From Bro to Sissy Sub Pt. 04

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Part 4 Drew Makes a Radical Choice

Author’s Note: this is a story of consenting adults; no characters under the age of 25 and despite the bondage and S it was now hard to think of her as my wife.

My curated Jayden experience was limited. Master Magnus had let me have him only twice in the month and half or so, since Jay had popped my cherry. Both times were great, but not quite as satisfying as the first. Magnus limited our time to one hour. His cock was out and in me practically from the moment I opened the door until he left. We used up every minute to the last in-coitus. The sex while amazing felt obviously constricted.

The house arrangements turned out very different from originally proposed. He decided to take his condo off the market. He would install his slut in the house around the corner from me, and come out on weekends occasionally, or as the mood struck him. Flora and I would be free to meet, as long as we agreed not to have sexual contact—which, at this point, neither of us wanted from each other.

I was nervous about this development and what it might mean, but I thought it best to leave it to Master’s providence. The movers arrived on Thursday, unpacked and arranged the furniture; and the couple would come after work Friday evening. We were to “celebrate” together: dinner from a swanky downtown restaurant, followed by other “entertainments.”

Dinner was just the three of us, but Jayden would join us for drinks after. I guess part of the “entertainments.” We had “private matters” to discuss during the dinner, he said, to explain why Jayden would be joining us later.

He texted when they arrived; I was touching up my makeup. After almost two months of aggressive hormone therapy. I could not yet call what was happening on my chest “breasts,” but something was definitely developing there. And my testicles and clitty, had thankfully shrunk. I was no longer having erections, it would spasm when I got excited, but I no longer had pain from the cage, which was now a considerably looser fit.

I was feeling very sexy as a woman and looking forward to the first round of surgical interventions still a few weeks away. My libido had calmed some, since that first night with Jayden, which tweaked my clitty. When I thought about it, it was like experiencing it for the first time, and knowing I would get it again made it easier to bear the wait. I was still horny, despite the hormones; it had been a while, but the desperation, the urgency, was lessened.

At their door with a nice bottle of wine, I held it out to… his slut, who opened the door; she pointed me inside, without much greeting. She dressed… like a hooker. She wore:

a white blouse with red polka dots, a collar and lapels, prominently featuring her big fat tits and tied below revealing most of her midriff. The skirt might have been six inches long, ending at the point where her visible thong created a cameltoe in the front. Her ass cheeks hung just below the hem, when she stood up straight. With the slightest bend, her prodigious ass became visible, divided in half by the thong. Emblazoned in red on her right asscheek were the words: “Nasty Ass Bukkake Bitch!” The rim of a buttplug just visible; the thong holding it in place.

She had on white mid-thigh hooker boots, with impossibly high heels. Having always worn flats, she was still shaky in the heels. Makeup matched clothes: bright crimson lipstick, dramatic eye makeup. Her lips, always rather thin, were pumped up, like a blow-up doll.

We sat to dinner, which she heated and struggled served, bringing things in balancing on those impossible heels, but managed it and sat with us. Master Magnus led the conversation as we ate, making small talk in familiar tones. He asked after my work. And I said things were relatively quiet. He asked about her work, and she said laconically, it had been busy. It was clear she didn’t want to be there; or more accurately… she did not want to be there with me. He gave a her a sharp look, and she smiled insincerely.

“Whore… the little cuck sissy faggot has a boyfriend. Who’ll join us later.”

She had seemed not quite present—miles away—but her curiosity was obviously piqued at the comment. I realized he had not said anything to her about anything.

“Hmmm, really?”

“Yes, little sissy, tell my whore about your new beau!”

“Uhm… ermm, I don’t know if I’d call him that, Sir. His name is Jayden, he’s 25, tall, dark and gorgeous, with a fabulous cock!” I said pointedly, her Botoxed lips agape.

“How did you meet this… new beau, cucky faggot?” He asked, dripping sarcasm and disdain.

“He was my masseur at the transcenter, where I go for gender affirming treatment.”

“Uuurphn, uhmm.” She responded like a cartoon character, struck dumb, and her whole façade seemed to fall away. Kartal Escort “Really…??” She asked incredulously.

“Yes, I’m scheduled to have my first surgery in four weeks.”

