A few months ago, I started a new job. The job took me around the country, often to locations far from home, where I would stay in some easily forgettable hotels, which usually, at least, were blessed with free WiFi. I would generally arrive the night before attending client meetings the next day.
This gave me many opportunities to enjoy my old hobby of cross-dressing. Now, I am straight, but - for as long as I can remember - have enjoyed the thrill of dressing as a woman. I have never gone out in public, and my wife has no idea, so it is a very private hobby, except that recently I have taken to appearing in chat rooms, always with my face hidden. Only very occasionally would I find a woman in these chat rooms, and they would usually work out I was a guy quite quickly. However, I found I was quite turned on by the reaction of some guys who were slower on the uptake. I would happily get into the character of a lonely housewife and could lose myself in that fantasy while some random bloke tossed himself off in the belief I was really a woman. Over a few months, I had secretly expanded my wardrobe and had eventually even got a makeup starter kit.
One trip took me to some instantly forgotten town in the Midlands, where I stayed in some hotel, which was part of a faceless chain. I ate a rapid dinner and, excitedly, headed up to my room to get dressed up for an evening of playing. I, fortunately, checked my work email first to read that the first meeting had been cancelled and so I could have a lay-in as my first meeting was now not until 11:30, the next day. This meant "extended playtime" for me.
That evening, I found a few partners to play my games with, but nobody really exciting. There was one woman who took a while to work out I was really a guy, then was quite curious asking me a load of questions. I think I nearly convinced her to flash her tits for me, but the connection froze- which was deeply frustrating.
By 1:00 am, I was feeling horny, quite daring, but unsated. I thought of the extra time I could have in bed the next day and decided to take my games to the next level and do something I had never dared to do before. I decided to take a walk along the hotel corridors en femme. I spent some time over my make-up. It wasn't very good, but it did make my face look a bit more feminine - if I squinted.
It took me some time to finally pluck up the courage - I am not particularly brave and was petrified by the idea that someone might see me, but I also recognised the thrill it was giving me, the adrenalin coursing through me. I spent a full minute peering through the spy hole in the door, before opening the door a crack and peerIng out. Then I put my head out and looked both ways along the corridor. Deserted. I could feel my heart pounding.
A thought suddenly entered my head: suppose I had a heart attack out there and was found in drag. What would be said to my family?! I was being silly. It was the middle of the night, nobody was around. I took a few deep breaths - well as deep as my tight black corset would allow - and stepped through the door. I slowly closed the door behind me. At the last possible moment, I remembered my pass key. I had nearly locked myself out. I dashed back inside and picked up the card and kissed it. Lipstick smudged on it, which made me chuckle and lifted my spirits. With my key now in my hand, I stepped back to the door, gave another look up and down, then walked out of the door into the still deserted corridor, hearing the door click behind me.
Already the thrill of what I was doing was beginning to override my fear. I walked along the corridor towards the lifts, trying to concentrate on walking well, and as femininely as possible in the unfamiliar shoes. I am tall, so had got shoes with not much heel, but even the two inch heels felt very tall to my untrained feet. I tried to swing my hips as I walked and loved the sound of my stockings rubbing together. I realised this was the furthest I had walked.
I turned the corner at the end of the corridor into a shorter corridor, which had a large mirror at the end of it, and the lifts off to the left. I watched my reflection advance. I noted that my legs were too splayed when I walked: I had observed women tended to put one foot much more in front of another. I went back to the start of the corridor and did it again. Better, but my arms were wrong. Ah! Women tend to let their arms swing back further. I tried that, but had got it wrong - I looked like a footballer warming up! I tried it again with my arms closer to me. That looked much better, don't forget to sway my hips. This time, it looked good. If I ignored the dodgy makeup, I would have believed it was a woman walking towards me. A sexy one. I walked right up to the mirror and - in a moment of spontaneity - kissed it, leaving a smudge of lipstick. I giggled, enjoying the moment...
