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Changing My Luck, And Other Things

A date with a trans woman makes a guy change his direction.

“Hey there, hard-on,” a melodious contralto voice asked, “you got a light?”

I looked over at the tall black girl next to me and saw she held a cigarette between two long-nailed fingers, angling it in my direction. As I fished the lighter out of my shirt pocket, she stepped closer. I flicked the Zippo's friction wheel and she moved even closer as she bent over to touch the cigarette tip to the flame and suck it alight.

She was taller than me in her high heels, but she was right about one thing: I did have a boner. It had come on me almost naturally, from watching both the way she filled out her tight, gold lame' skirt and how she moved inside it as she walked ahead of me up Broadway toward the Plaza.

Then, as we stopped at a traffic light on Front Street and I walked up beside her, she made her move. I saw that the front view was as dramatic as the rear view had been; large, round, high breasts filled out her red-and-gold top admirably.

“Thanks, Sugah,” she said as she straightened up, then exhaled smoke from the side of her mouth, all the time looking directly at me, a slight smile on her face.

Her smooth mahogany cheeks, long mascaraed gold-tipped false eyelashes, reddish sparkling eye-shadow and high-arched penciled-in eyebrows all told of the care she took in applying her makeup that night, as did the arrangement of the long, flowing black wig she wore. Her face retained a teasing smile as she held my gaze, then she fluttered her eyelids - for my benefit, I supposed.

“You busy tonight, Sugah?” she asked and cocked her head to one side. By this time, her skirt and leg were pressing up against the fabric of my Levi's along my thigh.

Smiling slightly myself, I just shook my head. “Are you?”

The question was out of my mouth almost automatically, before I could stop it. But I really didn't care that night even though I knew, as did all the other sailors and Marines in civilian clothes there on Broadway that this “girl” was really one of the bevy of “He-Shes” that often paraded around downtown San Diego.

“Why, no, Sugah,” she said, intertwining both her arms with my right one just as the light changed and we stepped off the curb to continue across the street. Two other He-Shes, one white and one black, that this girl had been walking with smiled knowingly at each other and angled their pathway slightly from ours to give their companion and me a bit of separation.

“You look like you was happy to see me, baby,” she said, glancing down at the bulge in my Levi's. “Wanna have a party?”

“Well,” I said, walking along with her as she held my arm in her firm grip. “That kinda depends.”

“Depends on what?”

“You know what,” I said.

“The price?”

“Yeah,” I said with a chuckle. “How much is this going to set me back?”

“Well, I tell you what I'll do for ya, Sugah,” she said, taking a deep drag from her cigarette, then flicking it away, half smoked. We had stopped on the sidewalk now and the two other girls walked on. “You're so cute, and sweet, and sexy and all...”

She smiled at me and I smiled back, a little embarrassed. I looked down at the sidewalk for few moments, then back up at her. She really did look feminine. In fact, I would say she was just plain gorgeous. Beautiful, dark brown—almost black—eyes made up in a style that made her look like an Egyptian goddess; a sable Nefertiti come to life.

“Why, I don't think I'd charge you anything, Sugah.” She laughed. “Just pay for the room.”

“Just the room?” I asked.

I was shocked. Even though I'd never tried approaching one of these types of “Ladies” before, I always assumed they would charge a good deal for their favors. I was used to whores, of course. After three years in the Navy in San Diego and in Charleston, South Carolina, plus numerous trips down to the flesh-pots of Tijuana, I considered myself quite familiar with prostitutes and their ways. But, like any man, I was still hoping to find that whore with the proverbial “heart of gold” that makes for such good Hollywood fare but is almost never found in real life. Or at least, I had never found one like that.

“Why sure, Sugah. You just rent us a room that we can use for our little party, then afterward you can go on home and leave me the key.” We started walking up Broadway again. “That way, not only does it not cost you very much, but Chiffon and Brenda, there,” she nodded toward the other two He-Shes, who by now were several yards ahead of us, “can use that room, too, when they find dates. After we're done, o' course.”

“But what if I don't want to leave afterward?” I asked. “Suppose I want to spend all night with you?”

She laughed with genuine good humor, throwing back her head. I could see some evidence of an Adam's apple on her brown throat: giving away her true gender. Still smiling widely, she lowered her gaze again and the illusion returned.

“All night?” she went on. “You really think you could handle a girl like me for all night? You that much of a stud, Sugah?”

I laughed and shook my head. “No,” I said. “I ain't any kind of stud at all. But I've never been that much of a fan of that 'Wham. Bam. Thank you ma'am' kind of sex. I kind of like to snuggle and cuddle a little bit afterward. Pillow talk. Get to know the person I'm with. That kind of thing.”

