Maid To Pay free porn video

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Yay! The day had finally arrived. I'd been terrified and excited in equal measure for the months leading up to today. Unfortunately little did I know that today was going to go very differently to how I'd planned. First let me jump back to how this all started. I've been a crossdresser since I was a kid, but unfortunately I was always a bit of a fat kid, who grew into an overweight,tall and well-built man. As a result I never really got the knack of dressing enough to be all that passable. When I met my wife, Jo, a few tears ago I was honest from the start about the crossdressing, and thankfully she was quite cool with it. Even going so far as to allow it into the bedroom, where i was often allowed to wear some kinky underwear during sex (PVC basque, stockings, that kind.of thing). In fact the sex was often quite fruity, frequently involving some mild BDSM and (very) occassionally Jo would also use a small strap-on and fuck me in the arse. Basically, she was an amazing wife and I've always counted my blessings since the day we met. However, sometimes these things are not enough are they? I'd never really dressed fully, and certainly never in front of Jo. Partly this was due to the fact that i'd been at my most overweight since i met Jo, which brings with it both a low self esteem, but also a difficulty buying sexy clothes that are fairly comfortable. But also this was because i knew it was almost a step too far for Jo. She was cool with the lingerie and the kinkier sex, but she said that seeing me fully dressed and not looking like myself would freak her out a bit. The desire in me wouldn't really go away though, so eventually I approached Jo with a question. I asked her if she'd let me dress up fully one day, if I managed to lose a large amour of weight. She really wanted me to lose weight and we'd been trying everything, but I just didn't have the willpower. I reckoned that if I had such an important goal, then maybe this diet might last the distance. The plan would be for me to be a French maid for the day, in the hope that such a silly outfit (and running around cleaning the house, feather duster in hand), may just be bizarre enough for her to find it all funny, instead of worrying. Well, that and i'd always fantasised about wearing a maids outfit; especially a PVC one. After a fair amount of deliberation Jo eventually agreed, just so long as the day went by her terms so she could call a halt if she was uncomfortable. So finally the big day arrived. 10 months later and 70 pounds lighter and to be honest I was a bundle of nerves. A nice, slim bundle of nerves admittedly!. Jo had been over the moon with my weight loss, and her happiness (and the thought of this day) had really kept me spurred on. Jo had got up a fair bit before me that morning as i'd been out for a few beers for a friend's birthday night before. I went downstairs and found Jo making breakfast "Morning honey," she said, "your big day has finally come around and I thought i'd treat you to a big breakfast. I'm really proud of you and your diet. When you've eaten that, head into the living room. I've laid out the outfit we bought, with a few extra additions of my own." With that I began to devour my breakfast as quick as possible, really intrigued to find out what these extras were. Jo and I had bought a PVC maids outfit online a couple of months before, along with some lacey white lingerie and some black patent court shoes. I had an old wig from when I used to mess about with dressing a few years ago, which I was planning to use. Clearly Jo had decided differently. When I walked into the living room, I saw that she had decided on quite a few changes. Laid out neatly around the room were a multitude of items. The PVC maids dress was there, but next to it was a white netted petticoat that would make the skirt part stick out at a ridiculous angle. Gone was the white lacey lingerie, instead there was a black PVC waspie with 6 suspender straps and a pair of lace-top stockings. Next to that was an amazing pair of black PVC knickers with lots of white frilly lace at the back. Even better, the PVC seemed double sided! Topping all this off was was a wonderful long, slightly bob-cut blonde wig and a pair of silicon breastforms. Clearly I was in a but of shock at the whole ensemble as Jo walked in and asked why I was staring. "Bloody hell sweetheart, where did you get all this?" I asked. "Well I figure if we're finally going to do this it may as well be done right," she replied. "And I really am proud of you." All I could really say was, "Wow!" "Right, aren't you going to take your clothes off and get started?" asked Jo. I stripped off in a flash and made my way over to the clothes. "Ah ah ah, what do you think you're doing?" she said. "You want to spend the day as a girl and no girls have that much body hair, I want it gone. And I mean ALL of it!" "But honey," I replied, "I've never done that! I have to shower with my mates after football and they'd all see!" "Tough, can a very disinterested reply. "I told you when we agreed to this, that's its my rules. And my rules say I don't want to see a hairy-legged French maid walking around. And don't forget the rest. I don't even want a bikini line, I want it all gone. Now snap to it". I sloped off to comply, wondering just how long i'd need to leave it before I played footy again. Starting with an electric trimmer, I swiftly moved onto a razor and it wasn't too long before I was as hairless as i'd been since birth. To be honest, once I'd moisturised it felt great. It even left me wondering what excuse I could give the guys if I were to keep things this way! I headed back downstairs and found Jo sat at the kitchen table, with lots of cosmetics strewn around. "Sit yourself down and lets get started" she said. I sat down and just let it all happen, wondering happily how i'd got so lucky marrying this woman. I'd not really dabbled too much in make-up in the past, and on the few times I tried I looked dreadful; so I was excited to know how this would turn out. Slowly Jo applied the works. Foundation, blusher, eyeliner, a dark eyeshadow, stick-on lashes, mascara and a seemingly very red lipstick with gloss. Now I was really intrigued with the results! Clearly pleased with her work, Jo then took one of my hands and began to glue on some insanely long nails. "Before you start whining about your mates again, these will come off with a bit of effort, so don't worry." Once she'd finished she pulled out some bright red nail varnish and set to painting my new nails. 2 coats followed by a top gloss just to make sure I didn't chip them apparently. With my nails still wet, and under orders to not touch anything until they dried, Jo led me back into the living room where my new outfit was still neatly laid out. "Stand there honey and keeps your arms up. And look after your nails. I'm going to dress you." 