“Are you sure about this?” I asked. The dildo was big: thick and long and ribbed. I’d never been penetrated before—unless you count her two slender fingers, which only went up to her knuckles.
“It’ll be fun,” she said. And then she started trying to push the fake cock into my ass. I clenched hard, my heart suddenly pounding. “Relax,” she said as she twisted and pushed on the dildo. I didn’t think it would go in, but somehow it started to enter my body. I clenched again, and then she looked at me. “I said relax.” She had a seriousness in her tone. So I took a deep breath and I relaxed. Then she pushed the dildo in further.
I closed my eyes and tried to control my breathing. I could feel my anus stretching wide—wider than ever before. It hurt a little bit—but I was more concerned with the fact that it felt good. There was a euphoria swelling inside of me—getting stronger and stronger. And that pain was starting to fade away. But I didn’t want Cassandra to see me enjoying the pegging. I didn’t want her to think that I was gay, or that I liked taking cock in the ass. But my God—it felt so good!
She finally let go of the cock. She used her own body to push it in further. Finally, our butts were pressed together. We were sharing long black dildo—and there was no dildo to be seen; it was completely inside of us. She started thrusting herself back and forth. I could feel the dildo moving around inside of me, rubbing its ribs against my anal walls. I tried not to squirm and I tried not to moan. I forced a smile and then I closed my eyes in an attempt to keep my composure.
“It feels so fucking good,” she moaned. I loved hearing her talking dirty. Suddenly the fake cock was feeling better than ever. I let a little moan slip, and then I covered my mouth. Cassandra started thrusting herself faster. Now I couldn’t control my moaning. All I could do was keep my mouth covered so she wouldn’t hear me. I took in long, deep breaths of air. And she kept thrusting herself.
And then I started thrusting myself, pushing my body towards her and then pulling back when she pulled back. She reached out and grabbed my throbbing cock. She started to pump it. “Fuck—you’re so hard, you little lesbian whore,” she said. Her eyes were glowing.
“Fuck my little pussy,” I said. And then I watched as her face lit up with excitement. “Fuck my pussy hard,” I said again. And her smile was huge. She clenched my cock harder and beat it faster. And between her stroking and the anal stimulation, I didn’t last long. I groaned and then I watched as my cock erupted, shooting tall strands of white into the dark bedroom air. The first few shots of cum landed on my chest and abdomen. The next few billowed out, rolling down her fingers. She let go of my hand and then she rubbed my cum all over her chest—saving a little bit for her tongue. I could feel a wetness around my bum. I looked down and saw the big puddle: she’d squirted all over my bed.
She stopped thrusting suddenly and she fell back to catch her breath. I could hear her smile in her breathing. I reached down and pulled the dildo out from my ass, and then I pulled it out from her pussy, allowing another bout of fluid out, onto my bed. Her pussy hole was gaping and content. I had the strange urge to bend over and lick it—so that’s what I did. She closed her thighs on my head and then said, “Clean me up, slut.” So I licked her wet hole for the next ten minutes or so while she squirmed and moaned and kept my head locked between her thighs.
Then after her second climax (and a good squirt on my face), she got up and went back to her bedroom without saying anything—as if she’d been sleepwalking or in some sort of strange trance the whole time. I went back to sleep, which wasn’t easy seeing as my bed was soaking wet all over from her constant squirting.
CHAPTER VIII
It wasn’t until my tenth day in the witness protection program that I was finally allowed to do whatever I wanted to do. Though there were still some restrictions—my Internet still couldn’t connect to most websites, and I still knew no one in town except for Cassandra. And I was still terrified that people would see me and know that I was really a man under the clothes and makeup—though that fear was dwindling by the day.
I went out with Cassandra a few more times. We were at the mall food court one afternoon when a man came up to our table and asked me for my phone number. I wasn’t going to give it to him—but Cassandra ended up doing it for me. “I’ll call you this weekend,” the man said. I forced a smile. He was handsome enough—an athletic build with short hair and a nice stubble beard. But I wasn’t interested in men, so of course I had no interest in going out on a date with a man.