“Ooooooooo,” she cooed. “You are the romantic one, ain't ya?”

We walked on for several steps. Suddenly, she stopped and turned toward me, moving even closer. Without thinking, I reached up and put my arms around her waist. It felt so natural to hold her that way. I could feel the warmth of her firm body through our clothing. I could also feel my dick getting even harder.

“Say, Sugah,” she said, looking down into my eyes. “You know what kind of girl I am, don't ya?”

I nodded.

“And it don't make no diff'rence?”

I shook my head, smiling at her. She certainly was lovely. One of the best-looking women I had ever been with. It really didn't matter to me what she had hidden underneath those clothes.

“You evah been with a woman like me before?”

“No,” I said after standing there, holding her a while longer. “But I've... uh... I've been... uh... been with... guys”

“You sayin' you gay?”

I shook my head. “I just take what I can get.”

“Well, Sugah,” she said, taking my hand in hers and pulling me along, crossing Broadway and heading toward the U. S. Grant Hotel. “Then you is just about to get yo'self somethin' special.”


And that's the way it happened, that spring evening back in 1971. There I was, at twenty-three, just one of the many horny young sailors and marines prowling the streets of San Diego in search of whatever kind of gratification I could get, the same as men in any other military duty station town at that time. Some of those servicemen found gratification in the form of drink, some with weed or other drugs, some with the whores in Tijuana or wherever and many, many of them never finding it at all.

Those that didn't find it were the kind of guys who ended up masturbating in the heads of barracks or ships or wherever they could find a little privacy. I had found gratification a few times with other guys, like I told Crystal (that was her name, I found out that night). But that involvement usually had only extended to blow jobs from the guys who picked me up when I was walking back to the base there in San Diego when I was going to my service schools, then later doing the same thing when I was assigned to a ship in Charleston, South Carolina.

I had noticed that the gay guys who picked me up and gave me blow jobs always did a much better job of sucking a dick than did the whores and even the few civilian girls I had ever had perform that service for me. But, curious at what it was like to suck a dick, I did suck on a couple of the guys who picked me up. But none of them had ever cum. So really, I didn't know what to expect from Crystal that night.

I should have been afraid of being rolled, I guess; of her pulling a gun or some other sort of weapon, then taking my wallet and watch and whatever other valuables I had. But I wasn't. Heck, I only had about $30 in my wallet anyway. But in 1971, thirty bucks seemed like quite a bit of money for a poor E-4 sailor like me.

But anyway, when we got to the Grant, I went inside to get the room while Crystal remained outside, leaning against the hotel's outside edifice; looking for all the world like a hooker on the make, which in essence she was, of course. The room cost about $20, if I remember right, which was five times what it would have cost me for a room at the YMCA. I know that is not anything like what a room would cost at the Grant, or anywhere else in downtown San Diego these days. But this was 1971; a far more innocent - and considerably cheaper - time.

After getting the room key, I returned outside. I only half-way expected Crystal to still be there—I'd been burned like that with whores before. But there she was, still looking lovely. But I noticed the other people outside the hotel were giving her a wide berth. I showed Crystal the room number on the key tag, then returned inside with her holding onto my arm as we walked across the lobby to the elevators.

I halfway expected her to be all over me in the elevator, but a couple of other guys entered the elevator at the same time, so we just rode up to the fourth floor in silence. The two other men didn't even look at us. Or if they did, it was out of the corners of their eyes.

When we got to the room and I unlocked the door and we went inside, I gave Crystal the key like I'd promised I'd do. She dropped it into the handbag she had slung over her shoulder, then quickly spun around and had her arms around my neck, pulling me to her before the door was even completely closed.

Her lips found mine and the next thing I knew I had a mouth full of tongue. I also felt her hands all over me; one sliding up my ribs under my civilian shirt and the other grabbing my butt.

Finally, we broke the kiss. “Don't you... Think we ought to...” I said.

“Go to the bed?” she asked.

“Yeah,” I said. By this time, my cock was so hard it was almost painful.

“OK, Sugah,” she said. She picked up her bag, then dropped it into a chair as she sauntered over to the bed, wiggling her ass as she walked, trying her best to look seductive and succeeding admirably.

I just watched her and reached down to ease the tightness of the fabric of the Levi's over my throbbing erection.

She sat down on the bed and looked at me, grinning. “OK, Sugah,” she said. “Show me what you got.”

I guess I was feeling a little feisty, instead of just horny, so I said, “Well, why don't you show me what you got.”

“What I got?” She asked. Whether the surprise at my suggestion was real or feigned, I wasn't sure. “You want to see what I got?”

I nodded. “Yeah,” I said. “I'd like to see if those tits are real.”

