Secrets and Surrender

Ben showed up for a while, staying at the far end of the table and not settling in overly long before heading off again. We didn't really talk at all while he was there, and Kylie studiously ignored him, but it was something. Awkward, but at least not overtly hostile or aggressive on anyone's part.

I could sense Kylie getting kind of restless next to me, and I couldn't blame her. Neither of us had been expecting company. Holding her hand under the table seemed to help some.

Toward the end of lunch, Kylie excused herself to hit the bathroom. I nodded and watched her slip away, then turned back to find Andrea giving me a concerned look from across the table.

"Kinda freaked her out, didn't we?" Andrea said.

"I think so, yeah," I said.

"Sorry. That wasn't the intent."

"No, I know. But, uh, what was the intent?"

Andrea shrugged. "I don't know. I can't speak for everyone, but a few of us have been missing you. You won't hardly sit with us anymore."

"Yeah, I've, uh--"

"Been busy. I get it."

"That and I honestly didn't think anyone was gonna care."

Andrea tilted her head and raised an eyebrow.

I winced. "Sorry, that kinda sounded harsh."

"Just a little."

"I might have issues."

"Don't we all?" Andrea murmured thoughtfully. She nodded in the direction Kylie had left. "Better go catch up. She clearly just wanted an excuse to leave."

"Yeah, uh... yeah. I should."

"You two can both hang anytime," Andrea said as I pushed to my feet. "Don't be a stranger."

"I'll keep that in mind." I forced a smile. "Thanks."

"Seriously. Go."

"Right."

I didn't know exactly where Kylie had gone, but I got kind of lucky and stumbled on her just coming out of the nearest bathroom. I took her hand and kept walking with her in a gesture smooth enough to even surprise me at the execution of it.

"Goddamn I need a smoke," Kylie muttered. "Fucking rain."

"Fucking rain," I echoed. "Sorry about the ambush."

"No. It's fine. It was kinda nice of them. I think. It's just me being a mess."

"A sexy mess?"

"Stop that."

"Sorry."

"They were mostly there for you anyway. 'Cause I stole you away and all."

I snorted. "Yeah, right. That's what happened. Still, it actually was kinda nice that anyone cared."

"You've been hanging with them all year. Bound to make an impact."

I sighed. "Maybe. I guess. It's all so confusing sometimes."

"Isn't it just."

We happened upon a secluded stretch of hallway, no one immediately in sight. Kylie pulled me in, trapping herself against the wall with my body, and wrapped her arms around my neck for a kiss. Our lips lingered in their comforting embrace.

"Woulda been so much easier if we both coulda finished the year with no one giving a shit, huh?" Kylie whispered.

"Easier, sure. Not better though."

"No. Not better." Kylie pulled back, an enigmatic smile teasing her lips. "Got some fun news, though. Was saving it for later, but..."

"What is it?"

"Well... my parents are kinda, like, out of town this weekend."

It took me a second to process the implication, but the mischievous look Kylie was giving me left no doubt as to the correctness of my final assumption.

"Are they really?" I asked while sliding a hand down to Kylie's butt.

"They are."

"That must be... lonely for you."

"Very."

"I'll have to come keep you company."

"Yes," Kylie said decisively while wiggling her ass beneath my sneaky groping. "Yes you will."

****

I got embarrassingly nervous and excited as the weekend approached. Some proper alone time with Kylie. Something we hadn't had basically ever. Not for real.

Along with the possibility of true privacy came my imagination running wild and thinking of what we could do with such power. My thoughts were almost universally dirty, of course, but there were a few more platonic ideas in there occasionally. Even if we didn't really get any sexier than we usually did, it'd be nice just to chill by ourselves for a while.

I sensed disaster just before leaving for Kylie's house that Saturday. I'd tried not to give anything away, nothing about how we'd be left unsupervised for an indeterminate amount of time, but I worried I must have failed somehow when I walked downstairs and ran into my parents before I could make it out the door.

Mom had a frown of concern on her face. Dad just looked super duper uncomfortable.

"Are you about to tell me I can't have a car for the weekend?" I hazarded, trying my best not to let my excited optimism falter. "You said I could."

Mom and Dad exchanged glances. My heart sunk further at the lack of immediate response. I had other options even if I couldn't have one of their cars for sneakily driving myself over to see Kylie, but it was unlikely that such a scenario happened in a vacuum of no other consequences.

"You're going to see... Kylie?" Mom asked hesitantly.

