Until his lawyer said, “Okay, well then we’re going to want your little girlfriend to testify in court.” Barry’s heart skipped a beat before plunging into his gut. He’d known it was a possibility with his new lie, but he never thought it would get to that. His optimism had assured him that there would be no day in court—though now that optimism was dwindling. He could still take the offer. He could sell his house, give her the $150,000, and then buy a cheap condo with what he had left… At least then he would have something…
Or he could see how far Lexi was willing to go, and how badly she wanted those tapes to stay away from her friends and family members. So he prepared a note and stuffed it into a bag along with a new outfit and a toy he’d purchased online: a long, black dildo that was much thicker and longer than anything he’d ever seen her use. He wasn’t including the toy as part of his blackmail. He thought of it more as a thank you gift, for recording the videos—and maybe as an early thank you gift for appearing in court.
CHAPTER VIII
Liam didn’t get much work done at school. He spent most of the day in the library, hidden in the corner with his laptop as he searched for every Barry Peters in the city. He even widened his search to find every Barry Peters in the province. There were fifteen that he could find—three who lived within ten kilometers of him. He had no way of knowing which Barry Peters was his tormentor, or if any of them were his tormentor. Maybe the Barry Peters name was just fed to him to throw him off. Maybe it was the name of a friend or some client on the other side of the world who needed some strange proof that he had a girlfriend at one point in his life.
But if Barry Peters was actually the blackmailer, then he had a pretty good idea of which Barry Peters was responsible. There was a Barry Peters who, according to Facebook, lived in the community on the other side of the woods behind Liam’s house. He was in his early thirties and he looked like a normal enough guy. He dressed nicely in his photos and he was decently well built. He had a handsome smile. Apparently he owned a house and had a decent job. But why would such a well put together man be out in the woods blackmailing eighteen year olds? Maybe that was just his fetish…
Liam went straight to that red box on his way home from school to see what kind of goodies were awaiting him. It was quickly becoming his favourite part of his day, like opening a fresh pack of trading cards—he had no idea what to expect, but he knew he was going to like it. Today’s outfit was a black lacy two-piece with a pair of lace kitty ears and a clip-on kitty tail. Liam snuck the outfit into his house, along with the big black dildo that made his heart pound. He wasn’t sure the dildo would fit in his tight asshole, but he was strangely excited to try.
It wasn’t until he was in his room that he discovered the note folded into the lacy top. His excitement was suddenly replaced by an increasingly familiar dread. “Kiss the window tonight if you’re willing to do anything to keep these pictures from your friends and family.” Liam wasn’t sure what ‘anything’ meant, but that didn’t stop him from kissing the window at the start and at the end of his nightly performance—just in case the watcher didn’t see the first kiss. He waited a couple of hours before wiping the lip-gloss off the window.
It was a quick show that night. Once he’d managed to stuff that thick black dildo into his ass, he knew he wasn’t going to last long. It felt good—too good. His cock had never been so hard and he’d never produced nearly as much cum in his entire life. When he pulled the dildo out, he felt empty and stretched out. He had a tough time walking the next day, as his butt was still sore from being stretched so wide. He told his friends that he’d fallen off his bike when they asked why he was walking funny.
He was so excited to see the red box that afternoon that he ran to it. He couldn’t wait to see which outfit was awaiting him, though he was starting to worry about storage. His black backpack was full of clothes so he was going to have to find somewhere else to keep the slutty outfits hidden. He opened the box and quickly pulled out an outfit that surprised him: a pencil skirt, a white blouse, a pair of black heels, and some costume jewellery. It was a nice outfit, but it wasn’t exactly sexy. It wasn’t something a stripper would wear on stage, and it wouldn’t be the cutest outfit to wear during a nightly show. So he read the note.
“Next Friday I need you to testify in court. You can wear this or something else; nothing too scandalous. But tonight, I want you to go out in this and get comfortable with being out of the house as Lexi. Leave the house at 9:00 PM. Go into town for a couple of hours. Have some fun.”
