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Making a Sissy By Jena Corso Edited by Angela Meyers Chapter Five Quickly the bib and sheets were off Justina as they pulled him from his feet and hurried him from the room. His legs were stinging as they practically dragged him down the hall and across the house as suddenly he was brought outside. Through some manicured gardens, their shoes clicked on well-placed huge chunks of slate as they rushed under a tunnel like rose trellis. As they came out on the other side, they entered a fabulous standalone solarium that was detached from the house and then through a flower filled entrance foyer into a private area of the elaborate conservatory. "Excellent timing, ladies," said Contessa, looking at her watch. "Let's begin lining up and you'll begin on que with the music. Here, Justina." Justin was handed a full bouquet. He was completely confused as women began hurrying into position behind him, all in pink matching dresses. "Mistress Contessa, I'm not ready," a girl from behind said as everyone turned as she came out of a back room with two workers carrying the back of her dress. "I'm sorry Mistress. This is just too much, and I can't do it." She looked beautiful in a huge bell shaped wedding gown with dark brunette tendrils and big full lips, beaming. "You'll be fine, Bianca," said Contessa, walking over to her. "These jitters are normal." "No, really," said Bianca, starting to shake. "It's all happened too fast. I'm not a girl. I'm a..." Before she could get out the word, Contessa slapped her across the face, shutting her up and then glared at all the girls in pink before returning her attention to Bianca. "No, you're not really a girl, Bianca. You're a woman now, and women have jitters on their wedding day, especially hormonal messes like you are sometimes," said Contessa, folding over her veil to cover her eyes. "Now it's natural to be nervous, and who wouldn't be knowing you'll be spending the rest of your life enjoying such a gorgeous well-endowed husband, but embarrass me and you'll be assured of spending a much different life than this one you're lucky to be gifted." "Yes Mistress Contessa," said Bianca, reaching under her veil and wiping a tear. "I'm sorry." "That's better, and you make a beautiful bride, dear," said Contessa, walking past all the girls inspecting them and stopping at Justin. "Justina, you'll be first, and all you need to do is walk slowly clutching your bouquet with both hands. You'll stop when you're near the altar, step to the side and then hold hands with the handsome ring bearer who'll follow behind you." "You want me to hold hands with a boy?" yelped Justin. "Don't be nervous, he's really almost a teenager, so much too old for a cutie like you but why wouldn't you?" smiled Contessa. "You're our flower girl. Now places everyone, and I must get to the altar to join our lovely couple." Behind his bangs they dropped a flowered headband and then the music started as they snapped in some clips. With a nudge from Miss Evelyn, he began walking from the conservatory out a French door down a white carpet as he looked up, seeing about fifty people seated on each side of the aisle. He was suddenly the flower girl at some form of arranged wedding, as he noticed a huge black man standing at the front in a tuxedo, as the obvious groom. There was Lynne standing at an aisle seat smiling, looking gorgeous next to Dirk holding hands as he walked, knowing that should be him yet instead he was holding a bouquet. He'd need to gingerly march up there before he was soon joined by a zit faced tween black boy almost his height. He'd have to stand holding hands with him the entire time while Contessa served as master of ceremony and judge, joining the happy couple as man and wife. Although he wasn't too sure if the bride was happy or not, but he'd seen the end result of a sissy being turned into a bride. He knew now this would be much more than any sexual game as he could barely stop quivering as he was worried sick about what was happening. When they became husband and bride, all he could do was search everywhere for an escape, but somehow all he could feel was exhaustion. His legs seemed to be weakening and his body feeling like he was about to pass out were sensations he couldn't shake as they walked up the aisle and people celebrated the ceremony's ending. As he passed Lynne, she winking at him while she was kissing Dirk, almost like she could care less about what she'd done to him and then Miss Evelyn grasped his hand as they reached the last steps before the conservatory. "Don't worry I got you, sweetie," said Evelyn, grabbing his waist. "I was looking forward to seeing you dance a little at the reception, but girls your age don't