“You’re so tight,” she said.
I didn’t have anything to say to this. I just kept my eyes closed and my breathing under control. I figured she would get bored soon. And I prayed that she wouldn’t notice the huge erection that was growing between my legs. But I couldn’t help it—she was pressing that bottle right into some sort of pleasure spot, making my legs tremble. I even started to moan against my will. She let another little giggle slip, as if she thought it was funny. But there was nothing funny about it. It was just humiliating.
“You like it,” she said. “I thought you said you weren’t gay.”
“I’m not gay,” I managed to say between moans.
“Well then why do you like it so much?” she asked.
“Because it feels good. I’m sure if a chick stuck a bottle in your pussy you would like it to—that doesn’t mean you’re gay.”
“I would like it—because I am gay,” she said with a giggle. “Well—I’m bi. Maybe you’re bi too.”
“I’m not bi. I’m straight,” I said.
“Okay. Suit yourself.” She pushed that bottle in deeper. Then she reached around with her free hand and grabbed my stiff erection. She pulled back my foreskin and giggled again. “Do you think Chris would be mad if he found us like this?”
“I don’t know—I’m not dating Chris,” I said.
“So he wouldn’t care if he saw someone else jerking off his girl?” She started laughing as if she just made the funniest joke. But I didn’t laugh with her. “How many times do I have to pump you to get you off, do you think?”
I didn’t reply. The euphoria was too intense. My legs were wobbling and my knees were trying to buckle. My heart was racing and the tingling in my shaft was intense. Now I was worried that I really was going to come, and just after a few pumps. Would she tell her friends that I was a premature ejaculator on top of being a cross-dresser?
I groaned and squirmed and then she tightened her grip on my cock. “Oh God!” I yelled. And then I started coming: blasting shot after shot onto that storage room floor. It felt so good—unlike any orgasm I’d ever had. It was so much more powerful and it lasted so much longer. In fact, after ten straight seconds, I was starting to worry that it wasn’t going to end, that I would end up passing out in my elated state. But the pleasure stopped as soon as she pulled that long tube out from my ass. I fell down to my knees and started catching my breath. She giggled as she tossed the bottle into the trash bin.
“That was fun,” she said. “I can’t wait to tell Darla.”
I suddenly sprung to my feet, despite my complete lack of energy. “Don’t you dare!” I snapped.
She rolled her head back and laughed loudly. “I’m just screwing with you, Joe. I won’t tell her. You’d better get back to your date. He’s probably wondering where you went.”
I slipped those sparkly red panties up my legs and then I put my grey sweater dress on over top. After all that, the least I could do was keep the lingerie for myself. I fixed my hair in the nearby mirror and then I said, “He’s not my date.”
She gave me a kiss on the cheek. “Okay, Joe. Okay.” I wanted to grab her and shake her and yell in her face that Chris wasn’t my boyfriend, but I knew it was pointless. I knew that a girl who worked a full time job wouldn’t understand the level of humiliation I was putting myself through for a measly hundred and fifty bucks.
I looked down at my long streaks of white cum underneath the little table. “You can clean that up, right?” I said. I smiled and then I left the room, unsure of what would happen to me on Monday at school. But I had a good feeling that Kelsey would stick to her word—though I suppose I had no reason I think that.
Chris was standing by the front of the store when I emerged from the back. “There you are. I was starting to worry that you ran away,” he said with a relieved sigh.
“I was just hiding out in the back. Is she gone yet?” I asked.
“She’s still around. I think she’s over by the service exit, so we should probably just double back through the mall,” he said. My stomach turned at the thought of going through the whole mall again. I knew that I was most unrecognizable but I also knew that my disguise wasn’t perfect. If Kelsey could recognize me, then anyone could potentially recognize me. And maybe some other people already had recognized me. Did I really want to double up the risk of being recognized? Or was it maybe time to face Chris’s mother head on?
