Education of a Ladyboi

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Education of a LadyboiEver since I can remember I have been a sissy. As a very young boi, I loved playing with dolls and other girlie things. I avoided the company of other bois my age because to be honest, they frightened me. They just gave off a threatening and hostile vibe that I went out of my way to avoid them. Instead I preferred the company of the girls. I took a lot of heat all the way through school, and after puberty I began totally embracing my femininity, by overt means, such as, wearing makeup, girlie clothing, and flaunting my transgenderism publicly. And while I was teased and bullied, most of my classmates had grown up with me and had gotten used to me as the school sissy, so I wasn’t harassed to the point that it got physical. Outside of school, I’d take it a step further and wear skirts and dresses, high heels, lipstick, women’s short shorts, and halter tops. And believe me, when I was all dolled up and looking whorish, I’d get lots of male attention! But I was very careful because there was a girl like me named Gwen who lived not far from me, and she ended up being offed because she was having sex with men, and when they found out that she had male genitalia, they killed her. I decided that if I was going to be a woman, I would do it openly, so that if a man did want to get with me, at least he’d know what he was getting. My first boyfriend was a black guy named James. He was 42 years old, parolee who live in a house with some of my classmate’s parents. So he knew what I was. He told me later that in prison, girls like me are turned out as whores and sold to men on the cell blocks. He said that if I were locked up with him, we’d both be rich. I’d catch him looking at me from the corner of my eye, and when I’d turn, he’d quickly look away. I had never had sex before, and I resolved to seduce James. Every time I was around him I’d give him sexy looks, and wiggle my hips – anything I could to turn him on. One day James came right out and asked me if I would go to a motel with him. We were at the mall and we were having coffee and holding hands. Anyone seeing us would have taken us for an interracial heterosexual couple. And even though James was old enough to be my dad, with makeup on I came across as in my early 20s. He told me that he would pick me up on Friday afternoon. He had already booked the room, and he said we had all weekend. to have fun.When Friday came it was a hot day. I was nervous because although I had dreamed and fantasized about it, this was going to be my first time having sex. I put on a pair of string bikini panties, a pair of butt baring short shorts, a lavender halter top, and 3 inch high heeled sandals. At around 2 p.m. I took a bus to the mall, where James was going to pick me up at 4. While I waited for time to pass I wandered around the mall, window shopping and getting a latte. Lots of men were hitting on me but I was saving it up for James. He was so cute and totally masculine, and best of all, he knew I was a ladyboi. When he showed up finally he was smiling and had a bouquet of flowers. “Oh, James! For ME??” I gushed. We drove to the motel, which was located the next city over. It was a really dumpy looking place in the ghetto, but illegal bahis James explained that in places like this, they don’t ask questions. James had already booked a room for the weekend, so we went straight to the room. I had purposely dressed like a slut because I knew James liked it, and as we walked across the parking lot and to the room, I went out of my way to laugh loudly and wiggle my ass. I wanted to attract attention, so that if any bitch was around she would know that James was my man.We got in the room and locked the door, and James closed the curtains. You looking fine, Keven,” he said. “Come here.” I came to him and he pulled me close. I was a little surprised by how rough he was. Up until now we had only been talking, but in the privacy of this room, I was about to find out what it is to be a woman. He bent his head to mine and our lips mashed together, his tongue snaking down my throat, his big hands cupping my ass. I reached and felt of his shorts, and felt the big hard bulge in his athletic shorts. I squeezed it with my fruity little hand and Jay groaned in pleasure. “Take off your shit,” he said, flicking my halter top with his fingers. “Take everything off – except the heels.”I laughed self consciously as I reached behind and pulled the string of the halter top and felt it come loose and drop to the floor. There was a sharp hiss of the intake of his breath as he saw my bare tits for the first time. “Oh SHIT, girl – are those fuckin tits for real?” They were real! See, I was born to be a woman, but somehow nature had fucked up and given me a penis and testicles. But when puberty hit, and I began to develop, it was as a young man, but as a WOMAN! My body was silky smooth, and my hips were big, and I had a set of natural female breasts that any woman would love to have. The feel of Jay’s big hands on my tits made me shudder with lust, and I felt my small penis getting hard as we kissed. “Take off the rest, girl,” Jay panted. I unbuttoned my short shorts and wiggled them past my feet, kicking them off. James reached over and grabbed my bikini panties, ripping them roughly right off my ass, and I stood there completely naked in just my high heels. “Turn around, baby – let me look at you,: James commanded. And when I did he whistled. Man! That ass and those tits do NOT belong on a guy!” he said. I watched as James stripped off his tank top and his shorts. Mmmm, what a beautiful body! All those BIG HARD MUSCLES! All he had on were his jockey shorts, and the bulge in them was fuckin HUGE! The room was dark except for the light in the bathroom. James told me to walk to the bathroom and then walk back. “Walk, sexy, Keven,” he said. “Walk like the bitch you are!”As I walked back to him, I could see he had his hand down his shorts. I was feeling the power that a woman feels over a man for the first time in my young life. “Take em down, James said nodding to his shorts. I hooked my thumbs in the waist band and slowly pulled down his jockey shorts, sinking into a spread legs squat, and pulling them off his feet. When I lowered the shorts past his hip, James’ huge throbbing cock had sprung up, standing straight up. “You ever suck cock?” James asked me, looking down illegal bahis siteleri at the naked Caucasian sissy in high heels, squatting