Sep 17 2013

Podcast #63

Pegging Paradise Podcast #63

❤ A refresher course on cleanliness
❤ The phone line is working! Call me!
❤ Where can I find a woman to peg me?
❤ His girlfriends sounds down with the idea but how can he let go and vulnerable?
❤ One more thing about where to find a women to peg me!
❤ Classes 9/22 & 11/3
❤ Bawdy Storytelling Los Angeles 9/25
❤ CatalystCon - Sparking Communication in sexuality, activism... 9/27-29

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Rating: 10.0/10 (1 vote cast)
Podcast #63, 10.0 out of 10 based on 1 rating


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  1. Hi Ruby,
    I am a 66 year old straight man who is investigating pegging with my wife of many years. She is open and willing and I have now been pegged a couple of times with less than stellar results.

    Maybe I am expecting too much. I am looking for this prostate orgasm, more intense than the normal “stoking penis orgasm”.

    We have used several approaches. Often we start out kissing and warming up with fingers. I find it interesting. However, my erection is not reliable. ( Usually reliable in M/F PIV sex) I may get erect but by the time we switch positions and get inserted I am flaccid. The missionary position is comfortable but I do not feel a building of urgency after 10 minutes.

    We have tried fingers, and I have tried an Aneros massager (30 minutes). All seem interesting but not erection generating or orgasmic. I should add that since my youth I have masturbated to orgasm stroking myself while wearing anal plugs or dildos.

    I would appreciate any suggestions.

    1. Interesting. Prostate responses differ for different men just as not all women have much of a G-Spot response. Could be that since you have been using anal stimulation when masturbating all along – the sensation you perceive a normal might be the extraordinary one for men who are new to prostate stimulation. And while the hands-free orgasm is held up as the “holy grail” of pegging, my best guess is that the same percentage of men are capable of having one as women who can attain a G-Spot orgasm without clitoral stimulation (around 30%). And as far as erection generating – prostate stimulation is not supposed to be erection generating! It is for some men, but other men have erections that come and go and other men cannot get an erection at all when penetrated. ALL THOSE examples are normal!

  2. I love this podcast format Ruby. Your whole being comes through you and I appreciate you sharing your journey. I felt like I had been wrapped in silk on a visit to an exotic destination. Enjoy the conference 🙂

    1. I so appreciate your kind words, Bonbooty…as well as the beautiful visual metaphor. CCon, here I come!

  3. i would love to get pegged by a hot strapon chick or two. they have to spank me first.

    1. It is good to know what you want – and how many!
      I love how clear you are about your prerequisite of spanking as a precursor to pegging.

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