A Christmas Wish Mishap: A Big Surprise (Patreon)

Intro

Sora had just arrived home for the Christmas break. He had never really liked Christmas all that much well he loved the sentiment of the holiday, the whole being together, the warmth, the cosiness, being with family. It just that for him that had never really been the case. His parents were the only members of his family who had moved here from Japan and they nearly always had to work. Both were doctors at the local hospital and sometime he had the feeling they lived to work instead of the other way around. He loved his parents, but they barely had time to spend together.

Something which had only grown worse since he started studying at college. He had a room in the dormitories so he only ever came home on holidays. He could have gone to college pretty close by, but he had wanted to see more of the country which is why he had applied to colleges across the country.

While it meant he saw his parents even less, it didn’t make that much of a difference and he had also kind of wanted to get far from home due to his bad highschool experience. He had often been teased for his name in highschool, it was a name that could be used for both boys and girls, but most Americans thought it was a girl’s name.

The fact that he wasn’t really big and manly didn’t help much with the teasing either. He had a rather pale Asian complexion, dark brown almond shaped eyes, jet black thick straight hair and a rather slim 5’7” body. The teasing hadn’t be too bad, but bad enough for him to want to leave all his highschool friends behind. As a result his breaks had become even lonelier, he barely had any connections left out here.

It didn’t matter that much though, he probably wouldn’t be living here for much longer anyways. He was 23 now and well on his way to graduating as a doctor himself. As soon as he did he would get his own place and settle where he chose. College so far had been a great experience for him. There he was accept as he was. He had a rather tight knit group of friends, both guys and girls all with a love for gaming like him. Out there he wasn’t teased anymore. People at college minded their own business way more than at highschool and his group of friends was a lot more open minded. They didn’t judge based on names or appearances, they all just liked having fun.

All in all college had been a real liberation, he had even dared to grow out his hair to the point where it reached just below his shoulders now. He had always kind of liked longer hair, but it wasn’t something he felt comfortable with in highschool. If he had done so he wouldn’t have heard the end of it.

Being home with Christmas might be a pretty lonely thing, but there were also perks to it. Thanks to online games he could keep in touch with his friends while they were with their families, and he could spy on his childhood crush again. Rosa, his next door neighbour. She was a stunning Hispanic woman, quite a bit older than him, but despite her age she hadn’t lost that beauty that had enraptured him.

Sora guessed she had to be somewhere around 5’9” tall with modest yet ample breasts, a bubble butt, long legs and a trim waist. He knew from party balloons he had once seen before going off to college that she had to be 36 years old now. Her thick jet black hair was wavy with an impressive length nearly reaching her bottom. She had a really nice blemish free tan skin and a pair of big vivid brown eyes.

She had always been beautiful, ever since she moved in to the large upper middleclass house next to where he lived. It wasn’t until he hit puberty that she really took his special interest though. As soon as he realised that his bedroom window was right across from hers he had spend days learning her routines. Pretty soon he had discovered when she changed clothes in the morning and evening as well as before her sport practices. She was a rather private woman though so the blinds always closed before he could see anything too revealing. Nevertheless what he saw was more intimate than how anyone else got to see her. Especially considering Rosa had been single all this time, he had never once seen her have anyone but some girlfriends over.

Despite all the hot girls going to his college Rosa had always remained his one and true crush. He never managed to score a girlfriend, at least not yet, but Rosa was ever-present in his masturbatory fantasies. Other girls only got secondary roles mostly as he imagined in a trio with Rosa. Seeing Rosa again always was one of the heights of his breaks.

They might have been neighbours for a long time already, but they had never really met most of their neighbourhood was really self-centred, there were no big neighbourhood parties or anything. It wasn’t something he had missed really, but it would have been nice to get to know Rosa. Although with their age difference that was probably just wishful thinking, she would have probably seen him as being just a kid.

It was the 24th of December now, Christmas eve, it was slowly getting dark outside, but then again it got dark quickly this time of the year. Sora sighed as he looked down out of the window. Rosa was just arriving home from her evening run, unlike his parents who probably would be home at eleven o’clock at the earliest only to leave again before eight o’clock the next morning.

Although Rosa was dressed quite warmly in a lot of layers Sora couldn’t help but admire her figure. Even dressed warmly for these cold days Rosa kept up with her usual immaculate dressing standards. All of her layers were skin tight keeping her warm while showing off her perfect figure.

“Man I really wish I could be hers. I would do anything to be with her.” Sora said out loud as he watched her enter the house. Unbeknownst to him a Christmas spirt just passed over his house at that very moment, glowing red as it granted his wish.

With nothing to do all evening Sora waited for Rosa to move up to her room so he could see her undress. First her purple fleece came off, followed by her purple knee high compression socks, followed by her black long sleeved t-shirt, followed by her baby blue tank top, her baby blue leggings and finally her thick black tights. Stripped down to nothing but her plain white underwear Rosa disappeared from view as Sora sighed, having made a mental picture for later. For now he just started up his computer and went to his favourite solo game as all his friends had family parties to attend.

Chapter 1

Sora was very invested into his game when all of a sudden the doorbell rung knocking him right out of his concentration. Silently he cursed, who the hell could that be this late on Christmas eve? Whoever it was they could fuck off he thought as he went back to his game feigning no one was home. He had only just resumed his game when the bell went off a second time however. Clearly whoever was at the door wouldn’t leave him alone, getting up Sora decided he better take it so he could get this over with.

Already annoyed Sora headed down to the door, in his black sweatpants and white t-shirt which was his standard comfort wear when he wasn’t planning on seeing anyone anyways. Opening up the door he lead with an annoyed. “What…” But quickly trailed off as he saw Rosa standing in front of him in an elegant wine coloured figure hugging sweater dress, a pair of thick black tights and black ankle boots.

With a single cough he retook his sentence in the friendliest possible intonation he could manage, a slight stammer in his voice as he was face to face with his crush. “R…Rosa, hello, good evening, please come in its freezing outside. What can I possibly help you with? My parents aren’t home at the moment, but if I can help I’ll be glad to. I mean if you need my help that is. I would love to help you.” He rambled on before falling silent with a deep red blush, realising he was making a fool out of himself.

Rosa just giggled, she didn’t really know why, but she had felt the sudden urge to bake for Christmas. It wasn’t something she usually bothered with as she never really celebrated Christmas anymore. It reminded her too much of her old life, the family she had fled from since they couldn’t accept her for who she really was. Now that she could finally be who she really was she felt a lot happier than she used to yet she was still weary of entrusting people with it after her families terrible reaction to it. It was one of the main reasons she had remained single all this time as she had certainly had more than enough chances.

She had been all out of crystalline sugar hence her trip here. She didn’t even know why she went here and not to the house on the other side of hers. Her neighbours on the other side were often home, at least as far as she could tell judging by the light. This house on the other hand nearly always seemed empty and even now she had seen no sign that anyone was actually home.  Yet she had felt the urge to ring the bell two times even though she was pretty much certain no one had been home after that first time.

Seeing her neighbour in the doorway she was glad she had decided to come here. She knew her neighbours had a son, she still vaguely remembered him, but she simply didn’t realise he had grown out so cute. Rosa wasn’t really into men, she was more into women and although Sora was a guy there was something about him that made him look like he could be exactly her type.

Unexplainably intrigued by this guy she wouldn’t have batted an eye to before Rosa decided just to roll with it and see how it played out. “Thank you sweetie, Sora is it right? Well I was about to make a bunch of cookies for Christmas tomorrow, but I am all out of crystalline sugar. I wondered if you could spare some.” Rosa said quickly taking him up on his offer and stepping inside while Sora closed the door.

“Uhm, sugar, right. I should go and have a look. I’ll be right back.” He said before rushing off to the kitchen, he hoped his mom and dad still kept up with their usual habits. His mom always had plain yoghurt while his dad preferred his with a bit of sugar. Instead of buying two separate cartons they just had a big pot of sugar for his dad to sweeten his.

While Sora was off to search for that sugar, Rosa couldn’t help herself but look around a little just like hers his house didn’t look all that cosy, decorated for Christmas or otherwise for that matter. There were a couple of heirlooms and some pretty expensive looking furniture, but the house was lacking soul. On that front it was definitely different than hers, she just didn’t do Christmas. To be honest she felt quite sorry for the guy, must be hard coming home from college in an empty house like this.

Rosa’s exploration took her from the hall into the living room. It might be rude to be snooping like this, but she was sure Sora wouldn’t really mind. Thinking back on their meeting the guy looked absolutely taken by her. Maybe she could have some fun with that, it would definitely be a nice change of pace to flirt a little once more. Depending on how he responded she could even see how far she could push him, maybe just maybe she could convince him to get out his potential of becoming her type.

Once in the living room Rosa simply sat down on the big comfortable couch that seemed to be barely used. Meanwhile Sora had returned to the hall with the pot of sugar, a bit puzzled that Rosa was gone, damn, she was mad about his initial outburst wasn’t she? She had left because he had been too weird, that had to be it. Why couldn’t he just act normal for a second, anything to spend some more time with Rosa. To make sure that was the case he shouted once. “Rosa, I have the sugar!” He exclaimed.

“I’m here in the living room.” Rosa shouted back much to his surprise, why would she be in there, he hadn’t been all that long now had he? It got even weirder when he went in there and saw she had made herself comfortable on the couch. Not that he minded at all, it was just a little strange since they didn’t really know each other.

“Sorry for the intrusion, it’s just that I went for a run earlier and my legs are a bit tired. Hope I’m not to much of a bother.” She said kindly. It was a lie though, she could easily run twice what she had without getting too exhausted. After all she did make sure to keep in tip top shape.

“Oh uhm no, not at all, you’re never a bother, you can rest your legs as long as you want. I found the sugar.” Sora awkwardly said holding up the pot, not really knowing how to react. He certainly didn’t mind Rosa having made herself comfortable, if anything he’d want her to stay longer. Probably an idle wish now that he had brought what she needed.

“Thank you very much sweetie, can you put it here on the table so I won’t forget to take it when I go? I’ve never really realised how much of a cutie you have turned into over the years. You don’t mind if I linger a little longer do you? It’s a bit lonely over at my place and it’s honestly nice to have some company these days when everyone is celebrating together.” Rosa explained sweetly as Sora couldn’t help but blush brightly, he had never been called a cutie. It was kind of an embarrassing term yet he guessed it was a good thing if Rosa wanted to spend time with him because she thought he was cute.

“N…No, of course not, please feel free to stay as long as you want. It’s very nice to have company, you’re company is great. I love having your company.” He blurted out awkwardly as he put the sugar on the table before just remaining on his feet, not knowing if he should join her on the couch or what.

Rosa just giggled Sora definitely wasn’t a smooth talker. He was too awkward to take any initiative himself, probably fearing that he would mess up one way or another. Not that Rosa minded, in fact it only made him more appealing to her. She had always loved being the one in charge and Sora was practically begging her to take control of the situation, she doubted he would do anything around her without her suggestion or even a plain command even though he was clearly smitten by her. She guessed it was just because he was afraid of messing up.

“You know Sora, I’ve always enjoyed company the most with a glass of wine why don’t you pour us two glasses, red preferably and join me on the couch, I would love to get to know you better.” Rosa said testing her theory.

