What you can do is take the media URL from the first tweet and include that in the text of followup tweets. E.g. I created one tweet with an uploaded image, I then created a second tweet that included the media URL from the first tweet.
The media URL I used can be found in the first status object similar to this
status['entities']['media'][0]['expanded_url']
and the text of the second tweet then looks like this
Kitten two https://twitter.com/devbraham/status/857281142411710466/photo/1