“I know you weren’t visiting your mom. You know that right? I know you were at some weird religious camp for gay kids.”
He stared into my eyes and then he shrugged his shoulders. “It needed to happen. I’m not gay anymore, and that’s the way it should be. But let’s maybe not talk about it. Okay?”
“I want to talk about it,” I said.
“Please just don’t. I’m kind of tired. I think I’m going to go to bed.” I watched him shuffle off to bed. I told myself that he just needed another week or two—he just needed to be re-immersed into real life—surrounded by billboards of pretty women in gorgeous outfits. His brain just needed time to find its way back home from that camp. But after two weeks, he was still dull and lifeless. I was ready to give up, but then I got an idea.
I had to wait a few nights, as our parents were going out of town for another church event. My sister told our parents that she would be home while they were gone, but I’d already overheard my sister talking to her friends on the phone about a big party on the other side of town, so I knew the house would be left to just Nathan and me.
It was an anxious few nights, but they were well needed. I used that time to learn: watching video tutorials and practising different techniques while my family was asleep. I didn’t get a ton of sleep, but I knew there would be time for sleep later. Saving Nathan was more important than sleeping.
My heart was pounding the afternoon my parents left. I watched as the car pulled away, and then I watched on my phone as they made their way to the airport. While my mom was in the shower that morning, I turned on her Find My Friends (an app she didn’t even know about) so that I could track her, to make sure she wasn’t turning around and coming home. I checked the app a few hours later and saw that she was a few states away. It was 7:00 PM when my sister walked up to the front door, all dolled up with her purse at her side. “I won’t be home until the morning. Don’t you dare tell mom and dad.”
I smiled and nodded and then I watched my Find My Friends app as she made her way across town (I turned on her Find My Friends while she making lunch). I would check on that app multiple times through the night as I tediously got ready for my rescue mission.
CHAPTER XI
First I shaved my legs and my crotch and my armpits. Then, I rubbed myself with moisturizing lotion. I nearly used a whole bottle trying to get my body soft like a woman’s. I thought I felt pretty good. Then, I had to combine costumes to create something I could work with. I used the Playboy Bunny costume and the wig from the Catwoman costume (it was a newer Anne Hathaway model). The wig was long and straight and brown. I even wore the Catwoman ears, because the band helped keep the wig firmly on my head.
Then I spent the next couple of hours perfecting my makeup. I brought up those old makeup tutorials and watched them over and over as I carefully perfected each detail. The eyeliner was by far the hardest to get on right. And then I had to be careful not to overdo it with the eye shadow and the lipstick and the blush, so I wouldn’t look like a drag queen. I wasn’t trying to transform myself, I was just trying to look feminine.
I tried squeezing my feet into a pair of my sister’s heels, but they were too small. I couldn’t believe how small Nathan’s feet must have been. So I was stuck barefoot. Luckily, with the hair shaved off the tops of my feet, my feet looked surprising feminine, so I wasn’t too worried.
It was around 11:00 PM when I finally found myself in front of Nathan’s bedroom. I took a deep breath and looked down at my body. I looked as good as I was capable—which really wasn’t bad. My curves were impressive in that tight Playboy Bunny one-piece. With the bowtie around my throat covering my Adam’s apple, there wasn’t any clear giveaway that I wasn’t actually a woman—aside from my voice, which was still a complete mystery even to me. I hadn’t had a chance to practice it, so I was just going to wing it. I’d watched a few tutorials on how to sound more feminine, but I hadn’t been home alone to test the techniques—until now.
I took a deep breath and then I knocked on the door. I waited a second and then I knocked again. “It’s unlocked,” Nathan called out. I hesitated, looking down at myself again and I wondered: is this a bad idea? Was I attempting to undo work that was for a better good? Was I wrong to try and convert Nathan back to being his usual self?
Then I thought of Nathan sitting on the bed, reading a boring book, feeling empty inside and knowing that’s the way he would spend the rest of his life. I couldn’t let it happen. So I let myself into his room.
