“I don’t have any pyjamas. I don’t wear them; I’m neither seven nor seventy years old! Can’t I just keep this on, until going to bed?” I said, gesturing towards my current outfit?

“No. I don’t want you crying all over my clothes. And you need those as costumes, don’t you?” My sister replied.

“Why on earth would I cry? What are you going to do to me?” I queried in fake panic.

“Nothing. I hope you don’t. But trust someone who knows from experience, these girlie chats about boys often end that way.”

“Boy chats?”

“Yes, boy chats. Whether you like it, or not. That’s what we’re doing,” Claire reinforced. “You really do look beautiful by the way. Well done on your makeup, and maintaining it through the night. The adhesive on your boobies hasn’t lifted at all, which is good.”

“Thanks. I’m hearing that a lot - not the breast thing, the compliments. I think there’s a lot of piss taking going on.” I modestly answered.

“No, Sam, it won’t be that. And you’re going to have to deal with the pros and cons of looking hot. Trust me, you’re like, erm... the hottest girl that you’d see on a night out, like a model you see on Instagram promoting clothes from Pretty Little Thing, like, well, like me!” joked Claire, as we both burst out laughing.

“Oh, we had best keep the noise down. Mum went to bed about an hour ago with a migraine.” Claire suggested. “Anyway, pyjamas, black set in the second drawer from top in my dresser. I left them here last week. Slip into those, and come back down here. Oh, and keep your knickers on, I don’t want to see anything slipping out that a sister really should not see.”

“Like your brother dressed as a girl?” I asked.

“Away with you,” Claire instructed, waving me away with both hands.

“Is this the right set? I was expecting there to be more of it. They’re not that warm.” I asked my sister, who was now curled up on the lounge sofa, playing on her phone, whilst letting a bottle of wine breathe on the coffee table.

My sister looked up from her phone, and towards me in the doorway, “Yes, those are the ones. If you don’t like them, you can wear whatever you like, Sam. Grab one of your own tracksuits, if you’d prefer. Or, maybe try one of the other sets in my drawer or just grab a robe. I’m not forcing you to steal my clothes!” She said, her eyes returning to her phone.

“Okay, give me two minutes,” I said. “Get that wine poured!” almost skipping out of the room.

Well, the available robe wasn’t a warm one. Pretty, and felt nice to wear when I tried it on. Maybe one for some other time, if my sister left it here. There was a set of what I’d have called normal pyjamas, pink with a checked pattern. I slipped into those, leaving my bra and panties on.

Claire’s attention was again taken from her phone, as I stepped into the lounge, “Surprise, surprise... I see you didn’t choose your tracksuit. Is Goldilocks happy with her choice? Is it just right?” she asked, sarcastically.

I nodded, “They’re cute,” and sat at the other end of the large sofa to Claire, curling my legs underneath me. Not as uncomfortable as I expected it to be. Quite cosy, actually, as I gently stroked my hands on the on the soft feeling material gently wrapping my thighs.

“So glad we were able to meet the demands of Princess Sam. Anyway, how did the rehearsal go? Get ready okay? Remember your lines? Not fall over? Tell me what’s been going on.” Claire sat back, cupping her glass of wine, beckoning me to update her.

“So, sounds like it went well. Don’t know how it could have gone better. Apart from them not locking you out of the dressing rooms. I will admit, I’m surprised there wasn’t much teasing; boys today clearly need to upgrade their banter game, if you ask me!” Fed-back Claire, after I’d given her a thorough run through of how the rehearsal had gone.

“And that’s when it all went south; when we went to the pub after. I took some persuading to go, but once there shared some things I think I’d rather not have,” I added

“Let me guess? This involves your hunky chauffeur?” Claire asked.

I nodded, staring into my near empty wine glass.

“Only him?”

I nodded.

“Okay, and whilst I’m on a roll, you told him you were enjoying wearing girls clothes in the play?” said Claire, reaching for the wine bottle.

“Yep, and a bit more.” as I offered my wine glass to be refilled.

“Go on.”

I took a breath. “I accidentally told him I was enjoying it outside of the play, and not just the dressing up.”