Chris was already pulling me towards the direction we just came from. He wasn’t giving me a lot of time to process my options. So I just caved and went along with him. I looked back at the Victoria’s Secret and saw Kelsey waving at me with her little grin. I quickly pulled my hand away from Chris. He looked at me with a narrowed gaze and said, “What gives?”
“Let’s just get out of here—okay? Enough is enough already.”
I tugged down the skirt of my grey sweater dress, making sure it was fully covering any possible vantage point of the slutty red panties I had on underneath. Then I looked down at the multiple shopping bags Chris was carrying around and wondered what I was going to do with this big haul. Was I going to return it? Would they let me return it without Chris’s credit card? Maybe I could just hold onto it… Maybe it might be fun to try some of it on again.
A grin crossed my face, and then I pushed it away. I was letting this nonsense get the better of me. I couldn’t let Kelsey be right—I had to constantly remind myself that I really was just doing this for the money, and I deserved a hell of a lot more than I was getting… Did that make me an escort? No, no—I wasn’t sleeping with Chris; I was just letting him court me. But isn’t that what some people do with escorts?
“Hey Chris!” a voice yelled from across the open floor between us and the other side of the hallway. I looked over and then I wished that I hadn’t.
CHAPTER VI
Leaning against the glass ten yards away from us was Daniel Perkins. Daniel was one of our oldest friends. He went to every single one of my birthday parties until I stopped having birthday parties. He was part of the reason I was in this whole mess to begin with—though he didn’t know it.
One of reasons I agreed to Chris’s request to put on women’s clothing was because I knew that I could look like a convincing girl—and that was because of Daniel. Daniel had an older sister who lived mostly with Daniel’s dad out of state. But she still had a bedroom at Daniel’s house, just down the hall from Daniel’s bedroom.
It was during a sleepover one night, while we were playing hide and seek, when I had the idea to try on his sister’s clothes. I was hiding under her bed and there was a pair of worn panties lying next to my face. I loved the way they smelled: like perfume with a hint of pussy. I went back into that bedroom after everyone fell asleep and I put those panties on. I kept them on underneath my jeans until I got home the next afternoon. Then I stuffed them into the garbage with a pounding heart and prayed that my parents wouldn’t notice them when they came to take out my bedroom trash.
But that strange new urge didn’t go away. It was a month later when Daniel invited us all over for another sleepover when I started getting those crazy ideas all over again. Once again, after everyone was asleep, I snuck into that room and I tried on another pair of panties—and this time, I tried on a skirt as well.
Then I took it all off and cursed myself for succumbing to urges that shouldn’t have existed in the first place. I suppressed those weird feelings until a year later, when we were all at his house again. Everyone went to sleep and I was wide-awake, with the thought of that big closet filled with all of those soft fabrics and tight lacy garments. I fought the urge for a while, but I eventually caved, around 4:00 AM. I snuck over and I started trying things on. I found a big bag of makeup wipes in one of the desk drawers, so I decided I would try my hand at doing my makeup. I quietly drew on eyeliner and then I put on some eye shadow. Then I put on a touch of dark red lipstick and that’s when the door behind me opened up.
I froze, my heart tumbl
ing down into my stomach. I looked back slowly and saw Daniel’s mother. She was a younger woman—much younger than my mother, having had Daniel when she was still in high school. She stepped into the room and closed the door behind her. Then she said, “You would look much more feminine if you shaped your eyebrows just a little bit.” I was still completely frozen when she walked over and grabbed a pair of tweezers. “Want me to show you?”
“O—Okay,” I said. I was worried that I was about to throw up on her. She leaned in and started plucking my eyebrows. Then she showed me how to make my jawline appear smoother with some simple contouring.
She picked a dress out for me and then she watched as I changed into it. “Please don’t tell Daniel about this,” I said.
She smiled and said, “I won’t.” Then she left the bedroom and I never saw her again, because I never went back to Daniel’s house. I couldn’t bare the thought of seeing his mother again, knowing that she knew a secret about me that no one could ever know. I never got dolled up again—not until Chris begged me to be his pretend girlfriend.
