I had a girlfriend after my first divorce. I wasn't serious about her but she was very cute, long brown hair, brown eyes and about 5'2". She wasn't as white trash as her brother but just not what I was looking for.
I noticed her younger brother spying on us at least once as we had sex. HE was white trash. So I started fantasizing about putting on a show for him or even watching them together. But this girl would never go for it.
One night the brother and I ended up talking alone. He had been drinking and I got him to open up about his desires. At one point during the conversation I asked him if he'd like to fuck her. He got embarrassed but admitted that fucking his cute big sister was his biggest fantasy.
I then shared with him a plot that I had already come up with. It would take some timing and planning but we both thought we could get his cock inside his sister without her realizing it wasn't me. First, we would have to wait till she was drunk. She wasn't a big drinker and I didn't drink at all. So I never suggested that she drink and she never ordered too many in front of me. Next, we would have to get the brother in her bedroom to hide until we got back from our date. She lived with her uncle but this uncle's door was always open to his nieces and nephews. Last, he would need to already be naked so he could sneak over in my place without her hearing a third person in the room.
I guess it was a couple of weeks (of the brother badgering me about it EVERY time we were alone) but it seemed like forever. I was as excited about it as he was. Then I overheard her sister telling her about a new fruity drink at a local restaurant. I very casually volunteered to buy her a couple. The date was on! But the brother wasn't there. Now what? He was already out on the town with friends. He was an annoying little brother at times. The one thing that used to really get on my nerves about him was now the thing I was hoping for. He might see us out that night and come over to bother us.
He did, and it was while I was buying his sister those fruity drinks. As he approached our table I noticed he was looking at his sister's glass, this was no cola she was drinking. We made eye contact. I gave him a thumbs-up. Looking back, it was funny how fast he made up an excuse for his friend to give him a ride home.
So I started to relax. The plan was finally unfolding. I subtly suggested that she have another, then another. My excuse was that we were celebrating a new job she was getting. This prompted two of her friends to buy her a drink. The total was five or six adult beverages. She was slurring her speech pretty noticeably at this point. Perfect! After all, I wanted her compromised, not unconscious. "Check please."