“So, you are seriously doing this?” For a flash, her voice sounded like the Flora I knew.

“Oh, Flora… I am sorry. All these years I had no idea. I never really noticed anything different about… but I realize now, I was miserable as a man, though I didn’t really know it. I worked so hard to fit into my place in the world that I didn’t notice it wasn’t place at all. I can’t really tell you how much happier I am now, and how sorry I am for you for not knowing.”

After I said this, her persona changed toward me, and she leaned over and hugged me in a sisterly way, after that the mood relaxed some. We spoke less tensely and had some wine. Master Magnus, began to explain the parameters of our new situation. He informed her, though I already knew, that he would not exactly be living here. She seemed distressed with the information, but accommodated herself to the life of sub-slut.

He told me, I would be responsible for caring for her when he was done using her, as needed. I was a bit nervous for both of us on that front. He repeated that he would continue to curate my relationship to Jayden. As he was saying this, he got a roguish smile on his face and reached for his phone. He flipped through his picture, and laughed hardily. When he handed me the phone, I could see Jayden’s beautiful naked body, though his face was digitally disguised.

I hit play, and the twenty second clip began as he presented his unique cock to the face of woman on her knees, already covered with ejaculate. The cock popped in her mouth just a few times then sprayed a massive load all over her face getting some of it in her mouth. Intellectually, I knew this had happened, and that it “paid” for my time with Jayden, but I felt my spirit break a little, as I watched. Although, it was still aroused by it; the thought that he had spurted as much cum in my hole made my asshole twitch.

He showed the same clip to his slut, who made a mewling noise and asked, “is that your boyf… ooooh mmmmph!”

I decided to be proud, rather than ashamed. “Yes, isn’t he beautiful? He took my virginity with that gorgeous penis. Isn’t it fabulous?” I bragged. I couldn’t wait to get through dinner, and have my Daddy come. I hoped desperately that Master Magnus would let him fuck me tonight, in front of his slut, so she could watch me in my submissive glory.

Though she seemed to have forgiven me before, her face changed again when I mentioned virginity. I probably should have made nice, but I thought she was being unreasonable in her response to our situation, which was I couldn’t really help. He laughed hardily at my feminine bluster and said, “he’s a star, your Jay; look at that load. We have to conserve his… erm… energies, hah hah hah!” He laughed ominously.

He clarified that I would have to be punished tonight for various infractions: starting a relationship with Jayden, giving him and unauthorize blowjob, for the times I came during the bukkake, and to pay for Jayden fucking me. I was more than happy to be punished; I did feel guilty for my indiscretions, and I knew it was wrong. I was also delighted to “pay” for my night of passion and the short hours too; I didn’t really care how many lashes it cost.

The whore had already been punished, he declared. She had gotten 73 loads of cum in and on her, so she had been whipped 73 times. I would later see the results on her back. She had to admit that she had loved every single one. He was right; she was whore! She declared to me herself. I had a hard time counting the number of times I had come that night of the bukkake; some I couldn’t tell if it was the same one or multiple. I rounded up to seven to be sure.

We finished dinner and just sat around drinking in the living room; Master Magnus was randomly squeezing and teasing his slut’s tits, as she sat at his feet on the floor, the bell rang; he signaled me to get the door. I hadn’t seen Jay much, and he looked just scrumptious to me, wearing a tight black Tee with blazer over it. He kissed me hard at the door, and I welcomed him and led him to Master and his slut, now engaged in more deliberate sexplay.

She was on her knees between his legs, hands behind her back, suckling on his thumb. He made as if to slap her with the other hand; if she flinched, he would slap her hard. They both giggled gleefully each time he’d slap her, though she, groaned first.

I introduced Flora as His slut. Jayden was very gallant and debonaire; he reached down to the still kneeling slut, her hands still held behind her. She looked over at Master Magnus, who nodded and she met his hand with hers as he took it in his and kissed it. Then Tuzla Escort he leaned down and kissed her on the lips casually.

Then the most astonishing thing happened, which threw me for loop. Master Magnus stood up, leaned over, and as Jayden offered his hand, he pulled him close and kissed him hard on the lips. Jayden, however, didn’t seem surprised, he opened his lips, and they kissed for a moment.