“Yes of course, how could I have been so rude not to offer you anything, two glasses of wine coming right up.” Sora said as he rushed back to the kitchen, he couldn’t believe Rosa actually wanted to spend time with him, it was all he had ever dreamed of and more, just being around her made the butterflies in his stomach go crazy. He didn’t particularly enjoy wine himself, but the last thing he wanted was to seem weird to Rosa.

Returning with the two glasses he handed one to his gorgeous neighbour then looked shocked when she scooted a little to the side, leaving a small space between her and the armrest and patting it for him to sit down. He didn’t dare to refuse despite the place being way too narrow for him. He would be sitting way too close for comfort, closer than he would ever dare get to Rosa.

Awkwardly he did move into the small spot anyways, squeezing himself between Rosa and the armrest, his whole side in contact with Rosa’s. He was sweating profusely due to nerves alone. Rosa smelled so nicely of lilacs making him even more self-conscious sitting here in his sweatpants not even showered. If only he had known how tonight would play out, then again he could never have guessed in a million years.

Rosa on the other hand was smirking broadly, his nerves were just too cute. He was so easy to toy with and she loved it. “Cheers sweetie, to good company. So what is it you study if I may ask?” Rosa asked clinking their glasses together before taking a sip of her wine and resting one of her well-manicured French tipped nails on his thigh.

As wonderful as this all was Sora wished that the ground would swallow him whole, he was sporting a tent in his pants and Rosa’s hand was insanely close to it, he didn’t know how he would ever be able to look at her again if she found out. He really had to force himself to answer her question and after it Rosa was right back with another question. She proved really easy to talk to and before he knew it he was starting to relax a little as the small talk carried on.

Before he knew it an hour had passed by and he noticed Rosa’s glass was empty. “Could I get you a refill Rosa?” He asked politely comfortable enough to at least be a good host without being too awkward about it.

“That would be lovely!” She said releasing his thigh after all this time before handing him her glass. Wasting no time at all Sora went into the kitchen to pour her another glass of wine and readjusted his little below average erection in his pants, trying to make it less obvious. When he returned she had taken his place in the corner. It was honestly a little disappointing as there was no way he would be getting away with sitting that close to her again.

“Thank you very much sweetie, you know what always helps me relax so very much? A good foot rub, it has been ages since I had one. It’s honestly one of the things I miss most about a relationship.” Rosa spoke as she took her glass back.

“I could give you one if you wanted, I mean I’ve never really done so, so I doubt I would be any good, but I can definitely try if you’d like.” He offered, eager to get on a good note with Rosa. Surely he was imagining things, but could it be that Rosa actually liked him? Did he dare dream of becoming her boyfriend or was he just imagining things?

“Like? I’d love that, you better be careful sweetie or I might actually fall in love with you.” Rosa said with a wink leaving Sora stunned. Speechless he moved back on the couch, now at the other side of Rosa. The woman didn’t hesitate a minute to put her feet up on his lap, still in her elegant low heeled ankle boots. Gulping light Sora carefully unzipped them and took them off for her.

While he had been eager to help Rosa with her shoes he now realised in a moment of horrified panic that had been a huge mistake. Out of her shoe Rosa’s nylon covered foot rested directly on his lap, straight on top of his rock hard cock. There was no way Rosa hadn’t felt what was going on underneath her foot. Mortified Sora blurted out. “I’m so very sorry, I…” But he was cut short by Rosa.

“Shhh, don’t you worry, I’ll take it that you find me attractive? Well let me let you in on a secret, you aren’t exactly my type, but you’re very cute and you definitely have the potential to be exactly my type, all you’d need is a little change of… style let’s say. I do however like you a lot already.” Rosa said rubbing her foot back and forth over Sora’s pants covered cock making him moan.

What she had in mind for Sora’s makeover wasn’t something she would usually ask from anyone unless she was certain they liked it. It was certainly not something she would ever ask of someone she had just gotten to know, but for some reason she really wanted to make this work with him. She wanted to make it work, but on her own terms. It would only work if Sora bent to her wishes, but for some reason she was quite confident he would, despite how much it was she planned to ask of him. Usually she would back down out of this out of fear of getting a bad reputation around the neighbourhood, but for some reason she didn’t care about her usual cautions with Sora.

“Don’t you worry about this right here, it can be our little secret.” Rosa said cupping his hard cock with her foot, feeling it up before giggling. “With the emphasis on little.” It might be cruel to tease Sora like this, but she couldn’t help it. She loved the way his blush grew even brighter even though he relaxed a little realising he hadn’t screwed things up.

“Now why don’t we help each other out and trade a rub for a rub?” She asked starting to rub her one foot up and down his hard shaft while putting her other booted feet in his hands. With no other sound than a moan Sora released her other foot from its boot and started kneading her sole as best as he possibly could. It seemed to please Rosa as a moan escaped her as well.

“You’re not half bad at this Sora, I could definitely get used to this.” Rosa commented getting an awkward thanks in return which made her giggle. Was she thanking him for the foot job or the compliment? Whatever it was it was cute and rather funny.

Rosa was clearly enjoying herself while Sora’s mind was reeling. Was this a dream? A night mare? A wet dream? He didn’t know he was so confused. He didn’t know whether to be happy, excited, angry, shocked, or embarrassed. He didn’t like Rosa making fun of his cock, he didn’t particularly like having her feet on him or in his hands, but he simply couldn’t refuse her anything. Besides wasn’t this what he had always dreamt of? Being with Lena? Hell even getting stimulated by her even if it was with her foot and his cock was still in his pants. Sure he would have liked to see thing play out differently, but getting this kind of attention from Rosa was pretty great in and of its own.

Another thing that worried him was what she had meant with a change of style, it was rather cryptic and he had no clue as to what to expect. No matter what it was though he already made up his mind that he would do it if she’d ask. He would do anything for her.

“So Sweetie, why isn’t the house decorated for Christmas? You live here with your parents right?” Rosa casually asked as she pulled her foot out of his hands, replacing it with the one which had been rubbing his cock while continuing to rub his cock with the foot he had just massaged.

For Sora the conversation was right back to being awkward no matter how casually Rosa acted. The fact that he couldn’t form a sentence without moaning in-between didn’t help one bit either. He just tried keeping his answers as to the point as possible which kind of made it hard to build a real conversation. Their conversation was more like an interrogation of sorts with Rosa asking him questions, listening to his answers before answering her questions herself.

This continued for about twenty minutes before Sora got mortified all over again, his moans growing to a climax as his orgasm rolled over him. He tensed up completely as his cock started spewing cum into his boxers, yet Rosa just smirked and carried on rubbing until she was certain he was entirely done cumming.

Once she stopped she looked down at her watch and exclaimed. “Oh my, is it this late already? I really need to get going. Could you please be a dear and put my shoes back on?” Rosa asked as if nothing special had happened. That while Sora could only manage a weak yes, still recuperating from his orgasm.

Still breathing heavily he carefully put Rosa’s boots back on her feet after which she quickly put them back on the ground and got up. “In any case thank you very much for the good company, the wine, the sugar and the foot rub. I had and amazing time and from the looks of it so did you.” Rosa said before surprising him big time once more by kissing him straight on the lips, sensually working her tongue into his mouth in what was his first ever real kiss. She kept it up for at least a minute before breaking it off leaving Sora looking more smitten by her than ever.

“Oh also I have been thinking and I thought it was quite a pity that you’ve never had a Christmas like it should before. So here’s my idea, it has been way too long since I celebrated Christmas as well, it was about time I got over those bad memories so why don’t we help each other out and be each other’s company? We can celebrate just the two of us, maybe there’ll even be a be a happy ending.” Rosa said with a wink as she picked up the sugar.

Sora couldn’t believe what he was hearing, after all this Rosa still wanted to see him? More even she wanted to spend Christmas with him and even hinted at sex? This was absolutely amazing. Would he lose his virginity to this wonderful woman, his crush? If a little teasing here and there was all he had to endure then this was so worth it. Hell now that he had started to get to know Rosa he loved her even more.

Despite all that Sora simply stared up at her speechless, amazed and love drunk after his recent orgasm and that intense kiss. It made Rosa laugh. “I can take that as a yes I suppose? Clearly I short fused your brain, so in any case you can think on it and wait till you’re a little more clear headed. If you want to celebrate Christmas with me I would love if you could do me a favour and try that style I think you’d look absolutely amazing in. It would most likely require you to buy some new things, but it shouldn’t be too hard.”

“Think your answer through and if your answer is yes then I would be happy to welcome you over at my place at 9 o’clock tomorrow morning so I can take you out shopping for your new style. If you don’t show up I’ll just assume the answer is no.” Rosa said with an excited smile before showing herself out leaving Sora happy and completely amazed on the couch.

It took a while before he regained his senses enough to the point where he could actually start doing things again. Still in disbelieve of what had just happened Sora went up to the bathroom to have a shower and clean his cum covered crotch before retiring to bed for an early night, wanting nothing more than to be well rested for tomorrow.

His worries from earlier regarding that new style Rosa had kept hinting at without explaining a thing were far from his mind. The question wasn’t whether or not he would show up like she asked. The question was how he could make the best possible impression on her after this lousy introduction with his erection in his sweatpants. Impressing Rosa was what he thought of when slowly drifting off to sleep, dreaming about that happy ending she had hinted at.

Meanwhile Rosa baked her cookies and took the fake Christmas tree she had once gotten out form the attic. It wasn’t all that impressive but it would have to do. It was the best she had on such short notice as tomorrow with all other preparations there wouldn’t be enough time left for more and better decorations.

Chapter 2

The following morning Sora woke up way earlier than he usually did. He just couldn’t sleep any longer knowing he would get to spend his Christmas with Rosa. Or had that all just been a wonderful dream? It was entirely possible considering he had had a wet dream at least that was what his boxers were telling him. Somewhat embarrassed about this he got in the shower once more, giving himself a thorough wash.

Heading back into his room he had a hard time deciding upon what to wear, only to come to the conclusion that he didn’t have anything really nice. At least not nice enough to impress Rosa. In the end he settled for a black button up shirt, a pair of jeans and his nicest sneakers. After all he didn’t want to go in a suit as Rosa had said they would go shopping and that would be ridiculously overdressed.  Downstairs he wrapped a box of wine bottles to the best of his abilities, he couldn’t arrive empty handed after all and there was no time to buy a real present. Now all that was left to do was to wait for 9 o’clock to arrive.

It was 8:55 when Sora left the house, still a little early, but he didn’t want to be late at all. Besides he could no longer wait to see Rosa again. Feeling nervous, praying this hadn’t all just been a dream or he would really look like a fool ringing Rosa’s bell with such a huge present. Ringing it he nervously fidgeted in front of her door.

In no time at all Rosa opened up for him almost as if she had been waiting for this moment like he had. She looked beautiful like always, wearing a cream coloured knitted sweater dress that looked very cosy. It was pulled tight at her waist with a broad black leather belt. On her legs and feet she wore another pair of thick black tights and a pair of black leather ankle boots. The outfit while being cosy and not revealing in the slightest looked simply stunning on her.

