Caught you looking!

I'm normally the king of discretion. Normally. I mean, I wasn't particularly ashamed that I watched porn, I am only a man, but despite me knowing how normal it is, I was sure glad no one ever saw me do it!

It's one of those things that as a man, I'm secretly proud of. Weird, right?

I've been caught only one time. If I ever thought I would have been embarrassed being caught by my dad looking at a playboy, that pails in comparison to what actually happened.

My name's Taylor. I was single, two years out of college, with a job I didn't deserve, making enough money to get into all the trouble I wish I could have gotten into during college. Hanging out with my buddies a few nights a week, picking up girls occasionally, even keeping a few of them around for more than a week or so. Life was grand.

I was at work one day, trying to work on a project when my phone kept going off. Apparently the text thread between my friends was live, and I was missing out on it. But I was focused on getting the last part of my task completed, so I knuckled down and blocked my phone out.

When I finished, I sat back at my desk and opened it, reading back through the last 30 or so messages I'd got from the guys. It evolved from regular talking shit, who would fuck which pornstar, who still hadn't seen two chicks one cup... you know, normal, mature conversations between adult men. We were absolute pigs, and we knew it. One guy decided to shake things up however, and attached a video of a topless woman, swaying back and forth, cupping her tits. She was sexy as all hell, the kind of woman you wish you'd run into in the street and that she'd beg you to fuck her. About 10 seconds into the video, the camera shot widens, and just when you're wondering if she's full bush, landing strip, or shaved slick... you discover that this hot as hell woman also has a rock-hard cock that she reaches down and starts stroking.

Damn! That asshole got me! I exited the message app and looked around to see if anyone was watching or saw my reaction. Whew, I was safe. For reasons only know to the almighty, however, I found myself opening the messages back up and watching the video again. And again... and again. I couldn't figure out why I was watching it. Everything else drowned out, and I was pulled in, dangerously unaware of my surroundings.

"Hey, Taylor, can you take a look- Oh, shit!" I heard from behind me. I turned the phone over and slammed it down on my desk so hard that I cracked the screen. When I looked up, it was a girl that was on my production team named Jessie, with a shocked look on her face.

Jessie's the office hottie. She started at my office maybe 6 months after I did, and she was by far the most attractive woman there. Tall, long legs, tight ass, beautiful perky tits, with wavy blonde hair and makeup always on point. She always wore things that were office-appropriate, but that definitely showed off her curves.

Here's the thing about Jessie though: other than that, she was a total mystery to everyone there. Apart from occasional afternoons at the bar when work was over, no one knew the first thing about her, where she lived, where she was from, if she had a boyfriend... nothing. Her answers to personal questions were polite, yet coy; she was always able to redirect and make you forget you even asked her a question.

Of course, she walked up on the exact moment when not only was a hard cock showing on my phone screen, but it was an up close shot, spewing ropes of cum out of it. I wanted to dig a hole through the floor and bury myself right then and there.

"Fuck, Jessie, what?" I said, frustrated and embarrassed, I stood up and put my phone in my pocket.

"I-I'm sorry Taylor, I was just bringing that prospect report you asked for earlier. You said you wanted to review them today?" Jessie said, her face red and showing some embarrassment herself.

"Just leave it here," I said, pointing to my desk, "I'll get to it tomorrow."

With that, I stormed out of the office. I didn't want to be seen there anymore. Jessie saw exactly what I was looking at, how many people was she going to tell? I was never going to live this down. I walked down the street and turned into the first bar I found.

Sitting at the end of the bar, the bartender poured a double bourbon and set it in front of me. I drank slowly, trying to think through the situation. Jessie wasn't typically one that participated in office gossip, which made me breathe just a little easier. But, something this juicy? There was no way she was going to keep that to herself. I was going to have to talk to her before she was able to say anything to other people, and beg her not to. Little did I know that opportunity was coming much sooner than expected.

As I finished my drink, the door to the bar swung open, and the last person on the planet that I wanted to see what standing there: Jessie. I flagged down the bartender and ordered another double, as Jessie walked up. My drink arrived as Jessie took a seat next to me.