usually make it up that late." Just that quickly he was back in the carriage with his eyes feeling heavy and then ten yards of her pushing him through the gardens, he was out like a light asleep. "Good morning, Justina," said a new voice the next day. "Oh?" said Justin, cracking his eyes. "It's morning already?" "Kind of," the voice said. "It's very early." "And I'm still here?" moaned Justin, realizing he was in the big crib again and in girly pajamas. "And where's Lynne?" "I'm not sure?" said the girl. "But from what I know, you've only been here 2 nights and you remember me, right?" "I'm not sure I do? I'm so confused about everything," replied Justin. "Did you help change me or something?" "No, and that's how they keep you purposely. Confused and like a baby in the beginning," said the girl. "It's the hormones and the crazy chemical concoctions. I still can't explain it myself, but eventually you mature and get more aware of everything?" "What do you mean eventually?" moaned Justin. "I'm just here as punishment by girlfriend and her sister. I know they are just trying to scare me, embarrass the crap out of me, and this better be ending soon!" "I guess you obviously don't recognize me," said the girl. "I kind of figured you wouldn't in your current state, or really more like in my current state?" "Huhh?" sighed Justin, not understanding. "Well I guess even if you don't maybe you'll at least remember me? Maybe even remember my name?" said the girl. "It's me, George, or at least I was." "George?" asked Justin curiously. "George, in like I'm your girlfriend's sister's ex-husband and weren't you Justin?" said the girl. "Oh my gawwddd! And I am Justin!" yelped Justin, looking at him. "But you're like a ...?" "A girl? Well kind a. I'm a sissy, and I'm not sure what I'm going to be in the future, but I am what I am," said George, shrugging his shoulders. "But wait? I heard that she dumped you for being a cheater and a loaf?" said Justin. "She said she tossed you out?" "Well more like tossed me here," replied George. "And dumped me here to be sissified and away from my children. I learned she's a part time Mistress training under Mistress Contessa, and this is how she solved our marital problems." "And you're telling me this is how my girlfriend is planning on fixing our issues," gulped Justin. "This isn't just some punishment or crazy sexual game?" "Looks like she's already made quite the progress to fixing things, and you're well on your way," said George, opening his diaper and peaking in. "Miss Georgette, there you are?" yelled Contessa, standing in the doorway now, startling him. "I was looking all over for you and what are you doing here?" "Oh, I just heard a noise and walked in to check on her," said George closing the diaper, back pedaling. "She was up and obviously wet, so I thought it would be best to change her." "I see, but leave that to my staff assigned to her, and I guess you've now made a difficult decision into an easy one for me, Miss Georgette," said Contessa, looking at Miss Evelyn and nodding. "The papers please, Miss Evelyn." "Of course, Madam." Evelyn handed her a clipboard as Contessa flipped a few pages, signing. "I'll need you to bring this down to Mr. Ivanov for countersignature, and order the staff to get everything out the door at once," said Contessa, handing it back. "Now hurry along and instruct them to make sure they pack the essentials plus whatever custom made outfits can fit in the trunk. We'll ship anything else required, but I imagine a new wardrobe will be in store anyway. Then please tell Mr. Ivanov I'll be down shortly, since he'll be very excited we have a deal, but impatient since I know he has a tight schedule to keep." "Mr. Ivanov is here again?" gulped George. "And to see me?" "Well, yes. I expect you couldn't easily forget Mr. Vladimir Ivanov who you served wonderfully when he visited. He's here again and that's why I was initially looking for you," said Contessa with a big smile. "You know how he feels about you of course?" "Well kind of? Yes," nodded George, getting embarrassed and then thinking. "Wait, you're not talking about my stuff are you?" "Well darling, thing is I am, and you know he adores you so I've got some exciting news for you, Georgette," said Contessa, coming closer and touching his face. "You'll be on your way home soon." "Home, Mistress?" said George, surprised and excited. "He's helping me go home!" "Yes dear, to your new home and I couldn't be happier for you," said Contessa with a big smile on her face. "By new home you mean his home?" asked George stunned. "Like to leave there?" "Why of course," smirked Contessa. "You're a lucky girl, and I've signed off on it. In fact, he's here to take you home immediately." "But doesn't he