I watched as he swallowed and became redder. “I don’t know,” he said.
“How’s about this?” I leaned forward and kissed him on the lips. It was a strange feeling, kissing a man. His lips were a bit chapped and his patchy stubble itched my face—but he kissed back. That kiss lasted five seconds. Then I leaned back and looked into his eyes again. My heart was pounding absurdly fast. I was surprised that he couldn’t hear it thumping against my ribcage. “Well?” I said.
“That was nice. But—But I still don’t think I’m allowed to let you leave with that stuff. No offense.”
So I slipped a hand down, pressing my fingers down the front of his pants. He perked up and let out a gasp as my fingers slipped around his warm, smooth girth. I grabbed him tightly and began to massage him. I could feel his tip swelling as his veins began to pump blood into his shaft. His eyes were wide and his face was white now. He bit down on his lip and let out a little groan. I kept massaging, still staring into his eyes with a grin on my face. My hands were no longer trembling. I felt strangely powerful, strangely in control of the whole situation. I knew that I was going to get what I wanted. I knew that I could make Kyle do whatever I wanted. “Twenty-two-fifty—just for me,” I said.
His cock was already hard, already throbbing in my clenched fist. I pulled it out from his pants and then I pressed it up against my abdomen. I looked down and saw that it was red from my tight grip, but he didn’t seem to mind. I was pumping him fast now, focussing mostly on his tip, but occasionally reaching down to stroke and feel his whole shaft. His legs trembled and nearly buckled. He swayed slightly and let another little whimper out from his lips. “You can come on me, if you want,” I said. I was pressing his tip right against my red satin blouse. I could feel it rubbing against my abdomen. It was warm and throbbing intensely.
Kyle was looking around frantically, still squirming and trembling. Was he worried his boss would walk in at any moment? Was his boss just in the back room? Was I putting myself in an unnecessarily risky position—just for twenty bucks worth of groceries?
I could feel his girth bloating up. He groaned and clenched and squirmed and moaned. “I swear I don’t normally come this fast,” he said. And then I looked down just as his rod was squirting globs of white goo onto my blouse. I let a little giggle slip, though I’m not sure why. I should have been disgusted. I had to walk over a mile with a stranger’s jizz on my shirt. But in a strange way, I felt empowered. I felt like I could get anything I wanted. I felt sexy and strong. I knew that I was going to survive the winter without compromising my identity.
I let go of his cock. He stumbled back and grabbed onto the counter behind him. He quickly stuffed his rod back into his pants and cleared his throat. “Okay,” he said. “Have a good day.” He cleared his throat again. “Can I—uh—can I get your number maybe? Do you want to go see a movie or something?”
“I’ll see you later,” I said with a little wink. I picked up my heavy groceries and then I left the store. Once I was a few steps away, reality caught up with me. My heart suddenly started pounding and my gut became filled with nausea. I looked down and saw that big load of cum dripping off of my red blouse. Did I really just do that? Did I just jerk a guy off for twenty bucks’ worth of groceries? Was I really this desperate to remain dead in the eyes of my hometown?
CHAPTER IV
My money was gone—nowhere to be found, and I spent two hours looking around those woods where I made my dive. I was starting to think that the money fell out of my pocket long before I threw myself on the ground, or maybe it disappeared afterwards, when I was closer to the grocery store. Either way, with the big windstorm that was starting up, it was gone. I was officially broke. At least I had a few weeks’ worth of food, to at least last me until the New Year.
I managed to get the cum stain out of the red blouse with a bit of baking soda and lots of gentle scrubbing. I hung it up nicely where I found it, along with the rest of the clothes that I borrowed. As I closed the closet door, I told myself that I would never do it again—I would never put on women’s clothing and relive my embarrassing high school days.
As predicted by the meteorologists, the weather worsened over the next few days. Snow began to fall and ice began to coat all of the windows of the farmhouse. The news was issuing weather warnings and schools were being shut down. “This bad weather will likely last another couple of months, so buckle in,” said the news anchor. And I had no problem with that. I had a nice little den set up in the basement of that farmhouse, right next to the furnace room. I had my couch and my television and lots of blankets and up in the pantry I had all of my food.
