Letting Strangers In Pt. 02 Ch. 01

Letting Strangers In 2: Chapter 1

"Thank you for having me," I say, attempting an unpracticed curtsy before adding, "Sir~" with a giggle.

"Uh huh," Wolf says with a scoff, "You don't have to lay it on so thick. You're already mine." He steps back and begins to walk through the foyer, motioning with a hand to follow. He doesn't say anything, leaving me to glance around at the various artistically furnished rooms we pass in silence. We arrive in a modern kitchen with Wolf stopping to lean on the island in the center. He stares at me with a neutral expression that after a few moments makes me squirm.

"Uhhhmmnn..." I mutter glancing around in the awkward silence. "It's really nice. Your house I mean, umm inside... out too... also. Did you decorate?"

"Thank you sissy," Wolf says with a slight amused grin. "And no, well not most of it. I pay someone to come in every now and then to update things. I like a modern aesthetic."

He pays someone to decorate his house? Like regularly? What the hell does this guy do for a living? And what is he doing living in a small college town like this? Is this his thing? Using college students as a never ending source of fresh meat?

I keep glancing around now even more interested in the house I entered only a few minutes ago unsure of what I was doing or going to do.

Wolf pushes off the island and walks over to a door. "Please," Wolf says motioning to the island, "Leave the food on the counter, I'll put it away after we 'chat.'"

I lug the heavy bags up onto the counter and position them so they don't tip their contents. Wolf has already opened the door and is holding it for me to walk through by the time I turn around. "Oh!" I say hurrying through the door, "Sorry."

"You're okay." He says following me through the door into a large and lavish entertainment room. A massive television is hung on the wall. A pool table off to one side with a half bar behind it. Sprawling couches line the walls, matching coffee tables in front. The perfect space to entertain. This one room is the size of my entire apartment.

I stop and stare at the large flat screen. "Oooohh... shiiitt..." I whisper to myself as I imagine a group of people sitting and watching me fuck myself to sissygasm, watching Wolf fuck my brains out, watching me moan and drool and lick and suck. I know this is where he displayed all those videos. I start to get heated. I feel my clitty strain against its cage.

Wolf must have noticed me staring at the tv. "We can make it a thing," he says as he walks past me and sits down on one of the couches. "A screening of sorts. Invite a group over and show off the latest video we made, have you serve the event. Could be fun, no?"

I can't help but blush, brief fantasies of me serving my own porn screenings bubbling enough to make my stomach flip. "I mean... you would be showing them anyway right?" I ask.

"Getting to know each other already I see." Wolf says beckoning me over to the couch. "Only with your permission of course."

"We would have to make some more videos first. Pick the best one. Best of the month? That could be fun right?" I say stream of consciousness like before plopping down next to Wolf.

He raises an eyebrow at me, "That something you want to do? I'll add it to the list, easy enough. You already like being on camera, I can tell." Wolf continues looking at me questioningly, making me look down.

"Oh, yeah... I mean..." I glance back up at him and give a smile, "Like I said, it could be fun right?"

Wolf doesn't answer, he just stares, an eyebrow still raised. After a few drawn out moments he rolls his eyes and clears his throat.

"Ummmm?" I quietly mumble, confused, looking at him for direction.

Wolf clears his throat again and spreads his legs wide while shifting his hips forward. He shifts his gaze down to his crotch then back up to me. His bored stare drilling a movement out of me. Forcing me into action though I am still unsure of what exactly he wants. Without thinking I reach down and begin to stroke his inner thigh.

Looking to him for some guidance I am only met with his burdensome stare. After a moment he sighs and relaxes a little before asking "What the fuck do you think you are doing?"

Slightly shocked I stop my hands movements, "Oh, I mean... I wasn't sure... umm what you want me to do?" Still confused I begin to wilt.

Wolf rolls his eyes again. He reaches over and puts his hand on the small of my back, slowly but firmly pushing me to get off the couch. "I didn't bring you here to hang out you dumb slut." Wolf moves his hand to my shoulder and guides me to my knees between his legs. "I need my dick sucked, then we can talk if need be."

I am stunned as I kneel before him. So quickly the situation turned from casual to pornographic. And then it sinks in. This is it. This is what I wanted. This is what I want. I want to be this. A sex toy. To be used whenever, without objection, just pushed to the ground. I feel my clitty try to grow, strain against her cage and throb in defeat. My cheeks start to burn and my hands move on their own to Wolf's belt and button.

Slowly I unzip his pants marveling as the doorway to his manhood opens. I reach in and fish around, easily finding his fat, semi-hard member. I pull it out through the seam in his boxers and gaze in reminiscent aww at the thing that marked me as a true sissy only yesterday. "Mmmmm," I moan as I gently stroke it, feeling the veins start to swell under my thumb. God it's thick, I think as it grows further, "I can't even wrap a hand around it..." I mumble.

This is the first time I've seen it. Sure I had felt it. Felt it to my very core. But seeing this bitch breaker accumulate mass before my eyes was beautiful.

