Pimped Out Sissy Finale free porn video

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The next text I received to worship Mistress Samantha came an agonizing month later. Once again it was short and to the point. I had to be at her place early in the morning, but this time along with my maids dress I had to bring something slutty. I had just bought a new purple PVC mini dress that I was eager to try on so I packed that and having made excuses to my wife left early for a day of servitude....and lots of pussy licking I hoped. I spent the day dressed as a maid alternating between cleaning the house and licking Mistress Samantha's pussy. She had not grown tired of having me between her legs in fact she had an insatiable appetite. Punishment for me when I had not cleaned something right was for her to sit on my face and have me bury my tongue in her permanently sopping wet pussy. Later in the evening Master turned up, he was immediately angry with Mistress Samantha for not having me ready for him. "I told you to have the fag all dolled up when I got here," he berated her. "Sorry Wayne....I forgot." She blushed obviously happy that she had had plenty of pussy worship. "Go get the fag ready," he demanded. In her bedroom I stripped completely and prepared myself to be a sissy slut. The corset was now a pink and black stripped affair, it was from a cheap shop and looked it. I dropped the D sized breast forms into the cups and marveled at my buxom profile in the mirror. To the four garter straps I attached black fishnet stocking ensuring they were straight. I then slipped into the figure hugging purple PVC mini dress. It was so short it was easy to see that I was a locked up sissy. I moved to the dressing table and made up my face....slutty as possible, dark eye shadow, big eyelashes......and of course cock sucker red lipstick, made even more slutty with an ample application of lip gloss. My cock throbbed painfully at the sight of those luscious shiny lips, I longed to play with myself because I had not been able to for three months. Makeup done I slipped on a long black curly wig and the finishing touch, six inch tacky black stiletto shoes. Standing I admired myself in the mirror and realized I looked just like a cheap hooker, it was then I noticed Mistress Samantha watching me. "You really get off on this don't you," she crooned and I could see the lust in her eyes. "Yes Mistress," I admitted truly. In fact she was right I am never happier than when I am enfemme. Now do not get me wrong, I did not want to be a woman, I am a submissive through and through. But to play the roles of the submissive female...maid...hooker now that was a submissive delight that had me throbbing fit to burst! Mistress Samantha ushered me back into the living room where Master Wayne was waiting impatiently. He brandished a cheap black dog collar at me and had me put it on, this submissive act had me blushing and throbbing in equal measure. Once it was fastened he attached a dog lead then jerking on it for me to follow him. "Get in the car fag!" he ordered. I followed him out to the car noticing as I did that it was dark, something I was grateful for considering the way I was dressed. He jumped into a pimped out boy racer car and having no other option I got into the passenger seat. He then drove me out to the outskirts of the town to an abandoned warehouse district pulling up alongside five or six other cars. Wayne got out of the car came around to my side before yanking me out with the dog lead. As I looked around I could see other cars some with their doors open and quite clearly the people inside were having sex, quite loudly in one case. Other cars were darker but furtive movements could be seen inside, I wondered if they were the voyeurs! He headed to an old bench and sat down before taking out his phone. Not quite knowing what to do I stood patiently waited until he noticed me again with a smirk. "On your knees fag!" he commanded. I obeyed without question my caged cock throbbing with the thought of the humiliation he was about to put me through. It was not long before a curious man wondered over. I looked at him whilst Wayne completely ignored him, he was over weight and obviously a cheating husband by his furtive looks around the area. "Hey Wayne.... this your new bitch?" He winked at me salaciously. "No fucking way...... this is my new sissy fag boi... wanna try her..... blow jobs only," he grunted not looking up from his phone. "Fuck yeah a sissy ... they suck cock better than most woman," he laughed. With that he began to unbuckle his belt before sitting himself on the bench in front of me. He then wiggled out of his jeans dropping them to his ankles. His thighs were quite fat and due to the jeans restricting his ankles I realised I was going to have to squeeze my head between them. I shivered at the thought of what I was about to do. It was extremely debasing but I was sinking into sub space. I could feel it washing over me, that sensation of guilty lust at what I was.....what I was about to do! I moved closer and got the scent of him, it was not unpleasantly.... Musky.... Manly emphasising my pathetic sissiness. At the touch of my hands on his thighs he groaned, widening his legs slightly allowing his six inch cock to pop up between his legs. Without preamble I took him in my mouth and swallowed him down to the root causing him to swear and groan in equal measure. With my nose pressed into his crotch I really got a hit of him and looking up caught his eye. He was lost to the lust of what I was doing to him, slack jawed and it seemed almost ready to cum. I winked salaciously.....falling easily..... too easily into the role of cock sucker. If I had not let his cock