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Chapter 14: A Beginner’s Guide to Round Two

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  Without further adieu, here's this week's chapter. Be warned, however, we about to get very NSFW!

  Rose

  I basked in the glow of Kyle’s warmth and strength, him holding me tight on his bedroom floor, the hot, salty fvor of his cum still fresh on my tongue.

  “So, I’m gonna need a breather before we can go for round two,” he said. “That okay, princess?”

  “Perfectly reasonable,” I said with a contented sigh.

  “I’m guessing you’re too full for a snack break?” he said.

  “At the moment, yes,” I ughed. “Maybe after the aforementioned second round I’ll have, uh, worked up an appetite again.”

  He kissed my temple, a gentle flicker of his burning passion that sparked through my skin. “Fingers crossed. What should we do in the meantime?” he asked.

  “You tell me,” I grinned at him, flicking his nose lightly.

  “God, you are such a fucking gremlin.”

  “Oh please, you love me,” I said. Then, immediately, I went quiet. And so did he. So did everything: it was like the sound had been drained from the building entirely. We sat there, the silence stranguting any hint of afterglow from either of us. The only reassurance was the sensation of his heart beating through his chest. One of us had to say something. Fuck, I was gonna have to say something-

  “I mean… I might,” Kyle finally spoke. His words were barely above a whisper, but I don’t think I’ve ever heard anything more clearly.

  I pulled myself out of his arms, turned around to face him, and took his hands in mine. “You… You don’t mean that.”

  “No, I… I think I do,” Kyle said sheepishly. “I’m not completely sure yet, but I might be… I might be falling in love with you, Briar Rose.”

  “Kyle, I… I don’t know what to say-”

  “You don’t have to say anything- I’m not even sure I’m saying anything, I’m just being honest with how I feel and I-”

  “I’m not real, Kyle,” I said softly. “You can’t fall in love with someone who isn’t real. All of this… Rose… She’s not a real-”

  “Oh come on, seriously?” Kyle groaned, standing up and letting go of me. It was like I’d just had an organ ripped out through my skin.

  “Look, I just… I want to be your girlfriend, but that’s kinda hard when I’m not really-”

  “You are a girl, Rose,” Kyle said, stomping out of the room and into the kitchen. “You are. You’re just trans-”

  “I’m not,” I said, following after him. “I want to be, but I’m not-”

  “Bullshit. That’s what a trans girl who’s in deep denial says,” Kyle said. “You want to be trans? You want to be a girl? You want to be my girl? Then just be that. Just be her.”

  “It’s not that simple.”

  “Why the hell not?”

  “Because I made a promise! I have to… I have to be my father’s son. Someone has to continue my family.”

  “Then continue it with me,” he said.

  “W-what?” I said.

  “Just saying,” Kyle said, reaching into the cupboard and pulling out a handle of whiskey. “There’s other ways to do that. You can even make it so the kids have your st name if it’s what you really want.”

  “A-are you saying you wanna have kids with me?” I asked, incredulous.

  “Yes!” he said, and then cringed. He swigged a gulp of whiskey while I stared at him. “No! Maybe! Sorry, I’m sure I’m all over the pce right now, I just… God, you’re so frustrating sometimes!”

  “Gee, thanks,” I said, leaning against the counter and standing next to him, arms folded over my breasts.

  “Look, Briar- you’re giving me the runaround. You say you’re not a girl, that you’re not trans, but nothing about anything you’ve done the past four months has exactly screamed ‘cis guy.’ You have boobs, for God’s sake. And you responded to my inquiries with ‘you tell me’- I shouldn’t have to tell you, but if you’re making me, I will.”

  I snatched the bottle from his hands and then downed a gulp, savoring the sweet and smokey burn as dread and joy ignited like rival fires within me. “Then tell me.”

