He also considered leaving the country. His dad was born in Austria, and he was pretty sure that meant he could apply for Austrian citizenship. But he didn’t speak a word of German, or any language aside from English. But how long would it take to learn? And would Sarah’s legal team track him down if he was hiding out in Austria?
Barry couldn’t hear Whiskey, so he whistled. The woods were silent for a moment, and then he heard his dog galloping towards him. Whiskey’s goofy face materialized through the trees, his tongue swaying from side to side. He mushed his wet nose against Barry’s leg. Barry gave him a pat on the head, and then he trotted off back into the woods, trying to find a bunny or a mouse or even just a really good stick.
Barry walked for longer than usual, his mind adrift with that same tiring anxiety. He pulled out his phone flashlight so he could see, as the glow of the city lights was far behind him now. He knew it wasn’t amazingly safe to be wandering out into the woods in the middle of the night, but it was nice to get away, to be somewhere that no one would ever find him. He could pitch a tent out in those woods and none of those letters from that damned lawyer would ever reach him. It was peaceful out in those woods, even if there were coyotes watching him secretly from behind tall trees.
Barry checked the time. He’d been out for thirty minutes and he was still walking straight out into the woods. He figured it was probably best to turn back now—and then he noticed a glow in the distance. So he kept walking. He had to climb up a muddle slope before he saw the source of the mysterious glow—
It was a lit up window. And not too far away was a porch light, flickering slightly as moths threw their delicate bodies at it. He’d reached Discovery Pines: a new community that had just opened up a few months earlier.
Barry had never seen Discovery Pines before, but he’d heard the ads on the radio. “Your new home at Discovery Pines will be so relaxing, you’ll forget you aren’t on vacation,” was their radio slogan. Barry always thought it was a stupid slogan. He’d seen pictures of the community on billboards in town. It was just another suburb with a big manmade lake in the middle of it. Looking at it now, he wasn’t terribly impressed.
Every house looked the same. The siding on the houses was cheap. The stone looked fake and the shakes looked like plastic. Even the grass looked strangely fake, and maybe it was. Barry knew a guy who had fake grass put in his back and front yards so he wouldn’t have to mow it. Ironically, he still had to water the grass, or it would start to smell as dog pee would stagnate on the false green blades.
Whiskey had wandered into one of the yards. He was sniffing around, trying to figure out where the hell they were. Barry tried quietly whistling him back over, but Whiskey kept sniffing around. He would have whistled louder but he didn’t want to alert any of the new homeowners. “Whiskey,” he whispered as Whiskey wandered up onto one of the decks. He started smelling the homeowner’s compost bin. “Get away from that!” But his whispers weren’t loud enough for the stubborn animal.
Barry took a step forward. His plan was to quickly grab Whiskey and then to disappear back into the woods before anyone noticed him. But he didn’t make it more than a step before a figure appeared in that glowing upstairs window.
It was a young man and he was naked. His skin was fair and his body appeared to be shaved smooth. Barry looked away quickly, now worried he was going to end up arrested and charged with voyeurism and prowling. With his luck, it seemed likely. So he ran quickly to grab Whiskey by the collar, and then he started running back towards the woods. He got Whiskey onto his leash and then he looked back again, though he wasn’t sure why he looked back. And that’s when he saw the young man slipping into a pair of red lacy panties.
Barry stopped, his heart pounding, and he found himself staring for reasons unbeknownst even to himself.
CHAPTER II
It had been a long time since Liam had last gotten himself dolled up. For two months, he’d resisted the urge to sneak into his sister’s bedroom to secretly borrow her clothes, and he’d kept his wig and makeup kit hidden in his locker at school. Every day he worried that someone would find that makeup kit in his locker, even though he was the only person who knew the combination.
