I Left My Boundaries in a Club

This story is fantasy... at least /part/ of it is. Some parts are grounded in truth, just with names changed; other parts are a what-might-have-been extension of that. Some time frames have been compressed as I don't think you, gentle reader, want to hear about people making trips to the bar, trips to the loo, or trips outside for a vape. And for those who were actually involved in the early parts, yes, I've rearranged and simplified some bits to make a better story.

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"The walk of shame huh?" I asked myself, as I stepped out of the lift and headed down the corridor, my heels in one hand, my other digging in my handbag to find my room key. "Never thought I'd be doing one of these..."

Arriving at my room I let myself in and found that, as planned, the air con had stayed on so it was nice and cool. I dropped the shoes by the wardrobe space and flicked on the kettle that I'd left filled with water. I'd left the tea bag in the mug, along with the sugar, and when I pulled out my small bottle of milk from the fridge all was ready for tea.

While I waited for the kettle to boil I took my wig off, put it on its stand, and gave it a spritz of dry shampoo and a light brushing. Just as I finished that my phone pinged, that really annoying default message sound that I keep meaning to change.

"Did you make it back OK?" was the message, from my friend Sandy, whose room I'd left not 5 minutes ago.

"Yeah, no problems babe. Grabbing a cuppa then bedtime. Thanks for a lovely night. Sweet dreams xxx"

"You too sweetie, give me a shout when you're heading down for breakfast?"

"Will do. Night night xx"

"Ni ni xx"

Putting the phone back on the desk I glared at the kettle; what is it about hotel kettles that makes them take so long to boil? I wanted my tea.

Muttering gently to myself about bringing my own damn kettle next time, I took my dress off over my head, gave it a shake, and hung it on the hanger. The shapewear was next, unhooking it and peeling it off, with a sigh of relief as the compressed bits of me relaxed.

The kettle clicked off as it finally boiled, so I poured the water into the mug, gave it a stir, and left it to steep.

Walking the few steps to the spare bed (I'd been "upgraded" to a twin, which actually worked better for me since I was sleeping alone and a single was enough for me) I dropped the shapewear in the "laundry" pile. Reaching behind myself I unclipped my bra, and leaning forward I took it, and my tits, off. The tits went upside down to one side ready for a quick wipe with a cleansing wipe, and the bra joined the shapewear on the laundry pile.

Normally at this point it would have been knickers, then stockings and suspender belt, but my knickers were in my handbag so I ignored them for now. Putting my right foot on the edge of the bed I unclipped the suspender clips and rolled the stocking down my smooth leg. Repeating the process for the left leg I threw the stockings on top of the bra. The suspender belt came off and joined them, and then I was naked, apart from my makeup and nail polish which could wait until I've had my tea. I grabbed the big fluffy towel from the bathroom and wrapped it round myself.

The tea had steeped sufficiently, so I took out the teabag, added a splash of milk, and sat down to relax and enjoy it.

As I held the mug, inhaling the comforting and familiar smell of freshly brewed tea, my mind started drifting back over the evening...

The evening really started when I walked out of my hotel room, heading down to the lobby to meet up with friends. I'd done my nails and makeup, got dressed, had a small(ish) gin for fortitude, and now it was time to face the world.

Standing in front of the reflective lift door, waiting for it to arrive to whisk me down to my friends, I was struck by how damn good I looked. Sure, I wasn't passable in the bright light of the hotel lift lobby, but the night clubs were darker, and to be honest, it wasn't about being passable. It was about expressing the femme side of my gender, about looking as good as I could, and feeling good doing it.

And honestly? I think this was the best look I've achieved in a long time. A knee length, little black dress, with lace sleeves and shoulders, coupled with black seamed stockings, and black pixie boots. Simple, but by God I looked good.

As I was turning from side to side to see how I looked side on, and check that my dress was level at the back, the lift arrived with a ping. It was empty as I stepped in, so I used the mirrored side walls to try to get a look at if my seams were straight. I was preoccupied by this and didn't notice that it had stopped again until the ping sounded and the doors opened.

