Meeting Sherry Chapter 02

Meeting Sherry

Written by SerenityInSound

Chapter 02

"So how come you got permission to not wear underwear? And why aren't you wearing underwear?" I asked Sherry during lunch. We were sitting with a couple of other girls, Lauren and Beth. I didn't have a consistent group at lunch, so it had ended up just being whoever was interested in meeting Sherry.

She had mostly recovered by now, though there was still a faint glow to her. She still couldn't quite look me in the eyes, which I privately found kinda cute.

"Mostly just 'cause I don't like wearing them. My parents experimented with nudism for a few years when I was younger. We don't do it anymore, but I could never really get used to wearing them again afterwards, and they never pushed the issue." She shrugged. "Plus it makes me feel kinda..." She started, before trailing off, shifting like she was embarrassed.

"Kinda what?" Asked Beth.

Sherry looked down with a bit of a shy smile. "... Sexy, I guess? Maybe it's just stupid trans stuff, but sometimes I struggle with... self-confidence and how I look and stuff. Thinking about how I'm vulnerable in that way relaxes me. Makes me feel desireable."

"Honey, that ain't trans stuff, I'm afraid that's just girl stuff." Lauren said dryly, though she gave Sherry a gentle smile, nudging her in a friendly way.

"Do you think going without undies would help us too?" Beth asked hesitantly, looking at Sherry. She sounded like it was a serious question though, which surprised me.

Beth was an absolute cutey, with a gentle demeanour and an oddly old-fashioned bob of blonde hair that seemed to somehow suit her really well. It had never occurred to me before that she might share that sort of problem.

Sherry kinda shrugged, but nodded. "I mean it's worth trying, right? Works okay for me."

"The teachers would never allow it." I sigh, feeling irrationally disappointed.

"They let her." Lauren pointed out.

Sherry shifted uncomfortably. "They sorta... made an exception for me. I think they really wanted me in the school."

"Why?" Beth asked, curious.

"I dunno. Supposedly I'm smart or something, so they wanted me, and were willing to let me make some demands." Sherry mumbled, playing with her food. "It's stupid. But I guess it did mean I don't have to wear undies, so it had some benefits."

"If you want to do it, just do it." Lauren said firmly to Beth. "They still have to be fair about how they treat us. If one person is allowed to not wear undies, then that should apply for everyone. I'll join you even, there will be three of us then."

Beth look a bit taken aback by the support, but gave a small nod. "I kinda... like the idea." She admittedly sheepishly.

"What about you, Alicia?" Sherry asked slyly, look at me with a grin. I stilled, suddenly feeling put on the spot as the three girls looked at me expectantly.

Could I seriously go without underwear? That was... I mean it was one thing for the cis girls, but for a trans girl... but then, Sherry was already doing exactly that, wasn't she? If I did do it, I wouldn't be alone.

"I want to," I admittedly, looking down. "but there is no way people wouldn't get... peeks, given what I have down there. This school is nice, but I still don't want to outstay my welcome if people start actually noticing I'm trans down there. Won't people judge me for it?"

"Nobody will judge you." Lauren insisted fiercely. "And especially not for being trans. If they do just tell me, I'll kick their ass."

I felt surprised at her vehemence. I've known Lauren for a few months now. She was tall, athletic, and passionate about what she believed in. She and Beth had apparently been best friends for a long time. But I had never realised she was so... protective, though. Not towards me, at least. It felt nice. An unexpected closeness I hadn't realised could be available to me.

"Alright. I'll do it too then." I agreed, blushing.

"Then all three of you are joining me?" Sherry said, her eyes sparkling. Beth gave a firm nod.

"Good. To be honest, it's actually super relieving, it's quite intimidating to be the only girl not wearing any." Sherry said sheepishly.

"So why'd you announce it to the whole class then?" I laughed.

"Well, if you're scared then you should face your fears!" Sherry insisted brightly. "I'd rather say it upfront than constantly be worried someone was going to find out. Because they definitely would, eventually."

That... actually really resonated with me. It was the same reason I had decided to be out and proud in this new school. I felt a bit seen, actually.

I spontaneously leaned over and gave Sherry a hug. She squeaked, not expecting it, but hugged me back. When I pulled away, she had turned bright red, looking embarrassed.

"Oh my god she's so adorable when hugged." Beth said in awe, staring at Sherry with stars in her eyes. Sherry blinked, and then was immediately glomped into another cuddle by Beth, who sat in her lap contentedly.

Sherry looked so happy yet embarrassed, like she didn't know how to handle the idea of being hugged. Beth was right, it was absolutely adorable, and I couldn't help giggling at her predicament.

