A brief introduction is in order; Mistress Alison is a good friend and a very knowledgeable and experienced Mistress, she has also been a frequent contributor to PDQ. She is now available to answer questions from both Mistress and sissies alike, assuming a respectful tone of course. These email conversations may well be included at some future date in PDQ though a request for privacy would be respected. Feel free to write her at email@example.com and please don't waste her valuable time asking "where / how can I find a Mistress?"
Dear Mistress Alison
My favourite method for punishing (and also teasing) my petticoated boyfriend is to remove his chastity tube and slap his penis and balls with an old fashioned wooden ruler. I always make sure I cover the largest possible area and pay great attention to the tip and the corona. I use fast light slaps and continue until it is a nice bright pink and he is crying. If it is time for his monthly relief, and I think he deserves it, then I release his left hand (he's right handed) and give him precisely two minutes to relieve himself. Whether or not he has managed to ejaculate, after his time is up he gets a generous squirt of antiseptic spray followed by a quick rub over with an alcohol wipe and then goes back into chastity until the next time.
However, I'm concerned that what I'm doing might have long term consequences. The last few times I've released him he has been unable to get fully hard again after his smacking and was nowhere near to coming when his allotted time was up. At some point in the future I shall probably want to use him for conventional sex and even further into the future I may want children. I definitely want to keep my options open and don't want to turn him into something useless in either department.
So, I would like to ask if you think if it is possible I've caused him any physical damage and if so what it might be. If not, how long do you think I can go on doing this without risk?
Reading your letter two things spring immediately to mind; I am not a doctor so if you suspect your boyfriend is suffering from erectile dysfunction, or any other medical problem, you should send him to see one without delay, and if you are concerned that something you are doing might be causing him damage or harm then stop doing it.
However, from your description of "fast light slaps" I would be very surprised if you have caused any lasting physical damage. The penis is like any other area of the body in that it will be damaged if you hit it hard enough for long enough, but in general it is amazingly resilient. You don't include any details about his age and general health or whether or not he is a willingly participant, but assuming that you could reasonably expect him to be sexually vigorous then I suspect the problem is largely psychological. Does he become fully erect on release from chastity? If he does then there is probably nothing to worry about.
You also say that you continue slapping his penis until he his crying, if he is in a state of distress, and if he isn't then a punishment hasn't served its purpose, then it is hardly surprising that he won't be thinking about sex and won't be wanting to play with his sore member. If you merely want to tease him then maybe you should try alternatives to impact play; repeatedly bringing him to the edge then applying cold or giving him enough pain to collapse the erection, the application of rubefacients (compounds of camphor, capsaicin, menthol, methyl salicylate etc) tickling, dripping hot wax, scratching, pins, etc and save the ruler for actual punishments.
I wish you both well.
Comment from sissymaid kitty
Please allow me to reassure you. I have been a regular recipient of penile chastisement with a range of instruments for the best part of a decade and have sustained no lasting harm, everything is still in good working order. However, a wooden ruler is very much a blunt instrument (no pun intended) and there are much more effective implements which I feel you should consider in preference to it. Mistress Alison has a special miniature multi tail flogger, known as a penis or willy whip, which is good for general use and covers a wide area. She has also used a standard riding crop (the rectangular flap at the end, properly termed a keeper, is the part that should make the actual contact), a special crop with a keeper shaped like a miniature hand, which is also good for putting red hand shaped marks on pristine buttocks, a tawse, her rattan nursey cane and even a metre long carbon fibre cane, which is incredibly severe, all without causing anything more than severe short term discomfort, some bruising, and medium term mild discomfort. Until the discomfort has subsided to a manageable level I am always very keen to avoid becoming aroused as doing so would mean my agony will begin anew.
If you take up Mistress Alison's suggestion about hot wax do not neglect to apply generous amounts to the pubic hair as having to comb it out afterwards is a mini punishment in itself.
I hope you find my remarks helpful.