"Not an unusual reaction to the first time seeing it," Wolf says, looking down at me with a smug smile. He pulls his phone out and taps a few times on the screen. I can't tell if he is filming me or just not interested in me but either way it turns me on.

"I didn't bring you here to worship it either. I am pent up, it's been a long day. Do your job. Whore." He says lazily.

His last word hits me hard, I can almost hear the lock on my cage clink as my clitty jumps and strains at its prison. "Yes Sir!" I say, shuffling forward until my knees are flush against the couch. I look up into the phone, still unsure if he is filming but I smile before I dive in.

My tongue lashes out at the head of Wolf's fat cock. I moan as I taste him, clean, fleshy, freshly washed with mint scented body wash. Saliva quickly coats him as I slip my lips around him. My eyelashes flutter as I stretch wide. Reminiscing for a brief moment of the day before when he fucked my throat raw with this monster.

Deep and deeper I go. I fill my mouth with him. Sliding my tongue back and forth along the underside of his cock as I inch down. I keep jerking him gently. My hand is desperately trying to wrap around his girth as he becomes fully hard. My fingers begin to tap against my lips.

I let my hand drift down, palm resting right beside his cock. I gently massage his balls with my thumb while I back off his cock. Once it is just the head back in my mouth I flick it with my tongue and moan. Now the fun can begin.

I oscillate my head slowly back and forth each time going slightly deeper. Saliva coats my lips as they glide, stretched wide along his devastatingly thick member. Veins like great tree roots almost vibrate my lips as my fleshy pucker moves back and forth. I look up at him and see him smirking down at me.

I moan, my clitty straining as I watch him stay perfectly still almost uncaring as I perform my duties for him. He is still pointing the phone at me, now I am sure he is filming. So I flash a quick little peace sign and wink then get back to sucking, though certainly a little noisier, a little more wet. I move my hand down between my legs and past the bulge in my pants that hides my straining clitty. The tips of my fingers find the plug through my tight jeans and begin to massage it gently. Moving it in small circles though burdened by the taught fabric.

"Mmmmmm," I moan on Wolf's cock as my plug prods my bitch button. I wish I had slipped out of my jeans. I wish I had something more substantial than a plug. I wish I was sliding up and down on something thick and meaty while pleasuring Wolf. Wanton thoughts tumble behind my eyes as I bob up and down kissing my grip each time as my own wet, sloppy, sucking sounds accelerate my racing dirty mind. I am nothing more than a horny slut impaling her face on a stranger's thick cock. On my Master's thick, veiny, meaty cock.

"I got places to be slut," Wolf growls, a hint of playfulness edging through, "This is about getting me off, you are wasting time on yourself. You can fuck your own brains out when you get back home but right now I need your 100%"

I freeze for a moment, blushing. I had been enjoying myself. I am really enjoying myself. But I know why I am here. Wolf has told me so many times over the past few minutes. I am here for him. I am a fleshlight. I am a cock sleeve. But toys don't slow down to prolong their pleasure. They have one purpose. To get someone off.

I take my hand off Wolf's cock and raise the other from my ass. I place them both on his hips, one glistening with my own saliva, and gaze up at him lustfully. Then I look down my nose and the shaft I am about to fit down my throat and take in a deep breath.

I can hear a smile when Wolf says "That's it sissy. You know what to do."

My clit flexes and strains against her cage as I slide up his length until just the tip is resting on my puckered lips. silently I rush forward. all the way until my nose presses, squished against his stomach. I can feel my throat bulge outwards as his thick cock forces the space it needs.

Wolf lets out a small groan of satisfaction right before I slide back off of him holding his head in my lips as my tongue lashes at it. I rush back down, emitting a lewd noise as his cock is forced far past my mouth and instantly slide back up. I do this a handful more times before I give up on trying to keep an airtight seal. I extend my tongue past my teeth, past my lips and move it back and forth rapidly as I slam myself down his length. licking the underside of his cock as I go.

Thirty seconds after starting my eyes are already blurry with tears as the room is filled with squelches and wet sucking noises emanating from my lips and throat. The occasional gagging noises pepper the soundscape in time with my losing focus as my mind slips from the task at hand to the cock in my throat.

"That's a good girl," wolf moans as he shifts his hips forward slightly. "Don't stop doing that until I cum."

"Mmmmm," I moan excitedly, doubling my efforts as I do my best to impress by facefucking the slut out of me, or into me. Whatever... I need that cum and hammering his cock into the back of my throat is the best way to get it.

Back and forth, up and down. Tears stream and blur my eyes as I feel the pressure build in my head, feel my cheeks heat up as I give up on breathing. Forcing myself to ram Wolf's cock into my sloppy sissy throat. I gag, I choke, but I don't stop for what seems like minutes though I know I couldn't last that long without breathing so I must be getting air somewhere.

