Milking Sissy free porn video

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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 I'm being pumped. I love that. The milking cup on my beautifully shrunken sissy clitty isn't really necessary either. It's been a long time since anything came out of that other than my watery precum. But that too is there out of ritual and familiarity. The gentle suction though does feel nice. What feels heavenly though - aside from my Master's cock sliding past my collagen-puffed lips or filling my sissy ass, that is - is when the pumps start running and my milk lets down. I've been so pickled with all the hormones and lactating drugs for so long I can hardly remember a time back when my breasts weren't full to the point of bursting. It's gotten to the point he's putting me here in the milking stall twice a day. Recently, he's been talking about upping my dosages to get me milking three times a day! I don't know if I could stand the bliss from that. I sure am willing to try it. I love pleasing my Master. In any way he wants of me and especially if he wants me to yield that much milk, then I will! The feeling as my milk starts coursing through my puffed up and oh-so- sensitive nipples is a pleasure that's difficult to do justice describing. It's like a really long and wonderfully drawn out climax. I think real girls could best understand that than other guys. Not that I'm still a guy, that is. Not now. Not with these huge milk filled tits. Not with this surgically altered woman's body. And certainly not with my wonderfully limp sissy dick. A year into all this - or was it two - I'd come so far along that he decided to test things one last time. He milked me then in a different way than I'm milked now. He had me all nice and strapped into this rig and then he inserted this dildo sort of thing into my boi pussy and began massaging my prostate - or my sissy g-spot as he likes me to call it. We'd done this lots of times before when he had my sissy clit all well caged up. And every so often he'd collect the fluids he oozed out of me so he could analyze them. Normally, he'd have me lick them up off the collection plate he'd have positioned under me. When the results came back from that last time he was very happy and that made me happy too! He finally told me what that was all about. Each time he'd collected samples he had them checked at his lab - he's a biochemist of some sort, I think - to see if there was any maleness left in my sperm. That last time he checked was the third time in a row that the results came back entirely negative. It meant that all the sissy hormones he'd been pickling me with had finally had their effect! I was neutered! I was so happy about that! From how hard the bulge was in his pants, I could see it turned him on to! Finally, we'd gotten me to the point of being completely de-maled and even more a sissy! As he took me into his arms that moment and kissed me, my emotions broke and I felt this massive wave of pleasure roll over me. I was having a "sissygasm" without my Master even having his cock in me. It was wonderful for the both of us. Especially as this meant that we could move on with the next phase of making me into his ultimate sissy fuck toy. That is; pumping me full of even more hormones and chemicals until I not only sprouted bigger breasts but ones that actually did lactate. My little A cups were the cutest things ever but so long as my testes still put out their boy hormones - however little that might be - we couldn't get to where we both wanted me to be. Once neutered though, we could! I really did swoon at that news. A few minutes later, when he had the first shot of the new hormones ready, my Master was so excited about it that he had to take a moment to get a hold of himself to do the shot right. After that we fucked like the passionate lovers we are. Me, his submissive sissy fucktoy and him, the dominant Alpha Male Master that he is. Even thinking about that day still turns me on. And it's been several years now since then. It did take a while and we did use some of that stem cell "grafting" to really get my breasts big enough. But, now they are. It took a lot of self control on my part not to work my nipples raw trying to squeeze milk out of them before my breasts were really ready. I wanted it that bad. And my self-control really wasn't that good. Toward the end there, in the last month or so before I did start lactating, it got really bad. My tits were really big by then. Their weight was actually turning me on and my nipples itched all the time and were super, super sensitive. My Master could tell what was going on. So, he took matters into hand - and I love it when he does that, even if it can hurt a bit in the process. He strapped me into the conditioning bench we'd set up. It's a really fancy rig he made himself. The whole thing can rotate such that I can be on my back with my legs up for fucking - and for like when he "examined" me and gave me all those sissyjuice hormone shots right into my balls - or facing down with nothing but that straps holding me in place. That, and just about any position in between. The pads on it are like the ones they've got in old people's homes that you can lay on for days without sores developing. He calls the thing his conditioning bench as that what he does with it to. He has strapped me onto it and into it and then he gives me a couple more shots of his own special "girly juice stuff," slips the headphones on to me and I'm soon drifting off in a wonderful haze with his wonderful voice filling my ears and my mind with all his wonderful commands and instructions and everything. I remember, distantly, doubting him when he told me he would change my personality this way - or change anything else about how I thought or behaved. I know he's wrong. I've not changed at all. I've always been a sissy submissive and I've always wanted a