And I even had a plan for my next grocery shop. I’d located a nearby pawnshop—a three-mile hike. I found a few old iPhones in one of the kitchen drawers. They were out-dated, but they worked. I figured they would be good for at least fifty bucks—enough to pay for the rest of my winter stay at the farmhouse. And I figured the family who owned the house wouldn’t miss the old devices.
It was three weeks later when I decided it was time to make the trip to the pawn shop and the grocery store, to stock up for the rest of the winter, even though I still had a week of food left. I tried to think of a way to get it done without getting dolled up, but I couldn’t think of any other solutions. One more dress up wasn’t going to kill me.
The weather had let up; the wind had stopped and the air was nearly ten degrees warmer. The cold was supposed to return quickly, so I knew I only had a small window—and the boredom was starting to drive me crazy. I needed a day out of the house if I was going to keep my wits for the rest of the winter.
I spent the morning getting ready. I knew my adventure would take at least a couple of hours, so I made sure that I was prepared. After doing my makeup, I filled a little purse with makeup supplies, just in case I needed to make a few touch-ups between the pawnshop and the grocery store. I curled my wig, making it look more realistic. Then, I got dressed. I went with the black leggings again, seeing as I still couldn’t fit the tight jeans and I wasn’t about to wear a skirt out in the cold, even though the weather wasn’t quite as unforgiving. I found a cute beige sweater; it was baggy, hanging over one of my shoulders, leaving one red bra strap exposed. I kind of liked the look though—it was a bit sexy, just in case I needed to use my looks to get what I needed.
The first time I went out, I had my boxers on underneath my leggings. But that looked ridiculous, and I was lucky that Kyle didn’t notice. I couldn’t take that risk again, so I put on a sleek pair of red panties, to match my bra. They were tight, but they didn’t show through my tight leggings, so they were exactly what I needed.
I grabbed a beige toque to match my sweater and carefully slipped it onto my head. It helped make my wig look more realistic, and it also helped to pull my whole outfit together. I put on the same tall black boots I wore during my first sissy excursion, and I even accessorized a little bit with some costume bracelets, some rings, and a fake gold necklace. I spent a few minutes posing in front of the mirror, building up the confidence to go out.
I looked unrecognizable. I looked like a woman. And for once in my life, I was happy about it. I felt strangely calm, not worried at all that I would be recognized. Maybe I could spend the whole day out—not just at the pawnshop and the grocery store. Maybe I could grab a coffee from a café. Maybe I could get a drink at a bar. Maybe I could walk around a park and feel the presence of other humans for at least a few minutes. Maybe I could experience what it was like to not be a pariah.
But first, I needed to stock up my pantry so that I had a safety net. I grabbed those old iPhones and I grabbed my wallet. I left my male clothes in a bag in the basement, next to my couch bed. I should have brought that bag with me.
I left the house without much hesitation. I didn’t stumble in the heeled boots. I felt like I was quickly getting used to them, and I still found them to be even more comfortable than my ragged boots, which I left by the front door of the house.
&n
bsp; I wasn’t in a rush. I had my white parka on with my hands stuffed into my pockets. I was enjoying the warm sun on that calm winter day. I felt strangely peaceful. I didn’t even flinch when cars drove by me. One man even stopped next to me and asked if I wanted a ride. “I don’t mind walking,” I said. And I was surprised that I didn’t even hesitate to use my girly voice.
The man nodded and drove off, and I continued on my way. I passed the grocery store and found myself inside of the town where I grew up. There were a few people out on the streets, running errands. It occurred to me that it was a weekend—a rare warm weekend in the middle of a cold winter, so it made sense that many people would be out. I tensed up for a moment as I walked by a small group of people. Then I relaxed as they casually smiled and nodded in my direction. No one took a second look at me—except for a few guys, who took a second look down at my body, completely fooled by my disguise. But I couldn’t blame them. My disguise even fooled me a couple of times as I passed reflective store windows. I even made myself jump as I looked over and caught my reflection.
