Big U Pride Ch. 05: Pledge Week

With every thrust, my doubts were pushed out of my mind. My fears were pushed out of me. I was made new and complete by this. Each thrust was life-altering.

"Oh please, oh oh please."

That's when he spoke to me, the first words he had said since he took me.

"You're a sissy now, Britney."

He was right, so right. I moaned as I heard it, and said back to him. "Take my virginity, Sir. It's yours."

He instructed me then, "Call me Daddy."

So I repeated myself, "Take me Daddy, make me yours."

He thrust harder at that. I squealed as that, wanting him so badly. He pumped into me, faster and faster.

"Oh fuck, oh fuck, Daddy yes, Yes!" I screamed. The neighbors must have heard me then. I didn't care, I wanted the whole world to know that I was a sissy and I was getting fucked by an Alpha and I was loving every second of it.

"I'm your sissy, Daddy! I'm your sissy!" I shouted in joy. "I love your big cock, ohmygod I love it so muuuuuuch!" My last word dragging out as he pumped harder.

I wrapped my legs around his back as he pounded my hole. I felt like I was being pounded to heaven and back. I didn't think this could feel better.

That is, until I felt him push all the way into me, his balls resting against my ass. I had done it, I had taken his entire length into me. I was his sissy fuck-queen.

I stared into his eyes, wanting my words to be heard deep within his dominant brain.

"Breed me, Daddy. Please please please fill me up and breed me. PLEASE!" I begged of him. Truly, honestly, just begging for him to fuck me good. He did just that, his hips slamming into mine, the slapping noises of our skin reverberating throughout the room with my moans.

He pounded me so hard that my body was pushed up the bed with each thrust, with him coming along with me. We ended up with my head on the pillows while he grabbed the headboard with one hand and my hips with the other and fucked away.

I truly understood in that moment, what it was like to give up everything I considered normal or correct or standard. All those conventions I had adhered to all my life, not tossed into the wind. I said goodbye to my old life, and took up on the ship to sissydom, sailing on the winds of pleasure on the seas of emotional bliss.

He slowed his pumping and looked at me.

"You're crying, Britney." He said.

He was right, I was. Tears of happiness streaming down my face.

"I'm just so happy, Mr. Steele. I'm just so fucking happy."

"Of course you are, doll." He said, stroking my head. "This is what you were born to do."

I tightened the pull of my legs around his back, bringing him closer to me. Still tearing up, I whispered into his ear.

"Please, please fuck me, fuck the Brian out of me, and Britney into me." I asked of him.

He didn't even respond, instead he slammed his fists into the bed and slammed his hips against me, his cock burying into me. My eyes rolled into the back of my head and my eyelids. Somehow my body translated pain into pleasure, and pleasure into the ultimate high. I just let loose, screaming and moaning with abandon as he fucked me good. I was his, I was his plaything, his fucktoy. Nothing could come close to matching this feeling. Or so I thought.

"I knew you'd love it." He said to me.

I moaned back,"I really do, oh so muuuuch".

He picked up his pace, furiously fucking my boipussy. I was barely screaming words anymore, my shouts of "oh yes Daddy1" turning into "ohfuckyesfuckohmygodIlovethisdon'teverstop", a long unending stream of praises for him and pleading for him to own me more. I just surrendered to him completely, letting him use my body for his pleasure. That gave me pleasure I couldn't have even dreamed of.

I don't remember what set me off. It may have been when I saw the strained look on his face as he concentrated on fucking me good. It may have been when I heard him roar in pleasure. Or it may have been when he shouted out, "Britney you're going to make me cum!"

Actually, I knew exactly when it was. It was the last one. That set me off in a way that nothing else could.

I had jacked off thousands of time in my life, familiar with the feeling of the male orgasm. The build up, then height then the release. But what I felt then, that was completely different. It was like a hundred small orgasms made their way from my gut down to my sissyclit, bursting one my one, little sparks of joy set off like grenades inside me. They built up, stacking one on top of each other, the power building up inside me. My sissyclit was just pouring out cummies at that point, a steady stream of my juices pouring down my little sac.

Was this how girls cum? Was this what I would have missed had I not become a sissy? How could someone go through life without knowing this feeling? How could someone go any day without craving this every fucking second?

But just when I thought that was the height of pleasure, Mr. Steele slammed into me and roared, his cock swelling inside me and starting to shoot cum inside me.

That's when it really happened. The gratification, the life-affirming, the purpose-making moment of feeling a man orgasm inside my boipussy, all of it matching the culmination of my feminine pleasure.

My entire nervous system was hijacked by the strongest explosion of pure pleasure that rocked my body and mind and soul, waves of pleasure bursting out from my quivering boipussy and taking hold of my entire body as I moaned in guttural release. His cum drenched my insides as I went into spasms, my body shaking in rapture.

