Side Hustle

I work for a company that can be a bit like a meat grinder. For some people, it's a decent job and for others they hate it and move on pretty quickly. I work in the software development department and we turn ideas into code, to say it's one of the more heavily impacted departments would be an understatement. There are eight of us in the department and just two that have managed to stay with the company for more than a year. So seeing new people come (and go) was nothing unusual.

My name is Tyler, although everyone calls me 'Ty', I'm an average guy I suppose, but I want to tell you a very not-average story.

Early one Monday morning, an HR person brought a cute blonde into the office and introduced her as Terri Harper, a newly hired software developer. While there hadn't been a lot of women coders that had worked for the company, there had been enough that seeing a woman on the team wasn't a huge deal. Terri was cute, her blonde hair felt a bit below her shoulders and if I had guessed correctly, I would have said that her natural hair color was a medium brown based on her roots, her eyes seemed animated, excited, just taking in everything in our curiously decorated office-space. She was led to a desk one seat away from mine and everyone introduced themselves.

Afterward, I rolled my chair over to her desk and let her know that she'd be working on a project that I was the Lead on and gave her a quick description of how everything worked. Being a normal guy, I quickly looked for a wedding ring and found nothing. While it wasn't something I ever actively pursued, there have been times that I have dated co-workers. Interestingly, those relationships have never been as awkward as what I've heard from others.

As we chatted, I quickly realized that Terri was very intelligent and her questions really made me think before I answered. Within five minutes I decided that she'd either last a month and quit, or she'd become a rock-star here. A bit before lunch, one of the other coders named Craig came over and asked where I wanted to go for lunch. Craig and I had been taking our lunch breaks together for a few months, and our lunches were either focused on work-topics or everything BUT work. It was a Monday and I knew today we'd be discussing work stuff that we wanted to finish during the week.

"Want to join us?" I asked Terri, she would be working on the same project and this would be a good way of getting her jump-started. We walked to a diner nearby and as we ate, completely out of the blue, Terri said 'I don't think I've met everyone at work yet, but so far, I think I'm the only Trans woman there.'

I looked over at Craig who was staring directly at me, I'm sure he was just as gobsmacked as I was, but I looked over to Terri and managed to calmly say 'That may be.'

We finished lunch and as you may expect, I wasn't looking at Terri the same way I had been before her announcement. I had never met a Trans person before and now I had a Trans co-worker. When we got back to the office, she excused herself and disappeared into the Ladies room and I walked back to our space. Craig stopped next to me and grabbed my shoulder, when I looked at him, he quietly said 'Fuck dude, she's hot as hell and now I can't stop thinking of fucking her brains out. What the fuck is wrong with me?!'

I grinned and nodded a bit, she was hot as hell and before she said that she was Trans, I had imagined her moaning under me, but now... Now it was more complicated.

It wasn't that I was transphobic, I just couldn't imagine touching another persons dick. As cute as Terri was, the thought of her sucking my dick or me fucking her was fine in my head, but I knew that I could never mess around with someone elses dick, regardless of how cute she looked. Maybe that made me transphobic, but I knew I was attracted to her, just not 100% of her.

The first week went by, and things were normal. Lunches always happened with Craig and Terri, but that Friday, Terri had other lunch plans, so it was just the two of us. Today, we weren't talking about work stuff.

"I'd bet a thousand dollars she gives the best blowjob in the state." Craig said with a huge grin.

"Maybe." I answered, Craig and I had talked about women before, even some explicit stuff, but it felt like Craig had turned it up a notch with his talk about Terri.

"Do you think her tits are real?" He asked.

Terri had smallish breasts, but not tiny, I'd suppose possibly a B-cup. Being clueless, I just figured she had gotten a boob job. That was the first thing Trans women typically had done wasn't it?

"Ty, I know it's fucked up..." Craig said and then looked around and leaned forward before continuing "I've got it bad for her dude, I really wanna fuck her."

That night, I masturbated while imagining Terri kneeling in front of me, sucking my dick.

