The Chief Pt. 01

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Young crossdresser is recruited into a new lifestyle.
4.3k words
4.58
50.6k
41

Part 1 of the 3 part series

Updated 09/22/2022
Created 07/25/2014
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When I was 19, I was still trying to figure out what I wanted to do with my life. I had just dropped out of college and was working construction in my home town. Construction work was hard, but I liked it. The guys I worked with were cool. It was honest work and it paid enough for me to keep my head above water. It was also a "manly" pursuit, and that was important to me at the time.

I had always been insecure about my masculinity. I had a skinny, delicate build. (You know, the kind that's always picked last for football teams in P.E.) I made good grades, and these days, I suppose I'd have been called a nerd. I was always intimidated by big, athletic guys. Bigger boys had always picked on me, and I was never big enough to fight back, which didn't do much for my self-esteem. Having two older sisters and no brothers didn't help, either. But the other thing that didn't help my own sense of masculinity was that ever since I was four or five years old, I had been trying on my sisters' underwear. I couldn't figure out the appeal, except that when I tried on a pair of panties or a slip, it was like I was taking a vacation from the constant burden to "be a man." I loved the cool, smooth feeling of the fabric, and even though I felt guilty afterwards, I borrowed panties every couple of weeks.

After high school, I went to college, majoring in geology, but after a couple of semesters, I knew I hated it. The only problem is that I couldn't figure out what I DID want to do, so instead of wasting any more of my time and Mom and Dad's money, I dropped out, planning to return when I had a better idea of my life's direction.

Construction jobs were easy to find, and like I said, it was a good way to earn a living for a young kid. And, of course, it was "masculine." Most of my co-workers were really good guys, but there were others that made me feel like I was back in high school. They would make fun of my size, or my delicate facial features, and a few of them made comments about my "cute little bubble butt." Some of them laughingly speculated on how I would be in bed, and a few offered to find out. Those "offers" were always delivered in a crowd, so I knew they weren't serious, so I usually responded with, "It'd be the best you ever had, pal!" or something like that. I knew that if I didn't show I was upset, they'd stop soon enough.

But it DID upset me, and even worse, it made me feel funny inside when they'd make wisecracks about my butt. What was really confusing was that there was a part of me that wondered what it would be like to be a girl with another man. Some times, I wondered what would happen if I took up some guy's "offer" of sex. They'd probably beat the crap out of me, and I knew I wouldn't ever respond that way, but late at night, I'd slip into a pair of panties and stockings and fantasize about one of those big burly, hairy construction workers treating me like a girl, giving me release from the constant effort to be masculine.

My dad, knowing that construction wasn't going to be a lifetime career for me, suggested that I check out joining the military. I didn't really want to be cannon fodder, but on the other hand, I had always liked flying, and the ocean had always fascinated me, so the Air Force and Navy sounded intriguing. One afternoon, I went by the Navy recruiting office to see what it was all about. It was in a little storefront shopping center, and the guy behind the front desk was very friendly. I told him that I wasn't interested in signing up right away, but that I was just checking out my career options. He suggested that I talk to "the Chief." And that's when I was introduced to Chief Howard. He was a tall, very well-built black man in a crisp khaki uniform with lots of service ribbons and brass insignia.

"Get your young buns back here and let's have a talk, young man!" he said with a broad smile. He extended a large hand and I introduced myself. Chief Howard was one of those guys that I had always been intimidated by. Big and masculine, with an aura of being in complete control. When we shook hands, my hands seemed tiny compared to his. He was a little scary, but there was something in his smile that was open and friendly and accepting, and a twinkle in his eye hinted at a sense of humor. Strangely, I felt comfortable with him, and something else... admiration? excitement? I held his gaze for the longest time. It was like he was looking right through me, but at the same time, he seemed completely accepting of everything he saw.

We talked about the Navy and educational opportunities, what basic training was like, and what life was like onboard a ship. The Chief seemed very interested in me, and asked about my life experiences, what I had studied in college, and what I wanted to do with my life. I figured this was pretty standard behavior for a recruiter, but I enjoyed his interest anyway. He told me something about his life growing up in a small town in Mississippi and how the Navy had opened up a world of opportunities.