“Ah there you are sweetie, I’m so glad you could make it. My cookies turned out amazing, but those are for later. For now I have something to show you before we head out to get party ready. Please follow me.” Rosa exclaimed giddy with excitement

“S…so am I, uhm where should I put this? It’s a present for you. You know for our party.” Sora awkwardly said holding up the wrapped box.

“Oh yeah sorry, I was getting ahead of myself. I was just so excited at the prospect of what I was going to show you. You can put it right there in the hall so you can put it under the tree when we get back. You didn’t have to get me anything though, but I am very grateful that you did, now please follow me.” Rosa said.

Sora was glad Rosa was so excited, he really wondered what she had in store for him, but any excuse to spend more time with her was so worth it. He was very surprised when Rosa started heading up the stairs. She had hinted at a happy ending, but was she going to make it a happy beginning. Staring up at her amazing bottom he certainly hoped so. A hope that only increased as Rosa opened what he assumed was her bedroom if his orientation didn’t deceive him.

Eagerly Sora followed her inside, but once he did he was confused. Rosa was standing next to her bed. She didn’t make the slightest attempt to get undressed or anything, instead there was an outfit pretty much like the one she was wearing displayed on the bed. “So what do you think? I thought it could be cute to go twinning on our little excursion. I once bought this dress online, but it was a size too small when it arrived. I didn’t bother sending it back, I just bought a new one and now I’m very happy I chose to keep it, it should fit you perfectly.” She exclaimed excitedly to a shocked Sora.

What the hell was this supposed to mean? She couldn’t be serious right, there was no way he was putting this or anything even close to this on. He was shocked that Rosa even dared suggest something like this, yet he didn’t want to hurt her feelings or his chances with her. “Look Rosa, I’m not a girl, I can’t wear that, let alone go out wearing that.” He said as politely as he could.

“Why not? I think it would look gorgeous on you. I’ve always been into girl, or at least girly looking people and with your pretty face, your figure and that gorgeous hair of yours I believe you would make a very cute girl. It’s what I meant with a style change. We’re headed to the salon first so I thought I might better give you this outfit already. I mean you can definitely pull it off already, but the festive makeup look I have in mind for you will look very out of placed with how you’re currently dressed.”  Rosa explained as Sora’s shock only grew.

“Makeup? A Salon? Rosa I’m not a girl, and I don’t want to be one or dress like one either. You’re asking way too much of me. Please don’t ask me to do this.” He said, for some reason unable to flat out refuse. This was going very far. He should put his foot down, but he couldn’t refuse her anything.

“Aw please Sora, do it for me, I would love that. You’re a great guy, and I would love for you to be mine, my girly boyfriend, or girlfriend no matter how you’d like to call it. It’s just that I’m not really attracted to you like this . I’m sure I would be if you looked girlier though you really do have the potential and I would love to see that potential come out. I know you like me, I’ve seen the way you look at me. You also want to be with me don’t you? Well, this is your change I promise you won’t regret it, I would love to have a girlfriend as cute, fun and interesting as you are.” Rosa gushed without losing her excitement.

It was a bridge too far for Sora though. The idea of trying on something girly was just too much. It brought back so many bad memories about being teased with his name back in highschool. Yet for some reason he just couldn’t bring himself to refuse despite wanting to refuse badly he just couldn’t do it. The sacrifice was too big even for having a chance with Rosa but he couldn’t voice or resist it. After all his wish which had been granted and set this all in motion had clearly stated that he’d do anything to be with her.

“I…I, okay, I’ll do it for you.” He finally ended up saying. Excited beyond believe Rosa instantly pulled him into a tight hug, giving him a quick peck on his cheeks.

“Thank you so much sweetie, I simply know you’re going to be perfect for me. I knew you would come around. Oh this is going to be so much fun, you’re going to make such a cute girlfriend, I can hardly wait.” Rosa squealed, keeping the hug going for a couple of minutes before finally releasing him and going to the bed where she picked up a pair of black lacy hip hugger panties which she handed to him.

“There we go, you can put these on for starters, I promise I won’t look, at least not unless you want me to. You can’t dress like a girl and not go all the way now can you? The panties might be on the big side for you, but they’ll fit more or less.” Rosa said with a wink, looking forward to how he would look in them. Rosa would never push anyone against their will, especially not in such a way, but due to the granted wish she desperately wanted to make this work. She really wanted to make Sora her ideal partner.

Stunned Sora looked down at the panties. He couldn’t believe he was holding a pair of Rosa’s panties while that would have been amazing just yesterday he now just wanted to throw them away knowing they were meant for him to put on. God he couldn’t wear panties, much less let Rosa see him in them, but that was exactly what was expected from him and he knew it. Unable to refuse Sora slowly stripped out of his clothes and put on the panties, the flimsy fabric feeling so strange on his crotch and bottom, so much different than boxers did. His cheeks instantly turned beet red, he couldn’t believe he had actually put these on. Not wanting to say he had put her panties on he just coughed lightly to drag her attention.

Turning around Rosa instantly squealed. “You look amazing sweetie, this was such a good idea. There’s still a lot of work, but I know you’re going to look absolutely amazing. I suppose you’ll be glad to know that I take this twinning rather serious down to the panties and everything.” Rosa added with a wink as she made a mental note about his body hair. It would have to go, at least his face was cleanly shaven.

Sora’s blush only grew, at least Rosa was excited and seemed to like what she was seeing. It was also quite exciting knowing what panties she was wearing, but the way in which he found out wasn’t at all. He felt like such a fool and considering the remainder of the outfit this was only the start. Soon the tights followed after Rosa gave him pointers on how to put them on. After the tights came the dress and finally the belt to pull in his waist giving a slight illusion of curves.

One look in the mirror was enough to confirm his fears, he really looked like a flatter, Asian version of Rosa, his longish hair and smooth somewhat androgynous face looking quite girlish on their own paired with this outfit. He was shocked to admit he made a pretty girl, especially with this outfit covering up all of his body hair, helping his girlish look along. This was not at all what he wanted. Rosa hadn’t made him, the option to step away had always been present, but it wasn’t one he was able to take for some reason.

Rosa on the other hand was exhilarated with Sora already making quite a cute girl in a similar outfit as her. It showed a lot of promise for the makeover plans she had for him. “I knew it, just look at you, you make such a cute girl already. I might have trouble keeping my hands of you until we’re alone later today. You might be a little flat, but I like my girls in all shapes and sizes.” Rosa gushed as she gave Sora another passionate tongue kiss just like she had yesterday before they said their goodbyes.

He didn’t know how to feel about this all. On one hand he absolutely didn’t want to dress like a girl or look like one. These panties were just weird, so was how open this dress felt between his legs or how the soft nylon clung to his legs in quite an exciting way especially wen they rubbed together. On the other hand he loved being this intimate with Rosa, the woman he had dreamed about for as long as he could remember. She was a wonderful kisser and a wonderful woman in general. Her excitement also helped a little with the embarrassment he felt standing in front of her like this.

“Heavens would you look at the time, this has turned out to be way too much fun already, but we must really get going now if we want to have a long afternoon and evening to enjoy each other. Put on your shoes, I doubt we have the same size and I don’t have another pair like this laying around, but your sneakers will work fine with the rest of this outfit. We might not be able to twin completely, but it’s close enough.” Rosa exclaimed waiting till he did as she had asked before grabbing his hand and pulling him back down with her.

Sora’s nerves grew quickly as they approached the front door, he couldn’t go out dressed like this, what would people think of him? Rosa didn’t leave him much of a choice in her excitement though. She just grabbed her purse, pulled him out of the door, closing it behind them before opening her car. Sora didn’t need to be told what to do. He just rushed to the passenger’s side and got in mortified about being seen like this, how could Rosa do this to him?

She followed soon after, way more at ease, a big smile plastered across her face. “I knew you would come around, so eager to get going?” She tease as she gave his tights covered thigh a playful pat before leaning in for yet another kiss. It seemed to Sora that she certainly hadn’t been lying about the attraction bit, she was all over him now.

“Uhm Rosa, could we maybe just blow this whole makeover and stuff off? You know we could just head back inside and celebrate like this, in our twin outfits. That would be fun.” Sora tried wanting to avoid having to go out like this or worse, get a full makeover like Rosa had claimed they were going for. He might not be able to deny Rosa anything, but he sure as hell could try to change her mind.

Rosa on the other hand was stubborn, trying her best to make this by bending Sora to her needs and desires, changing him into someone she wanted to be hers. “Nonsense, you look great, but you can look so much better with a little help. Besides this is a celebration, I was thinking about something more themed and festive. I already have my outfit and I have the perfect idea for yours as well, something to match rather than to twin this time.”  Rosa said, driving off, out of their neighbourhood and towards the city before he could utter another word of protest.

Chapter 3

The drive to the city wasn’t terribly long, but filled with nervousness for Sora, every minute took him further and further away from home with only his current girly outfit to cover him. His nerves peaked as the car stopped in front of what looked to be a very pink salon. Eagerly Rosa got out of the car walking around it to open the passenger door and pull a somewhat reluctant Sora out. “Come on girl, this will be fun, I know you’re nervous, but do it for me please. I have such cute ideas for your new look, please just humour me and go along with it alright?” She asked as she marched him into the salon, breaking his resistance as he didn’t want to deny Rosa this.

In the salon they were nearly instantly greeted by a cute Hispanic girl in his age. She was gorgeous although both her outfit and makeup were a bit over the top. It was nothing compared to her ridiculous lisp once she started speaking though. “Hallo ladies, I’m Angel what can I help you with today?”

“I was wondering if Suzan’s here, I’m an old friend of Linda. It’s for a makeover for my girlfriend here and a mani-pedi for myself. There are somethings I want to discuss with her about his look though.” Rosa said, giggling softly as Angel performed a curtesy before mincing off to get Suzan.

While Angel was gone for the moment Rosa turned her attention back to him. “Alright sweetie, this is probably going to be a little bit scary, but I really really want your makeover to be a surprise so I don’t want you to see yourself before the finished result so you can get blown away by just how amazing you look and so you can admit I was right. Consider your makeover a Christmas gift from me to you. If you agree it would literally make me the happiest woman in the world. I promise it won’t be anything you can’t undo.” Rosa explained despite how she was pushing him she looked like she genuinely cared about him.

No matter how much he wanted to though he couldn’t deny her request. It was a bit reluctant, but eventually he said “Alright then. If it means so much to you then I’ll do it.”  All he could think about however was what he was getting himself into, was all this really worth a woman like Rosa? He really liked her and he loved being with her, but having to change so drastically was very hard.

“Great, you’re absolutely the best, oh I’m going to spoil you so much at our party, it’s going to be such fun. I can’t remember the last time I looked forward to Christmas this much.” Rosa exclaimed before pulling him in for yet another passionate kiss. It were things like this that made Sora feel like it was more than worth it. Rosa’s affection could really make his worries wash away, make him think only about how great being with her was. The moment the kiss ended however his worries were back as a way older heavy set woman in a similar uniform like Angel arrive. Hers was rather formless, all down to business and comfort though.

