diff --git a/example/example14.cpp b/example/example14.cpp
index f7f176a18..6a33ba775 100644
--- a/example/example14.cpp
+++ b/example/example14.cpp
@@ -29,4 +29,6 @@ void init_ex14(py::module &m) {
 
     m.def("return_void_ptr", []() { return (void *) 1234; });
     m.def("print_void_ptr", [](void *ptr) { std::cout << "Got void ptr : " << (uint64_t) ptr << std::endl; });
+    m.def("return_null_str", []() { return (char *) nullptr; });
+    m.def("print_null_str", [](char *ptr) { std::cout << "Got null str : " << (uint64_t) ptr << std::endl; });
 }
diff --git a/example/example14.py b/example/example14.py
index aef9923f0..08f5d46a5 100644
--- a/example/example14.py
+++ b/example/example14.py
@@ -4,6 +4,8 @@ import sys
 sys.path.append('.')
 
 from example import StringList, print_opaque_list
+from example import return_void_ptr, print_void_ptr
+from example import return_null_str, print_null_str
 
 l = StringList()
 l.push_back("Element 1")
@@ -13,6 +15,7 @@ print("Back element is %s" % l.back())
 l.pop_back()
 print_opaque_list(l)
 
-from example import return_void_ptr, print_void_ptr
-
 print_void_ptr(return_void_ptr())
+
+print(return_null_str())
+print_null_str(return_null_str())
diff --git a/example/example14.ref b/example/example14.ref
index 38a27e173..7554a5ebd 100644
--- a/example/example14.ref
+++ b/example/example14.ref
@@ -5,3 +5,5 @@ Back element is Element 2
 Opaque list: 
   Element 1
 Got void ptr : 1234
+None
+Got null str : 0
diff --git a/include/pybind11/cast.h b/include/pybind11/cast.h
index dddd40a2c..5ddfdf76f 100644
--- a/include/pybind11/cast.h
+++ b/include/pybind11/cast.h
@@ -391,6 +391,7 @@ public:
         int err = PYBIND11_BYTES_AS_STRING_AND_SIZE(load_src.ptr(), &buffer, &length);
         if (err == -1) { PyErr_Clear(); return false; }  // TypeError
         value = std::string(buffer, length);
+        success = true;
         return true;
     }
 
@@ -399,6 +400,8 @@ public:
     }
 
     PYBIND11_TYPE_CASTER(std::string, _(PYBIND11_STRING_NAME));
+protected:
+    bool success = false;
 };
 
 template <> class type_caster<std::wstring> {
@@ -428,6 +431,7 @@ public:
 #endif
         if (!buffer) { PyErr_Clear(); return false; }
 		value = std::wstring(buffer, length);
+		success = true;
 		return true;
 	}
 
@@ -436,11 +440,19 @@ public:
 	}
 
 	PYBIND11_TYPE_CASTER(std::wstring, _(PYBIND11_STRING_NAME));
+protected:
+    bool success = false;
 };
 
 template <> class type_caster<char> : public type_caster<std::string> {
 public:
+	bool load(handle src, bool convert) {
+	    if (src.ptr() == Py_None) { return true; }
+        return type_caster<std::string>::load(src, convert);
+    }
+
     static handle cast(const char *src, return_value_policy /* policy */, handle /* parent */) {
+        if (src == nullptr) return handle(Py_None).inc_ref();
         return PyUnicode_FromString(src);
     }
 
@@ -449,18 +461,21 @@ public:
         return PyUnicode_DecodeLatin1(str, 1, nullptr);
     }
 
-    operator char*() { return (char *) value.c_str(); }
-    operator char() { if (value.length() > 0) return value[0]; else return '\0'; }
-
-    template <typename T>
-    using cast_op_type = typename std::conditional<std::is_pointer<T>::value, char*, char>::type;
+    operator char*() { return success ? (char *) value.c_str() : nullptr; }
+	operator char&() { return value[0]; }
 
     static PYBIND11_DESCR name() { return type_descr(_(PYBIND11_STRING_NAME)); }
 };
 
 template <> class type_caster<wchar_t> : public type_caster<std::wstring> {
 public:
+	bool load(handle src, bool convert) {
+	    if (src.ptr() == Py_None) { return true; }
+        return type_caster<std::wstring>::load(src, convert);
+    }
+
 	static handle cast(const wchar_t *src, return_value_policy /* policy */, handle /* parent */) {
+        if (src == nullptr) return handle(Py_None).inc_ref();
 		return PyUnicode_FromWideChar(src, wcslen(src));
 	}
 
@@ -469,8 +484,8 @@ public:
 		return PyUnicode_FromWideChar(wstr, 1);
 	}
 
-	operator wchar_t*() { return (wchar_t *)value.c_str(); }
-	operator wchar_t() { if (value.length() > 0) return value[0]; else return L'\0'; }
+    operator wchar_t*() { return success ? (wchar_t *) value.c_str() : nullptr; }
+	operator wchar_t&() { return value[0]; }
 
 	static PYBIND11_DESCR name() { return type_descr(_(PYBIND11_STRING_NAME)); }
 };