I had never been particularly sociable, and truth be told, I had always felt uncomfortable meeting new people, but there was something about the Chief that put me at ease. He wasn't like anyone else I had ever met before, but I liked him, and he seemed to like me, too. (Although I knew they probably trained recruiters to make prospective recruits feel special.) But there was a feeling in the back of my mind that I couldn't figure out. It was kind of scary, but I was drawn to the Chief, and it felt right, and somehow exciting, to open up to him about my life and feelings.

The Chief gave me a test, one that was a lot like those "fill in the oval with a Number 2 pencil" tests I had taken to get into college. He got up and walked around to my side of the desk and leaned down to show me how to complete the test. Leaning down next to me, I became aware that his hand was on the back of my chair, almost like his arm was around me. Normally, I would have been uncomfortable with such closeness, but when I felt his hand on my shoulder, I wanted to lean into him. What was THAT all about? I became aware of the Chief's aroma. He smelled clean and musky and very manly, and I think he might have noticed my long intake of breath as he leaned in close. I must have blushed, but the Chief just smiled and acted like nothing was unusual.

Before I knew it, three hours had gone by. The funny thing is, I wasn't in any hurry to leave. I don't know how interested I was in the Navy, but I really felt comfortable around the Chief. I told him I liked the idea of signing up, but that I wanted to consider it awhile and to spend some more time talking about it.

"Well, let's continue this over supper, then," he said. "I can come by and pick you up in a couple of hours and I'll treat you to dinner." I couldn't get the words out fast enough to agree, and he gave me one of those quizzical, knowing looks that made me think that he knew more about what I was feeling than even I did. I went home and took a shower, all the time feeling way too excited.

Drying off from the shower, I noticed my smooth, hairless legs. A couple of days ago, I had shaved them because I liked the way they looked and felt in stockings. Something about having smooth legs excited me even more than usual. After drying off, I went over to my underwear drawer and almost pulled out a pair of boxers before catching a glimpse of lace at the back of the drawer. I had a naughty, frightening thought: an image of going out to supper with a strong, masculine man like the Chief while I was wearing pretty, feminine lingerie went through my mind. No one would ever know, and I could almost pretend that I was on a date. I put the boxers back in the drawer and pulled out a pair of pink nylon, lace-trimmed bikini panties and slipped them up my legs.

On an impulse, I went back and pulled out a package of nylon stretch stockings with reinforced toe and heel, then pulled out my little white garter belt. I had an enormous erection as I slipped the stockings up my legs and fastened them to the garter belt, fantasizing about my "date" with the Chief. I put on jeans and a polo, then reached to put on socks. I admired the dainty look of the nylon reinforcement on my toes and heels. What a shame it would be to cover up that look with thick socks! With a guilty thrill, I set the socks aside and put on a pair of loafers. As long as I was careful and didn't show too much ankle, no one would notice that I was wearing nylons under my jeans.

Chief Howard came by at 7. He had changed out of his uniform but hadn't lost any of his strong, powerful bearing. He was wearing crisply pressed slacks and a fitted shirt. I found myself admiring his triangular build, with broad shoulders tapering down to a trim waist. I really hadn't noticed men's bodies much before, and I may have held my admiring gaze a little too long. I caught myself lingering, looking at his waist, wondering what he looked like underneath... Then quickly looked back at his face, but all I saw was that friendly, open smile, with maybe a twinkle in his brown eyes. Had he noticed?

We went to a local Mexican restaurant and the Chief picked up the tab. Over enchiladas and beer, he told me about growing up in some pretty rough neighborhoods in Chicago, playing football in high school, and when that didn't get him a scholarship, the Navy being his way out. He had been around the world several times, and he had some great stories about Tokyo, London, and dozens more exotic places that I had only dreamed of visiting. I could see why the Navy had assigned him to be a recruiter; he made it all seem very appealing. And he seemed to think highly of me.

"You aced those intake tests, kid. The Navy keeps an eye out for young, smart guys like you. You could pretty much pick your own assignment." He asked about my interests. I had always been fascinated with submarines, and told him so.