'This is brilliant' I thought, as Jo first went for the PVC waspie and clipped it around my waist. It was more like an underbust corset that really pulled me in tight, and Jo gave it a good few pulls to make sure it did. Next she had me lift a leg ad she knelt in front of me and raised a stocking up my leg, clipping it to the suspender straps. Much as I was actually feeling a little silly stood there, I could help but sport a massive hard-on as I watched Jo run the second stocking up my other leg. I looked down at her with a huge grin, and she looked up at me with a sly smile. As I was hoping, she moved her head and slowly took my cock in her mouth and began to move her lips up and down the shaft, all the while looking up at me and smiling with her eyes. Having the time of my and feeling like all my dreams were coming true, I closed my eyes and enjoyed what was happening. As soon as I closed my eyes, I felt an agonising pain as Jo bit down hard on my cock. "Arrrgh! What the hell?!" I screamed as I jumped back with a sore and rapidly declining erection. "They're be none of that yet honey," smiled Jo. "I know you too well, as soon as you've got your rocks off you lose all interest in this kinda thing. And you've got work to do for me remember. Now come back her and let me finish your uniform." Begrudgingly I moved forward again and Jo stood picked up the freakishly large breast forms and moved behind me. She placed them onto my chest and I felt some wetness on my skin. "What's that?" I asked. "Oh just some medical glue." "GLUE?" I almost squealed. "How are we supposed to get them off?" "Not to worry, I have some adhesive remover that works fine. And until later you're just going to have to keep me pleased won't you," she said with something of an evil grin. I grumbled a little, but was amazed to look down and see a really realistic set of massive tits, that were so heavy they were already starting to pull hard. Clearly reading my mind, Jo placed a black, semi see-through, underwired lace bra and connected it at the back. This whole experience was becoming more and more wonderful by the minute, bitten cock aside of course. Next Jo had me step into the big ruffled white petticoat and she pulled it up around my waist. This was followed by a rather ungainly attempt to put on the sexy-as-hell black patent knee-high boots. Once they were on I realised they weren't quite as intimidating as first thought. While the heel was a good 4 inches, it was actually chunky enough not be as lethal to an amateur as a stilletto would be. Next came the bit i'd been looking forward to the most, the dress. jo had me hold my arms up as she slid the dress over me and pulled it down and out over the pettitcoat. It was amazing! Tight across my massive tits and coming out at a silly angle over the large ruffled petticoat. It was everything i'd dreamed of and fantasised about. Nails now happily dry, Jo pulled some long PVC gloves up my arms. They were a type with the fingers ends missing, so they still showed off the long red nails. Onto the last few pieces, Jo then tied a white satin apron around my waist, followed by the piece de resistance: the wig. This was fitted, wiggled and generally played around with until Jo gave a satisfied nod, followed by the addition of a white satin and lace hairband-type thing. Jo stepped back and tried to supress a laugh. "Haha you're gonna love this honey. I think all your embarrassing little fantasies have just come true. I'm just gonna go get a mirror. Plus, I forgot something." With that she walked out left me standing, and nicely creaking, in the middle of the room. I was struggling to come to terms with just how well today was going, and just how much Jo seemed into it all. And all the creaking, mixed with the frilly petticoat was starting to give me a hard-on again. It was then I noticed we'd forgotten the knickers. Just then Jo walked back in holding a long mirror and carrying a small bag. "Honey, we forgot the knickers," I said. "They're coming," she said. "Just need to sort something out first. Now, what do you think of the job I've done?" I looked at my reflection in the mirror and gasped...... I looked amazing! If by amazing you mean i looked like the sluttiest, sissiest tranny maid you'd ever laid eyes on! My new slim figure, combined with a stunning make-up job, the dress and the wig all came together to hide all traces of my manly self. Jo had worked miracles. "Honey I...I...I look....." "Like a total fucking sissy slut fag?" she laughed. "Well i wouldn't have quite put in like that, but yeah!" i grinned. "Aren't I good to you sometimes?" "Hell yeah," I said, smiling. "Right, lets just get things finished," said Jo, "and if you've got another hard-on it better be gone by the time I pull your knickers up, or you'll get more of the same." I didn't need telling twice, as my cock went flaccid almost on cue. Jo grabbed the PVC knickers and knelt in front of me with with the small bag she had. I couldn't actually now see what was going on as the petticoat pushed the hem of my dress out so much. I felt Jo's hands around my cock and balls and then felt something solid clamping around. "What's going on down there?" I asked, slightly concerned. "Be quiet and stand still or this might hurt," came the reply. With that I pretty much froze in place. In short order, something hard was slid over my cock and I felt and heard something click into place. "There, that should do it" she said. I put my hand down there and felt a complicated plastic contraption....she'd put a bloody chastisty device on me!!! "Honey what's that all about?!" I gasped. "I told you before sweetie, my rules today. If you want to get any sexual kicks out of this, its on my terms and at a time of my choosing. That cage is padlocked, so unless you play ball you ain't getting your rocks off for a very long time!" she said laughing and attaching the keys to her necklace "Just in case," she winked. "Now lets get those knickers on and we're done and we can set you to work." With that she got me to step into the knickers and pulled them up. When she'd finished she started to gently stroke and rub my balls and arse through the PVC and then began to nibble on my ear. The effect was pronounced. My cock almost immediately stirred in response, but had nowhere to grow. The feeling was a mixture of pain, discomfort and enjoyment. It was frustrating as hell and I can't say I was too impressed. It must have shown "Aww little sissy feeling all grumpy and frustrated?" chuckled Jo as she moved away. "Just not what I was expecting for today really. Is keeping my cock all caged up really neccessary?" "Look you, for years I've listened you tiptoeing around your true fantasies, and don't think for a second I haven't check out all the porn you look at and the stories you read. "Don't lie to yourself, you love the idea of bring properly dominated and humiliated, and if we're going to do this, and if you're really going to pull me into a full tranny session, then you'll damned do what I say. I'm going to have some fun in all this too, all these sex games we've had have almost always been about you. Well fuck you, this is actually my day, not yours. I'm just giving you what i know you fantasise about at the same time. Lets call it a win-win situation shall we? "And in the meantime lets re-address the ground rules. There aren't any for me. You do what I say, when I say or you will NEVER indulge your kinky little desires around me ever again. And I mean, ever! No crossedressing, no strap- on fucking, nothing. Are we clear?" I was a little bit taken back by this strong side coming from my wife and just stared at her in shock. The thought of losing all those fun things that make our relationship so cool, and that I really need to stay sane, was horrifying. #SLAP# "I SAID ARE WE CLEAR?" demanded Jo. Cheek stinging, and completely in shock, i simply looked at the floor and nodded. "There's a good sissy," said