Kevin becomes Kelly.. My Kelly

Do you know what it's like be stuck in a dorm room with a male roommate, in an all-male residence hall, during a dry spell? When you can't even masturbate because either your roommate is around, or you have homework or studying to do? I'll tell you what it's like. It's like being starved. Red-blooded guys like me need a woman's touch. We need to be between their legs, making them utter sounds only real men get to hear. We need the warmth and softness of a girl, or we go insane.

And I was going insane. I hadn't jacked off in a month. A month. And I hadn't been able to score. Either I fucked things up, or luck came in and fucked it up for me; there was no getting laid. It was wearing on me. My grades were beginning to slip, and I was getting irritable.

"FUCK. FUCK. FUCK. FUCK!" I tossed my Xbox controller onto my bed, to my right.
Even my game was suffering.
"You alright? Losing never used to piss you off this much." Kevin was my roommate, and he was the more sensitive between us. He had a way of speaking his mind, too. For the moment, his words pissed me off even more.
"Fucking armor-locking motherfuckers." I leaned back in my chair, exhaling.
"Yeah, they're bastards, but c'mon, you're overreacting. Something else is wrong."
"What does it matter to you?"
Kevin looked at me, his brown eyes resolute. "Because it’s been miserable in here for the last few weeks. You just sit in here and fume and snap at me when I try to chill you out. Things used to be relaxed around here."

I knew he was right; I was making things tense in our little room. But it pissed me off even more to hear it. I didn't like being told I was wrong, or at fault. I didn't always take it well.
"Goddamnit you whine a lot." I stood up and grabbed my jacket. I needed to leave. I wanted to get away from the accusations, even if they were right.
"And you can't face facts when it comes to yourself." Kevin turned in his chair, leaning across the back of his chair.

I put on my jacket, and approached Kevin. I wanted to hit him now, I was so mad. His smarmy, know-it-all demeanor needed to go. I looked down at him, and he didn't flinch one bit. I was bigger than him. Stronger than him. But I couldn't hit him. And he knew it. I was always a bit of a softy, and I always had a soft spot for him. He was after all, my only real friend on campus. The only guy who got me, who I could hang out with anytime and feel comfortable with.

"I need to go. Get some air. I'll see you later." I turned to leave, but Kevin was faster. He leapt for his shoes and jacket as well, and I was nearly out the room when he came up behind me. "Not without me, big guy."
I sighed, waiting outside the door for him. "Fine." I couldn't help but smile. Kevin's charm was disarming, and in a word: cute. I didn't feel ashamed to admit that to myself. And he cared. Such a rare quality these days. Guys need support too. And it's great to have that one guy who can help you out.
"Where we goin'?" Kevin said, now leaning on me with his hand to get a shoe on.
"Figured I'd grab a drink."

"You were gonna sit at the bar, alone? Seriously, James?" He looked at me. I just shrugged.
"Wouldn't be the first time. Won't be the last if this dry spell keeps up." We walked out, down the hallway, and into the entry area. Down the steps, we found our way outside in the cool, winter air.
"So that's what this is about? Getting your dick wet?" He gave my arm a small punch. It didn't hurt, but I acted like it did.
"Hey!"
"Damnit Jim, I thought you were depressed or something." He stuffed his hands into his pockets, and blew a lock of his brown hair out of his face.
"I might as well be. I'm horny as fuck and I haven't even gotten my rocks off for a month!" We headed for the parking lot.
"You can't...take care of that yourself?" He looked at me as he approached my car. I didn't make eye contact.
"I've tried."
"How hard is it!?"
"When you're around, and with my busy schedule? Nigh-impossible." We got into my car.
"Oh. Sorry." He looked down at his lap, as we pulled out of the space, and started on our way to the nearest bar.
"Don't worry about it. It's not your fault. I'm just unlucky." I glanced at him, and he smiled a bit. Good. Even though it bothered me, I didn't want him to feel bad.

We drove in silence for a long while, arriving at the bar without a word. We entered the bar, and I held the door open for him. He gave me a smirk.
We took a seat, settling into a booth and removing our jackets. The waitress eyed us both up with some interest. I smiled back, and Kevin only offered a small grin.
"What can I get you two?"
Kevin tapped his lips in contemplation, and I simply watched him. It was amusing for some reason. I guess you could say I thought it was cute. I simply waited for him to answer.
"Uh, just something sweet I guess. Rum and Coke." I smirked at him. He glared at me.
"I'll have Wild Turkey, on the rocks, please. And put his Rum & Coke on my tab." The waitress nodded with a smile and took off.
"Hey, I don't need you to p-"
"I've been a dick, man. I'll pay for your drink. It's fine." He glared at me still, but it was his playful kind of glare. He pouted a little.
"Fine."