He was used to getting dolled up all the time—almost every night. At their old house, he had a whole suitcase full of his sister’s clothes hidden under his bed, and he kept his makeup kit stored away in a bag at the back of his closet. He would wait until everyone went to bed and then he would get dressed up. Once he was dressed up, he would do his makeup. He never did his makeup first, in case his sister or his parents were taking longer than usual to fall asleep. He knew he could get changed quickly, or pull a blanket over his body—but he couldn’t wash makeup off quickly. Sometimes he wouldn’t even bother with his makeup; he thought he looked pretty good without it, but he knew he looked better with it.
But when it came time to start packing for the big move, Liam wasn’t taking any risks. While he was home alone, he snuck all of his sister’s clothes back into her closet and then he packed up his wig and makeup kit and brought them to school. He wasn’t willing to let them be found during the packing and shipping process.
Liam kept his cross-dressing a secret. It was more than a secret. People tell their close friends their secrets, but Liam didn’t dare to tell anyone. If his friends and family found out that he liked to wear panties and skirts and lingerie… he would rather be dead. Though he sometimes fantasized about telling everyone. And in his fantasy, everyone was fine with it. But he knew that reality would be much different than his fantasies.
Now, Liam looked down at his red lace panties, which were his own—the first piece of his own female wardrobe. He bought them online and had them shipped to a neighbour’s house, who he knew was out of town for the month. He carefully tracked the package and then snatched it from his neighbour’s mailbox just minutes after the mailman put it there.
He walked over to his closet mirror and admired the panties. It was the first time he’d put on a pair of panties in months. He would have put them on much sooner, but there were complications when they moved into that new house in Discovery Pines. The house wasn’t finished when they moved in. Workers were still coming in every morning at 7:00 AM and they weren’t leaving until 9:00 PM. It took six weeks before they finally put doors in the doorframes. And it was hard to secretly get dolled up when there are no doors to hide behind. So Liam had to be patient.
Even once the doors were up, Liam still had to acquire clothes. His sister was in no rush to get settled in her new bedroom. For two months, she kept all of her things in moving boxes, leaving her closet empty. She was too lazy to unpack everything, and she only ever wore the same three outfits anyway. So all of the skirts and dresses that Liam’s sister never wore remained hidden away in boxes, and Liam knew better than to try and dig his favourite outfits out while his sister was out of the house. She might not notice the missing outfits when she finally got around to unloading those boxes—but Liam wasn’t satisfied with ‘might not’. He knew she wouldn’t notice a few outfits missing from the back of her closet once they were stashed away.
But finally, she got around to unpacking (with some help from their mother). And Liam was finally able to sneak in and grab what he needed without nudging anything out of place. He snuck his wig and his makeup kit home and he stashed everything away in a discreet black backpack in the back corner of his closet.
And finally he had everything he needed to get dolled up in peace. He was excited. The new house was much bigger and the insulation was much better. He didn’t have to worry about thin walls and creaky floors. For once, he had his own en-suite bathroom, so he could get his makeup washed off without having to bound across the hallway, just a few feet from his sleeping parents’ bedroom. And now he wasn’t even on the same floor as his parents; they were downstairs, across the hall from his sister, and he had the upstairs all to himself. And to sweeten the deal, his bedroom window no longer looked right into the nei
ghbour’s bedroom window. Now, his window looked out at the woods, so he didn’t even have to bother closing his blinds.
Once in his red panties, he slipped into one of his favourite outfits: a red plaid skirt and a charcoal grey tank top. He usually wore a bra stuffed with socks, but in the past few weeks he’d noticed a bit of breast growth. He’d been secretly taking hormone pills for nearly a year, and the effects were finally starting to show. He stood profile to the mirror and he straightened his spine. The slight bumps of his new breasts were just barely noticeable. He smiled but his heart skipped a beat. How big would they be in a few months? How big would they be in a few years? At what point was he going to have to fess up to his family? He couldn’t just wear baggy sweaters for the rest of his life—or could he?
