1.

I rooted through the foot locker, looking for something I’d considered wearing since I got up that morning. I set aside some of my clothes, which Gabby looked through like she’d never seen them before, despite the fact that she’d bought most of them for me. I’d paid her back for all of them, but still. I pulled out a pair of tops I’d never worn before and finally found what I was looking for.

“Okay, there is no way I was anywhere near you when that was bought,” Gabby said as she saw the slinky black dress I was holding. “Why haven’t I ever seen it before?”

I giggled. “I got it at the Goodwill, told the clerk I was buying it as a Mother’s Day gift. She seemed pretty jealous of Mom because of it, too.”

“Uh, yeah, I can bet. Do you know how long I’ve been looking for just the right LBD?” She took it from me and held it against herself. “And you find the perfect one for you when you don’t even have the assets to show it off? Girl, you are lucky.” She handed me back the dress. “This would be a big deal for anybody, but you’re gonna do something that a lot of natural born girls haven’t done yet.”

I pulled my shorts down. “Seriously? It can’t be that much of a big deal in a girl’s life.”

She shrugged. “It’s not, really, I just wanna exaggerate this moment.” She walked around me and I felt her grabbing her my bra. “Now, off with this.”

I pulled away from her. “What?! Why?”

She looked at me like I was crazy. “Um, look at it this way. The straps on the dress are like twigs, and the straps on the bra are like trees. Wearing that bra under that dress is like trying to hide the tree with the twig.”

I blushed. “So… Ya mean I have to go braless?”

“Girl, you’ve been crossdressing for years, this can’t be new for you.”

“I didn’t need a bra when I was crossdressing, I only wore them when I wanted to go with the full package.”

“Well, you’re just fine without a bra now. You’re perky enough to go braless for fifteen minutes while you wear that dress.”

I sighed. “Okay, but… Just let me take it off, okay?”

“Jeez, what’s up with you?”

I was starting to freak out a little bit. I didn’t want to outright tell her that I thought she was into girls. “Uh, nothing, just… Having somebody grab my bra was a little weird.”

She sighed. “Oh. And here I thought this was gonna get weird.”

I chuckled nervously. “Weird, right.” I turned away from her and reached behind to finish unhooking my bra. I pulled it off and then I was pulled around face-to-face with Gabby and she was staring at my boobs. “What the hell are you doing now?!” I screeched, quickly covering my breasts.

“Kenny, dear, please. I’m looking at you naked.”

“Why did you just call me dear?”

She shrugged. “It’s what my mom told me when she wanted to teach me how to do my first self examination.”

“That’s not what this is about, is it?”

She shook her head. “No, I just wanna see what your tits look like.”

I was certain I was red as a beet. “Why?!”

She reached out to touch me, but I pulled back. “C’mon, I know how to handle boobs, I’m not gonna hurt ya. Don’t you get how weird this is, Kenny? The only guy friend I have now has bigger tits than I do, this is intriguing to me. Are you telling me that if I was to suddenly turn into a guy, you wouldn’t be even a tiny bit interested in seeing how big my dick was?”

I shook my head rapidly. “No! Why the fuck would I be?!”

She shrugged. “I dunno. I thought guys had literal dick measuring contests all the time.”

“Not literal dick measuring, just metaphorical.”

She sighed. “Whatever, just lemme see the boobs.”

“Why?”

“Kenny, I’m not gonna do anything weird, just lemme see ‘em.”

“Letting you see them is weird enough!”

“Why? It’s not like seeing naked tits is something I don’t do everyday.”

“Seeing my naked tits is something you don’t do everyday!”

Gabby grabbed me by the shoulders. “Look, Kendra, you’re only going to have these magnificent mammaries for another five hours, you’re not risking anything by letting me see them!”

I clutched at my boobs a little tighter. Ignoring the fact that I thought she liked girls, it was still creepy as hell that she wanted to see me topless. “Just, please, no looking, okay?”

She sighed again. “Fine. You get this dress on and then we’re gonna have some fun.”

I gulped as she turned away from me. The concept of “fun” worried me.

2.

“Oh, baby, you look fantastic!” Mom said, amazed. I filled out the dress a little more than I thought I would, and my legs were completely exposed, to say nothing of the cleavage I was showing off. I smoothed the dress under me and sat down at the kitchen table.

“Thanks,” I said, nervously. Gabby sat down across from me, and Mom sat at the remaining seat. “I didn’t honestly think this would look good on me.”

“Please, girl, everything looks good on you,” Gabby said, an odd sparkle in her eye. “I just wish I looked half as good as you do in those outfits.”

I felt myself blush. “C’mon, you’re hot enough.”

“Whatever.” She leaned back in her chair. “So, when does your cousin leave?”