at his feet.”First time,” I answered him, taking the rigid cock and running my pouty rouged lips all over the head. James groaned in pleasure as he felt my wet mouth engulf the entire head of his cock, my tongue swirling saliva around it. Oh GOD – this is what I had dreamed of and fantasized about for so SO long! I had watched enough porn to know what a man wants, and I put my heart and soul into that blowjob!, As I sucked James’ cock and hairy balls, I ran my small fine boned hands all OVER his BIG HAIRY LEGS! Oh what a FUCKIN PUTA! James ran his fingers through my long blond hair and gathered it up, pulling it to a tight top knot, and he began using my head as a cunt. He put his other hand under my small heart shaped chin and began fucking my head, and with each stroke, pushing that hardon deeper into my throat, until I was making these crazy loud gagging noises, like: “YERK YERK YERK YERK! and almost vomiting. Now what we were doing began to feel almost uncomfortable, and I tried to ease my head back a little, but those big strong hands had me in a vice like grip, and a small part of me now began to know the fear of being a woman. Then he eased his spit covered joint out of my mouth, gooey strings of saliva hanging between his cock and my mouth. tears were streaming down my cheeks and I was coughing. Jay took my chin in his fingers and tilted my head up to look at him. I was shocked because instead of the kind and loving guy that had been courting me, I saw anger and meanness in his eyes, and while I was thinking all this, he hit me – hard. I raised my arms up to try to protect my face, but he pushed them aside, and he gave me a beeting. I was screaming hoarsely and begging him to stop, but he told me to yell all I wanted, because no one was going to care about some whore getting her ass wipped in a crack motel like this one. He grabbed me and pulled me over his knee, my arm twisted up high up my back, until I thought I was going to faint from the pain, and he spanked my ass so hard it was a mass of broozes for weeks. Then he relaxed and lay back on the bed in the darkness, looking like a naked muscle bound GOD! “Go get me a soda from the machine,” he said. I almost couldn’t believe what I was hearing. I had just got the beeting of my young life, and I was crumpled naked on the filthy floor, sniveling and snot and tears running down my face, and now he was telling me to go fetch him a cold drink. I was young then, and confused, but this was to be my first lesson about what it was to be a whore. “Go on now,” James said. “Put your shit on and fetch that soda.”Numbly I dressed and James told me to hand him his pants. I stood shaking and crying as he calmly took the money out and handed it to me. “Make it a Doctor Pepper,” he said, ” and if you do it right I might save you a swallow.”Just before I opened the door, James said, wipe your fuckin face and don’t go out there pouting. And don’t even think about running, because when I catch yo ass I will give you the beet down of yo life. You got that?” I wiped my face and nodded. “I canlı bahis siteleri SAID – did you get that, motherfucker??’Yes, I mumbled, trembling in fear.”Yes?? Yes WHAT – bitch?”Yes, Daddy,” I said, hoping that was what he wanted to hear, and apparently it was, because he waved his hand. “Go on now and hurry yo ass up. I’m fuckin thirsty!”I stepped out into the hallway and headed up to the lobby by the front desk. A fat black woman was behind the desk, and when she saw me she raised an eyebrow and smiled knowingly. “Y’all ok, shugah?” she said. I forced a smile and nodded. I got the Dr. Pepper and walked past the desk and back to the room, where James was waiting. As I neared the door, part of me was thinking that I should run. Who knew what James might do to me next? But his warning scared me more than the prospect of more beetings. I opened the door and slipped into the darkened room. “I got your cold drink, Daddy,” I said, in my most ass kissing voice. “It’s nice and cold, honey!”I t better fuckin be, he said. Anyone say anything to you out there? I shook my head and stood next to the bed as James lay back scrolling through the channels and gulping down the Dr. Pepper. He glanced over. “Oh shit – I said I’d give you a swallow! Here,” he said handing me the almost empty can. The air condition wasn’t working and I was hot and sweaty and thirsty. I greedily drank the few ounces. James looked at me. “Get naked and get in here, girl, he said, patting the mattress beside him.I stripped nude and crawled over him into the bed. ‘Mmmmm,’ I was thinking, He is so fucking FINE!’ I ran my hand over his sweaty bare chest, and down to his erect cock, and I gave it a sexy choke down near the base. “Get down on it, bitch,” he said. I began sucking his cock again – nice and juicy! My upper lip was really swollen up, but James said that it made the blowjob even hotter. I was crouched between his legs and licking his nuts and sucking them into my mouth. James raised up his big hairy legs, exposing his ass hole. “Kiss it,” he ordered. I was disgusted but afraid, so I pushed my face close and planted a kiss right on his moist anus. “Lick it up, Keven, James said. I filled my mouth with saliva and I began eating him out! And the next thing I knew my little penis was getting hard. I ate out his anus, sucked his toes, and mopped his sweaty chest and armpits with my white bitch face. I was squeezing his joint, and I asked him to fuck me. We were making out nude and he raised his body and got up on top of me, pushing my skinny legs apart and back. “Put em up, sissy – raise em up,” James said. I raised my legs up high and he put them over his big broad shoulders, so that now it was my anus that was exposed. We were kissing and I felt the head of James’ hard cock pushing up against the mouth of my raw cunt. There was a searing pain as he ripped into my bowels. I shrieked in pain but I was pinned to the bed by his weight – completely helpless and this big naked ainimul raiped me.But then, slowly, the pain abated and his thing began to feel good inside me. He was crushing me in his mighty arms and fucking me hard – so hard that my head was ramming up against the wall and I was crying out in a mix of hot pain and sweet pleasure. Suddenly he tensed and yelled out, emptying his cum deep into my guts! Then he rolled over and had me massage his back and legs for hours. I was beginning to realize that being a woman was going to be harder than I thought.

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