"OOOOOOOOHHH DAAAADDDDDYYYYY!!!" Was all I could manage to say. I wasn't even conscious of what I was doing, just victim to sissy glee. It was like someone had injected pure pleasure into my veins, like it was a drug. And I was hooked. I was a cock-crazed nymphomanic, moaning and screaming to my heart's content as I floated into sissy heaven.

I slowly came down from that high, my shakes becoming smaller as I did.

I was still crying, but now I was laughing too. Crying and laughing and smiling.

Mr. Steele looked down at me with a knowing look on my face.

"Do you understand now?" He said, knowing that I would get what he meant.

I nodded, wiping the tears from my eyes as I did. "I do...I do...I am a sissy. I am a sissy. I am a sissy." I repeated it over and over, knowing that I was changed from the inside-out. There was no going back now, even if I wanted to. And I sure as hell never wanted to go back. All I wanted was to feel what I just felt again. All I wanted to do was worship men like Mr. Steele to show them that I could be the perfect sissy for them, to have them take me like Mr. Steele had just down.

Then I hugged him close and said over and over, "Thank you, thank you, thank you."

He laughed and kissed my neck. "It was my honor, Britney. To be your first. To give you your first Sissygasm."

So that's what that was, a 'sissygasm'. Well, I wanted to feel it again, and again, and again. I would chase that feeling every opportunity I had.

We stayed like that, necking and kissing, as I felt his cock soften inside of me but never come out. After a while we fell asleep.

* * * * *

It was still dark in the room when I woke up. I was still naked, my body on its side, draped over Mr. Steele's naked form. My body felt so sore, like after the hardest workout anyone could ever have.

My hand was on his muscular chest, rising up and down as his chest heaved with his slumberous breaths. This was an immensely erotic feeling, lying naked with this man here.

But I wanted something in that moment. I wanted to feel sissified again. It was like I had had my first hit of a drug and I would do anything to get high again. I was addicted to that feeling, the joy of having a man inside me.

My hand slithered down and grabbed Mr. Steele's cock. Even soft, it was heavy in my hand. I lifted it gently and started stroking it. He remained asleep but his cock very much came alive. It hardened to my touch, each stroke firming it up. I struggled to wrap my hand around it as it came to full staff. This cock was made to tame sissies!

I sat up, never letting go of his cock, and then stood over him before crouching down above his hips. I tilted the cock towards my hole. I didn't need to worry about lube, since his cum was still leaking out of me, lubricating me nicely.

I pulled the cock up against my asscheeks. Mmmm, the warmth of his cock felt like a roasting campfire against my skin.

I slapped the thick cock against my cheeks playfully. His cock felt so heavy! Pointing the cock up and letting it slide right between my cheeks, I reveled in how good it felt to have a big cock like this to dominate me. I shook my ass up and down, letting the cock enjoy my full sissy ass. God, it felt like it just got harder!

But I wanted more. I eased my ass back until I felt the cockhead against my hole. It felt like I was trying to inhale a pipe with my asshole! I felt uncertain, wondering if my hole would open up to him. One step at a time, one step at a time.

Easing back more, I felt the crown breach my boipussy. "Nnnnnnngh," I uttered. I start breathing in short stabbing breaths. I backed up a bit more, the head driving into my hole, until the whole cockhead was in. God, he felt bigger than he did last night!

Ok, that was always the hardest part. I looked back. Oh my god, there was so much cock to go!

I started squatting more, taking another inch. This thing was re-sizing my boipussy already! It felt so warm, so thick. I rose up a bit, feeling the cock ease out of my hole. Then I went back down again, letting out a little "Aaaaaaah". I did that a couple times before stopping. I had to take more of this. I eased another inch in then came up again before squatting down more and taking a couple more inches.

Each time I took some more it was like I could barely breathe. I was so focused on this task, so focused on getting this cock fully in me. The pain was exquisite. There was such pressure in my ass, like a throbbing pain but one that felt earned. As if this was the silence before the storm of pleasure would break loose.

I looked down at Daddy, he was somehow still sleeping. Wow, only an Alpha male could sleep through this. I must have had about 5 inches of cock in my boipussy. I tried forcing more in but I felt some resistance. That made me feel so worried! Was I going to be able to take the whole thing?

"Calm down, gurl. You managed to take 5 thick inches in you, that's a good start! See what you can do with just those 5 inches!" I thought to myself.

I eased up and down again, feeling this cock pull my insides around. My boipussy was wrapped so tightly against his cock, it was like a perfect sheath for his tool. Up and down, up and down. I started going faster. The pressure and pain eased up, and gave way to a new feeling. The nerve endings in my boipussy must have turned on all at once because I was in a new world of pleasure! It emanated throughout my body, making my skin tingle and my head light! Oooooh, this is gooooooood!

Faster and faster, I bounced my ass on those thick 5 inches, and I must have fit a couple more inches in with my fast movements! I was bouncing up and down 7 magnificently thick inches of Mr. Steele's cock and the pleasure well inside my asshole was bursting! Oh my god, this was so much fun!

