It turns out that condition (T) is, indeed, sufficient for the $27$ lines (distinct and intersecting as expected) to lie on a cubic surface.
To see this, consider the lines $a_1,a_2,a_3,a_4,a_5$ and $b_6$, where the labeling is as in note (2) of the question: $a_1$ through $a_5$ are pairwise skew, and $b_6$ intersects all of them. Choose $4$ distinct points on $b_6$, and $3$ distinct points on each of $a_1$ through $a_5$ also distinct from the intersection point with $b_6$: this makes $4+5\times3=19$ points in total; since there are $20$ coefficients in a cubic form on $4$ variables, there exists a cubic surface $S$ passing through these $19$ points. Since $S$ contains four distinct points on $b_6$, it contains $b_6$ entirely, and since it contains four points (viz., the intersection with $b_6$ and the three additional chosen points) on each of $a_1$ through $a_5$, it contains these also.
Now $b_1$ intersects the four lines $a_2$ through $a_5$ in four distinct points since $a_2$ through $a_5$ are pairwise skew; and since these four points lie on $S$, it follows that $b_1$ lies entirely on $S$; similarly, $b_2$ through $b_5$, and finally $a_6$ (which intersects $b_1$ through $b_5$ in distinct points), all lie on $S$. So $S$ contains the "double-six" $\{a_1,\ldots,a_6,b_1,\ldots,b_6\}$.
So far, property (T) has not been used, only the incidence relation. Now it remains to see that the $c_{ij}$ lie on $S$. Consider the intersection line $\ell$ of the planes $a_i\vee b_j$ (spanned by $a_i$ and $b_j$) and $a_j\vee b_i$ (spanned by $a_j$ and $b_i$; these planes are well-defined since $a_i$ meets $b_j$ and $a_j$ meets $b_i$, and they are distinct since $a_i$ and $a_j$ are skew): this line $\ell$ must be equal to the $c_{ij}$ of the given configuration, because $c_{ij}$ intersects both $a_i$ and $b_j$ so property (T) implies that it lies in the plane $a_i\vee b_j$, and similarly it lies in the plane $a_j\vee b_i$. But $\ell$ also lies on $S$ for similar reasons¹, in other words, $c_{ij}$ lies on $S$, and all the given lines lie on $S$.
Finally, $S$ must be smooth because it contains the configuration of $27$ lines expected of a smooth cubic surface (it is easy to rule out the case where $S$ is a cubic cone, a reducible surface or a scroll by considering the intersecting and skew lines in the double-six; and every configuration where $S$ has double point singularities has fewer than $27$ lines).
- Let me be very precise here, because at this stage we don't know whether $S$ is smooth (so we can't invoke (T) directly on $S$). We have four distinct lines $a_i,a_j,b_i,b_j$ on $S$ such that $a_i$ meets $b_j$ and $a_j$ meets $b_i$ and all other pairs are skew. Call $\pi := a_i\vee b_j$ and $\pi' := a_j \vee b_i$ the planes generated by the two pairs of concurrent lines, and $\ell := \pi\wedge\pi'$ their intersection. We want to show that $\ell$ lies on the surface $S$. If $\pi$ or $\pi'$ is contained in $S$ (reducible) then the conclusion is trivial, so we can assume this is not the case. So the (schematic) intersection of $S$ with the plane $\pi$ is a cubic curve containing two distinct lines ($a_i$ and $b_j$), so it is the union of three lines: $a_i$, $b_j$ and a third line $m$ (a priori possibly equal to one of the former). Consider the intersection point of $a_j$ and $\pi$ (which is well-defined since $a_j$ is skew with $a_i$ so does not lie in $\pi$): it lies on $\ell$ because it is on both $\pi$ and $\pi'$; and it must also lie on $m$ since it is on $\pi$ but neither on $a_i$ nor on $b_j$ (as the two are skew with $a_j$); similarly, the intersection point $b_i\wedge\pi$ is well-defined and lies on both $\ell$ and $m$; so $\ell=m$ lies on $S$ (and we are finished) unless perhaps the two intersections considered are equal, i.e., $a_j,b_i,\pi$ concur at a point $P$, necessarily on $m$. Assume the latter case: $S$ must be singular at $P$ because the line $m$ through $P$ does not lie on the plane $\pi'$ generated by two lines ($a_j,b_i$) through $P$ (i.e., we have three non-coplanar tangent directions at $P$). Now symmetrically, if we call $m'$ the third line of the intersection of $S$ with $\pi'$ (besides $a_j$ and $b_i$), we are done unless $a_i,b_j,\pi'$ concur at a point $P'$, necessarily on $m'$ and necessarily singular on $S$. The points $P$ and $P'$ are distinct because $a_i$ and $a_j$ are skew; and they are on $\ell$ because they are on $\pi$ and $\pi'$; and the line joining two singular points on a cubic surface lies on the surface, so $\ell = P\vee P'$ lies on $S$ in any case. (Phew!)
What I still don't know is whether there are configurations of $27$ distinct lines with the expected incidence relations and which satisfy neither condition (T) nor its dual (viz., whenever three lines pairwise meet, all three meet at a common point), and in particular, what are the irreducible components of the space of configurations. (I also don't know if there is a way to substantially simplify the tedious argument given in note (1) above.)
Best Answer
I decided to have a go at finding a parametrisation by following the instructions of Coray and Tsfasman (reference in my comment above), using Magma. Amazingly enough, it works, even working generically with $a,b$ variables.
Here's what I did. Working over the field $K(\omega, \sqrt[3]{a^2b})$, find the three singular points of $X$. Writing $c = \sqrt[3]{a^2b}$, they are $(0:c:a/c:1)$, $(0:\omega^2 c:\omega a/c:1)$, $(0:\omega c:\omega^2 a/c:1)$. There's an obvious rational point $(1:1:0:0)$. The Cremona transformation $f \colon \mathbb{P}^3 \to \mathbb{P}^3$ associated to these four points can be found by linearly mapping them to the standard basis points, applying the standard Cremona transformation $(1/X_0: 1/X_1: 1/X_2: 1/X_3)$, and reversing the linear map. It turns out that $f^{-1}(X)$ is (modulo some rubbish supported on the four planes where $f$ is not defined) a quadric surface $Y$, defined by $$ X_0^2 + \frac{1}{3a} X_0 X_2 + \frac{1}{27a^2} X_2^2 + \frac{1}{27a^2b}(X_0-X_1)X_3. $$
The surface $Y$ has an obvious rational point $(0:1:0:0)$, so projecting away from that gives an isomorphism $Y \to \mathbb{P}^2$. The inverse of that isomorphism, composed with $f$, gives a rational map from $\mathbb{P}^2$ to $X$. The equations are (cut & pasted from Magma):
I'm sure these can be tidied up a lot, but notice that they are at least defined over the original base field, since $c$ only ever appears as $c^3$.
I'll post the Magma code (only 20 lines) if anybody's interested.