“My daughter just turned eleven and she wants to start wearing makeup. I’m against the idea to be honest, but my wife keeps insisting that all the other girls are doing it.” He tried to force the biggest smile he could. But he felt off, as if the girl could see right through him, as if she knew he was actually looking for himself. He looked down at his plastic bag and could see a tinge of purple poking out. His heart fluttered into his stomach.
The store clerk smiled. “Well most teens wear makeup these days—and lots of pre-teens like your daughter, too. I would recommend this kit here. It’s got all of the essentials.”
“Perfect, I’ll take it,” Terry said without even looking. He was too overwhelmed, too out of his element. He just wanted to get out of there so that the embarrassment could start to subside. It wasn’t until he was back at his apartment that he realized the store clerk probably could see right through him. There were kits for sale at the makeup store that were obviously for young girls: pink kits with pictures of Barbies and whatnot on them. But that’s not what they sold to Terry. The kit in Terry’s hands now was more mature: all black with fancy gold calligraphy. The brushes were all thin and fragile-looking, and there were no instruction manuals with anything. So it took Terry a good couple of hours to figure out what it was all for, and how to put it all on. It took the rest of the night before Terry was satisfied with his new look: a smoky cat eye look with carefully filled-in eyebrows.
He never realized how blue his eyes were until he had that mascara on his eyelashes. And he’d never realized how big and stunning his eyes were either. With a bit of red lipstick, he looked like a completely unrecognizable person. “Looking good, sugar,” he said with his surprisingly sharp female voice. He caught himself grinning in the mirror before turning to his plastic bag to pull out the highlight of his night: the prostitute’s purple lingerie.
It fit nicely, and it looked good even without socks stuffed into the chest. He did a few poses in the mirror and suddenly felt a naughty sexual energy flowing over him. How many men had came on that little outfit? How many cocks had rubbed up against that tight lace? Terry reached down and ran his fingertips between his legs, feeling that well-used and well-fucked fabric. His cock was suddenly rock-hard, throbbing, and leaking.
He quickly retrieved his black steamer handle and his little bottle of lube. He was ready and excited for another round of ass fucking. But before he got the handle lubricated and in his asshole, he teased it with his tongue and pressed it into his mouth. He gave it the hottest blowjob he’d ever watched in a mirror and then he didn’t bother with the lube—he didn’t need it. His saliva was enough for his tight little asshole. It hurt just a little bit at first as he stretched wide to accommodate the faux-dildo, but after thirty seconds of thrusting in and out, it started to feel good. He wanted to make himself come again without using his hands. He wanted to fill that tight little outfit with warm jizz, and this time it didn’t matter if it didn’t come out. He could just tell Sheila he wasn’t able to salvage it—she was going to throw it out anyway. Hell, maybe then he could keep it for himself. Maybe he would just tell her it wasn’t salvageable regardless of whether he could get the cum and candle wax out.
He felt it coming. His body tensed up and a jolt of warm euphoria overwhelmed his nerves. He started squirming and trembling and then he felt his warm go splattering across his chest. “Oh God,” he groaned as he rolled onto his side, his eyes nearly rolling into the back of his head.
And then he caught a glimpse of himself in that full-length mirror, looking beautiful and amazingly convincing. He found himself frozen, obsessed with his own reflection. Was he really that convincing, or was it just a good angle? He moved and found himself mesmerized once again. The purple lingerie looked so good on him, like it was made for his curves and his perfect bum.
CHAPTER VI
Terry was beginning to scare himself. In a matter of days, he’d gone from being completely disinterested in trying on women’s clothing, to not being able to think of anything else. Every time a girl came into the shop with a sac of clothes, he would dig through it, hoping to find pretty clothes he could take home and try on. He was always disappointed when the customers said, “I need these back later today.” But still, by the end of the day, he had six sacs to take home with him—six sacs that could have been cleaned in the store, but Terry wanted to save for the privacy of his own apartment.
