Confessions of a Transsexual

by heather_tg

16 Dec 2009 5063 readers Score 7.4 (12 votes) PDF Mobi ePub Txt


I got home early in the morning wearing the black clogs that Sammy had picked out for me, white thigh-high leggings, red and black plaid schoolgirl miniskirt - probably more accurately called a microskirt because it was so tiny, white nylon thong, and the sheer-white tie shirt that ties in the front. The shirt was like a half-shirt, leaving my tummy uncovered and consisting of only enough fabric to wrap around my DD breasts and then knot it between them and since it was sheer it was almost as though I really wasn't wearing a top anyway. You could see my nipples from clear across the room through it. And, of course, I was now a platinum blond. I unlocked the door trying to be quiet. I was tip-toeing through the marble-floored foyer as I carry my clogs. I hear Rod call me from the den, 'Baby, is that you?' I turn the corner and stand in the doorway to the den. I whisper, 'You're up?' Remember, Rod hadn't seen me since I became a platinum blond. Rod responded, 'Wow, you look hot.' I couldn't hide my smile. I thanked him. Rod asked, 'When did you decide to become blond?' I couldn't tell him the truth that Sammy bought the hair color for me and demanded I use it. I responded, 'I don't know, just the other day.' I added, ' You really like it?' Rod smiled and stated, 'Yeah, I really like it. It makes you look slutty.' That wasn't exactly the answer I was looking for, but I guess I'll take what I can get.

He got up from the sofa and grabbed my hand as he passed by me. 'Let's go out,' he declared. 'Okay,' I responded. I threw my clogs back on. We briskly took off down the street. He made his way down the street with me in tow. I could hardly keep up. We went three blocks to a seedy neighborhood with about twenty prostitutes lining the streets. Two or three girls came up to Rod and greeted him. They handed him money and he conspicuously counted it aloud. Rod then introduced us, 'Jasmine, Sunshine, Tabitha... this is Katie. Teach her the ropes.' I guess Rod gave me a new name in an effort to protect me. Jasmine was a beautiful brunette that looked like she must be of maybe Arab or possibly Indian decent. Sunshine was also a brunette, but I learned later that night that she was native American. Tabitha - everyone called her 'Tabby' for short - was a beautiful blond, blue-eyed goddess. I was definitely humbled by these three gorgeous ladies. The fact that they allowed me into their clique meant so much to me. After Rod left, Jasmine was the first to speak. She went about naming things that Rod liked and then listed things Rod did not like. She added, 'You are probably here because you pissed off Rod somehow. You better get used to this lifestyle unless you have family to go home to.'

Since they were sharing, I too decided that I'd share with them that I was tranny. Upon hearing my admission, Sunshine exclaimed, 'No, get out!' I couldn't contain the laugh, but I began laughing and responded, 'No, seriously, I thought you knew.' Sunshine did 'the check' by grabbing my groin, 'Oh my god girls, she's not kidding!' she exclaimed. Tabby interjected, 'You look great!' I found it impossible to hide my smile again, 'Thank you, Tabby,' I replied. That's when I confessed my intimidation of these three goddesses. They assured me that we should stick together and consider each other sisters because life on the street was hard enough without making enemies. Tabby added, 'Besides Rod makes it easy for us to treat each other as family - he practically insists upon it. We are all former girlfriends here, right?' Sunshine quickly chimed in, 'Yeah, you're right about that.'

I felt a little weak so I asked the girls if they had any 'medicine.' Jasmine pulled out a needle and said, 'Yes, I have some right here.' I confess, the needle intimidated me. I responded, 'I've never received a shot before.' The three started laughing. Sunshine proclaimed, 'Oh, don't be silly, we're all doing it.' The weakness I felt began to just consume me and made me feel nauseated. I agreed to the shot so Jasmine and I ducked behind some nearby hedges. What a mistake. That was the beginning of the end but I just didn't know it. I was so blazed I don't remember the next eight hours. I just remember waking up nude in some guy's hotel room with a three tattoos. At least the guy was black, so I'm sure I had a good time. I got a 'tramp stamp' in my lower back. The other tattoos were permanent ruby-red lipstick and permanent black eyeliner. I was pleased with the handiwork of all three I have to admit. I got dressed and gathered my things before sneaking outside. I stopped in the doorway and thought I'd better check my purse to see if I'd been robbed. I was surprised to find that there was almost six-thousand dollars in my purse. Curiosity got the best of me, so I looked at the man asleep in the bed then at his pants hanging on the back of the chair. I briskly found his wallet and opened it to find - a police officer's shield! The guy was a cop! I checked to see if he was awake. I also read his name again hoping to commit it to memory. I looked back in his wallet and found it stuffed with five-hundred dollar bills. I decided to take two more... besides there were so many stuffed in his wallet that I figured he wouldn't miss two more. I quietly put the wallet back in its pocket and began to sneak outside when the phone rang. I was dressed like a stripper - in my slutty little schoolgirl outfit that Sammy bought for me. Since it was bright outside I wasn't too eager to go parade around especially since I had nowhere to go and I wasn't eager to see Rod at that moment. I decided to stand there inside the hotel room especially since the phone was ringing. He summoned me over to the bed after getting off the phone.

