He couldn’t spot that garden gnome.
And he was just about to give up and turn back when a nearby light suddenly flicked on. Barry froze. He wanted to quickly sprint back into those woods before anyone got a good look at him, but he wasn’t able to will himself to move a single muscle. Slowly, he turned his head towards the source of the new light.
It was coming from inside one of the houses: a glowing upstairs window in an otherwise black structure. Barry stared at the window for a moment before recognizing the curtains hanging at the window’s edges: it was the same room from the week before. And not even five seconds after this revelation, the young man appeared in sight, walking across the room in his pyjamas.
Barry quickly hurried back towards the woods so he could watch from the safety of a tree. His heart was pounding and his brain was begging him to turn around and leave. He still couldn’t figure out why he wanted to watch so badly. He knew he was watching a young man and not a woman, but still he couldn’t bring himself to look away.
He had a feeling his strange obsession with watching the young man had something to do with his hard times with Sarah. Surely she’d tested him until he’d finally snapped, and now this was a repercussion of his newfound broken mental state. He let go of Whiskey’s leash, allowing the dog to trot off into the woods to do a bit of exploring while his owner watched a stranger from behind a tree.
Barry squirmed as his mind struggled between morals and urges. He hated himself for being a peeping tom, but he just couldn’t help it. The young man was so strangely fascinating. What would make a young man want to put on women’s clothing? And why was he doing it at such a strange hour of the night? Did anyone know about this young man’s secret? Or was Barry the only one?
He watched as the young man pulled off his pyjamas, leaving him standing naked. His legs and crotch were shaved smooth. If the young man was keeping his cross-dressing a secret, how was he keeping his shaved legs a secret? Did he have a good excuse, or did he just always keep them covered? Barry watched as the young man stepped in front of his closet mirror and stared at himself. The young man reached down and tucked his cock between his legs, making himself look impressively feminine—impressive because he wasn’t wearing makeup or a wig or even a skirt. He was just a naked man with no body hair, yet somehow he looked like a woman.
Maybe it was the slight lumps on his chest. How were those possible? Were they tiny implants or were they just soft pecs that looked like breasts? All of these questions kept Barry strangely fascinated and unable to look away. He had the perfect vantage point; up on that ridge, he could see everything above the young man’s calves.
He felt awkward and gross watching at first, until the young man had a pair of panties covering his cock and his blonde wig covering his short brown hair. Then, it suddenly didn’t seem so awkward, even though he knew he was breaking the law. Barry looked around often, making sure there weren’t any neighbours emerging from their houses. He knew he wasn’t completely safe, even behind that tree with his back to the dark forest. There could easily be another insomniac out walking his dog.
So Barry kept his body low. He kept the collar of his jacket up near his face and he was ready to run at a moment’s notice, though he was afraid that he might freeze up again at any potential conflict, like when that light turned on.
The young man was now slipping into a black dress. It was a tight fit, but it fit him perfectly, showing off his impressive hips and his cute little tits. His nipples were erect and visible all the way from those dark woods. Barry saw the young man’s cute feet briefly as the young man stepped up onto the bed. He wasn’t putting on makeup tonight, but he didn’t necessarily need it—though a bit of mascara would have made a big difference.
Barry waited for the young cross-dresser to do something, but the young cross-dresser just remained on the bed. He pulled out his laptop and appeared to be casually surfing the Internet—just going about his nightly business while wearing a black satin cocktail dress. He twirled his blonde hair with his pointer finger. Ten minutes went by.
Barry finally willed himself to stand up and leave, realizing he wasn’t just being a voyeur—he was being a full-blown stalker. He wasn’t just watching some free sex show, he was watching a young man while he casually surfed the net. Barry had no business lingering around in those woods, so he started to turn around. But then the young man finally did something—
He reached down and pulled up the skirt of his dress, exposing his panties and the big bulge hiding inside of them. He rubbed his fingers down the length of his bulge and then he reached in and fished his cock out. Barry found himself settling back into his place. Now he couldn’t leave. Now he had to stay and watch.
He’d heard of transgenders and cross-dressers before, but he’d never actually seen one before. Whenever the topic came up at work or on television, he always thought about the hairy Freddie Mercury lookalikes who stood and smoked outside the local gay bars, covered in body hair, with broad shoulders. He never thought of a petite, gentle looking young man whole smooth skin and a soft face. He didn’t think that a trans chick could actually look like a real chick, but this trans chick was awfully close. Even with her cock out, it was hard to see her as a man.
Barry watched as she stroked her shaft. Pink light flashed on her face. Barry assumed she was watching pornography, or maybe she was sharing webcams with a guy somewhere in the world. Though she seemed too timid to be sharing herself, even with the anonymity of the Internet. There was something about her mannerisms and the way she held herself that made her seem like the timid type.
She laid her head back and her lips parted. It was hard to see her now, so Barry had to stand up carefully on a fallen log. She was firmly pulling her cock up towards her sternum. She had a big cock—especially for a girl. With her free hand she reached down and fingered her butthole. She was only sticking the tip of her finger in—it seemed to be enough for her.
