a couple times. No hunger at all.

Buck did not return home that night, though I was terrified that he would, I was so beaten that I felt like I had been in a car accident. Everything hurt, but. somehow I passed out anyway. Pure exhaustion I guess.

Our house was an old Florida 1 bedroom wood frame house. Micky lived in the bedroom, with air and comfort, and usually Janice, while I lived on a converted porch, with no ac. Buck stayed on the couch in the living room, and Old Bill slept in a recliner. But when Buck came home after work the second night, it became clear that my bed was now Bucks’ bed which I shared at his discretion. By day 3, I was at least up, showered and able to walk with slow painful short steps. I had cleaned the bed and had fresh sheets.

But my hopes for an uneventful night, and that Buck would now move on and leave me alone, were dashed when he walked in, acknowledged everyone else, and said “hi bitch, miss me?” He grabbed me and kissed me full on the lips in front of everybody, even forcing his tongue into my mouth for a long humiliating minute. Taking me by the wrist, he led me away saying “come on sweetie, let’s go make some noise!” I began to cry again, regardless of my audience, pleading that my ass was so sore, and that I just started being able to walk again!

Buck said “ Better get used to it bitch, I’m not going away. You’re my bitch now.” With that, he dragged me to the bedroom, ripped off my shorts, bent me over the bed, and used me rough like a cheap whore. It hurt as badly as the first time, and I sobbed, screamed and cried again. Regardless, he tore apart my asshole, plowed through my intestines, and shoved my stomach halfway up my throat, before emptying another quart of hot sticky cum into me. It felt like he squirted strongly 5 different times when he came. It was so obvious how much he enjoyed dominating me, squashing my masculinity. Then he just left me there like that, facedown in the bed, legs hanging over, ass red and covered with cum. He went to shower and eat, and watch TV before returning. I had finally made it into the bed proper myself after trying several times, and when he came back he just pulled me into his chest and spooned me like before. And in the morning, he fucked me long and hard, this time face down into the bed. After he had finished, when he left for work, I lay there and understood that he was really not going away, that I was indeed Buck Buchanon's bitch, and this was truly going to be my new life.

And thus it went for a couple of weeks or so. Fucked most nights and mornings. I got better at it, better able to handle it, it didn’t hurt quite so bad, I was able to walk after. Not that it would ever not hurt, he was too big for that, but eventually it got to where it didn't hurt as much, and got ok after a time of fucking. Although my asshole felt like it would never close right again, and I put paper towels in my underwear because of the leaking. It became sort of normal for me, and my housemates. The house fell into the new routine, it was just that there were some changes. Buck slept in my bed, not on the couch. I was now a sissy faggot, subjugated to Buck Buchanon. There was nothing I could do about it, Buck had me dominated in every way. I really had nowhere to go, no car, no job, no money. And I was scared to **** of him. I sold weed sometimes for Mickey, but that was chump change. Mostly I just tried not to think about it, getting high with Mickey or Janice whenever I could. Surprisingly, my relationship with them didn’t really change all that much. At first.

A week or so after this, I overheard Buck, Mickey and Janice talking about something, and caught my name. I said “hey what's going on,” and caught strange expressions. Buck, of course, just looked like Buck, but Mickey looked amused like a big joke was at my expense. Janice, on the other hand, looked really animated, excited, and a little predatory. I didn’t like the look I got from her. The next night I found out why.

We had a rare dinner together, the four of us. Something was up, I could feel it. As we ate, there was an air of expectancy. After eating, Buck pushed his chair back a bit and said “come here bitch,” which fearfully, I did, standing next to him as indicated. He said: “no, I mean come here bitch,” and he pulled me down onto his lap. I was horrified. Everything he’d done to me thus far was behind closed doors, except kissing me once and dragging me to the bedroom, and though I knew my housemates knew what was going on, he had not humiliated me this badly in front of everyone. Until now. “Spread your legs,” he ordered, and dying with shame, I did it. Reaching into my underwear, he began fondling my penis and balls, pulling and squeezing gently. With Buck, that was terrifying enough because I never knew when he might hurt me, or yank me into the air screaming by my little testicles. But he just continued to fondle, and despite my humiliation, I began to stiffen. Everyone else just ate desert like everything was normal and nothing weird was going on. Then they cleared the table, and returned and sat down, like they were all going to watch a show.

