Helper Sissy Hubby - Chapter 1 free porn video

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Helper Sissy Hubby - Chapter One: Tittie Crazy ? by: Sexy Wifey "What's this, honey?' I innocently asked my husband, pulling a lacy underwire bra from the bottom of his sock drawer. He turned beet red and stammered a few things about how my underwear must've gotten mixed in with his. "But dear, you know I don't usually wear anything as lacy and racy as this!" I was smiling, now. I'd known all along that he liked to dress up in women's underwear. And now, I had the 'goods' on him. I asked, "Did you really think you had me fooled all this time? That I wouldn't know you were waiting until I left for a few hours, and then dressed up and jacked off?" I was a little mad now, because sometimes I was horny, and he'd already relieved his sexual anxiety without sharing it with me! That was all going to change, NOW, and I told him so. "No use denying it, sweetheart! I've driven off, waited a few minutes, and watched you through the bedroom blinds. I've seen you all dressed in your lace bra, breast forms, crotchless panties, garterbelt, stockings, high heels, and wig, with a big hard-on, jacking off until you came! I've even watched as you turned upside down in the corner, and jacked yourself off into your own mouth! You really could've shared all that with me...I think it would've been fun to help!" When I said 'would've', his eyes dimmed, but they opened right back up when I said, "I'll help you come, right now, but first, get busy and put on all your pretty things; ALL of them! I want you to use an especially large amount of your breastform glue. I don't want them to come off until I say so! And this time, use some of my makeup. If you want to look like a woman, REALLY look like one!" I left the room, and went to the kitchen. When I came back about 15 minutes later, there he was, all hot to trot, and, I must admit, he looked fairly convincing as a woman, except for one thing... a HUGE raging hard-on stuck out from under his lacy slip! I knew he was mine, now! "My goodness, darling! Why didn't you ever tell me that women's clothes turned you on so much?" I laughed and reached over to stroke his erection a few times. When he moaned and pushed it towards me, I stopped and said, "Not so fast, my little Sissy Hubby! First, before I help you cum, I want you to promise me that, one, you will NEVER dress up again except for when I tell you, and don't worry; there'll be a lot of it...maybe even more than you might want; and two, that while you're dressed up, you'll do whatever I tell you to do; it wouldn't be anything that would really hurt you... I just want you to understand exactly WHO is in control of this dressing-up situation!" Of course, by this time, my husband wanted, needed to come so badly, he would've agreed to anything. "Yes, yes, I'll do anything you say, just PLEASE let me cum!" I smiled and took off my blouse, then my bra. He's always had a thing for my titties, anyway. What man wouldn't? they're 38D with perfect nipples, if I do say so myself. "What I want you to do, my little sissy husband, is to jack you off on my titties!" His eyes REALLY lit up at that remark. "Not so fast! You haven't heard it all, yet. I know that you'll eat your own cum. I've spied on you and seen you do it. Tell me, when you're upside down, jacking off into your own mouth, what are you fantasizing about? Tell me, NOW!" I reached out and jacked him off, a little faster this time, to encourage his answer. My husband admitted, shyly, "Well, I was imagining that I was sucking on a man's cock, and then that he was coming in my mouth. That's why I swallowed it." "How interesting. My husband, all dressed up in a garterbelt, nylons, a brassiere, glued-on falsies, high heels, and of course, a wig, lots of makeup, RED lipstick, long nails wrapped around a big cock. Jacking it off. Sucking a big hard dick. Making it shoot cum in your mouth. Swallowing someone else's sperm, not your own? Hmmm. I think I'd like to see that. I think I'd like to help. I'd like to make certain you went through with it. I'd like to jack off a big dick into your mouth myself. I wouldn't stop until it was too late, until he was spurting in your mouth, and you HAD to swallow it all!" I was thinking that this could be even better than it was turning out. "I see that my Sissy Hubby likes the idea. At least, your dick likes