From Bro to Sissy Sub Pt. 02

Each time I had little more control of the pitch. Once I had the pitch right, we worked on cadence, timbre, and other speech traits, like ending sentences with a hint of a questioning tone. After that, he engaged me in conversation and had me perform my womanly voice. Always adjusting my tone as we spoke, waving his index finger up if my tone got too low.

We sat close to each other, as he adjusted my mouth and watched lip and tongue movements as I spoke. I stared at his rugged handsome and distinguished face. His voice was honeyed gold with a deep resonant tone. As I spoke to him about my situation and described my submission and arousal, I fantasized. This time with Sam Johnson as my dominant.

I think he could sense what I was thinking. My little clitty was aching in its cage again, and I wriggled around in my chair to adjust it. I was sure he could tell; he kept giving me alluring smiles. Let me just talk and talk with that same beneficent smile. Pointing up with his long thing index finger when my pitch dipped down.

We seem to be done with the voice work. He leaned in and squeezed my thigh; his touch was like fire; I was ablaze with desire. I could barely breathe and stopped speaking. He leaned in and timidly approached my lips with his. A million thoughts went through my head, most of them about Magnus and my submission. But they couldn't stand up to my yearning to open myself to this handsome man. I wanted that kiss even if I would get punished for it.

He kissed me harder than Jayden and more possessively. He took control of my mouth completely. Jayden's was more of a dance; this was more forceful and one-sided. I let him kiss me, but soon his hand was reaching up my short skirt. I wanted to open up down there as much as with my mouth, but I knew this would be too far. I had to stop and remind him of my submission to Magnus.

I managed to wriggle out of the kiss; it took every ounce of will power to stop the pleasure he gave me and try to be a dutiful sub bitch. Getting kissed by a man was drastically different than kissing Flora. What thrilled me most was the feeling of being taken. But I had to stop him.

"Please, please, Mr. Johnson... I-I-I... can't. I told you about Magnus."

"Ummm, you are a cute little sissyboi, but you're a fuckin' little tease, you know that?" He leaned in to resume his kiss, but somehow, I managed to work up the strength to resist.

"Okay, little girl. But... uhm... you would like... yes, honey?"

"Oooh, yes, Mr. Johnson! But... you know..." I nodded, and put on the poutiest little girl voice he had shown me.

"I'll call Magnus."

He took out his phone, and I could make out Magnus's basso profundo even through the tinny cell. I was trembling with sexual excitement. If Mr. Johnson asked, I was sure to get what I wanted. I was so on edge all the time now, always aroused, but not allowed to come.

"Yes, she's right here..." He put the phone on speaker.

"Hey, little sissy. Let me hear your girly voice!" Master demanded.

"Hello, Master Magnus, how are you?" I chirruped, as I had just been practicing.

"That's fantastic! Sam. You are a miracle worker, my friend. So, what...? You're angling for a little reward for your efforts, Sam? Is that it?"

"Well, I can't see the harm, Magnus. You got yourself one cute little sissy, here. Tell you what: I'll remove my fee..."

"Okay, Sam, but you can't fuck her and you can't make her cum. I want to keep her dry for a while, you understand. And that sweet little virgin hole is worth more than your fee."

"Okay, what about striking her?"

"Oh, sure... knock yourself out; I think she's a little painslut. Hey, cucky sis, you don't mind if Sam abuses you a little bit, maybe whips you?"

"No, Sir! I'd love it. Master, but, please, may I..."

"Come? Aww, tch tch, no, little sissy. Sorry! That's not in the cards for you today. But I want you to be a very good girl for my old friend, Mr. Johnson, don't let him fuck you, and don't you come, or I'll be very disappointed and have to punish you. Understand, little sis?!"

"Yes, Sir. Master Magnus... thank you!"

"Ooh, you sound so fucking sexy, Drew. Great job, Sam! Will you record your session, for me?"

"You got it." Mr. Johnson cooed.

He put the phone down and looked at me like a catered lunch. That look excited beyond my wildest dreams. I couldn't wait to serve Mr. Johnson and his cock. I couldn't wait to feel him down my throat or whipping or spanking me. I just hoped I could keep from coming. I had gotten so close already with just the plug; this situation was so charged, I feared failure. I didn't care about being punished; but not disappointing Master was suddenly my prime directive.