We got our drinks, and bullshitted about a lot of things. School, jobs, parents, Reach. Then we came back to the subject of girls, which Kevin's always been evasive with. I never pushed it, and he was happy to talk about my love life. Just not his.
"Why don't you go for the waitress? You can be charming when you need to be."
"Yeah, I don't know if she's my type."
"Not your type? I thought you wanted to get laid. Seems like you can't afford to be picky, Jim."
I sighed. Maybe I was just nervous. More than I was used to being.
"I need another drink."
And so we had a few more.

"Why don't you have a girlfriend, Kevin?" The barlight casted a red-purple neon glow on the table, but I could see his expression. He hesitated.
"I'm not judging you man, I just wanna know. Nerves? Holding out for that one girl?"
"You could...say that I guess. Both."
"Well, how do you know if you don't go out and try to find her?"
He was silent. I finished my fifth Turkey on the rocks, savoring the taste.
"Because I like guys."
I looked at him, wide-eyed.
"Oh. Wow. Uh..."
"Guess that answers the question, right?" He looked down at the table.
"Yeah."
"This isn't gonna make things weird is it?"
"I wouldn't think so. I have no problem with you being gay." I didn't. Why should I give a shit? Still my best friend, y'know?
"Well, I'm not exactly gay either..."
"What?"
"It's hard to explain..."
"Hey man, I've got time."
"Don't you have class tomorrow?"
I sighed. I did have class. But I didn't care. I needed a break. And it sounded like Kevin needed to talk, so...
"It'll be fine dude. Let's talk." He looked away, unsure. He blew some hair out of his face.
"You wanna get outta here?" I figured he wouldn't want anyone overhearing. Figured he'd feel safer back at our place.
He nodded, with a small smile. So I paid our tab, and we left. Once again, the ride was silent, though not uncomfortably so.

We arrived back at our room after the cold walk, and I sat on my bed. He sat next to me. It was probably closer than I would normally be comfortable with, but Wild Turkey is a hell of a drink, and I was chill with it.
"So, what did you want to know." His big brown eyes looked into mine.
"You said you liked men, but you weren't gay. Not sure I understand."
Kevin sighed, and he crossed his legs. He frowned, looking around, as if the will to speak was somewhere in the room.
"You can tell me, Kevin. You know I'm cool with just about anything, and I listen."
"You do, don't you?" He smoothed some of his hair behind his ear, in a feminine gesture. I flinched. When I saw him there, legs crossed, brushing hair behind his ear, frowning, I saw someone vulnerable. It made me want to help. It also made me see Kevin differently. He looked almost...like a girl. I shook my head. A girl? What the fuck was I talking about?
"I've always felt different, Jim. Like, I don't belong in this body." His voice was quiet, softer than usual. I snapped out of my confusion. I had to tread lightly; I didn't want to upset him.
"What's wrong with your body, Kevin?" I reached out, and placed a hand on his. He flinched then, and looked at me, with his big, brown eyes, surprised.
"I feel like...I'm not a guy, Jim." He looked away from me.
"What do you mean? You are a guy."
"No, I feel like I'm a woman. In a man's body."
I looked away then, realizing finally what he meant. I had heard of people like him before. I didn't know how to react.
"You still OK with me now? A room transfer isn't that big of a deal, I'd understand Jim."

I didn't care. I cared about him too much. And now he needed support more than ever. If I rejected him after hearing his secret, it'd tear him apart.
I held his hand tighter, giving it a squeeze. It was all I could think of.
"No, Kevin. It's cool with me. I'm not sure I understand, but you're my best friend, and I don't just get rid of people because they're different."
Kevin smiled then, squeezing my hand back.
"Thanks. I've never told anyone. Not even my parents."
"Good thing I'm such a great guy, then, right?"
He beamed a smile then. His eyes trailed down my arm, to our clasped hands. My eyes followed, and I soon realized how tightly I was holding his. I gently released it, and cleared my throat.
"Sorry about that." I rubbed the back of my neck, more than a little bashful.
Kevin scooted closer to me, and spoke in a hushed tone, "You know, I've always had a thing for you, Jim."
I froze. What did he say? I couldn't look at him.
"One secret too many?"