"The Silent Service, huh? How do you feel about being cooped up with nothing but other men for six months?" I couldn't tell for sure, but when he asked that, there was something suggestive in his tone, and those eyes seemed to see right through me... Maybe it was just me; I had been distracted by him all day. He talked a lot about life aboard ship, never saying anything overtly suggestive, but making a life around other men sound very appealing. At that moment, the idea of being off at sea surrounded by hundreds of men like the Chief seem wonderful... What was WRONG with me?? I was supposed to be straight! A normal man! Sure, I liked to put on panties and fantasize about men, but that's all it was, just a fantasy. Deep down, I was a normal guy. But at the same time, every time I looked at the Chief, and heard his deep, smooth voice, something inside me went...tingly.

Supper took a couple of hours, and when the Chief suggested we continue talking over at his place, I stumbled all over myself accepting. He had a nice, modest house, clean and well furnished, and he offered me a beer and turned on the TV. He seemed very interested in me and my background. I told him about growing up, and going to college, and working construction. Maybe it was the beer, but I even told him about the construction workers making fake passes at me and talking about my bubble butt.

"Did that bother you much?" I told him no, and he said, "Well, I can see why they did it - you do have a tight little butt." I must have blushed, because my face suddenly felt very hot, and I couldn't think of anything to say. It turned out I didn't have to. I was sitting on the sofa next to him with one leg crossed over my knee, and he placed a hand on my ankle.

"Those aren't socks are they?"

Oh, FUCK... I was busted! Wearing fucking NYLONS in front of THIS man! Me and my stupid crossdressing... I was mortified. I looked like a pansy little pervert and failure in front of this man that I wanted to impress, and I felt like crying, of at least falling into a hole, but then he slid his hand up my jeans, feeling along my ankle and calf, and he said, "I'm glad you dressed up for me. Why don't you let me see the rest?"

He was breathing more heavily, and his voice became softer, but he still had that smile, like all of this was just for fun, not too serious, and even though I was still humiliated and frightened, I stood up and kicked off my shoes. He looked at my feet a long time, the reinforced toes and heels in plain sight, then he undid my belt, and took my jeans down to the floor. I heard his sharp intake of breath as my garter belt, then panties, then the tops of my stockings come into view.

"Man, you got pretty legs like a girl, baby." He ran his hands up my legs, then he reached behind and squeezed my buns in his big hands.

"Those hardhat guys were right, baby, that is a sweet little ass. Turn around for me." I turned around and faced away from him, practically feeling his eyes burning into my backside.

"That shirt doesn't look right with those stockings. Take it off and turn back around for me." It was like he was ordering me, and I should have objected, but a new kind of feeling was taking me over. After a lifetime of wanting to be in charge, I suddenly wanted to be subservient, to do whatever this man wanted so I could please him. I took off my shirt and stood in front of him clad in nothing but garter belt, panties, and stockings, and I wanted him to think I was... pretty...

"Aw, you are a sweet, pretty little thing. You got me all excited. You think you can take care of me?"

"Yes..." I stammered. My head was spinning with fright and humiliation and desire and I could barely speak.

"Let's see about that..." The Chief stood up, and towering over me, and he unbuckled his belt and pulled off his slacks. He wasn't wearing any underwear, and I saw his huge, black cock for the first time. I had seen plenty of cocks in gym class, and I always thought they looked ugly. But this was different. This one wanted me. It was about half hard, dark brown like milk chocolate, at least eight inches long, thick, and uncut, with a tight ball sack surrounded by a thatch of black pubic hair with just a couple of gray hairs mixed in. I couldn't look away, and I found that my mouth was watering.

"You see anything you like, honey?" he said as he rested his warm hands on my shoulders. I just nodded. He took off his shirt and sat back on the couch, naked, and spread his knees apart slightly. His body looked chiseled, with tight, rippled abs, huge shoulders and arms, and muscular legs. Every contour on his smooth black skin showed the powerful muscles underneath.

