by D. L. Savage
Mia was studying on the same course as me, which was how we’d first met, but unlike me she seemed to be swimming in cash and glitzy new possessions. She even rented her own apartment, while I lived in the cheapest, crummiest dorm room imaginable. Maybe she had some secret billionaire boyfriend, I wondered occasionally, because in the whole time I’d known her, I’d never actually seen her with a guy – even though I knew she was straight.
I found this out the hard way, on one of our first nights hanging out together. I’d had a crush on her, and while I wasn’t exactly handsome in a rugged alpha kind of a way, girls had often told me I was ‘cute’ (even ‘pretty,’ which did little for my macho self-esteem), and so I knew I wasn’t terrible looking, at least.
And after one two many Jack and Cokes – all on Mia’s tab, of course – I leant in and tried to kiss her.
“I’m sorry, Jacob,” she’d smiled back at me, actually pretty cool and unphazed about the whole thing, “but you’re just not my type.”
“Let me guess,” I’d sighed. “You go for that whole bulging bicep, chiselled jaw, six-foot-something look, right?”
“Fraid so,” she’d grinned, her pretty blue eyes sparkling in the low light of the bar as my hopes of getting with her quietly sank away.
I knew I couldn’t even try to compare to something like that. I was skinny as a rake – always had been, no matter what I ate or how many push ups I did in my room – and my facial features were not much better. Okay, so they were symmetrical, and ‘cute’ – but they certainly weren’t rugged and manly in the way that Mia and so many other girls I met obviously craved.
After that early awkward encounter, I never made a move on her again, and instead we became really good friends. She had a great sense of humor, and as I mentioned earlier, she always picked up tab. It was a lot of fun hanging out with her, even if occasionally I got frustrated – mainly when girls assumed we were together, which was probably one of the reasons I was still painfully single, at an age when I should probably be fucking my damn brains out.
And sometimes, I got frustrated too at how easy Mia seemed to have it compared to me. It just seemed like if you were a hot chick, then things fell into place. Money, sex, the works.
And actually?
One weird night, I discovered that my suspicions were true ...
2
“So come on, Mia,” I blurted out, one boozy evening as we sat a little drunk at a bar near campus, “where the hell do you get all your money from?!”
I knew it was a little crass just to flat out ask her like that, but she’d just been showing off her brand new MacBook and I simply couldn’t keep my curiosity to myself any longer. I kinda suspected she’d tell me to go to hell. But instead, she smiled that naughty, cheeky smile of hers and said, “Guess.”
I sat back in my chair for a moment, running the many possibilities through my mind, trying to come up with the most likely one.
“You have some secret old dude somewhere, some rich billionaire who’s in love with you,” I said finally.
“Nuh-uh,” she grinned.
“Okay, your parents are loaded. They won the lotto or something?”
“Jacob!” she laughed. “You met my parents last month. Did they look loaded to you?”
I had to admit, the homely couple who’d said hi to me, that afternoon I met Mia downtown didn’t look particularly well off.
“What then?” I sighed. “Not porn?”
“Nope,” she grinned, obviously enjoying teasing me.
“Come on, please, Mia,” I groaned. “You’ve had so much money, ever since I’ve known you. Let me in on your secret. Is it something that I could do, too? You know how fucking broke I am all the time ...”
At these words, something changed in Mia’s expression, like she was really thinking about what I’d just said. Now it was her turn to sit back in her chair and mull things over. After the longest, most excruciating pause, she leant forward again, placing her elbows on the table, her voice dropping to barely more than a whisper as she said, “You really want to know what I do, Jacob?”
I nodded, feeling a strange prickle of excitement at the idea of finally being let in on the big secret.
“Then come to my place tomorrow night, eight o clock sharp and I’ll show you.”
And with that, she picked up her glass and knocked back the last of her drink, then pushed herself up from her seat.
“I should probably get some sleep,” she said, still looking at me with that weird new intensity. “And I suggest you do, too.”
She leant in and kissed me on the cheek, pausing again to look at me – as if assessing something – then gave me a knowing wink.
“See you tomorrow night,” she murmured, almost in a sexy way, then turned and strutted out of the bar, heels clicking on the marble floor.
I don’t know how long I sat there, running over the crazy turn of events of those last few minutes, my head spinning.
What the hell had just happened?
Tomorrow night was Saturday, a night – I realized then – that Mia was always ‘busy’ whenever I’d tried to hang out with her.
And there was something about her tone in those final minutes – something playful, mischievous, even a little teasing that suggested she was having fun with this, at my expense.
Mia wouldn’t put me in some totally fucked up situation, would she? I thought to myself nervously, as I finished the rest of my drink and then started to head back to my dorm.
If only I’d known back then what I was letting myself in for. Because it was stranger than anything I could’ve ever imagined ...
3
I spent all of Saturday in a weird mood, just hanging out in my room, unable to really concentrate much on anything in particular. I had essays I should be writing, and there were groceries I needed to go into town to buy, but all day I just hung around, mulling over those weird final few minutes at the bar with Mia. In my memory, it seemed dreamlike now, almost like it didn’t happen.
