Cometh The Sissy (Part 1) free porn video

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Cometh the Sissy (Part 1) Stevie "No. No fucking way." "Ahh, c'mon honey. It'll be so much fun! It's about me not you. I just need you there as, well, sort of a training aid. I promise you that you'll love it." "It's gross, seriously, some fat old man, what the fuck are you thinking about?" "It's about power. Control. Desire. I want to see if I can do it. You'll out all day and I'm doing my online classes and shit, there's only so many dildos and vibrators. I want to transform an older, out of shape man into a simpering sissy, I want to fuck his ass with strap-ons, keep his cock locked up, have him suck my pussy all day and give me rim jobs on demand. I want to make him up to look like a screaming sissy fag and have him beg me to get fucked. And of course I want him to suck your cock. I promise you, he'll be perfect, just a cumdump for you, and a plaything for me. I can tell, really you're into this, you just don't want to admit it..." Laura was sort of right. She didn't know but I was practically addicted to sissy porn. I loved fucking her of course, she was unbelievably good, but I wouldn't turn down the chance to have a go with one of those beautiful shemales with a perfect cock. Who wouldn't? I'd even try sucking cock if it was attached to one of those lovelies. But some old man? Just thinking about it made me sort of sick. On the other hand, it seemed to be a cost-free way of occupying Laura. Everything else she's suggested would make us broke. Maybe some old fart would even pay for the privilege... "If you're talking about old Len down the road, he's loaded. His wife passed away nearly ten years ago now and her family owned a huge amount of land. I'm thinking, would you ask old Len to pay for all the fun he's going to have with you?" "Now Stevie, that would be prostitution! I'm no whore! Well, except when we're in bed and I get to suck on your big old cock. Remember that scene we did in the motel? I loved dressing up like a street hooker. God I came hard that night. Or when you were a robber and pretended to rape me? Fuck that was good. I creamed all over the..." "Focus Laura. I have to go to work. Fine, you get Len to suck your pussy and fuck your ass with his tongue and make him buy you a strap-on to fuck his ass. I don't care if he pays for a wig and makeup and sissy clothes. But I don't want anything to do with it and he has to be out of here when I'm back. You win as always, but I'm nothing to do with your perverted plans. Agree?" She giggled. "Oh Stevie, my hard-bodied big-dicked boyfriend, of course! He'll get me all juicy for you so I'll attack you all night long. You'll see, it'll work out for both of us." "Well, I better not see old Len here in panties with a cock cage sucking your clit wearing a wig when I get back tonight." "Mmm, you'd be so lucky! Good bye dear." *** Laura I waited until I heard Stevie start up and drive his F-150 pickup down the road before I got up and opened the closet door. Jen (close enough to Len) looked adorable, all red in the face, the ball gag still in place, eye wide in silent pleading. He was standing up, wrists zip- locked together behind his back. He was stark naked, his tiny dick shrunk so it was barely there, his gut hanging over, undoubtedly feeling very sorry for himself. "Poor little Jen, I'm so sorry but I wanted you to hear direct from my man. Still some work to get him to fuck you but as he has no objections to me training you, it's a good start, right?" I caressed his fat ass and rubbed up against him. So much work to do... I unhooked his ball gag and wiped his mouth. Before he could complain I gave him a ferocious kiss, pressing up against him and pushing my knee between his legs. He was about as tall as me, 5'7", so we fit together well. I pulled back, biting his lower lip, then stuck my tongue in his ear. He was moaning by now, his little clit sticking into my stomach. I was wearing a thin, transparent pink top (a present from Stevie) and little matching pink panties that were more of a thong. "Little Jen likes being in the closet, don't you? Your little clit is all stiff. Do you want to stick it in me? Do you want me to lie back, wrap my legs around you and bounce up and down while your tiny pencil shoots deep inside my pussy?" "Oh Laura, please please oh God let me, oh..." I laughed and squeezed his nipples, hard. Jen just moaned. I led him out into the bedroom and pushed him onto the bed, then cut his zip ties to free his hands. He reached for me and I slapped his hands away. "Bad Jen! Let's go over the rules again. I'm the boss, you're my toy. You're here because I love to train sissies. You are my little pet, you never touch me without permission and you follow my every order, no matter how perverse. Any refusal and you walk away. You're not here by force, you can leave at any time, but if you do you never return, that's it. Do you understand?" "Yes, yes of course I do Laura. But I've been in there for hours, listening to Stevie fuck you, I'm so horny, please..." "Please what, Jen? Oh I know, you want to clean me up, right? Great idea! Let me get these panties off. Sniff and lick - good girl! Do you like it when I rub them over your face? Here, is this what you want?" I spread my legs wide and beckon Jen over. "Sniff, good girl. Get your nose right in there...yummy, right? Stop trying to fuck my bed, if you come without my permission you go home forever, Jen. Better...no, just sniff and tell me what you want." "Please Laura, please let me lick you." "No." "Please...please let me lick you, your pussy, to lick, to...to clean you, to eat all the come inside you." "Better. Keep going." "I need it so bad, Laura. Let me suck your pussy, suck Stevie's cum out of you, I want to cover my face with it, to stick my tongue right up inside you and get all of his yummy cum out of you and in my mouth. I want to suck your clit with his cum all over your pussy lips, to make you come with my tongue inside you, to, to..." "Good girl Jen. Get me interested, lick the outer lips first, ah, yes, gently like that. Oh yes, now tease me with the tip of your tongue, yes, now suck that inner lip into your mouth. Can you taste him yet? Thought you could. Now stick your tongue right in. Pull back, show me...ha! I knew he left a big load up there, now lick it all up, swallow it down. What kind of man eats another's load out of his girlfriend? A sad pathetic loser, just like you Jen! One with a tiny little prick. Do a good job and I might let you get it from the source. Just think, a hard, shiny cock in your mouth. You'd love that, wouldn't you Jen?" He was getting better at sucking me. It's been nearly a month now since I acquired my sissy slave. It was so fucking easy, I knew where he drank and I let him take me to his house. I teased him mercilessly for hours then had him jack off over my tits then lick it all off as I laughed at his small size. Then a couple of hours of him eating me, pussy and ass, and coming all over his mouth. Quick learner, flicking my clit, thumb in my ass, fingers on my G-spot, and even sweeter with him desperate to come. "Suck my clit you fag. Yes, ahhh...and fingers, oh yes...nice and slimy, take them out and suck them clean, pretend it's Stevie's cock, yes suck them, now back in...so close, harder, ahhh...you fucking fag, suck my cunt!" I came all over his face, forcing out the rest of this morning's cum from Stevie's fuck which Jen eagerly licked up. He's been in the closet since about 6:00 AM when I snuck him in and had a very loud, verbal fuck with Stevie. It was a nice step up for Jen and aside from an hour in the afternoon I had him all day. I had a good set of toys - I loved to strap a dildo onto his face and fuck myself silly with it. I also liked to play with his body to torment him. To be fair, in just