Strangers in a Bar Pt. 01

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.

"Take it away, Maestro," I say, relieved that I was able to come to my senses enough to say something witty. I sit back in my seat to give you the stage and to keep myself from staring at your breasts. Instead I look at your back. The skin here is soft and pale, and freckled as well. I notice that I don't see a bra strap. The tight top you have on is cut to accentuate your breasts and possibly provides enough support on its own. Or maybe you just wanted to go out without a bra. Are you wearing pantie? I imagine your nipples rubbing against the fabric that I want to reach out and touch as you try to get the bartender's attention with your tits. Does it make you feel sexy to be able to do that? Are you turned on right now? I start to get hard again. I look at the TV behind the bar showing a baseball game. Your martini glass is empty. You may have already had a few cocktails.

It doesn't take long for the bartender to get over you. Amazing, but not surprising. "I'll have another. Vodka martini. Dirty." You lean back and add, "I think this gentleman needs something too."

Gentleman. Would you say that if you knew what I was thinking just now? I lean forward. "That sounds perfect. I'll have the same please." You didn't order something blue, green or red with "tini" added at the end. Again I'm impressed. You truly are a unique flower in a field of heavily made-up daisies.

The bartender gets to work, and I turn to you. "Thank you. That's a hell of a trick you've got there." The weight on my chin isn't as heavy as before, but I still have to concentrate not to look at your tits. It's not that hard though, considering I can look at your beautiful green eyes instead.

"You're very welcome," you say. "But it's not my trick. I like to think of myself as using their own power against them." You use your thumb to discreetly point down the bar at the aforementioned group of MILFs. I smile broadly at your sarcasm. I look in that direction and then scan the bar again. It seems to be mostly tighty wrapped MILFs at the bar now and men talking to them.

"I see what you mean about getting the bartender's attention. What's going on? Is it ladies night or something?" I know what's going on, I've come to MILF central, but I act dumb.

"Ha! No," is all you say and lean forward to get your newly delivered drink from the bar. You plop back in your seat as you attempt to take a drink, but the movement is too abrupt and you spill a little on your chin and chest. I can finally look down as I watch the liquid drip off your chin and run in between your breasts. I think about that being my cum as you struggle to swallow my load. I am hard again. I turn and grab a napkin off of the bar.

"Uh oh. Here you go." You put your drink back down. You wipe your chin and chest. I look conspicuously away as you push the napkin into your cleavage to catch the runaway.

"Ugh. Thanks." You look embarrassed, which makes me feel so much better. I realize you're nervous too. I laugh a little. You look hurt.

"Oh. No. I'm sorry," I say reaching out and touching your upper arm. It was an instinct. I quickly pull it away. "I'm sorry. I'm not laughing at you. It's just..I...You were looking so cool and collected and then...I apologize." I can't really explain that my laughter was relief at realizing you were a regular person like me, instead of the sexy, mature goddess I was imagining. I turn away and take a drink. I think I may have just blown it again.

Instead of putting the wet napkin, that had just been between your breasts, on the bar, you hand it to me. I dispose of it after I note the warmth on my finger tips.

"No, you're right," you smile. "I was trying to look cool and nonchalant. Did I pull it off?"

"Oh yeah. Totally."

You laugh. Phew, that was close.

Now the ice is broken. Both of us realize the other is nervous and it makes us both feel more relaxed.

"I'm Sean," I say, holding out my hand.

"Carissa," you respond taking my hand gently and smiling warmly. "It's nice to meet you Sean."

"The pleasure is all mine, Carissa. And thanks again. Here's to using your power for good." Our glasses clink.

We both relax into a casual conversation. First it's about the weather and the sports that are on the TV behind the bar, then about the other clientele at the bar, then our kids. You are witty and sarcastic, which I love. I'm witty and sarcastic too. We both laugh a lot, but I'm careful not to add too many of my own comments about the other women. I don't want to accidentally push a button.

We talk for about an two and a half hours and you use your tits to order us a couple more rounds. Neither of us are pounding down drinks. I am drinking water in between martinis to try to keep tomorrow's hangover at a minimum, and to make sure that I don't get too drunk to fuck—maybe. You start following my lead and drinking water too. I hope that your reasons are the same a smine. Both times you order drinks, you use your tits to get attention. I lean back to give you the spotlight and to keep myself from getting caught staring at you. I feel a sense of pride being at the bar "with" a woman who's able and willing to use her looks this way, and at least partially, for me.

The first time, I sit back I look at your waist. Through the tight material of your top I can see a slight roll appear at your side moving around to your front. You've got a little layer of fat around your midsection, which for a woman your age and given your large breasts is perfectly natural. In fact, I imagine that it would give your exposed stomach a softness that would be alluring as you lay naked on a bed with your breasts free and parting to the sides. I get another hard-on.

The second time, you scoot back in your seat as you learn forward to put your tits on the bar. The motion pulls your light skirt tight against your ass. I can't see a lot, but I can see the top of what looks to be a beautiful lush rump. I don't see any panty lines. I imagine that you're wearing a lacy thong that has worked its way up between your ass cheeks. That while you've been talking to me you could feel the soft material rubbing against your sensitive asshole and taint. That each time you laughed, your panties got a little tighter on your mound, putting a little more pressure on your clit, and working a little further up between your pussy lips. That your panties are now damp from the sensations you were feeling while you looked at me, and you can feel the heat growing inside you. My hard-on is now raging and begging for attention. I hope when you turn your attention back to me you'll notice it.

But after the last fresh round of drinks arrive, I see you notice something behind me. Your eyes get wide and you say, "Oh shit," as you turn quickly back towards the bar, away from me. Before I can say anything, I hear a high pitched whine over my shoulder.

"Carissa!. Oh my God. What are you doing here? I heard about John. I'm so sorry." A petite woman with large tits squeezed into a tiny dress swoops past me. She is tight, toned, and tan. She is a total knockout, but nothing about her looks real. Hey eyes, her skin, her forehead, her lips, her tits, her tan, probably even her ass, are all so perfect as to defy believability. But hell, a lot of guys would rather fuck a doll that looked like that than a real woman. I don't understand those men.

You turn and with a fake smile and a high-pitched "Lexi, oh my god," you give her a hug. I can see dread and panic in your eyes as you look up at me. "You look so great," you tell her, pulling away from the hug.

"I know, right? I've been working out. My new private instructor is a real drill sergeant. But it's worth it." She runs her hands down her slim waist. "You should give him a try. I'll give you his number." She steps back and turns to me. "Who's this?" she says slyly. "Are you two together?"

Your mouth is open and you don't know what to say. I look at Lexi like she's a nuisance.

"Uh. Hello," I say in mock confusion. "I just came up here to get a drink. Would you like to take this seat?" I get up with my new drink and I'm sure to brush my declining hard-on against her ass as she squeezes by me to get in my seat. She doesn't react to that at all. It's like I'm no longer there now that she realizes I'm not with you. I give you a wink and you look relieved. Is it just my imagination that look you disappointed as I walk away? Talking to you has been fun and exciting. It's been so long since I've felt this way, I can't even remember. I hope, I pray, that I get to talk to you again.