pop from my mouth I was sure he would have cum there and then. "Jeeze......jeeeze," he gasped. His breath was coming hard and fast so I allowed his cock to pop from my mouth. He sucked in mouths full of air getting control of himself....just. I started licking up the shaft before kissing the head, always keeping eye contact. I kept him just on the boil for quite a few minutes before he begged me to suck him. It was strange having this kind of power but I realise he was not an alpha male... Just a randy husband after a quickie. Well as soon as I took him in my mouth it was quick.... and surprisingly copious! I had to swallow three full mouth full before he withdrew his cock contentedly. "Shit she IS!! good," he gasped to Wayne. "Well if you want more give me your contact," stated Wayne. They touched their phones together and there was a beep signalling the swapping of data. The man stood up pulling his jeans up has he did and ambled off. Shortly after a man of about Wayne's age appeared. "Sup Wayne?" he drawled. "Got a sissy fag I'm breaking in.... wanna blow job," he retorted. "Yeah sure my bitch never gives blow jobs," growled the man....boy.... what was I thinking he was a man compared to me, I blushed at this thought. "Tell me about it," was Wayne's reply. "Does she do deep throat?" "With a bit of persuasion," laughed Wayne. So the man took the place so recently vacated by the fat guy. I had to admit they were poles apart. This man was definitely an alpha... arrogant and sure of himself in his youth. I blushed deeper at his arrogant sneer as he dropped the jogging pants he was wearing. As he did I could understand why because his cock was rock hard and ten inches long. He chuckled as my gaze fixed on the monster cock. "I think the fag is salivating for some man cock!" he growled waving it in my face. To my shame I WAS salivating and my cock was throbbing fit to burst. He opened his legs wide allowing me access and I eagerly obeyed. Now this really sent me into sub space, a dominant alpha demanding my worship..... Heaven! I reached out my tongue and tasted his almost hairless balls. To my surprise they were only slightly salty and if anything tasted soapy. He watched me a sneer on his face as I first licked and worshipped his balls and then up the long hard shaft before swallowing the Plumb sized head. He gasped with surprise at my eagerness but the sneer never left his lips. Taking hold of my head he shuffled to the edge of the bench seat sending his cock to the back of my mouth. I tensed knowing exactly what he was about to do and realised I had to do exactly the opposite and so I relaxed. He must have felt this because he rammed his cock down my throat. I gagged in response tears welling in my eyes but there was nothing I could do to stop him. Fortunately Wayne's previous face fucking had lessened my gag response but still tears rolled down my face much to his and Wayne's amusement. He held me there my nose hurried in his public hair. "Shit I love a bitch who can take a cock," he laughed. He eased the hold on my head and allowed me to let his cock pop from my mouth attached only by a string of saliva. I gasped in as much oxygen as I could and then took him back into my mouth. To my surprise I managed to take him fully into my mouth passed the gag reflex without too much trouble! I knew it would be harder to make him come this way so I resorted to sucking half way down his cock and massaging the rest with my hands. As I expected when his climax started to build he took over the rhythm fucking my face brutally. "Yeah take it fag..... Suck my big fat cock!" His rhythm increased as he verbally abused me revelling in his domination. "Fucking sissy l'm gunna shoot my load straight down your throat!" I felt the tell tale sign as his balls tightened and his cock swelled. And as he bragged he shot his load straight down my throat so that the only taste that I got of him was when he pulled out. To my shame I felt cheated, I wanted to taste his hot salty spunk in my mouth. It was then I realised I truly was in sub space, theirs to do with as they wished! At that point I would in fact do anything they ordered me to.... and thank them for it. The man broke my humiliated reverie by wiping his satiated cock across my face before nudging his phone with Wayne's. "Get fucking cleaned up!" was all I got from Wayne. Luckily I had brought a small purse with me that contained the essentials. When I looked in the compact mirror I was stunned to see what a mess I was. I was just finishing up applying a thick coat of cock sucker red lipstick when the next man arrived. And so it continued through the evening. At one point a woman Wayne seemed to know quite well offered to suck his cock and so after winking at me we knelt side by side worshipping manly cocks. I sucked cocks of all sizes and even a couple of pussy which I thoroughly enjoyed. Wayne even disappeared to go and fuck another woman ordering me to make sure I got their details after they had fucked my fag mouth! Exhausted after a full evening of debasement I was ordered back to the car and driven back to Mistress Samantha's place. "You did well tonight you pathetic fag...... I got plenty of contacts so I guess you're going to be busy," he quipped as I headed back to my car exhausted. "Oh and don't say a word about the bitches I shagged to Sam," he growled. "Yes sir," I mumbled I guess he was not counting the blow job! As I was about to get in my car Mistress Samantha opened the door in her underwear and then turned on her heels. Watching her ample bum sway my cock throbbed painfully and I knew exactly what she wanted. I was summoned again a month later with a very short text message simply stating an address and