Letting Strangers In Ch. 02 of 04

Letting Strangers In -- 2/4

"On the bed." He instructs, "Kneeling." He lifts my legs one after the other, placing them on the bed near the edge so I am kneeling with my feet over the edge, legs spread so my pussy is at the same height as his crotch. He holds a shoulder with one hand while pushing me forward with the other until my face and chest rest on the bed. The perfect breeding position. He let's go of my shoulder and beings both of his hands down hard on my presumably already deeply red ass. He steps away for a moment and I hear some light clattering to my left. I dare not ask, nor do I care.

"Lube?" he asks.

"Uh... Y-yes please?" I say, though I would have given in if he said no.

He laughs, loud. "No, you dumb fucking slut. Where is your lube?" still laughing as he finishes his question.

I blush, slightly humiliated, "Bed side table, second drawer... sorry..." I say, embarrassed.

I hear the drawer open, close, and then the sound of a bottle being popped open from behind me. I'm not sure how much he poured on me, over me, but I am sure that it was very... liberal. I could feel it run down my taint and over my cage. He spreads it around my hole with his hand, dipping his fingers into me, shallow, but enough to coat the inside of my ring.

The is a pause in action, but after a moment I hear the cap snap close, followed by a thump of it landing next to me. I hear what can only be the schlicking of Wolf massaging the lube into his cock, it continues for a while, I hope he is getting hard for me.

The wet sounds stop, nothing can be heard, just my own heart beat as blood flows downward towards my brain, I hold my breath. Then a shuffle, footsteps? I squirm, tingling with excitement, whimpering in protest for the wait.

Then I gasp, I don't even mean to do it, I have been known to play up my vocalizations but not this time. Wolf presses his legs against the back of mine, puts his hands on my hips, the pushes forward. His cock glances off the edge of my pussy, almost a hole in one. It slides up nudging my tail bone. He stays like this, grinding back and forth, playing in my lubed up crevice.

"Alright," Wolf says, prodding at my hole. "This is it. You ready to take the final step? After this there really is no going back. Once you get bred by a real man that is it. You are locked into the sissy life. Nothing will ever. EVER. Feel as good as what you are about to feel. This will change you, or... unlock what you have kept down for so long. No going back. Are you ready?"

I shiver, his words hit deep, I know I want this. All the hypnosis, the porn, the dressing, the shaving, the workouts, the diets, growing my hair out, perfecting my deep throat skills, daily anal training, the list goes on and on. It's all for my sissy side. All for cock. All just to get used. All just to get fucked. Just like I am about to be. I am so fucking ready, I have waited far too long to let this side of me out. This is it. This is me, I am about to be fucked into another existence.

"I am so goddamn, fucking ready." I say wiggling my hips and ass against him.

"Beg," He says, teasing my hole, edging closer to slipping in. "Beg me to make you a true sissy. Beg me to fill you up. Beg me to open your eyes, your mind, your holes." He slaps my ass, a prompt to begin.

I am desperate, and even though deep down I know he is going to fuck me no matter what I say, his words make me feel anxious. What if he leaves? What if after all of this he says I am not good enough? That I don't truly want it? That I don't deserve to be a sissy?

No! I scream, internally, defiant. This is who I am, he has the key to let it out. I will let it out!

"Look at me." I say to wolf. "Look at the steps I have taken. Remember all the compliments you gave me, about my body? About my ass? About me?"

He chuckles, massaging my ass. "I sure do." He replies.

"Then you know. You know this is who I am, or... who I am meant to be." I am vibrating, nervous and determined, I need this. "Do I not look the part?"

Wolf sinks his fingers into my plush ass cheeks. "You sure fucking do." He says.

"Then please, please make me a sissy, in here." I say, though I have no way of motioning to my heart or head. "Make me a sissy inside, I don't just want to look the part, I don't just want to act the part. I want to be the part." I push my ass back against him to drive in my words.

"Fair enough, all good words, but..." He slaps my ass hard. "I told you to beg. Not fucking whine about your feelings. Now. Beg." His hand slams down on my ass again.

