Needing Leah Ch. 02

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Leah's roommate knows her secret...does she enjoy that?
3.3k words
4.55
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Part 2 of the 10 part series

Updated 10/22/2023
Created 07/16/2023
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The story so far...

18-year-old Liam Weber has been sent to Bryner academy in England, after his parent's insistence that he get "the best education possible", and Bryner turned out to be the only private school that accepted his scholarship...however, once Liam reached Bryner, he discovered it was an all-girl's school, and that they had his name listed as Leah. Did his dad do that on purpose? Will it count as fraud if the school finds out? His roommate Ellie agreed to help disguise him as a girl while Liam figures out what to do...but it's a dangerous secret to try and keep and Liam isn't quite sure if he can trust his roommate...

2: Dress and Discovery

I really wasn't comfortable with the idea. I was even less comfortable with the devilish smirk on Ellie's face. She looked like she was enjoying the idea, but why? Only moments ago, she'd seemed furious at me.

"Ellie. I don't know..." I said, slumping down onto what was to be my bed for at least a night or two.

"Do you have a better idea? I don't know anything about the law either, but you're right; this could be fraud. You're faking your identity to steal a scholarship that could've gone to someone else."

"I didn't mean to! My parents set it up, I didn't know this was a girl's school until you told me, I swear!"

She dropped down on her bed opposite. "Well, your parents must have known? How desperate were they to get you into a private school?"

I didn't want to answer that. It felt my face blushing at the embarrassment of the situation. They couldn't surely have done this deliberately? My dad had always been desperate for me to get a good education. Would he do that at the expense of my identity? I shuddered a little.

"Can't I just skip classes or something? I mean...I mean do I really have to dress as a girl?"

She giggled. "It's not that bad."

"It is a bit. It's kinda humiliating."

"Why?" She frowned. "You're all big ego and Mr. Macho, are you? You want to drink beer and play football and say manly things? You don't look very macho."

I lowered my gaze. She hadn't needed to say that.

"It's only humiliating if people find out, isn't it? So long as everyone just thinks you are a girl, then there's nothing to worry about. You'll just seem totally normal."

"What if they do find out?"

She giggled again. She brushed a stray lock of red hair behind her ear. "Follow my rules and they won't, I'll make sure."

I didn't feel confident. Recognizing this, she got up and moved towards me, leaning forwards to put a hand on my shoulder.

"Hey, come on. I get this must be tough for you. I'll help, though. I'll get all the clothes you need, I'll help dress you and do your makeup. Try and see the fun in it all. Even if it's not what you want, it can be a bizarre adventure for a few days."

I appreciated that. She stroked her hand down my shoulder. It felt nice. I could smell the perfume from her neck. Her breasts were right before me. If I raised my head, I would've been just inches from her face. Perhaps sensing my gaze, she cupped my cheek and lifted my eyes to hers.

"You understand that you owe me for this, right?" She said in such an odd mix of playful affection and cold warning, that I couldn't quite make out the meaning. "I'm sticking my neck out for you, I expect your gratitude."

"Ye...err...yes, I..." Before I had even formulated whatever question was on my confused mind, she stood up again.

"Now come on, Leah. I'll pick out some of my clothes for you to wear today, you don't look any taller than me, even if you've got a small build. There'll be classes tomorrow though, so we'll have to get your measurements for uniform."

"Do you have to call me Leah?" I asked.

"It's supposed to be your name."

"Yes, but here? When no one else is around, can't I just be me?"

She shook her head. Her smile this time was less cold and more playful. "You have to get used to the name. If you get called Leah in the register and you forget to respond, it's going to look weird, honey." She turned and began pulling through her wardrobe and drawers for clothes. Reluctantly, I stood up.

"Can't I just wear what I'm wearing now? Jeans and a top are fine, aren't they? I mean you're only wearing shorts and a top."

"I'm wearing these because I go running in them, then I take a shower and change into something nicer. You don't know what an all-girl's school is like, do you?"

I shook my head. Quite obviously, I didn't know.

