How Gay Will He Go? (Part Two: The Medium Round)

jaypablo Love that tight hole Dec 2, 2022
terbernt I love looking at D-REL Aug 16, 2020
hungucttop A surprisingly sexy, hairy butt.... Apr 17, 2017

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.

In Part 1, you watched as D-Rel allowed me to explore every inch of his naked young body, and even agreed to stroke my dick! Now discover what NEW challenges lie in store for D-Rel as I continue testing this straight boy's boundaries to determine just "HOW GAY WILL HE GO?"

[SPOILER ALERT: If you enjoy the element of surprise and want to discover for yourself just how far D-Rel goes in this second round, DON'T READ AHEAD!]

D-Rel's first challenge in the "Medium" round is KISSING!

I give him the choice between allowing me to kiss him on the surface of his lips (without reciprocating), or (for higher pay) KISSING ME BACK and submitting to some deep and intimate tongue-action. To my great relief and excitement, he agrees to the latter!

D-Rel looks absolutely terrified as I grab his cute face in both hands and pull him toward me for his very first guy-on-guy kiss. I kiss, lick, fondle, and suck on D-Rel's incredibly soft, pliable lips - savoring each second as if it might be my last. I push my tongue past his lips to explore the inside of his mouth, pausing occasionally to nuzzle D-Rel's neck and suck on his sweet young tongue.

While I get lost in the moment, D-Rel clenches his eyes shut in disgust and looks like he might throw up any second. He even holds his saliva in his mouth and runs to the bathroom every few minutes to spit!

"I'm not going to swallow my spit that's been in another guy's mouth!" he explains when I ask what he's doing.

But don't let D-Rel's "misery" fool you! He's actually a very cooperative and talented kisser, opening his mouth to give my tongue easy access and even poking his own tongue past my lips for its first tentative exploration of another man's mouth. And even though D-Rel's facial expressions reveal nothing but repulsion and disgust, his dick stands straight in the air the entire time! If you're as turned on as I am by the idea of a cocky straight boy becoming aroused against his will by the very same things he swore he could NEVER enjoy, then you're in for a real treat with this scene!

I remind D-Rel that he's free to quit any time and walk away with the money he's already earned, but he says he's determined to persevere. "I still haven't made enough money to get the car yet!" he explains.

I turn up the heat with the next challenge: nude "dry-humping."

I pull off my boxers, lie back on the futon, and pull D-Rel's tense, naked body on top of me. D-Rel begins grinding his crotch against mine while awkwardly kissing my neck. I wrap my arms around him in a tight embrace, then run my hands up and down his backside, paying special attention to those flawless double-mounds of flesh rising so enticingly into the air.

It's by the far the "gayest" thing D-Rel's done until now, and while D-Rel's MIND is well aware of this fact, his DICK clearly couldn't care less! As it rubs against my dick, balls, and pubic hair, it grows to full hardness once again and in no time D-Rel is humping me like a young bull in heat! I grab the camera off the tripod and get a nice close-up shot of D-Rel's large dick smashing against mine. Watch carefully for a beautiful shot of both our HARD dicks dripping precum at the same time!

Before moving on to the next challenge, I try to get D-Rel's reactions to what just happened. Despite all evidence to the contrary, he still refuses to acknowledge getting any pleasure from his first gay encounter.

"You're a DUDE!" he exclaims over and over, as if repeating that fact will make his dick go suddenly soft and spare him any further embarrassment.

D-Rel's next challenge is to receive his very first blowjob from a guy. I ask D-Rel what he thinks getting head from another man will be like. "It's gonna be weird!" he replies, but says he's open to giving it a try!

D-Rel leans back on his elbows and watches straight porn as I kneel between his legs on the floor and move in for my first taste of that fresh straight-boy dick. Knowing this might very well be my only time between D-Rel's legs, I WORSHIP that young black cock like a monk bowing in prayer - licking, sucking, and slurping until my jaws ache! With a little bit of coaching from me, D-Rel even smacks that big ol' thing against my cheek, nose, and lips! Of course I also can't pass up the opportunity to taste those dark, heavy balls, inhaling their musky teen-boy scent as I nuzzle, lick, and roll them around in my mouth!

At first D-Rel stares blankly at the TV, but I soon catch him looking curiously down at me from time to time as I bob up and down on his dick. He tries to seem indifferent and unaffected, but it's obvious to me and anyone watching that he's actually ENJOYING his first blowjob from a guy! There's even a funny moment when I ask for his honest reaction and he can only bring himself to mumble that "it feels weird." When I threaten to stop what I'm doing, however, he finally admits that it feels "alright."

Now I'm usually not one who enjoys sucking dick for a very long time. But it's also not every day that I get to be the FIRST man to taste a hot straight boy's dick, so I wasn't about to squander such a rare (and EXPENSIVE) treat! I lie back on the futon and instruct D-Rel to kneel over my face. Taking his dick in my mouth, I grab his ass and encourage him to fuck my face! I swallow as much of that big dick as I can - even gagging a few times in the process - as the horny straight boy uses my mouth like his own personal pussy!

The final challenge in the "Medium" round is for D-Rel to let me LICK HIS ASS!

Until now, NOBODY has been anywhere NEAR that most private and protected part of D-Rel's young body, not even his numerous girlfriends! But for the right price he grants me the privilege of being the first!

It's amusing to hear D-Rel's inability to understand how anyone in their right mind could want to do such a "disgusting" thing. I do my best to explain that some gay men think of assholes in the way he thinks about pussy, but I don't think he accepts the comparison! And of course no words can convey to D-Rel just how fiercely I've been fiending for a taste of HIS pretty little pucker in particular!

I nearly slip into a state of shock as D-Rel lies flat on his stomach, his ripe upturned ass just BEGGING to be groped and smelled and devoured! I instruct D-Rel to look over his shoulder and tell the audience at home what he's about to let them watch me do.

"You 'bout to lick my ass, man!" he explains in a sexy, embarrassed voice.

You really have to witness for yourself D-Rel's surprising and unforgettable reaction to having his ass eaten for the VERY FIRST TIME! Watch as my tongue tastes, licks, and probes that sweet virgin asshole in several positions....

[SPOILER ALERT: If you don't want to know about one of this scene's hottest surprises, DON'T READ AHEAD!]

I can tell you that there are a variety of hot and hilarious facial expressions. I can also assure you that D-Rel's tight teenage hole is by far the SWEETEST I have ever tasted!

But you'll have to see for yourself what leads up to D-Rel gasping, "What the hell?!?" after unexpectedly blasting cum all over his stomach and chest! That's right, the self-proclaimed "homophobic" straight boy BUSTS A NUTT from another man's tongue lapping hungrily AT HIS ASS!!! The look on his face after it happens is ALONE worth the high price I paid for this scene! It's one of those classic, unscripted moments that make amateur porn so much fun to watch and will have you rewinding to re-watch it again and again!

The scene concludes with me asking a stunned, embarrassed, and very confused D-Rel for his reaction to what just happened. After a brief but interesting discussion, I ask D-Rel if he's ready for the final and most challenging round.

"MAYBE....depending on what it is!" D-Rel replies in a shaky voice, his courage and ambition from the start of the shoot quickly fading.

To find out just "how gay" D-Rel ultimately goes, stay tuned for the third and FINAL round, coming soon!

Categories: Ass-Eating, Big Dick, Director: Michael Galletta, First Times, Interracial, Older/Younger, Oral-Only, Straight Boy
Details: Oct 19, 2009 102 min
Photo of D-Rel
Photo of Michael Galletta
Michael Galletta

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