He pulled me onto the bed with him and quickly subdued me. He violently tore my panties off. I tried pushing him away and telling him, 'No,' but he just ignored me. Although I was pushing against him with all my might, he overpowered me and pulled me close. I felt his erect cock grind against me. I told him repeatedly, 'No... no,' but he began nibbling on my neck and began kneading my breasts with his free hand which honestly began feeling good to me. However, I again tried to show my displeasure by yelling, 'I said no!' He again ignored me and grunted - grinding his erection onto me even more vigorously. He gave me a deep, wet kiss; and shortly afterward I felt the head of his cock on my anus. I squirmed under his weight, but it was no use. He grunted as he thrusted his cock into me. He pulled me close. I whimpered as he penetrated me and he began to ravage me tirelessly. He rhythmically churned his hips as he impaled me again and again with his massive rod. My whimpers slowly became coos as the whole bed seemed to creak and sway with the pounding he inflicted upon me. I decided I should just submit rather than continue to fight him so my 'Nos' slowly became 'Oh Gods' and 'Yes.' Knowing that I'd submitted emboldened him. He then began sucking on my neck as he fucked me. It felt good, but that is when I realized that he was marking me. He was putting a hickey on my neck. He moved down to my left breast and began suckling it very heavily. I manage a 'no' but it's too late... now I had a hickey on my neck and left breast. Suddenly he released inside me. I recited what Jasmine told me hours before that I should say to a customer. That's when he turned on me and cuffed me. I was shocked. 'What are you doing?' I ask. 'This is YOUR cum inside me, do you realize that?' I remind him. Without saying a word he guided me around the corner to an unmarked car and put me in the back. We drove just five minutes away to his precinct.

He escorted me inside into the police headquarters and I had several men whistle at me as I walked through the crowd. They took all my money and belongings. Apparently Rod was not going to bail me out, so they locked me up in a holding cell. They also discover an outstanding warrant I had for shoplifting. They initially threw me in with the women, but after frisking me and discovering my penis they put me in a holding cell by myself.

I was awakened that night by a fat, ugly, white guard who opened his fly and ordered me to suck his cock. I knelt before him and stroked him perhaps two times when he exploded on my face. He just laughed and laughed. He thought that to be the funniest thing - his jism covering my face and that's when he informed me, 'Bitch, you're going to prison. I'm just your warmup.'

My holding cell was only two down from the men's area. My miniskirt was so short that even standing upright a little butt-cheek showed, so regardless what I did - it was difficult to avoid flashing people. I decided to untie my top and shake and shimmy for the men and I bend over a few times before they raised so much noise that they attracted a guard. Of course, I had my clothes back on before the guard got there. Nighttime arrived again. I'm awakened this time pinned facedown to my mattress with a hand covering my mouth so I can't scream and a dick up my ass. This was my first rape. Whoever it was stunk. They smelled as though they hadn't showered in days or perhaps even weeks. As he impaled me with his cock he talked to me asking me if I liked it and insulted me for teasing him. He threatened me not to tease him again. Minutes later he finally came inside me, then he disappeared. I just lay there and wept because it occured to me that my life had drastically changed.

They confiscated my slutty, schoolgirl outfit finally and gave me an orange jumpsuit. I wasn't even allowed to keep my hoop earrings. Being a transsexual made it difficult for the state to find me a place to put me. I ended up going to the men's prison, but they attempted to isolate me from the other prisoners. Of course, regardless how hard they tried, if a prisoner had connections, if he wanted to see me, he could. It was my first day in prison and a prison guard came to my cell and advised me that it was my time for a shower. I followed him to the showers and I got undressed. As I made my way into the showers a massive nigger emerged. I have only once seen a nigger as dark as he. He was ebony - not chocolate or mocha - but black in skin tone. Each of my breasts is about the size of my head but his hands were so huge that when he kneaded my breasts he easily enveloped them with one hand and the contrast between his hands and my tanned breasts I confess was arousing. He wasn't too cute or handsome in the face, in fact, I'd say he was rather ugly, but his body was very well toned. I had never in my life seen such a specimen as he. Each of his arms were the size of my waist. He had to be close to seven feet tall. He and I were alone in the showers and we were both nude. He blocked my path by placing a hand on the wall and I turn to face him, looking up - I was petrified. He took his other hand and placed it to my other side effectively pinning me against the wall. I had nowhere to go unless I tried to go between his legs, but he had a beautiful, black cock dangling there before me. He said, 'I'm Malcolm. This is my prison and I offer you protection. I know who you are and I know why you're here. I hear through the grapevine that you like black cock. Is that true?' I simply nodded as I bit my bottom lip. I was scared shitless. He could kill me so easily if he wanted to. He began fondling my breasts and licked my face as he continued, 'I'll grant you protection if you swear allegiance to me and you become my bitch. As my bitch you will enjoy certain perks because like I said - this is MY prison... I own it.' I muster a response, 'Yes Sir.' 'Sir?' he said inquisitively, 'I like it. Let's get started.'

