It all started one night when I was out for dinner with my family. My wife Lana and I, along with my brother and his wife, two sisters and their husband and fiancΓ©, were celebrating my birthday. We all get along well, and we have a good time when we're out. This time, however, my wife and my older sister were pregnant, and they ended up leaving after dinner. The rest of us went upstairs to a Jazz bar.
After a few drinks, the others had left, leaving just me with my little sister Lisa and her fiancΓ©, Todd. We ordered a bottle of champagne, and after drinking one glass, Todd suddenly looked a little green and excused himself. We both laughed, knowing that he was likely in the bathroom returning his champagne.
Moments later he came back, said a quick goodbye and left. My sister and I sat next to each other in our cozy booth and listened to the music, sipping our champagne. I looked over at my little sister.
Lisa is 11 years younger than me, and was the result of our father's second marriage. She was now 22, and was absolutely gorgeous. What made her even sexier was her personality β she loved to have fun, which is why we got along so well.
As you may have guessed, I had a little bit of a crush on her. It wasn't something I'd ever act on, and it didn't affect our friendship, but it was definitely there. She looked over and saw me watching her and smiled.
"What?" she asked?
"Nothing," I said. "Let's dance." I grabbed her and pulled her onto the dance floor.
We danced with each other and other people, having a great time. Occasionally we'd rub our bodies against each other, and once she started grinding her ass against me, but it was all just her being playful. We danced and drank for hours, and when we finally sat down we noticed we had finished our third bottle of champagne.
We were sitting very close to each other, and I could feel the heat coming off her body. We were talking about general stuff, nothing earth shattering, when her friend Alissa came over. She was a waitress at this club and one of the hottest girls I'd ever seen. She and Lisa had been friends for a long time, and I had always wanted her. She slid into the booth beside me.
We talked for a bit, though it was mostly Alissa and Lisa leaning across me to talk to each other. Both of them placed their hands on my thighs for balance, and after a minute, Alissa said she had to leave, kissing me on the cheek and rubbing my thigh softly. I watched her go, admiring her ass swaying as she walked. I turned to see Lisa smiling at me.
"What?" I asked, knowing I had just been busted.
"You're married, you know," she said.
"I can still look," I said, grinning.
"Just don't do more than that," she said, but she was still smiling.
"Yes, mom," I said. She hit me in the shoulder, hard.
"Seriously, you wouldn't cheat, would you?" she asked, now more serious.
"No, never," I replied. "Well, almost never." The champagne was having a definite effect, loosening my tongue.
"What do you mean, almost never?" she asked. "Have you? Cheated?"
My wife and I had been married for three years, and I had never cheated in that time, and really never expected to. But I had my 'List', a small number of women that I would make love to if given the chance. I had never told anybody about the List.
"No, I haven't," I answered.
"But you would?" she asked. She wasn't angry, but seemed curious.
"Listen, we probably should stop talking about this before you get me in trouble," I said.
"Why? Tell me, would you cheat?"
I sighed, knowing I'd give in eventually. "I might, if it was the right person," I replied.
She looked at me, her eyes wide. "Really?" she said. "Who's the right person? Is it somebody specific?"
"Yes," I said. "But I'm not telling you who they are."
"THEY?" she said, grinning again. "There's more than one? Oh my god, you have a list!" She grabbed my thigh just above the knee and squeezed. "Come on big bro, tell me!"
I squirmed as she ticked me, trying to resist. I knew that between the alcohol and her persistence I'd give in anyway, so I decided to tell her one of the names.
"You have to swear not to tell anybody," I said. "Not Todd, not anybody. Ever. Promise?"
"David, I have secrets you would not believe," she said, using my name as she rarely did. "I promise, I won't tell a soul."
"And just because I say a name doesn't mean that I'd really ever do anything," I said.
"Okay," she said impatiently. "Just tell me!"
"Alissa," I said. Her eyes went wide.
"Really?" she asked. "You want to fuck Alissa? My friend Alissa?" Her hand was back on my thigh, not tickling anymore, just resting. "Yes," I said. "I have for a while. But it's not just fucking. It's..." I realized where I was about to go and stopped.
"What?" Lisa said. "It's what?" She was getting excited, I could tell.
"Nothing. Listen, we should stop talking about this," I said.
"Why? Are you embarrassed?" she asked. "Come on, bro, we've always been friends, just pretend I'm one of your guy friends and tell me. I can promise it's nothing I haven't heard before." She rubbed my thigh softly and I felt things stirring down below.
"Okay," I said, taking a deep breath. "It's not just fucking. I feel like I have a spiritual connection with her. It's not love, but it's not just sex. I can't really explain."
She looked at me and was smiling even wider now. It was kind of freaky.
"What?" I asked her.
"She wants to fuck you too," Lisa told me.
"What? Really?" I said. I was truly surprised.
"Really," she said. "She has for years. When she used to sleep over, she'd watch you shower."
"What! How?" I asked, incredulous.
"The attic was above your bathroom, and if you looked through the light fixture you could see everything. She would go up there and wait for you to shower. She'd watch you and masturbate. You probably made her come two dozen times."
I was stunned, both by what my sister had told me and the bluntness of her statements.
"She told you this?" I asked.
"Not at first β I mean, she couldn't hide that she was watching, but I used to watch her watching you." As I realized what my little sister was saying, I felt my cock grow hard. She was watching my reaction.
"So you used to watch your friend masturbating?" I asked. I couldn't believe we were talking about this.
"Hold on," she said. "We're not done talking about you. Who else is on the list?"
"No," I said, smiling and shaking my head. "That's all I'm telling you. I've already told you too much." She put on her fake pouty face.
"Pleeeeeeease?" she said in her practiced whine. It made me laugh. I shook my head.
"Okay, then how about this,"" she said. "Tell me who else is on the list and I'll let you watch the video I took of Alissa masturbating with a dildo that she's pretending is you." I spit my drink across the table.
"WHAT?!?" I yelled. Several people looked over. Lisa just nodded. What she suggested, if true, was so completely offside, but irresistible at the same time.
"Really?" I asked. She nodded, and I could tell that the video was real, as was her promise to show me. I came to the only decision I could.
Okay," I said, and took a deep breath. "Sara."
She looked at me for a minute, and then her eyes went wide. "Our sister Sara?" She said.
"Sister-in-law," I corrected. Sara was my brother's wife, and I had wanted her since the very first time I saw her.
"Holy shit," she said. "We need some shots." She called the waitress over and ordered six shots of tequila.
"Sara, really," she said. "That's pretty hot." She saw Alissa walk by and called her over as the shots arrived. We each did two shots, and Lisa whispered something in Alissa's ear after the first one. Alissa did her second and whispered something back in Lisa's ear, and then turned and left without looking at me.
"She's embarrassed," Lisa said. "I told her I was going to show you the tape."