The Chief Pt. 02

I awoke the next morning to the aroma of bacon frying. I was alone in a strange bed, and for a moment, I couldn't remember where I was. Then it all came back to me. It hadn't been some vivid erotic dream. I was lying in another man's bed, naked except for a pair of pink nylon panties. My stockings and garter belt were discarded on the floor, and my male clothes were...somewhere? Oh, God, what had I done? The memories came back to me and I realized that I had lost my lifelong struggle to be a real man. Dressing up had always been a guilty little diversion, but last night, I had given up my masculinity entirely and acted... like a woman.

I got up and went to the bathroom, catching a glimpse of myself in the mirror. I saw the skinny, undersized frame that I had always hated, but then I realized that maybe it was okay to look like this. Instead of skinny and undersized, maybe I looked "slim" and "delicate." Somebody seemed to find me appealing, and last night, I had been on my knees in front of him, sucking his dick. I had swallowed his cum. My stomach tingled as I realized that I had part of another man inside me now.

My boy clothes were somewhere in the living room, but after all that had happened, there didn't seem to be any reason to put them on. There wasn't much to hide, at least not to this man. I walked into the kitchen wearing just my panties and saw the Chief, wearing a pair of boxers and a tight khaki tee shirt, fixing bacon and eggs.

"I told you I'd make you breakfast, sweet cheeks. You want some coffee?"

"Please."

"How do you take it?"

"Black." We both smiled at the unstated joke as he poured me a cup. There was a battle raging in my mind, as a lifetime of insecurity and habit and struggle was being overshadowed by the Chief's presence. The old habits were losing; I found myself wanting to kiss him.

"You look nice," he said as he turned away from the stove and stood in front of me, then leaned down to me and kissed me deeply. My arms went around his neck as if they had a will of their own, and our bodies pressed against each other, and I felt the heat of him, and his muscles against me, and the large bulge of his manhood against my stomach. We might have gone at it again if the bacon hadn't been ready.

What the hell had happened to me? I was straight! I dated girls! Except for my little panty fetish, I was a normal guy, and somehow, in the course of one night, I had become a... what? A faggot? A cocksucker? (Yes.) A girl? I didn't know what I had become, but the feel of the Chief's body made me feel all submissive and sexy again, and there was no question that I liked it.

"I meant what I said last night," he told me over breakfast. "I don't want to make you feel bad, but you're real pretty for a boy. With a little makeup and fixing up, you'd make an even prettier girl."

"I... I've never done that before. I wouldn't know how to put on makeup."

"You never even tried on a little lipstick?"

"Well..."

"Ha! I thought so. Tell me about it." The Chief was making me remember and confess things that I had always been ashamed of, but that damn seductive, accepting smile of his made it seem like I could tell him anything. I told him about experimenting with some of my sisters' lipstick and mascara when I was younger, and how I wasn't very good at it.

"Makeup is tough. Most sissies overdo it and look like clowns. You just need someone to show you the right techniques. I can introduce you to my sister; she's a cosmetician. She could teach you a lot."

"Your sister knows about...?"

"That I like ladyboys? Yeah."

"Chief, are you...gay?"

The Chief chuckled. "You tell me. I always dated girls. Still do sometimes. A few years back, I was on the Nimitz and we made port in Pattaya, Thailand. A few buddies and I had a long liberty, so we went to Bangkok for a few days. That's when I saw my first ladyboy."

"You mean like...transvestites?"

"A lot more than just transvestites. They start out at an early age and take training to be girls, in and out of the bedroom. They take hormones and their bodies develop like women. They still have male gear, but they have sweet little breasts and firm little butts."

"But they're still boys... or, or men, right?" I asked.

"No way. They've given up their manhood completely. They're more female than any natural born woman ever could be. Maybe that's what the appeal is for me - they've chosen to give up their masculinity entirely. They're delicate, and slender, and they move like women, and they make love like women, not because they were born that way, but because they've chosen to do so. There's something really sexy about that. That trip to Bangkok was when I decided I liked girls who used to be guys. If that makes me gay, then I guess I'm gay, but I know that when I'm with a ladyboy, or a sissy, I feel like I'm with a woman, and I treat her that way." In spite of the events of last night, I felt a little inadequate being in competition with these hormone-enhanced asian beauties.

