CuriosityKilledTheCat

5 hours ago, nate_sf said:

Hiring a guy to try or learn something new is a great idea. Like @DWnyc mentions, it is a good way to try things without the pressure or reactions you might get from a guy you've met on an app or somewhere.

Let the guy you're hiring know what you want to try and learn, and let him know you're being truthful (so he knows it's not just a "first time fantasy" ploy, though he'll figure that out soon enough).

I'm curious though why you say you are feeling pressure to fuck. Don't do something just because you think everyone is doing it or it's expected. There are plenty of things to do besides fucking, and lots of guys are just fine with that.

But then again, fucking can be really awesome, and it sounds like you have a guy in mind who you'd like to try it with. You can do it.

I suggest you post in the Deli forum asking for recommendations for someone to show you the ropes, and be sure to say where you are located. I'm sure you'll be able to get some recommendations.

Thank you for taking the time and giving me your helpful perspective.  The truth is, if there wasn't someone I like who I know is into getting fucked, I wouldn't be inquiring now.  I am relationship-oriented, so I feel like you should stray from your comfort zone to ensure your partner is accommodated.  I kind of know it's not right and I shouldn't, but I somehow feel insufficient for not having engaged in anal before.  Then I see 20-somethings who have done it hundreds of times, and I feel like trash, haha.

Thanks again for your advice.

Good evening everyone -

    I am a decent looking 40-something in athletic shape.  I've been with guys before (making out, oral, frot, j/o), but never fucked.  To be honest, I've never had the urge to.  However, I feel some kind of pressure to do so.  There's a guy I like, and I know he's a bottom.  I don't know "how" to top, and I don't think I could ever be a bottom.  I was hoping to perhaps hire someone to "teach" me this skill of topping and was looking for guidance or suggestions with this.  Thanks!

- J