Janice, practically jumping out of her chair with excitement, said: “now Buck?”

Buck nodded, still pulling on my little penis, which was now half hard. Janice jumped up, went to Mickey’s room and returned, first with a pile of clothing, and then a box, both of which she set on the table. I realized that they were girls' clothes. I was later to learn they were a sundress, shorts, a couple skirts, some tops. There were two bras and several panties. Girly socks and sneakers. A two piece pajama set. A pair of white heeled sandals and a pair of cowgirl booties. And the box contained bath and shower stuff, scented soaps, razors, feminine antiperspirant, shampoo and conditioner. And there was perfume. All girly. All scented. I did not like where this was heading. Now his kneading became stronger, and a bit painful.

“You have new orders, bitch. Janice is now the boss of you. Anything she tells you to do, you say: yes ma'am, and you do it without question, or you will regret it with me. Clear?” I nodded miserably. She is the boss of you and is going to train you to be my sissy bitch and act like I want you to act. Mickey and Old Bill apparently thought this was hilarious, while I was thinking of how I had to find a way to escape this place and run away. “Time for your first order, Ms. Janice,” he declared.

Janice looked at me, completely predatory now, and gave me my first order. “ Take these clothes and the supplies into your bedroom, and change into the white bra, panties, put on the dress and sandals, and come back out here. Hurry sissy!”

I said: “Wait, what, you must be out of your mind, hell no I won’t...”

Before I even finished speaking I was jerked up, rushed to the couch by Buck and Micky, **** face down into the couch across Buck's legs. My pants were ripped down rendering me naked and **** in front of everybody, and Buck set to spanking my exposed ass, really hard. It hurt like hell. Quickly I was sobbing, screaming and pleading for Buck to please stop this, it hurt so much! After a couple minutes of that, sobbing like a 6 year old, snot rolling down my face,

Buck finally stopped. “Now pay close attention this time bitch, or I will give you something to really cry about. Janice is the boss of you, you say yes ma'am and do anything she says or I will beat you. Do you understand this time?” I nodded my head vigorously. But he wasn’t done. “Ms. Janice, sissy needs some discipline from you so she knows how things stand.” And fetching a hairbrush from the box, she came over and began to hit my burning ass with it, again and again. Oh that hurt! Again with the begging, pleading, crying and screaming while I twisted and turned, trying to escape that infernal brush, while the men held me firmly, ass easily accessible to her punishment. It stopped eventually, but then she spit on the handle, and shoved it into my asshole, further humiliating me.

“Clean your face sissy,” Ms. Janice ordered, throwing my underwear at me. “Don’t you dare remove that brush until you get into your room, it’s yours now. Brush down your hair with it.” I looked into her face, looking to see if she was joking, but she was resolute, not kidding a bit. I looked at Buck, and Mickey and even Old Bill, and knew my place.

Buck said:, “what do you say when Ms. Janice gives you a command, bitch?”

And I looked at her and said “yes ma’am.” Meekly I arose, mincing in pain from my tortured ass, and with the brush lodged in my asshole, went to my room and began to inspect my new clothing.

Stripping off my jeans, underwear, and t-shirt, I discovered that Janice, er: Ms. Janice, had purchased everything in the right size for me. The panties were, well, girly panties, and sparse, barely covering me, but they fit. Utterly defeated, I pulled them on, and the bra, which was even more humiliating. The socks were small and frilly. But pulling on the dress really brought home my plight. Crying softly, I brushed my curly hair down upon my shoulders, lingering as long as possible. I had a lot of hair, but it was really curly and usually it stayed up in a wiry afro. With brushing though, I could bring it down to frame my face, and lay it further down across my shoulders. Privately, it dawned on me that it was kind of cool, the dress looked good on me, and I was a little thrilled to be in girly clothes. But I dreaded anyone ever seeing me like this. I would have done anything to avoid going out there, dressed like a girl, in front of everybody.

But Ms. Janice called “what the fuck is taking you so long bitch? Get your sissy ass out here for inspection right now, if you don’t want another spanking.” So I lay down the brush, took a deep breath, and walked out to present my sissy self to my former friends and my New Daddy.

