Mom calls me in to talk first. I’m wearing a frilly white dress with a bow on the collar, along with a white training bra with a blue bow on the front, and white leopard print panties.

“So, is this how you like to dress?” my mother asks.

“No! The girls made me do this!”

“Hmm. I see. Well, you’re my son, or child, anyhow, so I just want to let you know that, no matter what you choose, I’ll support you.”

“I don’t chose anything! I was forced to do this!”

“If you say so. You certainly looked happy back there, anyhow. And you do look rather cute. If you ever decide you need your own clothes, let me know, and we can go shopping.”

“I don’t!”

“That’s alright. Anyhow, your father is going to want to talk to you, too. Good luck with that.”

My mom pats my hair, careful not to mess it up after my sister and her friends spent so long working on it. She walks out, and gives my father a stern look, warning him to take it easy on me.

My father walks in, sits down on the edge of the bed, and sighs.

“Son, this isn’t going to become a regular thing, right?”

“Of course not! Men should be manly!”

My father nods his had. “I take that to mean that you’ll be cutting your hair, then. Anyhow, what is done is done. A real man must honor his bets, no matter how humiliating. But in the future, I expect you to be more responsible! Think about how this reflects on me!”

“I won’t cut my hair, but I promise that I’ll be more careful in the future.”

My dad sighs a deep sigh, and stands up. He looks me up and down with a disgusted expression, then walks out. All in all, that could have been way worse. I didn’t even get yelled at! I’ll be sure to be more careful with my bets in the future so that I don’t disappoint him!

As I walk out of my parents’ room, my sister comes and grabs my hand, dragging me back to her room for more dressing up.

“Have you decided on a name, yet?” Eve asks as I’m dragged into the room.

“What?”

“Surely you don’t expect me to date a girl with the name Trevor?”

I shrug. “This is only for one day. It doesn’t matter.”

“Hmm, sure. What about the name Tiffany, then? If it doesn’t matter, you may as well go with it.”

“I would prefer not to, honestly.”

“Oh, come on, Tiffany!” Alice says, dragging me to her closet. “This is supposed to be fun! Just relax and go with it!”

I groan. “Fine! Whatever! Let’s just get this over with.”

I try on dozens of different outfits over the course of the day. Skirts, dresses, short shorts, one and two piece swimsuits, leotards, panties, bras, all kinda of things. I hate to admit it, but I’m having fun. I spin around, and the skirts and dresses flare out. It’s an interesting sight to behold. Also, I really do look nice in these outfits. And they feel so nice, too…

I smack my face to snap myself out of it. That scares the girls, who all jump back in surprise.

“What was that for?” Julia asks.

“Nothing.”

Soon after, my mother calls us for dinner. I’m dragged to the dinner table wearing a black skirt with buttons on the side and a bow belt, a black and white striped ¾ sleeves t-shirt, stripped leggings, and stripped panties and training bra of the same color. My father gives me a disappointed look as I sit down, careful to smooth my skirt under me, but says nothing.

I eat carefully, not wanting to drop any food on the clothes and dirty them. I know that my sister would cry, and I would get in trouble. That’s the last thing that I need right now.

“So, when are you girls going home?” my father asks, probably hoping that once they go home I can go back to my regular clothes.

“I was hoping we could sleep over!” Julia says. “After all, we don’t get to have Tiffany with us every day! We want to have as much fun with her as we can!”

“Tiffany,” my mother says, slowly. “I see. Well, I see no harm in it. Just make sure your parents know.”

“Of course! We’ll call them after dinner!” Eve says.

“I’ll let you borrow my phone.”

After we eat, my mother lets the girls borrow her cell phone and call their parents. They’re all ok with it, so the girls are all jumping up and down, giddy as school girls… which, I guess they are.

My mother brings out the sleeping bags for the girls. We have friends sleep over often, so there are plenty of them. We set the four bags up in the living room, with two side to side, and the other two foot to foot. I’m sleeping next to Eve, and Alice is sleeping next to Julia.

“Does this mean I’m going to really be part of this?” I ask.

“Of course!” my mother says. “The girls are all so excited because of that precisely! I suggest that you just have fun and make the most of it.”

I groan, but don’t complain. I can’t go against what my parents say, so I just put up with it.

The girls drag me back to my sister’s room, and start deciding on what I should wear for the sleepover. I end up wearing a green and yellow striped sleeping dress with frills on the arms, neckline, and hem of the skirt. It goes to just above my knees. I also wear matching panties, with frills on the legholes and top.

