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Henry couldn’t believe he was doing this. It’s not that he didn’t have options, or prospects. He had plenty, they just weren’t… what he was looking for. Never mind the fact that he couldn’t exactly put into words exactly what it was that he was looking for, he just figured he’d know when he saw it.
And he knew he would only find it by going right to the source. It was no surprise to him that Pez was familiar with this website, being of generational wealth himself and practically made of money long before Henry had even gotten his business off the ground. He had tried to get Henry to join several times in the past, but Henry always insisted that he was comfortable just casually dating and seeing if it goes anywhere.
Now, with his 40th birthday right around the corner, he had yet for anything to stick. He created his login for the website, promising connections with other men looking for similar arrangements.
He setup his profile, keeping everything brief and truthful.
Henry, 39
Author & CEO of Fox-Mountchristen Publishing
Seeking young, fit companion
He attached a few photos that he and Pez had carefully selected to encapsulate his vibe. The first was a mirror selfie in a well-fitted custom designer suit, the second photo was him playing in the park with David, the third was an action shot of him in a polo match, and the fourth was a shamelessly shirtless selfie because as Pez had put it, he may be pushing 40, but his body didn’t show it.
Once he clicked ‘save,’ the website directed him to a landing page with hundreds of younger men’s profiles to scroll through. He scrolled, saving a handful of men’s pages as potential options. One man caught his attention so aggressively, he almost choked on his tea.
Alex, 23
Pre-law student at NYU
Young & Hung
This kid must be confident to have ‘young & hung’ listed on his profile. From what Henry could see in the first photo, he had every right to be. It was a shirtless mirror selfie (shameless), the top of the photo just cut off above a teasing smirk. The bottom of the photo cut off in the best worst place possible, right above the base of his cock. His washboard abs were on display, traveling down into sinful V-lines, leading the way to a thatch of pubic hair that seemed very well kept for a boy his age. He could see the dark pinkish brown base just at the bottom of the frame and almost had to surgically remove his jaw from the floor.
He swiped to the next photo, this time a full-face shot (but still shirtless, of course). Alex had the most captivating, deep brown eyes that Henry had ever seen complete with the most sinful eyelashes a man could possibly have. His smile reached his eyes so much that they nearly squinted with the expression. His hair was pushed back in thick, dark curls that Henry couldn’t help envision tangling his fingers in.
In the third photo, Alex actually had a shirt on (shocking). But he might as well not have, because it was a mirror selfie in the gym that showed his shirt completely soaked through with sweat. His tongue poked teasingly out of his grin in this one, winking at the camera. Henry’s eyes traveled down to the tiny running shorts Alex was wearing, and that was precisely the moment of no return.
‘Hung’ was right. Jesus Christ, Henry could practically make out every vein in the boy’s cock the way it pressed against the shorts. He must have been hard in this photo, right? How else could the print be that… aggressive?
Henry had seen all he needed to see, and he opened a new direct message to Alex. His thumbs hovered over his phone’s keyboard, frozen and suddenly terrified of what to say. There was a passing moment where Henry worried that Alex was a catfish, but there was a thorough vetting process before he was even allowed to sign up for this site. He imagined the process was the same on the other end.
Finally, he began typing…
Good evening, Alex
I am quite impressed with what I see on your profile. If you are amenable, I would be honored to take you out sometime and work out an arrangement that would be mutually beneficial for us both.
Best,
Henry Fox
He hit send before he could second guess himself, and went back to scroll through other profiles. He barely had the chance to make it through two more young men before a notification popped up at the top of his screen. Alex had already messaged back.
Wow, you really are a writer. Such a formal way for you to tell me you think I’m hot ;)
The feeling is mutual sweetheart, and I would be so fucking amenable to that idea
Henry’s heart fluttered at the endearment; such a forward approach from the young man. Every part of him wanted to invite Alex over tonight, but he really wanted things to be special for him. He wanted to show him everything he had to offer when it came to their first date. Pick him up with his private driver in his blacked-out town car, treat him to an exquisite dinner, perhaps gift him a token of his gratitude in the form of jewelry or something of the sort.
One thing was for sure, Henry knew he had to be upfront about what he wanted from this arrangement if he wanted to take things any further.
I want to make it explicitly clear, Alex, that this arrangement would ensure that you live a very comfortable life. I expect nothing in return but your company, and believe me when I tell you that I get everything I could possibly want out of just making sure you are taken care of. If this is something you are comfortable with, then we can proceed.
If any of this makes you uncomfortable, then we need not go on further, and thank you for your consideration.
He didn’t have to wait long, as Alex’s text bubbles popped up just moments after the message was delivered.
Henry… you do realize you reached out to me on a sugar daddy website… right? Lol I’m comfortable with all of it. More than comfortable. I have plenty I can offer you, too.
Now they were getting somewhere… And now that Henry got the initial jitters out of the way, he was dying to know what exactly Alex was offering up.
Well, yes, it does seem you are quite confident in your offerings. After all, the tagline “young and hung” speaks volumes. Unfortunately, your photos leave a little too much to the imagination, dear.
He hesitated about including an endearment at the end of his own message, but he didn’t want to be over formal and weird the kid out immediately. He tried to match his energy a little bit, even if it felt slightly out of character for him. He liked the character he was playing though, this growing confidence.
Can’t give away the goods for free, Henry. You should know that ;) Plus, I would have enjoyed seeing a little more skin in yours, too.
Shit, I didn’t realize you’re almost 40
Henry momentarily panicked, thinking Alex was going to back out of the situation due to his age. He didn’t have to worry for long, because Alex’s next message was immediate.