She began to lose her smile a bit at that. A little bit of doubt began to show on her face. She looked down at her chest and gave her head a little bit of a shake. She lifted her head again and shimmied her shoulders a bit, making her breasts move some under the blouse. “Don't they look real?”

“Sure they do,” I said, walking up to the bed. She looked up at me and smiled again, reaching out to the belt of my Levi's and swiftly undoing it, then starting to unbutton the waistband and fly.

I reached out and cupped one breast in my right hand as she worked. It did kind of feel real but it was hard to tell through all the cloth of her clothing. I wondered if it really was flesh.

By this time, she had my pants completely unbuttoned and began sliding the denim fabric down off my butt. I wasn't wearing any underwear. As the Levi's moved down, my erection sprang up toward her face.

“Why, you go commando style, don't you, Sugah?” She said, laughing and looking up at me. Then she turned her attention back to my dick. She grabbed it with one hand, turning in back and forth as she inspected it. “You ain't very big, are ya, Sugah?” she said.

“I know,” I said, nodding, a little embarrassed at my six-inch erection.

She looked up at me, smiling widely again, her eyes twinkling. “But like they say, Sugah. Anything more than a mouthful's wasted.” She then went to work, eagerly slurping the head of my dick into her mouth and continuing down until it was buried in her throat as far as it would go.

It felt wonderful, of course. I hadn't been sucked in a long time. But after sliding her mouth up and down on it a couple of time, she slid her lips back up to the tip and let it spring out of her mouth, making a “pop” sound as it did so.

“Oh, baby,” she said, looking back up at me again. “You got a nice dick, there, honey.” Another mischievous twinkle was in her eyes. “But you said you wanted to see what I got, didn't ya.”

I didn't want her to stop, but I nodded. “Yes,” I said. My voice sounded phlegmy and constricted in my own ears. I cleared my throat and went on. “I'd love to see what you have,” I said.

“OK, baby,” she said, standing up. “I'd love for you to see what I got, too.”

With that, she pulled the hem of her skirt up to waist level, exposing her pantyhose and the white panties underneath with a decided bulge in the front, then pulled the hose and panties down and letting her penis spring up, just like mine had done earlier.

I was a little disappointed, I guess. Her dick wasn't much bigger than mine and only semi-erect. It was probably only about five inches long in its present semi-flaccid state and not terribly thick. Now, I was fairly familiar with black dicks from showering with black men in barracks or back in high-school gym classes and, like everyone, had noticed most black guys seemed to have larger penises than white guys like me.

That wasn't always the case, though. I remembered one black company mate in boot camp whose dick was also rather on the small side, maybe even smaller than mine. But he had been a rather heavy-set guy and I had also observed that many fat guys, whether black or white, seemed to have smaller penises.

She looked over at me and smiled faintly. “You disappointed, Sugah? Ya know, not all black guys have big cocks. We come in all sizes, just like you white boys.”

She slid the panties and hose down, stepped out of them, then leaned in closer, putting her hand back on my dick. I reached out and felt hers, then she leaned in and kissed me again, exploring my mouth with her tongue.

My Levi's had already slid down around my calves and, after slipping off my loafers using my feet, I kicked my legs free of them. Slowly, Crystal and I sank down onto the bed, then lay out flat on it, all the while kissing passionately. I let go of her cock and my right hand roamed up under her blouse. When my hand got up to her bra, the kissing stopped and she pulled her head back away from my face.

“Why don't I take this stuff off,” she said, then sat up, turning her back toward me. She quickly peeled off the blouse over her head, which left her wig a bit askew, but she straightened that up quickly, then reach around toward the back of her bright red bra.

“I'll give you a hand there,” I said and reached over and quickly unhooked the fasteners as she arched her back. And as I unfastened her bra I noticed slick ridges and smooth, shiny places where scar tissue covered her back.

Her hands and arms came up to the bra and she held it there, then looked back at me over her dark shoulder. A sad expression crept over her face.

“'Fraid you gonna be disappointed again, Sugah,” she said. “They ain't really real.”

With that said, she lowered the bra. I could see the cups were filled with foam rubber shaped like tits. She turned slightly back toward me, then took away the bra completely, revealing her black chest with wide-set male breasts, but breasts with slightly more heft to them than a normal man's.

“This part's real,” she said, cupping the flesh in her hands. “I been takin' some stuff to make 'em bigger. The rest of it ain't.”

The nipples on the dark chocolate aureoles in the center of her milk chocolate breasts were erect, but that was probably just natural. Heck, my tiny pink male nipples were almost always erect, too.

She looked at me imploringly. “You sure you don't mind, Sugah?” she asked. There was almost a pleading quality to her voice.