"People can be really bitchy. You want to look really pretty for your first impression, otherwise you'll get teased, which will only draw more attention to you. The last thing you want right now is bullies."

The thought made me shudder. Bullied by a bunch of girls. That on its own felt humiliating, but it was more than that. It was the thought they might uncover my identity. They would do worse than just bully me, then.

"Right. Put these on."

A tight-neck black top with a silver strip down one side. A pink draped skirt, white stockings, and a pale-red, padded bra.

"Maybe it's not the best impression, but I've had to pick things that keep your body hair covered, for the moment. We'll do something about your hair later."

I looked at her, bemused. "I don't need the bra, do I?"

"The bra will give you padding. I'd give you some silicone pads, if I had any. We'll just stuff it with some of your clothes. Get some."

She clicked her fingers as she said that, pointed at my bag. With a sigh, I unzipped it, then froze. I rummaged underneath the books and laptop. Nothing. No clothes at all. I felt stupid. How could I be that stupid? How could I forget all my clothes?

Then it hit me. My parents had packed the bag while I slept. They took everything I'd need from other rooms around the house, then I was supposed to add anything from my bedroom I'd need, which obviously meant my clothes. Waking up at 4am with a taxi driver at the door, however, I'd completely forgotten.

"I-I don't have any clothes. I think I forgot them." I said, blushing a deep red.

"Really?" She giggled. Somehow, that seemed to please her. "You look cute when you go red, Leah. You don't even have socks? No boxers?"

I shook my head.

"So you've only got the boxers you're wearing now?" When I nodded, she grinned. She turned again to the drawers and pulled out a pair of briefs. Pale-red, cotton knickers to match the bra. "Put these on as well."

"Really? Can I just keep my boxers on? I mean no one's gonna see them."

"You can't wear and sleep in the same boxers, especially if you might be stuck here a few days. That's disgusting."

"I can handwash them in the evenings?"

"And wear what while you wait for them to dry? Besides, you need to feel as much like a real girl as possible. Method-acting, Leah. If you don't seem girly enough, you'll give yourself away."

"I know, but I don't really..."

She cut me off with a glare. "Leah, I asked you to do as I say. Understand? Put them on then tell me when you're done."

There was threat in her voice. It startled me. Her voice had cracked like a whip. For a second, I almost laughed, thinking she was joking. Her glare was an icy fury, however. I realised then that she knew a secret that she could ruin my life with, should she ever wish to. Perhaps I really, truly did owe her? Perhaps I was trapped in her debt. The thought twisted a knot in my stomach. "She wouldn't do that. She wouldn't use this as leverage over me." She might. I didn't know. I barely knew anything about Ellie. "What have I gotten myself into?"

She walked out into the ensuite and closed the door behind her. Humiliating as it was, I undressed my current clothes, placing them on the bed. First, the panties. They were soft to feel, much softer than my boxers; delicate with a deeper-red lace trimming. I put both my feet through and began to pull them up, wondering if they'd even fit. As I raised them, however, something happened I didn't expect. My penis was getting hard. Only a little at first, but as the soft fabric reached my balls and I tried to stretch the knickers over myself, it became fully erect. I was only just able to fit it, with the elastic pulling down against the end of my penis, caging it. My balls felt tight, as well. They were pushed close together, and pulling up the back of the panties had forced them into a wedgie.

Why was I erect? I certainly wasn't enjoying the experience. It felt humiliating. It felt uncomfortable. I felt miserable at having to do this...and yet I was erect. I couldn't get rid of it. The tight pressure of the fabric only made it worse and I felt myself throbbing.

"It'll go in a moment." I told myself, picking up the bra. I held it over my chest and tried to hook it behind me. I couldn't do it. I stood there for at least five minutes, trying to manage the hook, wearing red knickers that barely covered me, feeling more pathetic than I'd ever felt in my life. The erection, at least, had eased a little, enough that it looked more like a flaccid bulge than a clear erection. I dared to call for Ellie.

