He Didn't Know I Was Transgender

Greetings all; in my stories my characters exist in my head, but there might be real life inspirations for some of them. Who knows?

Anyways, my regular readers know that I enjoy writing about the transgender experience from different perspectives. I try not to misstate the reality of being transgender too much.

The phrase "He didn't know I was trans" is often used by transgender women as a humble brag, when they're talking about having been hit on by a guy who thought that they were a cis gendered woman.

In this story a guy tells the transgender woman who he was attracted to that he didn't know she was trans, but it wasn't because he thought she was cis gendered, it was that he believed she was a gay man.

~~

I'd driven down to Savanah from Atlanta on Sunday evening so that I could be at my customer's offices at eight a m Monday morning. Two men and a woman were waiting for me in the main lobby when I arrived. They stood off to the side while I registered with the security officer and received temporary credentials that gave me access to the building.

Once I was done I took a deep breath and prepared to deal with whatever vibe I'd feel from them. I always assume that everyone thinks I'm gay as soon as they lay eyes on me, and rightfully so. You see, I have one of those faces that was meant for a girl. Couple that with my pixie haircut, arched eyebrows and smooth skin, and you can see why they come to that conclusion.

Actually I'm good with that, because I prefer for them to believe that about me rather than having to deal with their reaction if they knew I was transgender.

As I was walking the few steps to where they were standing a big burly guy gazed into my eyes as he said, "I'm Bryan, the facilities supervisor. I'm the one you've been talking to on the phone."

The way he was looking at me made me wonder what he was about. He was over six feet tall and he had to weigh at least 250 pounds, which is one of my types.

I responded to him saying, "I'm Mardi. It's good to meet you Bryan," then I held our eye to eye contact and I felt a chill run down my spine.

"This is Arnie, my team lead and Katie from IT," he said, looking at each of them as he spoke their name.

"Nice to meet you," said Arnie, who was a bit older with crows feet at the corner of his eyes and a long white beard.

"Good to meet you too," I replied.

"Hi there," said the rubenesque Katie whose eyes were sparkling as she looked at me.

"Good morning," I said cheerfully.

I always expect some awkwardness when customers meet me for the first time, but they'd made me feel welcome. We then went into a conference room and had a meeting where I laid out my plan for how I hoped the week would go.

Once we were finished Bryan said, "Mardi, Arnie is going to be your right hand man. If there's anything you need just let him know.... Arnie you take good care of Mardi for me now, you hear." Then he gave me THAT look again.

"Yes sir, loud and clear," responded Arnie.

Katie grinned at me.

I momentarily showed my femininity when I gave them a big toothy smile.

At that point Bryan excused himself and Katie led me to the data center where I'd be installing the application our company had sold to them

When I was assigned the project I was excited about getting to hang out on River Street after work every day, then drive back home Friday afternoon. However all of those plans were ruined when a glitch on the customer's network slowed me down most of the day. I ended up staying on the job until eight p m Monday night just so I'd feel like I got something done.

When I made it to work on Tuesday morning Bryan and his boss were waiting for me. The boss was concerned about the possibility that the project wouldn't be finished by Friday which would cost him more money if I had to come back the next week. I promised him that I'd do my best to get all of the work done as originally planned. Bryan stepped into the hallway with him for a moment then he came back into the computer room with me.

"I heard that you worked until eight last night," he said.

"Yes I did," I confirmed.

"Did you eat any breakfast this morning?" he asked.

"I had a piece of fruit and some juice," I replied.

"Alright, I'll let you get to it," he said as he turned to leave. "Don't skip lunch like you did yesterday," he added before closing the door behind him.

"Yes sir," I responded softly.

I didn't see him the rest of the day, but I did ask Arnie to grab lunch for me so I could keep working. Taking a short lunch break paid off and I felt comfortable about leaving at six p m, plus Arnie wanted to go home to his family. I was off work in time to go to River Street but I was too tired, so I grabbed a salad on my way back to the hotel.

~~

I went to bed early Tuesday night, but It was still hard to roll out of bed Wednesday morning. I made it to work on time and found that Bryan had breakfast waiting for me.

"Bryan you didn't have to do that," I said, smiling automatically.

