12 comments/ 47915 views/ 45 favorites Alex to Alexis Ch. 01 By: TransPrincessMorgan Thanks to Jack Murphy for being our volunteer editor! Enjoy! ***** Chapter 1: Feminization Alex was late home again. Once, maybe twice would have been acceptable, but this was the third time this month. His mother, Daniella didn't know what to do with him, especially considering her other children, the eldest, Hannah, who was 25, and the youngest, Amelia, who was barely 18, behaved exceptionally! Both Hannah and Amelia regularly achieved top grades and never saw trouble, so why was it that the middle child Alex was so unruly? She suspected it to be something to do with the absence of his father. He had walked out on the family shortly after Amelia was born; he contributed a portion of his vast wealth to them without ever showing up. Hearing him slam the door shut, Daniella decided to reprimand her son. "Well, well, well. What time do you call this, young man?" Daniella sternly asked her son. Alex shrugged and barged through the hallway, knocking down Amelia's rucksack. "Outta my way, sissy", he snarled to his younger sibling. Daniella and Amelia shared a concerned glance as yet again, Alex slammed the door to his room. He had once been such a considerate child; what had happened? Daniella realised that she needed to formulate a plan to discipline her son as his school would provide no assistance since summer vacation was coming up, and she would need Hannah and Amelia's help. The girls sat at the dinner table that evening while Alex played his horridly loud records in his room. "I'm sure you are all aware that your brother's behaviour is utterly inexcusable, and needs to stop", Daniella began. "He's so mean", whined Amelia. "Some means of discipline are necessary if we're ever to get through to him", Hannah said. "Perhaps you could try contacting the school?" "No chance", Daniella rebuked. "They've been useless so far in addressing his behaviour; this is something we need to take into our own hands, after all, there are three of us and only one of him". "Maybe we could confiscate something of his?" Hannah attempted. "Tried, tested, and failed. His record collection, his comics, grounding, nothing gets through. We need something draconian, something serious this time", Daniella sighed. Amelia whined again "We're never going to get through to him; to him we'll always be sissies". A glimmer struck across Daniella's eyes and a smirk arose, which Hannah noticed. "Care to share mom? If you hadn't noticed, we're all out of ideas," Hannah moaned. Daniella smiled knowingly, "Amelia's right; to Alex, us girls will always be sissies. But what if, and bear with me girls, but what if, we lowered him to our level?" Amelia frowned, perplexed, "What, we make Alex a sissy?" Hannah eyes shot up too, "We sissify the boy!" sharing a giggle with her younger sister. "Now, now girls, calm down. This seems clever right now, but we're going to have to think this through. I mean, how are we going to debase your brother to the point where he sees us as equals?" Daniella pondered. "Or, as superiors," Hannah added, "After all, this is supposed to be punishment." "Okay girls, it's brainstorming time, feed me your ideas and let's see if we can about pull this off", Danielle replied to her two enthusiastic, mischievous daughters. They debated for hours on how, when and why to do it, but slowly, and surely, they made their plans. Alex returned home from school late again. But this time, his family were prepared. "Outta my way, siss..." Alex was cut off by his mother's stern voice. He knew this time, it was serious. "I have had enough young man. Enough. I cannot bear to look at you. Playing football again, young man? Just look at all that mud in your hair and on your clothes. Stick them into wash and take a shower. I'll deal with you when you're out," Daniella demanded. Alex knew better than to mess his mother about when she was in these moods, so he threw his uniform into the laundry bin and got in the shower. Once the water was running, he noticed something was amiss and yelled "Mom, where's my body wash and shampoo?" Daniella yelled back "You'd used it all silly; use Daniella's it's just as good, and don't you dare disobey me, boy." Slightly frightened now, Alex applied the shampoo and conditioner to his shoulder-length brunette hair and massaged, before rubbing his slim body with the girly shower gel. Alex had always been self-conscious of his body - he'd picked