He immediately spun me around, spit on his hand and shoved a finger up my ass. He spit on his hand again and rubbed my anus vigorously - penetrating me again with his massive fingertips. He grabbed me by the hips as I felt pressure on my ass. He thrusted forward and I felt a sharp sting as he impaled me with his cock that is the size of my arm. I gasped as he penetrated me with that massive cock. He churned inside of me - rhythmically battering me with his gargantuan cock. I moaned and panted as he pummeled me with his enormous tool. He started coaching me, 'Oh yeah, Bitch, there you go! Just like that! Arch your back for me! Oh yeah! My little black cock slut!' It actually turned me on the way he talked to me. Within minutes the pain subsided and being fucked by his enormous staff was extremely fulfilling. I decided then during our first time together that I might actually enjoy being his bitch. Between mighty thrusts I was able to get a sentence out, 'I-I-I th-i-i-ink I'll l-i-ike be-e-eing your bi-i-itch.' He chuckled and started fucking me even harder. I couldn't breathe so I just stood there bent over and took his cock the best I could. He responded, 'I think I'm going to like you being my bitch,' and he just cackled. With that he grunted and exploded inside me, but he withdrew his massive cock quickly enough so that he shot much of his seed onto my ass as he grunted again and again. 'Oh yeah.. oh yeah, bitch. You're mine! Now... now we'll lay down the rules. You are mine... M-I-N-E... mine. You will do everything I tell you to do. You are my sex slave. If I want to watch you fuck someone else and I tell you to fuck someone else you will do so. I will provide you protection from everyone - including MY niggas! Anyone that messes with YOU, messes with ME... understand? I will provide you with everything you will want or need while in this penitentiary. I'll elaborate further tonight.' 'Tonight?' I asked timidly. 'I told you, I own this prison,' he declared with a grin.

'Here,' he said as he offered me a small bundle. I looked at him intensely. 'What is it?' I asked. He smiled and said, 'Sleep in this for me.' I started to look at the package, but Malcolm added, 'Wait to open this once you get back to your cell.' I teasingly motioned him to come here with my finger as though I want to tell him something. He bent down to me so I threw my arms about his neck and kissed him passionately. That really surprised him, but I could tell that it pleased him. He squeezes my ass as he picked me up off the ground and we kissed deeply and passionately as my feet dangled about a foot off the ground. 'Oh yeah, I'm going to thoroughly enjoy you,' he told me.

That night I was asleep in my cell lying face down on my bunk. I had fallen asleep that night wearing Malcolm's gift. When I got back to the cell I tore open the newspaper wrapping and the linen string. I was giddy with excitement when I saw it. How he got this inside the prison walls I have no idea, but it was a pastel-pink teddy. I tried it on and it fit beautifully. The set included a pink corset with garter, sheer pink shawl, pink bikini panties and pink thigh-high nylons. I felt so submissive... so playful... so sexy wearing his gift. I was awakened by jerk on my panties. Before I was given the opportunity to fully awaken this mass crashed on top of me. I couldn't move because someone was lying on top of me and they held my hands out over my head while my face was buried in my pillow. I felt pressure on my ass. The pressure shifted slightly to the left then to the right. He found the sweet spot and thrusted deliberately inside of me. I wanted to scream. The pain was intense. He began grinding inside of me, churning away rhythmically. My coos and moans grew louder and louder as he impaled me with his massive cock. 'God damn, Bitch! You're so tight!' he exclaims. He exhibited so much power and dominance over me. There was nothing I could do even if I wanted to. Of course, I didn't want to. I was in heaven. I have never felt so alive as I writhed and squirmed under his weight. Pretty soon I heard my moans echo throughout the cellblock which drew a few comments from other inmates. Within minutes Malcolm exploded inside of me as I gyrated my hips - working his cock. 'God Damn, Bitch!' Malcolm said excitedly. Malcolm allowed me to roll over onto my back so I could wrap my legs around his waist and we kissed passionately - our tongues swirled about in each other's mouths. I cooed as he lay on top of me kissing me overpoweringly. My fingers I ran through his nappy, oily hair but I paid it no mind because I love him. I knew that it was in his arms that I belonged. There was no resisting Malcolm. I whispered, 'I love you, Malcolm.' He kissed me harder and deeper and whispered, 'You can't help but love me, Bitch. I own you.' Each of his fingers was about the size of my arms and his arms about the size of my waist. He was a beast, hence everyone's nickname for us: Beauty and the Beast. We were inseparable. Well, until he would tell me he had 'business' to conduct. Like the loyal plaything I did exactly as I was told because, for one, I fear the consequences if I were to anger him.

