So he went into the back of his shop and started searching for anything. There were a few sacs that had been sitting in the back corner of the shop that he’d been meaning to take to a donation bin—sacs of clothes that were dropped off and then never picked up again. It happened from time to time, usually with older people who either forgot about their clothes or, God forbid, passed away. But occasionally there were clients who didn’t come for their clothes for other reasons: because they couldn’t afford the bill or because they decided they didn’t want them anymore.
Most of the sacs at the back of the shop were filled with old ladies’ cardigans and old men’s suits—but there was one bag that had more along the lines of what Terry was looking for: dresses. They were all matching bridesmaids dresses, all blue, all different sizes. There was one in the bag that was perfectly Terry’s size. He tried it on there in the back of the shop.
It wasn’t the most flattering dress, so Terry used a pair of scissors to cut the cheesy flower decoration off of the shoulder, and that helped. Then he brought the dress into his little alterations corner to make it a bit shorter, and to make the straps a bit thinner. It took him a good hour and a half, but the work was worth it. The dress suddenly didn’t look so ‘prommy’. Now it looked more like something a girl would wear out at the clubs—or what Terry was going to wear out at the clubs.
But the outfit wasn’t complete. Terry didn’t have panties, he didn’t have a bra, he didn’t have shoes, and he couldn’t wear his wig and baseball cap combination again, as it didn’t exactly compliment a nice dress. So Terry made a few stops on his way home from work.
His first stop was at a woman’s shoe store. He was embarrassed walking in, and even more embarrassed when the store clerk asked him what size his wife’s feet were. “About the same as mine, actually,” he said. And then he watched the clerk’s lips curl into a smile—she knew the shoes were for him. So his face was dark red as he tried on shoes until he found a nice pair that fit. They were about one hundred bucks.
Next was the costume shop, which was a few blocks out of Terry’s way. They had a whole section of wigs, which was essentially reserved for drag queens when it wasn’t Halloween—and it wasn’t Halloween. Terry had no fake story for the store clerk at the costume shop. He thought about lying about a wife with cancer who needed a wig, but he knew that would be a stretch, especially when the clerk asked for his wife’s head size and Terry would have to say, ‘About the same as mine.’ It was better to not lie about a terrible disease.
So he said nothing. He just went to that wall and awkwardly asked the clerk to take down the long brunette wig that closely matched his own natural hair colour. The clerk asked no questions before taking the wig down and fitting it on Terry’s head. “I think we need something a bit tighter,” said the clerk before disappearing into the back room. Terry’s face was dark red as he left the store, but at least he was leaving with a high quality wig that would last him years.
Terry’s final stop on his way home from work was at the lingerie store. He went in to get a single pair of panties and a bra, and he ended up leaving with five pairs of panties, two bras, two slips, a lace bodysuit, and a garter belt with a pair of fishnet stockings. It was a hefty bill, but Terry just couldn’t help himself. He didn’t even bother lying to the store clerk at the lingerie store. He just said nothing as he collected his items and paid the bill. At the counter he noticed a little bottle of perfume, so he bought that as well.
He had a quick bite to eat at home before running a bath so he could freshly shave his legs and armpits. Then he quickly got himself dolled up, slipping into a pair of red panties and a matching red bra. He admired himself in the mirror for a few minutes. It was amazing how feminine he already looked, just wearing some women’s undies. He didn’t even have his wig or makeup on yet. It was hard to believe he’d never noticed his feminine figure before. Had he always had it? Well it didn’t just come out of nowhere…
Terry got to thinking: maybe all guys are born with a potentially sexy physique. Maybe being feminine is more about the pretty clothes than the body a person is born with.
Next, Terry did his makeup. He took his time. It was still early in the night, and he wanted everything to be perfect. He went with that same look: the smoky cat eye look, with a few minor alterations that he’d learned about while doing some research on his phone at work. Next came his blue dress, which he’d altered a little bit too short. The bottom cusp of his ass was hanging down, but he didn’t mind. He knew guys would like it.