Liam’s heart was suddenly pounding after a moment where it wasn’t beating at all. What did his tormentor mean, ‘go out in this’? Was Liam actually being blackmailed into leaving the house as a woman? How could he do it? His parents would still be up at 9:00 PM, in the living room with a view of both the front and back door. And what if they decided to check on Liam before going to bed?
Liam took a deep breath and read the note again. He wasn’t so worried about his parents—he could survive a bit of punishment if they realized he’d snuck out. He was eighteen after all—old enough to go out at night. He was more worried about being out as a woman, for the first time ever, and possibly being seen by a friend or someone from school. What if they recognize him? What if word gets out that he likes to get dolled up and pretend to be a woman? Then all of this blackmail hoop jumping was for nothing…
But what other choice did he have?
During dinner, Liam pretended to be exhausted. He even faked a nod off. His mother asked him if everything was okay. “I just stayed up late last night studying for this test, and now I have to stay up late again tonight,” he lied.
“When’s the test?”
“Tomorrow,” Liam said, even though there was no test.
“Studying is important, but sleep is more important. You won’t do well on the test if you’re exhausted.”
“Maybe you’re right,” Liam said. His mom was a teacher at a nearby school, and she’d given him the same lecture before.
So after dinner, Liam went into his room and stuffed pillows under his blankets. Then, with his parents still awake and buzzing around downstairs, he started getting ready. He carefully crept through his room gathering everything he might need. He put his wallet into a little purse and then he started getting dressed. He saved the wig and makeup for the end, just in case he had to perform an emergency disrobing. He was about to start doing his makeup when he heard the heavy footsteps of his father coming up the stairs. He panicked and jumped into his bed, throwing himself under the covers and then realizing his female wardrobe was all over the floor. But his father’s footsteps were at his door now. All he could do was hope that his father wouldn’t see the clothes.
But luckily, Liam’s dad didn’t come in. He walked by and went to the closet at the end of the hall before heading back down the stairs.
Liam decided it would be better to do his makeup elsewhere, maybe in a public bathroom on his way to the bus that would take him into town. So he packed his makeup supplies into his purse and then he got his wig onto his head. He spent the next five minutes carefully scaling down from his bedroom to the back yard. It was slightly past nine—he hoped he wasn’t too late for his cruel blackmailer. As he touched his feet to the ground, he wondered if the blackmailer was watching from the woods now. Liam was too afraid to look, too afraid to see the glowing eyes of some twisted voyeur. He didn’t want to see his rival’s face. He liked to think that his tormentor was a normal-looking guy with some well-intentioned master plan, but he knew it was more likely that his tormentor was some overweight, sweaty mouth breather who liked the stroke his cock from the dark safety of the woods.
But Liam had to go into the woods to get away from the house without being seen. His heart raced as he ran within twenty feet of the hidden red box. He didn’t look over at the box, worried the blackmailer would be sitting there watching. He kept running until he was a good half-mile from his home. Then he emerged from the woods and slippe
d between two houses, onto the sidewalk that would bring him to his bus stop. But first, it would bring him to a small grassy park with a public bathroom. There were two young boys playing basketball on the small cement court. They didn’t notice Liam as he slipped into the women’s bathroom and locked the door.
Liam wasn’t wearing the pencil skirt and blouse that he’d gotten that afternoon in the red box. Instead, he went with something more casual, saving the pencil skirt outfit for the apparent court date, which was still a giant mystery. Tonight, Liam was wearing one of his go-to outfits: a black tank top and his favourite red plaid high-waisted skirt. He had his hair tied into two tight French braids. It was what he considered to be his classic look—and he also considered it to be his most convincing look. If he was going to go into town undetected, sporting this look was his best bet.
The light in that public bathroom wasn’t ideal, but it was good enough that Liam was able to complete his transformation into Lexi. He went dark with the mascara and dark with the eyeliner, and then minimal everywhere else. He did a bit of contouring on his nose and cheekbones, just to make himself a little bit more unrecognizable.