Until suddenly I heard the soft ping as a lift arrived, before I could react, the doors began to open. I was trapped, with nowhere to go; nowhere to hide. I pressed myself into the corner. I was just beginning to believe that it was empty when a woman stepped out of the lift. She stood and swayed slightly, obviously quite drunk. I willed her to turn right and not notice the shape hiding in the corner. I believed she could probably hear my heart thumping against my ribcage, as though trying to escape. She looked right, away from me, then in awful slowness, turned her head back to the left towards me. She suddenly saw me and started. She blinked a few times and tried to focus on me. I stood paralysed as a frightened rabbit as she staggered towards me, peering at me.
"Hello. You alright? I'm a bit pissed...!" She slurred, coming towards me. Then as I moved away from the corner, standing upright: "Oooh! Very tall...!"
She still advanced on me, peering at me.
"Hang on, are you a bloke? You are, you're a bloke! Oooh, are you a traverst..., transverse..., a whachamacallit?!" She asked. I was mortified. She was being quite loud, so I shushed her. It sort of helped, as she shushed herself:
"Sshhhhh! Shhhhh! It's a secret. He.... She.... Ummmm? Nobody must know. Ssshhhh! Are you gay then? Why do you like wearing women's clothes? You look verrrry sexy!" And she giggled.
I could have run away at that stage. Maybe I should have done. But maybe I was worried she might call out. Also, she didn't know me, I didn't know her, what did I have to lose? Emboldened by my anonymity, I decided to answer her instead. I explained I was not gay - far from it. I explained that the clothes made me feel very sexy - didn't she feel sexy when she dressed sexily. She thought about this, her brow furrowing prettily under her mop of dark curly hair. She nodded.
She was now standing quite close to me, looking up into my face; she was only about 5'4". Then she got the giggles looking at me.
"Who did your makeup?" she suddenly asked. "It's terrible!!"
I could have reacted, but realised that her makeup was very good, and suddenly I heard myself agreeing with her, explaining I had no experience and asking her to do my makeup for me, to teach me....
She considered for a moment, then giggled. "Sure, why not. It will be a laugh!" A thought suddenly struck her, and she furrowed her brow again, looking serious. "You're not one of these weirdos, though?!" Solemnly I shook my be-wigged head, with its badly daubed on makeup. The irony lost on her, if not on me!
So we walked back to my room, girls together.
Back in my room, she looked at my small collection of makeup. She tutted. "Hmmm, I need to get some things of my own. I'll be back in a minute." And so saying, she left. I sat there, wondering what I was doing, wondering if she would come back and whether she would bring the hotel manager back with her. Then there was a knock at the door, and she was back with a more comprehensive makeup kit. I could scarcely believe that she had returned.
She somehow seemed to be less pissed now; more focused on the job in hand. I sat on the edge of the bed and she took her jacket off - she was in business attire: a short, tight skirt suit, white blouse - and sat in the chair opposite me. She spread her makeup tools out on a table next to her. She started by taking off the existing makeup, working away on my face, leaning in, with her legs crossed. Once she had finished scrubbing my face with various wipes, she started working with powders and creams and asked about what I did when I was dressed.
After a moment's hesitation, I decided in for a penny, in for a pound, so told her about the various chat rooms, like Omegle, Chatrandom and Chatroulette. I described how I try to be as feminine as possible for as long as I can. I explained about people exhibiting themselves on the sites and that, although I was not gay, how I got excited by the fantasy I spin; how I got excited by the excitement of my partner on the cam.
Once I had started to talk, I found I could not stop. I had never told anyone about this hobby of mine before. I realised that she had stopped working and was sitting, brush in hand, listening to me. I wondered what her reaction would be. Finally, she asked if I ever revealed myself and I explained that I did show my dick at the end of the cam session and that I generally got one of two reactions: one that they liked it and one that they would swear at me and stop the session.
She nodded, but didn't say anything, just got back on with my makeup.