Did I have one too many drinks and imagine it? I started to wonder, the image of her strange smile flashing into my brain for what felt like the thousandth time that day.
But at around six o clock, a new message pinged onto the screen of my cellphone, from Mia of course: Still on for tonight? 8pm sharp ;-)
I paused before I replied, wishing she’d told me a little more information about what it was we’d actually be doing. Why the hell did it have to be like this, like some sort of weird game?
As I picked up the phone and texted back my reply – Sure, see you later – I realized my hands were actually shaking a little, like some part of me knew deep down that this wasn’t going to be normal.
As instructed, I knocked on the door to Mia’s apartment at eight pm, sharp.
I couldn’t help but feel like this was some kind of date – even though I knew the thought was ridiculous – and as such, I’d spent my last hours beforehand primping and preening in a way I never normally did, shaving, shampooing my hair, scrubbing myself for an extra long time in the shower, and putting on my best black shirt and jeans.
But when the door opened, the way Mia looked totally blew me away.
Holy shit! She looked like she was dressed to go to some awards ceremony or something, clad in the slinkiest little black dress, her blonde hair done in ringlets, her neck encased in a black choker and her face made up in vampish, smoky makeup.
“Wow, you look great!” I croaked when I saw her. I wasn’t even trying to hit on her – I was just speaking my thoughts aloud.
“Thanks,” she grinned, “Come in.”
I followed her into the apartment, unable to stop myself from quickly checking out her perfect ass, which wiggled at me as she walked, shown off by that figure-hugging dress. There wasn’t the merest hint of a panty line, and I couldn’t stop my brain from imagining the sexy thong or g-string Mia must be wearing right now beneath her outfit.
I’d always had a strange fascination with girls’
underwear. Not in some creepy, panty-sniffing way, you understand. It just seemed so ... different to what us guys wore. I couldn’t imagine what it might feel like to wear something like that, a little strip of fabric sitting between your butt cheeks all day, instead of the baggy old kinds of cotton boxers I normally wore.
It was the same with shoes, too. Right now, Mia’s feet were encased in a pair of crazily high, strappy black heels, while mine were in the only pair of beat up sneakers I owned.
The things girls did for fashion, I thought to myself with a shake of my head as I followed her towards the open plan lounge-cum-kitchen, where I noticed she’d already opened a bottle of what looked like Champagne.
“I suggest you have a drink,” she said, pouring out two glasses and handing one to me.
What the hell was that supposed to mean?! I thought, another pang of nervousness shooting through me, my frustration building again as I wondered why she still hadn’t told me what we were going to be doing this evening.
“I also suggest you take a seat,” she added, nodding to the plush leather sofas.
“Okay,” I said, hearing a jangle of nerves in my voice, as we walked over to the couches, my heart starting to drum in my chest and my head spinning a little as we sat down, facing each other.
I took a long sip of champagne, feeling the silence growing between us, as Mia just sat there looking at me, with that weird expression on her face again, until finally I couldn’t take it any longer and I blurted out, “So tell me. What is it you actually do, Mia?”
She lifted her glass to her lips and took a long, slow sip, obviously enjoying teasing me, eking out my frustration for as long as she possibly could, before she spoke.
But what she said next was something I never would have guessed ...
4
“I’m a sissy, Jacob,” she said, like it was the most normal thing in the world – like I should already know what that word meant. But the truth was, back then I had no fucking clue.
“You’re a what?” I blurted out, my head reeling.
“A sissy,” she repeated, rolling her eyes. “Do I really have to spell it out for you?”
“I’m afraid so,” I replied, still total confused.
I watched, my heart pounding, as Mia elegantly placed her glass of champagne on the glass coffee table that separated us, then got to her feet. And then, to my surprise, she began pulling up her dress, inching it up her slim, toned legs, uncovering first her black stockings, then their silky tops, and the smooth tanned skin of her thighs.
I couldn’t tear my eyes away from her, my heart pounding as the slinky dress got higher and higher, until finally she’d pulled it up far enough to uncover a pair of black silky panties.
A pair of silky black panties with a small yet definite bulge in them.
“Wait, what?” I croaked, unable to believe my eyes. “Is that what I think it is?”
At my words, Mia just giggled, reaching to her thong and casually tugging it aside to reveal a small pink cock and balls, totally shaven – as tiny as a little kid’s. I couldn’t stop staring at her junk. It looked, well, feminine even though it was obviously a dick.
“Oh my god,” I whispered, as my head span with all this new information.
Mia – the hottest girl I knew, the girl I’d even made a pass at myself was in fact a ... guy?
Suddenly a lot of things made sense. Her height. Her tolerance for alcohol. The fact that she always wore either a choker or a roll-neck sweater or a scarf or something to hide her Adam’s apple.
“So, you’re a ... a man?” I blurted out, my head still reeling.
“Oh come on, Jacob,” she sighed with a disapproving look, tugging her thong back in place and adjusting her dress once more, “I thought you were a little more progressive than that.”
