From Junior Cuck to Sissy Pt. 08

Disclaimer: All characters in this story are 18+. They are all ending high school and starting college.

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It had been four whole days since Daniel's last visit, and I had to admit I felt a bit anxious. Lana had me practicing a lot with her dildo, either under her controlling hands, or under my own, as she insisted I had to start "masturbating" this way, instead of touching my "dicklet" as she was tenderly calling it lately.

Of course, the practice included much more than the dildo, like dressing my sister's clothes all the time (well, the little femme clothes she had, anyway), combing my hair, applying makeup, and painting my fingernails and toenails.

She even started me on skincare, which I didn't even know existed, and my fully shaved skin was feeling softer to the touch, which I noticed as I was touching my body a lot! She encouraged me to look at myself posing in front of the mirror, slowly touching myself, pouting my lips, and smoothly moving my hips. Fully made up and wearing lingerie only, I felt aroused and sexy.

And then it finally happened. I almost fainted when she lightly informed me that Daniel AND his friend were coming in minutes! Of course, she did tell me just after a dressing session, so I was all dolled up already. Once again, she was careful not to allow too much time to panic.

I was terrified, but she took care of the final touches on my lipstick and hair, trying to distract me until the intercom rang. She answered and waited for them at the apartment door.

Here I was, trembling in fear before having my first sex date with a Man!

I heard them approaching, Daniel entered as Lana clutched his neck and kissed him, while his friend waited at the doorstep. Filling the doorstep. A huge, BLACK Man. I gulped down and felt goosebumps as he set his dark eyes on me across the room. I couldn't hold his gaze and looked down, blushing like crazy, embarrassed, thinking he might just laugh at my silly dress-up. I considered running and hiding in my room when I heard Daniel talking to Lana: "Hey babe! I missed this bubbly ass of yours... Oh, this is my friend Kordell. I guess you can introduce him to your faggot boyfriend" he snickered, receiving the usual punch in his arm from her, while she invited Kordell to come in.

He entered the room, nodding a greeting to Lana, whom I noticed ogling him with interest. That immense bulge of muscle walked towards me and stretched his hand, greeting me, "Hi there. My name is Kordell. Pleased to meet you", he said with a low, manly voice, but with a sweet tone. I looked at his huge hand and nervously stretched mine, which seemed tiny in comparison. I was about to shake it, but he grabbed my fingers, swiftly lifted them to his lips, and kissed them.

I must have blushed intensely at the feeling of his tough skin and the sweet kiss on my hand.

"You are so beautiful... What's your name?" He asked me. And my heart stopped there. This immense, handsome black man considered ME beautiful... Really? I could not believe what was happening, and thought I was about to wake up and realize this was all a weird dream.

He smiled and asked my name again, my hand still on his. "I'm... My name is Sam", I stuttered.

Then Lana, always on top of the situation, invited both men to sit down and asked if they wanted a drink. Daniel plunged onto the sofa and accepted a glass of whisky, but Kordell asked me what I preferred, and as I said water was fine, he told Lana that a couple of glasses of water would be ok. Then he asked me if I wanted to sit on the sofa, waited for me to sit down, and only then sat next to me. He was a Gentleman! I had never expected a Man to behave like that towards me! It felt strangely good, though.

While Lana was preparing drinks in the kitchen, he looked at me and started making small talk, while he was obviously checking me out, making me feel very shy but appreciated. He asked if it was my apartment, and told me he liked it, and then he told me he liked my outfit, too. His voice was soothing, and he was very close, towering over me, but so gentle that I was less afraid than expected.

Once Lana got the glasses, she sat on Daniel's lap and started kissing him, while he immediately started grabbing her tits and ass. They started making out in front of us, and Kordell noticed I was a bit uncomfortable, so he kept lightly talking to me, asking me about how I met Lana, and then about our studies.

Of course things progressed quickly and the next time we looked at them, Lana was already on her knees and sucking Daniel's cock.

