Between a Fag and a Hard Place LOL

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Benjamin
Dec 02, 2025 03:56 PM 0 Answers Ask A Question!
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Hi Sam,

My name is Arturo, 35, bisexual Alpha. I've been married to a woman and had 2 relationship with submissive men. All of them were great and one thing in common: I am always the Alpha and they were all very good subs for me.

But now I have a tricky situation in my life. I am single and went out a few times with a very nice woman. Her name is Julia, 38, great body, nice boobs and ass. She really knows how to ride dick and give me head. We have been thinking about having something more serious, but haven't yet decided on becoming official boyfriend/girlfriend.

Since I am still single, I always hunt for girls and fags on apps. Last week I met a really sexy twink on Grindr. 21 y old, total faggot. He texted me saying he was horny and sent me an ass pic. I don't usually fuck guys his age, I usually prefer fags over 30, but I was too horny and he had a great ass, so I didn't even ask for his name, just sent a dick pic and my location. In 30 minutes the fag was on his knees in my living room giving me head. I fucked him on my couch and shot a nice load on his face. The slutty twink looked at me after I finished on his face and used the tip of his finger to move all my cum from his cheeks to his mouth. What a sexy slut.

We took a shower together, had a nice time, and then I asked for his name. He said "Leo", I introduced myself as well during our shower together, and before leaving my apartment he asked if he could follow me on Instagram. I said yes because I was already planning on fucking that boy pussy again. When I followed him back, his first pic was a birthday cake with a "21" candle on top of it from just a few weeks ago. Then I thought "wow, he just turned 21 and sucks dick like a pro, he's a natural born cocksucker. The next picture was himself holding his birthday cake and my sexy Julia was kissing his right cheek. I was really surprised to see her there, and thought that they were probably friends from work or from school.

Imagine my surprise when I saw the description of the photo saying "thank you for everything you do for me, mommy. I will always love you." I couldn't believe what I was reading at first, but it all made sense when I put things together. When I told Julia in our first date that I do not have children, she told me that she had a "little boy", and that her first boyfriend from high school impregnated her and disappeared and never met his own son. She looks much younger than me, so in my mind, although I knew she was 38, I imagined that a boyfriend from high school would have been no more than 10 or 12 years ago, so I thought her "little boy" was an actual little boy, not a slut begging for cock and cum on Grindr LOL But everything made sense: She is 38 and got pregnant in 2003. Leo is 21 and was born in 2004.

I panicked for a few minutes, texted Leo and told him the truth. He was shocked when I told him that I was bisexual and was going out with his mother, but he didn't get mad at all. He just said that it was not my fault and that he had no idea either, so I should not blame myself. He got playful in our messages and said "well, now I can call you daddy beyond the bedroom", treating everything as a big joke, but I was really panicking with this situation. I wanted to take that woman for me as my partner in life and I had literally fucked the ass of her son and shot a big load on his face.

I don't know if I am too old-fashioned or if Leo is a total slut, but he is seriously considering that we can still see each other and just pretend nothing is happening. He wasn't embarrassed at all to say that he would be really happy to see me with his mother, but if I need a relief his ass would be available for me too. Then he said "I love my mother, I just want her to be happy and she deserves to find a nice husband to take care of her, but I also know that you are a man and you have your needs, so what's the problem?"

And now I wanna hear from you, Sam. I 've been following your work for a while, and your opinion matters a lot to me. I know it sounds like a gay porn plot, but this is literally my life right now.

Just a final observation: Julia hates taking facial and she doesn't do anal at all, while Leo has an amazing fag pussy and loves feeling my cum on his face. And shooting my load on another person's face is by far the thing that turns me on the most, maybe even more than breeding (although I love to breed pussy and ass). I know I am sounding selfish and you can call me an asshole for that, but the thought of having a nice smooth ass to fuck and a fag always willing to take my cum on his pretty face makes me hard, I'm not gonna lie.

In your opinion, if I decide to be with Julia but from time to time dump a load inside Leo's ass, is it too big of a risk that Leo will just tell everything to his mother if he gets upset for any reason? Most importantly, do you believe that nature gave me the right to have a beautiful woman by my side while also keeping Leo as a side cumdump, or am I an asshole just to think about it? Leo is VERY open to be his stepfather's cumdump, so for him it wouldn't be an issue at all. But I am the one who should make the decision.

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