By: Kokopo618

"Hey, what's up dude?" I ask, walking in to the kitchen, seeing my roommate make his protein shake that he makes every morning.

"Nothing much, just about to head for the gym," He says dumping protein powder into his flask.

"Cool, cool," I say still looking at him. He's got an amazing body, I mean, I'm a guy, but damn. I guess going to the gym all the time pays off.

"What's wrong, Ryan," Jack says, turning to me.

I smile. Not only is Jack, well jacked, but he's also very emotion healthy. He always seems to pick up on when I'm feeling down, "Nothing it's just.."

Jack sets his shake aside, and approaches me, "It's just what, come on we're bros, you can talk to me."

"I'm just feeling a little insecure," I say blushing, I've never been that emotionally open, especially with other guys, but I feel comfortable with Jack.

"Insecure, why?"

"Well it's just, that, you know, I'm not in the best shape, I can't put on weight no matter what I try," I say looking down at my body. It's nothing like Jack's, where he is covered in muscles and definition, I'm skinny, I've got some definition, like how my waist is smaller than my chest or thighs, but nothing that screams masculinity.

"Bro are you serious, I think you're in great shape," Jack says smiling so genuinely at me, making me blush at his sincerity.

"Dude, stop, I'm so not," I say spinning around, showing Jack my small body. The only place that fat accumulates on my body are my ass and hips, "Look at you, you're drowning in muscles, I would do anything for a body like that. It's perfect."

Now it's Jack's turn to blush, "Can I be honest with you, dude?"

"Of course," I reply, thankful our conversation topic has switched from me to him.

"I'm a little insecure about my body," Jack says in a quiet voice.

I giggle, "Haha, very funny." I look at Jack, but his eyes fall to the floor. Oh my, he's serious. I take a step closer to him, "Hey, hey, I'm sorry. I'm just a little confused is all, how could you be insecure about your body?"

"Well it's just that because the way I look most people think I'm a dumb jock, or some kind of douche bag. I feel like they don't see the real me."

It's strange seeing my huge strong roommate be so emotional with me, I feel the need to comfort him, "Hey, that's not true. You're like the sweetest guy I know."

"Really?" He says, returning to make eye contact.

"Definitely," I say putting a reassuring hand on his arm, "If anybody sees you as anything different that's their problem."

Jack smiles, "Thanks man, I'm really glad we can talk like this, I feel like I can't talk with anybody sometimes."

"What about your friends?" I say as my hand still rests on Jack's arm.

"The guys I work out with are too concerned with their egos to be open," Jack says.

"Let's make a promise. Let's always be open, there's no sense in keeping our emotions all bottled up. If we're feeling bad about something we should just say it," I say gently rubbing Jack's arm. It feel good to be able to help my strong roommate, it feels like he's always helping me, it's nice to give back.

"That's a really good idea man," Jack says looking into my eyes, "I should get going, have a good day, alright."

