For the most part, I was able to roll with pretty much anything that F could throw at me. As her hunger for increased dominance grew, F became very interested in chastity, orgasm denial, ruined orgasms, and milking. Her take on it seemed a bit different than most chastity enthusiasts. F was slightly interested in the control aspects, especially since she began to feel that all males should be controlled in such a manner or they will only get themselves in trouble. This view meshed with who she was.
Her deeper interest revolved around removing any and all forms of sexual pleasure from a sub.
-Only the Domme deserves that type of pleasure, so the sub should be content if her needs are met.
-If the Domme gets another type of pleasure from denying her sub any form of sexual pleasure, and since her pleasure is the only one that matters, the sub should gladly sacrifice his pleasure in favor of hers.
F was starting to get a bit terrifying, but I continued to encourage her since I wanted her to keep growing as a Domme. I was very resistant to the idea of losing sexual pleasure, but it always made her happy to take something by force and watch the look on my face as it happened. Our journey down this path are the only times where I was unable to endure, but not for reasons other than the obvious ones.
I know that F was doing a lot of research on these topics both on the internet and by reaching out to local Femdom couples she knew that practiced it regularly. She would often share her findings with me and I could tell when something got her juices flowing. I was instructed to learn as much as I could as well. F wasn't really interested in KTB's, thankfully, heavily because of the chance for serious injury but also because if a sub could learn to control his erections, that's one less thing for her to take away.
Short term chastity is something I had no problem with the concept of. I thought it was hot and the fantasy turned me on to have Mistress literally holding the key to my sexual release. F was on another level completely.
"I read something that I liked. Most employees get 2 weeks of vacation a year. Since it's a sub's job to please his Mistress and since following an orgasm a sub loses focus for about a week, doesn't that mean a sub only deserves 2 orgasms a year?"
"A male orgasm is like Santa Claus."
"If you're good he brings you whatever you want?"
"Hah, good one. He comes once a year if you've been nice and gives you a lump of coal if you've been naughty. Have you been naughty or nice, slave?"
I received an email with a link that we would talk about later. It was to Mistress Lori's Chastity Tubes.
"Apparently the only really secure tube type chastity device is to have a piercing." I cringed.
"Really?" I feigned ignorance.
"Yes. These ones even have a break-off screw option where you can fill the hole with epoxy and the screws break off inside so they can't ever be removed. Isn't that great?"
"I don't know if I'd say, 'great.'"
Since F didn't have any experience with chastity, we decided to start small. I purchased a Houdini style device at first since I thought it would entertain F to use it in conjunction with the real fur handcuff covers we had.
Now for the TMI part of the post that is important for this segment:
1. I'm not circumcised. I would have to get circumcised to get most of the piercings used in chastity. This also requires more frequent device removal for cleaning and carries an increased risk of edema.
2. I'm a grower, not a shower. Shower penises stay relatively the same size flaccid vs. erect, but they get hard. Grower penises are small when flaccid and increase in both size and stiffness when erect, usually in the magnitude of 2-3x. Mine is probably in the realm of 3-4x.
3. I have a "high and tight" scrotum, rendering almost every tube style device a poor fit.
4. I have some baby fat on my upper crotch that just never went away. It basically gives a small pad between the surface layer of flesh and the true base of my penis.
5. My pubes grow at an angle. Keeping a cleanly shaved crotch inevitably leads to regular infected ingrown hairs. If you are wondering why this matter, just try putting on the majority of sub-$500 devices with medium to long pubes and you'll understand immediately after the hinges and joints have yanked out a dozen hairs or so. Having to stay cleanly shaven for a device and battling infected ingrown hairs was indeed a problem.
The Houdini was not a good choice as a first device. It weighed a ton. It was easy to pinch skin in the moving parts. It would cut off circulation when closed as tight as it had to be to stay on. The maximum amount of time I could wear it before I got some "there's something really wrong here" pain was about 20 minutes. That was the first of many expensive mistakes in regards to chastity.
Next up was the CB-2000. F had me order the pink one. This model had the solid ring design. If I went with a large ring, my scrotum wouldn't stretch far enough to avoid being pinched. If I went with a small ring, it would take me 10 minutes just to get my junk through it and it was too snug. We tried just about every combination of ring size, spacers, etc. The end result was not great. With a small ring and short spacer the friction would cause sores and pinching, even with lube involved. With a longer spacer it would work fine until a testicle would decide to pull itself through... VERY painfully. With a large ring and short spacer, it would crush a testicle. With the longer spacer, it again would be fine until a testicle would pull through. Our limit with this was approximately 2-4 hours depending upon the ring combo, number of arousal attempts, and the temperature.
Shortly after, the CB-3000 was available as a "cage only" option and we gave that a try. The base of the cage was a lot smaller, so it might work. We used it with the existing rings from the 2000. With this I could go 4-6 hours but then the cage would either rub open a sore at its base or a testicle would pull out. I ordered up the hinged rings that were standard on the 3000 and while it was a lot easier to get on, the exact same thing happened.
Thankfully, F was present when just about all of the failings happened, so she knew there wasn't any exaggeration on my part. One of the testicle pull-throughs happened while she was playing with it. She also saw the sores when she removed it once after I wore it on a 3 hours shopping trip. Unfortunately my ability to endure this just wasn't there.
This got her thinking about a full metal belt, but after spending nearly $500 on devices, it was a large leap of faith to drop $1000ish on something.
While all of this was happening she was aware that I would need to be milked for prostate health. Since having anything in my anus was on my list of hard limits, she scoured resources for other means. I found a method for a combination ruined orgasm/milking that expelled the prostate but didn't relieve any sexual frustration that was relatively simple. With her permission I tested it twice daily for a week. It was actually kind of amazing. After 3 days of a repeated tease and denial procedure I was able to get semen to just leak out with a soft flow (like a weak urine stream). I would drain everything and deflate my testicles but I would stay completely erect and just as frustrated. This may have been the magic answer.
On day 5 I was going to give it another test. As I worked my way up, all of a sudden my penis just started draining semen. There was no build up, no "I'm close" feeling, I couldn't even control the stream. It was like someone peeing with no bladder control. The muscles had forgotten how to build up tension and release. This scared the shit out of me. I shared the results with F.
"Mistress, I think this method will make it so that I can never have another orgasm ever again. Is that something you would want?" My mind raced, "please say no, please say no, please say no."
"I don't think you should do it anymore then, slave. If you can't have an orgasm, how is chastity supposed to scare you? I will keep it in mind though, in case I ever feel you deserve that in the future."
Bullet dodged. I received permission to try and "repair" what had been done. I'm not 100% certain, but I believe the method I had been experimenting with had caused an over-stress of whatever controlled the release of semen from the prostate. After repeating this several times over a short period of time, it responded by simply relaxing itself and allowed things to flow without requiring a pressure/force build up behind it. It took me 5 days to get things working correctly again, and 20+ attempts to finally get back to something that would qualify as an orgasm.
The next thing F tried was ice. This would be the second time I couldn't meet her expectations. I have a lot of muscle mass and the muscles are very tight. Couple that with a slew of injuries from sports, a car accident, etc. and my body just doesn't hold up very well. Some of F's Domme friends used ice to yield a pleasureless ejaculation for their method of milking. We tried this a few times, using ice to numb out the penis and testicles but continue to apply stimulation. I was never able to ejaculate in this state, but I did manage to end up having back spasms, leg cramps, and other miscellaneous painful ailments that led to an immediate break in the play.
We didn't ever go further, around this time things started to get complicated.