man like my Master to make my outsides match who I really was on the insides. I humor my Master about this. He just happened to come up with those "subliminal conditioning messages" that really didn't tell me anything new about myself or anything different than who I was already. I think it's all just his way of telling me it was okay to let out my inner-self to share with him. I don't think he needed to be so elaborate with this rig or the messages he has playing into my ears when I'm on that sissyjuice. But, it makes him happy to do so and I love making my Master happy! So, I just play along. That time he strapped me in, he set in a new shunt into my arm, and hooked up an IV bag. I could tell then that this would be another extended session - days, perhaps - that I'd be on the bench. He put some syringe into the feed on the IV line and I soon felt that familiar wonderful warmth and haze coming over me. My Master leaned in then and kissed me nice and deeply. "I know it's been rough for you princess. So, I thought I'd help you get past this last time. It's only going to be a few days now until your body finally clicks in and you become the Milking Sissy I want. So, I'm just going to put you under until then so you don't stay so frustrated." he purred into my ear as he held me tight. I could only blubber my thanks as I really was beside myself with how my breasts felt. He smiled at me, stood back and rotated the bench around so my mouth was in the right position. I instinctively opened up to take him in and soon enough his wonderful cock was sliding deep down my throat. My Master knows me so well. With his cock in me I soon calmed down and focused on pleasing him. Seeing that I'd attained that "sissy bliss" as he calls it, he pulled himself out of my mouth and once again rotated the bench around. I didn't have long to wait until he'd slid his cock into my boi cunt. A wave of pleasure washed over me and I had another sissygasm when he began flicking my nipples as he pistoned that cock into me. It was heavenly. We made love like that through another deep sissygasm for me and, at last, a wonderfully deep cum for him. I love when he shoots inside me like that. I really can feel his hard cock throbbing inside me and when he spurts his cum it always sends me off to! Of course, that just means for more sticky and watery precum oozing from my sissystick. But we both love that wet mess there. After we both climaxed from his fucking me so well I really began drifting off into the wonderful haze of what ever it was he had injected into the IV. My Master kissed me deeply again and put in my headphones so I could let his voice run through my mind as I floated along. The rest of the time became very hazy for me. A happy haze. He later told me he kept me that way for two weeks! He hooked up a catheter onto my limp sissystick so I wouldn't make a mess when my bladder got too full. And as I was hooked up to the IV for nourishment, there wasn't anything coming out of my backside except lube and his cum. I later woke up and came out of that wonderful sissy haze as I lay in his bed. He'd washed me and combed out my hair. My Master truly is so good to me. I was very weak and very, very hungry. As I began to stir he came into the room and had his arms all wrapped around me. It felt so good to be in those big strong arms of his. I squirmed happily as I felt his cock harden and, soon enough he placed the head of his shaft onto my rosebud and pushed himself in. I squealed with sissy joy as his cock went in to its hilt. As he rocked back and forth in me, he leaned forward and kissed me deeply. I melted at that. As I usually do. Then he leaned back and smiled broadly. "You ready sissy?" he asked. I was still not quite myself after having been on the bench for so long. Knowing this, he reached out and placed a hand on one of my breasts. Even his touch felt soooo good. But then I realized how different my breasts felt. They really did feel heavy. And... tight. Before I could figure any of that out... my Master squeezed his hand and all of a sudden I felt a shiver run all the way through me and my nipples became even more alive. And then it happened. As he squeezed my breast I watched this thin stream began to spurt out. It was milk! Milk from my own huge sissy breasts! I was milking! I was his Milking Sissy! Finally! I cried out in surprise. I cried out in pleasure! I cried out in relief! Finally! He squeezed a bit harder and even more came out! Then he leaned down again and placed his mouth on my nipple where he began suckling. The sensation of his drawing milk out through my nipple was too much! The awesome intensity of the pleasure of it drove me over and I screamed out my huge sissygasm climax. I bucked hard on the bed and writhed around as he continued to fuck me and continued to suckle on my huge sissy tits. It was incredible! I was out of my mind with pleasure. I was screaming from one sissygasm to the next. I never wanted it to end. It was beautiful. I was so blissed out that it took me a while to realize that he had stopped. We'd been going at it for a while and he'd switched from one swollen tit to the other, fucking me deeply all the while. I'd climaxed again and again. Finally, he'd both drained me and himself. We'd made quite the mess. Happily so. He laid himself down with me and we got all wrapped around each other. I was so delirious with pleasure that I was babbling almost incoherently. The only way he got me to stop was by kissing me hard, deep, and long. Laughing, he said "You're just as I thought you'd be. I've really created the sissy of my dreams. You are a cock hungry, utterly submissive, completely de-maled and now, you're also a milk heavy sissy cumslut. Damn, but I do love you!" I began crying again and buried my face in his broad, muscular chest. I was in bliss and we both knew why. Later, after we'd recovered and I'd gotten some solid food in