Jo softly as she gently carressed my stinging cheek. "Here, you'll need this today," said Jo, handing a pink feather duster. "And these too," she said as she threw me the car keys. "You're driving." "What the bloody hell do you mean I'm driving?!" I demanded. "I can't go outside dressed like this, someone could see me!!" I pleaded. "You really do need some training don't you?" replied Jo calmly. "Let's go through this one more time. You WILL do as i say, or all your fun, kinky little games are over for good. In addition I'm not letting your cock out of that cage if you don't do as i say. Let's see you playing football with that on and showering with the guys. Which reminds me....." Jo trailed off and produced my mobile phone from her pocket and immediately snapped a couple of pictures. Horrified, i just stood there with the realisation i'd created a monster. "Yes, it probably is as bad as you think. If you don't behave, not only do you suffer the other punishments, but these pics are being loaded straight into your football team's Facebook page. It's you choice sweetie." To be honest, stood in the middle of the room, cock caged and wearing the sissiest outfit possible, all the fight just went out of me. It's hard to stand up for yourself in that situation. Eventually I nodded and walked towards the door. Jo grabbed her coat and a large bag and went to the car first. Once in the car she waved me forward and I just ran, or should I say 'tottered' down the drive to the car and went to open the driver's side door only to find it locked! Jo was sat in the car laughing and snapping photos as I pleaded to be let in. After what seemed a couple of terryfying minutes, but was actually probably just few seconds, she let me in. I jumped in quickly and slammed the door shut. I sat there shaking for a little while and glaring at Jo, who just chuckled. The next problem was the dress; it really wasn't conducive to sitting behind a steering wheel. After much faffing I eventually managed to get it under control and i started the car. Having never so much a been out of the house dressed up before, i had no experience at all in driving in high heels. It took some getting used to, but after a while i got the hang of it. Luckily I have an automatic car, rather than a manual, which helped immensely. Not sure where the hell we were going, I just followed Jo's directions. We left the town we lived in and hit the motorway and drove for about 30 mins before Jo got me to take a slip road and head towards another town. Dread started to knot up my stomach.....we were heading towards where we work and where many of our friends live! Sure enough my dread began to become panic as I realised we were driving to the house of a lady called Lorraine, who was a friend of mine and Jo's from work. In fact she was good friends with each of us before we got together. As we pull up on her driveway, I felt like breaking down in tears and almost begged as I pleaded with Jo "Please don't make me go in there honey" "Oh honey it'll be fine, I'm sure you won't let me down. And you know what happens if you do. So here's the score....you WILL walk up to the door and when it is answered you WILL curtsy and you WILL say 'Hello Miss Lorraine, my name is Lisa and I will be your sissy maid for the day'. Anything less and that's it. Understand?" There wasn't really anything I could say to that, so I just nodded meekly and got out of the car with Jo and took the few steps to the front door of one of my closest friends. I rang the doorbell and stepped back, acutely aware of my attire and steeling myself against what was to come. After what seemed an age, Lorraine opened the door and paused, looking me up and down with an appraising eye. Feeling about as humiliated as I thought I could ever be, I stepped back, pulled out the hem of my dress and awkwardly curtsied. "Hello Miss Lorraine," I said quietly. "My name is Lisa and I'll be your sissy maid for the day." There, i'd done it. Now if I could just get in the bloody door then the humiliation could end. How was I ever going to look Lorraine in the face ever again? ....And why was I naive enough to think the humiliation would end here?! We walked into Lorraine's house and I followed Jo and Lorraine into the living room. "Well aren't you just a sexy little thing," said Lorraine. "Jo, you said he would be coming dressed as a little sissy fag, but I had no idea he'd look so damned slutty aswell. Though I suppose I should say 'she' looks so damned slutty!" she laughed as she walked into another room, leaving me alone with Jo. "What's going on honey?" I asked. "Why did you involve Lorraine and how am I supposed to look her in the eye at work on Monday?" "Don't you worry about MISS Lorraine" she said, emphasizing the 'Miss'. "She's always known about your crossdressing, but never said anything to you. Apparently she noticed you playing with a bra strap one night when you were out drinking, before me and you even met. Once we started dating she mentioned it to me, and since then I've told her most things. When she mentioned your rapid weightloss i told her your reward was to dress as a maid for the day. She laughed so hard at the thought of you dressed like that and asked if you were available for outcalls to clean her house instead. So here we are. Miss Lorraine and I are going to sit in the conservatory and enjoy the sun whilst being waited-on by our own personal sissy maid. So you will be both maid and serving girl. Now I suggest you go and visit the little girl's room and get yourself ready for your shift. Oh, and if I were you, i'd 'empty' myself while I was there" she winked. I slopped off to the toilet and did as suggested, though its not like I needed much encouragement, I was terrified by the latest turn of events! I had to sit down to pee anyway, as the bloody chastity device meant i couldn't pee like a man. I caught a look at the device in the mirror and saw that it was made of a clear plastic, so I could see my cock trapped inside. I think that made it even more humiliating than if she'd used some kind of metal device, or something equally opaque. God I looked bizarre in the mirror. I could easily have stayed in the bathroom for the rest of the day, but thought I best not to keep my newly-wicked wife and friend waiting. I made my way back out to the living room to find Jo waiting with her bag in hand. "OK sissy, come over here and turn around with you hands behind your back," she said. I duely obliged and almost immediately found my wrists handcuffed behind my back. "Just so you don't interfere," whispered Jo in my ear. Next she bent down behind me and attached something tightly to the ankle part of my boots. I couldn't quite see what she'd done, but from the clinking sound I could tell that she'd attached a chain between them. Just how short I couldn't tell. Next Jo placed a red ball gag over my head and pulled it really tightly back into my mouth. I felt her tighten the gag, followed by the ominous sound of a lock clicking into place. I tried to talk, but all that came out was a mumble of rough words. This just made Jo laugh. "That works then! Your gag is locked so its not coming off anytime soon. We can't have any back-chat from our new sissy can we? "I've also locked a very short chain between your ankles, so you can only take small lady steps until I say otherwise. Should be good for a laugh, after all we don't want your cleaning to be too easy." This really was going from bad to worse, i'd stopped having any fun ages ago, but Jo had more shame yet to dish out. She slowly turned me and moved me towards a chair, which took a little while as walking was really constrained by the tiny little pigeon steps I had to take. Jo then pushed my body so I was stood leaning over the back of a chair, with my arse stuck out towards her. 