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Can't I Have Them Both?

Can't I Have Them Both?

Can I Make This Work?
Waking up to the sound of my alarm blaring, I roll over and slam on it. Of course it doesn't go off, just crashes to the floor. I know I shouldn't have stayed up so late last night playing video games, but what can I say? Too late now, I suppose. I reach down to pick up the clock, seeing the time blinking at me.

Getting out of bed, I grab the shower before anyone else can. I know what it’s like in this household in the mornings. My two sisters will fight like crazy for the bathroom. I get why, but I can do what they can in my bedroom. They are the only ones in my family to know of my secret lifestyle. At least at home, at school, I can be who I want to be.

I change into a pair of jeans and a t-shirt, before looking for what I really want to wear today. I stuff the clothes into my bag. I can change at school. This has been going on for about three months. At least in public it has been. I’ve been dressing up as a girl for a few years now. But, after the help and encouragement of my sisters, I started to in public, also.

There is something sexy about wearing girl clothes. It’s something I can’t explain, it makes me feel pretty. I watched both my older and younger sister growing up, being able to dress in all kinds of stuff that I wanted to wear. They, of course, did dress me up from time to time as a girl. I’ve always worn my hair long, and have been in touch with my feminine side. No one in my family seems to mind, but I don’t tell my parents I do it in public.

It never seemed like it was something to be ashamed of. No one at school gives me a hard time for it either, which I’m grateful for. I’ve heard of some really bad stories about cross dressing and being either bi-sexual or gay. I’m bi-sexual, I love the idea of being with both girls and guys. I’ve been in relationships with both, I don’t prefer one over the other. I get on well with them equally.

When I get to school, I go to the men’s room and change into what I packed. I opted for some hip hugging jeans, which curve my arse well. The shirt is simple, nothing too different than what I’d normally wear. It’s just in a girl style. The biggest thing I made sure to grab, are the heels. They are a simple black pair. Now, I’m not a guys’ guy. I have a naturally girly body. I’m very thin, with soft features. I could easily pass for a girl, if dressed to the max like one.

My makeup on, looking good, feeling amazing, I rush to class, when I hear the bell ring. I make it without being late, as the teacher isn’t even in class, when all the students settle in. We all begin to talk about the upcoming weekend, which happens to be a long weekend, teacher workshop and all.

The teacher finally walks in. Behind him, is this cute, shy looking girl. She looks to be all of five feet tall. Her long dark hair curls around her face, almost like she is hiding from the world. I don’t know why, but she is beautiful. Her eyes catch mine, looking at me. I can tell what’s going through her mind, making me shift in my seat.

“Good morning class, sorry I’m late. We have a new addition to the class. This is Rose, she’s new to town, just starting school this week. Everyone please be kind to her.” He states the obvious, like we’re all going to start throwing things at her and calling her names. She is still looking at me, I'm glancing at her from the corner of my eyes. I can’t help but wonder if she’s ever seen a dude in girl clothes before? “Do I have someone who is willing to show her around?”

I quickly nod at him and raise my hand, “I’ll help out, if she doesn’t mind.”

I don’t know why I’m offering, but the girl is intriguing me.

“Thank you, Jack. Now, before we begin, Rose, why don’t you tell us about yourself?”

The look on her face is priceless. She turns bright red, almost looks like she is going to sink into herself even more. “I, um, well…” She blushes deeply, “my family and I moved here last week, my dad is in the Military and we move around a lot. My brother and I just started here today. We’re twins, but we’re nothing alike. At least looks wise, in every other sense we seem to be. I own tons of music and hope to one day become a singer. I’m rather good, I think. Umm, my family and I have a dog we call Kitty because that’s what we thought she looked like when we bought her. It just kind of stuck.”

She trails on for another few minutes, before looking at the teacher in hopes that was enough. He smiles, telling her to take a seat. She does in a hurry, looking grateful that she can. She sits down next to me with a long sigh.

I turn and smile at her, “he does that to everyone, but I’ve never seen anyone blush as much as you did. Not good with crowds?”

“Hah, um, no, not so much. I guess I should learn, if I ever want to be a singer though, huh?”

“Yes, you should,” I grin at her, enjoying her company already. “I’m Jack, it’s nice to meet you, by the way,” I reach out to shake her hand, she blushes again.

