I shimmied my panties down, exposing my anus. I kept my thighs pressed together, so he wouldn’t see my dick or balls. I got the panties down to my knees and then I awkwardly pulled my calves up so that I could pull the panties up and off of my body completely, without showing my cock to my mysterious date. I looked back at him. “Do you want to smell them?” I asked.
Finally, he moved from his place. He took a few careful steps forward and then he grabbed the panties from me. He brought them up to his face and he smelled. “They smell nice,” he said.
“Why don’t you take your sunglasses off?” I asked.
The room became silent again. He stared at me for a moment, and then he slowly reached up and grabbed his sunglasses. He hesitated for a few seconds, and then he pulled them off. And that’s when I recognized him.
CHAPTER VIII
I wasn’t in a motel room with a stranger. I was in a motel room with Devin, one of the men responsible for getting me into this whole mess. Devin—the boy who made me dress like a chick as a joke was now hiring me as a prostitute because I was dressed like a chick. And was this his thing all along? When he made me put on that little red dress, was he satisfying some sort of sexual craving? Did he go home and jerk off to the thought of me after that day? Or was the sight of me in a dress what turned him into this monster?
“What is it?” he said. Apparently I was staring at him with terrified eyes. I blinked quickly then I looked away.
“Nothing. What do you want me to do now?” I asked. I felt like I was short of breath. My heart was pounding powerfully and my mind was spinning quickly.
He tossed the panties down on the bed next to me. “Pick them up,” he said. I grabbed them. “Now stuff them into your asshole.”
“What?” I said.
“You heard me.”
It took a moment to truly process his request. My mind was still reeling over the fact that Devin was standing in a room with me—hiring me—making me into his whore. It was no wonder he was being so secretive, so careful to make sure that no one saw me with him. Devin was a popular guy. Nearly every guy in school wanted to be him, and his entire reputation would be destroyed if people knew that he was sexually aroused by boys in skirts.
“Well? What are you waiting for?” he said.
I reached the panties back and pressed them between my butt cheeks. I had no idea how I was going to get them inside of me, but I had to try. Using one finger, I started to push the panties against my asshole. But I couldn’t seem to make my hole open up to accept the lacy garment. I kept trying, pushing from different directions. It wasn’t happening, so I tried something different. I spat on my finger then I reached my finger around back. I rubbed the spit in circles around my hole, and then I tried the panties again. After a little push, I achieved penetration. I perked up and felt that soft fabric suddenly inside of me—just a tiny bit inside of me, but enough to make a gasp slip out from my lips.
I heard Devin exhale. I looked back and saw that he now had his pants down around his ankles and his cock in his hand. He was stroking himself while watching—and I could see that his cock was throbbing and getting harder. I really was arousing him! The boy who made my teenaged years so miserable—now I felt like I had power over him—the same power that I had over Kyle.
He was keeping his distance from me because he was intimidated by me. He wasn’t keeping his hands off of me because he didn’t think that he was worthy enough to touch me. He didn’t think he was in my league, and it was obvious from the redness in his face. What a tremendous feeling! My chest was suddenly filled with a powerful warmth. I felt so confident and so sexy.
I pushed those panties further into my asshole. I squirmed slightly. I’d never been penetrated back there before, so even just the girth of my finger was shocking—but it didn’t hurt. I kept pushing, stuffing more and more of those panties into my body. I had to pull my finger out momentarily to grab more lace to push in. It was only a minute before I had more than half of the undies inside of my ass. I looked back again and saw that Devin’s cock was completely erect now, throbbing intensely as he stroked it up and down.
“If I push any more up, they’ll get lost in there,” I said.
“Turn over,” he said.
So I turned over, sitting down on my ass, feeling the panties rubbing around against my anal walls. It was a weird and strangely arousing feeling, though I had no idea why.