live in Russia? You're saying he's taking me to Russia!" George yelled. "Yes Miss Georgette. His wife has approved, and he's paid handsomely for you," said Contessa, matter of factly stretching her fingers and looking at her long nails. "You'll live well in a house as grand as this one, but of course garner all the attention instead of just being one of my darlings." "You mean clean the huge house by myself, be his sissy slave and probably his personal sex toy," gulped George. "Well I don't know anything about what other staff he may employ, nor do I care Miss Georgette," said Contessa. "But what I do know is you'll certainly be more than just a servant or his personal sex toy. Of course he was impressed by your oral skills or you wouldn't have been selected, but I know he isn't planning on keeping you only for himself." "Oh no," said George as he swallowed hard. "He's got four boys from eighteen down to ten that will absolutely adore you as they develop into men, so a delicious sissy like you will be the perfect release for them after you complete your chores each day," said Contessa, touching his chin as she cupped his face. "Now ladies, please escort Miss Georgette down to Mr. Ivanov as your things are in his limo by now and his private plane a waits. Congratulations dear, and what a wonderful life lies ahead of you now." "Contessa, pleasss," George pleaded as he was quickly ripped from the room. "Well then little one, I hope she didn't disturb you this early, but now that that nuisance has moved on let's turn our attention back to you sweetie," said Contessa, softly patting his head. "We planned on getting you up early anyway and Miss Lynne has picked out quite the beautiful Easter dress for you to wear today. Doesn't that sound exciting?" "What is going to happen to me?" asked Justin. "Where is Lynne, and please tell me this is almost over?" "Oh she'll be along soon enough," said Contessa playing with his hair. "But in the meantime while I go down and make sure Mr. Ivanov gets a proper send off, Miss Lynne and I have decided you looked darling in all those curls last night that maybe we'd do something a little more permanent. Doesn't that sound delightful?" "Delightful?" shivered Justin as she stretched his hair on the left. "No please, none of this can be permanent like it was with George. Please, no more." "Relax Justina, no two sissies are alike dear, and my suggestion to her was regarding your need for a much more appropriate haircut you'll now be getting," said Contessa, snapping her fingers to her staff. "That darling will at least send you on your way to a much more normal life after today, so hopefully you'll eventually show a maturity that of course none of us have seen in you yet." "Oh you will. I prom--" cried Justin as a binky was shoved into his mouth to quiet him. They clicked the locks on the wheels at bottom of the changing table and then began wheeling him from the room as he was lying back staring up at them. He reached up, feeling that the little pigtails were now full sized at each side of his head, as all of last night's curls had being tied up while he slept now swinging from atop each ear. With two turns of the corridor, they had brought him into a brightly lit room and then quickly pulled all the snaps stripping off his pajamas. He looked around, realizing he was in some form of home salon as they dropped him in a big red leather chair in only his diaper before wrapping a cape around his neck and clicking the pedal raising the chair. Quickly he realized it would be nothing like getting a haircut at the crowed salon at the mall, as instead in came a flamboyant sissy with bright pink hair and lips, immediately sizing him up. "Begin the process Miss Ameli,a and I will be back shortly," said Contessa from behind. "Yes Mistress," said Amelia in a deep, scary voice. Justin was as confused as he was scared, as she began by dampening his head with a spray bottle and then pulling out each pigtail. As his head grew extremely damp, she combed through every inch of his head and then stunned him as she proceeded to trim away some of the length. In no time his hair no longer touched his shoulders, as he could do nothing but sit as she began layering. Was this part of them turning him back into a boy was all he could hope for as he sat watching significant chunks slide down his cape, never having his hair this short since high school. She said nothing when she finally put down her scissors, dropping down his chair back as suddenly his head was in a sink. After she washed and conditioned it, scrubbing it thoroughly before she raised his chair back up and then he realized what Contessa meant about this being more permanent. This would be no boys cut, as Miss Evelyn dropped down a