Letting Strangers In Ch. 01 of 04

Letting Strangers In - 1/4

Author's note:

This is inspired by a true story, everything up until the first insertion is 100% true. After that it is up to you to decide where creative freedom came in. The act of meeting like the main character did is extremely dangerous. If you are interested in similar things, do it with someone you trust. Go get a coffee with them first, make sure they are mostly sane. The themes in this story are heavily based in the sissy fetish. If crossdressing is not your thing, if humiliation is not your thing, I advise you to look elsewhere.

Thanks for taking a look!

Letting Strangers In - 1/4

I know, I know. I fucking know. This is how you end up getting murdered, this is how you end up kidnapped and sold into, well... you know. But I just... I can't help myself, the idea of giving up control like this, letting a stranger into my house like this. It melts me, I am so tingly, my heart is racing, and my face feels like it is on fire. Heat; fidgety, nervous, exciting heat. Despite everything I shouldn't be doing, here I kneel on the soft carpet in front of my bed. Handcuffed, blindfolded, and plugged, oh god the plug.

I met him on a dating app after months of edging myself to the point of deviancy. My profile was filthy, calling myself slurs, asking to be used and abused, it screamed cum craving whore. It was Perfect. He called me a slut, called me sexy, said he wanted to fuck my holes until I passed out. I loved it, I wanted it, and I craved it. Sane? Maybe not. But desired? More than anything.

I like to think I led him to ask to meet me. But who knows. For the niche that I fell into, I was hot, desirable. Or so I had been told. His username had something to do with a wolf, and he was voracious in pursuit of a meeting, fitting for his namesake. We set a date: today. I told him what I wanted to do, he loved the idea, who wouldn't. A fuckdoll restrained and waiting, perfection after a long day at work. We set a time: any minute now. I would hear creaking up the stairs outside my apartment, hear footsteps in the main room, hear them get louder, then muffle as they crossed onto the carpet. Then he would be here, the wolf would be here.

Ughh, I guess this is what porn addiction mixed with a propensity for being a submissive crossdressing bitch does to you. I got it in my head that this is what I deserve. But I also want it to be what I deserve. I want to be the type of person that let's guys do whatever they want to them. I want to be a whore, just a couple of holes, a masturbation device. Maybe my wishes will come true.

I am in my third year of university, and have been crossdressing for a while, at least since the winter of my first year. I got fucking good at dressing myself. It helped that I was small, petite even, I could go to different women's clothing stores and actually pick out things that fit. I was flat up top, but my lack of muscle meant that I could pass as just that, flat. I worked on my ass diligently though, running, biking, squats, bridges, anything to push my form a little bit more feminine, and it worked. Paired with some estrogen boosting supplements and diet I was hella trap.

I had bought dildos, plugs, sometimes I would wear them all day. To class, with friends, to the store. It felt so good knowing that I was being a slut and no one could tell. That I was preparing myself for the day I rented my holes out to the highest bidders and lived my live as a fleshlight. I was no virgin, though it's not like I was a breeding bull either. A few cases of intermingling with both sexes here and there. But it was always lacking, never what I wanted. I wanted to be owned and passed around, worn out, gaped, filled.

That is when I found sissy stuff. I know it was all just a fantasy, probably. But it appealed to exactly what I wanted from my sexual life, from my whole life. Subservience, humiliation, cum addicted degeneracy. I started watching, listening, and practicing hypnosis. I know, it only works if the person wants to be hypnotized. But I fell firmly into that category, I desperately wanted to be hypnotized, I didn't want to think anymore. I wanted to serve, I wanted to be fucked. I wanted to be addicted to cock. And it worked. My life didn't fall apart, I was still able to function, but all of my free time was occupied by cock, by learning how to dress better, by makeup, by shaving myself smooth. And mostly, by training my throat and asspussy for the day I found and owner, and later when he shared me with his friends. I can't wait.

I think I am perfect for the sissy life. I am small, for a bio man that is. 5'4 with weak shoulders and decent enough hips. I never was able to grow much hair on any part of me other than my head, which is a plus because I hate shaving and the less I have to do, the more awesome my life is. I have been growing out my hair since I started crossdressing, much to the chagrin of my parents and peers. Whatever... if only they knew. Anyway, it reaches my nipples now, nearly jet black and straight. I love it, there are so many hairstyles I can do now, so many ways to look sexier. Though right now it is loose. I want him to be able to grab it and hold it how he pleases. However he pleases...