"I'll have what he's having, please," Jessie said to the bartender, who poured hers and set it on the bar. Jessie was wearing a pencil skirt with a white blouse, and some heels that did a great job showing off her legs and ass. She pulled her drink a little closer to her and ran her fingers around the rim of the glass.

"So..." Jessie started.

"Jessie, I really don't want to talk about it," I said, looking down at my own glass. I was tempted to drain the entire thing and throw cash on the bar before walking out. I did none of those things, but instead just sat there in my own shame, next to a total smoke show who was undoubtably judging me. After a few minutes I finally broke the thick silence between us.

"Sorry for yelling at you in the office," I mumbled to her.

"Oh, Taylor, that's ok. I know you didn't mean it," Jessie said.

I took a pull of whiskey from my glass and sat it down, looking up at Jessie's face for the first time since she took her seat. I noticed that her expression was unreadable.

"Jessie... would it be too much to ask for you not to tell anyone about this?" I asked. I tried not to sound too desperate but I felt like I was begging.

Jessie slowly picked up her glass and held it in front of her. Realizing she was going for a toast, I picked mine up as well and we clinked them together. "Here's to keeping secrets," she said, smiling.

I sighed in relief. "Thank you so much... I'm embarrassed that you saw that."

To my surprise, Jessie turned the glass over and drained the bourbon instantly. I decided to follow suit.

"I didn't know you to be a whiskey drinker, Jessie," I said honestly.

"Yep, fun fact about me!" She said, flagging down the bartender and ordering two more. She sipped on this one, and so did I, not wanting to get piss hammered drunk on a weeknight.

"So can I ask you what that was all about? That video?" Jessie said. I figured if the secret was kept between us, I was already embarrassed enough and so I'd just add onto it.

"It was a video that one of my friends sent in the group chat to troll us," I said, "But for some reason, I watched it over and over again. Can't even begin to tell you why."

"Those group chats can get pretty wild, can't they?" Jessie said. "You should see girl groups," she said with a small grin.

I hadn't ever imagined what girls talked about in their chats, but hearing her say that made me believe that they must be pretty raunchy as well.

"So," she said, taking a sip from her glass, "did you think she was hot?"

"I don't know, I guess?" I said. "I only watched that video like 10 times before you caught me."

Jessie laughed. "Taylor, it's ok. Trans women can be extremely erotic, so don't beat yourself up that you checked one out." When I heard her say that, my mind went to a place of Jessie having a wild romp with a hot trans girl, getting her pussy demolished by a hot girl cock with her tits rubbing up against another equally awesome pair.

"Thanks, Jessie. I guess I did think it was pretty hot. Honestly, you didn't strike me as the one that wanted to talk me through something like this, it would have almost been too much to ask had we never spoken about it again, but I appreciate your understanding... and discretion," I said.

"We all have our secrets, Taylor. Even me," Jessie said, taking another drink.

I couldn't help but laugh a little. "I don't doubt that! We've worked together for almost two years, and the only thing I know about you is that your name is Jessie, you're good at your job, and you like whiskey!"

Jessie grabbed a napkin from the bar and pulled a pen out. On one side of the napkin, she wrote J-E-S-S-I-E.

"This is how I spell my name." Then she turned the napkin over, and on the other side, she wrote J-E-S-S-E.

"That is how my name used to be spelled," she said quietly, looking at me. "Tell me what the difference is."

"Well, with the 'I', that's typically how a girl spells that name, but without it, that's how a guy spells it," I said.

She leaned a little closer to me. "Exactly."

Either due to the whiskey or my lack of comprehension in general, it took a few seconds before it started to dawn on me.

"Holy fucking shit... Jessie, are you-" I stopped talking, but I reflexively looked down toward her lap.

"Trans. Yes."

"Holy fucking shit," I said again. I just looked at her.

"Now we both know a big secret about each other," she said.

"Holy fucking shit." Apparently my brain had fallen out on the floor.

"Are the only words you know right now, 'holy', 'fucking', and 'shit'?" Jessie asked me.

It took another few seconds for me to catch back up. "Sorry... I swear I will never tell anyone what you just told me."

"Good," she said, "You'd be surprised at some of the reactions I get when I've told people in the past. They haven't always been... great."