Janice said ”oh how cute is that?”

“That’s more like it,” said Buck, “Good work Janice. Come here and give Daddy a kiss sweetie.” And mortified, I did just that, moving to Buck and offering my face for a kiss. He stuck his tongue deeply into my mouth, and I let him, trying not to cry again. He pulled me into his lap and held me. “Ok peeps, go get all of his boy shit out of there.”

Again I protested; “wait, what?” and I began to struggle, but to no avail. He was so strong, and held me there easily. I could only watch as Mickey, Ms. Janice and Old Bill went back and forth from my room, bringing out all my clothes and piling them on the living room floor. All my underwear, jeans, surf shorts, t-shirts, everything male that I owned. My shoes, sneakers, and boots too. Even my cologne. Everything from my room that a boy would have.

Florida stays light out really late, so it was still daylight when we all trooped outside to the picnic table to have a little clothes burning party. Of course, I didn’t want to go outside dressed like this, nor did I want everything male I owned to be burned. But who asks a little sissy bitch what she wants? They brought out beer and weed, not that I would get any, and proceeded to make quite the party out of it. They heaped my stuff in the fire pit, and all popped open a cold beer while they put lighter fluid on my stuff. Buck handed me a pack of matches and said “light it up bitch.” To my horror, the neighbors from upstairs and next door called over and said, “what are you guys doing?” and when they heard, they all started laughing at me and joined in the party while I cried and tried to light the matches. My hands were shaking so badly I just couldn’t do it. So Buck took them and lit them, holding them to the pile, and a cheer and more laughter went up as the flames grew, devouring all my stuff. Buck pulled me to his side on the bench, and put his arm around me. He fondled me at will, stroking my shoulders, legs and butt, pinching my nipples, plunging his hand between my legs under my dress to fondle my penis and testicles. He rubbed my asshole through the panties until I had a wet spot. A dress and panties, of course, offer no defense to groping. He even kissed me out there, in front of everyone, like I was his girlfriend. The sweet smell of marijuana surrounded us as the daylight faded and my last connection to my manhood went up in smoke. The fire burned low, my stuff was gone now, for good.

After a long deep kiss, Buck announced: “well, time for bed honey.” and to my surprise, picked me right up to carry me to bed. The man was so strong. My dress hung down for all to see my panty clad ass. Again, so ashamed. Nothing else to do, I tried to retreat mentally into a back corner of my mind. Buck carried me to our bed, pulled the dress over my head, kissing my body, my nipples, my tummy. He stuck his tongue down my throat, and kissed my neck, my ears. He pulled down my panties, and fingered my asshole while he licked and sucked on my penis and testicles. He took my whole manhood into his mouth, and I knew he could bite it all off if he chose to. He turned me around, bent me over and deep tongued my anus. At this point, I couldn’t deny it. Even horrified, I was clearly ready. I could not believe it, but I was hot and ready, and wanted to feel the head of his cock against my asshole. He turned me around again, pulled me onto his lap, and lowered me onto his rock hard cock. I was so ready it slid right in, without as much pain as usual. I did not recognize myself. I did not expect this to happen. What was going on? He moved his face for my mouth, and I willingly opened it and began to entwine my tongue with his. He thrust up into my bottom, and I began to move in time to him, lifting up as he sunk and withdrew, lowering as he thrust upward into me. Time disappeared, it was just open and receive, lift and return again, and again. Here and there, I was aware that my penis squirted and driibbled. Finally, I felt the familiar heat and swelling of his cock, but before he ejaculated, he pushed me up, and then to my knees. He placed his cock into my mouth, and fucked my face for a while before swelling again, gagging me. this time to blast his enormous load down my throat, filling my mouth with cum. I tried to swallow, succeeding only partially, and hot sticky cum spilled down my chin and neck. Buck wiped the cum over my face and mouth, and more over my penis and testicles, and yet more on my asshole and butt cheeks. Next he got us into bed, spooning me again as I’d come to expect. But, this time I wasn’t crying. My pelvis, tummy and ass felt wonderful, warm and slightly throbbing. My senses were filled with the taste, feel, and smell of cum. I felt completely satisfied. And I cradled the strong arm that held me tightly to him with my own arms. I quickly fell asleep, slept deeply and long, and awoke feeling, well, kind of yummy…

Buck awoke with morning wood. There was no need for lube, I was still soaked from last night. Lifting my legs by my ankles, he entered me much more easily, and lay atop me for a long, slow fuck. He was deeper inside me than he (or anyone) had ever been. Long thrusts and short thrusts, rapid fire and ¾ time, he fucked me. His mouth claimed mine, as well as my face and neck. Finally, he shot another improbable load deep into my rectum, and I rolled to my tummy to bask in the warmth and keep the load as long as possible.