As he walked through his apartment door, he realized he wasn’t going to get much sleep, even if he decided not to try on the various outfits—his addiction had left him with more homework than he could handle.
But of course he spent the next few hours trying on different outfits. He put on a cute skirt and a tight cardigan while he made himself dinner, and then he ate his dinner wearing a black satin cocktail dress. He was digging through the sacs for a third outfit when he had a peculiar idea that brought him to his laptop computer. It only took a little bit of searching before he found out hormone replacement drugs could be purchased for cheap on the black market—almost as cheap as a bottle of Advil.
And then he closed his laptop hard as his sensibilities returned to him—at least for a short moment. His heart was pounding. For that short minute, he was actually considering it. He was actually about to navigate over to the Dark Net to buy himself some hormone replacement drugs, so he could have his own breasts and a softer voice and softer skin and fuller hair...
It was almost 11:00 PM and he had none of his work done. So he got started, one piece of clothing at a time. Whenever one piece of clothing had to sit on the steamer for an extended period of time, he would use that time to get changed into a new outfit. It was his eighth outfit of the night that pushed him into his bedroom where his old steamer handle was waiting for him.
It was a black satin babydoll slip, dropped off near the end of the day by one of his prostitute clients. It was soft and used and adorable, and it had a little pair of crotchless panties built in. His cock hung out from that crotch hole, and he was erect within minutes of putting the outfit on. This time, he couldn’t stop himself from stroking his shaft—and he came faster than he’d ever come before.
He finally got to sleep around 5:00 AM, just an hour before his alarm went off. So he spent his Friday dozing off behind his desk. Thankfully, there were never many clients on Fridays. And that Friday wasn’t special. Terry ended up falling asleep behind his desk around 10:00 AM and he wasn’t woken up until 2:00 PM, when one of his usual clients tapped him on the shoulder and said, “I need these clothes cleaned. They’re brand new, so I don’t want to run them through the machines.” It took Terry a moment to come back to life. He shook his head and processed the client’s words, and then he accepted her wardrobe bag.
“No problem,” he said.
She was a prostitute, like many of his usual clients, but she was one of the high-end ones, the ones that call themselves escorts. As soon as she was gone and Terry was awake again, he looked through her bag and his eyes lit up at the sight of the beautiful white dress inside. And there was a pair of white heels. Terry occasionally found shoes and jewellery in wardrobe bags, as people tried to keep their outfits together.
Terry looked around to make sure the coast was clear, and then he brought the shoes out from the bag and placed them on the ground. He tried to wriggle his foot into the left shoe. It was tight but it fit. He looked around again and then he stood up, bearing his weight on that heel. It wasn’t nearly as uncomfortable as he was expecting, though maybe he would change his mind after walking around for a few hours in the heels, which he was already planning on doing around his apartment.
There were a few hours left in his day—a few hours before he could get the pretty clothes home so he could have his fun. He had a few more clients come in with more pretty clothes, but he didn’t make the same mistake as the day before—he cleaned the clothes in the shop and stuck to the single bag he planned on taking home. If he didn’t get his sleep, he knew he would do something stup
id, like accidentally send a picture of himself in pretty women’s clothing to his mother.
It was during his final open hour that he noticed one of his clients out on the street, starting her night of work. She was only on the street corner for five minutes before a sleek black BMW pulled up and commissioned her for a job. She hopped in the passenger seat and the car zipped away. Terry’s heart stuttered as he imagined himself in her shoes—literally and metaphorically. He couldn’t even imagine how frightening and exciting it would be to have sex with a stranger, for money. He knew the girls who did it—they never seemed afraid or worried. Maybe it wasn’t as scary as it looked. Maybe it was actually fun. Terry enjoyed having sex—having sex for money actually seemed like the perfect gig.
He closed his shop down and started his trek home. He walked quickly, excited to get into the expensive and pretty wardrobe, which he also had to clean and steam before going to sleep for the night—and sleep was important. He couldn’t go another night without getting eight hours of sleep.
