「Person screwing within annulus cockring」can obviously be performed ONLY ON AN INDIVIDUAL BASIS, the SINGULAR CASE since only one male person can use the device at a time. Chinese sources list the meaning as a classifier for people or objects in general, and in that respect perhaps elements are「person coagulated, clotted, physically hardened up」(and therefore in need of a cockring for screwing) without reference to age in years, or「person with smegma」or「person with prostatitis.」Prostatitis prevents the blood vessels used to engorge a penile erection from fully closing, hence the「occurrence a number of times with person screwing」to require a cockring as a remedy for erectile dysfunction:「person with cockring, tool of ten men in orifice any number of times.」Also likely, given the prevalence of sex slaves in China previously, glyph depicts an INDIVIDUAL with such a slave captured and enclosed for his exclusive use.
Nevertheless,「person clotted and hardened, enclosed old crap in penis cavity, accessed through a screwing orifice」as the treatment of prostatitis of an INDIVIDUAL (decidedly not group therapy):
「…[M]any wives, girlfriends, male lovers and just plain friends have learned how to do drainage. Providing that nails are clipped and a non-latex surgical glove (available widely at drug stores) lubricated with K-Y® jelly, is used, little harm can come from trying. However, if you have acute epididymitis, you should not do drainage.」
「If the man is [lying] over some pillows or kneeling, stomach down, and the 'drainer's' hand is facing the floor, all one has to do is curl one's finger slightly and feel around, and the outline of the prostate gland can be detected. Stroke as firmly as possible from the outside to the lower center. Stroke very, very slowly and firmly, so that the contents of clogged acini are squeezed out.」
「The drainee will be very uncomfortable. This is not fun. It might be a good idea to place a towel under the drainee, because stuff does come out. It might take several sessions before you both get good at this. Talk while it is happening. The person being drained may have some trouble expressing himself due to groaning, so the drainer should pause (without withdrawing) if the person being drained seems to have something to say.」
「After the first few sessions some added burning may be noted, due to what is being drained. This will improve. Also, some blood in semen may be noticed at first. In this case, back off on the pressure and frequency of drainage and go more slowly. Blood is not a positive sign, but it should also not be a cause for panic.」
[ https://www.prostatitis.org/wifedrainage.html 2013-09-02 ]
「Selling services priced the old-fashioned way, in orifice」or「selling services of an old(er) orifice」suggests a ONE-OFF affair, i.e., the SINGULAR case rather than plural, someone with whom nothing is promised to be repeated, or is a ONE-TIME ONLY offer to an INDIVIDUAL, something on a CASE-BY-CASE basis.
「Person old in orifice」「person」who is still with an「old orifice」「person with enclosed screwing orifice」and「person screwing with revolving returning, many times in enclosed orifice」suggests some form of monogamy, that is to say, having only ONE INDIVIDUAL as an intercourse partner either sexually, socially, or both ways, the SINGULAR CASE. Note that one way to facilitate becoming an「old person」is by not schtupping (ejaculation into a birth canal or other attainable orifice) around and dying young from contracting a disease, in other words by being continuously MONOGAMOUS sexually, returning to the same physical orifice(s) until old, revolving in a cycle many times with one INDIVIDUAL, and not with plurality, buddies, or ewe.
On the contrary,「person clotted」to whom services are being sold would need a ONE-OFF price on a CASE-BY-CASE BASIS, since the infectious condition would significantly increase the risk and hence the corresponding monetary reward to the shaman or pimp who may lose that girl as the result.
「Person enclosed and old」as an older man now all alone, surviving INDIVIDUALLY and doing everything PERSONALLY to maintain his daily life and activities. A「person hardened」may be fairly difficult for other people to live with, hence remains a sole INDIVIDUAL and living SEPARATELY, having become 'hardened up' in more ways than one, such as becoming hard-headed, or due to urethral scarring from infection when younger, or coagulated prostate fluids.
Perhaps「person hardened」may depict someone in armor, and for best results armor should be custom-made, PERSONAL, ONE OF A KIND for each INDIVIDUAL for the best fit and not shared with others, used by only one person. Armor may incur damage unknown to the owner during use by another and become unreliable, or not be available when needed immediately, its shape and freedom of movement may change and so diminish practiced skills in battle, etc. Armor made for someone else likely would not fit well, anyway. Note that this glyph is also used as the designation for counting military units, troops in armor (箇), and for counting scars that are often harder and stronger than surrounding tissue.
A rather odd and fanciful combination of elements perhaps, but「service provider (仕) with enclosed (囗) cavity (凵)」also suggests having only ONE INDIVIDUAL as a client, such as the shaman or pimp reserving a favorite concubine for a lord's PERSONAL USE, or, a lord always with a favored concubine (…well, almost always—we said it was fanciful): COUNTER FOR OBJECTS, THINGS, PIECES, LARGE CHUNKS OF STUFF.

External source definitions …excluding politically incorrect concepts and other meanings deemed offensive today; may include extended definitions, euphemisms, and mnemonics)
Chinese: individual; this; that; size; classifier for people or objects in general
Japanese EDRDG: individual, counter for articles
Unihan extended: numerary adjunct, piece; single