Sissy Mistress free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
"Did you finish that report fag!" "Yes." I handed the report that I had spent all night and into the early hours this morning completing to Jonathan. He snatched it from my hand and headed straight to the boardroom. Jonathan was the spoiled son of the owner of the company I worked for. He was in fact my manager and a complete prick! No doubt he would be passing the report off as his own to the board and getting all the praise for a job well done. His father was a traditional man and a billionaire, he had insisted that his son work for his moneys so that he would get a better understanding of its worth. Jonathan had other ideas and so since he controlled my bonuses and shifts he realised he still did not have to do any work. Not when he could get some low paid mug to do it for him. So to his Father he was a hard working industrious young man, to me he was the prick who had me do all his work. I even had to cover for him when he was off fucking one of the women in the company. Having not had to really pass any courses in college he had spent most of his time playing football and screwing the cheerleaders. Now that he was "working," for a living things had changed very little. Since he is built like a football player all the women swoon when he takes any interest in them, and trust me the only interest he takes is to get into their knickers. The reason he calls me a fag is because unlike him I have few friends and I am shy around women. Oh, and the one time I had to interrupt one of his fucking sessions in the printing room because his father was on his way to Jonathan's office. He was in the print room fucking someone's personal secretary when I burst in on him. He pulled out in shock thinking I was someone else. "WHAT THE FUCK! .........FAGGOT." His cock was hard and very, very big....around ten inches long. It was also slick with pussy juice, so of course my gaze was drawn to it. "See I knew you were a fag.....staring at my cock.....wanna suck it fag!" he laughed. "No....no...I.....I couldn't.......your father is heading to your office," I changed the subject. That took the wind out of his sails; he quickly pulled up his pants and barged past me. The woman blushing was pulling up her panties as I left. I must admit I did think about his cock after that, mine only being around 5 inches hard was tiny in comparison to his. No wonder he was such a hit with the women.....well that and his father's money. Jonathan came to see me after his Father left a wide grin on his face. "The old man just wanted to compliment me on how well I was running the department. In fact I am getting a pay rise and a better company car.." I felt like punching him in the face considering I had done all the work. "So fag boy did you like my real man's cock," he snickered. I blushed with embarrassment and to my horror my cock got hard. Fortunately he was diverted by a pair of tits before he saw my blush....and my erection. So this was why I was known to him as fag boy. A few hours later Jonathan came out of the meeting room his father patting him on the back. I could tell he was getting all the plaudits for my work, in fact he looked over at me and winked ........the bastard! resigned I got on with my own work which as usual was suffering because I was doing all of his. Jonathan had even had the gall to call me into his office to reprimand me for my work. When I pointed out I was late because I was doing his work, he suggested I might think about getting a job elsewhere. Of course the prick knew the job market was tough and I would just have to get on with it. Rather humiliatingly I had to apologies and assure him I would get my work up to date. Which is why I was up late most days doing his! At the end of the day Jonathan appeared, he was in a rush because the latest PA, a sexy blonde had offered him a night of entertainment if he drove her home. He slammed a couple of stacks of paperwork down on my desk and headed for the door. As he did he called over his shoulder, "The report I need at the end of the week so you have some time.....but the financials I want on my desk in the morning!" And he was gone. Despondently I realised that I was going to be up until late again to get his work done. "He is a real prick," commented Rosanna. Rosanna was one of my work colleagues, she was a rather plump lady. I secretly loved her figure and would have given anything to worship it. Unfortunately she had not shown any interest in me. I on the other had admired her and would do anything for her. I think you may have gotten the picture by now that I am a submissive. In fact though I would never have told him so Jonathan was half right. I was bi-curious, the thing was the male would have to be dominant! Although Jonathan was that he was also very arrogant and a complete prick, which put me off completely. "Yeah but what can I do," I answered meekly. "Well if he asked me to do his work he would get the back of my hand," she quipped. Rosanna had every reason to hate Jonathan as much as I did. He had told her despite the fact that she had no interest in him that he did not fuck fat women. She had threatened to report him and he had threatened dismissal, he won of course. I knew I should have been more assertive; perhaps inform his father what he was doing. I realised however that his father would probably tell me to stop complaining he was simply delegating. I shuffled all the papers together and headed home. After dinner I set to work on the financials. It did not however take me long to realise there was something wrong. There seemed to be two accounts. I was puzzled to start with then I realized there were in fact two sets, the real accounting and a second set which belonged to Jonathan. From what I could tell he was transferring money to his own account from the company. My heart beat faster when I realized what I had; this would really change how Jonathan treated me! I also realised that Jonathan would probably find a way to wriggle out of this so I had to build up a better case and find more evidence. Jonathan was always in late so the following morning I searched his office, no one said anything because I was always in his office dropping off reports. Being an arrogant person he had not hidden the evidence very well so I took it and made photocopies of everything. I put everything back including the financial accounts he had not meant to give me so that he would not suspect anything. That night I looked through everything I had in detail and realised the enormity of his cheating. He had amassed fifty million dollars in an off shore account which was not to be sniffed at, but what really sealed it was the fact he had majority shares in a rival company, a company that was aggressively trying to buy us out. So with a very happy feeling I went to work the following morning. I knew Jonathan would be coming to my desk for the financial report and when I saw him coming my heart skipped a beat. "You better have those financials done faggot, I need them now," he demanded. "I have them here," I said nervously handing him my evidence. He snatched it from me and started reading. "This is not.....what the fuck," his face grew red. "So the faggot has teeth......" he hissed at me. "Do you think the old man is going to worry about fifty mill.....that's pin money," he sneered. "You may want to read the last few pages," I suggested. When he read the evidence of the company shares the colour drained from his face. He grabbed me by the arm and hauled me into his office. I thought he was going to beat me up and realised I would not have stood a chance! "Okay fag boy how much do you want!" he demanded. "First you