Terry was halfway home when he remembered it was Friday and he didn’t have to open shop until noon the next day. He had tons of time to enjoy the night—tons of time to enjoy the adorable outfits that were in that wardrobe bag.
CHAPTER VII
Terry was having fun, trotting through his apartment in the heels, feeling the soft satin against his skin. He was starting to get the little feminine mannerisms down, and his voice was getting better with each passing night. He would stand in front of the mirror and talk, sometimes for over an hour while admiring himself, trying to figure out how he could be just a little bit more convincing.
He found himself sitting closer and closer to that mirror, trying harder and harder to figure out which of his facial features were obviously male. Even his Adam’s apple didn’t seem apparent anymore. Had it ever been apparent? And his shoulders seemed so narrow—but were they ever broad?
His voice wasn’t terribly convincing, but aside from that, he was sure he could pass. But there was only one way to know for sure. He walked over to his window and looked down at the street. Groups of men and women flocked in every direction, going from bar to club to pub and back again. As Terry looked down at the street, he saw a pretty woman wearing a short skirt. A carful of men pulled up next to her and whistled. “Looking good, darling!” one of the men yelled, and then the car zipped away as faces turned red all around.
And Terry wondered what would happen if he went out on the street. Would people recognize him? Would they be able to tell that he wasn’t really a woman? Would he get catcalled like the pretty woman in the short skirt? He looked over at the mirror to decide if he was truly convincing, and then he caught himself smirking with dark red cheeks.
Maybe they wouldn’t buy him as a woman, but they certainly wouldn’t recognize him—so what was the harm? What did he have to lose? If they did buy him as a woman, and he did get catcalled and hit on, then he was only missing out by hiding out in his apartment. How could he pass up on the opportunity to show off a thousand dollar dress?
He reached for the handle of his front door, and then his heart began pounding. Why was his heart pounding? No one was going to recognize him, so why was he nervous? He took a deep breath and realized his heart was pounding with excitement, not with fear. He couldn’t wait to be a woman out in the real world, and not just in the safety of his own apartment.
He opened the door and stepped out with eyes closed shut. He was too afraid to open them, too afraid to see his neighbours staring back at him, wondering why he was wearing a woman’s dress and makeup and a wig. He was relieved when he opened his eyes and saw nothing but closed doors. He took a deep breath and started down the stairs, moving carefully as he’d never navigated a staircase in heels before.
But he managed to make it to the bottom without falling. As he went to open the door at the bottom of the staircase, one of his neighbours beat him to it. “Sorry,” she said as she moved to the side. And then she looked Terry up and down with a peculiar look that was foreign to Terry. All Terry was able to do was force a smile. He knew he needed to brush by her and get out of there before she had too much time to look at him, but he couldn’t move.
“Thanks,” Terry said in his feminine voice, finally breaking free from his paralysis. He skirted past her and rushed towards the door.
“Wait,” she said, making Terry’s heart stop for a moment. He turned around slowly, still with that painfully forced smile on his face. He was regretting everything: leaving his apartment, putting on the dress, getting into cross-dressing in the first place.
“Yeah?” Terry said softly, hoping his voice wasn’t giving him away anymore than his look already had.
“I love that dress,” she said. And then she looked at Terry’s feet. “And those shoes. Where did you get them?”
Terry squirmed. Was she teasing him or was she serious? Could she not tell that he wasn’t actually a woman? “Saks,” Terry said with his soft, feminine tone. “See you later.” He turned around and got out of that building as quickly as he could. And he didn’t feel safe until he was three blocks away from the building, three blocks away from the neighbours who saw him on a regular basis.
