Our DM isn't sure on this, and neither are we. We can't find any specific rules that deal with it.
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6Please consider adding detail to the body text of your question. The title should really summarise what you're asking in the main body, not be the focal point of the question. What makes you, your group and/or DM think this is or isn't possible? What rules specifically have you looked at or are confused about that makes this unclear and thus ask this question? The more detail you can give us - within reason - the better tailored the answers are going to be to help your specific situation. – Purple Monkey Apr 30 '17 at 23:16
1 Answers
The Beholder's Telekinetic Ray does not deal damage
This is regardless of the Fly speed of the creature. What the Telekinetic Ray does is restrain the target if they fail their Strength save, and then move them 30 ft in any direction.
A Flying creature does not take Falling damage
See this answer, which quotes PHB 191, Flying Movement.
If a flying creature is knocked prone, has its speed reduced to 0, or is otherwise deprived of the ability to move, the creature falls, unless it has the ability to hover or it is being held aloft by magic, such as by the fly spell.
If the Beholder used a Telekinetic Ray to move a flying creature above a pit and then releases it with the intent of letting it fall to its death, if it's being held aloft by the Fly spell, it stays afloat.
If the target has wings instead and so it has a mundane, non-magical way of flying, as the target is being released from the Telekinetic Ray's effects, the Restrained condition is lifted. This grants the creature its speed back, including its Fly speed. Since it wasn't knocked Prone, then it can remain flying.