time. Nothing else, not what to wear, who I was....... Servicing... Serving... humbling myself to. I looked up the address and realised it was not far from the shop where I had first debased myself. It seemed like a life time ago now. Along with the text there were two videos of me sucking cock like a whore! I had not realised Wayne had been filming me, and he had deliberately picked the times when I was deep in sub space and obviously enjoying myself. With a shudder the memory came back and my cock throbbed painfully. I realised I had not been out of the cage for over three months. It was lucky that my wife had not wanted sex, but it was still very frustrating. I packed all the things I thought I might need and headed out to my appointment. The house was in the wealthy part of the town, a detached house in its own grounds. I realised the owners had plenty of money to do whatever they wanted. I rang the bell and waited patiently having decided to leave my bag in the car and come back for it if it was needed. I could here the click of high heels and imagined a scantily clad maid tottering to the door, my cock throbbed painfully. Not for the first time I wondered if I was ever going to get released! The door was opened by a lady in her late fifties dressed in a red silk kimono style dressing gown. I looked into her eyes and mine popped wide as my mouth dropped open. There with a wicked smile on her face that was the woman of my dreams...... well wet fantasies for the past few years! It was the wife of the shop owner and her wicked grin grew even wider at my shocked reaction. "Well, well, well.... look what we have here, all these years wondering what it would be like to have you as my slave and here you are curtesy of my daughter...... Mistress Samantha to you." I stood there mesmerised both at the sight of her and the fact that she had thought about me being her slave. "Well don't stand there gawking, follow me slave," she ordered. She turned on her heel and after a few steps headed up a wide staircase. I was left to close the door and scuttle after her. I quickly caught her half way up the stairs and took my chance to ogle her. Although the kimono was loose I could still see her figure was rubinesque just the way I like them. Occasionally I got a flash of pale white thigh and white gossamer stocking, yes stockings. My heart was pounding and my cock was throbbing painfully at the sight of her. She entered a very large bedroom dominated by a huge four poster bed. It was to this she headed loosing the kimono as she went. My heart beat out of my chest at the sight of her ample behind. The dark crease framed by the two frilly suspenders that descended from the brilliant white corset she was wearing. The corset pulled in her figure but to my joy could not contain it, only emphasising the curves rather than restricting them, I drooled. She was wearing white thong panties I could see the rear strap descend into the dark place where I so much wanted to put my nose. My cock throbbed fit to bursting at the thought that I may just get to do that. The white gossamer stockings shimmered and begged to be caressed by a loving slave, me if possible. Her heels were relatively low at four inch and glossy white, they shaped her legs deliciously! She did a delicate pirouette and I nearly died. If I thought the rear view was delicious the front view well it nearly blew my mind.....and other things. The corset that looked exquisite from the back looked sensational from the front! My eyes were immediately drawn to her breasts, the corset having squeezed them then thrust them out at me like two ripe melons. The edges laced with white frills that barely covered the strawberry sized nipples. The bodice pulled in her ample frame but still allowed for the ample flesh to ripple. Once again the frilly suspenders framed a place of worship. The white thong equally as narrow at the front as at the back. The material barely covering ripe luscious pussy lips on a pussy that was obviously shaved. "Like what you see," she smirked breaking me from my lustful reverie. "Oh yes Mistress," I breathed reverently. "Okay since you have had your fill of ogling me time for me to get a look at you...STRIP!" she commanded. Nervously I started to strip, this was a dream come true! How many years had I fantasised about this woman and all along she had wanted to dominate me, my caged cock twitched at the thought. Once I was naked her grin grew even more. "Oh it is so adorable...and so small!....." she chuckled. I blushed bright red but she continued. "I think I have seen baby dicks bigger than this..." My cock twitched at this humiliating remark causing her to chuckle. "It seems your clit....yes clit is getting excited...but then you love this don't you worm?" She paused allowing me to wallow in my humiliation. "Yes Mistress," I simpered. "Mistress Tanya." "Yes Mistress Tanya." "No wonder your wife never bothers having sex with you.....I assume you are an excellent pussy licker to make up for your.......SHORT... cummings," she laughed at her own joke and I squirmed. I also realised that I did indeed give my wife more pleasure with my tongue than my cock.....clit! "How long have you been wearing the cage?...." "Three months Mistress." "Oh poor dear you must want to cum so bad........and how long since you had sex with your wife?." A cruel grin lit her lips as I had to think hard about that one. "Ermm....about six months Mistress," I answered blushing even redder. "Oh the poor dear she must be really desperate.....unless she's got something on the side." She winked at me. "No Mistress she has always been faithful," I retorted wondering if I had overstepped the mark. Mistress Tanya did not bat an eyelid as