"Alright," I say smiling, watching him leave our apartment. What a nice guy, it's crazy that he doesn't have a girlfriend.

~~~~~

"How was your workout?" I ask setting down my Switch controller as Jack enters the apartment.

"Really good," Jack says joining me on our couch, "Wow, I like your hair down like that. Whacha playin?"

"Thanks," I says, running a hand through my hair, normally, I wear it in a manbun or ponytail, but I decided to let it down tonight, "Mario Kart."

"Cool. Cool. Hey listen, I have an idea," Jack says turning to me.

"What?"

"Well are you still feeling insecure about your body."

"Yeah.. especially with your hunky ass around here," I say trying to inject some humor into my earnestness.

"Well, I was thinking back to my early days, when I first started working out, I was small like you, and I was insecure."

"What did you do to make it better," I ask.

"It just went away, and I think it was the time I spent in locker room. With a bunch of shirtless sometimes naked guys walking around, I just realized everyone is their own shape and it's not a competition."

"So you want me to hang out in locker rooms?" I ask.

"No silly," Jack says giving me a playful punch on the arm, "I was thinking that we could take our shirts off, and kind of just get it out in the open. I think it would help."

I bite my lip, "I don't know, we're both two straight guys. Isn't that a little homo."

"Not at all, and if it helps your insecurity, isn't it worth it? I don't want you feeling like all insecure in your own home. Our home."

I smile, Jack is so sweet to even think this, I'm a little conflicted, but I think it over and it makes sense. Maybe if I saw Jack shirtless, I wouldn't feel as weak by comparison, "Okay." I slowly reach for the hem of my shirt, and pull it over my head. I reveal my upper body, my tight tummy, slender arms, tiny waist. The only thing that's got some fat is my slightly flabby chest. I look at Jack, whose eyes are transfixed on my body.

"I know I already said this, but you've got a great body, I can't believe you're insecure," Jack says.

I blush, "Oh stop stalling, take your shirt off."

Jack smiles, and in a fluid motion he pulls his shirt off.

"Oh my," I gasp. I stare at Jacks body. His rippling muscles are even bigger than before. It must be because he just came from working out. His beefy pecs, and large shoulders look like they were sculpted from marble. Oh gosh, he's even got a six pack. I look up to his eyes, realizing I've been silent staring for minutes, "how do you feel?" I ask.

Jack is quiet for a moment and looks a little confused. Then he grabs my small hand in his, and places it on his chest.

"What are you doing?" I say quickly pulling my hand away.

Jack looks nervous, scared and confused as to how he offended me,"I thought you asked how do I feel?"

I giggle, "Oh you silly hunk. I meant how do you feel emotionally. I didn't mean I wanted to feel you up."

Jack blushes, "Oh... I'm sorry."

I smile so he knows I'm not mad, "Don't be sorry. We promised to be open about our feelings, I guess it doesn't hurt to be physically open."

"Yeah," Jack said, though I could tell he was still embarrassed. I didn't want him to feel uncomfortable.

"You know what, I touched you, maybe you can touch me, you know to make it not weird."

Jack perks up, "Well okay. I guess that'll make it even. Alright." Jack reaches out his large hand, and places it gently on my chest.

"Wow, your hands feels really warm on my flabby chest." I say frowning, realizing that my chest is not as appealing as Jack's hard pecs.

"Focus on the positive bro, you're skin is very soft," Jack says cupping the fat on my chest pushing it up gently.

I smile, "see now we're even."

Jack pulls his hand away, and my chest jiggles back into resting position.

"Can I play?" Jack asks gesturing to the game.

"Oh that's right, of course dude," I say, having almost forgotten I was playing. I hand Jack a remote.

"Do you always play as Princess Peach?" Jack asks, after selecting Mario as his racer.

I blush, "Yeah I know it's kinda lame, but I've been playing as her since I was a kid."

"It's not lame at all, princesses are badass," Jack says in his classic always positive way.

I giggle, "that's what I always say!"

The race begins, Jack does better than I expected, maybe I just assumed because he's so strong he didn't play video games.

"I'm coming up on your tail Princess!" Jack says, leaning forward.

"Oh no you don't," I say playfully swatting his arms to distract him.

"Stop that," Jack says laughing, reaching out with his own hand swatting at me. His hand finds my chest, and he squeezing my excess fat.

I let out a gasp, and start giggling, "Stop, you're messing me up."

Jack keeps squeezing me, he even ventures to my nipple, pinching it gently. I can't stop laughing, it tickles.

It would be a little strange out of context. Two shirtless guys, touching each other while playing Mario Kart. But we were just messing with each other. Being bros.

The race ends, with me in first, and Jack right behind me. Jack tosses his controller aside, "Alright Princess, I submit, you've bested me."

"That's right," I say playing the part of an entitled Princess, "now kiss my ring."

Jack takes my hand in his, I'm not wearing a ring, so he bends over slightly. Gently pressing his lips against the back of my hand.

I giggle, as Jack looks up smiling at me. He returns to my hand giving it multiple quick kisses, "I am yours to command my sweet Princess." I laugh again. Jack is so silly. He lets go of my hand, "up for another round, Princess."

First I'm a little confused, thinking he meant another round of his kisses, then I remember the game, "Yes, let's go again. Maybe this time you'll beat me."

"Have you ever thought of cosplaying as a Mario character?" Jack asks as we begin the next race.

I smile, Jack remembered my interest in cosplaying, "No, no, I haven't cosplayed in a while. Have you ever done anything like that?"

"Well, sure if you count Halloween. I was particularly proud of one year I went as a Scottish warrior. Kilt and all."

I pause the game, "I have to see this, do you have any pictures?"

Jack pulls out his phone, "Yeah, let me see here... Oh here's one." Jack shows me his phone.

"Oh my, look at you," I say smiling, "I bet the girls loved seeing you shirtless like that. You look really good. You make that kilt work."

"Thanks bro," Jack says putting his phone away.

"How did the kilt feel?"

"Uh good, why do you ask?"

"Of no reason," I begin, I consider leaving it at just that, but we've been so open lately, I continue, "I've always kinda been curious about dressing like that. Like feeling the air on my legs, in a skirt. It seems freeing, you know."

"I never thought about it like that, but yeah, maybe you should start wearing skirts, Princess."

I giggle at his suggestion, even though he's having fun with me, I know that he wouldn't judge me if I did wear skirts. I unpause the game.

"Maybe we oughta make this round more interesting, how about whoever loses has to reveal a secret," I say.

"A secret, alright Princess, you're on."

After a hard fought race, and more playful touching, and nipple squeezing on the part of Jack, I remain victorious.

"Damn, now I have to tell a secret?" Jack asks.

"Not yet, first things first," I say holding out my hand limply.

"Of course, my apologies Princess," Jack says, holding my hand kissing it. He ups the ante, by pulling me by the arm, as his kisses move from my hand up my arm. I giggle at the sensation.

"Now your secret," I say smiling at my friend.

Jack blushes, "Well it's kinda embarrassing,"

I clap my hands together excitedly, "Tell me, tell me."

"Well I haven't been with a girl in a while..."

"Okay," I say waiting for him to finish. I haven't seen him bring a girl over for well ever. I guess I just assumed he was getting laid elsewhere.

"And I'm kinda insecure because I'm out of practice. Like I haven't kissed anyone in so long, what if I forgot how?"

"Jack, you're so silly. How could you forget?"

Jack smiles, "Well I didn't say it was a rational fear."

I frown, Jack was so accommodating in helping me get over my insecurity. I wish I could help him in return.

"Maybe, there's a way you could practice." I say without fully thinking out what I was saying.

"How?" Jack asks turning towards me.

I bite my lip, looking around the room, my eyes land on my hand, "umm, maybe we could try this." I hold my middle and point finger out. "These fingers, the top and bottom lip."

"I guess we could try it," Jack says reaching out, steadying my hand. He leans in gently pressing his lips against my fingers, it tickles, "It just feels like fingers."

I pull my hand back, I open my mouth, and stick my fingers down my throat, coating them in saliva. I pull them out, again presenting them to Jack, "Now try."

Jack kisses my fingers again, "Now it's just wet fingers. I don't think this will work, thanks for trying though man." Jack says, and I can hear the disappointment in his voice.

"What about, I don't know, ...my cheek?"

"Your cheek, I don't know. I mean, we're both straight."

"Well obviously, but it's not gay if you're practicing for a girl. It's the opposite of gay, come on, you helped me out. Let me help you." I scoot closer to Jack. I put my hand on his large arm, squeezing gently.

Jack looks at me, he brings his hands up to my head, holding me in place, he leans forward, planting a kiss on my cheek. I giggle. Jack pulls back, "what?"

"Nothing, It was good. I think. It's kinda hard to tell."

Jack laughs, "Well I'm sorry Princess, let me try again." Jack returns to my face, kissing my cheek again and again, "Is that better, my lady." Jack says smiling.

I laugh at his silly joke, "I've had better."

Jack tilts my head by my chin, so we're facing. He smiles at me, and I grin in return. He leans in, kissing me full on the lips. My eyes go wide, his eyes are closed, as his warm lips interact with mine. I part my lips accepting his kisses, I tilt my head further, opening my mouth to allow our tongues to explore each other's mouths. Jack's hands hold my waist, as mine encircle his neck pulling him closer.

Jack pulls back, "Was that better, princess?

I giggle, "Yeah, I'm noticing an improvement. Do you feel better?"

"Yeah, I definitely feel more confident. Thanks bro."

I wipe my lips, and smile, "hey, what are friends for."

