The man supposedly named Randy started pushing his hard cock into my ass. I clenched at first as my mind raced. I could still stop him. There was nothing stopping me from spinning around and saying, ‘I’m not going to do this.’ I could leave and Erin would never know how to contact me to tell me how disappointed she was in me. She couldn’t be disappointed anyway—she was the one who set me up for this without my knowledge or consent. But I wasn’t spinning around to stop Randy. I was still bent over, still with the tip of that hard dick pressing into my butthole.
I took a deep breath and looked into Erin’s eyes. She was smiling and looking more beautiful than ever. She clenched my hand tight, making my heart throb. “You okay?” she asked.
I nodded my head and returned the smile. “I’m good,” I said, and then I unclenched. Randy slid in suddenly, stretching me wide and filling me completely. I gasped and clenched momentarily, but I knew I could take it. I knew I just had to power through the first few thrusts and then there would be nothing but pleasure. So I bit my tongue and forced my anus to relax, and he slid in further, rubbing his veiny cock through my anal passage. I could feel my rim stretching to accommodate the thickness of his girth, but it didn’t hurt much. There was a generous coating of lubricant on his condom-clad cock, so there was no tearing. I still clenched Erin’s hand tightly as he sunk deeper and deeper. I swear I could feel his tip pressing up through my stomach—he was certainly big enough.
Then I took another deep breath and relaxed even more. A tingling of pleasure flowed through me. His cock was pressed against that amazing spot and I remembered how much I liked taking it in the ass. His big, warm hands were holding my hips tightly, pulling me in towards his crotch. I could feel him throbbing inside of me. He was horny, and that horniness was for me. In a weird way, it was nice to know that I was the one making him so horny. I really was pretty in that lingerie and makeup. I wasn’t just pretty—I was sexy. For the first time in my life, I was above average at something. And so what if other men would scoff at me if they knew—first they would have to know before they could scoff, and the only way they could know was if I wanted them to know. I was convincing—terrifyingly convincing. Maybe I’d found my true calling. Maybe the combination of all the things I was once horribly terrified of—prostitution, transgenderism, anal sex—was exactly what I was good at in life.
Maybe Angie leaving me was the best thing that ever happened to me.
Randy started thrusting, grunting every time his hard pelvis slapped against my soft ass. I could hear myself moaning. One of his big, muscular hands dug underneath me and grabbed my cock firmly. He started to stroke and massage me, and it felt nice. I never thought that having a man massage my cock would feel so good—especially not a buff, muscular man—but he knew exactly how tight to hold and how hard to rub. Maybe I was a little bit bisexual—though is it really considered bisexual to like the intimacy of a man as a woman?
Erin crawled forward and pressed her lips against mine. We kissed. He tongue slipped into my mouth and wrapped around mine, the way I liked. I loved the way her nose felt nestled against mine, and I loved the sweet taste of her gently flavoured lip-gloss. I especially loved the way she cradled my face gently with her hand.
She pulled back and smiled with dark red cheeks. Then she looked up at Randy. “Fuck her harder,” she said before looking back at me with a big smile. And I couldn’t help but return the smile.
Randy started pounding me harder, making my whole body slide slightly up the bed. He had to pull me down with both of his beefy hands so that I wouldn’t get away from him. He was much stronger than me. He could have easily held me down with just a couple of fingers.
I was moaning loudly now, squirming and clutching at the bed sheets.
Without pulling his cock out from me, Randy managed to pull me up to my feet. I wobbled in my heels but managed not to fall. “Suck her off,” he said to Erin, and Erin didn’t hesitate. She crawled forward and grabbed my cock with her pretty finger. She started quickly, picking up where Randy left off, jerking quickly with a tense grip. She leaned forward and plunged my cock into her warm, wet mouth. She bobbed her head while slurping. Saliva ran down my ball sack and dripped onto that hotel floor. “Just like that. Suck that fucking cock,” Randy said while looking over my shoulder. He thrusting harder than ever, getting every inch of his massive throbber inside of me with every plunge. And my God, did it ever feel amazing. My whole body started to tremble as an incredible euphoria began to pulse between my legs. I squirmed and my knees buckled, but he held me up. I started to scream and clench, but that didn’t stop the orgasm—nothing could stop that orgasm.
