Letting Strangers In Ch. 04 of 04

I relieve myself and set up my shower hose douche, quickly but thoroughly cleaning myself out before lubing up and slipping my plug back in. It feels good to be filled, feels good to be full. While brushing my teeth I avoid my reflection like the plague, I know I am dishevelled and aged a few years by the effects of sleep that haven't worn off. It will only add to the disappointment that has come from staring at the reflective glass.

Usually I would change into clothes more or less marketed towards guys, but today I just can't bring myself to do it. I don't have anything that I could really wear outside when it comes to women's clothing. It is all a bit too short, a bit too lewd, but I wasn't planning on leaving my apartment any time soon, so I slip into some sheer leggings and a loose fitting top to lounge around. I do check myself in the mirror, and if I keep away from my face, all I feel is warm contentedness as I turn and pose in different ways.

Once satisfied I step to my bedside table and pick up my phone. Upon swiping it open I see Wolf has texted me a few times.

'Thanks for the pic slut, hope you have a good night.' The first one says.

The second one, 'Everyone is in love with you sissy, the video was an absolute hit. So many requests to spend some time with you, I might need to rent you out. A lot of women interested as well, if you re Bi.'

I hear my own heartbeats in my ears as I read the second one, people want me? Rent me out? Women? I'd never been popular, but I guess this is the life of a slut, of a whore.

The third text says, 'Sissy, Let me know when you are up, I want to set some rules for you.'

I don't waste much time digging through the meaning, and swipe onto Wolf's contact info, pressing the call button and bringing my phone to my ear. While I sit on the edge of my bed, it rings three times.

"Good morning sissy." Wolf's voice comes through peppy, happy even.

"Good morning daddy." I reply.

"Just wanted to touch base with you," He starts, "I know things can be overwhelming when relationships like this start, I want to make sure you are not regretting anything, I am not a total monster and I want to know if there were any limits crossed, any limits you want to set."

I let out a yawn, still waking up, slowly. "Nnno, no I don't think so..." Still thinking of anything I didn't like or wouldn't want to do. "I can't really think of anything that you did that felt bad, or if it wasn't pleasurable, didn't reinforce my sissy side. I really liked it." I smile to myself as I finish, I really did like it.

"I am glad I could make your first sissy experience so fulfilling," Wolf says, a little impatient. "But I mean for the future, anything you wouldn't want to do? Cause if you say anything is open... well... I'd be wary of what I can come up with."

My chest shakes as a nervous laugh leaves my lungs. "Oh... right..." I say trying my best to think. "Like... I'd rather not play around with scat. Blood play and cutting are not something I am into. And I would prefer if you didn't fuck me literally in public, but like hidden, or in the woods is fine." I pause, searching for something to add to the list but can't. "I... think that is it. I am pretty open."

"Reasonable," He says. "Nothing that will impede my use of you at least. Just a second." I hear a clatter and some taps and clicks of metal wear, a sizzle. A few moments later wolf returns. "Sorry, cooking breakfast."

"No problem," I say with a giggle, wondering why he apologized to his sissy for that of all things.

"So, hypothetically," He starts. "If I was to ask you to get a piercing, a tongue piercing for example, or a slutty tattoo, you would be okay with that?"

I gulp, heat rushing from my chest to my face. "If you wanted me to, I would, I am your sissy. As long as it's not a face tat, I think it would be okay."

"And in the future, if let's say I wanted to pay for body mods. Body hair removal, lip filler, breast implants. You are young enough, so maybe hormones instead of implants. Either way." I hear another clatter and a sizzle before he comes back. "Would you be okay with that?" He asks.

I think some of the blood drains from my face, my heart thumps. "Fuck... That is pretty... extreme." I say quietly, but the more I think about it the more I feel myself flush, like it is something I desire. "But... I think I would be okay with it, I would look more like a sissy should with all that going on." I swallow a lump that was forming in my throat and remember the feelings that flowed through me as I stared into the mirror last night. "I would look more like me..." I add quietly.

"Oh, sissy..." He says, his tone leaning into a caring intonation. "If it's what you want it doesn't need to be in the future. If all you need is a push I can be that. We can decide on that later though. I just wanted to see where your head was at, and set a few ground rules. Just a sec, it's done." There is a clatter and after a minute or so Wolf comes back to the phone. "I hope you know how to cook, cause if you ever stay the night you better bet you'll be cooking me breakfast as a thank you."