He turned my face to his and said: “what do you say sissy?” And I said: “thank you Daddy, have a great day!”

That day, Ms. Janice went through my new supplies, and sent me to the shower to shave everything I could reach except my pubes and the hair on my head. Then she got my back, and everywhere I missed or couldn’t reach. She trimmed my pubes to a cute little puff of hair above my penis. There were wipes to prevent a rash, and lotion to soften my skin and smell nice. Then we hung out all day, doing some housework, getting high and tanning in the yard. I had to wear my bra and panties tanning, even though it was of course outside and neighbors would see.

That served to further feminize me with embarrassing tan lines, but at least I had fun. The neighbors came by and said hi, which was really embarrassing, but I was getting better at being embarrassed. Janice said Buck would love my new tan lines on my smooth body.

The next night, I was sent to bed early as Buck and Ms. Janice huddled up again. That was never a good sign. I was dying with curiosity when Buck came to bed I tried to press him for information, but he threw me over the edge of the bed, pulled off my panties and gave me the cheap wore fuck, doggie style. Quick, rough, and not much fun for me. “When you need to know something, I will fucking tell you. Now get in bed. ” he said and didn’t even spoon me til later that night. In the morning he was out the door and gone when Ms. Janice woke me up.

We went out to the table where she had a tape measuring roll waiting. She had me stand while she circled my package with it, and then grasped the head of my penis and stretched it out to a humiliating 3 inches long. “Panties, bra, shorts and crop top today bitch. Clean the bathroom. It better be perfect when I get home or you will lick the inside of the bowl clean with your tongue, understand? “A meek “yes ma’am,” was my response.

All the while, people were coming by regularly to buy weed. I had formerly been a salesman, but was now relegated to bitch status, so Old Bill took over my role. Regardless, all these people saw me anyway, even though I tried to hide, and I was humiliated on a daily basis. These were people who had known me all my life, and I knew that the word was out everywhere, This cat was not going back in the bag, ever. I felt more and more of me slipping away. Who was this in girly clothes, doing women’s work around the house. Who was it that arched to take Bucks’ cock deep into my ass, savoring the blast of hot cum inside, basking in the warm afterglow? Who was it who loved the way my legs felt, shaved smooth and silky? My brain couldn’t process it. What was happening to me was both terrifying and exciting at the same time.

About a week later, I came out for coffee to find Ms. Janice at the table, having coffee and a smoke, and a strange object was on the table. It was pink, so I knew it was for me.

What is that?” I asked.

And she introduced me to my new chastity cage. “Come here and drop your skirt and panties.”

Which I did with the usual yes ma'am. She placed the bottom around my penis and testicles, against my pubis. It had a hinge in the middle, and a piece of rubber tubing that slid over the hinge, preventing pinching. It fit pretty tightly. She had me spit on my penis, which she then worked into a metal tube, also pink, and about 2 inches long, which, with some moving of skin and prodding, she fitted it snugly to the base ring, and locked the device closed. My manhood was completely locked up in this little pink contraption! Then she took out her breasts, and bumped and moved the device between them while I strained and began to grow. Ms. Janice had truly wonderful breasts. She put my hand upon her breast and I began to feel her skin, her nipple, the heft of her breast. I got as hard as the cage allowed quickly. At the 2 inch mark, which was not very far, I ran out of room and my dilemma became apparent. I could not achieve a hardon while I was locked in this device. She gave a murmur of satisfaction, attached the keys to a light chain that nestled between her magnificent breasts.

“Ok sissy, pull up your skirt and panties. After breakfast, clean the kitchen, including the floor. Oh, almost forgot, wait a second.” Returning from her room she brought a box of pills, 6 or 8 different bottles. “From now on, you take 2 of each of these at night, every night, never miss, got it?”

