The First Time – Take it SLOW

One thing I have been hearing about over and over lately is couples who rush through the period of time between getting excited about trying out pegging, and the first time the actually do it.

Slow Down!

There is so much to learn and so much to enjoy during that space of time! Not only will you really miss out if you rush through it, your initial experience with pegging might be more awkward and difficult as a result. So many ‘firsts’ happen, too! You don’t want to miss a one.

Erotic Anticipation

I’m big on anticipation. If I could give lovers a timeline to follow from when they share that first exciting moment of embracing the concept of pegging, feeling all that eagerness to explore, to the actual moment of insertion, it would look something like this. (And while this is addressed to the givers, please read on if you are a receiver!)

Sample Timeline

  • For the next 5 or more times you have sex, explore the receivers ass as a part of your foreplay. If you want to try rimming for foreplay, but aren’t sure about sticking your tongue in their ass, try a dental dam – they are sheer and ultra-thin – your partner won’t be able to tell the difference. Use fingers and plenty of lube. Gloves are optional. Take it really slow, make it a sensual experience. Stay in communication and have fun. Giggle and laugh if you feel like it. Sometimes exploring new territory is funny and it’s okay to feel nervous or self-conscious. Go so slow that they are arching their ass back to meet your fingers.
  • Around the 3rd or fourth time, once the receiver can easily take a couple of fingers, use the beginner dildo that you bought for pegging. You can hold it in your hand and discover what angle, depth, and speed sends them to the moon. This is what you will be trying to duplicate when you strap it on!
  • Spend one evening staying in. Pair that beginner dildo with a harness. Now put it on and wear it while you both cook/eat dinner, watch TV, or clean the kitchen. This gets you used to putting it on and seeing how it feels to have a cock! It also teases the fuck out of your receiver to watch you wear it. Heh heh.
  • Finally – this is the night. The receiver cleans out. They have no fear whether they can take the toy or not – that’s already happened. You know what you are aiming for after playing with the toy and your fingers. You are used to wearing the harness and cock and know how to put it on. The blanket is on the bed, because you’ve done this before. The lube is handy, along with a towel, and you are ready to begin pegging…


  • Write and tell me how it went and I will play the music for you on my next podcast!

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