me, and after we'd changed the sheets, he explained to me how things now were. My milk had finally "let down," obviously. And I would now be producing it as long as I was taking the special hormones in the shots he gave me each week. Well, for the past two weeks he'd been giving me those special hormones on a daily basis and that's what finally brought my glands to this point. "Initially," he told me as I was still wolfing down my meal, "we'll only need to milk you about once a day. But with the dosage you're on and with your metabolism, we'll soon have you up to twice a day." I moaned with lust at those words. Twice a day like what we just went through? Oh yes! My Master smirked at that as if he could read my mind and all its sissy thoughts. "I don't think either of us could take doing that twice a day. But it will be wonderfully intense for you none-the- less." Once I'd finished my meal and worked up the energy he showed me the equipment he'd set up during the time I was floating on the bench. It was a series of metal pipes bolted together to form a framework into which he'd shackle me so I wouldn't thrash around and hurt myself accidentally as I was being milked. The sight and the thought of those hoses and milking cups being suctioned onto my huge tits was enough to make my sissyclit twitch happily and ooze more of my sissycream. He smiled and told me that I'd had enough for that day and that I needed my strength if I was going to be milked so regularly. I pouted but realized I really was still exhausted. My Master led me back to my bed and we got me all set up. I wiggled my hands into the bondage mitts and he hooked them up to the straps coming up from the sides of the bed. The ankle straps were next and I was soon well secured to my bed. I've gotten very comfortable with this and actually like being so well immobilized. He tells me this reinforces my need to be passive and submissive. I like that for that's what I am - passive and submissive to please my Master. He slipped the earphones on again and kissed me deeply as he secured the blindfold over my eyes. I was soon fast asleep as his wonderfully commanding and dominant voice echoed through my mind and ever deeper into my subconsciousness. Over the next several months my breasts really filled out. The growth of the mammary glands within them and their constantly producing all that milk really puffed them up. I kept going up in cup sizes and Master kept changing the size and shape of the maternity bras he had ready for me to wear. He's so considerate like that. I was soon back doing my usual exercises to keep myself toned and in shape - "A fit sissy is a happy sissy. A fit sissy makes her Master happy. A happy sissy makes her Master happy. A happy Master makes his sissy happy. Always be a happy sissy. Always be a fit sissy" - is one of the mantras he played for me through those headphones. He's so silly that way. I knew all that from the start! It was nice to hear all that however. It's always good to know that the thoughts I was already thinking were exactly the ones that made my Master happy. I love making him happy. Anyway, my fitness routines always had lots and lots of stretching exercises to keep me limber and toned. Being a flexible gurl for my Master means he can bend me over and take me so much better and often! I also was doing lots and lots of leg work to keep my legs nice and sexy for him and to keep my butt so perky and fuckable. My Master loves how bubbly my butt is - "Just like you, babe, nice and bubbly all the time!" he's told me! But now the exercises also included more back strengthening ones. As my milky breasts got bigger and bigger I really needed that lower back strength. Then, one night some several months after I'd started milking, Master strapped me into the special bondage frame that he made for our playtimes. This time it would be playtime with him and his friends. First though, he helped me into my favorite latex body suit. It was all nice and shiny and smooth and sexy black latex with cut outs for my breasts, my sissy cunt, a hole which he'd pull my little sissy stick out through for it to be on display in the pretty cage I wore over it, and then holes for my eyes, nose and mouth. I was all shiny and slick and smooth in that latex. It took a while to shimmy into it even with the lube and all. But it was worth it. And besides, Master liked squeezing me into the thing and that always got his motor running. Fun thing about the latex is how easy it is to wipe off cum from after I would give him a nice sloppy blow job for having worked so hard to get me into the outfit! He then laced on these knee high latex ballet heel boots and then laced on these opera length latex bondage mitts. It took some careful stepping and balancing for me to step into the bondage rack for I could hardly move in the latex bondage suit I was already in. Then he locked the rack around me. He had me in that rig for when he invited his friends over to show them how my milk had really come in. I missed having his friends over. I liked his friends. They were such real men. Not as manly as my Master but, close. And they definitely knew how to treat a sissy fucktoy like me! I'd scamper about them in some silly little maid's outfit or some silly cheerleader's outfit or some silly schoolgurl's outfit or in some silly sissy nighty thing. Whatever Master told me to dress in. By night's end it really didn't matter as whatever I'd been wearing would be long since pulled off of me by those men. And my sissy cunt would be nicely stretched from all their fucking me. My mouth would be sore as would be my throat! I loved it! I didn't ever need those messages playing in my ears to tell me I loved it. I knew it always! That night however, what was on display for his friends was his new "Milking Sissy." I couldn't have been happier to be on display like that for him. I was ecstatic when my Master was showing