I looked over as she sat on the bed, half turned toward me as I lay across it, propped up onto one elbow. Her face was still lovely, though the makeup was slightly smeared from all the kissing we'd done and with the wig topping off her face, she still looked like a lovely woman—at least from the shoulders up. I smiled at her, then shook my head.

“No,” said. “I don't mind at all.” I wasn't really sure if that was true or not, but I said it anyway. “Like I told ya, I've been with... guys before.” I leaned forward and took one of her nipples into my mouth, sucking on it and running my tongue over its surface.

While it was true that I had been with other guys, it had only been rather quick blow jobs given to me in cars or motel rooms by lusty gay guys who had picked me up. I had also sucked on a few of those guys, too, yet never to orgasm. This was different. I had almost sought out this contact as I watched Crystal walk up the street, then boldly walked up beside her. She had looked and moved like a woman then. And I was horny. So what made this wrong?

Nothing, I decided. Still sucking on her breast, I reached over and let my hand rub lightly across her bare back. She turned fully toward me, reaching up with her hand to hold my mouth against her breast for a while, then lying back down on the bed and nestling into my arms.

I raised up my head to her face and we kissed again. We continued kissing as her hand trailed down toward my dick again. She grasped it and lightly moved her hand up and down the shaft. She kept kissing me on the mouth for a while, then began taking her lips down my face to my chin, then my neck, down my chest... Then she sat up again, needing to change position.

“If you don't mind, Sugah,” she said, “I'm gonna take this wig off. It's hot.”

She reached up and pulled the wig up and over the top of her head, revealing short, closely cropped black hair, then bent back down to place her mouth on my erect, straining penis again.

I just laid back down flat on the bed and enjoyed it. I reached out my hand and rubbed it over her bare back as she sucked me. I could feel those hard ridges and slick spots I'd seen earlier and wondered what they were.

Crystal moved over a bit, turning slightly, presenting her package to me. I looked over at her dick and balls, then began to caress the scrotum. Though her semi-erect penis was not especially large, her scrotum was. I licked on it, then ran my tongue along underneath the shaft of her penis. She turned some more and I was now able to reach the head with my mouth. Her cock was circumcised, like mine and it seemed to be getting harder. It slid easily into my mouth.

Sucking slightly, I moved my mouth and lips slowly down and then back up to the head. I popped it out of my mouth, then kissed the tip, running my tongue over the hole. I knew I wasn't an expert cocksucker, but I was at least trying. But what really surprised me was the fact I was enjoying the whole thing. The taste, the feel of her now hard dick felt great as it slid into and out of my mouth.

Crystal, though, was an expert cocksucker and her machinations on my dick had me close to cumming. I groaned and suddenly, she stopped. Raising up, she said, “No, no. Don't cum yet, Sugah. That's not where I want you to.”

She quickly got up and walked over to the chair where she had left her purse, reached inside it retrieved a small black cylinder, then walked back over to the bed. I watched her and noticed her dick was becoming more flaccid, swinging slightly back and forth as she walked.

“Move into the middle of the bed, Sugah,” she said and I complied.

She climbed onto the bed, moved over me, straddling my body with her legs, then began applying lube from the cylinder to her asshole and my erect, throbbing dick. The touch of her hands and the cool, slick lube on my cock felt wonderful and I almost came right there, but willed it not to. But when she positioned herself over my erect member and began sliding down it, the sensation was even better. Finally, she was all the way down. She folded her legs down beside mine and began riding my dick with a slow, rocking motion.

“Ooooooh, God!” she moaned as she rocked. She looked down into my eyes again. “That feels soooo gooooood!”

It certainly did. I thrust up with my hips as she rocked back and forth and soon we were in a wonderful rhythm.

She looked down at me, biting her lip, I could see. Her eyes rolled back in her half-closed eyes as she rocked — seemingly in ecstasy. I could see her panting — enjoying the feeling of me inside her.

I was feeling pretty damned good myself as I helped her rock back and forth. Though most of my attention was directed at Crystal's face, I did glance down a couple of times and watched her semi-soft cock flopping up and down as she rocked. Soon, I could feel my orgasm building. “I'm gonna cum,” I told her.

“Oh, yesssss,” she sighed. “Do.” She looked down at me and smiled. “DO IT!”

My orgasm was intense; the jism squirting up into her ass as she kept rocking. Crystal's head lolled back as she kept smiling, enjoying the feeling of my semen squirting into her. I found myself thrusting upward still, trying to get as deep into her as I could.

Finally, she collapsed on top of me, my still-erect penis finally coming out of her ass as she lay down beside me.

“That was wonderful, Sugah,” she purred, breathlessly. She snuggled in beside me. “You are sooooo good!” She was breathing heavily as she regained her composure. She looked at me and smiled.

