Dating, relationships, The Lifestyle

Be a Top’s kind of Bottom, and A Bottom’s Kind of Top.

Dear T,

I’m just starting to try this whole gay thing out, and I was wondering if you could offer me some tips.  I’ve been in a two month long relationship, and have yet to have sex.  As I prepare to take that step with my boyfriend, I’m seeking some advice.  Like what advice would you offer to someone that wants to be a great bottom?  And actually, what advice would you offer to someone that wants to be a great top?  I think I have an interest in being versatile.

Thanks for the help,

Gay Virgin96


I Ain’t Saying You a Gold Digger, But Are You Messing with Broke…?

Dear T,

I have a quick question.  What classifies someone as a gold digger?  My friends call me that from time to time because I won’t date anyone that doesn’t have a certain amount of coin.  However, I don’t think that makes me a gold digger.  I think that just makes me a guy that has standards.  But what do you think?


Off The Runway89


Supporting What Doesn’t Make Sense!

Dear T,

My best friend has been in a relationship with this guy for about 6 months now, and I can’t stand him.  For the life of me, I cannot understand why they are still together.  There are plenty of reasons for my friend to dump this guy.  For starters, this guy claims to be in between jobs, and has been taking money from my friend for a month.  Then there is the fact that the guy constantly talks to my friend about being too feminine.  When I’m around them both, my friend tries to butch up and be something he’s not.  And to top it all off, dude has cheated on my friend.  I keep telling my friend to dump his ass, but he can’t let him go.  How long am I expected to tolerate this man and not cuss him out?  I appreciate the advice.


Angry Woe

Dating, The Lifestyle

“Yo, Let Me See Your Booty!”

Dear T,

Can you please tell me why sending nudes or partial nudes seems like a must now a days in dating? I’ve tried pursuing things with a couple of guys over the past few months, and a few days into texting back and forth with each of them, they want me to send nude body shots of myself. Are naked selfies just an expectation of building a relationship now?


Chi Town’s Finest

The Lifestyle

Top or Bottom, How Do You Know?

Dear T,

I’m new to this whole gay thing, and kind of confused.  I’ve been doing research, so I know the difference between a top and bottom, but not sure how to tell one from the other.  My instinct tells me if a guy acts like a guy and likes guy things, then he’s a top.  And if a guy acts like a girl and likes girly things, he’s a bottom.  However, the more dates I go on, and the more I’m around gays, the more I realize my instinct is wrong.  Can you tell me how you can tell the difference?


Baby Gay11