Your body is so fuckin sexy, I never would have guessed
Okay, that answered that, then.
This old thing? I suppose my hard work continues to pay off, then. Couldn’t help but admire your photo in the gym. I can tell you take good care of yourself, Alex.
I do what I can, but I could definitely use someone to take care of me in other ways…
Attached was a photo that nearly made Henry swallow his tongue. It was shot in Alex’s own POV, legs outstretched on what appeared to be his bed, wearing nothing but boxers. His legs were muscular and covered in delicious, dark, thick hair. The tent in his boxers was utterly indecent, as were Henry’s thoughts.
What is it that you need, darling? Textbooks? Money for the subway? Groceries delivered? Just say the word and I’ll run my card.
Very funny (though I would love to circle back to all of those, actually)
I’m just wondering if you can help me take care of this current situation
Another photo, this time with Alex’s hand down his boxers. Nothing was showing, but it was clear that he was gripping himself beneath the fabric. Henry could definitely play this up, especially with the response his own cock gave at the idea.
Hard to say, I think I’d have to see what’s really going on to get all the details. Can’t help if I don’t know what I’m working with, pet.
He wanted to desperately to say more, but he wanted to give Alex room to take it however he wanted.
Fuck, that’s really hot actually. Okay, shit. Sorry it’s hard to type with one hand ;)
It was even more gorgeous than Henry imagined. Alex sent a photo with his boxers pulled down and tucked just underneath his balls. He gazed at Alex’s massive hand wrapped around his even more massive cock. This thing was like a third leg, and Henry couldn’t help but finally free his own dick from his trousers. He palmed himself lightly, imagining the weight of that monster cock in his mouth, pressing into his throat. Or better yet, pressing into his arse repeatedly, driving him into the mattress. He must have been too lost in his own fantasies, because Alex messaged again before he had a chance to reply.
Get distracted over there, sweetheart? I know it’s big, hope it doesn’t scare you off
Christ, Alex. The opposite. I can practically feel it in my gut.
Care to share? I showed you mine, it’s only fair to show me yours ;)
Henry obliged, positioning his dick as attractively as one can, slightly pulling back the foreskin so that Alex could see he’s uncut, but also show off his shiny, leaking tip.
Would probably eclipse mine, pet.
Think you could take a video for me? Want to see how you like to be stroked
Alex sent a video back a few moments later, this time with no accompanying text. No, this was worse. His voice sounded wrecked on video, a deep, slightly southern drawl that made Henry’s dick harder with want.
“Fuck, baby. I’m picturing you instead of my hand. Would you like that? What would you wanna do first?” His hand stroked up and down lazily, and Henry watched as the veins flexed in both his dick and his arm as he worked himself. “Bet you want it between those pretty lips I saw, hmm? I bet you’re fucking incredible at sucking dick.”
Henry decided to send back a little video himself, this time positioning enough to show himself jerking off, as well as show his lips that Alex had clearly taken a liking to. It didn’t hurt that in between the two was his impressively toned torso. In the video, he licked his lips before saying, “You’d certainly be the biggest I’ve ever had. Not sure I could take the whole thing. Not unless… you forced me to,” he finished the video by biting his lower lip. He knew when he looked good, alright.
Alex’s next video picked up where he left off, but he was stroking much faster now, the sound slicker than before. “Started leaking so much when you said that, fuck. Can you hear how wet I am for you? All because I imagined fucking your face. Tell me what else you want to use this dick for, Henry.”
Hearing Alex say his name was, embarrassingly, almost enough for him to come on the spot. He kept it together and recorded a video in the same position as before, making sure his cock and his lips were in frame. “I’m almost afraid to say, darling. I fear you’d break me in two with that thing. I wouldn’t be opposed to the challenge though. Think you’d have to start by working me open on those incredible fingers. Christ, Alex, I’d probably need three or four before I could take you.”
“Fuckin love that, Hen,” Alex’s next video started. “Love you tellin' me how much you want this huge cock. You take care of me like you said before, and I’ll take care of you, just like this…”
Alex’s voice trailed off in a moan as he fucked up into his fist one, two, three more times before he was shooting a massive load all the way up to his hairy chest. Henry listened as Alex whined and grunted what sounded like, “Fuck yeah Henry. Fuck, take that dick,” and that was what sent Henry flying over the edge as well.
He was coming before he knew what hit him, spilling his own release over his hand, and dripping onto his stomach. Alex’s video finished with him turning the head of his dick directly toward the camera, showing Henry the twitching hole that was still trying to squeeze every last drop out of Alex. Henry’s own cock jerked helplessly in response, milking him for everything he was worth.
Finally, he had the brain power to take a video to respond to Alex. His cock was softening in the lower half of the frame, foreskin rising back up to cover the head. His stomach was covered in his own come, and as soon as he hit the record button, he swiped his fingers through the mess. “I’m sorry I was a little late on the recording, love. How could I resist the obscenity you’ve just sent?” He brought his fingers to his lips and sucked them clean, hoping this would have the desired effect on the young man. “Mmm,” he moaned around the digits, “If you were here, I’d be making you lick this up. You’d be a good little pet and do that for me, wouldn’t you?”
He hit send. This was probably the most outrageous exchange he’d ever had over text, and he already couldn’t wait to explore more of this with Alex.
Speaking of the young man, Alex’s own video response showed his full face, eyes sparkling and soft in his afterglow. He smirked as he pulled his own thumb into his mouth and sucked on it pornographically.
“Bet we’d taste good together, baby.” He winked, and the video was over. And so was any chance of Henry backing out of this arrangement.