“Hello and welcome to my salon, Angel here told me you were looking for me. Something to do with a makeover for your…” Suzan started off before being cut short by Rosa who quickly interrupted her. She knew how Linda was against sissies, loving nothing more than to humiliate them at least those she thought deserved it which were a lot of guys. You didn’t need to do a lot wrong to deserve it in her eyes. She guessed that was something Suzan would do as well given her affiliation.

While Rosa like the sissy look as far as clothing and the like were concerned she didn’t want to humiliate Sora, sure she loved doing a little teasing here and there, but above all she loved him and that he was doing all of this for her. “Yes, I’m here for a makeover for this amazing cutie here. I want it to be a complete surprise however so I’d like to discuss this in private.” Rosa stated firmly.

Suzan was clearly taken by surprise by this statement or being cut off like that for that matter. All she had wanted was to poke some fun at this guy. Pretty much her entire client base was made up out of sissies and people with some other form of non-conventional relationship. It always gave Suzan an opportunity to make fun of and dominate someone, something she loved doing.

Nevertheless the client was queen so while she wasn’t all that happy about being cut off so rudely she decided to indulge this woman, even more so because she was a friend of Linda. With Linda being her main sponsor and supplier of clients she couldn’t afford to offend her. “As you wish, please follow me.” Suzan said dryly, she didn’t want to offend Rosa, but she also didn’t want to act like she liked her.

As Rosa followed Suzan somewhere out back Sora was left alone, standing there looking awkwardly. This Angel was cute, pretty yet there was something off about her. She just looked too ridiculous for his tastes. Choosing between her and Rosa would be one of the easiest choices. He was so happy that Rosa seemed to have such in interest in him, despite his discomfort about her wishes regarding his appearance.

When Rosa returned to him she had a big smile on her face. “Apparently there are a lot of request to keep the final look a secret and since working in her branch with a blindfold or such a thing is pretty hard she has found an amazing solution, these opaque contacts. With them on you won’t be able to see a thing. I know how scary that must sound considering where we are, but I would really love to be there for the grand reveal. So can you please put them on for me? Now there are going to be a couple of piercings in your new look as well, but don’t worry, if you really want to you can decide to take them out later allowing the holes to close back up.” Rosa explained to the mortified Sora, this was getting more and more extreme, but seeing her hopeful look he just couldn’t say anything but a short okay.

Excited out of her mind Rosa pulled him in for another hug and kiss before allowing him the time to put in the contacts making the world around him dark. It was honestly scary. “There we go, you’re going to look so amazing. Now I’ll be going after my mani-pedi, but Suzan here is going to take very good care of you that much she has promised me. I do have a few more errands to run to really make this Christmas awesome.” Rosa said leading the blinded Sora into the backroom of the salon where she helped him out of his clothes and onto a padded table.

His nerves were reaching new heights every second as were his doubts about whether or not this was worth it. He should have refuse, or at least argued, but he simply couldn’t refuse Rosa who had such enthusiasm. It wasn’t even like he could blame any of this on her as he had given in pretty quickly to all of her demands.

What followed nearly straight after on that table made him regret this all even more. Something strange, warm and gooey was applied to his legs, then there was something stuck to that gooey mass and followed by a painful yank that made him feel like Suzan was trying to pull his skin off. At least not seeing how naked he was made this a little less embarrassing, but that embarrassment would have been overshadowed by the pain rather quickly anyways.

This painful application and tearing process continued for a while and it felt like not an inch of his body was saved from it. It had started with his legs, but moved up to his groin, his chest, his arms, even his butt crack, beard area and eyebrows hadn’t been saved. His skin was lightly burning all over once it was done, a slight discomfort left, but one that was quickly resolved as he got rubbed down with a soothing lotion that strongly smelt of Roses. The careful application of the lotion felt great.

Still blind he was helped into something that felt like a very loose light weight kind of dress, that felt a little like the smocks at the barber which he guessed this was the fabric felt way more titillating for some reason, nearly erotic on his skin. He was helped to his feet and led around until he was seated I a nice comfortable chair. Still pretty much naked safe from this smock. Once there a lot started happening at once all of a sudden.

There was something cold applied to his toenails, while that was happening something with he guessed aluminium foil was done to his hair. There was a short break for his hair then which was followed by warm blow-dryers all around. Every step made him more and more nervous about how he would end up looking. Especially when the he felt something on his earlobe followed by a short sharp pain. A process that was repeated in his other earlobe, before finally being repeated once more on his tongue which had been pulled out with pliers. Much to his shock he could feel a hard metal ball sitting right in the middle of his tongue. It was far enough back to prevent a lisp.

He barely had time to process everything as the work on him just carried on. The blow-dryer got removed and the work on his hair started right back up, this time with scissors. Meanwhile his fingernails were being worked on with something that felt very much the same as what had happened to his toenails. Finally when all seemed pretty much done his face got attacked by a whole array of brushes and other things he couldn’t quite place.

Suzan was just finishing up his look with a makeup setting spray when Rosa returned to the store squealing in delight the moment she saw Sora and the way he was looking now. She simply couldn’t get enough of how good he looked right now, something she instantly voiced. “Oh my god you look simply amazing, I can’t wait to show you just how cute you look, you look even better than I first imagine but right now we have no time to waste. Let me help you get dressed again.” Rosa said as she pulled him out of his chair and back to the backroom.

Very gently she helped him out of the smock, an embarrassed look instantly spreading on his made-up face as he realised he was standing before his crush completely naked in makeup and whatever else they had done to him. It got a giggle out of Rosa. “There’s no need to worry sweetie. I love that you’re doing all of this for me, you really are perfect and I couldn’t have wished for better company to celebrate my first Christmas in ages.” Rosa comforted him as she helped him back in the outfit he had arrived in. For some reason it felt strange on him now. The panties and especially the tights felt a lot more intense on his skin, in a weird good way, yet one that worried him as well.

Fully dressed Rosa pulled him back out in the salon, gently holding his hand as she strung him along. Now that he was blind he had to trust her, something he didn’t mind that much. He loved walking hand in hand with him. “Suzan and Angel, the two of you really did a terrific job, I couldn’t have been more pleased with the result, thank you so very much.” Rosa said as she paid for everything before pulling Sora out to the car. The short moment where he was outside was one of the most nerve-wracking of his life although he guessed he now looked more in sync with his outfit.

“Alright, sweetie, our next stop is at the clothing store of a very dear friend of mine. She’s a little eccentric, and I don’t condone everything she does, but she has been a huge help to me and others like me. There’s no need to worry, she’s a real sweet one if she likes you, and from what I’ve told her she loves you. It’s the last stop we have to make and then we can go ahead and have our party.” Rosa explained what was going to happen to the nervous guy in her passenger’s seat.

A few moments later the car stopped and Rosa guided him out of the passenger and almost straight into a store where they were nearly instantly greeted by a very excited and happy sounding woman. “Ah Rosa, it’s so good to see you again, it has been way too long. How are things. Is this here the one you were telling me about? I’m so glad you’ve found someone worthy of your love, you deserve it. He looks marvellous indeed, so cute in your twin outfits, and I bet he’ll look even better in that outfit you requested. I’ve got it all ready to try on so shall we?” A woman’s voice spoke.

“It’s great to see you too Linda, this here is Sora. He’s the best thing to happen to me all year. You could call it a Christmas miracle if you wish. We have barely started to get to know each other, but he has gone to such great lengths to make me happy already. No one has ever done anything like this for me. I can’t wait to see him in that outfit you have ready.” Rosa exclaimed as she followed Linda to the back of the store, pulling Sora along by his hand. He couldn’t help but feel a bit frightened about what his outfit was going to be. His embarrassment was only alleviated slightly by Rosa’s sweet words and even the slight admiration in Linda’s voice. Whatever it was he was going to be dressed in he did feel rather at ease with these two women.

“Why don’t you have a seat Rosa, I’ll take it form here.” Linda offered, ushering Rosa to one of the comfortable chairs in front of the stage. She then took over Sora’s hand and helped him up the stage and behind the curtain.

“You know Sora, I really think it’s amazing what you’ve already done for Rosa. I can’t think of any guy willing to go to such lengths just to make his girlfriend happy. It really is heart warming to see and while I know Rosa’s request haven’t been the easiest she’s more than worth it. She’s an amazing woman as I’m sure you know.” Linda said softly so Rosa wouldn’t hear as she helped the nervous guy out of his current clothes.

“Th…thanks, I’m not entirely sure about all of this, but I can’t really say no to her, I mean she’s so amazing and I just want to make her happy. Seeing how happy she is about all of this does alleviate some doubts, but it’s a huge step.” Sora exclaimed voicing some of his insecurities, feeling like they were safe with Linda.

“I can definitely understand that, I admire that you’re trying this hard. All I can really say is to wait and see for a little while, get comfortable, see how it goes for a bit and then revaluate whether or not it’s worth it.” Linda replied.

“That sounds like a good idea, getting comfortable is a little hard like this though, knowing how much has changed already without having a clue as to what has actually happened. Also I was wondering if you might have an idea for a good present for her. I only really met her yesterday late after all stores had closed already and then this morning I left straight away for all this, I haven’t had time to buy or even think about a present.” Sora asked awkwardly as Linda started dressing him in the outfit she had laid out for him.

The outfit felt weird and especially the first piece felt very restraining around his waist, almost too much for comfort.  He blushed under the layers of makeup as he felt something like the tights being rolled up his legs, only these reached up to his upper thighs, they also felt way thinner and way more electrifying. Making matters worse he couldn’t help but get an erection. Linda just acted like she didn’t realise in order not to embarrass him. Opposed to a lot of guys coming here she really respected Sora for what he was doing to make Rosa happy. “Well that’s very sweet of you too ask, but I wouldn’t worry about it too much. What you are doing is the best present you can give her.” Linda said.

Following the stockings were a pair of panties they felt very soft and slippery, honestly kind of amazing which didn’t help his erection one bit. They had the annoying property of being thong styled and riding very far up his bottom. The dress that was then pulled over his head had to be the worst of all. Unlike the sweater dress the skirt on this one was very short. So short that it ended above the tops of his stockings.

There after there was some more fumbling around the waist of the dress before something was put up on his head and last but not least his feet were guided into shoes that forced his feet in a very awkward position. These had to be high heels and his balance on them was terrible, even more so without the use of his eyes.

After his initial questions he had remained rather quiet, but now he just needed to voice his concern to Linda. “Uhm Linda, I’m not quite sure these shoes are a good idea. I mean I feel very insecure standing in them and I wouldn’t want to end up in the hospital like this.” He said awkwardly.

Linda just shushed him. “Don’t worry about those heels, I’ll be here to make sure you don’t fall and Rosa will be more than willing to help get you to the car and all. Besides, I guess you’ll spend most of the party inside anyways so I doubt you’ll need to stand much. Now let’s go show you off to Rosa, I’m sure she’ll love the final result. Also when you get your first look I guess it’ll be a lot to take in. Just try to give it the benefit of the doubt, give it a chance and don’t be afraid to enjoy yourself.” She tried putting him at ease.

Her words didn’t give him much confidence as to how he would like how he looked, but he guessed it could do no harm if it was just a look to share with Rosa and if she would be ecstatic like she had been all day so far.

