<p>"An Enquiry after Stretchit in Gloucestershire, or the Sailor's Reply", an innuendo-laden English caricature of ca. the first decade of the nineteenth century, which comments on a few young women who were daring enough to ride horses astride, rather than sidesaddle (as was considered appropriate for females during the 16th through 19th centuries).  Part of the intended humor is supposed to come from the encounter between the genteel (though boldly daring or "fast") young lady and the salty British tar.
</p><p>Dialogue and text in image:
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<dl><dt>Young lady</dt>
<dd>"Pray, Sir, is this the way to Stretchit?"</dd></dl><dl><dt>Signboard caption</dt>
<dd><i>To Stretchit</i> ☞</dd></dl><dl><dt>Sailor (in stereotypical bell-bottoms)</dt>
<dd>"Shiver my top-sails, my Lass, if I know a better way."</dd></dl><p>(Note that the signboard is roughly shaped to resemble a hand with a pointing finger, the common directional indicator at the time — see <a href="//commons.wikimedia.org/wiki/File:The_overthrow_of_dr._slop.jpg" title="File:The overthrow of dr. slop.jpg">Image:The overthrow of dr. slop.jpg</a> for a more elaborate version — while equivalent modern signage would include an abstract arrow symbol instead.)
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The main joke was that it was not expected or approved behavior at the time for women to have their legs widely spread apart in public for any reason.  (In other words, the sailor is commenting on her manner of riding, rather than the direction she is going; and the pun on the place name "Stretchit" with "to stretch it", implying that riding in such a way would stretch the woman's vagina.)
Unknown 1800-1810 artist
English engraving c. 1800 - 1810.
The first upload was scanned from one of the early twentieth century <a href="https://en.wikipedia.org/wiki/Eduard_Fuchs" class="extiw" title="en:Eduard Fuchs">Eduard Fuchs</a> <i>Karikatur</i> books by User:Churchh.  Second upload is from UK National Maritime Museum at <a rel="nofollow" class="external free" href="http://collections.rmg.co.uk/collections/objects/138542.html">http://collections.rmg.co.uk/collections/objects/138542.html</a> .  See also <a rel="nofollow" class="external free" href="https://www.britishmuseum.org/collection/object/P_1935-0522-10-78">https://www.britishmuseum.org/collection/object/P_1935-0522-10-78</a> for a different 1803 caricature with same theme.