"Why don't you kneel down and get to know me better, sweetheart?" I dropped to my knees in an instant, leaned forward, and found myself face to face with his crotch. He smelled like soap and just a little bit of sweat. I felt his hand on the back of my head, not forcing me, but guiding me closer to his crotch. I breathed deeply, taking in the aroma of him. Just before my nose touched his crotch, he took his hand away, letting me set my own pace. I was beyond rational thought. Any memory of masculinity or manhood or embarrassment was overwhelmed by the sensation of kneeling submissively in front of a man, dressed in feminine clothing, taking the part of the female for the first time. My heart was racing, and I was dizzy, but I wanted nothing more than to be a girl for him, to give whatever part of my body he wanted so I could please him. I had admired his masculinity all day. It was a masculinity I could never achieve, but I didn't want to. Right now, all I wanted was to lick... his... cock.

And I did. I ran my tongue along the underside of his shaft, feeling it growing and getting firmer as I did so. I buried my nose into his sack and kissed his balls, licking and kissing, then I took his big cock in my hand.

"You doin' just fine, honey. Let's see how good you can suck a dick now." I looked at the huge shaft and hesitated. As soon as the tip passed my lips, I would forever be a cocksucker. I had already compromised my masculinity, but this was irreversible. Calling someone a cocksucker was the worst kind of insult, but as I looked at his cock, my mouth involuntarily watered again. I didn't care about insults, or what other people thought. At that moment, being a sissy, effeminate cocksucker sounded like the most wonderful thing in the world. I wanted to be a pansy. I wanted to be submissive and act like a girl with a virile, masculine man, giving my body to him and doing whatever I had to do to bring him pleasure. His cock looked beautiful to me, and with only a little bit of fear, I formed my lips into a cocksucking "O" and let the tip slide into my mouth.

"Oh, yeah, baby, that's it. Work your daddy's dick, honey." I moved my head up and down on the shaft. "No teeth now. Wrap your lips over your teeth." I did as he said, and held the tip of my tongue over my lower teeth, forming my mouth into a comfortable, moist receptacle for a penis. Making my mouth into a pussy. The Chief put his hand to the side of my face, not forcing anything, just caressing me as I worked him. His dick was silky smooth to the touch, yielding at the surface but firm and hot beneath. As it moved in and out of me, I let my gaze travel up past his patch of pubic hair, up to his muscular abs, to his pecs, pausing to look at his dark nipples, and then to his face, seeing his eyes looking straight into mine. There was a fierce authority there, but what made me want to lose myself to him was that same friendly twinkle in his eyes.

He was unquestionably in charge; I had given myself over to him, and he was utterly dominant over me, but the look in his eyes let me know that it was all okay. Nothing about what I was doing was "normal." Somehow, it was better than merely normal. It was as if I was embarking on a whole new, rare way of life (which I suppose I was!), but he made me feel fortunate to be a man who could function as a woman. Other men couldn't imagine putting on women's dainties, much less wanting to, and yielding to another man sexually, but here I was, on my knees in front of a man, feeling the tug of my silky stockings against my smooth thighs, the nylons tickling my toes and feet, feeling the smoothness of my panties against my butt, pursing my lips around a man's penis and bobbing my head up and down like a whore, or a bride, gazing into his eyes, submitting myself to him. Acting just like a real woman.

I must have been doing something right, because he started moaning and gently thrusting his hips. "That's just right, baby. You doin' just fine. You a sweet little white pussyboy. You like that big dick?" I nodded and tried to smile around his cock. "You keep that up for daddy." He became less and less verbal, thrusting his hips more rhythmically, and he held his hands on each side of my head, not really forcing himself, but keeping me positioned just where he wanted. He started fucking my mouth in earnest, and it was an effort to keep myself wrapped around him, but all at once, I felt his cock swell, and he gave a spasmodic jerk and my mouth was full of semen, hitting the back of my throat and making me momentarily gag, but I realized it was him, his essence, his sperm, and I didn't want to lose it. The taste and texture was unfamiliar and not very pleasant but I remembered that this was what girls tasted when they sucked dick. I wanted to know what it was like to be a girl, and girls swallowed. I backed off his dick, and one last shot hit me on the cheek, and I held his come in my mouth, looked at him...and swallowed.

"Oh, fuck, girl, you got me inside you now." He wiped the droplet of come off my cheek with his finger. I took his hand, licked it off the tip of his finger, and swallowed again.

"Damn, baby, you a hard core sissy. And you are natural cocksucker. You mind me calling you that?"

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