Chris walked over to the glass barrier. “Hey!” he called out. “What are you doing here?”
“You told me to meet you here. We’re supposed to see the new Star Wars movie,” Daniel called back.
“What? Was that today? I forgot about that.”
“I’ve literally been texting you for the past hour, you asshole.” Daniel looked around. “Hold on, I’m coming to you.” He had to walk down about twenty yards to reach the nearest bridge connecting the two sides of the isle. During the wait, I looked at Chris, suddenly feeling suspicious of this whole charade.
Did Chris bring me along so that all of his friends would think that he had a girlfriend—and not just his mother? Did he know that half of our school would be at the mall for the big sales? Did he bring me to that Victoria’s Secret because he knew Kelsey was working there? Did he want absolutely everyone to think that he was in a relationship—or did he have nefarious plans?
Was it possible that he brought me just to humiliate me? Was he hoping that I would be recognized? Was he secretly texting everyone to come and bask in my horrible humiliation. But why would he do it? Weren’t we friends? Did I recently do something to him that made him want some sort of emotional revenge?
Daniel walked up and I took a step away, looking away so that Daniel wouldn’t see into my eyes. If Kelsey recognized me, then Daniel would have no problem recognizing me. I’d spent entire nights with Daniels over the past decade—Kelsey was just a chick who had been in some of my classes over the years.
“This that girlfriend you’ve been telling me about?” Daniel asked. I didn’t look over, instead pretending to be infatuated with a dress in a store window.
“Um, yeah—this is her. This is Riley.”
I closed my eyes and took a deep breath. I actually kind of liked the name Riley, but that was beside the point. I turned around slowly and forced a smile. “Hi there. I’m Riley,” I said, making a small wave.
“Hi Riley,” said Daniel. “I’m Daniel—Chris’s friend.”
“Right—I think he mentioned you,” I said. I looked away from him quickly, not wanting to give him enough time to recognize me.
“Well maybe your pretty girlfriend wants to come and see the movie with us. What do you think, Riley—want to come see the new Star Wars with us?”
I forced a smile. “That sounds great, but I actually need to be going here. Chris was just walking me to my car.”
“Oh, c’mon. It’s still early. If we go now, we can get good seats.”
Chris looked at me, as if he was expecting me to bail us out of the awkward situation. Why wasn’t he the one sticking up for me? Why was he making me open my mouth, putting my reputation on the line? I wanted to give him a swift nudge to the gut with my elbow, so that he would smarten up and act like a man. But instead, I said, “I actually need to buy a dress for an event this weekend, and the store I want to buy it from closes in two hours. By the time the movie’s over, the store will be closed, and if I go now, by the time I try on and buy the dress, the movie will be full. But maybe let’s set something up for another time.”
Daniel nodded his head slowly. He was looking into my eyes now and his gaze was starting to narrow, as if he was starting to recognize me, trying to place my face in his mental database. I looked away quickly, before he could connect too many dots.
“What about you, Chris? Do you want to come with me?”
Chris hesitated. “I was going to help her pick out a dress. You don’t mind, do you? Maybe we can see the movie tomorrow.”
There was a silence. Then, Daniel shrugged his shoulders. “I guess we’re going dress shopping,” he said with a strange amount of enthusiasm. “Want me to carry any of those bags for you?”
“I—I’m okay,” Chris said. I looked at Chris again, giving him a dirty look so that he knew that I was pissed about the situation. Why couldn’t he just drop some balls and tell Daniel to screw off so he could enjoy his date with his girlfriend. It would have been as easy as saying, ‘Sorry, I don’t get to see Riley often, so I’d like to spend this time with her alone.’ But no, he had no spine—and I guess I shouldn’t have been surprised. This was the same guy who orchestrated this whole thing so that he didn’t have to admit to his mother that he was lying about having a girlfriend. This whole situation was pathetic, and for some reason I was the one facing all of the repercussions. Chris should have been the one getting pegged in that back room at the Victoria’s Secret.