I cry out from the force of the last slap. My heart is beating heavy in my chest as I prepare to beg like a deranged whore. "Please, wreck my pretty little sissy pussy with your thick fucking cock. Please fuck me until I collapse. Please leave me sore and gaping for days. Please, please, please, pllleeease..." I can feel his cock grow a little harder as I beg, I can't help but smile. "Please use me like the whore I am, destroy my pussy, batter my bitch button, red and raw, black and blue. I don't care just please, please please fuck me like the nasty whore I am, then fill me with your cum and make me a true sissy slut. Please... Daddy..."

"Well shit," He says, pulling his hips back and removing one of his hands to guide his cock. "That was all you had to say. Wasn't so hard was it? Say hello to your brand new life, you fucking slut."

The angle is perfect, I know this time he means it, now he isn't just teasing me. His head begins to spread me as Wolf pushes forward. I whimper, he isn't even inside yet, his head isn't even in. It keeps spreading me. I can feel the burn, the stretch. He is definitely wider than the plug, maybe another half in diameter, though it is hard to tell.

I start to reflexively pull away from the insertion, he hooks a hand in my hip and pulls me back, holding me in place.

"Easy there girl, still got a ways to go." He says, groaning at my tightness. I can only reply with a whimper, but try to still my hips.

I don't remember it being this thick in my mouth. I thought that after all the play with the plug, after all the lube, after all my training... But I guess nothing can help it when the real thing is just too thick. Well, maybe not too thick, it is uncomfortable, but the stretch isn't painful, not yet at least. I can only imagine what my hole looks like right now, stretched to the point that every wrinkle disappears, just smooth pale pink skin.

"How you feeling down there sissy?" he asks with a touch of concern.

I huff, trying to control my breathing, trying to stay still for him, trying to still my instincts to move. "D-doing okay... This... is what I... I need this." I say, dredging up enough resolve to push back on him gently.

"Mhmm," He grunts in agreement, pressing harder into me, slipping a miniscule amount through me ring. "You sure fucking do, you are so fucking tight."

The agonizing slow push is over in an instant, after what seemed like an eternity I was getting close to quitting, the stretch was almost, nearly, too much. That instant that my ring slipped past his head and started to suck him in, I let out such a loud, whoreish, moan that I am sure it was heard from the street. He was in, He was in, He was in! He is in! This is it, now all I have to do is accept whatever he throws at me. Now all I have to do is take it.

"It's a shame sissies don't stay this tight forever. Though I am sure we could add some kegels or whatever to your routine to keep you from getting completely fucked out." He slowly plods along, creeping deeper into me, spreading me wide around him as he does. "Unless of course you want to go down that path, always gaping, always drooling lube. Massive plugs stuffed in you around the clock to keep the loads from dripping down your legs."

I let out a desperate moan as his fat head slides past my bitch button, creeping deeper. His dick is so thick that is it screwing up my ability to judge depth. I can't tell how much of him is in me, how much is left to go.

"I know, I know. I bet it would feel good for you to keep taking bigger and bigger dicks until your hole can't quite close anymore, even after weeks of rest." He stops his forward motion and quickly pulls back a half inch making gasp, caught off guard. Then, just as before keeps pushing in. "Maybe once we both get more established, once I have some more free time, I'll have you come live with me. Get you some tattoos, maybe a brand, fill out those lips, give you some nice big tits, then I will rent that mouth out for favors. You'll come back from your... errands, leaking like a faucet, begging me to mess you up, begging me to destroy this hole, begging me to make you even more worthless than you are, make you loose, pliant, bombed out."

His dick worms its way deeper, so fucking deep into my ass, as his words worm their way into my brain, intoxicating and somehow desirable. I am about to respond that I would let him do all of those things to me right here, right now when I feel his legs, his pelvis, begin to press against my ass. He closes the distance past the barrier of flesh, squishing my round ass down to the bone in order to get those few extra inches of his cock into me.

It feels like he is pushing the air out of my lungs, it's hard to breath, I gasp as he bottoms out. His cock wasn't tremendously long from what I remember, but the way his is pushing, it feels like he has hit a wall in my ass, stretching my pussy out of its regular shape. With how hard he is, any deeper would most likely be painful, but for now it is just a dull pressure deep inside.

The first draw had me moaning the entire pull. I could feel my ring cling to him, feel as his cock tried to turn me inside out, feel as the bulging head of his dick dragging over my buzzer. As his head started to spread me ring, I couldn't help but feel so empty. I giggled happily when instead of pulling out of me he slid back in, all the way in. Slow, but not as slow as before.