“All girls like men—even the lesbians secretly like men,” she said. And I believed her because I was convinced that she was a lesbian. Though at the end of the day, I wasn’t really a woman. And the thought of even kissing a man made my stomach hurt.
It was the next day when another man came up to us while we were walking down the street. But this man came for Cassandra’s number—Cassandra told me later that no stranger had ever asked for her number before. But now she was wearing a short dress that I made her buy, and she was turning heads around every corner. She gave the guy her number, and I found myself feeling strangely jealous. I did my best not to say anything, or show any signs that I cared—but it was difficult. I found myself making fun of the guy for the rest of the day, even though he seemed like a nice, normal guy. “He was kind of short. And his hair was a mess,” I said.
“He was kind of cute,” she said.
“I don’t know—maybe. If you’re into that kind of thing, then go for it.”
Cassandra laughed. I think she could tell that I was feeling a bit jealous. She ended up reaching down and grabbing my hand: a bit of a consolation prize. But it was nice, so I took it.
“I’m going camping with some friends this weekend,” she told me. And I thought that she was about to invite me, so I was disappointed when she said, “So you’ll be on your own all weekend. Think you’ll be alright without me?”
I forced a smile. The thought of being alone was scary, but I knew that I would probably just end up lounging around the house all weekend, avoiding the outdoors and people in general. “That’s fine,” I said with my big, fake smile. And for the rest of that week, I hoped that I would end up being invited along on the camping trip—but she never invited me. Maybe she was worried that her friends would be able to tell that I was really a man, and then they would mock her for hanging out with some weird criminal tranny…
She left on Friday morning. She was on her way out the door when I got out of bed. “Leaving already?” I asked.
She smiled. “See you on Sunday night.” And then I watched her run out to meet up with her friends—and I realized I really did have the weekend all to myself. I could do anything. I could go to the mall on my own, walk around the park, or even the busy city streets. Or I could head down to the bus depot and get the hell out of town. All of the charges against me had been dropped. The police could track me down if they wanted to, but legally they couldn’t force me to return to Cassandra’s house.
I was technically only there for my own safety—based on the strong recommendation of the American police force. And maybe that was for the best. Maybe running away wasn’t the best idea. Maybe staying in California as a woman was the best place for me while Steve and his gang was still out looking for me.
I spent that whole Friday in the house, sitting around, counting down the minutes until Sunday evening. It was a warm day outside and people were out in droves. It was a long weekend and most people had the day off. I went out to the pool and I sat around for a bit. I went for a quick dip, but while I was swimming I realized that I much preferred simply sitting by the edge of the pool, evening out my tan.
I tried reading a book, but Cassandra had nothing that interested me. Then I looked up the nearest bookstore. There was one just a couple of miles away—a twenty minute walk at most. I thought about making the walk, but my heart stuttered at the thought of passing all of those people in the streets. So I stayed inside, meandering around the house, counting down the minu
tes.
It was noon on Saturday when I finally caved. I couldn’t just sit around the house all weekend. I needed to get out or I was going to lose my mind. So I got myself dolled up and then I took off for that bookstore, to get myself a book that I could actually force myself to read. I stopped at an Internet café along the way. I paid five bucks to use the computer for an hour, and then I spent that hour looking at all of the websites that were blocked at my house. I looked up Steve Anderson’s name, to see if there was any update. Apparently he was still at large.
I almost logged into my Facebook, but then I hesitated. What if they could track where I logged in from? What if Steve had a team of computer geniuses trying to track me down, so he could murder me the way he murdered Rupert Andrews?
So I closed down the computer and I carried on towards the bookstore. I got a few looks from guys in the streets: smiles and nods and even a wink from an older man. I found myself blushing and smirking like a little girl. I felt much better about being out alone once I finally reached the bookstore.
