The Proposition free porn video

The proposition. "I have a vacancy you might be interested in," she murmured. "Oh really," I responded not paying too much attention as I was trying to fix her laptop. "For a sissy maid......my maid.....if you want it?" she quipped. Now she had my attention as my eyes popped open with shock. I watched a smile curve her lips as my heart skipped a beat. I was shocked, stunned.....excited, this was a dream come true! But why was I so shocked. Well the request had come from a work colleague! Lana was not a close work colleague, she was an out worker only coming in to company occasionally. Usually as in this instance when she needed her laptop repaired. "I'll let you think about it....." she quipped as she got up and left, leaving me shocked and stunned. We were friends on Fetlife so she of course knew all my kinky fetishes, especially my desire to be a sissy maid, but I did not think she was interested in me. She returned a short time later as I had just finished sorting out her laptop. In the little time she had given me I had agonised over my answer. I so much wanted to do this, that is was more than a wish, it was a hunger! The one thing that held me back was that I was a married man, happily but for our sex life! I blushed when I told her I had fixed her laptop; she took it and waited patiently. "I....I...thank you for the offer, but I'm married.....I can't," I stammered. "But we both know you WANT to do it.....I have seen your Fetlife profile....." She emphasised the "want" and she was of course right! "You have until next Monday..." she turned and left and I watched in awe the sway of her bottom. Lana's curvy in all the right places and although I had ogled her body on occasions I had never done anything about it, I am a married. This being Friday I knew it would mean I would be stewing over the question all weekend which I did finally coming to an answer. She called me at work Monday morning, I took the call on my head set so that I could hide in the store room to talk to her. "Hello Davina...." I blushed at the use of my sissy name. "Well do you have an answer? I could hear the mirth in her voice. "Yes.....yes....I would like to fill the vacancy," I stammered, relieved to be saying it. "So ask properly," she demanded. Relieved that I had taken the call on my head set I answered. "Please may I take the position of your sissy maid," I replied meekly. "mmmmm....now go and sit back at your desk and ask me again," she laughed. I gasped realising she must have known from my confident answer what I was doing. Nervously I returned to my desk looking around as I did. Fortunately there were very few people in at that time of day. "Please may I take the position of your sissy maid," I replied once again, even meeker than before. "I should make you shout your answer but I won't. Remember I know a lot about you so let this be a lesson. Yes you can be my sissy maid...I will see you tomorrow morning eight sharp," the phone went dead. Tomorrow I agonised, no time to prepare myself then! Shortly after a text arrived detailing her address, I immediately booked a taxi for the following morning. That evening I secretly prepared a bag for the following day. In it I placed my pink shiny high heels, white holdup stockings, full pink frilly knickers, pink satin corset, pink curly wig and my pink PVC maids dress.....well she did say sissy maid! To lift the skirt I packed my froth of petticoats. I also included makeup, lace gloves, maid's hat and apron. Since I have quite a hairy body I jumped into the shower late at night and shaved until I was smooth as a baby. My wife would notice of course but she would assume I had simply had a dress up session. She tolerated this.....just, but did not get involved. Nervously I waited for the taxi the next day, my wife sets off for work before me so she would simply assume I had gone to work and know nothing of my secret liaison. Lana lived on the posh side of town but then her job paid well. I nervously knocked at the door and waited. Lana opened the door with a smile and ushered me inside pointing out that I was to change in the upstairs spare bedroom. "You have thirty minutes then I want you downstairs in the living room standing at attention for inspection," she commanded. "Yes Mistress," I answered hurrying upstairs. I quickly unpacked my things knowing thirty minutes was going to be a push. The first item to go on was the corset, I gasped at its cool silken embrace. I breathed in pulling the laces tight as I did, then repeated the same process three more times until I could hardly breathe. The tight silken embrace had my pulse racing and my cock fit to burst. It had been so long since I had dressed and I thrilled at the feeling. Sometimes I pitied women, to have this feeling every day so that it became mundane. Oh I know a corset was not your ever day clothing but the feeling of soft stockings on freshly shaved legs....delicious, and as for the soft caress of knickers my cock