From Bro to Sissy Sub Pt. 01

He pushed on my back until I arched, and I felt a cold and wet drip down the crack of my ass, and then the warmth of his fat fingers massaging the lube into my hole. I tried again to resist by wriggling away, but I was limited by the belt around my neck, and he held me down and forced me to open my ass to him, with my hands tied behind me. He pushed first one fat finger then another into may asshole. This was making my little dick really hard. It was aching from how long and how hard it had remained, without being touched.

There was some pain from his fingers pushing through my sphincter, but it mostly felt really good as he opened me up. Once he had lubed and opened my hole up, he took Flora's hidden dildo and slowly and persistently pushed it into my hole. When he had pushed it all the way to, he flipped the switch and set it on low, and it hummed inside me; The warm buzz all through my body felt fantastic.

It was overwhelming having walked in on him with my wife, and now feeling more aroused than I had ever been in my entire life. He tied some rope around my waist and then between my legs to hold the dildo in place, then pulled on the belt to make sure it was secure and patted my head.

"Drew, you're a sissy sub. Do you know what that is?"

"I'm not sure, Magnus." He tweaked my nipples, gently at first, but increased the force until I was near tears.

"Sissy, you will call me either Sir or Master. Do you understand?"

"Yes, Sir! What is a sissy sub?"

"You've spent your life thinking you are a man. Even I thought so, but you're not really. You're not attracted to women. You find them appealing, but what you really want is to be like them. You are intimidated by real men and want to serve them as a woman in a submissive role. I don't know yet how much, but you need to be feminized; turned into a girl. You may just need to act and dress like a girl (role-playing) or you may need more than that. But, don't worry honey, we're going to find out and get you what you need.

"You were never going to succeed as a man because you don't have the right equipment--and not just talking about the tiny little clit, you think is a penis. Plenty of little to average hung men are not sissies, like you. Had you been a real man, you would find a way to please your woman and yourself sexually.

"There are things you could do about a small penis. But you... you can't get hard even with a gorgeous piece of ass, like this fuckin' whore here. Yet, you have no trouble maintaining an erection, watching me dominate your slut wife, in front of you, with a big dildo up your ass? Do you see how you're a sissy, faggot?"

"Y-y-y-yes, Sir," I answered sheepishly, my penis again betraying me, drooling as he further humiliated me.

"You also enjoy being humiliation. You could have found a way, but you have no ideas because it's not in your nature; you were waiting for a Dom to tell you what to do and use his power over you make you come, like a girl. Don't worry, my little sissy bro; I'm going to help you."

I tried to protest this and deny his diagnosis, but I couldn't deny how turned on I was, or how I kept trying to get a better look at his big cock lolling around, while I pushed back on the dildo vibrating pleasantly in my asshole. He caressed my face tenderly and put the same fat fingers he used on my ass in my mouth and made me suckle them. I should have felt humiliated, but I found it reassuring. I sucked on them gently until he abruptly took them out.

"I'm going to fuck and abuse your whore wife now, my cuckold sissy. You probably won't come from that dildo in your ass tonight yet, while you watch me with your wife, but you will get close, and eventually will. But... if you are going to come from it, let me know first; ask permission, okay, little sis? Otherwise, I will have to punish you for being a bad girl. You don't want that, right?"

He said this kindly, but as if I was wayward child who needed guidance. I shook my head absently, then said: "No, Sir!"

The sudden gender switch should have bothered me more, but I really didn't want to be a "bad girl" and was instantly intrigued by the idea of having an orgasm without touching my peenie. All of my reactions seemed contrary. I should be angry, mortified, embarrassed, but I was aroused, lustful, and eagerly obedient.

"That's very good, sissy Drew."

He got up on the bed between her legs in a half-crouch/half crawl, until he could reach her spread pussy. He leaned in, and with a swift almost imperceptible motion he landed a slap right on her mound. She recoiled, pulling her ropes on all four corners at once and letting out a sharp yelp and grunt. I could feel the bed quake from her reaction, but she thanked him for hurting her, her voice low, deep and gravely from lust. She was sobbing quietly from the pain.

"Whore! Whose pussy is this?!"

"Your pussy, Sir. Thank you, Sir, please, Master, may I have another." He smacked her pussy again and she screeched louder.