As I’m there, the girls also get changed. My sister wears a short sleep dress that is pink with kitten faces on it. Julia wears red and blue pajama shorts and a matching red top with a cartoon character on it. Eve sleeps in just her black panties and a black camisole with a bow on the neckline.

We all move to the living room, and start chatting for a bit as my mother does some clean up. There’s some kid’s movie coming out soon that they’re all excited for. I’m not familiar with it, but the shirt that Julia is wearing has it on its front. They’re considering going to the movies one of these days, and want me to come with them. Not likely! Even if Eve is my girlfriend now, I don’t have any interest in seeing a kid’s movie.

“I’ll take Eve out on a nice romantic date one of these days!” I tell them. “When I do, we’ll watch a romantic movie, not a kid’s movie! And I’ll show her just how much of a man I am!”
“Uh, huh…” my sister says.

“Whatever you say, Tiffany,” Julia laughs.

Eve picks up the hem of my dress, taking a peek at my panties. “Hmm…”

“Eep!” I shriek, throwing my hands over my panties so they don’t see them. Everyone laughs at me.

We play board games for a little bit, but the girls have been seriously tired out from the wrestling and all the excitement in making me crossdress. It isn’t long before they’re pretty much wiped out.

My mom claps her hands. “Okay, girls! I think it’s bedtime now! You’re not the only ones who need to rest, I have work tomorrow!”

“Night, mommy!” Alice says, giving mom a hug.

With that, we all get in our sleeping bags, and I, at the very least, try to fall asleep. I feel awkward in these clothes that I’m not used to sleeping in. It’s tough to fall asleep, as I keep focusing on my clothes. But I’ve been worn out by the girls, so it isn’t too long before I start drifting to sleep.

Just as my mind is starting to shut down, and my eyes flutter closed, I hear some movement below me. I crane my neck down, towards where my sister’s sleeping bag is. It takes me a second to figure out what I’m looking at in the darkness, especially with me being so tired, but as I figure out what exactly is happening, my eyes shoot open, and I’m wide awake.

Julia has crawled out of her sleeping bag now that she thinks everyone is awake, and is leaning over my sister, kissing her. My sister reciprocates, then pulls away for a moment, and moves out of and then on top of the sleeping bag so that she can move easier. Julia returns to kissing my sister, with one hand on her upper thigh inside of her dress, the other laying on her breast. Alice holds one hand on Julia’s lower back, and the other on top of Julia’s hand on her chest. I hold my breath, careful not to make any sound.

“That’s kinda hot, huh?” Eve whispers into my ear. I nearly shout, but she throws a hand over my mouth to keep me quiet. “Stay quiet, idiot! You don’t wanna disrupt them… I certainly don’t. This is the best part of any sleepover. Except this time, I have a girlfriend of my own to play with…”

Eve carefully turns me towards her, and then leans in to kiss me. She’s mostly leaning out of her sleeping bag, but I’m still stuck in mine. After a few seconds on kissing, she slowly and silently crawls out, then kneels over me, pinning my hips down with her knees, and pinning my arms down with her hands. She bends down, and kisses me for several more seconds. When I open my eyes again, my sister and Julia have stopped making out, and are staring at us. Notably, Julia is still atop my sister.

Eve sees that I’m staring back at them, and she cocks an eye at them. “What? You think I never noticed you two going at it during sleepovers? Please! At least this way I can have my own fun instead of just watching you two, not that I ever really minded watching…”

The girls consider this for a while, before crawling over next to us, and then returning to making out beside us. Eve lets me crawl out of the sleeping bag, then gets right back on top of me. I’m not sure what to do, so I just let her have her way with me. Unfortunately, it doesn’t go any further than kissing. Even just that, though, especially with my sister and Julia right beside us making out basically right in our ears, is super hot.

Maybe crossdressing isn’t so bad if it can get me this… No. No more thoughts like that! I have to reclaim my manliness!

I fall asleep sometime later, and my mother shakes me awake. I’m sleeping on top of the sleeping bag, sideways, with my dress clumped up, revealing my panties to the whole room. My parents are both watching, as are the three girls, giggling.

“I think that it’s time to get changed,” my father says.

I don’t waste any time running over to my room and throwing a t-shirt, boy’s underwear, and shirt on. I return to the living room to help put the sleeping bags away. Once that’s over, I return to my room to do some pushups. My manliness will make a great return today!

As I walk into the room, I notice the girl’s panties and clothes on the floor. I pick the panties up, and feel them in between my fingers. They’re so soft…

“Uh, Tiff- err, Trevor?” Eve says. I turn around, hiding the panties behind me. “Your mom wants me to tell you to throw your dirty clothes in the wash. That includes those panties you were feeling.”