I was aware of the close intimacy between us as she was doing my makeup, sitting facing and close to each other, our nylon clad knees occasionally touching, occasionally rubbing together when she turned to pick up another brush, or pen. We were close enough that I caught glimpses down her blouse as she leant forward. I began to notice her more as a woman - not sure why I hadn't already. The fear of when I was caught, probably. She was quite pretty, her hair in close-up was wavy more than curly, now I looked at it. I guessed her age to be mid-30s, maybe ten years younger than me. She had a nice enough figure, quite wide hips, but slim-waisted - I guessed she didn't have children, although she was wearing a wedding ring.
She leant in even closer now as she began to do my eye makeup, putting a hand on my shoulder to steady herself. I could feel her breath on my face, smell the sweetness of the drink she had been consuming a few hours ago. I began to get turned on by the situation, the closeness to this stranger, the conversation and the occasional glimpses of her flesh down her blouse. It was hard to hide my growing excitement in the short, tight Lycra skirt I was wearing. I had tucked as best I could, but as I became aroused, my dick unfurled, getting caught up with the knickers I was wearing. My skirt tented very obviously. I tried to shift in my chair to hide it, but only succeeded in making my discomfort, and my arousal more obvious. I caught her looking, and smirking.
Finally, she finished my makeup and had me stand up and look at the results in the mirror. I gasped in astonishment. You could almost not tell I was not female - my face looked beautiful. Almost, as the tent sticking out the front of my skirt kind of gave it away!
Almost coyly, she suggested that I went on cam and would I mind if she were to watch. I asked if she wanted to join in, but she shook her head and sat in the only armchair in the room. I lay out on the bed and positioned my laptop and camera so that we could both see the screen, but she was out of shot. She watched fascinated as - for the first time in my life - I positioned the camera to show my face.
I started the search for a partner. An old, fat guy showed up first, so I moved on. There were a couple of cameras, just filled with some guys' dicks, then I got to a younger, more good looking guy. He had a t-shirt on and the camera was focused on his upper half, not his cock. "Him?" I asked. She nodded enthusiastically. - keen to see what would happen next. He was already reacting to the unusual site of a beautiful "woman" on cam with him. I guessed he had been on the site for some time and had got bored.
"Please don't go...!" Was his first, hastily typed message. So we began to chat.
It was ideal for me, as he didn't get straight into trying to get me to flash stuff at him, so I had time to tell him my fantasy story: how I had found this site in my husband's internet history and had been on previously when I said I had been turned on by all the fit men wanting my attention. How this was my second time on, how I had put on sexier clothes, but was still quite shy. He was being very nice. He said he was twenty six. I said I was thirty five (she said I was a liar!). Eventually, he asked whether I wanted to play. She told me to ask him to take his shirt off, and thus, our roles became defined: she would give instructions, either for me to type, or for me to do (I had the mic muted).
As the young guy and I start playing together over the cam, I could see that she was getting turned on too, she was moving around in the chair, one hand pressed on the outside of her skirt, the other playing with her tits through her blouse. She was pink-faced and breathing quite hard. By now, I had shown him my tits (moobs work quite convincingly when partly concealed by the hair from a long auburn wig) and my panties - hiding my cock with my hand, as I had often practised. Eventually, I typed to him to say I had a couple of surprises: firstly I revealed my cock to him, telling him how hard he had made my "clit". It was partly true, I think that knowing she had been watching me had made my cock harder still. His reaction was good. He laughed and said I was still very hot. Then I said now for my second surprise, and I reach out for her hand and turned the camera to face her - quite slowly, so she had time to escape, but she didn't move.
Her skirt had ridden up somewhat, as she had turned and twisted, revealing her thighs. She waved coyly at the astonished man on screen. Then, unbidden, she got up and joined me on the bed. I made room for her. Her position caused her tight, business skirt to ride up revealing her white panties through the darkness of her tights. Both the guy on screen and I watch as she began to rub her sex through the combined material of her knickers and tights. I could smell the hot sweet scent of her arousal as she pressed her fingers to her pussy and rubbed harder. The guy on screen was now masturbating furiously and I began to do the same.
