Though as he went to sleep that night, he couldn’t help but wonder how he might look in some of the other cute dresses that were on racks in the shop, waiting to be tried on.
CHAPTER V
Quinn felt her gut turn as she stared at that message on her computer. It was from Jeremy: a man she’d heard so much about from so many different people. Now, after so many years of only existing as an elusive name, Jeremy was out looking for Quinn. He wasn’t out trying to kill her or hurt her, or even to confront her about anything serious.
But the message was still seriously concerning. How did Jeremy know to look for Quinn at Finn’s? How did Jeremy even get Quinn’s name? If Jeremy—a guy Quinn had never even met in her life—could find out her name and where she liked to hang out, what was stopping Quinn’s family from tracking her down? Was her reputation becoming too well known?
Quinn’s family didn’t know about Quinn’s secret life, which had slowly turned into her regular life. They thought she was still Michael—and she was still Michael was she needed to be, whenever her family was in town visiting, or whenever she had to make a Skype call to help her mom set up the cable box. And she had to be Michael whenever her old friends reached out to her—even they didn’t know about Quinn. And it was best that they remained oblivious to her new female lifestyle.
Quinn knew the name Jeremy from Larissa—her ex-girlfriend, from back when she was still just Michael. Larissa would always tell Michael about Jeremy—how similar they looked, how similar they sounded, and how similar they acted. It took Michael a couple of months before realizing that Larissa just wished that she were dating Jeremy. She even moaned his name during sex once, which made all future sex very awkward and uncomfortable for Michael. So he broke it off with her. “If you like this Jeremy guy so much, why don’t you just go and date him?” Michael asked.
Larissa was too angry to answer, but Michael always wondered what her answer was—or if they did end up dating after Michael broke things off with her.
In a way, it was because of Jeremy that Michael discovered Quinn. It was a normal summer afternoon and Michael got a call from a friend who had seen Jeremy at the mall. “I kept waving at you but you wouldn’t wave back. What gives?” the friend said. He sounded legitimately frustrated.
“It was my doppelganger,” Michael insisted. But the friend refused to believe it.
“The guy I saw at the mall looked exactly like you—and I mean exactly. Because it was you. I just don’t understand why you would lie to me about going to the mall.” It was a conversation Michael was unfortunately used to.
“What was I doing at the mall?” Michael asked.
“Working.”
“Working where?”
“At that clothing store next to the food court. The one with the big blue sign. I can’t remember what it’s called.”
“And you know I don’t work at the mall, right?”
“I didn’t think you did, but apparently you do. Look, man, if you’re having money troubles, you can tell me. I can help. My dad’s company is hiring and they will pay you way more than the mall can pay you.”
Michael tried again to convince his friend that he saw a doppelganger and not the real Michael, but the friend just wouldn’t believe it. But it got Michael wondering: do this Jeremy guy and me really look that similar? So Michael decided to make a trip down to the mall to investigate.
But he didn’t want to cause any trouble for Jeremy. He knew that just by showing up at the mall, he might complicate things. Maybe Jeremy’s boss would see Michael wandering around and think that he was skipping work. But more than anything, Michael didn’t want Jeremy to notice him spying.
Michael had always been terrified of confronting Jeremy. He was scared that everything his friends had told him was true: that Jeremy really was the same in every way. The thought of talking to a near-clone was a strangely chilling thought. Michael didn’t want to know what he sounded like to other people, and he didn’t want to know how he came across to his friends—because apparently this Jeremy guy didn’t just look the part, he played the part too.
Michael was even hesitant to go and see Jeremy. He wasn’t sure he wanted to know how he looked to his friends, even from afar, but the curiosity had grown too strong. It was time to see Jeremy for himself.
So to avoid being recognized, he started to concoct a disguise. He searched his basement and found a wig and an old coat. He tried both on, but he just ended up looking like a playground paedophile. So he looked around for different outfits. He found another wig, but it was for one of his sister’s old Halloween costumes. It was long and blonde, and meant for a roller derby chick costume. Michael tried it on as a joke, and then as he stared at himself in the mirror, he got an idea: he could dress up as a woman and go to the mall.
