Straight 24-Year-Old Answers Your Questions About His Engagement To Wealthy Sugar Daddy

A Reddit user recently took to the anonymous online forum to conduct a comprehensive AMA (Ask Me Anything) thread titled: “I’m a straight 24 year old male who is engaged to a wealthy 51 year old man. I’m in it for the money (and he knows that). I have no interest in a relationship with a woman, so I figure why not. AMA.

The young man received hundreds of comments and questions from curious members of the site. Here are a few of the questions he answered:

Do you have sex with each other?

Yes, we have sex.

Do you engage in one night stands with women?

Yeah, I can still hook up with women just so long as I don’t bring any home with me. So either at their place or a hotel or something.

What’s the point of getting married without a romantic connection?

You’d have to ask him I guess, since I’d ask what’s the point of a romantic connection in the first place. FWIW I kind of fake one for him, although he knows I’m faking.

Are you the top or bottom?

Usually I bottom but sometimes he wants me to fuck him.

One user asked how much his ‘sugar daddy’ was worth, to which he estimated he had somewhere in the neighborhood of 11-12 million dollars.

The revelation led one user to ask the following questions about the pitfalls he might face if his sugar daddy lived for another 20, 30, or even 40 years:

Do you swallow? Would he be considered handsome by other gay guys his age? Do you worry that you may get too old for him and he’ll divorce you for a newer model?

Also, are you ok fucking a guy and being married for the next 40 years of your life (in the case he lives to 90) for the final payout?

Yeah, I swallow if he finishes in my mouth. I’d guess he looks alright for his age but I don’t think most younger gay dudes would be throwing themselves at him (although who knows, the younger-older thing seems to be kind of a thing for gay dudes). He actually seems to be more about the “relationship” than just having sex with younger dude so I’m not too worried about that.

Yeah, I’m pretty okay with it. Plus I don’t have to work now and I can afford to buy whatever I want (or rather he can afford to buy whatever I want).

Related: Confused College Bro Asks Internet For Advice After Spontaneous Gay Hookup With Best Friend

And then, there was this fascinating story by another straight man who had a similar experience as the 24-year-old original poster.

(Throwaway) Straight, male, always and forever.


I had an “opportunity” to be in this position when I was in college. Old guy, 78, would always come into my work, (every day) and talk to me. Figured he was just lonely, wife had died, no kids, etc- just a rich geezer with nothing but time… or maybe nothing but free time with the time he had left.

Got to know him pretty well after about a year of daily small talk. He grew on me- he was a good guy, and slid me $5-$10 each time as a ‘tip’. He’d tell me about his 5,000 sq ft. fortress down the road at the top of Mount Blah Blah Blah; his steam room, indoor/outdoor pools, etc. etc. etc. He’d bring pictures, which surprised me each time- I think he could tell I didn’t fully believe certain things he would claim to have, as it would generally be the next day that he’d shock me and bring in proof. His shit was nice- easily one of the most well decorated Mountain Cabin/McMansions … kind of a Davey Crockett Chic I guess.

Anyway, one night I was walking out to my car after closing, and he was there parked beside me. Kinda freaked me out, not in the “oh no what should I do? Halp!” way but in the “Hey man!? What are you doing creepin around here ya old fart?!” He started telling me about his declining health, (which I had known nothing about until then) and was talking about needing a caretaker.
More or less: “I’ve got 6-12 months left, 10% chance I might get 2 years. I’m not going to a home/hospice and I need someone to take care of me, someone I can trust. (This bold part is verbatim) Also, I haven’t told you this, but I’m gay. I don’t know if you are, and I couldn’t care less. I have nothing left to lose, I’ve lived a full life, and I’D TRADE IT ALL TO SPEND THE REMAINDER OF IT WITH YOU. If you can fully commit to giving me this happiness, we can drive to [his lawyers in the next city over] and sign all the paperwork to transfer everything into your name. You’ll be surprised how much this is- you will be set for life. All you have to do is give yourself to me while I’m still alive.”

During his 5 minute speech, (that he clearly had practiced) I was initially smirking with confusion. I remember feeling my jaw slowly drop against my will as he progressed through his spiel. He recognized me awkwardly shifting my weight around, but powered through completely undeterred like a man on a literal fucking mission. When he stopped, I was uncharacteristically silent for about 15 seconds, and while this guy starred into my soul, I reached in to start my car to let the engine warm.

