Hi Sam,

I have a question but I feel like I need to have a thorough explanation of my background to get to it, so if you wouldn’t mind, I’ll tell my story here.

I’m a 54 year old man who is married to a woman for 25 years now.  Seven years into my marriage I got curious about gay sex; I guess, that seven year itch was a real thing.  Anyway, back then, all I knew of were the personal ads section of Craigslist under Men looking for Men.

I would read personal ads there and those were enough to get my fantasy going – these would be enough fodder for me to jerk off with and I’d be good for a while.  A while changed drastically from a few weeks, to a few days, to a few hours.  I ended up spending so much time on Craigslist that I knew most of the frequent posters already. Eventually, even the ads that I would find hot would progress (or regress) from just imagining some local guy in my area getting it on with another man to more kinkier stuff — like, those involving BDSM.

Eventually, one specially horny night, I ended up replying to an ad from a Dom Master who was looking for “students” for a “submission class” he was forming.

I was surprised when Sir reaponded. We corresponded for several weeks and Sir was disappointed there weren’t enough responders to his ad but he was happy to at least have me.

His domination over me took several more weeks online (think email, not apps) before Sir had me meet him at a motel.

I was told to wait for him naked and prostrated on the motel room floor, head against the carpet and told not to move.

It was a day of many firsts for me.  I became a cocksucker that day, a piss swallower, and a cum bucket. Though, Sir left me an anal virgin still. And all this transpired while I was blindfolded.  So, I haven’t even seen my Master’s face then.

It was only after a couple more in person sessions that I finally saw his face, it was when he took my ass pussy on my marital bed without my wife ever finding out.

My last session with him, he had me spend overnight and him and his friends used me several times in so many ways I hadn’t even imagined possible.

After having experienced nothing like it in my life, one would think I would have found my calling then and started a new life as a faggot.  But that wasn’t the case, I soon found myself reeling in shame and guilt.  I swore off all faggotry and even anything remotely gay. Though I wasn’t always successful, I was determined to stay straight for the rest of my life.

Now almost two decades later, I find myself back where I was. Instead of Craigslist, there are apps now.  And just like before, I was just a voyeur to the chats and groups and porn, I slowly started chatting, then sending pics and vids of me here and there. Next thing you know, I am serving men again, albeit, all online only.

Thing is, I found a Dom who is local and he is naturally dominant and seems to understand my situation well.  He wants us to meet, he wants to use me in person. He promises to use me as the faggot I was meant to be.

Part of me wants to meet him. But I am scared.  I don’t know if I want to actually meet this Dom only to feel the same guilt afterwards.  Also, I don’t know if I still have it in me to be the faggot that Sir deserves.  After all, I am much older now.  Is it like riding a bicycle?  Will I again naturally know what to do and be able to do what Sir asks if me? Will I still be able to take what Sir plans to do to me?

He is open to discuss the situation and we have but I am still apprehensive.  I don’t want to ruin the life my wife and I have built but also there’s this opportunity that I don’t often have.  What advice can you give this closeted faggot?

Thank you

Thank you for the question!

I will say that being a faggot is just like riding a bike. You don’t forget what your purpose is or how you’ve been trained. It just takes re-engagement.

Your feelings of guilt are natural, especially for fags in your situation. And frankly, that’s probably healthy for you. 

But what are you trying to protect at this point? You already risked your wife and marriage years ago.

I think the shame you’re feeling is the same shame that led you to marry a female in the first place. That shame is still making your decisions, unfortunately. 

I have little confidence that you’re going to make a significant change in your life and actually experience the fulfillment of this purpose that has followed you throughout your life.

My recommendation is for you to put this away and forget it. Just live the rest of your life in the trajectory you’ve already charted for yourself. It’s simpler, and will cause you the least anxiety. 

Have a question? CLICK HERE to ask!

An update of my situation dealing with my previous hometown friend.  I appreciate the advice you gave but just wanted to give some clarification I don’t think I ever saw myself as an alpha even tho I was a vers top I just saw myself between an alpha and beta-dom just unlabeled until this point in time.

Since college ended for me I returned to my hometown for the summer where he’s no longer my neighbor but still not too far away. When I got back I actually ran into his mom at the grocery store and found out he’s actually going to the college I just finished. It gave me the perfect excuse to dm him because I was honestly stressing on how to casually text him after so long of not keeping contact.