“It’s nice to meet you as well, Jack. Thanks for offering to show me around. Most people are forced into doing that kind of stuff. I’ve moved seven times in the last few years, it’s a first.”

“I don’t know, just figured it would be easier than making someone who didn’t want to, right?”

We talk for a few more minutes, before getting the look from the teacher to settle down. Class goes by all too fast, I ask Rose for her schedule. I notice we’re in a few of the same classes, which makes it easier to show her around. When we leave class, we bump into her brother. She introduces us. His name is Matthew, who does, in fact, look just like his sister. He has the same soft features she does. I can’t help but think how beautiful he is. He is only a few inches taller than his sister, though.

It turns out that he is in a few of my classes, even sharing one with both Rose and I. He is just as shy and sweet as his sister. I can’t help but liking them both very quickly. I think I could even fancy them. Yes, both of them. I’ve never had the pleasure of being with a sister and a brother before. Neither of them mind the fact that I am dressed in girl clothing either.

Over the next couple of weeks, I get to know them both. I do with them together and alone. With the weekend finally coming, I offer them both to come visit me at my place. I have spent a lot of time with them and figure it could be fun to hangout, outside of school as well. Now that they are all settled into their new house, they can have some fun.

They agree, after asking their parents. Their parents said they could, as long as we get our homework done. We all agreed, knowing that wouldn’t be a problem.

When they show up, they meet my parents and my two sisters. Jessica and Julia both are pleased I’ve made new friends. I don’t really have many, I’m a really big loner. They’ve seen the twins at school, but they’ve not been introduced properly. Jessica is a senior in school and Julia is a freshman. The school is big enough not to bump into one another often. We can go days in school without seeing each other. We see enough of each other at home as it is, even if we do get along.

I’m very close with them, since I never had many friends growing up, I depended on my sisters a lot. Both were always kind to me, not acting like the typical sisters, pushing me away. I don’t know what I’d do without them. Now, don’t get me wrong, we still bicker and tease each other, we are normal, after all!

Matthew, Rose and I are hiding out in my bedroom, playing video games, talking about their moving around. They’ve been all over the country. I’m rather jealous, I’ve never left this one place, known it all my life. They both agree they like the fact they’ve seen so much, but hate moving around, losing friends and being forgotten so easily. Friends always claim they’ll keep in touch, but don’t after about a month.

Hanging out with them, I can’t help but really think I couldn’t choose which one I’d fancy more. I like them both the same, but for different reasons and some the same. Rose, being so cute and short, reminds me of someone I could see myself with. Her hair is a beautiful reddish brown, with dark eyes that sparkle whenever she smiles. Her skin is soft, I would know, she likes to hold hands with me a lot.

Matthew has darker hair, but not by much. His eyes are just as dark as his sisters. He seems to be into me, but I can’t tell. I’ve wanted to outright ask him, but I don’t know how to go about doing so. I know I’ll find a way somehow. Over the last few weeks, he shows signs that he is. Maybe he is just curious as to why I dress like a girl. Maybe he is bi-sexual or even curious himself? I want to find out.

Dad comes in, asking the twins if they want to stay for dinner. They tell him if it’s not a problem, he just nods, saying we’re ordering pizza. We can keep hanging out in here. They call their parents and let them know, they’ll be home later. When the food arrives, we all huddle together on the floor, watching a DVD.

The lights are off, the shades pulled closed, the room is dark, with just the glow of the TV. We’re all engrossed with what is on the screen. I’m sitting between Matthew and Rose, as we eat our food. It’s a scary film, making us each jump and giggle at each other, when we get scared. With the food done, we’re snuggled close still, watching the film. There isn’t much talk, we’re too into the film. However, I feel a hand reach for mine, I think it’s Rose, but it’s not, it’s Matthew. He pulls it towards him and onto his lap. He rests it just right, enough for me to feel his cock through his jeans. I can tell he is hard, glancing at him, he grins. I see him blushing, though it’s dark.

I try to keep focused on the film, so not to be obvious to Rose. Matthew moves to unbutton his jeans, the soft sound of his zipper coming undone makes me squirm. What is he thinking? What does he have in mind? I can’t believe how suddenly the shy one is becoming so daring. I find it so sexy, that I become rock solid.

