From Bro to Sissy Sub Pt. 03

That seemed to assuage her fears somewhat, but she was trembling on the stand. He explained to her that it was a bondage bukkake gangbang, including describing the genre. She was really trembling after that, like a frightened rabbit. She pleaded that she was not ready to be shared and could he just whip her for punishment and fuck her again instead, please...?

He told her he would punish her, for resisting, but she would still have to do it. He went to the cabinet and picked out a flogger and gave her ten whacks with it, making her beg for each one and apologize for being insolent. She agreed and sobbed, begging him, to please not let the faggot sissy witness her fresh humiliation. He agreed. She thanked him though still sobbing emotionally.

"You must learn, whore, all you are to me is sexual property. I could share you as I see fit, and you must accept it; that's what your submission means. You can refuse, but that would end this relationship. Would you like me to untie you and send you back to the sissy cuck."

"No, please, Sir! I'd much rather stay and please you, Master."

"Okay, I will keep the sissy out; but it is for my own reasons, not to protect the bit of pride you're holding on to. I'll take that last bit of dignity away from you, when I feel like it."

She sobbed harder, and he patted her face lightly and introduced the massive head of his cock to her open mouth. She opened wide and swallowed down like it was the elixir of life; her mood changed instantly, and she was soon moaning and groaning. The camera panned out to her undulating hips, her legs straining against the harness as she fell to worshipping his cock. He used remote controls for the cameras. He caressed the back of her head and let her have his cock at her own pace and depth. She moaned happily.

He raised the monster up with his hand and let her suckle on his big balls. She tried to work both of them in her mouth, but couldn't quite manage it at that angle. She licked up and down the shaft. Then, he drove his cock back down her throat and reached behind her and squeezed her generous buttocks. And explored the chasm between until he found her butthole. The camera angle switched to her back side, as his fat fingers began to explore the rim of her hole.

He pulled her butt cheeks apart really wide... and there... inside, round her hole was a tattoo that read "Property of MM," the em's in a calligraphic font. She was moaning loudly on his cock now and swirling her hips around begging for more of his fingers. He pulled her off his cock and gave her another hard kiss and moved around to her backside. He put his cock up to the edge of her hole and stopped.

"Bitch, what do you want?" He plunged his thumb into her hole as he asked.

"Ooooh, Sir. Yes! Fuck my ass again with that beautiful monster, please!"

He wasted no more time, driving his cock deep in her ass in one smooth move. She cried out, in obvious discomfort, but it was already tinged with lust and pleasure. As he pulled out and began re-entry, she screamed out: "YES, yes yes yes yes yes yes, fuck yes!" and grunted like an animal as he hit bottom.

He pulled back on her long hair and used it as reins to push himself harder and deeper in her hole. She was moaning like she was building up to something and he stopped dead, with the tip of his cock just resting on the rim of her gaping anus. She gasped for breath and tried to roll her hips to nudge the penis in, but she was fastened too well.

"Whore! Listen carefully. Tonight, more than twenty men are coming here to fuck, use and abuse you how they want. Their only limitation is they have to come in your mouth or on your body, not in your nasty holes. Tonight, you will truly become my whore; our friend Maxxxon will pay a hundred dollars for each load you receive. I know you will love it because you are such a nasty ass cumslut.

"I'm so sure, I'll make you a deal, whore. If at the end of the night you are not begging for more and loving being abused by these men, I will never share you again. But if you do like it, I will punish you with one stroke per load for being such nasty fucking whore. Sound good?"

"Yes, erm... Sir. Master, may I ask you a question?"

"Yes?!"

"Did you ever share my sister, like this?"

"Oh! Tch, aww, no honey... Your sister was not a whore, like you; she was my wife. And not a true submissive, though she sometimes role-played for me. She was more of a Domme herself, we fucked a lot of whores like you together, and she loved to peg the cucks too. But no, she never got fucked by any man, but me. That I knew about. Ha ha ha!" She was sobbing silently.

"Sorry, but you asked. It's not a fault; it's all in our nature, you have a subslut nature; she didn't. Now, beg me to whore you out to all these men tonight, bitch!"

"Pleeeath, Zir, eegthegh make me a whore to all these men. But, please fuck my ass, Master." she sniveled. Her nose running from sobbing.