me off that night. And the looks on their faces just made me even happier! I was surrounded and helplessly bound before all those hungry, hungry wolves! Helpless prey before them. Helpless milk filled prey! I've managed to cum just from thinking about that night. Thinking about it while pushing one of my big toys in my sissy cunt and working my thick nipples as I remember that night. The men were fascinated by what he'd achieved. I couldn't really follow what he was saying about the DNA or RNA or "stem cells" and crisper ("No my sweet, that's 'CRISPR'" he always reminded me) and all those other things he was saying to them. I was just so proud to have pleased him. That and feeling the increasing pressure in my breasts. Master had deliberately not milked that day yet. I was being milked at least once a day by then. Sometimes twice. And it had been a whole day since last he'd gotten me in the milking stand. The pressure was really getting bad! But I stayed with it. I wanted to make my Master proud! Eventually, he got done talking about all the procedures and science stuff and medical stuff he'd done with me. And done to me. Then he turned to me in that rig and gave me a nice deep kiss. I swooned at that. I love being kissed by my Master. It makes me so happy when my Master kisses me. He then cupped one of my breasts and rolled it a bit with his fingers. He'd done this lots of times by then and knew just exactly how to get me to express my milk like that. Quickly, the droplets popped out through the glands in my nipple and then began dripping. He squeezed a bit more and streams of milk jetted out from my nipple. That felt soooo good! I whimpered as the joy washed through me. He leaned in and kissed me some more. "Good gurl. Good gurl. You're my good gurl. That's it baby. Enjoy this. You're my good Milking Sissy. My good, good Milking Sissy gurl." He purred. I shivered as I felt a climax roll through me. The sensations were that much. My milk coming down, the fondling he was doing on my breast, my being shown off like some prize milk cow, his kisses, and his praise. Oooooh... his praise. He was happy with me. My Master was happy with me! I was being a good sissy gurl! I was making my Master happy with me by being his good Milking Sissy gurl! Oooo! I felt my sissy stick throb as my climax continued and I knew there was a pearl of my precum drooling out through my chastity cage. Even through my eyes lidded with the pleasure rolling through me I could see Master's friends as their hunger grew and the lust became fiery. I ached for that. "So, as you can see, I've successfully completed these alterations and she's now lactating quite heavily. I expect that within the month she'll be up to a gallon a day from each breast. The only question is how her liver function will be maintained with the dosage necessary to keep that lactation flowing at that level. I monitor her on a twice daily routine and have been able to maintain excellent precision as a result. Mentally is another question." He smiled at that, squeezing my breast a little tighter which sprayed more milk out and made my eyes flutter from the increased pleasure. "I honestly don't know how much more she can stand" he chuckled. "She's in a near constant euphoric state and her dopamine levels are constantly well above normal. She'd otherwise be in severe dopamine depletion by now but I've handled that with by applying artificial dopamine within the lactation mixture." He kissed me again and then turned back to his friends. "Once I have her stabilized and her process normalized I'll move on to the specifics of the lactation composition. I estimate another six months of adjustments there and then I'll have her at the production- ready state." I couldn't follow what he was saying. I was just panting from the pleasure and wanted his hands back on my breasts as the pressure was building again. "And the compounds won't be degraded?" asked one of his friends. "No, they won't. If anything, they'll be enhanced. And all '100% natural,' as it were" he laughed again. So did his friends. "Goddamn!" one of his friends expressed "A milking sissy who's milk will make other sissies! I never thought you could make it happen!" My Master seemed to be even happier at the man's statement. "That's right Chris, her milk will be the absolutely perfect chemical compounds to feed to your boy, David, to gently transform him into exactly the sort of sissy gurl you've wanted for yourself. The combination she'll produce here will have both a neutering effect and make the subject more mentally pliable. And the more of her milk they consume the faster the process will take place and the more feminized and docile they'll become." He said happily. "Her milk can be substituted for regular milk, correct? So it could be used in place of regular milk in protein shakes or ice cream or coffee creamer or..." another friend asked. "Or anything else that involves dairy milk." My Master finished for him in reply. "Homogenizing will degrade the compounds so I recommend against that. But a direct substitute would be quite effective." "Damn.... Switch out the milk Louis pours into those energy shakes of his and..." another friend wondered aloud. "And he'll not only soon be the happiest little fuckbunny ever but he'll have sprouted wonderfully perky tits of his own. Perhaps not as big as the ones on my beauty here. But easily a handful just with the milk substitution. And once you have him at that point, mentally, his consent to other enhancements would just be a given." My Master continued. "Now, gentlemen, as you can see, the milk production in such volume does come with some price to be paid if its extraction is... delayed. And I think my gurl here has been more than considerate in enduring that delay. So, how about we all enjoy what she's worked so hard at providing us, eh?" He asked his friends happily. "Uh, you just said her milk would