The Hotel Experiment

By the time I left college I was already spending much of my spare time on the Internet, looking at porn, chatting and caming with strangers and sharing photos of myself wearing my mum's and my big sister's clothes. I was open with my friends about being bisexual, though none of them seemed to believed me. But I never told anyone, well no one I knew anyway, about my desire to dress and be as girlie as possible. I told lots of strangers on the Internet though, I would chat and cam with strangers when I was alone in the house. Often they would ask me to meet them, a hotel was usually the location of choice, but I was always too scared. Then one day a guy suggested, as I was so timid, young and inexperienced, if I was unsure about meeting someone, I could spend a night in a hotel alone, just to try it out. The thought stuck in my head and the more I thought about it, the more it made sense.

So I found myself sat on a train late one afternoon, heading to a nearby town where there was a large hotel, one of a common chain of hotels, right by the train station and I had a room booked for the night. I had told my mum I was visiting a friend and filled my backpack with everything I thought I would need. My bag was very heavy stuffed full as it was with my laptop, a little make up, the outfit I was going to wear, my butt plug and a tube of something to help get the plug in, and a couple of bottles of cheap wine. The wine was mainly because I was nervous and thought it would help.

I had never checked into a hotel myself before, it was very busy at reception. There were lots of people in smart suits all around, it seems there was some sort of conference going on and I felt very out of place in my jeans and baseball cap. I was handed a folded piece of card and directed to the elevators around the corner. I pressed the button and the doors opened almost immediately. The tiny box already had three guys in it and looked very full.

"Room for a little one." The guy nearest the door said, and moved to the side to make room for me. I was to shy and nervous to decline. Even though the last thing I wanted to do was get into a box with a bunch of strangers. I stepped into the lift and turned to face the door. As I turned my backpack bumped against one of the men. The wine bottles clanked together loudly, I shrugged the bag off my shoulders and down between my feet, the bottles clanked again. I reached over to press the button for my floor, even though it was already lit.

"Someone's having a party tonight..." one of the men said, I blushed and looked down awkwardly to avoid eye contact, hiding behind the peak of my cap.

"Just as long as you don't keep me awake all night." the guy next to me said, and the others laughed. A moment later the doors opened, I looked at the guy who had moved over to let me in the lift. He was smartly dressed in a grey suit, white shirt and colourful tie. His short get hair was receding, his head and face were very tanned and his salt and pepper goatee beard was short and tidy. He was taller than me, must have been six foot plus and a bit overweight. He had a nice face and he smiled at me when he noticed I was watching him. I blushed again, grabbed my bag and headed off down the corridor quickly.

My room was third door on the left. When I got there I opened the folded card I had been given at reception, took out the piece of plastic that was the key and dropped it into the slot on the lock. I tried the handle, but the door wouldn't open, the little light stayed red, I tried the handle again, still no luck. Then an arm reached around me and took the card out of the slot, then put it back in and out again quickly. The little lights changed to green and the door opened, I turned and the man from the lift offered me my key back.

"It's so you don't leave your key outside I think." he explained.

"Thank you" I mumbled, took the key from him and shut myself in my room. It was the cheapest room they had and so I wasn't surprised it was tiny, but I was surprised by the somewhat loud and constant hum. There was a small bathroom to the right and beyond that the room opened up a little so it was just big enough for a double bed and a dressing table. I flopped onto the bed, feeling tense and a bit stressed, wondering if this had been a good idea. Soon I had calmed down and felt like a drink, there were two small glasses on the dressing table, I opened one of the bottles and filled a glass with wine, then sat on the bed, listening to the sound of trains and the humming, messing with my phone for a while.