"Mmmm, so fucking thick," I say, laying thick the purr of lust. "I didn't know if I was going to be able to take it."

He laughs, the clenching of his abs causing his cock to jump in me delightfully. "Awww, that is so fucking cute. To think I would have stopped until I was deep inside you is ridiculous. Especially after you told me to destroy this tight little hole and make you a sissy." He massages my ass as he speaks, his fingers digging into my curves. I moan, he always knows what to say, always knows how to make me tingle. Make me feel like a sissy.

His hips kiss my ass, and again he presses into me, pulling on my waist to dig himself deeper. I groan as he stretches me lengthwise around his cock. That dull pressure the beginning of an arousing ache. My ass is so tight around him that I can feel every vein as he drags himself out of me, slower than when he went in. Again he doesn't take himself all of the way out, just lets the flare of his head stretch me a little bit more before diving back in.

His pace is quickening, or, at least it is when he thrusts in. now each time our lower bodies meet I am pushed forward a little, the deepest final inch of his dig now minimized to a tiny thrust at the end of his stroke. He still drags himself out of me, agonizingly slow. It gets to the point where his is actually fucking me on the way in, making me cry out as his half second thrust reaches bottom. On the way out I whimper and squirm, I wish he would stop teasing me. A single cycle takes ten seconds, but ninety five percent of that is spent dragging my insides towards my exit.

"Please..." I whimper to him without saying anything more.

He completely stops his movements and digs his fingertips deep into my backside. "What was that?" he snarls. "Do you need something?"

"I... Just... your teasing me... I can't take it, all this waiting..." I say, quietly, submissive. "Please..."

He slaps my ass so god damn fucking hard that I buck and jerk forward away from him, his other hand and the clenching of my pussy around his thick cock keep me in place. "What the fuck are you?" he asks, slamming his hands down again.

I squirm under his slaps, unsure if I should answer, or how to answer.

"Holy shit... you really are dumb." He whips his hand down again, the clap is thunderous, I squeal. "I asked what the fuck you are? Answer me."

I talk through teeth clenched from the stinging in my backside. "I... ummm... I am a sissy, a whore, a slut, a hole to be used."

Wolf spanks me, before gently massaging the spot he just slapped. "Uh huh," He says, "And how should someone use a sissy whore's holes?"

I am fearful of another spanking, unsure when I give my answer. "Uh... anyway... anyway they want to?"

He slams into me, jamming his cock as deep as he can possibly make it go. My eyes bug out and I groan through my teeth. "Good," he says, starting to withdraw painfully slow again. "Now shut the fuck up and let me use you anyway I want to."

"Guhhhh..." I groan. "Yes Daddy... Use me..."

Wolf continues toying with me for what seems like minutes. He is relentless in his pacing. Deep blistering thrusts in, and the slowest fucking velocity possible when he draws himself out. I want to scream at him, tell him to fuck me, beg him to fuck me, but we already went through that. He must be getting off on denying my needs, this can't possibly be as good as just straight up fucking me, at least for him that is.

Finally, with a pop, he lets his cock slip out of my hole. With nothing in it, my pussy tries to clench closed, but after the plug play and the warm up fuck, all it manages is a few half winks. I feel so empty now that he isn't in me...

"Wow," he says, sliding his finger around my gape. "I still can't get over how perfect your hole is. No way it's naturally this pink. Is it? Ah, doesn't matter. It'll be red in a few minutes." He taps his cock on my hole, the quiet slaps reaching my ears as he prepares for the next stage. "Bout time don't you think?" He asks.

"Yes!" I cry out, excited, making him chuckle. "I mean... umm... If that is what you want Daddy. Please use me to get off. Please dump your load in your personal cum toilet."

"Will do, you nasty little whore." He says, sliding the head of his cock into me. "Will fucking do."

~ ~ ~

Honestly, it took me a few moments to figure out what was happening. Everything was shaking, his legs were slapping against me, his balls slapping against my taint, the head of his cock battering the depths of my pussy. I could hear myself groaning, could feel myself squirming, but hadn't eyed clued in that Wolf had instantly gone full throttle.

It is a blistering pace that knocks the frame of my bed into the wall, a beating percussion perfectly syncing to his thrusts. My moans take on the qualities of screams, the bulging head of his cock just keeps digging into my buzzer each time he slides in or out. It makes me feel like I am going to squirt, I know I am already leaking.

