I Own You Now Sissy

I Own You Now, Sissy

When I saw his ad online, I was instantly intrigued by the headline. It read: "DOM MASTER SEEKING SISSY SUB FOR TRAINING." There was a pic attached of a headless man dressed in black leather holding a pair of steel handcuffs in one hand and his massive cock in the other. Now, I was used to seeing ads like this, and most of them were either dreamers or scammers; married guys who liked to dress up while their wives were away and masturbate while chatting with other guys on the internet, or scam-artists claiming to belong to huge international conglomerates of Dominants who will invite you into the fold for a few hundred dollars. Having been in the scene for over a decade I'd learned to spot them from miles away, and often blocked their profiles without conversation. But this one seemed different.

"EXPERIENCED DOMINANT ALPHA-MALE SEEKING SISSY FOR SEXUAL OWNERSHIP, TRAINING, AND RAW FUCKING. NEWBIES NEED NOT APPLY!!! PM ME WITH A LIST OF YOUR HARD LIMITS AS WELL AS PICS OF YOURSELF DRESSED FEMININE, WILL ONLY RESPOND TO THOSE WHO ARE EXCEPTIONAL."

I hardly saw myself as exceptional (I was too tall and broad shouldered to be passable), certainly not as hot as some of the MTF folk coming up in the scene who were half my age, skinny, and had long natural hair. I responded to his ad anyways, and was surprised that he responded within an hour. We agreed to move the conversation to a private chat room where he instantly dove into my experience and preferences.

"How long have you been sucking cock?"

I blushed at the question, the abruptness of it. "I dunno, 20 years or so?"

"Have you always done it dressed as a sissy?"

"No. That part is fairly recent, though I've been secretly wearing panties for as long as I can remember."

"I figured as much," he wrote. "That's always the story with sissy faggots like you."

My hands left the keyboard and I sat back on my sofa, reading and re-reading the words on the screen. Sissy... faggots...

After a moment, he acknowledged the potential insult; "Have I offended you?"

"A little," I admitted.

"Oh no, don't misunderstand me, I don't mean EITHER of those words as an insult. I think our generation was brought up to see anything less than totally masculine as a weakness of some kind. Little boys on the playground will call other boys sissy to hurt their feelings, just as teens will use the word faggot to insult each other or even to entice someone to fight them physically, as a test of their manhood and their place in the social hierarchy. Same goes for the word "bitch" inside the prison community. In the movies prison sex is rarely consensual, and the person getting fucked isn't valued, but that's not the case at all. In fact, bitches in prison are HIGHLY valued and protected by the inmates. Makes sense when you think about it, if you're facing a life term in prison and you're never going to be with another woman then you'd better get used to having a man suck your dick or else it won't be getting sucked period. Bitch, sissy, faggot, slut, cunt... these are all words I use to address my submissives, should you become one of them."

His explanation made sense, and my reaction to those words wasn't his fault; it was how society had raised me to react. In the grand scheme of things they described me quite accurately, so I made a mental note to disregard their connotations outside the context of communication between a Dom and a sub.

"Thanks for clarifying," I wrote. "I can live with that."

"Good. So... my potential cocksucking-sissy-faggot-bitch, you like to wear women's panties, why is that? What is it about them?"

I had already begun to type when another message from him stopped me. It said: "Don't say you don't know. That's not acceptable."

I deleted what he knew I had written and thought about it for a moment before responding. "Whenever I put them on, I feel sexy. Sexy and at the same time I feel vulnerable."

"Good answer. I know exactly what you're talking about. Do you know why so many attractive females like to wear skimpy bikinis at the beach?"

"I don't know, to get a good tan?"

"That's just window-dressing. Think about it. Name another place other than a strip-club where it's entirely acceptable for a woman to parade around in what amounts to nothing more than a bra and panties. An attractive woman knows that men are looking at them all the time, and most of the time they're imagining fucking them and imagining them naked. As a society, we've decided that it's acceptable for women to wear next to nothing as long as they're standing on sand, and it's acceptable for men to LOOK at them doing it. Whenever a sissy like you puts on a pair of sexy panties, you get a little taste of what that attractive woman on the beach gets to experience every single day. You get to see yourself as desirable."