A slight surprised shriek escaped Sora as Linda suddenly put her arm under his armpit. It only made her laugh a little. “Sorry Sora, I wouldn’t want you to fall, this is how I can best support you.” She said before carefully guiding him forward back through the curtain and onto the stage in front of Rosa.

“Oh my god Linda, it’s perfect, like always you’ve outdone yourself with your cute outfit designs, of course it also helps you have such a cute model. Thank you so much for putting up with this for me Sora, you look just amazing, I can’t wait to reveal your new outfit to you. Linda, I hope you don’t mind, but I want to get home as soon as possible, we’ll have to really meet up some time to catch up, Sora simply looks too good not to take home right away.” Rosa gushed.

Linda just laughed. “I completely understand, have a nice Christmas the two of you. I need to get going myself, my Christmas party should start any moment now. Oh and Rosa, take care of him will you, I imagine he isn’t quite used to such heels so you’ll need to support him.” Linda exclaimed.

It got a laugh out of Rosa as she joked. “That won’t be a problem at all, I wouldn’t want to let such a cutie move even an inch from my side. I’ll take over from here. Have a nice Christmas yourself and say hey to Stephanie from me.” She said before taking Sora over from Linda and carefully guiding him off the stage, out of the shop and into the car.

The way back home Sora got showered with compliments on how great he look and how amazing it was that he wanted to do this for her. He wasn’t really all that sure that was a good thing though considering Rosa was into girls, could he really make a believable girl? He didn’t know how to feel about that.

Excited out of her mind Rosa quickly pulled up in the driveway and led a nervous Sora into the hallway. “Just stay here for a little bit sweetie, I’ll be right back. I’m going to change into my own outfit and then we can go for the grand reveal, this is so exciting.” Rosa said before he heard her rushing upstairs, leaving him alone with his thoughts.

All alone Sora didn’t have a lot of opportunity to worry too much about how he looked, for one it didn’t really matter that much with how happy Rosa seemed and her being the only one here. Secondly, he needed all his concentration to keep his balance in these insanely high heels.

Chapter 4

It ended up taking Rosa about 20 minutes to get ready herself, her approach was announce by the loud clicking of heels coming down the stairs. Now that he was standing in a pair of his own Sora had a real appreciation for how difficult that must be. The butterflies in his stomach fluttered wildly once more as he felt Rosa rest her hands on his bare shoulders. “Let me help you take those contacts out, I think it’s best you stay away from your eyes yourself right now.” Rosa said as she started fishing the contacts out of Sora’s eyes.

They were standing in front of a full length mirror in the hallway and the moment Sora could see he let out a loud gasp. All he saw in the mirror were two gorgeous women, one of them he realised much to his discomfort and shock was him. She or rather he was the girliest of the two, girly in a way that made him fear he couldn’t just undo this like Rosa had claimed.

His hair was cut into a structured long bob maintaining its shoulder length. The usual jet black colour now sported some ombre highlights in a decisively feminine manner. His face simply didn’t look like his own anymore either. His once rather bushy brows were now neatly shaped in a rather full yet elegant fashion. They weren’t two bad on their own, but combined with the strategically used highlighter, the hot pink lipstick making his lips look rather plump, the soft pink smoky eye shadow, the long lashes, the winged eye liner and a light rosy blush he couldn’t quite tell if it was makeup or his own showing through the foundation, he definitely looked like a young woman with some exaggerated makeup. His earrings came in a pair of pink candy canes dangling off his earlobes.

This theme of hot pink mixed with a nearly white powder pink followed throughout his outfit. The only things he couldn’t see was the solid hot pink satin corset, tied off at his back with a length of powder pink satin ribbon creating his thin waist. It was tied of with a big bow at his back, sitting above his thong style hot pink satin panties. The waistband of the panties was trimmed in powder pink fake fur adorned at the sides with a hot pink satin bow.

What he couldn’t see was the least of his worries though since what he could see was more than bad enough already. The main piece of the outfit was a hot pink velvet dress. It was strapless, starting just underneath his armpits trimmed there in powder pink fake fur, a hot pink bow sitting at the middle of his back. At his waist the dress was pulled tight by a cream coloured broad lacquered belt with a big gold buckle. Underneath that belt the dress stopped clinging to his body, the skirt puffing out big time helped by some petticoats. All in all it stopped at his mid-thigh, lined at the bottom with powder pink fur as well. Smaller hot pink bows sat evenly spaced in this trim.

The skirt was just enough to see the end of the hot pink garters coming from the corset. The garter tabs ended in hot pink bows gripping the powder pink fur tops of his stockings. The stockings themselves were sheer, made up out of a hot pink and a powder pink strip spiralling upwards making his legs look like candy canes matching the way his now inch long acrylic nails were painted in alternating hot pink and powder pink diagonal lines.

On his feet were a pair hot pink lacquered ankle boots with a thin five inch tall stiletto heel. The top of the boots was trimmed with powder pink fur. Combined with the Christmas hat made out of hot pink velvet with a powder pink fur trim at the bottom and a powder pink fur ball hanging of the end completed his outfit.

Rosa was dressed quite similar, although her outfit was a more classic Ms. Santa one compared to his pink monstrosity. It was way more straight forward with less bows, but definitely outrageously sexy the main eye catcher of her makeup were her fire engine red glossy lips, and her dark smoky eyeshadow. She wore a pair of red candy canes in her ears, matching his, just like her nails were painted the same as his only in red and white.

Her dress was a simple red velvet tubular one without the puffed up skirt, it was trimmed in white fur both at the top and bottom, clinging to her perfect figure amazingly, it only got accentuated by the broad black lacquered belt with the a big gold buckle. Just like his the dress was outrageously short though only just long enough to hide her panties. On top of her head sat a more classic red and white Christmas hat.

Unlike his her stockings were made out of red sheer nylon instead of two colours, they ended in white fur tops holding themselves up instead of needing garters. They went into a pair of black leather knee high boots ending in white fur tops, just like his ankle boots hers had a thin five inch stiletto heel keeping their height difference intact.

Eventually it was Rosa who broke the stunned silence. “You look good enough to eat don’t you sweetie? Thank you so much for doing this yet again, I couldn’t have asked for a better Christmas present.” Quickly spinning him around she pulled him in for another kiss more passionate than any he had gotten before clearly loving the his new look.

Sora on the other hand wasn’t all that happy with how girly he looked, not even here in private, how the hell was he even going to undo all of this? His strong reluctance was somewhat broken by the kiss however as he softened in her arms. Maybe this wasn’t all that bad either. Rosa looked outrageously sexy as well.

When the kiss broke Rosa could see his insecurity, but she wasn’t going to let him speak up. Instead she wanted to distract him, take his mind of the shock and slowly let him ease into it, relax a little before she would ask how he felt. Grabbing a tight hold of his arm she pulled him to the living room. “Let’s get this Christmas party going sweety, you just sit here and wait for me okay?” She asked as she guided him down on a couch getting a confirming nod before she walked off to the kitchen.

Still stunned Sora just stared in front of him at the modestly decorated Christmas tree, some presents sitting underneath including the box of wine he had brought over. Was this really a good idea? Just look at him, he looked like such a girly girl, hell even his figure looked girlish with how that corset pulled in his waist and how that puffed out skirt gave him the illusion of a booty. This was not what he wanted, but Rosa seemed to love it.

His thoughts got interrupted when Rosa returned with a plate filled with tasty looking appetizers, two of each, a bottle of champagne and two crystal glasses, only the best for this special evening. Popping the bottle she poured the two glasses, and handed one to Sora, taking place next to him on the couch, their legs touching. “Merry Christmas to you sweetie, I’m so glad to be celebrating Christmas again considering the company.” She exclaimed genuinely clinking their glasses together.

Taking a sip of her drink she was right back on his case with a question, which was followed by another one and one thereafter. Slowly but surely with each casual question Sora was starting to relax a little at a time until the point where their conversation was growing more natural once more, just like it had yesterday evening.

Despite his intense wardrobe change Rosa’s casual way allowed him to forget about it and simply just enjoy the good company, good food and drinks. The ways in which he got reminded of his outfit were mainly positive. It came in the sense of an electrifying feeling of his own nylon legs rubbing together whenever he moved them or even rubbing up against Rosa’s. It was a strange but very pleasant feeling. So was Rosa’s warm hand that often came to rest upon his thigh.

As he kept growing more comfortable and the alcohol slowly started working, lowering his inhibitions a little at a time. It came to a point where he even started subtly searching out these strange pleasant sensations himself, intentionally rubbing his leg up against Rosa’s a little more, feeling her thigh, god he still couldn’t believe he was so close to the woman he had crushed on for so very long. It was a feeling that soon overpowered his doubts about this all as he became a little more touchy and a little more comfortable around her.

This change didn’t go unnoticed by Rosa either as she herself grew a little more playful in return, rubbing her hand up and down his thigh seductively instead of just resting it there, she even went as far as to cup his rock hard cock through his panties after inching further and further up his thigh for a few minutes.

It cause him to moan followed immediately by a deep blush, skilfully concealed by his makeup, but the mortified look on his face betrayed him. Rosa just giggled giving him a little peck, allowing him to relax again after fearing he would be scolded for his hardon. “I could be wrong, I could be right so please tell me Sora, you’re starting to like your outfit don’t you?” She asked teasingly grabbing his cock through his panties again.

Her teasing only solidified his blush, but after not worrying about it for over two hours now and in fact enjoying the new weird but pleasant sensations he couldn’t really deny it. “It’s not half bad I guess. I mean it has its perks. Some parts of it are quite fun. The biggest perk of them all is obviously that you seem to like me so much in this outfit. I’ve really been enjoying our time together.” Sora admitted.

“You can’t believe how glad I am to hear so sweety, it warms my hard really. I was afraid I pushed things a little too far despite how amazing you look. I do genuinely want you to feel good and at ease, I know this is probably shockingly early, but I think I’m in love with you, I would love to call you mine.” Rosa said with another gentle peck on his cheek.

Sora couldn’t believe what he was hearing, this was a dream come true, it was all he ever wished for. He had sacrificed a lot, but hearing those words from Rosa’s mouth filled him with joy. A joy that soon got slightly disrupted by a point of worry. “I love you too Rosa, but for us to be together does that mean I have to wear these clothes all the time?” He asked a bit scared of the answer, not even knowing if he could or would even want to say no even if that was the case.

It just earned him a giggle. “Well of course not sweetie, we could shop for more casual things for you to wear, even your old clothes if you really want. Still I would appreciate you dressing up nicely when it’s just the two of us, what do you think does that seem fair, does that seem like something you’d want?” Rosa asked, a hopeful look in her eyes.

He hesitated for just a moment, doing this once was quite a big sacrifice already, then again like he had confessed it was not that bad and if it was just something among the two of them he guessed he could deal with it. He certainly wouldn’t mind to have that feeling of his nylon legs rubbing together more often, or the sheer adoration with which Rosa treated him.

After his short hesitation it was pretty easy to come to a conclusion. “I would love to dress up like this for you more often Rosa. If it makes you so happy then it’s only a small price to pay. While it is indeed still early I’d love to be yours.” He said.