I started feeling better, so poured my second glass of wine and checked out the room. The large window went almost from floor to ceiling and pretty much filled the end wall. It overlooked the train station, the flat roof of some other part of the hotel, and a load of noisy air con units. So that explained the humming. The TV mounted in the corner seemed to work, there was nothing on. The bathroom was small, very new looking and very warm. I decided I may as well get changed, I used the loo, then took a shower making sure I was clean and smooth all over. Wrapped in a big warm towel I went back to the bed and emptied my bag onto it. I tied my wet almost shoulder length dark brown hair up in a small towel and sat in front of the mirror mounted on the wall. I put on a little black eye liner and some dark brown eye shadow. Then covered my lips in scarlet lipstick before adding a couple of dabs to my cheeks and rubbing them in so my cheeks were all rosie. My fingernails were not very long, but I painted them a deep red anyway and drank a little more wine as they dried. I let my hair down and dried it with the hotel dryer, my dark brown wavy hair falls in a natural messy bob sort of style that I like. So, happy with the look so far, I had another swig of wine, and started getting dressed.

First I put the towels back, and stood naked in the bathroom, I had borrowed my Mums perfume body spray, "Romantic Spark" who knows maybe it would spark a romance, I used it liberally. Back out in the bedroom, I wrapped the white satin suspender belt, my Mums, around my waist. It was quite deep, with plastic ribs to stiffen it and it pinched my waist just right. Next I slid the black stockings up my smooth, pale legs and attached the belt to them. Then I picked up the little white cotton bra that had been my sisters, held it around my chest, back to front so I could fasten it, then span it around and slipped my arms through the straps, adjusting the straps on my shoulders carefully and the tiny cups over my nipples. I stepped into the matching little white cotton panties, slid them up over my stockings and bare thighs, then over my bottom, tucking myself in carefully.

I checked myself out in the mirror and realised it had got pretty dark, so I turned on the lamp on the table nearby. I went over to the window to close the curtains, but when I looked out at the station in the distance I thought, well no one can see in really, it's too far, so why bother. And, to be honest, the thought of someone watching me kind of excited me anyway, so I made sure the curtains were as wide open as possible. I wondered around the room in my underwear for a bit. Had another drink of wine, setup my laptop on the dressing table, laid out the skirt and blouse I was going to wear and tidied all my other junk off the bed. I heard a noise in the corridor outside, so went to the door and pressed my eye against the little spy hole.

To the left I could just make out two figures stood talking in the corridor outside one of the other rooms. A moment later a third figure appeared, and all three walked by my door. It was the three guys from the lift earlier, I stood in my sexy lingerie watching them and giggled to myself, "what would they say if they could see me know" I thought. I could hear their voices as they waited for a lift, but couldn't make out what they were saying, a moment later, they were gone. I went back to the table, had another drink and decided to finish getting dressed.

I picked up the white blouse first, my sister had worn it for school a few years ago, it was tailored with little cap sleeves and button fastening from the bust down to the waist, it was quite close fitting and showed off my figure. Then I stepped into the skirt, also from my sisters school uniform, but it looked more professional than that. The top part of the skirt was tight with a fake belt feature and hugged my waist and hips, while the bottom part was pleated and just long enough to cover my stocking tops. I tucked in the blouse and slid my feet into the black four inch heels I had borrowed from my Mum. I took my watch off and put on a few cheap bangles while I checked myself in the mirror again. Happy with how I looked, I had another drink and started up my laptop.

It didn't take long to log into my favourite sites, turn on my web cam and I soon had lots of viewers. I told them I was in a hotel room and they all wanted to know where. I teased them, and myself, by showing off my panties, and my bottom. I took the plug from my bag and showed it to the web, dipped it into my wine before sucking it clean for them, I was having a great time. I drank more wine and got myself and some total strangers, really worked up.

Everyone could see my panties bulging and some even noticed the small damp patch on the front of them where my boyclit was starting to leak with excitement. I climbed onto my knees on the chair, so they could see my bottom as I pulled my panties down, then I started to finger my tight little hole. I took the tube of lube and made myself good and wet. Then I put some on my toy and eased it between my cheeks, all the way inside me until just the fake white crystal on the end of it could be seen glinting in the lamplight. Giggling and feeling very naughty, I pulled my panties back up and sat down on my toy, wriggling and squirming on the chair with it pushed up inside me.

