Chapter Text
Dean Winchester was a man of simple pleasures. He loved living life in boxers and a bathrobe or less. And his career in the porn industry guaranteed it so well that he retired at 40 to live out his years comfortably, with all the time in the world. Now, he filled up his life with custom cars, classes at the community college, and sports. Everyone outside his close circle of people were shocked when he retired. He was in his prime as Bruce Kent, the handsome bisexual who started out as a timid bottom in gay porn.
By the time he was in his mid twenties, he was masculine without being a meathead. He caught the attention of a few companies who competed to sign him. Temptations, the company whose contract he chose, gave him a 3 million dollar contract for 12 films a year. They agreed to his terms of choosing the costars and sex acts while the writers and directors at Temptations would create the story line. He was happy renewing the contract year after year as the awards kept coming in. He made a few good friends and got to fulfill some awesome fantasies of his. He had a 20x15 foot poster of the groundbreaking film King of Lesbos in his living room. It was a film that just had lesbian scenes of Charly Candi, Joanna Harlot, Ruby Diamond, and Megan Diamond playing castaways on a tropical island while the native, Bruce, was watching. Although women didn’t really do it for Dean, he could see the eroticism of watching four gorgeous women pleasuring each other on a beach with a setting sun behind them.
Nothing really led up to his retirement, though. There wasn’t anything that made him feel in danger or unhappy. He simply woke up one day and just didn’t want to pull his dick out in front of a camera. Dean talked to his agent, Gabriel, about it and Gabe started up the process of turning down new jobs. Becky and Chuck at Temptations were bummed to hear about Dean’s decision. Becky was looking forward to casting the story lines where Bruce Kent was in older authoritarian roles. They ended the contract amicably and sent out press releases to the fans and media about Bruce Kent going into retirement. His fans reacted from hurt to outrage but thankfully nothing too scary came of it.
Once the hubbub died down, Dean moved on with his life. He still stayed single with casual dates but after being so sex-centric for over two decades, he needed a break. Unfortunately, his front porch would always have a package or three each week from some porn studio hoping to coax him out of retirement. Most of the time, the packages were of crappy DVDs of terrified young porn stars. He couldn’t bear watching them. Dean would send those DVDs out to the organizations who helped porn workers get proper representation. It was the most he could do.
Sometimes there would be a diamond in the rough. A cute boy or a handsome man that Becky knew was Dean’s type. Those DVDs would go into his spank bank. Dean currently had a dozen DVDs on that shelf. All were audition solo pieces of the men in their rooms getting themselves off with their hands or toys. A few were shy while most were turned on by the exhibitionism.
By the third year of Dean’s retirement, the amount of DVDs sent to his house in Beverly Hills had dwindled drastically. His spank bank had 16 men and he was content with it.
Until that fall day when he got a package from Becky. There was a long winded letter from her that explained that it would be a one time deal and the DVD was of the guy, Jimi Cox, acting in his first high production film that was “FOR BRUCE’S EYES ONLY!!!” Dean raised a brow. Jimi Cox sounded like a run of the mill porno name. He tended to stay clear of those but if Becky was this enthusiastic but polite enough to not barge into Dean’s house and force him into this film, he might as well watch it.
He loosened his bathrobe once the DVD was whirring inside the player. Soon a slender pair of creamy legs in white lace appeared on the 80 inch TV as a decent soft piano soundtrack played. Dean let out a soft moan. He only ever confided his love for crossdressing men to Becky during a drunken holiday party. He thought she wouldn’t remember. She did and he was okay with it.
The camera zoomed out as those legs crossed and uncrossed themselves. Dean felt a small twitch in his groin as manicured fingers ran down the tights to the straps of some killer white designer shoes that belonged on a runway in Milan instead of a porno. The heels shown on the HD screen looked like they were ivory. Becky wasn’t holding back on the production value. As the shoes fell to the persian rug, the camera finally panned up to show more of this Jimi Cox. The hands on the screen were unbuttoning a sheer robin egg blue blouse that wasn’t hiding a lace bralette at all. Dean nearly pumped a fist in victory when the camera got a shot of Jimi’s jaw line and startling pink lips. Dean would’ve thought they were tinted with makeup but he could see that they were chapped and in desperate need to be wetted by his tongue. He watched them move into a slow smile as Jimi’s hands finished unbuttoning the blouse.
Finally the camera zoomed out completely to show messy black hair and blue eyes. Dean was now sold on the idea of doing a film with this beautiful creature. Jimi stood up to continue undressing. The blouse fell down to join the white shoes. Dean groaned seeing soft hints of a six pack and a black happy trail that connected the white lace panties to Jimi’s belly button. The music faded by the time Jimi took off the bralette. The pretty boy on the screen spoke in a voice that opposed his appearance, “Hello, Bruce. I’ve been a fan for long time. I remember being little and seeing that hot big man on those movie covers. The movies I wasn’t allowed to watch. Sometimes he would be in my dreams.”
