It was yet another drunken night, Steve and Tony as usual talked about all sorts, most of rubbish. Good friends at school, both had graduated at different Universities and met back up for the summer.
The topic as usual turned to sex and who they fancied, the usual friends and celebrities were mentioned.
At that point Tony asked:
"Honestly, which real woman we know over 45 do you really fancy?"
There were the usual mum jokes, but then they started putting some serious thought into it. A range of ex teachers, neighbours and family friends were considered at length, in the end each had made a choice.
Steve picked a family friend called Anne, a curvy brunette in her mid 40's with a bubbly personality. Despite the age gap, they had always gotten on well and she was interested to catch up with what he was doing. Looks wise she was quite similar to Sarah Palin.
After consideration, Tony admitted he'd had the hots for his neighbour Margo, the Chair of the Women's Institute for years. She was often at his house organising institute business with his mum. He thought she was around 50, married to a high flyer with grown up kids.
She was blonde with hints of white beginning, about 5ft 9 inches with green eyes. Not classically beautiful, but there was just something about her he couldn't quite put this finger on. Maybe it was the prim appearance, the classic vintage 50's look (hair up and fitted pencil skirts and tight sweaters), her confident 'I'm in charge manner' or the fact she was so totally out of reach.
They discussed the merits of each at length and somewhere in the drunken conversation dared each other that they had to try and flirt with the woman of their dreams before they met next Friday.
The next day, Tony was nursing a hangover, he recalled the previous night's conversation and dismissed the idea as nonsense, but it kept niggling away at him through the day. By the time Sunday arrived he thought he might try if the opportunity arose, if nothing else just to put Steve on the spot. Margo had come over as usual, but his mum was always near. When Margo mentioned needing some work done on the house, Tony volunteered saying he needed to earn some cash over the summer.
As a result Tony found himself at Margo's house on the Monday morning, being given a growing list of jobs which would keep him busy for a few weeks. When he had the chance Tony checked Margo out, she had a curvy figure in the usual pencil skirt and matching jacket which kept well hidden what seemed liked some impressive breasts. As usual she wore heels and everything seemed perfectly trussed up and formal. She seemed to rustle as she walked and Tony pondered about if she wore tights or stockings.
She seemed to relax with him there and they chatted more easily than he anticipated.
Margo mentioned going to an event and struggling to pick up an outfit. Tony thought this might be his chance; he stumbled over his words and blurted out:
"You would look great in whatever you wear."
Then there was silence... Margo stopped dead and looked at him quizzically, Tony blushed desperately trying to think of something to make his comment seem less stark and failed. Eventually Margo smiled saying:
"Well that's lovely of you to say, thank you."
Tony was gutted, but at least it didn't seem to bother Margo too much and he could win his dare. Actually if anything she seemed to relax and chat more, she asked about college, friends and girlfriends and shared more of her background, not quite the stern ice queen she initially presented.
He started making good progress with the interior paintings and enjoyed the breaks in Margo's company. He loved her classic looks and styles and enjoyed checking her out when she wasn't looking, especially her rather full but shapely ass.
A few days later, Margo asked Tony to sit for a chat; he didn't think anything of it until she said:
"About your comment the other day and the fact I have noticed you looking at me at times."
Again Tony was mortified and desperately trying to think on his feet.
Margo continued:
"I'm wondering if those things suggest you are attracted to me?"
Tony:
"Ah right, I'm sorry, I didn't mean to stare and I thought it might be nice to give a compliment."
Margo as direct as ever, responded:
"So you aren't attracted to me?"
Tony stumbled again:
"Yes, no I mean... sorry, yes you are attractive, can I just stop talking?"
He then blushed, feeling like an embarrassed school kid asking a girl out for the first time.
Margo smiled and seemed to relax within herself:
"Good, I'm pleased we have cleared that up, so tell me, what would you like to do about it?"
She seemed to know just the thing to say to embarrass Tony the most.
"Well, I would like to get to know you, I mean if you weren't married and mum's friend and everything."
"Hmmm, interesting, I am going to need to tell my husband,"
"What, no, don't do that, he'll kill me and it's not like we have done anything, I just fancy you and looked a bit."
Margo stood:
"I need to think about what is best, we will chat again tomorrow, don't worry about it, let yourself out".