by D. L. Savage
“Think we’ll have to give you another shave, darling, and maybe a face mask too.”
“Sure,” I replied, giving myself up to the process and totally trusting her judgment.
She stepped back to consult with another woman for a moment, and then they both set to work on me, first shaving my face then applying the facemask which had to be left for a few minutes. While it was doing its job, Candy asked me exactly what kind of a look I would like.
“Something cute and fresh? Or maybe sexy and vampy?”
“I really don’t know,” I said, with a shy shrug. “I trust you to do whatever you want.”
“Okay then!” she chuckled. “I think I have an idea or two!”
Once the facemask was washed away, she and the other woman went to work – first applying foundation and then some rouge and other powders to my cheeks before focusing on my eyes, using all kinds of pencils and brushes. I didn’t even really know what they were doing to be honest, never having paid much attention to makeup before – even when Jenny was doing hers – but I vowed to pay more attention in future, maybe even learn a few of these magic techniques myself.
In what felt like no time at all, they were finished.
“Okay, what do you think?” Candy asked me excitedly.
I’d had my eyes closed for the final part, so that they could attach fake eyelashes, and when I opened my eyes and stared into the mirror I felt like I was looking at a total stranger. It was the weirdest sensation. Because there in front of me was ... a girl. A sexy girl.
“Wow,” I gasped.
They’d applied the make up in such a way to make my face look slimmer and more feminine, drawing on subtle shadows around my cheeks and really bringing out my eyes, which looked so big and brown now. And my lips looked full and were done with a sexy pink gloss. I couldn’t help but pout at myself, admiring my totally new face.
“I love it,” I smiled.
“I’m so glad,” Candy laughed. “I was worried I’d gone a little too far, but you have such great cheekbones, I really wanted to accentuate them ... Now, we just need to find your brand new hairdo!”
She took my hand and helped me out of the seat, and as we walked over to the wig counter, I found myself subtly trying to copy the way she walked, one elegant foot in front of the other, back straight, shoulders back. It no longer felt right to walk like I had been – just slouching around like a guy. No, now I wanted to be elegant and sexy, to suit my brand new face.
“And who’s this gorgeous little thing?” the big buxom woman at the wig counter asked Candy.
The two women turned to me expectantly, waiting for me to introduce myself to them.
“I’m ...” I began, then stopped.
It didn’t feel right to say my real name (Henry) anymore, because ... Well, I just didn’t feel like a Henry. And there and then I knew I needed a brand new name.
I don’t know where it came from, but I just opened my mouth and out it popped: “I’m Hailey,” I said, somewhat shyly.
“My,” the large friendly lady laughed, looking me up and down, “what a pretty name for such a pretty little girl!”
And again, I felt a flush of pride at the simple compliment. Yep, I was really and truly enjoying this.
“I think I have just the thing for you!” the lady continued, turning and taking down a glossy auburn wig, with flowing curls. “Try this on for size.”
I let the two women fit the wig onto me, primping and preening it, and it felt so strange as the long silky brown hair flashed against the tingling bare skin around my neck and shoulders.
“So ... What do you think?”
They gestured towards a long mirror in the corner of the store, and I walked up to it nervously. But I had no need to be nervous. It was amazing. Again I couldn’t help but smile and pout as I checked out my new image there in the mirror. The wig suited me way better than I could have ever imagined, making my skin look even paler than it did already, the russet color really complimenting the daring black cats-eye eye shadow that encircled my big brown eyes perfectly.
“Gorgeous,” Candy whispered playfully in my ear. “You’re a real little sex-kitten, you know that?”
I giggled as she nudged me in the ribs.
“Now let’s get you all dressed up, what do you say?”
I nodded happily, letting her once again take my hand as she led me over to the other side of the large room – to the pretty dresses and shoes and lingerie.
“Now d’you have anything particular in mind, Hailey, or do you want me to choose a few things for you to try on?” she said gently when we arrived.
“I’d like you to choose,” I said, glad to give myself up to her expertise.
“I was hoping you’d say that,” she laughed. “Oh I’m having such fun!”
“Me too,” I giggled.
“Now you run along to the changing rooms over there, there should be plenty of stalls free, and I’ll be along in a little while with some pretty things for you to wear!”
* * *
As I waited in the pastel pink changing room for Candy to return, I looked around me and listened to the soft sexy music that was playing, my whole body tingling with anticipation. There was a large mirror on the wall opposite and on one wall was a mysterious little slot, like you might put a coin into it. Next to the slot was a small rectangular panel, the same pastel pink as the rest of the walls.
But most of the time, I just checked out my brand new reflection, feeling so girly and sexy and feminine – my beautiful new face and long silky brown hair framing it. Now I just needed some clothes to complete the picture!
I’d given Candy my waist and shoe size and she’d assured me she would take care of the rest.
Just then I heard a friendly knock on the door. I padded over and opened it and there was Candy, carrying a whole armful of colourful clothes.
“Here you go, sweetie!” she said, handing them over. “You want a hand trying them on, or should I just leave you to it for a little while?”
“I think I’m good,” I smiled back, realizing what I wanted most was a little time alone now.