can stop calling me fag boy," I demanded back. The sheer fact he was trying to broker a deal made me realise I had him. Now was the time to give him my demands. "I don't want your money I want you at my place seven sharp tonight." I snatched my arm away from him and left the office not giving him time to answer. I was sure he was completely confused as to what I wanted but I did not care. He left shortly after giving me a dark look as he went. Rosanna commented on the argument but I just told her he had not liked my latest work and I had to do it again. She tutted in response and called him a prick. That evening I prepared myself for the encounter. I was not sure whether he would turn up and even more unsure what to do if he did not. To my surprise he turned up at seven on the dot and I ushered him in. He looked quite cocky and seemed sure he could get a deal that was best for him. "Okay Dave...I can call you Dave......" I nodded. "So how about I give you a million and you give me everything you have," he grinned. I was annoyed that he thought he could do all the bargaining. So I quickly put him in his place. "No......here's the deal...." I countered. He seemed taken aback that I had refused his deal but I went on. "Tonight in my house you will do everything....everything I tell you to do. There will be no refusals. You have three strikes after that everything I have goes to your father....." I smiled inwardly as a puzzled look crossed his face. "If you can get through the night I will give you everything I have and you can destroy it.....understood?" He nodded not sure where I was going, I must admit I reveled in his unease a completely new feeling. "Okay take all your clothes off," I ordered. "What strip naked!" he gasped. I cocked an eyebrow at him. "Okay....okay...." he started to strip. "That was not a strike was it?" He asked almost timidly. "No......then put this on." I had done a little online shopping and could not wait to see him in his attire for the nights fun. He looked at the leather trousers and grimaced. Naked I had a chance to check out his body. He had an athletic body but I must admit it was his cock that drew my attention. Even soft it was larger than mine and I knew once it was hard it would be about ten inches. I wonder what it would take to get him hard, snapping out of my reverie I handed him the trousers. He struggled to put them on as they were very tight. The front was laced to restrict his cock but it was the rear that seemed to fluster him the most. In fact it was the lack of a rear, you see the back of the trousers were cut away to expose his bottom to the world. I could see on his face that he had a thousand questions but I just let him stew. I had one more piece to his attire, when I brandished them he turned pale. I dangled the handcuffs before him glowing with pleasure at the look of fear on his face. He knew that once they were on he was completely at my mercy. "Put your hands behind your back," I ordered. I saw him flinch and then his shoulders dropped and he complied. I quickly snapped them in place, and then inspected him. He stood still, and, was that a shiver of fear I saw? I smiled realising that he must be thinking I was a faggot and now that I had him at my mercy.....well! I could see the outline of his cock pressed against the lacing and to my surprise he blushed at my stare. "Kneel," I ordered. Nervously he got to his knees. Then without any explanation I headed to the bedroom leaving him on his knees. Since I had worked for this moment I had also done a little online shopping to gather the attire I was about to put on. Never Have I worn anything like it. As I said I am a submissive, well I also have a passion for maid's uniforms, the girlier the better! This new outfit was however a completely different ball game. In preparation I stripped naked my body has very little hair and any I have I shave off. To my chest I attached a pair breasts forms, not too big but ample enough to fill out the corset. This was the first item I put on. It was made from very thin soft leather, deliciously cold as I slipped it on but soon warming. I had to breathe in deeply to fasten it at the front but marveled at the waspish hour glass shape it gave my slight figure. It was paneled in light pink leather front and sides, the piping bright pink for contrast. The fastenings at the front covered by white lacing that ended with a pink bow between my fake breasts. The breasts which sat nicely in the white satin material that made up the cups of the corset. The corset also had an attached collar, it was white leather studded with diamonds piped in pink and edged with white lace and attached to the corset between my breasts. Next with shaking fingers I pulled on the panties. They were also soft pink and white leather to match the corset. The pouch that hid my sissy dick was attached to the waist band of the panties with metal studs covered by a pretty pink bow. On the front white panel of the panties was a bright pink heart. So when I wanted to get access to my sissy dick all I had to do was pop the studs. The rear of the panties were a simple G-Strip affair the centre strap falling between the cheeks of my ass and caressing my sissy pussy deliciously! Next came the boots and I really drooled over these. Soft pink leather again save for the toe caps that were white with a pink bow. The boots had six inch heels and hugged my calves up to my kneels where they flared out reaching half way up my thighs, high at the front lower at the back. Three white straps spaced at even intervals up the boots secured with heart shaped buckles added bright pink bows to these deliciously sissy boots. I had a coat and hat to put on but first I had to apply some makeup. As I sat down I wondered what Jonathan was thinking....doing. I was certainly making him wait.....and hopefully sweat. The makeup was light and very, very sissy. Pink lipstick, pale glue/green eye-shadow and lusciously long lashes. The final touch was a big blonde wig that fanned out in massive curls around my head. Content with my makeup and eager to get back to Jonathan I slipped on the coat and hat. The coat was soft pink leather in the style of a circus master, the cuffs ending in soft white fur the collar white ruffles. The hat was again pink and white leather and like a military peek cap in style with a large heart shaped pink diamond where the emblem would be. The peek studded with diamonds. I took a few seconds to admire myself in the mirror and enjoy the rush of blood to my sissy dick. The feeling of power was quite the aphrodisiac! I picked up the last two items of the outfit, white gloves and pink leather riding crop all adorned with pink bows and headed back to Jonathan. When I stepped gracefully into the room remembering to take small steps and swish my ass his jaw dropped open in amazement. "Like what you see?" I asked in a low voice. "I...I...wow amazing." To my surprise I saw his cock twitch in the tight confines of his trousers. Then a grin split his face. I realised taking in my attire he must have assumed that he was going to fuck me! boy was he in for a BIG surprise! He made to get up. "No stay where you are.....slave." It was amusing and thrilling to see the grin disappear. "As I said you will do everything I say...." "Where is your phone?" I demanded. "In my jeans pocket...why?" I did not reply I just retrieved his phone and his wallet. The first thing I did was clone his contacts to my phone, then I surfed the internet for just what I wanted, having found it I dialed a number and made a purchase using his credit card. I could see he was dying to know what I was doing but I wanted to make him sweat. "Okay I have ordered you a surprise but