“Why are you stopping?” Chris whispered. Though I’m not sure why we were both whispering—it’s not like Chris’s mother could hear us. Better safe than sorry though…
I looked around and spotted a door next to the women’s shoe section. “Over there—let’s go.” I grabbed Chris’s hand and we ran to that door. It was unlocked, so we slipped inside. The room was dimly lit and full of boxes. On top of the boxes were pairs of shoes that never made it back into their boxes after being tried on by customers. I started undressing.
“We’re just going to steal this stuff?” Chris asked. His face was pale.
“No—keep the tags and we’ll bring them to a cashier. We just need to shake your mom.”
“But the whole point of this is to make my mom think that I have a girlfriend.”
“Yes—and she thinks you have a girlfriend. Congratulations. Now the point is to get out of here without her getting any more clues as to who I really am. Understand? Now get changed. That sweater will look good on you, and it’s about time you get some jeans that fit properly.”
Now Chris’s face was turning from pale to red. He started undressing. I was already down to my panties and bra. I looked up and noticed Chris was looking at me. “What?” I said.
He looked away suddenly. “Huh? Nothing,” he said.
“What? You like what you see?” I asked jokingly, shaking my chest as if I actually had something to shake. Then I watched as his face really turned red and I realized that he maybe did like what he saw. “Ew,” I said. “Don’t tell me that you are gay. I mean—I don’t care. You can do whatever you want. But a little warning would have been nice before I took all of my clothes off in front of you.”
“I’m not gay!” he snapped. “You just—you really look like a chick. It’s weird.”
“I thought that was the whole point?” I said.
“Yeah—but you really look like a chick.” I wasn’t sure what he was getting at. A cold chill was creeping down my spine. There was an old mirror propped against the wall. I walked over and looked at myself. Chris was right. I really did look like a girl, even now as I stood in just a pair of red panties and a white bra. Even with my wig off and my short hair all ruffled up, I still could have passed as a woman.
And maybe that was part of the reason I couldn’t get a girlfriend. Girls don’t want to date guys that look like chicks. No girl wants to sleep with a dude with a better ass and better hips than her. Maybe it was time for me to start drinking protein shakes and hitting the gym twice a day. Maybe I needed to start rubbing some Rogaine on my face and chest, so I could cover up girly features with some thick, manly hair. But would any of that actually work, or would it just leave me looking like a chick with some muscles and a beard?
I looked away from the mirror. I could think of that stuff later. Now, I needed to focus on escaping that mall with my identity intact. I put on my new brunette wig and then I slipped into that grey sweater dress. The dress fit perfectly and it was amazingly soft on my skin. It even had a turtleneck to cover my subtle Adam’s apple, which was something I’d been paranoid about since leaving the house that afternoon.
But the outfit didn’t quite look complete. I looked around and spotted a pair of knee-length black heeled boots. They were swede and tight, but they fit surprising well—and they were much more comfortable than the heels I’d nabbed from my sister’s closet. “What do you think?” I said to Chris as I turned to him. I got to watch as his face turned red once again, letting me know that I looked pretty. “Okay, then let’s get out of here. We’ll grab some sunglasses on our way out.”
We slipped out from that shoe storage room and then we made our way to the cashier with our handfuls of price tags. I grabbed a cheap pair of big sunglasses off of a discount rack and tossed the price tag on the counter along with the rest. I also grabbed Chris a baseball cap, so that his mother wouldn’t recognize his scruffy hair. It was another three hundred dollar tab. Chris groaned but he still pulled out that credit card and paid for all of it. I leaned over and gave him a kiss on the cheek. “Thanks sweetie!” I said. And I swear I saw him crack a warm smile.
We walked out from that department store casually, wearing our new disguises, headed straight for that exit on the other end of the mall. “Did your mom text you again at all?” I asked.
Chris looked down and checked his phone. “Yeah. She still can’t find us,” he said. He showed me the most recent message: ‘Where did the two of you go? We can’t see you anywhere.’