I was staggered by his insight, and told him so. "I've never heard anyone say it like that before, but YES! That's exactly how it feels."

"You want men to see how sexy you are and desire you, that's why you dress up and post naughty pictures to strangers on the internet. You like that men want to fuck you, don't you?"

"Yes, I do."

"But I'm guessing that most of the men you've been with aren't gay and probably aren't actually bi-sexual, they're just middle-aged guys living in sexless marriages who aren't attractive enough, rich or charming enough, to get an actual woman at least as attractive as you are who will suck their cock or maybe even fuck on the first date..."

He wasn't wrong.

"... so they pretend you're something other than a guy dressed as a female-hooker, and they get to have an orgasm. And you get to pretend you're a female, albeit something of a promiscuous slut, and you can get some dick in you. Both parties are happy, and nobody loses an eye or a finger, right?"

Again, I couldn't argue. "Right."

"See, that's not what I am, not even close."

I found myself leaning towards the screen of my laptop, twitching in anticipation as a little circle spun in the chat box indicating that he was writing, and writing, and writing some more. When his message finally appeared, it took up a full page.

"Let me tell you a little about me. First, in case you're wondering, I'm 6'5", 220 lbs, and I have a 9" cock that stays hard for hours. I can cum up to 5 times in a single session with a sissy, which usually ranges from 8-12 hours..."

My guts twisted at the thought of it: 12 hours. I'd never been with a man for longer than 6 and we were asleep for at least half of it.

"... Only two things will stop play between us. One, if you pass out. Two, if you say our agreed upon safeword. Outside of that I'll be increasing and decreasing the levels of intensity based on both your verbal and non-verbal cues. This will NOT be a matter of you just laying there while I fuck your mouth and ass, I will be playing you like an instrument. Every thrust, every slap on the ass, every word spoken will be like a note in my symphony. I want you to tell me your hard limits, now. Those will be the only notes I'm not allowed to play, and I'll have to adjust the music accordingly so I need to see if I can work with what your instrument can provide. That said, if I CAN work within those restrictions, I can promise the following things.

You WILL feel sexy and vulnerable. You will also feel used, degraded, humiliated and loved, all in the same session.

You WILL be safe and protected against all harm while under my control and care. You can stop the session at ANY TIME with a safeword, and what happens stays between us.

I WILL leave you feeling as though you've been fucked by a freight-train, your belly full of cum and your ass sore for at least a few days.

That's what I bring to the table. So, let's have those hard limits and see if I can hear the tune."

My heart was pounding in my chest nearly as fast as my fingers raced across the keyboard, as I wrote what would surely disqualify me as a candidate in his eyes. "Kissing, rimming, fisting, watersports, branding, sounding, punching, breath-play... " I paused, unable to think of anything else, but knowing I'd left something off the list. I hit the enter key and waited for his response, sure that he would say I'd listed a deal-breaker.

"I can work with that," he replied. "But for arguments sake, I'd like to run a few things by you. All I need is a simple yes or no, but I won't necessarily do them all anyways. I'm just trying to get a little insight into how you're wired. Kay?"

Excitedly, I replied, "Yep! Fire away!"

"I like my girls shaved bare, is that a problem?"

"No."

"Good. Do you swallow?"

My initial response was, "sometimes," but experience informed me that he wouldn't accept that. Glancing up at the pic of his cock I thought back to the dozens and dozens of men who I'd serviced in the past and swallowed for, and this man was far superior to them. I answered, "Yes."

"Do you consent to being tied up, handcuffed, or otherwise restrained?"

"Yes."

"Good. While restrained, do you consent to the following acts, answer for each please, being spoken down to or degraded?"

"Yes."

"Being struck on the ass with a hand, paddle, or belt provided the skin is not broken?"

"Yes."

"Being left alone while restrained either in the dark, blindfolded or otherwise deprived of your ability to hear, see or speak?"

"Yes."

"Being compelled to perform felatio, regardless of tears or discomfort up to and excluding use of a signal or the safeword?"

"Yes," I said, but then added, "but I'd want to know how to stop you if I'm unable to say the safeword."

"Easy," he responded. "Clap your hands. If your hands don't reach, then snap your fingers. The instant I hear either of those things, I'll stop what I'm doing and immediately untie you. Are you good with that?"