  “Rose,” he stared at me ftly, “You’re a woman. And I want you to be my woman. You’re driving me crazy, always dancing around me, trying to make me happy. But you need to stop acting like this isn’t making you happy. I need you to admit it. Please. Just for one moment, drop the game. Forget about the game. Just be honest. About who you are and what you want. Because you say you wanna make me happy: what will make me happy is if you’re honest about wanting this. Because yeah, I might be falling in love with you, and the ‘might’ is pretty much only a corolry because you keep trying to py it coy. So please. Just… Let me. And be honest.”

  I tried to take another gulp of whiskey, but he stole the bottle back and stared at me. Fuck, he was… He was serious. Oh God, I was deep into uncharted waters now. This warm feeling filled up my chest and my stomach, the fire of joy having won out over dread, a gentle fme that wanted to expand to my entirety. He wanted me. He wanted to love me. He wanted to be with me. He wanted me to be his woman.

  Did I want to be his woman? A part of me reflexively wanted to answer that with ‘I’m not really woman’, but the only reason I kept saying that was because… Was because of the promise I’d made to my father… Except I really hadn’t made it to my father, I’d made it to my mother. My very much alive mother who barely even acknowledged the existence of the son she forced me to be. The promise I’d made to my father was to be happy. And I was happy when…

  I was happy when I was with Kyle. And I was happiest when I was with him as…

  As…

  “I’m Rose,” I said before I could stop myself. “I’m a woman. I’m a trans woman. I’m Briar Rose O’Neil and I’m a woman!”

  The warmth overtook my entire body, thawing out parts of me I hadn’t even realized were frozen. All of the sudden, everything was… MORE. The feeling of my skin around my bones, my heart thundering inside my chest, the blood flowing through me, the sounds of the city’s nocturnal vibrations outside, the handsome hunk of a man standing next to me-

  MY handsome hunk of a man standing next to me, smiling at me like he was the happiest person on the fucking pnet. And all the warmth, all the light and joy inside me, just sang out when I was looking at him. “Kyle,” I said. And because it was him smiling at me, I couldn’t help but smile back.

  “Yes, Rose?” he said, setting the whiskey on the counter.

  “I’m trans.”

  He ughed. “Yeah, girl, I got that.”

  “And I wanna be your girlfriend. Not your pretend girlfriend, not just as part of our game- the game is fun, don’t get me wrong, I love pying it with you, but… I want more. I want it all. I wanna be your girlfriend. Do… Do you wanna be my boyfriend?”

  He cupped my chin and raised my head up towards him, towering over me in all his naked, adonis-like glory. “I very much want to be your boyfriend.”

  “That’s good,” I said, the fires of truth burning inside my soul and shining light over the whole damn apartment, and over every single memory tumbling about inside the byrinth. Suddenly the path forward seemed so simple, the treacherous, shifting hallways navigable. “Because I might be falling in love with you, too. In fact… I might already be there. I think I’ve been there for a really long time, but I didn’t realize it because… Well, because I’m an idiot.”

  He ran a hand through my hair. God, I wished it was longer. Wished it cascaded down my back and framed my face the same way my wig did. But I would get there- I could do that. I was allowed to do that. Having long hair would make me happy, the same way it had made my father happy, the same father I’d sworn to that I would be happy. I stood on my tip toes and kissed him, the whiskey on my breath going with his as I wrapped my tongue around his.

  “You’re not an idiot,” he whispered into my ear. “You’re a chaos gremlin, but yeah, you’re right, I do love that about you.”

  Emboldened by his words and my own revetions, I reached my hand between his legs and found… He was not yet ready for round two.

  “Eh, sorry about that,” Kyle said, his sheepish tone and expression returning. “Gonna need a little more time.”

  “We should probably stop drinking, then,” I said, pushing the bottle away. “I don’t know what else we should do in the meantime, though.”

  “I have an idea, actually,” he said. “Something to keep us occupied.”

  “What?”

  He cupped my cheeks and whispered once more into my ear, “I have weed.”

  “Oh, baby, you say the sweetest things,” I replied, my big, stupid grin returning.

