Meeting Sherry Chapter 01

Meeting Sherry

Written by SerenityInSound

Chapter 01

My name is Alicia, and I'm trans.

When I entered my new school, I made a vow to myself to never hide that fact. I had been transitioning for a while now, so it was totally possible I could. The temptation had been there.

At my previous school I'd received a lot of bullying when I came out. The possibility of that at my new school for sure scared me. But the way I figured, I couldn't hide it forever. I would rather be brave and forward, than cowardly and have my potential friends feel like I had tricked them.

And it worked! People took me at face value, got to know me as I was. Nobody bullied me, and I got on reasonably well with everybody. But unfortunately, something I hadn't foreseen was that my being trans put a certain... invisible wall between me and the others. They struggled to connect with me.

It was certainly nothing malicious, but it meant I struggled to make friends with anyone. Changing schools during the final year meant the friendship groups had already been established. Finding someone close, a best friend, was a long way off.

That was, until another new girl joined the class.

"My name's Sherry. I'm trans, I like girls, and I don't wear underwear." Was her explosive opening. Everyone in the class was stunned, everyone immediately whispering to the person next to them. The teacher was rubbing her brow with a long-suffering look.

Sherry was almost unfairly beautiful. Freckles, short messy hair dyed red, piercings, she was clearly going for a more tomboy look. The kind of beauty that I wanted emulate, and which brought butterflies into my tummy.

All my life, I had always made sure I had carefully curated long hair, pretty nails, polite and minimal makeup... I had always strived just to be the standard girl. I felt out of my depth just achieving that much, trying to blend in with the other girls around me. Trying not to feel too self-conscious.

Sherry had blown that preconception to bits just by existing - she wasn't just a trans girl trying to be feminine. She was clearly a girl who had looked at the idea of 'traditional femininity', and decided to say "fuck that" and gone off in her own direction.

Also, her skirt was short. Short enough that I couldn't help but glance at it, wondering how she avoided exposing herself, especially without underwear. I couldn't imagine it was easy.

Also, how on earth? Why did the teachers not care about her wearing underwear, in a skirt like that? That seemed wild to me.

When I tore my eyes away from her skirt, I saw her staring at me with a grin. I blushed and looked away. Apparently I'd been caught staring. Oops.

"Sherry was graciously granted leeway with certain uniform requirements by the headmistress." The teacher said in a tone that suggested she disagreed with the decision, but had been overruled. "It does not give anyone permission to act rudely towards her. If I catch anyone trying to take advantage, you'd best believe I will be punishing you just as I would with any other girl. Is that understood?"

There was a gentle chorus of "Yes miss." from the class. To be honest, I wasn't expecting any trouble. Everyone it this class was pretty nice, and all the boys had good manners with the girls. I'd never seen someone get harrassed or have their boundaries pushed.

During break, I went to greet her. I was honestly excited, with another trans girl in class, this was my chance to get a best friend! I was absolutely determined to get on with this girl.

"Hi, I'm Alicia." I said, giving a little wave.

"Oh, it's the girl who wanted a peek." Sherry grinned cheekily. I blushed furiously.

"I-I didn't- I- ... s-sorry. I was just wondering how you avoided exposing yourself." I stuttered.

"Hmm, well the short answer is that I don't." She shrugged easily. "Were you thinking of trying it yourself?"

My mind went blank for a moment. Could I go without underwear? It would be so... so outrageous! I would be so vulnerable, I wouldn't be able to help my classmates sometimes seeing me...

The thought was like electric through me, and within moments I felt my penis pressing against my underwear. There was a moment of dawning horror, when I realised where Sherry's eyes had gone.

"Oh, you're tr- ... uhh, you're like me." Sherry said in quiet shock, eyes wide as she stared at my crotch. I hunched over in mortification, trying to hide my growing erection. This was a humiliating way to introduce myself. I'd wanted to make a good impression, not... whatever this was!

"Here, take this, I'll help you to the bathroom." Sally said gently, holding her backpack out in front of me to cover up. I took it instinctively, feeling very self-conscious as Sherry wrapped an arm around me and cuddled me close as though I was feeling ill, guiding me to the door.

She was trying to avoid outing me, I realised suddenly. Sherry didn't know I was out, and had immediately gone into protective mode. The thought brought something warm to my heart, and I didn't comment as I let her guide me to the girls' bathrooms.

"Sorry. I hadn't meant to... well, I didn't realise it might be a little dangerous to tease you like that." Sherry said sheepishly.

"I'm already out as trans, you don't have to worry." I said, taking her hand. "But... thank you for protecting me like that."

"Oh. Uhh, it's no problem. I hadn't realised there would be another trans girl in this class. You're really pretty!" She said excitedly.

I blushed, "Thanks, you are too."

My erection apparently wasn't going down any time soon, and I shifted awkwardly, very aware of the tenting in my skirt.

"Do you want some help with that?" Sherry asked out of the blue, glancing down at my crotch.

... Wait, what the fuck?

I stared at her, and Sherry was quickly turning pale. "Uhh, f-forget I said that, I speak without thinking sometimes." She said in a strangled voice.

"By help, you mean..." I said faintly, not quite willing to believe that meant what I thought it meant.

"I-I just... well we're both trans girls, and you're super pretty, and s-since you were having a relatable problem I t-thought... nevermind." Sherry squeaked, looking mortified as she dug herself further into the hole.

Dear god, I was actually getting propositioned by the beautiful new girl in the girl's bathroom, what in the actual-

"Okay." I said, not quite believing what was happening.

"O-Okay?" Sherry asked, staring at me.