She peeled off her tights and pulled the gusset of her panties to one side and was now running her fingers along her pussy lips. I looked back at the screen, the guy had written: "Take them off PLEASE". I said this to her and she immediately peeled off her underwear, rolling her skirt higher, so it was round her waist, exposing her wide hips, beautiful rounded arse and scenting pink pussy, with it's neatly trimmed mound of dark hair. She now started to work her fingers into her pussy, first one, then two, lifting her arse off the bed in pleasure.
I slowed down the rate of my own stroking, to enjoy the show for longer, but I saw it was too late for the guy on screen as his cock jerked as his sperm shot from the end, his whole body jerking. She was watching him intently as she frigged herself. "Oh my god, I haven't seen a guy cum like that!" She said. The guy watched us for a while longer - his dick getting softer until he typed his thanks. Then he obviously nexted us, as another guy appeared, a bit fatter, a bit older, but already sporting an erection of quite some size. At the sight of the two of us, he started pumping away. The effect she was having on him, spurred her on and she began to frig herself with renewed vigour.
He typed a word in another language. She and I looked at each other. "What does that mean, she asked." "He wants to see your tits," I replied. I don't know if that was what he meant, but I wanted to!
She unbuttoned her white blouse, to reveal a lacy white bra, glimpses of which, I had seen earlier when she was putting my makeup on. She reached behind her to unclip it, matter of factly, but I said: "Do it seductively - watch his face". They guy's eyes were bulging and he was licking his lips hungrily. She laughed loudly, then slipped one shoulder strap off, then flicked the other one off playfully. He was leant forward, staring intently, absent-mindedly wanking himself as he focused on her striptease. She rubbed her tits through her bra, then put one arm across the front of her bra and reached behind with the other, but couldn't quite undo it like that. "I'll do it." I offered, without thinking. She put both hands on her tits and I knelt up and moved round half behind her, my cock poking out at right angles beneath my rolled up Lycra skirt and above my stockings. I looked at the image we made on the screen and my dick gave a twitch. I was aware that the end of my penis, glistening with precum was just inches from her smooth, slightly freckled shoulder. I wanted to touch her skin with it, to break that boundary, but the thought it might somehow ruin the moment stopped me. I reached down and unclipped her bra. She worked it loose with her fingers, all the time covering her breasts with her "hand-bra". I remained kneeling next to and slightly behind her, watching the image we made, watching the guy's reaction.
She began massaging her tits slowly, enjoying the effect she was having on the guy on the screen. He was staring fixedly, unblinkingly, wanking hard. I was stroking too, but slower - just enjoying the show. She was turning herself on even more, she was opening her fingers slightly, giving the guy glimpses of her nipples through her fingers, teasing the hell out of him. Then two things happened almost at once, she opened her hands so he could see all of her tits and he blew his load; three big jets of cum, all over his keyboard. "Wow!" She giggled. "I never knew my little tits would have such an effect!". We both laughed as we watched the guy trying to mop up his now sticky keyboard. Her tits were quite nice, milky white, with quite small, but prominent nipples. However the way she had teased the guy with them had done for him. Suddenly he must have cleaned the wrong button and his image disappeared.
"I wonder who will be next." She said - she was enjoying herself now. I stepped to one side and got myself re-dressed, doing my best to tuck away my cock so that I could appear again as a woman. She looked at me and followed suit, stepping away from the camera to do the same thing - although not putting back on her knickers or tights. We had just finished adjusting our clothing when the site found someone else. The image was just a small dick on a fat man, we flipped to the next, then the next, then another one.
After the fifth or sixth there was a very young looking guy in bed, with a sheet covering his lower half. Our camera was just showing my empty bed, with the covers rucked up. She moved back into shot and the guy started. I joined her too. The lad's mouth drooped open in surprise and his hand wormed under the sheet and he started fapping, his acne-ridden face turned towards us. "Careful. How old do you think he is?" I said. She looked askance at me. "I reckon he is only sixteen or seventeen," I said.