And then he realized he was three blocks away from his home, away from safety. He was now standing out on the street on a busy Friday night, surrounded by people who could see him—people who lived in the city, who probably walked by his shop all of the time. He’d never been so vulnerable in his life. He’d never been so exposed in his life, with his short skirt hardly even covering his perky bum. And what would he do if he sprung an erection? He hadn’t masturbated before leaving the house, and the lace of his panties were already beginning to arouse him—and so was the tight satin of the expensive white dress. Hell, even the heels were strangely arousing.
But he had to keep his composure. He had to keep his cock from hardening. He took a deep breath and looked around. Across the street was a busy club. A group of men stood outside with cigarettes in their mouths. Two of them were looking Terry’s way. One of them nudged another, and a moment later, all of them were looking Terry’s way. One of them smiled and waved. “The party’s over here, beautiful!” he called out.
Terry’s legs trembled. He smiled and waved back. “Thanks,” he softly called out—probably not even loud enough for them to hear. They went back to chatting, looking over every few seconds, probably trying to figure out why there was a woman in a skimpy dress standing alone on a street corner… Or did they think Terry was a prostitute? Did they think he was waiting for a job to come by? Terry’s heart stuttered again.
And what was Terry waiting for? Where did he want to go? What was he looking for? He spun around and tried to figure out if he’d lost his mind. And then he saw Granville Street, teeming with people, buzzing from club to club. He saw a bouncer letting a group of beautiful women skip a long line, and he saw a group of young men hitting on a group of young women. Everyone was having fun—and all of the women were sexy. Terry wanted to be like them. He wanted to be hit on and drooled over and slapped on the ass. So he started walking down Granville Street.
And he only made it a block before he turned a set of heads. “Where you going, baby?” a brown-skinned man asked.
Terry shrugged his shoulders, unable to hide the red-cheeked smile from his face. “Why do you want to know?” he asked.
“Is there room for a few more?” the man asked.
Terry just laughed and continued down the strip. He wasn’t headed anywhere. He was just basking in the attention, and loving the feeling of the cool air teasing up his legs and tickling his bare ass. As he stopped at a red light, he got exactly what he left the house for: a carful of young men whistling from their windows. “Show us your tits!” one of the men shouted. And of course Terry didn’t flash the men because he had nothing to show them, but he loved the attention. He loved that they singled him out and not the other fifteen girls who were standing on the same block, waiting for a little bit of attent
ion of their own.
Terry’s head was spinning with excitement. He was having more fun than he’d ever had as an adult. And that excitement was starting to scare him. A week ago, the thought of walking down Granville Street in a short dress and makeup would have made Terry shudder with nausea, but now he didn’t want to go home. He wanted to hit up that strip every night. And he wanted to take his new fun even further. He wanted to see just how much fun he could have as a woman, in his clients’ pretty clothes.
But for tonight, he knew he needed to cut himself off. He needed to get home, jerk off, and get to sleep so that he could wake up with a clear and straight head. He needed his sensibilities back before he did something stupid, before he marched himself in front of people he knew and cared for—people he didn’t want to know that he was a closer cross-dresser, like his family and his friends. So he made his way back home, basking in the final few minutes of his female glory. One of the people who lived in his building held the door for him—something he wasn’t used to, such a small gesture but so nice and refreshing.
It only took a few minutes for Terry to get off that night: a few anal penetrations and a few strokes of the cock, and cum was everywhere. He got the little dress nicely cleaned and hung before heading off to sleep. And then he dreamed about pretty clothes and stunning eye makeup.
CHAPTER VIII
It was an unfortunate Saturday when the only clients who came into the store were there to pick up their orders. No new orders, no new pretty clothes being dropped off. Terry had nothing to work with, nothing for his Saturday night, which he’d spent all morning looking forward to.
It was 4:00 PM when his shop was supposed to close, but Terry didn’t close, hoping some beautiful woman would come in looking for some last second dry-cleaning. All of the other dry-cleaners closed at 4:00 PM on Saturdays, so maybe being the only one open would bring clients in… But no one came. Terry was stuck with nothing on the most exciting night of the week.
Big Hard Girls Page 3