Of course, without the wig, she didn't look quite as feminine as she had before, but with the eye makeup and everything else, her face was still pretty. “Did you enjoy that, Sugah?”

“Oh, yeah,” told her. “That was great.” I leaned in closer to her and we kissed, lightly. “Did you like it?” I wanted to tell her I'd never had anal sex before, with either a male or a female, but didn't quite know how to broach the subject.

“Mmm-hmm,” she purred. “I always enjoy gettin' on top like that.” She lifted her head up and looked at me, still smiling. “You know, usually I just lie on my back and pull up my knees to let a guy fuck me, but when I noticed you was kind of small and all, I know that sometimes don't work that well.”

She must have seen something in the expression on my face because she quickly went on. “Oh, don't fret yo'seff 'bout that, Sugah. I'm kinda small myself. So I know how it is.” She smiled, broadly. “But you done goooood, Sugah. Real good!” She snuggled in closer, placing one arm over my chest. “What's yo' name, Sugah?”

“Roger,” I told her. “What's yours?”

I thought it ironic that even though we'd just fucked, we had never even exchanged names.

“Crystal,” she said, smiling. “I won't even tell ya my guy name, because I never liked it in the first place, anyway. So I'm gonna be 'Crystal' from now on. ” She looked away and the expression on her face hardened. “For the rest of my life,” she said emphatically.

She sat up on the bed. “Yeah, Sugah,” she said. “I'm goin' all the way. All the way, baby. I'm already taking that hormone stuff. I get it down in Mexico from a doctor I go to there. He shoots me up with that stuff. That's what's makin' my tits bigger...” she reached up to her chest and cupped them. …and what's makin' this thing...” she reached down to her penis with one hand and flipped it between her thumb and forefinger, “...not work so good anymore. Then, someday soon, I'm gonna have this damned dick cut off and made into a pussy. And if these tits don't get big enough on they own, I'll have 'em made into real tits with that silicone stuff. Then I'm gonna be a real woman, Sugah. Like I always been, deep inside.”

I finally found my voice, “You mean like... uh... Christine Jorgensen?” It was the only name I was familiar with in 1971.

“Yeah, Sugah,” she said, reaching down to where she'd tossed her wig when she removed it. She stood, then walked over to the counter where there was a sink and a mirror, just outside the bathroom. She started running water into the sink and tossed in a washcloth. She looked back over her shoulder toward me and smiled.

“I got you runnin' down my leg here, darlin',” she said with a laugh. “Guess I oughta get that cleaned up.”

As Crystal used the washcloth to clean up her backside, I just laid on the bed and watched her. After she finished, she used a towel to dry off, then retrieved her pantyhose and panties. She pulled on the panties, then sat down in a chair and put her pantyhose back on.

Next, she rolled the chair over to the dressing table beside the bed, sat down on the chair there and put the wig back on. The addition of the wig transformed her back into the Crystal who had first attracted me. She reached over to where her purse was lying on the floor, put it on the dressing table and took out a hairbrush and a makeup bag.

As she began restyling her hair with the brush, she said almost absently, to me, “Don't you think you oughta get yo'sef cleaned up a little, too, Sugah?”

“Yeah,” I said. “I guess I ought to.”

I rather reluctantly got out of bed, walked over to the sink, turned on the hot water and tossed another washcloth in to get it wet. All the while I was watching Crystal as she now applied herself to her makeup, which had gotten considerably smudged during our lovemaking.

As I washed my dick and balls, I watched her quickly put the makeup right again and soon her face was as lovely as it had been before. I was especially taken in by her lovely dark eyes. She looked totally feminine in the face again even though her still-masculine chest belied that appearance.

I reach over to where I'd tossed my jeans and shirt and soon had them back on, then went over to the bed and sat down to put on my shoes. From that angle, I watched in the mirror as Crystal worked. Soon, her eyes locked onto mine in the reflection.

“You was really good, Sugah,” she said, smiling. She turned in my direction. “I'm really glad I picked you out. You a great lover, baby. I really enjoyed that.”

I smiled a little self-consciously and looked away. “Well, I'm glad you did,” I said. I felt like I needed to say something else. “I enjoyed it, too,” I added. It sounded lame in my own ears so I continued, turning to face her reflection again. “I really did.”

“You said you ain't never been with a woman like me before,” Crystal said. “But you been with other guys?”

“Yeah,” I said. “When I was stationed on a ship in Charleston, I got picked up a couple of times by gay guys. And I let 'em... You know.”