it will take a while to get here, which gives us time to play," I smiled sweetly at him. I then moved to an armchair and bent over the arm my sissy ass flaunted in his direction. "Come and worship my ass," I ordered looking over my shoulder at him. I could see the look of reluctance on his face but with only the tiniest pause he shuffled across to me on his knees. I felt the slight touch of his lips on my flesh and it sent a ripple of pure pleasure through me. Was it the touch or the fact I was dominating him, I do not know but my cock throbbed! "Kiss harder slave I want to really feel your adoration," I turned the screw. He obediently complied and I felt stronger kisses on first one cheek then the other, then he paused. "Did I tell you to stop?" I demanded. I smiled when he immediately returned to kissing my ass cheeks. Whilst he was doing this I reached round and gently coaxed the strap from between my cheeks. I heard him groan but it was not in pleasure, he obviously reaslised what I wanted him to do next. I must admit my heart began to beat even faster, I knew I was pushing him but the thrill of it was intoxicating! "Worship my sissy pussy," I croaked lost in lust. "I.....I....Can't....." he stammered knowing the consequences of a no. "Pretend it's a pussy," I coaxed. "I don't lick pussy.....I'm a man!" he blustered. "REALLY!" I pushed him away from me as a wicked idea entered my head. I grabbing my phone this time and headed into the bedroom so he would. not over hear my conversation. Satisfied and pleased with myself I headed back to Johnathan. "Perfect," I mused to myself watching him squirm. "Okay Jojo......yes that's your sissy name for tonight.....you are now a sissy girl not a man." I could see he wanted to protest but I cut him off. "You have one night, you will suffer humiliation of that there is no doubt. But what is one night compared to the years you have humiliated me? Trust me if I reveal your illegal activities to your father and the cops there will be far more humiliating consequences. Especially for a pretty boy in prison....." I watched the colour drain from her face and watched her shoulders drop, she adopted a more submissive posture. "And since you cannot follow orders over the chair arm," I ordered. She complied without a word. I looked down at the pink globes of her upturned ass and my mouth watered. I really wanted to beat the hell out of her ass and my cock throbbed painfully with the anticipation. What made it even better was the fact she was shivering knowing what was to come. "Since you have been a bad girl you will get six strokes from the crop." SWISH.........CRACK! I gave her no time to anticipate and no mercy. She howled in pain and jumped up, hopping around the room holding her ass. It would have been funny but for the fact I was so turned on! "Get your ass over the chair," I barked reveling in my role. She reluctantly returned to her place and I admired the livid red mark I had left, that is going to bruise I mused. "Since you stood up we will have to start again," I smirked. I heard her gasp but she stayed in place. This time I paused allowing the dread to sink in. She knew she was going to feel the stroke and even worse she had to stay in position after. Her shivering had increased as had my excitement; my sissy dick was dripping profusely. SWISH.....CRACK! She stayed in place as she did for the next five strokes but only just, especially when I 'accidentally' laid one stroke over another. Finished I threw the crop on the floor and dropped into the chair beside her. With fumbling fingers I popped the studs on my panties and let my hard dick spring free. I watch with lust as her eyes grew round and the realisation hit her as to what I wanted from her to do next. "Suck my sissy dick!" I growled. She shuffled round wincing at the cuts I had just delivered and then moving between my legs lent in and took the whole of my sissy dick in her mouth. It was such sweet bliss I arched my back with pleasure. The sensation of her hot mouth was unbearable! "stop...stop...STOP!!" I screamed. She pulled back going onto her heels. "What did I do wrong?" she gasped. Panting for breath I could not reply for a few seconds. My passion was so high I knew that if she had sucked a second longer I would have exploded and I really, wanted to prolong the pleasure. "Nothing, you're just so good you almost made me cum instantly," I giggled. The look on her face was priceless....should she be proud or disgusted of her talents? Oh, that look made my balls boil! Regaining a little more composure I spoke. "Worship my sissy balls," I ordered. She looked a little reluctant but still complied and I squirmed as her hot wet tongue caressed my balls. I allowed her to worship for a while but I knew it was useless; in fact her ministrations were almost driving me to the point of climax. In the end I relented and got her to suck my sissy dick again. As I expected I was shooting my sissy juices after a couple of minutes of sucking. To my surprise I did not have to tell her to swallow it all, she did so without asking. I grinned down at her and she blushed....a girly blush! Satiated I allowed her to caress my balls giving me the time to catch my breath in anticipation of the next humiliation. I had noticed that she was breathing hard and although I could not see wondered if she was hard. Suddenly there was a loud knock on the door making us both jump. Pushing Jojo aside I went to answer the door my heart again starting to beat faster because I knew who it was! "That will be your surprise," I quipped mysteriously, mussing her hair as I passed. I opened the door to two rather large black men, the first stepped inside grabbing me around the waist. "Hello sweet cheeks, so you want some manly entertainment for the night," he grinned. The second man stepped inside closing the door and grabbing me from the other side. "Aren't you a sweet little thing," he quipped. I was wedged between two hulking black men and certainly felt small and sissy like. I blushed deep red at their comments and their roving hands! "Much as I would love to enjoy your company boys, no, you were hired to entertain my faggot friend here," I nodded my head towards Jojo. It was delicious to watch her squirm and my recently drained dick throbbed back to life. "Well, well, well what do we have here? A sissy fag boy ready to serve." "She likes to be referred to as a girl actually...." I laughed. "So Jojo say hello to......." "Leon and Jake," they answered. Leon moved toward the bound Jojo and I watched her shrink as he grew closer. He grabbed Jojo's head and mashed her face into his leather covered crotch. "Master Leon knows what fag white gurls want," he grinned. With that he began to unzip his trousers. I moved into the room watching Jojo's reactions. Her eyes were round and I could see she was shaking, her dick' however showed a different story. It looked to be hard but with the tight trousers it was hard to tell. As I was checking on Jojo's dick Master Leon popped his monster cock from his trousers, it was twelve inches at least and thick. Jojo's eyes grew even rounder. "Wanna suck it gurly," he growled waving in menacingly in Jojo's face. She violently shook her head. "Don't be shy...you know you want it." Jojo looked at me pleadingly, I shook my head and her shoulders slumped. Master Leon noticed the interplay and grinned. "What do you want Jojo," he prompted. "Please.........." her voice trailed away. "I think you boys should get comfortable," I giggled. I moved to Jojo and undid the handcuffs giving her use of her hands again. Now was crunch time, would she bolt for the door. To really test my control I spoke. "Why don't you help the boys take their clothes