feminize.." another of his friends questioned. "Oh, no! Not now. No, not even close. Those changes are many months away. Right now, her milk is as regular and safe as that which came from your own mother's breasts. And hers is quite tasty I can assure you. I enjoy it as much as I can myself! Here, let me show you." My Master replied and then turned to me again. His smile was so warm and the pride he had for me was so clear in his eyes. I just beamed at it. He then wrapped his mouth around one of my nipples and began sucking on it. By then, each of my nipples was as big around as one of his thumbs and easily an inch and a half long. He'd tease me about them almost being longer than what was left of my shrunken little sissy stick. They certainly got a lot harder when I was turned on than my sissy stick now ever gets! His lips felt heavenly on my nipple. They always do. And his sucking on it made me swoon with pleasure. In no time at all he had suckled out a mouthful and then turned to his friends. Swallowing it, he answered their doubts. "See?" he said, licking his lips "absolutely safe. I've no intention of becoming some sissified fucktoy, thank you very much!" he laughed. And his friends laughed to. Soon I had a crowd of hungry, hungry men surrounding me. Their lust was blazingly clear. And I was bound, helpless, before them. Helpless and with my breasts so heavy and swollen. Helpless in that slick and shiny latex bondage suit with my hands helplessly locked away in those latex bondage mitts. And with my feet trapped in those long lace up latex ballet heelded boots, even if I somehow got myself out of the bondage frame there'd be no way I could escape in those heels. I was bound and helpless and helplessly bound! And surrounded by hungry men eager to feast upon me. I was in heaven! One by one and then two by two they began having their taste of my milk. My milk coming from my huge and swollen breasts. Those hungry wolves were feeding on me. Those alpha predators were feasting on me. I loved it. The sensation of my milk being pulled through my swollen thick nipples was awesome. It was different from when I'm in the milking stand and the pumps are doing the work. The lips of these men were so much more sensual then those pumps could ever be. I was in deep, deep subspace from it all and the pleasure emanating from my breasts and through my body was almost more than I could stand. Through it all my Master was by my side, lovingly nuzzling my neck and shoulders as his friends took their turns feasting and feeding on my flowing milk. When they'd each taken their first feeding they started playing with my heavy tits. Squeezing them to see how far they could make my milk spray. Squeezing them to spray each other with my milk. They were all happy and enjoying themselves and I felt wonderfully, wonderfully objectified by it all. I was making them happy with my milk and that made my Master happy. I loved making my Master happy. Eventually, the men had their fill of my milk. At that point my Master kissed me again and asked me if I was ready to "entertain" his friends some more. I was so blissed out that it took me some time to focus on what he'd asked. I managed a dreamy little chirp of a "yes" and he laughed again. And he kissed me again. Then he loosened the frame and rotated it so that my head was in just the "right" position while my sissy cunt was also in the "right" position too! Once again, those alpha predators closed in on my helpless form. This time I was the one who wound up getting filled, not them. Though they did feast upon me - but in a different way! Later, after all his friends had happily spent themselves in my willing holes, and my Master had bid the last of them a goodnight as they left, he came back to me and detached me from the frame I'd been in all night. Their cum was drooling from my mouth and splattered all over my face. The cum they'd shot inside me was flowing out of my well fucked sissy cunt. My Master wiped away their cum from my lips and kissed me ever so deeply. I tried wrapping my arms around him as we kissed but the latex suit and bondage gloves were so tight and I was so tired that I just couldn't quite do so. No matter, his big arms fully engulfed me. Master maneuvered me to bed where he had his own private feasting on me. I'd produced some milk from between when he'd rotated me around to where my sissy holes were reachable and when he had me in his bed. So I once again had that ecstatic pleasure of being taken that way once again. I felt a bit bad that my sissy cunt was so completely fucked out by then that I couldn't work his cock in it as I usually could. My Master just smiled and fucked me harder. "Don't worry baby, you've made very happy tonight. So I don't mind if it's just sloppy seconds. Or sloppy, what is it now? Sloppy tenths? Twelfths? Hmm... There was eight of them in our group and I know that Ted and Dave were in you at least twice. And then there was Mike... was he twice or three times? Hmm..." he smiled down at me as he pondered how many times his gurl had pleased his friends. My Master wanted his sissy to always be pleasing to his friends. And if that meant his friends filled his sissy gurl up with their cum a whole bunch of times each night then that's just what I had to do! I giggled at that and my Master laughed as well. His cock did feel good inside me even sloshing through all the cum from his friends inside there. His fucking, his lapping my breasts, and sucking on my nipples, and milking me more had its effect. It had its effect on him as well as on me. He eventually spent himself inside me and I squirted some more of my watery sissy cream as well. We were both exhausted and lay entwined in each other as we let our climaxes glow throughout bodies. My Master eventually roused himself to fetch a plug for my sissy cunt. It was one of the larger ones as I was so dilated by then. I liked the pressure and