I paused to have another drink, I was feeling quite merry by now, and read some of the comments viewers had made. They seemed to be enjoying the show a great deal. One comment said I should go out onto the street and get fucked, he said I was begging for it. Well that was rude, but the idea of going outside excited me, I was surprised just how much it excited me, so I told them all I was going outside, just for a moment. I turned the laptop so that the web cam showed the door of my room, stood up, and walked toward it. I peered through the spy hole and listened carefully. There was no one around, but just as I turned the handle I remembered, I would need a key to get back in.

Giggling and feeling a little bit silly and tipsy, I trotted back to the table, picked up the credit card sized key and realised I had no pockets to keep it in. Still feeling a bit naughty, I turned my left thigh to the camera, lifted my skirt and slipped the key into my stocking top. Then turned and trotted excitedly back to the door. Again I checked, but it was all quiet, so I opened my hotel room door and peered out. All was quiet, so I edged my way out nervously, holding onto the door like a life line until eventually it clicked shut behind me and I stood in the corridor in my skirt, blouse and stockings.

At one end of the long dimly lit corridor was the lift, at the other end there was a sign for the stairs. I decided they were the safer option, so headed away from my room and down the stairs. About half way down I lost my bottle, and turned back. What was I thinking, there was no way I was walking through reception, with all those people, dressed like this. I was about half way along the corridor on the way back to my room when I noticed the lift was coming. I thought I could make it and headed for the safety of my hotel room, thinking it would go by to the floors above, probably. I was wrong, the lift doors opened when I was just a few steps away from my door. The old guy from earlier was inside, looking down at his phone.

He looked up as the doors opened, straight at me. I stared back horrified and watched as a range of expressions appeared and disappeared as he first noticed me, then checked me out, then recognised me and finally looked totally confused. I panicked, grabbed the door handle and then remembered, with a sinking feeling, where I had put the key. As the old man walked toward me along the corridor, watching me intently the whole time, now with a look of great curiosity on his face. I lifted my skirt, flashing my stocking top and bare thigh, and removed the card. I fumbled the card in and out of the lock, my hands shaking with nerves, the door opened and I shut it behind me quickly.

I took a moment to get my breath back and calm myself, then I turned and pressed my eye to the spy hole. I couldn't see anything, it was black, but a moment later the corridor came into view and the man from the elevator. Stood right outside my door. He looked down at the bottom of my door, then right at me through the spy hole. He raised one arm, his hand in a fist as if he was going to knock on the door. Suddenly his phone started ringing, he looked down at it, then answered it and moved away toward his room. He opened the door and stepped inside and I quickly opened my own door and peeped out as his door closed, making a mental note as to which room was his. I tried to listen in the quiet corridor, to hear him talking, but there was no sound.

Suddenly his door opened again and he reappeared, still on his phone, but carrying a folder as well now. I jumped back into my room and shut the door behind me, a bit too loudly maybe, and peeped through the spy hole again. He walked slowly along the corridor until he got to my room, then he stopped, and looked down at the bottom of the door, still talking to someone on his phone. A moment later he ended the call and put his phone away, looked up at the spy hole and, reaching out one arm, he softly knocked twice on the door. I froze, trembling with fear and nerves, he looked down, knocked again, then leaned close to the door.

"I know you are there..." he whispered "I can see the shadow of your feet" my heart was racing and a whole range of worst case scenarios were running through my mind.

"It's OK..." he said in a soft calm voice, which did a surprisingly good job of calming me down "I just want to talk to you, open the door..." Well, I took a bit of convincing, and even more summoning up of my own courage, but a little while later, I put the security chain into place, took a deep breath, and opened the door. I peered through the gap nervously, stood face to face with another person while dressed for the first time.

"Hi..." he said and smiled, I was too scared to respond, he took a long look at me then continued "I'm sorry, but I have to ask... you umm, you are a guy right?... the lad from the lift earlier?" I nodded. "Wow, you look great..." he said, in a somewhat surprised tone. "I wouldn't have recognised you, or thought... well anyway." his voice trailed off and he just looked at me for a moment, then glanced over my shoulder and into my room.