“Uh-huh,” she said, still peering at me as she touched up her lip gloss. “I know how that goes.” She turned over in my direction, hooking one elbow over the back of the chair. “But you did suck a guy's dick, didn't you, baby?” she asked. Her eyes locked onto mine.

For some reason, I couldn't look away. I don't know why. Maybe it was her honest nature that made me decide to be honest, too. “Well, I...uh...” I shrugged. “I did suck on guys a couple of times. A little... But never all the way.”

“Oh,” Crystal said, turning back to the mirror. “So mine ain't the first dick you evah had in yo' mouth. That right?”

“Uh,...” I looked down. “No,” I said. “But I never sucked one off... you know... All the way.”

“Uh, huh,” she said, reaching behind her to fasten her bra with the foam falsies inside. She pulled the cups into the proper position, then reached for her blouse.

After she pulled the top on, Crystal looked at me in the mirror, smiling slightly. “You know, Sugah,” she said. “I been lookin' at you. If you don't mind my sayin'...  You really awful cute.” She turned around to look at me, one arm crooked over the back of the chair. “You evah tried dressin' up, Sugah? As a woman, I mean.”

I looked down at the floor, unable to meet her eyes, now. “Well,” I said. “Just... Sometimes... Yeah.  When I was sixteen I used to dress up in step-mother's clothes.  Put on her makeup and everything."

“Why, I bet you looked real cute, baby,” she said.

I shrugged, still not looking at her. “Yeah,” I mumbled.

I didn't want to admit it, but not only did I look really good made up as a girl, And the whole experience always gave me a hard-on. I remembered how great the satiny underthings felt on my body and how I'd stand in front of the mirror dressed in her clothes and masturbate.

“Well, you oughta try it sometime, Sugah. With me and my girlfriends… We could dress you up real fine. 'Course, you might be kinda tall for a girl, but then, I'm kinda tall, myself. ”

I chuckled and turned my face toward her, shaking my head. “No,” I said, even though I really didn't believe it. “That ain’t me.”

Crystal turned back to the mirror and continued fixing her makeup. She would soon be back to looking the way she did when I first saw her.

“You oughta consider it sometime, though, Sugah.” looking at me in the mirror. “You got a real cute face and we could make you up to look like a real good-lookin' girl. Then you could go cruisin’ together with all of us… We could have lots of fun. We could teach you all the tricks o' actin’ like a woman.”

I was silent for a long time after that, it seemed to me. I was considering it, I guess, picturing it, myself dressed up the way Crystal had been. I remembered dressing in my stepmother's clothes and how it made me feel back then.

And admittedly, I'm not exactly the most masculine of men. At only 5' 9” I'm a bit shorter than many guys. Hell, even Crystal was taller, especially in her high heels. And I also remembered back in Charleston picking up magazines about cross-dressers a couple of times in some of the convenience stores.

Some of those “women” really did look good, just like Crystal and many of the other “He-Shes” I saw in San Diego.  And maybe seeing the women in those magazines and remembering how good they looked to me is what made me walk up beside Crystal tonight.

Finally, I shook my head, though. “I don’t think so,” I said. “That’s… That’s just not me.”

In the mirror, I could see Crystal smile as she applied eye makeup. “Hell, I didn’t think it was me, either, back when I was a Marine.”

This shocked me. “A Marine?’

Crystal laughed good-naturedly at my shock. “Yeah,” she said with a smile in her voice. “I was in the Marines. Oorah, and all that bullshit, ya know? Joined the Corps right outta high school to prove to ever'body I was really a man,... even though I knew deep down inside I wasn’t.”

“My god,” I said. “When was this?”

“Oh, I been out o’ the Corps 'bout two years, now. Got me a medical after they took that kidney out.”


“Yeah. It got tore up pretty bad from all the shrapnel and ever'thing.”

“In ‘Nam?”

“Yeah,” she said as if it was an obvious answer. “One-oh-five round went off behin' me and all that shit just tore th' fuck outta my back, Sugah. They thought I was gonna lose both my kidneys there for a time, but they managed to save one of 'em.” She chuckled. “Good thing, too, or I wouldn't be here now. I'd be dead. Or else hooked up to one o' them die-alisis machines for the rest o' my life.”

“My God,” I said. Now I knew what those ridges were that I'd seen and felt on her back: scar tissue. “Were you... in the hospital a long time?”

“Oh, just 'bout forevah, it seemed like.” She paused and a dreamy kind of look took over her face. “But that's also where I changed.”

I suppose a puzzled look was on my face as I gazed at her face in the mirror. Her reflection smiled back at me.

“Yeah,” she said. “That's when I realized I was really a woman inside and not a man anymore.”

She continued working on her makeup and hair while she talked.

