From Bro to Sissy Sub Pt. 03

He was holding my feet up; so, I took one of his hands and brought down to my hole, for him to finger my hole, while I swallowed his cock. He enthusiastically began to add more fingers and I used my own hands and arms to hold myself back to give him better access to my hole. What he was doing only made me crave his cock more in my ass. I was getting the feeling building up again, but I was finally free to just come.

I wanted to beg to come, for Jayden, but I couldn't get him out of my mouth in time. I felt my little clitty "erupt" and dribble out its tiny load, but inside, my orgasm was still ongoing, my ass and clitty were juddering and something spasmed inside me. I was having another sissygasm, and it was fantastic. I was trembling and gasping with his cock still in my mouth. He noticed and he caressed my face, the cock still in it, and then slapped me hard.

It was wonderful to feel his power, while still ecstatically quivering from the most intense orgasm I had ever had in my life. I felt so small and subservient. I wanted more. I nodded my head and look up for another slap. He smiled down at me and whacked me good a couple of times.

"Did you come, without permission, nasty sissy cuck bitch?" He pulled his cock out of me so abruptly it felt like it took my breath with it.

"Ooooph, aaaaaah, ummmm, fuuck! Yes, I did, I couldn't get you out my mouth in time, Jayden.

"Slaaap! Call me Daddy, slut, you should control yourself better! Slap!"

"Ooohhhph, aaaah, thank you, Daddy! Oooh, please, Daddy, punish me for not controlling myself, please, please?"

"Yes, whore!"

Jayden was the perfect lover for me. He was harsh, when I needed it, but not cruel; and he wasn't trying to manipulate me; it is purely for pleasure.

"Please, punish me, Daddy. I've been bad."

"Stay exactly as you are, sissy slut; don't move a fucking muscle." He warned and walked out of the room.

I tried to do as he said, though without him on top of me, it was difficult to maintain my folded position. I was so excited to be punished by him. I didn't know what he would do, but awaited eagerly dreaming what he might do to me. I wanted him to spank me, but I didn't want to make the suggestion, so he could do as he wanted. I was as close to how he left me as I could manage, when he came back in the room.

He brought a tote bag, I suspect supplied by Magnus, along with my cage key. I realized I had been outmaneuvered by Master Magnus. He planned this whole thing and probably given Jayden pointers. I wouldn't be surprised if Jayden had to pay him to fuck me. That would make me a literal a whore, and he would love that.

This let a little wind out of my sails; but he was letting me have a good time with a handsome well-hung man, who was going to pop my cherry tonight! It couldn't be much better, and I couldn't be happier. Jayden came to the bed with a long flogger. He ripped off my brand-new Victoria's Secret outfit (fuck!), and held up my legs with one hand and held the flogger ready.

"Beg Daddy to punish you, whore!"

"Oh, yes, yes, pleeeease, Daddy, punish me. Oooh, yes, I was out of control; strike me hard!"

He struck down at my fanny I felt the reddening immediately. I begged for more, and he struck me again. He struck me ten times with the flogger and made me beg for each one. I was red and sore down there, but it only made me want his cock that much more. He fondled my sore ass tenderly, while still holding my legs up.

"I'm ready to pop that ass cherry, whore. You want it."

Oh, I wanted that more than anything. I had an idea though. I asked permission to get something. It was my "Sissy Cuck Bitch" dog collar; I had him put it on me, and tie me to the same post Magnus had tied me, when he fucked his whore in front of me. I had him tie me in the same position, making sure I was choking.

With him on the bed, and me kneeling on the chest, I was in perfect position to suck his cock. As I was, he could fuck my ass from behind while pulling on the collar, choking me. He did as I directed and got on the bed and fed me his cock down my throat. With the collar choking me it took all my breath away. I encouraged to him to facefuck me, while I almost passed out.

It is impossible to know these things about oneself beforehand. I was thrilled to be in this position and having arranged it as I wanted. I knew I should cede control to my Dom, but the thrill of replicating the position was too much. His idiosyncratic cock was so delicious to suck. Something about the way it twisted around my lips and down my throat. He began gently, but was soon vigorously throat-fucking me, choking me pulling on my head, just as I wanted.