throbbed in anticipation. To cure this I pulled on the pink frilly knickers revelling in their soft touch against my angry erection, trying very hard not to play with myself. I slipped the stockings up my legs and adjusted them so than they were both at the same height and perfectly straight. Holdup stocking were easy to put on unlike stockings and suspenders but I knew I would constantly have to adjust them to keep them perfect. I took the PVC maids dress and slipped into it, now this was cold to the touch making me shiver, but I knew I would soon be warm when I got to work on the chores. I shimmed to get it into place and having zipped it up to the high neck fastened the three straps across the front wishing I had padlocks to lock it in place so that I would be at the mercy of whoever held the keys. Under the skirt I fitted the petticoats so that the hem lifted almost horizontally and my pink knickers were on display. I slipped into the pink six inch heels and tottered around the room getting used to the feel. I had to remember to place one foot across the other to give myself that sexy swish of the hips. Satisfied I returned to the dressing table and put on some makeup. Only light foundation, pale pink lipstick and pale purple eye shadow, nothing to slutty. I slipped the pink wig on smiling at my reflection as the pink bangs framed my now slightly more feminine features. Looking at my watch before I removed it I realised I only had five minutes left. I donned my maids cap and lace gloves then tied the white apron around my waist noticing to my consternation that it was creased from being in the bag. I smoothed it as best I could then taking one last look in the mirror.....adjusted a stocking then minced downstairs to the living room. Lana was sitting at a desk in the corner of the room working on her laptop. Not knowing quite what to do I moved to the centre of the room and stood eyes down. If she had noticed me she made no indication and so I waited.....I must say impatiently for her to inspect me. Whilst I waited I took the chance to ogle her heavenly figure. She had on glossy black stiletto shoes, these made her shapely legs more enticing, legs that were encased in sheer black stockings. I knew they were stockings because as she was seated demurely at the computer her black skin tight pencil skirt had ridden up her legs revealing red and black laced suspender straps. She was wearing a brilliantly white blouse that was unbuttoned low enough to give a tantalizing view of her ample cleavage. Rather shamefully my gaze lingered there. Finally she seemed to finish her work on the computer and then she stood smiling wickedly which made me think she knew exactly what she was doing. "So let's see how well you can present yourself," she commented. "Well one stocking is slightly higher than the other," she tutted. "Your apron is creased." I realised this was not going to be easy she was going to inspect every detail. She moved behind me. "Apron tails different lengths.....oh dear not doing very well are we Davina?" Despite admonishing me I could hear the mirth in her voice....and perhaps passion! My cock throbbed at the thought of exciting her and I wondered if it was the power she had over me or the fact she was no doubt going to punish me. This thought really got my pulse racing and my cock throbbing! She moved back round to the front. "Lift your dress and petticoats," she ordered. "Mmmm, getting hard in my presence is not allowed and also leaving a wet spot on your knickers!" I blushed bright red and simpered. "Sorry Mistress" "You will be.......lower your knickers," she retorted. She left the room leaving me in this humiliating stance and I knew she had done it on purpose further showing her command over me. She returned with a bag of ice cubes and a small pink device which I instantly recognised as a chastity device. "Hold this over your clit," she remarked with a grin. I blushed at the humiliating term for my cock and my cock throbbed harder however it was soon to shrivel as I placed the bag of ice cubes over it, once it had shrunk Mistress knelt before me and fitted the chastity device. "Good thing I bought the small one, it is a perfect fit...." she jibed. I of course blushed profusely. "Now the device will stay on when you are in my presence...no more lewd, though somewhat small erections..." she quipped turning the screw of humiliation. "It will also stay on as long as possible, I will provide you with a key but you will only remove it to have sex with your wife.....which it seems is not often...and for this reason only....understand!" "Yes Mistress," I replied meekly. I shivered at the thought of what this meant, yes I had tried chastity before but it had not lasted long due to my lack of willpower, how would I last when I had such a high sex drive I mused. Well since it was an order from Mistress I knew I would have to obey, but I did not relish the prospect. Since my wife and I had very little sex I knew I was now at the whim