off," I commanded. With a thrill that sent my cock throbbing she complied and pretty soon she was helping both men to undress, they of course took the chance to grope and tease her. Once naked I had Master Leon sit in the chair because he had the biggest cock. Master Jake was not far behind at ten inches but he was a lot thinner. I knew Jojo was a virgin so this would be easier for her. Once in position I could see Jojo glancing back over her shoulder nervously. "She's all yours boys," I said getting comfortable and pouring myself a glass of wine. "Lick my balls bitch," commanded Master Leon. Jojo complied nervously and Master Jake burst out laughing. "Seems like someone has been a naughty gurl," he taunted tracing the stripes I had left on her behind. She flinched at the touch still tender, he slapped each cheek causing her to yelp and moan. I watched with glee as Master Jake lubed up his cock for action. He then liberally coated Jojo's quivering puckered hole. I could not wait to see him sink the full length into Jojo and make her his bitch. I did not have long to wait, Master Jake was horny. He lined up his cock at Jojo's puckered hole ready to thrust. "Relax honey," he coaxed and began to push. I heard Jojo groan in pain but it was stifled as Master Leon mashed his balls into her mouth. With a sigh from Master Jake he popped inside and began to sink the whole length into her. I was on the edge of my seat watching the action and unconscionably rubbing my sissy cock though the leather. Once Master Jake was fully in Master Leon spoke. "My turn bitch.....time to deep throat some black cock." He looked at me and I nodded. Hell yes I wanted to see that long fat cock choking her. The pleasure of revenge was so deliciously sweet. I wanted her fully humiliated and knocked down several pegs. In the back of my mind I was hoping this would change her...bring some humility but I doubted it. So I was going to revel in the sight of her impaled on two dicks. As I expected the first few attempts had her gagging and saliva dripped from her lips. "Now I know you can take it.....and until you do, my friend Jake here is going to stay buried in that sissy hole," quipped Master Leon. Again and again the cock slipped into Jojo's mouth then finally it slipped into her throat and her face was buried in his crotch. The two men high fived over Jojo congratulating themselves. Jojo wide eyed and shuddering glance at me for mercy...I grinned and winked at her. She in return dropped her gaze. "Okay bitch time for some real fun." With that they began to rock backwards and forwards, the thrusts of Master Jake forcing her onto Master Leon's cock and vice versa. Finally I could take no more and got up to join the action. I knelt at Jojo's waist and began to unlace the crotch of the trousers. "It seems the boys are getting all the action," I cooed to her. "Want me to play with your sissy dick?" I asked innocently. her eyes grew round and she tried to shake her head. "I will take no answer as a yes," I giggled. She groaned a resigned groan which went up an octave when I grabbed hold of her sissy dick. It was not hard but then it was not soft either I noticed. Taking some lubricant that had dripped onto her balls I began to stroke in time with the strokes. Pretty soon she was groaning in time with the strokes and I knew she did not want that, to turn the screw I spoke. "Turning into quite the little cock slut." I saw her shudder at the remark and reveled in the humiliation I was inflicting. Master Leon was the first to announce his climax bellowing like a bull and shooting his spunk straight into her belly. I then watched closely for Master Jake's climax timing it so that sissy Jojo came at the same time, she did so screaming her release and then blushing profusely at the humiliation. I however had one wicked twist. I had caught her climax in my hand and offered it up to her. "Lick it up!" I demanded. I could see the complete look of revulsion on her face but she could not refuse. Her tongue snaked out and she tried to gather it in one go to get it over with. I pulled away, allowing her to take it slowly a bit at a time, my heart beating like a hammer at the sheer power I now possessed. The boys watched on, their bodies slick with sweat. "You can thank the boys by licking their bodies," I ordered. Without pause she did so, starting with their cocks I noticed. She had finished Master Leon and had just started on Master Jake when there was another knock at the door. "Ah, my final guest of the night," I looked at Jojo and saw the look on her face. She must have been wondering how I could humiliate her any more. Well she was about to find out, my cock throbbed painfully. I was definitely going to have to get her to suck it again.....and soon. Before I opened the door I put on my dressing gown so as not to startle my new guest. I opened the door and Rosanna was standing their smiling, her smile vanished however when she stepped inside and saw the lewd scenario. "What the fuck.....is that.....shit is that Jonathan!" She was shocked at what she saw but soon recovered her composure. "How the hell did you get him into this predicament," she quizzed me. Grinning I ushered her inside taking her coat. As I did I noticed Jojo had gone drip white. "I believe you have work to do," I ordered. Reluctantly she got back to licking Master Jake clean. Rosanna could hardly take her eyes off the action so I slipped out of my dressing gown. "Wow...look at you......" she laughed. "Quite the Dom......and I pegged you as a sub," she winked. "Ohhh I wish...for you," I blurted and then went bright red. Without batting an eyelid she continued. "Pour me some wine....and we shall see," she quipped. So as we drank wine and watched Jojo debase herself I filled Rosanna in on the details finally getting round to why I had invited her. "It seems Jojo here has never licked a pussy, and I knew you would be just the lady to teach her," I grinned. I turned to address the men as Jojo had finally finished her task. "Thank you gentlemen for your services, I am sure Jojo loved them. I will be sure to get her to add a large tip for a job well done.," I winked at Jojo. "Jojo, can you help the men get dressed and see them to the door," I ordered. We watched amused as she helped the two men dress get dressed. They took the chance to get some final groping and humiliation as she did. I retrieved her phone again and added a tip to the bill for their services. So with some relief I could see in Jojo's eyes she finally showed them to the door returning to kneel before us. "So never licked a pussy," mused Rosanna. Jojo blushed bright red but her now loose dick was hard, perhaps she was looking forward to the prospect. Rosanna stood and walked past her before sitting in the seat Leon had recently vacated. "Over here slave," she ordered. Jojo looked at me as if to ask for approval, or did she want me to say no....fat chance! I nodded and shivered as the look on her face change to one of resignation. She turned and shuffled between Mistress Rosanna's plump thighs. I could see the look of lust in her eyes. It would seem she was relishing the power she had over her once arrogant boss as much as I did. Slowly Mistress Rosanna rucked up her skirt to reveal first that she had stockings and suspenders on and a few seconds later her plump pussy encased in deep red satin panties. I could tell she was excited as the crotch of the knickers were slightly darker. My mouth watered and I could almost imagine the heavenly female scent. At that point I was extremely jealous of Jojo, I so much wanted to lick that pussy. "Lick me," She ordered in a husky voice. Jojo mashed his face against her knickers in what I thought was