Roger, Over and Out

I couldn't help it, I laughed a little. "For one thing, you're cuter than he ever was."

Roger cracked a smile, but soldiered forward. "I'm trying to say that I did keep other secrets from you. I'm not just pansexual."

I held up my hands. "Roger, you don't need to tell me anything you don't want to."

"But I do want to." Roger reached down and undid something, and started unwinding the torso wrap. "In for a penny, in for a pound. If I leave things unsaid, it'll just... muddy things. So let's just be open about it." The last of the wrap fell to the ground, and Roger stood there topless, displaying a pair of very pretty breasts, pert, firm, and mouthwatering. I was suddenly very aware that it had been months since the last time I'd been naked with anyone.

Roger reached down and pulled something from inside the front of his pants. It was a small latex mound that suggested the shape of a resting cock and balls. "I don't have a real penis. I wear this packer to make me feel... a little more manly I guess." Roger put the "packer" down on the nightstand. "As far as I'm concerned, I'm a man. I feel like a man, I identify with a man's wants and thoughts... I just happened to have been born with girl parts instead of boy parts."

He sighed, and kicked off his jeans to reveal a pair of boxer briefs, and what I would've called before then a set of "womanly" hips. "Before you ask, I'm not transgender. I don't want to change and get boy parts instead, or take hormone treatments, I just... want to keep on as I am. I like what I am. I like the term 'Gender-fluid' better."

"I'm not ashamed of my girl-parts, but I figured it would just be... easier to hide them. Let everyone just assume that I had a penis between my legs, and so they'd treat me the way that felt natural to me."

I nodded with each point, trying my best not to stare at Roger's rather lovely body. Now that the baggy clothes weren't concealing anything anymore, there were some nice curves on display. I swallowed and wrenched my eyes away from the pretty brown nipples, in time to hear Roger ask me, "Do you have any questions?"

By force of habit, I raised a hand as if I was in a classroom, and then immediately shook myself and lowered it, which drew a quiet chuckle from my roommate.

"Maybe a couple. If I say anything rude, please let me know." I shrugged, scratching absently at my bare chest. This is... kinda new territory for me, so I don't want to mess things up, or freak you out."

"Freak ME out?" Roger just stared. "I'm more... look, just ask. Ask me anything, it's okay. I trust you."

"You definitely want folks to use male pronouns for you, right?"

Roger nodded. "Even though I have these," he said, gesturing to his breasts, "I'm still ROGER. I'm still a He, a Him. I'm not... secretly a girl all along and wanting you to call me a girl name when we're in private, I'm a GUY. Just a guy with different sex parts, that's all. I'm not even a particularly butch guy, I'm a sensitive pansexual theatre geek, for Christ's sake... but I'm still a guy named Roger."

"I'm guessing that this is what freaked your mom out?"

"Yeah." Roger started pacing the room. "I was born with a different name, a really girly one -- I'm not going to tell you what, because that name doesn't matter, it's not who I am. Left it behind years ago." His breasts were bouncing gently with each pacing step, and I wrenched my gaze down to the floor to avoid staring. Roger continued. "When I was little, my mom used to laugh about me 'going through a tomboy phase', because I never wanted to wear the frilly dresses she picked for me. Instead, I wanted to hang out with the boys in my neighborhood and play boy games, like playing in the mud, or get 'boy toys' like Transformers. When I turned nine, she decided that this 'phase' had gone on long enough, and refused to let me do any of that boy-play anymore, and even threatened to throw out all my pants and replace them with skirts." He shivered. "I told her that I wasn't PLAYING at being a boy, that I *was* a boy. I didn't feel like a girl at all. Mom freaked out, and beat me half to death before Dad came home from work, saw what was going on, and immediately put a stop to it by pulling Mom off me and calling the cops."

"...Damn."

Roger let out a long breath. "Yeah. My mom can fucking die in a fire for all I care. She got arrested, jailed on child abuse charges, and Dad got a divorce as quickly as he could. And then we moved far, far away, because suddenly the old hometown wasn't very friendly anymore." He sat back down on the bed, causing another mouth-watering jiggle that I had to look away from. "I was lucky to have Dad. He totally gets me, supports me, and started calling me 'Junior' as soon as we moved to a new town. So I became Roger O'Malley, Junior. Legal name change and everything. Most kids in my situation don't get support like that."

There was a bit of silence for a minute, and Roger spoke up first. "Are... you okay? You keep looking away."