container of small thin rods next to his chair on the right, assisting Miss Amelia as she began setting his hair. Section by section little papers were folded over across small sections and then each tiny rod was wound in. Before he knew it, Vaseline and cotton had been added to his hairline that fronted countless tight little rollers and a stinky solution had been added to his head. There would still be no conversations the entire time his hair processed as up and down he'd be dipped into the sink. He was noticeably whimpering in his mousey little voice with the binky still in, yet all they did was ignore his grumbling until Contessa eventually returned. She walked over, looking down at him, touching his face as Miss Amelia unrolled a rod testing the spring of his apparent coils and then Contessa nodded, looking satisfied. They rerolled the rod and then dipped his chair back down as Contessa lifted the cape before parting his legs, opening his diaper. He could feel her manipulating his male parts, squeezing and shifting then around and then wanted to scream as he saw her hold up the metallic device. He watched her coat up the tool with some lube and then knew the feeling all too well now of the rectal thermometer entering his anus. After a gasp or two as it went in pretty far, it wouldn't be staying long as luckily ten seconds later it beeped and she removed it. "Wonderful," said Contessa, pulling out his binky and holding up an eye dropper. "Open up dear and the medicine has worked. This should be the last dose." "It's ok, I'm here sweetie," said Lynne, scurrying over, kissing his forehead as down his throat went the gross solution. "Oh Lynne," whimpered Justin. "I'm so happy to see you. Please can I get up now and go...." "Adults speaking, Justina," said Contessa, jamming a binky back in his mouth. "You suckle and stay calm please. Miss Lynne take a look dear." "Oh gawwddd," said Lynne, walking over and looking down, concerned. "Like marbles now." "You shouldn't be surprised dear?" said Contessa, dropping the cape back down. "We talked about this already. Papers please, ladies." "I know, but this has all happened so fast," said Lynne, watching Contessa take a clipboard from Miss Selena before scribbling a signature across the bottom of the page. "I'm not sure I'm ready." "It's time, Miss Lynne," said Contessa, handing her the clipboard. "She won't regress any further, and I'm ready to commence her training." "So you've fully accepted her," said Lynne, looking down at the form. "Just like that, and don't we need to discuss anything else?" "Yes dear, and no there are no discussions. That's how it happens and you cut the cord," said Contessa, making a cutting motion with her fingers. "Snip snip darling and we all move forward." "Oh gawwdddd," gulped Lynne, closing her eyes and scribbling her name. "But I can't watch." "Of course you can," said Contessa, rolling her eyes as they raised the back of his chair back more slightly now. "It'll be an important step for you." He was completely unprepared as they began restraining him, strapping down his arms, waist and then raising the bottom of the chair. "Stay clam," said Contessa, softly applying pressure to his chest. "It's just for your own protection and it will be brief." To each side they extended a leg rest, cupping his foot and then securing his ankles. They lifted his cape now using a clothes pin to pinch it off his bottom permanently like a pulled back sheet and then he watched her put on some latex gloves. "No, please?" yelled Justin, spitting out the binky seeing a long needle dip into a syringe before a touch on his cheek distracted him. "What is that?" "Sssshhhh," whispered Lynne as she come in behind him, softly rubbing his forehead and then kissing it. "You won't feel a thing honey. She promised me, and even I can't take it but you're ready already." He feel a soft pinch as the needle went into his private area and then quickly everything went numb. "Feel anything Justina?" said Contessa, looking down on him with what looked like a scalpel in her hands. Just the sight of it was almost too much to handle as he tried to answer but couldn't as she dipped it down from his sight. When she raised her left hand back up asking for another instrument, he noticed some red on her gloved fingers and it was the last thing he could remember before be passed out. He woke to the feeling of soft warm air on his neck and the sound of the hair dryer blowing through its big bulky diffuser. When it finally clicked off, he was a bit drowsy as he could feel Amelia's fingers against his scalp, picking through his hair and then she lifted his chin trimming his bangs. Once she brushed off the little clippings on his nose, he felt a snap at his left temple and