“Well then lover, how about we seal this with a kiss? Why don’t you jump on Santa’s lap?” Rosa asked with a smirk as Sora somewhat clumsily got up in his very tall heels. Rosa was right there to support and steady him from the couch though. She helped him turn around before pulling him in her lap facing her, a knee landing on each side of her hips while his body leant into hers as an intense make out session followed.

Neither of them could seem to get enough of it, enjoying the other’s attention and their closeness. Eventually like all good things it had to come to an end though, an end mainly meant to make the evening progress to more fun. “Why don’t we get dinner over with and carry on afterwards, I do have one more big surprise for you. Along with a couple more presents.” Rosa said with a wink.

Sora was all to eager to get off her lap, not because he was hungry, but because he couldn’t wait to find out what else the evening would bring. One thing was certain though, nothing could ruin his mood anymore. Rosa rose to her feet right after him in order to help escort him to the table since he still couldn’t properly stand in his heels learning to handle those could wait for another day though.

Dinner just like the appetizer was exquisite, the best Sora had ever had, served by Rosa as he couldn’t really walk back and forth from the kitchen on his own. It was shared together with some more intimate conversation, but if both of them were being honest they were looking forward to what would happen after.

When they finished the main course Rosa announced. “Why don’t you go to the couch while I clear the table? It’s a short trip so a nice exercise for those heels. If you feel like you can’t you can always call for help. In any case it’s time for dessert, and I have a very special dessert for the both of us to enjoy, I’ll bring it along in a minute, you just wait and be patient.” Rosa said with a teasing wink making Sora blush, the sultry way in which she had said it made him have his suspicions about what she meant with dessert and he was definitely looking forward to it.

Chapter 5

The way to the couch while short was a hard one. He didn’t want to disappoint Rosa so he really wanted to be able to make it on his own. After the guided walking he had done so far he was starting to get used to the heels, still it remained very tricky and slow for him to make his way to the couch, but with a lot of concentration and caution he managed.

While Rosa was making her way back and fort to the kitchen Sora patiently waited on the couch, lightly rubbing his legs together, filled with excitement and anticipation. He really hoped that Rosa had meant sex for dessert, his cock was already rock hard at the thought alone, or was that because of how good his smooth nylon legs felt?

Eventually after about ten minutes Rosa returned to the couch, but she didn’t bother sitting down next to him like she had before. In fact she looked slightly worried as she stood before him. “I guess it’s time for your big surprise sweety, I’m not like most women, but I hope that doesn’t come between what we have. What you’re about to see doesn’t change anything in regards of who I am, you’ll just know me a little better, so please keep an open mind and I really hope that doesn’t change what we have. In any case it is best to just get this over with.” Rosa said, confusing Sora with her worry.

Slowly but surely Rosa raised up her skirt grabbing Sora’s complete attention as he would finally find out what he had been longing to see for such a long time every time he had watched her undress through his window. Finally he would see her naked, he for one was already enjoying the provocative red satin thong. It looked so sexy on her, especially when she hooked her elegant nails into waistband to lower them.

When she did work them down her thighs however Sora couldn’t supress a loud surprised shriek when instead of pussy, a girthy rather big semi hard cock flopped out from between her legs only a couple inches removed from his face. It was only slightly bigger than seven inches, but it looked huge to Sora. He had never seen it coming with how expertly it had been tucked back. He couldn’t believe it, this woman he had lusted after for so long had a cock?!

Instinctively he moved back a little, seeing the hurt and disappointment in Rosa’s eyes as he did. It pained him as he really did care for her, but this, he wasn’t gay, surely Rosa would understand right? He had to say something though, something to put her at ease. To explain his reaction as no matter how shocked he was he didn’t want to hurt her. “Look Rosa, I’m sorry, you’re amazing, but I’m not gay. Why didn’t you just say so from the start?” He asked.

His explanation only seemed to make things worse though as her disappointment turned to anger. “Gay? I’m no man, having a cock doesn’t define me, I’m still every bit the woman you always thought. Were my genitals the only things you were after or what? Honestly what did you expect? Did you expect me to come over for some sugar and casually mention, oh and I have a cock by the way! What kind of introduction would that be? I’m so sick of being judged for what’s between my legs.” She raged.

It instantly got Sora into an apologetic defensive stance. “I’m sorry Rosa, I didn’t mean to hurt you. It’s just that I am very surprised, I didn’t imagine a cock would nearly hit me in the face when you pulled down your panties. Please, I was just surprised that’s all. Just please don’t be mad at me, just tell me how I can make it up to you I beg you.” Sora exclaimed, genuinely more concerned with having angered Rosa than he was about her cock.

“Well, I guess there is one thing you could do. You could prove to me that you were just startled by the surprise, but you still accept and love me for who I am. I think giving it a kiss would do.” Rosa said still looking a little angry and sceptical, yet a slight smirk also appeared on her face.

Sora was shocked hearing this, he couldn’t kiss it, he couldn’t kiss a cock now could he? Then again he guessed Rosa had a point, she hadn’t changed, just revealed more of herself, why did that more have to be a cock? He really didn’t want to put his lips against a cock, but he also didn’t want to see Rosa hurt and angry like this. Besides what would a little kiss hurt? He couldn’t bring himself to deny her request. So closing his eyes he inched forward and placed a quick kiss on the circumcised  head of Rosa’s cock. It felt warm, slightly wet with a subtle musky smell hanging around it.

Yet he couldn’t help but shriek again as the cock throbbed heavily once his lips made contact with it. This time Rosa wasn’t angry though, she just giggled. “Oh, I think it likes you, maybe you should kiss it some more, give it a suckle even.” She suggested with a wink, her breath sounding slightly laboured as she was getting so turned on watching how Sora who really had turned out gorgeous, kissed her cock, feeling his soft warm lips against it was heaven. She simply couldn’t be mad at him like this.

A heavy blush was quickly growing underneath Sora’s heavy makeup. Kiss it some more? Suck it? That was a bridge too far, but Rosa looked at him with such excited anticipation. Maybe he should do this a little, just so she would be pleased with him again, to really make up for his miss steps. What harm could it do? No one would ever have to find out right, besides if it probably counted as sex with Rosa which would definitely give him bragging rights. Just like he had never seen it coming, he guessed no one would guess Rosa did in fact have a cock.

Filled with excitement Rosa witnessed how Sora closed his eyes once more and inched closer to her cock. His soft warm lips soon made contact with her sensitive tip once more. Unable to help it Rosa let out a soft moan followed by another one rather quickly as his lips soon parted allowing the throbbing head of her cock to slip into his warm velvety wet mouth. God it felt like heaven, so much better than anyone she had ever taken home before.

After running from her awfully catholic family for not accepting her as trans she had moved here with pretty much nothing but her freedom to be who she was. In some of the group counselling’s she had attended she had run into Linda who was very sympathetic to her story. Linda had helped her get all her papers, had found her a place to stay and even found her an opportunity to attend college. It was Linda who had later helped her erect her business, delivering carefully planned diets to people’s houses, it had grown into a great blooming business affording her this nice house.

Despite all her successes and Linda’s support for who she was it remained a side of her she was cautious to show to people. A side she hid from most people around her. Her entire sex life had existed out of flings, girls at parties wanting to try something new, nothing serious, nothing wholesome, nothing like what Sora was offering her. For the first time she was actually having sex with someone with whom she shared a real connection, someone she really loved.

She felt somewhat bad for getting mad at him, his initial reaction had been the exact one she feared the most, the one for which she only ever had flings. If she was honest with herself she couldn’t really blame him, she doubted Sora had ever laid eyes on a woman like her and after all he had done for her she could imagine he felt deceived and shocked. If she was honest he had every reason to be mad at her and yet he had chosen to forgive her and even please her, proving his claims that he really wanted her to be happy, that he really loved her.

It was the best thing that had ever happened to her, even better than Linda in a way. She simply couldn’t be grateful enough to him. There were no words of praise that could cover how thankful she was, but praise was really all he deserved. “Mmm thank you so much Sora, that feels amazing, please don’t stop. I’m sorry I was mad at you, I really shouldn’t have been, not after all you have already done for me. You’re the best thing to ever happen to me and I hope you can forgive me.” Rosa said in between moans.

Sora felt so relieved hearing her praise instead of her anger, this was not at all what he imagined doing. Hell it was something he would have never done, or so he thought. It went against every fibre of his being, but Rosa was worth it though, she was right, cock or pussy she was still the same person. He loved the way she was feeling good and he wanted to double down on it, letting her cock sink deeper into his mouth, rubbing his tongue and as a result his tongue stud all over it.

Rosa was in heaven Sora was definitely unexperienced, nothing compared to the flings she usually took home, but he made up for it more than a bit with his eagerness and that delicious tongue stud. Besides he had sacrificed so much for her and offered her what no one ever had before, a true genuine loving connection.

Resting a hand on the back of Sora’s head Rosa really had to force herself not to start face fucking him. She had to resist as tempting as it was. “Mmm oh god Sora, you’re doing such an amazing job.” Rosa kept on praising him, her breath stocking in her throat as she was rapidly growing towards the peak of an orgasm. It might have gone off to a bit of a false start, but she loved how this moment was playing out. This was what she had been looking forward to all day long, seeing how gorgeous Sora had turned out had fuelled her arousal all day long.

“Baby, I’m going to cum soon I would love it if you’d let me cum in your mouth, it would please me so much, but I understand if you don’t want to. In that case now is the moment to pull away.” Rosa barely managed to get out through intense moans. She was so close, but after everything that happened she felt like she had to warn Sora, she didn’t want to ruin things between them by rudely cumming down his throat.

This warning kind of shocked Sora into stopping. The threat of tasting cum was a rather disgusting one, then again how bad could it be? He was kind of embarrassed to admit it, but sucking cock hadn’t been as bad as he had thought it would be. In fact he had enjoyed the way Rosa was clearly loving and praising it. So much even that he didn’t really want to stop, he craved her praise and moans.

It was this hesitation to stop that in the end meant a mouth full of cum. He had hesitated too long with Rosa’s about to cum cock still in his mouth for her to keep holding back. Startled by the sudden slightly salty, but not too bad tasting cum blasting in his mouth he nearly pulled back, but he was stopped by Rosa’s hand preventing him to pull off of her cock.

She moaned and squealed above him as she filled his mouth with blast after blast of hot sticky cum, not letting go of his head until her orgasm finally slowed down and eventually stopped. Her cock was already staring to go limp when she released his head, feeling quite embarrassed and apologetic. “Oh my god, I’m so sorry sweety, I didn’t mean to, I just mean if you pulled back when you tried to you would have ended up with a face full of my cum and that would have been a real mess.” Rosa tried to explain to him.

Sora didn’t quite know what to make of this, on one hand he was disgusted, on the other he was so glad he had been able to make Rosa cum. His biggest problem now was figuring out what to do with all this cum in his still open mouth, he couldn’t quite spit it out on the floor and he didn’t really want to swallow it either. He was stuck with a mouthful of cum looking up helplessly at Rosa.