it, because it's as hard as I've ever seen it! Now's the time! I want to beat you off onto my titties, and then get you down on your knees and lick all your hot cum off of my nipples." I was sitting on the edge of the bed, now, and I was pumping furiously away on his dick. It was bigger and harder than I had ever seen it! I began stroking it slower. "Now, really! Do you want to cum so quickly? Just think of all the hot cum that will soon be squirting out of your cock onto my pretty titties! Will you lick it all up for me? You will? Good! What if I were jacking somebody else's big dick onto my titties? Would you like that? You would? What if I made YOU jack it off for me? You'd do that if I ordered you to? You'd jack off someone else's big, hard dick onto your own Sexy Wifey's titties? What if I ordered you to make him cum? You'd make a stranger's big, hard dick shoot semen all over my titties? What if I ordered you to lick up all his cum after he came? Would you lick up all his cum, too? And would you swallow it all? You've promised that you would. You'd do that? Jack another man's dick off onto you own wife's titties, then lick up his come, all the time dressed in womens' underwear? This is just the beginning! I'll have you dress up, find big dicks to jack off onto my titties, and I'll watch as you suck them, and I'll laugh as you lick all their nice hot come off of me." I jacked him off faster. "Let me cum!" he begged. "Not until you promise me that you'd suck a dick for me, jack it off, and lick the come off my titties!" "Yes, I promise I'll suck a dick for you, jack it off, and lick the cum off your titties!" "Promise me you'll let me jack off a dick into your mouth and have you swallow all the hot come!" "Yes I promise to let you jack off a dick in my mouth and swallow all the cum!" "What if it was a huge BLACK dick I was jacking off? Filling your mouth, half-choking you? I wouldn't stop until he filled your mouth to overflowing with his sperm! There'd be SO much cum to swallow! Promise you'd suck black dick for me!" "Yes, yes, I promise to suck a black dick while you jack it off 'til it shoots in my mouth!" I was in complete control, now, and we both knew it. "Promise me you'll suck on a big dick until it's completely hard. Then, you'll guide it up inside me, watch it going in and out all the time he's fucking me, and then I want him to shoot his cum up into me. Then, you have to suck all his come out of my freshly-fucked pussy! I want you to suck someone else's sperm of of your Sexy Wifey's pussy! PROMISE!" "I promise I'll suck him, and suck you!, and suck all his cum out of you!" "Promise me you'll let me have you fucked at both ends! I want you to be on your knees, while I push a man's big dick up inside you, being ass-fucked by one big dick, and sucking the other cock. Then, I'm going to jack it off in your mouth! I'm going to make it flood your mouth with semen and force you to swallow all his cum, while the dick deep in your bottom fills your ass with cum, too! Promise me!" "I promise! Make me get fucked! Make me suck a cock while you jack it off into my mouth! Make me swallow his semen! Anything, just please, make me come, now!" "Cum for me! Shoot your hot cum all over my titties!" And boy, did he ever! It went everywhere! but mostly right on my perfect nipples. Then, I had him bend down, lean over, and start licking all that hot cum off of me. "What I want you to do, my sissy husband, is to pretend that it's someone else's come you're licking off my titties right now, because as soon as you do, I'm going to get on the 'phone and invite a few men over to have you make good on all these promises you've just made! You'll be licking cum and sucking dicks VERY soon!" As he finished his cum-licking, I asked, "Now, tell the truth. Would you really do all those things, and let me do all those things, or did you just say them so I'd make you cum?" He got really red, and really quiet. Then, my husband said, "I promised you I'd let you do, or I'd do, anything you told me to, and I will. I've often fantasized about all the promises I just made, and I'm getting hard again, just thinking about the possibility of some of them coming true!" And he was! He had a big erection again! Soooo...I had him freshen his makeup while I went out into the den to make a few calls. A half-hour later, I was all ready. I called him into the den. Mincing in on his high heels, my