From there, it became almost an obsession. I wondered if she had a guy or girl in her life. I wondered what it would feel like to push my dick inside of her, would it feel a bit like a pussy? She had to have had sex before, did she feel differently? I'd never had anal sex, though I had asked several ex-girlfriends, they always shook their heads or offered to let me fuck them in the ass if they could use a dildo on me first. So anal had been a mystery for me. I couldn't honestly figure out if I was attracted to Terri because she was Trans, or because she was cute, smart as hell, and a mystery.

Sunday night, I watched some porn with a Trans actress named Aubrey Kate, who looked a bit like Terri, but with bigger tits and tattoos. When the scene switched from oral and she got on her hands and knees, the male actor simply lined up his dick (which was the typical, big porn dick) and pushed it into her until it was fully inserted, very similar to pushing your dick into a well-lubricated pussy.

I closed my eyes and imagined Terri on her hands and knees, with her ass-cheeks spread and instead of a puckered asshole staring back at me, I imagined a cute, petite vagina with widely splayed labia. When I came, it was with a feral energy and I had to chuckle afterward, cleaning up the mess I had made of myself.

Monday morning, when Terri came in to work, she had on a skirt and a snug blouse. While she had kept the blouse buttoned right up to her neckline, the curves of her breasts were very obvious. She had caramel-colored pantyhose on (I couldn't let myself imagine she had stockings on, or I'd get no work done at all.) and heels that were sensible for work I suppose, but I wouldn't have complained if she had on stripper heels.

I wanted to compliment her, but worried it might turn into something weird for her. instead, she asked how my weekend had been, I told her I had spent it working on the house I had bought as a fixer-upper. It was a hobby of mine, my Dad had a talent for finding homes that needed a bit of TLC and then turning them into the kind of homes that sold quickly, turning a nice profit. Then finding the next house to work on. I'd learned plenty about home repair from him, and he had encouraged me to follow in his footsteps, this house I had bought was my first, and I was living there while I renovated the place. If you talked to anyone at work about my house project, they'd tell you it was my 'side hustle'.

"I can picture you in your coveralls, bashing on the walls of an old house with a hammer." She said with a light giggle.

"Oh? I have that vibe huh?" I asked.

She smiled and shrugged.

For the first time, I imagined kissing her. Taking her by the hand and leading her out into the hallway, then feeding my tongue into her mouth as I gave her breasts a close inspection to determine if they were store-bought or homegrown.

"What about you?" I asked. "You spent the weekend dancing, and shopping right?" I threw in my own little giggle.

"I did some shopping, yes. I bought this outfit and a few others. I see some of the women here like to keep their office-sexy game strong." She said while suddenly needing to try to straighten her skirt.

"It looks nice." I figured that was a safe compliment.

As we got to work, I stopped fantasizing about Terri and concentrated on fixing everything that had been found broken over the weekend. Before I knew it, it was coming up on lunch time and Terri scooted her chair over to my desk, then leaned close and in a low voice asked if we could grab lunch and if it would be possible if Craig stayed behind.

In a way, I knew he had been a bit less than professional and had been flirting with her, but more than that, he couldn't stop staring. You may be surprised to hear that an office with a large number of computer nerds will often include people with limited social skills.

I nodded and then went to find Craig to let him know that I'd have to miss lunch.

~

"Ask." She said as she sipped her bowl of soup across the table from me.

"Ask?" I repeated "That's kind of open ended."

"It was meant to be."

"Tell me why you didn't want Craig here." I figured it was a safe question that I likely knew the answer to.

"He's nice enough, but he creeps me out a bit too, like, he's being nice but I'm pretty sure he's a chaser."

"A chaser?"

"A guy that chases after women like me."

"Ahh, ok."

"You can go back to having lunch with him tomorrow, I just wanted you to know that I won't be joining you guys, it's kind of weird and I don't want him to think I'm interested in him like that."

I ate a bite of my burger and tried to think of what to say.

"I don't freak you out, do I?" She asked.

"No, but I'll admit, you're the first Trans woman I've ever met. So, there's something different about it all."

"Why? Do you think there's something different about meeting a really heavy woman? Or a bald woman? Or a woman missing a leg?"

"Yeah, I guess there is, but it's not like that."

