Side Hustle: Ending

I had spent the night at Terri's and to say my drive home was smooth would have been a lie. I just couldn't concentrate on the road or the people around me. Instead, I just kept asking myself more and more questions. It was a simple thing to say that I wanted to keep seeing her, but she was often very timid and unsure of where she stood with me. I don't know if it's because she's Trans or if it was just something in her DNA, it seemed pretty obvious that she had been heartbroken in the past.

But then so had I and more than a few times if I had to admit it. Still, I felt like I had to make a point to let her know that I was interested in much more than the sex we had shared, but I also knew that sometimes the road to hell is paved with best intentions. I knew that I could mess things up, if I tried too hard to convince her that things were perfect between us. Well, not entirely perfect, but I certainly understood that both of us had our pasts that had inevitably shaped our present. I had asked if she would spend the coming weekend with me, but I hadn't thought enough forward to know where we'd spend that time. I knew that I wanted both of us to be in what I supposed would be 'neutral territory.' I didn't want her to spend it at my house and I didn't want to spend it at her apartment. It felt like it wouldn't be fair to either of us and because of the added complexity of trying to figure out the 'what next' between us, I wanted us to be on equal footing and not to feel forced to agree, or disagree on whatever, or to feel like one of us had the added confidence of being in our respective nests.

To call my house a nest would have been laughable, it was old and had seen many decades over it's lifetime. In fact, it was the project that I retreated to at the end of my work days, to both restore, but also to occupy my time and it provided the convenient excuse that I knew it would. I didn't have time for women, after all, I was fixing up a major renovation on a very old home and there would be time for a possible relationship after the house had been restored and I'd sold it.

But my plan was to just buy another old home and start over again. It wasn't a sudden epiphany that if I kept up this idea of flipping homes, I'd never have time for anything else, maybe I just didn't want to admit it to myself.

I was in the house just long enough to shave and change into a fresh set of clothes, then back out the door with my second cup of coffee and back through the traffic to the office.

The other coder that I had always gotten along with at work, Craig was standing in the breakroom, when I stepped in and considered a third cup of coffee. It's funny how incredible sex overrides everything else, including the common sense to get to sleep at a decent hour on a work night.

"Hey Ty," he said and held out the pot "you look like you need a refill."

"Is it that obvious?" I asked, Craig was a good guy, a little rough around the edges when it came to women, but in my experience, the huge majority of men that worked in IT had similar 'rough edges' and I knew I was no different.

"Let me guess what you were up to last night." He said with a laugh and then stopped himself when he saw the look I was giving him.

"I'm happy for you bro, seriously, jealous, but happy for you." He said as he patted me on the shoulder and walked by.

~

Terri came in a few minutes later and as she had been doing since starting very recently, she offered a simple 'Good morning.' and got herself sorted to start her day.

I sat at my desk and wondered how she could seemingly switch between the very sensual woman I had first hand knowledge of, to being 'just a co-worker' with such apparent ease. It was nearly impossible for me to not just pull her out into the hall and kiss her like a starved nymphomaniac.

"Lunch today?" I tapped away on my phone and hit send.

"Sure, hey, did you still want to do something this weekend?" She sent back.

"Definitely." Was my quick reply.

"You're growing on me Ty." She replied.

"Good, I hoped I wasn't the only one that felt that way,"

"Is it cheating, that chatting like this, is a little easier for me, when it comes to some things?"

"You forget, you're texting a computer nerd, it's a miracle I can manage to speak at all without tripping over my words, especially when I'm talking to a very beautiful woman like you."

She sent the blushing emoji, and I decided to put my head down and try to knock out as much work as I could before lunch, so that I'd have some idea of where I'd like to invite Terri to spend the weekend.

But naturally, that plan went to hell as it seemed like one dumpster fire after the other all morning.

"So, should we take a chance and talk to each other, or do we just pull out our phones and text?" I asked as I sat across from Terri at the diner I usually ate lunch at.

She dipped a hand into her purse and with a grin began furiously tapping away on her phone. "I want to feel you inside me again."

