An Enterprising Barista - A local barista needs some extra money. I couldn’t say ‘no’. (erotic coupling) By henryswansonjade. Listen to the Podcast at Steamy Stories. I feel old. Especially being a “middle-aged” guy in a small midwestern college town, it feels like EVERYONE I see on a daily basis is half my age. I generally didn’t engage with many of the college kids, so it almost felt like they were in a different world than me. One exception was my local coffee shop. I’m a sucker for a daily routine, and I like to support local businesses, so despite the two Starbucks with drive-thru windows in town, I went almost every day to a local shop in our small downtown. One bonus to going in person is I got to interact a bit with the younger crowd in a natural way. Today I walked into my coffee shop and one of my favorite baristas was working. There were maybe 8-10 girls who cycled through the various shifts at the shop, and the owner had a knack for hiring a specific type of girl. College-aged obviously, but typically thin, outgoing, pretty girls greeted you every time you walked in the door. Anyway, the aforementioned favorite barista was named Kristina. She wasn’t the typical kind of vapid pretty girl who worked there. She was still gorgeous but had a smarter kind of confidence to her. She got my little jokes that I made every time we had to make small talk while my coffee was being made, she wasn’t afraid to dish out the occasional jab. I felt like when I got a smile out of her I had earned it. Today when I saw her she didn’t seem to be smiling so much. I ordered a breakfast sandwich and debating engaging her. The last thing I wanted to do was be a creepy older dude prying into the lives of the 20 year old barista. Or just being the douchebag who tells a girl she should be smiling more. But I figured I’d give her an opening to open up. “So, how’s your day so far?” Her shoulders slumped and she paused, almost like she was debating whether she wanted to open up to me. We had a friendly rapport but weren’t exactly friends. But sometimes people need to talk, and when she turned around her eyes were a little wet and I could see she was anxious to talk to someone. “Just the usual college shit, but my car is making noises and I’m afraid to take it to shop because I can barely afford rent this month, let alone some ridiculous car repair. Like, I know, such a cliché, single college girl working as a part-time barista has no money, but; guh, I need to find a second job and I just don’t have the time.” She paused, and I could tell she was starting to regret getting emotional. “Sorry. I hate money. It’s hard enough to get hours here to jibe with my classload, I just don’t know how I’m going to get a second job.” I looked at her for a bit, going over what I knew of her, trying to think of some way to help. If I’m completely honest, if it wouldn’t have been creepy as fuck, I just would have offered to fix her car for you. I’m divorced, have no kids, and managed a tech company I had founded several years back. I’m not rich rich, but was doing well enough that I wouldn’t notice paying a thousand dollars or whatever for her car. But even being the socially awkward nerd that I was, I realized that was not an appropriate thing to offer someone. Suddenly I had an idea. “Dogs!” I yelled out. She jumped a bit, startled by my outburst. “Sorry. I just remembered you love dogs. I just got a new puppy, plus my older dog, and work has been busy as shit lately, I could use someone to walk my dogs! I’ve been dreading trying to find a stranger to do it, but you’re… mostly not a stranger.” She briefly looked hopeful, but then deflated. “That sounds great but I don’t know how I can do it with my classes.” I stopped her. “I just need someone to come to the house once or twice a day, no schedule required. I’ll give you, like, 40 bucks a visit.” Her eyes perked up at that. I knew it was on the higher side for what she was doing, but honestly I was just trying to