I wandered the bookstore isles. I didn’t know what kind of book I was looking for. I went down the fiction isle and that’s when I saw a familiar face: it was Mikey, my old friend and fellow organization member. He looked over at me before I could turn around. He looked into my eyes and he smiled. I froze, my heart pounding and my stomach turning. “Am I in your way?” he asked.
I slowly shook my head. Could he not recognize me? He was looking straight into my eyes—did he not recognize my eyes? “I’m okay,” I said slowly in my feminine voice. Then I turned slowly and started to walk away.
“Wait,” he said. And then I froze again. I turned around slowly, forcing the biggest smile I could.
“Yeah?” I said.
“Do I know you?” he asked.
I shrugged my shoulders. “I don’t think so.”
“You look so familiar.”
“I get that a lot,” I said. My stomach twisted and gargled.
“Well you look awfully familiar. And I’m not just hitting on you,” he said with a big grin. “Anyway—have a nice day.”
I turned around and I left the store without buying anything. I didn’t spend any more time out that weekend. I went straight home and that’s where I stayed until Cassandra was back from her camping trip.
What was Mikey doing in California? Was he on the run from Steve too? Or was he sent by Steve to find me? I had a bad feeling it was the latter.
CHAPTER IX
Cassandra asked me to join her at the mall the next day, but I declined the offer. I told her that I was too tired to go out—which wasn’t technically a lie. I hadn’t slept at all that night. How could I sleep after being spotted by the gang that was trying to kill me? At least I assumed they were out trying to kill me—though maybe Mikey would spare me if he truly recognized me. Maybe he wouldn’t go and tell Steve that he saw me if he even knew it was me under the wig and makeup. But I wasn’t about to take my chances, just so I could peruse a shopping mall…
I spent the whole night trying to decide whether it was a coincidence or if Mikey was in my little Californian suburb for me. It was around 3:00 AM when I came to the conclusion that it was no coincidence. No one randomly decides to go on vacation to random small towns—unless Mikey was on the run from Steve himself.
The next day Cassandra begged me to go out with her again. “Bailey bailed on me,” she said. Bailey was her friend. “I can’t get my nails done alone.” I continued to resist, and then she started to become suspicious. “What happened while I was gone?” she asked, staring into my eyes.
My hands started trembling. I took a deep breath. “Nothing,” I said. “I just really don’t feel like going out.”
“Well too bad. I’m making you come with me. You can’t just sit around the house all day.” So she dragged me out of the house and we went to get our nails done. I made sure to grab the biggest pair of sunglasses I could find on my way out the door. And then I found myself flinching at every little sound. Whenever someone looked my way, my heart would start pounding.
It wasn’t just Steve I was worried about—and it wasn’t Mikey or Jeremy either. The organization had more members than I knew, and if Steve really wanted me dead, then there could have been fifty people searching the town looking for me—maybe even people I’d never seen before in my life.
Even the woman working at the nail salon had to tell me to relax. “You’re all tense. Try to enjoy yourself,” she said. But I was less tense in the nail salon. I didn’t feel too worried that someone from the organization was going to look there—or maybe they would look there, thinking I would be hiding in the least obvious place.
My heart continued to throb throughout the day. I found myself thinking: if Steve found out which town I was in, then he probably found out a whole lot more than that. Maybe he knew who I was living with. Maybe he knew that they would be dressing me up like a woman. Maybe he was already back at the house waiting for me.
So when Cassandra said, “Do you want to go see a movie, or should we just go home?” I quickly said, “A movie sounds good.” But the movie was a terrible experience. With every passing minute, my anxiety only became worse and worse. I tried closing my eyes and controlling my breath, but my heart refused to slow itself down.
When we finally returned to the house, I caught myself flinching as I passed through every door. A part of me expected a hit man with a knife or a gun or one of those cords that they use to cut throats in the movies (including the movie we’d just gone to see). Cassandra laughed at me. “Why are you so jumpy?”
“Am I jumpy?” I said, faking a big smile. “I don’t think I’m being jumpy.”
“You’re jumping all over the place.”
