Prostate Milking During Semen Retention

Should I do prostate milking during SR challenge...

It all depends on the rules you wish to make for your personal challenge. If you are going to follow the 21 Day Challenge rules, then the choice is yours as the rules don't really address 'milking'. There is further discussion about this in the 21 day challenge post, you may find some of that information helpful.

... is it considered cheating?

It isn't necessarily cheating unless you add a specific rule to make it so.

How would it effect SR and arousal levels?

Because true prostate 'milking' does not cause spasmodic orgasmic contractions an ejaculation (forceful emission of semen) does not occur. If done properly only the prostate is drained (prostate fluid comprises about 30%-35% of semen content). Thus, only a portion of your semen is released and it is not an ejaculation per se. A deeper massage can also induce draining of the seminal vesicles but is not required. Since no ejaculation takes place, the trigger mechanism for the normal hormonal cascade leading to the male refractory period is avoided. The particular hormone responsible for this is prolactin which neutralizes the feel good hormone dopamine. Dopamine is produced during the arousal phase and if it is not neutralized by prolactin or other hormones then your ability to retain arousal remains.

... would I feel drained/tired after milking?

If you were experiencing severe vasocongestion in the genitals (blue balls syndrome) then you will also experience significant relief post milking but your arousal will not fall to the level experienced in the post ejaculation refractory period. Indeed some men will feel only a very slight drop-off in their arousal level, though their ability to then achieve an ejaculatory orgasm may be temporarily impaired similar to the male refractory period.

If not when should I milk my prostate and can I do it with the helix classic or a different toy?

When you choose to 'milk' yourself is totally up to you and when you feel the need for temporary relief. The Aneros devices are prostate "massagers”, they may or may not be used as “milking” devices depending on the individuals involved. Self “milking” with the Aneros via ‘hands free’ manipulation is difficult as one usually needs to be very relaxed for the ejaculatory ducts to open and allow the fluids to flow out of the prostate. The stronger, more vigorous, muscular contractions needed to effectively move the massager create a level of tension which is antithetical to the relaxation of the gland ducts. It is possible to train the various muscle groups to alternately relax and contract to accomplish a “milking” but it will take practice. It is unnecessary to employ strong muscle contractions with your Aneros use as a “massager” to generate orgasmic feelings, hence you can employ it for many hours without triggering a “milking” response. 'Milking' your prostate of seminal fluids can be learned. You can read a short paragraph about Prostate Milking in the “Your Body” chapter of the Aneros WIKI. You can read a longer treatise on prostate milking technique and issues from Lady Lubyanka. There is also a well written blog by Andr. titled HOW TO MILK A BULL which gives step by step descriptions of the process. For those of you interested in more information regarding prostate milking here are some links to articles/websites I've run across over the years which I found helpful in my learning. 1.) Prostate Milking 2.) Self Prostate Milking for Health and Pleasure! 3.) Prostate Massage/Milking The male chastity community has developed a more focused interest in milking techniques/variations due to their limitation of traditional ejaculatory orgasms the following links are from such sites. 4.) Male Chastity Milking (Three Fun Ways to Do It) 5.) Different Male Milking Techniques for More Control 6.) A Lazy Domme's Guide - Prostate Milking

It seems every year there are more new articles extolling the merits of prostate milking so I guess the tide of social taboos against this activity is slowly changing. My own experience has revealed the conditions need to be 'right' to accomplish a true "milking" using your Aneros and without using your hand to manipulate the massager. Generally, you need to be highly aroused, your prostate needs to be full and engorged due to arousal (an erect penis from edging is helpful but not mandatory). You should be on the high excitement plateau just before reaching the PONR (Point of No Return), then using your sphincter and PC muscles start performing very strong, rhythmic, slow paced contractions with total relaxation between contractions. It is important to maintain your arousal level, through penile stimulation if necessary, but don't take yourself to the point of ejaculatory inevitability (PONR). This may take a long time and be somewhat strenuous but you will eventually get the ejaculatory ducts to open and the drip, drip, drip of prostatic fluid. The process may not yield much fluid nor be intensely pleasurable in relationship to the amount of energy expended, it can be done, but Aneros devices (regardless of model or size) may not be the best tools for this particular activity.

The best tool I've found for performing a thorough self "milking" is the Njoy 'Pure Wand'. The reason for this is tri-fold. First, you will be able to manipulate it precisely to massage and pressure not only the prostate but also the seminal vesicles which contain the bulk of seminal fluid. Draining the seminal vesicles will get you to that fully emptied feeling where as just emptying the prostate may leave you still aroused and desirous of further emptying. Second, you will be able to apply more pressure to force fluid movement out of the seminal vesicles and prostate than the no hands massagers (even with vibration) can do through muscle contractions alone. Third, you will be able to relax (an essential aspect of the process) while performing this manipulation.

I suspect having a professional masseuse do this would be much more pleasant as you could really just relax into the pleasurable release to be had. Good Vibes to You !

@Orgasmic19 I practice SR all the time now and feel that my Aneros sessions help me "release" some visible prostate fluid on occasion (but not always). Regardless, they are very enjoyable for me and mesh very well with the SR and "chastity" practices. And as @rumel has noted, prostate "milking" can definitely help with the "blue-balls" feeling as I can attest. Also, having no refractory period is a great "boost" to the continuing practice of SR and male chastity, and enables both to continue without pause.

I have no set "tool" for prostate milking and use any of my available Aneros massagers.

I'm a bit confused about how prostate milking is different than prostate massage

Posted by: @jjA3
I'm a bit confused about how prostate milking is different than prostate massage.

While other internet websites, blog posts & articles often use the term prostate massage and prostate milking interchangeably, I make a distinction, I use the term prostate massage as the act of manipulating the prostate through physical stimulation (an action), either with fingers, penis or other sex toys/devices. I use the term prostate milking (a result) as the emission of prostate/seminal fluids from massage action. Prostate massage by itself does not necessarily induce 'milking' but it may induce orgasms.

Good Vibes to You!

@Rumel knows! I can massage my prostate and get nice feelings and orgasms, and not a drop of fluid comes out of me the whole time. Or, I can use a G-spot wand and massage my prostate more directly and in a certain way and can milk prostate fluid out of me and not have an orgasm. In fact when I milk my prostate I usually don't have any sensation of orgasm at all. The feeling after it comes out, that relief-type feeling, and feeling of achievement, makes me have involuntaries and I can have subtle orgasms. But when I have major hands-free prostate Os I usually nothing milk-related comes out of me.