then the right before off came his cape. Ever so gently now frilly white pantaloons were lifted up over his diaper as he felt a strange tenderness once they hugged them in place. Next they lifted him to his feet as his socks and shoes were already on, and then oddly his legs were lifted into a big dress. Delicately they guided his legs inside the holes of the built in bottom and then up it came past his waistline. When they slipped his arms inside and then zipped him up, he heard a gasp from behind him as he turned, seeing Lynne. She was crying like the baby she'd made him become, as she held out her arms for him to come over to be hugged. "Oh myy gawwddd," whimpered Lynne as tears flowed down her cheeks. "Yes she's quite adorable," said Contessa, staring at their embrace. "Isn't she?" It hurt just to walk as he felt quite tender, yet after three steps he was tenderly hugged. The heartfelt moment lasted quite a bit until she pushed back and looked at him, trying to keep it together. When she stood up and stepped back, he could see his reflection in the mirrored wall and almost couldn't believe it himself. He was in a floral purple Easter type dress with pink and mint colored flowers, lavender lace edging, puffy cape sleeves and a thin lavender sash. From beneath the dress meant for an infant, white ruffled pantaloons poked out covering his legs, and mint and lavender crinoline puffed it out. White frilly ankle socks ruffled out from his lavender Mary Janes and his entire outfit was decorated in tiny pink bows. There'd be no signs of makeup on his face, yet his long lashes beneath is new haircut made his cheeks turn bright red as he stared at himself. Still present were his little bangs, except now they'd be trimmed much shorter across the middle of his forehead. Behind them a soft thin lavender headband with a huge purple glittery flower offset to the right, fronted short full springy curls as he'd certainly been given a tight perm. From the perm's chemicals, his hair had been lightened two or three shades just as his was as an infant, and the tight texture of a curls gave him an infantile look of a baby girl just beginning to grow out her hair as it was growing in. As girly and as infantile as they had made him before, this was easily the most radical change, as all his long hair had been sheared down to baby curls, and even worse something inside him no longer felt right as he felt weak and feeble taking just baby steps. "Oh gawwdddd.... I can't Contessa," said Lynne, wiping her eyes. "I just can't! I've gotta go!" "Go where?" whined Justin. "Just go Justina, and don't make this harder than it already is," said Lynne, turning away. "I'll always love you, and I've got to go. Right now!" Out the door she raced as Justin stood extremely frightened. "Don't worry Justina, she'll be fine and so will you," said Contessa. "It's always hard in the beginning, but worrying about being hard ever again is something you won't need to worry about." "Do not tell me that's what you were doing down there?" shivered Justin as his eyes bugged. "I saw the blood." "No dear, the little useless thing will be there until maybe someday when you're old enough to decide if you really want to keep it," said Contessa. "Some sissies do and some don't. But let's just say the little easter eggs you had down to behind it will no longer be found during the Easter eggs hunt, as lucky for you my princess they were already shriveled up and useless." "No," gulped Justin reaching down. "Oh it's fine my sissy baby. Think of today like a rebirth sweetie, and you look quite precious," said Contessa. "It never takes my girls long to adjust, but let's say we've got you nice and buttoned up down there while the little tweaks we may heal and sissies age fast, so it won't be long until you're in panties and forgotten they've ever existed." Eighteen months later. "Good afternoon sir," said Justin, curtseying as a tall man answered the door. "I'm Justina, and I was sent to begin here today." "Yes, we've been expecting you," said the man, opening the door all the way. "Please come in, and i'm looking forward to this day." Justin trotted in now wheeling two suit cases, in a full French Maid uniform. The classic sexy black satin short puffy skirt sat beneath the tight short sleeve bodice, displaying his ample cleavage. Atop it a frilly apron in white lace added a delicate touch, yet the black fish nets and pointy black stilettos told a much different story. Slutty ruby red plumped full lips were the focal piece of his heavily made up face, as dark eye shadows, thick curvy lashes and burgundy cheek bones had eliminated any prior juvenile appearance. He looked now like a young curvaceous woman that would turn heads as he sauntered past the