“Thank god for that!” Claire exclaimed. “At least you’ve started to be honest with yourself. Whether you wanted others to know or not, that’s much less important.”

“What do you mean? You think you knew, like James claimed he did, too?” I asked, shocked and confused.

“Yes, of course I did! You silly sod. If you were as smart as you were pretty, you’d be dangerous! I mean, let’s look at it, and just ignore everything over the past three weeks for just one moment - that means ignore all the stuff about you wanting to try on practically my entire wardrobe, wanting to practice wearing heels at every opportunity, video calling me late at night for feedback on your makeup trials, not being happy with either the first or second options of how we filled your bra, going out and getting your ears pierced. Ignoring all of that, which is going far, far above and beyond what’s needed to be in a school play, why else would you now not be wearing your own tracksuit? Why else would you choose to be sat in that position? Why else would we be having this chat? To those that know you, you’re an open book, Sam. And it sounds like this guy knows you pretty well.” Said Claire

“I was trying to do a good job; I just really enjoyed it all.” I said, as if I was being called out on something I’d done wrong, despite Claire’s warm, reassuring smile. “And James said I looked happy, that’s how he knew.” I said, staring deep into my now full glass of wine.

Claire smiled wider, her eyes going shiny. “You have done. So happy. You deserve it, too.”

“That’s what he said.”
Claire’s smile grew wider. “I think I’m starting to like this guy. Tell me about him, this could have some legs,”

“Legs?” I asked through narrow eyes.

“He could be boyfriend material. So, what’s his name?”

“Boyfriend? I don’t want a boyfriend. I, erm, I... Claire, I’m so confused.”

I think the crying went on for at least five minutes. Crying and drinking wine, simultaneously.

When Claire released me from the extended hug and soothing back rubbing she held my hands in her lap, and we sat facing each other, legs crossed on the sofa. “Sam, your happiness is the only thing that matters here. No one’s going to make you do, say or think anything you don’t want. Sorry if it has felt like I was leading you. No one’s opinion here matters. You do, however, need to be honest with yourself. Okay? Life is too short, to not take all the chances we might have, to be happy.”

I dried my eyes with the sleeve of the pyjamas, “I’ll try. But stop trying to be so deep, I’ve had too much wine to appreciate it!”

“So, what’s this guy’s name?” Claire went on.

“James. James Howard.”

“Are you joking? ‘The’ James Howard? The big guy? I know him by reputation! If you wanted him, you’ve got a proper hottie there. Half my friends used to go to the gym, just to perve over him working out,” Claire joked, and we both half laughed

“And he’s a nice guy? Other than what I’ve heard tonight? Treats his girlfriends well? He’s had girlfriends, right?”

I paused, before answering, “Well, yes, to all of that. He’s been one of my best friends for years. I’m so worried he will now hate me.”

Claire smiled, “You’ve a lot to learn about men, Sam.” Before quickly adding, “If you want to, of course.”

“Oh yeah, like what?” I queried, doubting her expertise.

Claire grinned, “You think this guy could hate you, because of some things you’ve shared with him? Right?”

I nodded.

Claire went on “Well, not from what I saw this evening, I suspect. But, bear with me on this, just answer these questions, all about tonight. Okay?”

I nodded.

“Okay. Did James touch you in a way he’s never done before? Just casually, I mean. Nothing weird!”

After some thought, “I guess he touched my knee. But then, that doesn’t mean anything; I touched his hand.”

“Right. Did he look at you, in a way he hasn’t before?”

“Hmm, no, not really. I guess he was more smiley, but I think he was trying to put me at ease - unlike these questions! I also don’t suppose he’s watched me walk to the door before, after giving me a lift,” I offered. “Although, not sure if I’ve even turned to look before. Probably just checking I didn’t trip over, or something.”

“Okay. Did he fail to spot other things going on around him? I don’t know, erm, maybe didn’t hear his name being called, or something? You know, a bit distracted.”

“I don’t think so.” I said. “I suppose we both didn’t notice when Martin didn’t return to our table in the pub. But he’s so flaky, he comes and goes.”

“Right, okay. Any slips of the tongue that he may have been embarrassed about?”