Kordell noticed my anxiety again, and this time he placed one of his mighty hands on my knee, asking me if I had done something like this with a man. I looked at him with fear, but his dark eyes looked deep into mine, calmly. I mumbled no, and then I corrected myself, "Well... only Daniel. Last time he was here with Lana..." and I surely reddened in shame admitting it, but I felt I couldn't lie to him.

He moved a lock of hair out of my face, passed it over my ear, and whispered, "Sorry about that... I know he is pretty nasty sometimes," and smiled. I smiled back and relaxed a bit. Then he passed his arm over the sofa, behind my shoulders, and asked me if it was ok to kiss me.

I could not utter a word, so I just nodded, and felt him getting close until his beefy lips touched mine, and he kissed me softly while his arm closed gently around me. I let myself be kissed by a man, and it felt surprisingly right. He was careful and sweet, and I opened my lips and let him kiss me harder, feeling his tongue invading mine.

I lost track of time, but I know we started caressing each other. His hands on my skin felt incredibly different from Lana's, but strangely enough, all my fears and concerns were gone, and I surrendered to his touch. And I touched him and, OH MY! His muscles felt like iron, and for the first time, I fully understood I was totally drawn to men... Maybe not every man, but this amazing man...

Soon, my hands had crept under his T-shirt, and I was relishing the feeling of his powerful pecs, down to his clearly defined six pack. I got to the top of his trousers, and I couldn't help my curiosity and kept going down until I felt the hardness of the bulge between his legs.

It felt enormous, and as his hand slipped under my hot pants and grabbed my buttock, my fingers followed his lead and slipped under his trousers and underwear. HUGE! When I felt its package with my fingers, I realized it was bigger than Daniel's! It scared me a bit, but also sparked my curiosity, and as he noticed my attempts, he raised his butt and helped me lower his pants. The thing jumped up, straight and hard. I broke our kiss to look at it, amazed.

"Do you like it?" he asked in my ear. I couldn't speak, but my hand instinctively closed over his cock. Tried to close, actually.

My fingers were not long enough to wrap the whole thing around. I tried squeezing a little, near the top, and they barely touched, but the sensation of its soft, spongy skin bulging around its hard core was incredible. My dicklet was nothing like that, and in my mind I could see even more clearly why Lana called it that, and could never consider me a Man. Kordell instead was The Man. I felt totally small and girly beside him, and I felt the same strong attraction that Lana described, so I dropped to my knees and started sucking his cock head.

On my knees, feeling his hand gently caressing the back of my head while I started sucking his cock, I felt completely submissive and happy. I remember hearing a gasp from where Lana was, and looking at her as I sucked, watching her make gestures to me while she jerked Daniel, in a mixture of envy and amazement about the size of my Man.

A mix of guilt and victory inflamed my heart and I started making an effort to sucking more cock, but it was too big, so I started licking him up and down instead, studying the veins and muscles of his cock like charting a map. It was incredible, so yummy and hard and jerkable... And he kept gently caressing my head without pushing, he just started kindly rocking his hips up and down, reacting to my passionate sucking.

As I relaxed and spit covered more of his pole, I could get more and more in my mouth, and I thanked all the practice with the dildo, which seemed so big before, almost like Daniel's cock, but was nothing compared with Kordell.

I was delirious sucking this magnificent cock, by then already able to guzzle almost a third of it, helped by his hand which got heavier and held me in place as he acknowledged that I was into it, as well as his pumping hips now pushing inside my greedy mouth. I choked many times on his cock, but I was relentless, and I recalled Lana telling me how much they liked that. My dicklet was very stiff inside my tight hot pants, but I only wanted to have more of his meat inside my mouth.

When he pulled my head off his cock I looked up at him, with begging eyes, but as he looked at me I got to listen to the moans nearby, and I saw Daniel standing behind Lana, fucking her ass as she was all all four over the couch.

I looked again at Kordell, hesitant, my hands still grabbing his cock, and he asked me: "Do you want to go to your bed, baby?". The thing pulsing in my small hand was pretty scary when I considered how difficult it was to suck it, and how tight my asshole seemed to be, but I was so horny and submitted to this beautiful Man that I nodded, stood up, took his big hand and brought it to my room.

