Going Girly for Christmas

by Chloe Cummings

  Chloe Cummings

  Going Girly For Christmas

  Copyright © 2019 by Chloe Cummings

  All rights reserved. No part of this publication may be reproduced, stored or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise without written permission from the publisher. It is illegal to copy this book, post it to a website, or distribute it by any other means without permission.

  First edition

  This book was professionally typeset on Reedsy

  Find out more at reedsy.com

  One

  The Gift

  ‘I wondered…,’ she started, ‘If for Christmas this year, your gift could be that you would let me try sleeping with a woman?’

  I was upset, of course, and hadn’t responded very positively. In fact, I might have even been outrightly mean about it. When I cooled off from the initial shock of the question, I realised that I needed to make it up to her.

  I wasn’t comfortable with her sleeping with someone else. We weren’t that kind of couple. It was fine for people who were like that, I’d never hold anything against them, but I had always thought that Sarah and I had been (and always would be) completely monogamous.

  I had, however, recently heard news of a service that would maybe solve this problem. This service took in men to get completely feminized, all the way from the shape of their faces down to the appearance of their genitals. Of course, such a drastic service cost a lot of money - but I had a secret: I had, unbeknownst to Sarah, been saving up money for us to get married (not that I had proposed or anything yet). Using that secret fund, I had enough to get feminized for the holidays, and then turned back shortly after. Nobody else would be any the wiser.

  I had never even considered that I would ever do anything like this. It wasn’t something I was particularly into. However, if it meant that Sarah could fulfill her wish to have sex with a woman without actually needing to cheat on me, then I would do it. I loved her enough for that.

  I told Sarah that I would be away on business for a couple of weeks leading up to Christmas Eve, but in fact I was undergoing the feminization program. I told her that I was going to miss her so much, and that when I got back, I wanted her to be ready for me to scoop her up to the bedroom for a marathon session. Little would she know that it would be her wish coming true.

  * * *

  I awoke at the end of the week. The process was finally complete, and I was actually becoming conscious enough to see the impact of it. The doctors, after checking that everything had been successful, left the room, for me to get “acquainted with my new body”.

  When I first looked down, my mind was overwhelmed with new senses.

  Locks of long, flowing brown hair fell to my shoulders as I moved my head, and I could feel the ends of them gently tickling my skin.

  On my chest, two substantial, perky, breasts hung down with a weight I had never experienced before. The nipples at their ends firmly protruded, like a little cherry on the top of a cake. As I gently swayed from side to side, so too did they. I understood, for the first time in my life, why you might want to hide your bosom away in something like a bra - there was a significant weight to them that needed supporting.

  But strangest to me of all was the lack of a penis between my legs. Now there was nothing hanging down there, instead replaced by a simple crease, two small mounds at either side. Just looking at it made my heart race, and I resisted the temptation to touch it.

  In the corner of the room was a full length mirror. I approached it, as I assumed many men had before, and got my first look at my full form.

  What stood out, most of all, was my face. In this female form, it was beautiful. My once bearded, full chin, was now thin, slight, lending the shape of my face an almost angelic feel. My thick, previously broken nose, was now a tiny button nose, little nostrils at the bottom. And my mouth was perhaps the most perfect feature of all. Full, pursed lips shone back at me, matching the rest of the face to a tee.

  Below, my figure was now slight too. My waist was now thin, giving me a stunning hourglass figure which I knew would be the envy of other girls. My hands, and feet, too had been shrunk down to match my new size. I flexed my fingers curiously - it was a weird sensation to have them so (relatively) small. Turning around to look at my rear, I was presented with a firm, round ass - the kind I always dreamed of touching, but maybe not of owning. Below that, I had long, thin legs - the type I would normally have had to pretend not to notice, or risk offending Sarah. But now that they were my own, I could stare as long as I liked…

  As I looked in the mirror, I couldn’t help but think it: I was an angel of a woman. Sarah was going to love this.

