The idea was (originally) conceived with trans!Bernard.
Mr. Dowd believes he has a right to his son and can use him as a bargaining chip in certain deals. But there is this condition that Bernard must be "pure" in order to pay.
When Bernard learned of his father's dealings, he decides to resolve this situation on his own and under his own conditions. A fake ID, a convincing disguise, and Bernard isn't willing to go home until he's used the condom he has in his wallet.
But he's not so lucky, and it's Gotham... Through a series of events (involving a bit of sexual pollen), Bernard ends up locked in a private room with a guy dressed as Robin. Bernard doesn't believe he has another chance like this, so he gathers the courage to offer his help to "Robin" with his problem. He manages to convince him, and really, it wasn't as bad an experience as he thought.
"Robin" didn't seem to have much experience either, but he was careful how he touched him (he didn't touch his chest, which Bernard appreciated) and he knew how to touch Bernard's sensitive spots quite tenderly. Bernard may have let slip a "Tim" every now and then, but he believes "Robin" didn't notice. Once they manage to "escape" from the private room, "Robin" disappears into the crowd of disguises, and Bernard is okay with that because he achieved his goal and it wasn't so unpleasant.
On the other hand, Tim is still euphoric about what just happened; he could blame the adrenaline from the fight and the slight pollen intoxication. But that doesn't change the fact that he accepted his civilian friend's offer to help him with his erection... and that it became his first time. Tim might have agreed because he felt comfortable doing it with someone he trusted, especially if that someone thought he was just some random guy in a Robin costume. But he also did it because of how Bernard asked him to; there was a slight urgency in his voice and a plea in his eyes that he found difficult not to accept.
Tim was careful and practical in order to finish quickly, but as things intensified and he couldn't take his eyes off Bernard, from obvious facts like his freckles in various places, even in the slight trembling of Bernard's eyelids when Tim touches his collarbone with the tip of his nose. He also thinks about how beautiful Bernard looks under the red lights of the private room, and that maybe he's very intoxicated because he can hear Bernard calling him "Tim". And that only makes him tremble and want to go faster.
When they manage to leave the private room, he disappears because it's better for Bernard to think he slept with some random civilian in disguise than with him. And Tim should be okay with this, and be able to lie to his face the next time he sees him, but when he does, he can't stop thinking about Bernard's trembling eyelids and Bernard looked so damn good under red lights.
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