It wasn't as if I didn't know what he was doing--"keeping me dry." He wanted me in a state of constant sexual privation and arousal. Despite the discomfort and the desperate desire, I was glad he was doing it. He had awakened my moribund libido; it was like I was making up for lost time. If he allowed me to come, it may have been less effective. I didn't want to disappoint him, but in part it was about going through the process for best results.

It was working because, since that night, I could hardly think of anything else. I'd fall asleep replaying the scenes with him and Flora, and my part in them, or myself replacing her. And I'd wake up thinking about a real cock penetrating my hole like plug. The desperation was exacerbated by situations like the one I then found myself with Sam Johnson.

He stood up from his chair and pointed to spot on the floor. I couldn't get on my knees fast enough and automatically placed my arms submissively behind my back, like a good little sissy bitch. He went around the room flipping lights on and moving equipment. He moved two video cameras on stands from a corner of the room to either side of where I knelt and turned on a camera affixed to the wall in front of me.

In front of the eggcrate, he pulled down large screens with a cityscape, as if looking through a window of tall building. This couldn't be just a personal shoot, I worried. I was nervous about that, but so aroused and eager for what he was about to do to me; I put it out of my mind.

I had on a halter top with a bare midriff, a push up bra with padding, and makeup that made my non-breasts look like something (a trick the makeup girl taught me) and a super-tight latex miniskirt, which made me look like I had the ass I lacked. Under that, I had white garters and stockings to just above the hem of the tiny skirt, with frilly white panties underneath.

While he darted about making adjustments, I knelt there, watching him and imagining all the nasty things I wanted him to do to me. Most of which were ruled out of bounds for this session by Master Magnus. And if some did come true, I would for sure break the no orgasm command.

He was finally happy with the set up and turned to me again. He kissed me in that delicious way, in total controlled of my mouth. This time stooping down as I passively looked up into his ice blue eyes and his rugged weathered face. He pulled away, and I saw he had put on a Lone Ranger mask, which made him look even sexier.

"You are submissive, my dear, yes?" He asked offhandedly, in a radically different voice than he had used before--a kind of "Euro-trash" accent.

"Yes, Sir." I said in my new girlie voice.

"You would like me to hurt you, yes??"

"Oh, yes, please, Sir."

"You want my cock, 'hore?"

"Oooh, yes please, I want your cock so much, Sir."

He had me take off my skirt. As I stood and wiggled it off, he spanked my bottom and grabbed my cheeks between the garters.

"Ummm, ummm," I responded, my mind drifting back Master Magnus spanking me and how wonderful it felt. I wanted the same from Mr. Johnson, now. I poked my ass out for more.

"Beg for it, slut!"

"Oh, yes, yes, please, please, Sir. Spank my ass, pleeease!"

He sat back in his chair and directed me to his lap. I hurried into position. "Whack!" It felt even better than Magnus. With the buttplug in, it sent shock waves directly to my prostate. My clitty swelled instantly. I could feel my buns reddening, the blood rushing. I wanted to ask for another, but it was getting me too excited too fast, and I was afraid where that might lead.

He pulled down my frilly panties and fondled my teeny clitty in its cage, from behind. It was rock hard, swollen against the cage. I moaned deeply. Had he done more, I'm sure I would have squirted. He reached behind him for a crop with a tiny leather hand, held my butt cheeks apart with one hand, and snapped it sharply on my testicles and caged clitty. The pain was shocking; I screamed loudly, then held my breath, but my erection went limp, thankfully.

"Owww, oooph! Oh, fuucck, thank you, thank you so much, Sir. I was close."

Despite the awful pain, I was very grateful to be stopped from coming, so I begged for more spanking. He gave a few more, maybe five, and then I had to beg him to crop my clitty again to keep from coming. It was worth it because I was able to enjoy at least five more strikes, before he stood me back up by the hair. I enjoyed his tender caresses on my sore burning cheeks.

He pointed down again, and I went back on my knees. He leaned back again, and brought back some thin rope, tied my hands behind my back, then stood before me with his crotch in my face. I could make out the silhouette of his sizeable--though not huge--cock, through the thin gabardine of his trousers. I leaned in intuitively, and he rubbed it all over my face pulling the back of head roughly.

He took off his belt and unbuttoned his pants, leaving the zipper up. He held the belt up and swatted my sore behind with it. I moaned and leaned forward to give him a better angle. The sharp swat against the dulling pain was electrifying. He struck me harder, and I screamed, as it lapped the crack of my ass and my tender raisins below. This was great because I could enjoy the pain yet instantly reduce the chance of coming. I thanked him.