'What now?' I thought, dreading what was to come. Sure enough, Jo pulled my knickers down to my knees. Oh Christ, she was gonna actually do it! And with our friend in the other room too! "Best you don't struggle now my sweet little sissy," she said as i felt her lubed-up fingers probing my hole. I tried to beg her not to, but even though she got the drift, the mumbling just made her chuckle again. First one finger was used, followed by a second and a third. I tried hard to relax to ease the discomfort, but it was nigh on impossible. In short order, Jo pulled her fingers out of my arse, but almost immediately i felt something harder and rubbery pushed against me. "In we go," she laughed, as she shoved the dildo into me. It felt pretty huge and long, certainly at the limit of what my arse usually takes.... but those times I'm usually really relaxed!! With one final push from Jo, I felt my hole shrink back around the dildo, realising it was actually a butt plug. That at least eased things, but I was still feeling pretty stretched and full. Almost immediately Jo whipped my knickers back up and pulled me back up to a standing position. "Now to make sure that stays where its supposed to," she chimed, and I felt the plug swell inside me... It was a bloody inflatable one! I moaned and winced as it started to feel like I was going to split, and when I let out a loud moan of pain, Jo immediately stopped and let a little bit of air back out. "Uncomfortable but just shy of being agony. Perfect!" she exclaimed triumphantly. She then fiddled around behind me and I heard another click. "Just in case you're wondering, I've clamped off the air tube and used a little lock, so you're stuck with this in your arse until we feel you have performed your duties to our pleasure. "Best you work your little booty off to make us happy baby," she whispered gently and seductively in my ear. "Let me just tie this to your pinny," she said as she tied a white satin pouch to my waist. "ALL DONE," shouted Jo through to the other room. With that Lorraine came into the room sporting a huge grin. "Lets see if it works then" said Lorraine, pulling out her mobile phone. 'what now?' I wondered. Not sure that I could take any more humiliation. Jo explained what was happening "When we were discussing how today was going to go, it occurred to us that if you were cleaning the house, you wouldn't be able to wait on us without us either come to find you or shouting. Which just wouldn't be fun would it? So that butt plug is powered by a small box in that little bag, and it responds to phone signals. Also in the pouch is my mobile. "Now Miss Lorraine is going to test it by giving me a call." Lorraine again gave a huge grin and pressed a few buttons on her mobile. There followed a pregnant pause as I waited for the inevitable and Jo and Lorraine were staring at me in anticipation. A couple of seconds later it hit. The effect of the swollen vibrator was almost agonising and I let out a huge moan as I doubled over. Jo and Lorraine just erupted in hysterical bloody laughter and gave each other a high 5. "Well I think we can safely say that works a treat!" laughed Lorraine. "I think our sissy here is ready for her orders. What do you say sissy? Are you ready for your tasks?" I was broken. This one last humiliation was the straw that broke the camel's back. I was stood in my friend's living room, wearing a PVC maids dress, bondaged, cock-caged and with her controlling a swollen butt plug vibrating in my arse. Yep I was certainly broken-in alright. I could only nod meekly to Lorraine as some tears of shame began to well-up in my eyes. "Aw don't cry sissy," said Jo. "You'll ruin my excellent make-up job!" Lorraine finally hung up the call she was making to the mobile attached to my pinny, and about 10 seconds later the vibrating thankfully stopped "Right, onto your tasks," said Lorraine. "Lady Joanna and I will retire to conservatory for the afternoon. You will immediately go and get us each a glass of wine from the fridge and bring it through to us. Then you are to set about cleaning my house. I want all rooms dusted and hoovered. All the beds stripped, and the sheets washed and hung out to dry. Fresh sheets are in the airing cupboard. Also I want all bathrooms and the kitchen fully cleaned. Everything you need is in the utility room. "Whenever your arse begins to buzz, you are to stop what you are doing and come straight to see us. Whenever you enter the room, you are to curtsy, and when we have finished giving you instructions you are to curtsy again before leaving." "Turn around," demanded Jo, and when I duely obliged she quickly freed my wrists from the cuffs. "Now, step to it!" she demanded, and gave me a shove in the back. I wasn't prepared for the movement and the tight chain between my ankles stopped me steadying myself. With depressing predictability I fell head first straight down onto the carpet. Stunned, I lay there as hysterical laughter came from behind me. "Wow what lovely frilly knickers you've got sissy, they make your arse look just adorable!" laughed Lorraine as, still chuckling, they walked off into the conservatory. "We'll start with a white wine sissy," came a shout, "nothing too heavy before lunch." Slowly I managed to get off the floor, which wasn't easy with the ankle chain on, and made my way into the kitchen. I opened a bottle of white wine and poured two glasses. Taking a deep breath I steadied myself and walked, well minced really, through the house to the conservatory. "Ah there she is. Just put the wine down over here please sissy," said Lorraine. I obliged, and once I had straightened back up I did my best effort at a curtsy and went back into the main house. Jo and Lorraine's laughter trailing behind me. Thinking I'd start upstairs, I somehow managed to make it up the staircase and set to stripping the beds; the gag, the cock-cage and that fucking inflatable dildo extra reminders of my shameful situation. Eventually I managed to change all the sheets and somehow get downstairs with the old sheets and put them in the washing machine. To be honest with you, I felt the first stirrings of enjoyment. Tottering around in the laundry room in my dress and heels was kinda what I had in mind for the day, and it was easy to forgot that I was acting the good little sissy in Lorraine's house, rather than mine. Figuring I'd do the dusting next I grabbed the feather duster and set to work. This really started fullfilling my little fantasy, but the first stirrings of a hard-on in my knickers put a stop to that. The restriction of the cock-cage bringing back everything that had happened that day and just as the feeling of utter embrassment came flooding back, I was nearly floored as the butt plus in my arse suddenly began to vibrate. 