“I was kinda out of it there for a long time, what with all the pain medication and everything. And afterward, people was kind o' teasin' me and ever'thing. Said I was cryin' an' carryin' on like a goddam woman or somethin'. At least that's how it started out. Then some of 'em... Brothers, even... Started call me a pussy. Sissy... Sayin' I was a woman. Wantin' to know if I'd suck they dicks and ever'thing. Wanted to know if they could fuck me, since I was such a sissy...” She shook her head, making the ringlets of hair on the wig jiggle.

“And...” she went on. “Since I'd already done that sort of stuff before... You see, Sugah, when I was sixteen, me and my cousin used to suck each others' dicks.  We nevah was into girls, neither one of us.  And I also let him fuck me in the ass... Oh, a bunch o' times...” She turned from the mirror to look at me directly. “And you know, Sugah... When I got to rememberin' those times, there in the hospital after I was wounded.., I got to rememberin' that I liked it.”

I think I started blushing on hearing that, remembering how good it felt with Crystal's dick in my mouth.

But Crystal didn't seem to notice. “I got to rememberin' that I really I did like suckin' a guy's cock,” she went on. “ And I really liked havin' a guy fuck me an' cum in my ass... It felt good, Sugah. It felt right. Evah time.”

“Well,” she said, turning back to the mirror. “That's when I just decided to just quit fightin' it. Quit tryin' to be a man,  Decided I really was gay. That I really was... deep down inside… a woman.”

I just sat there on the bed, staring at her face in the mirror. I wondered why Crystal was regaling me with her life story like this.

“So then, when they finally gave me that medical discharge,” Crystal went on. “I decided to stay down here in San Diego instead of goin' back home to LA.”

“That where you're from?” I asked.

“Yeah,” She said. “Compton, really.” She went back to her earlier subject. “So when I got out o' the Corps, I looked up some of them girls I met around here. I'd seen 'em walkin' around downtown when I was on liberty from the hospital. The trans-women. 'Splained to 'em what I decided. And you know? They took me in. Showed me all sorts o' stuff... Showed me how to dress, and walk, an' how to do my makeup... All kind of things to do to help me become a real woman.”

Finally satisfied with her appearance, Crystal turned to face me. “And you know,... We could do the same sorta things for you, too, Sugah. Show you how to dress real cute... Real sexy. How to walk... How to flirt with guys... All sorts of stuff.”

“But,... ..uh...," I stammered. "What do you do when you do talk to those guys... And... uh... They're attracted to you.”

“Well,” she said. “Most of the time, that's all it is, Sugah. Just flirtin'.”

“Yeah, but... What if they want to do more... You know...” I knew I was blushing for sure by this time. “Want you to... You know.”

“Suck they dick? Fuck ya?” She laughed. “Well, it don't usually come to that, Sugah. You can almost always put 'em off, somehow.”

“But if they... Or if you really like them, or something?”

Crystal laughed at me. “Why, then you just have to suck they dick, I guess.” She smiled broadly at my embarrassment.

“But I... I told you... I've never done that.”

“Well,” she said with the smile still on her face. “I guess you'd have to.”

“But....” I was stammering. “B... but...”

“Well, Sugah... You done tol' me you done sucked on one before. And you had my dick in yo' mouth tonight....”

“Yeah,” I said. “But....” I looked up at her. “We were....”

She just stared quizzically at me.

“And I... uh...” It seemed like I couldn't finish any thought I had. “You didn't...” I was looking down at the floor by this time but I could feel my heart pounding.

“What you sayin', Sugah?” she asked, her voice full of concern. “Did you wanna... You wanna... Finish the job?

I could only nod dumbly. I'm sure my face was bright red by this time. With difficulty, I looked back up at her. “I was enjoyin' suckin' on it earlier,” I said. “It... It's like you were sayin'... It felt... It felt... right.”


I kept remembering all the times I'd been with gay guys in Charleston and San Diego; the times I had sucked on them, even though none had ever cum in my mouth.  How it felt good. And about how I now frequently fantasized about sucking someone's dick while masturbating lately. How I sometimes placed a little of my own semen on my tongue afterward, just to see how it tastes.

My breathing was now coming in short, panting breaths as I looked imploringly at her beautiful face. “I really would,” I said slowly and softly. “I'd like to suck you off.”

Crystal sat with her mouth slightly agape, looking at me curiously.

She laughed, finally, shaking her head. “Well, I nevah... You really want to, Sugah?”

I nodded again.

“Well, she said. “If you really wanna.”

She stood up from the dressing table and walked over to where I was still sitting on the bed. Reaching up under her short skirt, she grabbed the waistband of the pantyhose and panties underneath. She pulled them down to her knees, bending over slightly as she did so, then stood back up straight.