Mom answered, “Tomorrow morning. She’s napping right now.”

Gabby and I knew that already, but there was no way Mom could have known that we knew. Our conversation proceeded from there to everyday topics: Mom asked Gabby about her parents, we talked about what Gabby and I planned to do over the summer, and just anything. It was no different than any conversations I had with my mom on a daily basis, but something felt different about it, and not just the fact that I was wearing a dress.

My thoughts began to drift. I began to focus on what might be different about this. I couldn’t get it out of my head. That was when I realized I was looking at Gabby’s chest on accident, and looked away as quickly as possible. She was wearing one of her tighter shirts, and it was stretched across her like it was holding on for dear life.

“Honey? You okay?” Mom asked.

I nodded. “Yeah, yeah, I’m fine. Just, thinking about stuff. And things.” I got up from the table and started for my bedroom. “I’m gonna get changed and go for a walk.”

“Okay, baby. Be careful! I’m sure there are some boys you’re gonna attract around here.”

“Yeah,” I muttered under my breath, “I know.”

3.

The sun was starting to set as I made my way back home. The walk did wonders for helping me clear my head, which was exactly what I left the house to do. I prayed that Gabby would be gone when I got back to the house, otherwise I’d actually have to talk to her about it, and somehow I felt our friendship wasn't surviving that conversation.

Unfortunately, my mind was made up for me when Gabby was leaning up against a street light a couple blocks away from my house. She had a weird look on her face. “Um… Are you okay?” I asked.

“No.”

“Why?”

“Don’t change back.”

I felt surprised, even though I thought this was the conclusion we were going to end up with anyway. “What? Why are you saying that?”

She rubbed at her arm. “Look, Ken… You’ve gotta have it figured out that I haven’t exactly had a boyfriend. Like, ever.”

“So?”

“I don’t like guys. Attraction-wise, I mean.” She looked away from me for a second. “C’mon, you’ve gotta have that figured out by now.”

I shrugged. “I sorta got the idea from earlier. And then the I wanna see your boobs thing didn’t help.”

“Oh, good, so this isn’t a total surprise for you. Please, please, ask your cousin to tell her witch that you wanna stay a girl.”

I folded my arms under my breasts. “Are you saying you wanna date me, but you don’t wanna date guy me?”

She sighed. “Basically, yes. I’m just not attracted to guys, okay? I’m gonna be honest and say I don’t even know if I like girls, but I like you as a girl. Does that make any sense?”

I took a moment to think. “It makes a little sense. But you could always ask Amy to have that witch turn you into a guy, y’know.”

She shook her head, rapidly. “No way. Just because I don’t like guys doesn’t mean I wanna be one. Guys have hair in places I like being hairless, and I happen to love playing with my boobs and fingering myself - speaking of which, you should totally try both of those things before you change back.”

I blushed. “Uh… I’ll think about it.” Granted, not like I hadn’t thought about it a lot of the day. “But, look, this is kinda weird, y’know? I mean, I really wasn’t expecting this.”

She nodded. “I know, but I needed to get it out. You’re the only guy I’ve ever had something resembling a crush on, and now that you’re a girl, you’re perfect. I… I know it’s selfish, but I want you to stay this way.”

I saw that she was serious about this. It was a look I’d never seen in her eyes before, and I’d seen all kinds of looks. The only words I could muster were, “I need time to think.”

4.

“I don’t know what to do.”

Amy had a surprised look on her face. She sat cross legged on my bed, a concerned look on her face. She rubbed at her chin. “This is serious.”

“I know.”

“You need to think about this.”

“I know.”

“And I think you really need to get a dog.”

I sighed. I clicked on another picture that the website showed of the Huskie. He was a beautiful looking dog, and the idea had crossed my mind more than once. “Really? Dogs are hard work.”

“All pets are hard work.”

“What if Mom doesn’t like him?”

Clearly, she’d been listening to the conversation, as I heard Mom shout from down the hallway, “Buy the dog if you want a dog!”

I glanced back over at Amy, who was doing her best not to burst into laughter, and I couldn’t blame her. I was almost there, myself. After about a minute, the both of us just gave up and started laughing loud enough that we could probably wake the dead.

Ten minutes of laughter and one email about the dog later, Amy and I were finally calming down. I started wiping tears from my eyes, as I’d been laughing too hard. When the both of us actually stopped laughing, I told her the one thing I’d been putting off ever since I got back home. “Gabby wants me to stay this way.”

Amy sat there looking surprised. “No way.”

“Yeah.”

“But, she didn’t seem like a lesbian.”

“I guess I’m the only guy she’s ever had a thing for.”

“Holy shit.”

“I know.”

“What are ya gonna do about it? I can text Ms. Malski, if you want.”

