**Intro**
So this is the first part of a story I wrote. And if you like it, feel free to take this as a roleplay prompt and message me!
**The Best Plans are No Plans**
It was Friday night and I didn’t have any plans, so I figured I’d do what I always did when it was Friday night and I had no plans… have a few beers, play Xbox for a while, and then browse the internet for a while until eventually browsing my way to some porn to jerk off to.
My roommates Jay and Tyler had tried to cajole me to come out to party with them tonight but I just wasn’t into the vibe of the noisy college bar they wanted to go to. Even during the summer when most of the students in town were gone, it would still get especially crowded on Fridays with students like us that kept their off campus apartments year round. Eventually I delayed enough where the guys took off without me and I had the apartment to myself to relax.
When I got to to the “porn” part of my Friday routine I got up from the living room with my laptop and headed to my bedroom. I stripped down into my dark blue boxer briefs, flipped off the lights, and slid into bed with the glow of the
laptop. The first thing I went to check out was the page for The Boss’s stream. The guys were still home and trying to corral me to come chase pussy with them, so I figured I’d catch the replay. Since Samantha and I had broken up the guys, like any good friends would, had been trying to help me get back in the game womanizing with them like we used to before I got coupled up. Tonight though, I wasn’t up for the chase, didn’t feel like having to take charge and court the girl, and punching in URL for The Boss’s seemed much more appealing.
**Ali**
Most of the time, The Boss’s guest star was a young college girl, and that was how I’d first discovered his strean. When I was still in highschool there was a bit of a scandal at my cousin’s school, a girl a couple years older than us, at that point at freshmen in college, went live with The Boss. When someone at his school recognized her, they shared it with some friends, and the vid quickly spread like wildfire amonst the students and alumni that knew her. Many even catching it live. When my cousin told me about the whole scandal I had to check it out for myself.
Her name was Ali, and although I didn’t know her at all, I must have watched that video and jerked off to it hundreds of times between when I first saw it in highschool, and now as a rising sophomore in college. It was one thing to see this girl revealing her beautiful curvy body in high definition, another thing to see her playing with the boss and orgasming on camera, but what really hooked me on the video was knowing how many people had been watching her live. Obviously with every porn star, real pros or amateurs, somedbody’s watched ’em, but something it being a girl from the next state over I was only a connection or two away from made it so much more real. And knowing that maybe a few hundred of the thousands of views were people she knew made it so much hotter.
Most of The Boss’s guest stars were like Ali as far as demographics were concerned, a beautiful white girl coming from her college campus. But that certainly wasn’t the only kind of guest. Black girls, asian girls, latinas, coeds, and yuppies, and 40 something MILFs. The only real common denominators were that they were good looking and in need of some cash.
**All Fun & Game**
The Boss’s show was certainly a good way to make some money. The basic premise of his show was pretty simple, a little like a game show even, and spelled out for the audience both for the entertainment value of the format and to encourage people to try and sign up to come on the show themselves. Simply coming on the show meant you were guarenteed at least $500 dollars in cash, without needing to show your face on camera, take off a stitch of clothing, or do anything remotely sexual. It starts out innocently enough, as a guessing game.
The Boss starts the stream welcoming all the streaming fans and thanking featured subscribers and patrons before he gives a quick intro to the shows format and then takes his seat opposite his guest star. In this initial shot together the pair is filmed in their chairs from the neck down, ensuring the guest’s anonymity while also showcasing their physique and (usually) anxious body language. All the guest has to do is guess what color underwear The Boss is wearing. Guess right the first time, and they walk away with an $500 just for stopping by. Things get interesting on the second guess, if they get it right they’ll will $750, but have to strip a later off before guessing.
Guests have 4 guesses total, and have take one layer off with each wrong guess until they’re nude, but with the stakes being raised for each guess they can win up to $2000 on the last guess. If they can’t get it right in four guesses, they’ll still walk away with $2000, but they have to serve the boss for an eager audience first.
The guest on tonight’s episode was a little out of the ordinary, but not the first of the kind. His name was Kevin. I’m straight, so the episodes featuring guys typically weren’t my bag, but sometimes I’d watch them out of curiosity, especially if I was feeling particularly horny that day. I figured I’d see how things play out with Kevin.
**Kevin**
I watched along through the intro as Kevin made his guesses, wrong each time. With each wrong guess a layer came off. His hoodie first, followed by his undershirt, then his jeans, and finally off went the boxers. After the last of the clothes comr off, The Boss adjusts zooms the camera out so Kevin is fully in frame, face an all. He’s smiling sheepishly as he cups his privates in his hands. “Alright then, don’t be shy, you’ve seen the show and know the drill. Hands on your head, give us a spin.”
