Talk To Tippy

Posted on: May 15th, 2013 by Madison Lake No Comments


Talk to Tippy for outrageously honest advice.  Call it the second opinion we all wish we had.  Unabashedley candid and insightful – trust Tippy for guidance with dating, relationship or sexual conundrums.  Yes, you can Talk to Tippy!


My delicious Cats and Kittens,  


We’ve had some interest in a previous topic – how divine.   So, since we’re lathered up, let’s carry on right through agitation, rinse, spin and then…repeat!  



Dear Tippy,


Since your column a couple weeks ago, I pegged my boyfriend for the first time. I recognize pegging’s not for everyone, but I just want to put this out there: if the mere thought doesn’t make you sick to your stomach, you should give it a try!


I’m an average normal woman who enjoys sex with a regular partner but there’s no doubt we wanted to find ways to liven things up a bit.  I had been thinking about it for a while and was quite intrigued that my boyfriend said he would consider it as well.  Pretty progressive for a heterosexual male (accountant) in his late thirties, isn’t it?


I just wanted to report in to say that with the right amount of lube, a lot of time, some humor and a dedication to the art of it all, it was magic.  We were both so turned on when we finally got the hang of it, (which was the second go ’round on the following day) we’ll never be the same.  Please share this with your readers.  Thanks, Tippy!



Beth and Barry Behind


Butt, Mr and Mrs Behind, how right you are!

The best reason to try pegging, of course, is that one or both partners are turned on by it. However, even if that’s not quite the case, the penetration reversal can be a real eye-opener (and other orifice-opener, obviously) for both parties in your standard heterosexual relationship. I feel like it’s a great way to fuck a mile in your partner’s shoes.

Here are some things to consider for each of you:

For the men:

-Things in your ass can feel pretty damn awesome. And if it worries you, it doesn’t make you gay to like having a dildo in your ass. It really doesn’t. It makes you worldly.  Take that.

– However, things in your ass can also feel bad. I feel like everyone knows this on some level, but it bears repeating. Anal sex can be a bit of a camel through the eye of a needle-type ordeal. You’re going to have to communicate very well about how you feel and what you’re willing to try, especially the first time.  Relaxation is the key.

For the women:

-Even for those of us who like to take control and ride our men into sweet, moaning bliss, it’s very different from standard Saturday morning intercourse.  It’s a lot more work. You’ll come to so appreciate the stamina that goes into swordplay once you’ve acted as the penetrating party.

-Positioning yourself in doggy style is hilariously difficult at times. Differences in height can really affect your success. Your best bet is to have plenty of pillows at the ready, for under your knees, then grab the hips and plunge away.  Don’t expect to be successful on the first try.

-Being gentle isn’t quite intuitive. It’s so tempting to start thrusting maniacally, but remember what you’re doing and do it with love.  You’ve got to take it slow. Most importantly, once you’ve passed the first hurdle of even getting tip in, it’s a good idea to just let it sit there for a little while your partner adjusts, then slowly work up to actually getting a rhythm going.  And Lord, if he coughs, you’ll have to start again!

-Lube lube lube lube lube lube lube lube.  You got that, right?

Other things for you both to think about:

Using a stiffer dildo will make it easier to penetrate, but the reduced flexibility in the shaft could make it less comfortable for your partner.

-Once you get the hang of it, try different positions, up, down, over things and my personal favorite, standing in the shower.

-Ladies, you might find that long fingernails are distracting to your lover when you’re trying to drive the bus with a firm hand.  Be mindful.

-Fellows, make sure you’re clean and you’ve been aware of when and what your last meal was.  Oh and a little rimming can be a great way to sensitize the area and help get you in the mood.   Mango flavored lube, perhaps?

Don’t let this be one of the things you regret not doing.  Oh, let’s talk more!!



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