I arrived at the hotel feeling slightly nervous. It was a warm summer’s afternoon in a new city. I’d visited year’s ago and so much had changed, but I found the hotel easily, it’s high up name visible as my train wound it’s way into the station. I didn’t drive, it would have been easier with my holdall heavy with heels, dress and everything but I was out to have my first ever ‘feminized encounter’ and my mind was racing. This was always going to happen I told myself, there was no backing out, the nerves weren’t strong enough to put me back ‘on that train’.
I checked in at reception it was a good hour after check in time and like a method actor I’d created a plausible story for why I was here at this reception, I believed it, why shouldn’t the spectacled thirty-something average looking receptionist. She finished her phone conversation and checked me in with as much interest in me or my story as a dental receptionist. She stepped away to collect my key and I admired the stockings her legs wore. Taking the key I walked towards the lifts thinking of my own freshly shaven legs sliding into my stockings.
Inside the room, I closed the door tight, dropped my heavy hold all by the bed and approving of the room he’d chose I saw the ‘do not disturb’ on the door knob and quickly put it on the outside. I checked the time, I was early by my plan, I gave a nervous shudder-sigh and let my nerves run a little……the same feeling ‘this was always going to happen’ rose up and quietened my nerves. Opening my hold all I glanced to ensure the door was locked as I laid out my feminine wares.
Stripping, I tossed my ‘male self, or character, into the hold all and sealed it and my masculinity inside. Taking my shave kit and mirrors for bum and back of legs into the small nice bathroom. I hadn’t shaved ‘neck to toes’ in six days, I wanted to avoid the chance of three day in stubble rash, I wanted to be smooth and rash free. Beginning with my chest and trunk I used soap as I always do, then shave gel for everything else starting with the face, not that I ever had strong beard growth, maybe nature had always known, maybe this was always meant to happen.
As I shaved carefully, it was a fresh mach3, I thought about how it had all began with that first email. God I was suspicious, but as the first awkward emails gave way to general closeness and then into deeper darker repressed desires I began to feel like a lost small boat, it’s motor still running, out in the bay moving directionless till by chance the current caresses it’s rudder to turn it and head it back to the boat yard beyond the beach.
This boat was in the shower, foaming the soap, looking down at my smooth shaven legs and purple toenails. I was smug, no razor burn to spoil this boats homecoming. Drying off with the fluffy towel against my shaven body, I longed to be in make up and had to calm my eagerness at lining up my supplies. An hour later I was finishing off, sipping scotch- he said I could, he liked it too and it was his brand none of that famous grouse for him. I put on my hair, he’d chose the style, expensive and a good fit so he could stroke and handle me without ‘slip’ to spoil the moment. On with my stockings and g. string after I taped back my cock, balls above – he wanted to release me when the time was right. Use plenty of microporous tape he said and I did. I liked the idea of being restricted, controlled in the most intimate way. My balls strained, ‘tough’ I said to them as I put on my heels and undid the adhesive for my pre painted nails.
Fifteen minutes later I laid chest down on the bed, facing the door. I could feel my breast forms warming up in the boob tube under my dress. I’d only sipped the scotch after all the make up was lovingly applied, so I was just relaxed. Outside the door I heard heavy foot steps, the jingle of keys, he’d arranged a second key and I’d double checked the lock was off before lying on the bed, the way I’d told him I would.
The door opened and he stepped gracefully and carefully in, not letting the door go wide. He was so slick like the Cary Grant type I’d wanted to be – or maybe I wanted to be with – when I was young. He smiled, it was a warm smile and like ‘that boat’ I knew I’d made the right choice. He simply said ‘hi’, I smiled and sighed a soft ‘hello’, he seemed to like it. He slipped off his tailored jacket and smoothly placed it to hang on the back of the chair by the dresser and my make up. He caught sight of the reel of microporous tape and picked it up, tossed it high and effortlessly caught it ‘tight?’ he asked. I took a sip of his scotch ‘very’ I said slowly, letting my buttocks sink a little into the bed. He came to me in a single stride, stroking my hair, down my back and circled his hand across my buttocks. Now the little boat knew for sure, as strange as the shoreline ahead might be.
