Letting Strangers In Ch. 04 of 04

"Hey Sissy," He says, "How is that hole feeling? How are you feeling?"

"Oh... ummm... It feels ok," I mumble, embarrassed as I squeeze my hole around the plug. "A little sore, but... I kind of like it. I'm good though, really good! Like... I feel, happy."

He laughs, loud and jovially. "Bahahaha, Yeah... fuck yeah it does." He says laughing some more. "I haven't gone that hard in a long while, you have got a hell of a talent for taking dick, and one slutty fucking hole."

I blush, mumbling something but unable to properly respond.

"I've got to admit, I might have been trying to push your limits." Wolf says, I hear some clinking in the background and someone else talking, he is in public. "I wanted you to tell me to slow down so that I could punish you later, but you didn't even flinch! I mean... you definitely flinched, but you took everything, fucking everything I could throw at you. You are a one in a million slut, that hole is gold."

I giggle, one of my hands drifting between my legs to massage the plug, heat rising. "I wouldn't have asked you to stop unless you were actually doing damage, but for the most part it felt amazing, and at worst, uncomfortable." I let out a moan as I push the plug against my button, putting on a bit of a show for Wolf. "I am a good sissy, you don't have to hold back when you are fucking me."

"Mmmmm..." Wolf moans, mixing in a purring growl, "You are a great fucking sissy... I am going to do terrible things to you, and that hole of yours. And you, my toy. Are going, to fucking, love it."

With emotions caught somewhere between nervous and excited, I let out a laugh. "Fuck me up," I say wantonly. "Make me yours."

"Ha," he says. "You are already mine and you know it. I bet you jumped on a dildo the second I left the building and fucked yourself until you collapsed. All while thinking about me, knowing how close you were, knowing that I could make you feel even better than your toy."

Quietly, I gasp. His words were eerily close to the truth, but... I guess it wasn't exactly a tough prediction after getting to know how my body works, how my mind works. "I..." I start, unsure what to say. "I had my first sissygasm. From my dildo, while riding it. After you left." I mumble, blushing, admitting.

"Oh!" Wolf exclaims, excited. "Sissy! I am so proud of you, the first sissygasm is always the hardest to obtain, but now. Now that you are over that hump, everything will fall into place. Soon you will be able to cum with your ass just as easily as you would from jerking your useless clitty. Plus! Plus, you are locked in chastity pretty much permanently. That'll help everything along. How did it feel? How did it feel when you finally squirted?"

I clench around the plug, groaning in reminiscent pleasure as I increase the pressure on the toy in my battered pussy. "I couldn't begin to describe it properly... It was like ten. No! One hundred! One hundred clitty orgasms all stacked on top of each other, and never ending, and pulsing through my entire body." My explanation devolves into moans as I recall my first orgasm as a gurl. "I honestly don't think... mmmm... I don't think I have ever felt something as good as that sissygasm. I don't think I will be able to stop chasing them. Fuck!" exclaim a little shocked. "Am I already? Addicted to sissygasms? To anal sex? Is that even possible?" The whole time my hand hasn't stopped moving the plug.

"Fuck me," Wolf laments, "That is hot, but I'd personally like to think that your sexual drive was always there, you just hadn't ever let it out of its cage. Now that you have... Pandora's sissy pussy is all I am thinking. I think you were always a whore with an unusually sensitive pussy and bitch button, but I guess it doesn't really matter either way. What's done is done."

Wolf's words hang over me like a summer sun, heating my body with a lustful blush. "Y-yeah... I guess." I say. "It doesn't really matter, this is who I am. And if people don't like it, they can fuck right off."

"That'a girl, I am happy for you." Wolf affirms. "Now, did you film it like I asked you?"

"Oh! Oh, yeah." I exclaim, setting the call to speaker as I thumb through my phone. "Fuck, Sorry. Just a second, it's a bit... way too large of a file for text. I am gonna upload it to a drive and link the file. Just a sec."

"Damn. I mean no worries about the wait. But how long were you fucking yourself for, how long is the video?" He asks.

I quickly check the specs as I wait for it to upload. "Ahahaha... yeah..." I mumble, embarrassed. "The video is 48 minutes, which mean that I was probably fucking my hole for... I dunno... 35 or 40 minutes. I didn't watch it back, just hopped in the shower."

