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Hoods and Hotel Rooms - Chapter 1 [Latex] [Crossdressing] [Anal]
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LoveofRubber99 is in Anal
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I start with the hood.

I always do. It makes everything that follows so much easier.

It's something of a crutch I think, a way of disassociating myself from what I'm about to do. Of separating me, the normal guy with ordinary tastes, from the pervert whose about to debase themselves in this hotel room.

I gather the limp rubber in my hands, bunching it up and spreading the opening wide as I bring it to my face. One of the (many) things I love about latex is the way it interacts with all of your senses, from the glossy shine, to the squeak and stretch of the material, or even the bitter taste. But at this moment, it's the smell that hits me first.

As I duck my face into the hood my nose is filled with the pungent odour of rubber. I breathe in deeply, letting it seep into me and feeling the familiar tingle of anticipation deep inside me. My cock twitches as I pull it tight to my skin, lining my features up with their respective holes. Fingers fumble with the zipper and I feel it tugging on my hair as I draw it closed, tightening across my face as I’m sealed in.

I glance at the rooms small vanity mirror and feel my cock begin to harden. The mask makes me anonymous, smoothing out the masculine lines of my face and leaving a shiny black doll in its place. My eyes are visible, framed with thick white lines and two small holes allow me to breathe with relative ease through my nose. My mouth too is unobstructed. I've often wondered about makeup and what those lips might look like with a vibrant red shade applied, but I've never had the courage to do anymore than daydream about the idea.

I take a few moments to smooth out the wrinkles and admire myself, my fingers idly toying with the hoods final feature, and my favorite. Beneath the mask is a short shock of dark hair, but now a vibrant plume of red erupts from the top in a high ponytail. I swish it back over my shoulder and consider taking the time to plait it, but a glance at the bedside clock tells me that luxury will have to wait.

With the hood on I already feel more comfortable and my excitement only increases as I return to the suitcase that lays open on the bed.

These little trips I take are almost always work related, so I do have to be careful what I bring with me and how I hide it. The top layer of my bag is always what you might expect to see from a middle class white man on the verge of turning 30. Pressed white shirts, a wash kit, a change of underwear, maybe a book. Right now, those items were neatly stacked on the bedside table, revealing the more… risqué items beneath.

These come out now and I lay them reverently onto the crisp white sheets. There’s more rubber, of course, but toys too. A small anal plug, a bottle of lube and a set of cock rings of varying sizes. It’s these items that are next in my rituals. I take up the bottle of lube, flipping the cap open and squeezing out a generous dollop onto the fingers of my left hand. I’ve already taken the time to lay out a fresh towel and kneel on it, resting the lube within easy reach as I spread my legs apart and reach for my backdoor. I give a small gasp as my probing fingers find their mark and introduce the cold gel to my exposed hole. I exert a little pressure, feeling the first finger slip easily inside, the lubricant warming quickly as the digit quests inside. I take it slow of course, slipping it in to the first knuckle, pausing, sliding it out, going a little further. This isn’t exactly new to me though, so it’s not long before a second finger joins the first stretching me that little bit further as they push deeper and deeper inside of me.

In the grand scheme of things, my fingers are hardly the largest thing I’ve ever taken inside of me but they still leave a sensation of emptiness as I withdraw them. The feeling is very much temporary though as I pick up the plug that will soon take their place. It’s rather small, intended to keep me occupied rather than fully stretch me out, and made of a soft pliable rubber. Its larger cousins remain back at home and a part of my wishes I’d been brave enough to pack one of those instead, but convenience and discretion had won out during my packing.

Once again the lube comes out and I take my time to spread it all over the plug's surface, all the way down to its flanged base. My freshly stretched sphincter offers little resistance as I slide it home in one motion, relishing the sensation as it settle into place. I let it linger for a moment, shifting my hips and adjusting to the feeling of fullness before grasping the base and gently pulling, exerting pressure until my ring gave up its grip and allowed the plug to slide free again. I repeated this process several times, gently fucking myself as I sought to stretch myself out further and thoroughly lube my rear passage.

My free hand dropped had dropped to my dick and I found myself stroking in time with the movement of the plug, the sensations overlapping and amplifying each other. I leaned forward fully, planting my hooded face on the towel and raising my arse up to the air as I worked the plug back and forth, jerking myself all the while.

I might have stayed like this, and ruined my evening plans in doing so, if my phone hadn’t pinged at the moment. I stopped instantly, realising how close I had come to getting lost in the moment and blowing my load early. I rose reluctantly, even with the towel, the floor hadn’t been kind to my knees and I took a moment to use the bathroom, washing the remaining lube from my hands and admiring my shining face and hard cock as I did so.

Back in the main hotel room the phone was still blinking its little notification at me. Unlocking revealed a new message, the one I’d been anxiously awaiting for days.

'On my way, what's your room number?'

I fire it off instantly. The reply comes back just as fast.

'Be there in 15.'

I lock the phone and place it back on the desk returning to the task at hand with a newfound sense of urgency.

Shorts come next. They’re latex too, as you’ve probably guessed, and liberally coated with talcum to help me ease them up my legs. It’s still not an easy process, and I once again wonder if shaving or waxing my legs would be worth it. As with the makeup, I’ve never had the guts to follow through on such a major step, but I can’t help but think it would be worth it as the tight rubber pulls and tugs on my leg hair. I get the waistband up around my hips and reach down to grab the lube once more. I spread a generous coating over my cock, which has remained stood to full attention, and guide into into the inbuilt sheath, groaning as I feel my length swallowed up by the tight rubber.

I long to toy with myself again but control my instincts, pulling the shorts so that they settle on my hips and seal the plug inside of me. Delicious. The cock rings come next. I slide them down my shaft so that they settle at the base of my cock, squeezing me gently. I wasn’t likely to soften anyway in this getup, but I love the way they make me stand proud and prolong my orgasms, so I never left home without them.

Time was ticking away, they’d be here soon.

Gloves were next, then stockings. Both required lots of effort, heaps of talc and prompting much grunting and swearing, but the finished article was worth it. I had enough time to shine myself up, running my now gloved hands across the rubbery areas of my body and bringing them to a dazzling gleam. The sensation was wonderful. The latex smoothly gliding over itself, easing creases, adjusting the fit. It was heavenly.

I had just enough time to take another look at myself in the mirror. The image staring back at me made my cock ache with desire.

I’m no pornstar, but damn if I didn’t wish I could have a go at the reflection facing me. The smooth, anonymous face, the splash of red dangling over my shoulder. My arms and legs encased in that shiny black material and of course, seven inches of rubber sheathed cock sticking proudly out in front of me. I’d indulged myself many times dressed like this, wanking and fucking myself whilst I stared at that mirror, tricking myself into thinking I was watching somebody else.

Tonight I wouldn’t have to watch.

Tonight I had a partner.

A knock at the door sent my heart racing and pulled me away from my reflection. I took a deep breath and checked the peephole, my hand resting on the handle. I froze there for a moment, knowing that this moment would change things. I could ignore it. Pretend I wasn’t here. Get undressed, pack it all up and abandon these perverted fantasies. Nobody would know. Nobody would judge me.

I opened the door.

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