"Ellie? How, how do you hook a bra?"

I heard her giggle again. "Can't you do it?"

"No."

The door opened. Coming out, she stopped when she saw me. "Looks like something's trying to break out of your knickers, Leah." She joked. It made me freeze, though she didn't seem to have recognised I was slightly erect. When I said nothing, she her smiled faded into a frown, as though I'd displeased her. "I'm trying to make light of the situation, Leah. You'll be miserable if you take this all too seriously."

"I guess."

She sighed, looking at me again. "This evening, I'm going to wax you all over. We don't want anyone spotting any hairs and, like I said, we want you feeling as girly as possible." She came close again. She stood behind and held the bra over my chest. I could feel her breath on the back of my neck.

"I can't hook it behind myself."

"It's easier, Leah, if you hook it over your stomach, then spin it round afterwards." She hooked it for me, all the same, then brushed a hand through my hair. "We'll have to do something about this, too. It looks uncared for."

Her touch, the intimacy of it. I supposed this was normal between girls. There should be nothing strange about one girl brushing a hand through another's hair. For me, it felt arousing. I wasn't used to a girl so close. My penis began to harden again. I found myself trying to think about other things, hoping it'd soften, but the pressure, the worry she might see made it difficult to distract myself.

"Now, put on the stockings. They have grips that should stick to your thighs." She said, heading back to the ensuite. "Then your bra will need padding." She returned with a roll of tissue and began scrunching bits up into small balls. "I'd rather not waste more of my clothes on you. You're lucky I've let you borrow any at all. You can pad it with this instead." I tried to keep my back to her as I pulled the stockings up.

"Done." I said, hesitant to turn around. I went to pick up the skirt.

"Good girl. Come on, then."

I didn't move. I froze, during which time she came over to me instead, standing in front with a scrunch of toilet roll.

"You can't wince when I say things like good girl. I'll have to keep saying it until you get used to it, otherwise when someone..." she paused. She was looking down. I closed my eyes, knowing what she was about to say. "Are you, are you turned on?"

It felt humiliating, having to silently nod.

"What the fuck, why?"

"I don't know." I mumbled, wanting to sink through the floor.

"Was it because I said good girl?"

I dared open my eyes again, finding her before me, smirking. She wasn't disgusted, at least. She wasn't calling me a 'little pervert' again. Instead, she seemed amused. I couldn't work out if that was better or worse.

"Were you hard before I said it?"

I didn't answer.

"Is it...is it the clothes?"

I looked away, which she took to mean yes.

"Well, I suppose that's kind of sweet." She rubbed my shoulder again. "Maybe becoming Leah is a blessing in disguise?"

"No." I tried to be clear on that. "No. I don't want this at all."

"Your body seems to want it. I did say, maybe it'd be fun." She giggled again, which made me feel pathetic. "Sweet girl. I was worried about letting a boy stay in my room. I didn't realise you were so harmless."

"I'm not." I almost said out loud, but just stopped myself. She began padding my bra for me, looking much more relaxed in my company all of a sudden. It was as though, in her mind, she'd decided I really was a girl now. All because her clothes turned me on a little? I'd never felt aroused by women's clothes before. Then again, I'd never worn them before. Either way, I was still a boy, I was still attracted to girls. I was still attracted to her...

I suppose there was a positive in that: how suddenly comfortable she'd become with intimacy. She was standing very close as she padded tissue into my bra. I kept trying not to start down at her bulge of breasts beneath her top. They brushed against me in moments, sometimes so much so, that I wondered if she was doing it on purpose. My cock felt pained; throbbing hard and yet penned back by the tightness of the panties.

"Leah?" She began, holding the skirt for me to step into.

"Yeah?" I did wince as she said that name, she was right.

"What if your parents won't let you transfer anywhere else? I mean this was the only private school you could get into, right?"

"Yeah." I said weakly, raising my arms a little as she fed the top over me. "I don't know. Surely they won't force me."