she had a strange mischievous twinkle in her eye. "Mmm we shall see about that after Paul has been to see her......" She must have noticed the puzzled look on my face because she explained. "Master Paul is my husband, who will be up later to sample your gurly delights," she chuckled at my shocked face. "Anyway enough talk....time to find out how good a pussy licker you are." She climbed onto the bed flaunting her ample bottom as she did and causing my mouth to water. She crawled to the top of the bed and sat among the pile of pillows. Opening her legs she beckoned me to worship which I gladly did. I crawled up the bed until my head was between her ample thighs, there I breathed in the heavenly scent of her. It was intoxicating, musky and aromatic....the scent of a horny woman. There is nothing in the world to beat this scent, it had my heart racing and my clit dribbling. I lent in and ran my tongue up the panty covered lips of her pussy. Because the thong was so skimpy I was able to lick panty and pussy at the same time eliciting a moan of pleasure from her. I was rewarded with my first taste of her, once again intoxicating.....all woman! The musky pussy juice coated my tongue and had me groaning with pleasure. "Such a devoted slave.....you love...no adore pleasuring pussy don't you slave?" she murmured. "Yes Mistress," I gasped. Very quickly the crotch of her thong was sopping wet from my saliva and her pussy juice but she wanted more. "I want that piggy tongue deep in my pussy," she growled. Without being asked I reached up and took hold of the waist band of her thong, she in turn lifted her bottom allowing me to pull them down, I watched my mouth watering a string of sticky pussy juice trailed from thong to her plump pussy lips. Then, as my new mistress decreed I buried my tongue deep into her pussy eagerly, her sticky pussy juices coating my face as I did. The taste was heavenly, musky.....womanly...... delicious and I groaned in unison with her. I spent several minutes lathing my tongue across her pussy lips gorging myself on her sticky, unguent pussy juices. Finally regaining my senseless I found her hard clit and began to play with it eliciting a yelp from Mistress. It did not take long to have a writhing on my eager tongue and even less to have her screaming her first orgasm. "My my you do have real talent with that tongue of yours......" "Thank you Mistress," I felt warm inside. "But then you need to with such a tiny clit," she snickered shooting me down. She allowed me to bring her to climax three more times before pushing me away. "Damn I am so horny.....I need a fuck," she growled. To my surprise she had me stand and then proceeded to unlock my cock......clit. My heart soared when I realised I was going to get to cum.....even more so when it would be whilst fucking this heavenly creature! She sat on the side of the bed and tilted her head examining my rock hard five inches. "Now that is not going to work," she murmured flicking my hardness. She got up and swayed seductively to the dressing table returning with what looked like a black dildo and some lubricant. Sitting once more she squeezed a small drop of lubricant onto the tip of my cock, I gasped at its cold touch. "Rub that in.....carefully.....no cumming sissy," she chuckled. Carefully I coated the rest of my clit with the lubricant, and like she ordered I did it carefully because I realised it would not take much for me to cum. She then took the black dildo and it was then I realised it was hollow! Taking hold of my clit she slipped the dildo over it pulling it over my clit and securing it with the attached rubber strap at the bottom around my sissy cherries. Just the act of her doing this nearly had me climaxing but somehow I managed not to. Looking down I now sported a ten inch black monster between my legs. Mistress took a hand full of lubricant and began to lathe it onto the monster and I realised to my horror I could not feel a thing! Satisfied that it was ready she crawled back onto the bed and arranged herself among the pillows at the top of the bed and once again opening her legs as she did. "Come on stud fuck me," she growled. Reluctantly I moved between her legs knowing I was going to get no pleasure whatsoever in fucking her. But then my submissive nature kicked in and I realised I was going to give my Mistress so much more pleasure than I ever could with my tiny clit. A thrill went through me and my clit throbbed aching shy of release. Gently I placed the monster cock at the edge of her plump pussy lips. All the while she watched me a wicked grin on her lips. "Careful now....you have never had a real cock so don't know how to use it....." The humiliating remark had me blushing and her chuckling. "Don't worry I will tell you if it hurts.....now fill me with that monster," she commanded. I slid the monster cock inside marvelling at how easily it slipped inside her, she must have been used to something this size which made me wonder about her husband.....how big was he! Soon the whole thing was inside her and she locked her legs around me keeping it there. "Mmmmmm I love the feeling of being soooo full!," she crooned. She made slight movements on the cock, slowly increasing until she could take no more. "Fuck me...long and slow," she demanded. I pulled out barely leaving the tip in and then slowly pushed back in to the hilt, she mewled at this. I continued with the same kind of stroke but slowly upped the tempo and she started to squirm. Soon she was gasping and crooning.....then she demanded it faster....screaming as her orgasm overtook her. I slowed the pace realising this was going to be hard work but she demanded I keep up the pace. Three orgasms later and slick with sweat