of my Mistress for release. "Bend over the table," she ordered. I moved to the heavy table that sat in front of the window and realised that as I was being punished I would be staring out into suburbia, it made me smile to think that hidden behind net curtains I was about to get my bottom spanked. The instrument of my punishment was laid on the table. It was a wooded paddle with the word "Spank," picked out in spiked studs. "Now Davina, please list the faults that require me to punish you," she commanded. "I....I....." for a moment my mind went blank then I blurted out. "Stockings not straight Mistress, my apron is creased Mistress.....apron ties uneven Mistress, having a hard clit......wetting my knickers......." I ran out of ideas. "That appears to be correct Davina...so that is five strokes and one for good measure making a total of six" "Yes Mistress........thank you Mistress. Mistress picked up the paddle and chuckled to herself as I shivered at what was to come! "Don't worry Davina as it is your first punishment from me I will be using the none studded side" I sighed with relief and then squealed in pain as. SWISH........SLAP! The first stroke landed on my unprepared bottom, I was so shocked I almost forgot to thank her. "One.......Thank you Mistress...please may I have another," I simpered. By the third stroke tears were rolling down my cheeks because although she looked petite the strokes were quite heavy. On the sixth stroke I simply thanked her and awaited further commands. "Okay sissy time to get some chores done, it can't be all fun and games...." she quipped. "Upstairs, start with the main bedroom...I want the upstairs done by lunchtime," she ordered. I realised this was my command to go so I pulled up my panties did a curtsey that made her smile then headed upstairs. The bedroom was a mess clothes and shoes everywhere and the bed unmade. I started with making the bed, putting on fresh bedding found in a cupboard on the landing. I then piled all the clothes on the bed and then hung the clean items back in the wardrobe, leaving a pile for washing. These I carried downstairs and after sorting out the colours put a wash on. The wardrobe I realised had a rack for shoes but it was not being used so I sorted them into pairs and started filling the rack, getting high on the scent of her heavenly feet. Surreptitiously I sniffed one of the shoes my cock throbbing painfully in its prison reminding me it was not a good idea but still I did. I noticed that some of her shoes were not polished so I headed downstairs to find some shoe polish. I found it and hurried back upstairs realising this would mean an excuse to intimately handle her footwear. By the time I has cleaned and placed them all on the rack the musky smell of her feet was ingrained in my senses and my poor clit was throbbing painfully....to be honest I was starting to enjoy the pain to my shame! I quickly dusted and vacuumed the bedroom, then headed to the bathroom knowing I was pressed for time. I had just finished cleaning the toilet when I heard her footsteps on the stairs. She entered the bathroom so I meekly knelt in the corner of the room head bowed. I heard her ruck up her skirt, then saw her panties drift into view as she sat on the toilet I had just cleaned. The bathroom was not very big so she was quite close to me, even with my head bowed I could see midway up her calves, I could in fact see my reflection in her glossy black stilettos . I heard the tinkle of pee and then she stood to wipe herself. "You may look," I could hear the smile. I looked up as she slipped her semi softness into her panties, I licked my lips subconsciously and she chuckled. "You want to taste me don't you Davina," her voice was quite husky and I guess she was turned on as much as me. "Yes Mistress," I gasped. "Kiss me," she ordered breathlessly. I leant across the gap between us and planted a devoted kiss on her panty covered bulge, I felt it twitch under my lips and I heard her sigh. As I kissed her I breathed in her musky, heavenly scent...the scent of arousal and I shuddered my clit fit to bursting! Almost reluctantly it seemed she pushed me away. "Get on with your work sissy..no time to dawdle!" she admonished pushing down her skirt. I finished the rest of the work upstairs in a haze of erotic frustration, that one fleeting touch had set my arousal blazing, I truly want to worship my Mistress. Finished I presented myself before Mistress Lana. "The upstairs chores are complete Mistress," I simpered. Without looking up from the computer she commanded. "There are items in the fridge to make me a salad for lunch and I would like a glass of wine." "Yes Mistress," I curtseyed and headed into the Kitchen. The salad was quick and easy to make and after finding, mats and cutlery I laid the table that just that morning I had been spanked over. As I was laying the table I noticed Mistress had gone upstairs, no doubt to check on my work. I had just placed her lunch and wine on the table when she