husband couldn't believe what he saw! I was REALLY his Sexy Wifey now! I was standing there with my top still off, and my pretty titties that he was so proud of me showing. I had on nothing but thigh-high stockings and black stiletto-heeled pumps, and beside me, in a line, were four men with their pants off! Seeing my tits and pussy had made them begin to get hard, all of them. I told the men, "Now, the only thing you need to worry about is coming. You will each get to come; I promised all of you that before you came over." With that, I sat on a low stool, and beckoned my sweet little cross- dresser over. And I also had the men, all four of them, get in line by us. "Here's the deal, Little Miss Lace! You and I make all these guys come on my titties. Then, if you lick all their cum off me really good, I'll jack YOU off onto my nipples, and you can lick your OWN come off of me, too! But we have to service all these big dicks, first, before you can cum! Open your mouth, you sissy-husband, you, and suck on this first dick until it's hard! Do as I say!" My lacy boy did as he was told, and I stuck the cock of the first man into his waiting ruby-red lips. I could hardly believe my eyes! There was my own husband, all dressed up in lacy women's underwear, with a big dick in his mouth! I began moving his head back and forth, causing the guy's huge cock to slide in and out. It didn't take much of this stimulus until the cock was rock-hard. I pulled him back off of the dick, and began masturbating it directly over my chest, while he waited. Faster and faster I jacked it off, until the guy arched his back and shot two big jets of cum right onto one of my nipples. Quickly, I aimed the head of his dick at my other breast and jacked off three more squirts of his cum onto it. But he just kept coming! There was MUCH more than I'd thought there'd be. It almost completely covered my tits, down around the sides, and a huge pool of come in between them. I looked over at my little sissy, and obviously, he was surprised, too, and apprehensive. "What's the matter?" I teased. "You're going to get more than you fantasized about, I think. Well, you said you wanted to lick someone else's come off my titties...here it is, and don't you miss a drop of it!" Then, with cum starting to run down the curve of my titties, all around my nipples, and down under them, I ordered my sissy-husband, "Lean over here and suck and lick all this fresh cum off your Sexy Wifey's beautiful titties, my little cum-licking sissy!" We all watched as my husband lowered his head and began to lick at the cum. I soon had him sucking all that hot come off of each of my perfect nipples, licking it off the undersides, sucking up the big pool of cum from between them, swallowing it all. One by one, the guys lined up, and after I had my husband suck each one of them to complete erection, I jacked them all off onto my tits. And, after each one came, I had him lick me clean. I made him lick all of the cum off my titties, after I jacked off those hard dicks. The third dick, I had HIM jack off for me. He thought he was going to jack off the big dick onto my titties, then have to lick the cum up, but I had other ideas. As the man began to spurt onto my nipples, I quickly covered the head of his cock with my mouth and sucked all his come out. Then, I leaned over my sissy husband. Everybody watched as I let the cum flow out of my mouth and down into his open red lips. Only THEN did I make him swallow it! I fed my husband cum from a dick that he had jacked off himself into MY mouth, while he was all dressed up in women's underwear, and in front of an audience of several men with hard-ons! It went differently for the last one. He'd been waiting to come for so long, that when I had dear sissy-hubby start sucking his cock, he started to shoot off in my husband's mouth, right at the deep end of my pushing his head down! We laughed, and I said, "Since it's already happened, you'd better suck him completely off for us. THEN, I'll let you come!" And he did, too. "Now, remember," I said. "You absolutely can NOT take your mouth off their cocks, no matter what happens! I'm going to make them shoot all their hot come into your mouth, and you are going to suck their dicks while I jack them off! You look SO good with a big dick in your mouth, and you'll look even better swallowing all the semen I'm going to jack off into it. I am going to