"Do you think any of the other girls would be interested in joining us?" Lauren asked thoughtfully.

"I can convince them." Beth said, shifting so that she could face the rest of us while still comfortable in Sherry's lap.

"U-Umm, Beth you're sitting on my-" I heard Sherry whisper quietly, her face bright red.

"It's fine." Beth whispered back, interrupting her.

"No but. M-My skirt's bunched up, it's directly touch-"

"It's fine." Beth insisted again. Her cheeks were also a little rosy.

Sherry didn't bother trying a third time, just wrapping her arms around Beth and settling down with a heavy blush.

Lauren was looking at them amused. "So when should we start our little commando club?"

"Maybe tom-" Beth started, but I got there quicker.

"No time like the present." I said softly, staring at Beth and Sherry. My tummy felt hot. Not quite... horny. Not like I'd expect, but more... like my whole body was on edge and waiting for something.

Jealousy? No, that wasn't right. More like... I felt like I wanted this to happen. Right here, in the dining room, while nobody was paying attention. I wanted to up the stakes.

Beth went bright red and quiet. "Umm. Well-"

"I'll start." I said with a smile. I looked around me to see if anyone was watching, before sneakily reaching up and pulling my panties down.

It was only after I'd bundled them up and sat back up that the fear hit me. It was like a shock, some part of my brain waking and recognising what I'd just done. I'd been focused on making Beth do it, but now suddenly I realised I was pantiless in the middle of the dining room and it was... god, I could feel every nerve ending.

A stray breeze could expose me to the world, I realised. My skirt wasn't short, but it wasn't long either, if I didn't pay attention to keep it covering me properly...

My face felt warm. Lauren and Beth were both staring at me. "Your turn." I said softly, trying to ignore the overwhelm that threatened to take me over.

Lauren was the next to follow suit, slower. Her skirt was pretty long, so she didn't seem as uncomfortable as I felt. "Now you Beth."

Beth looked between the two of us, her cheeks dusted pink. Finally she nodded slowly. "Cover me please." She mumbled.

Me and Lauren both obediently scooted our chairs to either side, so that Beth and Sherry were not immediately visible.

Beth took a moment to gather her courage, before lifting her hips and pulling down her panties. Beth's skirt was longer than Sherry's, long enough to cover them both just about, but Sherry's bare crotch become totally exposed during this little maneuver. Her skirt was all bunched up and exposing her to the world, her dick hard and pointing up at Beth. She must have been pressed directly into Beth's crotch, I realised.

And as much as Sherry played confident, I could see that this was really pushing her limit. She looked deeply embarrassed to be exposed to me and Lauren like that, red to her ears, and having no idea how to handle it.

When Beth sat back down quickly, her breath hitched in time with Sherry's. Beth's face turned red as well. Beth didn't blush quite like Sherry did, but it was obvious that something had happened.

"What?" Lauren asked, her legs pressed together tightly.

"N-Nothing." Beth tried to play off, giving a shaky laugh.

Lauren was having none of that and, giving another little look around, quickly pulled up Beth's skirt before Beth could stop her.

There both of us could see clearly, that the length of Sherry's cock was pressed right up against Beth's crotch, wet from her juices. The tip was pushing up into where I expected her clit to be.

They were about an inch away from penetrating fully. I swallowed, wondering if I felt relieved or disappointed.

"It's fine. Not a big deal." Beth said breathily, covering herself back up.

Sherry had gone silent again, not a word coming out of her. I patted her arm sympathetically, and her hand reached out to grab mine, entwining our fingers. My heart felt warm, some part of me really glad that she had reached out.

It was stupid, we had only met today, but I still felt like what had happened earlier meant something to me. It was complicated. I felt a bit guilty at having pushed her into this situation, but from what I could tell Sherry seemed to be doing okay.

"Let us know if it's too much, okay?" I murmured, and Sherry silently nodded in agreement. Beth suddenly looked guilty, like she had forgotten the girl under her was also experiencing this. But when she tried to move, Sherry's arm held her in place, not willing to let her leave. Beth bit her lip, but settled back comfortably.

We quietly started chatting about other stuff, keeping the fragile tension between us going. Until I noticed something.

It was subtle, but I could see Beth gently tilting her hips forwards and backwards. Rubbing the two of them together, I realised. Not enough to do much, probably, but enough to feel nice.

"This is so crazy." Lauren whispered faintly. She'd seen what they were doing too.

Beth looked a bit embarrassed to be caught, but kept going, and I could hear her and Sherry's breathing begin to get heavier.