“We?” I asked.
“Uh, maybe my dad is with her—or maybe my brother,” he said.
My heart stammered. Now there were multiple people looking for us and threatening my reputation? I tried to remember why I agreed to this nonsense, and then I remembered the big pay out. Though I was starting to think that Chris wasn’t going to pay me anything after buying me so many dresses and shoes and sunglasses and records and milkshakes and so on. Hopefully he would at least let me keep everything, so I could return it for a profit.
Chris looked around carefully. “Do you see them?” I asked.
It was a moment before he replied. “No,” he said. So we kept walking. Finally, that Apple Store was in sight. I could see that small door between the Apple Store and the Booster Juice: the service exit.
“We’re almost there,” I said.
Then Chris reached down and grabbed my wrist, stopping me. “She’s up ahead,” he said.
My heart stammered. “Where?” I said, trying to spot her. The mall hallway was busy and I couldn’t even remember what Chris’s mother looked like, but I couldn’t see anyone over the age of thirty in front of me. Was she in one of the stores? Was she looking our way? Would she recognize Chris, even with his baseball cap and his sunglasses?
“Let’s hide out here, just for a few minutes,” he said, tugging me towards the Victoria’s Secret. I was surprised that he picked a lingerie store, of all the nearby options. Maybe he wasn’t looking where he was pulling me, or maybe he thought his mother would never look in a Victoria’s Secret for him. “Just pretend to be looking through the racks,” he whispered in my ear.
So I casually walked over to a nearby rack and started to sort through the different little outfits. And I had to admit: there were some cute little numbers on that rack. I even pulled a little black teddy out and found myself wondering how it would feel on my body.
There was a tapping on my shoulder. I looked back, expecting to see Chris, and then I found myself face-to-face with Kelsey Addison—the little blonde girl I’d been going to school with for nearly twelve years, since we were in Kindergarten. “Can I help you find anything?” she asked, staring right into my eyes.
I shook my head quickly. “No,” I said. “I’m just browsing.”
She looked down at the little black teddy in my hands. “That one’s new. It’s so adorable. It would actually look super cute on you,” she said. “You’re allowed to try it on, as long as you leave your panties on.” Then she leaned in closer to me. “And if you aren’t wearing panties, I won’t tell anyone.” She smiled and my heart skipped a beat.
“Thank you,” I said, nodding my head again.
“No problem,” she said. “Oh, and we got a few other new things in. We haven’t even put them out yet, if you want me to show them to you—they’re in the back.”
“I think I’m okay. I’m just here with my boyfriend.” I regretted saying the words as soon as they left my tongue.
I watched as Kelsey looked over at Chris and said, “Is he your boyfriend?”
My legs were beginning to shake. I wanted to run out of that store—and maybe I was better off facing Chris’s mother. At least if Chris’s mother realized who I really was, there was a chance my classmates wouldn’t find out. If Kelsey realized who I was, then I was doomed. “Um, yeah, that’s him,” I said.
She looked at me with a smile. “Him and I go to school together,” she said. Then she leaned in close to me again. “To be honest with
you, I always thought that he was gay. But if he’s with a beautiful girl like you, he must be straight—right?”
I nodded my head. “Yeah. He’s straight—super straight. Though I guess I can see why people might think that he’s gay,” I said. My heart was racing fast. I was starting to worry that it was going to suddenly stop and I would drop dead in that lingerie store. Oh God—that would be so humiliating for my parents, finding out their son died in a lingerie store while dolled up in his sister’s clothing. I bit down on my tongue and tried to get a hold of myself.
“Well then come with me. We just got this two-piece in and it’s so sexy. It’ll drive Chris wild—I promise. C’mon—come try it on.” She started walking away, towards the back room. And maybe it was a blessing in disguise. Maybe this was my chance to get away from the snooping gaze of Chris’s mother. So I followed Kelsey into that back room.