fullness of it as he popped it inside of me to hold all that man juice up in my sissy cunt. He then undid the little flaps on my latex hood that were over my ears and popped in the little earpieces. I squirmed happily at that. I knew it wasn't necessary but I knew it pleased him. So I happily took the sissy pill that he handed me and kept it on my tongue as he shifted around and brought his cock up to my lips. I lightly but completely wrapped my lips around his cock and looked up at my Master. It took a moment but he then was able to release and wash down that sissy pill with his golden nectar. It's always a turn on for me when he does that. It's just my being more of a useful sissy for my Master. A useful sissy is a happy sissy. The voices in the earphones always tell me that. But I always knew that too! We were both so tired from the evening that Master thought it best just to leave me in the latex suit all night. It had built in straps and attachment points so binding me up was a quick thing. And it also meant that I could snuggle with him as we slept. My Master is so loving that way. That was one helluvanight for me! My Master was right too. He's always right. I'm such a lucky sissy to have such a loving Master! Right on schedule my milk flow became quite regular. And soon enough he had things balanced out such that my milk was exactly the right composition he wanted. I was happy with that on one level. I was pleasing my Master and I knew my milk being the right way made him very, very happy. I also knew that with my milk being that "special milk" - being "sissy milk" - that I'd soon have other sissy sisters to play with and share the job of having such Masters with. But while I was "in production mode" - as my Master called it - that meant he couldn't suckle me like we were used to. I pouted at that. He knew how good it felt for me when he had his lips wrapped around my nipples and pulled my milk out from them that way. He was tender in comforting me about it but, as always, my Master was firm in his control of me. Which is how a sissy like me needs to be controlled - firmly. I still missed his lips on my breasts though. It took almost two years of being "in production" before my Master finally decided to "change the mix" back to just normal milk. And then to "dial it down" to where I only needed to be milked but once a day. I missed - dearly missed - the sensations of being pumped the twice or three times a day I'd been going through for those years. The bliss of all that milk flowing through me is almost indescribable. Especially when my Master would take his "Milking Sissy" like "a bull mounting his prize heiferette!" My Master fucking me while also milking me never failed to touch off a blissful sissygasms within me. He even had this latex body suit in Holstein colors and pattern. Setting the nose ring hurt but once I'd healed from that he'd have me slither into the suit, clip a leash to my nose ring, and "lead his prize Milking Sissy down to the shed to be milked like all the other cows in the herd!" It was silly and being on all fours took longer than walking upright and my "mooing" like a cow only added to how silly it was. But it came to turn me on something fierce. It turned him on to. He mumbled something about "objectifying" me was so "decadent" or something like that. I wasn't able to pay much heed to that as he already had the pumps on my distended nipples and was balls deep in my sissy cunt by then. So, I was too busy having another sissygasms to follow what he said as he climaxed deep in me. It was when one of his friends brought over his own "milking sissy" that my Master told me I could take a break from being the only Milking Sissy in the herd as there now two of us in that "herd" and she would take over for me in producing the sissy milk. She was cutie too! I vaguely remembered her as being the submissive boy of one of Master's friends. Then he'd been a very sexy muscular stud muffin, almost as tall as my Master and with a cock that was actually bigger! He was one of the few black men I'd met who lived up to that disgusting racial stereotype of all black guys having huge dicks. Most don't. The few that do are the ones doing porn. My Master has a wonderfully full and thick cock but he's not at all offended to acknowledge that his isn't the biggest in the world. It's the most wonderful cock though - it's my Master's cock and everything about my Master is wonderful! Seeing the submissive now was quite the change. She was gorgeous! That lithe and muscular body of hers was now all soft and smooth curves. Still toned, like mine, but so much more girlier than before. Her breasts were wonderfully large and full. Not as big as mine but, mine were still swollen with all the milk I was producing. And that beautifully big cock of hers was now just a small pretty decorative thing adorning the space between her thighs. It was perfect for her! The silver chastity ring her master had locked around her little clitty set off her dark chocolate skin beautifully. I'd wondered where Master had been spending such late nights for the past many months. Now I knew - he'd been helping his friend create another milking sissy! I didn't realize at the time what that would mean for me exactly. I was just happy for her as I knew how much joy it was for me to be a Milking Sissy and how much it pleased my Master. So, she had to be pleasing her master to! She certainly seemed happy enough. The way she looked up at her master was the same as how I look up at my Master. So, she must be at least happy at how he helped her let her inner sissy out and finally be her true self. I wondered if her master was silly enough to also use those little recordings playing in her ears like my Master did with me. Eventually my Master and her master let us gurls play with each other. The two men sat back to watch as us milking sissies began to enjoy each other. Her master