a month he'd lost a good deal of weight and his legs and ass are a bit more toned but he had a long way to go. His homework of edging to sissy porn seems to have worked as he no longer violently objected when I told him what awaits him, that his future was full of cocks, cum, sucking and anal sex. The last pet I had was still with a big hairy bear, I think I hear wedding bells for that lucky couple. "C'm on up here you sweaty girl. Yes, you liked that, did you? You're all hard and wet. Did you clean yourself like I said? Let me check...yes, nice and lubed back there. So wet and slippery. Is this nice? What about two fingers? Oh, you're dripping already! Now suck my fingers clean, good girl." "Here's the plan for today - we both have a shower together to clean up a little, then I help you shave all over, neck down. Special smelly cream and I have a few razers for the delicate parts. Then I help you get dressed - yes, I got the lovely clothes from the web I told you about, using your credit card, and a beautiful wig. Not cheap but you need the best, don't you Jen? I also treated you to a full set of makeup, no fair using mine. I'll help you but mainly I'll be showing you what to do. Practice my girl! Next time you have to do it all yourself. Shaving as well, use a mirror." "Yes Laura. I, I want to pretty for you..." I gave him a kiss. "Ah, those videos are helping, aren't they Jen? Yes, so pretty, so desirable. Once we've done all this we'll get something to eat and I might just fuck your ass. You'd like that, right Jen? Fuck it slow and gentle, then hard and fast, then pound you until you finally come all over yourself. Sound fun?" *** Len Fun? Did that sound fun? No, it sounded horrible. I need to walk away right now. That fucking tease, I'm better off on my own, back to my comfortable life, escort agency 'dates', and pigging out on comfort food (OK, yes, fast food then...KFC deliveries, pizza and burgers). Laura is knock-dead gorgeous but so what? She won't let me fuck her, she just likes teasing me and now she wants to turn me into a girl. Not a girl, a sissy, and a homosexual. WTF?? So do I walk away? I just drool as she talks about what she's going to do to me. Shaved, moisturized, perfumed, wig and women's clothes, and then made to have sex with her boyfriend. The big, hunky Stevie. Hunky? Yes, all muscles and tats, with a big cock he certainly knows how to use. Damn all those videos...edging to sissy and gay porn definitely did a number on my head. I like women, women like Laura, not large men, oiled and sexy. But if I could just touch his ass, maybe lick it... Laura got me into this mess. Flirting, touching, wow, just swept me off my feet. I never imagined that I'd be eating the slimy remains of her boyfriend's ejaculation from her pussy. Or fucking her ass with my tongue. Just thinking about it turns me on, her knees up, legs spread, beckoning me over to clean her up. Even the first night she had me sucking her toes. So kinky, so very perverted, so delicious. I'd been wary since my wife died of golddiggers and Lord knows there's enough of those. Laura is just degenerate, she wants me as her plaything, it's not about money. At least I don't think so, she has me so captured, body and soul, that I can't tell anymore. I keep flashing back to that first night, when she finally let me come it was all over her lovely breasts and she make me lick it all up. I didn't even get soft, it was so, well, dirty and forbidden and...exciting. "Yes Laura. I, I want to look pretty for you..." Oh God, yes, I wanted her to pound my ass with her strapon. She'd tease me with it, making me beg, before finally pushing it in. It hurt so bad the first time but not so much now. What would the real thing be like? Ass up, head down, all smooth and lubed, Stevie behind me, slapping my ass then pushing into me, grabbing my throat as he pounds me over and over, so hard and fast and deep, aaaahhh... "Earth to Jen! Stop it girl, focus, we have work to do!" We had a shower together. We got each other clean but then I was pushed to my knees to give her a quick orgasm with my mouth then I had to wash her again. Laura paid a lot of attention to my ass, complimenting me, so I guess the hours of lunges and situps and core work is starting to make a difference. That and the salads and vegetables and slices of chicken breast. "OK my lovely sissy, all clean, more or less. Put this smelly cream on everywhere but you should avoid your intimate regions unless you want to be screaming for hours. I'd probably enjoy that but it's not what I need from you just now. Leave it on 10 minutes, apply a fairly thick layer evenly, we don't want you patchy. Wash it all off, pat dry and I'll be in for the next stage." I did exactly what Laura said. It got warm but didn't sting except a bit on my underarms, and I was relieved that she didn't tell me to put it on more delicate areas. Once the hair was gone it was amazing, my legs and arms were so smooth. Even my chest, which didn't have much hair to begin with, was so sensitive. I was playing with my nipples when Laura walked in. "Ha! You dirty girl, I knew you'd like being smooth. Stop that, if you want something to do suck these." She was wearing sheer black panties and nothing else and held her breasts out to me. I put my head down and sucked each nipple in turn until she pushed my head away. "Enough, we can't have you get me all wet and bothered again, it's time for our chores!" I sat on a small plastic chair she put inside the shower and she put a sweet smelling gel over my cock and balls and surrounding area. She gently shaved me, teasing me the whole time. "Sissies have to make sure they're always nice and smooth. If you're good I'll get you a playdate with another sissy and the two of you can pet each other for hours. Men have hair here, not sissies. Oh look, your little cockette is excited. Shall I give it a little kiss? Mmm, what if I slip the head into my mouth for a second? You like that sissy Jen? Enough, on the floor, ass up. In future you'll do this on your back, legs up, with a mirror to shave everything, but just this once I'll do it for you." Laura rinsed me off and put some flowery-smelling pink moisturizer all over me. "Good girl, you're definitely getting toned just a bit. Keep to that diet - shouldn't be too hard, just veggies and lean meat, no alcohol, no desserts. You have all the dessert you need between my sweet legs, don't you Jen? There, how does it feel?" "It's...wonderful, Laura. Smooth and shiny, I have it admit I feel a little girly now." "Just wait until your nails are done and we get you dressed. First, come here." She pulled me back into the bedroom, spread her towel over the bed and pushed me onto it. "Lay back, good. I'm in the mood for this..." Laura pulled out her strapon that fits around my head, the obscene penis pointing out of my mouth. There was a smaller one that fit inside my mouth. "Yes, nothing like fucking your pretty mouth. There, a bit of lube, now...ahh, I love how it stretches me out. God that's good. You'll never be able to do this with your little clit, will you Jen? But you will certainly feel stretched when Stevie's cock goes into your ass. Now suck that cock in your mouth." She was facing the headboard and I could see, up close and personal, the huge cock moving in and out of her pussy, soaking wet, her clit standing proud of her lips as she rode the penis sprouting out of my mouth. I held her hips as she bounced up and down. "I normally don't finish from intercourse Jen, it's a myth that women in general can orgasm that way, but if I rub myself like this, yesss..." She flicked her clit with her long red nails and then rubbed in circles around and on top of it with the heel of her hand. "You fucking sissy, fuck my cunt with your face, that's all you're good for, oh jeez, ahhh..." I thought I was going to dislocate