she allowed me to come to a halt. She pushed me away and then rolled onto stomach presenting her ample bottom to me. At the sight my mouth began to water, looking back over her shoulder she grinned. "What do you want sissy?" she asked mischievously knowing full well what I wanted. My gaze was captured by the ample orbs, the dark scented crease.....in fact I could see that her pussy juices had trickled between her legs and coated the soft puckered hole. I groaned and gave in to my submissive nature much to her amusement. "I want to worship your wonderful bottom Mistress," I crooned in a state of submissive bliss. "Kiss it first.........then your piggy tongue can get to work cleaning me," she demanded. I needed to more asking, I began to kiss the velvety soft orbs covering every millimetre in my ardent devotion of my Mistress. However my need to taste that dark rosebud was very strong and soon my tongue was descending into the musky delight. "Eagerly little piggy aren't we," chuckled Mistress. I could not answer my tongue was tasting and delving with abandon. Filling my senses with the taste of her, equally so in that I was licking pussy juice and the dark flavour of her rosebud. I fell further into subspace and my dildo sheathed clit throbbed in frustration. Soon I had lapped up all the juices and my tongue started to snake further into the tight rosebud eliciting a mewled of pleasure from her. "Perfect sissy, now fuck me good and hard doggy style.......fuck me like only a man can...." she demanded. "...if you can," she quipped. I bristled at this remark and was determined to do exactly as she demanded. I placed the monster cock against her sex swollen pussy lips and thrust in with all my might. In this position the monster easily slipped all the way inside and I winced as my sissy cherries were crushed by my efforts. "Are you going easy on me," she quipped sadistically knowing I had put a lot of effort into that stroke. Maddened I pulled out and began to hammer her pussy with all my might. "Much better.....now come on stud FUCK ME!!" she growled. I rammed her pussy with the monster dildo the effort causing me to pant like a whipped dog and much to my relief she began to scream her orgasm to the room. However she was soon demanding more....harder...faster. She came twice more before finally falling in a heap on the bed allowing the dildo to pop free and me to gulp in oxygen. I felt like I had just sprinted a marathon and it took me all my effort not to fall on top of her. As it was I rocked back on my heels and heaved heavy breathes willing my beating heart to come to a sensible rhythm. What seemed like ages later Mistress stirred. "Mmmm I have been playing with you for quite a while, time to prepare you for hubby." Mistress had me stand in front of her a wicked grin on her lips. "Don't you dare cum sissy." She slipped the ring from around my sissy cherries and then began to slide the sheath slowly from my clit watching me avidly as she did. I drew in breath and gritted my teeth because the sensation had me on the brink of climax. So much so I wanted her to simply whisk it off, but she wanted to tease me so took her time. I breathed a sigh of relief as it finally slipped off and I had managed not to cum. She seemed disappointed which had me wondering what the consequences of failure would have been. She stood and then ordered me to lie on the bed with my arms by my side. Strangely she the cuffed my wrists to the bottom of the bed. She then cuffed my ankles before pulling my legs back over my head. It quickly became apparent why she had tied my wrists to the bottom of the bed. As she tightened the bonds my upper body was pulled under me and I was left staring at my rampant clit dangling above my face. I groaned as I realised what was going to happen eliciting a chuckle from her. "I think you may have guessed that I am going to let you cum haven't you sissy...." "Yes Mistress." ".....and where do you think it's going to go sissy?," she tightened the screw. "In my sissy mouth Mistress." "Yes exactly that sissy, and don't you dare get any on my sheets," she commanded. She moved away before coming back to brandish in my face what she was going to use to make me cum, it was a six inch dildo with a handle. The handle was strange in that it was rather fat, much fatter than the dildo itself. I almost sighed with relief at the size of the dildo because I had played with butt plugs around the same size. Mistress must have noticed this because a mischievous grin lit her lips. She pressed a button on the top of the handle and to my surprise the dildo started to unfurl until it was about ten inches long and four inches round. I gasped realising it was now quite a monster and was going to hurt. Moving to the bottom of the bed she knelt between my legs looking down at me and making a great show of lubricating the monster! To my relief she allowed it to reduce to its smallest size before slipping it inside me, there was slight pain but nothing too bad. "Mmmm seems like sissy is used to having something in her sissy pussy!" She pressed the button and I felt it grow slightly. She then began to pump it up and down inside my.... my.... my sissy pussy and to my shame I began to enjoy it. At the size it was it was just hitting my prostate at the end of each stroke fuelling the fires of my excitement.... although not quite getting me there. Mistress knew this but kept on going a wicked grin on her lips. I wiggled and squirmed trying to get the spot and in the end had to mewl.... "Please Mistress." "What do you want sissy." "I want more Mistress." "What! Bigger.........you slut!" "Yes Mistress." "Thicker...." she chuckled. "Yes Mistress I want it all," I gasped. She pressed