“Come sit by me, Jay!” Master Magnus said in a jolly tone. “Sissy, get us some real men drinks… two Scotches…” He said, while looking over at Jayden for confirmation.

Jayden flashed his lovely smile and nodded to confirm. They wanted ice, and the icemaker in the living room bar was not hooked up yet, so I had to go into the kitchen. When I returned, the slut was kneeling between them, both playing the slapping game, while she massaged their cocks through their trousers.

“Ha ha ha… look, the stupid cunt still flinches, like it makes a fuckin’ difference.” Master Magnus was saying, as he slapped her again. All three cackled in delight at her stupidity.

Her face was aflame with red, and her hooker makeup ran down her face, as her eyes flooded with tears. She now had on a dog collar, like mine; hers read “Cum Whore Bitch!” Attached to the collar was a heavy chain leash. Jayden pulled on it to start his turn at the flinching game.

I brought their drinks and set them on the coffee table in front of them. They took a break from torturing the poor slut. Master Magnus took an ice cube out of his drink and slowly ran it along her bright red cheeks. She mewled with appreciation and opened her fat lips like a carp, begging silently for Jayden’s thumb to suck, ready to go back to the game.

Instead, Jayden pulled down his zipper and pulled out his big spiral cock and yanked on her chain until she was swallowing it eagerly. I was very jealous about to faint from shock. Master Magnus called me over to his other side on the couch, to watch him let the whore devour my “boyfriend’s” cock.

“Little sis, I’m afraid I have some bad news for you. Sissy, I was about to say, he’s going to perform tomorrow, so we don’t want him to get too spent tonight. I want to let the whore get a taste of him, and that’s all he’s going to be able to do tonight. But the good news is you get to watch, while we both fuck the whore. Isn’t that nice, little buddy?”

“Yes, Master. Sir, then, may I please suck your cock??”

“Aww, no honey… Not just yet, little sissy. I have to admit you are looking really good, but I’m gonna wait before I let you have my big cock.”

As he said this, he reached over to Jayden, who had his cock down Flora’s throat, pulled him down, whipped his cock out, and plunged it down Jayden’s throat. As my “beau” was bobbing up and down on the fat cock, Master guided me to my knees so I could see the action up close. Jayden was an accomplished cocksucker and seemed happy swallowing the big cock.

It seemed, my punishment was mixed: to watch as “my wife” and my “boyfriend” were used by my best friend and Master to humiliate me. We soon moved the party down to their newly crafted basement playroom. There, I was stripped by both men and strapped down, by neck and knees—ass high in the air—to a platform about crotch height. Both men came over to me and gave my ass a healthy squeeze and a few slaps. I preferred this to watching Jay get what I so eagerly wanted. I wanted to be punished, ready to be hurt and suffer rather than ignored.

Master Magnus held a large flogger in his hand, while Jayden was working his fingers into my hole, pleasantly opening me up. I pushed back against him with what leeway I had, my neck strapped down, such that I was facing straightforward. I was looking forward where the slut was waiting on her knees, hands behind her back, staring back at me with a sour look. Master interrupted my view and spoke to me in an instructive tone.

“Sissy, we’re going to punish you now, but I am going to leave how much up to you. See this?”

He held up the big flogger and swatted down my back with it as a test run. He didn’t do it very hard, but it stung. One lash struck me just at the top of my ass and sent shivers through me.

“I’ll be striking you harder, how many of those do you want?” I really didn’t know how to gauge; it was an impossible question. I didn’t care how much they hurt me; I was looking forward to the attention.

“Sir, I just don’t know, please, would you decide…. Strike me as hard and long as you would like, Master Magnus!”

“Okay, little sissy, as you wish. How about you Jayden, would you like to strike the sissy? You wouldn’t mind if Jayden punished you too.”

“No, not at all, Sir! Please, I want to feel vulnerable to you both. I’d like that very much.”

“Okay, honey, beg for the first strike.”

“Please, Anadolu Yakası Escort Master I want to feel your punishment so bad.” I sobbed as I pleaded for it.