Kevin laces his fingers at the top of his head. His body was thin, toned, but undefined by any any real muscle. This was usually the kind of build with male guest stars. Starting with a wide shot the camera zooms in as it pans down his body starting at the face and on down the tuft of light chest hair, his smooth tummy, and a modest happy trail from his navel leading to Kevin’s soft cock. “Not much to write home about there, eh folks?” The Boss says. While more of a flirt with the ladies, The Boss was more teasing with men, especially when it came to how they measured up compared to him. No one was ever bigger than The Boss.
Kevin spins around slowly and the camera stays zoomed in on his tiny, soft ass before zooming back out as he finishes his 360. The Boss comes back into frame from behind the camera, he approaches Kevin and Kevin reacts with a soft nervous little laugh from what must have been a wink from The Boss. The Boss turns to face the camera with Kevin, lightly smacking his bottom once before pulling Kevin in close behind the waist.
“A Friday Night Show means our first activity is going to be determined by you guys with our fan poll so let’s check out the results” The Boss says as a production assistant flips the results of the live poll up onto the screen. In the 10 or so minutes since the start of the video, over 5,000 people watching the live stream had casted their votes. Of the eight poll options, “Makeover” was the winner by a comfortable margin of 30% over the 2nd place choice. This result was pretty typical for male guests.
“I like the way you guys think!” The Boss says when he sees the results “With a boy like Kev here you know the best place to start is with a little makeover. Since Kev’s our only guest tonight and I don’t want to keep ya’ll waiting waiting we’ll make it a quick one.”
The Boss glances down quickly “… and if that stiffening little cock on him is any indication, I think Kevin may just have some much fun here tonight he’ll probably be coming back for another episode where Cara can do him up real pretty” Cara was the show’s production assistant, most of the times with male guests, she’d do their hair and makeup to feminize them for the pleasure of the Boss and audience.
Kevin’s simple makeover started with him getting spread eagle on his back on the bed in The Boss’s home studio, with his wrists and ankles tied to the four bedposts. An overhead camera shot let viewers watch as the Boss used a small personal razor to quickly shear off the lihjt amount of body hair Kevin had on his underarms, chest, and crotch. When done The Boss ran his hands along Kevin’s freshly smooth body, stopping at his cock to give it a little tickle with finger. The Boss then untied him from the bed before having him put on a pair or lacey white panties, a garter, a stockings.
With the first activity- the partial makeover- complete, the Boss addressed the camera again before letting Kevin spin a little wheel, the kind that comes with a game like Twister to, to determine their next activity. Ordinarily there would be a few spins from the foreplay wheel before things would really start to open up. By this point watching, I’m pitching a tent in my boxer briefs. Maybe it was because Kevin didn’t look as much like a dude anymore or maybe it was just the voyeurism thing, or maybe it was because I hadn’t been laid in a while, but the video was really turning me on this time.
**Reaching Out**
I went ahead and skipped ahead in the video, eager to get to get to some of the more hardcore action. My favorite shots in The Boss’s videos always came from when he’d take his guests doggstyle. Multiple cameras would be set up, showcases two camera angles at a time. One angle was from the side, another from behind, one from above, one taking a closeup of the guest’s face to capture their reaction to the Boss’s notoriously laege cock, and the last down between the guest’s legs. The Clitty Camera, as it was called regardless of the guest’s sex, was there to capture squirting orgasms of women and prostate orgasms of men. Such orgasms had come to be expected by fans of the stream, even coming from those who’d never experienced orgasms of that kind before.
I slide my underwear down and pull out my cock and begin to jerk it as I watch The Boss work his magic. It was rare for me to actually jerk to streams where he had a male guests, very rare, but on a couple occasions I had done it out of curisoity and intense sexual frustration. When I had typically I imagined myself in The Boss’s role, but this time it felt different, to my surpise I found myself imagining being in Kevin’s position.
I thought of being dominated and not dominating. I thought of being taken, not taking. I thought of being watched. I thought about being paid to be watched. It all felt so intoxicating. I quickly let go of my cock and stopped myself from cumming, and clicked the back button on my browser to leave the video. I thought about pulling up Ali’s video, or finding some other guy on girl stuff to get off to on another site…
Instead, I clicked the button reading “Apply to Meet The Boss”
Source: reddit.com/r/eroticliterature/comments/hj0z6b/showtime_with_the_boss_from_str8_to_sissy_on_cam