When he’d starting taking the hormones and the hormone blockers, he assumed the courage to come out with eventually come to him. But now, he was more terrified of coming out than ever before. Shortly after they moved into the house in Discovery Pines, Liam overheard his dad saying, “Thank God our kids aren’t gay.” He said it after meeting the gay couple, who lived just a few houses down. Apparently they’d spent the last four years waiting to be approved by an adoption agency. Until that comment, Liam never thought his dad was homophobic. Liam never really knew how his dad felt about gays and lesbians and bisexuals and transgenders—he was always too afraid to ask.
But he couldn’t turn back now. He’d been taking hormones and hormone blockers for a year. He was committed. His body had already undergone changes that were permanent. And he loved the idea of being a girl, even if it meant keeping it hidden twenty-two hours of the day. Though he was starting to worry about his voice; it was starting to change, getting higher and softer, and it was getting harder and harder to deepen it.
He didn’t want to think of any of those issues right now. Right now, he just wanted to enjoy getting dolled up for the first time in what felt like forever. Once he had his little outfit on, he put his wig on. It was tied into two tight French braids, which he decided to keep, as they looked really cute with the outfit. He slipped into his new en-suite bathroom to do his makeup. He took his time, not feeling tired or rushed, or worried that his parents would wake up and come into his room. He started with mascara, then he put on a bit of eyeliner, and then he went heavy with the eye shadow. He dug out his concealer but he decided not to put any on. His skin looked surprisingly clear and, thanks to a year of HRT, his skin was softer than ever. So he finished off his look with a bit of lip-gloss.
Then he found himself back in his bedroom, in front of his full-length closet mirror. He looked at himself from different angles, admiring his progress. Feeling confident in the insulated walls and his new distance from his parents’ and sister’s bedrooms, he whispered to himself in his most natural girl voice, “You’re looking so cute.” He smiled.
And then he remembered that he owned a toy that he’d never used before. It was another gift he bought for himself online months before: a small vibrating dildo. It was a discreet toy, which was disguised as a small lamp until you unscrewed the base and pulled out the pink cock. Liam had used the dildo many times before, but never with the vibrator turned on. When he bought it, the website insisted that it was a silent vibration, but Liam disagreed. It was a loud unit, and he’d never been able to use it, worried it would be enough to wake up his family. But now, he felt more confident. He bent over with his back to the mirror and he lifted up his skirt. He pulled aside his panties and he started to wiggle the cock into his ass. He took a deep breath and then he pushed the on button.
It started to vibrate. It didn’t seem as loud as it used to—though Liam had a feeling that was just because he wasn’t so paranoid in the new house. He pushed the cock deep into his butt, until he felt the tip buzzing against his prostate. It was only a few seconds before his legs started to tremble. His cock was already hard. It never took much to make his cock hard once he was in a pair of panties.
He took a deep breath and looked over his shoulder, admiring his curvy ass, which was gracefully accepting that pink dildo. He thrust it quickly into his butt and his legs began to tremble harder. He moaned and then quickly turned his face and mashed it into a pillow, so no one would hear his moaning—not that he was too worried. He’d done a few tests over the past few weeks, putting music on in his room before casually meandering through the house to find out how loud he had to be before he could be heard. Even when he had his speakers set to their loudest setting, his music wasn’t easily heard downstairs.
But he still wasn’t about to take any chances.
He pressed that vibrator against his prostate and then he used both of his hands to jerk himself off: one hand massaging his balls and one stroking his rod. It didn’t take long. Thirty seconds later, he was trembling all over with an intense euphoria pulsing in his cock. He looked down just in time to see white streamers erupting from his cock, making a mess of the side of his bed. Usually he would have put a towel or two down, so there wouldn’t be too much mess—but this night he’d been too excited to think ahead.
Now, as he stood up, he felt embarrassed. He made a real mess of the side of his bed, and he couldn’t exactly sneak down to the basement to do a load of laundry. So he wiped up what he could and then he flipped his sheets over to hide the cum stains. He quickly put away his dildo and then he locked himself in his bathroom while he washed off his makeup.