beat these big dicks off until they FILL your mouth with cum and you are going to swallow the entire load and I will continue to pump their cocks until they're completely finished cumming. Only then will I let you cum!" I reached under his slip and began jacking off his hard-on. "You'd do that for me, wouldn't you? Suck cocks for me, I mean? I'd let you come on my titties if you would suck dicks for me!" He moaned, and I knew he wanted to cum, but I was insistent. "Say it! Say you'll suck dicks if I tell you to!" "Yes, yes, I will! I'll suck dicks for you!" "And swallow their cum? Will you swallow their cum?" "Yes, I'll swallow their cum, too!" "All right, then." "What about sucking these cocks until they're hard, then opening my pussy lips and guiding other cocks into me, dick after hard dick? Will you do that?" "Yes, whatever you say!" "All right, then," I said. "Will you watch as the big dicks fuck me deep, and fill me full of cum? Then I'll want you to get right over here and suck the cum out of me. There will certainly be a pussy full. Will you do that, my little sissy? Will you suck someone else's cum out of my pussy?" "Yes! I'll watch you get fucked. I'll suck their cum from you!" I said, "That's my good sissy. The first thing I want to see you do is to suck on this dick while I jack it off into your mouth. Then, I want to watch you swallow all his cum!" While I and the guys all watched, my sissy husband knelt there between the guy's knees in his bra, garterbelt, nylons, lace slip, high heels, red wig, makeup, the works, and finished by sucking all the cum out of that big cock while I jacked it it off! "You do that so well, the next time I bring some men over, I won't even bother jacking them off... you'll just have to give them all blowjobs, while I watch!" I got so that my titties were even with his dick. "Shoot for me! Shoot your come all over my pretty titties! Then, you'll have to lick it up! And THEN, you WILL have to swallow their cum! You may feel differently about all your promises after you come, yourself, but we'll make sure you can't back out of them!" And he did. He shot and shot and shot! Everyone applauded, and everyone watched while he licked up every drop of cum off my titties! The guys all rested for a while, and then I asked my husband, "Do you remember just before I let you cum on my titties, that you would suck dicks for me? You would watch me get fucked, and suck sperm out of my pussy? Well, I sure do, and that's exactly what I want to see you do, NOW! I want you to give a blowjob to this first guy, and I want to watch you swallow all his cum. Then, we'll move on to you getting a dick hard for me, and putting it inside me while you're still all dressed up in your women's clothes." He got down on his knees, and I pushed the first man at him. This guy's dick was already hard from listening to our conversation. He knew he'd get to cum again! My sissy husband opened his red lips and took in the first big cock. He started sucking, tentatively at first, but at my urging, soon his head was bobbing up and down. Just what I wanted to see! He began sucking harder, causing the big cock to slide in and out of his mouth. More and more, faster and faster; then he reached in with his red nails, and began jacking the guy off. I was watching, egging him on, as my own sissy husband sucked and jacked off a cock. I knew this big dick was going to cum soon, and it did. The guy grabbed the back of his red wig, and held his dick deep down my husband's throat, shooting spurt after spurt of hot cum into his mouth! I loved watching him sucking a dick, swallowing its cum, just because I told him to. And there were three more of them left for him! "I think that this second one is going to be extra lucky, because he's extra big." My Sissy Hubby was still on his knees. "Open your mouth again, and get this guy really big and hard, because you're going through with your promise to get a man hard for me, then put him into me. And you KNOW what happens after that!" My poor darling just nodded. "Tell me, my little Sissy Hubby, WHAT happens after that?" He timidly said, "I have to watch as he fucks you..." I continued, "And then?" "You'll make me suck on you." "Why?" "Because I have to suck all his sperm out of you." "That's right, my little sissy. You have to suck all his sperm out of me. First you have to get his dick big and hard, then you have to spread my pussy