He pushed in and fucked her hard and fast with no intention of slowing or being gentle. She was soon moaning again, and begging to cum and be fucked harder and deeper, though that had to be impossible. He let her come, but kept pounding away at her until he was about to come, then unceremoniously, pulled out of her ass and raced to her front. She opened her mouth wide, but he seemed to aim all around her mouth with only a small part of his huge load landing on her outstretched tongue.

She lapped up at the cum around her face, but with her hands tied could only manage to get what was immediately around her mouth. She was left with quite a bit of ejaculate dripping from her face, as he rubbed his slimy cock all over it. He pulled away leaving her a gasping mess; he reached down and pulled up the ring gag, dangling from neck that would force her mouth wide open, and tightened it in back.

"I have details to attend to, whore! I expect you to perform for our guests."

"Yeth, Zhir. Dhank uuu, Mssser!" She slurred through the ring gag, still shaking from her orgasm.

He walked away and another camera captured him as he walked out the door. On the "scoreboard," in behind the door Master Magnus put a single hash mark, for the first load, and the screen went blank. As I stared at the screen, I realized this was not the video they would be selling online; this was just for me, to show me his point.

I had been whimpering and sobbing through most of it. Her feelings toward me and disregard for my feelings hurt deeply. I felt stupid that I had demanded to talk to her before the bukkake. Magnus's story checked out better than I thought it could; there was a change in plan and he did seem to be trying to engrain his dominance and lack of romance in her head. And maybe that could lead her back to my arms, at least platonically, but now I wasn't so sure I wanted it.

None of this made my decision easier, I was half-tempted to call Jayden and run away with him as he had suggested. She didn't really seem to want to see me again, and I was getting very little of Master's attention. Though I felt a sudden twinge in my teeny package when I thought of how he had humiliated me having me suck all those cocks and then get passed the building staff and out in public a complete mess with my ribboned caged clitty sticking out.

It was the following Friday, before I finally got a call from him to talk about our situation. He started by saying he had spoken to Roxanne. He said he was delighted with my decision to pursue gender reassignment. He was willing to compromise on the cause. He was magnanimous if not downright jolly in tone.

"My little sissy Drew. I just want you to be happy. As long as you know you'll still belong to me when you are a sexy little tranny gurl."

"Master?!" This had to be the best time to bring up the Jayden situation.

"Yes?"

"I have to confess..."

"What is it, little sis?"

"Well, there is this guy, Jayden. I met him at the spa..."

"What!? Are you going to tell me you let another man fuck you, bitch?"

"Well... not exactly..." I proceeded to tell him the story as honestly as I could and he listened, kind of as my old friend, for a minute."

"Okay, sissy. Obviously, that cannot continue to happen. I will have to punish you for it, and you have this Jayden call me to talk about restitution. I was going to invite you to watch me with my whore tonight, and maybe even let you come, but now you will have to wait until next week.

"I've made you and appointment with Dr. Harris for tomorrow morning. You can say you are doing this for you, but you are going at my pace. Normally, you'd have to wait months, to get started, but this Dr. Harris is willing to speed things along."

"Yes, Master! Thank you for being so understanding."

I was happy to agree to his terms. I was so sure I wanted to go ahead that I couldn't wait to get started either. I went to my appointment wearing a tight business outfit—a short tight skirt, a white blouse and a blazer. I was getting better at makeup, so I didn't make myself look like a clown. The very swanky clinic was open until noon on Saturday, and I had an 8am appointment. Dr. Harris was a large round man who look at me like I was a Happy Meal.

Once in his office though, he became ultra-formal, officious even.

"So, Ms. Forde, my friend Roxanne recommended me to you, and I know Mr. Menard. I've treated a couple of his... uhm... 'friends'. I'm sure you know, but it's my duty to tell you that while I am aware of the relationship you have with Mr. Menard, if you choose to proceed, I will be your doctor, with all the implications of a doctor/patient confidentiality. I cannot speak about anything you tell me in confidence, even to him.

"As an example, I understand that Mr. Menard wishes you to proceed rather quickly with this process. There are sound reasons to be cautious in this situation, and I will warn you of consequences, were we to proceed. Also, he has sent pictures of what he would like the final results to be. I assure you that will be entirely up to you. I will give you different options, including his choices."

