“I think I’m almost done,” I said. “Just one more last wipe and… Yep! It’s all done.” I spun around to show her the dress, which was now just wet and no longer stained. “It’s good that we got to it before that wine got too dry.”
She was still sitting on the edge of that bed, staring up at me with that adorable smile and those glowing eyes. “It looks good,” she said without moving. And I figured it was my chance to make a move. I put the dress down and I took a careful step towards her. My plan was to sit next to her, wrap my arm around her, and then kiss her. Then I would get into that blanket wrap of hers and we could rub our naked bodies together. My heart was pounding. I was about to lose my virginity, and what a girl to lose it to!
“Wait,” she said before I could take a second step. So I stopped. “Aren’t you going to try it on?”
And the question took me by surprise. I looked around. “Try what on?” I asked.
“The dress.”
I stared at her for a moment before letting a laugh slip. “Funny,” I said.
“What’s funny?” she asked with a straight face.
And I paused, looking back at the dress. “It’s a dress,” I said.
“Yeah. I want you to try it on.”
“W—Why?”
“Because it would look good on you, don’t you think?”
She stood up, letting her blanket fall down onto the mattress. And there were her bare tits—just as perfect as they were in my imagination, complete with perky nipples. She didn’t even bother covering herself as she walked past me and grabbed the dress. She held it up. “I think it would be so hot if you put it on,” she said. “Don’t you?” And she was looking at me with a serious face, as if she wasn’t suggesting something that was completely crazy.
“Hot?” I said, my heart stuttering. “You want me to put it on?” I was staring at her tits now. I couldn’t look away, no matter how hard I tried. They were too perfect. Her whole body was too perfect. It wasn’t fair. How could I say no to such a perfect specimen?
She was wearing nothing but red lacy panties—or maybe it was a thong. It did nothing to cover her perfect tush, and it hardly did anything to cover her plump pussy. I could feel drool tickling the corners of my lips. My head was spinning.
Was she drunk? Had she taken some sort of drug? Why did she want me to put on a dress?
I didn’t think too much into it. I was desperate to make her like me. Though as I pulled that white dress over my body, I couldn’t help but wonder if this was why all of her many relationships ended. Was this her kink? Did she like dressing her boys up like girls? No, no—she was always the one doing the breaking up, not the other way around. Unless she was breaking up with guys because they wouldn’t put on the dresses… No—even that sounded crazy in my head. Jenna was a beautiful, funny, and intelligent woman. She wasn’t a crazed lunatic. There must have been some sort of explanation.
I was shocked when the dress actually fit. I wasn’t a big guy, but I assumed that I wasn’t a women’s medium. Apparently I’d assumed wrong.
“Now do a spin,” she said.
So I did a spin.
“Keep your back straight. And smile. It’s a dress—you’re supposed to look cute in it.” I felt like an idiot, but I was prepared to do anything the beautiful naked woman told me to do. She stared down at my crotch, which was covered by the little skirt of the dress. “Take off your boxers. They’re ruining the illusion,” she said.
Again, I didn’t protest or resist. I reached under my skirt and took off my boxers. I figured she was just trying to get me bare down there, so that there wouldn’t be anything in the way when we went to have sex. So I was surprised when she reached down, pulled down her panties, and then handed them to me. “I’ve been wearing them since this morning. I hope you don’t mind,” she said.
And then I stared at them for a moment before looking back at her. I couldn’t remember the last time I’d blinked.
“Well?” she said. “Put them on. Don’t mind that they’re a bit moist.”
I slowly stepped into them and slipped them up. And they were a bit moist, as if she was turned on by watching me put on her dress. I looked down at her bare slit now and it was glistening. She really was horny. I laughed nervously. “How do I look?” I asked, playing along with her strange fetish. I still wasn’t sure if this was serious or if she was just mocking me. She had no reason to mock me, unless she was secretly angry about the dress. She never struck me as the vindictive and mocking type. She never hung out with the mean girls and she had a reputation for being nothing but kind to everyone.
