Compare Painting 14A with this one, #43, which presents an alternate view of the first transfer from the Gemini-B through the tunnel into the pressurized module. The Gemini-B is stubbier and thus proportioned more realistically than in Jacobe's other paintings in this collection, but it has the red nose section that Jacobe seems to have insisted upon.
This image, like #5 and 7, is a photograph of a painting instead of an actual acrylic painting. Like them, it probably predates the rest of the collection. It shows the pilots wearing the David Clark Co. Gemini G4C space suit (at left in photo below) instead of the Hamilton Standard MH-5 MOL suit (at right in photo below). The G4C was worn during weightless testing in 1966 because it was the most advanced current space suit but David Clark proposed a modified version for MOL, with more flexibility and a modified helmet permitting greater visibility. The MH-5 and its flight variant the MH-6 also embodied these modifications and were selected for MOL use in early 1968.
This image also appears to repeat Jacobe's error in #11 of switching the roles of the crewmen. Flipped horizontally, the image more realistically shows the co-pilot would being first through the tunnel into the MOL at the beginning of the mission; he would also be the last out at the end of it. This would have been consistent with the established Gemini roles of the command pilot, in the left seat, maintaining spacecraft control while the right-seater performed spacewalks, operated the computer and so forth. This was also the crewman order used by the Air Force in weightless tests of tunnel transfer techniques during parabolic airplane flights in 1966 and in most aircraft flight operations.