I nodded “yes ma’am. What are they?”

Ms. Janice said “sissy pills for a sissy is all you need to know. Bucks gonna give you a shot in the ass once a week, and I don’t mean with his cock like we can hear him doing every night. Take 2 of each right now, which I did. Go put them in your room and clean the kitchen like I told you.”

Again, “yes ma’am,” from me.

I looked quickly as I opened the bottles and took 2 of each. With a sinking feeling I recognized estrogen, but the rest were various herbs and vitamins. I was more concerned with my new cage at the moment, as I hurried to clean per Ms. Janice orders. It was very snug around the base of my package, and my testicles. My penis was ok, unless it tried to grow.

Now a word about The Girls: I’d known both Donna and Cindy for most of my life. Donna was very unattractive, and had run the gamut of things a girl can do that I found unsavory. Multiple abortions, live sex dancing in scummy clubs and theaters, lots of jail time for ****, prostitution, living with repulsive guys. She had actually once been Old Bill's live-in back in the day, and Micky and I had to take her for an abortion because Old Bill was too busy getting high. Lank hair, saggy breasts, bad skin all over. Not a girl for me, but ok to get high with I guess. Cindy was another story. Dark eyed, long straight brown hair, she had a good amount of Cherokee bloodlines. She had a rocking body and great laugh, with a very kissable mouth. We had history, and I still wanted her. We’d hooked up for a while, but it just kind of fizzled out, probably because I was a stoner, with no ambition.

And here they were, one day, at the table smoking weed with Janice, Mickey, and Old Bill. I heard them laughing from my room, and just died. I’d recognize Cindy's laugh anywhere. I was dying with shame, I was so embarrassed. Not many places to hide in my little room, but I resolved to wait it out until they left.

Until, of course, Ms. Janice called “sissy, come out here.” And that is what I had to do. I was in the shorts again, with a little halter top and a bra. Panties, and of course, my new nemesis, the little pink chastity cage underneath. I was hating that thing those days because my penis kept trying to get hard, and it hurt confined in a 2 inch metal tube. I got away, mostly, with not having to wear it in bed because my squirming and whimpering kept Buck up when he wanted to sleep. I’d tried to get the thing off, but to no avail. When Ms. Janice locked it on, it was on there until she or Buck unlocked it. Buck was the only other person who could take it off. End of story.

Anyway, when I came out like that, Cindy and Donna laughed and laughed. Old Bill and Micky were also enjoying this new humiliating outrage. Ms. Janice had me unbutton and lower my shorts, and the new girls oohed and ahhed over my shaved ass and legs. Then they pulled my panties down too, feeling my ass and legs and exclaiming over the cage. I was crying softly with shame. To have Cindy see me like this. The conditioner Ms. Janice had smoothed my hair some and now it lay across my shoulder blades.

“How cute, but he needs some makeup, don’t you think?” I couldn’t believe Cindy said that, I thought we liked each other. So Donna and Cindy put makeup on me: they did my eyebrows, put on eyeliner and mascara, and finally applied lipstick to my lips. When they were done, they all sat back and stared at me, I couldn’t imagine how ridiculous I must have looked. They all looked at each other kind of strangely for a long minute.

Donna said, “Oh my God, we have to show him.” With that Donna and Cindy each grabbed a hand and pulled me to my bedroom mirror. And I was stunned. I did look good. I would fuck me. Well, you know what I mean, when I was a real boy I would have been attracted to the girl peering at me from my mirror. I loved that, it excited me! I never would have imagined I could look like this. I guess it proved to me I really was a girly boy, a sissy cum dump.

Then we all went back to the table and got high, and Ms. Janice said “you know, I like this a lot, I think we’re a Girls’ Club,” and they laughed and clapped, obviously delighted. I just sighed, who knew where this latest development might be headed, but it wasn’t like I had a choice anyway. Everything they did, every humiliation, every step down the sissy rabbit hole was overshadowed by the reality: I would do it or get the shit slapped out of me by Buck. Or worse. I was too afraid to say anything but “yes ma’am.”

“What shall we do with the new Girls’ Club and our sissy boi toy?” Ms. Janice posed, and a slew of humiliating ideas were discussed. They almost all included a feminized me, in public.