Wolf's hand firmly tangles into my hair and grips, pulling my head back and off his twitching cock. "Open." He commands as he takes his cock in his other hand and strokes it vigorously.

I can see his glistening head engorge, his veins standing like roots under his skin. I feel like I can almost see the blood pumping as he approaches the edge. My jaw drops and I stick out my tongue, mewling quietly as his grip pulls my hair so delightfully.

His hand shlicks five, ten, fifteen times before Wolf tenses his abs quivering. He lets out a low groan of sanguine relief, his body folding forward slightly as his cock jumps in his hand. Once, twice, and then a jet, hard and white splatters into my cheek and over my lip. And then another coating my eye and dripping beside my nose.

Again and again, he cums and cums. Some lands in my mouth, some lands in my hair, Most covers my face. Eventually I am fully glazed, the last of his cum dribbling out over my tongue as I blink my one uncoated eye and giggle. I lean in and lick the head of Wolf's cock, then wrap my lips around it and suck gently. Catching him squirming as I lick and suck his sensitive head.

Eventually he pulls me off his softening cock and I swallow the small amount of cum I managed to gather in my mouth. I am slightly disappointed I didn't get to swallow it all but that isn't up to me and I still got some cum. I go to wipe a glob of cum off my chin but Wolf slaps my hand away.

"Nuh uh," he says with a devilish smile "I just painted you up all pretty, the least you can do is wear that home don't you think?"

I lower my hand. "You want me to..." I blush, unable to finish my sentence.

"Yes, slut." He says as he lets go of my head and tucks his thick and satiated cock back into his pants. "All the way home, and with a couple pictures as proof. Two on the way and one when you get there"

He stands and stretches his back, leaving me kneeling facing an empty couch blushing heavily under my mask of cum. There was an intense heat blushing my cheeks at the thought of it. Truly an embarrassing, perverted task. It was still early. It is a college town. There will be a minimum of tens of students walking about. There is no way to get home without being seen. Though the thought does titillate I can't help but protest.

"Are you sure?" I say meekly, still staring at the couch.

"What?" Wolf says, as if he couldn't quite hear. "What did you fucking say slut?" A snarl.

I begin to turn to him, still kneeling, still so much lower than him. "I..." I start "It's just... it's so busy I umm... so many people will see?"

He laughs, amused, toying with me "And?" He asks and stares waiting for a response.

"I mean..." I say squirming, "it's embarrassing, or... I mean... what if I run into someone I know?" I glance up at him to see him smirking.

"Hmmm, first a quick question." Wolf says, "Are you not a sloppy little cum craving sissy slut?"

I blink, and flush, and swallow. Tasting the remnants of his cum in my spit. "Yes... I am" I answer after a pause.

"What are you?" Wolf says with a grin.

"A sloppy little cum craving sissy" I answer shyly.

He tuts. "Louder." He orders.

A take a breath and look him in the eyes "A sloppy little cum craving cum covered sissy slut." I say loudly.

"And what do you think people will see when you are walking back to your apartment?"

"A sloppy little cum craving sissy." I say.

Wolf laughs, and says "Good, so you understand why you have to do it then? Can't have people getting the wrong idea about you now can we?" He stares at me, letting me know that to say no, while not being out of the question would be a huge disappointment.

"Okay..." I say, blushing deeply as I ponder what I must do. "Okay, I can do that. It'll be fine."

Wolf laughs again "Well of course it will be fine, it's just a few minutes walk home. But..." he pauses and stares at me with a crooked smirk. "Because you seem so keen on it now, let's spice it up a little shall we. Nothing too crazy though."

I just stare at him, regretting speaking up but also... dealing with a nervous excitement bubbling as my master, my keyholder, my daddy, and my owner winds me up and tortures me so.

"Both of those pictures on the way home. You have to get someone else to take them. A different person each time." He smiles as he talks. "Sound good? Just ask two people on the way home to take a picture with your phone of your beautiful cum covered face."

I blush deeply, now there is no way I can avoid people now. At the absolute least, two people in my town will see me frosted and glazed, dripping or dried but obviously creamed.

"Sound good sissy?" He asks but orders.

"Y-yes," I say stuck in my thoughts and blushing. My exhibitionist and submissive sides fighting against my reason. I know I am a pervert. Wolf knows I am a pervert. But this is another level. This is public humiliation. And my conflicted feelings mean I must be into it at least a little bit. But that doesn't change the fact that I have to show it to other people. Show how much of a slut I am. Not in a video or a picture but in person. A random person.