It was the perfect plan: no one would recognize him as Michael and no one would recognize him as Jeremy. At the very worst, people would look at him and think he was a tranny—but at least they wouldn’t know who was behind the makeup.
Michael had never been the shy type; so getting dolled up wasn’t a big deal. He didn’t even bother being too secretive about it. He went into his sister’s bedroom while she was on her computer and he grabbed some makeup and a few different clothing options. She didn’t even notice—or maybe she didn’t care. He returned to his room and started getting dolled up.
He started by drawing his eyeliner on thick, and then her started to darken around his eyes with a neutral eye shadow. He went dark with his lipstick, and then he played with contouring to slightly change the shape of his face, to ensure he wouldn’t be recognized. Then he wiggled his body into a muted yellow dress, which came all the way up to his throat but left his back totally uncovered. He was surprised to discover his feet would fit into his sister’s heels—as long as the toes were left uncovered (his toes hung over the edge of the shoes a bit, but it wasn’t too noticeable).
And then he stood back and looked at himself in the mirror. He was suddenly frozen and speechless. He was staring at a convincing woman—for the first of many times.
Then he noticed the time. He’d been getting dolled up for hours. It was late now, and Jeremy was probably done his shift at work. But Michael went to the mall regardless. Jeremy wasn’t at that clothing store. Now a girl was working a solo shift. Michael went into the store, just to see if he could find an employee of the month photo or something, to see if Jeremy really did look just like him.
Then the girl tapped him on the shoulder. “Are you looking for Jeremy?” she asked.
He became tense. How could she know? He stared into her eyes and tried to come up with some sort of excuse. “Excuse me?” he managed to say, straining his voice to sound more feminine. It was easier to make a girly voice than he’d expected.
“You must be his sister, right? Twins?”
Michael forced a smile. “Cousins, actually. I guess our family just has really strong genes.”
“I’d say. I can tell him that you came by—we have a shift together tomorrow morning.”
“Oh, don’t worry about that,” Michael said. “I’m just here to browse.”
The girl perked up. “Ooh, we just got a new line in that would look so cute on you. I want to buy all of it, but I don’t have the body for any of it. But you do.” She led Michael across the store to a rack of colourful dresses and skirts. And then she insisted that Michael try them all on. And for some reason, Michael tried all of them on. He even ended up buying a couple dresses and a skirt and a blouse and a handful of panties and a couple of bras, which he planned on padding as soon as he got home.
“What’s your name?” the girl asked.
“Quinn,” Michael said, picking the first name that came to his mind.
“I wish I were as pretty as you, Quinn,” she said with a warm smile. And after that trip to the mall, a day didn’t go by where Michael didn’t dress up as Quinn. Even when he was just home alone, sitting and watching Netflix, he would put on some lingerie and
a nice pair of heels, and he would feel more relaxed than ever before.
He made new friends as Quinn—some who knew he was trans and some who were either oblivious or didn’t care. Many of his friends were also trans, and they liked to hang out at Finn’s, the local gay bar. Her trans friends all liked men, but Quinn liked girls—she liked girls so much that she liked being a girl.
And being Quinn had another major bonus: as Quinn, she didn’t have a pesky doppelganger anymore.
CHAPTER VI
Quinn wasn’t sure what to do about that message on her Facebook from Jeremy, so she left it untouched, pretending as though she never received it. She tried to think of which friends could have tipped Jeremy off, and she wondered if they were out tipping other people off as well. But she knew that the only way she would ever know was by asking Jeremy—and that was a barrier she wasn’t ready to cross.
She’d been happy for the past couple of years, since she’d started transitioning into becoming a woman. After two years of hormone replacement therapy, she had small, soft B-cup breasts, and her voice was even more convincing than ever before—but she was still able to clear her throat and sound manly enough if her family was in town. She didn’t plan on going any further with her transformation—no breast implants and definitely no chopping between the legs. She liked being able to switch back and forth whenever it was convenient, even though it made some of her trans friends frustrated for some reason. And she especially liked that no one in her family and none of her old friends knew about her secret feminine life.