"You like my big dick, cocksucker?!" He shouted and kept slapping me for good measure.

I nodded enthusiastically, and moaned, loving his cock, the choking and slapping. Fuck! I am definitely a nasty cocksucker. I was really proud of myself to have his giant cock all the way down my throat without gagging too much, even as he wrenched on the collar choking me. I had no gag-reflex to speak off; a natural born cocksucker!

When he was done throating me, he positioned himself behind, opening my hole one last time he worked a ton lube into it and onto his glorious cock. He pushed in hard and fast, just like I begged. I needed and wanted to be broken-in, to feel the burning pain of his cock rending my hole apart. I felt my fuckhole open up to him, the pain was incredible, searing hot, but as he settled in, all that pain turned into lust. I was thankful the plug had prepared the way for him.

I begged him to ravage me, to wreck my hole. He pulled my head back, choking, to kiss me hotly again as he began his motion, as he removed what little claim I might have left to manhood. I was getting ass-reamed by this gorgeous man with an enormous cock, and my teeny clitty dripped precum and stood hard as could be. As he started fucking me, I could feel that curve of his cock augur into me. It was just delicious. Every time he went in, I waited for that little twist his cock would give my hole. Unlike with me and Flora, I was sure I was no longer a virgin.

I urged him to choke me by pulling down on my shoulders. I knew I'd like it even more when close to passing out. I just loved how vulnerable to him it made me feel. I wanted to be completely vulnerable to Daddy. To give myself to him, as a special right to my body. He was now doing more to me; his cock was driving me crazy. I was using what little air I could get to moan for him, to let him know my appreciation, and beg him to ass fuck me harder.

I was lightheaded and high from lack of oxygen. He fucked me ruthlessly; I did not need to remind him I was a sissy cuck bitch. I was delighted to be under his control.

"Please, Daddy may I come, for you, pleeeaase?"

"Wait for me, bitch; I'm gonna come too! OOOhhgh!"

"Ooooh, yes, Daddy, fill my hole with cum! Fuck me, Daddy OOOh!" He pulled my head back and kissed me deeply as he started to come.

We came together. If I hadn't already gotten there, his cock spasming inside me would have driven me over the edge. What an amazing feeling to have a part of someone else's body inside me spasming as if it were alive. It was contracting and spewing its spunk. Each time it would recoil and then blow again. My insides were filled with his cum.

He slowly pulled out and brought me his slimy softening tool to clean with my tongue. I devoured it, licking him clean. But he soon left me hanging on the post, to go clean up, then went in the kitchen to get a beer. Somehow, I loved this; I felt so used and insignificant hanging there by neck with my ass destroyed, his cum dripping out of me. I felt so deliciously humiliated, continuing to quake from the orgasm.

I hung there waiting and enjoying the afterglow of being ravaged and left behind. I can't quite describe why that detail was so arousing to me. Again, it was partly the humiliation of being used, abused, and treated like just a receptacle for his needs. Deep in my hole I could still feel the impression of what his big dick had done to me, like an indentation on memory foam, but I also felt empty and eagerly anticipated being filled by his cock again.

When he came back, he had me spread my cheeks to show him my gaped asshole, so he could take a picture on his phone, for Master Magnus. He showed me the picture; I couldn't believe my little teeny hole could opened up that wide. He untied me and let me clean up, and we crawled into bed together. We never really stopped making out; he fucked me three more times that night. I came multiple times during each.

He fucked me slow and sensuously, so I felt my little hole being pampered and loved. I laid on his chest and kissed him. Then, he rolled over me and had me open my legs wide to accommodate him. While kissing me deeply and sensuously, he slowly ground his spirally penis back into my hole. I was still gaping open and the pain was minimal. My little hole was so happy to have its new favorite guest back.

He went into me balls deep, but the motion was totally different. He was sliding in and out like waves in the ocean, gently massaging rather than ramming my prostate. I couldn't stop moaning and groaning into our hot kiss. I began to match his movements rocking my hips to accentuate his probing. We undulated like one large serpent slithering on the bed.