Rosa couldn’t help but giggle seeing him like that. He looked so cute, awkward yet hot with her cum in his mouth. It really made her heart flutter like never before. “Let me help you take care of that sweetie.” Rosa said as she knelt down before him, planting another kiss on his lips, this time tasting herself off of them. For a long couple of minutes they switched the cum back and forth until it has pretty much been spread evenly and swallowed by the both of them during their kiss. When Rosa opened her eyes again she smiled seeing Sora’s blush.

“You did so very great sweetie, and I really can’t wait to spend more moments like this with you. You really are the best.” Rosa encouraged him again as his blush just grew even deeper red. He was glad Rosa was so happy, but he had a bad feeling that he would be sucking cock more often going forth, especially if he stayed with her. At least if it stayed with sucking. His blush grew even fiercer imagining it wouldn’t.

When Rosa got back up Sora’s eyes instantly went back to her cock. It had gone nearly completely limp by now, still it remained impressive. Rosa was obviously a shower and not a grower. He couldn’t believe he had really taken that thing between his lips. Hell he still couldn’t believe that such a gorgeous woman like Rosa actually had a cock, especially such a big one, quite a bit bigger than his just below average cock which was rock hard beneath the puffy skirt, not able to make a tent through the petticoats.

He was dressed like the girliest girl, he had just sucked a cock and yet he was rock hard. It was all so confusing. He guessed Rosa was right, what was between her legs didn’t really change the woman she was and he had crushed on for so long. Besides if you didn’t think about all concepts like man woman, gay or straight, then was sucking a cock really worse than eating a pussy? It was just different right? Maybe he should just try not to think about it too much and just think about it like making love with an amazing woman like Rosa was for sure, cause after everything he still loved her so much.

His staring at her cock didn’t escape Rosa’s attention either, she loved seeing it. Despite his apprehension earlier, she had certainly appealed to his curiosity, that much was clear. “If you want you can have a better look at it sweety, I certainly wouldn’t mind you feeling it up and observing it a little closer. Just be warned, it might grow hard again if you do.” Rosa said with a wink and a giggle.

“Euhm uh, no thank you, not right away, I mean I’m good. I don’t mean this in a bad way, I mean your cock is amazing, it’s just euhm not right now.” Sora stammered blushing fiercely, your cock is amazing? What was he even saying, god he just didn’t want to insult her.

Rosa didn’t seem to mind in the slightest. She just giggled loudly once more, Sora was so cute, all blushy and awkward, cute and sweet as she could imagine he probably hadn’t fully come to terms with being a cock sucker just yet. “As you wish sweetie, all you need to do is ask. In any case, let’s go over to the presents shall we?” Rosa asked as she stepped out of her panties all the way.

Sora’s eyes went as big as saucers, just what was Rosa planning on giving him? It soon became clear when she picked up the panties and handed them to him. “Here you are, I know it isn’t a lot, or all that special considering the fact that you now have panties of your own, but I really wanted to give you these. Call it what you will, a trophy, a memento, our naughty secret… Just something to look back at our first of hopefully many dates to come. “ Rosa explained as Sora looked at them with a big smile, before awkwardly looking down.

“I would like to give you something as well, but oh well that box is all I have and you seem to have way more packages under the tree. It’s just this all happened so suddenly and well, I didn’t really have the time to get you much.” Sora said feeling rather awkward about this whole gifting moment.

“Don’t you worry sweetie, you already gave me way more than I could have ever wished for to be honest, I’m so surprised and honoured that you even brought me something on such short notice. If you do feel really bad however I won’t complain if you want to give me another blowjob.” Rosa winked, her cock still on full display since she hadn’t bothered lowering her dress again.

When Sora just blushed she laughed. “You don’t have to sweetie, I was just messing with you, now how about a real present? One you can unwrap I mean.” She said as she walked to the tree, her naked bottom on full display, wiggling seductively in front of him, only getting all that more spectacular as she bent over at the waist to pick up a neatly wrapped present, the wrapping paper was red and white resembling a candy cane with a big dark green festive bow on top.

Handing it to Sora, she looked on with excitement as he opened it up. It was by far one of the most special presents she had for him. Not on the content front but definitely when it came to meaning. Sora was a bit confused when the box opened inside there was an elegant rather thin black collar made out of braided black leather. The buckle at the back looked like it was made out of silver and so was the ring at the front, a ring off which there dangled a sliver heart, the name Sora engraved in the front.

Seeing his confusion Rosa explained. “As you may, or may not have noticed yet, I kind of like being in control. It goes a bit further than just being assertive as well and I kind of love a submissive partner. In that regard it would mean a ton to me if you decided to really be mine and wear that collar for me. If you do however I’ll be the one to decided when and if it comes off again. I’ll become a bit more demanding and I will take more liberty in doing with you as I please. Don’t you worry though, I’m none too harsh, teasing and having fun is more my style. You can also always say it when something goes too far for you or you are uncomfortable with something. Let’s say our save word could be candy cane because you look so delicious, so what do you say?” Rosa asked filled with hope as she looked down at the amazed guy who once again had to face a huge surprise.

It was a present that she hadn’t been completely sure she would give until just now. This wasn’t something Rose took lightly, not at all, but Sora had definitely earned it. What he had done for her was simply amazing and she wanted nothing more than for him to be hers.

Today had been a real rollercoaster already, but despite his reservations he had to admit that Rosa had been more than worth it already. This was a big deal though, but maybe it was for the best. He felt too awkward voicing his wishes or making demands. Hell his cock was rock hard and despite having gone out of his way and comfort zone to please Rosa he was still terrified to ask Rosa to take care of him, he was even scared of letting her find out. Maybe letting Rosa take control would be for the best. That way he could just go with the flow and hopefully get off himself. He sure as hell wasn’t going to ask for it himself, besides his cock was straining hard, if he was honest with himself he quite like the idea of being Rosa’s and being at her mercy.

“I… I would be honoured. Would you please do the honours?” Sora stammered nervously as she rose to his feet in front of Rosa and handed her the elegant collar. He felt an intense rush as he saw the excitement on Rosa’s face turn to a determined smirk. Taking the collar from him she gently fastened it around his neck, pulling it tight but not to tight, just enough to remind him it was there.

“Very good choice my slut. I promise you won’t regret this.” She said before rather aggressively grabbing his chin and pulling him in for another intense kiss. When she broke off the kiss she instantly pushed him down to his knees until his face was at the height of her cock. “You may kiss the tip to seal the deal.” She smirked, this time it sounded more like a demand than a request. It was both scary and thrilling for Sora. This was really happening. Leaning forward he planted a gentle yet firm kiss on the tip of Rosa’s limp cock, feeling it twitch lightly.

Stepping over him Rosa sat down on the couch where he had jut been sitting. “You may refer to me as Mistress going forward my dear little Sora. Now why don’t you give your Mistress her present? I’m curious to see what you have gotten me.” Rosa said with a renewed confidence, sweet as ever yet with a demanding touch. It made Sora’s heart beat faster.

Doing his best to walk to the tree without falling Sora picked up the big heavy box he had packed. Carrying it towards the couch gave him a very hard time, unsteady on his tall thin heels. He barely made it as Rosa quickly took the package from him before he would fall, placing it down on her lap and grabbing his chin to plant another quick kiss on his lips.

“I…it isn’t much Mistress, but I wanted to give you something and…” Sora started stammering nervously yet again, feeling a thrill when he called Rosa Mistress, but he got cut short by her.

“That’s the last time you bring that up, or would you like to get a spanking sweetie. Like I said, I’m flattered that you brought me something, so don’t feel sorry. Why don’t you go pick out another present? You can choose which one.” She said with a smile, pretty excited to see his reaction to all of them. It were just a few things thrown together quickly while he was having his makeover.

Slightly hesitant Sora walked back to the tree, he was nervous seeing all these presents left for him, feeling bad that he only got one for his Mistress, but he knew better than to complain about that again. He picked out a similarly packed rectangle, not the largest of the bunch but definitely not the smallest either. “You look simply delicious bent over like that.” Rosa teased as she felt her cock harden a little more.

With his present in hand he carefully walked back to Rosa who pointed down at her feet. He blushed slightly as he sunk to his knees in front of her. “You may thank me with a kiss as well sweetie.” Rosa exclaimed excited as she opened her legs slightly revealing her slowly hardening cock.

While she hadn’t explicitly said it Rosa’s intention was clear, blushing fiercely underneath his makeup Sora blushed and leaned forward to once again kiss the tip of Rosa’s cock. Kissing a cock wasn’t something Sora ever considered doing, it was something that used to disgust him, but Rosa made it feel weirdly exciting in a way. She let out a soft moan as she instructed. “Alright, you may open your present.”

Opening her own present Rosa was happy with the case of wine, the one from yesterday she had enjoyed so much. It was a sweet thing to give her, but not all that personal. “Thank you so much sweetie, you didn’t have to. I’ll enjoy this present a lot. How about you? Do you think you’ll enjoy your present?” She asked, more excited about his reaction to his present than her own present.

Sora was looking stunned at what he had just opened. It was a package of five butt plugs, they were shaped like an egg, with a bit of a pointier tip than a typical egg. Each had a narrow base leading to a sort of bar which Sora guessed would fit perfectly in a butt crack. Each plug was made out of stainless steel. While the smallest one looked manageable, the biggest one looked huge and scary, nearly as big as his fist if he had to guess.

“Well… uhm, thank you I Mistress.” Sora replied not really sure how to feel about this. After everything he guessed his ass was the next logical step, but it was one that scared him more than sucking cock did, what would it mean if he got fucked by a real genuine cock? Having given himself to Rosa he guessed it was inevitable, still it was something he wasn’t at all looking forward to. It was something he had never even been remotely curious about despite having overheard friends speak about how great a finger up the butt while getting a blowjob could be.

“You should be a little more grateful honey, you don’t know how hard it has been for me to be with you all day long with you looking so cute to boot and not bend you over to take that cherry of yours. I’m dying to try out that cute butt of yours but I have controlled my urges for you. You’re not ready yet sweetie, and I don’t want to hurt you, but we’ll surely going to work towards getting you ready which is where these babies come in. If you’re plugged I can’t fuck you even if I wanted to, so here’s the deal either you ask me to fuck you or you ask me to plug you. Once you are at the third size I think you should be able to handle me.” Rosa explained, when Sora looked up he could see her cock was once again rock hard, making her words all that much scarier.

The threat of getting anything up his bottom was nearly enough to get Sora to use his safe word, the only reason he didn’t was because he knew Rosa wouldn’t like this. Besides no matter how scary this all was, Rosa was also making it somewhat exciting, despite not wanting to he guessed he would find out whether of no something up his ass did feel good as he spoke up. “Could you please plug my bottom Mistress?”

“With pleasure sweety, just hand me the box, turn your back to me and hold onto your knees. I’ll take care of it for you.” Rosa said sweetly, sensing his nervousness. She tried to make this as fun and easy as possible for him. It might not be her cock, but at least she would be sinking something in that cute butt of his already. Besides she could have a way closer look of his butthole swallowing that plug than she could of her cock entering his bottom.

Nervously Sora handed her the box and got into the position Rosa had asked, his bottom right in front of his Mistress on full display in the thong styled panties. Wasting no time at all Rosa pulled the bows at the side of the panties, making them come free at his hips and fall open. Apparently those two bows were all that kept his panties on making them very easy to remove. He blushed realising that Rosa must see how hard his cock was as well judging from the cool air he felt on it.

