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"Still a virgin, then?" my friend Craig teased me one afternoon when we were hanging out at my apartment.
"Um..." I paused.
Was I? I honestly didn't know at this point. I certainly was far less sexually inexperienced than I had been a couple of weeks earlier, in the days before Destiny, the Amazonian black babe, had taken my own erotic destiny in her hands. But had I actually lost my virginity? What did that even mean anyway? Yes, I had still not managed to get my dick inside Destiny's, or any other woman's, pussy. So, I guess maybe I was still a virgin.
"So, you are then, loser?" Craig laughed at the length of my non-communicative thought.
"I guess... Does anal count?" I asked, carefully not mentioning whose virgin ass had been on the receiving end.
Had I lost my virginity by allowing Destiny to shaft me anally? It sure felt like giving something of myself up when my ass got plowed for the first time. But does anal virginity count the same? And does having a toy like a strapon dildo inside you count the same as real penetrative sex with a human organ? After all, you can't pop your cherry with a vibrator. Can you?
"No," Craig said with a confidence that was not matched by any actual experience of his own, "To lose it, you've got to get your dick wet. Got to screw that pussy, not anal."
"You did anal with that black babe?" asked my other friend Matt as he entered the room with something in his hand, his tone was clearly impressed, "Does she have a friend she'd introduce me to?"
I laughed. I wondered if he would want to be in my place if he knew the full truth. Or maybe he would. I didn't know. Perhaps Matt would be as easily turned as I was to being on the receiving end, if it came from the right busty black hottie.
"Are these her panties?" he went on, revealing what was in his hand: the pair of lacy white open-back panties I had worn while Destiny pounded my tight butthole.
"Hey, where did you get those?" I said, trying and failing to snatch them back.
"They were on top of your laundry basket."
"Are you keeping souvenirs?" Craig jumped in, managing to do what I didn't and grab them from Matt.
"What are you doing looking in my laundry basket?" I demanded, in a question that went unanswered.
"Mmm, smell that black girl pussy," said Craig, holding the panties to his face and inhaling, "I bet she was wet wearing these."
I didn't think I could bring myself to admit that he was inhaling my own stale cum, the juices I had ejaculated from my own tiny dick while wearing those panties. I mean, I had grown to love the taste and smell of my own cum, but I couldn't exactly expect my friends to feel the same. And I had no idea how they would react to me wearing panties. Either the ones in Craig's hands or the pink satin thong I had on beneath my jeans at that very moment, the one that felt so good against my little dick that I had to try and focus on something else to stop it getting hard.
I hadn't realized that last time with Destiny, when she had told me I belonged in panties, how much I would get into it. After I had got home then, still wearing the cum soaked assless underwear that had been a feature of my first anal pegging, I had cast them aside, assuming that was the end of it. But I hadn't been able to stop thinking about how good and sexy it felt wearing them. Men's underwear was so bland and functional. Women got to wear beautiful things that flattered them. My pert round butt had looked good dressed up by the criss-crossed pattern of the open-backed panties. My little dicklet had enjoyed being tucked into sensual lace. There was no reason for me to not keep enjoying that feeling. If I wore panties under my clothes, nobody would know but me. It would be my sexy secret. Before I knew it, I had found myself browsing lingerie stores online. And, once the world of sexy panties was opened up to me, I couldn't resist. I ordered a whole heap of them and had been wearing panties non-stop for days.
My friends had been completely unsuspecting that I wore a pretty pink thong, while they discussed details of my masculine exploits with a gorgeous nubian beauty. I was still wearing the same thong later that evening when I arrived once more at Destiny's apartment. And it was not so easy to keep it hidden from her.
"Wow, you really are a kinky little panty boy," she laughed, having made me strip down to my underwear in her bedroom, "I can't believe you went out and bought your own!"
I blushed awkwardly, standing there naked except for my pink satin thong, while a gorgeous, powerful black woman looked me up and down with amusement. The thong was baby pink with black lace embroidered trim around the waistband. Inside, pressed against the soft sensual fabric, my little dick was semi hard and, if anything, the mockery of a beautiful woman was making it stiffer. Destiny was dressed in nothing but a black satin chemise, with lace detail around her dark cleavage. The shape of her large nipples showed through the thin fabric, exciting me even more. The lace trimmed hem of her chemise brushed just above her knee and I wondered if I could see the outline of her dangling, swinging strapon. I had no idea how tonight was going to go. I still longed to lose my virginity in a way that involved my dick in wet pussy, but I couldn't deny yearning to feel something hard invading my butt too.
"You know, L.. Logan, you have pretty cute taste in panties. That thong really does make your cute twinky ass look good," she smirked, slapping her dark hand over my pale ass cheek, "I guess that will make the next part easier."
"Next part?" I asked, curiously.
"Well, we know you love wearing panties and taking it like a little bitch," Destiny went on, still with that triumphant smirk that showed who was the boss here, "It's about time you fully looked the part."
