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The Road Less Traveled

[[names changed to protect the naughty]]

After a series of back-and-forth messages over the last three nights, he was finally ready to meet. "Sam" had contacted me through my personal website, apparently having been extremely intrigued by some of the photos I had uploaded.

Sam himself wasn't bad looking, being in his late fifties, a little over six feet with a solid build and dark hair with a touch of grey. He had dark eyes with a somewhat stern look that I found very magnetic. "I've never been with anyone but females before," his first email began, "but I've always fantasized about finding a younger boy willing to dress up for me and serve me as a girl. The younger, the better. I picked you because I've never been with anyone Black before, and I was infatuated by your smooth brown skin."

Now, I'm in my late twenties, but I've maintained a thin, light frame through regular bedroom acrobatics and a careful diet. So I could easily pass for a college freshman if necessary. In fact, I have a powerful attraction to older lovers, and I've managed to specialize in satisfying "mature men who desire the intimate company of a feminized boy." A few more messages followed in which he agreed to the fee for my time and sent me his address. And most importantly, Sam wanted to meet at eleven tonight, which gave me just under two hours to get myself together.

After inspecting my closet for a few moments, I picked out a couple of outfits matching what he'd requested in his earlier messages and packed them in my garment bag, then started the shower. As the bathroom began to fog up, I started lotioning my body with depilatory cream, making sure to cover every strand of hair from my neck down to my ankles. After a ten-minute wait, I jumped in the shower and rinsed off. As the last of the hair vanished down the drain, I gave myself an enema to make sure my kitty was squeaky clean, then soaped up and rinsed off again. In another five minutes I shut off the shower and drained myself, making sure to wipe down once again. After letting myself air-dry, I oiled down my entire body with perfumed moisturizer and trimmed my nails. By then it was almost game time, so I brushed my teeth and slipped on an over-sized t-shirt with jeans and tennis shoes, gathered up my bag and headed out--stopping just long enough to send Sam a text that I was on my way.

Thirty minutes later I was passing through the main gate of his community. His home was quite nice--a three-story detached townhome with a terrace on the upper level, with an excellent view of the downtown skyline unobstructed by any of the dozen or so similar homes on the lot. Sam gave a ring as I parked just outside his garage, telling me that the door was open. I got out my car with my bag and went inside, meeting him in the foyer. I followed him upstairs to one of the bedrooms as we made some small talk, checking out the decor and noting with a little amusement that Sam was married with two teenaged girls. He hadn't mentioned that, not that it really mattered to me. He followed my gaze and read my mind. "Yeah, they're out-of-town for the next three days," he explained. "Drill team competition."

"I don't really care, daddy," I murmured. "As long as I don't have to worry about any interruptions." I slipped up closer to him and brushed a hand over his chest. He flushed and broke stride for a bit.

"You're being bad already aren't you?" he breathed.

"That's why I'm here," I whispered, burying my face in his neck.

Sam turned around and pressed me against the wall, lifting my head up for a very long and hungry kiss. "You smell very good, angel. I love that."

I kissed him for a few more beats, then broke off. "Don't you want me to get prettier for you, daddy?" I whispered, watching his reaction carefully. Sure enough, he looked both guilty and lustful at my last words. So much the better.

"Yes, you're right, baby," he said, stepping back and letting me escape. "You can use that bedroom--" He pointed to the room just ahead. "Just call me when you're ready."