returned. "Well there are quite a few mistakes but I can only say that was maybe because of the limited time..." I sighed thinking I had got away with not getting another spanking....I was wrong. "Still you should have made a better effort even in the limited time you had....... I was however impressed with my shoes, shiny and clean...... no doubt you sniffed them whilst you were doing it," she smirked. My very red blush was all she needed for an answer on that one, she picked up her wine and took a sip. "Well since the table is unavailable, bend over and touch your toes!" she commanded. Once again I was subjected to six strokes although this time they seemed even harder but that may have been the fact my bottom was still tender from the earlier spanking. Finished she commanded. "Clear away the lunch things and clean the Kitchen," she ordered. As I was clearing the table she returned to her computer. I then spent the next hour cleaning the Kitchen to ensure it was spotless in the hope of both pleasing Mistress and saving myself another spanking....... I was not sure my bottom could take it. When I had finished I returned to find Mistress sitting in a leather chair obviously awaiting my return. She pointed to the floor before her. "Kneel," she commanded. My heart skipped a beat as I realised I was finally going to be able to worship her. A wicked grin creased her lips as she watched me scamper into place, but I could see by the lustful look in her eyes that she was just as ready as I was. To further frustrate me she ordered. "Remove my shoes and massage my feet." I moved closer and slipped of one and then the other shoe, she sighed and wiggled her toes, I sighed as well as I inhaled the subtle musky scent. "I know heels make my legs look good but they are a pain to wear over a long period," she murmured. I picked up her left foot and began to massage it and tempted beyond measure was soon kissing and worshipping it with my lips as I continued the massage. I felt her unfasten the stocking and then it fluttered down to pool around her ankle. I removed it and carefully set it aside. Now that my lips and tongue were tasting soft skin, the taste filled my mouth and senses and my cock throbbed painfully. After a short while I took her right foot and did the same and she helped by unfastening the stocking, soon however she grew tired of my ministrations and ordered. "Up Davina, I need those eager kisses and tongue between my legs," she growled in a husky voice. I of course eagerly obliged, sliding my head between her slightly parted legs. She did not move them very far apart so my Head was squeezed tightly by her soft thighs, I realised this was because of the tightness of the pencil skirt. I was glad however of this because it meant that in such close confines the aroma of her arousal was even more pungent! I breathed in deeply drinking her in and groaned with pleasure, then delicately I kissed the rock hard bulge, she in turn groaned with pleasure. I suppose considering what I have just described I should explain. You see Lana until a couple of years ago had been Peter now she is a transgender female and happy with this situation. So now you might see why the act of becoming her sissy maid had even more meaning for me. As a submissive wearing women's clothes, in my case a maids uniform and also taking a submissive female maids role is the ultimate turn on for me. And to have a Mistress who is a dominant male transitioning to female as a Mistress....my Mistress, well that is just heaven! A dream come true so to speak! She must have noticed the pause as I mused about my current situation revelling in the joy of it because she squeezed my head tighter. Carefully I kissed my way up her silk encase cock and as I reached the bulge that was the bulbous head my tongue detected the wet spot her arousal had created. Eagerly my tongue licked out moistening the area further and causing her to yelp with pleasure, at the same time as a new taste of her filled my senses. My ministrations on her silk encased cock head seemed to push her over the edge because she began to wriggle her skirt up. "Take off my panties!" she husked urgently. I quickly found the waistband and was soon pulling them off. Freed of both panties and skirt she opened her legs wider and I was granted the sight of her cock. It was about eight inches long and quite fat, my mouth watered at the sight of it. Without bidding I returned to worshiping her taking her hairless balls in my mouth, once again she gasped and I realised she was extremely turned on, as was I. It was at this point I realised I was about to suck my first cock and I shivered at the prospect! Once again I kissed my way up her cock this time having the pleasure of tasting her as I did, the taste was divine. Once again at the bulbous knob I noticed a tear of pre-cum, looking up into her eyes I stuck out my tongue and lasciviously tasted it. Her eyes rolled in her head and she groaned long and loud her head falling back. I