So life went on a while. I lived fem 24/7, kept hairless, lotioned, and scented. Ms. Janice inspected me all the time, making sure I was smooth and caged. My waking hours were spent in chastity, unless I was showering or getting fucked. I got fucked most nights and mornings, took care of my hygiene tasks, prepared the food, cleaned the house, and hung out with Ms. Janice and now Donna and Cindy. Sometimes other girls came over too. Cindy mainly, but Donna and the other girls schooled me every day on becoming a girl. How to walk, how to sit, how to get in and out of a car. No more standing to pee, ever. They brought clothes from home, heels, We tanned in the yard, and Donna bought me a bikini of hers. We were close to the same size. I took my meds every night. Buck gave me the first shot, I guess because he enjoyed taking the destruction of my manhood one step further. But he tired of it quickly and Ms. Janice gave me what I came to find out was estrogen, and testosterone blockers, once a week, and later, twice a week. I didn’t really see much change from that at that time, except I definitely felt weaker, and more emotional. Old Man Bill got caught skimming weed and money, so Mickey beat him up and kicked him out. The upshot for me was that now I was back to selling a lot of the product, which meant interacting with lots of people, many former friends from all aspects of my life. This was my home town. There were many humiliating scenes.

At one point my family insisted upon seeing if I was ok. Buck let me know he would hurt them if I let on that I was being **** or that I was unhappy. He threatened to kill them right there if I tried to use the visit to get away. So my family came over, saw me dressed like a girl, talked to me a bit and left shaking their heads. I felt myself fall further down the rabbit hole that day.

Buck agreed to let the girls take me out to a beauty salon, as long as I was in chastity. It was my first trip out since being turned, now almost 2 months. I was summoned to the living room after the party and informed of the outing, but also that “permanent makeup” was to be applied at the salon, and that I was to appear eager to get it done with the beautician. I had not been out of the house since Buck turned me, and though I was bored of homemaker duties, I was terrified to go out in public as a girl. They made me wear this old romper of Cindy's which meant it was too short. The bottom of my ass cheeks hung out at every movement. I was in thong panties, the front was visible too if I wasn’t careful. They ushered me out to the car, and off we went. When we got to the salon, I did not want to get out, but they just dragged me into the sunlight, and across the parking lot to Karen's Mane Event, for women. Once inside though, it wasn’t embarrassing at all. Karen the beautician made it totally comfortable. I actually enjoyed it. She did my eyebrows, eyeliner and lipliner permanent.

Before she did, she looked at me and said: “Are you completely sure you want to do this? It will be permanent, and there is no going back.” I could feel Ms. Janice grip my arm a bit painfully.

I nodded and said “yes, go ahead please.” She began, and I could literally feel more of my maleness slipping away like sand in an hourglass. She did a much better job of it than anyone else had so far. She did some stuff for my face, some blush and concealer (did I mention I wasn’t too good with drinking and driving? I had a couple accident scars, fortunately nothing too big). She did the rest of my eyes, lips, and nails. And it looked good. I could not believe it was me in the mirror. Best yet. Buck liked it so much he fucked me two times that night plus once more in the morning. He stayed home from work and we got high and fucked all day. No cleaning, we watched movies and had pizza delivered too. I hadn’t been out of chastity that long in forever, it seemed. I had several sissygasms, though I could have them in chastity too.

Now I started being allowed to go to the grocery, escorted and caged of course. Most of the time in a too short skirt or skimpy dress, the romper, or really distressed jean shorts with embarrassingly situated holes. Always with a thong or panty top visible in the back. The point is, despite my embarrassment, I got a lot of positive reactions from men there, and my confidence about looking passable grew. The permanent makeup made getting ready a lot quicker, and better looking too. Of course, the register was always a shit show, because I had to speak, so if I had been passing, that was over. In the beginning, Micky and Janice escorted me, but then Donna and or Cindy came. The latter were more fun, more relaxed girlfriend time. There were definitely aspects of “being a girl” that I truly enjoyed.