I laugh, genuine and breathy. "Of course daddy. My holes are yours, cum is my reward. I would feel bad if I didn't do something extra."

"Good little sissy, you know your place." I hear him chew something, "As for rules, I've thought of five, should help keep things nice and heated. They are to be followed at all times unless I explicitly tell you otherwise. Understand?"

"Got it." I nod reflexively, knowing he can't see.

"Rule one and two should already be familiar to some extent." He says. "Rule one: You must always ask permission to cum. Sissygasms are the ultimate reward for girls like you, they are a treat and must be asked for, never taken. That means if you are masturbating your sissy pussy, or letting some rando nail you, you have to contact me in order to cum, or get orgasm approval in advance." He pauses to chew. "Now, accidents happen, maybe you meet someone at a party and they are plugging away, and you happen to squirt. You will be punished, of course you will, you broke a rule. But the punishment for cumming and telling me will be far less severe than if you don't and I find out. Sound good?"

I blush, every single orgasm for the foreseeable future will be not only known by wolf, but controlled by him. "Yup," I respond in the affirmative.

"Rule number two." He says, "Is about your cage. It is a permanent part of you now. It is the one true symbol that a sissy can wear to show what they are. It signifies the uselessness of your clitty, and invites people, and yourself to look for other ways of pleasure. 24/7 for the foreseeable future. That being said, hygiene is key, and like I told you, I will be unlocking you, let's say... once a week to clean and shave the parts you couldn't with it on. If you get hard while it is off, you will be punished severely. If you somehow manage to cum while you are unlocked, the measures taken to correct your behavior will be drastic."

"Of course," I say, an itch creeping along my locked clitty as I think about permanent chastity. "That makes sense."

"Good, now, Rule number three." He says continuing the briefing. "From now on, you are to wear a plug at all times. It is to become just as much of a staple of your unclothed form as the chastity cage. You will wear it to sleep, to eat, to bath, to lectures, to work, at the gym, everywhere. All the time. I will monitor the fit as we progress your tight little hole to the perfect pussy it was made to be and I will adjust the size and length of the plug accordingly. I just want to make sure that you are always stretched and ready to take a dick at a moments notice. Lubing up the plug each time you have to remove it should make it so that you are never dry either, always ready for dick. I am sure this rule is more of a bonus for a slut like you though, huh?"

"I don't mind it." I say with a laugh. "I like feeling filled up, and anything for you daddy."

"What a delightful little whore you are sissy," As he matches my laugh with a chuckle. "Rule number four: If I call, or text, or drop by your house, you stop what you are doing and you attend to me. You are my sissy and your place, your purpose, is on and around my cock. I'm not a lunatic though, life happens, but it better be a fucking good excuse, those excuses better come few and far between. If I need my balls drained, I am coming to you cause I know there won't be any fucking around. I'll dump a load in one of your holes, you will thank me for it, and we can both get on with our day. We will still have longer sessions where I have some fun with you, but a sissy is a fleshlight for men, and I am gonna use you if I need it."

My clitty flexes against its cage as he explains the rule, pussy twitching as he refers to me as a fleshlight, his fleshlight. "That rule sounds fun..." I moan, "I'll make sure I'm always ready for your cock."

"Well, that is good to hear, it also brings us to the last rule." Wolf says, taking a gulp of something. "I am changing your diet, well... maybe. I don't know if you already are, but if you are not then rule number five is that you are a vegetarian from now on. For better or worse, a sissy has a pussy that is different from other girls. A sissy needs to take extra care when keeping her pussy clean for daddy and random men. Cutting meat, and the fat that comes from it will help tremendously with that. We are both adults, accidents happen, but this'll keep those to a minimum. Remember that you serve men now, you serve me. You holes are for our pleasure, for my pleasure. You best do your best to make it as pleasurable as possible."

"B-but... bacon?" I say sadly. "Tacos?"

"Not anymore sissy, not unless they are fake or made of tofu or something." Wolf says with some added snark. "And don't let me catch you cheating or I'll buy you a cage with a urethral sound so you lose control of your bladder and leak piss all the time."