By being his bitch afforded me greater respect and security. In fact, he somehow got my hormones into the prison so I never had to stop taking my estrogen. I had one or two of Malcolm's thugs follow me around everywhere. Within two months time everyone in the prison knew me as 'Malcolm's Bitch.' Every night Malcolm visited me in my cell and fucked me relentlessly. There were nights that I knew I was the grudge fuck - Malcolm taking it out on the white bitch. He would be so rough that he had me screaming and crying, but I knew he loved me. Afterward he would lie on top of me - pinning me down to the mattress as he covered me in wet, sloppy kisses. I whimpered under his massive frame as he held me every night. However, that's why it surprised me when he told me of his decision to share me. 'Share me?' I inquired. 'Yep, 'share' you,' he said. 'What am I to you?' I asked. It slipped out before I thought. I regretted asking it as soon as I heard it leave my mouth. Without hesitation he said, 'I own you. You are my property.' The horror was so crushing. The realization of what I'd become. 'Here,' Malcolm said as he put out his hand to give me something. He dropped two hoop earrings into my palm. I squealed, 'My earrings!' Malcolm responded, 'Sorry Sweetheart, no... Rudy made these for you... I believe from paperclips.' I took a closer look at the earrings and I still couldn't tell a difference.

That night I was sleeping on my tummy when he came into my cell and practically tore off my panties. Again, a sharp pain shoots through me as I have an engorged cock viciously impale me again and again. I cooed and moaned and then he spoke, 'Damn, Bitch...' The voice... I knew that voice and it wasn't Malcolm. I turn to look and I see DJ, Malcolm's top lieutenant who quickly covers my mouth as he pounds me with his cock. Within a few minutes he came inside me - grunting. DJ explains, 'You're the only white ho around here who can sate my appetite, Bitch! Malcolm needs to appease his lieutenants and that's where you come in, Bitch!' He then spits on me and starts spanking my ass with his bare hand again and again. He strikes hard and fast. I am reduced to tears as I beg him to stop. My cries and pleas for him to stop echoed throughout the cell block. Malcolm had nine lieutenants and I couldn't help wondering if I was going to have to endure this nine times. After mercilessly spanking me, DJ snuggled with me for a few minutes, but aggressively he climbed back on top of me and fucked me again as he groped my body. He kneaded my breasts as he skewered me mercilessly. There was no doubt that I was a grudge fuck for DJ. I think he derived more pleasure from my tears than from my 'pussy.'

About a week and three lieutenants later my two bodyguards thought it a good idea to gangbang me. They must have thought I'd become the biggest slut ever to be willing to fuck around on Malcolm. Malcolm is huge... he is almost seven feet tall and probably weighing close to four-hundred pounds. For someone to cross him would surely be suicidal. Apparently no one thought to tell these two men that my fucking his lieutenants was actually Malcolm's idea. Upon seeing my rendezvous with one lieutenant after another, my bodyguards decided they too wanted to fuck me.

I went to go bathe like I normally do, but rather than wait outside the showers like they normally did I found them nude with me. Without uttering a word they forced me to my knees and I started sucking both nigger cocks. I switched back and forth until finally one of them walked around behind me and had me stand up. He eased himself inside of me while I sucked his partner's cock. So I was there bent over with a cock in my mouth and another in my ass simultaneously. My cries and moans were muffled due to the cock in my mouth, but they were apparently loud enough to be heard outside the cell block. Within minutes I found an additional two erections dangling before me. The bodyguard in my mouth - his last name was Rice. As soon as Rice came in my mouth another nigger dick took his place. That shower took about two hours due to the fact that I had three fuck my face and another two fuck my ass. I never told Malcolm, but after that day those two bodyguards became my lovers too gangbanging me whenever they could.

by heather_tg

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