lips and steer his huge cock into me. Then, you must watch as he fucks me to an orgasm. And finally, I want you to suck all his hot cum out of me." He looked a little unhappy, but not very, because I noticed his dick got rock-hard. He did as he was told, and started sucking the guy. Soon this strange cock was at full attention, at least 9 inches long, but I was eager for my sissy hubby to see me take it. I wanted it to be a real closeup, so I had him lie on his back, and I straddled him so that my cunt was over his face. I then motioned for our cock-man to approach. He straddled my husband's head, and I said, "Go ahead, Sissy Hubby, put the nice man's cock in my pussy!" I felt his red nails spread my lips, and the head of the man's huge cock entered me. "Hold my lips open wider. I want you to see every inch going into me!" I ordered. He did as he was told, and little by little, I was FILLED with cock. Finally, it was all the way in, and slowly at first, then with more and more speed the man began to fuck me while my sissy husband's face was inches away! "I hope you like what you see, my sweet," I teased as I was pounded again and again by the monster. I could tell that I was going to have an orgasm, and I told my sissy so. "Sissy, this big dick is going to make me come!" "Oh, yesss!" I cried. I WAS coming, as big as I ever had, and part of it was that I was being fucked so well, knowing that my husband was getting off on watching the big cock going in and out of me, but part of it was knowing that I'd be making him suck the guy's cum out of me. I wanted him to take that big step, and I knew he'd do it for me. The man tensed up, and began shooting his cum into me. Several hot spurts, and I could tell they were big ones, filled my pussy. "Get ready and open your mouth, Sissy Hubby," I said. My pussy began to leak cum onto my sissy's tongue, and he swallowed it. "Here it comes, Sissy. Catch all his sperm. It's very warm," I ordered, as the big cock pulled out of me. I watched as several globules of semen dripped out of my cunt lips into his waiting mouth, then I began pushing the sperm out of my pussy.. I watched as a stream of it flowed out of my pussy into my sissy husband's mouth. "Be sure you swallow it all, sissy! There will be more cum to come!" I giggled. The third and fourth guys were more than ready now, and I was more than ready for them to have their turns at my hubby. "I've decided that I'm going to let you come on my titties again!" I announced to my husband. "Get up here and straddle my chest." When he did, I began to jack off his dick, and motioned for one of the others to come close. His dick was right in my sissy-husband's face. I ordered him, "Open your mouth and start sucking this dick!" Soon, it was rock- hard. I motioned to my husband's garter-framed ass with my eyes. The guy caught on right away, because he pulled away, and went behind him. Another dick was thrust immediately into his mouth, so he had nothing to say about what happened next. I watched his eyes grow wider and wider as the big, hard cock was pushed slowly, inch by thick inch up his ass! I kept stroking his cock, and told him, "I'm going to make you cum on my titties again, but this time, there'll be a dick coming in your ass, and another one shooting into your mouth when you do!" The men began picking up their pace, pushing alternately into my sissy husband's mouth and up his ass. First, the dick in his mouth would be thrust further down his throat, then the big cock in his ass would be shoved in as far as it would go. I saw the man fucking my husband's mouth tense up, and then the man in his ass grabbed him and jammed his dick in all the way. I jacked off his cock furiously and leaned over and started jacking off the dick in my husband's mouth, too. I wanted to make SURE there would be cum squirting into his mouth as he came on my titties! He shot his cum onto my tits as both his mouth and his bottom were filled with cum! I laughed and said, "It finally serves you right, after playing at being a woman for all this time! I loved making you take a hard dick at both ends and watching my 'poor sissy husband' getting fucked and sucking cock!" I ordered him to swallow all the cum as the big dick was pulled from his ass. Then, as we all watched and laughed again, my husband, all dressed up in his womens' underwear, licked his own cum off my perfect nipples. See Chapter Two !!