I sighed. "Yeah. That was the plan."

Mom looked at Dad again, but he shook his head. "Don't look at me," he said. "This is your conversation."

"What is?" I asked, even as I dreaded whatever answer might follow.

Mom took a moment to steel herself. "Carter, sweetie, I've, uh, learned something about Kylie. From a friend. Something I think you should know."

A moment of confusion and continued anxiety flashed through me, then a sudden calm. I almost felt amused, except that my tummy was still kind of fluttery and nauseous.

"She's trans," I said calmly.

"She used to be..." Mom stopped, only belatedly processing what I'd said.

"I know," I said. "You thought I didn't?"

"Well... you never said anything."

"Why would I?" I shrugged. "Wasn't relevant."

"But... but... she's... you..."

"Use your words, Mom."

She hesitated, folding her arms in a gesture nearly as uncomfortable as Dad still looked. "If you're happy--"

"I am. Thanks for worrying. I guess." I nodded toward the door. "Can I go?"

Mom didn't answer. I looked toward Dad. He clenched his jaw, then took a deep breath and relaxed it.

"She seems like a nice girl," he said.

"She is," I agreed.

"Keys are on the hook where they always are."

I smiled, small and cautious, but genuine. "Thanks, Dad."

Mom stepped aside for me, clearly not totally happy with the way the conversation had gone, but I wasn't sure there even was a good way for it to have happened.

"Don't stay out too late," Mom said softly as I passed.

"Oh, I almost certainly will," I replied cheerfully. "See you tomorrow!"

"That's not funny."

"Wasn't a joke."

I grabbed the keys to Dad's car and scooted out the door before I could be called back to account for my glib exit.

****

Kylie met me at the front door to her place. I was momentarily taken aback by her outfit, though very appreciative of it at the same time.

"Ooh, a skirt, huh? Don't see you in one of those very often. Or ever."

Kylie smiled shyly and did a small spin back and forth. "I'm not usually brave enough. Does it look ok?"

"Looks great to me. But why don't you take it off so I have something to compare it to."

She put her hands on her hips and cocked her head while giving me A Look. "You goof. That's about the worst seducing you've ever tried."

"Yes, but imagine if it had worked."

"No thanks."

Kylie beckoned me inside and started showing me around. It was a somewhat wasted effort because I was still mostly watching her. Her skirt wasn't indecent by any means, but it was new on her, and somehow the way she moved in it attracted my gaze quite effectively.

Her legs were bare beneath the skirt, excepting a pair of cute socks on her feet. Her top, while again not indecent, was tighter and less covering than I was used to on her, showing off more of her arms, shoulder, and neckline. I couldn't be sure about her choker, but it seemed like it might be new too.

It wasn't clear whether it was an outfit donned for my viewing pleasure, or whether Kylie was just trying something new while there wasn't going to be anyone else around. Maybe both, I supposed.

Once Kylie realized I wasn't paying any attention to the tour, she gave it up and led me to the living room. She sat me on the couch, then turned the tv on and got a show playing. I continued to mostly watch her. That skirt was oddly captivating, every twitch of it sparking interest in what lay beneath.

She sat down next to me, slipping under my arm for some close snuggles. It took us both less than five minutes for the show she'd put on to be made irrelevant background noise.

We feel easily into our practiced routine of making out and feeling each other up. It was exciting and liberating both to be somewhere new to me, fearing that we'd be caught, but knowing that actually had the space entirely to ourselves. I loved it.

The new thing for me was getting to slip my hand up Kylie's skirt. She'd never given me a chance to get into her pants before, but this time I technically didn't have to.

Grabbing her butt through her panties was a whole different game to feeling it through her jeans. So much less in the way, such a warmer, closer, softer feel under my palm.

Kylie seemed totally fine with me getting just as obsessed as I wanted with my newfound access. She still didn't want me straying too far front, though. Not that I would have expected otherwise.

"You've kinda got a thing for my ass, huh?" Kylie breathed in between kisses.

"I'm fond of it, yes."

"Mmhm. Fond. Right."

"I might... like it."

"Just like?"

"... love? I love your ass?"

"You don't sound sure."

"Well... I can't really be sure. This is the first time I've gotten to your panties, and I still haven't been under them."

Kylie kissed me again, softly biting my lip and tugging at it before releasing. "You want more?"

"Basically always."

Kylie repositioned herself and sat down firmly in my lap. I groaned as her body weight settled partly atop my cock. I could feel hers pressing against me too, but decided not to mention it.

