You seem to have a handle on the most likely reasons:

• One interpretation is that he's insecure and needs validation.
• Another is that it's a power move to keep you in line by letting you know he has options so don't step out of line, or he'll access those other options.
• He may just be egotistical and likes to brag.

Next time he brings it up, just calmly ask him "I'm not sure why you are telling me this. What am I supposed to do with that information?"

You could also go with "yeah, I get a lot of offers too" and when he gets upset, respond with "oh, I thought we were sharing."

No matter how you slice it, it's a douchy maneuver.

Sounds to me like he wants to brag and is suddley letting you know that he has Options

Girl, just flat out tell him you don’t care about how many invites he had before you two met. If he’s stuck on his high horse, then I would move on. Be with someone who respects you, and the current, not the past.

It's most likely a brag, meant to convince either you or himself that he's a catch. He may also be inviting you to share more details of your own past. Either way, I wouldn't dignify it with a response. If it doesn't stop, and if you find it unbearable, end the relationship.

Ask him why he KEEPS telling you this.

Tell him to stop. I told my wife about a coworker who let me know she was available once and it did not go well, so I stopped.

Say "oh, same here," then nothing else. If he freaks out at you for saying that, you know he's doing it to keep you insecure.

Then you can say "well, I don't want to keep you away from your other options," and then cut him loose.

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He wants you to know he has options. He wants you to feel insecure, like you have to fight to stay relevant in this relationship.

Honestly? He's 33 and this is high-school mean-girl behaviour.

Dump him. You're worthy of so much more.