I took one step in, my heart pounding, and then he looked up at me. He froze, his eyes becoming wide and his cheeks becoming pink. “W—What are you doing?” he said, his lips parting slightly.
I cleared my throat before attempting my first female voice. “I just wanted to hang out,” I said. My voice was more shaken than expected, but I don’t think I sounded bad—just nervous as hell. “Want to hang out?”
I watched as he swallowed and cleared his throat. “Um, this really isn’t a good idea. You, uh, you look good and all, but I really can’t. I promised I wouldn’t.”
“You promised who?” I asked.
He shook his head. “Really. This isn’t a good idea.”
I walked over to his bed, ignoring him. I took a seat on the edge of his bed and then I threw a leg over his lap. My legs were clad with fishnets. He stared down at my leg and then he looked away from me completely. “Seriously. I think you should go,” he said.
“But I don’t want to go. I want to spend some time with you. Don’t you want to spend some time with me?” I asked. My heart was pounding hard now. I was worried I was about to slip into a full-blown panic attack. But somehow I managed to hold myself together.
“I’m not gay,” he said.
“Do I look like a man?” I asked, and then I felt my lips curl into a smirk.
He looked at me. “No. Not at all. But—But you are.”
“Not right now I’m not. And last I checked, there’s nothing gay about a man being with a woman. Right?” I ran the tip of my finger down the length of his arm.
I watched as he took a deep breath. “You’re wearing that perfume,” he said.
“You like it?”
He nodded his head. “It smells good. But seriously. I think you should maybe leave.”
“Tell me you don’t think I’m sexy and I’ll go.”
He was silent. He bit his lip and then he cleared his throat again. “You’re sexy,” he said.
“I said tell me you don’t think I’m sexy.”
His face was dark red now. “But you are sexy. Okay? Isn’t that enough.”
I leaned over and kissed him on the lips. I knew that I was kissing a man now—a man who wasn’t dressed up like a girl. His hair was even short now, and he’d let his leg hair grow out. Yet there I was, locking lips with him. And he was kissing back—but just for a few seconds. Then he pulled away. “No—it’s not right. I can’t do it.”
“Who says it’s not right?” I asked.
“The Bible,” he said.
“And since when do you care what the Bible says?”
He looked into my eyes. He looked tormented, but at least he had an expression. At least he was still alive and not just some dead robot. There was another long silence, and then he leaned forward and kissed me. He grabbed my sides and pulled me down onto his bed. He was starving for my body and he was finally allowing himself to feast. We kissed as he held me down, feeling my body, caressing my smooth skin. He started sucking on my neck, giving me a hickey that would be a pain to cover up for the next few days. And then he reached down and started rubbing the bulge between my legs.
“You look good,” he said, and then he kept sucking my neck and rubbing my cock.
“Thanks,” I said. I did my best to undress him while he made love to my body. I was so happy, seeing him back to his usual energetic self. I’d done it: I’d rescued him from his questionable religious lobotomy.
He leaned back and quickly pulled his shirt
and pants off. His cock was already erect and throbbing. I wondered if he’d gotten off at all in the past few months. I sat up and I pushed him onto his back. Then I looked down at his throbbing member and I smiled. “Just relax,” I said, and then I sunk down.
I’d never sucked a cock before, but I was happy that his would be my first. I stroked it gently before leaning in and allowing it into my mouth. It felt warm against my tongue. The throbbing was intense, but I kind of liked it. I bobbed my head up and down, exploring his girth with my tongue. I caught myself smiling when he started moaning. He was enjoying himself, leaving me feeling beyond satisfied.
I managed to get his whole cock into my mouth (by pressing a few inches into my throat). I pressed my nose into his pubic hair until I gagged, and then I continued sucking his tip. I tasted his sweet pre-cum and he groaned again. I had a feeling he wasn’t going to last long.