His nerves only increased as he heard some ominous movement behind him, driving up the anticipation of what was about to happen. Eventually he heard a loud pop making him yelp slightly. It was followed by something cool and slippery being dropped right on his puckered hole as Rosa held his butt cheeks apart. Soon thereafter Sora felt something cold and hard against his bottom making him squeal once more. With a little bit of pressure and a loud grunt from Sora, the well lubricated plug made it’s way up his well lubricated bottom.

It felt weirdly full, not too bad at all, the small smooth object hadn’t had much trouble invading his virgin hole, the lube more than enough to easily overcome all resistance his hole could put up. It was small enough to just be noticeable without being painful or uncomfortable. This wasn’t so bad at all.

“There we go, all nice and plugged up. That wasn’t so bad now was it? Not at all I suppose as you are still hard as a rock. Let me take care of that for you.” Rosa said as she caught him completely by surprise, reaching one hand around his hips to grab onto his cock while her other grabbed onto the base of his plug, gently moving it in and out as she started stroking his cock.

Unable to help it Sora let out a near instant moan, Rosa’s hand on his cock felt amazing. Especially given how overly excited he had remained throughout. The toying with his plug felt weird, definitely not, bad, if anything it felt weird in a good way, but he couldn’t bring himself to admit it that he liked how it felt. Rosa much about how he thought the plug felt though, she simply moved it in and out in cadence with her other hand stroking up and down his cock. If she wasn’t going to fuck him just yet, the least she could do was toy with his ass a little, besides a plug this small couldn’t feel bad.

“Mmm there we go, honey, that feels good doesn’t it? You love how your Mistress makes you feel don’t you? How she plays with your ass and your cock. You don’t need to answer sweetie, just relax and enjoy the…” Rosa said being cut short by a loud moan as Sora ended up cumming, rather prematurely, but she decided not to rub it in. She didn’t mind all that much to be honest cause she loved doing the fucking way more than she liked taking it. Besides from the way she felt the pull on the plug while Sora was cumming she could already tell he was going to be a great fuck.

Sora on the other hand was mortified, he couldn’t believe he had came so quickly and so intensely at that, the combined sensations along with the fact that it was in fact Rosa stroking his cock were too much for him to handle. Not only that, but he had messed up Rosa’s floor as well, a few thin strands of cum, sprayed on the hardwood floor before him as he came back down from his orgasm told the entire story.

Letting the plug slide back in place Rosa gave his bottom a playful pat and spoke up. “I’m glad to see you enjoyed yourself sweetie, now why don’t you go over to the kitchen, there should be a box of wet wipes in the first drawer on your right. Take one or two and clean up your mess before it stains my floor will you.”

Blushing severely Sora instantly rushed to the kitchen to go and get the wet wipes as requested. When he returned his jaw dropped to the floor. While he was gone Rosa had taken off her skimpy dress all together and apparently she hadn’t been wearing a bra. Her full perky breasts were on full display and so was her well maintained flat stomach, she looked stunning yet somewhat scary with the huge cock sticking up from between her legs.

“When you are done cleaning the floor, I have something else that could use some cleaning. I was thinking about a good tongue polishing maybe.” Rosa smirked as she used one of her well-manicured fingers to push her cock forward a little solidifying her point. Sora just blushed making quick work of cleaning the floor, returning to the kitchen to drop the dirty wipes in the trash before going back to Rosa, the plug felt so strange while walking. It brought more of a wiggle in his awkward unsteady step.

Right when he returned Rosa opened her legs wide as an invite for him to go and sit right between them. He felt awkward doing it, but he did anyways. Soon he found himself within inches of her cock once more. While he had sucked her off before, he remained pretty much as reluctant as before. There was just something so intimidating about being so close to such a big cock.

This time, strengthened by knowing he was okay with this and strengthened by the fact that he had willingly become her sub, Rosa wasn’t as patient anymore. Moving a hand to the back of his head she drew him in closer to her cock. “There we go sweetie, just open up and take as much of it as you can. You do want to please your Mistress don’t you?” She said more demanding yet sweet.

Sora didn’t put up any resistance, he just opened his mouth as ordered and let Rosa guide him down on her cock. He nearly instantly got a taste of her precum already pearling on the tip. It tasted slightly subtler than the taste of cum still in his mouth from her last load. All went well until the tip of her cock hit the back of his throat. It made Sora gag and try to pull back, but Rosa kept on pushing.

“I’m sorry sweetie, but one requirement for being my sub is to take all of my cock, don’t worry though, you get enough practice.” Rosa giggled as she pushed down while bucking up her hips to drive her cock all the way down his throat making him gag violently. She did so five times before easing up and letting him set the pace.

“There we go, a little practice each time and you’ll learn to deepthroat in no time. I won’t push you anymore, now it’s your turn to set the pace.” She said gently stroking the back of his head as the shocked Sora slowly recuperated, bobbing his head up and down about half of her cock which was what he could comfortable take. Throughout sucking her cock he was very aware of the hand resting on the back of his head, afraid it would push him down again, but it didn’t. It just stayed there gently stroking his head.

After a little while of sucking at his own pace, getting Rosa to moan pretty loudly Sora started to think about what she had said. If she really wanted him to be able to deepthroat her then maybe just maybe it would pay off if he tried forcing himself a little, it would also help making the exercise Rosa had given him at the start easier in the future.

Trying his best he tried forcing Rosa’s cock down a little further than really comfortable It made him gag lightly, but the more intense moan he got from Rosa was great encouragement. Looking up at his Mistress he blushed, very pleased with himself as he saw the love drunk eyes looking down at him past her amazing breasts. She might have a cock, but she was such a great woman. “You’re so very cute like this, the best Christmas present I could have ever wished for.” She spoke between loud moans as she gently stroked his hair.

This carried on for a while until all of a sudden Rosa’s moans and she herself grew to a climax. It all happened so fast all of a sudden, this time without warning Rosa held the back of his head very tightly, not letting him back up. What followed was a first jet of cum filling his mouth, rapidly followed by a second, a third,… By the time her orgasm stopped and she eased her grip Sora had a mouth full of cum. It was kind of shocking, but also not that surprising, he had known this would probably end in a mouth filled with cum.

When he tried to pull off of Rosa’s slowly softening cock he was halted however. Her satisfied face turned into a playful smirk as she spoke. “No sweetie, you can’t pull away until you swallowed, you should be grateful for your tasty present.”

Blushing fiercely Sora did as instructed and swallowed Rosa’s entire load this time. Feeling him swallow got another load out of Rosa, but finally she did let go of his head. “Mmmm that was so very good baby, why don’t you go and get yourself another present from under the tree? You’ve earned it.” Rosa exclaimed, deeply satisfied.

Scrambling back to his feet Sora returned to the Christmas tree, picking out another present of the dwindling bunch. As he carried it back to her Rosa patted her lap, signalling him where she wanted him to open it. With a blush he sat down across her lap and started unwrapping his present while Rosa supported his back gently stroking his thigh with her free hand.

With the packaging removed Sora was right back to blushing. Inside the package there was a dildo in a clear plastic box. It looked slightly familiar for some reason. “Here you are sweetie, a perfect replica of my cock for you to enjoy. If you go back to university we’ll probably have to miss each other for a while, but like this I’ll always be with you, besides, it’s good practice.” Rosa explained with a wink.

She then pointed to a certain package and said. “Now why don’t you bring that one over next?” It was said in a tone that made Sora fear for it’s contents. Just like all his presents so far he guessed this one would be rather sexual. Taking place on Rosa’s lap again opening up the present he was a bit confused to see a whole array of straps with a ring in the middle.

For this one Rosa’s explanation was very necessary, but when it game Sora’s blush only grew fiercer. “This sweetie is a strapon harness, the dildo I just gave you fits inside that way you can still experiment with whomever you like without having to cheat on me. You could let them fuck you with my cock.” Rosa said with a wink before bursting into giggles.

“I mean I don’t want to spoil your potential experimentation phase, but that ass is mine. If I’m right and you are going to enjoy anal as much as I think you are then this one will come in handy, besides you already told me you weren’t into men so a dick you know is better than a generic plastic cock isn’t it? Of course you can still fuck who you want when I’m not around, you have my permission, all I ask is that you do so safely.” Rosa said reaching under his skirt and cupping his cock.

“In fact why don’t you go grab that present over there next?” She said releasing him and pointing to yet another present. Sora didn’t really know what to think about what she had just said. It was somewhere a relief that he would be free to do as he wanted when he was so far away from her once the break ended, yet at the same time he doubted he would make use of the privilege.

The next present turned out to be a box of candy cane like condoms. It was followed by pair of sheer white holdup stockings, hip hugging white lace panties and finally a white chiffon nighty, simple yet elegant. None of his presents were anything he ever thought he’d get, just like so much that had happened since yesterday evening. It had been a lot to process, it had been intense and yet despite all his reservations he couldn’t say that he regretted what had happened today. In fact he was very excited to see what his future with Rosa would bring.

“It’s getting late sweetie, why don’t we go to bed and have some rest? We have all Christmas break long to enjoy each other after all. You can send your parents a text explaining you’ll be spending your break with a friend tomorrow, for now just let me help you change into your nightie.” Rosa said as she slowly started to strip Sora out of his sissy elf outfit which she just dropped to the floor. Especially being helped out of the corset and the heels felt like such an amazing relief, even if he was almost sad to see his stockings go, there was something about them that just felt so good.

Luckily Rosa soon helped him into his new stockings, showing him how to put them on, a very delicate matter as far as he could tell. The panties and nightie soon followed before she took his hand and lead him up the stairs nearly naked herself, straight into the bedroom he had spied on so many times before.

“It looks much better from the inside than it does from across the fence doesn’t it?” Rosa teased with a wink, letting him know that she had known all along about his spying. It instantly made him blush the worst yet today.

“I…I…” Was all Sora was able to stammer, completely mortified that Rosa knew about his perving habits.

It just made Rosa giggle though as she quickly stepped out of her own boots and pulled him into bed with her. “Don’t you worry sweetie, I’m just messing with you, I thought it was kind of cute, besides if I really minded none of this would have happened. In any case let’s go to sleep, since I can’t fuck you just yet fun in the bedroom will have to wait.” Rosa teased as she gave him a kiss pulling him in close to her as she pulled covers over them and shut off the lights.

Sora’s mind was going crazy with thoughts as Rosa turned him around making him her little spoon. Her breasts pressing into his back, their nylon legs rubbing together and Rosa’s hard cock pressing up against his bottom. “You can take care of that tomorrow sweetie, now get some rest.” Rosa whispered, gently humping his bottom for added effect, Sora’s own cock was rock hard as well, but he guessed that would also have to wait. Not that he minded that much.

His wish hadn’t played out how he had imagined it at all, but in the end he couldn’t deny he wasn’t happy with how it had. Rosa on the other hand usually wouldn’t even try with a guy who wasn’t made up prettily on his own, but to her big surprise Sora had turned out perfect. Both of them slowly drifted off to sleep imagining how their relationship would continue.