I realized I cannot fit my answer in the comment space.
As several people pointed out, the concept of "size" is too vague for a mathematician. Consider first the simplest case when the two objects are coins. In this case the concept of "size" in unambiguous: size is the radius of the coin. So we have two coins $S$ (small) and $L$ (large) of radii $r<R$. Suppose that we have two concentric circles circle in the plane of radii $\underline{r} <\underline{R}$. Assume their common center is the origin of the plane. $\newcommand{\ur}{\underline{r}}$ $\newcommand{\uR}{\underline{R}}$ The location of a given coin is specified by its center.
The concept of randomness is very important in these issues and this is where it gets tricky. I will first assume that you're comparing coins with centers located in the bigger circle.
The coin $S$ will fit inside the small circle if its center is located at a distance $\ur-r$ from the origin. Thus the probability that such a coin fits inside the small circle is
$$ p_s=\frac{\pi (\ur-r)^2}{\pi\uR^2}=\frac{(\ur-r)^2}{\uR^2}. $$
Similarly, the probability that the larger coin $L$ fits inside the smaller circle is
$$ p_L= \frac{(\ur-R)^2}{\uR^2}. $$
Since $r<R$ we have $p_s<p_L$ as you have correctly guessed.
Now let me change my assumption. Suppose that I only look at coins that fit inside the bigger circle. A large coin fits inside the big circle if its center is located at a distance $\uR-R$ from the origin, and a small coin fits inside the big center if its center is at a distance $\uR-r$ from the origin. The probability that a small coin that fits inside the big circle also fits inside the small circle is
$$ p_s= \frac{(\ur-r)^2}{(\uR-r)^2}. $$
Similarly, the probability that a large coin fits inside the small circle is
$$ p_L= \frac{(\ur-R)^2}{(\uR-R)^2}. $$
It is less obvious, but again, $p_s<p_L$.
Suppose now that we have two irregularly shaped coins $S$ (small) and $L$. I will say that $L$ is larger than $S$, if we can rigidly move $S$ inside $L$. This involves rotating and and translating the irregular coin $S$ until it fits a region previously occupied by $L$.
Suppose that we look at all the positions of $L$ and $S$ inside the big circle. We denote by $p_L$ the fraction of those positions corresponding to $L$ being inside the small circle. Define $p_s$ in a similar fashion, as the fraction of those positions of $S$ corresponding to $S$ being inside the small circle. Your claim is that $p_S<p_L$. I am inclined to believe that it is true, but I cannot think of an argument.