"Of course, daddy," I said. "Give me twenty minutes." I stepped into the room and pushed the door nearly closed, leaving it cracked open a couple of inches. I spread my outfits over the bureau and began stripping off my boy clothes, knowing that Sam was watching from the hallway. I paced back and forth naked for a bit while I pretended to decide which outfit I wanted to wear first. I held up a pale lavender pleated tennis skirt with a matching corset, then laid then aside. Then I sat on the edge of the bed and tugged on a pair of white crotchless suspender pantyhose, having decided against wearing any underwear. Next I slipped on the tennis skirt, turning about before the mirror to admire the way my ass filled out its rear. Standing bare-chested before my reflection, I could already feel myself slipping into my sissy persona, but I had a few more things left to do before I could let go completely. I turned around and put on the corset, lacing it up tightly to narrow my lower torso to a far more womanly shape. Reaching in my bag once more, I put on a short dark auburn wig, with the ends just reaching my shoulders. Finally I slipped on a pair of lavender platform sandals with five inch spike heels. All that was needed was a little makeup to complete my look. Over the next few minutes I applied a little concealer, light purple eyeshadow, eyeliner and lip gloss. Checking myself out in the mirror one more time, I saw Ashley, the hot black transvestite slut, ready to please her daddy. I just needed one last thing. Pulling out a packet of lube, I squirted the contents on my fingers and worked them into my pussy, getting it fully greased up. I felt my clitty stir uncomfortably, but managed to will it back down. I'd be releasing it soon enough.

I sat back on the bed facing away from the door and said softly, "I'm ready for you daddy." Sam burst in with no delay, stopping short a few feet away and just staring at me in disbelief mingled with incredible lust. Seeing that, I couldn't resist and squatted down in front of him, reaching up to pull down his pants.

Sam had one of the tightest bodies I'd ever seen on an older man, and I wanted to feel it yesterday. As soon as his pants hit his feet, he grabbed the back of my head and pulled me forward, grinding his crotch on my face. "Lick my balls, whore," he ordered. "And don't miss a spot."

I couldn't help but do so, quickly becoming even more aroused by his strong scent. I licked my lips to get them slicker and brushed them all over his sac, then flicked my tongue out to its full length and tasted his hot nuts. Humming to myself, I placed my hands on his thighs to brace myself and ran my tongue all over his tremendously hairy balls, licking up the thin sheen of sweat covering them and kissing them gently. I let my spit run over my lips to his sac, then licked that up too. Between licks I kissed and sucked them gently, feeling his dick start to harden where it laid across my face. His grip on the back of my head tightened and he crushed himself against my lips. His smell was beginning to drive me crazy, and within seconds my clit had hardened to its full seven inch length, lifting the front of my skirt in a most unfemale fashion. But I barely noticed that, as he shifted and began slapping my lips with his dick, leaving smears of lip gloss all over it. I opened my mouth to receive it, but then he suddenly slapped me hard with his free hand. I froze in shock, which got me another slap as he rasped, "I didn't say you could taste my cock yet, bitch. Have you asked me for it?"

I shook my head, and he slapped me again, this time hard enough to sting. "Well?" he glared down at me as I frowned in feigned confusion.

"Please, may I taste your cock?" His response was another slap that made my eyes water.

I tried again, still pretending to not understand. "Please Daddy, will you stick your beautiful white cock in my sissy mouth?"

Again he slapped me, finally growling "Are you a slow learner, you silly bitch?"

I tried once more. "Please Daddy, I need you to fill up my whore mouth with your beautiful white cock. I'm a dirty black cock-hungry slut only useful for serving you as you see fit." I closed my eyes and opened my mouth again, sticking my tongue out. I then felt both his hands on the back of my head, gripping me tightly and holding me absolutely still while he guided his semi-hard cock into my cock. I heard him sigh as he began urinating down my throat, lightly at first and then at full force. I started moaning as he filled my stomach with his hot piss, delighted that he remembered my most private fetish, yet the one I craved most. I hardly ever got this kind of treatment, and it was completely blowing my mind. After half a minute his flow trickled off and I gently sucked out the last few spurts. I licked my lips clean as he pulled his dick free, then held it in front of my face as he stroked it gently. "Much better," he said. "Now you're going to eat my cock until I'm ready to fuck that tight black ass."

