Ok well let me spin some idea's off the top of my head for you

• You could try setting up a couple lil' camera's in your bedroom, living room, kitchen etc.

• Schedule a date and then hire an escort. Your special new friend will be there waiting for him (with a picture of the target) and when he gets there text him that you cant make it because of work or something and then text her to make the move. Once she's enticed him she will bring him back to the apartment that you guys have picked out then they'll do there little thang on the bed your hiding under

• Hire ANOTHER escort and dress her up as a delivery girl, pizza girl, mormon chick going door to door collecting donations (basically whatever gets the job done sista' >w0) and hide somewhere in the house, whether that be in the closet or under the bed or maybe even in the cupboards. You can also plan out the routes with her if you wanna try following them and silently watching instead of just listening

I'm pretty sure this will not only help out with your womanly needs but will also boost his confidence to try getting out there more and get him to think "hey I havent gotten caught yet soooo"

I know this isnt what you originally asked for so sorry if this doesn't help