I coughed. "I'm trying not to stare at your breasts. They're... really something. Sorry."

Roger looked down at his chest. "They are?" When I nodded vigorously, he just gave them a thoughtful look. "Huh. Never thought of 'em like that. Usually just bind them down to keep them out of my way."

"Honestly?" I looked back up into his eyes. His big, expressive blue eyes. "Seeing you manage all this, I feel silly about my own hangups. Ever since prom, I've..." I suddenly clammed up, shocked at the words coming out of my mouth.

Roger leaned forward. "Ever since prom... Oh. Do you want to talk about it?"

The trust in Roger's eyes cracked something in me. "No... but I'm going to, because I feel like if I don't talk about it soon, I'm going to fall apart. Does that make sense?"

He nodded.

"She humiliated me. She told my entire world that I had a tiny little prick that wasn't good for anything, that I could never satisfy anyone. And I'm terrified that she's right." I looked down at my crotch. "I don't have some massive Penthouse Forum foot-long pornstar dick. I don't have anything special. I feel like... maybe I'm just nothing down there." I pointed to Roger. "And you... you've got a whole different set of parts from what feels right to you, and you're managing it! Like a pro! You're okay with yourself, you're calm, you're chill, you're... beautiful. And my dick fear just seems... stupid."

Roger's face blushed bright pink. "Well... your friends Roy and Mitzi seemed to like what you're packing, right?"

I nodded. "My brain keeps telling me that they were just giving me a pity fuck, and that they didn't really like what I did. Roy's a lot bigger than me, he made Mitzi scram like a banshee that night."

Roger absently cupped one breast. "I bet that if you asked Mitzi how she felt, she'd say some pretty nice things about your, ah, performance."

I shrugged. "Probably. I'm just... caught in this loop. My brain says my penis is worthless, I feel like crap, I try to tell myself that's not true, then I feel like crap for even being willing to listen to that cheating bitch's words in the first place, then I remember how no one's touched me all summer, not even Roy and Mitzi, and then I worry that Jessica was actually right... and it just starts all over again." I put my face in my hands. "I feel like a broken record."

Roger's voice was right there, he'd gotten up and was standing in front of me. "Ishmael, do you trust me?"

I nodded, not looking up. "You've put a lot of trust in me already, and it's not even been a week. But yeah, I trust you."

His voice was gentle. "How long is your penis?"

I only paused a moment, still not looking up. "...Five and one third inches erect."

"That's a normal size. Right in the average range. Nothing to be ashamed of at all."

My fingertips massaged my aching forehead. "I know that. I've looked it up. But... it still feels useless. I know, it's irrational. It's stupid."

"Your feelings aren't stupid. But I have... an idea. Ishmael, look up."

I did, and Roger was standing right in front of me, his fingers hooked into the waistband of his boxer briefs. "I'll show you mine if you show me yours."

I was completely at a loss. "What?"

Roger toyed with the waistband. "I've never taken off my underwear in front of anyone. Ever. I've never felt safe doing that, until now. I think I'd feel safe taking these off in front of you, because you haven't judged me once since we met. For all that I talk about how I'm not ashamed of having girl parts, it's still... a little weird not to have the 'right' parts. And so I don't let people see them. But it's okay if you do." He pulled down the waistband, revealing a beautiful sight. Pretty as a pin-up, with everything neatly trimmed to an even patch of soft curls... and visibly wet. I swallowed, and Roger kept going. "If it helps, think of this as paying back some roommate-dues, because you've definitely done more in that regard than I have, even though I brought it up."

I looked up into Roger's face, and his hand caressed my cheek. "Let me see what you have, and I'll let you know what I think. I'll be kind, but I'll be honest, I promise. And then... I really want you to hold me tonight." His fingers ran through my long hair, and I shivered -- I hadn't felt someone touch me like that in... forever. "I've had a pretty scary experience tonight, and you've opened up a lot, and I think we could both use being held. Skin to skin, right here. How does that sound?"

As Roger stood there, I felt my brain ticking away like a clockwork machine. I'd always thought Roger was good looking from the moment I met him, but I'd immediately slotted him as a "Dude" in my mind, which meant that I instinctively held back on that attraction. Old habits, I guess. And now Roger was standing in front of me, breathtakingly naked, in a feminine body that was hotter than any past girlfriend or porn-driven fantasy. Roger was still a "dude", but the curves and the breasts and all the "girl parts" details were giving my mind a swift kick. I was attracted to Roger. I wanted Roger to hold me. I wanted to be naked with Roger. It didn't matter that we were both guys, regardless of parts... and then I realized it really didn't matter if Roger had girl parts or not. I just wanted Roger, because Roger was amazing.