I certainly was. "Yes, that'll work."

"Good. Now, onto some things that we shouldn't have to discuss, but unfortunately we do. Have you ever had an STD?"

"No."

"Do you get tested?"

"Yes."

"Can you provide proof if asked?"

"Yes."

"So can I. Have you ever had anal sex without protection?"

I let out a sigh and answered, slightly ashamed. "Yes."

"Provided that I am clean, will you consent to that with me?"

"Yes."

"Good, because I intend to breed you like the bitch you are. I want to use my cum as lube for the next time and fuck you until you're full."

Shifting in my seat, I asked, "I hope you're not going to hurt me too badly."

"No, not too badly. I'd work you in slowly for the first round, then get progressively more rough as we go. It's of absolutely no benefit to me to tear up your ass during the first round and make you use your safeword or signal to me that you're done. I want you to last as long as I do, which for our first session will probably be at least four hours."

Four hours... I thought, looking at the pic of his thickly veined cock and wondering if I could handle it for that long.

"So..." he wrote after a minute had passed, "would you like to hear what I have in mind for your sissy holes?"

"Yes, absolutely."

"I want to come into your bedroom while you're sleeping, I want to find you sleeping in sexy lingerie. I'm going to get my handcuffs on you, and then I'm going to fuck your holes until I'm done. I'll be taking short breaks in between rounds to get cleaned up and prepare, but you'll remain in cuffs until I either finish with you, or you say the safe-word. When I'm done I'll take off the cuffs and lock the door on my way out. Now... what do you say to that, slut? Think you can handle it?"

Aside from leaving my door unlocked for a stranger I'd just met on the internet, it all seemed pretty reasonable. My building was equipped with cameras so I wasn't too worried about him robbing me, and he didn't seem the type to trick someone into meeting so he could beat the shit out of them, so I answered, "Yes, I think I can handle that."

"Good. When we make our date, I'll want you to shower right before bed and shave your body bare. Do you douche your cunt?"

"Yes."

"Excellent. Make sure you're prepared to get fucked for several hours. Then, put on something sexy, unlock your door, and go to bed. I won't tell you exactly when I'm coming over, but it'll be between say midnight and two o'clock. Does that work for you?"

"Yes, that works for me," I answered sheepishly.

"Okay then... let's figure out a night and make this happen."

* * *

The date was set for the preceding week; Saturday sometime between eleven PM and three AM. I was dressed in a red satin nightgown stockings and matching panties, and topped off with a wig of heavy red curls. I was still awake at two o'clock, listening, waiting for him to come in. Laying there under the covers, I tossed and turned, grinding my hips into the mattress and fantasizing about what he might do to me. At some point, I fell asleep and quickly dropped into a dream that I was being pursued through a cemetery wearing nothing but a pair of panties. I could hear the voices of the men chasing me of which there were several, but I couldn't tell how many there were, or what their intentions were.

I was still running from them when I was snapped out of the dream by the cold hardness of handcuffs being snapped around my wrists. I lifted my head to see him faintly by the light I'd left on in my kitchen; he was standing over me dressed all in black and holding a thick black butt-plug in his hand. "Hey, you made it," I said. "What are you going to do with..."

He jammed the plug into my mouth before I could finish speaking, and began winding out black electrical tape from a roll he produced from his pocket. He wound the tape around my neck and mouth, preventing me from speaking, and more importantly: from spitting out the plug even though I was gagging on it.

"Shut up, you cunt," he hissed at me, before exiting the room, leaving me laying there with hy wrists cuffed securely behind my back, and the rubber butt-plug almost in my throat. I'd never gagged so hard in my life, and a terrifying thought occurred to me: what if I puke with this thing stuck in my throat? I was contemplating the idea that I might choke to death when I saw him return through blurry-eyed tears. He approached the bed and removed the crotch of the pants he was wearing and I could make out the size and massive outline of his flesh contrasted against the black outfit.

"Want me to take that out?" he asked quietly.

I nodded vigorously.

"No," he said after a moment. "I think I'll leave you here a while longer."

He turned to leave and I began to thrash and plead with him as fresh tears sprung from my eyes. He stopped short of leaving the room, turned back, and approached the bed. "If I do that for you, I expect something in return. Got it?"

I nodded emphatically.