"I'm with some friends right now. You mind if I let them watch? Else I'm probably not gonna get around to it until later tomorrow." He pauses, letting me think.

"Oh... Ummm... I am... not sure..." I say slowly. "My face is in it, and... I mean..." At that moment the upload finishes and I copy the link into the text que, ready to send.

"Hey, I get it if you don't want to share it," He starts, taking a reassuring tone. "But they are all super chill, all into similar things, all know what I get up to. They would be the guys and girls I would call up to come and help me fill you anyway. I'd never straight up give them the video, just let them watch. You are my sissy now, and they are gonna see you in person sooner or later, it'll just be an appetizer. Do you mind?"

A little on edge I pause to think, Wolf seems to wait patiently. In the background I hear people taking, cutlery, laughing. "I suppose... I'm okay with you letting them watch." I say, though my heart thumps in my ears. "G-go for it."

He laughs happily. "Such a good sissy, I am lucky to have met you." He says, I can hear his smile through the phone. "I'm gonna hang up for now to watch the movie. I'll call back once it's over. See ya slut." He says hanging up before I can reply.

"I... wonder if that was a good idea..." I say, mumbling to myself as I turn on the T.V. and drift off to garbage, into perverted dreams, twisted with sin.

~ ~ ~

"FUCK!" I groan, looking around the room before realizing that what woke me up was my phone ringing and buzzing on my chest. I swipe to accept the call and bring it to my ear. "Hello?" I say.

"You, my perfect, filthy, little slut. Are fucking incredible." He seems genuinely proud as he speaks. "I know it's probably bit early in your sissy life, But you could be making huge amounts of money putting on shows like that. Your slutty makeup, smudged from a hard fucking. Your cute feminine moans and cries. Your slutty outfit. And fuck me, the way you were fucking yourself like you were possessed."

I blush, unable to form any words, and just giggle.

"I threw the video up on the big screen." He says as if it was the obvious thing to do. "Not one single soft dick in the room, hell even all the girls seemed wet from your display. You have a lot of new fans in town, you are one popular slut. Don't worry though, they are all chill like I said. No one is going to out you as the sissy who squirted like a whore, I mean, unless you want them to."

I laugh nervously, but my hole twitches around the plug. "I... did they really like it? Was it really that good?"

"Are you fucking kidding? Did you not watch it? Er... Or... Right, guess you didn't." He responds, "That was top tier amateur porn, and like... you had proof that you were enjoying it and not just making a show. You were leaking like a fucking faucet the whole time, and then when you finally came, I mean the proof was right there in bright white gooey strings. Fuck you ate so much of your own juices, and cleaned off the dildo, and your fingers... such a dirty whore, I love it."

I think I hear someone agreeing with Wolf in the background, as if they are listening to the conversation. Which is a little embarrassing to say the least.

"I swear to god, just think about releasing some stuff. Doesn't have to be this video, doesn't have to have face, it'll still blow minds. That hole of yours, that voice, the way you writhe when you cum, everyone will know it's real."

I am starting to get excited, a heat building in me as Wolf praises my masturbatory skills and performance. "I'll think about it, but I am happy to just make videos for you... and... I guess your friends... for now."

"Definitely do, you could be a star, have fans in every city waiting to fuck you if you happen to travel out there..." He trails off, thinking about other things, maybe gesturing to someone at the gathering. "Anyway, I am happy you got to have a sissygasm, proud even. You are a good sissy, I am going to push you to do things you never thought you would. I can tell you are the adventurous type."

"Uhhh..." I start, unsure. "O-ok, I... Will do my best to be a good sissy toy for you to play with?"

"You better, I've got your keys, you are mine." He says. "Plus you know I can make you cum like the whore you are, that has got to count for something."

"I am committed..." I say, swallowing some nerves. "To trying my very best... To being your sissy, to being a good sissy."

"Good girl, that is all I can ask for." He says laughing. "I gotta get going though, some people are calling me over. Oh, and I forgot to tell you. I filmed our session, me using your holes. Would you like a copy?"

"Y-you filmed it? All of it?" I ask my heart sinking. "I never said you could..."

"Comes with being a sissy. I get to use you however I like, it is your job to take it." He states. "Though, If you like, I can delete it. Bit hypocritical though considering you just let fifty or so people watch you fuck yourself to sissygasm." He snickers at the last part.

