That First Time!!!

Hi T,

I heard about your blog from Instagram, and decided to hit you up since you keep things anonymous and all.  I’m not really out the closet or whatever yet, and don’t have friends I can ask about this whole gay lifestyle, so I’m coming to you.  Here’s the thing.  I’ve never had sex with a man.  I’ve always wanted to, but never did because I knew what that would mean.  But now since I have started to accept that I like men, I think I’m ready.  I started messaging back and forth with this guy I met on one of these apps, and we’ve been talking about meeting up.  Crazy thing is, I’m really nervous.  I probably shouldn’t be because I’ve had sex with girls, but I am.  So do you have any advice for a virgin gay?  I mean what was your first time like?


Gay Cherry Poppin

Hello there,

And thanks for writing to me.  I find myself laughing as I write this response, thinking about my very first time with a guy.  It was a bunch of poking and prodding, a lot of awkward moments, and some ill placed laughter.  I would spare you all the details, but since you asked, here you go.

Picture it! Junior year of college! Barely the big 2-1. (Yes I’m speaking in my Sophia Petrillo voice LOL). This freshman I had been mentoring for a few months one day told me that I had been naïve.  He said he had been flirting with me for a while, and I hadn’t been paying attention; so, he decided to just tell me he liked me.  To be honest, I didn’t even look at him in that way until he said something.  Once I “opened my eyes,” I realized that dude really was fine.  He had a gorgeous smile, surrounded by the sexy grown man goatee, nearly flawless bronzed yellow skin, and a butt one could bury his face in and suffocate.  Thought I try to give you a visual of my first, who I now will refer to as BC.

Anyway, after a week of talking and setting things up, the night came when BC was supposed to come over to my student apartment.  I remember spending so much energy planning that evening.  After all, it was not only my first time with a man, but his as well.  I had sent my roommate away for the night to his girlfriend’s place, because I didn’t want to worry about being caught in the act.  I went to the student health center that week and loaded up on items for a quasi-safe-sex kit.  I mean I grabbed condoms, lube, and dental dam.  And not knowing that much about the whole enema thing, I nearly starved myself that day so I wouldn’t “paint” if I allowed him entry, if you catch my drift.

Once I let BC into my apartment, we made some small talk, then got down to business.  We started making out right there on the sofa in my living room.  Shirts began flying off, and penises stood at attention.  I stopped kissing him briefly, only to lead him to my bedroom.  And that’s where things got awkward.

We attempted to perform oral sex on one another with the dental dam, and had no idea what was going on.  I remember draping it over his “fun stick” and thinking how it looked like I just covered his piece with a Fruit Roll-Up, except let me assure you, it didn’t taste like a Fruit Roll-Up.  And then when it was time for the real intercourse, I remember taking my thing and just shoving it in there.  I mean the grunt he made when I did that was nothing sexy at all.  So I pulled out, and attempted to reenter his hole only to poke him in his balls.  LOL!

The kicker of the night was the explosive climax.  I wasn’t use to another guy’s semen on me, and I didn’t want his juices on my sheets.  This is embarrassing, but I’ll finish sharing my story.  I actually made him bust the infamous “nut” in the plastic trashcan next to my bed.  I’m just thankful for evolution and maturity LOL! I can now say I’ve improved greatly from that first night, and no longer offering up trashcans.

Going forward here are my suggestions.

  1. Don’t go into this encounter thinking just because you’ve had sex with women, that you are going to be a pro at having sex with men. Typically, the anus is tighter than a vagina, so you can’t ram your thing up in a guy like I did.  And just because you’ve had sex with women, doesn’t mean you were good at (no offense).  However, try to go into the situation with just the right amount of confidence and humility.
  1. Remember safe sex. Use a condom!
  1. Don’t rush into having sex with this guy. Take your time and get to know him.  You may discover that you don’t want to remember him as being your first.  Well first man anyway.
  1. Make sure you check out my post on what makes a top a good top and a bottom a good bottom ( ). I think you will find some helpful information.

As always nothing but love,


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2 thoughts on “That First Time!!!”

  1. Gay Cherry Poppin says:

    Yo man thanks a lot! And not a trash can though lmao!

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