up too many of his mother's genes along with his sisters. The wash was feminine; it smelt of roses, and to his alarm, his body hair rubbed straight off and rinsed down into the plug. Below his hairline, he was now completely hairless. Probably best not to say anything; he'd get teased like crazy. Toweling off the moisture, Alex stepped outside, wrapped the towel around his waist and headed to his room. He peeked into his wardrobe but was surprised to find Hannah or Amelia's clothes there and not his own. Turning round to call for his mom about the mix-up, he was given a minor fright to find her in his room, closing the door behind her. "Ugh, mom... What are you doing here?" Alex stuttered. "I'm here to teach you a lesson son. You might have noticed your perfumed body, or new wardrobe. Its time I taught you learned what we go through..." Daniella continued evasively. "What the..." Go away mom Alex murmured. Daniella smirked to herself and said to her son "Well, if my boy wants privacy... Oh well, at least pass me those two glasses of water by your bedside table for the wash." Confused, but certainly not wanting to piss off his mom anymore, Alex held the two glasses of water, but before he could react, his mom ripped of his towel, revealing his hairless nude body. Alex struggled and protested as Daniella snapped pictures on a camera laughing to herself as Daniella caught his humiliation. Eventually, he put the glasses down, pulled the towel up and tried to regain his modesty." "Delete those shots, mom," Alex demanded, stutteringly. "Oh no. Oh no, oh no, oh no. I don't think so Alexander, these photos are going straight to your sisters. I'd like to see what they'd make of this." Realising he was trapped, Alex submitted. "No, please no! Fine mom, you got me. What was this punishment?" A wicked grin flashed across his mother's eyes. "Well, if you insist," as Daniella approached Alex's wardrobe and extracted some items. A teal crop top, a short leather skirt, some tights, panties, what looked like a tub of clay, a bra, some breast inserts, and a pair of pink 6 inch heels. Alex gulped. "Mom... Please, no," Alex stammered to his mother's delight. "Well Alex, are you sure you want your sister's to see?" Reluctantly, Alex conceded to his mother's punishment. Daniella began by dipping into the jar of clay and telling Alex to spread his legs. He complied, shamed beyond compare. His mother grabbed his small, limp dick and tucked it down near his tight pink hole before she applied the clay over his crotch, making sure not to cover his asshole. Smoothing it out, she began to contour it, and it looked damn near natural. Once she had done plastering it to his crotch, she drew a thin line down the center that, from a distance appeared to be a vagina. She then asked him to begin dressing, and he pulled the panties up, which happened to be a thong, until he felt the string fit snugly between his cheeks. With the clay molding, it was impossible to tell that there was a penis under the panties, and the slit his mother had drew in even gave him a realistic camel toe! Then, she began slowly rolling the nylon tights up his smooth soft legs, showing him the correct technique to avoid any runs. Next, the leather skirt came up. It barely covering his ass, and he knew if he bent over his tight young cheeks would be on display for whoever was behind him. Next, his mother grabbed the silicone fake breasts and began to apply a sort of glue to the flat end. Once she had spread the adhesive liberally across the silicone, she planted the breasts firmly onto her son's flat chest, holding them there to make sure that the glue took. As soon as his mother let go, Alex could feel the weight of his new breasts on his lower back, and as his hands went up to feel them, they were surprisingly realistic. As his mother put on his bra, Alex felt a portion of the weight lifted, and he breathed a deep sigh. Afterwards, his mother had him pull on the crop top, and Alex was deeply embarrassed by the amount of cleavage and midriff it showed. Daniella had nearly completed her son's transition into her daughter. Makeup came next. Alex protested of course, but threats to his masculinity through the pictures humiliated him into accordance. Eye shadow, mascara, blush and a bright pink shade of lipstick were all used before Daniella asked her son to strap into a pair of pink heels. She giggled to herself, remarked "Ta-da!" and showed her son to the mirror. Wobbling in the high