But that was all at risk now.
She did her best not to think about it, but her best wasn’t good enough. Those fears constantly crept into her head: the image of her mother’s face when she realized her only son gets dolled up and hangs out at the local gay bar.
It was earlier than usual when Quinn decided to venture down to Finn’s to have a drink, to take away some of the anxiety that had been tormenting her all daylong. Finn’s was surprisingly busy considering it wasn’t even 8:00 PM yet. Quinn went straight to the bar and ordered a stiff drink. She didn’t recognize the bartender—probably a girl who ended her shift before Quinn’s usual arrival. But apparently the bartender recognized her. “It’s Quinn, right?” she said.
She was a petite blonde with a cute smile and a jet-black choker around her neck. She had a teenaged look to her, but at the same time she seemed impressively mature. “Yeah,” Quinn said. “How did you know that?”
The little blonde giggled. “I know you,” she said. “Well, I know of you. Everyone talks about you, and I’ve seen you around here before.”
Quinn’s stomach turned and she felt her face turning pale. It was exactly what she didn’t want: people talking about her. She was comfortable with her secret little life. She didn’t want to have it ruined. “Oh. Hopefully you’ve only heard good things,” Quinn said.
“Basically just how pretty you are,” the little blonde said. “I’m Katie, by the way.” She reached her hand over the bar and then Quinn noticed the tattoo on her wrist: a little Chinese symbol inside of a dark box. She’d seen that tattoo before, on a little blonde young man who frequented the bar.
“I’m sorry, I know you,” Quinn said, still looking at that tattoo.
Katie looked down at the tattoo and then back up at Quinn. Her cheeks were red now. “Yeah. I’m trying out something different. Kind of inspired by you, actually.”
“Really?” Quinn asked.
And the girl’s cheeks turned even redder. “Yeah. What do you think?” She stepped back from the bar and did a little spin. Her short skirt lifted gently up into the air, briefly teasing her bum. Her legs were perfect and her figure was cute. But her bust was too big for her small frame.
“You look really cute.”
“Thanks,” Katie said, blushing even more. She went to pour the drink. “I hope you don’t mind me saying this, but I’ve always had a bit of a crush on you.” She poured a second drink and then slid one of them towards Quinn. She lifted the second drink up. “The first one’s on the house. Cheers.”
Quinn downed her drink. The little blonde bartender did the same. The drink was far stronger than Quinn was expecting. She nearly spat it out across the bar, but she managed to hold it down.
“I put in a little extra vodka to give it some kick. I hope you don’t mind,” Katie said as she went to pour a second round. She made the second round just as strong. But Quinn didn’t mind—it was exactly what she came to the bar for. The girls had their second drink together and then Katie went to pour a third round. “Hell, that round was on the house too. Just don’t tell anyone.”
Quinn spent the next two hours at that bar, only leaving occasionally to use the bathroom. It wasn’t even 11:00 PM when Quinn could feel the liquor softening the muscles in her legs. She wobbled slightly and couldn’t quite walk in a perfectly straight line. Katie was suddenly beside her and there was a new bartender behind the bar. “I would love it if you could give me some pointers,” Katie said. “I just love the way you do your makeup.”
Quinn smiled and felt Katie’s hand in hers. She knew that this Katie chick was trying to pick her up, but she didn’t mind—until they were back at Katie’s place and Quinn remembered that Katie wasn’t actually a woman. She was a little blonde gay man—though Quinn knew that she wasn’t one to judge.
She’d never been with a man before—she’d only ever been with biological women, even as Quinn. She’d never felt a cock that wasn’t her own, and she wasn’t sure she wanted to. But now she was tipsy and feeling experimental. And she didn’t want to let her little blonde friend down. But first, she showed Katie a few makeup tricks, which was hard with her blurry liquor vision.