I thanked him for his honesty and ethical approach and felt reassured that the professionals Magnus had sent me to seemed to be legitimate, even if willing to bend the rules. The doctor had me undress and took pictures of me from different angles and for different purposes and loaded them onto his computer.

Started with my face, he showed a manipulatable 3D image of me today and the very attractive model Master Magnus had sent. He superimposed her picture over mine and showed me the kinds of things he would need to do to my face to get me to look like her. He said the goal was not an exact copy, but would bear a resemblance. He made his own suggestions and we arrived at a compromise.

On the face, we agreed on "minor brow work," rhinoplasty for a more delicate nose, implants to raise my cheek bones and jaw "softening." He would shave my bony Adam's apple, and the voice change operation. As far as the rest, he was putting me on an aggressive hormone therapy regimen first, and we would see what developed.

This would result, in reduction of my already teenie peenie and testicles, even less body hair and a rounder softer figure. Potentially a decreased libido. I would develop breasts, but in the end, he thought I would probably need implants because of my age, and what Master Magnus had in mind for me (again reminding me it would be up to me).

She showed me images of my future self with different sized breasts. As for the bottom half, it was best to wait for the hormones to do their job and reassess, but he thought it best to do that at the same time as the breasts if we were doing it. One big recovery instead of two.

He said there would be other "interventions" such as specific exercises to round out my bottom and perhaps corseting for a curvier figure. I left the office feeling somewhat overwhelmed, having signed a bunch of forms that I was not doing this under duress and understood the potential side effects, et cetera. Again, Magnus would be covering the entire treatment plan. I also had a purse full of pills to take and an appointment with a personal trainer.

Checking my feelings, as I got into my car; I was anxious and nervous, of course, but truly I was, was overjoyed! The whole decision thing was over, and I was proceeding down a path that felt right. I had some time before I had to get to the gym for my first session with the trainer, so decided to do some shopping in a Victoria's Secret; I got a lot of nice silky panties and some lingerie. I felt so excited and feminine.

I got to the gym, the trainer was gorgeous, muscley, but not like those guys who can't put their arms down because their "guns" are so big. He had more of swimmer's build and was wearing spandex compression shorts; the outline of his large penis nestled in a half coil, like a codpiece distracted me the whole time. I couldn't believe how often I was checking out men's crotches these days. Hardly a man passed me whose bulge I didn't check out.

He also knew what I was there for, and who had sent me. He was very sweet guiding me through the sequence of exercises is to do to get "thick!" Thankfully, the stress of the exercises calmed my little clitty down, and I could rest from the pain he had been causing me. I realized something about myself, I, of course, didn't know before—as I felt myself positively dripping from my clitty from watching him. I am really attracted to black men.

As I watched my buff trainer squat and thrust, to demonstrate the exercises, I couldn't resist biting my lips and imagining slurping on the fat cock I could see through his tight shorts. What was happening to me? I was always on the verge of being horned up. Wearing the buttplug and the clitty cage didn't help. They continually reminded me of my condition.

We finished the circuit and he left me alone to go through my first reps. Again, he too was very professional, but I could tell, he wouldn't mind if we had a roll on the mat together; I certainly wouldn't. I got home in the afternoon with takeout, from a city restaurant. I was all horny from the doctor and the workout with that fitness god.

I had to do something; I couldn't settle my mind on anything that didn't lead me back to how I might get off. It had been three weeks since I had been in a cage, and had only been allowed to come the night of the bukkake, which felt ages ago now. Normally, that would have meant nothing to me, but now I was in constant state of arousal, even with the pain it caused. My clitty didn't care; it just pushed against its cage like a prisoner trying desperately to break out of solitary. I was eager for the hormones to help with that.

With much trepidation and nervousness, I texted Master Magnus, to say I wanted to talk about how the appointment had gone. I figured I could bring the conversation around to getting some sort of relief. He texted me back right away, to wait a half hour for a call, and, for once, called right on time.

"So, how'd it go, little sis?"

"Good, good. I feel good, he was very thorough. I've started the hormones already, and I went to the gym with the trainer. That was fun!"

"Yeah, I bet. You know, he's gay, don't you?"

"Oh, who... the doctor?" I said, playing dumb, but wondering what that meant to me now.