my neck as she slammed into my face hard as she could until finally she screamed and held herself still, the cock buried inside, her pussy spasming around it. After a few minutes she eased herself off and lay down next to me. "Oh that was glorious. Let's get that off of you." Laura unhooked me and gave me a sloppy wet kiss. If she had just rubbed her leg against my cock I would have lost it but she always seems to know how to keep me from coming. "Good girl. Now clean me up with your talented tongue. Slowly and gently." I took my time and after about 20 minutes she had another orgasm, not as explosive this time. I was desperate to come myself. "Please Laura, I've been a good, a good girl. Let me finish please. I'll clean up after myself, I'll lick it all up, just let me come, I'm so desperate..." Laura laughed. "Poor little Jen. I'm too tired to rape you. I suppose you'll fit better into your panties without that little thing sticking out, but I know you and you'll just get another stiffy as soon as you start getting dressed. Hmm...I know, lay back and turn around, legs facing the headboard. Yes, now put your legs up the headboard, up onto the wall, scoot forward so your ass is up there, further. Ah, now you got it, legs straight up. Yes, you're looking right up to your little friend. A bit of lube...is that nice when I touch it? Let's get some into your nice clean ass as well. You like my finger there? What if I push it right in?" I was panting now, so close, and my clit was leaking, dripping down onto my face. "Ahhh, yes, ohh..." I was moaning and whimpering. Laura took both hands off. "Too soon. Stay like that. Here, suck my fingers, first taste that precum. Yummy, right? Now these, I know they're a bit stinky but I don't give a fuck. Clean them up. Good girl." Laura went back to teasing my balls and little cock, toying with my ass, sometimes putting her fingers inside, sometimes just teasing my hole. I kept a steady drip of precum. Finally I think she got bored. "Enough, we can't stay here all day. Open wide. Wider! More!" She slapped my ass, hard, then stuck two fingers in deep and jacked my little cock with her finger and thumb. "Come for me sissy, now! Come into your sissy mouth! Now!" And I did, spasming uncontrollably over and over, spraying all over my face. Laura kept her fingers deep inside my ass, wiggling them as she milked my cock with light pressure and I lasted a long time, squirting and then dripping down onto my face. "Good sissy, now eat it all up..." Laura scooped up my cum and fed it to me. I'm definitely getting used to the taste, I even like it in a weird perverted way. "Just wait until you get it direct from your boyfriend's cock, deep down your throat, holding his balls as he spurts over and over. You can't wait, can you Jen?" I was already starting to get hard again. "Yes Laura, I do want to suck a real cock. I can't believe it, I'm already excited again, this is why I'm here, I've never known anything like it. Make me your sissy, fuck me, own me, make me do anything, please mistress, I love all of it, I love you..." Laura laughed. "About time you starting calling me Mistress. And you better love me, you fat fag. You were so easy to break, it's obvious you were born to this. Now go clean yourself up and we can finally get you dressed, you big sissy." She kissed me but then bit my lip so hard I thought it would bleed. *** Stevie I thought, who am I kidding? - as I drove my truck out of the driveway. Laura was terrific but I'd like nothing better than to see Len, or Jen as Laura calls him now, dressed as a sissy, shaved and with a wig. Hell, I'd like to join him. We could wear little skirts showing our asses covered with little pink panties, and we could tease each other, then I'd suck his little nipples and work my way down to his hard, dripping cock, then I'd... Shit! I nearly hit that little Honda. What's happening to me? Big man indeed. I'm nearly where I want to be at the gym, toned as fuck, nice muscles and without all of those steroids the other guys take. Working construction, good money out here, especially with so little outgoings. Fantastic girlfriend, a real looker and crazy in bed. Why aren't I satisfied with what I have? I can't blame Laura, not really. I was into this sissy stuff before we met. Her talk of how she loves seeing men together, especially as shaved, crossdressing sissies, just solidified my semi-obsession. Massive secret of course. Even with all the LGBTQ-friendly environment these days, my life would be over if anyone found out. At least that's what's in my head. Even if I'd love to walk down the street holding hands with a pink-clad sissy, our bulges proudly showing as we swished into the supermarket, it ain't gonna happen. But maybe in a bedroom, we could touch each other, I could massage oil onto his perfect ass as I hold his cock in my greasy fingers and... Fuck. I'm definitely obsessed. I should get some of that Obsessed perfume. I'm hard now just driving into work thinking about kissing some sissy, rubbing up against him, pulling him into me as we kiss and... Luckily I'm here. A long day of construction work. Just as well I'm not attracted to men, these good old boys do nothing at all for me. No idea why but it does make it easier. I need to talk to Laura. She's the kinkiest person I've ever met. She told me that she likes women, men, everyone and everything. She's so horny she'd fuck the bedpost and she can suck the chrome off a trailer hitch. She's the one that's taken Len as her sissy slave. I'm nobody's slave but I wouldn't mind a go at a sissy. Len is just a fat old man, but maybe Laura can transform him. If she can't then no one can. Maybe I *would* fuck him. Laura says he's lost weight and is toning up. I'm not sure, I suppose any hole would do but it's not my fantasy. I want to be dressed up as well and play with another smooth sissy. I want us to tease each other. I want to bend over with my oiled ass in the air and have a sissy beg to rim me. To drive him mad with desire until we can't stand it anymore and embrace, our panty-clad cocks rubbing against each other as we whimper into each other's mouths. Then have him across my lap and slowly press two fingers in his lubed ass as he tells me what he is, what he wants, admits his secret desires and I... "Stevie! What the fuck! What's wrong with you today? Wake up man! The scaffolding won't build itself! If you're drunk so help me I'll fire your ass!" "Sorry boss, I'm on it. Drunk? In the morning? You know me, all good! Just got Laura on the mind..." "Well wait until you're home! Having said that, if I had her at home...well, whatever, do your job!" *** Laura While Jen gets cleaned up and puts on more moisturizer, I thought about Stevie. We've been together for nearly three years now. He's a nice guy, genuine, kind and funny, and fantastic in bed. Big cock and knows how to use it. But there's something else there, something that caused me to keep this relationship going and move in with him. My first relationship for more than a few months, ever. Sometimes he just looks at me and gently strokes my body, almost like a woman would do. The number of times I've fallen asleep with him caressing my legs after a mammoth sex session. And then there's his fascination with my clothes, especially sexy skirts and tops as well as lingerie. Hmm...maybe my big strong manly boyfriend has a secret. Gives me a few ideas to try out. And those nights when I'm asleep and he's on his computer. What exactly is he up to? I can't believe that I'm feeling randy again already. I used to think that there was something wrong with me but these days I've just got used to it. It's very rare that I don't come at least 5-6 times when Stevie is at work. I just can't help myself. I have so many toys and come so easily, it's just part of my day now. Oh, a few minutes while waiting for something to cook, that banana looks tempting... Or a woman newscaster showing a bit of cleavage, get some oil and tweak my nipples, then slam myself on that dildo stuck on the chair... All the time. Just as well that I'm not in an office, I'd be the office slut from day one and probably would get fired within a few days. Instead I have a decent inheritance and a good diversified portfolio including property which is more than enough as I don't have expensive tastes. My tastes run more to sticky semen and the moisture from an aroused pussy. So no offices for me, but even visiting my financial professionals can cause a bit of scene. I've toned that way down now, no more raping my brokers. 