Newbie Question – Supposed to Feel Good?

A while ago I asked my girlfriend if she would be okay with pegging, and surprisingly she agreed. After that we stopped by a small sex shop to pick out a cheap beginner's harness set, with a tiny dildo (we ordered some lube online). This was all well and good, but when it came down to the act it didn't work out too well. I'm not sure what went wrong, be it the positioning, the harness, or what, but it wasn't really doing anything for either of us.

I guess the point of this message would be to ask for advice from an experienced pegger, in hopes that you could help out two people who have no idea what they're doing. Any tips would be greatly appreciated.

Dear Reader,

First of all, points for you and your girlfriend. You for asking her about pegging. Your girlfriend for being game to try it! First times are usually a bit awkward, so no worries.

Your something that will give you pleasure when she pegs you. I suggest that first you and your girlfriend do some exploration with her fingers. What you want to do is see if she can locate your prostate with her finger.

Here is a chart to help you understand what she will be searching for. I drew a purple line where your finger goes (Hey - it's late and I wanted to have some If the man is laying on his back, the woman's finger should be making a "come hither" motion...sort of like if you crook your finger at someone when you want them to come to you. As the woman you want to stroke the roof of his ass, so to speak. You will feel a small bump. Some say it's the size of a walnut but it can vary. The prostate gland will become much more prominent with stimulation, as it fills with fluid...but finding it when you first start is not so easy sometimes.  If the man is on his hands and knees, the woman's finger should be stroking the bottom wall of his ass. The prostate is located on the wall of the anus closest to the stomach. ( When I do this to my guy, I use my middle finger simply because it is longest, and his prostate is located fairly deep in his ass.) He will know when she finds it (he will swoon) and he can help guide her to the right place. Think of it as a "search and find" mission!

The reason I explained all that is because the prostate gland is what brings the man pleasure in his ass. Becoming familiar with how it feels and where it is will help you experience more pleasure from pegging. Prostate stimulation is a sensation that some men have to get used to. Your prostate will get more sensitive and responsive to pleasure the more you massage it and stimulate it, so no worries if the first couple of times you don't feel so much. Men are all different when it comes to pegging. Some feel intense pleasure the first time, others need to practice a little.'s my guess as to why your first pegging encounter left you fairly unimpressed.

  • It is possible the dildo was too small and didn't reach your prostate. (She can find it with her finger and then try to use the strap-on to stimulate it.)
  • It is also possible that your prostate needs waking up with your girlfriend's loving finger to massage it.
  • It is possible that the position she was using  with the dildo was the wrong angle and your prostate was not getting enough stimulation. (Laying on your back or hands and knees both work fairly well to start.)

As far as your girlfriend not hearing the angel sings on her first try at pegging, some women don't.  There are some lucky ones who can come just from the pressure of the base of the dildo against their clit (has to be positioned correctly and the right harness to begin with). Or they use a dildo that can hold a bullet vibe inside of it and that pushes them over the edge. Other women just like the power exchange, and other things as well. Here are the things I love about pegging. Do I get off? Not yet (working on that). But I am so wet when I am done with him that I'm practically dripping. I love it! Let your girlfriend read that article and it may open her eyes to all the pleasure that can be had from a simple pegging.

In short, practice, explore...have some fun. And do it all while staying in good communication with each other; what feels good, what doesn't...what blows your socks off!

Let me know how it goes....

Happy Pegging,

Ruby Ryder

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