heels, Alex saw himself and blushed severe red, never having felt so pathetic in his life. He actually looked like a little girl in his costume. But Daniella's plan was not yet complete. "Very good now sweetheart, I'm sorry that mommy had to punish poor Alex, your punishment is nearly over," patronised Daniella, before blindfolding her son. "Ugh, mom, what's going on please?" Alex murmured pathetically. Daniella grinned, knowing that her blind feminised son could not see. "We're going to play a little game, dear. I'm going to play one of your records, and you're going to tell me which one. Sound fun?" "I guess," Alex said as his mother put on a loud song. As the music played, Daniella signaled to her daughters waiting patiently outside to silently enter Alex's bedroom and tiptoe inside, whilst poor blindfolded Alex couldn't hear. After a few seconds, Alex eventually blurted out "Mom, please, you're not going to show me to Hannah and Amelia like this, are you? Please mom?" Knowingly, Daniella began "Why of course I wouldn't do that to you, sweetheart," in which point Alex smiled to relief. His mother then began again, this time, her voice tinged with evil sadism that made Alex shiver. "Why would I show you off to them, when they have been here all along to admire their beautiful new sissy sister!" Daniella exclaimed with delight. Terrified, Alex ripped off his blindfold to reveal both Hannah and Amelia standing before him, wetting themselves giggling at their pathetic, dressed up sissy brother. To his horror, Hannah was holding a camcorder and Amelia holding her camera, snapping pictures at an alarming rate. Beginning to tear up at the humiliation, Alex attempted to walk past his sisters and out the door, only to teeter and fall because he was unused to the ridiculous high heels he had been forced to wear. On the ground, he could hear his sisters chanting "Get up Alexis!" Alex began to bawl at this point, truly humiliated down to his core. His mother helped him up back onto his feet, before bringing him close and hugging him tight. Even with those ridiculous heels his mother was still several inches taller than him. "Shhhhhhhh", she said, "If you don't stop crying you'll ruin your makeup!" At that Alex began to bawl even harder; Hannah and Amelia began giggling and groping their new sister. First their hands gravitated towards his bubble butt, and they lifted his leather skirt to get a better view for the cameras. They pulled the thong to the side, exposing his rosebud and his prosthetic vagina for everyone to see! Amelia, being especially devious, placed one of her fingers against Alex's hole, applying a gentle pressure, causing Alex to yelp. She wouldn't penetrate him, not yet, but she did just enough to make him squirm in his mother's tight embrace. "Please", Alex cried into his mother's bosom, "not there, I'll do whatever you want, please just don't make me do that" "But that is what we want little sis", said Hannah, "but don't worry, we'll be gentle at first, we wouldn't want to ruin you!" Daniella smiled knowingly at her daughters. "Well girls, why don't we begin how we said we would, huh?", before extracting a little pink rubber butt plug from the dresser along with a bottle of lube and grinning at the family. "This little thing might make our cute daughter Alexis a little more uncomfortable, but it is, unfortunately, a necessity. Girls, if you could please restrain your sister", and at a nod, Amelia and Hannah held their sissy brother by the arms tightly while their mother lubed the plug. Bending him over to protrude his little bottom for mommy to see, Daniella carefully pulled down his skirt and panties just enough to force the little plug past his tight virgin rectum, before it slid smoothly into the rest of his ass. Alexis moaned and sighed deeply, discomforted by his hole being violated, though his sisters took this as a sign of pleasure. "I thought my sister might be a thirsty cockslut," Hannah giggled with Amelia. "You needn't worry about that, Alexis; Amelia and I have something planned for you this evening." "Indeed they do," Daniella confirmed, "But until then, I want my sissy daughter fulfilling her punishment. Now Amelia, fetch the restraints." Amelia skipped out and returned with a few lengths of chains and collars. She then proceeded to restrain Alexis with Daniella whilst Hannah locked the collars around her sissy's ankles, wrists and neck, before organising the chains. The chain between his