“Sure thing,” she grinned. “Oh, and one more thing,” she added, leaning in close, “take this.”
She handed me a mysterious little pink token.
“Just in case you want a little somethin’ extra,” she added with a playful wink. “Okay, you have fun now! Take as long as you like!”
And with that she left me alone, closing the door behind her, leaving me there in that pretty pink room with a whole armful of fun new clothes to try on. I started looking through them – a silky white blouse, a navy pencil skirt, a pair of dangerously high looking stilettos in a shiny black. But my eye was caught by a sexy slinky pink dress that looked like it would cling to my body. There was also a padded bra and a pair of cute thong panties – both in a rich silky purple.
I felt another shiver of excitement as I shook off the robe, uncovering my freshly waxed and clean body beneath.
First I pulled on the thong panties, once more feeling the strange yet pleasurable sensation of the fabric sliding between my butt cheeks and cupping against my balls and cock, leaving a thick bulge at the front.
Next I clipped on the bra around my waist, the way I’d seen Jenny do sometimes, before sliding it up and around, hooking my arms through the straps, the padding giving me the appearance of having a small yet perky pair of breasts.
I checked myself out in the mirror – wow. I felt a strong flash of excitement at my sexy new reflection and soon I could feel my cock growing and swelling, the bulge getting larger in the panties, but the stretch fabric still containing my cock.
Finally I pulled the sexy pink dress over my head, sliding the clingy fabric down over my body, smoothing and pulling it into place.
My new look was complete.
I was no longer Henry – no way. There in the mirror was a brand new girl. Sexy and slinky, fun and playful, a naughty little smile on her full, sensuous,
glossy lips. There in the mirror was ... Hailey.
Then I remembered the mysterious little token that Candy had given me. I glanced down at it, sitting atop the remaining pile of clothes. I figured it must be for that slot in the wall. Perhaps when I put it in it started a light show, or maybe turned the mirror into a TV or something.
I remembered Candy’s words: Just in case you want a little somethin’ extra ...
Whatever did she mean?
Figuring there was only one way to find out, I nervously approached the coin slot and dropped the token into it. There was a soft bell sound, a pause and then a mechanical whirring sound, as the rectangular panel slid away leaving a hole in the wall at about waist height. And as I knelt down before it to peer through and try to figure out just what the hell was happening, something happened that I really didn’t expect.
Because all of a sudden, a big black cock came sliding through the hole, right towards me.
* * *
I almost fell back in surprise, staring in total shock at the sight of the cock, poking through the hole – jutting upwards, totally erect, the head glistening in the dim light, the shaved balls tight and full beneath. For a moment I thought it was maybe some kind of toy, but by the sheer heat I could feel coming from it, radiating in waves towards my face, I knew for sure that this thing was real.
I didn’t know what to do, as I knelt there, staring at this thing.
I mean, part of me was more than a little curious, but at the same time I had so many other thoughts and emotions running through me.
If I touched it, did that mean I was gay?
What if someone came in and saw me?
But then my thoughts turned to Jenny too. I didn’t want to betray her trust, but at the same time, wasn’t she probably playing with the cock of a big hunky stripper right this moment, too?
It was so confusing.
And then my glance was distracted by my reflection in the mirror – it didn’t even look like me. I wasn’t me anymore. I was Hailey. And what Hailey wanted was to touch this thing, to reach out her fingers and stroke it, to feel its smooth silky warmth.
I took a final deep breath, then turned my focus back towards the dick, which was still totally hard, jutting up as if ready for me to play with it.
I reached out my hand and softly clasped it in my fingers, registering first just how damn hot it felt, then how hard. It was easily twice as large as my own dick, which was still snug and tight in my thong, and as I began to slowly stroke the cock, I felt my own cock tingling with pleasure too.
And the more I stroked it, the harder it seemed to get, if that was even possible. Soon I fell into a rhythm, lost in the sensation of simply kneeling there, dressed in my sexy tight fitting dress, stroking this big black cock. With my other hand I began cupping the balls too, softly massaging them, feeling their snug weight in my palm. And before I even knew what I was doing, I’d spat on it, in order to give my stroking hand a little more moisture – just the way I’d seen sexy slutty girls in porn do.
I licked my lips in anticipation, as I realized I wanted to at least give it a little taste too. After all, it looked so delicious, right there before me. I parted my glossy lips and stretched out my tongue, guiding the cock towards my open mouth, shivering as I felt its heat and weight on my tongue, and as I closed my lips gently around it, feeling the delicious way that big hot head totally filled my pretty little mouth, again I felt a jolt of electricity between my own legs, like some invisible hand was playing with my cock too.
With a breathy sigh, I started to suck, first slowly and sensuously then faster and faster, quickly getting lost in a steady rhythm, my lips sliding up and down the shaft, my tongue dancing against the underside of the head, the big meaty cock filling my mouth and even nudging occasionally at the back of my throat. I began to feel it pushing and pulling back too, and I realized that its owner was trying to fuck my mouth.