"Good, I am glad!" Wolf says, "Now, I've got a present for you. Get up, take off your pants and panties, I'll be right back."

~~~

As I wait naked from the waist down I feel his cum slide, congeal and soak into my skin. There is just so much of it. The smell and feeling of it making my heart skip, my cheeks blush, and my clitty throb. I don't know how long, but soon I will be walking around town dripping with his seed. Marked by my owner, a true slut.

It only takes another minute or so for me to hear Wolf's footsteps thud softly back into the room. He sees me and instantly smiles, admiring his work and my caged clit.

"You look so fucking hot in that, the perfect little slut." He prowls around me then harshly brings his hand down to my exposed ass cheek, a cracking slap that leaves a hand full of my plump girlish ass in his squeezing fingers. "And this ass, I cannot get enough."

He stands behind me and breaths into my ear. "I am going to take this little whore ass to places you cannot even imagine." He leans down further and licks my necks from my shoulder to my ear. "You don't know yet the depths of your depravity. But oh... sissy. I am going to show you just how deep you can go."

I blush and squirm under his tongue, tilting my head to the side to give him leeway as I press my ass against his hand trying to grind. He spins me to face him and I see in his hand a large pink buttplug. Maybe 50% bigger than the one I have in me now. A Jump for sure.

My eyes widen, and flick from the plug to Wolf and back. My cheeks blushing at the thought of putting it in me, Of HIM putting it in me. I feel my pulse pound in my groin. Feel my clitty try to grow and the delicious restraint of the cage. I feel my pussy spasm faintly against the plug whether it was in preparation or defence of the next intruder I couldn't say.

"Over here," Wolf says as he walks the few steps to the couch. "Bend over the arm here." As he motions to the high thick arm of the leather couch.

I step over to him and glance back before I fold myself over the arm. It's tall enough that just the tips of my toes are left on the floor.

"Good girl," Wolf says softly.

I can feel his breath on my bare ass as he leans down. He runs a hand over it with an approving whistle before saying "Damn, that is marvelous work. Your ass bruises beautifully. I am going to be spanking you all the time now."

I hear the telltale clinking of someone undoing their belt. My muscles clench and I get shivers. Is he gonna fuck me again? Is he going to utterly destroy my sissy pussy again like he did last time? Am I about to be slammed into this couch like a piece of meat until he pours another load in my hole?

Sadly the answer is no. He leans over me and puts the belt around my neck. Sliding it through the clasp until it is tight around my throat, restricting my breathing ever so slightly. I reach up to feel the belt, but a hand slams down onto my still tender ass.

"Ah ah ah, little slut." Wolf says placing a soft heavy object on the small of my back "No touching, hands behind your back."

I move my arms behind me and Wolf maneuvers them so my elbows are bent at 90 degrees. Forearms high across my back and my hands near my biceps.

"Hold them there." He says picking up the object again, "I don't feel like getting any restraints right now"

"Yes sir," I mumble, adjusting my hips over the arm of the couch until I was comfortable.

I feel Wolf lift the long end of the belt off of my shoulder where it rested and pull it taught. Immediately my breath is restricted, not enough to be any real hindrance but just enough to add the hint of a wheeze to my inhales and exhales.

CRACK!

His hand whips against my beaten ass hard enough to make me cry out had it not been for the simultaneous tug on the belt around my neck turning a yell into a croak.

SmackSmackSmackSmack!

"Fuuuuck..." I groan while wheezing against the belt, and biting my cum covered lip. His brutal strikes agonizing my already bruised backside. He tugs harder on the belt to silence me. I can feel my face growing red as my breath is put on hold.

I'm not sure how long he was spanking me, or how many spanks he rained down. But the edges of my vision were growing dull by the time he eased up on the belt.

"Good girl," Wolf praised, "I want you to remember me every time you sit down, and every single day. I am going to be telling you to spank that ass if we can't see each other. I want it red and raw at all times."

I take a few deep breaths and grind my hips against the couch as the tingling fire on my cheeks makes my clit strain against her cage. I only get a few moments of reprieve before Wolf tugs the belt tight and my lungs have to struggle again.

Wolf trails his fingers down my back and over my ass, then down my right leg before slipping between and moving back up. Eventually he makes contact with my cage and grabs my whole sissy package in his large hands. He squeezes hard enough to make me jump and squeak.

"Look at that tiny little sissy clit. Locked up and useless just like it should be." He growls teasingly as he releases my cage from his hold and trails his fingers up across my sensitive skin until they meet the plug I am wearing.

"This is where your use, your purpose comes from," he says as he presses the plug further into my pussy making me moan. "This slutty little hole will bring you so much more pleasure than that useless thing you used to jerk. I bet you even used to fuck with the tiny thing didn't you?" He smacks the plug and I moan loudly. My arousal steeply increasing as he talks dirty about me.

He smacks the plug so hard that it shakes me to my core "Fuck! Oooooou... fuck me!" I cry out jumping forward into the couch, unready for such an impact.

"I asked you a question sissy," Wolf says tugging on the belt. "Did you use to use your pathetic little sissy clit to fuck?"

