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In the eighties, my girlfriend and I lived below this 48 year old guy that lived with his 87 year old mother. He was socially awkward and we felt bad for him. One night we were entering our local video store to rent a "movie" and he was coming out with a black bag. That's what they put adult movies in. We had small talk, he was clearly embarrassed. My girlfriend friend took control and said don't be, it's cool, we're here for one too. Have fun. We started having him down for cards, a beer. We agreed my girlfriend should invite him down when I'm not home and make up things she needs help with. Then, give him a thrill. No bra, loose shorts, bend over and show him her underwear. Things like that. She faked a toilet running excuse a couple of times and left her used underwear on the floor. She took a Polaroid of them (no cell phones) and then said she was running to the basement while he fixed the toilet. Sure enough, the underwear was moved. We got him really drunk one night and asked him to take some Polaroid pics of us, for better angles. He ended up jacking at our kitchen table while watching. My girlfriend tossed him her underwear and told him it was cool. Have some fun. It was pretty hot.