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—Preliminary note: The form curb is sometimes used instead of kerb—as in, for example, the noun curb-crawl (cf., below, quotation 1.3) and the verb curb-crawl (cf., below, quotation 2.1).

1-: Primary meaning:

The primary meaning of the verb kerb-crawl is: to drive slowly along the edge of a road.

This verb is composed of:
– the noun kerb, designating the raised edge of a pavement which separates it from the road;
– the verb crawl, meaning to move along very slowly.

Likewise, both the noun kerb-crawl and the verbal noun kerb-crawling primarily designate the action of driving slowly along the edge of a road.

The following are three early occurrences of the noun kerb-crawl and of the verbal noun kerb-crawling used in this primary sense:

1.1-: From Laurence H. Cade’s motoring column, published in The Athletic News and Cyclists’ Journal (Manchester, Lancashire, England) of Monday 15^th December 1924 [page 7, column 5]:

FELIX IN A FOG.

London has been glorying in a prolonged dose of its own particular pea soup fog, and transport has been all higgledy-piggledy for two or three days. […]
[…] When I awoke to the morning of the first day of fog I trotted out Felix from the garage, because Felix seemed better suited to the conditions than my other steed. She is a Ner-a-Car which will potter along at four miles an hour without a jar.
There is much to be said for a simple machine which will give you riding comfort and protection at a mere crawl, and at such times as the weather is as it is at the time of writing, Felix will certainly be in commission for the kerb crawl to which she is so well adapted.

1.2-: From the column In and About, by ‘Puck’, published in the Huddersfield Daily Examiner (Huddersfield, Yorkshire, England) of Saturday 30^th May 1925 [page 2, column 4]:

A Taxi-cab Experiment.
It will be interesting to observe the progress of a new scheme which is proposed in New York. A different colour, it is suggested, shall be assigned to the taxi-cabs belonging to each separate owner. Thus patrons will be able to choose the hue that has given best service in the past. But perhaps it has been overlooked that this is not likely to be the consideration that will affect women “fares.” They will most certainly choose a colour to go with hat and coat or dress. Lucky the owner who chooses next season’s fashionable colour for his cars. There will be no kerb-crawling for his drivers. And unlucky the poor fellow if that tint goes out of fashion quickly, for no woman of taste will be seen within such a demode conveyance.

1.3-: From the column A Special Correspondent’s Log, by Trevor Allen, published in the Westminster Gazette (London, England) of Friday 20^th January 1928 [page 7, column 1]:

Stroll down Piccadilly towards noon, as I did yesterday. What a comparative peace and solitude! Society and Leisure emerge from residential Kensington and Mayfair, mentally blinking at the light. They have that bath-room gloss which tells you, beyond doubt, that tea and toast were served—probably in bed—an hour ago.
The taximen, an infallible register of manners, are really only beginning to pack the ranks in earnest and sally forth on their diurnal curb-crawl.

2-: Specific meaning:

The verb kerb-crawl soon came to specifically mean: to drive slowly along the edge of a road with the intention of soliciting people for casual sexual activity or (now more typically) prostitution.

Also in relation to this type of activity:
– the noun kerb-crawler designates the person (originally and most typically a man) who drives;
– the adjective kerb-crawling refers to the person who drives;
– the verbal noun kerb-crawling designates the action of driving.

These are, in chronological order, the earliest occurrences that I have found of the verb kerb-crawl and derived words used in reference to the intention of soliciting people for casual sexual activity:

2.1-: From Six Miles An Hour Called “Reckless”, published in The Border Cities Star (Windsor, Ontario, Canada) of Monday 16^th August 1926 [page 9, column 2]:

Stewart Trudell, 316 Drouillard road, Ford City, achieved the distinction of drawing down a fine for reckless driving at a speed which he declared was six miles an hour. The fine was imposed by Magistrate W. A. Smith in Sandwich police court this morning and amounted to $10 and costs.
It appeared from the evidence that Trudell started “curb crawling” with his car, directly in front of a street car. Sandwich police testified that he and his companion were leaning out the right side of his car, ogling women on the sidewalk, while a street car directly behind their crawling vehicle was unable to get by, despite repeated signals. Magistrate Smith warned the accused that obstruction of traffic constituted reckless driving, and attention to the sidewalk, rather than the roadway, meant recklessness, at any speed.

2.2-: From the column Brighter Lincoln, published in the Lincolnshire Echo (Lincoln, Lincolnshire, England) of Monday 2^nd April 1928 [page 4, column 1]:

A certain class of man who has a car is a dangerous kerb-crawler who lies in wait for innocent flappers. In some places he is carrying on a game that has to be stopped somehow. I am not inventing this. Sensational evidence about it has been given to the Street Offences Committee in London.

2.3-: From the Sunday Mercury and Sunday News (Birmingham, Warwickshire, England) of Sunday 20^th May 1928 [page 5, title & column 2]:
—Remark: This article contains not only the noun kerb-crawler, but also three occurrences of the adjective gutter-crawling (cf. footnote about the Oxford English Dictionary):

PILLION GIRLS AND “KERB CRAWLERS.”
Police Action Possible in Midland Town.
EVENING PARADES.
From Our Own Correspondent.

