Trans Damsel Stories - The P.I.

Story Info
A private investigator is hired to find a missing girl.
10.9k words
4.06
3.8k
4

Part 1 of the 3 part series

Updated 06/11/2023
Created 01/05/2022
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Writing erotic fiction has been a lot more fun than I expected. This is my longest story yet! I plan to do a couple more of these, exploring more peril scenarios with trans damsels in distress. I really love the genre and I feel like this has been excellent writing practice. I love bondage and peril I'm really excited to share this work. Thank you for reading!

Story:

The drive from the city was long, but idyllic. The long stretches of highway lasted for hours, but before long it gave way to the pristine woodland, shrouded in mists. My car was loaded with clothes and gear, I knew I would be gone for a while. I drove through forested hills, the small towns dotting the road grew even smaller and fewer between. The mist was growing thick, and it was getting hard to see in the darkness. Finally, I could see it. The town was by the sea, small, and covered in a blanket of fog.

I hardly saw any cars in the streets, and there were even fewer pedestrians. I followed the GPS and eventually reached my hotel. It was a small four-story building, and there couldn't have been more than five or six cars parked in the carpark. I zipped my leather jacket up tight and stepped out into the misty evening with my black boots. The receptionist almost seemed surprised to see me. They clearly weren't used to having many guests.

I could feel his eyes watching me as I stepped into the warm lobby. I wasn't sure if it was with attraction or the need to show interest in a guest. Just in case, I unzipped my jacket to reveal my low-cut sleeveless white bodysuit tucked into a pair of short denim shorts. I walked up to him and booked my room.

"Sounds like you'll be in town for a while ma'am. Is this trip going to be for business or pleasure?" He asked.

"Business. Though I suppose I could always find time for pleasure." I giggled. I was trying to see if I could use my looks to my advantage with him.

"I don't know that we've had many outsiders stay longer than a couple of days. I hope you enjoy the stay in our town." He didn't seem interested.

"Hey, it's funny you mentioned that! I heard about this hotel from my niece, I think she stayed here a couple of weeks ago. Maybe you remember her? She's a pretty young thing, blonde like me but a little shorter. Her name's Sarah. I think she should be 19 by now. She told me she loved it here." I leaned in so he could see that I wasn't wearing a bra.

My breasts were on the larger side, and they threatened to spill out over the top. I saw him peek at them, but he seemed unmoved.

"No, I don't recall seeing anyone like that. Maybe she came on a different shift from mine." He passed me my room key.

"Oh, that's a shame. She told me she liked staying here." I turned to leave.

"Ma'am?" He stopped me.

"Yes?"

"Some of the locals here...they don't appreciate too many questions from outsiders. Just a friendly hint." He then returned to typing on his computer.

I took off my jacket and walked to the room with my suitcases, making sure he could see my petite round ass through my shorts as I went around the corner, but I'm sure he didn't look up. My room was on the first floor. The hotel used physical keys, not like the ones with key cards that you could find in the city. Turning it, I found my room to be quite pleasant looking, much nicer than anything I expected. I thought I would be staying in a grungy motel with small and dirty rooms, but the room I had was spacious and clean.

I draped my jacket over the back of a chair and removed my boots. I sighed with relief, as my feet were so much more comfortable. The room had a queen-sized bed with a TV and a clean, spotless looking bathroom. There was a closet for me to stuff my suitcases, and I slipped out of my shorts, letting them fall to the floor. I looked good in the bathroom mirror, especially for my age. I kept my blond hair short, and my body in shape.

My ass was gorgeous, well-shaped by the white fabric of my body suit, and my tits were made to look even bigger by my slim build. My cock was small, tucked away into a pocket in the lining of my bodysuit, and my balls only barely made a bulge. I sighed with exhaustion from the travel, and I was also ravenously hungry. Even a town as small and quaint as this had pizza joints, and I ordered myself a pie on the phone.

I desperately wanted to shower and sleep, but I had work to do. I unpacked my laptop from the suitcase, lounging on the bed as I worked. I reviewed the case I'd traveled all this way for. A wealthy family had come to my office in the city, offering a huge payout to help find their daughter, Sarah. Like I'd told the receptionist, she was a pretty young blonde, just finished with her freshman year at college. She had bright green eyes and liked to keep her hair in braids. She decided to go backpacking to celebrate the end of the year.

The last place she had been seen was in the foggy New England town where I was now staying. From my research there wasn't too much known about the place. It seemed like its main industry was fishing and the occasional tourist. Suspiciously, hers was not the first disappearance to be traced to the town. There didn't seem to be much of a pattern to who went missing. The list I made included men and women, young and old. There wasn't much attention drawn as these disappearances were sporadic, and far apart in time. Something was up.

The possibilities raced through my head. Serial killers, organized crime, trafficking, and slavery rings were all possibilities. None of these scenarios were good, and I had to work hard to figure this case out. As I was deep in my work, the phone rang. It startled me, as I'd been absorbed in my notes. With anticipation, I answered. It was the pizza guy.