"Thank you Daddy, for letting this sissy slut serve you," I said, still keeping my eyes closed. I felt him push his fully hard dick between my lips, slowly forcing it deeper until I felt the head brush against the back of my throat. I tilted my head forward a bit and he continued to push it deeper, getting the next three inches inside me. Once my lips brushed the hair of his crotch, I knew he'd made me swallow his full eight inches of hardness. My whole body was covered in a thin layer of sweat and I was feeling feverish with horniness. I couldn't stop whimpering and moaning as Sam began fucking my face unmercifully, mashing my lips painfully against his crotch and barely giving me time to catch a breath. Every few minutes he'd pull out, smack his cock against my lips and across my cheeks, then jab it back in my throat and continue thrusting. For someone who had been vanilla all his life, Sam certainly had the right instincts.

"That's right you black bitch, eat this fucking cock," he rasped. "I know you've been needing to taste it ever since I first talked to you. Swallow all that pre-cum, slut. I'm going to fill you up with my cum and then make you beg for some more." He pulled out and I took another quick breath.

"Mmmmm yessss Daddy, that's exactly what your sissy bitch needs," I moaned, fogged up with lust. "I've been dreaming of sucking down all your cum. Please give it all to your slut, please please."

Sam shut me up again by plugging my throat with his lovely dick, fucking me faster and harder. "Fucking nasty whore, your hot mouth is going to make me cum--aaaahh aaaaah eat it you bitch. Eat my cum slut. Ooooh..." His voice broke up into a series of moans and shouts as his balls exploded, emptying a massive load of sperm into my mouth. Held in place, I swallowed the first five hard shots as they flooded over the back of my tongue, then held the last few spurts in my mouth. As he pulled out, I kept my mouth opened wide so he could see me proudly displaying his cum on my tongue. I held it there as he wiped his wet cock over my forehead and cheeks. After he finished, he ordered, "Go ahead and swallow it bitch." I did so, licking my lips clean and then thanking him for letting me suck his dick. Sam grunted in reply, then turned around.

I knew what I was expected to do then. I spread his ass open and kissed his hole deeply. He shivered and gasped at the feel of my lips on his dirtiest place. I knew already that his wife absolutely refused to rim him, but I had no such reservations. In fact I liked being made to lick a hot ass even more than sucking dick. He jerked as he felt my tongue touching the center of his asshole. The nasty bastard hadn't tried too hard to clean it beforehand, either, and his strong scent filled my nostrils. "That's right, worship my ass, you fucking slut," he muttered, leaning forward to give me better access. "That's exactly where you belong, with those big sexy lips sucking on my hairy asshole. Isn't that right?"

"Yes, Daddy," I agreed with my face wedged between his cheeks. "It's my place to serve you by worshiping your ass." He answered by holding my face in place, and I began sucking and kissing his hole harder, then working my tongue inside him.

"Ooooooh yessss slut, that's so good," he moaned. "You're doing so well, don't stop. Can't believe how much you're enjoying this. I'd never stick my tongue inside someone's shithole, but you love it don't you?" Shortly afterwards he began pumping his ass slowly up and down, trying to get my tongue in deeper. At that I reached down and began fingering my own ass, first with one finger and then adding a second. Suddenly he stopped and moved away, then shoved me flat on my back on the floor and sat directly on my lips. I started tongue-fucking his ass faster, feeling him open up completely as he relaxed. While I rimmed him, he reached down and began squeezing and twisting my nipples through my corset. I hissed in pain, but kept eating his hole as he squirmed and moaned softly. Fifteen minutes later he stood up and pulled me to my feet. My lips were smeared, so I quickly took a tissue and wiped them off, then reapplied my lip gloss while Sam quickly stripped completely. Once he finished, he stood in front of me with his cock fully hard and leaking again. I paused long enough to ask permission to suck his cock again, and he held it up for me to slide my lips over it. A few minutes of sucking had gotten it slick enough for his purposes and he bent me forward across the bed.