"You need to eat more than a piece of fruit all morning, that's why you're so skinny.

"I'm slender," I protested just before taking a bite of my sausage croissant.

"Uh huh," he responded while peering into my eyes intensely for a second. Then he said, "I have to run. I'll talk to you later."

"Sure, and thanks," I replied, while returning his gaze again.

My software installation went smoothly all day, so I was finally able to look forward to leaving work at five and going over to River Street to eat dinner. However those plans changed when Bryan came into the restroom when I was walking out of a stall after I'd sat down to pee. "How's your day going? he asked jovially as he stepped up to a urinal while unzipping his pants.

"Good, for a change," I responded with a smile

"Does that mean you're getting out of here at a decent time?" he asked.

"Yep, I plan too," I replied as I looked at myself in the mirror after washing my hands.

"Are you doing anything after work," he asked, putting his dick away while turning from the urinal and giving me an accidental glimpse at it, I think.

"I'm finally going to get to go to River Street," I said as though I hadn't seen him, though my mouth was literally watering.

"Aw crap, I was hoping you'd say no," he responded.

"Why is that?" I asked, looking up at him.

"Wednesday night is all you can eat crab night at A Quaint Little Seafood Place out on Tybee Island," he said with a hint of excitement in his voice.

"Hahaha," I laughed at his enthusiasm, then said, "Well, I certainly don't want to miss out on that."

"Are you sure?" he asked.

"Yep. Besides, River Street will still be there tomorrow.

~

As I drove back to my hotel I found that I was actually excited about going out with Bryan. I liked the little bit I knew of him, and I appreciated that he was nice enough to host this contractor from out of town. Deep down I suspected that there was more to it than that, and if I'm honest I didn't mind his interest. With that in mind I decided to put on one of the androgynous outfits I brought with me, rather than dressing in men's clothes.

~

Bryan smiled big as he watched me come out of the hotel wearing a white oversized boyfriend shirt on top of a compression shirt that hid my breast, jeans, a ball cap, and sneakers.

"Hey there," I said, smiling as I climbed into his truck with him.

"Man, you look great," he said, a little bit wide eyed.

"Thank you Bryan," I responded with a warm smile.

~

A Quaint Little Seafood Place was right behind the dunes, with a great view of the beach and the ocean. It definitely was a good spot to take a date I thought as I took in the view, the various sounds, and the smell of the ocean while we sat on the patio.

"Bryan I'm really glad you brought me here," I said randomly as I snapped another crab leg in two.

"It's my favorite place to eat on the island," he replied while chewing. I could see that he loved eating, which made me grin.

After we, and that primarily means he, had eaten five pounds of crab legs we ordered a beer in a carryout cup and took a walk on the beach. The stars were out by then, the rhythmic sound of the ocean waves coming onto the shore were soothing, and the running lights of a cargo ship that could be seen on the horizon made me think about cruising to some exotic location. It was the romantic atmosphere I'd like to share with my lover.

I was pulled back to reality when Bryan said, "I've never met anyone like you."

"Oh really.... is that a good or bad thing?" I asked.

"It's a good thing," he replied with a laugh.

"What's so unique about me?" I inquired, genuinely curious about what he'd say.

He looked at me and licked his lips before saying, "You might not like me saying this, but you're a pretty man and you look damn good in those jeans."

"Haha," I laughed for a second, then said, "I'm not sure what to say to that." Then we stopped walking and looked at each other for a moment, and I thought he might try to kiss me which I didn't think would be a good idea being that he was my customer, so I started walking again. After we took a few steps he grasped my fingers and held them until we reached a trashcan where we threw our empty cups away.

We continued walking until we were about a half mile away from A Quaint Little Seafood Place. We'd turned around and headed back towards the restaurant when we heard a moan. Bryan put a finger to his lips to signal me to be quiet, then he led me to where the moan came from. There behind the dune was a woman sucking a guy's cock.

"That lucky sombitch," whispered Bryan.

I glanced at him, then I looked at the woman's head bobbing up and down and my competitive juices began to flow. I was already in a mood and watching them setoff my imagination.