"How's that?" she asked.

"Better." I got both hands under her skirt, grabbing and massaging her ass from both sides. "Definitely better."

"Good."

As I kept fondling Kylie, she started rocking back and forth, grinding in my lap. I moaned into her mouth as she found just the right spot to rub against me, and I used my grip on her bum to guide her back when she strayed from it.

I managed to pull Kylie's panties down past her butt, exposing her bare cheeks to my continued explorations. I squeezed and caressed her ass to my heart's content, getting us both hornier and hornier in the process. Once I felt brave enough, I dipped a finger between her ass cheeks and felt out her butthole, pressing softly and drawing little circles around it. That more so than any fondling seemed to excite Kylie and get her all wiggly the way I loved.

"Bad boy," she chided softly.

"That's me."

"That's my bumhole."

"Sure is."

"You're not supposed to touch me there."

I grinned. "You don't seem to mind."

Kylie bit her lip. "Maybe I don't."

"I think you want me to touch you there."

"Maybe I do." Kylie looked away for a moment while continuing to squirm as I anally teased her with my finger. "Maybe I want more, too."

My eyebrows went up. "More?"

She nodded. "More."

"Like..."

"We're all alone, you know," Kylie said quietly. "We could try it."

"And by 'it' you mean..."

"You know what I mean."

"I think I do. I hope I do." My pulse was pounding hard and excited. "But I don't want to guess wrong."

Kylie put her hand on my cheek, brushing her thumb across it. "It'd be my first time," she said. "And... and I think I really want it. Today. With you."

I kissed her thumb as it passed my lips. "Me too," I said breathlessly. "To all of that."

She smiled, slow and shy at first, then blossoming quickly into something full and beautiful. She kissed me fiercely, but without lingering. "You ready now?"

"Hell yeah I am."

Kylie bounced off my lap and took my hand as soon as I stood up after her. She led me away at an impatient clip, her skirt falling back to cover her butt after an all-too-brief flash of her backside with panties pulled partway down.

Her skirt was discarded almost immediately upon reaching her bedroom. She watched eagerly as my pants followed a similar path.

I wanted to take a moment and survey the scene, but she was more compelling than anything else in the room. Especially with her skirt pooling down her legs to the floor, and her panties still not adjusted. She caught me staring back at her the same way she was looking at me, and quickly spun around to display her ass instead of her barely covered erection.

"You've got such a nice butt," I said.

"Thanks."

"It gives me... ideas."

Kylie giggled and slowly crawled onto her bed, exaggerating every movement. "Good."

Her panties bulged at the front. Her wanton pose--head lowered, butt sticking out toward me--didn't hide much. I was pretty sure there was even some precum leaking through.

Luckily, her ass was still the most enticing thing in the room. It just simply wouldn't do to ruin the moment by focusing on the wrong area. She wiggled her bottom at me, drawing me in closer and closer until I was right on top of her.

I reached for Kylie's panties and gave them a small adjustment, tugging them down just a little more to better frame her bum.

"Leave them," she said.

"I know. I'm not taking them off. Yet."

"Ever!"

"We'll see." I discarded my shirt, then gently swatted Kylie's butt. "Make some room."

Kylie shifted and positioned herself so I could get on the bed behind her. I grabbed her ass, kneading and spreading it much as I had before, only this time it was right in front of me and I could see what I was doing. Her cute little butthole actually twitched in nervous and excited anticipation. It was oddly hypnotizing just to watch it react to my caresses.

I bent down and kissed Kylie's butt cheek. I had to hold her more firmly as she got all squirmy. It still wasn't enough when I swiped my tongue across her butthole and she moaned and wiggled even harder.

"Hold still," I said gently.

"I'm trying."

"I really don't think you are."

Kylie bit her lip and looked at me over her shoulder. Her hips settled down. "It's hard."

"I bet."

I licked Kylie some more, getting comfortable with tonguing her bum. Never having eaten anyone's ass before, I hadn't been totally sure I'd like it, but I really, really did. It tasted nice, and I loved the way she overreacted to every little thing. There was something delightfully fun and naughty about the whole thing, not to mention the promise of more yet to come.

"There's lube under the pillow," Kylie said softly.

I frowned. "Under your pillow? That's where you keep it?"

"No. I keep it with my toys. I just... wanted it to be handy."

"Planning on seducing me this whole time, huh?"

"Kinda, yeah."

"Well... I'm ok with that."

"Thought you might be."