"I know you're really just a fag slut good only for taking cocks and not a real girl," Sam announced, pausing every few words to spank my ass. "You're just a bitch that craves being fucked and used by real men. Right?"

"Yes, Daddy," I answered, hissing as he continued to rain blows on my ass. "You're right. I'll never be a real girl and can only come close by dressing like a whore and opening my holes for hard dicks." And that was true enough.

His relentless spanking stopped, leaving my ass stinging while he ripped open a condom packet and covered up. Seconds later I felt him flip my skirt over my waist, followed by his dick powering into my pussy. Then I felt his hands on my hips, gripping me tightly as he drove his cock fully into my ass, giving me no time to adjust to his thickness. The pain shot through my entire body, coming in waves as he pulled out halfway, then began fucking me with hard even strokes. But within a couple of minutes the pain had tapered off to a faint throb and I began to lose myself in the pleasure of feeling his cock grinding back and forth in my ass. My own dick began to leak steadily at the stimulation, staining my skirt, and I started pushing backward in time with his thrusts while squeezing my muscles around his cock. "This thick ass feels so incredible, bitch," he said. "I should have been fucking you black slutbois years ago."

"Thank you Daddy," I gasped out. "Your dick feels so hot in my pussy. Mmmmm don't stop fucking me, you're doing me so good Daddy." Sam began fucking me even harder. Obviously my encouragement and absolute lack of resistance was really turning him on. In a few more minutes I could felt him start to lose his rhythm and I knew he'd be giving me another load of cum really soon.

Without warning he jerked me over on my back and stripped off the rubber, then straddled my chest with the swollen head of his cock a few inches above my lips. Sam grabbed my neck with one hand and rubbed his cock back and forth across my slightly parted lips. Not even five seconds later he stiffened, tightening his grip on my neck and shouting "Cumming on your face, bitch--uuuuuh!" The first two shots streaked across my forehead, with the following ones criss-crossing my nose and cheeks and coating my lips. "Yeah, take all that cum, slut! Aaaah yessss that looks so good, you sissy whore." Again he took his dick and and carefully rubbed it all over my face, spreading his cum in a thin layer on my skin. My ass was still tingling and twitching from his drilling and that along with the smell of his cum all over my face had left my clitty painfully hard. Sam saw my hands sliding down to tease my ass and stroke myself, and he immediately turned around, grinding my asshole on my tongue more while he watched me masturbate shamelessly. In two minutes I was shuddering through a thunderous nut of my own, draping my fingers with streams of cum. He rolled to my side as I laid there limply, while he gathered up my cum with his fingers and painted my lips with it as the sexual tension continued to drain away.

"Thank you for letting you please you with my pussy, Daddy," I whispered, licking my lips clean again.

"You're welcome, Ashley," Sam replied. "Hope I wasn't too rough...I guess I got a little out of control. I have never, never been so aroused before."

"No I didn't mind at all," I said, kissing him on the cheek. "I know that was what you needed." While he rested I got up and began cleaning myself, rinsing my face and wiping down below. By then Sam had recovered.

"Thank you, angel," he said, embracing me and giving me a kiss. "That was everything I'd been wanting. That was just unbelievable."

I smiled brightly. "I enjoyed myself too, Sam. I'll come back whenever you need me." He nodded and reached for his pants, then pressed a handful of twenties into my hand.

"Oh I definitely will need you again, angel. I'm just sorry I didn't find you sooner. You're one of the sexiest bitches I've ever seen, I can't wait to have you again."

We talked for a bit longer as he asked me when I'd started dressing and a few other questions about my services, which I answered. A little while later I began gathering my gear to go on home. "So I'm gone, Sam. I look forward to seeing you again." He walked me to the door, and I made my way home quite satisfied with my $400 tip.

Once home, I had a few more emails waiting for me--the most urgent one from Sam, asking if I could come back and see him again the next night. Of course I answered him immediately, assuring him that I'd be there at the same time as before....

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