I choke, gasping as my upper body is raised solely by the leather around my neck. I can feel the blood rushing. Up and down, my clitty strains against its prison as my eyes roll. Oxygen loss and perversion making me moan out a prolonged "Yessssssss..."

Wolf holds me up for a few moments longer, "Couldn't quite tell if that was from being choked or an answer so why don't you try again sissy."

I take a deep breath before saying "Yes sir, I've used my di-" I pause reformulating them away from a bad habit "I've used my clit before, during sex... sir"

"And did you enjoy using this little thing?" Wolf says as he flicks my cage, rattling my bits.

I answer "I mean... yes? It was good."

Before the slap registers past my ears a searing pain blossoms on my right ass cheek followed by the same on my left. I whimper and squirm as Wolf caresses his marks.

"Wrong," he says with a laugh. "Though I am sure some part of you does want to believe that. But c'mon, that part must have been pounded out of you last night. You were going to cum from getting fucked by a real man, you made yourself cum on top of that dildo. You yourself said it was better than anything you had felt before. You say using that flimsy little thing was good? Try again sissy!"

He smacks both my ass cheeks again to punctuate causing me to cry out. "No..." I whimper. "No... it wasn't good, not compared to what you showed me... not compared to what I showed myself." Part of me knew this was just play. Of course fucking a girl felt good, of course getting blown was amazing. But the truth was that it really didn't compare to the intoxicating pressure that built when Wolf spurred my bitch button with his rod. Or the release when I popped my own cork.

Wolf digs his finger nails into my reddened cheek, "Good girl." He says with an approving growl.

His hand slips along my skin, uncharacteristically gentle in its glide. He dips it further and further towards my center. Taking time to tease me as he moves closer to the plug. I feel a pressure in my core as he pushes gently on the plug, digging it into my guts.

"Mmmm," he muses pleasurably. "I love watching that. The muscles of the perineum flexing as a sissy's hole clamps onto whatever it has swallowed."

The pressure lifts and I feel Wolf dig his fingers around the plug to grip and pull. I feel the bulbous shape of the plug drag against my insides as it moves fractionally outwards. I sigh in quiet pleasure at the mellow movement.

He keeps pulling. So, so slowly. The locking bulge opens me up from the inside as it gets closer to my slick ring. The toy has done its job throughout the day and it is quickly slipping out of me. Still the stretch it gives as it reaches its maximum girth is enough to make me whimper as my toes curl against the carpet.

Wolf chuckles and gives me a relatively light smack on the ass. My pussy clenched around the plug. He lets go and it is sucked forcefully back inside. I can't help but squirm at the involuntary clenching. All of my muscles working together to jab my g-spot with the bulge of the plug.

Just as I start to relax Wolf grabs the plug again and pulls. Faster this time, the plug stretches me out to its maximum in under a second before he switches and pushes it in just as fast.

I squeak and bite my lip as the plug bottoms out. He pulls it back even quicker. It feels like he is pulling parts of me back with him, the plug again stretching me out at its widest before sinking deliciously back in. It presses tightly against my most sensitive spot, my clit twitches in tandem.

"You ever wonder," Wolf starts as he picks up the speed of the plug moving it in and out quickly in small pumps. "Why some men... Well not just men I guess, let's be inclusive to your lot and others... You ever wonder why they have such sensitive prostates?"

I only moan in response. Half because I am focusing on the delightful pumping and half because I know it is rhetorical and he is just going to tell me.

"Good answer." Wolf chuckles, slapping me harshly on the ass. "But no I didn't mean what makes a good sissy, though of course they must have an overly sensitive pussy. No, that is more of a psychological question. No, I have met all kinds of male with this sensitive trait. Straight men, bi, gay, power bottoms, tops, small, large, effeminate, dominant, submissive, some huge, some with micropenises, really just all kinds. But it's not all males with this trait, It really is just interesting."

He finishes talking and all I can do is shrug, letting out a mewl of satisfaction that I am one of those people.

"You are a particularly special case though, I have only ever seen maybe three other people with sensitivity even close to as high as you." He pulls the plug out to its maximum width and leaves it there. Then slowly begins twisting it left and right.

The stretch paired with the heated friction makes my stomach clench. Something adjacent to pain but so much more delectable builds as my hole is pulled in unnatural directions.

"Ahhhmmmn..." I whimper my toes curling.

"That feel good sissy?" Wolf asks, adding back the pumping motion alongside the twisting.

The depths of my hole spin with the plug and I cannot help but let out a guttural moan as I twist in foreign directions. Wolf continues with this motion for a minute or two. Slowly pumping while rotating the plug through each stroke. The plug drags like a massaging knuckle over my g-spot and soon enough I feel what I can only describe as the faintest of trickles within me as pre begins to flow towards my clitty.

"Feels g-ood," I say, my breath hitching as Wolf finally allows the plug to pop out of my hole. Not fully out, but just past the widest part. I barely have any time to be disappointed that the fun is stopping before he pushes it back into me.

