The fantasy is always the same. It has been the same one since I was a teenager. The details sometimes change, but the premise remains.
I check into the hotel. Not an exceptionally large and popular one, but one out of the way a little. I get to the room and drop my bag; I draw the blinds and close the curtains. I put on some soft music and start to breathe. My bag has everything in it, my clothes, my hair, my makeup, a few outfits, and some other necessary items. I go to the bathroom and run myself a hot bath.
Yesterday I went to a salon and got a full body wax. It was painful, but worth it. After a while, my skin was numb to all the hair ripping. It feels so good to be smooth. Earlier today I went to a spray tan shop. Nothing excessive, just a light shade all over to even out my skin tone and hide any marks from the waxing.
I stand now in the bathroom, the smell of lavender bath soap filling the air, the steam beginning to fog over the mirror. I take off my clothes and slide in the tub. The warm soapy water splashes against my soft and smooth tanned skin. If I had any body hair left, they would be standing on end as my skin is still sensitive to the hot water.
I lie there for a bit, just letting the smell of the soap soak into my skin. I am sure to gently scrub every part of me, ensuring there is not trace of my former life left on me. After a few more minutes I get out of the tub and dry off. I immediately put on a lavender lotion, I find it is best not to mix too many scents together, so lavender it is. I massage the lotion into my arms and shoulders, my neck and chest, my thighs, legs, and bottom.
The first thing I put on are my panties. This is my favorite part. The black satin feels cool and smooth against my delicate skin. The fit just a little tight, but that is to be expected when a man wears women’s underwear. I get my makeup kit out and choose a nail polish. Nothing wild, but just a little pop of color. A dark red will look nice. I paint my toes first, blowing on them and leaving them to dry. It is okay if I mess a little, I am going to cover them up later. I take out the press on nails for my hands next. I neatly glue each one on. They are not garish or over the top, just long enough that they make my hands feel dainty. I paint them with the same dark red as my toes, being careful to keep them clean.
When they dry, I start on my makeup. I am not the best, but it is amazing what you can learn from online videos. Foundation, blush, highlights, smoky eye shadow and liner, a dark red lip liner and lipstick to match my nails. Pear earrings next, when I pierced my ears at sixteen, I never thought I would use them like this. With my makeup complete, I put on the scalp piece that came with my wig. It holds my hair in place, even when I move around a long. It also helps it look more natural and less obvious that it is a wig. I put my hair on and brush it out. Moments ago, I had a short crew cut, not I have wavy dark blonde hair that falls past my shoulders to wear a bra line might be. I think I look good. But I turn on the air as it is getting warm and I do not want to sweat at all.
I am almost done, and I know you will be arriving soon. I go into the bedroom and get out my stockings. Black, of course, and they roll up to my upper thighs. I pull out the garter belt and slide it on. I fasten the straps to the top of the stockings and adjust the length. I snap one of the straps against my supple thighs to ensure they are tight. Instead of a bra, I opt for a corset. It is black satin as well, with black lace designs around it. I am just able to zip it up in the back. This took quite a lot of practice before, but now that it is on, it cinches my waist tight and presses what flesh I naturally have on my chest up. I might be able to get away with just that, but I like to have a curvy figure, so I slide the flesh-colored gel breast forms into the corset. They stick against my skin and feel as it they are really mine. It is almost time; you are probably parked at the hotel by now and are making your way up. I slide into my dress. You guessed it, black as well. The neckline plunges at my chest and just covers the top of my corset. The bottom falls just below the top of my stockings. It is snug, it fits my curves, bit it is not overly tight. I opt not to wear my high heels this time. I do not want to be any taller than I already am. I give myself a look in the mirror and I am breathless at times. I do not clearly recognize the person looking back at me. She kind of looks like me in the face, but her hair and body are so different, maybe she could be my sister – if I had one. Or maybe that is what she would look like if she were born instead of me. I get lost looking at myself, carefully tracing every part of me with my eyes, I almost do not hear the knock at the door.