Without another word, I slipped off the rest of my clothes, and sat there naked on the edge of my bed. I looked up at Roger, not wanting to look down at myself just yet. "Hi."

"Hi." His voice was soft and lovely. "Can I... inspect it? I just want to look at it, touch it a little."

"Yeah. That's okay." Roger's hands were then between my legs, gently lifting up my length out of my curls, moving it a little here and there, as if to see it from different angles. It reacted to his touch, growing to that five-inch size.

"I think your body is lovely, Ishmael. All of it. Come on, let's just relax for a bit." He put my length down, and we climbed into bed together. He threw one leg over me, and I could feel his soft breasts against my ribs, and the warmth of his wet sex against my thigh. "This is really nice," he said, nuzzling in close. And I felt something inside me crack open, like an iceberg ripped open from within. I felt Roger's trust. I felt his attraction to me. I felt the wet lust between his legs. I felt his acceptance of me, broken record in my head and all. I felt safe. I felt virile. I felt like the words of some cheating high school harpie just didn't mean anything anymore. I felt... happy.

And I wept. It might have been for five minutes or for an hour, I couldn't tell you. But all throughout it, Roger held me close, and kept me feeling safe. I did my best to hold him close as well, to show that he was right to place his trust in me.

When it was over, I blinked away the last tears, and turned my head to look for Roger. He was right there, looking right back at me, giving me a quiet little smile, illuminated only by the moon peeking through our window, and everything just felt right. I know he felt it too, because we both leaned in at the same time, and just that first kiss alone nearly seared me down to the bone.

I'd never felt a kiss like that before. Ever. As our tongues danced, it was like I could feel this amazing person pour into me, warming me from the inside out. I reached up to caress one of the lush breasts rubbing against me, and Roger broke the kiss, arching his back in ecstasy. "Jesus Christ, YES. Touch me, Ishmael. Touch my body, please."

Who could say no to an invitation like that? I slid down, and took one nipple in my mouth while lightly pinching the other, and was immediately rewarded with two hands running through my hair, urging me onward with a firm and hungry grip -- and very hungry words. "Fuuuuck, no one's ever done this to me, Ishmael. I...oh god... I like to tweak them when I masturbate, but I can't lick them like that, don't stop, don't stop..."

Taking the hint, I pinched the other nipple a little harder, and Roger made the most adorable cross between a moan and a squeal. My rod was as hard as steel, pressed against Roger's thigh, and I felt more attractive and alive than I'd ever felt before. I'd made this beauty cry out my name, and I was on top of the world.

I leaned over to swirl my tongue around the nipple I'd just been pinching, and let my hand drift lower, to caress Roger's hip. He took my hand in his, and guided it lower still. "More, Ishmael. I want to give you everything tonight. Touch me. Finger me. Give those girl-parts a wet workout." The pad of my thumb found the raised mound of Roger's clit, and I gently caressed it as my fingers teased his drenched opening. I reluctantly relinquished my liplock on the most gorgeous breasts I'd ever seen in my life, and kissed my way along Roger's neck as I whispered to him. "Are you ready, Roger?" My fingertip lay poised between his outer lips, and he responded by spreading his legs as wide as he could.

"Do it," he said, and I obeyed, pulling another breathy gasp from my new lover as my finger plunged deep into an ocean of tight lust. My thumb kept up its caress on the clit, and the sound of wet thrusting filled our room, turning me on even more. Roger pulled my face upwards for another scorching kiss, and started attacking my ears with a barrage of licks, nibbles, and urgent need. "Put in one more... fuck, yes. Just like that. Harder, Ishmael, harder... holy mother of God, I'm coming, I'm gonna come for you, you're gonna make me...FUUUUUUCK!"

Roger's tight pussy clenched hard around my fingers, his thighs shaking as pleasure ripped through him. He muffled his cries by burying his face into the crook of my neck, licking and sucking in a way that I knew was going to leave one hell of a hickey in the morning -- but I loved it. I would wear that hickey like a badge of valor, and I could feel my cock throbbing with arousal as Roger's orgasm thundered through him.