eagerness, but maybe it was an attempt to get it over with. In any case Mistress Rosanna was not impressed. "Gently fool!" she admonished. Seeing my chance I picked up the discarded riding crop. When Mistress Rosanna saw it her eyes lit up and she stood brushing Jojo aside. I saw Jojo catch sight of the crop and she groaned. "Adopt the position!" I ordered with a wicked grin. I could see she was reluctant, was it the fact she was going to be punished by a woman or that she was still stinging from my strokes. "Wow, looks like someone left their mark here before me," she laughed. "So six strokes to start with.....then you can try licking my pussy again." "Please can I try again now.........Mistress Rosanna," she whimpered. "What and miss all the fun.....I don't think so." SWISH......CRACK! The stroke landed without warning and I could see Jojo struggling to stay in place. Mistress Rosanna is a big woman and it looked like she was not pulling her strokes. "Thank your Mistress," I commanded turning the screw. "Thank you Mistress Rosanna," she replied meekly. God it made me so horny to watch her demean herself before Mistress Rosanna, knowing that she once said she never fucked fat women. I was surprised that at the end of her punishment she had tears in her eyes, her sissy dick however had shrunk. "Now shall we see if you can do a better job," commented Mistress Rosanna as she again seated herself. Jojo eagerly got between Mistress Rosanna's legs but this time her ministrations were a lot more delicate. I watched her plant delicate butterfly kisses along her thighs until she reached her panty covered pussy. I was so jealous at that moment so I decided to get in on the action. I moved behind Jojo and lifted her onto her hands and knees. She shuddered no doubt anticipating what was to come. Mistress Rosanna looked into my eyes and winked. She then wiggled out of her panties and cast them aside. I popped the studs on my panties and allowed my sissy dick to spring free again. It was hot and turgid, ready to fuck. I noticed Jojo was well lubricated from begin fucked by Master Jake so I knew I would easily slip inside. I lined up my cock and let it rest there feeling her quiver under me. It was a feeling of such power, knowing that I was going to be doing the fucking. I realised that I had never fucked anyone in the ass before and it sent my pulse racing, as I sent my sissy dick plunging into her pussy. At the same time Mistress Rosanna mashed Jojo's face into he pussy and screamed her orgasm. I was almost oblivious to this as I reveled in the sensation of Jojo's hot wet pussy. It was tight and so so hot that it nearly made me shoot after just one stroke! However I manage to gather my faculties and not explode. I remained motionless buried fully in her watching Mistress Rosanna's heaving breasts as she came down from her orgasm. This in its self, had my pulse racing! Finally I managed a few strokes and then a steady tempo, in the meantime Mistress Rosanna had Jojo return to gently licking. Together we headed for another orgasm, curious I reached round and found that Jojo was rock hard, she flinched as I stroked her and I would have loved to make her cum but I could not get the angle. I had to satisfy myself with the knowledge that the arrogant prick from the office was gone, in his place a girly cock loving, pussy eating faggot. This thought drove me over the edge and I climaxed, watching me then had the effect of making Mistress Rosanna climax. I wonder if she was thinking about how low I had managed to take the arrogant prick from the office? Satiated I popped my sissy dick from her pussy. "You got some cleaning to do," winked Mistress Rosanna. I grinned realising she had really taken to domination.....hopefully I would benefit from that. Jojo was quick to dive between my legs and start licking. When she had finished I sat on the seat beside Mistress Rosanna, Jojo knelt before us looking expectant. "You know Jojo you have been a good girl so I think you should be allowed to cum." I watched a hesitant smile grace her lips. I think it was hesitant because of my wicked grin. "Take hold of your sissy dick and wank it," I ordered. "But don't you dare cum until we say," added Mistress. She complied hesitantly at first then with more gusto as her climax built. "What do you think she is thinking about?" I mused. Mistress Rosanna laughed knowing exactly where I was going. "Oh, I think she is thinking about my pussy," she smirked. Jojo's eyes widened and she stroked a little faster. "No....it must be the thought of those big, black...cocks!" I retorted. Jojo flinched but carried on wanking. "Surely it must be the taste of my pussy juices on her lips," quipped Mistress. "Or it could be the taste of manly spunk," I laughed. "Please........." Jojo begged. "I also think she loved my sissy dick in her ass," I turned the screw. "Please......oh...please...Mistresses," she almost screamed. "So tell us what you are and you can cum," laughed Mistress. I got hard again! at the look on her face. She so much wanted to cum but she did not want to debase herself. "I'm a pussy licker," she whimpered. "And what else?" "A cock sucker," whimper. "And what do you love?" One final turn. "I love sucking cock and licking pussy," she gasped. "You may cum, but catch it in your hand," I commanded. I saw the look of pleasure turn to a look of horror but she was too far gone and groaned as she shot her load into her own hand. I cocked an eyebrow at her and she knew what to do. She put her hand to her mouth and slowly licked up her own sissy juices. '"Oh....wow, you got her to drink her own spunk," laughed Mistress Rosanna. Jojo blushed bright red but finished the job licking up every last drop. Reluctantly I spoke to Jojo. "Okay take your clothes into the bedroom and get dressed. All the stuff I have is in the file on the bed. Take it and leave." Jonathan did not talk or even make eye contact when he left. "You gave him everything," quizzed Rosanna. "A deal is a deal," I replied. "Well just thinking about tonight is going to get me horny for a long time," she smiled. "Speaking of horny, I saw the way you watched Jojo licking my pussy, bet you wished that was you...." I blushed unable to say anything. "Worship my pussy," she ordered. Eagerly I got on my knees and pleasured my new Mistress; I did so late into the night. later, exhausted and satisfied I got ready for bed, however I still had one more chore to perform. I switched on my laptop and got to work. The following day Jonathan arrived at my desk quite early. He slapped a thick document down. "Sign it." "What is it?" I returned. "Last night I saw my personal lawyer and he worked all night, at a high price I might add to produce this contract. Once signed if you even think about the stuff you have on me I will take you to the cleaners, oh I may go down but so will you," he hissed. I thought to myself why should I sign it, but then it had been a crazy night. I picked up a pen and signed. "Thanks FAG!" he snatched it from my desk and headed for his office. Over his shoulder he quipped. "I need that report on my desk today!" I watched him enter his office and shut the door, I gave him a few minutes to sit down, then I pressed the send button on my computer........then silence.....then swearing and crashing and banging. Rosanna pulled her chair over to me. "What the hell did you do?" she asked. "Well last night I recorded the whole session. I then carefully cut the video so that it looks to all the world like Jojo is a cock sucking faggot," I grinned. She burst into hysterics at this and in the background I could hear Jojo still cursing. "Fancy coming to my place this weekend.....I have a new maid to break in," I winked.