I thought he was going to crawl up onto the bed, to make me suck his cock. I kept my hand over my dick, knowing that he didn’t want to see it yet. He stepped up and looked down at my hand. “Move it,” he said. So I moved it, exposing my cock as my heart was sent aflutter in my chest. He stared at my dick for a moment before dropping down to his knees. He lifted up my shaft with a trembling hand, and then he leaned down and opened his lips. Suddenly, my cock was enveloped by the warm wetness of his mouth. I gasped and became tense. I don’t know why, but I didn’t see it coming. I figured he would want me to suck his cock—I never thought that he would want to be the one sucking.
He bobbed his head up and down for a minute, slurping his tongue around my shaft. It was a strange feeling, especially when his stubbly chin rubbed against my ball sack. He looked up at me and said, “Get it up,” as if I could control it on a whim. But I had to try. I closed my eyes and tried to imagine a woman between my legs—but I wasn’t able to muster up the thought of a woman. I could only think of Devin. I could only imagine his smirking face after he glued that wig to my head. Then, I thought of my own reflection, seeing myself in the mirror after I got home that afternoon, before I cut that wig out of my hair with kitchen scissors.
I actually thought that I looked good in that wig and red dress—that was the worst part about it. I didn’t take that dress off right away. I left it on for a few minutes, secretly wishing that I had read tits under that dress—secretly wishing that I could have just been a girl, so that my girly appearance wouldn’t have been so humiliating. As I stood in front of that mirror, I ran my hands through my hair and I puckered my lips, the way all of the girls were doing for their Facebook pictures. I caught myself smiling when I remembered the catcall I got near Morton Street. And then my dad came into the room and he never looked at me the same ever again.
But there were nights where I would think of myself in that dress. I would imagine myself on my knees, sucking big, hard cocks—cocks that were hard for me, because I looked so good. I would push those fantasies away, knowing they were taboo. But they would still come back from time to time. One time I even caught myself standing, completely zoned out, in front of a lingerie store, imagining myself in the strappy outfits that were on display in the store window. Then, when I came back to reality, I scorned myself for days. Thoughts like those weren’t welcome.
I opened my eyes, looking back down at the top of Devin’s head as he sucked my cock. He pulled his head back for a breath of air, and then I was shocked to see that I had a massive erection. I gasped and he looked up at me. “What is it?” he said as a bit of saliva dribbled off his bottom lip.
“Nothing,” I said. I still couldn’t believe that he didn’t recognize me. Or maybe he did, and he just didn’t want to admit it…
He stood up. His cock stood tall, nearly touching his sternum as it throbbed. I didn’t wait for him to ask before I slipped off the bed and sunk down to my knees. I grabbed his shaft and I started to stroke and suck him off. He reached down and gently slipped his hands into my hair. He even started to thrust his hips slightly, using my face like a sex doll, which I didn’t mind. Though he made me gag a few times by pushing his thick tip down the back of my throat.
“Shit,” he groaned, then he pulled his cock out from my mouth quickly and he stumbled back. He grabbed his cock firmly with one hand and stared down at it with nervous eyes.
“What is it? What’s wrong?” I asked.
He took a deep breath. Then he looked at me. “You almost made me come. I don’t want to come yet.”
�
��Okay,” I said. Then I watched as he closed his eyes and took another deep breath, tilting his head back as if he was trying to gather his composure. Was I really that close to making him burst? We’d only been in that motel room for twelve minutes or so, and I assumed that I was being paid for the whole night.
“Get back on the bed, on your back,” he said. So I climbed up on the bed. He climbed up on top of me. He stared down into my eyes for a moment, making my heart tremble. He was so close—surely close enough to recognize me. Then he looked down at my body. He started feeling me: pulling up my sweater and running his hands all over my skin. I closed my eyes. It actually felt kind of nice, like a gentle massage. His hands were strong and a little bit intimidating. He slipped one hand down and wrapped his fingers tightly around my cock. His other hand spent most of its time at my chest, squeezing my non-existent breasts. He groaned. I felt his warm, wet erection touch my legs a few times.