Finally, he got into his new heels and his wig. And then, once again, he found himself in front of the mirror, staring at himself, admiring his curves and his stunning features. He was sexy. He felt comfortable—like himself, as if for the first time in his life. He was ready to show himself off, ready to go out for the night, ready to try new things and feel that amazing excitement one more time.
CHAPTER IX
The clubs were intimidating. The line-ups were long and the women lingering around them were beautiful. And the men weren’t bad either—all jacked and handsome and constantly scanning their options. Terry knew he was making himself vulnerable by walking up to the front of that line to try his luck with the bouncer. He’d watched a few girls pull it off, getting let inside, skipping the line—but he’d also watched a few girls get rejected, being told to go to the back of the line. One girl ran away as soon as the bouncer told her, “No way. Back of the line.”
But Terry had to try. The thought of trying brought on that excitement that Terry had become so obsessed with. He needed that rush and he wasn’t going to get it unless he paraded himself in front of all those people. When the bouncer turned to look at him, his joints froze. He nearly stopped in his tracks and fell over like a stiff board. But he forced himself to carry on, and he forced himself to smile.
“Hi,” he said with his soft, meek voice.
“Can I help you?” the bouncer asked with a stone cold tone.
Terry cleared his throat and held his composure. “One of my friends is inside,” he said, and then he forced that smile bigger. The bouncer kept staring at him with that cold gaze. And then suddenly, he moved to the side and let Terry in.
Terry’s heart leapt up in his chest, pounding hard against his ribcage. He was let in, he was accepted as a beautiful woman! But was it a good thing? Was it good that society was accepting his delusion? Was it good that the world was allowing him to get away with this degenerate addiction?
A man bumped into him. “Sorry, sweetie,” the man said. And then he froze as he looked into Terry’s eyes. Terry’s heart stuttered, which he was getting used to. “Can I buy you a drink?” the man asked with glowing eyes.
Terry just smiled, and a minute later there was a drink in his hand. He drank it happily. He’d never been given a free drink before—but it wasn’t the last one he would get that night. It was only twenty minutes later when another drink ended up in his hand, but he had no idea where this one came from. He still drank it, not wanting to waste it. And then another drink came, and another, and another.
And soon, Terry was heavily buzzed, wobbling slightly in his heels, worried he was about to topple over or let his natural male voice slip out. He knew he needed to get out of that club and away from all of the attention for just a short period of time, so he could get a hold over himself.
He stumbled out from the club’s back door and he took a deep breath of fresh air in that cold, dark alleyway. His head was spinning, and not just from the liquor and the flashing lights. He walked down a short ways before coming across a window with a board behind it. He used the window to look at his own reflection, still in awe of how feminine he looked. It still didn’t seem real—it all still seemed like a strange dream that wouldn’t end, that he didn’t want to end.
He reached the end of the alley and looked down the road. His heart stopped momentarily as his gaze met the gaze of one of his clients: Sheila, the prostitute and owner of the purple lace lingerie. S
he was wearing it now as she stood on the street corner, wearing only a fur coat over it.
Terry had to remind himself that he was unrecognizable, especially from half a block away. Now he just looked like another woman enjoying her Saturday night downtown. He didn’t look like Terry, he didn’t look like Sheila’s dry-cleaner. She smiled and then turned back to the street, waving at passing cars. And she had the power to make every car slow down as men and women alike stopped to admire her body. Terry was sure that many of those men were considering her: thinking about cheating on their wives with the beautiful escort.
Terry started to casually walk in Sheila’s direction, drifting wide and out of her line of sight. He kept an eye on her, and then he noticed a few other prostitutes down the block, all waiting for jobs of their own. Terry backed himself against a wall near a bus stop, pretending to wait for a bus so that he could watch the night workers. He was only there for a few minutes, and in that time he watched as Sheila got picked up, as well as a few of her co-workers, if you can call them that.
The cars picking them up weren’t crappy old Buicks. The girls were being picked up by shiny new BMWs and the odd Lexus. These guys were probably paying these girls a lot of money for a night of fun—or even just an hour or two.