'Bad form' as one told me. Not that I go around raping people. I can shop without jumping on anyone, and aside from fondling the vegetables and fruit, my supermarket trips are incident-free. It's just that sometimes I meet sexy people and, well, sometimes we both just want a quick fuck. You'd be surprised at the number of lonely women who welcome the opportunity to suck my clit. A huge number of straight women watch and get off to lesbian porn. Almost all of them are quick learners and are much more perverted than most men who usually just want to stick their dick in a hole. Some of the overweight lonely wives are the most perverted. Insatiable. At least once they're with me. There's this one, Sheila, who gets off on being humiliated, mainly about her weight. Comes in rivers over bodyshaming. And the vacuum from her mouth, it's just incredible. Maybe if I give her a call... But I digress. Jen was looking adorable. Well, Jen would never pass unless one happened to be falling down drunk, and even then it's very unlikely. But definitely the look I wanted...thigh-high pullups, white, with pink frilly panties complete with a sheer panel in front. A too small top, pink with a large glitter 'Princess' across the front, and a little frilly skirt to match the panties. Blonde wig with little curls, and pink strappy heels. I went to town with his makeup, thick and embarrassing but not clownish, more amateur hour. I hate those men who end up with white circles around their eyes - ever try YouTube? It ain't rocket science after all. His little pecker is hard and leaking, looking very cute in his frilly panties. I had to tease him but more importantly, to get him to agree to all of this. Open his eyes in case he's still in any doubt as to his needs. "Oh Jen, you're just adorable! And I can see you're loving it too! Look at you with your blonde curls, candy apple red lip gloss and eyeliner. The only thing you need know is a face full of cum, your makeup ruined and your throat sore from a cock ramming in and out. Is that what you want?" "No Laura, I love being around you. I'm only doing it because you want it. I'll do anything to spend time with you, you know that..." "Oh Jen, come and sit down next to me. Good girl. I like to stroke you even more now that you're so smooth. Spread those thighs apart, yes, give me access. You like that when I stroke you just with my fingertips, through that little panel? It's like little windows on business envelopes, I can see your little clit, all hard and wet. No, just lightly, I don't want to mess up your pretty panties. Now suck my two fingers of my other hand, good girl. Use your tongue, pretend it's your little lover and you're sucking his cock. I'll need to be even more careful now with you slobbering over your pretend cock, you're even more excited." "Ah, even better. I need to switch over to your little balls otherwise you'll cream everywhere. It's only us two here, just us girls, why not admit it, Jen? You want a little playmate. Someone just like you, all wrapped up pretty with a little hard cock. You want to play with it, rub against it, your little panties pressing against each other, then lay down together and lick and suck until you get a mouthful of cum. Kiss and share it, then maybe suck each other's toes before moving on to his smooth, lovely ass...am I right?" I took my fingers out of his mouth. "I...I don't know Laura. I'm horny all the time now, I'd fuck anything and anyone. Maybe if there was someone like me, all dressed up, and gentle. I don't want to be raped. Just a sweet kiss. Maybe more. Ahhh...I'm so close, please..." Jen wasn't where I need him to be. Not yet. I pulled his panties to the side and teased his hole with my wet fingers. "Is this nice, Jen? Gentle enough? You and your little friend, all smooth and shiny like you, perfumed, in bed together. He plays with your ass like this. Kisses you as his finger penetrates your ass, just a little. You leak more into your panties as you moan, a whimper escapes your lips. You beg him to fuck you. He tells you no, not unless you take his hard, wet, dripping little cock into your mouth. What do you say?" Jen is panting now. "Oh God, yes, yes, please don't stop, anything, ohhh..." "Just a shame I don't have a cock for you to suck. Rim my ass." I push him away, pull my skirt up and get my head down with my ass up. God I wish Stevie was behind me to push his big cock in and fuck me silly, but at least Jen can stick his tongue up my ass. "What are you waiting for?" "Yes Laura..." "And I promise you if you play with yourself and come in your panties, I'm going to lock it up. Or maybe just find a better sissy who does what he's told. You don't want that, do you?" His reply was muffled as he was licking my crack. Jen took instruction well, he knows to start at the top and work his way down. I was close but I do love a tongue in my ass. "Good boy. Down the crack, yes, now tease my hole, all around. Yes, oh my, ahh...now push just the tip inside. This is what you're good for Jen, you little sissy, teasing my little rosebud. Now fuck my ass with your tongue, yes, shove it in there. Your little cock is much too small, Stevie stretches me out, I wish he was here fucking me but your tongue will have to do. Keep going you sissy, right in there. Yes, mmmm, just like that..." I reached over and picked up my eight-inch friend, wide and veiny, and pushed him inside my dripping slit. "Oh yes, I'm fucking myself Jen, a real long, thick cock pushing inside me. Keep your tongue in my ass, good boy, I'm nearly there, ahhh..." I was close enough that the cock pushed me over and I trembled and clenched as I came over and over, the waves crashing over me as I mashed that cock hard up inside. Finally I slowed down, pushed Jen away and lay down on my back, the cock still inside. "Take it out. Slowly, and clean it with your mouth." Jen worshipfully pulled it out and started to lick it clean. "You fucking sissy, you wish it was real. Now clean me up." Jen was so good, very delicate knowing I'd just come, concentrating on my inner thighs and outer lips. Eventually he moved inside and I had another couple of orgasms, smaller but sweet. "Enough! Now let's check." I sat up and pushed him down. "Hard to tell you're so wet. Do want to finish, Jen? To fill your little panties with cream?" He was so close, I just needed to imprint on his psyche. "This is my little slim boy just for you. It's all wet and gooey already. Legs up. Yes, let me slide it in. Good boy, all filled up. Can you feel it hit your special spot inside? Good, now I'm going to rub you through your wet panties. Round and round, just like us girls like it. Come for me with this cock up your ass, come in your sweet little wet panties, fill them with cream with your lover's cock deep inside you. Let go now, Jen. Come for me..." "Ahhhh!!!" Jen squealed as he filled his panties, humping against the palm of my hand. I rammed the plastic cock hard up his ass as he kept squirting. It lasted ages, almost like a woman as he heaved and rode the waves. I stuck my finger inside and wiped his cum over his lips. "Taste yourself Jen. Next time your sissy lover boy will fill your mouth."

