Our routine is for my Goddess @n2toys is to strap me down tight on the bondage horse I built. She has been binding me tighter and tighter lately which I Love; last night I suggested I think the cervical collar will also work on me while in the prone position on the horse - so that was added with ratchet straps attached in addition to the normal array of belts around my arms, legs, and torso. My Goddess also used some more ratchet rope attached to thigh cuffs which helped to open me up for access. I remained caged while my Wife first used Her finger to warm me up and then the njoy Pure Wand which She uses in a slow motion right on my prostate and is damn near automatic in milking me, well worth the cost. We also have a large black bowl that is placed below me on the ground to be milked into; we're not into cum eating but it's easier for me to relax knowing there's a container to catch things. Being unable to move at all, caged, and my head held rigidly is already intense; add my Wife milking me and I'm completely unable to do anything at all to prevent my body from being milked is such a major mind fuck!! Really intensifies the submissive feeling for me. I had already spent an appreciable amount of time worshiping my Goddess earlier in the evening, I could not wait for round two of worshiping after being milked like a pet.
How humiliating to be unable to move in any way to resist Her invasion! This takes submission to a much higher level!
Not yet, my Goddess has it planned for the last Saturday of this month - the night before I'm leaving for a business trip. Yep! And I LOVE every moment!
My Queen does not milk me as it is too labor intensive for her. Instead I am instructed to do so almost always in her presence while she videotapes and verbally humiliates me. Typically I am in a sissy baby dress with my diaper pulled down enough that my wee wee is exposed. Since I have tendancy to make a mess while milking my Highness has mitigated that by making me leave my diaper on. There is no need for an enema as any mess created by moving my NJoy wand in and out of my pussy is contained by my diaper and this also keeps my Mistress from being grossed out. Generally I have to be sissy free for atleast 10 days . If so I will dribble out a lot of sissies as I milk myself. I normally use my NJoy wand but I also have a pink glass dildo from LeLuv that works great as well. Honestly if I am nice and full I really do not even need a toy designed specifically for prostate stimulation. A good old fashioned pink dildo made out of silicone works just as well and is more forgiving inside of my pussy. I usually milk myself for 15 minutes or so. During that time I usually drip most of my sissies out but sometimes it comes out a lot in one big, constant leak. My sissies are collected on a pink Disney Princess plate that a baby would eat off of. Once I have completed my milking my wife will zoom in on my face and instruct me to eat my dinner. I must admit my Queen spoils me.
We approach it a little differently. My KH likes to take me with a strap on, and does so fairly often. When I've gone for a while (week or more) without an regular orgasm, I can experience something similar with the strap on. After being pumped for awhile (hitting the prostate with each pump) I will eventually feel something like an orgasm. I have a discharge of semen from my (her) cock, while its still in its cage, and without getting an erection. My wife/KH has noticed this and refers to it as my "girl orgasm". She is turned on by it as am I. She'll start talking erotically, telling me things like, "you must be a closet queer-you love getting fucked. It makes you come like a girl-you even squirt like a girl!" To be clear, she is NOT a homophobe-its just an expression of eroticism for us. And, maybe I am a little bit Bisexual! Anyway, we both get into it, but haven't really looked at it as Milking, per se.