ankles was short but just long enough to allow him to walk in small steps, the chain between his wrists slightly longer to allow him a decent amount of movement, and the chain running to his collar pulled the others tight if he moved his head back too much. Amelia looked at her bound sissy-sister, shared a smirk with Hannah and giggled. "What a pathetic silly little sissy girl we have as a sister," laughed Amelia. Alexis blushed scarlet red, with cheeks still tearstained. Amelia approached him, so that she was mere centimetres from his face. "I remember you called me a sissy not too long ago. Well who's the sissy now, huh? Well? Aww, don't cry for me sis, cat got your tongue?" Proudly smiling, Daniella took control. "Now now Amelia, patience. It may take Alexis some time to adjust to her situation." Every time his mom said 'her', it stung. "For now, perhaps its best for our sissy maid to do her job and tidy and dust this house, top to bottom," And so Alexis was sent on his way, struggling to totter around the house in sky high heels with chained ankles. His wrist restraints didn't offer much movement in terms of cleaning, but his sisters were just happy to have their conniving brother bound at their mercy, dressed up in their sluttier clothes. Everytime Hannah walked past Alexis, she made a point of lifting up his leather skirt to roam with her invasive hands, whereas Amelia found an old riding crop in the attic from Daniella's riding and jodhpurs days and found some amusement in whipping her helpless sissy until Daniella seized the crop and told Amelia to stop being so mean to her poor sissy-sister. It took Alexis some hours to tidy the house, with numerous qualms with his sisters playing with their new toy. Humiliated, weakened and exhausted, Alexis returned to his bedroom to see his mother once more. "Well, well Alexis; how did my adorable daughter find her first day as a sissy maid?" "Mommy." He hated calling her this. It was something he hadn't done since a toddler, but something she reinforced during his Sissification. "Its been difficult, but I think I just need to sleep now, maybe if I rest, I'll be a better maid tomorrow?" Alexis asked, hoping to appease his omnipotent mother. "Well..." Daniella smirked, rolling her eyes to feign deep thought. "As much as a good night's rest does sound, your sisters and I may well have other plans. Perhaps you should meet them in the playroom to... erm... play?" Alex to Alexis Ch. 02 Again, thanks to Jack Murphy for being an amazing volunteer editor! Enjoy! Chapter II: Acceptance This didn't sound good. Led by his mother's hand, Alexis clattered to the darkened playroom, to open the door to find the room unusually bare. The piano was still there, the wardrobe was still there; no television, no chairs... A weird piece of furniture dominated the centre of the room now. It looked almost like a carpenter's saw horse. The frame was lacquer black in color with padded red vinyl on its spine and the same red padding on small square platforms that adorned the lower area of all 4 A-frame legs. It also had several steel eyelets located on the legs. It didn't take a genius like Alexis to figure out that it would be for tying him down. "Mommy...?" Alexis nervously asked as Daniella lovingly walked her sissy to the mount. "Now, now Alexis, hush and don't make a fuss. Take of your clothes and do as I ask or I'll just have to force you to". Alexis complied, stripping of the layers of clothing she was wearing, leaving her naked besides her collar, which was still locked, and her bright pink heels. "Good girl", said her mother, which surprisingly delighted Alexis. She felt herself beginning to enjoy the positive attention from her mother, especially since the day had been so difficult so far. "Now climb onto the horse for me, okay?" Reluctantly, Alexis leaned a leg over the mount and sat on it like a horse, which is easier said than done in her sky-high heels. "There's a good girl Alexis," Daniella cooed in a motherly tone that was unfamiliar to Alexis, but comforting. "Now slowly, why don't you try lying down on your tummy? It's perfectly natural if it feels a little strange at first" Uncertainty, Alexis reclined on the padded sawhorse face down, head turned to the side, with her arms and legs dangling by the legs of the furniture naturally. She felt her fake breasts squish against the pommel, and the position that the horse left her in caused her butt cheeks to open and she shivered as she felt