  Surveying my body once more, my eyes lingered on my crotch. A big part of me yearned to touch those folds, feel what it would be like to orgasm in this form, or, failing that, even just be pleasured. I resisted: Sarah, I was sure, would show me all of this later, and this public setting wasn’t quite the right place for it.

  Putting the charge on my secret credit card, I left the feminization studio, and went to make my next purchase: clothes.

  * * *

  I couldn’t just turn up like this, of course. I was still wearing my old loose t-shirt, as well as baggy jeans which didn’t really fit me and I still had to hold up. This was not how I wanted Sarah, my love, to see her new gift.

  There was a shop in town that my girlfriend always liked shopping at, so I went there. I figured, when this process was reversed, she could then always keep whatever I purchased to wear for this week.

  Arriving in the store, my instinct was to head straight for the t-shirts and jeans. That was what I would feel most comfortable in, after all, especially considering my body was so foreign to me right now. Instead, I forced myself to walk over to a section full of beautiful dresses, which I knew was what she’d prefer to see me in.

  A young male shop assistant glanced at me, and then looked away, blushing. I was confused at first, until I looked down, and noticed the tips of my breasts protruding from my t-shirt, which was tight around this area if nowhere else.

  I blushed, embarrassed, and headed straight for the underwear section instead. A bra, at least, would make me a little more comfortable… and my nipples a little less prominent.

  I browsed through item after item, slowly learning how they could differ so much. Suddenly, I saw a lingerie set that I could only dream of seeing Sarah in. A tiny black lace bra-let hung above a little lace thong - a set which the model on the packaging seemed to pull off so comfortably. If I wanted to see Sarah in this, then I could only hope that this was exactly what she would want to see me in. I grabbed the set matching the measurements given to me at the surgery, and quickly hopped over to the dresses section, grabbing a little black dress that I liked the look of as well as a pair of flat shoes.

  When I went to pay, I was relieved to see that the counter was staffed by female cashiers, and - hopefully - none of them would be looking at my new bust. I paid, and asked the woman if I could quickly changes in one of their changing rooms.

  She nodded at my chest with a knowing look, ‘Maybe you better.’

  Embarrassed once again, I rushed to the changing rooms and stripped off my old, male clothes.

  Pulling the lingerie from the packet, I realized just how exposing it still was… but at least I wouldn’t be making any more young men blush, with my nipples being covered.

  I slipped my legs through the holes in the thong, and slowly began to pull it up my new, silky soft legs. The lace material was unlike anything I had worn before. It felt - and I hated myself for saying it - incredible. I pulled the thong up to my new pussy and shivered slightly as t
he lace touched the mounds. A small gasp escaped my lips as I felt the soft material on the place where my cock had once been. In my behind, a small string touched my asshole, and I felt guilty for the few seconds I spent thinking it, too, was pleasurable.

  I fanned myself with the cardboard from the packaging, trying to calm myself down. How did women manage it? How did they stay so sane, when even their panties so pleasurable to slip on?

  Next, I tackled the bra. I had, at least, prepared for this, watching Sarah as she put hers on. My breasts fit in it perfectly, now supported by this silky soft material.

  I turned and caught sight of a beautiful woman, before realizing that I was looking at myself in a mirror. I was incredible to look at, even I would admit. Imagine what it would be like to have a body like this permanently. Did those sorts of women ever get around to doing anything other than checking themselves out in a mirror?

  I forced myself to look away, and instead slid into the new black dress I had bought. I hadn’t really looked at it properly when I had picked it up, as I had been in a rush. Looking at it now, on my body, I could see that I was well suited to it.

  It was low cut, but a lace mesh sat over my cleavage, almost giving it an element of mystery. The cut of the dress hugged my petite body, accentuating my hourglass figure. The bottom hem of the dress sat just a few inches below my ass - perhaps not appropriate for a formal setting, but definitely perfect for getting Sarah’s heart racing.