'Oh fuck, here we go again,' I thought, and tottered into the conservatory. I stopped in front of Lorraine and Jo, who were sat on a comfy sofa, and curtsied as ordered. "Hey sissy, are you doing a good job with my house?" chuckled Lorraine. I nodded submissively and tried to just stare at the floor. "Is sissy enjoying herself? Is this the day you fantasised so long for?" asked Jo. I shook my head and continued to stare at the floor. "Awww bless," said Lorraine as I stood there, shame building and only the foundation on my face stopping me going beetroot red. "Well, we didn't summon you for a chat," followed Lorraine."More wine is required and we fancy some nibbles, so pop into the kitchen and prepare something ok?" Doing as expected I nodded, curtsied and left, going into the kitchen to prepare some snacks with all semblance of my previous enjoyment again banished. After returning to deliver the wine and snacks I once again set to the dusting, followed by the hoovering. Once again I actually began to enjoy myself. Its amazing how easily you can zone things out. Unfortunately once again my enjoyment was curtailed as the beginnings of my erection met the confines of the cock cage. After a few more buzzes from my arse, I had successfully managed a few more wine top-ups and the two girls were well on their way to drunkenness. By now the plug in my arse, which I and almost got used to, was staring to cause serious discomfort. This wasn't helped by the fact I moved onto cleaning the bathrooms, which considering my bondage meant I was on my hands and knees. It was while on my hands and knees that the next episode started. I was trying clean behind the toilet when I felt an almighty #WHACK# on my arse cheeks, which made me jump out of my skin and bang my head on the loo. Looking around I saw Jo standing behind me with a big grin in her face. "Hehe couldn't resist with that cute little arse stuck up in the air" she laughed. "Don't let me interrupt you sissy, you carry in cleaning around there while I use the loo. I went back to my task, trying hard to forget I was so damned immasculated as Jo pisses right next to me. While she was doing so I felt her lean over and undo the lock holding my ball gag in place "Sit up a bit sissy," she demanded as she took the gag out of my mouth. To say I was relieved was an understatement, but this feeling only lasted for a split second..... "No point wasting paper," said Jo "you're going to lick me clean." Really, I just couldn't see how today could be any more demeaning! However, knowing the consequences I duely obliged and leant my head back so Jo could manoever over me. She lowered her nicely-trimmed fanny onto my face and I began I lick slowly, the taste of her musk and her piss filling my senses. I was surprised to find that I was somewhat enjoying the experience, as this was the kind of thing i'd fantasised about; just without the piss taste obviously! I began to lick more intently, licking her clit just how she likes it, and occasionally sticking my tongue up into her fanny. Jo started moaning intently and began to grind herself harder onto my face. This continued as she built to a crescendo, with the only downside for me being my cock struggling against the confines if its cage. Jo's moaning built and built, until she suddenly stopped. There was a brief pause and then she bucked and moaned as her orgasm took hold. She ground right down onto my face so I couldn't breathe, and her goo dribbled into my open mouth. "Well that was an unexpected pleasure," she said as her orgasm came to a end and she stopped shuddering. "Now be a good sissy and clean me up again." I obliged with a bit more licking and sucking, the scent and taste of Jo's cum strong in my mouth. Any thoughts that I may be given some slack after that service was quickly dashed as Jo once again attached the ball gag and locked it in place. "That will keep the flavour in nicely", she chuckled. "Thanks for that sissy, seems Miss Lorraine isn't the only one seeing some benefit from your girlie little desires today." "Oh and I think you missed a bit over there." She pointed as she walked out and left me kneeling on the floor. After a little while I went back to cleaning, while mulling over that last turn of events. Even with the general humiliation and cock-cage and butt plug, I couldn't help but come to the conclusion that I actually really enjoyed that particular experience. But it wasn't making up for everything else that had gone on. I still couldn't come to terms with the fact that my wife had so efficiently immasculated and sissified me and then shown me off to one of my own friends. And one I had to see at work on Monday aswell. Not to mention she had essentially pimped me out as slave labour! I wasn't even getting the sexual kicks i'd hoped for; which would at least have been some recompence. Determined just to get through the day I continued to clean and it wasn't to long before i'd finished all my chores. It would have been quicker too had I not had to keep answering the call of my butt plug. Not too sure what to do with myself, I tottered through to the conservatory where Jo and Lorraine were laughing about something or other. By now they were both pretty sozzled and I did my customary curtsy when I entered, and then just stood there waiting for instructions. "What is it sissy?" asked Jo. "Have you finished your jobs for the day?" Feeling slightly pleased with myself I nodded and tried say, "Yes Lady Joanna." It may have been seriously mumbled, but they got the drift. "Looks like she's fully broken in and knows her place," said Lorraine. "I was expecting more of a fight when we first spoke about it, but I guess you're right Jo; she really is into this." I kinda mumbled that I wasn't, but they paid no attention. "Go and prepare us a platter of nice cheese and biscuits," said Lorraine. "I think its time for more nibbles." I duly curtsied and went to the kitchen and set to work, not even registering how easily this was now coming to me. I prepared a large platter of different cheeses, biscuits, crackers and some fruit and went back to the girls. "As you have nothing else to do, I think you should just kneel down here and hold the tray. You Can be our own living table" said Lorraine. Somehow I managed to kneel without tripping or spilling the whole tray everywhere, and Lorraine and Jo set about the food and simply carried on chatting as if I wasn't there. This very odd situation went on for about 15 mins; me just sat there looking straight forward and them just going about their girlie afternoon. Eventually I was told to take tray away and bring back some more wine. Once again I did as instructed, with all the correct curtsies. Seeing out the end of the day was my sole focus at that moment but unfortunately I let myself get distracted..... While I was pouring some wine into Lorraine's glass, Jo leant forward and gave a playful pat on the arse. The surprise was enough to make me jump and to my horror I missed the glass and spilt some wine into Lorraine's lap. As I jerked back in shock, I also then managed to tip some more wine down her trouser leg and shoes. Oh shit!! "You clumsy little bitch! Look what you've done!" erupted Jo. I stepped back, feebly mumbling my apologies. But Jo launched out if her chair and forced me down into my knees. Immediately she bent me over, pulled up the ruffles of my petticoat and began to spank my arse really bloody hard. "How dare you embarrass me like that you silly little slut," she shouted, "call yourself a maid!" all the while slamming my arse #WHACK, WHACK, WHACK# Very quickly my arse cheeks were stinging and my face was flushed with the embarrassment. And pain. Occassionally she would catch the bottom of the butt plug, which