With one hand on my hip to keep me in place, Wolf reaches forward and winds my hair into a pony tail around his fist. He moves his hand from my hip to the chain between the cuffs and lifts me up off the bed with both hands. My scalp stings, the metal cuffs digging into my wrists, while he just keeps pummelling my tight little hole.

"FFFFfffffucccckYYYEesssssdddDDaddy..." I moan through gritted teeth as my cage flops back and forth below me, my arousal just keeps fucking growing, but my clit had stopped trying a long time ago, hanging useless and leaking. "Tha-an-a-a-an-ank Yyyyyooou." Moaning words, the syllables are broken up by his aggressive fucking.

Wolf laughs sadistically, yanking my head back by my hair so that I am closer to him. "Thank you for what?" he asks, the question given with the addition of a few particularly hard and deep thrusts.

I squeal, my toes curling. It takes a few moments before I can get enough breath to answer. "For, for, for making me feel goo-oo-oood." I manage before having to go back to moans and whimpers.

"Well..." He says pausing his onslaught and drawing his cock all the way out. "You." He slams it in, all the way, as fast and deep as he can before pulling it out. "Are." He does it again. "Very." And again. "Fucking." And again. "Welcome." He switches back to fucking me continuously again, aggressive, hard, without any care for me it seems, not that I mind, I am loving it.

His pace is similar to before, but his thrusts impact with more force, knocking me forward so that he has to pull me back by my cuffs and hair. His cock pounds me at my pussy's limit, a dull ache spreading inside. I feel the line of viscous pre swing and stick to my leg as my clit bounces around in every direction under me. It feels good, feels really good. Like, fucking amazing good. I can feel him pumping my sissy juice through me as he batters my bitch button. My moans are basically nonstop at this point, I am seeing stars behind my blindfold. But for some reason, I just don't know If I will be able to cum like this. It's the ultimate sissy goal, the sissygasm, but I'm just not sure if it's achievable, not yet at least.

The slap of him against me is starting to sting, starting to burn. I shiver every few seconds, trying best to keep still, trying my best to be a good hole for Wolf. But it is hard, he is hard, he is fucking me so goddamn hard. I love it, the pace, the force, the depth, his width. But fuck me is it a lot. I am not sure how much longer I can stand it without melting into myself, without becoming a fuck puddle. Truly becoming just a hole to use.

As if we were linked, and right on time Wolf starts to let up. I can hear him breathing hard, and to be fair, it was minutes of some of the most intense fucking I think a person can muster, so good on him, but he was either going to bust, or need a break.

He begins to pull his cock all the way out of me, I feel my hole try to close before he sinks all the way back down in a single thrust.

He pulls all the way out again, and let's his cock rest upwards between my cheeks, gently rocking his hips in a grind. "Your pussy is made of velvet, I could fuck that slutty hole all day long." He says, praising me while he releases my hair, making my scalp ache as the tension is relieved. "I think I have decided," he begins, moving beside me to start changing the position I am in. "I am going to take your keys after I am done here. You are too good to let go, and I don't want to see you slip back into your false life. I want to push you further. I know you want that too, don't you?"

I let out a small, gasping whimper at his proclamation, I hadn't thought about giving up my keys. I mean I had fantasized about it. I am sure every sissy has, but I never really thought about what it would mean to actually give them up. Not this early at least, not to the first guy who bred me. I mean, his cock is perfect, not too long, but mouth wateringly thick. And the way he treats me is fantastic, rough, cruel, degrading, yet somehow I can tell he is sane. He knows we are just playing, I don't know why but I trust that he would stop if I asked if, If I truly told him to. In terms of possible key holders, he is far from a bad choice.

Wolf slips two fingers into my ass and darts to my bitch button, pressing hard and swirling his fingers. "I am guessing you need to me to finish what I started before you make you give an answer." He says, swimming his fingers in rough drumbeats against my buzzer. "Though judging by the puddle of your juices below your cage, you've already made your decision."

Puddle? I think to myself, moaning as he drums my g-spot with his fingers. Had I really been leaking enough to make a puddle? I mean, I felt it slowly moving through me as he battered my button earlier, but a puddle? Can I even produce that much pre?