  I checked myself up and down once more before leaving the changing room. I had definitely done well; Sarah would struggle to resist me.

  On the way out the store, I passed a display of high heels, and I felt guilty for wearing flats. I could definitely do better if I upgraded, but I didn’t feel like I could do that, it was too far, even considering everything that I had done already.

  I shook my head, and left the mall.

  Two

  Coming Together

  When I arrived on my street, I could see the lights on in my house. Soon, Sarah passed the front room window, wearing my favorite dress of her’s - a little red velvet mini dress. I felt a stirring in my loins as I thought about what I would do to her in that thing. I bit my plump red lip as I fantasized, before finally approaching the door, hips swaying.

  I retrieved my phone and messaged Sarah. ‘Hi honey, I’m just outside. Hope you’re ready for me ;) xxx’

  I heard a ding-ding from Sarah’s phone inside as she received the text, and then scuffling as she ran for the front door.

  The door opened, and Sarah stood there in front of me. I looked her up and down. I had missed her body. That red dress hugged her thin figure, much like my own, and her long blond hair was curled beautifully, falling down past her open shoulders. On her feet, she wore high red heels, that matched her dress and accentuated her long legs.

  Sarah’s face dropped when she saw me.

  ‘Oh, I’m sorry, I was expecting someone else,’ she said.

  ‘No, Sarah!’ I announced, ‘It’s… it’s me, Mike.’

  Sarah looked at me, confused.

  ‘I got myself professionally feminized, at that new service. Just for the holidays, then I’m going back. I’m… I’m your Christmas gift!’

  Sarah’s mouth dropped as she recognized me in my new, girly form.

  ‘Oh my god, Mike? You look…’

  ‘Do you…,’ I started, ‘Do you like it?’ I braced myself in case her reaction was about to be incredibly negative.

  ‘You look… incredible!’

  Still her mouth hung open, but she stepped aside to allow me inside our home.

  I walked into the hallway, and turned to face her. As I did so, I noticed her checking me out, staring at my ass while she bit her lip.

  ‘You look… oh my god…,’ she kept repeating, over and over, absolutely floored. ‘You did this for me?’

  ‘Well… who else would I do it for? Not like I’ve been secretly wishing for this all this time, is it?’

  ‘Honey, I love you so, so incredibly much, that you’d do this for me. And you look… you look so incredible, too! I’ll…’

  She trailed off, fanned herself to cool down. I could see her face growing red.

  ‘I’ll pour us some drinks, shall I?’

  She gestured for me to lead the way to the kitchen, and I felt her gaze on me from behind as it swayed left and right with my legs. A bit part of me really enjoyed it.

  Sarah removed a bottle of Sauvignon Blanc from the fridge, and poured two glasses.

  ‘Oh…,’ I started, ‘No whiskey for me?’

  Sarah tutted. ‘Of course not. Whiskey’s not exactly a girly drink is it? No, it’s wine and cocktails for my beautiful girlfriend from now on.’

  I wasn’t quite sure I enjoyed being called “girlfriend”, but I said nothing.

  Sarah went quiet, just continued looking me up and down with an expression of intense desire on her face.

  ‘Oh, fuck it. I can’t pretend any more,’ she said, and then grabbed me by the waist, pulling me close. ‘I can’t help myself any more, I need you. I need you right now.’

  She put her lips to mine and we began to make out, more passionately than we ever had done before. My hands moved up and down her body as I felt her up, and she did the same to me.

  Sarah put her hands through my hair, held my head as she forcefully kissed me, her tongue making its way down my throat. Slowly, her hands began to move across my body, first to my breasts, which she squeezed firmly, and moaned while doing so. Then, her hands made their way down to my ass, where she began again to squeeze, and I enjoyed her using my body in this way. I could feel my crease becoming wetter and wetter as Sarah played with my new form.