He pulls my hand down into his jeans, I can’t help but caress him. He’s so hard, but I wonder what Rose would think if she knew? Is it weird I think it’s a turn on, she might find out? I start to stroke his cock, feeling how thick he is. I like the feel of him, picturing him inside my mouth now. It makes me shift, squirming a little closer towards him.

Slowly, I begin to jerk him a little faster. I can tell it takes all he has not to moan. I’m not even sure how he does it. I moan when I jerk my own cock. I try and focus on the film, but I can’t. I’m too into what is going on. Rose is none the wiser. I feel how slick my hand is moving along his shaft, fucking hell, and his pre-cum is just all over the place. I want to taste him!

Within a moment, he begins to come. I see him coming all over his boxers, letting out a sound just in time as a scary moment happens in the film. Nice timing, I’d say. When he finishes, he tucks his cock back into his jeans, smiling at me. Did that just happen?

After the film is over, Matthew and Rose tell me they need to leave. They can’t be late, or they’ll be hell to pay when they do get home. Later on, I get a text from Rose telling me I should have worn girly clothes today, I explain to her why I don’t at home. She tells me that I should on Monday. She thinks I look so sexy with them on. I can’t help but almost die, blushing so hard.

I change into something girly, thinking of both Rose and Matthew, and begin to jerk my cock. The idea of both of them going at me at the same time turns me on so much. I want to suck on Matthew’s cock as I fuck Rose at the same time. I know it won’t ever happen, but it can in my mind. The lacy panties I use to jerk off with, feel so soft. I bought them because I know how nice they’d feel when I felt them against my cock.

Monday comes far too fast, but I make sure to look extra pretty for Rose. When I see her in first period, she giggles, telling me how great I look. It turns me on, making me want her all the more. I can’t get her out of my mind all through class. When the bell rings, I grab her hand and pull her towards the boys’ bathroom.

“Where are we going, I can’t go in there,” she tries to protest, but I pull her in anyway.

“Don’t be a chicken, come on.”

The bathroom is empty, shockingly. I take her to the end stall, the handicap one, closing and flicking the lock securely.

“Well, fine, now that you have me, what do you want to do to me?” Her eyes grow wicked, almost teasing.

“If it’s up to me, you’d be on your knees sucking my cock under my dress. I made sure to look extra pretty for you,” I announce, a bit cocky.

“Is that what you want, Jack? For me to suck your cock into the back of my throat, make you come so hard you’ll feel like you’re going to explode with need?”

“I'd rather actually explode with need, if I’m to be honest,” I jokingly say.

“Fair enough, we only have four minutes before next class though. I can’t skip class, my dad would kill me,” she moves to get onto her knees as she says this.

Holy shit, is this really going to happen? I can’t help but get so hard thinking of it. I didn’t bother to wear any boxers, instead wearing panties. When Rose lifts my skirt, she sees how hard I am against them.

“Like that?” I whisper down to her.

“Oh, I do, it’s so sexy,” she purrs out, sliding them down just enough. My cock springs up, facing her, she leans in and begins to suck on just the head of my cock.

The sensation of her warm mouth makes me moan. It isn’t long before she goes full on, sucking my cock, taking me deeper inside her throat. The girl is clearly skilled at what she is doing, because I feel as though I could come already.

“Fuck, I’m going to come, if you keep sucking like that. Don’t stop, please,” I beg, whimpering.

She doesn’t either. She sucks harder, a little faster, knowing we’re running out of time. When she suddenly uses her teeth, I let out a sharp gasp, moaning, I come so hard. She sucks deeper, taking me to a whole new level. It feels amazing, gripping the wall for support. When I stop coming, she licks me clean, quickly.

“Is that better?” She asks, as though she knew all along that I wanted her.

“Hell yes,” I giggle, feeling silly.

“Good, now let’s go, we’re going to be late.”

We rush to our next class, I still feel high as fuck, loving the orgasm she gives me. Now, I wonder how well her brother can do. I wonder if I can convince him to suck me after class later on. Is it wrong that I want both of them like this? It doesn’t feel wrong!

At lunch, we hang out at our usual table talking. Everything seems normal, everyday for us. I can’t help but think about it though. My next class is with Matthew, I want to take him to do the same thing I did with Rose this morning. It makes me horny, pre-cum drips from the tip of my cock. When Rose leaves to head to her class, Matthew and I go to ours.

“Hey, I need to go use the bathroom, I’ll be a sec,” Matthew states.

“I’ll go, class is still a few minutes away.”