smiled to myself knowing that although she was the Mistress it was I who was in control now. I also retained enough sense to know that as soon as I took her into my mouth she would explode. So instead of sucking her, my lips moved down the shaft lubricating it with my saliva as I went. Then taking hold of the shaft I began to stroke. For a brief moment I wondered what it was going to be like to taste another's spunk, I had tasted my own of course but I knew this was going to be a whole new experience. So with a sigh of pleasure from me and a gasp of joy from her I took her in my wet eager mouth. The effect of course was instant, her cock began to swell in my mouth and I knew she was coming.....that and her keening scream! The first pulse of spunk hit the top of my mouth and then gushed down my throat, despite knowing it was going to happen I almost choked barely swallowing in time to take the first mouth full. As I did the taste and texture filled my senses making my cock throb in its prison! It was salty...metallic and not unpleasant, the sticky texture meant that it seemed to coat my mouth and throat lingering deliciously. I took this in as a second load filled my mouth which I quickly swallowed, a third and fourth load followed. I was surprised at just how much spunk she produced against what I usually shot, mine was definitely pathetic in comparison! I blushed as I made this observation and also at the fact she was watching me avidly drink down her juices, a wicked grin creased her lips. "I definitely needed that," she winked. I licked my lips and the last of her juices from the bulbous head of her cock noticing as I did that she was still hard! I was careful not to lick too hard knowing how sensitive her cock head would be at the moment. "Well now that I have marked my property....." She paused watching my blush deepen as it sunk in as to exactly what she meant. It seemed I was now hers to do with as she wished. I shivered at the thought and my cock throbbed painfully. "Time to turn you into the girly sissy you were meant to be..." she snickered. "Yes please Mistress," I simpered. "Off you go upstairs, remove the dress and then present yourself in the bedroom how you think best!" She winked. I hurried upstairs as she went to the Kitchen to refresh her drink. Removing the apron, gloves and hat I then shimmed out of the dress. So in heels stockings and corset I made my way nervously to her bedroom. For a second I stood frozen staring at the bed, then I had it. I moved to the bed and placing my hands on it lowered my head so that my plump bottom was seductively on display. I would have liked to have said pert bottom but at my age most things are becoming more rounded. I heard her footsteps on the stairs and shivered in anticipation, it seemed I was going to experience yet another of my fantasies, to get my sissy pussy fucked! My cock was dripping with excitement as I wondered if I would be able to come just by getting fucked, a sissygasm as it's called. Oh I did hope so with all my heart! She entered the room and as I looked coyly over my shoulder noticed she had removed her skirt and blouse. Her curvy figure was laced tightly into a black and red silken corset. It was pulled in tight just like mine giving her that shapely hour glass figure I love. Her breasts presented by the half cups of the corset looked succulent and I licked my lips at the thought of being smothered by them. She grinned at me and remarked. "I might have known you would have picked this pose you hussy," she chuckled. She moved quickly to me and removed my knickers exposing my tender red bum which she delicately caressed making me groan. "Are you ready to be fucked," she growled. "Oh yes please Mistress," I pretty much begged. She moved to the bedside cabinet and then returned behind me, seconds later I felt the cold gel drip onto my throbbing sissy pussy. I felt her finger play around the edge making me mewl to feel it inside and then slowly it did, making me sigh. "Oh what a tight little pussy you have Davina," she crooned. "Yes Mistress," I sighed. It was so strange to feel something warm and living inside my pussy, I regularly used butt plugs and really enjoyed anal play but this was a whole new level. I realised that I could not wait to feel her cock inside me, she noticed my impatience. "Patience sissy, I have to get you warmed up first, otherwise it will be painful," she chided. "Yes Mistress," I gasped as a second finger joined the first. Two became three, and then four and I groaned as she pushed them in knuckle deep and then slowly began to fuck me. It felt very pleasurable and I started to think that maybe, just maybe I was going to get to cum! Slowly she slipped her fingers out and there was a pause as she wiped her fingers, then I felt the tip of her hot hard cock against my pussy lips. Then with a quick push the bulbous head was inside. Because I was wet and warm there was very little pain as she slipped inside and we both groaned in unison. Then