even took off the silver chastity tube on her sweetly soft sissy stick so that I could wrap my lips around it. I dimly remember attempting to do that back when she'd still been a boy and I had gagged on its length and thickness. I managed it though! My Master had told me to throat the boy's cock and I did it! His tool made my eyes water and my makeup run. But I did it! And I pleased my Master in the process. That day I was easily able to swallow up her whole sissy clitty and roll it around sweetly in my mouth. She was doing the same with my sissy clit as well. It felt heavenly. Especially with our masters standing above us watching us two sissies lick and suckle on our small sissy sticks. They then had us switch to suckling something bigger and harder than our little sissy sticks - our nipples! My Master and his friend talked about how my sissy milk wouldn't have any "negative effects" on her as she was producing the same sissy milk herself! Soon I was in my favorite position - on my back with my nylon clad legs up in the air - with her heaving breasts right over my face. I had to use my arms to hold my breasts up to her mouth so that she could get at them while her nipples were in my face - literally! In the meantime, her master had mounted her and was filling her sissy cunt. My Master was plowing mine as well. From the noise our masters were making it was clear we were pleasing them! From the noises she was making, I knew she was loving being milked just as much as I was loving it! After our men had gloriously filled us with their seed they sat back to watch us two milking sissies continue lapping away at each other. I'd never drank so much milk like this. My breasts were big enough that I could easily suckle myself but I rarely did that. "Don't want to waste that special sissy milk there, gurl!" my Master had told me. Now though, I was draining as much as I could from this new milking sissy. It felt soo good! Even beyond the bliss I felt after I've sissygasmed again and again I knew this time was something different. It was a wonderfully warm and floating and serene feeling. And it was from all that milk I was nursing from her beautiful breasts. I'd never sampled enough of my own milk to experience this bliss. That my milk was so special that it could make other people happy like this just made me glow inside. Eventually, my milking sissy partner could no longer hold herself over me. The pleasure had been that intense and the effects of my sissy milk coming directly from my breasts was too strong. She collapsed happily onto me. I was happily floating along from the effects of her sissy milk as well. Our masters just smiled down as their two milking sissies as we cuddled each other in our sexual and milked out haze. It was a wonderful way to spend an afternoon. Nowadays it's just my Master and I for my regular milking. Once a day makes it more special. But, as I'm not "in production" we can have more fun with the milk and the milking. Some days he doesn't use the milking rig at all but milks me by hand. It's a lot slower that way but so much, much more sensual. I can still fill up a milking jug - if he aims the spray from my teats well enough. But his fingers quickly get all wet and slippery with my milk so he has to keep grabbing and "manipulating my udders" to get the spray aimed right. Of course, I can't keep still when he's doing all that as it feels so wonderful. He has to smack me on my ass to get me to stop shifting 'round. "Silly cow! Hold still dammit! Hold still or I'll rope you in place!" he'd laughingly threaten me. I'd make a show of obeying him but then the sensations of his pulling on my breasts would get to much and I'd be to wiggling again. My sissy ass would get nice and red and stingy from his spankings. What I liked best with those milkings though would be when he mounts me. He will slip around behind me - we've made a mess of the milking enough by then that we're both wet and slippery from it - and then drive himself into me. I'm turned on enough by then that I easily accept that wonderful cock of his in one smooth thrust. Then he lays across my back and reaches down to once again get hold of my pendulous breasts. He'd be nuzzling the back of my neck as he'd start talking oh-so-dirty to me. Rocking his cock deep inside me, rolling across my "sissy G-spot" with each stroke, and slowly pulling on my tits to pull down milk with each stroke there, he'd start telling me what a good Milking Sissy I was. That he was going to leave the nose ring in all the time. That he was going to come up with some new chemical compound to inject into me that would change my skin color to be just like the Holstein I was. And other chemicals to let me grow cute little cow horns on my head. Pretty little ones to fit my being a pretty little sissy gurl. A pretty little Milking Sissy gurl. And then he'd have me grow a tail. A tail just like a regular milking cow. A tale he could use as built-in handle to pull me onto his cock even harder and deeper.... It was the stuff of fantasies. It was the stuff of dreams. His words and his promises of how he was going to change me even more to please him... Ooooh... They always did it. His words, his milking me, his cock filling me. His arms wrapped around me. His skin touching me. His taking me. His changing me. His Mastering me. Oooo... yes... that always did it. Did it for the both of us. My climaxes would just roll through me. So many and so deep that my legs would start shaking with them. As he got close he'd rear up and mount me truly. Hammering into me until my arms gave out and I'd fall onto the pad with only my huge breasts propping me up. His hammering would force milk out of my tits until I was sliding in it. And then he'd cum. A nice roaring climax that was matched with my girlish whimpering. I loved it. I loved my Master. I love pleasing my Master. I loved being a Milking Sissy for my Master!