I had a flashback to dancing on him at the strip club. I was bouncing on him now like I bounced on him then. I was his little sissy stripper.

"Aaaah! Aaaah!" I squealed, getting louder.

That woke him up. He looked up at me and smiled at me.

"You are insatiable, Britney. An insatiable little sissy."

"Yes Daddy yes!"

"You're gonna be trouble, I just know it." He said, and gave my ass a playful spank.

I was bouncing like a madwoman on this cock and loving it! "Oh my god! Oh my god!" I put my hands on his muscular chest and shook my ass faster.

"You know what you are, sissy?" He asked me.

"What, Daddy?" I asked.

"You're dick drunk, truly and utterly dick drunk."

I moaned and kept riding him, bouncing faster on him. I was dick drunk!

"Ahahaha!" What was that? Omg, I was giggling! I was bouncing on this cock and giggling like a little slutty bimbo! I reached back and undid the scrunchie in my ponytail, letting my hair cascade down.

"Daddy! Daddy! Daddy!" I squealed in joy, my head flung back and eyes looking to the sissy heavens.

I had to have more of this boipussy-destroying cock.

"Oh yes, oh god, mmmmm ooooooh!" The air stolen from my throat as I sank down further on Mr. Steele's thick dick.

I sank down further, oh god his cock was conquering new regions of my boipussy.

"Ooooh it feels so...goooooood" I managed to say before feeling my thighs againsthis. I did it, I had taken his cock to the root!

"Good girl!" He said to me. That for some reason made me feel so fucking good to hear.

I held myself there, basking in the glory of this moment.

Mr. Steele's hands grabbed my asscheeks. He slapped my left cheek hard, my ass jiggling wildly in response. Fuck, he was showing me how much he owned this ass!

And then he just took over! He rolled my ass up and down while pistoning up with his hips.

"OOOOH FUUUUCK!" I yelled, surprised by this onslaught. He wasn't holding anything back, just pounding his new sissy property with abandon! And I wasn't complaining! I was seeing stars as his cock rubbed against my sissy button in my boipussy!

This was a new version of 'Pussy Power'. This was a man making my whole body into a pussy, meant to pleasure him. And I wanted to be the perfect pussy for him.

"Ooooh oooh oooh!" I brought my thumb to my mouth and bit it gently while looking down at him. I moaned girlishly as I felt his cock take me to new heights. I was getting close. I had just had a sissygasm hours earlier but I felt myself building up to a new one! Wait, could sissies have multiple orgasms like girls could? I was about to find out.

"Daddy! Yes Daddy! Thank you Daddy! Oooh thank you Daddyyyyyyy!!" I trailed off as the words were stolen from my mouth by his jackhammering into my hole.

He had set off a trigger in my brain, I felt my orgasm shoot from my boipussy throughout my body, climaxing in my head.

"AAAAAAAAAH" I moaned loud, feeling my sissy juice burst from my sissyclit like a volcano.

"Oooooh" I kept feeling the afterglow of that wonderful assgasm trail out. Oh god, it was like my body was stretching this orgasm out, making me feel warm and full and perfect.

"Oh thank you Daddy, thank you so much!" Where girls may take a rest at this point, this sissy knew her training. I hopped off of the cock and immediately placed myself back between his legs and licked all over. I needed to make him cum, I needed to taste his cum. I needed to make him feel good, to thank him desperately for fucking me good, for letting me have his cock.

Then I heard it, "AAAAAGGGHHHH" Daddy groaned loud. Shot after shot after shot of cum jettisoned into my throat. It bathed my mouth in sticky goodness. I sank back down on his cock with my mouth, which somehow remained hard, and felt the cum drip onto my tongue. What a feeling. It was so thick, and salty and had such a pungent odor. I hoped the taste would linger for the rest of the day, the rest of the week. I wish I could bottle this and drink it.

I fell back asleep like that, my head gently nestled between his legs, my lips gently kissing his spent cock. This was happiness.

* * * * *

I woke up the next morning expecting to find Mr. Steele, but he was already gone. On the nightstand there was a note.

It read, "Sissy Britney - I saw something amazing last night. I saw a sissy come alive. I saw the birth of the next greatest Cheerboi. It was a true honor to get to have you, to be your first. You are special, and I can't wait to see how you serve Big U. this year. But don't forget, you're always welcome in my office hours. We may not get much studying done, but I know you'll earn yourself an A+"

I giggled at his joke, his throwback to the night in the club.

Then my phone dinged. I got up, my muscles sore beyond belief, my tender hole throbbing. I found my phone on the ground and picked it up. Opening it, I saw a new notification in the Cheerboi App.

I opened it, it was from the "Alpha Room". It was a text from Tyreke. I opened it. It was a dick pick, his hand wrapped around his big black cock.

The text read, "I don't think it can wait another day to get re-acquainted with you, Britney."

I thought to myself, "I better get back to campus - the men need me!"

* * * * *

To be continued...?