I looked up at him, and he looked strange. There was definitely fear in his eyes. But also a confidence. No, hopefulness.
"I..." What could I say? 'Fuck you Kevin, you queer?' That's not even what I wanted to say. I didn't know what I wanted. He was vulnerable, and I wanted to help him. Make him feel better. And even more distressing...I didn't want to say no. I didn't have the kneejerk reaction I expected. Maybe I liked him too.
Before I could get much further, Kevin grabbed my hand and moved into me. He placed his lips on mine, and chills went up my spine. I froze, my eyes wide, but he held his ground. His lips were soft, warm, and inviting. I couldn't resist for long, and with a groan of approval, I leaned into him, kissing him back.
His arms threw themselves around my neck, pulling me harder against him, and I went nuts, unable to control myself. My hands grasped at his small, taut waist line. He purred a little against me. As our lips pressed and slid against each other, I felt a stirring between my legs. I was getting hard, and I didn't care that I was kissing another guy.

Kevin took it up another notch, his tongue delightfully invading my mouth to play with my own. A flash of heat ran through my body, and I grabbed at him, holding him closely.
Then, as suddenly as he started it, he withdrew, and leaned back. I still held him against me, and he looked down at my arms, smirking a little.
"Wow." I said, almost breathless.
"Wow indeed. You're a great kisser." His brown eyes brimmed with mischief, his arms still around me.
"You're pretty good too...uh..."
"Uh what?"
"So what...do we do now?" I searched his eyes.
"We keep going, if you like." He gave a short giggle, tempting me with his eyes.
"I...wouldn't mind that at all, actually."
"You sure? I still have a guy's body..."
"I'm willing to experiment."
Kevin grinned then, and he gave me a quick kiss before sliding his arms off my shoulders. He wriggled in my arms, trying to get out of them. I reluctantly released him, and smiled as he ran about the room, checking his dresser for something.
"What're you looking for?" I leaned back on my arms, watching with amusement.
"Several things, all of which are surprises."
After a few moments, he bundled some things up and walked up to me. He stole a quick kiss, giggled, and headed off to the bathroom. "I'll be quick! Promise!"

I licked my lips, and leaned forward. My hand reached down to adjust my pants. I was getting stiff, and it was uncomfortable with it in more ways than one. I could never have seen this coming. I had just made out with another guy, and enjoyed it! Not to mention...I maybe be close to sleeping with him too.
I sat, these thoughts and more racing through my head, until Kevin came back in. He sauntered into the room, his hips swaying a bit.
"You just needed to go to the bathroom? I thought you had a surprise." It was then I noticed he was wearing a little bit of lipstick.
"I do." His voice was a little higher now, and he began undoing his pants. Beneath, he wore a pair of black, lacy panties. He tugged his pants down with this thumbs, bending over. He stepped out of them, his legs soft and shaven smooth. I couldn't believe how sexy they were. A little bulge lay beneath the cute black underwear.
His put his hands on his hips, and sauntered up to me, with a sexy little walk, his brown eyes glinting with devious intent.
"And you can call me Kelly, big guy."

I was in shock. In the short span of a few minutes, my best friend Kevin had become Kelly. Kevin was a slender guy, with soft brown eyes, medium length brown hair which he swept down in typical emo/hipster fashion. Kelly was adorable. She was smoothly shaven beneath her clothes, wearing black lacy panties.

She even had a semblance of curves. Beneath Kevin's baggy clothes, hidden, was a delicious figure.
Kelly stood in front of me, beaming down at me. She shifted her weight onto one of her hips, and placed her hands at her sides.

"So? How do I look?" I couldn’t begin to describe. I could still see Kevin in there, but there was more. For me, there was a woman standing in front of me. She was a **********ish in figure, but she was smooth, curvaceous, and projected an aura of powerful femininity. My hands reached out, and gently touched Kelly's naked legs, feeling their warmth and smoothness. She beamed even wider down at me, noticeably leaning into my touch. Her rosy lips parted a little.

"You look..." My eyes focused on the little bulge beneath her panties. I knew it was a penis. And I knew I didn't like guys. I was pretty sure, anyways. But I looked up to Kelly then, and our eyes locked. Maybe it was the fact that I had an opportunity to screw, and my brain was overriding my reason. Maybe I didn't want to hurt Kevin's...or Kelly's feelings. Maybe both. But I felt something when I looked into Kelly's eyes. Maybe sexuality is more complex than just "I like men" or "I like women." Maybe gender is more than just what body parts you do or don't have.

Besides, I couldn't deny how hot Kelly was. And seeing as how...willing she was, a cock wasn't going to bother me much. She was woman enough for me.