"Does the 'hore enjoy breath-play?"

"Ooooph! Whah??"

"Do you want to get choked, faggot?!"

"Ummm, yes, please, Sir. I'd love that."

My mind again went back to Magnus, watching while I dangled from the bedpost. I had loved that; it made me feel so vulnerable and open. I can't explain, even to myself, why this vulnerability was so alluring to me, something about giving up complete control, helplessness.

"Beg for it, slut!"

"Please, please choke me, Sir. I'd really like that, oh, please!"

He wound the belt twice around my long thin neck. Holding both ends, he pulled until I gasped. I was getting about a tenth of the breath. He pulled me by the belt toward his crotch. I knew he wanted me to lower his zipper with my mouth, but had difficulty coordinating thought to movement. As he moved me around it, I'd bite down and miss it. The lack of oxygen reduced my concentration.

I finally bit down on the hard plastic tab and pulled down. I got the zipper half way, but lost my grip. The exertion and lack of breath was making woozy, but I persevered, and soon I had his meaty cock flop out in front of me, and I inhaled that musky man smell I love so much. I immediately went for it, wrenching on the belt to get my tongue on it; but he yanked me back.

He took both ends of the belt in his left hand and used his right hand to slap my face. There was less pressure on the belt now and I could breathe a little easier.

"Did I say you could lick my cock, faggot?"

"NO, Sir!" Slap, slap.

"I'm sorry, Sir. May I please suck your cock?" Slap, slap, slap.

"Thank you, Sir. Pleeeaase, may I suck it???"

He held it out to me, giving me just a bit more leeway with the belt. His cock was not as big as Master Magnus's monster, but it was just perfect. I couldn't measure, but if Magnus's was a foot long, Mr. Johnson's was maybe eight-nine inches, but thick. He was circumcised, which made his penis look beautiful... just perfect, like it was carved by an artist.

I licked the bulbous head first, round and round with my tongue, with my lips holding on to it, then I took it down a little at a time. I wanted to be ready; so, I watched instructional videos on giving head and porn too. had practiced fellating Flora's old dildo daily, which was nearly identical to Sam's cock, so I had no problem with it. The real thing was so much more satisfying. I could feel it hardening in my mouth and the warmth was delightful.

Though my favorite part was his sensual moaning. I worshipped his cock for a while and wanted him to take over. I buried myself on it and held it down my esophagus, (it was so satisfying taking his cock balls deep), until he had to pull it out himself and start fucking my throat. He slowly increased the pressure on the belt. I was choking and having a harder time taking him deep. This is what he wanted, my choking and struggling must give his cock pleasure; so, I let him and kept calm so as not asphyxiate.

"Oh, fuck, you're such nasty little sub faggot. I wish I could fuck you, whore."

"Who ya telling?" I felt like shouting out except the cock assaulting my throat wouldn't let me.

I loved what he was doing to me. I couldn't get enough of that cock, and he was a virtuoso dominant, making me feel vulnerable and subservient. I was getting close again, and needed another whack on my clitty to be safe. I didn't relish the pain, but being filled at both ends like this and his humiliation and deft touch was going to get me in trouble. I pulled back away from his delicious cock, missing it instantly.

"Sir, please, please, pleeeaase, my clitty, Sir. Help." I moaned, gasping.

He understood right away and without missing a beat reached for the crop and whacked me nice and hard. I leaned way back and pushed my crotch forward to make sure he struck his target. I screamed again, but thanked him profusely, as I felt myself go limp inside the cage. It hurt bad, but I couldn't be sure how long I could keep it down; so, I begged for one more. He was happy to oblige, then shoved his perfect cock back down and continued to throat-fuck me.

Not much later he shouted: "I'm fuckin' coming, fag 'hore!" I hoped he would fill my mouth with his cum; I was eager to taste it, but he pulled out and sprayed wad after wad on my face. I got to taste a little bit licking my lips and around my mouth. He finished coming and let me clean his perfect cock, before he stood me up, untied my hands, put my skirt and blouse back on, and hustled me out of the door, ordering me not touch his cum 'til I got home.

I was embarrassed and ashamed the long three blocks to my car. I came across quite a few people, but kept my eyes down the whole way. I'm sure some noticed, but luckily no one said anything. I got in my car and drove home as fast as I could. My little clitty was bulging against the cage almost the whole way.