I shiver at the thought of something being shoved into my clitty. "Ughh... I... fine..." I say, disappointed. "I guess I am gonna have to throw some food out then..."

"Ha, no need to throw it out," Laughing, as he takes another gulp of whatever he is drinking. "I'm gonna need my dick sucked later tonight, you can just give me what you were going to throw out. Hell, I'll even toss some money your way, I know meat is costing these days."

"Oh, ok!" I say happily, swayed by the money, and the prospect of swallowing more of Wolf's sperm.

"Meat is also linked to testosterone production, so better to cut it out for that as well." Wolf says. "All those sound good? I'm probably gonna add more as we go on, but I think that is a good starting point for now, yeah?"

"Actually," I say, my voice pitching up with nerves. "Can I... I would like to add a rule, if that is okay."

"Sure, I mean maybe... depends on the rule." He says. "Let's hear it, if I like it then I'll add it."

I let out a nervous sigh, "Ok... ok..." my mind racing as I try to motivate myself to say it, to lock myself into it. "Ok... I want to... I want you to force me to... to... to wear feminine makeup from now on, 24/7, or... maybe not when I am sleeping as that is bad for the skin, but from when I wake up to when I sleep. I just want to look feminine and I don't without makeup and I realized that I don't really like my reflection without it, and I really like my reflection when I do have it on, and it makes me feel good and like myself, and... and... and... I'm not sure if I will be able to stick with it unless I have a push. It's kind of scary to think about changing, the conversation with my friends and family, the looks... But I am sure under the threat of punishment I won't falter, I'll change, my outside to reflect my insides."

Wolf doesn't say anything, letting me stew in silence for a few long moments before letting out a deep breath. "Wow," He says, "Quite a little rambling speech there... Don't get me wrong, it is a perfect rule, just not one I usually implement until you are further along, but... Fuck it, if it's what you want, why not. Consider it done, if I catch you out of sleeping hours without makeup, more than that, without feminine and well done makeup. I will punish you. And just to make sure you are following rules two, three and six. I want a pictures of your cage, your plug, and your done up face every morning. Does that satisfy you?"

Rippling anxiety courses through me, freezing my lungs until I shake off the nerves with a stretch. "Fuck me... Ummm yeah... holy shit... I guess this is it now..." Slowly a smile starts to spread across my face. "This is it now..." I repeat.

"Nah, whether it was today or a year from now, you were going only be wearing women's clothes and makeup at some point. Least we can get to the fun stuff sooner this way." He says with a chuckle. "Actually... I mean I saw your makeup when you took off the blindfold, I would say you are already femme enough to pass. People are just going to think you are a woman wearing men's clothes if you do the makeup the same or better as yesterday. Why not just change your wardrobe as well? It's not gonna change how people look at you other than making you look like a more fuckable woman."

"I guess you are right..." I say hesitantly, nervous about such a quick change. "But I don't actually have that many articles of clothing that I would consider feminine. And most of what I do have is far too lewd to wear outside, or like... day to day. And I don't really have the money at the moment to expand it to a healthy wardrobe."

Wolf laughs, and somehow in a way that makes me feel foolish. "Is that all?" He says still snickering. "Looks like I am gonna have to take you shopping then. If my sissy wants to dress like a proper sissy, I can't have them wanting for clothes. Are you free this coming Saturday?"

My breath catches. "Wait... isn't that a little much? A whole wardrobe? That's hundreds of dollars if not more, isn't it?"

"So? You think I can't or won't drop that much on you? You know how much laser hair removal is? Body augmentation?" Wolf's words bite as if he is annoyed, but I think he is just playing it up a bit. "It was gonna go this way eventually, If you want to dress like a sissy now then I am happy to do it. Means I can show you off more readily. Hell, let's call it payment for the top tier porn you sent me, I am going to be hanging on to the video of your first sissygasm for a long time. That and the video of me crushing that sissy pussy are well worth a few thousand dollars alone. If you keep up the good work you will never be wanting for anything sissy related."

Looks like I am well on my way to having a sugar daddy, or at least someone who wants to invest in my sissydom. "So we are going to go shopping, together, then? Will you be picking out my wardrobe?" I say, imagining a collection of lewd garments under Wolf's guide.