Barry felt his pants tightening. Was he aroused by the sight? He had to reach down and feel to believe it—he actually had an erection. He laughed and shook his head, realizing he was discovering something about himself. He didn’t mind being attracted to a trans chick. At least she was cute. At least she wasn’t some two hundred pound drag queen.
She stroked her cock elegantly—far more elegantly than any man could stroke his cock. She pushed her hips up into the air and her lips parted wider. Her cheeks turned red and then she pulled her finger out from her asshole and reached for a handful of tissue paper. She pressed that bundle of white tissue paper to the tip of her cock and then her body shuddered. She was coming. She slowly brought her hips back down to the mattress and her shoulders relaxed. She remained still for a few minutes, her chest heaving, her nipples still erect and pushing against the soft satin of the dress. Then she got up and threw that bundle of tissue paper into the toilet. She started getting undressed, and Barry knew it was his cue to leave.
He knew his cue to leave was five days before, when he first saw that young man in the window. He should have never stayed to watch, but he couldn’t help it. And now he felt even more helpless. Now, he was already planning on making the trek out to Discovery Pines again the next night. He had nothing better to do and he had nothing better to look forward to.
And it was nice to escape the anxiety Sarah filled him with, even if it was just for thirty minutes or so. He was sick of constantly thinking about Sarah and her lawyer and the upcoming court date. He was sick of constantly staring at his bank account, wondering how he was going to come up with all that money to scrub her from his life.
As Barry made his way home through that dark forest, an idea occurred to him. At first it seemed like an evil and cruel idea, but then he thought more about it and realized it may be his get-out-of-jail card. Maybe it was a bit mean, but maybe it would mean saving his house and his bank account and all of his future paycheques. A slight grin crossed his face.
CHAPTER IV
It had been a whol
e week since Liam had started cross-dressing again after his prolonged absence. He was excited—the new house was perfect. He had all the privacy he’d always wanted. Even the little lock on his bedroom door made all the difference—a little extra peace of mind as he got himself dolled up. He’d even started getting dressed up during the day, which he’d never done before—only ever when his parents were out of the house and his sister was occupied. It was extremely rare that she would ever come up to his room, so from time to time, he took the risk.
Liam was on his way to his room to try on a little dress he’d nabbed from his school’s drama room when his sister called his name. “There’s a package here for you,” she said. She was in the kitchen holding a box.
Liam’s heart skipped a beat and then fluttered down into his stomach. He quickly tried to remember if he’d ordered some lingerie or some makeup online. He never had any of his sissy supplies sent to the house, but maybe he made a mistake. Maybe he accidentally put his own address in the shipping details instead of a neighbour’s address, with a fake name… But he couldn’t remember ordering anything, to his house or to another house.
“Well do you want it or not?” his sister said. She was leaning against the counter, drinking a coffee.
Liam forced a smile. “Sure. I don’t remember ordering anything though,” he said. He took the box and gave it a shake. It was light, as if there wasn’t much inside. As he started towards his bedroom, he noticed there were no stamps on the box, and no markings from the post office or USPS. There wasn’t even a return address. It was just a box with his name and address. Liam didn’t have much experience with the post; he’d mailed a few letters to a pen pal back when he was in elementary school, and that was about it. But he knew you had to include a return address or the post wouldn’t deliver the package—at least that’s what he thought. Maybe he was wrong…
He closed the door to his room and then he locked it just to be safe. His heart was still trembling in his gut. A cold sweat bathed the back of his neck, but he wasn’t sure why. He kept telling himself that he had nothing to worry about, yet he continued to worry.
Using a pair of scissors, he opened the box. It was filled with crumpled up paper—about ten wads—and a small thumb drive. He took the thumb drive over to his laptop. As he inserted it, he noticed his hands were trembling. He took a deep breath. There were a couple of files on the small thumb drive: a zipped folder labelled ‘PICS’ and a little text document labelled ‘READ ME FIRST’. Liam followed the proper order by opening the text document.
“Hello beautiful. Thank you so much for your nightly shows. For some time now, they’ve been the highlight of my day. I hope this message doesn’t come as too much of a shock.” The letter continued but Liam’s vision suddenly became blurry as a ringing started in his ears. He quickly looked down at the bottom of the letter to see who sent it, but there were no names. He navigated back to the folder and tried right clicking the text document, to see if the sender’s name was encoded into the metadata. Then, he unzipped the folder and saw the pictures: pictures of himself, taken through his bedroom window, in makeup and lingerie. He didn’t look through the pictures—the thumbnails were enough. He realized he hadn’t taken a breath in almost a minute, so he took one now: a big, long, deep breath. He had to force himself to take another. He could feel the colour draining from his face. He’d never fainted before in his life, but he suddenly felt like he was about to for the first time.
He went back to that text document.