"If they do, I don't mind, ok?" She began lifting the skirt up my legs, very, very slowly. "I find it kind of cute. I'll look after you." She was crouched low. She brought the skirt up to my waist. It was loose enough to hide my erection, but she used her hands to pull the skirt taut against me, until the bulge appeared.

"Would you like me to look after you?"

I didn't know what to say to that. In the silence, she took a hand and gently tapped against my bulge.

"Would you like that, Leah?"

"Err...I..."

"You'll have to follow all my rules."

"W-what rules?"

She tapped at my penis a few more times. A little amused smirk appearing on her face, especially when I squirmed faintly on the spot. I was so turned on. She was right there, touching it. So gently, so lightly. I wanted her to move her hand under the skirt, or to pull it down. Her face was so, so close...then she stood up.

"My rules." Her smile turned deceptively sweet. She kissed me lightly on the neck. "It wouldn't be fun if I told you the rules in advance, would it? I'll give you a tour round the school, Leah. Then we'll get lunch and sort out your school uniform for tomorrow. Let me just take a quick shower and get changed first, ok?"

I nodded and watched her disappear behind the ensuite door. It was only as she left that I realised I'd been holding my breath. Out came a deep exhale. She had been teasing me. She must have been, that had to have been deliberate! She had found amusement turning me on, only to walk off and disappear.

I sat down on the bed, feeling more aroused than ever. I was dressed as girl now. I felt my breasts. They were only stuffed with tissue, but I still liked the feel of them. I squeezed a little, then ran my hands down the black top. I got up and looked at myself in the mirror. I did look like a girl. I was myself but...but different. "But Leah." I thought, turning round to see the rest of my shape. I didn't want to think of this as me. It was humiliating if I was still Liam. If I could try to think of myself as Leah, then maybe this would feel normal? I lifted the skirt up. Even my arse looked like a girl's; tight and pert, with a slight jiggle when I shook it. The panties were still caught between my cheeks. I went to adjust them but it was difficult when the panties were so tight. I decided I liked the feel. I turned forwards again, feeling my breasts once more. My erection had not faded in the slightest. It hurt. More than anything, I wanted to touch myself. I wanted to stroke, still wearing the outfit. I could hear the shower running in the other room. I considered it. I wondered if I'd have time, if I'd be able to manage a tour round the school, wearing all this, feeling so horny, without first getting it out of my system.

Then I heard the water stop. My chance was gone. I was going to have to endure somehow. I was going to have to walk all round the school, walking past other girls, being dressed as one of them; throbbing with arousal, and somehow ignore it. Even worse, Ellie had enjoyed teasing me. A sudden dread rose up my chest. "What if she wants to tease me more while I'm out? What if that's going to be one of her rules?"

Hope you all enjoyed chapter 2! So sorry it's taken forever to upload! I actually uploaded it 20 days ago but it got stuck in pending and after nothing resolved, I decided to delete it and try uploading it again now...so hopefully this reaches you all quicker!

Again, I should technically apologise about the slow pace but hey! There's fun in being made to wait the way Leah is. A lot will be coming soon. Pleasure, punishment, some interesting twists but the more we establish Leah and Ellie's relationship, the more the good scenes should land. I want there to be a real dynamic that develops between them, and I think that's really what this chapter has focused on establishing.

Let me know if you have any thoughts, questions, feedback. If there's anywhere you're hoping or worrying the story might go, if you'd like me to pick up the pace for chapter 3 or build a little more suspense first. Either leave a comment or feel free to email me.

- Serra

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monasissymonasissy8 months ago

Beautiful so far. I am happy for Leah.

SouperKev777SouperKev7778 months ago

Very amazing, keep up the good work.

GimliOakensGimliOakens8 months ago

Ok. I think this is going to be very enjoyable. I love it so far

SerraShadesSerraShades8 months agoAuthor

Thanks! Chapter 3 has been uploaded, so it's just the wait for it to be approved. Hopefully not too long

AnonymousAnonymous8 months ago

I think the pacing is good! Is it long till the next chapter?

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