"Then what is it like?"

"You're putting me on the spot here Terri."

"What we say here stays between us, don't worry, I won't report you to HR." She said, and laughed.

I took another bite of my burger and worked to form a statement that wouldn't offend.

"It's hard to imagine that you weren't born, the way you look."

"Why?"

"Because I'd never guess that at some point, you weren't."

"But that's the truth of it. Still, you don't seem freaked out by that."

"Who am I to judge? I suppose it's hard for me to imagine not wanting to be the gender I was born as, no offense."

"None taken, for me it was hard to imagine BEING the gender I was born as."

I nodded and chewed.

"Let's play a game." She said "We ask each other a question, and if it's too awkward, we tap our fingers on this table, I'll got first. Why are you spending your weekends fixing up a house instead of partying like most other guys?"

I chuckled and said "Okay, I'll agree to play."

She just smiled and waited.

"It occupies my time, I like having the goal of getting it done. It's like work, but it's work for me and not someone else. I'm my own boss and I can take a day off working on the place if I want to, or take a week off if I'm being really lazy."

"What happens when you finish? Sell it and buy another house?"

I nodded "Hey, is this a back and forth game or do you just keep asking questions?"

"So you're forever living in a house that needs repairs, do I have that right?" She asked, clearly ignoring my question.

"Yep, pretty much. Okay, my turn." I said, and watched her. I still didn't know what I could ask, she almost felt like being introduced to a new species.

Before I could ask, she tapped her fingers on the table.

"Huh?" I asked, puzzled.

"Go easy on a girl, okay?" She asked gently.

"Hey, come on. I'm not an asshole."

She sipped the last of her soup and watched me.

"My Dad got me into this stuff, when I was a teen, he said that I could either pay other people for the rest of my life to fix the things that break in a house, or I could learn how to do the work myself. He said that I didn't have to wait for things around the house to break, that I could buy houses that already had plenty of problems and practice on those. Growing up, I think he probably had bought at least a dozen homes that he fixed up and so I guess it rubbed off on me. Though, this is the first house I've bought."

"It's okay to ask me questions Ty, I just hope they aren't centered on what I have between my legs."

I nodded, but felt like anything I'd ask, on a personal level might be too personal, so I decided being a bit vulnerable might make her feel less concerned.

"I guess I'm not great at relationships and so fixing up the house is a simple way of avoiding potentially awkward social situations."

"You're saying things so I tell you things." She declared.

"That's how conversations work."

"Ask."

"When did you know? Like, when did you know you had to stop living like a guy?"

"I never felt like how I imagined other guys felt, puberty was when it all came to a head. I transitioned when I was sixteen and I won't horrify you with what the rest of my high school time was like after that. It's been difficult and unlike you, I don't have a house that needs a bunch of repairs to occupy my weekends with."

"No guy? Or girl?" I asked.

She shook her head.

"Same."

"Is this the part where you ask for my number, or just ask if I want to grab dinner sometime."

"Would that be terrible?"

"Probably."

"I can't tell if you're being serious." I wondered, and asked her.

"I guess we'd just have to find out."

"Let me by you dinner."

"Okay, but I want to see this house you're fixing up."

"Why? Are you thinking about getting a fixer-upper too?" I asked.

"She smiled, and shrugged. "Maybe."

~

"Can I offer a single suggestion and not hurt your feelings?" She asked as I drove us to one of my favorite seafood places.

"Sure." I answered, and a million thoughts raced through my head.

"You'd be doing me a huge favor, if you just treated me like any other woman going out to dinner with a guy."

"Have I treated you any differently?"

"We weren't going on a date earlier."

This was going to be a date, she was right.

The meal was delicious and the conversation flowed easily for most of the evening, there were a few embarrassing moments, but I managed to not make a fool of myself. When we finished, it was dark and I began driving us back to work, so Terri could get her car and drive home. I pulled into the lot next to her car and she opened the door and slid out. Part of me was thankful, having worried there might be an uncomfortable end to the date, but the other part of me felt upset, I wanted to kiss her.

She held the door open and leaned inside the car and said "I'll follow you."