Same as Sissy Mistress Videos

4 years ago
  • 0
  • 35
  • 0

Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
  • 0
  • 39
  • 0

Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

1 year ago
  • 0
  • 27
  • 0

Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
  • 0
  • 34
  • 0

Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
  • 0
  • 40
  • 0

Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

3 years ago
  • 0
  • 36
  • 0

Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

1 year ago
  • 0
  • 46
  • 0

Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

1 year ago
  • 0
  • 49
  • 0

Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

4 years ago
  • 0
  • 33
  • 0

Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
  • 0
  • 33
  • 0

Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
  • 0
  • 46
  • 0

Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
  • 0
  • 32
  • 0

Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
  • 0
  • 36
  • 0

Sissy Farm 20

20 Sissy farm List of Characters. Me. Michelle A Natural transvestite sissy. Janice My Younger sister Aunty Bev Janice and My mother's Sister. Mistress Janet Headmistress of the young lady's academy Doctor Shirley Williams. My endocrinologist. Miranda. A very effeminate Sissy sales assistant. Miss Stern Miranda's mistress who owns the shop. Peregrine AKA Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James AKA Auntie Jamie Peregrine's...

1 year ago
  • 0
  • 37
  • 0

Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty...

4 years ago
  • 0
  • 28
  • 0

Sissy Velina

I walk into the living room of my master. I am completely sissified and wear a very frilly sissy maid outfit. My 6" white leather peep too high heels have thick leather straps around my ankles and are closed with medium sized padlocks. I wish I knew where my master holds the keys. On my lightly sun tanned and smoothly shaved legs I wear white sheer seamed stockings and with a nice lace band at the top. At the back the pink seams end with large pink girly satin bows. Just above my...

3 years ago
  • 0
  • 57
  • 0

Sissy Rules Reads like a proper job description

(Found this on the internet... #65 seems especially made for me) Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows...

1 year ago
  • 0
  • 39
  • 0

Sissy Rules

Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows big fake titsRule#14: A sissy is a pro cock suckerRule#15: One is...

2 years ago
  • 0
  • 43
  • 0

Sissy Julian Chapter I Beginnings

Here we go again. Some boys simply are sissies. This is the story of one of them. It is not a story of discovery, although there is much of that, but rather a tale of a lovely boy's trip to self-realization, albeit a tad 'forced.' If lots of frilly sissy boy and girl outfits, super swishy behavior and a little sex, not to mention dominant women, are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fictional fantasy work. No references...

