The algebra $A:=\mathbb{C}_\sigma^\xi[G]$ is the universal $\mathbb{R}$-algebra that
- contains $\mathbb{C}$ and symbols $\{u_g \mid g\in G\}$ such that
- $u_g u_h = \xi(g,h) u_{gh}$ and $u_g z u_g^{-1} = {^g z}$ holds, where I use ${^g z}$ as a shorthand for $\sigma(g)(z)$.
This is an example of a "crossed" $G$-graded $\mathbb{R}$-algebra, i.e. an algebra that is equipped with a decomposition $A=\bigoplus_g A_g$ such that $A_g A_h\subseteq A_{gh}$ (that "$G$-graded") and $A_g\cap A^\times\neq\emptyset$ (that's "crossed"). An ordinary group algebra $K[G]$ is an example, a twisted group algebra $K^\xi[G]$ is also an example. Your example is a little bit different than those two, because the degree-1-piece is 2-dimensional over the field, not the field itself. One particularly easy example is the $C_2$-graded crossed $\mathbb{R}$-algebra $\mathbb{H}=\mathbb{C}\oplus\mathbb{C}j$ (which is also a special case of your assumptions for $G=C_2$)
Crossed, $G$-graded algebras are nice to have, because you can do Clifford theory with them: The degree-1-piece behaves very much like $K[N]$ behaves inside $K[G]$ for any normal subgroup $N\unlhd G$. In fact: That's one example - Take any $G$-graded algebra and define a $Q:=G/N$-grading by setting $A_{gN} := \sum_{h\in N} A_{gh}$. If you do that with $A=K[G]$, then the degree-1-piece in the $Q$-grading is exactly $K[N]$.
In your example, let's have a look at the normal subgroup $N:=\ker(\sigma)$ of index 2. The degree-1-piece of the $Q$-grading on $A$ is the twisted algebra $A_N:=\mathbb{C}^\xi[N]$ (just considered as an $\mathbb{R}$-algebra). This is one complication fewer and assuming you understand such algebras well enough, one can count the representations of $A$ by using Clifford theory.
The grading group acts by conjugation on modules of the degree-1-piece. The appropriate generalisation of Clifford's theorem now tells you that for any simple $A$-module $V$, the restriction $V_{|N}$ of $V$ to $A_N$ is semisimple and the occurring simple constituents are a single $Q$-orbit that all occur with the same multiplicity $e=e_V$.
This leaves us with only three cases
$U=V_{|N}$ is itself simple.
$V_{|N} \cong U\oplus U$ for some simple $U$ and conjugation switches the two copies of $U$.
$V_{|N} \cong U_1\oplus U_2$ for two non-isomorphic, but conjugated simple modules $U_1, U_2$.
In that case $I_{U_i} = 1$ and $V$ is obtained by induction from either constituent, i.e. $V=\operatorname{Ind}_1^Q(U_i) = A \otimes_{A_N} U_i$. Conversely: The induction of every simple $A_N$-module $U$ with $I_U=1$ is a simple $A$-module whose restriction back to $A_N$ splits into $U$ and its conjugate.
To count real and quaternionic representation, note that $Q$ also acts via conjugation on $\operatorname{End}_{A_N}(X)$ for all $A_N$-modules $X$ and that $\operatorname{End}_A(X)$ is precisely the space of $Q$-fixed points of this action.
Consider in particular $X=V_{|N}$ and note that $\operatorname{End}_{A_N}(U) = \mathbb{C}$, because $\mathbb{C}\subseteq Z(A_N)$ so that every module is automatically a $\mathbb{C}$-vector space and the $A_N$-action is by $\mathbb{C}$-linear maps, so that we can apply Schur's lemma for finite-dimensional algebras over the complex numbers.
Let's look at $X:=V_{|N}$ in the three cases:
1.) Then $\operatorname{End}_{A_N}(X) = \mathbb{C}$. The only possible actions of $Q$ are the trivial action and complex conjugation. $V$ cannot be quaternionic and $V$ is real iff it is the latter.
2.) Then $\operatorname{End}_{A_N}(X) = \mathbb{C}^{2\times 2}$. If $Q$ acts $\mathbb{C}$-linearly, then it must act by conjugation by Skolem-Noether. If it acts semilinearly, then it acts by conjugation followed by complex conjugation. Because it switches the two copies of $U$, the conjugating matrix must be of the form $X=\begin{pmatrix}0&\ast\\\ast&0\end{pmatrix}$. The linear case gives $\mathbb{C}$, the semilinear case $\mathbb{H}$ as fixed point space.
3.) Then $\operatorname{End}_{A_N}(X) =\operatorname{End}_{A_N}(U_1)\times\operatorname{End}_{A_N}(U_2)=\mathbb{C} \times \mathbb{C}$. The conjugation permutes $U_1$ and $U_2$ and so must flip the two copies of $\mathbb{C}$. Again, because there are only two $\mathbb{R}$-automorphisms of $\mathbb{C}$, we only have a limited number of ways, this can happen:
$$(z,w) \mapsto \begin{cases} (w,z) \\ (\overline{w},z) \\ (w,\overline{z}) \\ (\overline{w},\overline{z}) \end{cases}$$
with fixed point space
$$\begin{cases}
\{(z,z) \mid z\in\mathbb{C}\} \\
\{(r,r) \mid r\in\mathbb{R}\} \\
\{(r,r) \mid r\in\mathbb{R}\} \\
\{(z,\overline{z}) \mid z\in\mathbb{C}\}
\end{cases}
$$
In the first and fourth case, $V$ is neither real nor quaternionic. In the second and third case, $V$ is real.
To conclude: The number of real representations of $A$ is the number of simple $A_N$-modules that are $G/N$-invariant, extend to $A$-modules with the above $Q$-action, plus the number of simple $A_N$-modules that are not $G/N$-invariant and have the right $Q$-action, divided by two