  ***

  We sat on a bnket id over a small patch of our building’s ft roof, looking up at the scant shards of starlight that broke through the miasma of light pollution. Kyle (my boyfriend, my fucking boyfriend, holy shit I had a fucking boyfriend and I was his girlfriend and I just holy fucking shit) sat next to me, grinding flower and packing a bowl into a gss pipe.

  “I really shouldn’t do this too often,” I said. “Don’t wanna risk damaging my voice.”

  “Fair enough. We don’t have to if you don’t-”

  “No, no tonight is a special occasion,” I said. “Should we count today as our anniversary?”

  “Seems appropriate,” he said, sprinkling a bit of kief over the top of the bowl.

  “Cool. April 3rd it is,” I said.

  Kyle (who was my boyfriend, my boyfriend boyfriend boyfriend omigawd) handed me the pipe and lit the bowl once the shaft was securely in my mouth. Heh. I did so love putting shafts in my mouth. I inhaled a puff of the acrid smoke, letting the haze pour through me and cloud over my mind and body. It only added to what I already felt, the endless fields of joy and hope and possibility. Anything was possible. I could be the person I wanted to be, the woman I wanted to be, the one I’d been denying wanting to be for so damn long. And God, what had I been thinking? Trying to deny it so long had just been ridiculous. I was fucking ridiculous.

  But that didn’t matter. I’d arrived, and here I was, arm in arm with the man who’d helped me get there.

  I passed him the piece, and he took a puff of his own, blowing out a mouthful of delicious smoke like a dragon. “So, I gotta ask,” I said. “When did you figure it out?”

  “During our first video call date,” he said immediately, handing me back the piece.

  I breathed in, long and deep. “That obvious, huh?” I exhaled.

  “Yeah. I didn’t recognize you instantly, but from how you were acting, I figured it out pretty fast. At first I just thought you were some trans girl who looked vaguely like my roommate, but then you mentioned the clean apartment thing, and it clicked.”

  “Heh. Yeah, that sounds about right. And you were mad?”

  “At first, yeah, I was furious,” he said. “I remember thinking ‘how stupid does she think I am?’”

  “I don’t think you’re stupid, Kyle.”

  “Really?” he said. There was no malice, nothing accusatory, just pin and simple shock.

  “Yeah,” I said, holding onto the piece, not giving it back to him just yet. “Kyle… You’re probably the smartest person I know, besides maybe Violetta.”

  “That can’t possibly be true-”

  “It is,” I said, putting a hand on his shoulder and furrowing my brow. “You work so damn hard and you know so damn much and you’re always thinking a dozen steps ahead of everyone else. Are you too clever by half sometimes? Yeah, but I’ve no ground to stand on there whatsoever.”

  “I just… I really thought-”

  “Do you think you’re stupid,” I said, handing him back the piece and lighting it for him.

  He took a long, pensive hit, so much so that he coughed a bit before answering. “... Yeah. Yeah, I do.”

  “Well now that’s just silly,” I grinned, shimmying over to him and rubbing his back. “Gonna have to work on that.”

  “Rose, you don’t have to-”

  “Babe, you helped me admit I’m trans, the least I can do is help with your low self-esteem,” I said. I cuddled up to him, nuzzled his neck while he took another hit. “You’re the best man I’ve ever known, Kyle Duggan. And God as my witness, I want you to to feel like the best man you’ve ever known.”

  He handed me the piece, and while I puffed, he said, “That one is gonna be tough. Best man I never knew was my dad. I can’t really compare to him.”

  I breathed out. Oh goodness, was that a nice high. “Hmmm. Well, then I see I’ve my work cut out for me. Challenge accepted.”

  He gave a jovial ugh, and well, you know how I respond to that. “Everything really is a game to you, huh?”

  I kissed him, then said, “Only if you’re down to py.”