her tight hole exposed to the room. "Now Alexis, this next part might be a little difficult, but I want you to trust me. You know that I'm your mommy and I would never do anything to hurt me daughter?" "Yes mommy" Alexis trembled, frightened and unconvinced. Daniella smiled reassuringly. "Well Alexis, for the sake of your own comfort, I am going to lightly strap your ankles and wrists to our horsey here". "Okay mommy", Alexis replied hesitantly, as she felt Daniella attach the straps around her ankles and wrists tight enough to restrict her from all movement, but not so tight as they were uncomfortable. Properly restrained, Alexis knew what was coming next. She would be taken, like the sissy that she was, and there was nothing she could do about it. Alexis, to her own surprise, found the situation erotic, however the prosthetic clay pussy covering her small cock prevented her from getting hard. She heard her mother somewhere in the room, and it sounded like she was undressing but Alexis' position didn't allow for much head movement, so he couldn't see what exactly was going on. Satisfied with her daughter's transformations, physical, mental, and emotional, Daniella knew that her daughter was ready to be taken like a girl, and after undressing completely, she put on her 6 inch long, realistic looking lubricant ejaculating strap-on. Alexis jolted a bit when she felt her mother behind her, beginning to caress her plump little ass. Alexis moaned as Daniella squirted an ample amount of lubricating oil onto her butt, before beginning to spread it across her smooth, hairless cheeks and legs. When Daniella reached her daughter's tight, virgin hole, she was reminded of the pink butt plug that had been left in from Alexis' chores. She pulled it out slowly, making sure not to make Alexis uncomfortable by the movement in her bowels. On the contrary, the friction inside of Alexis caused her to moan in pleasure, to which Daniella smiled, knowing that this was going to be sensuous for both of them. Eventually the plug came completely out, leaving Alexis with a slight gape in her hole, a quality that Daniella found incredibly arousing. Daniella began to insert her fingers into her daughter's tight hole. Starting with one, Alexis felt her mother's fingers penetrate her. Alexis quickly became accustomed to the single finger, so Daniella added another, and soon after that another, along with another squirt of lube. Alexis was in a state of absolute bliss as she felt her mother's fingers inside of her tight ass. As she moaned and squirmed against them, she cried out "More, please mommy, I want you to fill me up more!" "Do you trust me Alexis?" Daniella asked her daughter. Alexis replied "I completely trust you mommy." To this, Daniella began to slowly rub her fake cock between her daughter's smooth, oiled cheeks, before placing the tip at the entrance of Alexis' pleasure hole. Alexis allowed a slight whimper to escape her as she felt her mother begin to slowly apply pressure to her hole. Soon, the head of her mother's strap-on was inside of her, and Alexis moaned at the new sensation. Daniella began working her strap-on cock slowly into her daughter's tight young hole inch by inch, and Alexis was enjoying every second of it. After what felt like an eternity, Daniella's rubber cock was all the way inside Alexis. Alexis moaned as she felt her mother bottom out inside her tight young ass, and even louder as her mom began to pull out, picking up speed. Soon, Daniella was pumping in and out of her daughter, making love to her like no one had before. Alexis felt her ass involuntarily squeeze her mother's hard cock, it was filling her up like nothing ever had. She knew then that this is what she wanted, it wasn't just forced on her. She loved being fucked! Daniella was see sawing in and out at this point, loving the feeling of her new daughter's boy-cunt around her cock. "Talk to me baby", said Daniella, "Tell me what you're thinking while your mommy makes love to you". Unable to properly move due to her restraints, Alexis felt herself begin to spasm from the pleasure, as she answered "I want you to fuck me mommy, I love the feeling of your hard cock in my ass!" Feeling like it was time for one final surprise, Daniella reached under her juicy rubber cock and began to toy with the balls, which were filled with hot, sticky fake cum! With one final thrust, she buried her hot cock deep inside of her new daughter's ass, before squeezing the balls