He smacked her pussy a few more times less hard, and then began to finger her roughly with first one, then two, then three fingers. Then, he used two fingers from each hand and pushed them in her hole and spread it open. She was undulating her body against the restraints and moaning wildly. Magnus made sure I could see everything from my perch; he had turned the lamps on both sides of the bed and the overhead lamp in the room. I could see and hear how wet her pussy was as he massaged more and more fingers into her open hole.

He suddenly straightened up from being on all fours working her pussy and leaned back toward me and pushed the fingers from her cunt into my mouth. I sucked on them willingly and lapped up my wife's juices from his fingers. It was mouthwatering to me, and I pushed back against the dildo to emphasize my pleasure.

Then he turned back to her and crawled further up her body, until he got to her magnificent tits. Nora and Flora were similarly built, but my wife had by far the nicer breasts. They were big and round (taking up the majority of her chest). Her nipples were simply spectacular, big round bulbs, much darker than her fair skin. They were taut and stiff with arousal then, and he twisted them around between his thumbs and index fingers, like he was tightening a bolt. I could see the pain on her face, and heard her say:

"Yes, yes, yes, oh Master, hurt my titties, please. Harder! Yes, fuck, fuuuck!"

He was happy to oblige and now held up one breast by the twisted nipple and used the other hand to slap at it, then repeated the process with the other. He let them go, and just pummeled them with slaps and punches, while she continued to scream in pain, and encourage him to further abuse her gorgeous tits.

When he was done, her tits were covered with bruises and red marks. He seemed ready to fuck her and positioned himself at her entrance, but the angle of her legs was too awkward. He untied her legs from the bottom posts. Leaning over to me as he untied her from my post.

"Oooh, cucky Drew! I'm about to fuck your dirty whore wife's cunt, right in front of you! Are you excited to see my big cock fuck your wife's hole?"

"Yes, Sir!" I couldn't believe it myself, but... I actually was! I was eager to see his big real man cock explore my wife's vagina how I never could.

"You know, I've only fucked her a few times, mostly she's been sucking my cock. She was so tight that first time; there was a lot of blood; I think she might have still been a virgin, sissy. I don't think your little clitty ever pierced her maidenhead. Oooff! She was tight! That's why I gave her that dildo in your ass; she was so tight; it was uncomfortable for my big cock. I'm sure you never had that problem, huh, sissy?"

He re-tied her legs at the knees to the upper posts above her arms. She was splayed out with her hole beckoning. He moved in, and I could barely see her under him from my position. I managed by partially choking myself to maneuver the belt down so I could just catch her still tight hole open up to his cock.

He pushed through, and she shrieked, as he had not eased in at all, but pushed that foot-long steel rod into her with all the force of his big man body. She screamed out "Oh fuck, oh fuck, oh FUUUUCK!" a word I had heard my dainty, soft-spoken, wife say maybe twice in the years we had been together, and now seemed a regular part of her speech. Then... "YES! Fuck my dirty fuckin' cunt with you big fuckin' cock, Master, please!"

He needed no encouragement and began to assault her hole with vigor. He didn't warm up to it, or build up momentum; he just started wailing into her full force, full speed and all the way out and back in. I could only see by leaning hard against the belt and choking myself, but I couldn't keep my eyes off what he was doing to my wife. I would only stop peering when I felt light-headed and thought I might pass out.

I could see a froth building up around the base of his fat cock as his pace aerated their effluvium. Her very loud moaning no longer bore a trace of pain he inflicted, now it was pure pleasure. She continued to repeat "yes, yes," "fuck my pussy" and "thank you for fucking my dirty cunt, Master," and making these delicious moaning noises.

"You are dirty filthy fuckin' whore, bitch. Tell your husband how much you love my big cock!"

"Oh, sissy. He is fucking me so fuckin' good. That big fucking cock is turning me into goo, honey. I love his cock more than anything in the world. I'm sorry, Drew; I can't help it, I'll do anything for it. Ooooph, mmmm! Fuuuck my cunt hard, Master! Take it; hurt me with that fat cock, Sir!"

"You hear that, little sissy cuckold? She loves my cock more than she loves you. That shows just the kind of filthy fucking slut you have been keeping from her true nature."

He took this opportunity to smack at her tits and face alternately, and pinch her nipples again hard like before. Her sensual moaning turned to whimpering as he increased the violence, while maintaining an impossible pace thrusting into her full throttle.

"You don't mind me giving you pain, while I fuck your nasty hole, bitch?!"

"Oh, no, Sir, please. I love the way you abuse me, thank you, Master, just please keep fucking me hard!"