~~~~~

"Goodmorning beautiful princess," Jack says, sliding his arms around my waist from behind.

I turn my head back to look at him, "Still calling me princess? Are you ever gonna let that go?"

"Probably not, dude," Jack says leaning in kissing me gently, "Thanks again for helping me practice last night."

I'm a little caught off guard by the kiss, but I suppose we've torn down that barrier already. Besides I could always use the practice, for when I get a girlfriend. "You're not wearing a shirt?"

"Yeah, I figured why not, you know. As long as it's alright with you?"

"Yeah," I say feeling the warm from his chest against my back, "no complaints here. Now let go, I'm making us breakfast." Jack doesn't let go, so I turn back towards him, kissing him firmly on the lips, "get a move on, big guy."

Jack let's go of me, I feel his warmth and strength leave me. I continue making our breakfast. A small serving for me, and a large one for him. Jack quickly gulps down his food, quickly after I set it down. Jack wordlessly grabs his bag, and keys, heading for the door.

"Leaving so soon..?" I say.

Jack sets his bag down, he approaches me. He pulls me in by my waist, no space between our bodies. He leans down as I tilt my head up at him, parting my lips. My hands find his neck as we kiss. Our tongues dance between our mouths as we taste each other.

"I'll be back soon," Jack says pulling away.