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Sissy Therapy

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

1 year ago
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Heathers Sissy

Heather's SissyMy husband, Bobby, is standing with his nose in the corner, quietly sobbing, as he contemplates the ill-advised temper tantrum that he threw this afternoon. His sobbing is due to a very sore bottom, for which I take credit foróalthough to be fair, my favorite wooden paddle should also take some of the credit too.I'm not sure what it was that finally sent Bobby over the edge today. It could be the fact that I arbitrarily extended his sentence of chastity for another month, or it...

3 years ago
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The White Sissy Slave Society A Walk into Sissyhood

The White Sissy Slave Society: Sold into Sissyhood By Meeah Soo They were standing in a small group, drinking beer, smoking, and laughing. I could hear the rap music thumping aggressively from their boom-box. I could see them watching our car. It was late, well after midnight, and this particular park was no place for a white sissy to be at this hour. I've never been a physically or mentally strong person. I'm very easily intimidated. And there I was in a tiny plaid mini and white...

4 years ago
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My Girlfriend madd Me a Sissy Part3

Here's the 3rd part of my story, I hope I didn't make you guys wait toolong. Hope you enjoy, its best read one handed ;-)My Girlfriend Made Me a Sissy - Part 3-------------------------------------------------I lay on Jess' bed waiting for her and wondering what would happen forages. She was in another room getting ready for her new lover, I wasalready dressed up. Pale blue, see through panties and matching bra, ashort black skirt and a blue vest top. With my make up done to show off mypretty...

2 years ago
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Sissy Stepmother

Sissy Stepmother A Pantyboy Profile INTRODUCTION Cheryl here. You remember me. The 20-year-old pantyboy extraordinaire. Every man's naughty, secret, wet dream. Raconteur without equal. In "Service" and "Test Driven," I told you about Amy and Judy, two of my lovely roommates, fellow pantyboys and like me, covergirls for "Panty Boy," the only publication worth buying, besides some of those Spermco comic books about us "special boygirls" and the "Sunday New York Times." And Panty...

3 years ago
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My girlfriend made a sissypart1

Hey guys this is my first story ....hope you all like it ...When I was 18, in spite of my shyness and not being in anyway incrediblyattractive, I somehow landed myself a girlfriend 2 years older than me. Iwas quite short for a boy then, around 5'7 and very slim having not yetdeveloped much muscle. I had shoulder length brown hair and bright greeneyes and I simply couldn't believe my luck in getting this girl. She wascalled Jess, a beautiful redhead with a body to die for and an appetite forsex...

4 years ago
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Sissy Mission 4 Southern Belle Sissy

The Sissy Mission series consists of short-short stories designed to give ideas for domme/sub play, solo "outings," or just for your reading enjoyment! The goal is to have a dozen vignettes. --CA Sissy Mission 4: Southern Belle Sissy By Cheryl Alison Mistress believes in community service. So when she dropped the ad on my desk at home, I knew that I would be a faithful community servant within a short while. The ad read: Southern Belles Needed The Ladies' Auxiliary needs...