“I wasn’t doing anything!” I tell her, lying my ass off.

“Really? It certainly looked like something to me. But don’t worry, I won’t tell anyone.”

“Thank you! You’re such an understanding girlfriend!”

“You didn’t let me finish! I won’t tell anyone, on one condition… but before that, keep in mind that I’m the boyfriend in this relationship. You’re my cute little girlfriend. Right now you look like a girl wearing her big brother’s clothes. Anyhow, I just want to wrestle with you for a bit. That’s fine, right?”

“Huh? Yeah, sure! I love wrestling!”

I go to throw the dirty clothes into the laundry, then run to meet with Eve in my brothers’ room. She’s there, already changed. She’s wearing a black sports bra and black boyshort panties. She throws some clothes at me.

“Your clothes still aren’t cleaned, so you’ll be wearing that.”

I hold up the pink hello kitty panties and training bra.

“Are you kidding me?”

“I could also just tell everyone that you were rubbing those panties earlier. I’m sure they would understand.”

I groan. “Fine! Just this once!”

“Twice, now, actually.”

I glare at her, then step onto the bed. She joins me, smiling deviously.

This time around, I’m prepared for her! I get three wins in a row, and though she manages one win off of me, I get my revenge, winning another two in a row! I’m on a roll! I wish I was doing bets today instead of yesterday, I wouldn’t have ended up crossdressing!

Eve sighs. “Jeez, you’re just too good. I think I just got lucky yesterday. But how about we keep trying? Two out of three falls, loser has to do whatever the winner wants! No exceptions!”

“Fine! No way I lose today!”

Eve tackles me down, and pins my shoulders down with her hands, and my hips down with her knees, like she did last night. I blush as I recall that memory, and in that short moment, she counts to three, and I’m quickly down one. But that’s fine! She can have the first win! I’ll win the next two easy!

We stand back up, and face one another. This time, I tackle her down first, but she rolls away before I can pin her, and grabs my leg. She twists me around, forcing me onto my stomach. She sits on my back, and holds my leg right between hers, rubbing up against her hips. She pulls back on my leg, leaning back on me and trying to make me submit.

I thrash wildly, trying to get her off of me. I kick at her groin, and she grimaces for a second, but it wasn’t a hard kick, and she doesn’t have boy bits like me, so she doesn’t let go. I’m forced to submit, as the pain is just too strong. I can’t handle it. I’m nearly on the verge of tears, but Eve crawls up to my face, and puts my head on her lap.

“Shh, it’s okay, baby. No need to cry!”

I push myself away from her, and shake my head. “I wasn’t crying! And I demand a rematch!”

“Why?”

“Because that wasn’t fair!”

“How so?”

“You caught me off guard!”

She considers this. “How about we do the final match? We can consider this one void.”

I nod my head, and the two of us stand up and face one another again. This time, as I go to grapple her, she drops down, and pulls my panties down. I yelp, and reach down to pull them back up, but as I do, she rolls me up, and gets the three count.

“That’s cheating!” I shout.

“Pull your panties up.”

I do as she says, and then sit on the edge of the bed, arms folded.

“I won three times. Are you prepared to pay up?”

“Fine!” I throw my hands up into the sky. “What do you want?”

“I want Tiffany to come with me on my double date today. Alice and Julia are a couple, and I can’t be third wheeling. We’re going to watch that Super Mega Pets movie we were all excited about yesterday.”

I groan. “Fine. You won, so I’ll pay up.”

“Good. Let’s get to your sister’s room so we can choose your outfit. Don’t bother changing out of those panties or the bra, you’ll be wearing those to the movie.”

I sigh, and pull my shorts and t-shirt on over the bra and panties. I then follow Eve to my sister’s room, where Alice and Julia are making out on the bed.

“You better be happy our parents are off at work,” I tell them.

“Did you get her to come on the date with us?” Alice asks.

“Of course! It’s just as we planned”

I squint my eyes. “What do you mean, just as we planned?”

Eve sticks her tongue out. “Easy! I just had to stroke your ego first, let you win some matches! Then when you were confident in yourself, I challenged you, and won!”

“That’s evil!”

“It’s genius, that’s what it is! Now, are you gonna complain, or are we gonna get changed?”

I groan, and let the girls dress me up. I’m wearing a pink pleated jumper skirt with cats on the bottom and a pink long sleeve t-shirt beneath it. I’m also wearing white thigh highs and pink flats. The girls do my hair into twintails, with flowers at the end.

