A Weekend Away - Day 1

Your hands slide across my back, rubbing more of the oil into my skin as you massage my muscles. I can feel little moments where your naked flesh touches mine, sending little jolts of excitement through my body. I can tell that you're wearing at least panties simply from the occasional moments where the material touches me, feeling like a scratch compared to the smoothness of your skin. Even though my head is tilted to the side, the blindfold is blocking every hint of light from the room. I keep losing myself in my own thoughts, asking myself questions about this situation that we find ourselves in. Ordinarily, I would be the one giving you a massage... there's an almost unnatural feeling to being pampered, if that's what this is. I can't help but run simulations in my brain about possible outcomes. Is there a catch? Will there be a punishment for accepting this? Is it a reward? Time already feels like it's losing meaning, even though it's only been 10 minutes. Maybe 15? Certainly not any more than 20! However long, it's safe to say that the beginning of our weekend together hasn't started quite how I expected it to. The visions of being spanked, degraded, and humiliated are a stark contrast to this moment.

I let out a small sigh or moan as your thumbs dig into the backs of my shoulders, homing in on the tension. Even behind the blindfold, my eyes are rolling to the back of my head, as my breathing becomes slower, deeper, and heavier. I find my brain feeling foggy... or maybe clear? An almost trance-like state where the physical world dissolves and our bodies feel connected, pulsing gently along to the meditative music that fills the room. I'm somehow hyper aware of every physical sensation, and yet I'm not feeling it on my body but rather as sparks of light within my mind. Colours that bounce and zigzag depending on the pressure.

Sometimes it feels like my senses are stronger than normal. Maybe I'm just imaging it. But I know that you're not wearing any perfume or deodorant today. I can tell. The massage oil appears to be scentless, but even the lavender candle burning on the side isn't masking the natural musky smell that enters my nostrils and ignites an already spreading arousal within my body. I don't remember when the natural smell of your body became so intoxicating to me, but there's something almost primal that awakens inside me, an ancient arousal trigger that fills me with desire and need. A need to obey orders. Orders that are currently non-existent. You haven't said a single word to me since turning the music on. But when your right thumb presses into a knot in my back, forcing out a loud sigh as my body tenses and then relaxes, it's almost as if you can read my mind as you lean in close and whisper three words.

"Good boy! Relax!"

That's all it takes. Just three words! And suddenly my relaxed, tired body starts waking up. I feel my heart pump blood to those tingling areas as the fireworks in my brain ignite, explode, and send colours flying throughout my consciousness. But almost as quickly as the excitement peaked, I feel myself sinking back down deeper than before. Almost like a hypnosis trance that brings you out slightly, only to drop you down much, much deeper. I start to imagine that you're using my pre-installed hypnotic triggers to send my mind deeper and deeper into trance. Somehow, it feels like that's what you expect -- for my brain to leave my body behind, subject to your whims and completely at your mercy.

Each new part of my body that you work feels more intimate than the last. Even sliding your fingers between mine feels spectacular. My calves, my thighs (especially my inner thighs), my shoulders, my back. And while I do have sparks of arousal, I am becoming blissfully mindless. Even as you slide my underwear further down by ass so you can massage my cheeks. There's an initial spike of arousal, a little cock twitch, a moment of light in my brain. And then calm. My brain barely even reacts as my underwear slides down my body and off my feet, because your oily hands immediately massage and relax my ass, thighs, and calves. I tell myself that no matter what the outcome, this has been truly worth it. And my only reservation is that I want to return this relaxation to you. I'm sure you'll make good use of me this weekend.

You guide my body up into the air by gently lifting my hips, and before I know it, my abdomen is being supported by cushions. But all it takes is another grip of my ass with your firm, slippery hands to distract my brain as my consciousness drifts away again. I can feel my ass cheeks spreading slightly as I adjust to it being raised in the air. Your thumbs slide between my cheeks as your massage them, grazing across my asshole as you squeeze. My brain barely registers the fluid movement of your hands across my body. I feel like a puddle that your hand is stirring, splashing, and spinning.

You slide something over my right ankle, and then over my left ankle. But my brain only focuses on the warm sensation as you slide fresh, warm oil up my legs, over my ass cheeks, and across my back. The movement of your hands create a sensation in my brain that feels like waves slowly crashing onto a beach. And as you kneeling or stand close to my head and massage my scalp, I hear those powerful words again.

"Such a good boy! So relaxed!"

You slide something up my right wrist, and again with the left wrist. As you let go of each one, I find that my arms are being slightly pulled towards each corner of the bed. It's not uncomfortable, not by any means. If anything, it only adds to the relaxation -- like wearing a weighted blanket. My brain is aware of the slight tension, but as you rub more oil up and down my arms, the sensation melts into my mind puddle.

"Feel how heavy your body is! You couldn't move now, even if you really wanted to... but we both know that you don't. You want to stay right where you are. Try lifting you arms a little, just to feel how heavy your body is."

