I have a tremendous amount of hesitation about writing this post, but it's things that are stuck in my head at the moment and this is probably the only way to purge them. Each of the following events would have fallen in with the Reflections posts. The first would have happened between Parts 2E and 2F. The second following Part 4C. The third following 5B.
Putting this out there... is really hard. To be honest, I can't believe I'm writing it. I feel an extraordinary amount of shame and embarrassment by talking about it, but why hold back now?
It will need a little bit of extra context that may fall under TMI, but it's related. I've never had an orgasm during sexual intercourse. It has never been permitted of me. We always have gone until she was completely satisfied. This made things a bit unpredictable since we never knew she was ready to stop until she was ready to stop. After a couple of hours of putting forth my best efforts and holding back, sex would be over, and my plumbing would be fairly backed up by that point. If she felt I earned it, I was allowed to orgasm via masturbation. With F this always occurred in the same way, with my slave seed going into the toilet. With T, it was either into the toilet or together in the shower. With K, even though we didn't have intercourse, there was plenty of buildup and making a ritual of my masturbation was what she enjoyed.
The First Events
In the events at the end of 2E, K broke me. We talked about it often. I would cry about it to her. It was a part of me I didn't want to face. She was set on her process. Some days I would resist her a lot, other days I could barely put up a fight. It didn't matter. K had made me her sissy slave. She had made me admit to it out loud. She was conditioning me.
I know that I've posted these pictures before, but now that I'm actually admitting to the how, when, and why they were used, I feel all screwed up inside. This picture was taken many years ago when I was asked to catalog some things. These are very similar to the items K had me purchase in 2E, although they are real fur instead of faux and the original gloves were a different color.
When my psyche couldn't handle what was happening, I would cry. K would continue to push. The more that I resisted, the harsher she would be. Each day, she would order me to masturbate in front of the mirror wearing these while she watched me on cam and we were connected on speaker phone. Each day, more teasing and humiliation. She would masturbate and talk to me. She would ask me questions and make me answer. Forced answers... each time pushing me a little bit farther.
"Keep stroking it. You really like this, don't you, sissy slave?"
"Did you just say no to me?"
"Please, Mistress, don't do this."
"Tell me you love it."
"Please, Mistress, I don't want to."
"I love it, Mistress..."
"What do you love, sissy slave?"
"I love you, Mistress."
"Quit fucking around or I'm going to punish you. I dare you..."
"I love the fur, Mistress."
"That's not good enough."
"I love being a fur sissy slave, Mistress."
"That's right, sissy slave, because that's what I want you to be."
"I love you, Mistress."
"I think your attitude is still a little bit off. I think you need to edge 10 more times before I'll allow you to cum."
"Yes, Mistress, I'm sorry."
"You should be sorry, sissy slave. This time beg for it."
"May I please cum, Mistress."
"Please Mistress what? And if you say 'don't do this,' I'll beat you until your ass turns black."
"Please, Mistress...I can't."
"Refuse me one more time and you'll be standing outside on the street corner wearing that."
"Please, Mistress, make me your fur sissy slave."
This was a fairly normal exchange. I can't pinpoint exactly when I would start to cry, but it would happen when I knew I was defeated and couldn't resist anymore. I would just cry. If she asked me what was wrong, all I could reply with was "I don't feel okay." This continued for a few months on a daily basis until 2F happened. Having an orgasm in tears just became... normal... for me.
In hindsight, I was just unable to cope with the identity that was being forced upon me, even if I did enjoy it on some level.
The Second Events
With F, following 4C, our play sessions would always end the same. Me masturbating into the toilet, F behind me, pinching my nipples from behind while watching over my shoulder and talking to me. F didn't need me to answer anything she said, I was often gagged and she would simply make up voices and answer back for me. Over time my slave outfit grew from our shopping trips. The skirt from 4B is pictured with it:
"Look at the pathetic little sissy boy, he's so turned on by being dressed up. Oh, I'm not a sissy, I'm only dressed this way because you made me. Liar. Why are your cheeks so red? Oh, yeah, because they should be. Playing with yourself with a hard-on while dressed up like a slutty bimbette. I would laugh if I saw a normal woman dressed like that, but it's even funnier on a sissy boy. I think next time we'll take you shopping dressed... just... like... this. Oh, please Mistress, don't make me do that. Would that be TOO humiliating for a sissy like you? I don't think it's any more humiliating than cumming while dressed like this, do you? You're lucky I even let you cum, sissy boys should be locked up. Are you crying, sissy? Too much shame? Boohoohoo, waaaah, I can't bear the shame of being this humiliated."
This type of speaking would continue for the duration of my masturbation and orgasm. If/when I cried she would laugh and humiliate me even more. This was my standard method of orgasm for a couple of years. It really made me feel bad... but at the same time it really turned me on. It's weird to say that... that "I just got used to having an orgasm while being humiliated into tears."
The Third Events
In the events of 5B, I don't know if it's better to say that T broke me, I broke myself, or I gave her permission to break me and she did. Either way, following the events of 5B, T wanted to continue pegging me. She wanted this to become our standard sex. As I mentioned in that post, I cry every time something is up my butt and T wanted to stretch me so that I could take a bigger strap-on. If there's a time that I just had to sort of "shut down" to bear with something and keep from running away, it was this process. T was hoping I would "learn to like it," so during the process it mostly occurred in the shower together with her violating me with her fingers or a toy while having me masturbate. I would cry every time but she would press her breasts up against me, grab my nipples from behind, and have me jerk off, trying to "overwrite" the violation with pleasure. This continued several times a week for a couple of months.
I have to think about why everything in my head is so dark. Why do I get aroused by these deep dark fantasies of cruelty and being broken? Are these fantasies a result of these experiences? I can't quite figure it out for certain, but at some point, it became normal to orgasm while being forced to tears. I know this shouldn't be normal... and I feel fairly screwed up about it. I probably have to find some way to cope and accept this as a part of who I am... I just don't know if it's something I'll every be really comfortable with.