"Nah. I'll pick out a few things, but I want my sissies to develop their own style. I want you to try to impress me." He pauses, "How about this. You are coming. We are going to get you a whole new wardrobe, and then I am going to come back to your apartment and gather up all of you old clothes and help you throw them out. Sound like a plan?"

I gulp, "Y-yes daddy," I say with a stutter. "I am excited to go shopping with you, to get sissy clothes, to finally be able to dress the way I should."

"Good girl," He says cheerfully. "Let's add that to rule six, or maybe make it rule seven. Doesn't really matter. From Saturday on, you are never allowed to wear boys clothes again. To anything, ever. Honestly it seems a bit extreme so early on, but you are eager, I am sure you will be able to cope. If not... well, you won't have anything else to wear, so... good luck slut."

Nervous laughing stutters my breathing, in four days I won't even be able to hide my sissy side from my friends and family. Sure I can just say I am trans, and... I might be but it is still a change. That being said, I can hide the absolute perverse side of my newfound sissy life, but the subtleties will soon be out there for everyone to see. It is a good thing I am cute and petite, at least I won't get as many looks, and the stares might be generally ones of want instead of confusion.

"Alright, nice chat slut." Wolf says, already wrapping up the conversation. I get the feeling that there is no room for emotional connection in this relationship. Just transformation, and perverted, degenerate sex. "You know the rules, and although you don't know the specifics of punishment you should know that breaking the rules will have severe implications. And yeah... that is all I wanted to talk to you about. I'll send my address when I need you to cum over so I can dump a load down your throat. Should be around seven or eight, be ready. See ya later sissy."

"Bye Daddy," I moan wantonly, "And thank you!"

"For what?"

"Helping me see who I really am, pushing me towards it, and most of all..." I let the sentence hang for effect, licking my lips. "For your fat fucking cock."

"Ha," He says, unable to hold back a laugh. "Bahahaha, You are welcome you fucking cock addicted bimbo. I am going to fuck your skull so hard tonight your ears will be ringing." He promptly hangs up the phone as soon as he finishes his promise of brutality.

"Holy shit..." I whisper to myself. "Holy shit, This is crazy. I've got a daddy now, maybe even a sugar daddy. A daddy who actually wants to use me, who actually wants to treat me like a sissy and doesn't just want to fuck me. Fuck yes!!! This is awesome. Kinda scary... but... Awwwwesome." I fall back onto my bed, hugging my phone to my chest as I pulse with excitement. My dreams are finally coming true, a real alpha man who will turn me into the drooling set of holes I am meant to be. No retreat, just surrender.

I smile, giggle, laugh. Happy, excited, nervous. A tear roles down my cheek. A happy tear brought about by fulfillment.

~ ~ ~

I spent the morning before lectures started grooming myself. I was about to go out in public with makeup on for the first time. I didn't have any women's clothes so I wanted to be as cute as possible. Long straight hair brushed and tucked behind the ears, a few bobby pins to keep it held. I toned down the makeup from the slutty look I had put on for my first meeting with Wolf. Just a classy feminine look, with some extra contours to negate my more masculine features. I was delighted to see my true self in the reflection of the mirror, it calmed me, cut the nerves that were building. I chose the tightest pants I could find. Still a little too baggy, unisex at best. With nothing to go up top, I just threw on a hoodie and t-shirt. Tom-girl look for the win.

I sent a pic of my outfit and makeup to Wolf, saying that I was going to class soon. He said that the makeup was cute, and that I might even get hit on by some lesbians wearing that particular outfit. I also sent him a pic of my plugged pussy and caged clitty, I don't really think he needed the proof, there is no doubt in my mind that I will be following his rules to the best of my abilities.

Lectures were decent, no one in town or on campus really stared at me. Though I did get way more casual glances than usually. Many eyes skirting my body as I passed, mostly guys eyes. I wasn't quite as good at taking notes as I usually am. My mind kept wandering to deviant places, clitty attempting to rise in turn as I stewed in them.

Luckily I didn't run into any of my friends, though I am sure a few people recognized me, and rumors travel fast. I have another day to come up with a monologue to explain my changes, and that is all that matters.

When I get home I ask Wolf in a text if it is okay to remove my plug to masturbate. He says 'Of course, don't be afraid to train that hole, just ask permission to cum, and plug when you are done.' I spend an hour or so watching sissy porn on my phone while fingering my pussy before I break to do some studying.