Suddenly, he pushed me over, rolling me onto my stomach. He quickly rolled over me and straddled my backside. His hands grabbed my ass cheeks and he squeezed. “I like your tail,” he said, playing with my cotton Playboy Bunny tail. Then he pulled my tight one piece to the side, revealing my asshole. “It looks tight,” he said.
“It is tight. I’m a virgin back there.” My heart continued pounding.
“Well I’ll be as gentle as I can,” he said.
“Just not too deep,” I said as he pressed his saliva-covered tip up to my puckering hole. I closed my eyes and tried to control my breathing. He started pushing in. It hurt a bit at first, but only for a minute. He started thrusting in and out, stretching my tight rim wide. He held my hips firmly. I clenched the pillows on his bed with both of my hands.
With each penetration he sunk deeper and deeper. I had to remind him not to go too deep a few times, but after a few minutes, his pelvis was pressing against my butt and he was fully inside of me. It felt nice. He was pressing against my prostate, making my legs tremble. It felt good—far better than I’d expected. I tried to squirm but he held me firmly in place. “I’m close,” he said. He came down harder and faster, his pelvis slapping my ass red. “I’m really close.”
A euphoria was swelling in my crotch. I grabbed the pillows tighter and I screamed into one of them. My legs wriggled but he didn’t stop. I didn’t want him to stop. That euphoria was growing stronger and stronger and I couldn’t wait to see just how strong it could get.
And ten suddenly I felt a hotness in my cock. My whole body trembled and then that hotness released and then I felt a wetness. A few minutes later I would discover that I came all over Nathan’s bed.
“I’m coming,” he said with a groan, and then he pulled out and I felt his hot cum blasting my back, soaking through the thin fabric of that Playboy Bunny costume. I felt empty but still teetering in my euphoric state. I squirmed and moaned and then I rolled over and we kissed.
Nathan moved out later that month, into his own one-bedroom apartment on the other side of town. I lived at home for the next year, though I spent most of my time over at Nathan’s house. We never came out officially—Nathan never came out as trans or gay or bisexual. And I never came out as whatever I was—maybe all of those things or maybe none of them. There was no point in coming out because we never thought it was anyone else’s business. We knew what we were and we kept it between ourselves.
Nathan had a huge walk-in closet, which we kept stocked full of the cutest and sexiest outfits. I started growing my hair long (wearing it tied up when I was out, and wearing it down when I was with Nathan), and Nathan grew his hair back out too. His hair grew much quicker than mine, but I soon learned that I looked pretty cute with medium-length hair.
We spent many nights together, taking turns dressing up. Sometimes we would both dress up and fuck like a couple of horny lesbians. And sometimes (though it was rare, when we were feeling exceptionally lazy) we would just fuck without getting dolled up. But getting dolled up was half of the fun, so we rarely missed the opportunity.
It took about a year before Nathan told me to go deeper. “Stick your whole cock in me.” I couldn’t believe his petite body actually took the whole thing—and he took it like a champion, while dressed up like a slutty little club girl.
Sometimes we would go out together, dolled up and pretty. Nathan would get hit on more than me, but I still got my share of attention. It was surprisingly rare that people would realize we weren’t really woman, but we weren’t going out to fool anyone—we were just having fun.
I finally moved out a year later, into an apartment a block away from Nathan. Though it was a pointless transitional apartment, seeing as I continued to spend all of my time over at Nathan’s house. My place just became a glorified shoe closet until we finally moved in together—a two-bedroom at first, so our parents wouldn’t freak out, and then a one-bedroom six months later when we decided we didn’t care what our parents thought.
Because it didn’t matter what they thought. All that matter was that we were happy—and we were.
THE END
BOY TO GIRL
Out for a walk one night, Barry spots a peculiar sight in the window of a house: a young man putting on women’s clothing. Out of curiosity, he stays to watch, and he watches until the young cross-dresser is cleaning up his bed sheets. On his way home, he realizes the young man might just be the solution to all of Barry’s legal troubles.