“Sorry,” I murmured, feeling my face flush with heat.
It was true, I did think of myself as forward thinking, and was usually pretty careful with things like personal pronouns and so forth. But this was Mia, my friend, a person I thought I knew ...
“But I still don’t understand,” I said. “So you’re a, uh, sissy. How in the hell does that afford you such a luxurious lifestyle.”
“That’s the fun part,” she grinned, sitting back down and taking a sip of her champagne. “I had you convinced, didn’t I? You thought I was a hot chick, right?”
I nodded.
“Well, let me tell you, there are a lot of guys out there who’d love to spend time with a girl like me. A girl with a little something extra between their legs. Sure, any guy can put on a wig and makeup and call himself a sissy. But a girl like me? I’m as rare as they come.”
“So what are you telling me?” I croaked, even though I already knew the answer. “You’re an ... an escort?”
“I prefer the term hostess,” she grinned back. “But if that’s what you want to call it, then yes. I have a client base. A very carefully selected and exclusive client base, who reward me for my hospitality.”
“But I still don’t understand,” I murmured. “What does that have to do with me? Do you need a ... a bodyguard for tonight or something?”
“No silly!” she laughed, her blue eyes sparkling. “I want you to work for me. I think you’ve got what it takes, Jacob. I think you could be just like me.”
“No fucking way,” I blurted out, pushing myself to my feet, my head reeling and my heart pounding so hard it felt like it was about to burst out of my damn chest. “No fucking way in the world. That’s insane, Mia. I’m not doing ... that.”
I set my glass down with a clumsy clink on the coffee table then turned to leave, to get the hell out of there, but as I was making for the door, she called out after me, “Five grand, Jacob. Five grand, just for tonight.”
I stopped in my tracks, halfway between the door and the couch, unable to stop myself from turning back to face her, watching as her mouth curled in a grin – a grin that said Now I’ve got your attention.
“Five thousand dollars,” she taunted, hands on her hips, blue eyes blazing, “for a few hours of fun. You wanted to know what I did to make all that money? Well, now I’ve told you and I’m offering you the chance to get in on it, too. But if you walk out of that door, don’t think I’m going to give you a second opportunity. So make up your mind, Jacob. What do you want to do? Shit or get off the pot?”
I stood there, frozen, looking from the door, to Mia, then back again.
Could I really do this?
Could I really become a ... sissy hostess?
5
“But how would I even be convincing, Mia,” I said, marveling at the fact that I was even considering such a crazy idea.
“Don’t worry,” she smiled, her expression softening a little. “I’ll guide you, every little step of the way. So, you want in?” she added, with a cheeky grin.
“Maybe,” I sighed, wringing my sweaty hands together, unable to believe what I was saying.
The idea was totally crazy, no question about it. But at the same time, five grand, for one night?! That was more money than I’d made all fucking year, working any kind of shitty part-time job I could find.
“Come and sit down and let me show you something,” she said, beckoning me over.
She sat down once more on the plush leather couch and I felt myself moving towards her, almost like I was in some kind of dream – my body doing things out of my own control, like some part of me had already made the decision.
I did as she said, taking a seat right next to her, watching as she picked up her brand new, rose gold iPhone and started tapping at the screen with her fingertips, her long shiny nails making little ticks on the glass as she did so.
“She that guy?” she said, turning the screen of the phone to face me.
I stared at the photo she was showing me, of a very plain looking boy, about the same age as me, with shaggy strawberry blonde hair, a fuzz of stubble on his cheeks, and big blue eyes. He looked a little like me, in the sense that his featu
res were more on the feminine than masculine side, but apart from that, there was nothing particularly remarkable about him. He could have been anyone you might pass on the street.
“That’s me, Jacob,” Mia said. “The old me, anyway. That photo was taken just over a year ago, back when I was drab, borking old Mark — before I took the leap and became Mia full time.”
I stared again at the photo in total disbelief. Now that she’d told me, I could see it – see the same cheekbones, the same eyes, even the same shaped lips. But holy shit, she’d done such an amazing job on her makeup, on her whole look, that if you didn’t know what you were looking for, you’d think they were two totally different people.
“That’s incredible,” I murmured, an impressed smile creeping across my features.
“Thank you,” she beamed. “And you know what, Jacob? I think I could do just as good a job on you as I’ve done on myself. If anything, I think you might turn out even better. You’ve got such a pretty face. I really think you could look stunning.”
“This is crazy,” I said, my heart booming, my head spinning.
“Just let me try at least,” she said. “Come on, what have you got to lose?”
She pushed herself to her feet and offered me her hand.
I looked up at her, at the girl I’d had a crush on for the longest time, my buddy Mia, who was still stunningly beautiful, even though I now knew her secret. And there was something about her expression, something warm and friendly there, something that told me that despite everything – despite all the crazy things she’d just told me - she still cared about me too, was still looking out for me, and that she just wanted to help me, finally get me off my ass and improve my life, once and for all.
