diff --git a/ddtrace/internal/wrapping/context.py b/ddtrace/internal/wrapping/context.py
index 2e5be4b1013..2389631106a 100644
--- a/ddtrace/internal/wrapping/context.py
+++ b/ddtrace/internal/wrapping/context.py
@@ -13,7 +13,13 @@
 from bytecode import Bytecode
 
 from ddtrace.internal.assembly import Assembly
+from ddtrace.internal.forksafe import Lock
 from ddtrace.internal.utils.inspection import link_function_to_code
+from ddtrace.internal.wrapping import WrappedFunction
+from ddtrace.internal.wrapping import Wrapper
+from ddtrace.internal.wrapping import is_wrapped_with
+from ddtrace.internal.wrapping import unwrap
+from ddtrace.internal.wrapping import wrap
 
 
 T = t.TypeVar("T")
@@ -406,6 +412,44 @@ def unwrap(self) -> None:
             _UniversalWrappingContext.extract(f).unregister(self)
 
 
+class LazyWrappingContext(WrappingContext):
+    def __init__(self, f: FunctionType):
+        super().__init__(f)
+
+        self._trampoline: t.Optional[Wrapper] = None
+        self._trampoline_lock = Lock()
+
+    def wrap(self) -> None:
+        """Perform the bytecode wrapping on first invocation."""
+        with (tl := self._trampoline_lock):
+            if self._trampoline is not None:
+                return
+
+            def trampoline(_, args, kwargs):
+                with tl:
+                    f = t.cast(WrappedFunction, self.__wrapped__)
+                    if is_wrapped_with(self.__wrapped__, trampoline):
+                        f = unwrap(f, trampoline)
+                        super(LazyWrappingContext, self).wrap()
+                return f(*args, **kwargs)
+
+            wrap(self.__wrapped__, trampoline)
+
+            self._trampoline = trampoline
+
+    def unwrap(self) -> None:
+        with self._trampoline_lock:
+            if self._trampoline is None:
+                return
+
+            if self.is_wrapped(self.__wrapped__):
+                super().unwrap()
+            else:
+                unwrap(t.cast(WrappedFunction, self.__wrapped__), self._trampoline)
+
+            self._trampoline = None
+
+
 class ContextWrappedFunction(Protocol):
     """A wrapped function."""
 
diff --git a/tests/internal/test_wrapping.py b/tests/internal/test_wrapping.py
index 3610f0d452a..40e048f5bf3 100644
--- a/tests/internal/test_wrapping.py
+++ b/tests/internal/test_wrapping.py
@@ -10,6 +10,7 @@
 from ddtrace.internal.wrapping import is_wrapped_with
 from ddtrace.internal.wrapping import unwrap
 from ddtrace.internal.wrapping import wrap
+from ddtrace.internal.wrapping.context import LazyWrappingContext
 from ddtrace.internal.wrapping.context import WrappingContext
 from ddtrace.internal.wrapping.context import _UniversalWrappingContext
 
@@ -926,3 +927,42 @@ def foo():
 
     new_method_count = len([_ for _ in gc.get_objects() if type(_).__name__ == "method"])
     assert new_method_count <= method_count + 1
+
+
+def test_wrapping_context_lazy():
+    free = 42
+
+    def foo():
+        return free
+
+    class DummyLazyWrappingContext(LazyWrappingContext):
+        def __init__(self, f):
+            super().__init__(f)
+
+            self.count = 0
+
+        def __enter__(self):
+            self.count += 1
+            return super().__enter__()
+
+    (wc := DummyLazyWrappingContext(foo)).wrap()
+
+    assert not DummyLazyWrappingContext.is_wrapped(foo)
+
+    for _ in range(n := 10):
+        assert foo() == free
+
+        assert DummyLazyWrappingContext.is_wrapped(foo)
+
+    assert wc.count == n
+
+    wc.count = 0
+
+    wc.unwrap()
+
+    for _ in range(10):
+        assert not DummyLazyWrappingContext.is_wrapped(foo)
+
+        assert foo() == free
+
+    assert wc.count == 0