I hope it happens for you, jack. Hint: be chaste for a very long time prior and edging often leading up to it will help too. It's the coolest thing to watch as a Domme, but it's pretty anti-climatic (pun intended) for the sub. Just sayin'.

I like this toy, https://www.lelo.com/hugo, but it mostly edges people than actually milking. It depends on the person.

Still fun.

The Lelo toys are so sleek and elegant in design. Thanks for sharing about this one. Question: does it stay in when the sub is in on all fours or laying down? My experience with the Rude Boy and similar toys is that they slide out and you have to manually hold them to hit the "right spot". If this one stays in better, I am all over it.

That again depends on the sub. Most it stays in, but some, have, erm, been more dialated.

Good to know. Thanks!

Thanks for the good wishes Mistress Ay and for the helpful tips. I am definitely going to find a Domme who is knowledgeable about this. Wish I had a return trip to Atlanta coming up, hopefully I would be able to convince you to experience this with me.

At the hands of Mistress Ayn and the Ladies of FemDom Mansion, i had my first milking experience, albeit unintentionally. Mistress Ayn had warned me that this experience would require much practice and thus was not on the agenda for me but during my birthday gang bang at the Mansion, i discharged - unbeknown to me at the time. i was drained but without any pleasure whatsoever. It was a fantasy come true although different than what i expected. Thank You Mistress Ayn and Her dear Friends at the FemDom Mansion.

Prostate milking to perfection. I love it and hate it at the same time.