When her cock escaped the confinement of her underclothing, it sprang up slightly, tenting the gold lame' skirt a bit. She pulled the fabric of the skirt up out of the way, stood right in front and presented her brown, semi-erect cock to me as I sat forward on the bed's edge.

“'Course, I ain't 'zactly sure how hard it's gonna get, though,” she said.

I didn't care. Her cock was beautiful, I thought. Mahogany brown shaft but with the head slightly lighter in color, the scrotum darker—almost black. I put the fingers of my right hand under her ball sack and hefted it a bit, making her semi-rigid penis stand up a bit higher. I kissed the head, then licked a bit of pre-cum from the hole.

But soon I sucked the whole thing into my mouth, feeling it slide in over the tongue. As I began sucking and moving my mouth up and down its length, the cock grew harder and firmer. I could feel Crystal's hand on my hair, just like I had run my hand over the heads of other guys as they sucked my cock.

Oh, my God, I thought to myself. I'm sucking a cock! Really sucking it! And a black cock, too! Oh, my God! This is GREAT! I really am a queer.

“Oh, yeah,” Crystal was saying as I sucked away. 'You doin' good, Sugah. You doin' everythin' just right. You so good at this, baby.”

I kept sucking away, my saliva flowing all around Crystal's hard dick and some trickling out the corner of my mouth. She began humping my mouth in rhythm with me bobbing on her cock.

“Mmmmmmmmm,” I heard myself moaning as I sucked and making slurping sounds as her dick plunged in and out of my mouth.

I sucked and smacked and moaned and swallowed my excess saliva for a long time, it seemed, but I enjoyed every minute of it. I looked up at Crystal as I sucked, just like I'd enjoyed seeing other guys and women look up at me as they sucked on me.

Crystal smiled lovingly back at me. “Oh, yeah, Sugah,” she moaned. “Yeah, baby. YEAH!”

I felt Crystal's cock hardening and swelling in my mouth, the dick now tasting sweeter than ever, then felt the hot, sweet sperm begin to squirt into my mouth and throat. I nearly gagged, but suppressed it and started swallowing as she came in heavy spurts. Finally, the spurting subsided a bit and I retained the last bit of cum in my mouth, savoring its flavor. I pulled off Crystal's quickly-softening dick and stood up. I put my arms around Crystal and kissed her, sharing the cum I still had in my mouth.

Crystal kissed back with gusto. Finally, we broke the kiss and stood there looking into each other's eyes.

“Oh, baby,” Crystal said, smiling at me. “You done that so goooooood!” Crystal said, breathlessly. “You sure you ain't nevah sucked anybody off before?”

I just smiled at her and shook my head.

“Well, you a natch'l at it, Sugah.” She waddled back over to the vanity with her pantyhose and panties still around her knees then grabbed a washcloth the wipe away the trickling cum on her dick. Satisfied, she pulled the panties and pantyhose back up, then smoothed out her gold lame skirt.

She turned back to face me and smiled broadly. She walked up to me and hooked her arm around mine.

“Thank you, Crystal,” I told her. “That was great.”

“Yes, it was,” she purred in my ear. “That was fabulous.” She hugged my arm tighter. “You know,” she said. You almost make me wanna reconsider becomin' a woman. Just so's you can do that again.”

I smiled at her and chuckled.

“You all ready to go, Sugah?” she asked me.

I was. I looked around the room to make sure I hadn't left anything. Crystal walked to the counter where her purse was, picked it up and slung it over one shoulder. She turned to face me. I just stood there, looking at her. She was back to looking just as fetching as she had been when I first saw her. She looked great!

We walked to the door of the room together but stopped as we got there. One last hug and one last, light kiss. We opened the door and walked out. Soon we were back on the street in front of the Grant.

“Come with me, Sugah,” Crystal said as we walked out of the hotel and started to the crosswalk arm-in-arm. “We'll go meet Brenda and Chiffon at this club we go to. Give 'em that key you done give me. Tell 'em you gonna be joinin' us.” She looked over at me. “You do wanna join us, don't ya, Sugah? Gettin' all dressed up and goin' cruisin'?”

I shrugged. The idea was interesting. Thinking about dressing up like a woman did appeal to me—being like those cross-dressers I'd seen in those magazines in Charleston. I could feel a bit of stirring in my crotch as my dick started to harden a bit at the thought.

“Yeah, Sugah,” Crystal said as we walked. “You gonna make a real cute girl.” She paused for a bit. “Any idea what you gonna call yo'self? When you all dressed up and ever'thing?.”

I laughed. “How about 'Sugar,'” I said.

“Sugah?” she said with a laugh. “Why, that's a real good name for ya, Sugah. How'd you evah come up with that?”

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