inch after inch she slipped inside until her balls nudged mine! As I grew accustomed to her length and width I felt the need for her to fuck me but she remained still much to my frustration. One of the things l really love when filled with my favourite butt plug was to hump up and down on it, I desperately needed that feeling now! So I started to wiggle my bottom eliciting a chuckle from her. "What do you want my sissy hussy!" she quipped, I could hear the amusement in her voice. "Please Mistress, I want you to fuck me," I pleaded. "You beg so sweetly," she giggled. I blushed at how desperately I needed to be fucked, had wanted this desperately for such a long time! She slowly pulled out and then slid straight back in, we both again moaned with pleasure. So ever so slowly she increased the tempo and although I loved the feeling of being fucked by her I realised that I was not going to cum. Quite suddenly she slowed to a stop and I found myself humping against her too keep the feeling. "On your back hussy..." she commanded. "I want to look into your eyes as I fill you with my juices," she crooned. I could tell she was very close to climax and that made me happy. Even though I knew I would not get to cum, the act of giving someone else pleasure was pleasure enough for me! I rolled onto my back and grinning she placed her cock at my eager waiting pussy. Then looking me in the eyes she slipped it in to the hilt and I groaned with pleasure. However at this angle her cock raked my prostate and I realised there was the slightest hope of my sissygasm, my eyes popped open in surprise causing her to chuckle. "I guess we found your G spot...." she chuckled. "I do love this...." she said looking down between our legs. I followed her gaze and watched her sex slick cock slide in and out of my pussy. It was such a marked difference to my tiny pink locked up clit and then it hit me....that is what she meant. I blushed deep red at the humiliating remark and my tiny clit twitched. "See what I mean..." she snickered. "Here I am fucking my sissies pussy while her tiny clit is locked away and helpless....delicious," she laughed. I must admit I loved to watched videos with alpha males fucking sissies in chastity it was one of my favourite fantasies, and now it was happening to me. I groaned with joy as she upped the tempo obviously turned on by her observations. I wished with all my heart that she would fuck me long and hard but I knew she was close, I on the other hand was not quite there. I felt the change in tempo and she made three long thrust groaning loudly as she did, filling me with more of her juices. Satiated she slowed to a stop but remained inside me. She reached down for something on the floor and picking it up brandished it before me. It was a bright pink butt plug, about five inches long and two at its widest. "Something to remember me by," she winked. She pulled back and her cock popped from my well fucked pussy only to be replaced by the butt plug. I yelped as the widest part stretched my battered pussy and then wiggled as it slipped pleasurably into place. "Come," she ordered heading to the door. I hurried to follow realising as I did that I was waddling due to the intruder in my pussy. I also got a shock as I started to move, there was something inside the butt plug! Mistress giggled at my gasp of shock and said over her shoulder. "I hope you like your new friend, it's hollow and has a ball bearing inside. As you move so does the ball bearing." She disappeared through the door and I followed getting turned on as I did by this new sensation. In the bathroom I found her trying to unlace her corset, so I helped her to unlace and remove it. She stepped into the shower and handed me the shampoo as she wet her hair. I was then allowed to wash and rinse her golden hair before she handed me the shower gel a grin on her face. Eagerly I placed a large amount into the palm of my hand and then began to wash her glorious tits causing my clit to throb painfully. I wondered if these wondrous globes where an act of surgery or hormones. Mistress smirked as I revelled in the touch and I wondered if I was taking liberties. However the smile on her face said different so emboldened I took more gel and wrapped my soapy hands around her semi hard cock and balls, eliciting a pleasurable sigh from her......she also started to get hard again! "I wish I could but your taxi will be here in thirty minutes," she murmured regretfully. I washed her back and the succulent globes of her bottom before she rinsed off the soap and allowed me to dry her with a soft towel. With fifteen minutes to go I returned myself back to my male self and headed for the door. She followed in a pink dressing gown. "I will see you again," was all she said........commanded. I hoped so because I knew she would be the one letting me out of chastity even though I had the key. I wondered if a few weeks...months of chastity would provide me with a sissygasm when next she fucked me....I hoped so!