Not being able to grow much hair other than the top of my head is also a plus when it comes to makeup, smooth skin, less concealer, less everything. More of that natural look. And I was getting fucking good at it. I swear people wouldn't be able tell, or at least would have to triple check if I walked by them on the street with makeup and my hair down. Even more so if I was dressed up, though I doubt I would wear what I am wearing today on the street.

Black stockings, that go way too high, they are open in the back, with wide fish netting, windows onto my fair skin. Somehow it makes them seem more lewd than they are. A coral(ish) skirt with a long waist that I pull up way too high, it lengthens my legs while also rendering any modesty the skirt could have offered obsolete. A thin, tight, grey, ludicrously cropped sweater covers my chest to just below my nipples, it is impressive what the eye does when the prize is teased. What it imagines to be there when it wanders. I like to think it would make someone want me to have tits. I wish I had tits... Some underboob with this top, mmmm...

I am wearing a nice lacy black thong. I love wearing panties, nothing makes me feel more fem then when all the prep is done, all the makeup, shaving, plugging. And then I slide those soft garments up my legs, complete. What doesn't make me feel fem, what brings me the most shame as an aspiring sissy. Is what the thong hides. It's not like it's massive. It is just above average. But every time it gets hard in my panties and forms a bulge I just can't help but wish it was smaller... I wish it was smaller. I wish my clitty actually looked like a clitty instead of this god damn sausage...

That's why I started wearing the cage, as of now, I have been wearing it for about a week, though I take it off to sleep. It makes me so happy knowing that it can't get any bigger than the cage. And even though the cage isn't small, it is at least cute and a nice shade of purple. My clit might not be tiny, but I think it is pretty when it is locked up. The cage was uncomfortable at first, but my clitty has learned to stop getting as hard when I am aroused. And holy, fucking, shit, am I aroused right now. Happy that I am locked up and waiting. I hope Wolf appreciates everything that I have done to get pretty for him. For now I wait.

~ ~ ~

My patience is wearing thin, but he is only a few minutes late as far as I can tell.

Creaking... Creaking? Creaking!

Creaking, the sound of old warped steps worn smooth around steel nails. Someone is here, I hope it is him and not one of my friends. What an embarrassment that would be. I was getting close to the point of pulling off my blindfold and sending him a message, but now, I am on fire. My clitty surges and presses itself hard against its small plastic prison. The feeling is exquisite, though nothing compared to what I feel in my chest. Heavy, wet, nervous pressure, the culmination of so many weeks, months, years of waiting squeezing my heart. I am so fucking aroused right now it feels like I am sweating, my skin tingles with sharp pinpricks.

I hear the door open, no knocking, just like I told him. It is him. It is him. Fuck me... it is him. Can I do this? Is it too late to turn back?

No! This is what I want. I am a slut to be used. I want him, it doesn't matter what he does, I want this.

Just like I imagined, heavy footsteps across the floor in the main room. I know he can see me now, see me waiting through the doorway. He stays silent, I let out a small whimper. I want him to acknowledge me. Say something, anything. But there is nothing, even as he walks onto the carpet, closer and closer. I can feel the vibrations of his steps travel through the floor and into my knees and feet. I shudder along with the floorboards that lie under the carpet, closer and closer, then past me, towards my bed. I hear a light knock of something being placed on my bedside table. Then footsteps back to me.

Then nothing. Then silence. He stops, leaving my heart to take over, thundering in my chest. Surging through my ears. Everything louder than it should be. I let out a long breath, I had forgotten to breath, everything was so hot. He is so close, I swear I can feel him. Just out of reach, if I leaned forward would I touch him? Is some of the heat coming from his body? His legs? His crotch?

I told him earlier not to ask. I told him that if I didn't like anything I would let him know. Cutting through the silence, crisp and clear. The sound of him undoing his belt, lightweight metal clacking. God, fuck me, the zip of his pants, I swear he must have seen me shudder. I am breathing hard, part of me is trying to calm down, another just wants to lean forward, start moaning, start telling him to fuck me, asking, begging. I hear the sound of fabric sliding down, the muffled thump of his belt hitting the floor along with his pants.