"If I take that out, you're going to suck my cock until I cum, and you're going to swallow it. If you don't... the plug goes back in for a while and then we'll try again. I can stay hard for hours so we'll keep trying until you get it right. Understand?"

I shuddered at the thought of repeating this exercise, and I nodded that I understood what he expected of me.

He yanked the tape, stretching it until it fell around my neck like a collar, and in one swift motion he slid the plug out of my mouth, grabbed the back of my head, and slid his hardened cock into the place the plug had been and began to fuck my face.

I choked and coughed at the same time, blowing my own spit out of my nostrils like snot and it ran down my upper lip onto his cock where it served as additional lubricant.

"Harder, cunt," he growled. "Suck it harder, and use your tongue. Don't be shy, I know you're a cock-sucking faggot and you've done this before. So DO it."

I did my best to comply; swirling the tip of my tongue around the head of his cock and squeezing my lips hard around the shaft as I tried to maintain suction. "That's better. See, I knew you were a cock-sucker. How many cocks do you think you've sucked?" he asked rhetorically. "A dozen? Fifty? A hundred? A thousand?"

I thought about that for a second while he continued to pump my face.

I'd been sucking guys' cocks for about twenty years. On average I'd say I met a new guy to play with about once a month. Of those guys, the vast majority came back at least twice more before guilt over their infidelity or perceived homosexuality, and while a few became regulars and received a dozen blowjobs over the next year several did NOT come back for more, so in the end I used three blowjobs per guy as my baseline.

Twelve guys, three blowjobs per guy: thirty-six blowjobs a year.

I honestly felt that number to be lower than the reality, but I went with it.

Thirty-six a year, multiplied by ten years was three-hundred and sixty. Or, seven-hundred and twenty over the course of twenty years. Damned if he wasn't close. And if it was seven-hundred, it really COULD be a thousand because, well, some years were much busier than others.

I thought about that for a minute while he fucked my face: I've sucked a thousand cocks.

Well, not really. I'd potentially sucked cock a thousand times, which is a little different than having performed felatio on a thousand different men, but I realized at the end of the day it wasn't that different. On about a thousand different occasions I'd allowed a man to insert his erect penis into my mouth and stimulated him until he reached orgasm.

It seemed impossible but the math checked out.

Even if I could go back and discount the dry spells and the few no-shows over the years, we are still talking about what... eight-hundred, or nine? Suddenly, the term I so easily took offense to, that of "cock-sucker", seemed abundantly appropriate. Because anyone who'd done that as many times as I had could only be described in one way.

I began to taste the cum leaking out of him as he got closer to climaxing. Suddenly he stopped thrusting, and held his cock in his fist and jammed my head down on it. "Here it comes, your sissy-faggot. Here it comes..."

Hot cum splashed the back of my throat in long ropes as he jammed my head down on his cock, his body jerking in short spasms as he unloaded into me. "That's it," he said through a moan. "That's a good little slut."

He abruptly yanked his cock out of my mouth and climbed onto the bed atop of me. I felt his hands on my ass followed by the abrasive pulling and tearing of my panties being torn off. I almost protested; those panties had cost me $25 but within a couple of seconds he'd torn them off of me so it became a moot point. He balled them up and jammed them into my mouth, using two fingers to shove them deep into my palate until I couldn't get my tongue under them to push them out. I became aware that I was now naked from the waist down except for the stockings on my legs. I felt him spread my cheeks and spit on my exposed hole, and I thought to myself, "He can't be ready to go again already, can he?"

He wasn't.

A moment later I felt the rubber tip of the butt-plug pressing into me, and once he'd found the sweet spot he shoved it inside of me, hard, and gave my naked ass a hard slap. "There, I'm going to give you some time to get used to that."

He left my room, closing the door behind him and plunging me into darkness. I laid there whimpering and groaning from the discomfort. The cuffs were digging into my wrists, the panties jammed dangerously far into the back of my throat, and now the searing pain of the plug invading my exposed ass.

I heard the toilet flush followed by the heavy sound of footsteps clomping down towards the kitchen. A moment later I heard my fridge door slam and footsteps returning. My bedroom door opened and he came inside, pushed the door closed behind him, leaving it open just a crack so he could see me by the light coming from the kitchen.