I looked up to see a middle-aged woman standing just outside the doors, looking very elegant in her evening gown. I realised I'd arrived at the lobby. Standing up straight I stepped forward, with a confidence I didn't entirely feel, but hey, fake it till you make it right? She smiled as she stepped to one side to let me out and commented "Nice dress."

"Thank you," I threw back over my shoulder with a polite nod as I kept going along the corridor, round the corner, and down the steps into the lobby.

Looking around I spotted my friend Sandy, in her green dress, with a floofy skirt and big ruffled petticoat, sitting on the seating near the door. I sat down next to her, we chatted for a few minutes, and then the rest of our party arrived and we headed out.

As the group of us walked down the street towards the first night-club I was hit with a mixture of emotions. I was buzzing, my first night out on the town Dressed; I was nervous, for the same reason; I was excited, as I'd been flirting with Sandy for a couple of weeks and we'd discussed boundaries, and I had no idea how it was going to play out. Interestingly I wasn't specifically worried about being out Dressed. That area of Anytown is known as the Queer Quarter, the night club staff and bouncers have all got a good reputation, and I was with friends.

The first club we went to wasn't really my scene; it was a bit crowded, and a bit loud for my tastes; although it was lovely to see so many trans folk and allies, out and about and just being themselves. The crowded nature of the place had one... well, some would call an advantage.

I was stood next to the bar, with people pushing past behind me. The space between the bar and wall was probably about two and a half people wide, which meant it could get friendly at times. And there was when I had my first bum squeeze from a stranger. I have absolutely no idea who it was, I don't even know if it started out as deliberate. It may well have been opportunistic. And while it was non-consensual, it did give me a buzz knowing that someone had found what was under their hand interesting enough to pause for a quick fondle.

We moved away from the bar and found a corner where there was a bit less foot traffic. And that was where I had my first consensual bum squeeze while en-femme! Sandy had positioned herself so she could put her hand on my bum, and gently squeeze. That was something different. I'd never had my bum squeezed by another crossdresser before, and I found I liked it. A few seconds later I tried to return the favour, but because of the layers of petticoat it didn't have quite the same effect.

It took me a few seconds to work out how to do what I needed to do, but I was able to pull enough of the skirt and petticoats up to allow me to slip my hand under and run my hand over her bum cheeks. It was a bit of an awkward position, as I had to lean over a little to one side, but that brought my head nearer to hers and we had our first, brief, kiss.

We stood there for a couple of minutes, people watching and chatting with the others, while caressing each other's bums. As I said it was a bit loud, but eventually a decision was made and Sandy leaned in towards me and said "we're going to go over the road to Futura."

I nodded, and took my hand back, pausing to straighten out the back of her skirt, and headed outside. The air outside was quite a bit cooler and I got a delightfully cool sensation at the top of my legs, between where my stockings stopped and my knickers started. That sensation is part of why I like wearing a skirt with stockings.

Looking around I spotted the main entrance to Futura and started heading towards it. Sandy called after me and as I slowed down she pointed to a set of stairs to one side of the main door. Catching up to me she explained that the stairs go up to the second floor which is quieter and has proper booths.

I followed Sandy and the others up the stairs and over to one of the booths - we ended up with three of us on each side of booth, Sandy was on my left, with Mary to her left, on our side of the booth. Drinks were obtained, and the proverbial "good time" was happening. Suddenly I noticed a hand on my hand on my left leg, just resting there. I glanced down casually and spotted that it was Sandy's hand. I figured I would return the favour, but because of the petticoats she probably wouldn't feel it if my hand was just on the skirt of her dress.

I reached my hand down, crossed over her arm, and gently teased up enough of her petticoats to get my hand on her leg. She twitched ever so slightly, as I gently moved my hand up her leg until it was at about the same point as hers was on mine, which turned out to be the boundary between the top of her stockings and her bare flesh.

As my hand was moving, hers started to move down my leg until it encountered the bottom of my skirt, at which point she hooked a finger over the edge and started to draw my skirt up. This sent a thrill through me and I realised why she'd twitched. This was decidedly erotic.

