It felt so good, unlike anything I’d ever felt before. I groaned and squirmed and then I heard myself say, “Jesus fucking Christ, that feels so good!”
She stumbled back and then I felt that same hot rush running down the inside of my left thigh. And she remained standing behind me, catching her breath. I looked back at her with a big, stupid smile on my face. “That felt so amazing,” I said.
She was staring at my ass, watching her creampie fall down to the ground. “You know—you would make a really cute girl. You’ve got the perfect curves.”
The comment made my skin tingle. “What did you just say?”
“Roll over so I can see your face,” she said. So I rolled over and then she crawled on top of me.
I laughed nervously. “What are you doing?” I asked.
“You would be so pretty as a girl. You need to let me do your makeup,” she said. My heart was pounding hard all over again. “I bet you would even fit into my clothes.”
“I’m sure I wouldn’t do them justice,” I said awkwardly.
“No—you need to let me give you a makeover. You would be so cute. What are you doing tomorrow night? We’ll meet up again. Maybe we’ll even have sex again—on the house. Just let me do your makeup.”
It was a hard offer to refuse. I didn’t exactly want a tranny whore to give me a makeover, but I wasn’t going to turn down the sex—especially after having the best sex of my entire life. “Okay, I guess so,” I said.
Besides—the thought of being sissified made me terribly uncomfortable, and I was desperate to try everything that made me terribly uncomfortable.
CHAPTER VI
I was starting to become genuinely concerned for my sanity. I hardly slept that night—not because of guilt or dread or regret, but because I was excited for my next date with Erin. The more I thought about her dolling me up, the more eager I became. I was curious to know if she was right, or if she was just messing around with me. I got out of bed a few times, just so I could stare at myself in the mirror. I always did have a smaller build, and my facial features were soft—my jawline wasn’t rugged and girls would always tell me that they wished they had my nose back in high school. So maybe Erin was right.
I’d never been interested in cross-dressing. In fact, the thought had always made me ill with discomfort. I never understood why a man would want to get dolled up. But now I thought about Erin, and how convincing she looked. I thought about all of the traps I fell for on the porno websites, and then I thought about Cary, who trapped me on Tinder. Maybe I could be like one of them. Maybe I could be convincing too, with a little bit of work.
But is that what I wanted? Did I want to be convincing? Shouldn’t a man want to look like a man and nothing else, no matter what clothes he puts on his body? Why was I feeling so excited? Was I seriously so addicted to adrenaline that I was now losing touch with my own manhood?
I didn’t focus much at work that next day. I spent most of the day staring at the clock. Whenever I was sure that I was alone, with my office door closed, I practised my voice. If I was going to get dolled up, then I needed to have a half-decent voice—right? I found myself on YouTube, watching transformation videos. The guys in the videos didn’t look too different from me. There was even one guy who looked like he could have been related to me, with the same nose and same cheekbones. Maybe Erin was right—maybe I would pass as a convincing woman.
My ass was still a bit sore from being fucked. Whenever I thought about our little romp, a smile crossed my face. I felt so naughty. I slept with a prostitute—a tranny prostitute. But I didn’t regret it. It wasn’t weird when we were fucking, and it didn’t seem weird now as I was reminiscing at my desk. And that seemed to be the pattern: everything I was terrified of turned out to be surprisingly harmless. Erin was just a person, just like Angie and just like that brunette I met on Tinder. It no longer seemed like there was anything taboo about the fact she was trans—though it still seemed a little bit taboo that she was a sex worker, though it’s not like anyone was forcing her in prostitution. As far as I could tell, she was completely independent. I don’t even think she had a pimp. With the Internet, are pimps even still a thing?
I showed up early for my date with Erin—if you can even call it a date. She was ready for me, with a big smile on her face as she opened the door. “I didn’t think you were actually going to show up,” she said. “I thought you were just entertaining me when you said you would come.”
“I figured it’s worth a try. I want to try everything at least once,” I said.