He slipped one hand up, to my neck. He gently closed his fingers around my throat, and then he started to squeeze, cutting off my airway. I tried to squirm free, but he was holding too firmly. I couldn’t move. Was he about to kill me? Was this the end? Would he fuck my dead corpse? Would the police find me in the most humiliating way possible: dolled up and full of cum?
He suddenly release my throat and I took a deep breath of air into my lungs. Maybe he was just showing me how powerful he was—reminding me that he was the one in control, and not me. After that moment, I remained very still, unless he told me to do otherwise—like when he told me to roll over onto my stomach.
He grabbed the little bit of panties sticking out from my ass and he began to pull. It was a weird feeling as the lace slipped out from my hole. He brought the undies up to his nose and sniffed before letting out a satisfied exhale. Then he grabbed both of my butt cheeks and spread them wide. “Your hole is so tight,” he said.
“I’m a virgin,” I said, though I’m not sure why I said it. He didn’t reply. He was still for a moment, then he released my cheeks, letting them slap back together. I was too afraid to look back at him. I knew what he was getting ready to do, and I wanted to pretend like it wasn’t about to happen. I knew it would be over soon, especially if I already had him on the verge of climax from a couple minutes of sucking.
I felt his hard snake push up between my cheeks. His tip began to grind against my hole. I closed my eyes tight and took one more deep breath. Then I heard him groan as he pushed forward. His tip suddenly penetrated my asshole. I gasped and clenched. He used his hands to pry my butt cheeks wide, so that he could watch my virginity disappear.
He sunk deeper and deeper and deeper. It didn’t hurt, but it didn’t feel right, like everything was stretching—maybe permanently. I swear I could feel his tip passing up my abdomen, up near my sternum. I felt like his tip suddenly clogged my throat, making it hard to breathe. I was relieved when I felt his pelvis press up against my ass. “You took the whole thing,” he said, sounding surprised. I didn’t know what to say back, so I just remained silent.
Then he started to pump, grunting with each penetration. I could feel his veins throbbing inside of me. I could feel his tip swelling and his shaft bloating. He held onto my hips firmly with his big fingers. His big hands made me feel small and weak. A warm drop fell on my back—presumably his sweat. I could smell his musk: a manly scent with a hint of yesterday’s cologne.
I could feel my anus pulling up and down, trying to hug his cock as it pumped in and out. I was worried that he was going to leave me with a dangling asshole—stretched wide and long. Would it eventually tighten back up, or would I have to start wearing diapers?
“Shit!” I groaned. My cock was unbelievably hard, throbbing against the motel bed sheets. The tingling inside of me was intense, though I wasn’t sure why, because I wasn’t even touching my shaft. I clutched two handfuls of bed sheets and pulled them towards myself. Devin was slamming down harder and harder, grunting louder and louder.
I reached back and put a hand on his ass. His muscles were all hard and flexed. I looked back and saw veins throbbing on his arms and on his red face. He was holding back. He was just moments away from erupting inside of me.
I wasn’t sure if I was ready for it. I was scared it would hurt, or that it would feel gross. I’d never had a foreign substance deep in my asshole. I’d never felt cum oozing out from a stretched wide hole. Was my ass going to be sore for the next week? Would I even be able to satisfy another client in the next few days, or would I spend the next few days recovering on that bed?
Devin yelled and then I felt the hot blasts inside of me. I gasped and clutched the bed sheets as tightly as I could. His entire rod was inside of me and his pelvis was pressed hard into my ass—so hard that he was pressing me down awkwardly into the cheap mattress’ springs. His cumshot didn’t seem to end. I could feel it building up inside of me.
Then he suddenly pulled out, rolling off of me and hopping up to his feet as if he was suddenly in a big hurry to leave. I tried to roll over, but my body was limp. Pleasure was tingling down my legs and back and throbbing in my ass. I felt empty, and I could feel that huge load rushing towards me anus; it had a long way to go still before it was pooling on that bed.