I read the message, my dick began swelling and I just looked at her and said "I can't stop thinking about you."

She mouthed "me too." and that was it, I knew it was early days and we still had so much to learn about each other, but it was almost like that "I want us to be together, exclusively." talk that most people have after their heads and hearts connect.

"Free this weekend?" I asked.

"Not any more." She answered, and reached a hand across the table towards me.

I took her hand and said "I planned to find something nice, something romantic away from our homes, just so we could...."

"I want to spend the weekend with you at your house, I want to help you fix it up." She said, interrupting me before I could tell her that I didn't think of a romantic place as i was trying to fix more problems than I hoped for on a Monday.

"Thats hardly romantic." I countered.

"Trust me." She said, with a knowing expression.

"I won't try to talk you out of it, I guess I can picture you with paint flecks on your nose, I might have to bathe you and clean you up."

"I can get on board with that." Her smile wasn't going away and my crazy Monday morning faded into nothing.

"I want to get your input on something, it's not really so much about 'us', well it is, but..."

"Okay." I said and squeezed her hand.

"I'm not sure it's a great idea for me to keep working at the same company you work for. It's really hard for me to pretend we just work together, you distract me and I think that, well sooner or later people will catch on that wer're..."

"We're what?"

"Is 'seeing each other' too much?" She wondered.

"Maybe not enough." I answered back, quickly.

"Be serious."

"I am, you know the house thing, it's just an excuse for me. I mean, yeah, it makes sense and I know if I have my Dad's smarts about selling houses, I'll be able to turn a good profit, but... It gives me an excuse to not get involved and it feels like I'm involved."

"I don't like pretending that nothing is happening between us at work and it makes me wonder if whats happening, is the same for you, as it is for me."

"I'd hate not seeing you throughout the day, even if we were just acting like generic co-workers."

"How much do you love your job?" She asked.

"I don't love it, I was running around like a chicken with my head cut off this morning, Mondays here suck if you haven't already noticed." I complained, I had mentioned at the beginning of this story, the company I work for was kind of a meat grinder, most new people didn't last long, there was plenty of stress to go around, and it never actually felt like we were doing anything new, just always fixing things that weren't behaving the way we'd planned.

"I have and I suppose that leads me to my next question. If you got fired today, would you be able to make ends meet till you found another job?"

"Sure, I suppose so. I've got a pretty decent-sized network, I've had plenty of recruiters try to poach me, okay, now I'm curious, where's this going Terri?"

"The company I worked for, before starting here is a circus. They only lucked into starting a business at just the right time and hired a guy that became the IT Manager who should have been working for big tech a decade ago. That Manager and I had identified dozens of areas that we could have been doing better, smarter, and simpler. The problem was, the owner wouldn't hear any of it. Instead, he wanted things to stay in their current circus-mode as long as the money kept flowing in. Well, I had toyed with the idea of starting my own business, taking the lessons I learned while there and improving the way we had hoped to. A smart guy like you, working with a smart woman like me, I'd like to talk to you about it this weekend. The bottom line is, if we could keep our hands off of each other till after dinner each night, we could launch in less than three months, I have a lot of contacts too Ty, I think... I think if we actually did this..."

"If we did something like that, I know a guy with a big old house that could double as an office." I said with a crooked grin.

"Am I terrible to leave you hanging like this till this weekend?" She asked.

"Not at all, you'll be spending the night at my place tonight and I figure that with the right amount of kisses, I could have you spilling the beans before this weekend."

"Kisses, and something else too.." She said and licked her lips just a bit.

~

The rest of the day was much less frantic than the morning had been and it gave me plenty of time to wonder about Terri's idea. I'd never put much thought into running a business, it seemed like such a gamble and no promise that it would pay off. Then I laughed out loud and a few people turned to look in my direction.

What promise did I have that the house project would pan out? What promise did I have that I wouldn't be hit by a truck on the way home from work? There weren't any promises in my life, so why did I imagine I needed one now?