"No, I can't imagine they have." The initial shock was starting to wear off, but as my brain started properly working again, it now flooded with questions that I didn't think were going to be appropriate.

"What are you thinking right now?" She asked me.

"I uh... I'm not real sure. I hope I'm not offending you or anything, that is just really surprising. Ok," I said, finally able to gather my thoughts.

"I don't think anything different of you now than I did 5 minutes ago. I have some questions... that I think I'm not going to ask just out of respect. Otherwise, you and me are good," I said.

"I'm glad to hear it!" Jessie said, "and thanks for not automatically hating me."

I felt a rush of sympathy toward her, knowing that it wouldn't be a surprise to her had that actually been my reaction. People can be shitty, I guess. I also felt a new connection form between Jessie and myself, it had to have taken a lot of trust for her to tell me something like that, not knowing what my reaction might have been.

We got up to leave the bar. As we walked out, I stopped and looked at Jessie. "I do need to say one thing, probably while this whiskey is controlling my mouth, because I won't be able to work myself up to say it again."

"What's that?" Jessie asked.

"In a million lifetimes, I would have never guessed that you were trans. I don't know how you take that, but I mean that as a compliment."

Jessie smiled at me. "I definitely take it as a compliment, Taylor. Have a good night!" She said.

"You, too!" I said.

--

When I got into the office the next morning, I was relieved to realize that no one else besides Jessie had seen how I departed the day before, so there was no suspicion that anything happened. I was now confident that I could trust Jessie, with her revealing to me that she was trans... a fact that I still found hard to believe. I passed her work area on my way to mine, and she looked up at me with a smile and "Good morning!"

I worked through the morning, reviewing the report Jessie was trying to give me the day before, and doing some purchase audits, making some minor changes and sending them all off for approval. I was about to go out for a cup of coffee, when I opened my desk drawer, looking for a charger I normally kept there.

I found the charger, but something else caught my eye. It was the bar napkin that Jessie wrote her name on, but this time on the side spelled j-e-s-s-i-e, there was a phone number. I quickly took the napkin out and put in my pocket, then turned in my chair to Jessie's desk. She looked up at me with her usual smile, but then she subtly winked at me, knowing I'd just seen what she left me.

I walked down to a coffee shop and sat down with my drink, unfolding the napkin and looking at the number. I pulled out my phone and programmed her number, then opened up the messaging app. But what would I say to her? I thought about it until I looked at my watch and saw that it was time to go back to the office, then closed out of it without sending her a text.

I finished the work day in a regular fashion, chatting around the office, even stopping by Jessie's desk to make small talk, which was normal for me. With nothing planned for the evening, I headed back to my apartment.

Later that evening, I pulled out my phone and opened it to Jessie's number to send her a text.

-Hey, Jessie, it's Taylor.

No sooner did I put my phone back down, when it dinged.

-Hey, I was wondering when I might hear from you!

So she was looking forward to hearing from me? As the thought crossed my mind, it occurred to me that I was looking forward to talking to her more. I text her back.

-I was thinking about minding the three-day rule when it comes to texting a girl when she gives you her number, but I decided to forgo that lol!

Her reply:

-I'm glad you did. I'm going to grab a drink tomorrow after work, care to join?

Was she crushing on me? Did I even like her like that? I mean... I had zero experience with trans women, it was something that had never crossed my mind. I knew I wasn't gay, but for some reason the fact that Jessie had a dick wasn't frightening to me, it was actually intriguing.

-I'd love to, same place as the other day?

She responded in the affirmative, and that was that.

--

We both decided that it was no one else's business at the office that we were going to meet after work, so we kept things discrete throughout the day. When I saw Jessie clearing her desk before leaving for the day, I did the same. As she passed me on the way out, she stopped by.

"Still good?" Jessie asked.

"Still good," I replied, smiling at her. "I'll catch you in just a few."

I walked into the bar 20 minutes later and found Jessie sitting at the corner table. The lights were low and the ambience was nice, not loud and perfect for a good conversation. I walked up to the table and sat down.

"I ordered you a bourbon, didn't think you'd mind," Jessie said, pushing a glass over to me.

"I don't mind at all, thanks!" I said with a smile which she returned warmly.

"So Taylor, has the shock worn off?" She asked politely, taking a sip of her own drink.

