How Gay Will He Go? (Part One: The Mild Round)

jaypablo Great tease of that ass, love it Apr 7, 2022

After several weeks of difficult and exhausting negotiations, I finally succeeded in convincing D-Rel - the very same 18-year-old straight boy who only wanted to do sex scenes with females and declared up-front that he "didn't want no gay niggas touchin' him sexually" - to come back for a "gay for pay" scene!

I decided to set the scene up as a "Fear Factor"-type game show called "How Gay Will He Go?"

The premise was simple: D-Rel could earn a VERY large sum of money by agreeing to participate in a series of gay-themed "challenges" (written out in advance on index cards). These challenges were divided into three rounds - "Mild," "Medium," and "Challenge" - based on their increasing levels of difficulty. For every challenge he completed, D-Rel could earn a cash prize and get himself one step closer to going home with the maximum pay for the day. How much or how little he ended up doing would be totally up to him! He could refuse to do any or all of the challenges, but each activity's cash value would then be subtracted from his total for the day. He'd be free to quit at ANY TIME during the shoot and STILL walk away with the money he'd earned from the previous challenges.

Enjoy a front-row seat as I film this fulfillment of the ultimate fantasy shared by any gay male who's ever lusted after a straight boy like D-Rel and wondered just "how gay" you could get him to go if the price was right! If you're only interested in hardcore gay action, then this ISN'T the scene for you. If, on the other hand, you're turned on by watching the countless subtle and surprising ways that straight boys will compromise their "straightness" for cash, then this is a scene I guarantee you will never forget!

D-Rel sits nervously on my futon and I ask him a few questions before we begin. He insists that he's never done anything sexual with another guy, not even playing around as a kid. When I ask him what changed his mind about doing a gay scene after refusing so vehemently up until now, he explains that while surfing the web a few days earlier, he'd found a car that he really liked and realized doing a scene for me was the fastest way he could earn the money to buy it.

I explain the general rules for the day's unique "game show" shoot, and remind D-Rel that how far he goes (and how much money he earns) is totally up to him. As a little extra motivation, I give him a sneak peek at the huge wad of cash that could potentially be his by the end of the day. As he stares wide-eyed at the thick stack of bills, he grins from ear to ear like a little kid on Christmas morning and tells me that he's determined to go home with the maximum cash reward!

[SPOILER ALERT: If you enjoy the element of surprise and want to discover for yourself just how far D-Rel goes in this FIRST of the three rounds, don't read ahead!]

I pull out the first index card for the "Mild" round and read aloud D-Rel's very first challenge: He must let me take off all of his clothes and give him a full-body nude massage. D-Rel seems hesitant to give another man that kind of intimate access to his body, but he agrees to it nevertheless!

My heart pounds wildly in my chest as I take a seat behind D-Rel and pull his tense, reluctant body against mine. D-Rel closes his eyes tightly as my hands roam across his fully-clothed body.

I remove D-Rel's clothing piece by piece, still stunned to be disrobing this boy who'd once seemed so hopelessly out of my reach! I caress and explore his beautiful body, savoring every inch of his smooth, warm skin. I also clutch in my trembling hands the firm flesh of that sweet teen-boy ass I'd only been able to admire from a distance up until now!

Long before I've even THOUGHT about touching D-Rel's dick, it's already rock-hard and straining toward the ceiling! D-Rel's facial expressions might convey stoic endurance, but his BODY tells a very different story. Is it possible that somewhere deep down, this cocky black teen actually ENJOYS the sexual attention from an older white man?!?

D-Rel seems understandably confused and embarrassed by his body's reaction. "I was picturing you as a girl," he tries to explain in a shaky voice.

One of my favorite parts in D-Rel's solo "audition" is when he stares seductively into the camera and talks about all the freaky things he wants to do with his female fans. D-Rel's second "challenge" of the day asks him to do something similar - only this time with his GAY fans more explicitly in mind!

D-Rel begins playing with his dick and looks hesitantly into the camera. "You want this body, don't you....GUYS?" he asks with obvious embarrassment as he utters that final word. It's a hilariously awkward and tentative beginning, no doubt. But with a little bit of coaching from me, D-Rel grows more comfortable and ends up putting on a VERY hot and memorable show!

Watching a self-declared "homophobe" like D-Rel try his best to anticipate what his horny gay audience wants to hear will make you laugh out loud while reaching for your dick at the very same time! D-Rel shows off his hot teenage body and talks about all the nasty gay things he'll let you do to him. He turns around and proudly displays his tempting young ass, even spreading his butt-cheeks to give you a glimpse of a virgin hole so tiny it can barely be seen!

"You can do WHATEVER you want to me!" he promises in his raspy adolescent voice.

I'm confident you'll be as amazed and turned on as I was by some of the shocking and creative and VERY GAY things that come out of D-Rel's mouth without any prompting from me! I've already jacked off to this footage more times than I'd like to admit!

D-Rel's next challenge asks him to continue teasing (some might say TORTURING?) his gay audience by sucking on his fingers and playing with his ass. Words can't do justice to just how unbelievably hot it is to witness D-Rel shoving his fingers seductively in and out of his mouth while running his fingers up and down the tight virgin crack of his ass, even poking them against his sweet tiny hole.

Watch carefully and you'll catch him rolling his eyes as if thinking to himself, "I CAN'T BELIEVE I'M ACTUALLY DOING THIS!"

The final challenge in the "Mild" round is for D-Rel to give and receive a "handjob."

I sit behind D-Rel and pull his body tightly against mine once again, reaching around to play with his dick and balls while he watches a straight porn DVD.

Horny for my first real "conquest" of the afternoon, I scoot out from behind him, yank down my boxers, and wrap the hesitant straight boy's fingers around my hard throbbing dick!

Seeing those skinny brown fingers wrapped so tensely and clumsily around my dick is a beautiful sight to behold - and of course the feeling is infinitely better! We sit side by side like that for awhile, jacking each other off as D-Rel steals quick, curious glances at my dick. I savor this dizzying intimacy with the straight black boy of my dreams, and try my best not to cum too soon!

As the "Mild" round comes to an end, D-Rel looks a little stunned, disoriented, and even a bit out of breath. I bring a smile to his face by reminding him how much money he's already earned, and give him a hard time about enjoying himself more than he'd like to admit! So far he's tackled all of his challenges with relative ease, and still seems determined to earn the maximum pay possible! But this "Mild" round is just a tease, an athlete's "warm-up" for the actual game....

Stay tuned for Part 2 (The Medium Round)! Discover what new challenges lie in store for D-Rel as I test this straight boy's boundaries to determine just "HOW GAY WILL HE GO?"

Categories: Big Dick, Director: Michael Galletta, First Times, Interracial, Older/Younger, Straight Boy
Details: Oct 10, 2009 77 min
Photo of D-Rel
Photo of Michael Galletta
Michael Galletta

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