I had no idea that she worked at the mall. I always assumed that she was one of the rich kids, like Chris, who just got a big allowance every month and that’s why she was always coming to school wearing new clothes, with her hair always done up and her nails freshly manicured.
The back room looked a lot like the shoe storage at the department store—except instead of stray shoes laying around everywhere, it was women’s underwear: a dangerous place for a high-school-aged male.
Kelsey grabbed the two-piece she was talking about. It was a dark red colour and a little bit sparkly, shining light even though there wasn’t much light in the room to shine. “Try it on,” she said, holding it out towards me.
“I’d better not,” I said. “But you’re right—it is super cute.”
“C’mon. Just try it on for me.”
I laughed. “I don’t really have any money to spend, and Chris has basically gone broke spending money on me today.”
She stepped forward with the little outfit and a grin on her face. “Try it on for me or I’ll tell everyone at school that you’re Chris’s girlfriend.” She was staring into my eyes with that evil look. My legs started to wobble in my tall boots. I took a breath of air in as I started to feel lightheaded.
“W—What did you just say?” I asked.
“Do you still go by Joe when you’re a lady?” she asked.
“Please don’t tell anyone. I’m just doing this for money. He’s paying me. It’s a long story,” I said. But I was still using my girl voice. No matter how hard I tried, I couldn’t shake that voice now, as if it had become natural over the course of the last hour.
“I won’t tell anyone, if you try this little outfit on for me.”
I stared at the tiny lacy two-piece. Then I looked back up at Kelsey. “Why?” I asked.
“Because I spend six hours a day at school bored out of my mind and then I come here and spend another eight hours bored out of my mind. Do you have any idea what I do all day? I help old ladies pick out bras that are the right size. I mean—how hard is it to just measure yourself? We literally have a measure hanging by the bra rack, but these ladies can never seem to figure it out. So I want a bit of excitement—sue me. Get undressed and try on the lingerie.”
I took another deep breath. “You promise you won’t tell anyone?” I said.
“I mean—I’ll probably tell Darla because we tell each other everything. But that’s the only person I’ll tell. I’ll tell her not to tell anyone.”
“Please don’t. You know that she’ll tell everyone. Darla has the biggest mouth in the school.” My heart was fizzling somewhere in my gut. I felt sick. I wanted this nightmare to end. I was praying for the moment when I sprung out of my bed and realized it was all just a bad dream. But it wasn’t ending. She was still standing there, staring into my eyes with that horrible grin.
“Try on the lingerie and we’ll talk,” she said.
So I snatched the little two-piece and then I pulled off my grey sweater dress. I felt awkward as I reached around and unclipped my bra, letting it fall to the floor, exposing my flat chest. I felt the strange urge to cover my chest, as if I actually had something to cover. I slipped into the red sparkly top. Then I went to slip the bottoms over my panties.
“No—take the panties off. You don’t wear panties over top of panties—that’s just weird,” she said with her grin. I started to turn around, and then she said, “No, no—do it facing me.”
“This is sexual abuse,” I said, narrowing my eyes.
“You’re welcome to go,” she said. “I’m not forcing you to stay here and I’m not taking pictures of you. You can either do what I say or you can leave. It’s really very simple.”
I closed my eyes and tried one last time to wake myself up from the nightmare. When I opened my eyes, she was still standing there, with her hands on her hips and that smirk on her face. I had to go through with it. I couldn’t let the whole school find out about my sissy mall excursion—even though it was now looking like that was inevitable. I had to give myself the best chance possible. So I reached down and slipped my panties to my ankles, exposing my cock and ball sack. I took the panties that matched the bralette and I quickly pulled them up, even though Kelsey had already seen everything.
She took a step back and looked at me with a growing smile. “See how cute you look? You have to buy that. I think he’ll really love it.”
“I’m not actually dating him!” I snapped. “I told you, he’s paying me because he wants his mom to think he has a girlfriend. I’m not gay.”
“You don’t exactly look like the type that likes girls,” she said.