I grabbed some Thai food on the way home after work and Terri was waiting for me on the front porch, her big smile made my heart skip a beat and I know it sounds silly, but I hoped everyone in the neighborhood saw the beautiful woman, waiting for ME to get home.

Once inside, we sat at the kitchen table and both of us talked about everything except Terri's plan to start a business.

"Can I ask a loaded question?" She asked.

"Sure."

"Where are 'we' in six months?"

"Sitting right here."

"In that case, you need a new kitchen table and chairs, these won't last another six months."

"Hey! These are antiques!" I feigned being upset.

"Exactly, they're old, and falling apart."

"Seriously though, I can't see a week into the future, so I sure cant see six months. I can tell you that I hope we're doing this very thing then though, sitting down, having a meal, feeling comfortable and really enjoying each other's company."

"Define 'enjoying each others company' for me."

She was putting me on the spot and we both knew it.

"Last night, you thought I was going to grab your dick, let's talk about that." I said, I could put people on the spot too.

"How many woman have you ever met with a dick Ty?"

"Just you."

"How many women have you known, that you wished had a dick, instead of a pussy?"

So much for my plan.

"Not the answer you want, but, I haven't wanted anyone to change who they were. I've never asked someone to lose weight, or to get a boob job, or to wear more heels, or to wear sexier lingerie, I'm happy enough just to have the person."

"I don't like it, because it's the one part of my body that makes me different from other women, it reminds me every day. It's a part of my body that I still haven't gotten to terms with but the thought of having them take it off terrifies me."

"Okay, well easy enough to just leave it right?"

"It's not that simple Ty, but I know what your trying to say. Let me try to explain it like this. Let's say when you were 10 years old you had a really bad accident, and you had a big scar that you hid because it embarrassed you and you wished it wasn't there. Let's say it was someplace you could hide with your clothes on, but as soon as you got naked, you couldnt miss it and whoever you were with couldn't miss it. That's how I feel about what I have between my legs. What I have there, is what you have there, but I'm not like you Ty, I haven't been since I was much younger, so it would almost be like someone playing with that big scar, does that make sense?"

"It's hard for me to imagine being in your shoes but I can't imagine a time, sorry, maybe this isn't the best compliment, but, I just can't imagine you as a guy."

She smiled at that, then held up a finger and cleared her throat. She was silent for a few seconds and then she said 'Hello' but the voice wasn't Terri's at all, it was deeper and seemed completely out of place coming out of her. I'm sure I must have had the strangest look on my face. Terri blushed deeply and then dug back into her food.

"Still, thats not who I see. I suppose I just want to know, without any doubt, that you are getting something out of us fuc... out of us being intimate together."

"You can say that we're fucking Ty, it's okay. We're fucking. Also, I do get something out of it, getting fucked is what feels natural to me, fucking someone, especially a man, would be almost comical for me to imagine. Maybe in time it won't be such a sensitive thing for me, maybe I'll get to terms with it, but for now, just know that I've loved having you fuck me and thats more than enough for me."

I tried to make sense of it, but I realized that in at least that way, we were very different people. My concern was one that wasn't selfish, I imagined having sex with a woman I loved deeply, but never letting myself orgasm when we made love. In a confused kind of way, it felt like that was what Terri was doing to one degree or another. But she had explained herself and as I said, I have never been one to try to change people.

"Tell me about this idea of starting a business."

"Only if we can cuddle while I give you all the details." She said with a grin.

~

Terri was up early enough to drive back to her apartment to change for work the next morning, but I made her promise to pack a bag with several changes of clothes to keep at my place. She said the same right back to me and so I took an old gym bag while it was still really early in the morning and filled it with two different sets of clothes and then made a mental note to buy a toothbrush, razor, shaving cream and deodorant after work to add to the bag.