He struck me much harder than the test run. I was screaming and grimacing. I felt the lashes and welts all over. He moved out of the way so Flora and I were eye-to-eye as he flogged me and made me beg for each strike. Each time he’d strike me, she flinched and closed her eyes, but said nothing. I stared back at her and when I could get myself under control after the strike would make a face to convey the pleasure and pride I felt being struck.

Jayden never stopped fingering my hole, opening me up. Then, I felt him push something bigger than his fingers into me. It wasn’t his beautiful cock but a dildo attached to fucking machine. At low speed, it firmly thrust the dildo in and out of me. I pushed back as hard as I could against the strap, to get more into me, while Master flogged me and made me beg for more. I was happy to; I begged with gusto for more, wanting to out-sub the bitch whore.

Once the machine was fucking me steadily, Jayden around to my front and wiped my tear-streaked cheeks. He wrenched my head up by my hair and kissed me deeply. Even distressed from the flogging and twisting my strapped neck around, I returned Jayden’s kiss eagerly. It made me feel warm all over. My little dicklet spasmed in its cage, though it couldn’t harden.

The feeling in my ass was unbelievable; it was like precision fucking, hitting my prostate just right every time, mechanically but somehow sensuous. Master was striking me at will. He was hitting me quite hard, but I barely noticed; that magic machine pumping pure joy in me. Jayden pulled away and let my head go back to position. It left me gasping; I missed his kiss already.

“Jayden, you wanna strike the sissy bitch faggot?”

“Oooh, yes, Sir!”

“Sissy, you don’t mind if Jayden takes a turn punishing you, do you, bitch?”

Oh no, I didn’t mind, at all. I wanted it. I had hoped for it, since they brought me in here and tied me down. I felt so helpless, so exposed, so vulnerable. I felt like Magnus for all his bluster held back some, taking it easy on me. In a way he had not done with Flora. I wanted to convey to Jayden that I would like him to hurt me more than Magnus had.

I wanted to give him that something extra; more than to Master Magnus, something special just between us, right in front of them. I was looking right into the whore’s face; she had barely blinked watching me trancelike. She smiled or grimaced occasionally, but not at me really. Her mind seemed distant, but she followed every motion with her eyes. Jayden was about to ask me to beg for his punishment. I drew him closer with a whisper; he leaned in to hear better.

“Daddy… please… I want you to really hurt me. Please, I want to come from your punishment. Please, strike me harder than him, make me come for you… just for you, Daddy; just for you!”

He smiled from ear-to-ear, that devastating smile of his, and I smiled back.

“Beg for it, whore!” He sneered loudly, as he moved around to my side.

I pushed back on the dildo slowly exploring my ass and steeled myself for this first strike, and begged for it. It hurt so bad; I was instantly shuddering and sniveling. I knew Master Magnus had been holding back. I felt vindicated; I looked at Magnus’s whore, and she seemed finally to come out of her trance and was looking back actually at me. I smiled at her through my anguished sobbing. Then ostentatiously begged for the next strike.

Jayden was great. He continued to strike at the same pace and then turned the machine up just enough. My little clitty was straining in its cage still trying, but failing to stiffen. The pressure in my prostate was building I could feel myself moving closer to an huge orgasm. I was screaming out as he struck me and begging for more and harder. I was going to come, but rather than beg I just declared it, mostly to Flora, who was still on her knees less than five feet from me, with Master Magnus now behind her leaning over mauling her big tits.

“OOoooh, fuck, Daddy. I’m gonna fuckin’ come, Daddy, one more, please, Daddy!!”

My whole body was quivering, and my tiny clitty felt completely engorged, but still not hard. Inside, the feeling in my hole was amazing; the intruding dildo felt like it was burrowing into my bowels and the constant tapping on my p-spot was making it hard to think of anything else. The effect of the flogging was more psychological than physical. The physical pain was there, of course, but the vulnerability was my real sexual driver.

I felt so exposed and naked; two big strong men had been battering me. But I had turned that pain into pleasure, and I felt invincible. Musclebound Jayden had struck tiny sissy me as hard as he wanted, and it made me come in the most explosive way ever in my life. And… I gave him that; given him total control of my body and to work out his fantasies on me, and still come for him. I felt triumphant, looking over at Flora, about take Master’s cock down her throat.

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