the button and began to fuck me and although it started to feel good it was still not big enough to satisfy. "More please Mistress," I begged. "You cock hound." She winked and then pressed the button and held it there. I felt the dildo unfurl to its full size inside me as she began to pump it up and down. The feeling was now sensational. I was so painfully full yet the size meant my prostrate was now being constantly massaged. My climax was coming on at a pace and she knew it because she slowed the pace right down causing me to almost howled my frustration. "No please Mistress......I need to cum.....please!" I begged. "Mmmm but sissies don't cum," she snickered, this turned to a laugh when she saw my face. Did she mean to say that I was not going to be allowed to cum, no wonder she laughed, the look on my face must have been one of sheer horror. "No airhead.....sissies don't cum.......they sissygasm," she prompted. I felt completely humiliated by this dominant woman which only fuelled my need to cum.......sissygasm. she continued to fuck me but ever so slowly watching my face avidly, obviously watching the play of emotions across my face. "Please Mistress....please may I sissygasm," I begged total debasing myself and sending a thrill to my clit. "Well since you asked so nicely dear of course you can, but remember my warning." She began to increase the tempo and once again my sissygasm built. As it was I noticed my hard straining clit dangling above my mouth. Mesmerised I watched the pearl of sissy juice there expand and then start to drip. Almost in slow motion I watched the syrupy string stretch and then snap. Unconsciously I stuck out my tongue to receive it, it landed hotly on my tongue and I tasted myself. That was the trigger, I began to spasm and watch my sissy cherries crinkle. The first wad of white sissy juice squirted forcefully into my mouth and I squealed my pleasure, two more followed landing squarely in my mouth. The final two lacking the force of the others landed on my chin and chest respectively. She continued to pump my sissy pussy forcing the last few drops of sissy juice from me before allowing it to pop free. "There you go sissy, what do you say.....manners....not with your mouth full," she chided gleefully. I swallowed the quite substantial mouth full of sissy juice and answered.. "Thank you Mistress....oh thank you for giving me my first sissygasm." A knowing smile lit her lip as she realised how easily she had made me refer to all of my male parts and functions as female.....this realisation also hit me with the post orgasm.....sissygasm guilt I blushed....but stayed hard! Mistress released me from my bondage and commanded me to stand by the bed. "Now let me see I know Master Paul likes his girls slight and girly....well you are definitely shaped more like a girl than a man," she chuckled as I blushed. She swayed to a set of drawers and after a brief search returned with my new outfit. First she handed me what appeared to be a pair of plain white full cotton knickers, the legs and waist edged with candy pink piping. However when I looked closer I found the rear of the panties were open in a heart shape that would expose most of my bottom, again edged in pink. I quickly wiggled into them knowing my bottom was completely vulnerable a fact that had my clit rock hard in its soft embrace. She handed me the bra which was bikini style, the straps laces of candy pink and the cups tiny triangles barely large enough to cover my nipples. The final humiliation was the skirt which was in essence a belt of gossamer frills that did not cover the tiny bulge I was making in my panties and floated at the slightest breeze. Mistress had me pose before the mirror just I think to humiliate me....it had the desired effect. I looked like a pathetic wannabe sissy virgin. But I guess that was exactly the effect she was going for! Mistress once again returned me to bondage on the bed but this time my legs were slightly lower and she placed a pillow in the small of my back. She must have seen my puzzled look because she spoke. "I think I have played with you long enough.....I think it is time for Master Paul to sample your delights. She disappeared and I was left wondering what was going to happen next. Of course I knew exactly what was going to happen next and my clit throbbed back to life. Tied as I was I did not hear him enter the room so jumped at the sound of his voice. "Mmm that looks like a tight boy pussy," he chuckled. He then appeared at the side of the bed. He was wearing a kimono similar to Mistresses only in blue. I had only seen him behind the counter before so I had no idea what he really looked like. "I hear my wife has been having lots of fun with you..... and I can see you've been having some fun of your own," he lent forward and scooped up some of my sissy juice that had landed on my neck. I expected him to put the coated finger in my mouth but instead he opened his kimono and daubed the tip of his rock hard ten inch cock with it. He then allowed the kimono to drop from his shoulders revealing his body fully to me. For an older man he was well toned and I could see he worked out. There was a little sag with age but not much. My attention was however drawn to his throbbing cock. Subconsciously and submissively I licked my lips causing him to chuckle. "I guess you want to wrap those sissy lips around my cock..... don't you sissy....." "Yes Master," I mewled. "Yes, watching the videos I know you are pretty good at it." He then grabbed his cock and began to slide it across my lips painting them with both my sissy juice and his pre cum. I stuck my tongue out to taste the heady combination and my clit twitched above me. Shamefully I hoped I