Fine but promise it won't get weird

Theirs a first time for everything

Tyler's POV

I looked out the foggy window next to my bed and paced back and forth for a few minutes. wow i'm really about to fuck my best friend and i'm slightly scared because what if i mess up. Well I already went to the store to pick up some lube and a condom so of course i'm topping.

Okay so now that i have everything in my night bag i guess here goes nothing. So I walk out the door giving my mom a kiss on the cheek goodbye telling her i'll be back in the morning.As i walk this empty street I start to feel nervous I mean in less than a few minutes i'm going to be banging my best friend me. Sure i had a crush on him a bit but still i'm glad he picked me for this, but let's hope i don't screw it up for us.

Since I've been walking I didn't notice I was already in front of his house so I took a deep breath and calmed down before i knocked and was greeted by his dad who might i say is a very scary looking man but is in reality a nice guy. "hey Tyler nice to  see you again James is in his room you can go right up stairs" he said with a smile and walked into the kitchen. I walked up the stairs slowly and then quickly ran to James room. He was laying down reading a Batman comic and his headphone in his ears. Then he looked up and smiled "Hey glad you came" he smirked and got up to greet me with a hug, i smiled into the hug and murmured a hey back. He got up to close the door and looked at me awkwardly and sat next to me playing with his thumbs and shyly looking up at me. "I have to wait until my parents fall asleep" he replied breaking the silence. I nodded and laid back onto the bed with him,so to pass the time we watched attack on titan and enjoyed whenever Armin freaked out about something or tried to wuss out.

So two hours later he went out to check if everyone was sleep and the coast was clear he shut and locked his door. "so what dress would you like me to wear" he asked quietly searching under his bed. I love the red dress it just fits with his blonde hair and pale skin "the red one" i spoke up and he grinned and grabbed it and said" i'll be back".

James POV

wow i'm nervous about this so I just turned on the water and splashed some water onto my face and grabbed a towel to dry it. I looked at the pretty red dress I was going to put on but first i have to put on some of my make up I took my hair out of the ponytail and let it fall onto my shoulders. I first applied some massacre and then some eyeshadow and after red lipstick. I carefully made sure my make up was perfect and brushed my blonde locks. I removed my clothes and boxers that held everything and slipped some panties on and adjusting my member comfortably in the panties. After that I slipped the beautiful dress onto my frame looking at myself and feeling Satisfied with my appearance.

I slowly unlocked the bathroom door turning the door knob carefully and quietly. Tyler looked at me mesmerized and said "wow you look amazing" I blushed and quietly said a thank you to him while walking towards him. "so how do we start"he asked curiously to me. 

I smirked and pushed him down onto the bed softly and he grunted quietly. I kissed onto his neck and left love bites down his neck he groaned a bit. I slowly took his pants down and slipping my hands into his boxer feeling his erected member and removed his boxers.Seeing him breath hard from my actions made me smirk at him and then I grabbed his shaft and begin to wrap my lips at the tip of his member and slowly sucking and swirling my tongue around it he let out a soft moan from his lips.

Tyler POV

Dear Jesus this feels good oh my god this is actually happening. I looked up to see him just sucking hard until his cheeks were hallow and he did his best to take all of me into his mouth and I could feel my tip hit the back of his throat and it felt so amazing that I let a few moans escape my lips.and James is so amazing at this then he removed his lips from it leaving me feeling cold. "why'd you stop"I ask breathlessly to him with lust filled eyes he asked "where's the lube" I pulled it out of my bag with the condom. He turned around on all fours and demanded "come on prep me please" so i took off his panties and squeezed some lube onto my fingers and first entered in one finger into his  hole.

He gripped the sheets and closed his eyes letting a girlish moan escape his red lips. Then I added another to stretch out and scissor and he gripped harder yelping quietly to himself. Then i added the third that had caused tears in his eyes is topped worriedly looking at him "Are you okay" I asked him worriedly. He nodded his head and continued so i took them out and opened the condom and slipped it onto my erected member and applied some lube onto it. I turned him around and he wrapped his legs around my waist he actually would make a beautiful woman then I lined up myself and slowly slipped some of me into him i pushed in back and forth slowly. Goodness he was fucking tight and then I pushed in a little farther and he relaxed a bit so I started to thrust into him and he moaned quietly and tried to be quiet as possible.

James POV

I gripped onto his back oh my god this was amazing i could feel him in me and then all of sudden he hit a spot the sent me moaning uncontrollably.  Tyler noticed what it did to me so he kept hitting it and just thrusted into be harder every time. " Tyler harder" I whispered so he did as he was told and went in harder and he hit really hard to the point my vision became hazy and couldn't see straight.

Tyler POV

Harder okay so i thrusted with all my might and just gave it all I could he moaned and I could see his lips quivering. Just seeing him moan underneath me squirming and moaning. Those beautiful red lips just moaning my name and asking for me to go harder. his red dress going up and his panties on the floor. I smirked and then i could feel in my stomach that i was ready to release. "Tyler i'm going t-t-t-o-o-o" he moaned and then he wrapped his hands around his member and stroked and released and after i thrusts in one last time releasing into him.

Both of our bodies covered in sweat and then James got up to change and came back. "that was amazing thanks Tyler that was awesome"he whispered excitedly "Yeah i know um i could repay you for it" I suggested he looked at me for awhile. "It's fine but hey so promise me something" he asked and looked at me serious. "Okay" i said and he continued and hugged me "Promise it won't get weird between us okay i enjoyed this but you know you'll always be my best friend okay" he whispered with a smile and i smiled back but now i'm starting to regret this because i sorta like him even more now.

Crap i've gotten into way deep but i said " I promise" and then he lay ed down and after a few minutes i could hear him quietly breathing and sleeping. Fuck James why did it have to be you.

"I love you James" I quietly whispered to him.