Halesowen, Saturday.
It is quite likely that ere long police action will be necessary in the Halesowen district in order to cope with the nuisance and annoyance which develops from the activities of the “gutter crawling” motor-cyclist.
[…]
The town has gained some notoriety in consequence of revelations made in a case at the police court some time ago regarding the conduct of pillion-riding girls.
If there were fewer girls seeking motor rides, the “gutter crawling” problem would solve itself automatically, but one might almost as well expect fish to live without water.
It is only necessary to traverse some of the main thoroughfares, particularly at the Quinton end and in the direction of Hagley, to realise the large reinforcements the “gutter crawling” fraternity are receiving week by week.
In some sections one can see groups of between 15 and 20 prowling motor-cyclists whose sole object is to scrape up a brief acquaintance with giggling girls.
Social workers are much perturbed at the increasing number of girls who parade the streets in the evening and who openly select their cavaliers.
Many of the girls are from quite respectable families, and their parents have absolutely no knowledge as to how their daughters spend their spare time.

2.4-: From the Sunday Mercury and Sunday News (Birmingham, Warwickshire, England) of Sunday 20^th May 1928 [page 5, column 3]:

AFRAID TO SPEAK.
Girl Victims Who Will Not Tell the Police.
By Our Own Commissioner.

The menace of the motorist or motor-cyclist who accosts women and girls and invites them to go for a ride into the country is believed to be growing.
It is not peculiar to one part of the country and Birmingham, like other populous centres, has to admit the prevalence of this perilous pastime. It is no uncommon sight to see motorists hugging the kerbstones in the centre of the city and on the suburban main roads, for the purpose (which is quite obvious) of attracting the attention of strolling girls.
The fascination of a motor ride away from the smoke and grime of the city is such that unsuspecting girls do not always stop to think of the risk of being left stranded miles from home if they have the courage to run away or fight against unwelcome attentions.
[…]
The growth of the kerb-crawling menace has immensely increased the difficulties of the police, who, it is understood, are powerless in law if the motor-cars used by the pests are kept on the move.

2.5-: From the column In Passing, published in the Sunday Mercury and Sunday News (Birmingham, Warwickshire, England) of Sunday 20^th May 1928 [page 6, column 1]:

On another page will be found a description of the difficulties confronting Midland police in restricting the dangerous activities of motorists who tempt unwary girls into accepting joy-rides into lonely country districts. While the introduction of legislation in order to punish “kerb-crawling cads” appears undesirable as further complicating the laws respecting public morals it seems high time that public opinion was aroused to the necessity of protecting respectable girls from the clutches of marauding gallants on wheels.

The verb kerb-crawl occurs in the following article describing an interesting inversion of the traditional roles associated with this type of activity—this article is from The People (London, England) of Sunday 12^th May 1929 [page 5, column 2]:

THE “LIFT LADIES” WHO WILL—LIFT ANYTHING THEY CAN
When you go to Paris don’t accept a lift from a woman in a car near the Bois de Boulogne.
From “The People’s” Correspondent.

Women with real feminine ingenuity are giving a new turn to the game of robbing light-hearted holiday-makers in Paris, near the Bois de Boulogne.
So don’t “walk along the Bois de Boulogne with an independent air,” as we used to sing when we were children.
These women have all the appearance of “le vrai monde,” as the Paris Smart Set is called, and they are usually found “kerb crawling” on the grand [sic] boulevards or the quiet avenues abutting on the Champs Elysees in the early hours of  the morning.
Their special prey are well-dressed foreigners, who look as though they have just emerged from some night resort and are worth robbing.
Pulling up beside their victim, the ladies smilingly offer the wayfarer a lift on his way home, and as it is not every night that one meets such smiling charmers in a stray car, the offer is generally accepted.
The victim seats himself beside one of the ladies, while the other sits at the steering wheel.
The car then puts on speed, and before the passenger realises what is happening he is speeding to the deserted parts of the famous Bois de Boulogne.
In one of its quiet roads the car pulls up and the ladies who were so free with the offer of a lift proceed to “lift” all they can from the victim.
Occasionally they are aided by male accomplices, who are waiting near at hand in case the victim should be unwilling to “part,” but in most of the cases reported to the police the two bold bad ladies have “lifted” the spoils without male assistance.
Owing to the number of complaints, cyclist police are now patrolling the roads affected by these charming “ladies,” one of whom is said to carry a revolver.

Note: The Oxford English Dictionary (OED – 2^nd edition, 1989) has so far recorded gutter-crawling only as a U.S. noun and as dating back to 1945. What is puzzling is that the OED (s.v. kerb-crawling, noun, and s.v. kerb-crawling, adjective) does quote several passages from the Sunday Mercury and Sunday News (Birmingham, Warwickshire, England) of Sunday 20^th May 1928, but omits the occurrences of the adjective gutter-crawling in that issue of the newspaper.