Size Does Matter

Ok people, sorry to say but size does matter.

“Is he in me”? If you have to ask yourself that question during sex, then he is just too small…sorry. But to be quiet honest, I’ve only thought that like once or twice before. That is only because I learned how to stop the sex or divert it from anal penetration after seeing the size of the guy. Date number 2? I think not.

When giving head, it’s always nice to have at least a handful. This measurement is nice because it is so arbitrary and just depends on how big your hands are. I’m a big boy at 6’4″ and 200lbs so I guess my hands are a touch on the big side of the spectrum. It’s just nice being able to grasp a daddy dick and at least suck/lick the head simultaneously.

I’m a bottom who loves the feeling of a nice, thick, daddy dick in my ass.  On that note, I think girth ranks higher on my list than length. What’s the point on having a stiff noodle penetrating you? When the whole point of anal penetration is pressure on your prostate, you need enough girth to achieve that pressure.

Last thing, whatever penis we are talking about here, I think the most beautiful packages are those in proportion. It’s just nice to have proportionate things. Penises are no different. Proportion to the balls and proportion to the body, as well as girth to length ratio.

Call me a size queen. I prefer selective.


Will it ever work?

For a young man who is into older men (daddies), this has been a question that has haunted me ever since I came out of the closet at 22. In my experience this is a also a question pondered by daddies as well…at least the ones I’ve either slept with or dated. Can an intergenerational relationship be a long term relationship? or is it doomed from the beginning?

Firstly, I define intergenerational dating as dating between two persons that are at least 10 years apart. Simple. And if you haven’t figured it out yet, I’m talking about gay male relationships. 

I am 26 and I am attracted to men between 40-55. Is that a crime? No. Do many people look at my relationships or choice of men and ask “why”? Yes. Sorry… I’ll save that for topic for another day. Back to the question “will it ever work”?

I think the bottom line is that both parties must be on the same page. If I want a long term daddy, he better want a long term boy to be with, and visa-versa. It doesn’t feel all that good if you are just somebody’s flavour of the week or month. But if that’s what both parties want, then go for it. I’m currently into trying all the flavours I can get my hands on, or should I say mouth? 😉

In my experience the biggest challenge to intergenerational dating is the income gap. At the time of this post I’m an unemployed university graduate with a manageable, moderate debt load. For many daddies, this is very unattractive. I get that. But for me, I’ve only ever liked older guys. It’s not like I just switched one day when I became unemployed and am seeking to be taken care of or to become someone’s houseboy. Quite the opposite actually. I have my own goals and dreams and just seeking a nice daddy to share that with and to offer some guidance and wisdom along the way.

On that note, I think that’s a key theme for successful intergenerational dating….a daddy interested in mentoring a younger boy and a younger boy looking for the mentorship of a daddy. This can lead to interesting power dynamics in the relationship, so I think it’s important to be aware of them and to openly communicate one’s feelings. But again, if both parties are on the same page in terms of dominance, then we’re good to go.

“So when he’s 80, you’ll be 60. You’re ok with that?” I hear this or something similar all the time from my friends and family. My simple answer is “Yes”. For me this question is silly on so many levels. For starters, I’m currently 26 so if I make it to 40 with the same guy, that’s 14 years of being happily partnered! A huge success for me….lol. I can barely make it to date number 3 as of late, let alone 14 years! lol. Second, relationships are fluid. After that many years maybe the relationship will open up. Who knows. (note: i’m not into open relationships at the moment). And lastly, they are implying a 20 year difference is a bad thing. Why is it? The sex? Active stuff? I don’t know what they have in mind when they ask, but I know that I will have my own life outside of my relationship with a long term partner in terms of activities and hobbies. So the only thing I could see being an issue is the sex thing. But I’ve seen plenty of home made porn with silver daddies in them, so I’m not too worried about the sex later in life. 😉

In summary, If you want a relationship to work, it will work. No relationship is easy and requires input from both sides. Any type of relationship has it’s challenges, intergenerational dating is no different. It’s important to know what each other wants before getting involved at any level as well. If you want to date, say it. If you want a long term relationship, say it. If you just want to fuck, then say so. 😉

What other major challenges have you faced when dating outside of your generation?