"Are..." he paused, glanced up and down the corridor, then looked back at me and asked "are you alone?" my mind was screaming, don't answer, don't tell him anything, but suddenly I realised it was too late as my head had already started nodding. Another uncomfortable pause followed as the stranger looked me up and down, then looked up and down the corridor again, then turned his attention back to me.

"Would you umm..." he hesitated again, "would you like some company?" my answer was in every way accurate, part of me was screaming oh god yes, let him fuck you, you little slut. And another part was shouting, no way, he is a total stranger, you have never done it before, you just can't. I just shrugged.

"Ha Ha Ha..." he chuckled to himself softly "you don't say much do you..." I shook my head, "if you didn't look so scared I'd swear you were here working..." The stranger at my door didn't finish what he was going to say. Instead he took another long look up and down the corridor, then turned back to me. His expression had changed and was somehow more serious. He moved closer to the door, his right hand reaching through the narrow gap slowly, his fingers coming to rest gently on my stocking clad thigh. It made me jump, but I didn't pull away. I just stared down at his large sun tanned hand as his fingers moved in little circles on the outside of my thigh.

"Just tell me to stop..." he whispered " and I will". I continued to watch as, encouraged by my silence, his hand opened slightly so that his palm and thumb were now holding my slender thigh, moving up and down in a long slow caress. Down almost to my knee, then up again to the hem of my skirt. Each time his hand moved a little higher, and higher, lifting my skirt a little more each time until his thumb and fingers stroked the soft sensitive bare skin at the top of my thigh.

I heard someone whimper and felt my knees go weak. His hand continued up under my skirt, to my hip, his fingers toyed for a moment with the thin elastic waist band of my skimpy white panties, then he slowly withdrew his hand.

"Show me your knickers..." he suddenly whispered through the narrow gap of the open door, making me jump again, lost as I was in the thrill of his touch. He looked up and down the corridor again and tucked the folder he was carrying under his armpit. I moved a little to my left so I wasn't hiding behind the door so much. He looked back at me and with my right hand still clutching the door handle, I took hold of the front of my skirt with my left and lifted it up to my waist, displaying my stocking tops, white suspenders, soft smooth bare thighs and little bulging panties for him.

"Hmmmmmm..." a low rumble of appreciation seemed to vibrate from him, then he just said "fuck" and reached his hand out again, this time cupping my bulging panties, squeezing and rubbing my boyclit through the thin material. Again I heard someone whimper, he kept rubbing and I stared transfixed at his big sun tanned hand as it played with me. I was getting so excited now, I moved my legs apart a little and my hips started to squirm, grinding myself against his firm hand. I noticed his trousers were moving and looking up a little, I saw his other hand was rubbing a large bulge that had appeared in the front of his trousers and seemed to be growing down his right thigh.

His fingers pushed between my legs as he rubbed my panties and I ground my boyclit against his hand. I wriggled more and his fingertips pushed a little further, between my cheeks, and found my toy. I stopped moving, I had almost forgotten it was there, his fingertips explored it for a moment, then, realising what it was, he pushed it up into my bottom hard. I gasped aloud and moved my hips closer to the door, pressing my self into the narrow gap and opening my legs even more as his hand pushed between them and worked my little toy in and out. Suddenly there was a noise from the mans pocket as his phone started to ring again. He swore and pulled his hand away.

"Yeah yeah, I'm on my way back now" he said into the phone and turned his back on me to continue the conversation. Somewhere up the corridor another door opened and more voices could be heard, so I quickly shut my door and stood panting and excited behind it. I listened at the door and the sound of people talking in the corridor seemed to go on for ever. Eventually noise of movement and talking outside subsided, I removed the security chain and peeped through the spy hole, there was no one there. I opened the door and looked out, the corridor was empty. I waited for a while, but there was no sign of him, so I shut the door again, went back to the table in my room and poured myself a big drink of wine. The glass rattled against the wine bottle as I filled it, I trembled so much with nerves and excitement.