I could feel the pressure of his pelvis as it knocked into my teeny testicles, my clitty was engorged and dribbling goo. It took long to build to another orgasm this way for both of us, but the pleasure of that build up was divine. I could have done this all night.

He suddenly pushed in hard, then flipped us around so I was on top straddling him. I tried to keep to the rhythm he had established and succeeded for a while, but I didn't have his discipline and found myself jumping up and down on that colossal cock, ripping it into myself and on the verge of my another massive sissygasm.

"Ooooh, fuuck, ooooh, aaah! Oh, Daddy, sorry, please may I come? Oooh, pleeeease!"

He was so good to me. He let me finish coming hard on his cock, spraying his belly with my weak little cum. I pushed in one last time and collapsed on top of him kissing him in ecstasy.

I loved my new way of coming. I no longer had to fear preemies; it took a while to come, but when it happened, it was magical. My little clitty would spill, just a bit more than my almost continuous pre-cum, but inside it was like the Fourth of July! When I was done, he put me in the doggie position and fucked me hard and fast and slapped me and pinched my nipples. When he was ready to come, he hustled me around and came in my mouth, so I felt like a dirty cocksucking slut.

The following morning, I sucked him off when he got up and he came down my throat. We showered together, and he help me clean my insides with the enema, pushed the buttplug back in, and locked up my clitty again. Before leaving, I begged him to spank me and he obliged. With plug firmly in he gave me a wonderful spanking, which let me come one last time. The whole rest of the day, I was floating on air. A sissy could get used this. Master Magnus texted to ask how my evening was. "Wonderful!" I responded, thanking him for Jayden.

He also sent a theatrical release contract for footage of my blowing guys at the bukkake, I did not know they had gotten. Apparently, Flora and the men's faces would all be digitally disguised, but mine would not. He said, it wouldn't matter because no one would recognize me. He had a point, though I would look close to that from now on. I reluctantly signed it for him.

He gave with one hand and took with the other. I asked about... his slut. And he said he was taking a break from fucking her, while she recovered from the other night. Plus, he wanted to build up anticipation before her next "lesson."

He reminded me the "Jayden experience" would be "curated" by him. I was allowed to see him, but if anything sexual happened, I would lose the privilege permanently, he reemphasized "anything." He had warned Jayden, he said, and trusted him to obey instructions.

As it turned out Jayden wasn't paying "money" to fuck me; he was paying with his cock. Magnus had recruited him to do bukkake videos for L. Maxxxon, but Master Magnus would take 40% of his video pay; he clearly didn't need the money. It was a symbol of his control; once Jayden was in his orbit, he would control him, and me through him.

To Magnus, life was a giant pyramid scheme. If he could use two people to control two other people and so on... But it wasn't just two people; he was amassing underlings, who would fall into his thrall. Like, L. Maxxxon, the bukkake king, was beholden to him because he provided women and men to star in his films. Each of performer he provided had some tangential relationship to him, like Jayden.

Jayden was hot to fuck me from the moment he first saw me, still presenting as a "man." He was more than happy to be in those videos and get his big fat dick wet and get paid for it. But very soon Magnus would ask him to do something more and would sink his hooks further into him. He was a young handsome guy, he may be able to recruit other similar men, or women, or help to "guide" a cuck husband on the "right" path.

I wasn't happy with this aspect of it, but could do little. I didn't know about the sexual dimension, but at a more general level, I was well aware of this feature of Magnus's philosophy of life and personality. I could see his Machiavellian manipulations, but still... I was pretty happy with my small corner of his empire. I put my head down and went all-in on my transition process.

It had been two weeks since that night. And Jayden and I had spoken on the phone daily, but I didn't have to courage to meet him alone in person. I didn't feel safe around him because I wasn't sure I could keep my hands off him after how good he had made me feel and didn't want to lose him permanently.

We had managed one coffee, inviting Pam along as a buffer. I explained the problem to her, and she turned out to be an excellent chaperone—I guess you can't beat an Evangelical Christian mediator, transitioning into transgendered lesbian to acts as cockblocker. She allowed a peck hello and one goodbye, but no "hanky-panky." She was the kind of person that says "hanky-panky" non-ironically.