"I... I guess it's fine. I mean... you are right, I don't actually have a problem with the filming. I just would have liked to have been asked." I say submissively. "You can keep it, and I would like a copy as well..."

"Good girl." He says with a laugh. "And how about this, I am going to film and take pictures of many of the things we do together. But I will never post them, or give copies to anyone other than you without your permission. I will show them to people though, but I will have control of the spread. All of that sound good? Or maybe you aren't as much of a submissive sissy slut as I thought..." He hangs the last sentence out, a not so subtle manipulation of my need to serve him.

"I'm okay with all of that." I say with a sigh, though I feel my cheeks get hotter at the prospect of him sharing aspects of me in compromising positions. "If it makes you happy to show your sissy off, then please do it." I add with conviction.

"Oh! Such a sweet girl." Wolf says. "Then I assume you don't mind me showing the video of your first breeding to all these nice people? They have been asking to see it all afternoon."

A moaning gasp escapes my lips as thoughts of Wolf breeding me flash through my mind's eye. All of the things he got me to say, the loud screaming moans, the sounds of my hole getting demolished by his fat dick. "Y-yeah, I don't mind you showing me off." I say quietly.

"Perfect!" He exclaims. "I got to get going now. See you later you dirty fucking whore." Wolf promptly hangs up the phone before I can reply.

I pull my phone from my ear and stare at the screen. "What have I gotten myself into...?" I mumble as I drop the phone onto my lap. I feel like I am being used, but the thought brings a flush to my cheeks. I think I like being used.

I sit, reclining on my couch for a few minutes, when pulling me from my fantasies of Wolf's group watching me get fucked, a text comes through. It's from Wolf, a drive file link. 'Enjoy' he texts.

I reply with a quick thanks before opening the link and downloading the file. I immediately start it up. A side angle from what can only be his phone on my bedside table. I am kneeling in full view of the camera. I see wolf walk around to stand in front of me. His cock is out, and I blush realizing that this is the first time I have seen it as I was blindfolded the entire time he was using me. I think it is even bigger than I thought it was, decently long, but extraordinarily fat and bulbous. The perfect bitch breaker.

The moment I hear Wolf say 'open' I realize that this is going to be a very loud and lewd video. I contemplate going to get headphones, but I realize that all of my neighbors already hear the real thing. My little phone speakers were never going to get that loud.

I slip a hand between my legs and down to my plug, beginning a gentle massage as I start to lick and suck on Wolf's fat cock in the video. I've never watched myself perform on video before. Needless to say I am very excited, but I am pretty sure I don't have another anal orgasm in me, pretty sure all I am doing is setting myself up to be teased. For a brief second I wish I wasn't locked up, it is so much easier to just jerk it when horny. Then, however, I focus on myself in the video. I know my place, I never want to use my useless clitty again to get off. I am a sissy. I am a slut. I am a whore. I am a toy to be used. I am me, now truly me. No going back.

~ ~ ~

It is a long video, I hadn't realized how long the session was, but the video was over an hour. By the time it ended, it was already starting to get dark, and my stomach was growling with demand for food. I roll forward, and wince as all of my weight shifts to my ass, the bruises are definitely maturing. I know there are many more to come though, and the moderate pain excites me.

Standing with a yawn and a stretch, I walk over to the fridge. "Leftovers it is." I say to myself as I pull Tupperware off a shelf and slam the door closed. The microwave hums as I open my phone and stare at the picture of my gaping, well-bred hole. "Fuck me..." I say with a delighted shiver. "Today was so fucking good... Kind of feels like a dream..." For many years I had dreamed about something similar to what had transpired. Fantasizing as I dressed up, fucked myself with dildos, jerked off. Today was real though, I could tell because I wasn't in control. My dreams were always centered around me, always drifted exactly the way I wanted. Not today. Wolf was in control. I was his. I am his.

The beeping of the microwave snaps me to attention, and I gingerly hold the overheated dish as I walk back over to the couch to eat. I try to sit down gently, but my legs are tired and buckle. I almost drop the dish, too focused on not slamming my bruised ass down. I wince, but the feeling of pain carries a modicum of lust with it. I'll have to take a picture of the bruises tomorrow.