I can tell that his goal is to stretch me out as much as possible, as Wolf now only moves the plug about an inch inside me. Back and forth he pops the plug in, then pops the plug out. The muscles of my tight ring don't know how to react and the natural behavior of closing back around the plug lessens each time it pops in one direction.

As the seconds tick by a faint wet schlicking sound reaches my ears. My hole has become so relaxed to the prolonged bulbous insertions that it is mostly staying open. My sloppy sissy hole is so loose I can hear it. The thought of what it will look like when Wolf finally pulls the plug fully out makes my cheeks blush and clitty twitch.

Wolf picks up the pace and lengthens the strokes. I can tell that the plug almost leaves my body each time he pulls back and is pushed in deliciously deep when forward. The bulge of the plug thumps into my bitch button like a punch knocking thoughts of anything but submission and service from my perverted little mind.

It isn't long before I feel a little splash of something wet against my inner thigh. I can't tell how much I am leaking but with how good it feels I wouldn't be surprised if there was a little puddle under me or dripping streaks on the side of the couch.

I moan loudly, my fingers grasping at my own arms behind my back as I get lost in the pleasure. "Don't sssstop... It feels so good..."

"Oh you like that sissy?" He picks up the pace even more, causing me to cry out as he batters my hole with the plug. "Don't. You. Worry." He says emphasizing each more by pressing the plug as deep as my body will let it. "We are going to make each other feel so much, I am going to make you feel things you have never felt before, but..."

He pauses his speech but continues fucking me with the plug. "But..." he says, jamming the plug into me as deep as it can go and spanking me hard, "That's all for today." He then forcefully rips the plug from my hole.

I groan at the emptiness, my hole twitches but doesn't close. The cool air touches me in places rarely felt.

I hear some rustling, but don't focus on it much as I am still reeling from the rough toy play and prompt termination. I feel Wolf run a rand over my ass and trace a thumb near the edge of my hole.

He whistles as I hear a ping from my phone, "Wow, you just have the perfect gape, a perfect O, I can see your heart in there. Sent a pic to you, I know how much you love looking at your fucked out holes."

"And look at that," He mutters to himself, "You made a mess of yourself, leaking like a true slut no doubt."

Wolf wipes the precum off of my inner thigh and the couch then brings it forward to my lips. I let out a quiet moan and greedily lick my pride off of his fingers, savoring the taste of my own pleasure.

"Onto the hard part," Wolf says. I hear a cap pop open and know he is lubing up the large pink plug. It's nearly identical in shape to the one I am currently wearing, with bumps and lumps expertly placed for maximum g-spot stimulation.

My still gaping ass twitches in anticipation and excitement, but my chest tightens with a slight nervousness. It is surely the biggest plug I will have ever put in me. Will the stretch be too much? Will it burn pleasantly or like fire? maybe a bit of both.

Then just like that my thoughts are brought back to the present as a glob of lube lands just below my tailbone and starts sliding towards my eager hole. Wolf catches it with a finger and begins to rub it in gentle circles around my hole.

Biting my lip, I moan as he dips one finger into me, then two. As stretched out as I am, the fingers barely skim my ring. But Wolf gives them a nasty curl and forcefully mashes my button. I cry out and squirm, my juices literally flowing by the efforts of his practiced fingers.

I feel a little more lube being poured over his fingers and into my hole. He spends a few more seconds massaging my on-switch before moving on to fully coat my entrance. He pulls out unceremoniously and moments later I feel the tip of the plug at my door.

"Be a good slut and just relax," Wolf says provocatively, "Sissies are receptive no matter what. What is your purpose Sissy?"

"To suck and get fucked by Men, to swallow semen and drip cum, to serve and submit to dick." I answer without thinking, quick enough that it makes Wolf chuckle.

"Exactly, good answer slut." He begins to push on the plug.

The tip easily slides in, unsurprising as the tip is smaller than the biggest part of my old plug. But so quickly the progress slows as my hole stretches tight, keeping the wide invader out. My fingers dig into my palms as my hole yields little but the force increases.

Wolf lets up on the pressure, "Something I love about toys is that you can just keep getting bigger and bigger ones." He caresses my round ass as he presses the plug back into me. "Eventually of course the body maxes out but that is years down the line and with toys the size of your thigh."

I imagine myself sitting down, slowly sinking onto one of those huge novelty dildos, my stomach bulging to accommodate the massive intruder. lewd thoughts of what my hole would have to become to facilitate something that infiltrate my lust clouded mind and I can't help but drool at the thought. I feel the plug slip a little deeper into my lube soaked pussy.

Wolf lets put a low growling laugh, "Did you loosen up at the thought of taking something extreme? Does the thought of getting fisted being an easy task turn you on? At least your hole knows what it wants." He presses the plug even harder into my, lighting my little ring up with a stretching burn. " I'll take note of that sissy. I wonder what your body's max is..."

A moan escapes my lips and my hips roll against the plug. Wolf takes this as a cue and backs the plug off until just the tips is pressing into me, then proceeds to slowly fuck me with the length i have been able to take so far. Each time he moves the plug forward he presses a little bit harder, moving it millimeters deeper.