  He cupped my cheeks in his hand and pressed his lips to mine, slipping in tongue, feeling up the inside of my mouth. A familiar stirring returned to me. I always felt it when I was around Kyle, at least a little, but this was like dousing the fire with gasoline. I swung my legs around and wrapped them around his back, positioning myself in his arms. He put down the weed and ran his hands up and down my body, over the curve of my hips, across the tight ftness of my stomach, tracing my breasts. Oh, OOOHHHH. Lightning surged through me as he started to tweak my nipples, thumbing them, pinching them; as he caressed my breasts, mashing them together, digging his fingers into the softness of the orbs. How had I ever lived without these?

  As he pulled me further and further into his p, I began to notice something shooting through the soft fabric of his sweatpants. “Why Mr. Duggan, I’d say you’re ready for round two,” I grinned.

  He gave me the Look, and, pressing his forehead against mine, replied, “I do believe I am, princess. I do believe I am.”

  ***

  “You sure I can’t convince you to go bareback on this one, babe?” I said as I undressed once more.

  “Not unless you’re all clean down there, no,” he said with a sad smile. “Trust me, we can do that next time, though. I’m sure you want more of me filling you up-”

  “I really, really do,” I purred as I pulled down his pants and grabbed hold of his cock. God, it was fucking enormous. Just looking at it sent ever more of that primal lust stampeding through my body. “I want you to feel me wrapped around you.”

  “We’ll get there, I promise,” he said, kissing my forehead. He held up the condom. “Would you like to do the honors?”

  I nodded eagerly, then slowly but surely slid the condom over his gigantic rod. Sucking him had been amazing, and now I was gonna feel him inside my backdoor. Oh goodness gracious. I’d dreamt of this moment. I’d repressed so hard that I’d forgotten it, but I was absolutely positive I’d dreamt of this before.

  Once his sword was properly sheathed, I sthered on a generous helping of lube, then gave it a good squeeze and giggled as he shivered and groaned with delight. Seeing him happy made me happy, and I was determined to make him the happiest man in the world.

  He grabbed me by the shoulders and spun me around, arching me over his bed and gently parting my legs from behind with only his ankles. “Ready?” he asked.

  “Yes, darling,” I said, still purring.

  “Then here we go,” he said.

  The tip came first, pressing into the hole in a way that made me squirm. I bit my lower lip as more and more of him slowly entered me, a sensation of tingling pleasure and utter completeness filling the void of my soul. “Mmmmmm,” I moaned as he began pumping, slowly and gently. He was a virtuoso pying a cello, his massive dick the bow along the strings of my inner canal. Gently sliding back and forth, back and forth, each movement resonating through my body and filling me with more and more music.

  “Ohh, this is so much better than using a toy,” I said as he kept on pumping.

  “This isn’t your first time doing this,” Kyle said between groans and grunts of his own.

  “No, I, uh, have a dildo that I’ll sometimes use to masturbate,” I said in an embarrassed whisper. Don’t know why on earth that was anything to feel embarrassed about now that I was spyed out spread-eagle with my boyfriend (my fucking boyfriend holy mother of fuck) nine inches deep inside me, but I guess I really was a nice Christian girl at heart. “And, uh, a few of the girls I’ve been with have, uh, gone the strap-on route with me.”

  “I didn’t even know you’ve been with a woman,” Kyle said, and I could hear the amusement in his words as he kept thrusting and thrusting, slowly gaining speed and power. Oh, God, oh yes, oh YES.

  “Only three of them, all during college,” I said, my eyes rolling back as I started bucking my hips towards him, my hole pushing against Kyle as he pushed into me. I wanted this to be as good for him as possible- that was more important than what I felt.

  But fuck, this felt pretty nice for me as well.

  “Dommy mommy types?” Kyle ughed.

  “How’d you know?”

  “You’re just so damn subby, Briar.” “Heh. Got me pegged.”

  “Goddammit-”

  “Or did you wanna start poking holes in my story?” I chortled.

  “You’re incorrigible.”

  “That just seems like a pretentious way of calling me a gremlin,” I ughed, still bucking my hips in time with his thrusts. He was getting faster and stronger, more forceful, the shockwaves of pleasure growing more and more powerful.

  “Pretentious? Pot calling the kettle bck,” Kyle said. “You listen to jazz, for fuck’s sake.”