“Ha!” I half-laughed, reminded of his slip of the tongue. “He accidentally called me ‘babe’, when making a joke. But he quickly corrected himself. Nothing apart from that, and that doesn’t really count, it was just a slip of the tongue.”

“Okay. Final one of these. Did he show any extra care for you, or look out for you in a way he hadn’t before? Perhaps other than the supportive things it sounds like he said?”

“Yeah, I suppose he did,” I fed back instantly. “He supported me with his arm, back to the car, from the pub, after I half slipped on the steps on the way out.”

Claire thought hard. “The door on the train station side? Ah, that last step has claimed many a heel. It claimed Louise’s front teeth, when we were in our last year at St. Joe’s! Where was he parked?” My sister asked, randomly, I thought.

“Clifton Street. Just before the bridge. Why?” I wondered.

“Doesn’t matter. But have I got this right? He walked you arm-in-arm all the way? Down the High Street, past the Kings Arms and the bus station? Still busy with people around there, at that time?” My sister continued her random questions.

“Yeah, there was a band playing at the Kings, the place was packed and loads of folks smoking out front. And I suppose he helped me out of the car. But, if he hasn’t done that, I’d have had to either crawl out, or I’d still be there!” I joked, trying to ease what had become a noticeably more tense atmosphere.

“I’m getting another bottle of wine.” Said my sister, as she got up off the sofa, and headed to the kitchen.

“Sam?” she asked, as she topped up my glass on her return. “What do you think these actions could all mean?”

“Easy. Having thought about Claire’s questions, whilst she was away. That James is a really supportive friend. I told him as much.”

Claire nodded. “Yes, it sounds like he could be. How did he react, when you told him that’s what he was to you?”

“I can’t remember,” I lied to Claire, thinking his joke answer could be misunderstood. She was not there.

“Okay. Bear with me again. From what I saw and what you’ve told me, I think there’s a possibility James might have some feelings for you. My best guess? He’s fallen head over heels!” My sister surmised. “Now, I wasn’t there to see it for myself, but a guy behaving like that is sending some pretty strong signals; it may as well be written in a letter!”

I was left open mouthed. “Don’t be so silly! He’s not, you know, like that. He’s known me for years, I mean, we’ve double dated, for Christ’s sake! All that has happened tonight is I’ve shared somethings I didn’t mean to, whilst looking very differently to how he’s seen me before. I don’t know why you’re trying to make out he, what, fancies me?”

My sister doubled down, “If ‘looking differently’ means presenting as a beautiful woman, we’re on the same page. I can help find out for sure how he feels, that’s what big sisters are for. We don’t have to guess. What we do need to decide, is what we would do, if I was right.”

“How do you mean?” I was intrigued

Claire smiled. “Simple. If there was the tall, handsome, fit, charming, kind, supportive beefcake that was head over heels into you... is that worth exploring?”

“Exploring?”

“Okay, okay. From what I saw through the window, when you pulled up,” my sister paused for my acknowledgement, “if James had helped you up out of the car, into his arms, and kissed you passionately, would you have kissed him back?”

From how warm I felt, I could only guess as to what deep shade of red I had gone.

I took a deep breath, “Yes” I said quietly, returning to staring at my wine glass.

My sister gave an encouraging smile, “Okay. And your teasing or joking peck on the cheek, was that intended to encourage him to initiate something more?”

“Yes. I think it was. Yes.” as I turned to make eye contact with my sister.

Still smiling, my sister went on, “Well done. I know this isn’t easy, but I’m so proud of your honesty.”

I half smiled, “Proud of your sissy of a little brother?”

“Hell yes! And my beautiful little sister.” As Claire topped up my glass of wine.

“If you found that embarrassing, brace yourself”, she went on with a wink and lingering cheeky grin. “You need to picture this in your mind. Okay? Let’s assume you shared that passionate kiss by the car, you running your hands through his hair and linking them around the back of his neck, him holding you close, stroking your hips and squeezing your arse, he scoops you up and carries you into an empty house. You go upstairs, he strips naked, to expose his...”

“Woah! What are you doing?” I asked.