There was, indeed, a half-full bottle of lube under Kylie's pillow. I hadn't given it much thought before, that she might have played with her butt quite a bit, but it took some of the pressure off anyway. I was pretty sure it'd be ok, but I wasn't overly familiar with butt play, outside of porn. Kylie already having experience was reassuring.

And indeed, she very easily took a lubed finger. I was more hesitant about pushing it in than she was. It was tighter around my second finger, but again she took it nicely, and moaned as I delicately pushed my twinned fingers deeper inside her tight little bum.

"You're taking these pretty easy," I said.

"Is that bad?"

"Not at all. I like it."

"I've kinda played with myself a bunch."

"Mmhm."

"But it woulda been nice if it was you all those times."

"Well it's gonna be now." I kissed just above where my fingers slowly thrust in and out. "You're definitely ready for me."

"Hope so. I wanna be a good girl for you."

A thrill ran up my spine. "Kylie..."

"Well I do. I want you inside me. And... and I want to be able to take you. I want it to be a good first time."

"Understandable." I pulled my fingers back, marveling at the feel of them sliding free from Kylie's lube-slicked hole. "It'll be my first too, you know."

Kylie grinned shyly over her shoulder at me. "Nervous?"

"A little."

"Good. Not just me then."

"No. Definitely not."

"It'll be good," she assured me. She turned her head forward, arched her back, and wiggled her butt. The gesture was purely for seductive reasons this time. "I'll be a good girl for you."

"Hard to say no to that," I said, eyes locked on her cute butthole as it swayed back and forth.

"I should hope so."

I lubed my cock without taking my eyes off Kylie. Her wiggling hips became impatient instead of seductive, even in that brief period of waiting for me. She settled immediately as soon as I pressed my cock to her asshole.

"Ready?" I asked, probably unnecessarily.

Kylie flashed me the biggest, most pleading eyes I'd ever seen on her. "Please?"

"Goddamn," I whispered.

My cock didn't want to go in quite as easily as my fingers. Not at first. Once I pushed just right and popped past Kylie's outer ring, it went much easier.

"Yesss," Kylie hissed happily.

She was so tight around me, even just the first little bit of my cock as it entered her. Somehow, though, she wasn't so tight that I felt I had to stop, or that I might hurt her. She opened up just enough for me to keep working forward, to go deeper inside her bum.

"That's ok?" I asked.

"So good."

"Doesn't hurt?"

"Just a little. But that'll go away. I've done way worse when I was learning."

I stopped moving. "Do you want to wait a moment? I can--"

"Keep going!"

"I--"

"Please!"

I snorted and shook my head, then gave another thrust into Kylie's ass. She wanted more. So did I. It was a heavenly embrace around my hard cock, and it only got fuller and more all-encompassing the deeper I got.

Kylie took everything, right down to my balls. She cooed and moaned as she was filled up as much as I could give her.

"Mmm, yesss." Kylie gave me a heavy-lidded look of sexual contentment before burying her face in her sheets. She rocked her hips, bouncing slightly back and forth on my cock. "Make me your slutty girl."

"Isn't that who you already are?"

"Make me!" she insisted.

I smiled and squeezed Kylie's ass. She squeezed my cock with her inner muscles in return.

I knew what she meant. What she wanted. I was getting to understand her thinking about some of these things. Sex as a rite of passage wasn't exactly a new concept, even if it was generally questionable. If that was what Kylie felt she needed... well, that's what she was going to get anyway. And admittedly, there was a part of me that really got into the idea of claiming her ass and 'making her my slutty girl,' as she put it.

It wasn't easy or smooth to fuck her at first, since her ass didn't really want to let me go, but once I started thrusting and getting a rhythm going, her body cooperated better.

Kylie gripped her sheets and alternated arching her neck and keeping her face down. She didn't help much when I was pulling out, but she pushed back and gave my thrusts an extra oomph every time I buried myself back inside her. I tried slowing and down and making her fuck herself on me a bit, but she started whining and wiggling, and really couldn't do everything from her position anyway.

Her ass relaxed more as it got used to me, making my strokes nice and smooth after a while. I was able to fuck her in longer, harder thrusts, which she continued to encourage and assist.

"Fuck me good," Kylie moaned softly.

"I am."

"Make me your girl."

"You already are."

"I know. But make me."

I slapped Kylie's ass, assuming she'd like it. She did. I spanked her some more, whenever I felt like it, or whenever I felt she wanted it.