“You look okay. But you sound terrible. If you insist on talking, use a nice girly voice,” she said. She brushed past me, walking like a model on a catwalk. She bent over slightly at the dresser and fished a makeup box out from the top drawer. “Well?” she said. “Come on over and let’s make you pretty.”
And for some reason I found myself standing in front of that dresser and the makeup mirror that sat on top of it. The beautiful and naked Jenna stood behind me. She squirted some globs of flesh-toned cream onto her fingertips and then she gently rubbed the cream into my skin. “This is foundation. We always start with foundation she said.” And then she grabbed a black marker and told me to hold still. She stepped around me and then carefully drew on my eyes. It felt weird, but I didn’t resist. She’d never been so close to me before. I could smell her tantalizing perfume, and I could feel the heat radiating off of her amazing body.
Then she grabbed a few more products and rubbed, brushed, and drew them onto my face. I wasn’t paying much attention to the mirror. My attention was on her. Even though I felt very strange and uncomfortable, I didn’t want to forget this moment. I wanted to savour it. I wanted this moment to last forever. I wanted that smell to linger in my nostrils until the day I died. And my God, I wanted to reach out and squeeze those perky tits. But I managed to bite down on my tongue and stop myself from doing so, worried that would be crossing a line. Though she didn’t seem to mind my staring, even when I was staring at her pussy. A little dribble of fluid was running down her leg. Was she really that aroused?
She went into the en-suite bathroom and came out with a creamy product already squirted into the palm of her hand. I was surprised when she reached up and rubbed it into my hair, and then she started styling my hair, brushing it to the side like a French pixie cut from the sixties. I opened my mouth to ask her why she was doing this, and then I paused as I remembered her rule about speaking in a girly voice. So I made sure to use my best girly voice, which probably wasn’t very good (though it sounded okay to me). “So what’s this all about?” I asked.
“Don’t you think you’re so cute?” she asked, taking a step back and admiring me. She didn’t even seem to notice that she was completely naked, but she wasn’t stumbling around as if she was drunk or high.
I looked at myself in the mirror. And sadly, I had to agree with her. She’d made me look like a real girl. A cold sensation swelled in my gut as I took a step closer to inspect my face. My eyes looked bigger—and I’m sure that was intended. They looked somehow brighter, though maybe that was just a contrast trick. I bent forward even closer to the mirror to take a close look at the pink blush on my cheeks. It was blended nicely. I hardly recognized myself, and in a way that was a relief. Now I was less worries someone would come into the bedroom and see me all dolled up. There was no way anyone would recognize me—not unless they got up close and really inspected my features. But even my features weren’t terribly telling. She’d done some makeup tricks to my nose and cheekbones to make them look different.
Suddenly, she was behind me, her nude pelvis pressed against my bum. She pulled up the skirt of my dress gently and rubbed my ass with both of her hands. She let a little sigh slip out from her lips. I could feel the stubble of her little patch of pubic hair rubbing against my backside. I could see her face in the mirror. Her eyes were closed and her cheeks were dark red. I stood up straight and fel
t her tits against my back, and I could feel her heart pounding. I turned my head to give her a kiss, but she stepped back just in time.
I watched as she took a deep breath, as if trying to get control over herself. “I want to take your picture,” she said.
“You won’t show anyone, right?” I asked awkwardly, still using my girly voice.
She smiled. “Let’s face it. You probably want me to show everyone. Look in the mirror.” I looked in the mirror and she stepped up behind me, putting her chin on my shoulder. “You’re so pretty,” she said.
And then she stepped back again, this time with her phone in her hand. “Pose for me,” she said. I couldn’t say no—especially now that her tits were being pressed together by her arms as she held the camera out directly in front of her. So I smiled and started posing, feeling terribly awkward and stupid. I wondered how many guys had done this for her before. I wondered if these photos really would stay on her phone, or if I was making a giant mistake in my lousy attempt to get laid.
“Turn your back to me and look over your shoulder,” she said. So I turned my back and looked over my shoulder. “Look right into the lens. Good. Now look up at the ceiling and show me the whites of your eyes. Good—beautiful. You’re so cute.”
