So this is just a little thing I threw together for my friend who basically gave me the prompt for this. None of the updates will be very long and they will be sporadic. This isn't like a full blown story, just a cute little thing. (Although it is slowly turning into a story…) I also know I am not the best writer so please forgive my probably many mistakes (especially tenses).
But other than that, enjoy!
Comments are greatly appreciated.
Part 1
Dean Winchester was probably the manliest man around, or so any of his friends would say, and if you went to school with him you would probably be under the same impression. Dean was the stereotypical jock, the one who was the star varsity baseball player, the one who got all the girls, the one who listened to classic rock and loved cars, and the one who was totally, 100% completely heterosexual, or so it seemed.
But like every teenager, Dean Winchester had his secrets. They probably weren't your usually teenage secrets, the ones where you sneak alcohol at the parties or try to hide your porn magazines from your parents, or you slept with your best friends girlfriend. For Dean, his secret was in fact that he had a small stash of silky, soft panties hidden in a box under his bed, and whenever he was alone he would pull them on and enjoy the feel of the soft silk wrapping around his balls, and the feel of them tight in his ass crack. He would strut around thinking about how amazing it would be for someone to push him down and mouth the hard line of his cock through the panties. Dean also had to admit his ass look pretty awesome in those silky pieces of cloth.
There was one other secret Dean Winchester had and that was his giant fucking crush on the blue eyed teen who worked at the local retail store. On days when he didn't have to take care of Sam or if he wasn't at school late for practice or working; Dean would sneak over to the store and hide behind the racks of clothes just watching the boy. His name tag read Castiel from what Dean could see from the distance he kept, but Dean had started to call him Cas. This crush had probably been going on for about a month now and Dean still hadn't gotten the courage to go talk to Cas. He was sure that this was just a phase and it would all pass and he could forget that any of this ever happened and assure everyone that Dean Winchester was straight.
But you see things never really go as planned, especially not for a Winchester.
Finally It happened one Friday evening. Sam had come home and Dean had notice that yet again his pants were showing way too much ankle to probably even be called pants. Dean was pretty sure that if his brother didn't stop growing soon that they wouldn't have enough money left to buy him clothes. With a dramatic sigh, and a text to his friends to cancel their plans for the night, Dean drags Sam to the store to buy him some new clothes. To Sam, Dean was being his normally bitchy self, upset that he had to cancel his night out, but in all honestly, Dean's stomach was full of butterflies at the thought of getting to see Cas again.
When the two walk into the store ten minutes later, Deans eyes automatically search for that familiar tuft of thick black, messy hair, and piercing blue eyes but much to his disappointment, Cas is nowhere to be seen. Dean shoulders slumped forward and he pushed Sam off to go find his clothes while Dean wondered around the store sulking.
Eventually, the teen found himself wondering off to the women's apparel section of the store. Making sure no one else is around; Dean wondered over to the panties aisle and admired the assortment of different panties. He noticed a soft looking pair with lace and Dean couldn't help himself when he reached forward and pulled it out of the pile. His fingers let the material slide through them and Dean felt himself harden a little at the thought of how this would feel, how nice the lace would look around his ass and how soft the silk would feel on his balls. Dean was so lost in his thoughts he didn't hear the sound of footsteps approaching until the person clears his throat. Then a rough, deep voice, that caused the hairs on the back of Deans neck to stand up, says, "Can I help you sir? Are you looking for a gift for someone?"
Dean swallowed thickly and turned around slowly. He's pretty sure he was going to throw up when he found himself eye to eye with the blue eyed teenager, who was honestly standing way to close to be consider proper anyway. Dean took a step back, his face turning bright red. He stuttered over a couple words unable to meet that bright blue gaze, "I… Uh…"
Thankfully, Sam came around the corner then looking for Dean. "Hey Dean! There you are. I needed some help figuring out which looks be…" Sam was cut off though when Dean suddenly grabbed his arm after shoving the panties into the other teens arms. "Gotta go Sam, forgot I left the stove on" Dean said making a quick escape and leaving the teenager standing there holding a pair of soft pink lacy panties and his eyes watching Dean run away, face still red.
"Uh Dean what the hell? We had pizza for dinner the stove was never on" said Sam when they reach the impala. Dean just got in and slammed the door not saying anything. "Come on we're going to another store. I didn't like that one" he said ignoring Sams question. Sam knew something was up but he also knew his brother well enough not to say anything. For the rest of the evening, Dean couldn't stop thinking about those blue eyes.
...
The weekend went by quickly for Dean. Sam kept shooting him funny looks and tried to ask about Friday night again but Dean would just shut his bedroom door or turn his music up louder. Other than avoiding Sams pestering, Dean occupied his time by watching Doctor Who in his room and fan-boying (because he wasn't a girl) over it with his best friend Charlie, who was the only person that knew he watched the show. She was also the only person Dean had thought about talking to about his… strange kink due to the fact Charlie was a lesbian. But he was too much of a chicken to bring it up to her.
At night though, Dean would lay awake still hearing Castiel's voice ringing in his ears. On Sunday night Sam went over to a friends house for dinner and to study leaving Dean alone in the house. Once Dean was sure Sam was gone he slipped into his room and slowly slide the box containing his panties out. He picked his favorite pair, a light blue, with a lace lining that looked perfect on him. Dean slide the underwear on after removing his boxers. The material slide over his skin easily and after just a little readjusting sat perfectly around Dean's butt and balls. A slight sigh came out of Dean's parted lips as he admired himself in the mirror smirking. That's when Castiel decided to push his way into Deans thoughts and Dean could feel arousal shoot down his stomach as he thought about Castiel coming up behind him and giving his ass a light squeeze, whispering into Deans ear how sexy he looked.
A low groan escaped Dean's lips as he palmed himself through the soft material. His hard length was quite obvious now, straining in the material, barely being held in. Laying down on his bed, Dean spread his legs and rubbed himself through the material. Blue eyes floated through his vision and that rough sex god voice echoed in his ears as Dean reached over to his bed side and pulled out his lube. He'd only been brave enough to try this once or twice but right now he was suddenly feeling the need to have something inside of him. Pulling the material aside but not removing it, Dean circled his entrance with one finger before slowly pushing in. His head fell back and his mouth is opened in an "O" shape at the amazing feeling of being filled and stretched takes over. Slowly Dean worked himself open, low moans and grunts leaving his mouth and the occasional slip of Cas's name. Eventually he had three fingers in himself, the most he's ever had, and fuck does it feel amazing. The panties are still on, and by now they are digging into Dean's skin still keeping his length trapped. For some reason Dean can't bring himself to remove them, instead he takes his other hand and rubs himself through the material. A light friction is caused and it only takes a few more pumps and thrusts before Dean is coming while moaning out Castiel's name and imaging it was him inside of Dean.
Now exhausted and out of breath, Dean collapsed back against his bed coming down from his orgasm. Once his breath was caught, Dean looked down and frowned at the now soaking panties. Shit he was going to have to clean them.
Quickly Dean got up and removed the underwear. He hopped into the shower to clean himself and then ran the material under the warm water, gently working the mess out of them. Once he finished, Dean looked around wondering where the hell was was supposed to hang them so they can dry without Sam finding them since they shared a bathroom. Dean figured his closest will have to do since Sam doesn't come into his bedroom anyway.
After hanging the wet panties up to dry, Dean pulled on boxers and collapsed back into his bed. He stared up at the ceiling feeling slightly sore and completely exhausted. His last thoughts before he fell asleep are that he is completely and totally fucked, Cas was going to be the death of him .
