I’ve been using the Captain’s Wench as an ADS for almost a year and have also experienced discomfort similar to what you describe. I have, however, tweaked and refined the system somewhat over time so that I have no problem wearing it comfortably for in excess of 10 hours continuously without having to remove or adjust it. I will be happy to try to explain my mods and experience with the design.
In my experience most of the real discomfort results from the loose shaft skin becoming bunched or pinched by the wench strap. This can be minimized by first carefully smoothing the wrap and then stretching your unit out to it’s full length and pulling any loose skin back from the glans before wrapping the velcro Wench strap around it. I put the front edge of the Wench about 1/2” back from the ridge of the glans.
I use a baby sock with the toe cut off as a wrap under the wench. If you buy the “bobby sock” style, they will have an extended cuff that provides excellent cushioning. Leave the sock long enough to extend out over the tip of your unit, and it will provide additional comfort and protection in use.
I cut the width of the main velcro strap down from the 2” to 1 3/8”. This allows the gripper area to be smaller and closer to the glans, resulting in tension being applied over a longer portion of your shaft.
All edges and corners of the straps must be smoothed by cutting, filing or sanding to ensure there are no sharp portions that can dig in and “bite”
The forward portions of the gripper pads need to be tapered to a “ramp” slope using a razor blade or similar tool, again to avoid the digging in phenomenon.
If you plan on using the Wench after jelquing, I have found it highly beneficial to wait until the “pump” dissipates, or the Wench will be overly loose in a hour or so.
I have tried several different methods of applying tension, including elastic knee straps, rubber bands and weights. For my lifestyle, mostly involving standing or moving about, using a weight has been the most successful and trouble free. I have found that an 8 oz weight keeps my shaft fully extended and under constant tension, definitely preventing any form of “turtling”. I have had no problem with circulation, fluid buildup or chilling. Another benefit of this system is that it is quite easy to inconspicuously use a urinal when necessary.
I also use heavier weights for protracted periods, but find that as the weight goes up, the time without needing to adjust the wench comes down proportionately. I can wear a 16 oz weight for about 4 hours before adjustments are necessary. Larger weights also pose a problem due to the much greater pendulum motion that occurs, which invariably draws unwanted attention. Using weights work well in in most style of pants as long as they are not tightly fitted. I live in a very warm climate and am in shorts most of the time, and wear my Captain’s Wench at least 50 hours a week. I put it on in the morning, and don’t take it off until night.
Good Luck