I saw the pawnshop appear in the distance, and then I stopped. I pulled the old iPhones out from my pocket and a sense of guilt suddenly overwhelmed me. Sure, the iPhones probably had no value to the owners of that farmhouse, but they weren’t mine to sell. And maybe they did have value. Maybe there were photos on them that the family didn’t want to lose. Maybe that’s why they didn’t simply toss them in the trash. I couldn’t give away some family’s memories.
For nine months, I’d managed to stay away from the world. I didn’t exist to society, and I liked it that way. But now that wasn’t the case. Now, I had become a mooch. I was a lowlife squatter, stealing gadgets from drawers and stuffing my face with food that didn’t belong to me. This wasn’t what I wanted to be. I didn’t run away from home just to come back as a scummy homeless vampire.
So I turned around and started back towards that farmhouse. I was going to put the iPhones back where I found them. I could find another way to make some money for food. I still had a week’s worth in the pantry, so there was no immediate rush. Maybe I could wait until Kyle was working again. I could give him another handjob. I could let him come all over me, so that I could make it through another month. Sure, being coated with cum was a little bit degrading, but at least it was a way to earn a living. At least then I wasn’t stealing—I was just paying with alternative methods.
The thought of giving Kyle another handjob made my heart rate spike, but it also brought the strangest little smile to my face, as if it was something I was actually excited about. And maybe I wasn’t necessarily excited about the thought of rubbing another man—but I was excited about the idea of having so much power. I liked the idea of actually being wanted for once in my life—and noticed. I was so used to being ignored or laughed it. Being out in that teenager’s cute clothes and makeup and wig were actually a nice little holiday from the torment that I was used to receiving.
When I walked by the grocery store the second time, I saw Kyle through the window. His gaze landed on me and his eyes widened. I waved and he blushed. I could already feel that amazing sexual power that I had. I wondered if I would have the same power over other men.
I meandered over to the store and slipped inside. Kyle sat up straight. “Good morning—I mean—afternoon. Welcome to the store. How are you doing today?”
I looked around to see if anyone was lingering about, but the place was empty. “I was hoping to grab some more chilli ingredients,” I said with a little wink. His face darkened quickly and his lips parted.
“Well, uh, I just got paid, so maybe I can help you out.”
I walked around his little counter. He took a small step back from me, as if he was intimidated by my presence. And who ever thought that I could have an intimidating presence? I still couldn’t get over how red his face was.
“We’re just a bit busier than usual today,” he said. “So maybe we could do this later—at my place, maybe.”
“No one will see me,” I said. I sunk down to my knees, sliding my body under the counter. Then I began to toy at his belt. He looked down at me with a big awkward smile. “You sure you don’t want to wait until later?”
“I’m staying in later,” I said. “I’m out now.” I pulled down his fly and I reached in for his cock. Why wasn’t I more hesitant? Why was I letting myself do this? Was I a whore? Was I the Slut Boy they all told me I was?
Kyle’s cock was already half-erect when I got it out from his pants. He was clutching the edge of the counter firmly. I pulled back his foreskin and then I gave his exposed tip and lick with my tongue. He twitched and perked up suddenly. Then I heard the dinging of the bell above the door. “Hello there,” Kyle said to whoever just walked in. “Just let me know if you need help finding anything.”
“Alright,” a man’s voice said.
My heart skipped a beat. My head felt suddenly hot and my hands began to tremble. What the hell was I doing? Not only was I whoring myself out, but I was also risking being caught and arrested for public indecency—just for some cans of beans. How had my life devolved to this point so quickly? Why was I allowing myself to do this? Why wasn’t I stopping myself?
I kept tugging his cock, getting it longer and harder. I had a firmly grip around his girth. It was warm and throbbing hard. He was still squirming slightly with his bottom half, while trying to act casual with his top half. He looked down at me briefly with wide eyes, as if he wanted me to stop. But I knew that he didn’t actually want me to stop. I knew he liked it. I could tell from his intense throbbing and the drop of sweet pre-cum that was oozing out from his tip.