I take a deep breath and close my eyes. This is it, no turning back now. I give myself one last look in the mirror and run my fingers through my hair again and then walk to the door. I open it and there you are, just as you were last time. Brown leather boots fitted jeans and a forest green button up shirt. A dark gray jacket on top highlights the wisps of gray in your dark brown hair. A hint of stubble on your face, and deep green eyes that match your shirt. You smile and I offer you to come inside. You enter the room and I close the door behind you. You take off your jacket and invite me to sit on the couch with you. I offer you a drink, water perhaps, but you politely decline. We sit next to each other on the couch and I try to remember to keep my knees together as I sit. I smooth out my dress as I sit and about as soon as I am still on the couch, your arm is draped around my shoulders. It is heavy and thick, the weight of it pressing down on my shoulders and neck feels so good. It makes me feel so small inside your arm. Your other hand reaches across and rests on my mid-thigh. I rest my hand nearest you on your leg and I look up at you. You smile and close your eyes and lean your face toward me. I close my eyes and wait and feel you lips press against mine.
Gentle at first, but then firm, your beard stubble rubs against the smooth skin of my face. I feel your mouth open and I respond in kind. Your tongue enters my mouth, and my heart begins to race. It is an odd feeling at first, to be on the receiving end of such a kiss. When I am in my other life, I am the more aggressive as well, but I try to remember that I am the submissive one now and I let your tongue slide into my mouth and swirl against mine. The hand of your arm around my shoulders now grabs my arm and pulls me closer to you. Your other hand on my mid-thigh begins to creep higher and pull me closer as well. My hand on your leg was once still, but now feels movement underneath.
I feel you start to breath harder as your kiss gets more passionate and aggressive. Your hand on my thigh now reaches my butt and you squeeze it. I feel your fingers dig into my ass and my legs begins to quiver. Your hand slides down and finds the smallest bit of my thigh exposed between the bottom of my dress and the top of my stockings. Your fingers slide under and between the straps of my garter best and the dig into my thigh again. A flex of your arm and strong pull drags my leg across your body and you have me straddled on top of you. Your kiss never breaks and now both your hands start grabbing my butt, then my hips and waist, sliding up to my breasts and back. You begin kissing my neck and the top of my chest. My head tosses back, and I close my eyes in feeling your lips press against me. I bite my lower lip in ecstasy. Your hands rest on my cinched waist and I feel your hips buck underneath me. I push away from you and slide down your legs until I am on my knees in front of you sitting on the couch. Your eyes stare into mine and your hands run through my hair, “yes baby” you whisper as I unbuckle your belt. I open the button on your jeans and carefully unzip your fly. I grab your pants at the waist and slide them down to your knees. Your black boxer briefs are bulging with your cock and slide them down as well. Your cock once restrained now freely rises into the air, it filling and growing harder in just the moments after I moved your underwear. It stands tall before me now and is as impressive as the it was the first time I saw it. I take the shaft in my hand, my other hand rising to hold the side of your thigh. I pull it closer to my lips and press the tip gently against my lightly smeared red lipstick. I take the tip into my mouth and my tongue presses against it. I open my mouth further and let your now hard cock slide deeper into my warm wet mouth. My lips slide past the head and are now around the shaft, my tongue pressed hard and massage the understand of your hot cock. I gently stroke you with my hand, the nails on my other hand begin to dig into your thigh. I swallow you further and adjust my head so you cand slide to my throat. I bob my head up and down on your cock and you begin to breath heavy and groan deeply. Your hips thrust and force your cock further into my throat. My hand and head are synchronized as they slide up and down your shaft. My saliva runs down and allows my hands to slip and slide on your shaft as I jerk you off into my mouth. My hand slips further and I can wrap my hand around one of your balls and your shaft at the same time. I pull my head up to take a breath and look up at you. You let out a large deep moan “I am about to cum” you say. My head dives back onto your cock again and I slide it further into my mouth. I relax my throat and breath out through my nose, my tongue presses hard against the underside of your shaft. My hand squeezes your cock as I stroke you more. You grunt, your eyes clinched, I feel your legs tense and your body flex. Your cock is throbbing in my mouth and by the third throb, I feel the hot salty explosion in my mouth. Your hips buck and thrust and drives your dick further into my mouth. Your cum shooting into my mouth, it fills every empty space around my tongue. As your body relaxes and you sink back into the couch, I can finally breathe, and I swallow your cum. It takes two swallows to get it all and I still feel it drip down my throat.