He entered, tossed the remaining of his clothes around, displaying his chiseled body, which seemed a mix of good genes and lots of exercise, and then he sat on the bed and brought me closer, undressing me while kissing my body. Shaking in ecstasy, I let him do it, and helped with my hot pants, so tight that they carried down my panties at the same time, embarrassingly displaying my meager erection.

But as mortified as I was about him seeing that, he looked at it, caught it with two fingers that were bigger than my pathetic penis, and softly squeezing it told me it was "beautiful"! I glowed in shame and arousal, barely able to say: "Your cock is beautiful... Mine is... just..."

But he shushed, kissed my lips, and told me, "You are a beautiful whiteboi. Your clit is perfect, and you won't need it much, baby. Tell me: why is my cock much bigger than your clit?" I hesitated, my mind far from fully functional. I tried "Because you are a Real Man? Can I suck you again, please?" I begged, feverishly jerking this hot and hard pole that was my only focus right then.

"You are a smart boi", he smiled, and he pushed himself back over the bed, pulling my hand so I crawled over him until my face was close enough. He pushed my neck over his cock, which I devoured. By now he knew how much I could take, and far from panicking when I choked on his cock, I loved it. So he proceeded to fuck my mouth, pumping with his hips while his hand pushed my head down. It bumped on my throat and suffocated me, but it felt incredible, and he always got the timing right to release a bit and let me breathe, even as my eyes watered and I coughed several streams of spit all around.

While I kept sucking, he stretched an arm, grabbed my groin and lifted me as I was light as a pillow, rotating me around his cock until he dropped me on my knees straddling his chest, and then proceeded to grab my buttocks. I felt his meaty lips kissing my ass, and then his hot wet tongue started licking my asshole, strongly. I emitted a muffled sigh around his cock and felt frenzied by the sensation. He kept my mouth busy while his tongue pushed inside my hole, which involuntarily resisted for a moment, until it yielded and let him inside.

Quickly enough, I felt one of his fat fingers slipping in, too, prodding my internals and provoking more muffled cries from me. And when he added a second finger, it felt bigger than the dildo already. He kept moving them around and studying the spots where I vibrated the most, amused. Then he saw the bottle of lube on the nightstand beside the standing dildo, took it and poured some on my hole, spreading it with his fingers.

"Is this your dildo, whiteboi? Do you like feeling your pussy filled by cock?" he asked me, and I stopped sucking him to say "Yes" while licking his cock up and down.

"It seems you really like sucking my cock. Do you want something else, little boi?" He teased me. And I begged "Yes, please... Fuck me...".

He smiled with his lovely lips and pearly white teeth, and flipped me up once again, moving out and placing me back on my hands and knees, kneeling behind me. I turned back and saw him pouring lube on his cock and spreading it over its full length. "Please... be gentle... I never...", I pleaded, but he shushed me again and told me it would hurt a bit first, but I had to endure it.

Then I felt the humongous head of his cock pushing against my finger-stretched asshole, which didn't seem dilated enough. But he grabbed my hips and started bumping against my ring, slowly massaging it out, helped by the lube. At some point the first ring opened and he was pushing the second one, which resisted a bit more, and then, suddenly, his cock head was inside. Then he stopped the pumps and held there, slowly pushing in, enlarging my sphincter and making me sob. But I needed him, and he just kept going in, very slowly.

I felt fully stuffed, and then he started to retract a bit, then pushed back in, maybe half an inch. Two or three times, and my ass was burning, but something in me had cracked and I wanted more. He pushed deeper, then retracted, in and out, maybe a whole inch this time.

I noticed my erection was gone, and my dicklet was not just limp, but shrunken and curled like surrendering to the real manhood in my ass. Three or four times, and he got even deeper! My sphincter muscles yielded, embracing the girth of his cock. He pumped a bit faster several times, then got deeper yet! I started feeling my whole body trembling under his power, and my hurting groans turned into lusting moans.

Then he started pumping and moving my hips at the same time, like he was jerking off... with my ass! I felt like a toy... but it was so sexy! He kept pushing deeper, and I could not believe how full I felt. I knew his cock was huge, but inside me it felt gigantic, and so intense! The little fantasies I have had since watching Daniel fucking Lana in her ass were nothing compared with this.