man before putting down his bags and flipping his long, thick golden ringlets off his shoulders. "How wonderful?" said Justin, awaiting instructions as the man closed the door. "So where would you like me to start? Bathrooms? Kitchen or wherever you'd like sir?" "Well. I was thinking bedroom or better yet right here in the living room. So leave your bags there for now," said the man pulling him into the living room. "You could do the bathrooms after you clean my pipes and then fix me a sandwich." "Sure," smiled Justin, touching his crotch through his pants. "It would be my pleasure and that's easy. I'm an excellent cook as well for future reference, as well as quite skilled at pipe cleaning." Down went this new Justina, dropping to his knees and unzipping his pants with his long French nails. When he pulled it out, the guy was already rock hard, so when he dropped his pants to his ankles, Justina immediately swallowed him. Dirk was quite large, but he handled him no problem, taking him deep and bobbing up and down. Justina did all the work as he moaned, enjoying the service and then grabbed the back of Justina's hair, holding tight as he exploded into her mouth. "Really Dirk?" said a voice from behind. "Already?" "Oh come on, babe," sighed Dirk. "Isn't it what we hired her for, and don't spill any on the rug, Justina. My wife will freak the fuck out?" "Ahhh.... It's a fringe benefit for you, but not exactly," said the woman, folding her arms. "Lynne?" mumbled Justin, swallowing hard, seeing her standing there in a pinstripe business suit. "I mean Miss Lynne." "Yes, and hello Justina," said Lynne with a smile on her face, relaxing her stance. "Finish up honey, and he's right I won't be happy if you drip on my good rug, so lick him clean, then when you're done meet me in my family room please." Dirk pushed her head back down as Lynne exited the room with her brief case as he went to licking Dirk clean. When Justin thought he was finished, he was greatly mistaken, as Dirk spun him around, quickly becoming aroused again and spun him around reaching under his skirt. Like the good servant he had become, he allowed his panties to be dropped, stepping out of them and following Dirk's lead. The first love bite was a bit painful as Dirk bit down on his neck and then after a few hard nibbles, Dirk pressed him forward, mounting him and pushing inside. He stood just bracing himself against the furniture as he began pounding his ass with some vigor as Dirk hammered Justina as hard as he could. He moaned and groaned on command like a trained seal, taking his every thrust until finally he was finished, exploding inside him. When he ran that doorbell, he never expected that he'd be the hired help at his old girl friend's new house, let alone having being used as her husband's sex toy before he'd have to clean the place. When Dirk finally pulled out of Justina, he cleaned off any drippings and then asked what he wanted for lunch. He prepared a soup, salad and huge sandwich plus some nice sides. When Dirk's plate was finished and he did the dishes, he was delighted to walk inside to see Lynne. "Good afternoon, Miss Lynne," curtseyed Justin. "I'm honored to be here, and you wanted to see me?" "Yes please sit down sweetie, and I'm so glad you came," said Lynn, patting the couch next to her. "Come honey and sit." "Yes madam," said Justin. "And congratulations. I didn't know you'd gotten married." "Well thank you, and obviously you've met my husband," Lynne smiled as he sat. "I'm sorry if he didn't even give you a minute to get acquainted with your new surroundings, but he was so looking forward to seeing you again and well? It's been awhile for him." "Again?" asked Justin, a little confused. "I'm sorry Miss Lynne, but I don't believe I've ever... you know with him before madam." "Oh I'm sorry, and you haven't."replied Lynne, shaking her head. "Meeting him was what might seem like a lifetime ago for you sweetie, and Contessa did say those memories would fade but you still remember me, don't you?" "Yes madam. I didn't know at first I'd be here at your home, but just seeing you it's all flashed in my head," nodded Justin, a bit embarrassed. "Really?" said Lynne, a bit surprised. "Intertesting?" "Well I'm not so sure I'd call it that madam," said Justin, looking down, breaking eye contact. "But that seemed like it was also a lifetime ago? Some memories are faint and some are vivid, but I'm obviously a much different person now." "Yes," said Lynne, patting his leg. "And let's hope only the good ones are vivid." "Are the ones of you dumping me off and making me into a sissy classified as good ones?" asked Justin, getting emotional. "Cause some of those are still pretty vivid." "Ah those," nodded Lynne, taking his hands. "Well