1 year ago
  • 0
  • 38
  • 0

Sissy Crissi Chapter 3 Leroys Turn

Chapter 3 - Leroy's Turn But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upward, off my stockings, across my garter straps, up to where he cupped my round bottom in his palms. He then placed his fingers...

4 years ago
  • 0
  • 50
  • 0

Sissy discovers Part 5

Part 5 of the story about Sissy and her sexual awakening ****************Brad did not hesitate when invited to go over to Lisa’s. Sissy was not surprised. What young male would not want to hangout with a girl who flaunted her nude body in front of him only hours before. They decided to take the pontoon boat over as it is ten minutes by boat and almost 40 minutes by car. Evening cruses was a family specialty and Brad was good at handling the boat. As they pulled up to Lisa’s family dock Sissy...

4 years ago
  • 0
  • 31
  • 0

Sissy gracie Life begins anew

Sissy gracie, Life begins anew Chapter 2 As i stood to dress.. the first guy asked me.."So cunt.. you are wearing sissy clothes underneath and all lockedup. Do you have other clothes .. other sissy clothes?" 'ohh Yes Sir' i replied... "Good .. tomorrow.. bring the key.. and wear more.. i want to see you all sissified...... no pants.. just sissy clothes.. prissy dress.. stocking.. high heels.. make up... make your tits look big...... do it up...... and I will hold your key...

4 years ago
  • 0
  • 45
  • 0

Sissy thoughts 2 Questions From Sissies

1. I am about to have my first experience as a sissy with a Man! How can I make it more special for us both?A: How wonderful! You are at the very start of your new sissy life. It will of course be special and memorable, but to deepen the reprogramming of your still-forming sissy mind, try dressing as a sissy schoolgurl. Not only will it drive your Man wild with lust, but the symbolism of your costume, and the reality of the loss of your virginity will combine to kickstart stronger, more...

2 years ago
  • 0
  • 36
  • 0

Sissy Farm Chapter Twelve

Sissy Farm - Chapter Twelve By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA....

4 years ago
  • 0
  • 28
  • 0

Sissy Sally

CAUTION: This is a forced fem story. If this is not your thing, please move on. All rights reserved. Sissy Sally Sam Smith fretted anxiously at the kitchen table while he waited for his mother to return from the district attorney's office. How could he have been so stupid? Breaking into the new neighbor's house had been a disastrous idea from the start. Ms. Johnson was an attractive, impeccably dressed older widow who had moved into the house-...

3 years ago
  • 0
  • 36
  • 0

Sissy discovers Part 4

the continuing original story of a young girl finding herself****************************Breakfast was filled with the usual mumbles of ‘good morning” and banging of pots, sizzling bacon and gurgle of juice being poured into tumblers. Sissy and Brad avoided looks at each other at first, and then Sissy sat down across from him at the table and patted him on the head saying, “what’s the matter grumpy?” in an exaggerated baby voice. “Nothin’ - hand me that fruit will ya?” He replied and gave...

3 years ago
  • 0
  • 39
  • 0

Sissy School Part 2

SISSY SCHOOL - PART 2 By Missy Crystal I followed Mistress Mary back to her office. She left me standing in the middle of the room and sat down behind her desk. After ignoring me for a few minutes, she looked up and said, "I told you that you would be severely punished for disobedience." Crap, I thought to myself. I already have six strokes of her leather paddle coming. What did I do wrong? My face dropped. She smiled, "but I can also reward, when I am pleased with your behavior. You...

1 year ago
  • 0
  • 33
  • 0

Sissy Cruise 3

"We are going on a Caribbean cruise, in two weeks time......." stated my wife Penny. "Oh......Okay," I queried. "With Samantha and Tim," she finished. "Oh really." Samantha is a new friend in my wife's life. They have known each other for a couple of months, but they are already quite close and always scheming together. My relationship is mixed. It seems that the only time she talks to me is to point out my faults which is somewhat annoying. However she is very domineering...

4 years ago
  • 0
  • 32
  • 0

Sissy New Year

Sissy New Year I remember heading out to a New Years Eve party with a group of my friends from work. I remember stopping by a bar for a few, pre-party shots--well, several pre-part shots. I even recall the super-hot transvestite hooker that winked at me as we left the bar. I don't remember anything else after that. Which explains why I was so confused when I work up a few days later, blindfolded, tied up in a strange bed, with something hard lodged firmly up my ass and a big...

1 year ago
  • 0
  • 40
  • 0

sissy rules

A sissy must wear panties. He does not own any male underwear.A sissy may wear a bra and pink or brightly colored tights or leggings.A sissy must sleep in lingerie. If he does not have any, he must sleep naked.When alone, a sissy must dress as a girl. Good sissies wear lipstick while alone.A sissy always keeps himself free of facial hair, and is otherwise well groomed. He must always be presentable, ready to please. Good sissies shave their legsEvery morning after he wakes up, a sissy strips...

4 years ago
  • 0
  • 33
  • 0

Sissy Arm Wrestler

Sissy Arm Wrestler By Margaret Jeanette Margie Ware came home from working out at the health club she belonged to. She was wearing the blue dress she had worn to work. She always felt renewed after a visit to the health club. She tried to visit it at least two times a week. It wasn't easy as she worked overtime at least two nights a week. She always tried to make it on Tuesdays and Thursdays. She looked at her husband of six years sitting in the recliner dozing while the...

4 years ago
  • 0
  • 29
  • 0

Sissy New Year

Author's note: My stories generally featured a lot of forced femme, bondage and kinky sex--you know, the stuff that I keep hoping will someday happen to me. That is still true for this story, but this time around, the author in me decided to spend a bit more time developing the characters before commencing the full-on sissy sex orgy. I also wanted to write a story where the characters are well intentioned instead of simply being a rogue's gallery of perverted bastards. With that in...