CHAPTER III
It was five days later when Barry found himself back out in those woods, walking back towards Discovery Pines. For five days he tried to forget what he saw, and for five days, he tried to fight back the urge to go back. But on that fifth night, the urges were too powerful.
He didn’t know why he wanted to go back or what he wanted to see. It’s not like he enjoyed watching that young man frolicking around in women’s clothing. It’s not like he’d ever been attracted to men or interested in traps. But still, there he was, making the long hike through those woods in the middle of the night, just for a chance to catch another show in that same bedroom window.
He wasn’t sure where he was going. He knew Discovery Pines was west of his house, but he didn’t exactly use a map and a compass during his first trek out, when he accidentally discovered the small community. And it’s not like he recognized the trees or the fallen logs. But still, he figured he would be able to figure it out.
He had Whiskey with him, and he was ready to put Whiskey on a leash as soon as he saw the faint glow of the removed community. He didn’t want anyone to know that he was there, especially now that he was going to stare through a stranger’s window. He shivered at the realization that he was literally walking thirty minutes just to commit a crime—voyeurism was in fact a crime, punishable with jail time (he had looked it up a few days after the initial incident). But even knowing what he was doing, he still found himself doing it. He figured if he was caught, he could easily convince whomever he needed to convince that he was just out walking his dog.
When he finally saw that faint glow, his heart skipped a beat and he perked up. He knew it was unlikely that he would catch the same show again, even though it was the same time of night. He knew it was unlikely that the young man’s blinds would even be open again, but it’s not like he had anything better to do. He’d been unemployed now for four days, based on his lawyer’s recommendation. “If you aren’t making any money, then the judge is less likely to slap you with alimony,” Barry’s lawyer said. So he begged his boss to fire him, and he was successful.
But now he had nothing to do—nothing to do but wander around the house that would soon be sold to pay a woman who didn’t deserve anything. Barry tried not to think about her, but it was impossible not to. She was everywhere he looked. Even things that had nothing to do with her made him think of her—like his guitar. He bought that guitar years before he met her, but now he would probably have to sell it to pay off her absurd fees. He was afraid he might even have to sell his dog to pay her off—he wasn’t su
re he would be able to afford the dog food once she took everything he owned.
The more he thought about her, the angrier he became. He found himself wondering: if she was supposedly entitled to half of his assets, why did it seem like she was taking everything? Where did they come up with that $455,000 number? He bought his house for $350,000—and half of $350,000 is $175,000. So where did the rest of that incredible number come from? Barry had tried asking, but the lawyer’s answer made no sense, and Barry knew that he wouldn’t be able to make any sense of it, no matter how it was explained to him. Because the whole thing was completely nonsensical.
Barry noticed that familiar glow growing in the distance. He called Whiskey over and put him on a leash. Then he started creeping towards the light, his heart suddenly pounding. And for the first time in five days, he forgot that he was in the middle of a ludicrous legal battle. He forgot that there was a crazy woman trying to bleed him for every penny he had and every penny he would ever make. Now, he was only thinking about the crazy sight he’d seen almost a week before. Now, he was only thinking about that young man who looked surprisingly like a girl with a skirt and a wig and a bit of makeup.
Barry carefully climbed over the muddy ridge and found himself in an unfamiliar spot. The houses were clearly built by the same developer, but they weren’t familiar. There were a few porch lights left on, but now glowing windows. Barry knew he wasn’t in the same place and he wasn’t sure which direction the same place was. He looked both ways and tried to see if there were any recognizable landmarks. But there was nothing familiar. So he started walking down, along that ridge, looking at houses for anything familiar. He tried to remember if there was anything different about that house, aside from the sissy getting dolled up in the window.
He remembered a garden gnome in one of the flowerbeds. So he kept his eye out for that garden gnome. He couldn’t spot it yet, but there were still plenty of houses backing onto that wooded area. The community of Discovery Pines wasn’t huge—maybe one hundred houses in a large ring around a private manmade lake. Barry knew it would only take twenty minutes or so to walk around the whole thing.
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