I unloaded inside of Erin’s mouth. She gasped but she didn’t pull back. She closed her eyes tight and took every blast. I came so much that my load was spilling out the sides of her lips, running down her cheeks and dripping onto the floor.
“Swallow it,” Randy demanded. Before Erin swallowed, she tilted her head back and opened her mouth, to show off her gooey white prize. Then she closed her lips and took it all down with a big gulp. It was only seconds later when Randy started to grunt. His fingertips dug into my skin and he pulled med in tight. Then I felt his cock twitching as his condom filled up. I almost wished he wasn’t wearing a condom, so I could feel that amazing wetness splashing inside of my body—but I knew I was better safe than sorry.
He pulled back and I fell forward on the bed. My legs were like melting butter. I had no energy. The room became silent as everyone gathered their senses. And I remained still waiting for that harsh reality to return to me—waiting to realize that I’d just whored myself out to a complete stranger, while dressed in slutty lingerie. I knew that reality would sting as soon as it hit—it was just a matter of time before it sunk in.
CHAPTER VIII
Randy took off after leaving a large wad of money on the dressed. Once he was gone, Erin took that wad and handed it over to me. “You did all the work. I basically just watched,” she said.
“I can’t take this. It’s yours. He’s your client,” I said.
She laughed. “Don’t worry. I’ve got plenty of cash. Just take it. Use it to buy yourself a few outfits and some makeup.” I flipped through the wad. There must have been seven hundred bucks there. “He always pays for a whole night, even though he never sticks around for more than an hour,” she said. “He’s a good client—with a nice, big cock, too.” She giggled and then slipped into the bathroom to check her makeup. I followed her. I spent a moment staring at myself in the mirror, still shocked by how pretty I looked, and still shocked that I was spending the night as a transgender prostitute.
“That was fun,” I said.
“We’ll do it again sometime,” she said with her cute smile.
“I’d like that.”
And then I watched as she carefully touched up her eyeliner. I couldn’t wait to get my own makeup, so I could learn to do different looks. There was a whole world of possibilities ahead of me.
I felt awkward as I stood behind her, silently watching. But she didn’t seem to mind—or maybe she didn’t fully notice. “Are you okay?” she asked without looking at me.
“I’m just—I’m waiting for something to happen, but it’s not happening,” I said.
And then she looked back at me. “What are you waiting for?”
I took a second before answering. I looked down at her crotch and saw that her cock was still half erect, pushing out from her lingerie. I looked at myself in the mirror and saw my own cock, which was still hanging out, after being sucked and massaged to climax. I reached down and slipped it back into my lingerie. I liked the way it felt, being hugged by that tight lace. But that dread I was expecting still didn’t come. “I’m not feeling any regret,” I said.
“Why would you?”
I shrugged my shoulders. “Don’t you ever feel regret?”
“I haven’t felt any regret in a long time—not since I started embracing my feminine side, if you know what I mean.” She k
issed me on the cheek and then she went into the other room. She got herself undressed. She had a killer body with perfect curves. She bent over and pulled a cute red dress out from her suitcase. “Want to get a drink with me?” she asked.
“Sure,” I said.
She pulled a little black dress out from her suitcase and tossed it to me. “This will look cute on you,” she said. It was satin and incredibly soft. I couldn’t wait to feel it on my skin. But I didn’t put it on right away. I was still waiting for that dread to set in—still waiting for that regret to become obvious. But why wasn’t it coming? Was I really happy with Erin? Did I like being a sissy? Did I like whoring myself out? Was there really nothing wrong with being a trap?