“I’ve got this little dress that would look so cute on you,” Katie said. “It’s too big on me, but it would be perfect on you.”
The girls ended up in Katie’s bedroom. “Get undressed and I’ll find it here,” Katie said as she dug the little dress out from her closet. She handed it to Katie and Katie immediately noticed that it wasn’t the kind of dress a girl wears outside of the bedroom. It was a lace and satin babydoll that wasn’t even long enough to cover Quinn’s bum. But Quinn put it on regardless. Katie laughed.
“What’s so funny?” Quinn asked.
“You aren’t supposed to wear a bra under it,” she said. “Or panties. It’s a standalone outfit.”
Quinn looked down and knew that without her bra, her tits would be plainly visible. And without her panties, her cock would be there for Katie to see. But she had a feeling that’s exactly what Katie wanted. So she played along. She turned around so Katie could unclip her bra and then she shimmied it out from under the tight babydoll. Then she bent over and slipped off her panties. She took a deep breath before turning back to face Katie.
Katie’s face lit up and then it turned dark red. “You look good,” she said, her voice cracking slightly. There was a long silence and then Katie stepped forward, putting her hands on Quinn’s hips. “I hope you don’t think that I just brought you here to sleep with you,” Katie said.
“That’s exactly what I think you did,” Quinn said.
“Well then I hope that you don’t mind,” Katie said, her cheeks turning an even darker shade of red. She leaned forward and kissed Quinn on the lips. The kiss only lasted about ten seconds, and then Katie started to lower herself to her knees. She lifted up the short skirt of the babydoll and then she slipped her fingers around Quinn’s cock. She began to suck Quinn’s flaccid member, making it wet and hard.
And Quinn wasn’t sure how to feel. A biological man was sucking her cock, and she liked it. But would she like it if that biological man wasn’t dolled up and wearing a cute blonde wig? Probably not… Or maybe she would like it just as much. She reached down and gently cradled Katie’s head. She began to gently thrust her cock in and out of Katie’s mouth. And then she noticed Katie’s throbbing erection pushing out from her little dress.
Quinn had never been pe
netrated before, but she was a woman and she always thought that getting penetrated should be a sort of right of passage. Katie wasn’t too big—at least she the throbbing bulge between her legs didn’t look too big—so she thought that Katie might be the perfect first penetration. Quinn had never sucked a cock before either—but shouldn’t that be a right of passage too?
“You’re so big,” Katie said, looking up at Quinn as a strand of saliva connected her bottom lip to Quinn’s throbbing tip.
“Lay back,” Quinn said.
“What?”
“Lay back.” Quinn’s hands were trembling and her heart was pounding. She was about to do something that crossed a line she never thought she would cross. But there is a first time for everything…
Katie laid back and pushed her legs out straight. Quinn came down on her slowly, sinking low and gently pulling that skirt up to expose her throbbing cock, which had already slipped out from her tiny thong. It wasn’t a big cock, but it was a cock, and Quinn was always reminding herself that she wasn’t gay. But it was hard to remind herself now as she gently slipped her fingers around that warm girth.
She gently began to pump the cock, eliciting a soft moan from Katie’s lips. The cock didn’t feel nearly as strange as she’d expected. It wasn’t gross either, which was a pleasant surprise. It just felt like another part of Katie’s pretty, little body. So sucking it should have been no different than sucking one of Katie’s fingers, right?
Quinn took a deep breath and closed her eyes. She leaned forward and then felt the tip of the cock press against her lips. She became tense and still for a moment. Then she bit down hard on her tongue and opened her mouth, allowing that cock through her soft lips. She sucked. And she only sucked for a couple of minutes before she could taste the sweet tinge of Katie’s pre-cum. Katie had her fingers in Quinn’s hair, massaging her scalp as she squirmed and moaned. And Quinn thought it was kind of nice, making someone squirm and moan like that. It was far more satisfying than she’d expected.
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