would have a second.... Sissygasm when he fucked me! Because I was tied to the bed on my back there was no way of sucking him into my mouth fully. He settled for me sucking on the head swirling my tongue around it and getting him even more excited. When he could take no more he move to the end of the bed. I felt him stand on the bed and then he was towering over me. Obviously the effect was to further show his domination over me because there was no way he would be able to enter me from that angle. I shivered at this humiliation but my cock throbbed and twitched shamefully. He reached down and stroked me and I sluttish groaned at his touch. I watched as Mistress slathered his monster cock with lubricant then guided to the entrance of my boy pussy. As I said he could not enter me but he took great pleasure sliding his slick cock across the entrance and against my tiny clit and sissy cherries, once again the difference in size was humiliating. Having humiliated me to a bright red blush he knelt and I felt the tip of his cock against my wet boy pussy. Because Mistress had already fucked to climax his cock slipped inside easily but it was oh so much different. Unlike the dildo it was hot and throbbing, when he plunged it to the hilt and held it there I could feel the blood pulsing through it. He paused watching the reaction on my face. "I think our sissy boy likes having his sissy pussy fucked..." he chuckled. "Well they do say sissies are better than girls.... eager to suck cock... eager to have their pussies fucked.... never say no.... to anything," he snickered. As he was saying this the humiliation was making me even more hungry for him to fuck me....make me his sissy bitch. So much so that I began to wiggle my bottom causing him to chuckle. "Are you ready to be fucked........you little minx!," he growled. "Yes Master please fuck me," I begged. "Call me daddy..... and beg some more.... I like it when my bitches beg." "Please daddy.... please fuck me with your monster cock.... please make me your sissy bitch." I debased myself for his pleasure and to my shame my own. I had had my first sissygasm and wanted more!. At this Mistress stepped onto the bed feet either side of my head. She then lowered herself planting her sopping wet pussy over my lips and my nose against her brown puckered hole. I breathed in the scent of her causing my clit to throb. "lick me," was the simple order. I eagerly plunged my tongue into her volcanic pussy and wallowed in her hot sticky juices. All sound and sight cut off by her plump thighs, lost in a world of hot wet pussy and a throbbing monster cock filling me! Slowly he pulled out pausing as he hit my prostate to rock gently over the spot driving me wild. Soon I was bucking and groaning like a whore, meeting his rampant thrusts with my own. The fuck was long and slow and I revelled in the sensation, even managing to make Mistress climax. Soon I could feel my sissygasm building and realised he was also well on the way to climax as well. I felt the warm glow and my sissy cherries spasmed. Because I was tied more on my back my sissy juice splashed hotly onto my chest. My sissygasm seem to spark both daddy and Mistress off and soon he was bellowing his climax and filling my sissy pussy with hot sticky man spunk. I felt it gushing hotly inside me filling me up and marking me as his property..... His sissy bitch. At the same time I was drowning in syrupy pussy juice as Mistress squeezed my head between her thighs and mashed her pussy against my face even forcing my nose up inside her puckered hole! Satiated he pulled out and I felt the trickle of spunk down my crack. Mistress fell backwards onto the bed exhausted. He moved round and without hesitation I was cleaning his cock of his spunk and my pussy juice. The taste was dark and delicious and I revelled in the humiliation of the task. My cock throbbed and once again sprang to life causing him to chuckle. "Well I have an errand to run so I will leave you in Tanya's capable hands," with that he slapped me rather hard on the bottom causing me to squeal. My clit sprang to life giving away my perversion for being spanked not that they did not know all my perversions already. "I see my new girl likes to be spanked.... maybe we can play later," he mused before leaving the room. The hand print seemed to linger and soon that nice warm feeling set in causing my clit to twitch which was noted by Mistress. "You are such a perverted fag," she chuckled. She untied me from the bed and then beckoned me to follow her. We travelled down stairs and then through another door into the basement, into what appeared to be a suit of rooms. As we travelled downstairs I ogled her perfect bottom and tried to emulate her swaying walk, girl was I deep in sub space and loving it. As she walked she spoke. "Samantha did a fantastic job of trapping you and Wayne did okay sealing the deal but there is no way he is going to be your pimp. He is far too stupid...... "she sniggered. "No I think Samantha has had her fill of a bit of rough, I think it's about time he found out just how connected I am," she growled. From the intimation I was guessing it was not going to end well.... prison maybe?.....pimped out himself, now that would be poetic justice. "No my little sissy fag, I am going to be your pimp...." She must have heard my intake of breath because she laughed. "You don't think we got all this luxury from the shop did you?...... we have been running high class call girls for quite a long time..... Master Paul has quite a few connections and so do I thanks to a little bit of blackmail." I realized I was not the first man to be trapped by Mistress and Master. I was however the first to be added to their harem it