Terry wandered further down the street, venturing deeper into Vancouver’s nightlife. As he came closer to Davie Street, where all of the homosexuals hung out, he came upon a new block of prostitutes. But these girls were different—they were taller, some were broader, and a few had a bit of five o’clock shadow that their makeup couldn’t hide. These prostitutes were men—some made more convincing women than others. The sleek BMWs picked up the convincing girls and the rest got their turns in beater trucks and old VWs. But there was a market for all of them.
“Hey!” a male voice called out from behind Terry, making him jump and spin around. A man was staring at him, hanging out the window of a black Audi. He was wearing a suit and an expensive golden watch, which dangling down over his window frame. “How much?” the man asked. And it took Terry a moment to realize the man was talking to him.
Terry cleared his throat. “How much?” he asked awkwardly.
“Yeah, that’s what I asked—how much for two hours?” The man wasn’t bad looking—he was a bit older with some grey hairs. He was thin and he seemed to be nicely groomed.
Terry wanted to tell the guy to beat it, but he was suddenly overwhelmed by a curiosity—and Terry didn’t have the best track record when it came to fending off teasing curiosities.
CHAPTER X
The man’s apartment was impressive, on the top floor of one of the bigger buildings in the downtown core. Some of his walls were painted a deep red colour, the others were painted black, and there were quirky lamps everywhere. But nothing looked cheap. Even the hat rack by the front door looked like it had real gold embellishments on it.
Terry wasn’t sure how his legs were still allowing him to walk. His heels were starting to hurt, and the terrified trembling hadn’t gone away since he told the man, “Five hundred dollars,” back on the street corner. When he said it, he didn’t expect the man to agree so quickly. “Hop in,” he said without missing a beat.
But Terry didn’t get in right away. He was way out of his element, about to break through more boundaries than he was ready for: getting fucked by a stranger, getting fucked by a man, getting fucked for money—the list went on and on. But Terry couldn’t say no. For days, this had been his secret little fantasy—the exact scenario that played out in his mind whenever he pressed that black steamer handle into his asshole.
But now, his heart was stammering. He’d never been with a man before. He’d never even been attracted to men before, but now, for some reason, this particular man seemed irresistible, even though he wasn’t anything special. He was just rich and horny; Terry only cared for the latter. But he was terrified. Sure, before he got into the car he made sure to say, “I’m not really a woman you know.” He was surprised when the man laughed and said, “I figured, though you look stunning.” So now, Terry knew he didn’t have to worry about letting his masculine identity slip. He didn’t have to worry about dropping his feminine voice for a moment, or accidentally exposing the bulge in his little red panties. His client knew exactly what he was in for, and Terry was exactly what he wanted.
Terry was only a few steps into the room when the man walked behind him and put his hands on Terry’s shoulders. “I love your dress,” he said before slipping his hands gently down the sides of Terry’s recycled blue dress.
“Thanks,” Terry said softly. His body was tense. He was being touched by another man, a man who intended to stick his cock in Terry’s ass, a man who didn’t even have a name as far as Terry was aware.
The man wasn’t shy. Terry probably wasn’t his first prostitute experience. It was only a minute before the man tried to reach down between Terry’s legs. Terry, acting entirely on impulse, reached down and grabbed the man’s hands, holding them around his pelvis, terrified to let them go any further, even though it was exactly what the man was paying for. Terry didn’t like being reminded that he had a cock between his legs. He wanted to feel like a woman, and he felt like a woman when the man was kissing his neck and rubbing his erect bulge against Terry’s ass.
But Terry especially liked it when the man reached around and cupped Terry’s padded chest. He liked it when the man squeezed, eliciting a soft moan from Terry’s lips. “Your heart is beating so fast,” the man said with the palm of his hand against the centre of Terry’s ribcage.