"Yeah, sure the doctor, you fucking slut."

"Sir. I know I fucked up, but I've been a very good, otherwise. Haven't I?"

"Yes... where's this going, little sissy?"

"Well, I haven't had an orgasm since the... y'know, I am so horny I can't think straight, Master. Please, Sir. I need something, or I am going to go insane."

"I understand, little sis. And you have been really good, given the circumstances. Do you want that Jayden, to fuck you, sissy?"

"Oh, Master, I would love that more than anything, please... Sir, I'd be willing to get punished for it, Sir. I'll do anything, please, Master."

"I'll take you up on that, sissy. Go ahead and call him; I spoke to him already; he seems like a fine young man to pop your cherry, little sis. Clean yourself out nice for him, sweetie, like I told you. Have a good time, sissy, remember you will pay me for this later and you still owe me for Sam and the party." He hung up.

I texted Jayden right away, excitedly. He said he had been expecting my call and would be right over. I was flabbergasted, but didn't have time to dwell on it too much. I was running through the house straightening and then getting myself ready for truly losing my virginity. I tried on every outfit from Victoria's Secret twice. I had decided to go with my sluttiest look, when he rang my doorbell.

He barely got through my door, he was on me, kissing me passionately and hard, and I felt so free to just let him take me in that way, knowing I had permission. I tried to slow him down, just so I could savor it, but he picked me up by my hips, and I wrapped my legs around him and he carried me to the bedroom, as I guided him with my head, never letting him stop kissing me.

"Oh, fuck, honey. You are so fucking hot," he cooed.

He laid me on the bed and started to remove his shirt. I was going for his pants and he nudged me back gently.

"Wait... hold on..." he said, as he reached into the pocket of the jeans, I was prying off him.

"I have a surprise for you, sweetie." He said, in an excited tone and held up the tiny brass key.

He gave me his biggest, widest, toothiest, grin and reached down between my legs slipping my thong to one side and finding my caged clitty. He put the key in the lock and the little clip flipped open. Then, he maneuvered the cage off my clitty and let it finally free. He put the cage on the night stand and caressed my tiny penis, rubbing it, as if it were truly a clitoris. Then be knelt on the bed and put my whole thing, balls and clit all in his mouth.

It felt incredible, and my pee pee got as hard as it had ever been, but it seemed so insignificant in his mouth, like it was nothing. He pulled it out and began to lick my hole, which had been empty for the for the longest time in weeks. I had switched to the XL plug and was gaping whenever I didn't have it in, so he was getting his tongue pretty far up there. I was just laid back, enjoying everything he was doing to me. He moved up my body, moving the lingerie around to kiss my belly, my chest, my nipples, really hard for him. He bit them making me squirm.

Finally, he got to my mouth and just buried his tongue in mouth and down my throat. He had hugely long tongue it seemed to me. He kissed me as he wriggled out of his underwear, the last bit of clothing he had on. His big man cock was rubbing up against my little sissy clit, and I was loving the feel of it overwhelming my own little thing, making me feel small and femme.

I could taste my precum on his breath as he kissed me, the thought that he had me in his mouth made me almost faint. I wanted his cock in my mouth right away. I wanted more than the little taste I got the other time. I grabbed it with my hand and nodded my head to signal what I wanted to do. He was very obliging, but instead of crawling up, or having me kneel to it, he pushed my legs way over my head, folding me in half, with my ass up in the air. Then he straddled me and pushed his cock into my mouth from between my legs.

I was about to remind Jayden I was submissive, and he should feel free to do anything with me, when I felt his long thin hand slap at my upright peenie and tiny berries. The pain reminded me I was about to get fucked by a real man. I loved that he had done it without my having to explain. It was so thrilling not to be caged, to be able to get hard without the cramped cage. He may have wanted to get my clitty to go limp but tonight that wasn't helping.

I was on fire, I wanted him to do everything to me at the same time. I wanted him to come in my mouth, but I wanted him to fuck me too. I wanted more of his kissing, but I didn't want stop sucking his massive spiral cock. I wanted him to let me do everything I wanted, but I wanted him to make me beg, control, humiliate and abuse me, like Master had done. He was certainly pounding my throat, and I was enjoying it, but I wanted more.