"Class is going to be so uncomfortable this afternoon. I'm gonna leave the seat wet" Lauren muttered, squirming. Her legs were squeezing together rhythmically, matching Beth's timing.

I stilled. Shit, if lunch ended then me and Sherry would both be in trouble. We couldn't go to class with erections after all, especially without panties to contain it.

"I need to take Sherry to the bathroom." I murmured.

Beth and Lauren looked at me curiously. "We need to finish ourselves before class starts." I clarified with a blush. Understanding dawned on their faced.

"We'll help you. This is kinda my fault." Beth said sheepishly.

I was a bit reluctant to let them, since I wanted to suck Sherry off again, but I couldn't think of a good reason to say no. Plus, they'd be helpful for getting us there without our tented skirts getting spotted.

Beth and Lauren both took their duty seriously, making sure we were both protected. Sherry held my hand tightly as we walked there.

When we got to the girl's bathroom, Lauren smartly locked the door behind us. Something I probably should have thought of earlier, I realised sheepishly.

"Well. I-I guess you two should go do your thing." Beth said awkwardly, trying to be casual and lighthearted about it.

I stared at them both contemplatively, considering whether I wanted to take a leap. Finally, I made a decision, and knelt down in front of Sherry, putting my hand on her thigh. I could hear Sherry's breathing increase rapidly, shocked that this was happening in front of the other two girls.

I looked up at her questioningly, not wanting to unintentionally push her over the invisible line, and I couldn't help but feel relieved when she gave a tiny nod of permission. Sherry seemed to go non-verbal when overwhelmed, so I had to remember to double-check to make sure she was still feeling good about it.

I gently lifted Sherry's skirt to reveal her cock.

"Ohmygodohmygod..." Beth muttered, looking absolutely shocked at what I was doing. I could scarcely believe what I was about to do myself.

Beth and Lauren got close, kneeling next to us to watch. I could see them holding hands, fingers entwined. It suddenly occurred to me to wonder if they were a couple. I'd never noticed, but then I hadn't been that close to them before today. Maybe they were just private about it.

I started sucking on Sherry. I could taste Beth's juices on her cock, covering it in a sticky dew. I couldn't help the flush of arousal at the taste.

"C-Can I join in?" Beth blurted out. I stopped, feeling a bit taken aback. I hadn't expected them to want to join. But in retrospect maybe I should have. Beth had obviously been into it earlier.

I looked up at Sherry, who gave another little nod. "Sure. Have you done this before?"

"Never with a dick." Beth mumbled shyly, scootching forwards next to me. I held Sherry's cock out to her, and Beth tentatively wrapped her lips around it.

"Be careful not to touch it with your teeth. Firm but gentle." I instructed gently, as Beth gave her first blowjob. She was still holding hands with Lauren behind her.

"The head is the most sensitive bit. I imagine it's a bit like the clit." I added, and Beth quickly adapted that into her movements, focusing on pleasuring that part the most.

Beth quick got into the rhythm of the blowjob, and I could tell Sherry was feeling good. Beth was a fast learner.

Lauren got up and quietly whispered something to Sherry, before moving behind the girl. Lauren's hands reached under her shirt, playing with Sherry's small breasts. I could hear Sherry giving out small, cute whimpers. Her eyes were closed, and she leaned back against Lauren for support.

Deciding I wanted to join in, I began running my tongue up and down Sherry's shaft, kissing and gently suckling on her testicles. It was both awkward and deeply erotic to share a blowjob with Beth like this, and I reached out to hold Beth's hand. She squeezed it fondly, though neither of us let up from pleasuring Sherry for a second.

Finally, I felt Sherry begin to twitch. "She's close." I told Beth.

Beth nodded, and became even more determined. But she couldn't help the shock as Sherry exploded cum into her mouth.

"Hold it, don't swallow." I said softly. "Just let her fill your mouth."

Beth's mouth steadily filled with cum. I was honestly surprised at how much Sherry still had to give, given that she already cum once today.

Once Sherry was done, she felt back exhausted into Lauren, who hugged her sweetly.

Beth's mouth was full, as she carefully let Sherry's cock slip from it.

"Would you be okay sharing it with me?" I asked gently. Beth nodded jerkily her eyes wide, and I leant in to kiss her.

Beth's kiss was different from Sherry. A bit less submissive, a bit more playful perhaps. She was also, and I cannot overstate this enough, very good at kissing. I couldn't help but moan quietly, as we shared the cum between us, letting it swap between our mouths.