"Oh, yeah it has," I answered, "I still don't think I would have ever known had you not told me."

"That tells me that I did something right," she said with a laugh. She continued explaining.

"I never felt right in a boy's body, and it was like my body was aware of it. I thought it was just a phase that would go away when I started hitting puberty, but puberty really never came for me."

I tried to empathize with how that must have felt for her in her youth, the confusion she had when her body didn't respond the way she thought it was supposed to.

"So I haven't told many people this outside my family and a few close friends that have known me since I was a kid. But I want to be completely open with you, any question that you have, feel free to ask it," Jessie said.

"Ok... I almost don't know where to start," I confessed. "But I do want to say that i appreciate you trusting me, and I do want to know more about you."

"Thanks, Taylor, that means a lot! Since we met I know that you're a great guy, I'm just always unsure of how people feel when they learn about me. I think me catching you the other day made me think you'd accept me, and I'm glad I was right."

"Absolutely," I said, "I may not understand everything, and to my knowledge you're the first trans woman I've ever talked to, and definitely the first one that has ever told me anything about her."

Jessie smiled at me, and started telling me about herself.

"So my dad was never around. I used to be kind of bitter about it, but I think that might have been better for me all around once I became a teenager. My mom was really supportive of me, and helped me out a lot when I told her I wanted to transition. She put me on hormones when I was 14, so other than being a little taller than most girls, I essentially went through female puberty for the most part. My body developed like a girl's should, so I've never had any sort of surgeries or anything. I was pretty effeminate as a boy, so it wasn't a huge stretch when the hormone treatment kicked in and I started getting hips and breasts."

"So..." I said, not wanting to be offensive, trying to figure out how to word the question. She must have read my mind.

"Yes, I'm still fully intact. I have a penis and testicles, but they aren't big and don't work like yours do."

"So, like you don't get erections?" I asked bluntly.

"Nope," she said. "I haven't had one since I was about 16."

The image of what Jessie looked like naked flashed through my mind, and I was surprised, and even happy, to find that it was something that I wanted to see. Was it something maybe she wanted me to see? Hopefully I'd find out.

"I can still orgasm, but it's from prostate simulation, and I don't hardly ejaculate anything."

"So," I asked, "Are you eventually going to get it removed? Sorry if that's too personal," I said quickly.

"Not at all," she said comfortably, "Sometimes I think about having surgery, but I'm pretty good with how I am right now. Also, the recovery from that operation is really hard, and sometimes it doesn't work out very well at all. So as for right now, I don't want it, but I wouldn't completely put it out of the question in the future."

I sat looking at the woman in front of me. She was cool, confident and easy-going, drop-dead gorgeous, and trusted me. I was definitely growing more attracted to her, despite what parts she had.

"Thanks for telling me all of this, Jessie. I'm kind of glad you caught me, too." I said with a smile at her.

"So..." Jessie said with the first hint of nervousness in her voice, "You aren't freaked out by me?"

To both of our surprise, I reached across the table and laid my hand on hers. "I'm really not, Jessie. I still think you're just as much a woman as you have been the entire time I've known you, and to me, it doesn't matter what you were or what you have."

She smiled, the blood rising a bit in her cheeks to a cute blush. She squeezed my hand. "Thanks."

"Forgive me for being forward, but I've always been attracted to you, since you came to work with me. The last few days... haven't changed that." I said.

Jessie was quiet for a moment, leaving me hanging in the balance of my confession to her.

"Taylor," she said quietly, "That makes me really happy. I feel the same about you, it's just hard for me to put myself out there, I'm sure you understand."

"I do now, for sure," I said, "But I'm glad you did."

Jessie smiled at me. "So what now?" she asked, reflecting the same question I had now.

"I don't really know, Jess. Want to turn this into a real date?" I asked.

"I'd love that," she said. We got up from the table and paid for our drinks, and I led her out of the bar onto the sidewalk.

"Well the night is still young, are you hungry?" I asked her.

"I could definitely eat," she said, slipping her hand into mine. We walked a few blocks, our fingers intertwined and walking close to each other, her body sending sparks through my own every time she brushed up against me. I must have been smiling like a dummy, because she looked over at me with her own grin.