As I pull my head up again, I hear you breathing heavily, catching your breath. I keep my hand on your shaft and my other hand on your thigh as you rest. I kiss the tip of your cock again and lick up the saliva that as dripped down it and onto my hand. You let out a laugh of pleasure and smile while you look at me. I smile back, my eyes slightly wet as I recover from that. I stand up and you meet me there. You take my hand and wrap your other hand around my waist. You pull me close and kiss me gently. You pull up your pants and take me by the hand, you lead me into the bedroom.
You sit on the edge of the bed and have me stand in front of you. You slide my dress up and I raise my arms as your slide my dress over my head and let it fall to the floor. You lean back and look at me “you are gorgeous” you say. I blush and smile and look away. It always makes me shy when you say things like that. I stand before you, my hair draped on my shoulder, my corset still cinched tight, my garter still attached to the top of my stockings, my panties now straining to hide my own bulge, though not nearly as big as yours. Your hands grip my waist, and you press your face into my corset. You kiss up to my chest and kiss the tops of my breasts. Your hands move around to my back and drift down to my ass. You squeeze my ass and let out a grown. You stand up in front of me and begin kissing me again. As your kisses move to my jaw and down my neck, your hands move from my ass to begin gripping my thighs. You spin us around so that now I am next to the bed. You turn me around and bend me at the waist on the bed. As I throw my head back my hair falls on my back. I look back at you just in time to see you lifting your shirt over your head and dropping it to the floor. Your muscular chest and arms exposed, the course black hair of your chest traveling down to lightly cover your abdomen. Your hands travel up my thighs until they reach my ass and then you push me up onto the bed. I stay there on my hands and knees on the bed, my ass facing you. I hear your boots come off and the jingle of your belt buckle tells me your pants are on the floor too.
Your hands rest on my hips and I feel you slide up to me. The warmth of your body presses against the back of my thighs and I try to prepare myself for the next event. You massage my ass and squeeze my hips. You squeeze my ass repeatedly, each time I feel your hands drift towards my center. Finally, I feel your thumb slip under my panties and begin to inch its way to my hole. With a brief pause and slow breath, I feel your thumb creep inside me. I clench at first and then start to relax. You push it in a little bit more and I moan in the pleasurable discomfort. The feel of your rough callused hands on my smooth bottom sends sensations running up my back. I relax my hips a bit more and push my as further onto your thumb. “There you go” you whisper, “good girl.” I bite my lower lip again; I want to feel you inside me and am beginning to ache for the pain. “Please daddy” I pout. You remove your thumb, and you roll me over. I am sitting on the edge of the bed now, you are standing in front of me, your cock beginning the bounce as it thickens up again. “Get it ready for you” you tell me in a deep low voice. I look up at you and not breaking eye contact, take your partially flaccid cock in my mouth again. I try to make it as wet as possible, pulling up as much saliva as I can. As I moisten your cock, it grows hard in my hand and mouth, I spread the saliva up and down your shaft, each time taking it into my mouth to wet it some more. Your dick is not fully erect and hard, my spit dripping from it. You roll me over again and I lay my head on the pillow. You lift my hips and my ass up into the air. You kiss and nibble the back of my thighs and my ass. You pull aside my panties and I feel your warm tongue begin to lick the inside of my ass. The tip of your tongue flicks my little hole and then I feel it enter inside me. You kiss and lick my ass, making it wet. Finally, you pull my cheeks apart and I feel you spit into my hole. “Oh daddy” I moan.