I sucked him, getting half of his shaft inside of my mouth. He was bigger than I first realized. Even when I had his tip pressed against the back of my throat, I couldn’t get him inside of my mouth entirely. But I still sucked hard and bobbed my head fast. His cock became even harder, lifting up against the roof of my mouth.
“Hi there,” Kyle said to the man approaching the counter.
“Hey.”
“Is that all today?” he asked with a tense, high-pitched voice.
“Yeah—that’s it,” he said. Then I heard the beeping as Kyle rang the items through. I didn’t stop sucking. I kept bobbing my head, massaging his shaft with my puckered lips. I felt his veins with the flat of my tongue. I could feel him bloating and swelling. I bobbed my head faster.
“That’ll be—uh—thirty-five twenty-six,” Kyle said with an awkward voice. Then, without warning, his cock burst in my mouth. Hot cum shot into the back of my throat, almost making me gag. Kyle’s legs trembled and nearly buckled.
“You okay?” the man asked.
Kyle was slow to reply as his cock continued to unload inside of my mouth. I’m not sure how I stopped myself from choking loudly. “I’m fine,” he said. “I’ve just got this itch on the back of my neck.” He reached up and scratched his neck as I sucked the last drop out from his rod. Then I swallowed everything. It was sweet, but a bit bitter. It went down easily, but it left a lingering taste in my mouth, which I didn’t mind.
As soon as the man was gone with his groceries, I stood up. I looked at Kyle’s dark red face and I couldn’t help but laugh. “Was that okay?” I asked.
He nodded his head. “Aside from the fact that my old high school teacher just watched me come,” he said. And that’s when I recognized the voice of the man who just left. It was Mr. Finley, my old chemistry teacher.
“Mind if I just grab a few things and go?” I said.
He shook his head. So I grabbed another dozen cans of beans, a few cans of corn, and a couple bags of beef jerk. Kyle ran the items through and then he let me leave without paying. I’m assuming he took out his own credit card and finished the transaction.
I carried that heavy load all the way back to the farmhouse. But I didn’t make it to the door. As I stepped onto the large property, I noticed the truck parked in the driveway. Lights were on inside. I watched as a figure passed by the
living room window. The homeowners were home. My living space was compromised.
CHAPTER V
I found myself in the woods behind the farmhouse. My head was racing with anxiety. I knew I left my boots and my bag inside—but what else did I leave? A week’s worth of beans and beef jerky—maybe a can of corn… Was there any damning evidence in there? What about my wallet? I patted my pockets and found my wallet, with all of my cards inside. But what about in the pockets of my jeans? What about in my coat pockets? I couldn’t remember what I even had.
It was a few minutes later when a woman stepped out from the house. She was on the phone. I ducked down in the shadow of a log and I listened. “I told you: I don’t know! Someone’s been squatting here! What do you mean, how can I be sure? Yes—I’m sure that stuff isn’t mine, and it’s not Dale’s. Someone was sleeping on my fucking couch, Linda—of course I’m mad!”
I crept back, deeper into the woods, and then I watched for another half an hour. I had nowhere else to go. I couldn’t go back to my hut in the woods—not without a proper coat and a better pair of boots—and maybe even a pair of pants, seeing as my legs were starting to freeze in my leggings. But there was no way I would be able to get back into that farmhouse to retrieve my things. The sheriff pulled up to the house and went inside. I’m assuming they took my bag away as evidence. And was it possible they recognized my green coat? It was on me in that picture that was all over the town. What if the sheriff went to my parents and asked them if it was my coat? I didn’t want my parents knowing that I was still alive. I didn’t want them thinking that I was out squatting in people’s homes like some vagrant—even though that’s exactly what I was doing. There’s more honour in being mysteriously dead than there is in being a vagrant.
I crept away from the house. The sun was now dipping below the horizon and the temperature was dropping fast. I needed to think of something, or I would die out in those woods, only to be found later all dolled up with traces of cum in my mouth. Suffice to say, that was the last thing that I wanted.
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