He didn't disappoint, and soon she was moaning again, and as he sporadically abused her tits and nipples, she began begging to come, and her breathing, already labored, sounded like she might have a heart attack.

"Ooooh, ooh, mmm! Please, Sir may I come for you, please. You're fucking me so good, Master, I need to come, please??"

"I'm sorry, whore, but not yet." He stroked into her pussy a few more times considerably slower, then pulled out of her completely. "Wooooff! Shit, bitch that's one sweet tight cunt, but I want to finish in your other nasty hole. Did you clean yourself out, like I told you, whore?"

"Yes, Sir! Right after the cuckold faggot went to sleep. I am sooo ready, Master. I've been practicing with the dildo, like you said; please take my ass too. Open my fucking nasty asshole up, Sir, please! I don't care if it hurts! Fuck me hard!"

He turned his body around on all fours, straddled her head and pushed his big slimy cock down her throat. He leaned forward and used his big hands to show me her gaping pussy. He first slipped four fingers on his right hand in her wide-open hole and massaged them in, then added one from his left until he had eight fingers minus the thumbs of both hands slithering in and out. She was hyperventilating with the big cock in her mouth and her bottom was writhing around trying to push her pussy up for his attack.

"Look, at her nasty fuckin' gaping pussy, sissy! That's what my big fat cock did your precious wife. See how she reacts. Now, I'm gonna do the same with her other hole! Are you enjoying watching me fuck this whore, little buddy?"

"Yes, Sir," I said more eagerly and louder than I meant.

Having my asshole filled with that dildo humming all this time, as I watched Master Magnus dominate my wife's body had me in a fragile state. My teeny penis had been straining hard longer than ever in my life. I was leaking pre-cum copiously, and I couldn't much focus my mind on anything except those physical feelings and the drama unfolding before me.

Trying to work up the anger I felt upon discovering them, I would be instantly distracted by some new view or internal feeling that brought me back to my ever-present arousal. As I would come to realize later, the dildo was not generating enough force to stimulate my prostate into an sissygasm, but the cumulative effect of the humming and the delicious feeling of fullness, and the emotional emasculation kept giving me hints of how powerful it could be.

He was now pretty much fist-fucking Flora and making sure I had clear view. He coned the fat fingers of one hand and worked them into her dripping wet cunt.

"Oh, fuck, Sir, fuck, fuck. Ummmm, ooooh, aaaaah, ummm." She grunted, working his cock out of her mouth.

"You like me fist-fucking you, slut?"

"Oooh Fuck! Sir please, please fist-fuck me, Sir. Open up my cunt for your big cock, Master!"

He continued working his hand into her past his knuckles; she gasped and cried out as he finally went in to his wrist, and he was officially fisting my wife's tender pussy. He let it be there for a beat rotating it slowly and using his other hand to spread her goo on it. Then, he began to slowly fuck her, pushing further in with his fist to his wrist and pulling out. With each pump, he would go a little further in.

She was growling with his dick back in her mouth and her legs were shaking as he began to fuck her in earnest with his fat fist. She moaned wildly and tried to get her mouth free to say something, but he wouldn't let her, keeping his cock firmly planted down her throat. It was obvious she was in the midst of an intense orgasm, as her legs shuddered, and lower body wobbled violently and she moaned and grunted onto his cock.

When she had settled down, he pulled his cock out of her mouth and his fist out of her pussy. There was an audible plop, when he did, that scared me.

"Whore! Did you just come after I told you to wait until I fucked your ass?"

"I'm so sorry, Sir! I couldn't stop it, Sir, you made me feel so fuckin' good, and I couldn't ask. I'm sorry, please punish me, Master!"

"Slap!!!" he hit her now gaping pussy with great force, which made her shriek loudly, and start bawling and sobbing her eyes out. He gently caressed her injured mound as it turned crimson red. That's when I first noticed her pussy was utterly hairless. I had not exactly seen her naked pussy all that many times. The few times we'd had sex were in total darkness and under the covers.

I had seen her fully naked just a few times here and there, mostly by accident, walking in on her in the shower or changing; and even then, she'd try to cover up. For all I knew, she could have kept a bald pubis the past two years. As I pondered this important question, I realized Master Magnus was right: I had wasted a lot of her sexual life without giving her what she seemed to need. Master Magnus was playing her like she was a Stradivarius and I couldn't get a note out of her. Suddenly, my anger turned to terrible guilt.