1 year ago
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Sissy Puppy Fifi Part2

Chapter 2 I tried as best as I could to get comfortable curled up in the corner of the room. At first I kept squashing my tail which either caused the vibrations to start or pushed the plug further inside. I had eventually worked out the best position to lie in when Mistress appeared. "Time for bed Fifi," she said as she attached the pink lead to my collar. I was then led through the house and up to her bedroom. This was a strange feeling to enter her bedroom not in my usual maid's...

3 years ago
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Sissy Therapy

My advertisement read: MEN Interested in sex with other men but don't know how to proceed? Looking for a safe, friendly way to find out if this is for you? Obsessed by online bi/gay/sissy/crossdressing porn but frightened to meet someone? Is your marriage at risk because of your desires? I can help! One four-hour sexual therapy session will help you to decide if this is right for you, and will help you to understand your desires. Don't suffer alone, I can...

2 years ago
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SISSY DANI PART3

CHAPTER THREEMistress Jennifer and Mistress Susan's plans to create an entire"harem" of transformed men and boys continued apace. The lure ofTeasing Tammy (the transformation name of Susan's teen-agedbrother Tommy) proved quite effective. Each of the young men (theyoungest just 14, the oldest 22) the little tease brought back tothe home we all now shared was turned into a different kind offeminized sex-toy, all designed to please the Mistresses andtheir dominant friends.The little...

3 years ago
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My Stepmothers Sissy Daughter

My Stepmothers Sissy Daughter By Malissa Madison The dream was so real, she was being chased by some evil thing that thirsted for her blood. She was cornered with nowhere to hide. She felt its hot breath on her as she tried feebly to squeeze through a hole too tiny to fit. The hot breath as it pushed its nose against her bottom. It felt hot and wet, Wet? She woke with a start in full panic unable to stem the flow. All she could do was lay there and cry in silence. She'd had this...

3 years ago
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Stepmothers Sissy Schoolboy

One-Handed Reading: A Step-mother's Sissy School-boy This is a one-sided conversation between an (evil?) step-mother and her delinquent step-son. ------------------------------------------ Author's Note: This is not some attempt at a Pulitzer, or to make some earth shattering literary statement. Nope. If you are looking for deep characterization or nuanced subplots, move on. This tale is not for you. I love exploring verbal humiliation alongside being dressed. This is what I call...

4 years ago
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Sissy Stepson Part 1 Stepmothers Trap

Sissy Stepson Part 1 ? Stepmother's Trap Carl Monet was a shy boy of about 15 when his widowed father married Rita Parker. Mrs. Parker was 20 years younger than Carl's father Larry. Carl was very shy and sheepish toward his new stepmother and the new Mrs. Monet was rather cold and distant towards him. Carl's father was gone quit often on trips abroad for weeks at a time and Mrs. Monet was often gone shopping with her sister Maryann and her mother Regina. Carl was...

2 years ago
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Sharons Mistress Throws a Sissy Party

Sharon’s Mistress throws a Sissy Party(Prior chapter is Sharon’s Sissy Saturday)The next morning Mistress was kind enough to let me sleep in, but an alarm above the door to my little cell went off at 6:30, rousing me from a delicious dream of being naked and fucked in the woods by a handsome, dark-haired man who kept me as his personal sissy slave slut. I woke with the sensation of his hard cock filling my dripping pussy, and I realized I was still leaking cum from my day in the booth. I...

4 years ago
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Sissy dannis birthday party

My last "true life" story was about how I became Heidi's sissy crossdresser "Danni" - I only explained the initial experience of Heidi coming home to find me in one of her dresses - followed by spankings, punishment and eventually getting pegged by her wearing a strapon. Of course there is MUCH more to what happened next (like being taken out in public and going shopping, to hair salons, etc...), but I'd like to for now jump ahead to what happened to me on my 19th birthday. By then I...

3 years ago
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Sissy Therapy Case Study 2

Sissy Therapy - Case Study 2 Shelly's latest client is John who is obsessively addicted to smooth, shaved men's asses, ideally covered by skimpy women's panties. Shelly helps him to come to terms with his desires and learn a lot about himself as well. Oh, lots and lots of sex as usual... ;) Hi, I'm a sexual therapist. Sort of. No qualifications, my only experience is what I've gained on the job. This is my second 'case study' which took place a few months after I started. To recap...

2 years ago
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Crowd Sourced Sissy Spin OffMothers Milk

NOTE: This story stems from an incidental bit in the "Crowd Sources Sissy" story that a couple of readers seemed to be interested in having me explore further. It's just a starting off point. You do not need to read that story first to understand this new work, but of course feel free to read it to get the full effect. Enjoy! Crowd Sourced Sissy--Mothers Milk I knew that my husband had a sissy fetish long before I married him. For many, that would have been a bridge too far,...

3 years ago
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My Young Sissy brother for Mens Cum today

sharleesisterboyMY Young SISSY brother in Heat for Men's Cum, today!You used to prance around the house in your white underware, when Mom was gone, shaking your cute ass at me till I caught you, roughly, in My Big brothers arms and carried you to my bedroom floor. You giggled all the way, till I tossed you down on the dirt floor and you tumbled and smiled up at Me and lay on your tummy with your legs spread wide for Man-Cock. You know what I like to do to You, but, instead, I tie your wrists...

2 years ago
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Sissy Sisters Party

SISSY SISTERS PARTY by Throne Bob Clump, the friendly retired guy at the end of the street, was taking advantage of the mild weather of late Spring. He was sitting on his front porch enjoying a fine cigar. Or at least a cigar. Those fine ones cost a lot more than what he smoked. As he sat there, a car pulled up across the street, in front of the house diagonal from his. In the dimming light of dusk he saw two figures emerge. The first was a woman, quite attractive in a slender,...

3 years ago
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Sissy Girl Party

SISSY GIRL PARTY by Throne Danny felt so ashamed, standing there before his wife Melba in a pink and white party dress that would be appropriate for a nine year old girl, not a grown man like himself. He cringed inwardly and unconsciously took one of his short pigtails and wound it around his finger. His feet were shod in pretty ballet-type slippers, pink ones with little rhinestones on them. "You look so sweet, Dee Dee," she said with a smirk that he knew all too well. He had...