CHAPTER VII
It wouldn’t have been so bad if it weren’t for Daniel looking over at me every ten seconds. At one point in front of the mirror, while I was holding a dress up to my torso, I noticed him in the reflection behind me, staring at me with strangely wide eyes. I couldn’t help but think that he was on to me—or about to be onto me.
I looked back at him and smiled, and he looked away quickly. My heart was racing. Chris walked up to me holding a little pink dress. “I think this would look nice on you,” he said with enough volume for Daniel to hear.
I looked down at the dress. It wasn’t really my style. It looked like something a guy would pick for his girl: short but not in a cute way, and tight but not in a flattering way. “I’ll pass,” I said. Then I took a step closer to Chris and whispered, “You need to get me out of here. This is enough already.” Then I motioned to the video game store across the mall hallway. Three guys from our gym class were shopping around for a game. One of them—a guy named Bradley—had been going to school with us for years, and we all suspected that he was autistic. I’m sure he would only take a single look at me before realizing who I was.
“We just need to kill another twenty minutes,” Chris said. “Once that Star Wars movie starts, we can go.”
I took a deep breath. He may as well have been saying four more hours.
“Just try on a dress and take your time.”
So I found myself a nice little dress to distract me from the slowly ticking clock. The dress was cute—actually cute, unlike the pink dress Chris found. It was black with a long slit down the front, held together by crisscrossing strings. The dress was intentionally shorter on my left side than it was on the right, and it made my hips look immaculate. I didn’t just pick the dress because it was cute; I picked it because it was one of the more expensive dresses in the store, and I still wasn’t finished getting my revenge on Chris.
I especially loved how thin the dress’ straps were on my shoulders, almost like it was a strapless dress. It felt so soft and airy, even though it was almost completely tight to my skin. I had to awkwardly tuck my balls into my body so that I could defeat my bulge. If I were to ever wear the dress out, I would wear a pair of firmer panties… Not that I planned on ever wearing it out. In twenty minutes, I would be finished with all of this feminization crap.
I stepped out from the changing room. Chris was standing there and Daniel was across the store. “That looks amazing,” Chris said
loudly—almost comically loudly.
“Okay, cool it just a little bit, buddy,” I said. “The goal at this point is to not be noticed.”
“We still need to be convincing. If you stop being convincing, then this was all for nothing.” And it was a good point—though we could be convincing without yelling out to everyone in the mall, trying to get their attention. After my moment with Kelsey, I wasn’t so sure about my disguise. I was now worried that anyone who knew me could easily identify me—and maybe many of them already had identified me. I couldn’t help but notice that Daniel was looking at me again, from across the store, still with those judging eyes. He noticed me looking at him, so he forced a smile. “Looks good!” he called out.
“Thanks,” I called back. “Think Chris should buy it for me?”
“Absolutely. Chris, you’ve got to buy her that dress. It would be a travesty if you didn’t.”
I watched as Chris’s face turned a shade of white. He awkwardly forced a smile and then he nodded his head. “Yeah. Great,” he said with a monotonous voice. Then he looked at me with a scowl. I winked at him and then I slipped back into the changing room.
I didn’t get changed right away. Instead, I took a seat on the little bench and then I closed my eyes for a minute. What was supposed to be five minutes had turned into hours—and the clock was still ticking. I’d been blackmailed, humiliated, and tugged around the mall like a dog on a leash—and I wasn’t even getting enough money to buy half of a new PlayStation. This was definitely the last favour I would ever do for Chris. Hell—I was even considering the option of telling everyone at school what happened, just so that I could beat someone else to it. Because it was only a matter of time before Kelsey told Darla, and it was only a matter of time before Darla told one of her friends. Within a week, the whole school would know about my sissy excursion—but maybe I could laugh it off before then.
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