I am approaching 50, but most people seem surprised when I tell them that and say I look much younger. I dress younger too. Maybe that's all it is. For the last six months I have been working on my dad bod at the local rec center. I don't have a 6-pack or anything, but I'm lean and a little toned. On my 6'1" frame it looks pretty good, if I do say so myself. I put on some jeans, my best thrift-store shirt, the westernish one with the mother-of-pearl snaps, and my square-toed cowboy boots, and I head over to the west side of town. That's where the rich people live. I've been to several big-box stores in that part of town and they are always crawling with hot MILFs in yoga pants or something else tight that shows off their fit bodies. The stereotype is that they're all stay-at-home moms with nothing better to do than join the PTA and spend the day at the gym. I like to imagine that for some of them that works, but that for others their husband's still have to cheat with their 20 year old secretaries because that's the type of men they are-type-A assholes who are all about themselves and their money and what it can get them, which is anything they want. I'm looking for those women.
I go to one of those outdoor shopping areas with lots of high-end and specialty shops and plenty of restaurants and bars. My wife has taken the kids to the beach for a week, but I've stayed behind to work. That doesn't stop her from giving me a long list of things to do around the house while I'm "on vacation". I know that no matter how much of her list I do or how clean the house looks when she gets home, she'll find something to complain about anyway. She'll go to the beach for a long weekend and spend money we don't have and come home pissed off about something anyway. That's the main reason I didn't go. I need a break from her sometimes. Our relationship is congenial as long as we don't talk about money or my needs. It's been years since we've had sex. Not because she won't "put out", but because I am just not interested in her. I'm too frustrated, and angry, and stressed out, and frankly she really let herself go after we got married and there's just no turn-on there anymore.
I am lonely and horny. Maybe even a little desperate. I need something to make me feel alive again, like I'm more that an ATM/chore-machine. I want someone to look at me like I'm not to blame for something, everything. Even if it's just for a little bit. That's why I'm heading to the west side of town to a swanky restaurant/bar in search of another lonely, horny, desperate person to share some time with. I've been squirreling away money in an old shoe for an emergency. It's the only way I can save any money since my wife has access to my bank account. That money is now in my pocket. I feel like this is an emergency.
I pick a place that looks lively, but not crowded. I walk into the restaurant and I'm at the end of the bar, giving me a good look at it's occupants. I see you immediately. You seem to be alone at the bar and there's an empty seat next to you. You're pretty. Maybe you wouldn't be considered classically beautiful by society's often crazy standards, but you're definitely cute and possibly sexy, which is exactly my type. You have bright red lipstick on and large eye. Your dark brown hair is long, but pulled up into a kind of messy knot on top of your head with strands of hair falling out in different places. I have always found that kind of style extremely sexy for some reason. I can only see you from above your waist and up. You are wearing a tight white top that I assume is just half of a skin tight mini-dress. That's pretty standard wear in these parts, of which, I can see plenty of other examples around me. It's cut low and straight across your ample bust with wide straps forming a box around your cleavage. Your arms aren't skinny, but they aren't flabby either.
You see me looking at you and I quickly avert my eyes and continue to look down the bar and then around the restaurant. I'm normally pretty shy around women, especially pretty ones, so flirting and eye contact are not natural to me. I don't want to look away from you, I want to see more, but it's an instinct. I tell the hostess that I'm meeting friends and I walk around the restaurant like I'm looking for someone. This has always been a good way for me to enter a party or a crowded bar when I'm by myself. It gives me a chance to get the lay of the place and not look like I'm lost, which is how I feel. My path takes me past the row of seats at the bar. I look at you again. And again you make eye contact with me. I try not to, but the butterflies in my stomach send a cloud into my brain which shuts things down for a second and I look away again.
I make a circuit of the restaurant looking around with what I hope is a convincing "where are they" face, and don't look back at you. When I get back to the hostess I tell her I'll just wait at the bar. I turn and the seat next to you is still empty. It feels like fate. I take a deep breath and swallow hard. Here goes nothing. I walk over to you trying not to stare.
"Excuse me. Is this seat taken?" I smile.
You look up at me and smile back. "No, go ahead." You adjust yourself a little in an attempt to make room, or maybe move away. But there's really no place to go. Now that I'm close I can see your face. You look to be in your 40s with some lines around your eyes and mouth. Your big eyes are green and beautiful, which honestly just makes me more nervous about trying to talk to you. You have pale skin, but your clusters of freckles make you look darker from further away. They are on your cheeks and nose, and on your exposed chest and breast, and your arms. None of it takes anything away from your attractiveness; it makes you cuter. You have on makeup, but not a ton of it. That makes you stand out in this part of town, which is all about hair and makeup. I like what this tells me about you. I can now see that you have a loose, primarily red, floral print skirt. It's not short, but also doesn't cover up what looks to be a very nice pair of legs. Again, this makes you stand out from the other MILFs in the place. I like to think that the tight top you're wearing is an attempt at something new. I feel fate moving in my direction again.
I sit down and swing forward waiting for the bartender to notice me. I am too scared to look back at you or to say anything else. The butterflies in my stomach are fluttering wildly and that cloud is beginning to seep up into my brain again. I can think of nothing to say while I sit and wait to order. I hope you will meet me halfway. I need your help.
I continue to wait for a drink, sitting forward in my seat, arms on the bar. The bartender is young, probably in his late 20s. He's tall and good looking with sandy blond hair. He's chatting up a group of 4 MILFs sitting further down the bar while he pretends to clean glasses. They all have the hair and makeup and tight dresses typical for this place. One of them looks so toned I think she could be a professional athlete. I think that this bartender must get a ton of hot, mature, experienced pussy, and good tips. They must fuck the shit out of him. The thought sends blood rushing to my dick and I start to get hard.
"I don't think he can see you."
"Huh?" I say stupidly, turning towards you. The fog in my brain and embarrassment about my sudden hard-on has me extremely flustered. I feel like I'm going to blow this before it even turns into a thing.
"Your tits aren't big enough," you say smiling. I feel like I'm straining to keep my head up against a 200 pound weight attached to my chin that wants to pull my face down to look at your tits. I can only imagine the stupid look on my face.
"Let me help." You lean forward pressing your arms together and practically setting your ample cleavage on the bar. The way your tits move makes me think they must be real. Another uncommon trait for the local fauna.