was fucking painful. After a few more good whacks Jo stopped and, ordering me to stay on my knees with my face on the floor, left the room with Lorraine. I guess to get cleaned up. My arse was throbbing, but I kept myself firmly in the position I was left in. A few minutes later they came back in. "While I was helping Miss Lorraine dry off, we had a little chat about your punishment. And we've decided that not only do you need to help clean up, but that Miss Lorraine gets to exact the extra punishment. So firstly, you're to come over here and lick Miss Lorraine's shoes clean," Jo said as they sat back on the sofa. "And you'd better make a bloody good job of it, I want them sparkling." With that she unlocked the ball gag and removed it from my mouth. Not really knowing what else to do, and not really having the fight to complain, I began to clean Lorraine's shoes with my tongue. Let's face it, the humiliation wasn't really going to get any worse, so I just did the best I could and tried hard not to think about what I was licking. A really nasty job. "Open up sissy" said Lorraine as she moved her foot and pushed the heel if her shoe into my mouth. "Do it sexy bitch and don't hold the tongue". With that, she began to essentially fuck my painted lips with her heel, all the while smiling and laughing. I did my best to also lick the heel as she moved it in and out. In all honesty, looking upwards at a laughing lady as she heel-fucked my mouth was kinda interesting in a very wrong way. After a few minutes Lorraine seemed to lose interest in the shoe cleaning and the heel job and she made me stop. "Right, turn around you. My turn to dish out your punishment," said Lorraine. "and lift your dress." 'Oh no,' I thought. With that sinking feeling, I shuffled around and lifted the bottom of my dress. "Head down," said Lorraine, and I duly complied. "Now I'm going to spank you and you're going to count every single one of them and thank me. I know how many hits you're getting for being so useless, and you don't. And if you forget to count and thank me at any time, I'll start again from the beginning." Now this was really not good. She was my mate, it was bad enough having to generally do all this stuff in front of her, the clothes, the humiliations, everything. But for her to actually be doing the spanking now was just too much. But what the hell could I do? I just had to take it. WHACK 'One, thank you Miss Lorraine' I said WHACK 'Two, thank you Miss Lorraine' WHACK 'Three, thank you Miss Lorraine' ....and so it went on. Lorraine seemed to be loving it. Laughing away, sometimes double-hitting on both arse cheeks, even pulling back and twanging my suspenders. All the time I was counting and thanking her. All the time just wondering what had happened to my life. The pain and the shame were becoming unbearable, and tears began to run down my face. I think more from the shame than the pain, as I was also aware that had Jo not locked my cock away I might actually have been enjoying this. That made one really fucked-up positive feedback loop. Fifty. Fifty bloody spanks I took from Lorraine. My arse was so damned sore and battered that I didn't want to move afterwards. Once they made me stand back up though, the discomfort really kicked in as the PVC knickers and the swishy petticoat rubbed against my sore skin. "Well that's worn me out," chirped Lorraine, chuckling. "Poor little sissy doesn't look like she enjoyed that," said Jo with a big grin. "I actually think we should be going soon, but before you drive me home, I think Miss Lorraine should truely understand the depth of your shame and enslavement to us today" she said as she moved over to me. "lift up your dress to show off your knickers". I lifted my dress to another 'aaah how cute' from Lorraine, but suddenly Jo grabbed my knickers and pulled them down to my knees. What the hell?! I was so mortified I actually just froze in place. I stared at Lorraine, one of my closest friends as she took in the sight of my cock locked in this small, clear cage. This was one of my closest friends for heaven's sake. There was a quiet pause, before Lorraine simply erupted in hysterics in front of me while pointing at my caged cock. "Wow she really couldn't enjoy herself could she?!" she exclaimed with an ominous twinkle in her eye. "Joanna, pass me the phone." Oh. Fuck. A few seconds later, there I was, stood in front of Lorraine, in my sissy dress and displaying my shame, while a massive plug in my arse buzzed away. A huge moan escaped my lips as I tried not to double over, which just made Lorraine laugh harder and Jo smile from ear to ear. Well that was it. They really had capped the night hadn't they? "Right you, go get my coat and come back so we can get moving. Oh and leave your knickers where they are," said Jo. Desperate to just get out of there, I hobbled out of the room with my knickers around my knees and got Jo's coat and bag. When I returned, they had their laughter back under control and where discussing how much fun they had. When I was again stood in front of them Jo told me I could finally pull my knickers up. Finally. "Well I think that was a fun day don't you think Miss Lorraine?" said Jo. "Yes Lady Joanna, indeed it was. Bloody hysterical in fact!" replied Lorraine. "And what about you Sissy Lisa? Have you enjoyed your day in our service?" I couldn't reply, I just stared at the floor. "Whether you did or didn't, this day was all about you honey" said Jo. "I've seen the fantasy stories you read and when I told Lorraine we decided to put it to the test and see just how much fun we could have. So whether you did or didn't, you brought it on yourself. Now, as you've been such a good little sissy today I'm going to reward you when we get home." "Ooh really? What's her reward?" enquired Lorraine. "I've brought a huge new strap-on and when we get home I'm going to fuck her so hard she won't be walking properly for a week!" (Now that's more like it!) ....."Hmmm wouldn't mind seeing that one day," said Lorraine. "Well maybe next time!" said Jo as she looked straight at my horrified face. "Right. Take me home Sissy. And don't forget to thank Miss Lorraine for her hospitality" said Jo as she walked out to the car. Getting the hint, i turned to Lorraine and did the best curtsy I could manage. "Thank you for having me over Miss Lorraine, it was a pleasure being your maid for the day," I said meekly. "Its been a real pleasure Sissy, and a real eye-opener. I'd love to have you over again. Now you best run along and get Lady Joanna home, else you may not get the arse fucking she's got planned!" With that I turned and left, receiving a hard spank on the arse from Lorraine that nearly made me trip over as I tottered over to the car (Jo hadn't taken the ankle chain off) Driving home I had a lot to think over, not least of which was the fear a neighbour would see me when I got out of the car. But had I enjoyed the day? I don't see how i could. My arse was sore and I had been humiliated, abused and emasculated in front of one of my best friends. Its all well and good having fantasies, but reality is very different. Plus I was concerned that a monster had been created as Jo seemed too good at all that. And I was also a tad worried about the new strap-on she mentioned! When it comes time to look back on the day, I guess I may think it was enjoyable, but one thing was for sure........ I really wasn't looking forward to work on Monday.