Liam is a young man with a secret: when everyone in the house is asleep, he likes to put on his sister’s clothes for a bit of adult fun. But the fun comes to a sudden end one night when he receives a package from an anonymous sender, telling him to carry on with his nightly shows or lewd photos will be shared with all of his friends and family members. The arrangement seems cruel, until Liam starts receiving cute new outfits every single day.
But as the days go by, the blackmailer wants more and more.
CHAPTER I
Barry needed a walk and he needed a cigarette. His dog had also been pacing at the back door for the past twenty minutes, crying progressively louder, so Barry figured he would stone all three birds at once. He grabbed his pack of cigarettes, his lighter, and Whiskey’s leash.
He didn’t plan on using Whiskey’s leash, but he always brought it with him just in case. Whiskey was usually fine just wandering around the wooded area behind his house. But occasionally someone else would come by with their dog on a leash, and Barry got in shit once from one of his neighbours, an old man. “You know this isn’t an off-leash area, right?” the neighbour said with a scowl. A few days later, Barry received a complaint from the city, filed by an ‘anonymous’ neighbour. But Whiskey hated walking on-leash and Barry wasn’t too worried. They weren’t going to fine him without proof, and the old man certainly didn’t know how to operate a camera to obtain the necessary proof.
But some grumpy old man was the last thing on Barry’s mind. He had bigger problems than a crusty old neighbour. He had an ex-girlfriend who was trying to take all of his money—and he didn’t have much.
Sarah and Barry were roommates for two years, and they became intimate a year into their home sharing. One night after a booze-filled party, they fucked on the living room sofa, and when they woke up the next morning, they decided to give dating a go. A year later, Barry found out that she’d been spending drunken nights on the sofas of many different men, so he told her to move out. A week later, he received a letter from a lawyer, notifying him that Sarah wanted half of his assets. Apparently, after living together for two years in the province of British Columbia, they were considered common-law, giving Sarah the same rights as a married woman. Therefor, with their split, she supposedly had the right to half of Barry’s assets.
He thought it was a joke at first, until he received another letter from Sarah’s lawyer a week later with more demands. She wanted alimony on top of half of his bank account and half the value of the home he bought a year before he met Sarah: $455,000 to be paid out in total, plus $2,500 per month in alimony payments. The lawyer ended his letter by saying, “We a
re being generous. In my professional opinion, Sarah is entitled to much more than this.”
And for months, Barry had been battling Sarah without ever seeing her. He had to get a lawyer of his own and he managed to spend nearly ten grand in lawyer fees in just those few months. But his lawyer didn’t have much hope. “Technically, Sarah is entitled to half of your assets, but I’m hoping we can convince a judge that she shouldn’t get nearly as much alimony,” said Barry’s lawyer.
“Are you serious right now? Why should she get anything? We weren’t even really a couple. We were just roommates.”
“But you admitted that you slept together on a regular basis. That won’t look good to a judge.”
Barry tried finding a new lawyer, but he didn’t have the money to afford a decent one. So he took the little money he had left and he took up smoking and he started walking his dog a lot more. He used those long walks to clear his head, which he was trying to do now, though it was hard now, seeing as that morning, Sarah’s lawyer had called to let him know when the court date was. He had two weeks to prepare an argument for a judge. And if he were to lose (which seemed highly likely) then he would have only a month to sell his property to pay out his ex-girlfriend.
At least Whiskey didn’t seem too stressed out. Barry watched as he ran through the trees, his paws pattering on the dead leaves. It was a dark and moonless night, so for most of the walk, Barry couldn’t see his dog—he had to rely on Whiskey’s noisy footsteps. Luckily it was a quiet night, so even when Whiskey was twenty yards away, Barry could still hear him. He could even hear the sizzling of his cigarette as he took a long drag.
It wasn’t cold but his hands were trembling slightly—probably with anxiety. A part of him wanted to skip the upcoming court date. He could just send Sarah the money and beg her to drop the alimony request. At least then he could simply sell his house, give her the money, and then pretend like she never existed as he basically started his life over again.
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