It was time for a break. I had a slice in my hand, lying back as I decided to click on the TV. I liked to watch local news to get a sense of places when I traveled. It was of a shoddy quality, like something on public access television. The weather report unsurprisingly predicted more foggy, dreary weather with rain. There was something off about the anchors and reporters. They sounded strange and stilted. The stories were almost designed to seem boring, like there was nothing going on in the town. But there was a strange quality to it, like everything was staged to look like regular news but in an uncanny way.

I was too creeped out by this and turned off the TV, finishing my slice in silence. Finally, it was time for a shower. I slipped out of my bodysuit, and quickly washed myself. I had a hairless body in pristine condition. I took care to wash myself clean, soaking my breasts, and carefully cleaning my uncircumcised penis. Finally satisfied, I wrapped myself in a towel and basically collapsed onto my bed. Sleep came soon after.

I woke up, almost expecting sunshine, but all I could see in the morning was grey fog. I wondered how people could stand living in this weather year-round. I dressed myself for the day. The goal was to look sexy, but professional. I slipped on a sexy but comfortable set of underwear, wearing black panties with a silky white bra. I wore a short black pencil skirt that hugged tightly to my ass and a crop top that emphasized my breasts. I covered myself up with a black trench-coat. I liked that it looked as though I could be naked under it. I slipped into comfortable shoes and walked out the door.

My first stop was at the police station. An overweight sergeant sitting at the front desk accepted my credentials and waved me through to meet the detective. He had a real Dirty Harry look to him, though to my disappointment he kept his gun on his hip, instead of using the iconic holster. He had a loose tie on, and I could smell the fact that he was a chain-smoker.

"So, you're the one that called ahead?" He asked.

"Sure did. I take it your familiar with the case I've been assigned?"

"The parents called last week. The missing girl. Her name was Sarah or something. I told them the same thing I'm going to tell you, she's gone."

This was news to me.

"What happened?"

"I had my boys ask around about the girl. From what they gathered it sounds like she stayed in that hotel a couple of days, checked out, and they never saw her again. She sounded like a hiker, and probably got lost trying to go through a trail in the woods. She wouldn't be the first." He sighed.

I couldn't imagine anyone voluntarily going into the dark forests around the town. There had to be more to this.

"Is this what happened to the others? I've heard there's been a number of missing people who've been through here over the years." I mused.

"Something about the woods just draws people in." He shrugged.

"And has anyone tried searching for her?"

"If I sent out a search party with 40 people into those woods, about 10 of them would come back. Those woods are dangerous. She got lost in there and she's gone. There's no way someone like her would survive longer than a night there. I tried to tell that to the parents, but I guess they went and hired a PI anyway. I'm sorry you wasted your time."

I was immediately suspicious, but I was careful not to give anything away.

"I did come a long this way. Any chance I could look at the files? I need to tell the parents I did something."

"There's no point. We lock away files after we close them, and we don't show them to anyone who doesn't have a real badge. I'm sorry hun, but it's the policy. You won't find anything helpful in them anyway, it's an open and shut case."

"Hey I get it! Is there anyone I can talk to, that might have seen her?" I could tell I was starting to annoy him.

"Listen. I'm not a big fan of you PIs, it's all about money for you guys. But let me share you some advice about this time." He leaned into whisper. "Everyone here is fucking crazy!"

"What do you mean?"

"They don't take too kindly to outsiders poking around and asking questions. Do what you need to do to appease the parents, but then get the hell out of here. There's no girl here."

I was frustrated when I walked out of the police station. I didn't buy the detective's story one bit, and I knew there was more to this case. I needed to figure out where to find new leads. I sat down in my car, taking a minute to gather my thoughts.

"I could use a coffee." I muttered to myself.

I drove to the only diner in town, it was drab and almost looked decrepit. Parking my car, I was grateful for the trench-coat which kept me warm in the damp morning air. Inside, I could feel the stares. The townsfolk seemed like hardy, severe bunch. Their quiet conversations stopped the instant I walked in through the doors. I flashed a nervous smile and found an empty booth, as everyone returned to their conversations.

"New to these parts, eh?" The waitress who poured my coffee asked.

"That's right. I take it you don't get many visitors here."

She shook her head.

"Say, my niece came to this town a while back. I wonder if she stopped here. Would you remember seeing a younger blond girl? She was real pretty, and I think she'd be easy to remember if you're not used to seeing visitors." I must have struck a chord.

The waitress looked almost fearful. She shook her head and threw a menu on the table. I was onto something. I scanned the diner as I sipped my coffee. From the corner of my eye, I saw a man watching me from the bar. He seemed a bit younger than the rest of the crowd in the diner. I instinctively let my leg slip out of the trench-coat, almost teasing him. Maybe he'd be willing to talk to me. A light rain had fallen outside, pelting the window with small raindrops.

I was finished with breakfast when the man walked by my booth. He stumbled, threatening to slip and fall over before catching himself on my table. He carried on and walked out of the diner. He was quite handsome, with a thick beard and a face looking like it had been weathered by hard work. He wore a heavy coat and walked with a slight limp. I noticed a napkin on the table, by the spot where he'd grabbed the table.