I shook my head. “I don’t want to just make this decision now, if you know what I mean. I wanna put careful thought into this.”

“That’s a great idea, but you sorta have until midnight, which is only a couple hours away.”

“And,” Mom said, standing in the doorway, “you have to think about how that would affect more than just you and Gabby.”

I felt myself blush. “You heard that, huh?”

“I did. I assume you were going to talk to me about this, as well?”

I nodded.

“Good. I don’t want you making this decision lightly. If you stay Kendra, you’re running into a whole mess of problems with school next year, with getting your ID changed, with relatives. And that’s not even considering the anatomical problems you’re not having to deal with in your little twenty-four hour party here. Being female every day of your life isn’t the picnic you boys think it is.” That was said with a smirk. “I love you either way, baby, and you’ll still be my child either way, but think about everything that’ll change if you decide to stay Kendra.” Mom turned and walked back down the hallway, away from my room.

I sighed and turned to Amy. “Is there any chance your witch friend can give me an on/off switch?”

5.

Gabby started talking before I even had a chance to open my mouth. We’d agreed to meet at our usual hang-out spot, which would be a make-out spot to anybody else, as it was a hill that overlooked town. In fact, there were probably dozens of couples we knew that used this place as a make-out spot.

“I know what you decided,” she started. She lied down on the hood of the car, which had to be hot considering the temperature and the fact that I’d just killed the engine. “I know what you decided, and I’m just gonna havta be okay with that. I freaked you out earlier, didn’t I?”

I nodded. “Yeah, but, I haven’t made my decision yet.”

She sat up. “Huh?”

I crawled up on the car and laid beside her. “I said I haven’t decided yet. I’ve only got an hour and a half left, so I’ve got to make my decision soon.” I was holding a bottle of Mountain Dew and unscrewed the cap. “I’m sorta confused on where to go.”

“Look, I’ve thought about what I said before, and I really shouldn’t have pressured you like I did.”

I shook my head. “Don’t worry about it. I’m sure if it were you that was going through this gender change thing and I was the gay one, I’d probably do the same thing.”

She giggled. “Yeah, I’d just like to see you as a gay guy.”

I shugged. “If I stayed a girl, I’d be a gay girl.”

“Still. How much to which side are you?”

I shrugged again. “I dunno. On the one hand, we’re so close that I don’t think our relationship would be screwed over badly if I went back to being a guy. On the other, I can’t say the idea of dating you isn’t something I’ve thought about before.”

“Okay, the double negative sorta confuses me. So, are you saying that you have thought about dating me?”

“Yeah.”

“So, is this a 50/50 shot that you’ll stay Kendra?”

“Yeah.”

“Is there something I could do to sway your decision?” she asked with a smirk.

I laughed. “No. But there’s something we can do, either way.”

“Huh? What?”

I put the cap back on my Dew and dropped it to the ground beside the car. I didn’t answer her with words, I just rolled on top of her and put my lips on hers. Our tongues met quickly, intertwining. My hands gripped her face, and then I felt one of her hands on my boob. The feeling was really, really weird, but I just kept kissing her. That hand finally slipped under my shirt, and then I felt her fingers working their way into my bra. Her fingers rubbed at my nipples, which were starting to harden.

I let go of her face but I kept up the kiss. One of my hands went down to her shorts and I unzipped her. I slid my hand into her panties, completely on autopilot now, and inserted a finger into her vagina. I began to rub at her private area and pulled my face away before her teeth clamped down on my tongue.

“Ooh, sorry… You’re just… So good at this…”

The hand that wasn’t playing with my nipple moved to my pants, unzipped them, and worked its way into my panties. For the first time in my life, I felt a finger inside me. The sensation took my breath away, and then I started to feel the juices inside me flowing. Almost as if we were in sync, Gabby started to moisten up as well, and while the feeling was odd, it wasn’t unpleasant.

We were both moaning at about the same time.

I pulled my hand out of her panties and pulled my shirt and bra off, doing for her now what I’d refused to do earlier. She did the same, and I saw her exposed boobs for the first time. I brought my head to one and started licking at her rock hard nipple, which caused her to moan even harder. Once again, her hand slipped into my panties and I felt her finger inside me again.

Gabby pushed me away from her tits and then rolled us over, putting herself on top. She paid me back for my nipple suckling by doing the same to my boob, and yet another new feeling hit me straight in the chest - literally. The feeling of her tongue on my nipple and her finger in my cunt brought me to orgasm quickly, and this wasn’t the same as when I came as a guy. My whole body shuddered, as the pleasure rolled over me. I moaned so loud I was afraid somebody in town would hear me.

I kissed her again, our tongues touched once more, and then our nipples touched. The feeling was electric, erotic…

Exciting.