When I spun back around to continue posing, I noticed that she now only had one hand on the camera. Her other hand was between her thighs, rubbing her pussy. “Don’t stop,” she said. So I kept posing, pushing out my hips, moving my hands onto different parts of my body. I even held the skirt of my dress up slightly for one shot, teasing my red panties, which were still a bit wet from her damp pussy. Now Jenna was rubbing her snatch harder, pressing two fingers in deep. She was moaning slightly, so I didn’t stop. I cupped my non-existent breasts and squeezed, and Jenna moaned loudly. She was still taking pictures with her free hand, which was now trembling.
I blew a kiss at the camera, and that was it for her. A gush of warm fluid rushed out from her pussy and splashed on the floor. She bent over and shuddered and muttered the words, “Oh my fucking God.” And then I went over and took the phone from her hand. I placed it on the nightstand next to the bed and then I reached down between her legs to feel her dripping slit. She took my hand and pressed it hand against her pussy. “Fucking rub,” she said through clenched teeth. So I rubbed, and thirty seconds later, another warm gush of fluid was trickling through my fingers.
With my free hand I pulled my cock out. She grabbed it before I could get it close. She started to rub and stroke it while staring into my eyes. No girl had ever touched my cock before—and I’d never touched a pussy before for that matter. Though in the moment, it didn’t seem strange that I was achieving so many firsts while dolled up like a girl. Though I would wake up in the morning feeling rather strange about it.
I wanted to stick my cock in her, but I was too much of a virgin to make it. She pulled me closer by the cock and she spread her legs slightly so that I could penetrate her. But her hand just felt too good clenched around the tip of my dick. I ended up coming before I got it into her. I sprayed her pussy and her thighs with my hot load. “Oh my God,” I’m so sorry,” I said.
She was good enough to stroke me until she’d squeezed out the final drop of cum. And then she giggled, as if it was funny—and it probably was to her. “It’s okay,” she said. “I came twice anyway.” And then she looked up into my eyes with a grin. “I’m just glad you liked it.” I had a weird feeling that she wasn’t referring to her handjob. Did she think I liked wearing that dress? Did she think that I was happy in that makeup, with my hair styled like a little slut?
I smiled awkwardly and then she climbed into the bed, still covered in my cum. “Want to sleep with me tonight?” she asked.
I nodded my head, and then I started to pull down my panties.
“No, no. I want you to sleep in my dress,” she said. “Panties too—and the makeup.” So I climbed into the bed, all dolled up, and I got snuggled up behind her. We didn’t have sex—we just cuddled until we fell asleep. And then when I woke up, I was alone in that bedroom.
“Jenna?” I called out, the morning sun blinding my slightly as it poured in from outside.
There was no response. I got out of the bed. “Jenna? You still here?” I called out.
And then the bedroom door opened and a man walked in. “Oh, hey,” he said. “You need to get out of here. My parents are going to be home any minute. I have to get this place cleaned up. Oh man, I don’t know what I’m going to do. The living room is such a mess, and someone chipped up the countertop in the kitchen. What am I going to tell my parents?” He looked right at me, but he didn’t seem to notice that he was looking at a man in women’s clothes. I smiled and nodded and I brushed by him. There were still a few partiers with hangovers lingering around the house. The bathrooms were all closed and locked and I could hear people throwing up inside. I had nowhere to clean myself up, so I had to walk home dressed like a girl.
And I was ten minutes from the house when I realized I’d left my clothes behind. I didn’t go back. I didn’t want to risk facing my friends. So I went straight home. I snuck in the backdoor and I crept up the stairs towards the bathroom quietly. Once I was inside, I made sure that door was locked, and then I had the longest shower of my life, making sure every little bit of makeup was off of my face before I got out to hide Jenna’s dress and panties.