“You’re so adorable!” Eve shrieks. “I really have such a good taste in girls!”

“I’m a boy,” I mutter, though the girls just ignore that. They have their own outfits to pick, so they head home, and promise to meet back up later tonight.

I change out of the outfit for now while the girls head home to choose their outfits and prep for the double date. Don’t tell anyone, but I actually keep the panties on beneath my shorts after I change into my normal clothes.

When my parents get home, they’re happy to hear that I’m going to be spending time with the girls later today. They’re less happy to hear that I’ll be spending that time dressed as a girl again.

“This isn’t going to become a regular thing, is it?” my father asks.

“No! Of course not! I just lost another bet!”

“Maybe you need to refine your bets.”

Regardless of how my parents feel, or how I feel, a bet is a bet. So when the time comes around, I change back into my date outfit. The other girls are also wearing cute outfits, save for Eve, who actually looks rather handsome.

Eve is wearing black slacks and a red and black striped button up long sleeve shirt. She seems to be playing up the role of boyfriend. Julia is wearing a long white dress with lace on the bottom, and a black lacy jacket over it. My sister is wearing a dark green dress with flower shaped buttons on the front.

We arrive at the movies pretty early, so we sit around the concession stand area for a bit, talking about various things.

“So how long have you been dating my sister?” I ask Julia.

She blushes, and looks down sheepishly. “A while.”

“I first caught them making out probably about 6 months ago,” Eve says.

“We did a really bad job of keeping it hidden, then, since we just started doing that 6 months ago,” Alice says.

“You did a better job hiding the fact that you were watching us,” Julia tells her.

“Heh, well, I like to think I’m pretty sneaky!”

The movie starts soon after, and we get some popcorn and soda and head in. The theater is packed with kids, most quite a bit younger than us. We’re one of the few groups that doesn’t have an adult with us.

I sit down between Eve and Alice. Julia, obviously, sits down next to Alice. The movie is, well, let’s be honest, a kid’s movie. The plot is simple, the designs are cute but nothing special, and the dialog is corny. And yet they manage to get me to laugh quite a few times.

I hold hands with Eve the entire time. Similarly, Alice and Julia hold hands the entire time. Unfortunately, there are no romantic parts where I can share a kiss with Eve. I wish we had seen either a scary movie or a romantic movie, as that would be more appropriate for a date. Still, even if I want to deny it, I have fun. Sandwich me between two cute girls and I’m sure I’ll have fun no matter what, honestly!

As the movie winds down, Eve lets go of my hand, and reaches down my leg. She rubs my thigh, and leans in to me. In the dark, nobody can see what she’s doing. She leans in, and gives me a kiss on my nose. She then moves her hand to my butt, and gives it a firm squeeze. The lights come on shortly after, and we stand up to leave.

The theater is downtown, so after the movie ends, we head next door to a fast food restaurant, and discuss the film. Obviously we’re no movie critics, though.

“And when the llamas started talking to that guy? I absolutely lost it!” Alice breaks down into a fit of giggles as she remembers the scene. It was really random, but it was kind of funny.

“What was your favorite scene?” Julia asks me.

“Uh,” I pause a I consider. There were a few funny moments, and it was overall fun, but none of the scenes in particular really stood out to me. If I had to pick, though…

“I guess the part where that girl was falling off the cliff, remembered she left her stove on, stopped falling, ran home, turned the stove on, ran back, and then continued falling?”

“Yes! That was so good!”

We all laugh a bit as we discuss the film. Truth be told, with how weird and random the movie was, I worry for the sanity of the creators. You can’t be all right in the head to be an artist in the first place, but for a weird cartoon movie like that? You have to be extra gone.

My parents are expected to arrive soon, so I share a quick kiss with Eve, and my sister shares a quick kiss with Julia. I can probably keep acting romantic with Eve, but it would still throw my parents off to see me do that while dressed like this. And Alice absolutely cannot let our parents know that she is dating Julia. I don’t know how they would react.

“Hey, I have an idea,” Eve says. “We can’t let the fun end now, can we? We should have another sleepover!”

My sister gasps. “Yes! That would be so much fun! And Tiffany can join us again! Tiffany, what do you say?”

I roll my eyes. “Yeah, fine, I guess.” Seeing as I haven’t lost any bets, I don’t have to crossdress for this sleepover. And I don’t plan to, so I won’t be wrestling today! At least not for bets. And I’m sure the girls won’t wrestle me if I don’t wager something, so likely not at all.

My parents arrive, and we tell them about the planned sleepover. The girls will be going home first, but will meet up with us later. In the meantime, I’m just going to play some video games.