So I took my hands away from it, placing them either side of the hole, arching my back, on my knees, letting this total stranger fuck my willing mouth, each thrust he made making my own cock tingle between my legs, even though I hadn’t even touched it once.
As he thrust harder and harder, his big hot cock sliding back and forth between my lips, I moved my hands to my breasts, then back to my ass, feeling my new girly curves, my eyes flashing over to the mirror, and the sight of me there on my knees getting my mouth fucked by a thick glistening black cock was almost too much to take.
I groaned and shivered, feeling my own cock swelling now between my legs, still snug in my cute pink thong. I closed my eyes, lost in the sensation of that hot meaty shaft plundering my mouth, placing my hands back against the wall, feeling the cock growing even bigger and harder like he was about to explode any second.
I shuddered again. God, this felt so fucking good. And before I even knew what was happening, I started to come, without even touching myself, my tiny sissy cock squirting hot come into my panties.
And as I was coming, I heard a soft low moan behind the wall, too, and a moment later my mouth was filled with my sexy stranger’s salty creamy warmth, sending another shiver of ecstasy through me.
I groaned and shuddered, my orgasm so much stronger then I’d ever felt before, and it seemed to just go on and on, too, as the thick cock in my mouth pumped and squirted that delicious cream onto my tongue and down my throat, I could still feel my own tiny dick coming too, my panties now totally soaked through with my own warm wetness.
Finally I pulled my mouth away, swallowing back the huge creamy load, and I watched, trembling as that mysterious glistening cock slid back into the darkness, leaving me there alone, staring at myself in the mirror: my whole body still shuddering with pleasure, my makeup smeared, my silky curly hair a little mussed up, but the biggest naughtiest smile of slutty contentment on my cream-covered lips.
* * *
“You sure you don’t want to take these home with you?” Candy asked, as we stood in the lobby a little while later. She was holding the bag of clothes and my beautiful brown wig, and I was dressed once more in my regular everyday guy clothes, which now felt shabby and cumbersome compared to the slinky sexy outfit I’d been wearing just a little while previously. “After all, they are yours now?”
I was totally conflicted. Of course, I wanted to take my new outfit home with me, but at the same time, another part of me wanted to just draw a line under this experience and return to my old life – hopefully forever.
It felt dangerous, to blur the lines even further. After all, I was a married man, and even though I had this new side to me, should I really indulge it any further, at the risk of jeopardizing my marriage any further?
I sadly shook my head. “I’d better not,” I said, softly, and Candy nodded and smiled at me.
She’d obviously seen guys like me a thousand times before and totally understood my conflict.
“Well, how about this, sweetie,” she said quietly. “We’ll keep these things in a locker for you here. No extra charge. And if you ever want to come back and have a little more fun, we’ll all be right here waiting for you.”
“Thanks,” I smiled back, feeling a strange pang of sadness as I realized that my time at Sissy School was almost over.
And before I even knew what I was doing, I’d stepped forward and given her the biggest hug. She hugged me right back, obviously aware of my sadness and I had to do all I could to hold off from letting the tears trickle down my cheeks as a whole whirl of emotions flowed through me.
“You take care now,” Candy said, giving me a final little squeeze before stepping back away from me again.
“Thanks for everything,” I grinned back, just about keeping it together.
And then I quickly turned and pushed open the doors, stepping out into the parking lot, which was dark now.
As I stumbled back to my car, my brain was reeling from the experience and it quickly began to feel like the whole thing had been some kind of crazy dream. Had that really been m
e in there? And when I recalled the image of myself in the mirror – dressed as Hailey, that naughty, sexy slut, down on her knees, her glossy lips smeared with cum – it seemed more like an image from a porno movie than something that I’d actually taken part in.
I reached my car, unlocked it and climbed inside, turning on the engine and looking at the time on the dash. It was after midnight, and Jenny was coming back first thing tomorrow morning.
With a heavy heart, I pulled out of my parking space, casting one final look at that large anonymous building – again marveling at how normal it looked from the outside, no hint of the many wonders it contained – before I slowly drove home.
* * *
That night, I hardly slept. I tossed and turned, my thoughts flitting this way and that, every now and then checking the time, only grabbing a few hours sleep before the bedroom began to fill with early morning light. With a weary sigh, I pushed myself out of bed and decided to take a shower and make some coffee. It was still a few hours until I had to go to work, and I wondered if I’d catch Jenny coming home before I left.
As I pushed off my boxers and the t-shirt I slept in, and began to run the shower, my totally hairless body came as a bit of a surprise – again triggering reminders of last night, which now seemed like something from a distant fantasy. As I soaped myself, I felt a pang of guilt, and also worry that Jenny might comment on where all my body hair had gone, and why my normally hairy cock and balls were now totally hairless apart from a neat little rectangle of pubic hair. But I figured that she always kept herself shaved down there, and I’d just say I got bored and started experimenting. After all, it wasn’t like we’d even had sex that often recently – mostly likely she wouldn’t even notice. And soon the hair would grow back, and that would be the end of that.
I finished in the shower, then headed back through to the bedroom to take my suit out of my side of the wardrobe, trying to ignore the enticing view of all those pretty slinky dresses on Jenny’s side.