Erin was staring at me now. “You still look confused. Are you sure you’re okay?” she said. And then she laughed. “You know, if you decide you don’t like being a girl, then you can stop. It’s that simple. But if you think you like it, then give it a try. It’s not going to hurt, is it? Now get dressed—let’s go get a drink.”
So I slipped the black dress over my tight lingerie, and it felt just as amazing as I thought it would. Maybe I would like being a chick. Maybe destiny brought me to this hotel room. Maybe this wasn’t the end of my journey of self-discovery. And like Erin said—if I decided I didn’t like it, there was nothing stopping me from going back to being George. But as we made our way down to the bar to be hit on by cute guys, I had a feeling that I was going to like it. I had a feeling I was going to have a lot of fun as Georgia.
THE END
HOSTEL GIRL
Pete’s girlfriend breaks up with him days before their big European backpacking trip. It’s too late to cancel the expensive flight, so Pete makes the trip alone, terrified to face a strange continent by himself.
His ex-girlfriend was the one who made all the plans, so Pete isn’t sure where to start after he lands in Amsterdam. He even forgets to have his money converted into euros, so he’s lucky when he finds a hostel willing to let him stay, as long as he doesn’t mind sharing a bed. And he doesn’t mind sharing when he sees the beautiful brunette he’ll be sharing with—at least until he finds out that she’s packing more than what is in her backpack.
CHAPTER I
It was my first time over the ocean. It was my first time outside of Canada. Hell—it was my first time being out of the Greater Toronto Area, unless you include that time I went to Ottawa for a school field trip.
Now, I was in Amsterdam, surrounded by amazing buildings and street names I didn’t recognize. I was excited but terrified at the same time—but more than anything, I was surprised that I’d actually made it. After Tracy broke up with me, I really didn’t think I would end up making the trip out.
We were supposed to do the trip together. We both bought our plane tickets and planned our route: Amsterdam first, then Brussels, then Frankfurt, then Munich, then Vienna, then Budapest, then we were just going to wing it from there. We didn’t book our return flights—we were just going to travel until we ran out of money, staying in the cheapest hostels we could find so it would take an especially long time. We wanted to see the world. Tracy had only ever been out of Canada once before, and it was to see a hockey game with some friends in Buffalo, New York.
It was four days before the big trip when Tracy called and said, “I don’t think we’re working out.” I had no idea what she was talking about. It took me about three minutes to realize she was breaking up with me. For the longest time, I thought she was just talking about the details of the trip. It didn’t help that my reception wasn’t great because I was at work, in the third basement of a Toronto skyscraper, sorting through mail.
“You’re leaving me?” I said when I realized she was leaving me.
“Sorry, Pete,” she said. I was shocked and devastated. We’d been dating for six months, and there had hardly been any hiccups—just the one, when she walked in on me masturbating to pornography. It turned into a weeklong fight, because she believed that I should only be able to masturbate to pictures and videos of her—everything else was cheating. But that was early in our relationship, and I assumed she’d gotten over it. But maybe not. Before I could ask why she was leaving me, she hung up the phone. She didn’t pick up when I tried calling her back.
I had one day left to cancel my flight to Amsterdam—one day before the forty-eight hour refund limit. I had the number dialled in my phone, but I couldn’t bring myself to make the call. I kept clinging onto the hope that Tracy was just messing with me—maybe even testing me. She wouldn’t answer her phone, and she wasn’t at her apartment (I stood outside ringing her buzzer for three hours like a complete lunatic). Finally, when the realization began to set in that she really was leaving me, it was less than forty-eight hours away from my flight. I could either go to Amsterdam alone or say goodbye to about eight hundred bucks, which was a hell of a lot for me and my minimum wage mailroom job.