and blasting a load of hot cum deep inside and screaming out "I'm cummmmmiiinnnnggggg". Alexis moaned as she felt one hot jet of cum fill her ass, then another, and another, until the last drop. As Daniella slowly exited her daughter's hole, Alexis felt a bit of cum already beginning to leak out of her tight hole, making her feel more feminine than ever! "Did you like that sweetie?" Daniella asked lovingly, already knowing the answer. Breathless and blushing scarlet, Alexis managed to gasp "Oh mommy, it was beautiful!" Ecstatic with her son's transformation, Daniella approached her daughter and said "Then kiss it for good luck?" Alexis proceeded to plant a wet, lip-sticky kiss on his mother's dildo, tasting the delicious flavors of fake semen, lube, and her own ass. "I think it's time for the girls to have some fun with you sweetie" Daniella said loudly, obviously signalling Alexis' sisters to come in. Alexis was embarrassed that his sisters had probably heard his moans and cries if they were standing just outside the door, but she realized that they would likely hear much more if they had any of the talent that their mother had, and he had a sinking feeling that they were not going to be as gentle with her as his last fuck. As they walked into the room, he could hear them giggling about the position their new sister was in. "Don't be too rough girls", said Daniella, "We still want this to be a pleasurable experience" "Yes mother", the girls replied in unison. With that, they began to circle him, so that one of them was always in his restricted field of vision, and he began to notice how truly stunning they were. Both wore matching, realistic, black strap-no's that looked to be about 2 inches longer than the one Daniella had just used, and quite a bit thicker as well. As Hannah began to move towards her sister's ass, she ran her fingernails along Alexis' skin, causing her to shiver, and moan slightly. When she reached her sister's tight little ass, Hannah squatted down so that it was at her eye level, and spread those cheeks apart, revealing Alexis' already well fucked boy-pussy, which was gaping slightly. "Well, well, well, what do we have here, sissy slut?" Hannah mocked as she inserted a finger slowly into Alexis' tight hole, before withdrawing it to reveal globs of fake semen. Skipping back round to face Alexis, Hannah squatted back down to eye-level with her sister, smirking at her with a raised finger. "Care to explain yourself, cock slut?" she grinned at her bound sister. "Hannah, please!" Alexis stammered, but was crudely interrupted by Hannah exclaiming "Bon appétit!" before cramming the semen-soaked finger deep into Alexis' resisting mouth. Alexis squirmed, moaned and recoiled as his sister forced her to eat up the semen like a good girl, whilst Hannah and Amelia giggled at the humiliation of their new toy. When Alexis had sucked the cum coated finger clean, Hannah asked her to kiss the strap-on for good luck, before she aligned the fake cock with Alexis' bottom. Meanwhile, Amelia was taunting Alexis from the front, hovering the imposing cock merely centimetres from her face. As the tip of Hannah's dildo pressured its way into Alexis' still tight hole, Alexis sighed deeply, in a mixture of both pain and pleasure, as the final few inches slid in a bit deeper. In angst and ecstasy, Alexis moaned "fuuuuuuck", to which Amelia responded "I guess we've got a potty-mouth, don't we Hannah?" Amelia then scooped some liquid soap off the counter and squirted a dose onto her own cock. "We'll clean out that silly mouth of yours, sissy-girl!" Being called a sissy-girl was especially hurtful from her younger sister, but Alexis could not complain because she gagged harder as the foul tasting dildo forced its way into her struggling mouth. The bitter taste of rubber, soap suds and humiliation agonised Alexis in correlation with the bottom-fucking she was concurrently receiving from his older sister. The girls soon fell into a rhythm, one shoving their cock inside while the other was pulling out. They would always pull it out till it was only the tip left in, then slam them back inside of her, making Alexis feel all the more fucked. Hannah and Amelia reamed their sister's nubile holes for what seemed like hours, a never ending shower of pleasure for Alexis. She found herself falling deeper into her submission, moaning almost constantly, begging to be treated like the dirty slut she was inside. And she loved every second of it.