“I hope that you don’t stop your nightly shows after reading this letter,” the mysterious sender wrote. “In fact, I strongly suggest you continue your shows, unless you want these photos to end up in the hands of your friends and parents. And I would like it if you kept your blinds open. But don’t bother trying to spot me—you won’t see me.” Liam forced himself to take another breath. He couldn’t hear anything over the ringing in his ears—not even the knocking at his door. It wasn’t until his sister let herself into his room that he realized there had been someone at his door. He quickly closed that note and looked up at his sister. “What’s up?” he said.
“Didn’t you hear me knocking?” she asked.
“No,” he said.
“I just wanted to know what the package was.”
Liam looked over at his nightstand and grabbed the first thing he could see. “A new phone charger. I bought it on eBay for ten bucks like a month ago,” he said. “They charge like ninety bucks at the Apple Store.” He forced a smile.
“That’s a big box for a phone charger,” she said.
“I agree.”
His sister seemed satisfied, so she left, closing the door behind her. Liam waited until her footsteps were inaudible before he crept over to the door and locked it. Then he went to the window and shut his blinds before going back to his computer and opening that letter to read the rest.
“I would like for you to continue putting on your shows, every night. In the woods behind your house—about forty paces in, behind a fallen log—you will find a red box. In that red box you will find a new note every day—instructions. Please follow the instructions and I’ll make sure these pictures remain between you and me.”
Liam’s hands felt cold. He slipped them under his bum to warm them up, but it didn’t seem to help much. He tried to regain control of his breathing by taking a series of slow, deep breaths. Then he got up and went to the window and looked out at the woods. Even with the sun out, it was hard to see into those woods as the thick treetops blocked out the light. During the night, anyone on the other side of that first row of trees would be invisible.
After twenty minutes of anxiety-ridden silence, Liam decided to go out and see if the red box was real. Before he left, he looked at that text document note again, to make sure it was real and not just some horrible daydream that had come and gone. Unfortunately, the note was real.
He put on his shoes and casually meandered outside. Instead of heading straight to the forest, he decided to walk down the street, to a walking path that led to the woods. Then he doubled back. He though the detour would look more inconspicuous to anyone watching. He certainly didn’t want anyone finding that red box with the instructions inside—instructions that would probably give his cross-dressing secret away.
He looked around often, to make sure no one was watching. It took a while to find that red box out in those woods, but it was there, behind a fallen tree, nestled in a pile of leaves. He opened it up. Inside the box was a little French maid costume, complete with the frilly lace headband and white stockings. There was also a piece of paper and a pen. There was a note written on the piece of paper: “Please write down your shoe size. And take the costume for tonight’s show. Thank you.” So Liam wrote down his shoe size and left the paper in the box.
Liam felt his gut turn as he picked up the black and white French maid outfit. It was soft in his fingers. He was excited to put it on and feel it against his skin. But he was terrified to do it with a mysterious audience.
CHAPTER V
Barry wasn’t proud of what he’d done. But he knew it was a necessary evil.
He was now on his way to meet with Sarah for the first time since she’d moved out. It was a meeting scheduled by her lawyer, to try and come to a deal before going to court (to save everyone’s time an Barry’s money). Barry was hoping that he could plead with Sarah, but his lawyer told him that talking to her personally would be highly discouraged. He was going to try anyway.
When he pulled up to her lawyer’s building, he realized his situation was worse than he originally though. Her lawyer’s name was on the side of the large building, and his office was up on the top floor, looking down at the city. Barry’s lawyer worked out of a strip mall in the grungy part of town.
Barry had to buzz to be let in. His lawyer was already upstairs waiting for him. “Remember, don’t say anything unless you’re asked a question directly. And try to remain civil,” his lawyer said as they walked towards the m
eeting room where Sarah and her lawyer were waiting.
Barry noticed Sarah’s lawyer before he noticed Sarah. He was wearing a slick black suit with a dark red tie, and he had his hair slicked back, making him look like the villain in some World War 2 movie.
Sarah looked different. She had her long hair recently bleached blonde and she now had it tied up into a fancy-looking braided bun, which she probably had done by a professional. Her makeup was also better than ever before, also probably done by a professional. Barry didn’t know a lot about women’s shoes, but he knew that the ones on Sarah’s feet were Louboutins—probably worth over a grand. And her sparkling pantsuit didn’t look cheap either. By the looks of it, Sarah was already spending Barry’s money, positive she was going to win the case.
But for the first time in months, Barry had a glimmer of hope glowing inside of him. Sarah wasn’t necessarily going to win the case. In fact, she might end up owing Barry a lot of money. According to Barry’s lawyer, if Barry were to win, he would be entitled to counter-sue for expenses and damages. Maybe Barry would be the one wearing the expensive clothes at their next rendezvous.
“Let’s just make this quick,” Sarah’s lawyer said. “I’ve got a dinner at five and I want to make it to the gym first. My client and Mr. Peters were common-law partners after two years of cohabitation. Having been common-law partners, my client is entitled to half of Mr. Peters’s assets. We’ve already gone ahead and calculated the value of Mr. Peters’s assets at the time of the split. That number is $910,000. Split in half is $455,000.”
“Okay,” Barry’s lawyer said. “But they weren’t technically dating for the full two years. For the first year they were just roommates, and roommates can’t be considered common-law.”
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