Work & Pleasure – Part 1

Work & Pleasure – Part 1So this is part one of a new story I wanted to write, I like slow intros and lots of detail, as you’ll know if you’ve read my others. Part 2 will be a lot hotter, but hopefully you enjoy the “scene setting” too, it’s certainly not tame!—————————————————–A few months ago I had moved to a new town to help out a struggling branch of the company I work for. It was nothing special, but as a young single guy I was always picked for these trips due to my lack of commitments. I didn’t mind because it meant I got to see some new places, and got to stay in some fancy hotels! The main aim was to usually upgrade some office software, and help a few of the staff transition from one part of the office to the other. Again, nothing special, but the money was good and I was pretty much my own boss.My time on this one was pretty much over, and in a week or so I’d be able to head home. Until then, it was a normal Thursday evening in the hotel. Fresh from a swim in the pool, I ordered some room service and began to swipe through Tinder, hoping to maybe get some weekend fun. I wasn’t paying too much attention, it wasn’t going to be anything long term so I was just swiping and hoping for matches, and then it happened. The match screen popped up, and it was someone from the office, Claire. I had only met her at work a few times, she worked on the floor above and I hadn’t really dealt with them, but she seemed a quiet woman, maybe a little geeky. Kinda like Velma from Scooby Doo, in that she seemed to know the ins and outs of everything. She would often be hidden behind her desk, and when she was roaming the office she dressed quite plain. I didn’t want to unmatch, it would make the last week a bit awkward if we ran in to eachother, so I planned on just ignoring it. She had other ideas, and soon enough my inbox pinged. We exchanged a few pretty plain messages, I didn’t try to keep the conversation going but she always had a way of finding an opening. Every so often she would throw in half a flirty message, or a wink, just enough to keep me interested. I sent a picture of my fancy room service meal, and she replied with a picture of her bubbly bath with some candles. In the mirror behind her there was just a small glimpse of her ass, which I joked about. She replied with an embarrassed and funny message, and told me I should take her for coffee tomorrow after work to make up for it. Despite not planning to chat to her, especially meet her, I found myself looking forward to it as I drifted off to sleep. Friday at work was another fairly simple day, and on Fridays the company closed early so by midday I was on my way home. Claire had messaged me as I was getting to the hotel, and told me her favourite coffee shop, and that she would see me in about an hour. After a shower, I threw on some casual jeans and a shirt, before making my way to the Uber point and heading across the town to the coffee shop. Walking in I was greeted by that always amazing smell, and a large spacious cafe, but the most surprising thing was Claire. She was sat by the window in a booth, and she looked stunning. It was like a complete transformation, her perfect makeup framed by long black straightened hair. She wore a shiny PVC-looking skirt with black tights, and a cropped white top with some faint pattern across the chest. Her heels were tall shiny red patent heels, with her big toes peeking out from the small holes in the end. Her nails also red, matching her lipstick. I felt underdressed, and very attracted to her out of nowhere. “H-hi” I managed to mutter, still taking in her transformation. After some small talk a waitress came along to take our order, and along with our coffees we also ordered some light snacks. Her confidence seemed to have ballooned overnight, she even mentioned the accidental flashing in her pic from last night, and assured me she wouldn’t let me head home without seeing my ass too, followed by a cheeky wink. I became hooked denizli escort on her every word as she told me about herself, the way she played with her hair, and her cute mannerisms became more and more apparent. I had gone from 0 interest to 100, and then came the end of our coffee date. She told me she had evening plans, and that she would have to head home to get ready, so we both made our way outside and as I called for my Uber, she asked what I was up to in the evening. “No plans for little old me, maybe some more room service and waiting for another cheeky picture from you?” I joked. “If you’re really lucky” she returned playfully “But if you’re bored you should join me for drinks, it’ll only be me and a couple of girl friends. Let me know!” she leaned in for a hug, and a kiss to my cheek. Not wanting to seem desperate I headed back to the hotel and waited a bit before sending my next message ‘So if I was bored, and fancied heading out for some drinks, where would I be going? ;)’ and in no time came the reply ‘Well come to mine, and we’ll go together, it’s a nightmare to find?’. I was totally in here, just had to put up with an evening of girly chat and surely I’d be staying at her place. ‘Sounds good to me Claire, it’s been ages since I’ve had a proper drink. What should I wear / bring? I only have a suitcase of clothes, so nothing too fancy!’ I replied. Claire told me what I wore to lunch would be fine, she had a few “accessories” for me if I needed them, and maybe something to drink before we went out.Soon enough I was walking up to her door, bottle of wine in hand, which I almost dropped when she opened the door in a bathrobe! She was so cheery as she invited me in “Won’t be long, just got to do my makeup and getting ready will only take me 5 minutes. Pour yourself some wine, or there’s beer in the fridge!”. I took a beer, and we began speaking loudly from one room to another, before she asked me to top up her wine. She held the empty glass through the gap in the door, and I refilled it before returning. I nudged the door open with my foot, but it swung open more than I planned to reveal Claire in just her panties at her dresser. We both panicked, I tried to turn away, she knocked the door, and spilled a whole glass of red wine down my jeans and shirt. She quickly covered herself again, and we both apologised to eachother as she began to wipe me down. It was obvious my outfit was ruined, but she did insist on washing it. Stripping me down to my boxers, she joked how she’d finally get to see my ass, as I struggled to hide my growing cock. “This will never be washed, and dry again, by the time we have to go out!” I told her. She hurried my clothes in to her washing machine, and then as it filled with water I realised I was kinda stuck. I couldn’t go home in my boxers, and now it would be at least 2 hours until the machine released them. “Can I help tidy?” I asked “I think I got some wine on the floor?”. She thanked me as I knelt on the floor wiping up any traces, and as I finished I turned to see her applying the last of her makeup. Her eyes framed in perfect eye liner and mascara, and the dark red lips gave her more of a dominant look this time. “How do I look?” she asked, and as I began to answer she stood, letting her robe drop to the floor. She was wearing the most perfect lingerie, seamed stockings, wet-look panties, bra and suspended belt. I was in awe, still knelt on her floor as she approached. “Maybe you can help me get dressed?” she asked, stopping just in front of me. I stared up at her pussy, hidden by a thin layer of latex, and inhaled her smell “Maybe I can help you get undressed?” I winked. She took her seat by her dresser and beckoned me in, and I crawled towards her stopping at her feet again. “If you do a good job with my feet, and my legs, maybe you can earn a reward” she cooed, lifting a foot to my face. I began to rub and kiss, working my way up, but as I reached the top of her stockings she denizli escort bayan stopped me. “I have an idea, if you think you’d be willing to play a little roleplay?” she stared down at me, knowing I was desperate for some relief “Of course Claire, I love roleplay!”. I was imagining her as a nurse, or a secretary, but she had other ideas. “I’m talking about femdom, I love to feel in charge” she began “But you’ll love it I’m sure, you’ll earn your way to pleasing me in no time” she teased. I agreed to try it, expecting some fluffy handcuffs and maybe a spank or two, but she was more experienced than that! She told me she was going to get ready, and that she had some things for me to wear, and then we could head out. In no time she had covered her lingerie in a shiny PVC or latex dress, knee length, with some stunning heels too. My outfit was in a small bag, which I tipped on to the bed. Out fell some stockings, panties, trousers and tight white tshirt, and my confusion must have been obvious. She explained that it was just a game, I would wear the panties and stockings under the trousers, and no one but her would know. Any hesitancy soon went when she told me how turned on she was at the thought of it, and how she would be desperate to get me back out of the trousers when we got home. Soon enough we were ready to leave, I looked like a plain guy with my stunning shiny date. “One more thing, can you wear this for me, pleasseee” she kissed me on the cheek as she popped something small and plastic in to my hands. A chastity cage. “No way!” I hit back, and then came the offer I couldn’t refuse. “What about if I get you off first, you’re probably too big to fit in that anyway?” She slipped a hand down my trousers and played with my cock through the panties. In no time I was close, seeing her dressed like that would be enough for any man. She reached for a small glass from the side, and as I came she collected it in the glass. Any post orgasm bliss was ended when the plastic prison was locked around my cock, and just as we walked to the door she poured the glass of cum down the front of my trousers, before doing them up again. The gooey liquid filled the panties and some trickled down my leg, but in no time we were outside her house and climbing in to a waiting cab. I sat awkwardly as the cum and chastity cage began to irritate me. Claire held my hand, and kissed my cheek again, and I melted in her arms. She had such control of me and I hadn’t even noticed. I stared out the window as the cab passed many bars, before we stopped outside a bar called “LATE-X”. I’d never been in a fetish club, but that was about to change. We met one of Claire’s friends outside, and she was dressed in PVC too, a guy behind her had a woman on a leash, and my cock tried to grow but the cage reminded me I wasn’t in control tonight. We headed inside, and