He took a minute to stare at himself in the mirror, trying to decide if there was anything else he could do to improve his disguise, so there would be no chance of being recognized. And then he remembered he was likely being followed—there was someone lurking out there, waiting for him to emerge from that bathroom an get on with his night out. So he took a deep breath and stepped out from the bathroom.
The playing children were gone now and the sun was completely gone. Liam looked around but could see no one. But he still had to follow his commands, so he started towards the bus stop.
CHAPTER IX
Catching up with Lexi wasn’t easy. After Barry watched Lexi scale down from her bedroom window, he had to run back through the woods and then he had to take his car a couple of miles to make it to the bus stop before Lexi’s bus pulled up. When Lexi wasn’t on the first bus that went by, Barry worried that he’d missed her. When Lexi wasn’t on the second bus, Barry started losing hope. It didn’t help that he had to get on each bus to see the faces onboard, and then he had to get off at the next stop and walk all the way back before the next bus came.
He looked up from the book he was pretending to read as he stepped onto that third bus. He expected to see a bus full of strangers as he scanned the faces. And then he saw her, staring out the window, stashed away in the back corner of the bus. She looked over at him and then he darted his gaze away, terrified of making eye contact. He knew that she would have no idea who he was—just another guy getting on the bus—but he didn’t want her recognizing him in a couple of weeks when she came to testify in court. Not that it mattered whether or not she recognized him; she would be testifying either way, assuming she was still willing to play ball.
Barry took a seat near the front of the bus, on one of the sideways-facing seats, so he could keep an eye on Lexi. Lexi had turned her attention back to the window. Barry felt a lot more nervous than he expected. Every time she so much as repositioned her body, Barry found himself perking up, darting his gaze away, and becoming tense. He tried his best to play it cool when Lexi finally stood up and walked over to the door. He watched over the pages of his book as she pressed the ‘NEXT STOP’ button. He didn’t stand up right away. He knew that she probably suspected someone was trailing her, and she probably suspected that someone was on the bus with her. Barry looked down as she looked around before stepping off.
Thankfully about four other people stepped off the bus with Lexi. Barry did his best to blend in with them. He stalled at the bus stop until Lexi was half a block away, and then he started trailing her, sticking close to the building walls in an attempt to blend into the shadows. Whenever Lexi looked back, Barry did his best to look inconspicuous. He tried not to stop or look away suddenly, knowing that would be a sure-fire way to grab her attention. But it was hard not to react suddenly whenever her gaze turned back towards him.
He let her get a whole block ahead of him. She seemed to be meandering around downtown without any goals. Barry was just happy to see her out, to watch her passing strangers in the street so she could become more and more comfortable with being a woman in public. He watched as a few guys turned around and checked out her ass as they walked by. Barry couldn’t help but smile, but he also couldn’t help but feel a tad bit jealous, as if the men were checking out something that belonged to him.
Barry was surprised when Lexi slipped into a crowded bar. Though maybe it was a smart move. The bar was loud and the patrons were drunk, so it was probably the best place to blend in and remain unnoticed. And if anyone did notice her or try to talk to her, they wouldn’t be able to hear that slightly masculine tinge to her voice. Barry waited outside of the bar for a good fifteen minutes—peering in through the windows occasionally to make sure she was still there—before heading in himself. Lexi had taken a seat at the bar. She was drinking a vodka martini. Barry took a seat in a small, recently emptied booth, facing the bar. The previous patrons empty drinks were still on the table, as well as the crumbs from their French fries. But Barry didn’t mind. He wasn’t there to eat anyway. He was just there to keep an eye on Lexi, to decide whether she was ready for court, and whether she was committed to testifying.