I invisioned myself squatting down in front of Bryan and taking his cock out of his cargo short. It was burly just like it's owner and as hard as diamonds. I gave him a little sniff down there to be sure that he was clean, then I pulled his foreskin back and gave the head a good working over. It wasn't long before he was quietly moaning from deep in his throat. I then began to knead his nuts while using my mouth and my other hand together as I sucked his dick until I felt his ballsack tightened. At that point I took his cock out of my mouth and jacked him until he shot his load onto the sand.

I was roused out of my daydream for the second time in the last hour when Bryan touched my arm to get my attention and said, "Did you see that? I think he came and she swallowed it... let's go."

We quietly walked away, then headed back to his truck. When we got there he opened my door for me. While we rode back to my hotel I glanced at him several times as I thought about my daydream. I wondered if he was the kind of guy who would've gone back to work and told everyone, if I'd actually sucked his dick when we were on the beach.

~~

When I arrived at the job Thursday morning Bryan had breakfast waiting for me again. "I only brought you fruit this morning.... kind of figured you'd still be full after eating all those crab legs last night," he said and laughed.

"I... ate all those crab leg... Do I look like Bryan now?" I said and laughed too.

"Okay, okay, it was me," he acknowledged. "In any case, I enjoyed sharing them with you."

"Me too," I agreed.

"Alright, I'll let you get to it," he said, then he went about his day. I'm not sure if he said anything to anyone about our conversation when we're on the beach, but I didn't sense any change in the way people treated me. My work went smoothly again, but the day ran a little long because I wanted to finish the installation. It was six thirty that evening when I left the job, and I was still full of crab legs so I didn't bother with going to River Street. Instead I stopped at a fast food restaurant and bought another salad to take to my room in case I got hungry later.

By the time I arrived at my hotel I'd decided that I really wanted to go spend at least one afternoon and evening on River Street, so I stopped at the front desk and paid for an extra night's stay out of my own pocket.

~~

It took a lot of hard work to get there, but by finishing the project on Thursday I was able to spend my time on Friday training Bryan and Arnie on their new system as I'd originally planned. We finished up around two p m Friday afternoon, and after I said goodbye to them I went directly to my room to writeup my work summary and send my timesheet to our admin. I then put away my laptop and stripped out of the men's clothes I wear to work every day. My titties were relieved to finally be set free of the compression shirt that I had on to hide them.

Today I wanted to look feminine when I went out, so I took a bath instead of a shower to start the process. After getting out of the tub and drying off I spritzed myself with body splash. I usually don't wear makeup, but I made a concession to my rule and applied foundation, did my eyes, and painted my lips. For reasons I don't understand I don't like women's underwear, instead I wear men's bikini briefs. Once I had my business tucked away I put on a sleeveless swing dress and a pair of earrings.

After putting myself together I looked in the mirror and I saw a woman who most people probably wouldn't know was transgender.

~~

I stepped onto River Street around four p m and found it packed with tourists as it usually is. I joined the throngs of people, then spent the next couple of hours going in and out of souvenir shops reading the silly puns on t-shirts and looking for a trinket with Savanah written on it. I eventually bought a Pride tshirt and another refrigerator magnet.

I also stopped in both of the candy stores where they make pecan pralines and ate some of the free samples that were available to the public. After browsing the shops for another half hour I chose a restaurant serving seafood. The hostess seated me at a small two person table near a window. I was hungry and I knew what I wanted so I ordered right away, selecting a seafood platter, water, and a beer.

While I waited to be served I saw someone enter the restaurant who I thought I recognized. When he looked around the dining room searching for the hostess he made eye to eye contact with me and I instantly knew who he was. Bryan Cuthbert, the facilities supervisor.

I pretended not to be looking at him, but I saw him still looking at me when the hostess showed up, and I saw him glance at me a couple of times while he talked with her. Apparently he asked her to bring him to my table.

"Hi there," he greeted me tentatively when they arrived, then he glanced at the hostess for a second before saying to me, "You look familiar."

"Do I?" I asked, using my lady voice.

"Yes," he said, then he glanced at the hostess again.

At that point I decided to go ahead and own it. "I'm Mardi. Care to join me," I said.

"Hahaha, yes I would," he stated with a relieved look on his face as he sat down.

