Dean figured Starfleet tactical procedures could be applied to this situation just as for any other important mission.
The crew of the USS Impala had spent a busy few weeks hunting the pirates who had been marauding in their sector and were glad to finally have some down time to relax. A discussion on the bridge about Dean's holo-porn collection had yielded the surprising information that the android Cas-TL was a virgin. After confirming that Cas was "fully functional" and programmed with "multiple techniques" Dean completed the first step of the mission planning procedure: Determine the Mission. He then informed his crewmates of his intentions as step two of the procedure: Issue a Warning Order and over their protestations moved on to step three of the procedure: Make a Tentative Plan. After mulling over the options Dean had a course laid in for the planet Vegas XXVI as the fourth step of mission procedures: Start Necessary Movement.
When they arrived at the planet Dean scanned the listings on the various pleasure domes as the fifth step of mission planning: Conduct a Recon. He finally selected the King's Lair as the most likely venue for a successful mission.
Samsquatch made a bitch-face and refused to be involved in the mission. He volunteered to stay on board the Impala and keep an eye on the imprisoned G.
After beaming down to the opulent pleasure dome Dean dragged the reluctant Cas over to a table and ordered a pair of Venusian Rhapsodies for the both of them.
Dean evaluated the various workers circulating through the lounge and decided on a sweet looking Deltan as step 6: Complete the plan. Now that the objective was in sight Dean moved on to step 7: Issue the Operations Orders to ensure that Cas understood the mission, the concept of the operation, and his assigned tasks. Meanwhile Cas was doing a good impression of a panic attack for an android and would have hyperventilated into unconsciousness if he had actually needed to breathe. Nevertheless, Dean cheerfully sent the pair off and settled back to contemplate how he would pass the time while waiting for Cas's mission to be completed.
His musings were interrupted by a dismayed shriek and Dean took off down the hallway to see if there was a damsel in need of rescuing. He was shocked to find Cas caught up in a brawl that included 2 drunk Cardassians, a Ferengi in a feather boa, 3 Andorians in leather and chains, a Horta, and some being that looked like a pulsing red blob with shifting tentacles. Dean waded in to help his ship mate and then dragged Cas out the back door when he saw the grim-faced bouncers descending on the chaos.
Dean rubbed his sore jaw and contemplated the fact that Cas had managed something Dean never had: he had gotten them banned for life from a pleasure dome.
Not the "first" Dean had been planning.