In the various forced b scenes, how often does the guy end up swallowing? Is it sooner or later, or more or less expected on the first or 2nd scene?

No condom, always swallow.

Clarification and not all will agree. Having a condom used is the same a sucking a strapon. Just my opinion.

Not safe to do in the real world today but in my fantasy it would be with my Mistress arranging two bulls to spit-roast me with my Mistress guiding both their hard cocks inside me and having both of them cum deep inside me and yes swallowing is mandatory for a slutty sissy slave that I am. I am also kept locked in chastity since it is my duty to be used for their pleasure and not for mine.

Ive done this once, it was a basically a bucket list session for me and decided to pay for a test so that i felt comfortable swallowing. I think it was $150. Small price to pay for the piece of mind.

I agree it would not have felt the same with just a condom and the session was in the works for quite a while so wanted to go as far as we possibly could.

Glad i did it this way. Not sure if ill do another one. Logistics are kind of tough on these types of sessions and i kind of need the stars to align to be in the right mindset. But glad i have the memory.

See , I don’t see it as a risk. Today is certainly safer than it used to be. I am not naive. If you’re going to do it, do it.
You’ll be just fine. Although you may never forget that first squirt.

This week it will be one year since my Mistress provided an orgasm in a session. It was to celebrate my recovery from surgery. Six weeks later I was ordered to come over dressed as a sissy under my male clothes, blindfolded and tied down to her torture table in her dungeon. I soon realized another slave entered and she directed him to give me oral until I realized what she was doing. Every step of the way he did what he was told and a while later I exploded into his mouth while my Mistress made him lick, suck and swallow every single drop out of me. I have not had an orgasm since then only milkings and a few ruined orgasms. Tomorrow I begin 24 uninterrupted hours of dedicated slavery and service to my Mistress. We waited 5 1/2 years for this.

Once you do this once with a domme, is it likely that you'd go back for a solo session with just her? Seems kind of like going on vacation somewhere and trying to go somewhere less fun the next time.