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The bigger question is... why would he care if the game is gifted or if he purchases it himself? Sounds like someone that's planning to take your money, not do the trade, then block you.
There is funds gifting which you get a notification of gifting. But what you're doing is outside trading meaning the person could simply run with your items, and don't gift you afterwards. If you want to sell your items use the market place it there for a reason.
He just does not want it in his purchase history
Doesn't matter what your intentions are. If you are accessory to a crime or violation of the Steam Subscriber Agreement, you will be held responsible.
You are not allowed to charge money for Steam items outside of the Steam marketplace. The only way to sell or buy Steam items is over the Steam marketplace. Not trading.
So its bannable if you give items to them for them to sell for steam credits?
(also I may have accidentally reported you instead of replying. Sorry)
Here's the thing, if he doesn't want to do it that way, it's probably a scam. Only do the transactions through Steam and don't rely on 3rd party sites for any of it.