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

2 years ago
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Sissy tasks

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

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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Hubby8217s colleague

My name is payal and i am a young indian housewife living in canada. I have been told that i have a very sexy body. My husband loves to display my legs and my shapely boobs to his friends and in public. I am deeply in love with my husband. Like a good indian wife, i very rarely have the courage to disobey him. My hubby knows my weakness very well and freely takes advantage of the situation. We have only been married for a couple of years, and i have always been a devoted wife. He is a good...

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...

4 years ago
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Welcome Your Now a Sissy

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

4 years ago
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Femocracy A Sissy Maids Tale

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

2 years ago
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A sissy called Jezebel Part II

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

4 years ago
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407am Sissy

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

1 year ago
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Milking Sissy

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

3 years ago
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Unexpected Sissy Transformation

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

1 year ago
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Sissy and Paul

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

Mature
3 years ago
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Sissy School Part 6

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

3 years ago
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Sissy Farm Chapter Sixteen

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

3 years ago
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Sissy School Part 4

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

2 years ago
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My Daily Sissy Schedule Part 1

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

4 years ago
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Forever Her Sissy Chapter 5

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

2 years ago
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My Sissy Calling

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

2 years ago
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Sissy Farm Chapter Eleven

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

2 years ago
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Sissy Emma is turned

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

3 years ago
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My Sissy Schedule

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

2 years ago
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Forever Her Sissy Chapter 4 of 6

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

3 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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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

4 years ago
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Sissy Farm Chapter Eighteen

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

2 years ago
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Sissy Hypnosis Fun

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

2 years ago
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Sandys Sissy Maid

Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I...

3 years ago
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Online Sissy Training

Online Sissy Training I must admit that I was surprised, but also thrilled to get the email. "Hello Sissy Michelle;" it read. "Please excuse my impertinence in reaching out to you, but I have seen several of your posts on Craigslist, Fetlife and Adult Friend Finder. You always say that you are a sissy seeking dominant men who will train you to become a sissy cum slut. I am guessing that you have not found that man as of yet, because I keep seeing variations on the same ad week...

2 years ago
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A sissy called Jezebel

Part I - Jezebel starts her big day, serving as a sissy maid for the dominant females of hir family. We seen in depth hir morning routine, as sie gets her sisters and hirself ready for school. My alarm goes off at 5:30 in the morning. It is an old fashioned wind up alarm clock with the clapper bell ringer which would wake up the dead, or at least this sissy who had been dreaming sweet dreams of dancing in a full ball gown with hir Prince Charming. I turn on the light on my side...

3 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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Sissy gets a black master

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

3 years ago
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I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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My Sissy Secret

My Sissy Secret I got the text on Friday afternoon, just as I was heading home for the weekend. I glanced at my phone as I left the building and stopped dead in my tracks. I didn't recognize the number, but the text sure got my attention. "Hello Sean," it read, "or should I say "Sissy Sean." I was standing in the parking lot trying to decide whether to block this guy or just ignore the text when his next message arrived. "I don't know if you remember me," he wrote, "but I...

4 years ago
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Crowd Sourced Sissy 2

PREVIOUSLY ON CROWD SOURCED SISSY: A man meets a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. The guy decides that he wants to/needs to join her as a willing-to-do- anything sissy, so he starts his own website. He will become a perfect sissy by doing whatever his online fans demand. Crowd Sourced Sissy 2 My trip...

3 years ago
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Sissy Training at Last

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

3 years ago
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Sissy Farm 20

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

2 years ago
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Sissy Farm Chapter Fourteen

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

2 years ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told...

2 years ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told himself,...

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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Classroom Sissy

Classroom Sissy By Cassandra Morgan I did it! I got in! Me! Geeky Brad Hollins. I'm one of the 10! I'm finally accepted! I'm finally one of the chosen few! I never thought I had a chance. After all, more than 200 students apply for the 10 every year, and 190 of them go away disappointed. Only the finest minds at Calvin Coolidge Community College (CCCC) get a Golden Ticket. And I'm Willie Wonka! Whee! You've heard of the 10, haven't you? It's a secret honor society at CCCC,...

4 years ago
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Sissy Velina

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

3 years ago
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A Submissive Sissy

A Submissive SissyMy sissy slave husband, Princess, was in the process of paying his usual obeisance to my feet on a recent morning. It's always good to see Princess applying his tongue to my high heels and on this particular morning he was working extra hard to please me since he was about to beg me to not take him to the beauty parlor. He knew that it was unlikely that I would relent, nevertheless, the outings I arrange are so excruciatingly humiliating for the poor dear that he is ever...

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