One of the first questions I hear from ladies who are new to the concept of Pegging is, “Doesn’t it hurt?”

Now these might be ladies who have yet to explore posteriors in any serious fashion – either their own or the posterior of their partner. Yet sometimes I think that reaction is a direct result of their own ass having been at the receiving end of rushed and inexperienced fingers/cocks/toys.

It may indeed be a thrill (for both parties) after indulging in extended foreplay to thrust a cock fast and deep into a slick and wet pussy. Awesome. Just don’t try that with an ass…because all but the most experienced in anal play will probably experience pain, no matter how copious the lube. Key word for anal exploration…slow. Take your time, tease that puckered little hole until you can feel your partner pushing their ass back wanting more. You want them reaching for it, hot for it…because it feels so good. Take…your…time.

So how exactly does one go about teasing an anus? Thought you’d never ask.  Next time…”The Basics of Rimming”.

Thought for the day: Yes, a woman can fuck her man in the ass with a dildo and still be a “lady”. In fact the contradictory nature of combining the two can be seriously hot! “Madonna/Whore” much?

Some prefer their dildos to look realistic. Others enjoy finding one in their favorite color. This is the “Mistress” in shimmering purple by Vixen Creations. 100% silicone. And that’s me wearing it.

Ruby Ryder


  1. Ruby I may need some help. Background. I have several family members who have been diagnosed with prostate cancer. I saw my Dr and he diagnosed me with BPH. His suggestion was prostate massage. After talking to my wife she was not super comfortable with the concept. We watched a video and they suggested using a strapon. That is what led us to your site. After listening to podcast 102 my wife came away believing that because she is a larger woman we need a very long appliance and has since ordered the Tommy Gunn cyberskin dual density. The diameter of this kinda scares me. What do you suggest? Amul Nitrate? I want to enjoy the benefits of the prostate massage but don’t want to be in massive pain. Is there a thinner option?

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