We study application of convolutional codes to the randomized encoding scheme introduced by Wyner as a way of confusing the eavesdropper over a wiretap channel. We describe optimal and practical sub-optimal decoders for the main and the eavesdropper's channels, and estimate the security gap, which is used as the main metric. The sub-optimal decoder works based on the trellis of the code generated by a convolutional code and its dual, where one encodes the data bits and the other encodes the random bits. By developing a code design metric, we describe how these two generators should be selected for optimal performance over a Gaussian wiretap channel. We also propose application of serially concatenated convolutional codes to this setup so as to reduce the resulting security gaps. Furthermore, we provide an analytical characterization of the system performance by extending existing lower and upper bounds for coded systems to the current randomized convolutional coding scenario. We illustrate our findings via extensive simulations and numerical examples, which show that the newly proposed coding scheme can outperform the other existing methods in the literature in terms of security gap.