She leant forward and tapped the question on the keyboard. He replied he was seventeen. He interpreted our looks correctly and started typing away, pleading us to stay and play. "Flash him your tits if you must and let's move on", I advised, remembering how pathetically grateful I would have been to see real tits at his age. She laughed and unbuttoned her blouse while his hand busied itself vigorously beneath the bedsheet. I too - remembering he thought I was a woman - pulled down my top to reveal my bra. He goggled at the two of us. We both put our fingers underneath our bras and together counted 1-2-3, then lifted them. Her tits flopped out, my moobs wobbled a bit. As I leant forward to click on the NEXT button, my last view was of the goggle-eyed teenager as his hand was moving too fast for the camera to pick up. I had no doubt he would cum soon, and dream of us "girls" for months to come. His image disappeared and we just had time to sort our clothing out before the next image appeared.
This time, it was a fairly good-looking guy, shirt off to reveal a well-muscled torso, but with his lower half covered with track suit bottoms. "Ooh! THAT I like," she purred... He obviously liked what he saw too, as a wide grin spread across his face. "Can you hear me okay?" The sound came as a surprise, his voice a slow American drawl. We both nodded.
"Can he hear us?" She asked. I said he couldn't at the moment. "Let's leave it like that!" she said, and when he asked about our microphone I typed back that it wasn't working.
We chatted for a bit, him asking us questions, us typing the answers, but I could tell she was getting restless for some action. From his chat, I could tell that he was fully convinced we were both women. He asked if we were lesbian or bi. I answered I had never tried it. He said now was our chance to try... We looked at each other and giggled. He started asking us to show something - I typed back that she wasn't wearing knickers! He asked to prove it - she swore at me good-naturedly and knelt gradually spreading her legs so that her skirt rode up to reveal her neat, hairy mound and pussy. I asked what he was hiding in those jogging bottoms, and he flipped back the elastic and out popped a pretty huge, erect cock, which he slowly started stroking.
"Fucking hell, that looks nice!" She said, absent-mindedly rubbing a finger over her labia. I spread my legs too, the skirt also riding up, using a technique I had learnt to hide my cock behind my hand as I pretended to stroke my pussy through my knickers."I want you two girls to play with each other." He said. "You are soo hot."
"I'm not" I typed back.
"You are. You're hot!" He replied.
"Hot, yes. Girl, no" I revealed, moving my hand and pulling my knickers to one side. Out sprang my dick.
The guy leant forward, toggling at the screen. I noticed he was now pumping harder. "Oh... My... Fucking... God...!!!" He said. We both laughed at his expression. "I definitely want you playing with each other now!" I shook my head, but suddenly she had reached out and her small manicured hand had grabbed my dick hard and had begun to yank. I looked into her upturned face in shock and then she was kissing me hard, her tongue probing my mouth. After a moment's hesitation I was kissing her back, then my hand was travelling down her body to reach for that hot, scenting pussy. She was so wet already and getting wetter as we kissed. I began to frig her, sliding my fingers into her moist hole. She gasped before clamping her mouth back onto mine.
We were both so turned on, we nearly forgot the guy on the cam, until he suddenly groaned loudly. We broke off our kiss just in time to see him cum for us; jets of spunk firing from his jerking cock. His whole body jerking spasmodically, such was the strength of his orgasm.
We were so busy with each other, we barely noticed another guy appear on cam - staring open-mouthed at us. Suddenly she dived onto my cock, wrapping her lipsticked lips around my shaft and starting to suck me off. It was one of the most incredible feelings I have ever had. I had blow jobs before, obviously, but she was better than I could have believed possible. By now I was frigging her pussy so hard, I was in danger of developing RSI! Then all at once she suddenly started to climax, wildly and loudly, her whole body bucking to my touch. I too was about to orgasm and said so. "Not in my mouth!" she said, taking hold of my dick in her hand again. Just two firm strokes later I came all over my skirt. It was one of the most intense orgasms I had ever had. When it was over, I realised there was some old Indian guy on the cam, I wondered how many people had been on the cam and had seen us!