“Okay, cool.”

When we get into the bathroom there are a few other guys in there. I go down to the last stall, as I always do and pretend to go piss. The bathroom door opens and the room goes silent, except the sound of Matthew using the bathroom. After a second, he finishes, coming out and knocking on my door.

“Hey, let me in, I know you’re not peeing,” he stands at the door. I flip the lock and open the door. He pushes himself in, with a grin. “Now, if I recall right, I owe you something,” he states.

“Ah, what would that be?” I ask, a little confused.

“Just let me do my own thing, don’t worry. I’ve done this before.”

Just like his sister had done this morning, he moves to his knees. Is this really happening twice in one day? What the actual fuck, I can’t help but scream inside my head. He takes me into his mouth with a bit more greed than his sister did this morning, sucking on it

His aggression, his need, his want for me is so sexy, I want more. I grip his head, holding him close, and begin to fuck his mouth as he sucks. It makes him moan, he doesn’t seem to care about getting caught. This just leads me on to fuck him faster. I can feel the build up of my orgasm coming. I don’t want to, but do at the same time.

I’ve never done this before. I’ve never done anything at school, let alone with two people. Especially siblings! Oh, my lucky stars, I don’t know if I’m dreaming, but if I am, I don’t want to wake up. His tongue flicks, sucking me deeper, making my body go rigid, and I can’t help it. I begin to come hard. I come harder than I did this morning, unsure if he is better or that I am just more excited right now.

I don’t have time to think of it, as the sound of the bell goes off. We both dash to class, not wanting to be late. I know how strict their parents are, not wanting to get them into trouble. I’m not sure how I came across the kinkiest twins ever, but I’m glad I have. It’s double the trouble, double the win.

When I go home that day, I need someone to talk with. I talk to my sisters about what is going on. I explain to them that I do fancy both the twins, unable to choose which one I want. If I should even pick one, or just be friends with them. My sisters tell me that there is nothing wrong with exploring and finding out what I like, but that the twins should know I’m fooling around with both of them, in case they might have an issue with it. I never even thought of that. It’s clear they both fancy me, but what if they would be mad if they should find out they’ve been sharing me like that?

After a few days of trying to get my head in order with the right thoughts, I know I need to talk with them both. I, again, invite them over at the weekend. Both are more than willing to come over. I still am nervous, not wanting to hurt anyone’s feelings or get into a fight. I’ve never done this before, nor have I had many friends before.

When they show up, we go straight to my room. I tell them I want to talk. My parents are out for the evening, so I figure now is the best time to do it, just in case anything happens. Both my sisters are out as well, but know I’m here and what is going to happen.

At first, I begin to stumble, trying to explain what has happened. Both Rose and Matthew watch, letting me make a fool of myself. I try to explain the best I can, though.

It’s Rose who cuts me off, “Jack, stop, stop, listen. We both know already. Do you think we don’t talk? Don’t worry about it. We both fancy you and we both want you so don’t fret. We’ve agreed to share you. Unless that is a problem for you? I mean, it’s working so far, isn’t it?”

She says this, as if it’s something that people do all the time. I just sit there, unsure what to say. I even dressed up for Rose, knowing she likes me looking pretty. Matthew has never said one way or another, but I’m sure he doesn’t mind it. Can I do this? Be with both of them? They can be my twins? Are we going to date? Is this just friends with benefits? I don’t know what to even think.

“Look, don’t over-think it,” Matthew says, “we've never done this before. We just both liked you right off. We share everything already anyway, why not a guy as well? It’s not like it’s going to last forever, but we’re young. Let’s have some fun.”

Rose explains to me that they won’t do anything sexual with me at the same time. They’re not into the brother-sister thing but sharing me could be fun. We can all hang out as friends, like we already do and play as we have been alone. It almost sounds too good to be true, but both are serious about it, if I am. I just have to promise to keep dressing girly for Rose, but I find out Matthew likes it as well. How can I go wrong?

I give them a kiss each, telling them I agree, knowing that it’s something that won’t last forever. We all seem okay with it, though. We’re only young once, right?

I never thought in a million years that something like this could happen, let alone to me. I’m not going to give up the chance. I know it’ll be a little hard to balance out two people, but I think I can manage. After all, they know about each other, that makes it easier. Doesn't it?

Written By Poppet: For LushStories ONLY! 

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