And then she grinned. “Everything?” She laughed and then led me into her hotel room. She already had the room set up for me, with her makeup covering the bathroom vanity and her outfits covering the bed and dresser. She looked down at my feet and said, “What size are you? You look like a seven—is that right?”
“That’s right,” I said.
“Perfect. Then all of these heels will fit you,” she said, motioning towards the corner of the room where she had a dozen different pairs of heels. They were all tall and sparkly—and they all belonged out on the street, made to attract the type of man looking to pay for a little bit of sex. “But first—did you shave your legs?”
“Was I supposed to?”
She rolled her eyes. “Have you ever met a woman with hairy legs? Let me rephrase that: Have you ever met a woman you wanted to fuck with hairy legs? C’mon. I’ve got a spare razor in the bathroom. Get undressed—all of your clothes off. I’ll run the tub.”
It felt strange stripping in front of Erin, knowing that I wasn’t stripping for sex but to get the hair removed from my legs. “If you’re really into this, like I know you will be, then you can wax your legs in a week or so. The hair will stay gone longer if you wax. And once you wax enough times, the hair starts to stay away, at least a little bit.” I climbed into the tub and looked down at my hairy legs. It was June, the start of summer, the start of shorts season. If I shaved the hair off of my legs, people would certainly notice, unless I remained in jeans for the rest of the year. And was it worth it? Was I prepared to wear jeans for the rest of the summer just because I wanted to know if I could actually look like a girl?
I took the razor and started to shave my hair off in strips. There was no turning back now. I shaved as far down as my feet, even getting the little bits of hair off of my toes. I thought I was done, and then Erin said, “Your cock too—get rid of all that hair.” My heart stuttered, but I’m not sure why. I’d never shaved the hair around my cock before. I kept it trimmed, sure, but the last time there was no hair there, I was eight years old. She was staring down at me with that intimidating yet seducing look. I felt like I had no choice, so I carefully removed the hair around my cock and on my balls. She told me to stand up and turn around, and then she helped removed the hair between my legs and on my ass. She even spread my ass cheeks and got right in there, running that razor carefully over my asshole. “You’re already looking so much better,” she said, though I wasn’t sure if it was true.
I stepped out from the tub and looked in the mirror. I was strangely shiny without hair. Erin came up next to me and lifted up my arm. Without even asking, she started to remove my armpit hair. Now tank tops were off the table for the summer as well. She had a big smile on her face. “Oh my God, you’re going to look so cute,” she said. And I wasn’t sure whether or not I hoped that she was right.
Next, it was time to do my makeup. She dragged a chair in from the main room and told me to sit, facing the mirror. Then she grabbed a cream and started rubbing it on my face. “This is foundation. It’s important to get a good foundation first.” She explained everything as she went on. I did my best to keep up, but there was an absurd amount of information to keep track of. If this really was something I would end up doing again, I knew I would probably have to find some Internet refresher course.
I was shocked by how quickly my face was transforming—and I was shocked at how effortless it seemed to be for Erin. She woul
d only spend a few seconds with each product, brushing my face quickly and then moving onto the next thing. It was like watching Bob Ross painting, except instead of a stunning landscape, I was watching a beautiful woman emerging.
I was speechless. Erin was right—I really could look like a girl. And now, as I stared at myself as a girl, I wondered if I normally looked like a girl. Did I ever look like a guy? My eyes were so big and stunning. Were they always that way? And my lips looked so plump and soft—but all she’d done to my lips was put on a bit of gloss. Could gloss really make this big of a difference, or was I just seeing myself in a new light?
She left me to admire her work while she went to retrieve an outfit. She moved quickly, as if she was in a rush. She came back with a little lace teddy with a tulle skirt. “Try this on,” she said. “And say something to me in a girly voice. Tell me how much you love my cock.”