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1 year ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

3 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

3 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

1 year ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

1 year ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
2 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

1 year ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

2 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

3 years ago
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Cum Craved Sissy

Taking a quick look at the clock, I noticed that the delivery had run late, and I was immediately stressed at the fact that Mistress would be home shortly. I knew I didn't have time to shower, and there was certainly no time for much cleanup either. I just pealed the skin-tight jeans down, crumpled them up and buried them at the bottom of the hamper.I carefully pulled the bright yellow panties down my legs, trying not to make any more mess. I washed the creamy jism away in the sink, squeezed...

2 years ago
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Born a Sissy

Born a Sissy This is the story told by me "grandmother" and my grandson Timmy. Most of it is true and only some parts have been modified. It all started back in 1979 when Timmy was only 9 years old. He was a beautiful child that I loved dearly. Timmy's mother, my daughter, had him at the young age of 17. Being so young she was not quite ready to be a full time mother. She was just like any other teenage girl who had social obligations to meet. She was a good mother but I understood...

2 years ago
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sissy

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you!After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in place of course, and returned to the store. Not sure what to expect I walked slowly through the door.The salesladies smiled and said, "Look...

2 years ago
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From manager to sub sissy

Cindy was a co-worker; well actually I was Her manager. Even though I was Her manger, W/we were very close friends. As a matter of fact I still consider Her my best friend. Everyone in the office was sure that we were having an affair, but we were just friends. I must admit that I would have loved to have an ongoing affair with Her. I know that I am not near man enough for Her and I have always know that from the first time I saw Her. Eventually after being friends for many years, I...

2 years ago
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Irsquom my Wifersquos Sissy

My story starts 2yrs ago when l retired early from work, also at that time l was having trouble with my sex life, so went to see a doctor who informed me l was going through what he described as a male menopause which l never knew existed. My scrotum had shrunk and looked like a shrivelled ping-pong ball, my penis had retreated into my balls and could only be seen if l got an erection which measured almost an inch and with a cock that size l was finding it impossible to please my wife Jolie, so...

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