I slept very little that night, even with my bedroom door locked and my curtains drawn shut. Every little sound brought me into a fully upright and awake position. Whenever the floodlight outside went off, I found myself peeking out those curtains, just to see a branch swaying in the breeze, or a squirrel jotting across the grass.
The next few days were just as tough. Cassandra insisted on dragging me out of the house. Sometimes I tried to resist, and sometimes I was successful at resisting—but my constant resistance was starting to make her suspicious. And I didn’t want her to get too suspicious, so I occasionally went out with her.
The mall was by far the scariest place. There were hundreds of people, and many of them looked like they could be part of the organization. We were in a little clothing store and there was a man in a black coat staring at me the whole time. I tried my best not to look his way. But I caved a few times. I looked over at him once while he was slipping a phone out from his pocket. I wanted to rush him. I wanted to slap that phone out of his hand and strangle him to death. I wanted to bash his head into the wall before he had a chance to tell Steve where I was, and what I looked like.
He came up to me with a dull expression on his face. He reached down and slipped his phone into his pocket, and he started to pull something out. I braced myself, ready to dodge a stabbing or a shooting. How quickly could I move if he was really going to kill me?
He pulled out a piece of paper with a picture of a women’s jacket on it. “Hi. Sorry, but do you guys still carry this jacket?”
I stared into the man’s eyes, my heart pounding. “What?” I managed to say.
“This jacket—do you carry it?”
“I don’t work here,” I said.
“Oh,” he said, looking down at my body. “My apologies.” He walked away. And then I realized I was wearing the same colours as the store employees. He wasn’t trying to kill me. In fact, no one tried to kill me that week. And I found myself starting to wonder if I really had seen Mikey in that bookstore, or just a guy who looked strangely similar to Mikey. Maybe my identity and location still was a secret. Maybe I had nothing to worry about.
Or maybe they were just waiting for me to put my guard down.
CHAPTER X
It was Fri
day when Cassandra told me that she was going out to a party on the other side of town. “You should come with me—it’s going to be a lot of fun. There will be tons of cute guys there.” I had to admit that I wanted to check the party out. I had lots of cute little outfits that would have been perfect for a good house party—but I still wasn’t sure if there were violent gang members out looking for me, so I passed on the opportunity. “Your loss,” Cassandra said.
So I spent the evening at home by myself, watching reruns on TV, wondering how much fun I would be having if I was at that party with Cassandra. I got bored of the TV after a few hours, so I found myself in the bathroom, experimenting with different makeup techniques. I ended up creating a really pretty formal look, which I decided to complete by putting on my formal dress. I loved the way I looked, but I still wasn’t satisfied.
I went into Cassandra’s room and I found a pair of sparkly white heels, which matched the ensemble perfectly. Then I found some costume jewellery. I must have stood in front of the mirror for twenty-five minutes, just admiring myself: spinning around, smiling, posing, and wishing I had a reason to wear a dress like that out in the real world.
Then I heard the door close downstairs, and a series of footsteps entered into the house. My heart skipped a beat before pounding with merciless aggression. And then I heard Cassandra’s voice: “And this is my place. It’s not much, but it’s mine. Well, and my roommate’s, I suppose. Speaking of—where is my roommate?”
I felt stupid in the formal dress, but I didn’t have time to get changed completely. But I did have enough time to slip out from the heels before Cassandra brought the tour up the stairs. “Here she is,” she said. “And look at you—where have you been, dressed up like that?”
I felt my cheeks turn red. “I’ve just been messing around,” I said.
She grinned. “Well you look good. You would have been a hit at the party,” she said. “I want you to meet my new friends.” She leaned in close and put her lips close to my ear. “They’re really cute, and there’s two of them.” I would have declined Cassandra’ invitation, but before I could process what was happening, I saw her new friends, ascending the stairs to catch up with Cassandra. “Oh, here they are. Mikey, Steve, this is my roommate, Kylie. Kylie, this is Mikey and Steve.”
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