I cleared my throat and waited a moment for my embarrassment to settle. “I love your cock more than anything,” I said. And I found myself surprised by how feminine my voice sounded—way better than when I was practising at work. Erin nodded her head with a big smile.
“That was great,” she said. “But just try to sound a bit softer. You don’t have to be quite so loud—not while you’re getting used to everything.” So I tried again, and I watched as she made a big smile, letting me know that I really was sounding pretty good.
I slipped into the lace teddy. It was tight, but it felt good against my skin. She went and grabbed one of her bras. She pulled the pads out and handed them to me. “Try slipping these into your cups.” I did what she said. The added bust filled out my curves, giving me a fantastically feminine look. It’s amazing what small little details can do to an overall look.
The heels weren’t quite so easy. They fit perfectly, but I was hardly able to stand upright. I tried walking around her little hotel room, and I had to grab onto the dresser a number of times as my ankles wobbled. It didn’t help that the shortest pair of heels she had were four inches tall. But I had to admit: they looked cute on my feet. I especially liked her red pair.
There was a knock at the door. I perked up and my heart skipped a beat. Erin grabbed her phone and checked the time. “He’s early,” she said.
“Who’s early?” My skin suddenly felt cold. I looked over at the AC unit to see if it had suddenly turned on, but it was off.
“My client,” she said. She walked over to the door and reached for the handle. I wanted to tell her to stop. I looked around to see if there was another exit—maybe a fire escape—but there was only that door. “Randy. You’re early!”
I could see Randy towering above Erin. He was almost as tall as the doorframe, and about as wide as two Erins, without much fat on his body at all. “Sorry. Traffic was light,” he said. His voice was deep and booming. He looked over Erin’s shoulder and spotted me. “Oh, I’m sorry,” he said. “Am I interrupting something?”
“No. I hope you don’t mind, but I’ve got someone here with me today. I guess you could say that she’s in training. She’ll be watching.” She looked back at me with a smile. “And maybe participating, if she’s feeling up to it.” My heart swirled down into the pit of my stomach. Was this why she brought me here? To sweeten a deal with one of her regular clients? Was this some sort of humiliation? Was she really expecting me to participate? What did that even mean?
Randy stepped into the room. He slipped out from his suit jacket and stared at me for a few seconds too long. “You’re very beautiful,” he said. The comment took me off-guard. Was he just saying it, or did he really mean it?
“Thank you,” I said. I could feel my cheeks turning red. But why were they turning red? Was I really flattered by the compliment—even if it was real? Did I really want to think that I made a beautiful woman? Was that better than making for a manly woman?
Erin stepped behind the hulk of a man and started to rub his shoulders. “She’s new, so be extra nice to her,” Erin said.
“What’s her name?” Randy asked.
Erin looked at me, putting me on the spot. “Georgia,” I said, forcing a smile.
“That’s a pretty name,” Randy said.
Erin spent a minute on Randy’s shoulders before working her way down towards his belt buckle. She made quick work of it, pulling his belt out and tossing it aside. Randy took a deep breath and watched the experienced tranny’s hands as she unzipped his fly. I felt a little bit jealous. Maybe I had a bit of a crush on Erin, and a part of me hoped that I was the only guy for her. But I knew that was absurd. She was a prostitute and she had to make a living somehow. I wasn’t singlehandedly paying for her hotel room and all of her makeup and lingerie.
Erin shimmied Randy’s pants down, along with his boxers, revealing his long, thick cock. He was massive, and already throbbing. Erin took his cock and started to pull back his foreskin, unveiling his shiny, bulbous tip. He let out a sigh of relief. And I just remained still, watching the act from across the room, not sure what I was supposed to be doing.
Erin slipped around her date and sunk down to her knees. That giant cock went straight into her mouth and she started to suck. Randy closed his eyes and let out a long groan. “That feels amazing,” he said.