She was a beautiful woman nearing thirty, and I had basically kept her a "virgin" with my tiny ineffective peenie. I felt shame as I watched my closest friend provide her with more sexual satisfaction in a moment than I had our entire lives together. Meantime, I was verging on orgasm watching, with a dildo up my ass. He was totally right: I couldn't really be a man.

He had begun opening up her other hole, pushing his fingers in and massaging her beautiful ass. I was still in a numbed-out state, where I was perpetually building to a climax that would never happen. It was frustrating, but the dildo in my ass was so pleasant as it hummed away mildly. But what I really loved was that warm feeling of fullness in my guts.

Magnus suddenly paused his ministrations with my wife's butthole and seemed to get an idea. He leapt up off her face and rolled off the bed. He went around the head of the bed and untied both her legs and arms. He had her turn over and get on all fours and crawl backward toward the post to which I was harnessed. Her ass got so close to me that I could smell the sex on her.

Once he was happy with her placement, he angled her facing the post kitty-corner from mine, then had her get down in the front and pulled arms down under her. He tied her wrists together and pulled the rope taut around my post and tied it firmly. He positioned her legs to make sure they were spread wide and her back arched high.

When he was happy with this, he went around to her head. Her face was pressed down on the bed by her weight. He pulled her head up by the hair and slip a rope noose around her neck then let it down. He pulled on the rope until she gasped, and tied it to the post diagonally across from me.

"I want you gasping for air, whore, but not quite passing out. Is that tight enough?!"

"Aghgh, Thur, ss toooo aighght."

"It's too tight, slut?"

"Yghgh!" She tried to lift her head and nod, but couldn't.

I thought he might loosen the rope from the post, but instead he took her head in his hands and pulled against the rope, nearly choking her out, but stretching the rope to give her a bit more leeway. He laid her head back down and tugged at the rope around her neck. He also pulled on her hips to move her body ever so slightly forward tightening the rope around her wrist.

"How 'bout now, slut?"

"Beddeh, Thur." She croaked.

"Do you want me to assfuck you, whore?"

"Yeth, thir, pwweeeth!"

"You don't mind if I flog your beautiful ass first, bitch?"

"Oh no, Thir, pweeeeth, make ma aath yourths, Mathter!"

He took a small flogger out of the bag and straddled her facing me directly. Her ass was just beyond arm's length from me, maybe three feet, and he was half sitting on her arched back, maybe another foot and a half from my face.

"Aaaah, little sissy! I am having so much fun with this whore. Isn't she's magnificent!? Wait till you see how red and bruised this fantastic ass is going to get before I finish with it. You have no idea how much I enjoy hurting and humiliating sluts like this, and little sissy faggots like you. You want me to enjoy myself with her, don't you, sissy Drew? You want to be a good little cuckold sissy, for me?"

"Yes, Sir. Please enjoy her. I see how much she wants it. You were right I have been preventing her from enjoying a sex life."

"Good, little buddy, you are starting to see. Beg me, Drew! Beg me to flog your wife's ass for my pleasure!"

"Please, Master Magnus! Flog my wife's ass for your pleasure, please, Sir!"

"Awww, my little sissy friend. I am so glad you've come around so fast. Don't worry, Magnus will sort you out. You'll be happier as a sissy faggot, trust me. Should I beat her ass hard, sweetie?"

"Yes, please, Sir!"

He was looking right into my eyes (almost through them), as tears welled up, and I sobbed silently, gasping repeatedly.

"Aw, my little sissy. I know it's emotional. But it's what she really needs and wants. Isn't it, whore?"

"Yes, Master abuse me to please yourself!"

He reached out his giant hand and tenderly stroked my cheeks. I leaned out toward him to get more of his caress, choking myself to do it. He placed two of his big fingers in my mouth and let me suckle them again. I took them happily and whimpered on them until I had pacified myself. I wasn't exactly sure what particular thing had set me crying, but his digits in my mouth had a mollifying effect. It felt so pleasant to be full on both ends.

He pulled his fingers out of my mouth and moved them pointedly into her ass, and then he brought them back into my mouth. Now he put three fingers in mouth; he let me suck on them again, but then he began to slide them deeper and letting me choke on them. I tried to give his fingers a blowjob the best I could, but my cheeks kept getting filled with air, and I was having mini explosion of my lips flapping around his hand as I choked, until he pulled away.