"Where?" I asked confused.

"To your place, you said I could see your house."

I wasn't expecting company and the house needed to be straightened up, but if I made an excuse, I'd look like an asshole.

"You're going to have to excuse a bit of a mess, if that's okay."

"Like I said, I'll follow you."

During the drive back to my house, I couldn't shake the thought that she had intended to seduce me and I found that I wouldn't have any problem with that. If at some point during the evening she pushed her dick into my face, I'd just deal with it then. When we pulled into the driveway, I walked back to her car and waited for her to grab her purse and get out of her car.

"What will your neighbors think Ty?" She asked with a funny grin.

"They'll think that weirdo in the old house just hit the lottery." I said, it was only partially exaggerating.

"Good answer."

I held her car door open and closed it behind her and then led her up onto the front porch and into my house.

Every room had signs of the work I'd done on it, the only room that had been completed was my bedroom, which was very close to the size of the entire apartment that I had moved out of when I bought this house. There were drop cloths strewn about, in the dining room, recent drywall patches could be seen on the walls and again in the living room. The kitchen had new cabinets up, sink and counter top, but the linoleum floor was a mess and hadn't been started on yet. The bathroom had no hot water to the sink, but the shower worked fine as did the toilet. It was a strange mixture of embarrassment and pride showing Terri all of the work that I'd done and so much more of what I hadn't yet started to fix.

We sat on the couch and I wished I would have had some kind of alcohol that she preferred, instead she cradled a beer that would eventually go lukewarm before it was half-emptied.

"The bachelor-pad in progress." She said as she looked all around.

"Hardly." I laughed, then added "You asked me to treat you like any other woman."

She nodded "Thank you, you've been great."

I inhaled deeply, and just went for it. I leaned in and kissed her. Nothing sloppy or noisy, just a simple kiss on her lips and then I backed off.

"I'm better about asking forgiveness than permission." I said, suddenly emboldened that she hadn't recoiled in horror

She watched me for a moment and then just nodded.

For the next hour, we talked about our lives. I told her how my parents had divorced and how my Mother's drinking had led to my Dad spending more and more time on his fixer-upper house projects and when that stopped working, they just decided to call it quits. I told her how it affected me and how I lashed out and got into trouble, very nearly having been sent to a camp for troubled youths. I told her how the first woman I fell in love with changed my life forever and then how she broke my heart a year later. Terri told me about the hell she went through as a kid and then in high-school after the summer break of her junior year when the strange guy everyone expected returned to school as a girl. She said that she was attracted to both guys and girls and that she had been heart broken by both in the past. She asked me if my plan was to eventually find the right woman and have a family. I told her that I was worried about bringing kids into the world and how I felt like all of the changes I had seen over the last however many years didn't give me a great feeling of confidence that everything would be okay.

She looked at my lips and then into my eyes so I leaned in and kissed her again, this time lingering just a bit, no tongue, but a legitimate kiss. Her lips were like silk pillows and the caveman that lives inside of me imagined them gently sucking on my engorged dick.

"I should be going." She said.

"Are you sure?" I asked, but it sounded like I was pleading.

"We both know what happens if I stay."

I nodded.

"We should think about that, I want to tell you that tonight has been perfect Ty. It's all I can do to not start crying right now."

"What? No don't cry! I've had a really good time, hey.. promise me we can do this again."

"I want you to have a bit of time to think about it."

"I don't need any time to think about it." I countered, sure this was new territory, but Terri was so easy to be around, it felt like the only times I had a conscious thought that she was Trans, were the times she was talking about what it was like for her. Honestly, I had only seen her in the same way I would have seen any woman I was attracted to. If anything, it began to bother me that being 'curious' about her felt like I was just curious to find out what a Trans woman was like.

"That's because you haven't thought about it." She said and giggled. "I'll see you at work tomorrow." She said as she stood.

I followed her to her feet and stayed close, waiting for a sign.

"Kiss a girl goodnight?"

My lips were on hers a second later and then her lips parted and my tongue was in her mouth, which she gently sucked on.

Never in my entire like did I want to be inside someone else as badly as I did in that exact moment.