Mistress Ayn, I was thinking about Your byline. When, I asked myself, was the first time I actually cried, in a bdsm session? And, I almost immediately remembered. It was with a Mistress I saw only two times at the old Belle du Jour dungeon, more than 30 years ago.

Her name was Helen, and, if She told the truth, She was, in addition to a dungeon Mistress, a psychiatric nurse at a well known NY hospital for crazies. Her name was Helen, She was tall, broad, but not heavy, very well proportioned. Our first session was mostly talking before She gave me a spanking (which I did not much care for) and then She supervised my masturbation to conclusion.

I did not actively seek Her out as the Domme for my second session. I walked in unannounced and got to see who was available. When She came into the interview room She said: "oh you, good, we have unfinished business, I'll tell the manager you selected me." And, that was it. The receptionist came in a couple of minutes later and I paid the tribute.

Helen got me alone in one of the few dungeon rooms which had windows, though the shades were down when we started out, It was early evening, dusk time, and after I got completely undressed, She decided to open the shades and close the lights, making the session room very dim with a slightly eerie feeling.
The Mistress pointed out the building across the street where there was lighted windows and people still at work. "They can see us, you know, not our faces, but our shapes, and they can tell what we are doing" She said.

"Now," She directed me to go to one of the windows, to lean down and to hold on to the window sill, standing back from it, with my backside vulnerable to Her attack. She was wearing a strap on, which I had never had even seen before. She started slowly invading me, and I was whimpering. She told me to "shut the fuck up" and when I continued whimpering, She took a break from that activity, to assault my ass with Her hand and even Her fist. I was afraid She was going to push me through the window, and begged off.

She switched my position and had me kneeling before Her, and She methodically, carefully, bitch slapped my face. She instructed me to count the blows, "One, Mistress, thank you" "Two, Mistress, thank you." She said when i got to 20, She would decide whether to give me another 20 slaps or something else.

At 20, the first time through, She decided i needed additional slaps. At the second time, She decided that it was time for something else. She closed the shade most of the way, while leaving me kneeling before the window. Then, She went to the light switch, and turned it off and on and off and on again in quick succession. She explained that the blinking lights were a signal She gave to any interested observers across the street.

She asked if i preferred the light on or off and i said off. She left the lights off, then came back with Her strap on pointed right at my mouth and instructed me to suck it eagerly and with enthusiasm. i was a grown man crying then, the tears were not fabricated, they were flowing down my reddened cheeks, not from the pain of the bitch slapping i had taken but from the complete emasculation i had endured at Her hands.

i did not session for a long time after that event, and told myself that i did not ever want that again. When i returned months later to Belle du Jour as a regular customer, Ms. Helen no longer worked there, and i got assigned to a Ms. Vanessa, a very different Lady with Her own methodology. But, when i told Her i had previously seen Ms. Helen, Ms. Vanessa asked me whether Helen had made me session before the open window in the big room. When i said "yes" She laughed and asked whether i had sucked or taken it in the ass, and if Ms. Helen had left the light on.

Ms. Vanessa never repeated the initial stunt, but Her whole dominant attitude towards me, and years of sessioning which followed, was impacted by my admissions to Her about Ms. Helen turning me into a crying semi-public slut.

Fascinating encounter, second try. Crying can be very cathartic. I actually have had subs ask to be made to cry. Often they think that can be accomplished by pure pain. Seldom is that so. Usually it's from an emotional dredging - like your emasculation experience.

Mistress Ayn,
i have cried twice in sessions. There was pain both times in those sessions, but it wasn't the pain that prompted the tears. It was my emotions. Possibly humiliation might describe my emotion. i felt humiliated.
One of the Mistresses wanted me to cry at the next session. So, i faked it.
kickable

Exactly, kickable. It's the emotions, not the pain that usually get a sub to the point of tears. Often they don't understand why they are crying and are further embarrassed by it. However, with proper aftercare, the experience is usually very beneficial and ultimately memorable.

Faking it? Shame on you. I'd better never catch you doing that or I WILL give you something to cry about ;-)

Well Mistress Ayn,
The Mistress had a videographer in on the session and asked me to cry in the middle of the play. i didn't want to fake it, but i wanted to please Her.
kickable

Ahh, that makes a little more sense.