So i ended dming him about college and we just caught up for a while him asking about my college and me asking how high school has been since I left and actually got to making plans to hang out for a family dinner. Eventually, I mentioned how I saw his gym pic and how hes so lean and muscular and that he should train me at the gym since he has a better physique and looks stronger than me now. His response caught me off guard as said “Man yk I’ve been stronger than you since I was 14 remember when I beat your ass when you were a senior lmao” but played it off as a joke. I took your advice and agreed with him saying it definitely taught me a lot about myself before he asked what I meant. I didn’t elaborate on this in my first question but despite being a vers top a lot of the bottoms I fucked were power bottoms. Even though I didn’t like being degraded or dominated I realize now that after that moment in high school I subconsciously took a more passive role or at least less aggressive role in sex and also a lot of rope play I think came from me being bound the first time.

I didnt tell him all this yet but just said that it brought up submissive feelings in me where I liked helping other people achieve what they needed. He probed further and asked me if that meant I just liked being a loser. I admitted that I felt that way in his presence and he left me on read before texting me to go over to his place to talk out of no where. I was curious so I did when I arrived he immediately kicked me down and chokeholded me before moving onto different positions making me tap out multiple times. By the fifth time or so I finally caught my breath to ask what this was for and he said thus is what you wanted right and he’s doing this because he enjoys the thrill of making another man submit to him. At the end he had me bow down to him and verbally say that he was a better man than i could ever be. Before I left he said he had heard of guys liking being dominated from his friends and found it kind of hot that he had someone older he used to look up to be groveling at his feet.

We haven’t talked more as I think I am and he is figuring out what to make of all this. I won’t lie I still think I might be a top but just him specifically makes me so submissive and while his physique is impressive it isn’t the best yet I literally can’t stop staring at his abs. Is there anything I can do to proceed to let him know what more he can do.

This is a follow-up to THIS QUESTION.

Thank you for following up on your previous question! 

I commend you for trying some of what I suggested to you! I’m sure it wasn’t easy! 

The last time we spoke, I said this: 

“So i recommend that you write to him (you could call too, possibly) and feel him out. Be complimentary about his physique, and toss in some commentary about that incident. Be complimentary about his power, and hint that it was a major turning point in your life. Chances are, he’ll pick up that hint and want to know why. 

At this point, you’ll need to be a little brave and admit that the incident awakened submissive feelings in you. If he’s Alpha (as I suspect), he will pick that up and run with it.”

Obviously I nailed it. This is almost exactly what happened! In fact, he was straight-up telling you this when he said he “found it kind of hot that someone he looked up to would be groveling at his feet”. In fact, I think that entire final episode when he called you to come over and he wrestled you multiple times and asked you probing questions about your feelings was the opportunity he was giving you to admit what you are. The fact that he told you his Alpha friends have been talking to him about guys like you is a HUGE sign that he was probing you! 

Even though you did a good job in telling him his presence made you feel submissive, you held back too much. He was looking for something more explicit. When you didn’t outright confirm what he thinks you are (a faggot), he didn’t feel like he should push it. However, I do firmly believe (based on what you said happened) that he did, in fact, want you to admit to him that you’re a faggot.

You just didn’t take the chance.

It’s not over with if you still want to serve him. I want you to start a conversation with him (either text or voice) to tell him that you’d like to talk to him about your last encounter. When he invites you over, you kneel and kiss his feet. Ignore the resistant voices in your head and do it. He obviously wants this, and you’re going to give this to him. He’s going to ask about this, and you’re going to tell him that his power made you realize you’re a faggot. USE THE WORD, BE SPECIFIC. 

He’s going to know exactly what to do with you then. I promise. 

You can keep telling yourself whatever you want to believe about what you thought you were in the past. That’s all gone now. He’s a much more powerful Alpha – a true Alpha – and you need to finally submit to him and offer yourself.

He wants you to do that. 

Have a question? CLICK HERE to ask!

To my ears it sounds like my Man @ShawnMendes is trying to tell us he’s gay. Ordinarily a purely straight Man in his twenties doesn’t have this much conflict about whether or not he likes girls.

It’s okay, Shawn! Gimme a DM and I’ll help you!