“Should I just leave the money on the dresser?” he asked.
“Yes please,” I managed to say. I also managed to turn my head to watch him as he pulled a wad of bills out from his wallet. “There’s three-hundred there—your rate plus a tip.” He pulled his pants up and then he bent over and picked my panties up off the floor. “Can I keep these?” he asked.
They were my only pair—but I now had more than enough to go out and buy a few more pairs. “Sure,” I said. He stuffed the panties into his pocket, and then he left, leaving me alone with the room for the night.
So I had enough money that I could spend the rest of that week in that motel room. And now I knew where I had to go and what I had to do to get more money. I was set for the winter—and that should have made me happy. But I wasn’t happy. Now I just felt confused.
I found myself thinking about my parents. I couldn’t stop thinking about them—memories of them from when I was a child, when everyone seemed happy. My dad used to take me to the zoo and he would ask me if I wanted to work with animals when I was older. “No,” I remember saying.
“So what do you want to do?” he asked.
“I don’t know,” I said.
“Well you can do whatever you want to do. That’s the beauty of the world.” But apparently he didn’t mean it. There were exceptions as far as he was concerned—for instance, I couldn’t be a woman. I’d never felt more unwanted in my life when he saw me in that red dress.
I decided to spend half of my money on some new clothes that next day. I went to the mall and wandered from store to store, picking out a few cute outfits that would get me through the winter. I discovered that I looked amazingly cute in skirts. They made my ass look perfect. I even caught one guy staring at me when I was admiring myself in the mirror.
Then, when I went into a shoe store to buy a new pair of boots, I saw my parents. My mom was trying on a pair of heels and my father was lingering over her shoulder. He looked up at me and I looked away quickly. My heart started racing. I didn’t leave the store immediately—I didn’t want to look suspicious. So I pretended to look at a few pairs of shoes on the wall for a minute, with my back to my dad, and then I slipped out and hurried down to a health foods store that I knew he wouldn’t go near.
It was only a minute later when I felt the tap on my shoulder. I turned around and saw my dad, staring right into my eyes. I froze. I wanted to throw up. But at the same time, I was so happy to see him, so happy to know that he was okay. “I knew you were alive,” he said. “Your mother’s been worried sick.”
I opened my mouth to reply, but I was too overwhelmed. There was a lump the size of a fist in my throat—not that I could think of any words anyway.
“You should come around the house later to let her know
that you’re okay,” he said. “I won’t tell her that I saw you here.” He gave me a pat on the shoulder. “You look good, by the way.” Then he turned around a left. I was deeply confused.
Did my father not care that I was dressed up like a woman? Was he just pretending to be supportive so that my mom could see me again? Or was his disappointment in me just in my head? Was he ever really that disappointed in me? After he saw me in that dress, he went three weeks without talking to me. Then, he never looked at me the same way—at least that’s what I thought. But maybe that was just my own insecurities. Maybe he never cared about the dress thing. Maybe he wasn’t embarrassed about me, but embarrassed for me.
It was the next morning when I decided to walk over to their house. I slowly approached the door. I reached for the handle with a trembling hand. Then I looked through the office window and saw my dad’s desk. Sitting on the desk was a pile of fresh MISSING signs. Was my dad the one who was going around tacking them up everywhere? Was my dad the one who still believed that I was alive, even though the police had declared me ‘presumably dead’?
I knocked on the door and took a deep breath. I was wearing my wig and my white parka and a new skirt that looked amazing on me.
I heard someone approach the door. I stood up straight and bit down on my tongue. I was ready to face my insecurities. I was ready to come home. I was done with running away from the things and the people that made me uncomfortable.
THE END
SISSY FUN
Everyone is shocked when Liam marries Janie, a stunning model who is way out of his league—just three months after meeting. But she can’t be a gold-digger, because Liam has no money. So why did she pick Liam, a short, thin guy who still had his V-card the day they met?
Womanized Page 62