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Maid For The Family Part 3

Maid for the Family - Part 3 ? by: Sissy Sally-Anne Following on from Part 2... After pleasing Elizabeth, she took me upstairs to her bed. I could not believe how tired I was. My energy was gone completely. She asked me to strip and then dressed me in a long white silk nightdress. I slipped into bed and curled up under the quilt. "Sleep well, Jason," said Elizabeth, as she turned out the light. "We still have so much to do." Quietly, she left the room and when...

2 years ago
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Maid In Heaven

Hitting Puberty Welcoming all Readers from Indian Sex Stories dot net. I am new here as an author but been an avid reader of the stories many of you have contributed, thought of taking a shot at writing myself. What I am about to write, is a slow paced story, an indulgence and my flair with the world of Lust. As you have read “About me” in my profile, and just in case you haven’t, to cut the story short, I am today a 28 years old man, and my life till today has been full of sex adventures which...

3 years ago
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Maid Service

My husband and I enjoy travel and like to get away a few times a year. Being cold in the North we like to head south in January or February. This year we went to Florida to see the sights and do the regular tour that the tourists do. We booked into the Hilton at Walt Disney World and got busy seeing and doing all the regular stuff. On the fourth day we were there, my husband had booked a round of golf, that being his passion. My passion on the other hand is shopping and I was quite delighted to...

3 years ago
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Maid for a Day

MAID FOR A DAY By Tammy Richards I got my introduction to women's clothing courtesy of the Ohio State ? Michigan football game. You see, I'm an Ohio State alum and my wife Danielle graduated from the University of Michigan. Needless to say there's a lot of good-natured kidding back and forth between us, particularly during football season. A few years ago, we decided to have several friends from the neighborhood over for a party on the day of the big game. It turned out to be one...

4 years ago
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Maid to Please

Maid to Please I was thirty years old happily married and yet frustrated as I had a desire to cross dress on a more permanent basis but my day to day life tended to prevent it. I joined a web based dating service that specialised in the unusual and having shared my profile and my desire to become feminised in a controlled environment it happened. You see I am practical in terms of all manner of DIY and am a handy cook and good at housework. It occurred to me that a lesbian...

3 years ago
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Maid of Honor

Maid of Honor Janet L. Stickney [email protected] In many of the stories I had read on the Internet, being the bride in a wedding was a constant theme, a good one to be sure, but still, just fiction, and I very seriously doubted that any guy could actually pull it off with any realism; maybe, but probably not. I liked to dress up, and did so when ever I had the chance, starting from a very young age. I thought that I was moderately good at it, not perfect to be sure, but in my...

2 years ago
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Maid of Honor

Maid of Honor Janet L. Stickney [email protected] In many of the stories I had read on the Internet, being the bride in a wedding was a constant theme, a good one to be sure, but still, just fiction, and I very seriously doubted that any guy could actually pull it off with any realism; maybe, but probably not. I liked to dress up, and did so when ever I had the chance, starting from a very young age. I thought that I was moderately good at it, not perfect to be sure, but in my...

2 years ago
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Maid In Oaxaca Mexico 1

MAID IN OAXACA - MEXICO By Monica Graz PROLOGUE Patricia Martinez Torres is a pretty and highly intelligent Mexican girl in her mid twenties living in New York. Her father Diego Martinez Torres is a high-ranking diplomat serving at the UN Mexican delegation. Her mother Alicia Martinez Torres is 'old money'. She is the sole inheritor of vast pieces of land and properties in the southern state of Oaxaca at the vicinity of the town of Juchitan. In the district of Juchitan is the...

3 years ago
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Maid service

Hello all ISS readers! I am back again with a hot sizzling story. As u knows me I’m Abhishek Singh 18 male living in Delhi near mother dairy of pandav nagar. I will hope that u will enjoy the story. Mail me any comments, queries or anything on or My husband and I enjoy travel and like to get away a few times a year. Being cold in the North we like to head south in January or February. This year we went to Florida to see the sights and do the regular tour that the tourists do. We booked into...

Lesbian
4 years ago
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Maid to Please Chapter Three

This story contains material of a sexual nature. It has explicit descriptions of sex, bondage and non-consensual sex. If you are at all offended by this kind of story or are under age, DO NOT READ ANY FURTHER! Any characters in this story are the property of Jayne Dell. This story is written for the sole purpose of entertainment and is not written for profit and cannot be transmitted, reproduced or otherwise traded for profit. If you have any comments, want to get in touch, please...