2 years ago
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My Stepmothers Sissy Daughter part 3

My Stepmothers Sissy Daughter, part 3 By: Malissa Madison I woke up early, my wet diaper urging me awake as I opened my eyes. Mommy was watching me sleep, and I realized her hand was resting on the crotch of my plastic panties pressing the wet diaper against my skin. "Did Mommy's baby girl wet her diaper," she smiled at me. "We can't have you in a wet diaper now, mommy's just going to have to change that," she helped me out of bed and I climbed up on the changing table, putting...

1 year ago
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Wife and Sissy invited to a party

My wife and I were invited to some friends’ house on a beautiful estate in TX for a weekend party. While we were both well aware of the debauchery that could occur at the event, we had no idea how much participation we would both play. We were just getting off the plane to meet our driver when my wife handed me a slutty little maid outfit, and told me to go into the bathroom in the airport and change before we got out of the terminal. I did as she asked and then tried to walk out without anyone...

4 years ago
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A Sissy and Four Brothers

A sissy and four brothers -What is it like? Mother is very strict about separating me from 'the boys' but they've never experienced a 'sister' in the house before so there seems to be a lot of snooping around. A few of my readers have asked me for some additional information about farm life and living as a sissy with four brothers, and I'll respond to the question about seeing Jack again. Jack's mother called me and told me that I'd done wonders about boosting his self-esteem and she...

3 years ago
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Sissy Bachelorette Party

'You want it again?' She said, as she climbed between my legs, spreading them with the force of her knee. 'Yes Mistress.' I said, turning my head to the side. Her gloved hand grabbed my chin and turned it towards her. 'You want to be my girly lesbian bitch?' She said, as she tweaked my puffy nipples with her other hand, the dry latex chafing me. 'Yes Mistress - I want to be your girly lesbian bitch,' I rubbed my horny cunt against her stocking clad leg, ignoring the pain, wanting, no, needing...

2 years ago
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Sissy Julian Chapter III Further Development

Just when Julian's Lake Orenda experience seemed perfect, even if he is not about to admit it, circumstances change. But then Julian and the twins were very naughty boys, and we all know what happens to naughty sissies. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to...

4 years ago
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Mothers Sissy Teachers Pet

Mother's Sissy, Teacher's Pet By Sandy Brown January 15th, 2012 Dear Ms. Brown, I am Sandy's homeroom and science teacher. I thought I would mention to you that I noticed that Sandy had a small amount of nail polish on the base of his fingernails today. I assume that he was having some fun with you over the weekend, and that before he left for school you used nail polish remover, but inadvertently left some polish on. The color is very pretty, and I'm sure he looked adorable, but...

2 years ago
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The family ndash Sissyrsquos Babysitters Part

The family – Sissy’s Babysitters Part-2Sarah had left, I heard the front door close and her car drive off.....I couldn’t believe what was happening. Sarah and me had done some things, had fun with others, but she had dressed and prepared me not for ‘our’ fun...to leave and let her parents use me, they obviously knew about ‘our’ pleasures....it was James & Helen the couple that I sat with, talked to before marrying their daughter...was it something they always knew, or something they had...

4 years ago
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CDg Sissy Slut Cocksucker goes to local Adult Theater

I love dressing up whenever possible, which is not often enough. But, what I love even more is dressing up as a hot and wanton sissy slut cocksucker and then going to the local adult theater for some great XXX fun. I am not totally passable, but have been told my legs are fantastic and my ass is nice and tight with a hot tramp stamp just above my ass. Most guys say it's sexy as hell while they are fucking me. Fortunately, my wife had to go out of town for a few days and thereby giving...

3 years ago
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My Stepmothers Sissy Daughter part 2

My Stepmothers Sissy Daughter, part 2 By: Malissa Madison I lay there sleeping peacefully, feeling safe for the second time in so long I couldn't remember. I heard voices and I woke up, I was facing toward them on my side. A woman I didn't recognize but looked a lot like the girl in the diner said, "I think she's so sweet. I'm glad Dave brought you here last night. I was afraid to say anything about the bruises on your face, I didn't want to scare you." "Thank you Monica," mommy...

3 years ago
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Being Sissy To My Brother In Law

Jenny knows I love to wear her sexy undies and lingerie but obviously apart from her it was a secret kept from everyone else. One day while jenny was out, I was feeling particularly randy so went to our bedroom & rummaged through her panty drawers. My hand felt the smooth shiny material of a pair of red satin tanga panties and I immediately got a twitch in my flaccid cock. Satin are my favourite. I thought maybe a pair of stockings would be good too. These were in the wardrobe drawer and on...

2 years ago
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Being Sissy To My Brother In Law

Jenny knows I love to wear her sexy undies and lingerie but obviously apart from her it was a secret kept from everyone else. One day while jenny was out, I was feeling particularly randy so went to our bedroom & rummaged through her panty drawers. My hand felt the smooth shiny material of a pair of red satin tanga panties and I immediately got a twitch in my flaccid cock. Satin are my favourite. I thought maybe a pair of stockings would be good too. These were in the wardrobe drawer and on...

Crossdressing
4 years ago
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My sisters their friends and me their sissy Part 2

Part Four Jolt after jolt of electricity passed through my body. Each longer and worse than the one before it. I held my number two hole shut because I believed what Joy had said about losing any of the water. But the pain was becoming almost too much. I knew that in another jolt or two my control would be completely gone and even with the help of the big thing back there plugging me I was certain to lose that water. And there were two gallons in me making me look really pregnant....

2 years ago
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My sisters their friends and me their sissy

Part One My oldest sister Vickie, was 18 when my mom died. My middle sister Michelle, was 14 and my youngest sister Joy, was 11. I, Mark was the baby of the family at 7 and had been the only male in the house since father had passed away when I was 2. He left us well off and with his money well invested we lived very nicely indeed. We had a private tutor/governess, Ms Wells, a young lady of some thirty or so I suppose. A live-in housekeeper Ms Dee Dee, a French exchange student...