Once she'd pulled my skirt up sufficiently she put her hand on my thigh and started gently stroking my leg, moving between my stockings and the bare flesh, moving from the front, to the inside, and back to the front. I reciprocated, loving the feeling of the transition from nylon to skin, with the comparative roughness of the suspender strap occasionally making its presence known.

What made it even more erotic was the situation. Above the table, everyone was chatting, sipping drinks, laughing; below the table, Sandy and I were stroking each other's legs, and no one else knew what we were doing. At least if they did, there was no indication.

This carried on for a few minutes, very much enjoying it, until Mary needed to go to the loo so we all had to shuffle out. I sat back down where Mary had been sitting which put Sandy on my right.

We resumed our mutual stroking, pausing only to shuffle up a bit when Mary got back. A couple a minutes later I realised my hand was not alone... I'd slid my hand down the inside of Sandy's thigh when I felt a contact against the back of my hand. At first I thought Sandy had closed her legs up a bit and it was her other thigh. Then I realised it was moving... Mary was stroking Sandy's other thigh! I brushed my fingers over Mary's fingers to let her know I knew she was there, but this was a situation I had zero experience of, and no idea at all as to the etiquette of, so I just went with the flow and carried on caressing Sandy's left leg, occasionally brushing up the front of her knickers.

One more round of drinks later Mary called it a night and I had Sandy's thighs to myself, although by this stage I was in need of the loo myself, so I asked Sandy to move and headed off down the stairs to find the loo. The signage was good and I found the facilities with no problem. On my way there I was passed by a group of young women, one of whom slowed down as she passed me and said "you look wonderful" while looking at me. My second compliment of the night!

I called out "thank you" as I continued on my mission; if I'd not had such a pressing need I'd have stopped and chatted with her.

Matters dealt with I headed back upstairs where I found there had been a little bit of rearrangement of people, with Sandy now sitting where I had been, and the rest of that side of the booth empty. I slid in beside her and her hand went straight to my leg while I laid my handbag on the table and pulled my drink towards me. I returned the favour, and we resumed our mutual fondling. I suspected the others were well aware of what was going on by now and that added a further buzz to it. (I found out later that at least a couple of them did know what was going on.)

I turned to Sandy to say something and she leaned in and kissed me. With tongues, vigorously. I wasn't expecting that and probably didn't react as well as I might have done. I'm not used to tongues on a "first date" (not that it was a date, but I'm sure you know what I mean). My reaction, or lack thereof, didn't seem to change things though, her hand kept fondling and after we broke the kiss I also carried on fondling.

The banter carried on for a few more minutes, and then Nora and Martin said they were heading back to the hotel. Sandy looked at me, at my empty glass, at her empty glass, and back at me. "Fancy a nightcap back in my room? I've got some wine in the fridge," she asked.

I thought for a moment, considering how I felt, how turned on I was, how the conversations about boundaries had gone, about how I was feeling about the boundaries.

"Sure, that would be nice," I replied with a smile.

I slid off the seat, followed by Sandy, and the 4 of us who were left headed back to the hotel.

The walk back to the hotel was pretty uneventful, although at least one of us got wolf-whistled at, no idea which it was but I'm gonna assume it was me. (It was probably Nora actually!)

The four of us got into the lift, Nora pressed the button for 4 and looked at Sandy and me. "2 please," Sandy said. Nora looked at me with a quizzical look, so I added "me too", which caused Nora to smile as she pushed 2. I then remembered that we'd been talking earlier about which floors we were on and the different views, and I'd told her I was on the 3rd floor. "Ah well, we're all adults," I thought to myself.

Arriving at the 2nd floor, the doors opened, and Sandy and I got out. "See you tomorrow, have fun, don't do anything I wouldn't do," commented Nora.

"Well that leaves options wide open then!" replied Sandy. As the door closed I could hear a chuckle from the lift.

Sandy took my hand and lead me down the corridor. We arrived at her room, and she used her card to open the door. Entering the room she turned some lights on, keeping it not too bright, and headed for the little fridge. I kicked my heels off and hung my bag on a wall hook, before walking to the window and pulling back the curtain enough to take a look out and see what Sandy's view was. The back of the next building unfortunately, not very inspiring.