"Alright, bro," I say though my head is still swimming. That was some practice kiss.

~~~~

"Hey Jack," I say as I enter our apartment.

"Hey Ryan, I got something for you."

"For me?" I ask as I join Jack on our couch.

"Well remember how we were talking about skirts the other day, well I was at the mall, and I kinda splurged," Jack says handing me a bag.

"This is a lot more than just a skirt," I say thumbing through the bag, "Are these women's clothes?"

"They don't exactly make skirts for guys. I know, it's sexist."

"What about this," I say pulling a bra from the bag.

Jack blushes, "The sales lady was very convincing, she thought I was shopping for my girlfriend."

"And you didn't correct her?"

"How else was I supposed to explain buying a skirt?"

I smile, lean over and kiss Jack on the cheek, "Thank you."

"No problem bro, what do you got in there?" He asks pointing to the bag I brought in.

"A surprise," I say taking both bags and skipping to my room, gleefully.

I throw the bags on my bed, first I empty the one I got. It's full of make up. First I was just going to buy some lip gloss, so our practice kisses would be more realistic, but I got carried away. I bought foundation, blush, and mascara. I don't know what I was thinking. But now that I have it, I might as well put it to use. I apply all my newly bought make-up with the help of some online tutorials, then I empty out Jake's bag. It's got the miniskirt, the red bra and panty set, a white top, and a soft pink cardigan.

I put all the clothes that Jack got for me on, I assume he'll want to see me wearing all of it. It was so sweet of him to get me this, though I don't understand why he got women's clothing. I'm just a straight dude who is kind of interested in skirts. I take a final look in the mirror, making sure my panties aren't visible.

I mince my way back to Jack, "Hey Jack.." I say using a lighter softer voice.

"Ryan? Wow... you look... you look really good."

"Really? Thanks dude.. um..I really like it."

Jack gets up and approaches me, he lifts my small body on top of our counter, he begins kissing my neck as my hands find his chest, and I begin to feel him. Wow, he's really in the mood to get some practice in.

"Maybe we should take this to the bedroom," I whisper, "I mean, that's where you'll bring any girls you meet, right?"

"Yeah, okay," Jack says, leading me by the hand to his room. He lays on his bed, motioning for me to join him. I crawl up the bed, mounting him.

"I guess at this point, the girl would start taking off her clothes," I says as my small hands fiddle with the tie on my chest. I pull my top off, discarding it to the side.

"I have to thank you again for doing this bro, I think this will really help both of us," Jack says as I undress.

"I wanna make you feel really good, I want you to feel confident, Jack," I say.

Jack says nothing but, pulls me closer to him, and we start kissing. I can feel his cock under me, strangely it's getting hard, he must be thinking of a girl as he kisses me. I try to think of a girl, but Jack's firm kisses, his strong hands, and hard body allow me only to think of him. Suddenly Jack lifts me off of him, he spins me around. I lay face down on the bed.

"What are you doing," I ask, turning my head to look behind me.

Jack is squirting lotion onto his hand from the side table next to his bed. He begins to coat his cock with a layer of lube, "Nothing Riley, we're just going to try something new."

"Okay," I say as Jacks hand pulls down my panties, I feel the lube on his fingers gently massage my anus. Wow, Jack is really getting into our practice, he even called me Riley.

"Are you ready, Riley," Jack asks positioning the head of his cock right up against the opening of my love hole.

"Yes, Jack."

First it feels like it won't go in, it's too big, but the lubed up head pops in, filling me up, "Slowly, Jack, I'm not used to this," I remind him, grabbing the sheets of the bed tightly. There's pain, but it quickly subsides as Jack continues to stuff me, until the full length of his cock is buried deep inside me, "It's in me."

"Should we stop?" Jack asks.

I turn, "Don't you dare."

Jack continues, pumping away. He fucks me hard and good, sliding his thick cock in and out of my ass, as I helplessly moan in pleasure. He keeps a tight grasp on my waist, ensuring my body makes no other move aside from servicing his cock. But his grip on me is unnecessary as I gleefully thrust myself backwards keeping pace with Jack's own thrusts.

"I'm almost there, baby," Jack says squeezing my chest.

"I want it inside of me," I yell between moans.

Jack obliges, shooting thick ropes of cum deep inside me as I scream in pleasure releasing my own ejaculate on the sheets.

Jack and I cuddle as his cum slowly seeps out of my ass. I look up at him, and he smiles down at me. I kiss him on the cheek, "I think I love you bro."

"I'm so glad you said that, dude," Jack says firmly kissing me on the lips.

I giggle, "So, ready for round two?"

The End

Author's Note: I hope you enjoyed this stupid, sexy one off. Don't take this one seriously, I wrote it kind of like a shitty porn parody, where the two characters are very much in denial. Anyway, comment if you like, and thanks!