Ask Chad Gay Sex & Dating: Breakups, Small Ds, & Horny Roommates

September 15, 2025
ALEXANDER

Ask Chad Gay Sex & Dating: Breakups, Small Ds, & Horny Roommates

Hellooooo, Sexies!

Is it too early to put up those Halloween decorations? LOL. Well, we are wrapping up the pressure to have a pool party summer body just to head into the pressure to have a hot Halloween costume body. Can we ever just take a break and celebrate gaining a few pounds? The gay struggle is real! The truth is, we are so hard on ourselves and our bodies when a lot of us find other guys with some extra pounds cuddly and hot. Let’s just say, my Speedo went up a size this summer. Oh well, I love ice cream. I’m typing this while eating a salad and literally looking at Uber Eats on my phone. Sigh. Anywhoooooo -

Keep those dating, sex, and love questions coming in, Sexy Bitches, I love reading them! Just like my Sniffies profile says, nothing is off limits: [email protected]

Dear Chad,

I hate to admit it, but after dating my boyfriend for 8 years, I want to end it. It breaks my heart, but I’m just not happy anymore, and we fight day after day; there’s no sex, and I’m not feeling the love. I’ve thought long and hard about this, and I want to split. I can’t really pinpoint anything; neither one of us is cheating, there hasn’t been one major thing, I have just fallen out of love. I can’t remember the last time we enjoyed each other’s company. The only thing that keeps me in the relationship is my niece. My sister is a single mom, so I watch my niece a lot, especially on the weekends. She is extremely close to my boyfriend and considers him family, which he has become. She is so fragile, I’m worried what a breakup might do. The only time my guy and I don’t fight is when she is around. What should I do?

Breakup Brad,

Dear Breakup Brad,

Whoa, I usually get crazy or funny questions. This is pretty serious. Sorry you are going through this! You have to do what is right for you; otherwise, everything and everyone around you will suffer. Faking it, or just going through the motions, won’t get you anywhere, and resentment will build up, and you will eventually break up anyway, just probably in a more damaging way. As much as you love your niece, you have to put your needs first; otherwise, you can’t really be present for her. She can probably pick up on the tension between you and your man, even if she doesn’t show it. You can shower her with love and attention after the breakup and help her (and you) get through it. But trust me, sticking with someone you aren’t in love with is perhaps the most damaging thing you can do. It will affect your health, your job, your other relationships, and your own mental health. Get out of it! P.S. If you man hung? Give him my number! I’ll help him through it!

________

Hey, Chad!

I have been dating my boyfriend for about a year now. Sex is important to me, but it isn’t the only thing I look for. My guy is not hung, like at all. There I said it! I’m only a bottom, he is only a top. When we first started dating, he would apologize for his lack of size, and I told him it didn’t matter and that he felt good inside me. I lied. I can barely feel him in my ass and have been faking it. I think I’m done faking it. I need a top that I can actually feel. I love him and don’t want to break up, but my ass needs to be drilled! You know what I mean? What the hell am I supposed to do?

Anal Andy

Dear Anal Andy,

Bend over, I’ll show you a good time. Kidding! (Mostly.) Yikes, I’ve been in this situation. If you care about him, you’ll just have to make it work, or try including a third, or have an open relationship to get that big dick you crave. If you don’t want to open up the relationship, there are still some things you can do. You can add some sex toys to the mix and get a dildo that’s a size that works for you. Using that, with some great mutual foreplay, can make for a hot session. He can even DP you with the toy and his dick so he is inside you, but you can feel it. There are also dick extenders. It’s like a cap on his dick that serves as an extension so that he will feel the sensation of being inside you, but it’s actually part dildo. There is so much focus on anal sex in gay hookups, but there are many other things you can do for a great orgasm. He probably already has a feeling that you are faking it. Just be honest with him in a caring way and tell him you want to spice things up. Getting through this together will make you closer in the bedroom and in the relationship.

________

Hello, Chad!

I have a sexy roommate, and about a month ago, I brought a sexy guy home. We were all watching TV and having some drinks, and then this guy and I fucked my roommate. It was hot and fun, but that was it. We laughed about it the next day and thought that was that. Well, now every time I have a guy over, whether it’s a date or a hookup, my roommate knocks on the door or comes to join us in the living room, thinking threesomes are going to be a regular thing. It’s always uncomfortable when I have to decline, and also some of the guys I bring home are into it, so I feel pressured to say yes. I just want to be with the guys I bring over, just for me. I don’t want to feel like I have to include him all the time. He’s getting pushy and annoying. What’s your advice?

Cock Block Carl

Dear Cock Block Carl,

I’ve never heard of anyone complaining about too many threesomes with hot guys! I get it, though. You want your space, you want your privacy, these guys are your toys, and you don’t want to share. It makes sense. Your home is your safe space, it is your freedom space; you don’t need someone crashing your good times on the regular. You just need to lay down the law and tell him that there will be issues if he pushes it. Tell him if the door is closed or if you have company, that means private time, and he needs to leave you alone. He needs to respect your boundaries. If not, it’s time to evict! Be firm, and just know that since you are laying down the law, you can’t include him anymore, even if you want to from time to time.

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