Is that? Could it be? Quiet... so quiet. The sound of something being rubbed? Stroked? It's so close, I think I can feel the air being pushed, touching, softly caressing my cheeks.

"Open" Wolf says, deep and commanding.

I half expected Wolf to stay silent for the whole time, I gasp when he speaks. It surely is of normal volume, but it booms through me. I open without thinking, letting my mouth gape. I stick my tongue out past my lips, the perfect landing site for the delivery of my package. His package.

When it touches my tongue, I let out a desperate moan. The initial contact was like a spark that ignited the reality of the situation. I was truly about to be fucked. Everything that we talked about would come true. I was going to be his. I am his.

I go to lick it, but he tuts. I still my tongue and allow him, give him, entrance. He doesn't take it. With the tip of his cock he begins to rub. Up and down along the outstretched part of my tongue. I start to drool, I am sure the head of his cock is glistening as he moves it. He rubs in slow, wet, circles. From my tongue, along my upper lip, the back down across my tongue. Again and again, trepidation building in me. I just want it inside. 'Stop teasing me!' I want to yell, but I won't. It is not my place, I gave him my agency long ago, while we were discussing plans for today over text.

"Usually it's a bit of catfish when I show up like this," Wolf says, continuing to rub his cock over the edges of my mouth pussy. "But you, you are the real deal."

I let out a quiet high pitched moan, almost a squeal. Was that praise? Does he think I am good enough? Did I make him happy already? Did he say usually? God, I bet he does this a lot, I hope I don't disappoint him. Good thing I have been practicing.

When I feel him grab the back of my head. When I feel his fingers worm their way through my hair. When I feel him twist and grip the strands. When I feel him start to pull me towards him. I become numb. Not anaesthetized, not frost bitten. But the buzzing you get when a limb partially falls asleep. Deep vibrating pinpricks that radiate from his hand, through my scalp, down my spine. They spread and spread, reaching my fingertips and toes. Electricity in a few simple movements. This was it. There is no going back. In a mere moment, I will be a sissy, for life.

Deliciously, he pulls me forward; he slips over my tongue, past my lips which I close around him. He is thicker than any of my toys... fuck me. He tastes clean, smelling vaguely of mint bodywash. On the surface I am thanking him for the courtesy of a shower, but deep down, deep deep down, I think I might have liked it more if he didn't even care enough about me to wash first. Lavish me like the dirty fucking slut I am.

He doesn't move, and neither do I. I would be a statue if I wasn't shaking with anticipation, small nervous shivers. It seems like an eternity. I want it, I want more. Cautious, like approaching a wild animal, I pull my tongue back and slide the tip up across the head of his cock. Slow and gentle, just one single lick. He laughs, like the waiting was on purpose, like he knew I would be the one to make the first move. I lick him again, faster, with more pressure, something approaching a flick. I feel his response, the response I wanted. He tightens his grip on my head, on my hair.

"Use that tongue sissy, show me you want it and I just might fuck your throat." Deep, commanding. He speaks in a lustful growl.

Of course I obey, of course I do. I want it. It's just the head poking through my lips, plenty of room to run my tongue over him in long languid circles. I moan without thinking, and giggle when I do. I can't believe it is happening, that I went this far the very first time as a sissy. I try to bob my head, to get some lip and suction action in with my tongue, but he holds my head firm.

"Nuh uh," he says. "All you need to worry about is what you can do with that hole of yours..."

He leaves the end of the sentence hanging in an odd way, but I ignore it. I refocus on what I can do with my tongue. He is utterly covered in my saliva, a smooth, taught, pulsing mass of flesh and nerve endings. All mine to play with. And I do play with it, at least as much as one can with their tongue and tongue alone. Still, moments turns to minutes and my tongue begins to tire. I try, I really do, but each flick, each push, each swirl was losing its oomph. I was ready to move on.

The man clicked his tongue, at the very least feigning disapproval of my stamina. "Not very useful are you?" He says, with a sigh. "Now, let's see what the rest of this hole can do, before I get bored."

God, I know it should hurt. And maybe it does somewhere in me. But hearing him say I lack use or whatever, after basically giving it my all. The humiliation, the degradation. Fuck it turns me on. Like a furnace. My clitty jumps and begins to swell again, mashing itself against the inside of the cage, desperate to grow past its confines.