those were different times for both of us, but look at me Justina. I never dumped you off." "Are you kidding?" Justin said. "Honey, it was necessary and for your own good, but I never dumped you off," said Lynne. "I've thought about you every day." "What?" said Justin as she wiped his eyes. "Every day?" "Yup, every single day," said Lynne, taking a big scrap book from the coffee table. "Now look so you'll believe me." "That's me?" said Justin as she opened the first page. "Yup in the first dresses I ever bought you," said Lynne. "You were gorgeous with all those little curls and no matter what we put you in, you always looked so pretty. It was crazy." "Oh gawwdd," nodded Justin. "I remember them dealing with me in all those wild curls." "Yup, and look at you as a flower girl," said Lynne, turning the pages. "Then look how adorable you look in your dance school outfits, and then in your tutus for your ballet recital. I cried every time." "You were there?" said Justin as the memories were returning. "Of course, I been there throughout it all," replied Lynne, turning pages. "All the learning. All the outfits. All the hairstyles. And all the growing up! It's been amazing and heart wrenching." "You mean for me," said Justin, shaking his head. "Well yeah, but for me too," said Lynne, turning again. "I mean I was there for all six proms and even for the two where you weren't rented out for. Hell, I picked out all six dresses and even set you up with my nephew and my sister's cousin for two of their proms. I've seen it all." "But I haven't seen you there?" said Justin, amazed seeing the pictures. "Yeah well that's by design as they make us cut the ties when you begin your training, but I haven't been able to," said Lynne, closing the scrapbook. "Mistress Contessa allowed me some liberties to watch you mature while I sat without making any contact, in wigs and disguises. I've got quite the collection, that you'll see once you clean in my closets." "I don't get it?" said Justin. "If you cared so much about me, why did you force me into a life of servitude and just watch all these years." "Honey, I can still care and love you, yet I had to do what's best for you, so that's what I did," said Lynne, taking a deep breath. "And it may seem like a lifetime or years, but it's only been eighteen months. Sissies age about a month to a normal person years, so right now you're still a teenager as sissies go, and then within six more months you'll be back to your true age." "You mean I'm eighteen going on twenty four?" Justin asked, shaking his head. "Something like that and it's a confusing time for girls," said Lynne, raining her hand. "Trust me, I know from experience but a time I thought you'd need me." "Like I need you while I serve you?" said Justin, confused. "You mean a time where I'm old enough to..." "You don't need to go there, but yeah sure. Plus I really need the help right now both physically and with my husband." Lynne unbuttoned her suit jacket. "You see I'm pregnant, and I can't do as much as I'd like." "Oh," nodded Justin. "I see, madam. I've served many like that, and of course. I guess even under the circumstances I can handle all that." "Good, because if you work hard for me and some others for the next few months until your little brother arrives, then I'll have enough saved that you can move on," said Lynne, touching his hand. "I know that's what you'll want." "Move on?" asked Justin, confused. "Wait? My what?" "Yes honey," said Lynne as some tears rolled down his cheeks. "My plan is to adopt you, and he'd be your little step brother." "Adopt me?" Justin replied, stunned. "Yes," said Lynne, pulling out the papers. "In fact I already have and then once the baby is settled, then we'll settle your problems too." "My problems?" said Justin, completely confused. "Yes. A little snip snip circumcision for my son, and a big snip snip for my daughter so she can live the life she was always supposed to live, not just that of a sissy," said Lynne, rubbing his back. "I already have all that money saved, so by the time you're back to being twenty four, you'll be ready to live like any other girl." "Oh my gawwddd!" gulped Justin, looking down at the papers. "I've assumed your last name, and it already says female on the certificate." "Yes, you're Justina Juliette Jones now. You can thank Mistress Contessa. She's got friends in high places, some of which you've recently serviced, honey," smiled Lynne. "So I should call you mom, then?" Justin asked stunned. "Ahhh no. Stick with Lynne please," said Lynne," "That would be too weird, and still think of me like the same step mom that only eighteen months ago was changing your diapers." "Oh? Ok?" replied Justin before mumbling to himself. "And cut off my