She lay back exhausted on the bed. I switched the camera and laptop off. Then I took my cum-drenched skirt off. I moved the laptop off the bed and stood beside her, my dick sticking out of my knickers, above my stockings. She lay there on my bed, her blouse partly unbuttoned, skirt hitched up, knickers off, fanny presented to the world! She was nearly asleep from the exhaustion of her orgasm. I manoeuvred her gently below the covers, carefully taking her blouse and skirt off as I did so. I took my blouse off too and got into bed with her. At first, I was going to sleep in my wig, but then decided it was too warm and itchy, so removed it.
We lay cuddled up in the spoons position. It had been months since I had been intimate with my wife - we had been married a long time. Added to which this lady was much sexier. I love my wife, but I was imagining making love to this woman, who moments before had my dick in her mouth, creating sensations I didn't think were possible. I was getting turned on again by the thought that I was laying beside her, just dressed in my lingerie as she was in hers. My stiffening dick was now pressing against her knickers, as she lay in my arms. I could feel the heat of her sex through her underwear. She was asleep now, breathing softly and rhythmically. I wondered if I could just pull her knickers aside and slide my cock inside her. But realising that she was asleep, this would be wrong. She may even say that I attacked her! I settled for rubbing the head of my cock against her knickers, feeling her pussy, hot beneath the thin material. That felt very nice, but it wasn't long before I too fell asleep.
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When I woke up the next morning, she was lying facing me, a confused expression on her face. I wondered how much she remembered and asked her.
"I remember having a load of fun last night, learning things I never knew. Like how sexy a man in drag could be!" she smiled. Then, suddenly asked, "Did we fuck?"
"No," I replied honestly.
She pulled back the duvet and looked at us both in our lingerie. Suddenly, without warning, she reached for my morning glory, which was poking out from my black lace knickers and gave it a few solid tugs. Then without saying anything, and completely by surprise, she pushed me onto my back, rolled on top of me and, kneeling above my cock, with one hand, guided my cock into her already wet vagina. Silently she began to ride me - her eyes on my startled face. I had not even begun to move, she was doing all the work; grinding away, her mouth opening now, her cheeks reddening, her breathing faster, her eyes never leaving my face.
Suddenly she grabbed my long auburn wig from the bedside table and, not breaking rhythm, handed it to me. "Put it on, Michelle!", she ordered.
Startled, I did my best to pull it on. Then my body started, unbidden, to react and I started thrusting into her. Still our eyes never left each other. I could feel the heat from her pussy, her wetness was dripping onto my thighs. She was getting hotter. I reached up and slid my hands under her bra and onto her small breasts - feeling the stiffness of their nipples against the palms of my hands. I could feel the muscles inside her contracting on my penis and finally our gaze broke as she shut her eyes and threw her head back as she surrendered to her orgasm. I could feel the heat surging in me too, and made to pull out.
"Fucking cum inside me, you bitch!" She gasped through her orgasm, her thighs clamping me there, and so I did and my god, it was good. The sensation of my hot jism filling her sent her into another orgasm. With this one, she was making guttural animal noises in her throat. There could be no doubts from the rooms either side, on exactly what we were doing, and how much she was enjoying it!
When her second orgasm subsided she collapsed on top of me, our bras pressed together, she was still twitching as her muscles spasmed with the effect of an incredible orgasm. Then her lips were on mine and her tongue in my mouth. I wrapped my arms around her and we kissed long and passionately, before, just as suddenly, she rolled off me.
We lay there, cooling off, not talking. Finally, she said to me "you need to go and clean all that makeup off your face before you go to work. Go on. Go!"
As bidden, I got to my feet and went into the bathroom, where I started scrubbing my face. I stepped back out of the bathroom to say I was going to have a shower and did she need the bathroom. But,the sound of a click behind me told me the hotel room door had just closed. She had just left.
On the bed were her bra and knickers and also some items of makeup from her collection. She had written a little note on a sheet of hotel paper. "For your collection. Wear them and think of me...!", it said.
I never saw her again, but I followed her request, and whenever I wore her underwear and applied her makeup, it was like a talisman - I always had a good time...