“I’m sorry,” Terry said, though he wasn’t sure why he said it. The man laughed and went right back to kissing Terry’s neck, teasing his fingertips down Terry’s body towards Terry’s cock. Terry had the urge to stop him again, but he resisted. The man was much bigger than Terry, and much stronger. He didn’t want to make him angry. If the man snapped, he could easily kill Terry and get away with it.
Those fingers drifted over Terry’s pelvis, over his pubic bone, and down across his bulge. They teased up Terry’s skirt and then found themselves on his panties, massaging his cock as if it was a clit. The man rubbed his fingers in small circles, making Terry feel even more like a woman—and more like a slut. Terry let a long, soft moan slip out from his lips.
“You like that?” the man asked.
Terry nodded his head. His long brunette hair fell in front of his face as he looked down at the stranger’s hand under his skirt. “Shit,” he muttered. He liked it—he liked it too much. He couldn’t wait to get the man’s cock into his asshole. And he couldn’t wait to do this again and again. Who knew that being a prostitute could be so much fun? And for five-hundred bucks? That was more money than Terry made in a week, most weeks.
Terry was getting hard fast, but his little red panties did a surprisingly good job of holding him down. The man made sure to locate the tip of Terry’s cock as he continued to rub. Terry squirmed in his tall heels. And then he found himself reaching back, running his fingers down his client’s abdomen. He fought his fingers down his client’s pants and then located his cock. He was already hard—and he was big, much bigger than Terry, and much bigger than the black steamer handle that Terry had been using each night.
The man’s cock was warm—hot even. It was throbbing, and Terry could feel all of his veins. He only stroked the man a few times before he could feel a dab of warm moisture on the man’s tip: a small bout of pre-cum. The man probably wasn’t going to last long once inside of Terry’s asshole—assuming he could even fit inside of Terry’s asshole. It seemed unlikely now, as Terry could hardly even wrap his fingers around the man’s girth. But the man paid his money, and Terry was itching to get off as well.
The next few minutes were a blur. The man got Terry’s cock out from his panties, and then somehow Terry ended up on his knees, turned towards the man. That giant cock dangled in Terry’s face, making Terry’s heart stutter and his hands tremble. But still, he reached up and grabbed it and stroked it
and felt it throbbing. He brought it to his lips and his heart stuttered again. He was only able to fit half of it in his mouth before that tip was pressed against the back of his throat. He gagged a bit, but managed to hold his dinner back—even when the man grabbed Terry’s head and pulled it in tight to his pelvis. “You like that, you little slut?” the man asked through clenched teeth. His face was starting to turn red and his cock was throbbing even harder. He really wasn’t going to last very long.
Terry was only able to respond by nodding his head slightly. He could taste the drooling tip of the man’s cock, pre-cum oozing out onto his tongue. It was sweet, and a bit salty, but Terry didn’t mind it. He kind of liked it. He liked that he was able to make a man so hard.
“Get on the bed,” the man said, pulling himself back quickly, as if he was stopping himself from ejaculating prematurely.
Terry stood up and realized his legs were trembling harder than ever before. He looked down and saw that his cock was rock hard, holding up the skirt of his dress like a tent pole. And then he looked at the large bed with its black satin sheets, and he wondered: what the hell am I doing?
What happened? How had Terry degenerated so much in the span of a single week?
He looked over and saw his reflection in the mirror, and he suddenly remembered the woman who dropped the blue dresses off, two months before. He remembered her face when he told her how much it would cost to dry-clean all ten of the bridesmaids dresses, and he remembered her saying, “They didn’t even cost that much to buy.” He had a feeling she wasn’t going to be back for the dresses, or to pay the bill, so he only quickly ran them through the steamer.
And when he looked at the blue dresses back then, the only thought that ran though his mind was: are there any stains on them? And that was better—that’s how his mind should have stayed wired. Life was easy and simple back then. He knew his job and he performed his job and he didn’t get mixed up in stealing clients’ clothes or breaking the law by becoming a transgendered prostitute. Why couldn’t life be that simple again? How could Terry stop his degeneracy—or was it too late?
Big Hard Girls Page 4