I feel your warm body press against the back of my thighs and ass again and the tip of your throbbing hard cock presses against my hole. You slide in the tip and just that much makes me moan. The head of your cock breaks through the rim of my hole and I let out yell. You pause and then begin to push yourself further into me. Every inch my ass open wider for you and your cock feels hot inside me. You thrust again, this time causing me to lose my breath for a second. My chest heaving and my legs tremble. You drive forward again and now you are fully inside me. You squeeze my ass in pleasure and groan “oh you feel so good baby.” A tear leaves my eye and rolls down my face. You slide your cock out of my ass and then force it back in, much faster this time. When you are fully inside me again, you slap my ass and then grab a handful of my hair. You pull my head back and I let out a moan. You pull out of me again and instantly thrust all the way back into me once more. There was no pause that time, not moment to let me relax. You slid your cock in my ass like you owned it because you do. Another tear leaves my eye and more stream down behind it. The pain is immense. Each thrust brings another wave of shooting pain and pleasure up my back and abdomen. I scream into the pillow and bite the sheet to better be able to withstand your throbbing rod pounding in and out of me.
My own bulge at its limit, I reach under myself and begin to rug it through my satin panties. It does not take much, each pound of your pelvis into my ass, your deep growling groans as you do, my bulge begins to cream and a wave of pleasure washes over my body. I let out a long moan as I cum and this seems to only encourage you to fuck me harder. My panties are soaked, and I feel your thrusts get harder and faster. “Oh god” you cry. “Oh god… fuck…yes” you cry louder. You breathe deep and thrust hard into me again, you squeeze my ass and hips as you do, you finger buried into the soft supple curves of my bottom. You let out a deep and shaking groan and I feel the warmth explode inside me. It hurts to have you that deep. My legs are shaking, and my ass is numb from your spanks and grip. “Oh daddy” I pant, “your cum feels so good inside me.”
You are breathing heavily. I feel the sweat drip from your hair, face, and body as it falls onto mine. You pull your cock out of me and I collapse on the bed. My eyes and face still wet from the tears; I see you collapse next to me. I am lying on m side and you fall on your back. You let out a blissful laugh and smile up at the ceiling. I try to manage a laugh, but a shaken and whimpered smile is all I can conjure. You inch closer to me and I rest my head on your shoulder. My hand lands on top of your chest and my fingers run through your chest hair. You reach over and grab my top leg behind my knee and drape my leg across your body. We both lie there sweating and smelling of sex. My eye lids feel heavy and I close them for a few moments of sleep.
I awake a few minutes later and raise myself up to my arms. I look down at you, your face relaxed as you sleep. I lean in and kiss your stubble cheek, a smear of lipstick to mark the spot. I slowly get off the bed, careful not to wake you. As I stand, my legs wobble, and a reminder of the experience painfully shoots up from my center. I must hold on to the wall and door frames and gently walk myself into the bathroom.
I run another hot bath and begin to take off the lingerie. I unzip the corset and unbuckle the garter belt from my stockings. I sit down on the edge of the tub, the steam rising and filling the room like a clouded dream. I roll the stockings off my legs and toss them in the corner. Finally, I remove the cum soaked panties. My cum in the front, yours in the back. I daintily toss them in the corner with my toe, along with the rest of the clothes. The water level is just high enough, and I turn it off. I gently slip into the tub, carefully lowering my trembling body into the warm embrace of the water. I lay back and close my eyes again, replaying the last hour or so over and over again. I can still feel your touch on my hips, I can still feel you grip into my ass and thighs. I can still hear you groan and growl as you climax. The hot water of the tub reminds my hole of the trauma you delivered. And if I concentrate on it, I can still smell your musk from first releasing your cock from your pants. I remember how soft it felt in my mouth at first and the feeling of it growing harder as my tongue massaged it.
After the bath I dry myself off. I carefully use the towel to dry the wet ends of my hair from the tub. I lather myself again in the lavender lotion from before and I reach into my bag again. I pull out a pair of soft silk light pink panties and slide them on. A matching silk camisole slides over my head and drapes around my body. I am not wearing the breast forms anymore, but what flesh I do have on my chest slightly fills the breasts of the camisole. I turn off the light and exit the bathroom. You are still sleeping, and I slide under the covers next to you. I can not fight the pull of my eye lids any more and I drift off to sleep, my mind racing for what might come when we wake up.
Source: reddit.com/r/eroticliterature/comments/n4w53p/a_crossdresser_gets_a_hotel_room_to_meet_her