"But... You spent the night with me, and I'm not on hormones or-"

"Hold up there, baby girl! I already said I think that with a little help, you'd make a mighty pretty girl. A little makeup and growin' that pretty hair out a little longer. Gettin' it styled into one of those cute "unisex" hairstyles. Maybe cut you some bangs... Get you into bra and stockings, then a nice dress and some sexy high heels... Damn, girl, you'd be HOT! Besides, I don't like asian girls that much. I like my girls American."

"And white?"

"Yeah."

"That's kind of racist, Chief," I smiled.

"Well, maybe so, but you didn't seem too racist last night, baby," he chuckled. He grabbed behind me by the waist and pulled me to him again, and I giggled like a damn schoolgirl and his tongue slipped between my lips and he kissed me long and hard.

"Besides, you don't need hormones. It's like I was sayin', it's not so much looks as femininity." He looked straight into my eyes and added, "It's making the decision to give up their masculinity."

My heart skipped a beat (again!) as I realized just how deeply I might be pulled into all this if I kept doing this with the Chief. Last night had been strange and unfamiliar, but I had loved it, and I wanted to do it again. But how badly did I want it? Could I really give up my manhood entirely? Would he really want me to? How far would I have to go to keep him satisfied? More important, how far did I want to go? I had fantasized about prancing around in girlie clothes in the past, but this could be for real! Could I bring myself to turn my back on my previous life, give up dating women, and starting all over as a...

"Hey, baby, you lookin' way too serious. You need to spend the day relaxing with my sister. She has a spa and beauty shop in town. She knows everything about makeup. Not just that, but she can give you a full spa treatment. It's Saturday, but she'll make some time for her big brother and his new girlfriend."

"You said she knows about you and that you like..."

"Sissies?" He was making me admit it. To him and to myself.

"Yes," I said reluctantly.

"Yeah, she knows all about my girlfriends. She'll have a great time fixing up a pretty little white boy to be a pretty little white girl. C'mon, you've got the day off, right?"

"Yeah." I had been in beauty shops before, but never as a customer. The idea of going into "no man's land" and allowing a woman I had never met change my appearance scared me, but even stronger than my fear was the desire to know how I would look. Was the Chief right? Would I really be "pretty?" What would it be like to look in the mirror and see the image of a "real" girl, and not just a skinny boy wearing lingerie, looking back at me?

"You can wear those jeans and shirt on the way over; we'll get you some new clothes while we're there." The thought of what those new clothes might be thrilled and frightened me.

The Chief gathered up the dishes and said, "First, though, we both need a shower." He took off his shirt and added, "Why don't you take off those pretty little panties and let the Chief get you nice and clean?"

I shucked my panties in no time and went into the bathroom and turned on the shower. The Chief stepped in behind me, naked, and I got my first really good look at his body. I couldn't tear my eyes away from him. Broad shoulders, sinewy arms and legs, muscular chest with dark, quarter-sized nipples, a flat, rippled stomach, trim waist. His dark skin somehow highlighted the contours of his body, showing the muscles underneath. And that cock. Like black velvet. I had had it in my mouth last night. I had teased it, and licked it and sucked it until I caused him to have an orgasm. Then as he released, I had swallowed his essence, and it was still inside me. His cock was half hard, and I actually felt my mouth watering as I looked at it.

The Chief soaped up a washcloth, stood in front of me, and started gently and slowly washing my shoulders and neck, then my chest, lingering on my nipples, teasing them. Then he pulled me against him and washed my back. All the time, he was murmuring what a pretty girl I was. I just stood against him, my arms went around his torso. He took the soap and lathered his hands, then rubbed my backside, kneading my buns and working his soap-slicked hands into my crack. Slowly, so slowly I hardly noticed except for the pleasure, he worked his fingers farther between my buns and let one finger circle my hole. Little electric sparks radiated from my anus as his fingers teased, pressing against my virgin opening, then backing off, then pressing again.