As I worked, I kept warning myself to slow down with her, it felt like things were moving too quickly, but I wondered if that was primarily due to not having been in a relationship for a while. From everything I could tell, Terri didn't seem worried about the state of 'us' but there was still a bit of worry circling around in my head. Some days back we were out for dinner, when an older guy probably in his forties saw Terri and after his family left the restaurant, he came back and spoke with her at our table briefly. It caught me off guard and not that I'm particularly the jealous type, well, I suppose not moreso than most other guys, but what caught me by surprise was both his age, as well as how Terri seemed reluctant to say much, more than he was a friend and whatever had happened between them was over.

But there was more to that and I knew it wasn't my place to question her further. If she wanted to talk about it, then she would be the one to bring it up. That didn't help chase those thoughts out of my head though. I just couldn't imagine Terri with some married middle-aged guy and I suppose that made me wonder what that made me? As I said in the past, I'm not great at relationships and I suppose me overthinking things, in exactly the same way I was overthinking this, is at least part of the reason for that.

The problem was, there was something 'vulnerable' about Terri that was attracting me like no other woman had before her. At the same time, it wasn't a mystery that she had been with more people than I had, but that had always been the case in my experience. Women can get laid if they want to, regardless of their looks or personality, there's always going to be a line of guys happy to hit that pussy. That she was more experienced, but also vulnerable kept me off-balance a bit because it didn't make sense. Maybe it just meant she was shitty at relationships too and that really worried me, because we were certainly in some kind of relationship.

When I finally decided to just head in to work a bit early, I decided to take a bit of time and research what it would take to start a business, even if it was just a part time thing, sort of like my side hustle with the house. The question had to be where would I find the time? If things progressed with Terri the way I hoped they would, then I knew she would take up the majority of my time away from work, that would slow down progress on renovating the house and then how much time would be left to start a new business?

Like I said, I overthink things to a fault. By the time I took a breath, I realized that I had stressed myself out and the day had barely even started.

~

"Who gets the corner office with the incredible view?" Terri asked and then poked me in my ribs.

"That particular office is reserved for the CEO of the company, however the view is mostly made up of the neighbors trampoline and squealing kids when the weather is nice." I laughed.

"Oh, so then that would be MY office..." She teased.

"Absolutely, and as you're the CEO, I'd like to discuss a raise, you see I met this incredible woman, smart, sexy and impossibly, she's a techie, so I want to make a good impression and take her to nice places and get her nice things."

"Oh I see how this works, in that case, you can be the CEO and I'll ask for the raise." She smirked, and then we both broke out laughing.

I walked into the living room and grabbed a couple of bottles of water and flopped down next to Terri who had landed there a few moments earlier.

"Do you really think we could do this?" I asked.

"I think so, did you really want to try to get this started after working a full day, five days a week? That sounds like a recipe for fast burnout." She cautioned.

"I'm more worried about what happens between us, if all we do is work." I said, and rubbed her leg.

"Have you ever worked for yourself before?" She asked.

I waved my hand around in the air and said "I guess fixing this place up is working for myself, especially if I can sell it after it's done, though I suppose I'll ask Dad to give me some pointers on that."

"Do you talk to him much?"

"Not as much as I should, same with my Mom. How about you? Still talk to your folks?"

"I'm a bit like you, less close with my Mom than my Dad. They've always known I wasn't like other boys and they both handled it really well, but I guess the shock of Mom seeing me in a dress and then the first time I bought a guy home, I suppose it was too much for her. Dad just went with it and has always said he'd support me in any decisions I made and he's always been there so..." She shrugged as she finished speaking.

"Us misfits, huh?"

She chuckled at that.

"We're still on for hanging out this weekend right?" She asked.

"I'm happy to take you somewhere nicer than this old house, but if you want to just hang out here, we can do that."

"I want to do more than just hang out here, I want to help you work on the place."

"Seriously?" I asked, surprised, Terri didn't seem like a woman that had any interest in fixing houses.

"This house has a lot of character, I think about it, when I'm not thinking about you. I wonder who the first family was that lived here, and what their lives were like. I wonder if they had the same kind of complex life I've had and why they moved away. It's easy for me to get curious about old stuff like that I guess."