~ ~ ~

After dinner I head into my room and prepare my desk to study. Setting up my computer and some notebooks. To be honest, I don't get much studying done. I am constantly plagued by lustful thoughts and urges. My hips are ceaselessly rolling, swirling the pug inside me to the point that I start to leak, a damp spot forming in the crotch of my pajamas. Still though, some studying is better than none, it is getting to that time of year where every bit counts. After a few hours of struggling I feel like I have reviewed enough material, kind of, sort of... better than nothing? Whatever...

I open up a new tab and switch on some sissy hypno. Almost instantly I fall into a trance, I can't quite describe it, but they hit so much harder than they did even this morning when I was getting ready for Wolf. When they say I should only cum with a dick in my ass, or only have sissygasms, it makes sense, I have been there. When they says to let men use you, I know I will, I let Wolf use me. When they say to lock away my clit forever, I have no doubt I will, my keys are already with Wolf.

My free hand drifts down and absently fondles my cage until I realize what I am doing and pull it away. I force myself to be content with just grinding my plug against the seat of the chair. I know it is merely a tease, but it is all I can do at the moment, unless I want to lube back up and ride a dildo. Which I am fairly sure I can't. I'm just too tired.

The videos pull me into a deeper trance, and before I know it, I am jerked awake by my chin hitting my chest. The video I was watching had ended and the clock had moved an hour ahead. "Damn," I mutter, "Getting fucked is hard work..." I push my chair back and stand, glancing over at my bed, completely unmade to let the pool I leaked dry out.

I can still see the stain, but I when I walk over and touch it, it feels dry enough. Throwing some on some new sheets I spend a few minutes remaking the bed to my standards, lots of pillows for me to hug during the night, things to wrap my arms and legs around. Stand-ins for partners that I always assumed wouldn't be able to handle the sissy side of me. I doubt Wolf is the type of person to stay over so I can cuddle him, but you never know. Plus it doesn't really seem like we are monogamous so I can always find someone else. Either way, the bed is made and I walk to the bathroom to brush my teeth.

Just like before I stare at my reflection, something akin to disappointment bubbling in my chest as I turn my head this way and that. Was it because I had gotten used to the makeup making me look femme and slutty? Or something more clinical?

I brush my teeth with a slight scowl, trying not to look in the mirror any more than I have to. While I am brushing I realize it has been quite a few hours since I last peed. At the moment of realization, a burning urge builds, and by the time I spit in the sink, I have to run over to the toilet. I stand and rip my PJ bottoms partway down. "Fuck!" I exclaim as I grab hold of my cage. "Sit... Sit sit sit." I mutter to myself as I lower the seat and turn around. My bladder empties quickly and I sight with relief, grabbing some toilet paper to wipe my cage. It's not the first time I peed like this, but it is the first time it's felt complete, like this is the way it is supposed to be.

I stand and pull up my bottoms. I grab my phone on the walk over to the bed, and get an idea. Pulling my pants down I lay on the bed, stomach down with my legs spread a bit so you can see the plug and my cage. I contort, lifting my hips up, sticking out my ass while reaching around to get my lower back and thighs in the shot. I hit the shutter button a few times, hoping that one of the pictures is alright.

I relax from the modeling position with a sigh, lifting my bottoms back up to my hips and scooting up the bed to the pillows. It turns out the pics are all pretty good. The bruises on my ass are really starting to take form. The plug and cage are perfectly framed. Still I choose the best one and caption it 'Thanks for fucking me daddy, today was amazing' before sending it off to wolf.

It feels a little humiliating thanking someone for treating me like a whore, but the urge to indulge in those feelings is part of the reason why he treated me like a whore in the first place. The thought makes me blush.

I push myself up the bed, and slide under the covers before reaching over and turning off the lights. Sleep does not come as easy as I would have thought. For many minutes, I writhe under the covers as I reminisce and imagine. Multiple times my hands drift down to play with my plug, to massage my taint, it takes a great deal of effort to cease the teasing masturbation. Eventually, after a long fought battle for sleep. I do drift off. To lewd fantastical dreams, ones that surely would have brought about wet sheets if I hadn't been locked up and milked thoroughly.

~ ~ ~

Lactic acid sat in my muscles overnight, and I wake stiff and sore. I guess 45 minutes straight, of what was essentially hip thrusts is a little above my usually workouts. With a yawn and a cat-like stretch I roll out of bed and slouch towards the bathroom still half asleep. I feel an unwanted pressure as I arrive, the bane of all good sissies and bottoms alike. I remove my plug, languishing in the stretch my ring gets having tightened up somewhat though the night.