  So incredibly horny now, and about to beg for Sarah to take me, she started to move her hands again. This time, they moved around my waist, towards the hemline at the front of my dress, and she began to lift it up. Just as I could feel her fingertips brush my crease, she suddenly pulled away.

  ‘What’s wrong?’ I asked.

  ‘There’s just…,’ she held up her index finger to me, ‘One more thing I need before this fantasy is complete.’

  Sarah rushed upstairs, and I was alone in the kitchen. I couldn’t help but think of my pussy, soaking into my thong. I slid my hand down my side, and pulled up the hem of my dress. With my other hand, I hesitantly touched my vulva and immediately moaned as a wave of pleasure overcame me.

  Instinctively, I put a hand over my mouth, hoping that Sarah hadn’t heard the noise. When I heard nothing from upstairs, I continued, touching it more confidently now, starting to rub at my clitoris as I had Sarah’s so many times before. The pleasure was unlike anything I had ever had before, and as I rubbed, I moaned, as quietly as I could.

  Footsteps from upstairs. I quickly pulled my hands away from my crease and smoothed my dress down. As Sarah turned the corner, I scratched at my head nonchalantly, hoping that she wouldn’t know what I had been going. A sly smile on her face suggested that she absolutely did know what I had been up to.

  In her hands, I noticed she was holding something: a pair of six inch stiletto shoes.

  ‘Here,’ she said, ‘Put these on.’

  ‘I…,’ I began.

  ‘Please!’ Sarah pleaded, ‘I know you’ve done so much already, but this really would make everything perfect.’

  I looked her in the eyes, and she clasped her hands together as she begged. I couldn’t say no to those beautiful blue eyes.

  ‘Ok, fine,’ I said, and took the shoes from her hands.

  Wearing high heels was a very strange sensation, that, I thought, definitely took some getting used to. Sarah signaled for me to spin around, and I did so. I tottered around on these heels, and caught my reflection in the mirror we kept on the back of the door. If my legs looked good before, they looked otherworldly now, the added height making them look like they never ended.

  I teetered back over to Sarah, and let her put her arms around my waist once again. Silently, she led me
upstairs to our bedroom, and began making out at the side of the bed.

  Suddenly, Sarah pushed me onto the bed. Being weaker in my new body, I was unable to resist as she pinned me down by the wrists and began to kiss at my neck.

  ‘Dress…’ Sarah commanded through deep breaths, ‘Off.’

  Before I could make an attempt to do as I was ordered, Sarah was already doing it for me. She grabbed me, forced me on to my front so she could undo my zipper, and then pulled the dress over my head. When she saw what was underneath, she froze, in stunned silence.

  ‘You like?’ I prompted.

  As an answer, she began to kiss me once again, even more forcefully than before. I tried to remove my shoes, but Sarah slapped my hand away.

  ‘No! Those stay on, you little sexy minx.’

  Sarah removed her panties from under her dress, and moved up the bed to sit on my face. This was nothing that we hadn’t done before countless times, except… she faced my legs, bent over, pulled my thong away from my slit, and began working on me too.

  We both moaned in ecstasy over the next few… minutes? Hours? Who could keep track of time when you were in heaven like this?

  As Sarah worked on me more and more, I found myself increasingly unable to concentrate on eating her out. Instead, more of my time was being spent moaning into her, screaming for more.

  Eventually, she accepted that invite, and moved her crotch away from my face, so that I could instead concentrate on receiving this incredible pleasure that she was giving me.

  When we had been going for hours, we finally stopped for energy, laying next to each other on our bed in different states of undress. Sarah, still wearing her velvet dress (but nothing underneath) was panting with a grin on her face. I, on the other hand, wore only the stiletto heels that Sarah had commanded I keep on. I couldn’t help but feel sexy wearing only the shoes.

  Sarah turned to face me, resting her head on one hand as she gazed at me.

  ‘You know… when I said I wanted to have sex with a woman, you didn’t have to make it the hottest woman on the planet.’