seemed. "You are going to make a fantastic addition to our stable. I know lots of perverts who will want to play with a sissy like you," she smirked. I should have been frightened by what she had planned for me.... Indeed I was a little, but by clit throbbed at the thought and deep down I wanted this.... to be totally debased and humiliated by this dominant couple. My submissive reverie was interrupted when we entered the first room. This turned out to be the dressing room as she began to open doors. There was a wardrobe behind each, one contained maids dresses of all kinds and colours..... there was even a black rubber dress! A wardrobe containing rubber clothing of all types from full gimp to skimpy underwear, another contained dresses...... One which really caught my eye was like a costume shop! School girl, Lolita, nurse, nanny, maid, fairy... the list seemed endless. I was in heaven my heart pounding my clit rock solid and leaking duly noted by Mistress. I would have given my soul for the contents of this room. The only consolation as she led me to the next room was that I knew I would be getting to wear a lot of the items! The next room was a submissive's dream and sadists workshop. Bondage toys of every sort graced the walls as did bondage gear and punishment toys. It was here Mistress sprayed my cock with freezer spray and returned it to its bondage. However this cage was solid steel and far more secure than the one I had worn previously, she took great delight in showing me it was lined with tiny spikes. To test its effectiveness she lounges on a nearby couch and had me lick her to climax twice. By the end I was crying with the pain and frustration my clit was receiving, Mistress just chuckled at my tears. The rest of the rooms turned out to be play rooms....dungeon, classroom, clinic all for the enactment of perverted fantasies. A lot of them were my fantasies so my mouth watered and my clit got spiked. Mistress had me pleasure her pussy for a few more climaxes before she let me leave, assuring me she would be in touch soon. I arrived home exhausted to find my wife red and flustered, but strangely in a lively mood. I asked her what was for tea and she simply said, "ME!" dragging me upstairs. This was it, she was finally going to find out what a pervert I was. Once I was undressed she would immediately see the clit cage....and if she wanted sex! I knew I had to confess so at the bedroom door I tried to stop her pulling me to the bed. She came back into my arms and then whispered in my ear. "Honey Master Paul was here....." She let that statement linger. "I.....I," what was I going to say?.... I can explain. "He told me all about you......" So she now knew all my dirty little perversion, I should have been expecting divorce but that did not seem to be the case. "How you are is fag boy......what did he say.....his eager little cock sucker...," she smirked up at me and I simply looked down dumbfounded....he was claiming me as his gay slave!. "Well you always said you were bi curious....well not curious any more it would seem," she giggled. "I can explain....." "There is no need. Master Paul explained everything and then fucked me with his magnificent cock. Afterward he said he now had two bitches.....and I have to agree," she winked. Lost now I did not resist as she pulled me to the bed and opening her legs commanding.... "Lick me." I looked at the sex slimed and swollen pussy lips and was soon naked between her legs.

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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...

1 year ago
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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...

3 years ago
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She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

4 years ago
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100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

3 years ago
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Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

3 years ago
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Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

1 year ago
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A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

3 years ago
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407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

2 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

1 year ago
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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
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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
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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...

2 years ago
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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."...

2 years ago
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My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
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Forever Her Sissy Chapter 5

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

1 year ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
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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
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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...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

1 year ago
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Forever Her Sissy Chapter 4 of 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

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