“Sam, I was just trying to see if the thought of his hard cock repulsed or exited you. Because, let’s face it, men typically expect a bit more from their girlfriends than a kiss.” Claire went on.

I was so warm, “It doesn’t repulse me to think of it” I said quietly, feeling totally ashamed of myself, looking down into my lap. “When I lent in to kiss his cheek, after getting out of the car, it felt like he had a hard-on. I wan..” I stopped myself.

“Go on. What? What did you want to say?” encouraged Claire.

I took a deep breath. “I wanted to touch it, I felt kind of proud that I may have caused it,” I said at double speed, before grabbing my wine glass.

Claire smiled cheekily.

“Beep! Beep!” as I received a WhatsApp message.

“It’s James!” I said almost in fear to my sister; had he heard me? I panicked.

My sister gestured to my phone, encouraging me to pass it to her.

“Glad you made it to the house without me ;) I enjoyed tonight. See you tomorrow x” she read out, before scrolling through other messages.

“Interesting,” she said, “he’s never put an ‘x’ at the end of his previous messages.” As she passed me my phone back, grinning.

I started to type a reply.

“Woah! Hold your horses. This needs careful game management,” said Claire. “Type this... ‘Me too. Night.’ And put two large X’s at the end.”

I sent the message.

“And, the significance of that?” I asked

“Well, you’re not saying which of his two statements ‘me too’ is referring to. He’ll read that over and over, wondering if you’re also glad you made it to the house, or if you also enjoyed the evening. Saying goodnight gives you control of the conversation. And if he replies with anything less than two large kisses, I’ll... ah, there’s no point in finishing that, it’s a certainty!”

Almost as soon as Claire stopped talking, another message came through.

“Glad to hear it :) Goodnight XXX”

I smiled at the screen, and then peered over top of the screen, to look at Claire.

“Hand it here,” she instructed, offering out a stretched arm. Claire read the message to herself, then shut down my phone and put it on her side table. “Am I fucking amazing, or what? They can stick their grade C psychology A-level up their backsides; I should be writing the textbooks!”

“You’re definitely something!” I teased. “Can you pass me my phone?

“No. You’re not getting this back until morning.” She advised.

“You what?” I asked

“I’m not having you undoing all my good work, and sending a silly message. Done too often, and after less wine than we’ve had. Speaking of which...” as Claire emptied the last drops of wine from the bottle into my glass. “Oh. I’ll get another,” as she went off to the kitchen.

I sat and contemplated what had happened this evening. I couldn’t concentrate. I just smiled, but still felt anxious, or perhaps it was just excitement.

“What are you grinning at?” asked my sister as she returned with two glasses of what looked like Coke. “You look pretty pleased with yourself.”

“Still confused, more than anything. And where’s the wine?” I replied

Claire passed me the cold glass, “All gone. And that was the wine I bought for Mum, to replace what Louise and I wiped out the other week. That’s a rum and Coke.”

I sipped the cold drink, and was shocked by its strength. “Any Coke in this?” I asked sarcastically. “I’ve got school tomorrow.”

“Oh, man up!” Claire teased. “And how about you give school a miss tomorrow? Throw a sickie.”

“I won’t have to throw a sickie at this rate. Are you around?” I asked

Claire nodded.

“So, what would we do?” I followed up.

“I don’t know,” said Claire. “We’ll come up with something. Oh, I’ve just reminded myself, Louise is arranging a night out in Manchester this weekend; now you’re not tied up with sports, want to come?”

“Manchester? Didn’t she go to uni in Leeds?” I asked.

“No. You might be thinking of Louisa. However, we don’t talk about her any more. Don’t ask, it’s a long story. So, you up for a night out? I’m not forcing you, but I’ve a hotel booked; I could change it to a twin? It’s just a few bars, few cocktails. Maybe a dance. Fancy it?”

“Can I let you know tomorrow?” I asked

“Sure,” said Claire. “Got a better offer? Or perhaps waiting to see if one comes through from lover boy?” she paused. “Ha ha!” She continued. “I’ve never seen anyone turn red so quickly. We still have lots of work to do, don’t we?”