balls." "What was that, dear?" said Lynne. "Oh nothing, Miss Lynne," said Justin before mumbling to himself again. "And who made me suck off my step dad's dick." "You do know I heard both those things right?" Lynne laughed before growing stern. "But I guess yes to both and just because I expect some bullshit talking back from a hormonal teenager, doesn't mean I'll tolerate it. Understood, Justina." "Yes," nodded Justin. "Good, and just so you know adoption also means I paid handsomely for you, so you've still got quite a bit of serving and earning to do to pay off Mistress Contessa," said Lynne. "I'm well off, but you'll be working off some of that debt, young lady." "I'm sure," nodded Justin. "I'm sorry Lynne, and thank you." "Good girl," Lynne kissed his forehead. "Now go change into the nice red dress step mommy left for you? I want to see how it looks on you, as I might have you wear it for dinner?" "So no cleaning tonight?" Justin perked up. "No, I thought it would be best when Contessa gets here later that you're dressed," said Lynne. "You'll of course need to prepare dinner and serve us, but then you'll change to eat. It's extremely sexy." "Mistress Contessa's coming here already?" asked Justin. "Don't worry. Not for you, dear," said Lynne, throwing up her hands. "She's coming for supper and to pick up Dirk. He'll be useless in raising our child, and I won't need him with you around, will I?" "No, I can help with everything?" nodded Justin like a puppy dog. "And anything!" "Exactly, and then once she takes him from the equation, then you'll be able to focus on other men instead of wasting your efforts on him," said Lynne, tapping her chin. "I have a few boyfriends lined up." "I'll be dating?" Justin asked. "If you'd like to call it that sure, and of course only after a hard day's work," smiled Lynne. "I thought a few cute college studs should be good practice before your surgery, and good practice before you settle down and get married." "Married?" Justin shook his head. "Very funny! I thought I just got adopted?" "Who said I was joking? I've already been working on planning your wedding to my boss, and I realize you don't know the names of all the men you've blown, but he's been a good client," Lynne smiled. "He's dying to have you for himself, but there's really no rush while you work, go through some procedures and help with the baby. Really I figure once the baby is a year or so and we're all settled in at his mansion, you'll be ready." "You're saying you're adopting me to marry me off," gulped Justin. "Relax, he's filthy rich and really he won't live that much longer? But not just yet," said Lynne, cupping his face. "There's so much to do first, and his heart is strong for an eighty year old, so we still have time." "Ewwwww!" Justin said. "I think I'd rather be your little princess again. Please, life as a little sissy was so much easier." I'm so happy you felt that way. That makes me feel better about everything that's happened now," said Lynne, touching her chest, feeling good. 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My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

1 year ago
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Miss Lindas sissy

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

2 years ago
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The Misadventures of the Worlds Worst Sissy

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

2 years ago
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First time Sissy

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

Transsexual
2 years ago
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Im Not A Sissy

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

1 year ago
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Richard the Sissy

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

3 years ago
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The Lingerie Salesman Sissy

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

4 years ago
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son turned into moms sissy

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

3 years ago
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Cum Craved Sissy

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

2 years ago
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Born a Sissy

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

2 years ago
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sissy

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

2 years ago
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From manager to sub sissy

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

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