He unbuckled his trousers while the late afternoon sun glinted off his cuff links, he slid one tanned smooth but strong hand down into his trousers and played with himself a little, finger tips caressing his shaven balls while his penis wetly rubbed against his palm. He looked into my eyes I liked the way he did that, I’d hoped he’d do something like that. My cock strained a little, couldn’t get loose the pain made it go soft. He took his hand from his open pinstripe trousers and put it to my face, palm to my lips. I smelt his smell it was similar to me but pleasantly different, I strained forward, he let his palm cup my face and I licked his palm and tasted him- I just wanted to and it was good, I knew it would be, different to me, refreshingly different. I liked it, my confidence was brimming over and I could see he liked it too. I could smell his expensive aftershave as he unbuttoned his white shirt while I removed his cuff links. His shirt slid to the floor and he stepped out of his trousers and deftly laid them over the chair back with his jacket. I couldn’t help myself, I pulled down his silk shorts and his tanned cock rose up to my face. He gently took my head and I was grateful for all those times I’d sucked on my dildo’s. I imagined it was my own, as if I might feel what he felt, I let my tongue stroke beneath his head, my lips surrounding his tip while I swallowed his taste. I wriggled forward on the bed, he instinctively moved closer arching his back a little to lower himself, he slid into my mouth, the warmth distracted me for a second, I quickly had my lips over my teeth, he didn’t berate me, he was my first and my inexperience was novel to him. I gagged a little as he went deeper and he drew back a little, I couldn’t believe this was me, enjoying his heat, his scent, his taste mixing with my saliva and slightly, pleasantly stinging my mouth.
I reached out, stroked his thighs and buttocks, he gently put his hands to my upper arms and we stood face to face, he kicked off his shoes and slipped out of his socks, he was finally naked- my first naked man, his bare tanned toes touching my shaven, white stocking toes. We pressed our bodies together, I felt his stubble as we had our first kiss, he pulled away a little, smiled and came back for more, perhaps he’d noticed my lack of stubble as women had in my past. His hands smoothly unzipped my dress and it slid down to my amazement, just like in the old movies… but he had the touch. He slid his hands across the white boob tube holding my breast forms, I think he wished they’d be real, I know I did. Smoothly he threw the extra spread he’d asked me to bring across the bed and as he stroked my body he turned me, I slowly slid forward back onto the bed and lifted my legs so he could smoothly free my stocking legs of the g string. He gave a soft groan of satisfaction as he worked his lubricated fingers between my soft shaven buttocks, raising and parting my thighs as he went fingers deep into me. For a moment I was tight, concerned but he had a soft assured touch and I relaxed into the bed and let him open and prepare me. I was glad of my large butt plug fetish!. Then the moment came, I’d planned and never gone through with this many times and finally he slowly eased himself into me. It was as if he’d done butt plugs the same as me, he was ‘pleasure instinctive’, as he speeded up I felt the heat of his chest on my back, I shifted a little to improve the angle, he carried on and I realised this was where I wanted to be. He came loudly but with style and laid over me, taking his weight, his face alongside mine cheek to cheek.
After we’d enjoyed the moment he reached between my buttocks to the tape at the root of my penis, slowly he peeled it away and I steadily became hard, mine seemed somehow feminine to his strong tanned penis. He rolled me over, gave me a sexy smile and began to suck me harder then to my surprise he straddled me as he lubricated himself and then lubricated and wanked me so expertly I nearly came. Slowly he slid down onto me I laid back and closed my eyes feeling myself being taken into him, I had to smile and smile. My hips began to thrust knowingly and I felt my cum as it flowed down my shaft, he knelt over me and licked my shaft then we kissed and shared the taste of my cum lying side by side. ‘happy’ he asked. I kissed him again.