"You like that, baby?"

"Ye- yes..."

"You want me to go inside?" he whispered. My body was limp against his, my arms around him, feeling his now fully erect manhood against my stomach. I felt that urgent need to please him again and even though it scared me, I was ready to do whatever he wanted of me. I couldn't speak, so I nodded.

He soaped his hands again and worked his way back between my cheeks. My entire butt was slick with soap and water. His finger pressed against me again, not teasing this time, insistently pressing against my opening.

"Just relax, baby. The Chief's gonna make you feel so good, make you feel just like a beautiful princess." Something inside me gave in to the pleasure, and I yielded, and the tip of his finger popped into my ass. I flinched and he whispered to me again, and his finger advanced inside me just a little, opening me up. Then he withdrew, almost pulling out, then pushing in again, a little deeper this time. It didn't hurt at all, and I felt the warm water flowing over both of us, and the Chief's body against me, but at the center of it all was his finger inside me, gently thrusting in and out. I realized that I was being finger-fucked. I had finger-fucked girls, but it had never given me a hard on like the one I had right now. I was rock hard, all because a man was inside me. It was a feeling of submission, and giving of myself, but even as relaxed as I was, my own dick craved release. Almost like he could read my thoughts, the Chief reached around with his free hand and grabbed my erection and began slowly stroking it. I began to move my ass back against his finger, needing more of it inside me, bucking against his hand, and suddenly I squealed and gave in to a thunderous orgasm, almost falling had it not been for the Chief holding me steady. I was shaking, my knees weak, and I began to cry as I rested my head against the Chief's chest.

"Oh, that was so sweet, baby. You a sweet little sissy."

"I shouldn't like this so much, Chief!"

"Aw, you takin' all this way too seriously, baby! There's nothing wrong with having a little fun. You just learning different ways to have fun is all. Don't you worry about what other people think... They don't matter. You need to do what your heart tells you."

I was still scared, but what he was saying made sense. What if I never walked down this path? What if I never tried to find out who I really was? My whole life had been a struggle to maintain a facade of manhood. None of that had ever made me happy. Nothing had ever made me feel as good as having a big, black, gentle, masculine sailor hold me and whisper to me and work his way inside me. Something like acceptance came upon me, and I looked up at him and smiled, then soaped up the washcloth and began washing the Chief's dark skin, admiring the way the suds gathered in the contours of his shoulders. I washed his arms, then his torso, and then I went to my knees. I soaped his cock and his ball sack, and washed his legs and feet. Still on my knees, I looked up and watched the water run down his abdomen and trickle off the tip of his penis. I drank. I ran my tongue into the crease between his ball sack and his thigh, then took one of his balls into my mouth, feeling the wrinkled skin and pubic hair with my tongue. The Chief turned off the water, moved his feet apart, and moaned as I tongued beneath his ball sack, back to his taint. He was fully erect now, all, what? 9? 10 inches? It was a real man's cock, and I wanted it in my mouth again, to feel like a cocksucker, so I licked all the way up from the root, all along the underside, then slipped it in my mouth. Remembering my lessons from last night, I wrapped my lip around my upper teeth and used my tongue to coved my lower teeth as I slowly, lovingly, bobbed my head on his cock. My mouth was a pussy again, and I was a sissy little cocksucker, and I had just been finger-fucked and I had had an orgasm from being finger-fucked and I loved being a woman sexually. I wanted to get good at this. I tried to get his cock all the way down my throat and couldn't, but I made a vow to learn. My lips and tongue could felt every vein on his shaft, and the ridge of his corona. Even in the shower, the manly aroma of his crotch filled my head and gave me that now familiar, overwhelming desire to lose myself in pleasuring the Chief. I flicked my tongue on the underside of the tip, eliciting a flinch and a moan from him.

"Oh, baby... You doin' me ri- right... Ahhh... Suck that cock you little pussyboy... You like suckin' my black dick, baby? Tell me!" I looked up into his eyes, my mouth full of cock, my lips stretched around his girth, and nodded.