3 years ago
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Sissyboy Conversion Therapy

One The ProblemI know I have high standards, Doc, Matt Studley said to his ther****t, Dr.Freudist. But it s more than that. Dr. Freudist nodded and said, Um hum. Can I be honest with you, Doc Matt asked.They always ask that, Dr. Freudist said to himself. I ve been listening tothis guy ramble on about his issues for seven weeks, twice a week, andNOW he s going to be honest But Dr. Freudist merely nodded and said, Of course. This is a safe place. And then he waited.And waited.Finally,...

1 year ago
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Sissyboy Conversion Therapy

One The ProblemI know I have high standards, Doc, Matt Studley said to his ther****t, Dr.Freudist. But it s more than that. Dr. Freudist nodded and said, Um hum. Can I be honest with you, Doc Matt asked.They always ask that, Dr. Freudist said to himself. I ve been listening tothis guy ramble on about his issues for seven weeks, twice a week, andNOW he s going to be honest But Dr. Freudist merely nodded and said, Of course. This is a safe place. And then he waited.And waited.Finally,...

1 year ago
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Chrissie The Saga of a Lovestruck Sissy Maid

Chrissie by c.w. cobblestone BOOK ONE "Mrs. Martin" Part I My right leg had a mind of its own. Rebecca frowned. "Why you keep bouncing like that? What's wrong with you?" "Um, I ... I ... nothing." "Bullshit, nothing. Something's up; you been acting weird ever since we got back from Paris. What the hell's going on, Chris?" I balled my fists. Clenched my jaw. Closed my eyes. Drew a breath. Took the plunge. "Okay. Okay. It's just ... well, now that we're...

2 years ago
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The SissyMaster

THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

4 years ago
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2088 Its a Sissy World

2088: It's a Sissy World Charles Pauline - Data Processor Cindy Pauline - Charles' wife Ms. Miriam Jensdotter - Charles' Boss James Marie - Charles' work friend Ms. Marysdau - James' boss Creampuff - A Sissy Store Worker Babykins - A Sissy Store Worker Suzi - The Sissy Store Owner Butterscotch - Creampuff's Roommate Supervisor Gabriellez - Creampuff's Apartment Supervisor Janice and Roger - Passengers on the Looper Ms. Hardcastle - Milking Salon Director Nurse Hamilton - Milking...

4 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Six Another Sissy for Ms Rebeccas Household

Teaching the Sissy Maid Workshop at the MVP, Chapter Six: Another Sissy for Ms. Rebecca's Household? After the workshop ends on day one, Ms. Rebecca stays to speak with some of the women attending the class and gets an unexpected offer that offers her some incredible rewards if she can take ownership of another young male submissive who is displaying sissy tendencies. After the workshop ended for the day, I stayed for a while to give me a chance to speak with some of the women...

3 years ago
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The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

3 years ago
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Cocky Weewee Peepee Sissy Slut Training The Bladder Test

This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

3 years ago
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Meinen Mann zur Sissy erzogen

Achtung diese Geschichte ist noch voller Rechtschreib- und Gramatikfehler. Jeder der m?chte kann diese Geschichte als Vorlage nehmen und sie verbessern. Jetzt reicht es mir. Ich hatte die Internet Seiten meines Freundes gefunden. Er surft also st?ndig auf Adult Baby Sissy Seiten. Ich hatte mich schon l?nger gefragt warum er im Bett nichts zu Stande bringt. Das kann er haben, ich werde ihn einfach in ein kleines Babym?dchen behandeln bzw im Grunde verwandeln. Er war eine Woche zu einem al...

2 years ago
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Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

4 years ago
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A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

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...

2 years ago
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Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

4 years ago
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Forever Her Sissy Chapter 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. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post...

2 years ago
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Curiosity Spanked the Sissy Finale

You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

2 years ago
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Training Sissy Michelle

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my...

4 years ago
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Tweak Chapter Four Whats A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

3 years ago
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The Sissy Diaries My Two Mistresses

Dear Diary, Things were going so good for me. I got promoted at work, even though I know most people there don't like me because I'm quiet and reclusive. It's just that I can't get too close to anyone there and risk exposing that I'm a closeted crossdressing sissy. Still, I do my work and go home to my apartment and escape into my sissy world. Still, I decided that with my promotion and my increase in salary, I could afford a better apartment in a better neighborhood and that's where...

2 years ago
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Good Sissy Girl

Good Sissy Girl. I kept pressing myself backwards. Not much further to go now, I could feel the flare really stretching my lips now and that meant I was almost there. As the plug's biggest width popped past my sphincter and went all the way in I shuddered all over. It felt so full. It felt so good. "That's a good girl. Allll the way in..." my Mistress purred at me. I loved seeing her this excited. I loved turning her on. I loved that transforming myself for her turned her...

4 years ago
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Sissy School Part 3

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

2 years ago
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Dr Cooks Sissy Clinic The Begining Jade and Deans Experience

Dr. Cook's Sissy Clinic: The Beginning and Jade and Dean's Experience. By dirteesissy I gazed at Jade's bottom, as she raped her husband's ass with a 10" strap on cock. Her pounding of her sissy maid's hole, bordered on the extreme, somewhere between love and hate, she punished that sissy ass with long powerful strokes. Jade, dressed in just red thigh high P.V.C. boots and gauntlets of the same material, was making mincemeat of her hubby's derriere and I looked on with pride at my...

2 years ago
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Andrew The Unsuspecting Sissy Part III

ANDREW THE UNSUSPECTING SISSY PART III [email protected] MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN THROUGH THUSFAR..... ANDREW NOW DREW: SISSY SUPERSTARSOON TO BE HUSBAND TO JIM JIM : BILLIONAIRE INDUSTRIAL WITH A PENCHANT FOR SISSIES AUDREY: DREW'S STEPMOTHER AND OWNER OF THE MANOR SARAH: DREW'S STEPSISTER AND TRAINER VALERIE: DREW'S DOCENT TRAINER DR NEWMAN: MEDICAL DIRECTOR OF THE MANOR PENELOPE...

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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...

4 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...

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