"You look amazing." I meant every word.

And I think it hit her, because she flinched. She places her hands on my head, rubbing my ears and neck.
"I think you really mean that..." Her eyelids lowered a bit, lovingly looking down at me as her soft fingers played with my hair. Goosebumps erupted across my body.

"I do. I want you Kelly." My hands curled around to grasp her ass, taking each cheek in hand, spreading them and kneading them. God she was soft and warm.

Kelly's hands, as if to reply, then left my head, and traveled down my chest to my lap. She found and began petting the stiffness beneath that had been pinned to my leg.

"I can see." She smirked at me, and leaned in to kiss me. I happily met her. Her lips were delightful, and it made me even more stiff. My hips moved a bit against her.

She broke our kiss to look down. She licked her lips.

"Let's get you out of these, big guy." She kneeled then, at the edge of the bed, and began undoing my pants. I just leaned back, enjoying the sight. I was growing rather...enamored with Kelly already. And something else, a darker part of my mind, was delighting in the situation for different reasons.

Don't guys love it when a girl wants their dick? Everyone wants to be desirable in some way. I love it when a girl wants me. Especially when she wants me so bad, she'll do the dirtiest things to get my cock inside her. Kelly clearly wanted my cock. And the fact that I brought Kelly out of Kevin gave me a perverse satisfaction.
Kelly began tugging my pants down as I finished this thought, and my cock burst out as soon as it was able. Still, my boxers held it down a little.

Kelly pouted a little and stuck her fingers under the waistband of my boxers, and pulled them off, quickly. And my hard member was finally free, standing triumphantly. Kelly licked her lips, and her hands moved in to gently caress it with her fingertips. I stiffened even more, and exhaled a breath of approval.

"Wow..." Kelly was a bit wide-eyed, as her hands began running up and down my hot shaft. I moved a little in and out of her hands.

"Wow is right...have you ever done this before?" Kelly shook her head.

"Never even seen another guy's before, up close...I've wanted to, but I need someone I trust, y'know?" She looked up at me, a small, adoring look on her face.

"Well, how is it?"

"Its...great." With that, she leaned in, placing a kiss just underneath the head of my penis. I shuddered. She didn't stop. She placed kisses up and down my length, and soon, her tongue was running up and down.

"Fuck!" I began throbbing within her hands. I threw my head back, eyes closed, enjoying the sensations.

Then I felt what I had hoped for an entire month. Hot, soft wetness engulfed the head of my cock, and began moving down its thickness. I cried out. Kelly sucked, keeping her mouth tight. I looked down, to see her lips wrapped around my cock, and her slowly swallowing more of it, taking its time to tantalize me. I wanted to move, to begin fucking her mouth. To grab her face, begin bucking, and come in her throat. But I wanted to enjoy it. And I didn't want to fuck this up.

Then she hummed. A delightful noise come through her throat, and into her mouth. It resonated against my rod.

"Goddamnit!" She looked up to me, still humming, eyes knowing and mischievous. She went as far as she could down my length, with only an inch to spare. I was only average length.

"You sure you've never done this before!?" I looked down at her. She slowly, tantalizingly, removed herself from around me. She licked her lips, shaking her head.

"Nope, never! I just read a lot. And watch a lot of porn."

"Brains and Beauty, huh?"

She grinned, and stood. She climbed up onto the bed, straddling me, my wet, hard dick slicking against her butt as she settled against me. It was now I noticed that she was hard. A penis poked out of her panties, an inch and a half or so above the waistline. I couldn't help but think it was...adorable.

I removed my shirt, and immediately, her hands moved in to run up and down my arms, shoulders, and chest. I wasn't in great shape. I had a layer of fat. So you couldn't see my musculature all that well. My abs were hidden. But I did have a little definition. Kelly's eyes devoured my form with lust twinkling in their depths.

"You're so hot..." She began grinding against me, her butt teasing my cock, while her cock mashed against my belly. She let out a little, girly moan. Her pretty lips parted, and her eyes closed. I could only watch in wonder for a moment, but I knew I could do better. I leaned forward, kissing at her exposed neck. She purred, leaning her head against mine.

"I need you...now..." She breathed. Her right hand reached behind her. She spit on her left, and it followed. She pulled aside her panties, and rubbed her spit onto my throbbing self. I only waited, now sucking on her ear.

After a few moments, she moved my dick to her entrance, lifting her self up a bit. And she began sitting. She had already lubed herself up, though her hole still resisted. After a moment of pressure, I broke into her, and immediately plunged a couple inches into her ass.