While I’m in my room playing games, my mother knocks at the door, and I tell her to come on in.

“Are you going to be at the sleepover?” my mom asks.

“Yeah.”

“As Trevor, or as Tiffany?”

“As Trevor, of course!”

She pauses. “Are you sure? You seem to be having a lot of fun as Tiffany. Your face is so bright, and you’re seemingly always smiling.”

“That’s just because I’m around Eve! You know I’ve always liked her!”

“Sure. I’m just saying that no matter how you choose to dress when you sleep with the others, I’m supportive of you.”

“I’m a boy! I’ll wear boy’s clothes!”

“That’s fine. Wear what makes you happy.”

She leaves, and I’m left feeling annoyed. In what world would a boy like wearing girl’s clothes? I’m a man! A manly man! There’s no way I would ever wear girl’s clothes for fun!

I can’t get into my video games after that. I’m annoyed, and end up making tons of stupid mistakes. I head to my computer instead, surfing the web. I don’t have anything in particular in mind, so I watch a few Youtube videos, end up opening some Wikipedia articles, read one or two depressing news stories that certainly don’t help my mood, then end up on Amazon.

At first, I’m looking at a game that will come out soon. $60 dollars. Yikes. It’s supposed to be an awesome game, but I’ll have to wait until my birthday rolls around to get it. As I scroll down, there are recommended items based on what’s been looked up in the past. My sister uses my computer on occasion, so there are a bunch of girly clothes suggested. I sigh in annoyance as I scroll through the suggested clothes.

Wait, this dress is actually really cute. It has a sheer skirt over a lacy skirt, and a fancy lacy pattern over the top. The price matches the elegance at over 100 dollars. I could buy a collector’s edition of a brand new game for that price.

I browse some cheaper clothes. A few are actually really cute. I start imagining myself in them, before I stop myself.

“What the heck?” I ask myself. In what world does a guy browse girly clothes on Amazon?

Back to youtube! I’ll be safe there! I watch a few music videos, then a video based on my recommendations pops up. Based on my sister’s watch history, it suggests a fashion show for me. It’s actually a home-made fashion show by a pair of sisters, where each takes turn walking down the hallway as the other changes clothes. They seem to be about 10 and 12. I notice that one or two outfits are outfits that my sister owns. I find myself thinking about wearing them.

I’m watching a different fashion show when my mom knocks on my door. I close the tab, and tell her to come in. She looks at my computer, sitting at the home screen, and gives me a weird look. She then tells me that the girls are here, and that I should get changed. She drops off a basket of clean clothes, and leaves.

The basket doesn’t just hold my clothes. It has Alice’s clothes, too. My mom is giving me a chance to crossdress yet again. This time, though, it would be entirely my own choice. I hate how much I hesitate. I’m a man! There should be no question! And yet…

I carefully rummage through the clean clothes. I take quite a while deciding on my outfit, but I finally decide on a pair of flowery blue panties, a white training bra with blue flowers, and a purple sleep dress with blue flowers on it. I walk out to see the girls, who all look surprised and also ecstatic.

Eve is wearing black shorts with a floral lace design, and a green camisole. Julia is wearing fluffy pink and green striped shorts and a matching shirt. Alice is wearing a long yellow sleep dress that drags on the floor. It has poofy sleeves, and orange hearts across the top area.

“Tiffany!” Eve shouts out. “I didn’t expect to see you here!” She runs over and hugs me tight. Soon, the other girls follow, and my breath is being squeezed out from my lungs.

“Ow,” I groan. Finally they let me go, and I try to explain myself. “Well, we couldn’t have a guy at the all-girls sleepover, right? So I, uh…”

“Yeah, yeah!” Eve scoffs. “Whatever you say! I’m just happy to see my girlfriend again!”

I blush. “I’m happy to see you too.”

My mom smiles, and heads back to my room to grab the clean clothes and put them away. She says that she’s got work to do, so she’ll leave us to our own devices for now.

We play board games and chat until my mom goes to bed. I also show them some of the cute outfits I liked off of Amazon, and some of the fashion shows that I watched. They’re all surprised to see how girly I’ve gotten, but honestly, it’s just to much fun that I can’t help myself.

Now that my mom has gone to bed, we’re expected to go to sleep. We pretend to sleep for a while, but get up after an hour or so, and gather around in the darkness of the living room. I pull out my phone, and we get to the fun part of the night: ghost stories!

Of course, that ends up causing me to get no sleep that night... I guess it's just a good thing we don't have school tomorrow.