I close my eyes and focus on relaxing, on making my hole as receptive to this large intruder as possible. I play up my own moans and gasps as encouragement to myself, telling my body to make room, to open the door. Though it seems to have an effect on Wolf as well. His slow pumping picks up both in speed and length.

Each push the maximum radius of the plug gets closer to my threshold. Each time as a result my maximum radius increases as well. It feels like Wolf is trying to shove a watermelon into a tailpipe. Despite a now persistent burning stretch I can't help but feel my cheeks flush. This is just the first few steps in my journey, in my pussies journey.

"Back to what I was saying though." Wolf starts, leaning in to kiss my right cheek during a particular poignant push. "The feeling of that push into a tight sissies hole is exquisite. Seeing my thick meat slide inside is why I keep doing this. However a true sissy should have no resistance to her master's cock."

I feel my body tingle at the gentle kiss on my bruised rear, I am 100% sure I am a masochist but it's nice every now and again for comfort during hard times. I try to just focus on relaxing and trying to take the toy, but Wolf's dominant ramblings float into my ears as affirmations of my sissy self. Soon enough I am imagining Wolf's thick cock stretching me out.

Wolf continues slowly but forcefully expanding my hole, "Toys are where it's at once your hole becomes a fucked out meat chute. I still get so much pleasure from seeing a ring stretched tight around something, hearing a sissy hiss at the stretching, watching their body jerk as the toy pops in and invades. But once we are a few months in I know that you will always be stretched and ready to go for me so eventually a big plug or dildo will be the only way to see you stretch." Wolf pulls the plug all the way out and stretches my hole to the side with his hand.

He adds, "All I will need to do is flip up your skirt, or pull down your pants, or rip your tights. Then pull out whatever toy you have stuffed up there that day and plunge in. You will be so loose that those kegels will have to be active the whole time for you to feel anything" He positions the plug back at my entrance, "Are you ready sissy? I think it's time you took this toy right?"

There is a silence for a few moments before I realize that I am supposed to answer. "Yes Sir, Please help me with your gift." I lay it on thick but I don't feel quite warmed up enough to take it.

"Good girl," He whispers, hooking his fingers into the crook of my hip for leverage as he pushes the plug home.

"Fuck!" I cry out as the plug immediately meets a barrier and a sharp stretching burn clouds my thoughts. I can't help but clench at the thick invader.

Wolf tuts and lets up a little "Easy there sissy, you just gotta relax, it'll fit perfectly I promise. Ready?"

"Mhmm," I murmur while nodding.

Again Wolf pulls me back by my hip while pushing the plug forward and I groan loudly. I very nearly start to clench again, I balance on the edge with my hole twitching reflexively at the invader but holding on.

As is becoming apparent with Wolf, He is an expert when it comes to stretching out my hole. It never quite turns to pain but it gets damn near. My ring feels like a gasket, stretched thin and about to give. It seems impossible in the moment, but the plug keeps getting wider, the muscles in my entrance straining as I squeal and groan in attempts to relax myself further.

My legs, straining against the carpet, give out. Then like a punch that I swear makes me see stars, the plug rockets into me filling my void so thoroughly I can feel it in my bladder. It is such an exquisite pressure.

The previous plug felt good, and if it was played with I could feel it in my G-spot, but this one, this one is constant pressure, "Uuuuuuughmmm..." I moan, the air in my lungs feeling like it is pushed out by the plug. "It's... its so big... I don't even feel like I can move with it in."

Wolf massages my ass and gently taps the plug with his thumb sending vibrations through me. My hole tightens around the large intruder in spasms but there is almost no give. My muscles just clench causing the plug to crush my bitch button with a force unlike any toy I had used before. It is like I am actively milking myself each time Wolf caresses the plug.

I squirm against the couch, lost in the feelings of the perfect new plug hitting my most sensitive spot. I can feel juices flowing through me and leaking out of my cage. I want Wolf to give me more, to play with this new plug just like the last one. This stimulation is so intense that I never want it to end even though it is leaving me a drooling mess.

"Well..." Wolf says, as he continues to massage the plug into me eliciting moans from my open mouth, "I think that just about does it, for today."

Both of his hands slam down on my ass and the instinctive yelp I let out is quickly followed by involuntary writhing as I clench hard on the plug that doesn't give a single inch to my inner walls.

"You might be thinking slut," Wolf muses as he walks beside me and into my view. "Is the plug too big? How am I going to walk home with this thing in me? How am I going to spend the night with this is me?" I can visibly see an erection through his jeans, no doubt brought about from my yelps and groans as he slid the plug into me.

I must admit I hadn't thought about those things at all. I am barely managing the act of laying over the couch. I can feel my heartbeat in my bitch button as the increase in blood pressure causes a squeeze. My mind is split between the plug in my ass and the thick hard cock of my master right next to me and Wolf seems to notice this.

Wolf laughs mockingly "Can't take your eyes off it can you sissy? Don't worry you will get many more opportunities to drain these balls into your slutty little holes in the future."