When I got home, I wiped the cum with my hand and tasted some, most of it had dried, and I clean it off in the shower. I couldn't believe how aroused I remained. I could think of nothing but how I would have loved him to fuck me and come up my ass, and how desperate I was to come. And, how the humiliation of walking down the street as a cum-covered slut was so exhilarating to me. I felt a rush of adrenaline thinking of it and my clitty and ass twitched.

The voice training was an unparalleled success. I spent two hours working on voice with Mr. Johnson, and despite his insistence that it was performative, I felt much more confident about my transition project when I left than when I came in. He gave me some exercises to do for practice and said I could get a refresher any time I wanted (wink, wink).

I awaited Friday eagerly, when I could finally see my Flora again and watch our Master use and abuse her. Perhaps Master Magnus would finally let me come. I felt the pain of the cock-cage as my peenie tweaked at the thought. The rest of the week went by in a blur of expectation. It still felt strange for me, who could once go months without an orgasm, now aching for release all the time.

Live as you normally would, Roxanne had said. For me, that didn't involve too much outside activity. I worked from my home office, from early morning to lunch, then I'd either make a sandwich or order from a nearby deli. I might occasionally go to a coffee shop and have latte, while I worked on my laptop.

I knew it was wrong, but by Thursday, I was so lonely, I called Jayden and asked him to coffee. Flora and I had not spoken in almost a week and except for the exchange at Mr. Johnson's, Master Magnus had only texted, "Good, girl!" when I texted after mailing the key. I couldn't call either of them and couldn't talk to anyone else, without relating recent developments.

Jayden was delighted to hear from me. Of course, he would join me for a coffee. "Girl! You sound so hot, now, too!" We decided to meet half way between the city and suburb. I had to stop in a salon to have my makeup redone. I was still not good and ended up looking like clown.

When I got to the coffeeshop, Jayden was already there in a more private back booth. I walked over and he stood up to greet me. I leaned in to hug him, but he pulled me in for a kiss me on the lips, not crudely, but he slipped his tongue in, as I had reflexively opened my mouth to receive it. It was a nice kiss, gentle and warm. I was enjoying it so much, but had to stop it.

"Umm, Jayden," I heard my new "woman's" voice say. We sat down; he was all smiles and exciting me with the way he was leering at me.

He was studying me like hungry wolf, and I straightened to offer myself up. But then, I had to think about my situation. I couldn't do anything with Jayden, under current conditions, though I was so aroused and could feel my wee weenie painfully swelling against my cage again, my butt-plug sending waves of pressure, as my ass twitched eagerly at Jayden's kiss.

"Look, Jayden, I am sure you know I'm very attracted to you. If it was up to me... you need to understand my situation. I can't really start anything with you before I deal with it."

"So, this guy... your "best friend," is cuckolding and feminizing you, and owns your wife? That's some fucked up shit, girl. Why don't you just leave them two fools to each other, and run away with me. You look fine to me, just the way you are, sweetie!"

"I can't, Jayden. She is still my wife! And he's been my protector my whole life. I have to trust he has a plan and wouldn't just hurt me. And, I made a promise, which is important to me.

We talked for an hour or so, while we drank our coffees and ate pastries. He kept making moon eyes at me and propositioning me, and I felt like swooning, like in a Victorian novel at his handsome face. In the end, I got up nervously on shaky legs, and he stood, held me up, and kissed me again this time with even more heat. I melted for a moment and just enjoyed the kiss, but then came back to my senses and gently pushed him away.

"Tch, Sigh! Okay, Drew, girl. Just call me if you need to talk, or anything!" and he winked at me as I turned to go.

I had to tell Master about Jayden, but I had no chance. I was waiting to hear further instructions, or really anything from him. I knew he wanted for me to agree to transition into a girl for him, which I was close to deciding, but not sure I could say it was for him, though I had submitted to him. He wanted me to say I was so desperate for his cock, I would be feminized, but that wasn't accurate, though his cock was ever-present in my mind.

I was desperate to talk to Flora; the person I spoke to about life decisions. It seemed a semantic issue; I was submissive to him and eager to feel his cock inside me. I was interested in transitioning, but not really for the same reasons. After talking to Roxanne and the makeover, and how I had been feeling this week, I was becoming convinced, independently, I had never really been a man. I had conformed to gender norms that never suited me, and had been silently and obliviously miserable the whole time.