The flight was at 8:00 AM, which meant I needed to be at the airport no later than 6:00 AM. I didn’t bother setting my alarm, planning on letting the trip go away. But I ended up waking up without an alarm at 4:45 AM. I was wide-awake and I had nothing to do. My job was technically over. I’d given my two weeks notice two weeks before. I knew that I could go to my boss and ask for my job back, but I didn’t want to have to embarrassingly explain why I wasn’t going on the trip I’d been talking about for months. So I ended up getting out of bed, stuffing some clothes into a bag, and taking off for the airport. I caught my flight and found myself en-route for Amsterdam, alone, and very, very confused. I didn’t know what I was going to do. The thought of going sightseeing alone seemed strangely pointless and depressing. What do people even do when they travel alone?
I took the first bus leaving the Amsterdam airport for city centre. I had no idea where I was going, or if there were even any hostels at the city centre. Tracy and I had originally planned to just drift around, letting date determine where we ended up.
Tracy was really into all of that spiritualism stuff. She believed that a person needed to open themselves up to the universe in order to find their path in life. Apparently her path no longer included me. I didn’t feel too broken up over the breakup strangely enough. I never cried and I never went through that stage of thinking that I would be alone forever. More than anything, I was just upset that I was left to travel alone. I was upset that I was given no explanation, though I had a feeling there wasn’t a great explanation. Knowing Tracy, she probably meditated with a crystal on her forehead and then came to the realization that we weren’t meant to be. And maybe that was for the best. Maybe we were never really great together.
The sun was beginning to set once I was off the bus and looking around at downtown Amsterdam. I had no idea which direction was which, and my phone was dead because I’d left my charger at home. I left a lot of things at home when I quickly packed my bag. I meant to bring my laptop, but I forgot that, and I meant to bring a pair of headphones for the long flights and train rides—but I forgot those as well. I didn’t even bring a map, so I had no idea where to go.
I started wandering. It wasn’t long before I realized I was wandering into the famous red light district. There were already girls in lingerie standing out on the streets, waiting for clients—and some of them were shockingly beautiful. They were so beautiful that it was almost sad—though they probably made a good chunk of money in a day. I watched as one guy walked up to a girl and then the two of them petered off into one of the buildings to fuck. I found myself wondering how much a romp would cost. Maybe that’s all I needed to get the Tracy resentment out from my head. One of the girls made eye contact with me and I looked away quickly.
My heart fluttered and I carried on. I found a little restaurant on the street corner. I went in for a bite to eat. When I went to pay, the man looked at my handful of cash and said, “You can’t pay with that.” I realized I never went to the bank to get euros. I didn’t even know the value of a euro. I tried paying with my credit card, but it w
as declined. Apparently I had a card that only worked in Canada. Thankfully, the restaurant owner felt bad for me and let me eat the food anyway—or maybe he just didn’t feel like throwing it in the garbage.
Now it was late, almost 10:00 PM, and I needed to find somewhere to sleep. But first, I needed to find somewhere to exchange my money. No hostel would let me in without money, so I continued to wander the streets. One of the working girls gave me a spank on the ass as I walked by. “Want to have the best ten minutes of your life, sweetie?” she said with a thick accent. “C’mon—come party with me. I promise you’ll have a good time.”
“I’m okay, thank you,” I said. I could feel my face turning dark red. I bit down on my tongue and looked away from her. She was wearing sheer lace lingerie, which did nothing to hide her dark pubic hair or her pink nipples.
“You know where to find me!” she called out, and I kept on walking.
It was after 11:00 PM when I stumbled upon a small blue sign that read ‘HOSTEL’. I only had my Canadian money, but I needed somewhere to sleep. So I walked in and hoped for the best. “Can I get a room?” I asked. “This is all I have. I can get some euros in the morning, but nothing is open right now. I promise this money is real. I know it looks silly because it’s so colourful—but it’s really what our money looks like. And seriously, I’ll get euros in the morning. Just tell me where to go.”
The man behind the counter stared at me in silence for a moment, and it occurred to me that he probably didn’t speak English. Then suddenly, he just pointed up the stairs and said, “We don’t take Canadian money but you can go sleep in room nine. Tonight is free, as long as you don’t mind sharing if someone else comes in.”
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