Maybe he had loosened his grip. Maybe I had gotten used to it. Either way it got tighter, I can feel my scalp stretching with the hair he twists and pulls. Excessive, dominant, forceful. He begins to pull me forward, agonizingly slow. The slipping of my wet lips over the delicate intricacies of his skin, the peaks and troughs of what lay beneath, the snaking ranges of pulsing veins. Focusing on him entering my mouth pussy like a fiend, every detail was heightened. I wanted to remember my first cock as a sissy, I knew I might never see it, but fuck, was I ever feeling it.

I don't really remember the epic journey from tip to base, I was too focused on the topography of his member to care that it was going deeper and deeper. I feel my nose kiss the skin between his naval and cock. I feel the head of him tickle the back of my throat. I cough at the sensation, quiet and controlled. I want him to know that I trained, that I am a good girl. That my mouth can take it.

His cock is fat, my lips are gripping it in a wide O. It really is wider than any of my toys. I am glad, a real man, he is thicker than me, bigger than me by all accounts, though I am still glad I am caged. He isn't necessarily the longest man I have ever seen, but he is girthy, and to be fair, a lot of the times that is what matters.

He keeps pushing me. My nose squishes into his abdomen. His cock presses hard into the back of my throat, the pressure is wonderful. I gag silently, swallowing, the back of my throat flexes and moves around the head of his cock, the base of my tongue squeezing it up against the roof of my mouth. He pushes harder, forcing a few more centimeters into me before he truly bottoms out.

He groans and grinds my head side to side, grinds my face into him, grinds into my throat. Then with a sudden jerk he pulls me off his cock. The tug sends a stinging surge through my scalp. "Do you want this?" He asks, rubbing his cock over my lips and cheeks. Smearing my saliva anywhere that isn't covered by my blindfold. I don't really respond, I just let out a wanton moan, my tongue lolling.

"Do you want this?" He asks again, rapidly tapping the head of his cock on my nose.

"Yesssss..." I moan, "I want it so bad."

He laughs, condescending, more of a scoff. "Beg for it," Wolf says, pulling his cock away from my face and leaning my head back. "Beg me to fuck your worthless sissy face with my cock."

I moan, long and loud, I want him to know that I love how he is treating me. I love how he is treating me. Firm, degrading, humiliating, and oh so hot. "Please," I beg, laying on the sultry purr as best I can. "Please fuck me with your big cock, please use my mouth pussy, please fuck my throat."

"More," He says, "Tell me why you deserve to be skull fucked."

I purr, vibrating in my skin, breathing hard. "Because that is what all sissies deserve, because that is what I deserve. I am nothing but a... but a..." I freeze for a brief moment, trying to come up with the right words, the words that will make him turn me into an absolute mess.

"Nothing but a what?" He demands, his deep voice rumbling, rasping.

I take a long lingering breath, pausing to prepare what is about to come out of my mouth, and then hopefully in.

"I am nothing but a cum toilet, a place to dump your loads whenever you feel the need. I am nothing but a cock craving, cum drunk, bimbo slut! I deserve to be skull fucked because that is the only fucking thing I am good for, I deserve to be skull fucked because I am nothing but a sissy whore, a slut, a free use prostitute paid in full dripping holes and harsh, fucking, treatment! I deserve to be skull fucked because I want it, more than that, because I need it. I deserve to be skull fucked because I have been a good sissy slut, I have been practicing, now let me show you just how hard I can take it. Let me show you I deserve your cum!" I am breathing hard as I finish speaking, did I really just say all that? Wow, did I really mean all that? I... I think I did. I pout, and add one last word to the menagerie of self-debasement "Please...?"

This time he really laughs, bellowing, loud, amused. "Fuck me," he says. "I did not expect that, did you use your slutty little head to plan that out beforehand or something?"

I shake my head, I didn't plan it, but in that moment I for sure meant it, meant all of it.

He laughs again, and taps his cock on my nose. "Someone has been watching too much porn." Grating, he speaks. Degrading: his intentions. "But you are right, about all of what you said. Well, some of it you will have to prove. But about what you deserve? Fuck yeah, I can see it in you, hear it in your voice. You are meant for a life of cock. A life of getting fucked by any and every guy that wants you."