When we finally broke apart I could feel my face bright red, and Beth's eyes were absolutely smouldering as she looked into my soul.

We both swallowed our respective shares of the cum, and Beth closed her eyes as she savoured it.

"I've never tasted cum before. It tastes nicer than I expected." She said softly, and I could hear a hint of just how excited she was. "Saltier, too."

"Thanks for indulging me." I mumbled, suddenly feeling quite vulnerable. I looked down, embarrassed. I hadn't expected to be sharing my little fetish with others like this.

"I'll enjoy tasting yours too." Beth said with a smirk. My eyes darted up at her, shocked. It hadn't occurred to me that she'd want to suck me as well.

Beth pushed me back gently, and when I fell back I realised Sherry had made her way behind me, supporting my head in her lap. She leant down and gave me a kiss, a shy smile on her face.

When I looked back down, Lauren was kneeling with Beth. My pantiless crotch was exposed to them both, my cock pointing up.

"Never done this before." Lauren admitted sheepishly. "I've only ever been with Beth."

"Never done anything at all before break today." I admitted shyly. "Sherry was my first."

Lauren and Beth both looked at me, then at each other. I saw some silent communication pass between them.

"Tomorrow evening, do you two want to come over to my house?" Beth finally said. "We'd enjoy... playing more, with you both. If you like."

"Sounds fun." I said weakly, my breathe hitching as Lauren's hand stroked me gently on the thigh.

"It's a date then." Beth smiled, kissing the tip of my penis. Her and Lauren began pleasuring it from each side, their lips meeting in a sort of lewd kiss. Beth kept making sure they focused on the head, which was bringing me no end of pleasure.

It was kinda surreal, having these two giving me a blowjob. I knew them, I'd even had the occasional fantasy about them, but I'd never expected it to actually happen. They had both felt out of my league.

Beth was funny, cute, always well-dressed. Lauren was tall, athletic, hot. And above all, they were both just genuinely nice to be around. Despite being the only black kid in class, Lauren had solid friends and was well-liked, never letting the potential barrier get in the way. I'd honestly looked up to her, wondering how she'd succeeded to overcome that hurdle where I had failed.

Somehow, the surrealness only added to the pleasure when Lauren took charge of giving me the blowjob proper, sucking on me.

The girl I admired was sucking on me, and I just did not know how to process that.

Beth kept herself busy, shifting between kissing Lauren's cheek, the shaft of my penis, and playing with my testicles. It was a weird experience, having someone lick and suck my balls. It was... pleasant, but also made me feel a weird combination of safe and vulnerable. It was difficult to describe.

Between the two of them, they soon had me on the edge. I wasn't able to help it when my body started shaking, the orgasm running through me. It was Lauren that ended up catching it in the end, waiting patiently as her mouth filled with my cum.

Once she pulled away, Beth first took a moment to carefully clean the head of my penis of any remaining cum, sucking gently on me until she was sure she had it all.

And then finally her and Lauren started kissing, sharing my cum. A shudder ran through me, as I saw the two girls carefully and respectfully savour it. Their kiss was slow, gentle, and they were making sure none of of it escaped from their lips.

When they finally pulled back and audibly swallowed, I whimpered. My cum was now inside their tummies. Sherry behind me pulled me closer, hugging me.

"You're right, tastier than people make it out to be." Lauren finally admitted. "I didn't think I'd like it."

"Right!? Both our girls have super tasty cum." Beth bragged, pleased. "Funny how the tastes are distinct too, you could tell who was who by the flavour of their cum."

As hot as that was to consider, the thing that really hit me was Beth referring to us as "their" girls. It sent weird feelings through my tummy. I wanted to ask what she meant by it, but wasn't willing to break the mood.

"Thank you." I mumbled, a feeling of vulnerability coming over me. It had been really nice of them to do that for me, I hadn't been expecting it or anything.

"No problem, sweets. We should get you both to class." Beth said gently, as the three girls all help me stand up. I was surprised how wobbly my legs were.

Beth and Lauren both look surprised when I suddenly pulled them both into a hug. "I don't know why I didn't take the time to get to know you both sooner, you're really lovely." I mumbled with tears in my eyes.

"That's okay, we have plenty of time."Beth said sweetly, cuddling into me.

When I pulled away, I immediately turned around and glomped Sherry, who had been looking a little left out. "Really glad I met you, Sherry." I said, kissing her on the corner of her mouth.

Sherry turned red, but nodded, burying her face into the crook of my shoulder. I gave her a couple of minutes to recover from the emotional overwhelm.

Finally, we all headed to class.