"I'm okay with you helping." I said faintly. My emotions were a mess, was that a real offer? Was this just a joke?

Sherry nodded, pulling me gently by the hand to one of the toilet stalls. Once inside, we awkwardly stared at each other. Sherry's eyes were really quite beautiful, I realised. Dark blue flecked with hazel, I found myself sinking into them.

Sherry broke eye contact, looking nervous.

"You don't have to if you don't want to." I said, thinking she might be having second thoughts.

"No! No, I do, I just... haven't done this before." Sherry mumbled, kneeling down in front of me.

"That makes two of us." I teased shyly.

Sherry gave me a small grin, a glimmer of her beautiful confidence hidden behind her eyes. "First time for everything, I guess." And she reached up and pulled my panties down.

Lifting up my skirt, I watched with butterflies as Sherry stared at my hard penis. She gulped, and the sound sent an involuntary twitch through me. The head was slick with precum.

"Here goes." She whispered to herself, before wrapping her lips around me. I gasped, not expecting the warmth of the sensation. Her mouth was wet and hot, and as she bobbed her head it gave a delicious gentle friction that had me whimpering.

The sound of Sherry's sucking echoed lewdly, only adding to the sensory overload of my first blowjob. My whole body became that one point, my mind focused on the pleasure. I felt this beautiful girl's warm mouth, felt as her tongue swirled around my foreskin, felt her try to bring more and more of me into her.

It wasn't long until I felt right on the edge. "Don't swallow, just hold it." I murmured unbidden. I wasn't sure where the words came from, but in that moment I was too hot to care. Sherry gave a small, submissive nod in response.

Something in my mind caught onto that. Recognised that I was seeing a hidden side to this girl. Did she enjoy orders?

Moments later, I was filling her mouth with cum. She gave a little squeak when the first splash hit, but obediently accepted it all, storing it all in her mouth.

I guided her up to her feet, Sherry's eyes were glazed, her cheeks bulged with cum and flushed red. "Good girl." I praised. "Don't swallow. I'll do you, then we'll share, okay?" I said, staring into her eyes.

Sherry gave a little whimper, her breathing shaky, but she nodded. I smiled, giving her a little peck on the lips.

Kneeling down, I faced my first cock - well, the first from someone else anyway. She was slightly smaller than me, but hard and twitching, and a lewd smell of precum hit me. I could see it glistening over her head.

First a little kiss, pulling back to taste her precum thoughtfully. It had a very gentle flavour, slightly sweet. Then I engulfed her, doing my best to emulate what I had enjoyed from when she pleasured me. I had a fairly good idea of what was pleasurable for her, but still paid careful attention to what she seemed to enjoy the most.

I reached out and grabbed her hand, our fingers intertwining. I could understand where her submissiveness had come from now, there was something fulfilling and vulnerable about pleasuring a person like this. Listening to Sherry's quiet moans, muffled through the mouthful of my cum, was quite intense.

With me steadily pleasuring her, Sherry didn't last long. When she cummed, it was like an avalanche. Her whole body started shaking and twitching, and her legs buckled slightly as she pumped a huge load of sperm straight into my mouth. I felt my cheeks bulge, as I struggled to contain it all.

I listened in pleasure to her cute whimpers, savouring the salty-sweet taste of the cum. I'd tasted my own before, but Sherry's was different. Delicious and moreish and a unique flavour that I immediately associated with the beautiful girl.

Allowing her wet, softening cock to leave my lips with a gentle plop, I smiled up at her deviously.

My cheeks full of cum, I moved to kiss her, wrapping my arms around her trembling body. Sherry's eyes were wide and wet, as though she couldn't help but cry from the overwhelming emotions.

When our lips met I allowed her cum to spill out into her mouth, our tongues swirling in the delicious mess. I could taste our flavours mixing, our essence combined in this sacred ritual. Sherry met my tongue shyly, following my lead yet still obviously overwhelmed.

I could hear our heavy breathing, the unconscious whimper of the cute girl in my arms. We took our time in that kiss, savouring the taste. It was erotic in a way that spoke to something deep in my core.

I pulled back, taking a moment to swallow the cum in my mouth. It was thick and sticky.

Sherry stood silently, her eyes glazed in lust and her mouth open, displaying our shared essence filling it to the brim. Her face was a sticky mess where the cum had spilled out past her lips.

"Swallow it all, there's a good girl." I said gently, still hugging her close to me. I heard two audible gulps, as Sherry swallowed the large load. She'd ended up with most of it, I think, since I was a bit taller than her.

I reached a hand up to gently scrape up the cum that had leaked from our lips, pushing it all into hers. Sherry stood there compliantly, accepting all the stray drops of cum, swallowing them down too. Each time I gave her another little kiss.

There was a few more moments of me cleaning us up, wiping away any stray bits of cum and feeding it to her.

"Wow. That was pretty intense. I hoped you enjoyed yourself." I teased. Poor Sherry was still breathing heavily, trembling slightly.

My heart felt warm, and I wrapped her into another deep hug, which Sherry accepted silently, wrapping her arms around me. "You were a good girl. You did a great job. Shh..." I murmured, whispering little assurances to her.

Sherry rested her face in the crook of my neck. We stood like that for a couple more minutes, before the bell rang for the end of break.

Finally, I pulled away from the warm cuddle. Sherry's face was still red and she couldn't look me in the eye, but she looked calmer now.

"Come on, we've got to get to class." I said, giving her one last gentle kiss. Then checking to make sure we were both relatively decent, I pulled Sherry by the hand back to class. Both our fingers still intertwined, I felt her squeeze my hand gently.