"No, bitch. Say what you want." I pulled my head off of him, but continued to stroke him.

"I want your cock, Chief," I admitted, gazing into his eyes, seeing the look of superiority in his face.

"How do you want my cock, you little sissy bitch?"

"I want it in my mouth, down my throat."

"Where else do you want it?" he demanded.

"I... I want it... in my ass, Chief."

"No, girl. Once I tap you, it won't be an ass. Where do you want it?"

"I want it in my... pussy."

"Tell me what you want." I gave in. I forgot about masculinity and the words poured from me, as if someone else was saying them.

"I want your big black cock in my pussy, Chief. I want you to fuck me. Hard. I want you to lay on top of me and I want to feel your cock up inside my pussy, fucking me until you fill my belly up with your cum. I want you to make me pregnant. I want to have your black baby. I want to be your sissy fuck toy and wear panties and dresses and nasty lingerie and do whatever turns you on. I want to be a woman for you and have you take me and own me and use every part of me for your pleasure. I want every drop of your cum. I want it all over me. I want-"

The Chief exploded into my face. Thick ropes of semen shot onto my lips, cheeks, my eyes and chest. He shuddered, then held my head in his hands and rubbed it into his crotch, spreading the cum all over my face. The smell and taste of his cum was all over me, and I realized I had an enormous hard on.

We both sighed. Without any prompting, I continued to rub my face into his crotch, licking the cum from his cock and belly. I was overcome with the need to get as much of him inside me as possible. By the time I was done cleaning him, the Chief had recovered.

"Oh, fuck, sweetheart. You are amazing. That was intense. You doin' okay down there?"

"Never been better, Chief."

"Why don't you call me Michael? After that, I think we oughta be on a first name basis."

"Yes, Michael."

"And what should we call you? You need a nice girl's name."

"I... I don't know, Ch-, er, Michael."

"Why don't we try 'Joanne'? That's a pretty name. You look like a pretty little Joanne." I was even being given a new name, similar to my real name (or my old name?) but it was feminine, and it felt right somehow. "Joanne," the pretty little feminized cocksucker. I felt that familiar mixture of fear and excitement and freedom, and strangely, a relieved kind of calm as I envisioned myself spending time as a girl, not just with the Chief, but out in the world, in front of people. Wearing dresses. Shaving my legs. Having long, pretty hair. Wearing necklaces and bracelets, maybe even having my ears pierced. Having long eyelashes and painted lips and (I hoped) having a pretty girl's face. Getting used to wearing a bra. Having people treat me like a woman and reacting like one. I had a lot to learn. My hard on had disappeared, even without release, but as I anticipated the world that opened up for me, I felt a strange sense of calm.

The Chief turned the water back on and together, we rinsed the remnants of our sex away. As we enjoyed the warm water pouring over us, the Chief had an idea.

"You know, we got one more chore to do before we get out of here."

"What's that, Michael?"

"Well, you look mighty pretty, but let's clean up that stubble on your legs." He stepped over to the medicine cabinet and pulled out a razor and a can of shaving cream. I stood in the shower as he lathered up my legs, then shaved them completely smooth. But he didn't stop there.

"We'll make you smooth as a baby's bottom all over. Get you all perfumed and powdered and you'll be a pretty little thing." He lathered my crotch and carefully denuded by pubic hair. Then he had me bend over and spread my cheeks as he removed all my hair from the waist down. I had never had any chest hair to speak of, but he shaved my chest smooth. Then he had me lift my arms and shaved my underarms. I was now completely hairless from the neck down. After drying me off, he rubbed lotion all over me, and my skin felt tingly and more sensitive than it ever had before. After that, he sprinkled baby powder all over me, giving particular attention to my crotch and ass crack. My pussy? I could feel the draft from the air conditioning as it caressed my skin. Slipping into my jeans and shirt, the texture of the fabrics felt completely different. My skin was smooth and silky and... luxurious, and feminine. Every movement reminded me that I was hairless now. Like a girl. Like Joanne.

Michael rattled his keys and said, "C'mon, Joanne. Let's go see my sister."

*

Copyright 2014 by Aunt Joanne