3 years ago
  • 0
  • 53
  • 0

Sissy Farm Chapter TwentyOne

Sissy Farm - Chapter Twenty One - By: Beverly Taff List of Characters. Me, Michelle: A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Doctor Shirley Williams: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine, AKA. Uncle Penny: My transvestite uncle. (Aunty...

3 years ago
  • 0
  • 28
  • 0

Sissy Tammy

Sissy Tammy It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a child I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games. My...

2 years ago
  • 0
  • 31
  • 0

Sissy Julian Chapter VI Growing Pains

Sissy Julian - Chapter VI, Growing Pains by: sissystevie Yes, 'tis I, back again. If I can remember how to post this thing on FM. I came across a partially completed additional chapter to this saga, which I abandoned for personal reasons eight years ago, and thought why not? Thus, spurred on by some of your wonderful comments, I completed the chapter and may well complete the saga. There are just too many wonderful kinky - and romantic - moment to come. If you want me to...

3 years ago
  • 0
  • 31
  • 0

Sissy 101 Intro to Sissy Sluts

Sissy 101: Intro to Sissy Sluts One week before my freshman year at college, I received a letter saying that my class schedule changes had been approved. That struck me as odd because I hadn't requested any changes. Without explanation, I had been un-enrolled from two of my general studies classes. I was now signed up for SISGEN101 and SISHYP161--whatever that meant. I went online to the university's website. These classes weren't even listed in the general course description...

3 years ago
  • 0
  • 34
  • 0

Sissy Farm Chapter Nineteen

Sissy Farm - Chapter 19 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

1 year ago
  • 0
  • 30
  • 0

Sissy in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

3 years ago
  • 0
  • 32
  • 0

Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

2 years ago
  • 0
  • 38
  • 0

Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
  • 0
  • 40
  • 0

SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
  • 0
  • 44
  • 0

Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
  • 0
  • 38
  • 0

Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
  • 0
  • 30
  • 0

Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

2 years ago
  • 0
  • 31
  • 0

Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
  • 0
  • 38
  • 0

Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
  • 0
  • 59
  • 0

Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

2 years ago
  • 0
  • 36
  • 0

Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
  • 0
  • 32
  • 0

Sissy Farm Chapter Eight

Sissy Farm - By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James: AKA. Auntie Jamie, ...

2 years ago
  • 0
  • 54
  • 0

Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
1 year ago
  • 0
  • 27
  • 0

Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

4 years ago
  • 0
  • 32
  • 0

Sissy Julian Chapter V A Day at the Village

Julian spends a most interesting and eventful first day in Lake Orenda Village. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....

4 years ago
  • 0
  • 31
  • 0

sissy Britney serving Mistress Jeri James

About a month ago sissy was honored to meet and serve her Mistress.Mistress has been training me for a couple months to be her Britney sissy slave.Training included watching lots of sissy hypno vids along with BBC hypno vids.Learning to dress as Mistress likes, sucking dildoes to become a better cocksucker.Locked in Chasity, my chastity is a nub because my clitty is so small.Wearing butt plugs and once I got use to a size, I had to go purchase a bigger one to getMy pussy ready for large BBC.I...

3 years ago
  • 0
  • 21
  • 0

Sissy Fantasy

I waited for what seemed like hours and was probably minutes when I heard Masters voice. "Silly me I forgot to open it, better hurry sissy I don't think Jenny would be too pleased if the neighbors saw you dressed that way," he smirked. The car lights flashed and the boot unlocked. I grabbed the cases and hurried inside. As I was passing Master he handed me a package. "A present from Jenny....put it on when you change... and put my case somewhere safe but don't open it," he...

2 years ago
  • 0
  • 31
  • 0

Sissy Farm Chapter Nine

Sissy Farm - Chapter Nine By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James: AKA. Auntie...

2 years ago
  • 0
  • 33
  • 0

Sissy Gets A Black Master

Sissy Gets A Black Master I got up wearily from my long and exhausting night being fucked and punished by my new Black Master. As I awoke, I could scarcely believe that all those depraved things had happened to me. One minute I had been merely exchanging emails with a man, who could have been anywhere and the next minute, that very man was at my door, in my home, and then inside my body. Black Master, a man whose name I didn't even know, a man who looked to be about ten years my junior, had...

1 year ago
  • 0
  • 172
  • 0

Sissy Outed Brandon to Brandy

This is a story about seduction and transformation that’s written about a real-life sissy named Brandon Hippel, Brandon’s a cute little limp-wristed sissy-faggot from Abington Pennsylvania that loves to be humiliated and exposed online. She loves feminization, crossdressing, being exposed online, humiliation, anal play, degradation, being captioned, taking pictures, and talking to new people, so feel free to contact her through these various social media; Her kik is; HumiliationSlut2Her email...

3 years ago
  • 0
  • 34
  • 0

Sissy Stepson Part 6 Carolines Sissification

Part 6 - Caroline's Sissification Mrs. Monet was now going to really put the spurs to her sissy stepson and force him to live a life of sissified faggot. With Carl still lying on the floor with sissy cream stains all over his pantyhose and panties she began taking pictures of sissy stepson. "What are you doing, I want to change," said Carl. "Oh, no just because you popped your cookies doesn't mean its over, you pathetic faggot. I now have evidence what a pervert you are and I...

2 years ago
  • 0
  • 33
  • 0

Sissy Therapy

Sissy Therapy by Kate "Great practice, guys! If we keep working hard, we have a real shot at the conference title," Coach Jones addressed the thirty or so high school boys gathered around him. The boys were sweaty and tired, but the coach's praise momentarily raised their spirits. "Smith nice passing out there. Keep up the good work." Fifteen year old Billy Smith grinned cockily. "Sure, Coach. After all, I am the greatest!" The other boys moaned at Billy's arrogance. Coach...

Porn Trends