I looked at the hostess and smiled. She responded with a smile that was partly a smirk. I think she knew I was a man, but she thought that he didn't. She handed him a menu, then said your server will be right with you.

Our server was indeed at our table a moment later, "I'll have the Mahi-mahi special and a lite beer on tap," Bryan said to the server without looking at the menu.

"I'd told the hostess that I thought I knew you," he explained after the server walked away.

"Okay," I replied as I watched his eyes pan down from my face to my breasts and linger there before he said, "Man you're pretty, and those look real."

When he looked up at me and saw the sad expression on my face he knew something was wrong. "What is it?" he asked with a confused look on his face. "I didn't mean any harm."

"I know," I responded with a sigh.

"It's just that I've never seen a man with any that looked as real as yours."

"They are real. I'm not a cross dresser," I said matter-of-factly.

"Are you a woman?" he asked, looking really confused now.

"This is a bit awkward," I said.

"I'm sorry," he said.

You're fine, It is what it is," I assured him. At that point our server returned with our food. I looked at her and smiled politely, but I wish she hadn't shown up and interrupted me and Bryan's conversation at that moment. However I still greeted her warmly, then I went on about how good our food looked as she served us.

I was tempted to finish what I was saying when the server left our table, but I decided to wait. "Let's eat while it's hot, then I'll explain everything, " I said.

"Okay," he responded.

With that settled we enjoyed eating our seafood, mostly doing so silently other than making comments about our meal. When our server returned to check on us I stressed that we were paying separately. Neither of us wanted dessert after we'd eaten. I left the server a nice tip then I got up from the table.

"You seem taller," said Bryan when he stood up too.

"It must be the dress," I responded with an amused look on my face.

"Yeah," he responded.

"Let's go sit at the bar," I stated.

~

Once we were sorted at the bar and had our beers Bryan bit his bottom lip as he looked at me sitting on my stool with my legs crossed demurely. "Mardi, are you a woman?" he asked, repeating the question he'd asked earlier.

I must admit that I was flattered that he thought I looked enough like a cis gendered woman that he needed to ask, even though it's never been my goal to cause men to think that about me. That was neither here nor there at that moment though.

"Bryan, that's a simple question with a complex answer," I replied. "I'm a woman, just not a natural born one."

He squinted at me, then I said, "I'm a man who's transgender."

"Transgender.... what's the difference in that and being gay?" he asked.

"Only everything," I replied. "A gay man is just that, gay; whereas a transgender woman is a woman who was born with male parts."

"So you're a woman even though you have a dick huh," he said.

"Yes," I replied.

He drank the last of his beer before saying, "Would you like another one?" As he got the bartenders attention.

"I haven't finished the one I have," I replied with a smile to see how he'd react to it.

He kept his poker face for a few seconds, then the bartender handed him his beer. He took a sip, then smacked his lips I guess to show how good it was.

"Aren't you going to say anything else?" I asked.

"What's there to say?" he replied.

"Are you pissed-off at me?" I asked

"No I'm not. I haven't dealt with a transgender woman before is all," he responded.

"There probably aren't a lot of us passing as gay men," I conceded.

"Why are you doing it? he asked.

"Because I don't want to get my ass beat or worse by some man who's mad because he was attracted to me, and then finds out that I was born with a dick," I explained.

"That makes sense," he agreed.

"So.... do you think you could be with a woman like me?" I asked.

"I don't know how I feel to be honest. I'm not bisexual. This is complicated like you said," he admitted, then he finished his beer. We then sat there in silence for a moment, each of us looking at the other person then looking away until I finally said, "Do you want to go to my hotel with me?"

~~

We were silent as we walked the two blocks from the restaurant to my hotel. As soon as we were in my room I used the facilities and freshened up, then he went in there to get rid of some of the beer he'd drank. When he came out a few minutes later I was sitting on the side of the bed still wearing my dress. He walked over and sat beside me.

"I have something to show you, " I said.

"Okay," he replied.

He stared at me intently as I stood up and took my dress off, then let him get a good look at me. "Damn, you look funny," he said. "You have a woman's face and body, but you have a dick and a pair of nuts hanging between your legs."