The next big deal was a trip (the first of several) to the tattoo parlor. On my first trip I was tattooed with a tramp stamp: a vine and roses on my low back. It was definitely female, and definitely slutty. Additionally, my penis was pierced. The girls had to pretty much drag me in when I found out what was up, but a minor scolding from Ms. Janice and I submitted while they sat me legs spread on a narrow table, and held my penis for the guy to punch a hole in. It hurt pretty bad, but the real pain was the aggravating 6 weeks it took to heal. He put the piercing needle (more like a spike!) into the tip of my penis and punched a hole out the bottom, right where the helmet of the penis curves up and meets. A ring was inserted and attached with special piers. I could not get the ring out myself. With that stab right through my penis, another level of manhood was taken away, and my subjugation that much more complete. It fit perfectly through the pee slot in the end of my cage so other than occasional pinching, it was not an issue to wear with the cage. I was instructed on piercing care, as well as tattoo care, and home we went. Buck really liked both, and like I said, it was just the first of several trips. Ultimately, I ended up with my penis, both nipples, my tongue, my belly button, both ears and my nose pierced. I ended up with a tattooed ribbon around my right ankle, a bird on my left shin on the outside, a pair of matching bows on the back of each thigh, a heart that says “Daddy’s Girl” on my left ass cheek, Some writing under my left elbow along the bottom of my ribs that said clearly in two thin lines: “I am Daddy’s little slut, I live to suck his cock, ride his big cock, and eat his cum.” Hard to look manly with a tat like that, huh? Additionally, I have a butterfly on my left shoulder blade, and some stars with light rays on my right shoulder, going up my arm. And under my belly button, just above my landing strip, in a pretty script design but also clearly readable, the tattoo says “SISSY.” As with many of the indignities visited upon me, these were all permanent steps down the rabbit hole of feminization.

Ultimately my ears, tongue, belly button, nipples, and of course my penis, were all pierced and fitted with rings or barbells. I realized I was starting to cost a lot of money, so I asked Ms. Janice who was paying for all the meds, and tats, and salons. She told me Buck was, but “not to worry, we’re keeping a tab which you will pay back every penny of.” That was ominous, I didn’t want or ask for any of this stuff, it was probably adding up pretty well, and I had no idea what Buck could possibly make me do to “pay back every penny.”

Time passed. I was fucked generally once or twice every night. It still hurt some, I don’t think much of anyone could take Bucks’ cock without some pain, but now I was deriving a lot of pleasure too, and I knew I wanted it, even if I continued to act like it was an outrage committed upon me. I don’t know why I am like that, too afraid to admit my feminine desires. My role of sissy house cleaner, cook, and weed dealer was now the normal routine. Six months I had been on an aggressive regime of HRT meds and now I noticed changes. My muscles got smaller, my skin was softer, I now possessed a little feminine tummy, and it seemed there was more butt in my cheeks! There seemed to be some increase in my hips, my clothing fit was changing subtly. Clearly feminine breasts had begun, my nipples were larger and sore all the time. I could easily feel the “bud” under them, and the breasts themselves were now visible. Small, but undeniably feminine breasts were here. They were easy to see in a tee shirt, especially my nipples. My testicles had gotten about 50% smaller, and my penis, though mostly caged, appeared even smaller than before. I rarely felt it try to become erect anymore anyway. Any ejaculation I had was a sissygasm, and the color had become clearer and tasted sweeter, less salty. It had become easier to dehair, as less and less grew back to denude. I was feeling a little crazy, prone to cry easily, maybe moody. I felt some depression about my situation, and the changes **** upon me. A lot of loss for the old life that was forcibly taken from me. But I also had a lot of excitement and sometimes outright joy about my new life I had been given. Living 24/7 as a girl made me happy. My orgasms were better too. It seemed my whole pelvic area, loins to tummy and deep inside, my whole body really, all got super warm when Buck fucked me well. I felt so good after, I could just lay there glowing. Being spooned after with his cock still inside as I fell asleep made me a happy girl. I was constantly schooled in being fem, and everything from the way I walked, sat, and moved had changed to fem. As long as I didn’t speak, I could pretty much pass anywhere. Though my speech was schooled too, and was different from before. Even though I had been ****, abused, and humiliated much of the way, I felt gratitude toward my “captors.” Without them forcing me, I never would have explored my fem side. They have awakened me to a whole large part of myself that I would never have had the courage to explore.