After a few moments, he gently nudged my hand away, and I reveled in the feel of this tight pussy clinging to my fingers as I slid out. On a whim, I dipped a wet fingertip a little lower, just touching the edge of his ass, and his body shook in my arms as he called out, "Too much! Too much!"

I mumbled an apology as I pulled my hand away, wiping it off on the bedsheet before I wrapped Roger in my arms. "Sorry about that." I kissed his forehead, marveling in the smell of his hair, but he shook his head.

"No, it's okay. You're definitely going to do that again tomorrow night -- with my ass, I mean. God, yes." He gulped down air, and wiped sweat from his cheek with the back of his hand. "I just get really, really sensitive after I get off, so it was too much just then." His soft hand found my erection, and began stroking it. "How are you doing, sexy?"

I purred at the touch -- Roger definitely knew how to handle a cock, and I loved every second of it. "Best night of my life, gorgeous. Even if we stopped here, I'd be a happy, happy man."

Roger sniffed, and flashed me a wide smile. "Stopping here? Not on your fucking life, Ishmael." He moved down the bed, to curl up around my leg while still stroking me, my rod at level with his face. "I am quite proud of how good I am at sucking cock, and you're about to get the fruits of my labor." Roger's tongue slid from root to tip, and now my back arched with rich pleasure. He looked back up to meet my gaze. "But I don't want you to come in my mouth tonight. That, I'm saving for the wake-up blowjob you're going to get tomorrow morning." He gave my tip a kiss, in an almost comically dainty and delicate way. "Tonight..." He paused, and swallowed nervously. "I want to feel you come inside me. I want you to fuck me, Ishmael. I want you to be my first."

I caressed the buzzed side of his hair. "I'd be honored, Roger. You're so goddamn beautiful." Roger grinned in the moonlight, and suddenly my rod was surrounded by warm, wet, swirling ecstasy. I felt my eyes cross as I watched Roger's head bob up and down my rigid length, his cheek resting against my belly, and I let my head collapse back onto my pillow as I experienced the greatest oral sex of my life. Roger clearly knew exactly what he was doing, as I felt his hands, lips, and tongue manipulate my rod and balls like a virtuoso musician playing their instrument. He seemed to be enjoying himself as well, with cock-muffled moans escaping around his lips as he sucked me into levels of pleasure I'd never imagined.

After a few minutes, I could feel the heat rising in my length. I wasn't going to last much longer, but Roger sensed it before I could manage the presence of mind to warn him. He sat up, gently stroking my balls. "Ishmael, believe me when I tell you that I absolutely adore your cock." He looked down at my length, and smiled. "You fit perfectly in my mouth, you taste so good, and I love that little shiver you make when I deep-throat you. That bitch who dumped you was a fucking idiot." He smiled, and stood up, walking to the other side of the room to his dresser. "And now," he said as he pulled out a condom packet, "I'm going to give that delicious cock my virginity. Are you ready?"

"I've never been more ready for anything in my entire life, Roger. Get over here."

Roger stepped back over, and straddled my thighs. "You're tested, right?"

I nodded. "Last month. Totally clean."

"Good, same here." He moved up, and paused. "Ishmael... I'm going to put this on you... but can I feel it in me bareback first, just for a second?"

I reached up and flicked my thumb across one of his thick erect nipples. "Be my guest, lover."

Roger shifted position, took my length in hand, and carefully sat down on me, the lips of his pussy parting deliciously around my erection. "FUCK, THAT'S GOOD," we both cried out in unison. There was a moment's pause, and we both burst out laughing. "JINX!", we both cried out at once, causing another round of laughter, and then Roger called out "Jinx!" again before I could stop laughing. "You... mmm. You owe me a coke, mister," he said with a throaty growl.

Taking his hips in hand, I thrust upwards, savoring the feel of this tight wetness on my circumcised length. "Right after you wake me up tomorrow with that blow job you mentioned, I promise." I looked up into his big shining eyes. "How do you feel?"

"So good, I don't have the words... but I really should get this on you." With a sigh of regret, Roger dismounted, carefully opened the condom wrapper, and rolled the latex down my length, lovingly stroking all around me as he did so. That accomplished, he mounted me anew, and we both sighed happily upon re-entry.

We stayed like that for a long time. Roger gently riding me, the walls of our dorm room echoing with his gasps, my moans, and the soft wet sounds of our lovemaking. He braced his hands on my chest, stroking my nipples here and there as I did the same to his hypnotizing bosom. We were in no hurry at all, and it was glorious.