I carefully stepped towards the duo. I sunk down behind Erin, putting my hands on her shoulders. I watched as that long rod slipped in and out of that warm mouth, sliding across those plump, soft lips. I’d never been so close to another man’s erection before—unless you count Erin’s, though her cock was hardly manly. I watched for a moment before looking up at Randy, who was looking down at me.
“Suck her cock,” he said suddenly. And it took me a moment to realize he was talking to me and not to his date. He wanted me to suck Erin’s cock? A lump the size of a fist was suddenly filling my throat. I’d never sucked a cock before. I didn’t even know how. Was I literally supposed to suck, or just bob my head up and down?
Erin kept sucking his cock, as if she didn’t hear the demand. I was terrified of letting Erin and her date down, so I carefully got down onto the ground and crawled underneath Erin, who had her knees planted with just enough space for my head to slide underneath. I carefully pulled her little panties aside, letting her package fall out, onto my forehead. I shimmied a bit further, so that package was hanging down at my lips. Then I opened my mouth and allowed her cock into my mouth. Within seconds I could feel her throbbing and growing. It was a satisfying feeling, knowing that I was the one making it happen. I bobbed my head as much as I could at my awkward position—but mostly, I just played with her cock using my tongue, swirling around and teasing her tip. She gently let her bum rest down on my face, which I liked. I used to hate the thought of someone sitting on my face, but now it just turned me on. Now I was obsessed with that feeling. I wanted her to put so much weight on my face that I couldn’t move. I wanted her to grind her asshole and her ball sack all over my chin. She was rock hard in my mouth now—her cock pushing up against the roof of my mouth. She started to bounce slightly, fucking my mouth like it belonged to a sex doll. It was nice—I didn’t want the moment to end.
And then I heard Randy say, “I want to fuck your friend in the ass.”
“That’s up to her,” Erin said. She stood up and looked down at me. They were both looking down at me as I lay on that floor with saliva running down my cheeks. A man—a real, manly man with a big cock—wanted to fuck me in the ass. The thought was terrifying. And as that terror filled my heart, I knew I couldn’t say no. I knew that my addiction to putting myself in uncomfortable positions would win out in the end.
“Okay,” I said gently. My voice was hardly a whimper. Erin was suddenly helping me up to my feet, leading me over to the bed. It was all happening so fast. Was he really going to stick it in my ass? I looked back and saw Erin fitting a condom on his curved throbber. Would it even fit? Would it hurt? Would I cry out in pain?
Once I was bent over, Erin climbed up on the bed. She got her face right next to mine. She was smili
ng when she said, “It’s going to be good. You’ll like it. Hold my hand—squeeze if it hurts. It won’t hurt for long—I promise.” I felt strangely comfortable with Erin there, like nothing could hurt me. Her smile made my heart melt just a little bit. And suddenly, I felt the strange tingling of excitement crawling all over my skin. Then, I felt the warm, dull pressure of a thick cock pressing up between my butt cheeks. I felt his big fingers prying my cheeks apart, so that he could see the tiny hole he was about to stretch wide. My heart fluttered down into my gut and for the first time that afternoon, reality caught up to me.
CHAPTER VII
I realized what I was doing and how absurd it was. I was dressed up like a girl, with a prostitute, and about to be fucked in the ass by a complete stranger. How had my life come to this? What happened to my comfortable normal? Where was my comfort zone now? Was this what Angie wanted from me when she told me I needed to live a little bit? Surely this wasn’t what she was talking about, and surely this wasn’t what I wanted. The pendulum had swung way too far in the other direction.
I started thinking of all the possible repercussions of what I was doing. What if his cock was so big, he left me permanently stretched out? What if he tore me open and I had to go to the hospital for some humiliating medical help? What if I ran into the man in my normal life, and he told everyone that I was secretly a transgender prostitute? Or worse: what if I liked it? What if I liked it so much that I wanted to keep whoring myself out while wearing cute lingerie and pretty makeup? A grin crossed my face as I considered the latter possibility, and that grin made a strong dread grow in my gut.
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