“Well I am the type. Can I go now? Will you keep your mouth shut about this? I’ll give you a hundred bucks if you don’t say anything.”
She walked up to me and put her hands on my shoulders. “It’s okay if you like boys. That’s not weird or wrong or anything,” she said.
“I said I like chicks.”
She reached down and grabbed my hands, bringing them up to her breasts. I was shocked to feel that she wasn’t wearing a bra. I could feel her perky nipples pressing against the palms of my hands as she made me squeeze. She rubbed my hands in circles for a moment and then she let go, as if to see if I would continue without her forcing me. It was the easiest test in the world: I kept rubbing. I’d never touched tits before but I’d dreamed of touching them for my whole post-pubescent life. They were soft and squishy and even more amazing than I imagined.
Then I noticed Kelsey was looking down at my crotch. I looked to see what she was looking at. I had an erection, stretching the thin fabric of those sparkly red panties. “So maybe you weren’t lying,” she said. She brushed my hands away from her chest. “Well we can’t sell those bottoms anymore. You’ll have to buy them. No one will want to buy panties that had a boner in them.”
“I’m sorry,” I said, pulling the panties down quickly while covering my erection with my free hand. “I told you I was straight.”
“Bend over,” she said.
“What?”
“I said bend over.” She lifted up a long tube of Victoria’s Secret brand moisturizer. “I won’t tell Darla or anyone about this is you bend over. Keep those panties down.”
“You’re blackmailing me?” I asked.
She shrugged her shoulders. “I guess so,” she said.
I looked at that long tube, which wasn’t much thicker than my cock, and it was about the same length too. My heart stuttered—I knew she was going to try to stick it in my ass. And now I had to decide what was worse: the school finding out that I pretended to be Chris’s girlfriend, or taking a phallic tube in the ass for a couple of minutes in the back of a lingerie store. At least the tube option would be over with before dinnertime. The humiliation of the whole school learning about this embarrassing escapade wouldn’t end until well after graduation. So I walked over to the little nearby table and I bent over. “Just make it quick,” I said.
CHAPTER V
She opened up the bottle of lotion and squirted a bit onto the tips of her fingers. She giggled as she wiped that cold lotion on my
butthole. “You’ve got a great ass. What’s the secret?” she asked.
I didn’t reply. I kept my mouth shut and my eyes shut. I couldn’t decide if I wanted her manager to come through that door to find us. At least it would end, but it would be even more humiliating to have another person see me in this state.
Kelsey slapped my ass hard, making it jiggle for a moment. “Ouch! What did you do that for?”
“I couldn’t help myself,” she said. I heard her close the bottle of lotion. Then she pressed it between my cheeks. She rubbed it up and down the length of my crack, getting the outside of the bottle lubricated for entry. I took a deep breath.
“Why do you want to do this?” I asked.
“I let you squeeze my tits. It’s the least you could let me do.” She started pushing that bottle against my hole. I clenched at first, but I knew that resistance was only delaying the inevitable. I had to bite down hard on my tongue to force my anus to relax. And the moment I relaxed, she penetrated me. The bottle sunk in two whole inches and I let out a sudden whimper. It felt so big—so much bigger than it looked. I could feel my hole stretching. She stopped pushing for a moment. Now she stood there gently twisting it, giggling to herself as if embarrassment was hilarious. I bit down on my tongue again to make myself relax, and then that tube-shaped bottle sunk deeper.
“Does it hurt?” she asked.
“A little bit,” I said.
“I’ll be gentle.” She carefully pulled the bottle back before pressing it in again. With her free hand, she casually rubbed my bum, as if she was trying to comfort me—and it actually helped a little bit. I stopped biting down on my tongue and I managed to relax without causing pain to another part of my body. The pain in my ass started to go away, even though that bottle was sinking deeper and deeper. I tried to ignore the noise it made as she squished it in and out of me: kind of like a ketchup bottle that was just about to run out.
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