She opened the closet and took out some shopping bags, emptying their contents onto the bed. There was lingerie, stockings, makeup, heels, wigs, all kinds of pretty feminine things. Things that both excited and scared me a little.
"You want me to dress in all that?" I said, slightly aghast.
"Why not?" she replied, "You obviously enjoy wearing the panties. Why not a bra to match? Where does it stop? It's not unusual for a femboy twink like you to get all dolled up like a girl."
"But I'm not a girl or a femboy or a sissy or whatever," I said indignantly, "I'm a guy. A normal straight guy -"
"Oh, definitely," she reassured me, "That's what I'm trying to tell you. Normal straight guys like you dress up like this all the time. If a cute girl asks them to, that is. You wanted a babe who's way out of your league to take control of your erotic destiny, didn't you? Well, girls like me are only interested in guys like you the more feminine they are. You can't compete with real men in any of the ways that count, not with that body and certainly not with that pathetic, puny, panty wearing clitty cock. But with that skinny body, pretty face, and fine, fuckable ass, there's another way that you can please a woman: by fully giving into your femininity. Embrace it and show off your body the best you possibly can."
"By dressing as a girl?" I was not convinced yet, but Destiny could see I was wavering, "I don't know."
"Well, put it this way, you can either dress like a girl and get fucked like one, taking this big black dick," she said, grabbing her crotch to reveal the clear outline of her realistic thick strapon against the feminine black satin of her chemise, "Or you can leave now, never see me again and carry on the life of a tiny dicked virgin constantly rejected in favor of manlier men. It's your choice."
Put like that, I guess I didn't have a choice. There was no way I was going to give up being with Destiny, whatever that took, to go back to my own life. I had seen and enjoyed too much of being in the power of a beautiful busty black babe to not continue down the path she had pushed me onto.
"Fine," I sighed, "Let's play dress up."
"OK," Destiny grinned triumphantly, "Well, you've already picked yourself such a cute thong that it would be a real shame not to keep you in it. We're just going to have to find some other things to match."
To go with the pink satin panties with black lace trim, Destiny picked out a black bustier with pink lace detailing around the bust. As she helped me into it, I realized that it was a perfect fit. Destiny must have bought all of this girly stuff specifically for me to wear, nobody else. She must have had absolutely no doubts that I would agree to this. She had always seen me for who I really was.
There was no denying that it felt good in the black bustier. I enjoyed the feel of the soft sensual fabric against my tender nipples, but I also just liked looking down at my body and seeing something pretty. It made me feel good physically and psychologically. And that was just the beginning.
Next, Destiny fastened me into a black garter belt, the lace trimmed garters dangling over my pink panties, and handed me a pair of black sheer stockings. I rolled the stockings up my smooth, hairless, feminine calves and up to my thighs. The feeling was deeply sensual and truly thrilling. For a minute I was just completely lost in the moment. In my mind I was no longer here in Destiny's apartment, being commanded by a hot black babe to doll myself up. I saw myself as a beautiful young woman enjoying the sensual feeling of her hot body, of dressing herself in her sexiest clothing. It excited and aroused me to picture myself that way, whether Destiny was in the picture or not.
My reverie only lasted as long as it took to clip my stockings to my garters and for Destiny to hand me a pair of black strappy shoes with platform heels. I stood up and tottered awkwardly in the shoes, which nevertheless were a perfect fit for my feet. I practised a little taking a few steps - heel, toe, heel, toe, hips swaying - until I could at least move around the room. The feeling of my lace stocking tops rubbing together as I did so was immensely pleasurable. As I sat back on the bed and crossed my legs in a feminine fashion, I could tell how the platform heels accentuated the womanly shapeliness of my calves.
Meanwhile, as I sat there, Destiny continued making me over. She sat a blonde wig on my head, styled in shining shoulder-length waves and then proceeded to paint my face in makeup, blush and mascara. Finally, she took my head in her hands, just as she had when pushing that realistic black strapon down my throat, and extended another phallic rod to my mouth. This time, however, it was a stick of cherry red lipstick that she extended toward me, painting my mouth a shade that even I knew implied the wearer was horny and down to fuck.
And then she stood me up and walked me over to the bedroom's floor length mirror and I saw my feminized self properly for the first time.
I gasped as I looked myself up and down. I had never thought myself attractive, always been insecure about my looks. But the vision staring back at me from the mirror from beneath a tumble of blonde hair looked stunning. Honestly, I looked like a girl hot enough that a guy like me would never dream of approaching her. I was out of my league! Standing next to Destiny, we looked like two knock-out babes, one tall, black and curvy, one slender, pretty and pale, but both as desirable as each other.
"Well, what do you think?" she said, "How do you feel?"
"I'm pretty," I said in awe of myself.
"Not just pretty," said Destiny, "You look hot. I knew I saw that sexy slut potential the moment I saw that pretty boy ass across the bar."
I blushed, not used to being so admired for my looks.