I do as she says. And as I attempt to raise my arms, I realise that I can barely lift them. It feels like my wrists are being held down by cement, trapped against the bed as if magnetised to it. But this doesn't feel threatening or worrying, but rather freeing. My brain relaxes knowing that I can't move, therefore, I don't need to think about moving. I don't need to worry about what my hands are supposed to be doing or where my feet should be. I can just lie there, free, relaxed, and happy.

"Good boy!" she whispers again, as more oil dribbles onto my body, sliding between my ass cheeks. It feels like a different consistency compared with the other stuff. "Now, say thank you!"

"Thank you!" I reply immediately.

"Say, thank you, Mistress!"

"Thank you, Mistress!"

I feel and hear the wobble in my voice as I respond. We're returning to more familiar territory now, and as exciting that is, I can't help but wonder where this is going to lead. I still feel like my consciousness is lost deep inside my mind, disconnected from my body and the rest of my brain. There's a sensation not dissimilar to paralysis, and I can't help but wonder if you have been using my hypnosis triggers without me realising. Could they have been subtle? Did they appear in the music? Have I reached this deep mental state simply from the massage?

I hear moving around but my brain struggles to connect the dots. Fabric across skin. Latex against latex. It all feels so far away. So distant. Does any of it matter? My brain feels like a blank screen waiting for input. Waiting for YOUR input. Each word that leaves your lips creates the thoughts inside my brain. Guides me on how I should feel, what I should be thinking. Even as you stuff something in my mouth, it feels like I'm experiencing it through a hazy wall. The smell and taste immediately tell me that it's your panties. The wonderful taste only slightly tainted by what must be a tiny droplet of massage oil. But the smell manages to float up to my nostrils unhindered, making my mouth salivate and my cock twitch.

"Drop!" you say firmly, snapping your fingers, and I feel my eyes once again roll back in my head as I sink deeper into trance. Was this the first time you used one of my hypnotic triggers? The thought is so faint in my brain that I can barely ponder it before it vanishes. My mind sinks into a deep, relaxing pit. I feel like I've been swallowed up by the bed with no hope of clawing my way back.

You squeeze my shoulders and neck, and although I feel the latex gloves on your hands, it doesn't seem important. Your thumbs work their magic as your legs and waist press against my thighs and ass. Your hands move down my back, massaging every muscle on the way. I feel you squeezing my ass cheeks, pulling them apart, rubbing your thumbs up and down, around and around, only gently massaging my hole.

"Good boy!" I hear you whisper again, just as your thumb presses against my asshole and slides in. A wave of arousal crashes against my body, and I feel my cock straining against the cushions that are supporting me. My hole tightens around your thumb as I feel my body straining to adjust to the sensation. I can't help but let out another moan, a primal moan. The type of moan that without context, could be mistaken for pain. I feel your thumb moving in and out, around and around.

But it doesn't take long before your thumb has been swapped out for a toy. It feels like a butt plug. And as it slides inside me, I feel the stretch as it reaches the thickest part. And just as it passes that point, and my asshole shrinks back down around it, another wave of pleasure rolls over me. I can feel the damp spot on my cock where puddles of precum are flowing out onto the cushions. I can't help but worry that if I cum now, I'll be making quite the mess! My brain almost snaps out of its trance-state to wonder how much the Airbnb people will charge us if there cushions are destroyed by puddles of cum.

I hear you walking towards the top of the bed, with your gloved fingers trailing across my skin. You pull the panties out my mouth, and I realise how dry my tongue is from having the fabric in there for so long. I hear you removing a latex glove, followed by some wet sounds, and then soaking, delicious fingers sliding into my mouth. I recognise the taste immediately, and so eagerly suck every drop off your fingers.

"Can you taste how wet I am?"

"Yes, Mistress!" I mumble, your fingers still inside my mouth.

You take a few steps around the bed before returning.

"And what about now?"

The fingers slide into my mouth again, but the flavour is different. I still recognise it straight away as my precum. I hear you let out a little moan as I suck them clean just as eagerly.

"You like being my toy to play with, don't you?"

"Yes, Mistress!"

"You'll try your best to please me, won't you?"

"Yes, Mistress!"

"You want me to pull that plug out your ass so I can put something bigger in, don't you?"

"Yes, Mistress!"

"Beg me! Beg me to fill that slutty, needy hole of yours! Beg me to turn you into the leaking, drooling, brainless sissy that you always fantasise about being. Beg me to ignore your post nut clarity. Beg me to ignore you begging and pleading and moaning. Beg me to push you to your breaking point... and then just a little further."

"Please, Mistress... Please turn me into a sissy for your entertainment. Please..."

You interrupt my begging attempts.

"No, no, no, my little slut. You don't want to lie to me, do you? Be honest -- this has nothing to do with my entertainment. I have no doubts that you wish desperately to please me, and I can assure you that turning you into the perfect sissy certainly does... but you WANT this. You WANT the freedom from choice. You WANT DESPERATELY for me to help you be the most authentic version of yourself. To remove the masculinity that burdens you oh so much in your day-to-day life. Try again!"

