Only in a simulator.
A Cessna 152 is a slow, low-powered trainer. It has a never-exceed speed of 141 knots. So for that aircraft to be going backwards AND be overspeed, you'd have to going into a headwind that exceeded 141 knots.
These windspeeds only occur a) during hurricanes/tornados or b) the high flight levels. You're not going to get a 152 out of the hanger during a hurricane and with a service ceiling around 14,000 feet, you're not getting close to the flight levels, which start at 18,000 feet. I supposed you might see some 100+ knot winds on occasion between 14,000 feet, but again, you're not probably going to be alive to attain the necessary altitude.