"Here you go," she said from behind me. I turned to see her holding out one of the hotel issue glasses with white wine in it. I reached out, took it from her, raised it up in a toast and said "Cheers." We clinked glasses and I took a sip - it was not at all bad and I made a mental note to get the name of it from her.

Sandy put her glass down on the desk and sat down on the edge of the bed to unbuckle her shoes. She motioned to the office-style chair and suggested I sit down so I rolled it clear of the desk and sat down. Not the most comfortable of chairs, but I wasn't there for the chair. Sandy kicked her shoes under the desk, leaned forward, and picked up her drink.

We chatted for a few minutes, talking about the evening and the people and the venue. Sandy filled me in on some of the gossip that I'd missed, and we talked about other clubs and venues. As we chatted the combination of the eroticism of earlier, the buzz of having been out en-femme in public, and the alcohol, was all combining to make me feel... well... I wasn't exactly sure /what/ I was feeling; I was horny, I was excited, I was nervous, and (although I'm not proud of this) I realised I'd left some of my previous discussed boundaries in the club...

We were both near the bottom of our glasses, and I realised that if Sandy was respecting the agreed boundaries then it was on me to make the first move to indicate they'd changed. After one final brief mental wobble I internally said "fuck it", drained the last of my glass, put it down on the desk, stood up, walked across the room, and sat down on the bed next to Sandy.

She looked surprised at this, but clearly realised what was going on, as she also drained her drink, stretched out her arm, and put the glass on the desk. Turning her head she looked at me. We made eye contact. Something unspoken passed between us (a cliche, I know, but it happens) and she asked me "are you sure?"

I leaned forward and kissed her, my tongue flicking across her lips. She opened her mouth a little and her tongue poked out and tickled the tip of mine. Our lips moved against each other, our mouths opening more, our tongues pressing deeper and deeper into each others mouth. I put my hand on her knee and ran it up under her skirt heading for the top of her stockings.

She broke the kiss, causing me a little surprise, wondering if I'd misread things really badly. "I'm sorry, I really, really, need a pee, before we go any further!" she exclaimed. I chuckled, removing my hand from her leg and swinging my legs to one side, as she stood up and headed towards the bathroom.

I took a moment to collect my thoughts, thinking again if I was sure about this, listening to both my brain and my little head, and decided that I had started, so I was going to see how far I was prepared to go.

I stood up, lifted my skirt, and straightened out my cock inside my knickers, making myself more comfortable. Sitting back down I didn't tuck my skirt under me, instead I pushed it back a bit so I wasn't sitting on it. That would make it easier for her hand to explore if she wanted. I certainly wanted her to...

I heard the loo flush, and the water run in the sink, then the door opened and Sandy came back out and walked back over to the bed. She sat down next to me, turned, put her hand on my knee, and pressed her lips against mine. We went back to the way we'd been kissing before she went for her pee, and I put my hand back on her leg. We'd turned our hips towards each other and we started stroking upwards on each others legs.

Reaching the top of her stockings I kept going up the strap, expecting to find the edge of her knickers. Instead I found the end of her leg and the start of her hip. I ran my hand towards her inner thigh, and the back of my hand encountered what felt like her cock. She'd taken her knickers off in the loo!

While I was discovering this, her hand had gone straight up my leg to my knicker clad cock. In the time it took me to discover that she had no knickers on, she'd slid her fingers under the edge of my knickers and was stroking my balls.

Continuing the kiss, with a bit of additional passion, I turned my hand around and wrapped my fingers round her cock. I started gently stroking it up and down, loving the feel of it, soft skin, warm, firm.

Her hand moved out of my knickers, and ran up my cock to the top of them, then she pulled them down a little and took my cock in her hand. The feel of her hand inside my knickers was electric, and I could feel my cock throbbing as she stroked it.

I was as horny as I've been in a very long time, and I really needed to get my mouth on her cock. I was a little torn because I was enjoying things as they were, but the desire to have my lips round her cock was getting stronger and stronger.

After a couple of minutes I broke the kiss and pulled back a little. "Let me suck you?" I asked, gently and quietly.

"That would be lovely," she replied, "as long as I get to suck you too."

I kissed her briefly and answered "I certainly wouldn't stop you."