My wife and I both knew the best man at our wedding long before we met. When we were dating, we would often hang out with a shared group of friends, which included our future "best man".
Since Ellie and Jack were friends in their own right, it was always comfortable and fun for the three of us to catch a movie or hang out for dinner. Fast forward 29 years of marriage, and the three of us still saw each other frequently.
It had been a month or so since we last saw Jack, and over dinner one night after work, Ellie suggested that we should meet up for drinks. A few text messages later, we had a plan for Friday night at 7. He'd drive to our house, and we'd walk to the local together.
Luckys was a neighborhood place, and less than a mile away. Nothing special, but it was always full, and had a fun vibe. Since we could walk there, it was our go-to after especially long weeks.
Friday arrived, and Jack showed up right on time. We took the short walk and ordered drinks. Two whiskeys' neat, and a pinot noir for the lady. Just as we got our drinks a small round high-top opened up, and we sat down and toasted the end of a long week.
Even though we'd done this countless times in the past, Ellie started the evening more preoccupied than usual, and her drink was gone before mine was halfway through. She quickly got herself a second and didn't waste any time making it disappear.
Taking her lead Jack and I finished round one and got ourselves second drinks. In no time at all we were laughing and enjoying our buzz. In the background they were playing '70's rock music, and there was a hum from all the folks talking and having a good time.
After our second drinks were done, Ellie and Jack went to the bar to order more. Nothing out of the ordinary, but while they were standing next to each waiting for the bartender, I noticed Ellie put her arm around him, as if to console him. He'd been single for a long time, and since we'd briefly talked about it earlier, I assumed they were digging into more details.
Once round three was gone, I suggested that we should make our way home. They both agreed, and even though it was close, Ellie asked me to call an Uber, she was too drunk to walk.
Standing at the curb in front of the bar, Ellie was tipsy and put her arms around us both and belted out "Take me home boys! I always wanted two cute guys to take me home!"
She was smiling and giggling a bit, knowing how ridiculous that idea was, her buzz was clearly in full effect.
When we arrived home, she declared she was done drinking, and got herself some water, but Jack and I agreed on a nightcap. Since he was too drunk to drive, he asked if he could just crash on the couch. We agreed, and I poured two whiskeys, with the plan that all three of us would settle in the living room to watch a movie.
She scurried off to our bedroom as we queued up the movie. When she came back, she was dressed for bed, which meant she was in a tank top, no bra, and black panties.
I couldn't help but blurt out, "What?"
She smiled at me and offered, "He's seen me in a swimsuit, it's the same thing."
My buddy was speechless. Technically she was right, but somehow this was totally different. My wife has a great body, and dressed like this, little was left to the imagination.
I caught Jack's surprise, and in my drunken state, told him he might as well enjoy it and take a look.
He smiled and replied, "Well, yeah if it's OK, I think I will."
She was enjoying the attention and pulled up the tank to show Jack her tits.
His mouth was wide open, and blurted out "Wow, sorry man, but she's hot."
"I know!" was the only correct reply.
It was obvious Jack's cock was hard. Ellie was still smiling, and in a sultry voice said, "does anyone need a hand job?"
Jack replied, "You have no idea."
Now totally enjoying the tension she created, she started asking him super personal questions. Turns out Jack hadn't gotten laid since Miranda, and that was 2 years ago.
Looking at me, Elie said "Come on, let me stroke him off."
Drunk, horny, shocked, and now hard as a rock, I said, "Well. If you want to, go for it."
She walked over to the couch he was sitting on and put her hand on his knee.
Next, she took off her tank top, grabbed his right hand and placed it on her exposed breast. She spoke in a lower volume, and told him he could play with her tit's, but her panties were going to stay on, and if he took his pants off, she'd give him a hand job.
My buddy sort of looked at me and just said "dude?"
I knew he was torn, this was obviously crazy, and probably a horrible idea, but he clearly wanted me to confirm that I sanctioned the act.
He had no clue that I had already pre-approved of what was happening days ago.
A few weeks before while Ellie and I were high together and watching porn she took us down an unfamiliar rabbit hole. We don't usually, but that night she searched the site by the keyword "friend". We watched several videos in that vein and fucked for almost an hour. About halfway through she asked if I liked what we were watching. I was super turned on and agreed that they were hot.
She then asked if I ever wanted to do something like that. Totally shocked I replied, "I hadn't considered that before, but do you?"