it was like a giant party. Everyone seemed so friendly, encouraging and up for fun, and I began to feel more at ease. As the drinks flowed, I felt more and more at ease, enjoying myself and my new friends. We watched the stage performers, some women being dominated, and some guys being dominated, each causing my cock to strain hard in its cage. “Claire, do you think you could undo my cage, it’s starting to get real uncomfortable?” I asked in her ear, but she told me how she loved knowing I was ‘saving myself for her when we got home’ and began to grind herself against me. It was unbearable but she was SO hot I just couldn’t stop her. I put my hands around her waist and tried to feel her up, but she shrugged me off. “I like to be in charge, be a good boy and you’ll get your reward tonight” she winked back. I had never felt like this before, never been anything close to submissive, but I was totally under her spell. She would do all she could to tease me, kissing her friends and being as flirty as she could, until finally it was time to leave. “My neighbours have been real jerks recently, why escort denizli don’t we nip back to mine so I can get some bits and then go to yours?” she pressed herself against me and gave me a passionate kiss, our first proper kiss, and placed my hand on her ass. I squeezed, and enjoyed the kiss, but soon enough the cage was causing me to strain again. “I can’t wait to get this thing off, let’s go!”. The cab ride consisted of us kissing, and her rubbing my cage to tease me more. Once she had grabbed a bag, she was back in the car and we were heading to my hotel room. We ordered some room service and soon the door knocked with some snacks and drinks. Claire dangled a small key and told me to beg for it, which I did. Anything for release. “As soon as you please me enough, it’s all yours” She stepped out of her dress, and laid back on the bed. She poured a dribble of the champagne in to her mouth, and kissed me. Then some on to her chest, and I licked it all up. Before going any further, she reached in to her overnight bag and removed a blindfold, and some cuffs. “Please Claire, no more, I just want to get inside you” I pleaded, but she insisted I had to please her well enough, and release would be soon. My hands cuffed behind my back, she guided my face between her legs. Finally I could taste her, and she pulled her thong aside as I stuck my tongue deep inside her and began to lick away. She would reward me with dribbles of champagne poured from above, mixed with her own juices, and she was moaning with joy. She came hard, her thighs clamping my head against her pussy and forced me deep until finally she relaxed. It was my turn, and I couldn’t wait any more! She was fiddling with something, I could hear some rummaging, and then finally she removed my blindfold. She directed me to lay on the bed, and connected my cuffs to the edge of the bed. There I was stripped naked, apart from the cage, and my ankles secured to the bottom of the bed. “Time for your reward” she straddled my chest, and began to dribble champagne in to my mouth. I drank it down, and then she began to fondle my locked cock, this was it, and I was SO ready for release. My eyes began to feel heavy, and Claire climbed off of me, leaving me tied to the bed. “Maybe you’re too sleepy? I thought you wanted to fuck me?” she came in for another strong kiss. “Guess you didn’t want your release as much as you thought” she began to get dressed next to the bed, and all of my energy drained away. “It won’t last long” she told me “and I’ll see you Monday” she gathered the last of her things and as she was finishing her outfit, I fell asleep. I woke the next day to the sun shining through the window. I was groggy, with the hangover from hell. As I tried to remember the night before, my wrist tugged against the restraint and I suddenly remembered I was still tied to the bed. I looked down at the cage, still secured to my cock, and my stockings still up my legs. Next to the bed was a note, and some keys ‘Thank you for a wonderful night, you will get your release, just got to earn it’ and a big red lipstick kiss. ‘PS- the housekeeping will unlock you, I’m sure they’ve seen it all before!’Panic set in, and I began to thrash about. It was no use, the cuffs were secure and I knew what was coming next. Eventually the familiar knock at the door came “Housekeeping” came the call, and my heart sank as the door unlocked. She let out a small scream, and a very embarrassing 5 minutes later she had unlocked my wrists, promising to be discreet for a large bonus tip. Still wearing the stockings, and cage, I handed her some notes from my wallet and she left, chuckling to herself. I messaged Claire, no reply. I messaged again, no reply. “Please Claire, just give me the key and I’ll never mention any of this”….. Finally came a reply “I see you’ve managed to free yourself! You’ll get the key, Monday at work. I loved having so much fun last night, can’t wait to play with you again! I’m really busy this weekend, so just have to see you Monday. Claire xxxxx”I couldn’t believe it, I was going to have to stay like this for the weekend. I normally jerked off at least once a day, and I was so desperate from all the teasing. It was going to be one LONG weekend…. Little did I know it, but it was going to be an even longer week too…..