As Lexi finished her first drink, a tall man slipped up next to her. He flagged down the bartender and ordered Lexi a second drink. Then he took the seat next to her and started chatting with her. It was another good sign, but again, Barry felt a tinge of jealousy creeping into his gut. Lexi was his girl—his creation. He’d spent the past few weeks watching her, buying her clothes and toys, making her more and more comfortable with being a lady. And now some other guy was swooping in to enjoy all of Barry’s hard work…
But Barry knew that Lexi wasn’t his—she didn’t belong to him and he didn’t want anything from her other than her testimony in court, so that Barry wouldn’t have to pay out every dollar he had to his name plus more.
The man bought Lexi her third drink, and then he got up and extended his hand. Lexi shook her head but the man was persistent. Finally, he got her to her feet and led her over to the dance floor. Lexi’s cheeks were dark red as they stepped onto the busy dance floor. The man started dancing as she stood, embarrassed with a big goofy smile on her face. She looked around and then she started dancing. She wasn’t the greatest dancer, but she was cute. Barry noticed a few different guys looking her way from the safety of their tables, especially once she was twisting, making her skirt rise up to show off her long, smooth legs. Everyone was oblivious to the fact they were gawking over a biological man.
Another hour passed and Lexi had consumed another couple of drinks. She’d gone out onto the dance floor with a couple more guys, and she even had to dodge the kiss of one particularly drunken man. But she was having fun. Barry watched her closely as she stumbled towards the bathroom. Then he watched as one of Lexi’s admirers walked over the bathroom to wait for her to emerge. He didn’t waste a second once she was out of the bathroom, already with a stiff drink to give to her. She took it, and he insisted that she pound it back. The man was being pushy and Lexi was too drunk and fragile to fend him off. He got an arm around her, placing his chin on her shoulder, and then Barry watched his lips say the words, “Come home with me.”
Barry watched as the man’s hands caressed Lexi’s sides, up and down, wrapping around her body—his fingers moving closer and closer to her tits. She tried to push his hands away, but he was determined to get what he wanted. He gave her a nudge towards the door. Lexi was trying to be polite, but the man remained determined.
The man wrapped his hand around her wrist and started pulling her towards the back exit. Barry couldn’t watch anymore. He jumped to his feet and hurried over. He grabbed the man by the arm and clenched tight until the man let go. “Hey, what the fuck is wrong with you?” the man said. His breath smelled of bad whiskey.
“Leave her alone o
r I’ll snap your arm off of your body,” Barry said, staring into the man’s eyes. The man tried to pull his arm free but Barry’s grip was too intense. He tried giving Barry a shove, but Barry shoved back harder, slamming him into the wall. “I mean it,” Barry said.
So the man went docile and backed off. As soon as Barry released him, he scurried like a startled rat into the bar crowd, probably to find an easier target.
Barry turned and looked Lexi in the eyes. She was silent, staring back at him with her glowing beauty. It was the closest he’d ever been to her. Sure, he’d seen her up close with his camera before, but he’d never seen her like this, in the flesh, in vivid three-dimensions. She was beautiful and fragile and perfect in every way. “Sorry you had to deal with that,” Barry said before turning away and heading straight for the exit.
Barry had seen all he needed to see. Lexi didn’t need his help to get ready for being a real woman in court. She was ready. Barry got on the first bus heading back home, and he hoped that Lexi would get herself home safely.
CHAPTER X
The outfits only got better over the next week. Liam would rush home from school and head straight for that red box to see the treasures that awaited him. He couldn’t believe someone out there was willing to spend so much money on him. Nothing was cheap. Everything was high quality and beautiful—though it was all becoming very hard to store. Liam now had about fifteen different outfits stashed away in his closet: skirts, dresses, panties, shoes, and tons of lingerie. He could have filled two large suitcases with his feminine wardrobe—but two large suitcases would have been too suspicious, so instead he kept it all stuffed into backpacks and old shoeboxes. Some items he kept hidden under floorboards and most of the lingerie he kept hidden inside of his box spring, through a slit he carefully cut. But he knew that he was going to need a new solution soon if the outfits were going to continue appearing in that red box.
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