  “Touche,” I ughed, and the ughter came in time with a groan. God, even with the condom, I was still wrapped around him. I started pressing tight, clenching and bringing my legs close together as time began to blur.

  Kyle bent low, kissing my back, my neck, my cheek. I turned around and pnted one on his mouth, our tongues dancing together as his instrument pyed me like a damn symphony. His hands found my breasts, pying with them once more, tweaking and pinching my nipples while fondling them, all while he kept on thrusting deeper and deeper into me. I kept on thrusting too, ignoring certain other parts of my anatomy that I didn’t want to touch…

  But which Kyle evidently did, his hands sliding between my legs.

  “Darling, you don’t want anything to do with that,” I said, my throaty purr making the words sound less than convincing.

  “I won’t touch it if you tell me not to,” he said between breaths, “But I don’t have any problem with doing so. I take a lot of pride in pleasuring a woman, Rose. Working the clitoris is generally a good way to do that.”

  “But it’s not a-”

  “I disagree. All I see between your legs is an especially rge clit, one that looks like it could use some attention. Just tell me you don’t want it, and I’ll go back to your breasts instead. But if you do want it, I think I can find a way to make you enjoy it.”

  I looked him in the eyes, still thrusting back, still with him thrusting forward, and the rolls of pleasure that saturated my mind pushed out rational thought. I did want it. I’d never exactly loved that part of me, and I’d rather be rid of it, but at the same time, I couldn’t deny pying with it was a lot of fun. I couldn’t deny that I was curious about how Kyle’s massive hands would feel wrapped around it.

  “Okay,” I breathed.

  “Okay,” he said, kissing me gently on cheek, nibbling on my shoulder as he reached for my groin and took me in hand. He rubbed the underside with his fingers, and I whimpered as the warm shockwaves shot up through me from both sides of my taint. He circled his fingers around the sensitive skin, then grasped it gently as he began to pump it up and down while he continued his assault on my entrance. I did my part, and I filled the air with the song of my pleasure as he worked me more and more and more, working my clit with one hand and cupping my breast with another and nibbling on my neck while he kept on thrusting and thrusting and thrusting.

  I raked my fingernails over his back with one hand and ran the other through his golden hair, doing my part to make this good for him. And we… We were one. I was lost in him, and from the noises he was making, he was lost in me as well. I don’t know how much time passed, and I didn’t care. I never wanted this to end.

  As, I felt a pressure building up between my legs, and as if on cue, Kyle said, “I’m close, princess. I’m real close.”

  “Me too,” I said, a geyser welling up inside me, desperate for release. “I think I’m… I’m… OOOOOOOHHHHH!”

  An explosion of pure bliss overtook me as I sprayed all over Kyle’s bed sheets, and even through the condom wrapped around his cock, I felt the rush of seed coming out of him. Neither of us wanted it to end, but slowly, reluctantly, he pulled his gradually rexing sword out of me while the orgasm echoed through my mind, body, and soul. I rolled over onto my back and looked up at him as he carefully took the condom off and tossed it in the waste bin, then he grabbed me off the bed. “Gonna need to change the sheets.”

  “We can sleep in my bed tonight if that helps,” I said.

  “Princess, your bed is tiny, I won’t fit.”

  “Fair enough,” I ughed as he carried me to the bathroom. “Wanna shower together.”

  “Very much so,” he said, still panting, turning the water on, holding me tight against his chest while we waited for it to run hot.

  “There’s no might about it for me, I think,” I sighed into his neck, the delicious scent of his musk, like woodsmoke and sawdust, saturating my senses. God, smells especially were so much MORE now that I was on hormones.

  “Hmm?” he said, half-dazed with pleasure. Good, I’d done my job.

  “I love you, Kyle,” I said.

  He gulped, like he was astonished to hear me say it, and it was about the cutest thing I’d ever seen. But then all shock melted away, repced by an expression I could read more easily: relief, contentment, joy. “I love you too, Rose,” he said as he carried me into the shower.

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