"Please, Mistress... Please help me fulfil my deepest desires of being a sissy. I want desperately to look like a sissy, smell like a sissy, dress like a sissy, cum like a sissy, and be used like a sissy. Please help me be who I truly am!"

"Good girl" you whisper, sliding the plug out my ass. More precum pools on the cushions. You push the plug in and pull it back out, helping to stretch my tight hole, before pulling it out completely.

A new plug presses against my asshole, freshly lubed, and starts to slide inside me. I can feel almost instantly that it's bigger. And as my asshole strains to stretch around it, the leaking from my cock getting more intense.

"Just relax," you tell me, squeezing my ass, "Take a few slow, deep breaths!"

I follow your instructions by filling in my lungs with a long, deep breath, holding it, and then slowly exhaling through my mouth. As I exhale, the plug slides a little further in. And with another breath in, pause, and exhale, it slides in even more. And just as the plug reaches its thickest point and tips past it, my body once again explodes with arousal and pleasure. Another primal moan escapes my lips, as my breathing becomes short and shallow.

"Good girl! Look at you taking that big plug."

"I'm worried that I'm going to cum, Mistress..." I say hesitantly, feeling the all too familiar bubbling of orgasm below the surface. It wouldn't be the first time that I've cum from having a plug in my ass... or the second, third, fourth, or fifth. In truth, I'd lost count of how many times I'd been tipped over the edge by a plug.

"You're such a horny little slut, aren't you?"

"Yes, Mistress! I'm sorry!"

"Don't be sorry! I want you to be a horny, leaking mess. Incapable of controlling yourself. Maybe we need to milk you a little first. Empty those balls so that you can actually handle a plug in your ass without cumming!"

I feel your hand on the plug as you slowly pull it out of me. Each millimetre seems like an eternity, and I start to worry that I won't be able to hold back the orgasm. All it will take is that tiny flicker of tension that usually signals the beginning of the orgasm... and at that point, there won't be anything I can do. But luckily, the whole plug slides out without me tipping over the edge, despite the usual flow of precum.

You move my body around a little, removing the cushions from underneath me. My ass stays in the air as I move onto my knees, and my elbows support my upper body so that I'm in doggy position. The wrist and ankle restraints hold me firmly in place, so I'm limited as to how far I can lift my upper body, stuck in a raised-ass position.

You grab hold of my cock and stroke up and down a few times, squeezing out all the precum and smearing the puddles around on the head of my cock. As you let go, you reach around and wipe your hand on my face. I stick out my tongue to lap up my mess, but your fingers stay away from my mouth this time.

"Look at your little clit twitching away!"

Using two fingers smeared in precum, you start rubbing my frenulum. You don't apply much pressure, and my cock instantly goes rock hard, twitching against you, desperate for more stimulation.

"Please Mistress... I'm going to cum!"

You immediately stop all stimulation, letting out a little giggle while my body vibrates and shivers as little moans escape my lips.

"When you feel like you're about to cum, I want you to say, 'I'm a sissy cum slut'. Do you understand?"

"Yes, Mistress!"

"What are you going to say when you're about to cum?"

"I'm a sissy cum slut!"

"Good girl!"

You start stimulating my frenulum again, and I can't help but wonder if this does feel like clit stimulation. Unlike stroking, I feel the orgasm brewing deep inside me, not on my cock. And almost straight away, the intensity doubles and doubles. My cock strains against your fingers and I feel my balls tightening.

"I'm a sissy cum slut! I'm a sissy cum slut!"

You remove your fingers again, and this time, I can't hold back. There's a long pause as my body tries to hold back the ejaculation. Maybe I can contain it. Maybe I can control myself... but there's nothing I can do. My cock lets out some tiny twitches as cum dribbles out, occasionally doing little spurts.

My breathing changes as the sense of relief from the reduced pressure mixes with the frustration of a ruined orgasm. My cock is already shrinking, returning to its small, flaccid state.

You grab hold of it, and using some of my cum, you start stimulating the frenulum in the exact same way. My whole body convulses as it tries desperately to work out whether this is pain or pleasure. Your fingers apply barely any pressure and move at a medium pace, and sure enough, I start to feel another orgasm building. It doesn't take long at all before I find myself moaning and panting.

"I'm a sissy cum slut!" I moan out.

You let go. My cock twitches, my balls tighten, and I brace myself for another ruined orgasm. But nothing happens. I try to catch my breath, but you start stimulating my frenulum again.

"Beg me to let you taste this delicious cum!"

"Please Mistress, please let me taste my creamy load."

Without stopping the stimulation, two cum-covered fingers slide into my mouth.

Unlike fresh cum, the sensation is far from pleasant. It's cold, slimy, and unappealing. And yet, it doesn't dampen my arousal in the slightest. If anything, it makes me hornier.

"I'm a sissy cum slut," I say again.

You let go and another ruined orgasm dribbles out of my cock.

"I wonder how many of these we can collect," you tell me, "Oh, that's right my little sissy cum slut. I'm holding a glass underneath your cock... and you're going to be choosing which of your holes all this gooey cum goes into. Maybe we'll split it between both? But for now, let's keep on milking you dry!"