"You're definitely not a L.. Logan any more," she went on, "I'm going to call you... Lulu!"
And that was it. For as long as I wanted to be with Destiny, I was going to have to be 'Lulu'.
"And now you've let yourself get dolled up like a pretty little bitch, Lulu. It's time for your reward."
She lifted her black chemise around her waist to reveal the treat that we both knew was hidden there: a big, thick, realistic, chocolate skin-toned strapon dildo. And we both knew where it was going to go, a thought that made my own tiny panty-wearing dick spring to attention.
"OK, Lulu, time to get on your knees and show me you can swallow black dick just as good as the slutty white bitch you look like," Destiny commanded.
Unquestioning, I did just as she asked. I dropped to my knees and wrapped my slender white fingers around that swinging, veiny black shaft. I pulled the shining dark head to my painted scarlet lips and kissed it, leaving an imprint of red lipstick on the dark plastic of the dildo. Soon I was licking up and down that shaft like it was a chocolate lollipop, getting it nice and wet with my spit. And then my lips opened and it was inside my mouth, sliding deeper into me, then back.
I glanced across the room at the reflection in the floor-length mirror. It was almost impossible not to see a busty big dicked black shemale and a pretty, dainty blonde slut on her knees worshipping that huge dark meat. It was an image that I enjoyed, not just as a spectator but as a participant too. Destiny obviously liked it as well.
"There's a good little slut," she said as she started taking more control, fucking my face with her black strapon, "I always expected there was a dirty whore for big cock just waiting to get out of that twinky 'straight' boy body."
In my pink satin thong, my pale little dick was as stiff as it ever got as the tall, curvy ebony babe standing over me fucked my face with her realistic black strapon. But there was more to come. She pushed me back from my strapon cock worship and got me to my feet. The slick, wet, black hardness swayed enticingly between her legs. Grabbing me by the shoulders she span me round to face away from her.
"Bend over, bitch," she commanded, "I'm gonna nail that slutty sissy ass harder than you've ever had before."
I bent over the bed, my face against the mattress and pert ass, covered by the tiny strip of pink fabric and black garters, stuck in the air. Destiny positioned herself behind me, looking powerful and intimidating with the big black strapon between her thick thighs. She pushed my sensual stockinged legs wider open and then slid the gusset of my pink satin thong over to reveal my exposed asshole. She licked her long dark fingers and, in a moment, one was plunged deep into my hole, making me gasp and moan like the dolled up blonde slut I appeared to be.
It wasn't long of finger banging my stretched butthole with first one, then two fingers before Destiny decided to really go for it. She took her fingers out, pulled my butt cheeks open and shoved the thick black head of her strapon inside. Just like last time, the pain of being stretched out and impaled was a lot to take, but it was soon suppressed by the ecstasy of being filled from behind.
Destiny pushed deeper and deeper, further into me than ever before, until I was impaled on the full length of that incredible thick black cock. And then she pulled out, before slamming back into me. With her hands on my hips, dark fingers wrapped around where my pale skin met the black lace of my bustier, she levered herself so that each thrust inside me rocked my whole body. I quivered and shook as the black goddess behind me took complete control of my ass and my whole feminized body, plowing my ass like she was the real man and me the whorish girl.
I looked over my shoulder and saw the incredible power of a strong black body, her tits bouncing up and down in the black satin chemise as she plunged her huge black dick into my pert round butt, a look of determined power on her face. Past Destiny's shoulder, I could still see my skinny white body in the mirror, looking dishevelled but sexy in my black and pink bustier and sheer stockings, the curve of my feminine butt being penetrated by a masculine black rod. It was like watching a hot porno while also being the girl in one. I couldn't hold back much longer, I knew my climax was near.
"Oh God!" I moaned in a high-pitched, effeminate tone, as I pushed my ass back to meet her thrusts "That big black dick in my slutty butt is gonna make me cum."
"Rub your little clitty cock, slut," she commanded, "Rub that clit while I pound that boy pussy."
I did just as she said and reached between my legs, where my pink satin panties were already soaked with my clear pre-cum. As Destiny continued to take me from behind, my fingers slipped into the waistband of my panties and started to stroke my little but rock-hard dick. In a moment, that touch had done its job and my tiny cock was shooting streams of cum into my panties and all over my hand, more coming out with each deep thrust of that ebony strapon into my ass.
Finally, Destiny pulled out of my ass and left me to collapse onto the bed, still wearing a bustier, garter belt and stockings, my red lipstick smeared across my face and the blonde waves of my wig a little less neat than before. I took my sticky hand from my soaking panties and, without prompting from my curvy black mistress, licked every single finger clean of my slimy, salty juices, taking great pleasure in each mouthful.
Still standing, veiny black strapon dick swinging beneath the lacy hem of her chemise, Destiny looked down on me and smiled.
"You do make a very good little white slut, Lulu," she said, "I think you're finally ready."
"Ready for what?" I asked, but the answer for that would have to wait...
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