"Oh my god!" Kelly groaned past me, her hands quickly finding my arms. She clung to me as she pushed down, plunging my manhood into her warm depths. He nails dug into me. And I fucking loved it.

After getting used to my length and thickness, Kelly didn't spare any time. She begin grinding against me, and despite the tight fit, the lube did well to allow it. My hands gripped her ass cheeks as she rode me, and I searched her lips out for a kiss. She wrapped her arms behind my neck and pulled me in for a rough, wet kiss. Her tongue found mine, and she moaned against me. Her thighs clamped against my sides as we really began fucking. Her hips gyrated as her ass bounced up and down on my rod.

"Fuck...fuck!" She cried. I grinned, watching the spectacle, and begin bucking up into her. Hard. I leaned back on my arms for leverage, and my hips began crashing into hers with delightful wet slaps every time. Kelly's eyes went wide for a moment as she cried out again, and her arms and thighs clamped harder around me. She bit my ear as she groaned loudly with every thrust.

Like every woman I fucked, I wanted to make her explode, to give in to overwhelming pleasure, before I blew. Seems I was doing pretty well...

Kelly was mad with lust now, and her ass clamed roughly against my cock. Everything was hot and wet; we were sweating, fucking like complete a****ls. I bucked against her as she rocked me. Her own cock rubbed against my stomach roughly, lubed by the sweat between us. She exclaimed with every thrust into her butt.

"Fuck fuck fuck fuck fuck!" Her voice began to squeak out as she both ran out of breath and approached climax.

I gritted my teeth, plowing into my woman. I wasn't gonna last long at this rate. But I succeeded, as Kelly did, indeed, explode into orgasm. There were no words, only girly exclamations of ecstasy. She convulsed on me, her arms flexing around my neck, her thighs pressing against my hips, and her lovely ass becoming amazingly tight. As she grunted and cried out, her little cock spewed onto my belly and chest a nice load of white cum. I could feel the pulses of her prostate against my manhood.

I growled in pleasure, and I blew. My body stiffened and I gave one last, triumphant push against her soft butt before my cock began spewing its own strings of seed into her, coating her insides. Finally, the release I so lusted for. A month's worth of cum and lust spewed into my best friend's ass, breeding her. It was like getting rid of a demon, or lifting the world from my shoulders. Relief unlike any I had felt before.

We panted together, with our sweat (and other bodily fluids) mingling. Kelly settle against me, relaxing, purring a little as we shared the afterglow of our mutual climax. After a long moment of silence, Kelly spoke.

"Fucking-A."

"Fucking-A is right..." I returned. All of Kelly's weight was settled against my body, her form lazily d****d against it. The arms which she had used to so powerfully cling to me were still loosely wrapped around my neck, though one of her arms dangled.

"Guess you finally got laid, big guy." She lazily sat up, enough to face me. He butt pushed against me, and I shuddered. I was only just beginning to lose my hardness. She removed her arms from my neck, crossed them, and used them to prop herself up on my chest. She smiled slyly, her big brown eyes gazing at me mirthfully. She was beautiful.

"Guess we also know what to do if I ever get to be an unbearable asshole." I smiled back up at her.

"Mmm. I'm hoping you never have to be again. At least not when it comes to getting laid."

"I never thought you and I would be friends with benefits..."

"Would it bother you...?" I shook my head, tilting my head forward to kiss her. She made an approving purring sound against my lips.

"Not in the slightest."

"You know I'd have to be Kevin a lot of the time, right?" I nodded slowly. It didn't matter. I didn't view Kelly as any different from Kevin. It just felt like I knew Kevin better now. I thought Kelly was a cuter name, but the name didn't matter.

"I don’t care. You're my best friend. Maybe more than that..." Kelly grew serious then, nodding. She rubbed her nose with mine.

"I'd like to be more. I really like you James."

"I like you too." We locked eyes for a long, tender moment. She blushed a little and averted her gaze for a second. Smiling, I looked past her, at her bed at the other side of the room. She turned, curiously following my gaze.

"What?"

"I don't know if I could go to sleep tonight with you in a separate bed." I grinned at her.

"I'm your woman, now, huh? Need to keep me close? So I don't wander and philander?" I nodded, with a chuckle.

"All mine."

"Good. Let's push them together. I'd love to sleep next to you..."

I shifted beneath her, glancing down. Her cum still lie on my belly and chest, and her little dick and receded back into her panties. It was cute.

"Wanna take a shower first?" Kelly bit her lower lip, nodding.

"Only if you promise to get me all dirty again."