4 years ago
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Maid to Serve

For the second consecutive growing season, the monsoons had failed to arrive over the Indian rice paddies. Without the heavy annual rainfall, the Nalwali family had been unable to produce their customarily bountiful crop of top quality rice. It was the proceeds from the rice crop that allowed the Nalwali family to not only survive but to provide the resources to keep the land they farmed. For generations, the Nalwali family had produced some of the most successful rice crops in their region....

Interracial
3 years ago
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Maid Machiavelli

MAID MACHIAVELLI By Bea The young man woke gradually, feeling the soft hands work their way under the covers then undo his pajama jacket buttons. He then felt the softness of the fingers as they started caressing his tummy, breasts and armpits. He heard the whispered words vaguely, something about how smooth he'd kept himself. He came awake completely when his hair band was slackened and removed. Knew that his hair was being softly fanned out about...

2 years ago
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Maid Management

Philip was running out of time, he knew that he needed to be dressed and ready to greet his wife, Vanessa at 6pm, it was 5-15 and he was still 10 minutes from home. Finally his car drew into the drive and he rushed into their large house and up to the bathroom, shedding his clothes as he went. He shaved his face and checked his body was hairless. Moving quickly down the hall to the bedroom, he was surprised to find a lock on the door so that he couldn't get in, but then he remembered that...

3 years ago
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Maid And I Turn Into Sex Maniacs

Hi this is my first post in this website. I have never written before about my maid who ended up turning me into a sex maniac. I hope everybody enjoys reading this, specially the ladies. It all started when I was 18 and I had completed my studies in Delhi for 12th and had returned home to spend a few years relaxing and helping dad. The day I arrived I saw our maid Roopa and was left speechless. She looked to be in her forties but did not look old. In fact there was something alive in her which...

3 years ago
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Maid to be his

Maid to be his by Caitlyn Masked Android technology in the mid-21st century revolutionized almost all industries. At first the only thing limiting their use was the limit of artificial intelligence. Simple but dangerous manufacturing was regulated to the droids. Repetitive tasks were perfect for them. Next came putting androids in the place of non-humanoid robots because having a 'person' to look at was more comforting. Self-driving cars never picked up even though there were...

3 years ago
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Maid For The Family Album

Copyright,[email protected] Before you start this story a notice to the readers, Iam clearing out my video collection and they are classics, well you knowmy taste so why not e-mail me for a list, they are cheap, good and theselection play, U/K & USA Another story by Pagan Maid for the family album. It all started as a great idea, Trudy and Bob, Helen and Terryhad found their dream house. It was Terry who said, this has great potential,big and already divided, two beautiful big...

2 years ago
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Maid For Changes

Part OneDiane sat with her foursome drinking in the bar. Their golf round was cancelled as a downpour slammed into the clubhouse windows. The waiter came by, "Anyone ready for another?" Diane looked at her watch. It was four and she had already had three drinks. She looked over at her friend Julia."What do you think?""I have to meet Carl. I'm sure he's home early because of the rain and it's date night.""Oh." Diane knew what 'date night' meant to Julia. Her and Carl were going to fuck. Diane...

3 years ago
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Maid Service Requsted

Jennifer was so horny and she couldn't do anything about it. Alex had asked Jennifer to dress up in her tight little French Maid's costume. Not that Jennifer minded. She loved pleasing her lover to the extent that she would do anything asked of her. She had slowly dressed herself in the hotel room while Alex busied in the bathroom for the corporate meeting that would take most of the morning. Looking at herself in the mirror over the dresser, she admired the way the little black and white...

2 years ago
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Maid for the Job Chapter Eleven

Maid for the Job Chapter Eleven I woke with a start as the memories of the previous night's activities came flooding back, the pain in my used hole a further reminder of the assault that I had experienced. But had it been assault?! I could have tried to fight him off, I could have revealed Mrs Smith's plan, but I didn't, I allowed Mr Smith to use me as a sexual plaything just as his wife had done previously. Why hadn't I fought him off? Fear of exposure? Fear of further cruelty? But...

3 years ago
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Maid to Serve

For the second consecutive growing season, the monsoons had failed to arrive over the Indian rice paddies. Without the heavy annual rainfall, the Nalwali family had been unable to produce their customarily bountiful crop of top quality rice. It was the proceeds from the rice crop that allowed the Nalwali family to not only survive but to provide the resources to keep the land they farmed and provide for the education of their children. For generations, the Nalwali family had produced some of...

3 years ago
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Maid In Heaven

Hi guys, this is schmuk, coming once again to you after a really long time. After my initial 5 stories in ISS (How i finally attained my maid part 1 & 2, maid to taste, cook became my meal, deepa my sexual masterpiece), i got a lot of requests to write more. But i am a firm believer that the basis of my stories should be reality and not fiction. Thats why i have had nothing to write about for the last 18 odd months. All my sexperiences had come from steamy affairs with dusky maids during my...

2 years ago
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Maid in Heaven

I wrote this story a couple of years ago, and posted it on nifty.org. I have decided to post all my stories here, and this is the only one (and first) story I wrote outside fictionmania. Hope you like it! Chapter 1 I stood outside the bus with my friend Alex, and looked up at the hotel below the Swiss Alps. It was beautiful view. You see, my parents had arranged for me to work at my aunt's hotel this summer as a substitute gardener. My parents thought that it would do me good doing...

1 year ago
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Maid8217s Family Shares My Cock 8211 Part 1

This sex story is about my dominating maid Geeta. She is a 50 year old woman. She has a dark complexion, hanging boobs and a chubby body. I am a 22 year old boy who has recently got a job. Prior to my encounter with my maid, I have had sex with my Aunt Sona. It was a Thursday evening and my mom got a call from Geeta. After speaking with her for some time, my mom handed me some cash and asked me to go to Sanjay Hospital and give the money to our maid Geeta. She asked me to stay with her. Without...

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