I want to give a note and a tip of my cap to another writer I follow here. His writing impressed me and reminded me of a similar situation, yet it was not super sexual. I think and hope you will still find it entertaining.
First, understand who you are dealing with. We are a couple in our 60s who have been around the block a few times. Hopefully, picking up things along the way is as important as leaving a few behind.
We and most of our friends are football fans, and I seem to be the outlier, having my favorite since I was a young boy; the others support the local team, which is righteous to do. Between Dee and I, bets are often common, especially when the two teams occasionally meet. Not monetary wagers, as who needs that? The other one can not refuse a special favor or act. Always within her or my comfort zone, but it can be pushing it at times, and this was one of those times.
Most of our friends are beer fans; odds are, I have the least interest, but a cold beer is great on occasion. Most of those were drunk and at someone's home but known to be found at a local Brew House from time to time; we have many of them occasionally. For my winning the bet, I wanted Dee to be our Kellnerin, Beer Maiden. But more than just that, the costume and all. Dee barked at the idea, but I knew it wasn't going too far. Dee always had a bit of voyeurism in her, admit it or not.
Unknown to her, I bought the whole outfit and stored it away for the right time. I also made sure to pick the right friends to share it with, ones close enough to Dee's comfort and ones where it would not damage our relationship. To me, Tom and Cindy were perfect. Dee and Tom were the first friends going back to college; Tom married Cindy a coons age ago and became very close over the years.
It was some months later when the opportunity arose. The bet was made in January, and it was far too cold to play it out. Going out to dinner in May seemed perfect, yet unknown to anyone but me. We enjoyed dinner and returned to Dee's to shoot the shit on the back porch. Dee handed out a first round of beers, but I pulled Dee aside when the bottles got low, telling her it was time to pay up. Her "Oh, no" was met with my yes, yes, a bet is a bet.
When Tom released his obligatory 'Ahh,' meaning his bottle was empty, Dee headed in for another round. Cindy had just finished hers, and a good half remained for me. Then Tom started to tap his empty bottle on the arm of the chair; although he couldn't imagine what was taking so long, I knew exactly why. The backdoor swung open to Dee, who was all geared up as if fresh from Germany. She was met with light laughter, which stopped when she proclaimed, "He made me do it." (her finger pointing in my direction.)
"Oh, come on, Honey, you look beautiful."
She changed her frown to a smile when she said, "Do you think so?"
I was helped when the other two said she looked good in her garb. From then on, Dee fit into the role quite well. As it went from dust to dark since we began, I turned on more lighting so we could see better. It was admittedly clear to me, and not far after that, we could all see the small patch of hair over Dee's otherwise shaved pussy through the sheer fabric of her ruffled panties. I was sure Cindy also saw it from the blush on her cheeks. But Dee was none the wiser, not yet anyhow.
I could tell Tom was eyeing Dee's boobs, too, maybe because Dee was a full D while Cindy was perhaps a B cup. But they shouldn't be news to Tom; he knew her long before her breast reduction surgery. It could have been from Dee's hard nipples poking out the loose material of her blouse, a clear sign she didn't hate this.
Although these things only took minutes, all three finished their second beer, and I did my first. While Dee fetched another round and most likely the last, I took the opportunity, "Nice boobs, don't you think?" Tom looked at Cindy, not knowing or too afraid to speak; it was Cindy who rang out, "I always liked her breasts and wondered what they would feel like."
I knew what Cindy meant to have boobs that big. But that wasn't going to stop me from having fun with it. So when Dee returned, I told her, "Hey Baby, Cindy wants to feel your boobs."
Dee laughed while approaching them with their beers. "Well, go ahead, I guess."
Cindy: "Well, I meant to have them, but okay." With that, she cupped Dee's breasts in her small hands.
I jumped it: "That doesn't count. Pull them out. Flesh in flesh is the only way to feel them."
"Oh, you don't think I will? Want to bet?" Dee asked.
"Careful, betting is what got you here." l said--with that, Dee pulled at the elastic collar, exposing her top half. "Well, Cindy, here is your chance." Cindy looked toward Tom, reached up, and cupped Dee again, but flesh on flesh this time. Dee moaned to her nipples, stretching out, pulling the skin to higher limits. Jumping in again, "Get in there, Terri; Dee won't mind.
Tom didn't look toward Cindy for permission, and I guess he didn't have to because as soon as I said it, she gave up her grip on one of her breasts so Tom could join in. Massaging and even pulling at her nipples at times, we were all in new territory. That was when Cindy cried, "Oh my God, you're hard." (looking at Tom's lap)