I half nodded. “Yeah, I guess so. I’m really struggling to get my head around how I feel and also what it means. The alcohol probably isn’t helping me think straight, either.”

Claire shook her head. “As long as you’re not slurring your words, the drink can’t be hurting too much. Apart from your liver. All of us take time to come to terms with our feelings, but what exactly are you struggling with right now?”

I took a deep breath. “Okay, I’m guessing you realise this, but I don’t think I ‘am’ a girl. I don’t think that, how do they say it, I’m a girl in a boy’s body. Right?”

Claire nodded, “I’ve not assumed you’re a transsexual, that’s right. It’s only been three weeks since I assume these new feelings started to emerge to you, so do keep your mind open though. Remember those chances at happiness, yeah? So, what’s the problem?”

“The bit I can’t wrap my head, is what I would be, if, you know, if some of the things you have assumed came to be.” I told my sister.

It was my sister’s turn to look confused. “Really not sure I’m following you. Talk me through it.”

“Okay. So, you think that James suddenly fancies me, and vice versa. If you assume we dated, became a couple, or whatever, I don’t think he’d fancy me as a boy - which I would still be most of the time, like at school. I also can’t currently imagine myself being with a man, when I’m not presenting as a woman. I just don’t get how it would work. Would we kiss hello when I’m dressed as a girl, and fist bump at school? It’s all those sort of things I just don’t get.” I handed the baton to my sister, to fill in the gaps.

Claire frowned. “Erm, why does it matter? It sounds like you’re basically asking what would my ‘status’ be called. Let me summarise what I think I’ve heard... what do we call a boy that fancies boys when he’s dressed or presenting as a girl, and may or may not fancy boys when he’s dressed as a boy; and his relationship with another boy who may only fancy him when he’s presenting as a girl, or he might also fancy him as a boy too. Is that about it?”

“Erm, I think so.” I offered.

“Oh, that’s easy. That’s called being happy. Come on Sam, there’s nothing whatsoever to be gained by putting your feelings into someone else’s neat little pigeon holed boxes! You do what you need, to make yourself happy. Everything else, you do what we all do, and make it up as we go along!” Claire advised.

“Okay, okay!” I put my hands up in surrender. “I get all that. But, isn’t a bit, kind of, I don’t know, schizophrenic to engage with one person in two totally different ways?”

“No, not at all. Having different sides to your personality is not the same as having deconstructive and contradictory multiple personalities. And you know, lines get blurred. In your scenario, what does the boy have to do, to be considered in girl-mode in this relationship? Is a dress enough, or does it need makeup, too? Would high heels and a bit of makeup tick the box?” Claire was on a roll, and spotted I was confused. “See how ridiculous this all is? Happiness finds a way, Sam.”

“I get what you’re saying, I do.” I pleaded. “It’s just I’m playing over parts of my life in my head and can’t reconcile how they would work”.

“Well, that sounds like a bit of anxiety. You can’t worry about things that haven’t yet happened, and catastrophise them. Right, think of this - are you safe now?” Claire was pretty good at this, I thought.

“Yes, I suppose.” I replied

“No suppose about it. You are safe. That’s a fact. Of course, a plane could crash through the roof, the gas main could explode under the house, or all sorts of horrible things could happen. You can’t worry yourself with all those things that might, but probably won’t happen. You are safe now. That’s what I learnt from the counsellor I met with after Dad died. Love each day as well as you can, and only worry when you actually have something to worry about. Okay?”

Claire had taken Dads death a couple of years ago even worse than I had. She was very much a daddy’s girl, and things had gotten pretty dark for her at one point. I actually started to feel a bit selfish, worrying over what people would think of what clothes I was wearing, who I was holding hands with, or whatever I was doing. “Thank you Claire. I suppose it takes time?”

“It will. Baby steps. Anyway, I’ve run out of wisdom for one night, I’m off to bed.” As she lifted herself off the sofa, she leaned over and kissed me on top of the head. “Goodnight, Princess. I’m so proud of you, and believe me, Dad would be too.”

Before I could process what she has said, she was already heading upstairs.

“She’s taken my phone!” I thought to myself.