It was not only the stuffing sensation inside me, but the brute force of a Real Man overpowering me, and the embarrassing realization of my absolute inferiority, mixed with some kind of pride about giving him pleasure. After my catastrophic failure as Lana's lover (the only girl whom I got close to!) I was finally having Real Sex.

And we had a lot of sex that night. He kept fucking me doggy style for a long time, and once I got the hang of it, I started to back up on my own, enjoying his enormous dick, while my shriveled "clit" (as he preferred to call it), stood limp and started leaking thin, transparent strings of precum.

He was unrelenting, and I could not match his stamina, and at some point my arms weakened and I dropped to my shoulders, drooling over the sheets while he kept pumping my asshole.

A few minutes later, my legs could not keep me anymore, and he pushed me flat on my stomach, closed my legs, and started drilling me against the sheets, and I couldn't believe how big and hard it felt inside me! I could also feel his body against mine, even as he was supporting himself in his powerful arms, or else I had been crushed. The sensation of his belly bouncing on my buttocks was exquisite, and I felt totally dominated. He could have eaten me, like a lion feasting on a deer. He was my predator, and I was his happy prey.

He was sweating like a wild animal, too, and I was feeling the drops on my back, and the strong smell of his manly sweat only excited me more. From time to time his cock slipped out, and the emptiness sensation was quickly overcome by his reentrance, which felt easier and more pleasurable each time.

One of these times, instead of stuffing me again, he opened my buttocks and admired my gaped hole, "Damn, boi. This pussy is sweet and tight! I can tap that all night long!", but he plopped to the side, and grabbing my neck, moved my head back to his cock. He wasn't as gentle anymore, but I realized I liked to be manhandled like that, and I started sucking his delicious cock in the blink of an eye.

It tasted weird, between the lube and my ass, but it wasn't dirty, thanks to Lana's teachings. I milked him eagerly, desperate to taste his cum, and of course he understood my craving, and let me suck him hard while jerking his pole with both hands.

Quite soon I felt him tensing up and breathing harder, raising his hips rhythmically to fuck my mouth harder. Seconds later, he grabbed my head, keeping it still, and unloaded against my palate and tongue. It was so incredibly warm and silky, and... so copious! I wanted to taste it, but had to start swallowing some to avoid overflowing, and the whole thing was so exciting. I felt my slightly engorged clit leaking harder. It was almost like an orgasm, but I was not ejaculating, but oozing a thicker string of precum, which felt pathetic compared with the globs of semen he was still shooting into my mouth.

I kept swallowing and sucking and tasting his delicious cum, while I kept jerking his hard cock into my mouth. When I had swallowed his full load and was starting to worry about the night coming to an end, he pulled my arms and made me kneel astride his hips, telling me to sit on his cock.

Amazed, realizing he didn't need a break, I grabbed his cock, which was still as hard as before, and placed his head against my lubed hole, which was still so hungry! And once it was properly placed, I let myself down around it, stuffing myself with that strong masculine organ, feeling how my girly thing deflated and receded instead. His hands grabbed my waist and bounced me, teaching me how to ride him.

And I rode him, impaling myself and feeling incredibly tiny and fragile, but also appreciated as he kept pumping and enjoying my ass. My hands rested on his solid and ample chest, so masculine and powerful.

I rode him like this for a while, then he kept turning me around. He fucked me missionary, doggy style, making me kneel to suck him again. He fucked me against the wall, and at some point I found myself again on my belly over the bed, with him lying on my back, pumping my asshole to the hilt, very hard.

While I was drooling and biting the pillow, he shook harder, howled and I felt him bigger than ever in my ass, and warm, and slippery, and I felt my curled and limp clit gushing, this time a true orgasm provoked by Kordell's. Mine blew just a couple tiny shots of cum, but I had a long and shocking climax unleashed by his immense discharge into my rectum. Something I had never imagined.

After several messy pumps I noticed his dick finally softening a bit. Then his heavy body rotated away and to my side, and I just managed to move closer, kissing his dark and sweaty muscles while we dozed off.