With a tut, Wolf bends down behind me and grabs the old plug, then to my mild awe tosses it into a garbage can across the room. I can't help but think this is a bit of a waste but I hold my tongue.

"Won't be needing that one anymore," Wolf says as he turns back to me, "Thanks for the blowjob sissy but I need you to get out of here. I've got shit to do. If you are still wondering about the answers to those questions, here are the answers."

He reaches back and gently pushes the plug into me, "No the plug is not too big. Most likely slowly. And I don't care, you will find a way." He wallops me on the ass with a loud cracking spank, "Now get up and get dressed," He says flatly.

I jump at the sudden impact, biting my lip to distract myself from the sudden movement of the plug in my ass caused by my reaction. "Yes sir." I say as I put my hands on the couch cushion and begin to push myself straight.

Mind you this is no easy task. It seems that each minute difference in the angle of my hips causes a wave of spasms and delicious cramps to flow from my hole into my abdomen. Each shift is a little burning spark rubbing against my overburdened insides. Slowly but surely I straighten myself out, moaning and groaning along the way, discomfort and pleasure mixing in such a simple movement.

I look down and see a small area of leaked juices, streaks on the couch and drops on the ground. I reach down to my caged clitty and run my hand over the smooth plastic, gathering some of me onto my finger and bringing it to my lips. The sweet taste of my masculinity, each drop of pre and each squirt of cum as a sissy leads me further towards the goal of getting rid of it all, of being the perfect feminine creature I so desire to be.

Now the actual difficult part comes from walking over to my pants. It is at this moment that I realize that it isn't just the cum facial that will make walking back through town so difficult. I can tell that there will be very little I can do to make it look like I don't have a massive plug shoved in my pussy.

As quick as possible I step into my panties and jeans and pull them up to snugly cushion my clitty. And even though it isn't much, the added pressure of skinny jeans makes the size of the plug even more apparent.

He watches me with an intense lustful stare, saying only "Come," as I finish putting on my clothes. He walks off the way we came in and I jump to follow him, rushing before the plug bumping around inside me makes me slow my pace.

"Wait here," Wolf says as we reach the front door. He then promptly turns and heads off into another room leaving me alone.

It only takes a few seconds before I start feeling a little awkward. Not only am I standing in an unfamiliar foyer alone but I am also wearing a cum mask and what feels like a stick up my ass. I look around at the modern architecture but really can't focus on anything. Eventually my eyes drift down to my shoes, and with a sigh I start the arduous process of bending over and putting them on with such a large object in my slut hole.

Just as I am finishing the laces on my second shoe Wolf walks back in. "Trying to run off then?" He says with a sly smile on his face.

"Oh!" I say caught off guard, "Uhn... N-no... just getting ready I guess, I didn't really know..."

Wolf walks over and cracks a few fingers off of my ass making a loud snap but inflicting almost no pain. "Thought you might have wanted to flaunt your new facial to everyone as soon as possible," Wolf jibes "But no, I was just fucking with you. I really do have to be somewhere soon though so you will have to run off in a second here."

He looks me up and down, something he has done a few times over the visit, as if he can't believe he bagged such a catch. It makes me blush and squirm. I am not used to being stared at in quite that predatory way. I have been admired, desired, but never this. This is something new.

He clears his throat, "Here," He says, holding out a wad of cash "two hundred for the groceries you brought over, one hundred for being a little whore, and fifty for the pictures you are going to send me from your walk home."

"Whaaaa...?" I say as I reach forward and gingerly take the bills. I look up at him with a raised eyebrow.

"I told you I was gonna pay for the groceries. This life, the sissy life, has costs that a boi wouldn't think of. It can be expensive." He shrugs and reaches into his pocket, "You know what, here. A tip for the quality of the blowjob on top of being a whore." He hands me another fifty.

Four hundred dollars? Two hundred for being a sissy whore? I flush realizing that I was just paid for sex, that with accepting this I can technically call myself a whore, a prostitute, sex worker. My clitty throbs at the thought.

"Thank you..." I say shyly, folding the money and putting it in my pocket. "Sir."

"Oh you are so welcome you dirty little slut." He says, moving close while facing me.

He reaches around with both hands and at first I think he is going to give me a hug but then I feel his big hands plant on my ass. His fingers sink into the pliant flesh and keep squeezing till I think it might bruise. He then lifts me up, by my ass, and whispers in my ear.

"There will be plenty more opportunities to earn if you are up for it." He then drops me back to the floor and spins me towards the door. "Now get the fuck out of my house before I tie you up and invite some friends over."

He slaps me on the ass so hard that it pushes towards the door a step, I yelp and reach for the handle. "Yessir..." I say meekly, though briefly wondering if he actually meant what he said. I turn the handle and step out into the cool evening air, "Bye." I say turning around and waving.

He takes the door from my hand and waves back with a sadistic smile on his face. "See yah slut." He says quietly before closing the door behind me.