I can’t remember exactly how I said it, but Tl;dr: “First, I’m sorry to hear about your health; also, I think I appreciate the compliments and that you drove up here tonight to tell me this. I’ve had a long day, I’m going to go home and collect my thoughts, ok?” Shook his hand and left and quickly as I could.

The main road looped around the parking lot, so I had a view driving back by half a minute later of him standing in the same spot. The image of his motionless silhouette broke my heart/creeped me out in a way that nothing else had before or sense.

I got home, didn’t tell my roommates anything, went to my room. Rolled a blunt, grabbed my Makers Mark and climbed out my window and got fucked up laying on the roof with only my thoughts. I had a life changing option at my disposal, and these kinds of things don’t happen often- when they do, it’s usually without any warning and lacks choice.

I ran through so many scenarios/what ifs/etc, setting and breaking hypothetical boundaries in my mind.
Assuming I agreed:
What if he’s lying about being sick and lives 10 years? What if he’s lying about money? I’ll tell him it’s all conditional upon me seeing proof from his doctors/lawyers/financials/etc. What if I couldn’t go through with something halfway through “it”? What if I’m over thinking this and being unfair? What if this scars me the rest of my life? What if I like it, wait, am I gay? What if this ruins my future? What is my body worth to me anyways? How bad is it to just let someone entirely rent you for the next 6-12 months? What’s it like to be a commodity?

Assuming I decline:
What if I regret not doing this for the rest of my life? What if I never get another break in life again, and this is my golden ticket? How bad is it to just let someone entirely rent you for the next 6-12 months? What’s it like to be a commodity? What if I can’t say no, because he won’t let me? What if he’s NUTS? The lonely old guy who comes to your work talks to you everyday just showed up at your car after work and proposed to you, offering his fortune as a ‘dowry’… so yeah he’s nuts but what kind of nuts? Is he stable? Will he stay mentally stable? Am I at risk here? Who should I tell, and how??

What if I’m a fucking retard, spun on my roof trying to figure out how to answer a wedding proposal from a Male Scratch-Off Ticket because I’m dreaming and I’m about to wake up and none of this was real?

So, next day, he comes in around the same time, I tried to be normal and not address it initially, but he clearly had one thing on his mind– he had to know. He was different, I mean, completely understandable given all this, but this was a solemn different. I hadn’t decided overnight, and I had a running list of questions I had planned to ask him. I was in the middle of telling him about spending the night on the roof, and was about to suggest we grab a beer next-door once I was off work so I could get ‘details’ when he said softly, “If you can’t answer yes right now with before you draw your next breath then I know your answer and it’s fine”.

I was taken aback at how his tone almost felt sharp, and stammered a bit, searching for my words and just like that, he stuck out his hand.

I slowly shook it, confused.

“Take Care” he exhaled, turned on his heel and waddled out before I could respond with anything other than my default “Aright then, have a good one, see you tomorrow.”

I was shocked, relieved, sad, confused, and kinda hurt; especially as it began to dawn on me over the following days that his absence was going to be permanent. Since he’d started coming to my job every day, he literally hadn’t missed a day, rain, snow, shine. And just like that, he was gone- without any prior indication. I checked obituaries for a little while, but never saw him, which was probably for the best. I’ve thought about how different my brain’s thought were over that 18 hour period of time, and it’s somewhat unsettling to remember how drastically my life might have deviated from it’s current path, for better or for worse.

I’ve also thought “What if this guy was just the biggest troll nobody had ever heard of, and he knew it would fuck me up later in life to think that I had even considered being his Anna Nicole Smith or whatever?” Anything’s possible, but recalling everything prior to that night, eliminates that completely for me.

The worst hypothesis I’ve had, (one that I find new ways to repudiate each time) was that he drove straight home, took a bunch of pills, and drifted off in his prized steam room. That’s really why I checked the obituaries, and I’m glad this scenario never panned out- although I’ve had a few nightmare’s where I learn he’d just been decomposing in that sauna all this time and nobody had known.

Related: A Bisexual Man With Two Penises Answered Questions On Reddit AMA

h/t: queerty