CHAPTER III
I was too afraid to reach out to Jenna after that night. I looked her up on Facebook the very next day, and I considered sending her a friend request. But I didn’t end up sending anything. As soon as I saw a picture of her face I remembered how embarrassing it was walking home in that dress. If that’s what Jenna needed to get off, I wasn’t sure that was something I could do. For the first time, I could understand why Jenna wasn’t able to hold down a relationship. But now I really couldn’t understand why so many guys wanted her back so badly.
I found myself checking all of Jenna’s social media pages, making sure she wasn’t posting those photos anywhere. I was tempted to send her a private message, asking her to delete the photos. But still, I was too afraid to reach out to her, and a little bit confused as to why she wasn’t reaching out to me—and why she left without saying goodbye. Did she regret our strange little romp? Did I ruin everything by coming so quickly before I even got it inside of her? Or maybe I ruined everything by actually going along with Jenna’s dress up game. Maybe she actually thought I was into it and that was a turn off—but how could it have been a turn off if she was literally squirting down her legs?
I closed down my Internet and tried not to think about what had happened between us. I stuffed that dress and that pair of panties into the back of my closet and I tried to erase my memory of it entirely. And after two weeks, I started to forget about it. The image of Jenna’s naked body would cruise into my mind occasionally, but I somehow ended up convinced that it had just been a strange dream and not a real encounter at all. And maybe that’s all it was. As long as I didn’t look in the back of my closet, that’s probably all it was—a weird dream.
Another month went by and I felt a strange peace and relief that I hadn’t felt in ages. I was no longer obsessed with Jenna. Something had changed in my brain’s chemistry, and now I only thought of her as a cute girl, and not the woman I needed to be with for the rest of my life. I finally didn’t feel like I was holding onto any regrets, and I finally felt like I could go out and meet a girl and not be constantly comparing her to what could have been. I found myself looking around during my classes, admiring different girls, considering real futures with them.
And then I started feeling excited. In just a week, our town would announce the new Miss Beautiful. Every year, our town crowned a different girl as ‘Miss Beautiful’. It was kind of like a pageant, though they had stopped doing the actual pageant a few years back for budget reasons. Now, they just had girls submit themselves online, and then they announced a winner on public television. The winner would get a bunc
h of free stuff, and then the winner and all of the runner-ups would go from bar to bar for a week, meeting the locals—which I think was just an excuse for guys to hit on pretty girls. It was our town’s only big party, and everyone looked forward to it—especially the guys.
I’d already made sure my schedule was clear for the week of partying. I made sure I had no meetings or appointments. I wasn’t going to miss any big parties. I was going to go to all of them and I was going to mingle with the Miss Beautiful contestants, and I was finally going to lose my virginity. I was sure of it, until I turned on my TV to see who won the contest.
I became paralyzed with fear as a picture of me graced the television screen, and every other television screen in town. There I was, standing in that white dress, with my hair neatly slicked to the side. Either I was just having a terrible nightmare now, or that night with Jenna had really happened, and someone had gotten a hold of that picture and submitted it to the Miss Beautiful contest.
I had to rewind my television to see that it was real—and it was. That picture had really come up on the screen with the word ‘Winner!’ underneath it. The whole town had really just seen a picture of me in a dress.
I ran up to my room and locked myself in. I was even too afraid to turn on the light, so I just sat in the darkness with my knees pulled up to my chest. My phone was on the nightstand, about to start ringing at any second. I knew my friends would call as soon as they stopped laughing. I knew my father would call as soon as he stopped having a heart attack. Oh God, the whole town had seen me wearing a dress and makeup! They were going to think that I was some kind of pervert or something. I didn’t want people to think that I was a cross-dresser. I only put the stupid dress on because Jenna wanted me to—so that she could get off.
My laptop screen was glowing at me from across the room. I had a Facebook tab open, and I could see that there was a red circle in the corner, letting me know I had notifications. It was surely my friends, pouring into my page to leave their humiliating comments publically for everyone to see. My heart was pounding. I was going to be sick. I’m not sure how I wasn’t throwing up. I pinched my arm hard, hoping it would wake me up. But I didn’t wake up. I was trapped in a nightmare that was too real.
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