As Jimi spoke, his hands wandered his body until his fingers were lazily teasing his nipples, “When I was a big boy, my parents left me home alone at twelve. I knew what to do. Mm, I put one of the videos in the DVD player and fell in love.”
Dean was stunned. He couldn’t tell if this was some world class writing or an actual confession from this stranger. It was really fucking hot that he was the cause of Jimi’s first wet dream. Dean started to jerk his cock to the rhythm of Jimi’s nipple teases.
“He- ah! He took that other man and woman and made them have sex for him. I would close my eyes and believe that he was praising me for being a good slut for him.” Jimi started rolling his hips at an angle so Dean could see his bulge in profile. Dean remembered which film Jimi was talking about. It was one of his first threesome films and first time doing a scene with a woman.
“For a whole year, all I prayed for was for Bruce to eat out my pussy. I was too afraid to fantasize him fucking me with that huge cock in my tiny ass,” Jimi let out a whine before leaving his now deep pink nipples to slip off the lace panties. As he rolled the fabric down, he also took off the stockings. He was truly naked now. Without the femme illusion, Jimi was more of a lean athletic type. And Dean was all in on how versatile Jimi’s appearance could be.
Jimi moved to bend over the bed as the camera zoomed in on the pale ass that didn’t show signs of being hairy or waxed. Dean had spent enough time in the industry to see that this was a rare find of genetics. He sped up his fist around his cock to a medium pace. He wanted to last until the end.
“Then, for my sixteenth birthday, I got my own computer. I learned so much. I learned how to do this while watching your videos,” Jimi purred as he squeezed his ass leaving red impressions before spreading his cheeks to reveal his hole that looked well prepared without being distorted. “I would sometimes just hold myself open and ready for you while listening to you fuck through my headphones.”
Dean had to squeeze himself tight from feeling the rush of a premature ejaculation starting to blare in the distance. This Jimi was getting to be too much despite the fact that he was only 5 minutes in.
“Most of the time, I would fuck myself open with my fingers. It took me a few months to learn that sex toys were available to filthy boys like me. As much as I wanted a Bruce Kent dildo, I only got a slim dildo.”
That only reminded Dean of getting his cock cast for the dildo line based off of his cock. His brother thought it was the funniest and craziest thing Dean ever did during his 22 years in porn. At least Dean never had to admit fucking himself with one of the Bruce silicone dildos. He told himself it was an educational experience and a damn good one too.
All thoughts died in his head when he saw one of those hands leave the screen to come back with a light blue silicone vibe. It was thin but very textured and Dean remembered using the three settings on Joanna Harlot during a film.
“I hope you like watching me fuck my pussy with my toy. I got this one after seeing Erotic Experiments. It’s so small but so strong and makes my hole tingle with all the bumps.” Jimi started rolling it around inside himself and Dean could hear the soft hum. He could tell Jimi was hitting his prostate because then the man would give a whine that sounded like he had been on the verge of orgasm for days. The desperation became contagious and Dean groaned aloud.
“Dean, I wish you were here to fuck me or even touch. Or I could touch you with my fingers or mouth. I’ve been getting off on only you since I knew what that good tingle meant. Please, please, please!” Jimi let out a groan as he came. The camera was able to get the perfect shot of his balls twitching and length bobbing in the air coming untouched onto the sheets. Dean went to town on his own cock. Jimi used his real name. What the fuck? His orgasm came quickly as he watched Jimi collapse onto his side with his cock still leaking a small pool of cum on his hip. Dean watched Jimi move the cum around on his body and take a few licks before pouting.
“I wish I was cleaning your cum off of me. Well, I hope you enjoyed this. Call Becky and ask for Cas,” The man blew a kiss at the camera and then Dean heard Chuck shout, “Cut!” To Dean’s surprise, Cas then fell back onto the sheets with a huge blush
“Was that acceptable? I kinda got wrapped into it. You’re so mean, Rebecca. Making me jerk off to the sex god.”
“C’mon, Castiel! He’s going to love this! I think he’ll love to have a piece of your cherry pie,” the blonde woman winked at the camera. Sneaky Becky!
“But he’s never done virgin porn! It’s been one of his clauses since the get go! I can’t go and lose it to just anyone though.” Cas pouted but then grabbed the towel a production assistant handed to him. He cleaned himself up before wrapping it around his waist.
“Nah, you’re one of a kind and who knows, maybe he’ll get super possessive over you and you’re stuck with him forever!” Becky giggled as Cas gasped at her. Dean smiled as he watched them walk off the set.
Interesting.