I quickly took it and read it.

"Finish your coffee then meet me out back. Too many listeners here." The note said.

I felt a jolt of excitement. It reminded me of some of my earlier days as a private investigator, with secret meetings and hidden rendezvous points. I made sure to wait a bit to avoid drawing suspicion, before paying and tipping the waitress. The rain drizzled down outside, running off my trench coat. I could see the cherry of a lit cigarette out back and walked to the man, making sure that no one was looking. To any observers it would have looked like I was asking for a light.

"You're looking for the girl." The stranger gruffly observed.

I nodded.

"I remember her. She came by just a couple of weeks ago. Backpacking or travelling. She was in way over her head. I think she's still here."

"Well, what do you think happened to her? Where can I find her?" I was excited by this news.

"Don't know, and I can't say too much. There's eyes and ears watching everywhere in this town."

"What's going on here? Why is everything so weird?"

He shook his head.

"They've been here for years. Taking over. I can't tell you anything more, but there's a building just on the outskirts of town. I don't know what she was doing, but the girl was there. Be very careful, anyone could be watching."

He gave me the location then left. I stood there in the rain, lost in thought for a moment. Back in my car, I plugged the address into my GPS. I took a deep breath, feeling doubtful about whether I wanted to go through with this. A part of me wanted to take the detective's advice, checking out of the hotel, and driving back home. Who knew what I'd find at the house? But a larger part of me wanted to learn what happened to Sarah.

There didn't appear to be anything remarkable about the building. It was small, maybe three or four stories high and looked like it housed offices. There were no cars parked nearby or any other signs of life inside. It was abandoned. I tried the front door just in case it was unlocked but there was no luck. The back door was locked too, which is when my skills came in handy. After a few minutes of lockpicks, I was in.

The air was stale, and the office was surprisingly warm. I took the trench coat off, leaving it hanging on a coat rack. I explored the building, finding rows of empty desks and cubicles. It didn't seem like any businesses operated there. No decorations of any kind existed, and none of the desks had computers or signs of being worked on. I painstakingly searched each floor, looking for anything that could be a clue. Other than empty desks and chairs, there was nothing.

I couldn't find any papers, or notepads with scribblings on it. I started to write off the place as another dead end. Sighing, I was about to head out the way I came. I stopped in my tracks when I noticed something. A red light peeked under what seemed to be a janitor closet. I came closer, and the light was definitely there. To my surprise, the door was unlocked. I opened it and looked inside. It was a darkroom.

The room was cold, and there were photographs hanging on strings. I went inside to examine the photos and gasped. There were photos of Sarah, dozens of them. She was clearly unaware she was being followed. There were photos of her at the hotel and the diner, along with places I didn't recognize. More concerning were the ones of her in the same building that I was standing in now, looking confused. The last photos caused me to shudder with chills.

She was bound and gagged. She had been wearing a bright sundress in one of them. By the next one it was stripped off, and she was in nothing but a pink thong. I realized the first photos were taken from one of the rooms I just explored. The next few were taken somewhere else. She was stripped naked by then, and one of them showed her being pleasured with a vibrator. This wasn't good, I had to get out of there.

Shutting the door to the darkroom behind me, I sprinted out, to try to find an exit. In my panic, I got lost, unable to find a way out. I had to stop to clam down. I heard a car pull into the parking lot. I must have tripped some kind of alarm when I came in. I heard the door open, followed by heavy footsteps. There was no way to get out without being caught. I hid behind the nearest desk and held my breath.

"Why do they always pick the same hiding spot?" A menacing voice rang out.

I felt a large presence behind me. Before I could stand up, I felt the cold steel of a knife against my throat.

"You're coming with me." The dark, gruff voice commanded.

I felt a man's arm wrap around my neck, pressing hard. I tried to struggle, kicking, but I lost consciousness as the air was cut off. I woke up in a windowless room, with only a desk in front of me. I was tied to a chair. My wrists were tied together behind my back and my legs were spread, with each ankle tied to a chair leg. My crop top was pulled up, revealing my bra. I was completely exposed, with my skirt rode up so high I was essentially sitting on my panties. I was gagged with a rough piece of fabric.

The man who tied me up was wearing a ski mask. He was dressed in black and looked much bigger than me. I could hold my own in a tumble, but I don't know if I would have been able to get very far in a fight against him.

"This is what you get for asking questions. You think we wouldn't notice? A snooping little detective running around sticking her nose in our business." He sneered.

I moaned into the gag and struggled against the ropes.

"Oh, I know what you would say if you weren't gagged. Who am I? What's going on? What do I want from you? Et cetera."

I hated how predictable I'd been. He wasn't wrong.

"You'll have those questions answered in due time. It's not going to matter what you know when you're out of the picture."

I protested as much as I could, only getting muffled noises out through my gag. He looked me up and down as I writhed in bondage.

"You're a pretty one. I hope they do the ritual with you before they kill you. I'd love to see that."

I was confused, afraid, and a little turned on. I had to get out of that chair. I glared at my captor, trying to cover up my arousal with anger and defiance.

"Now, I'm going to go pick up some associates. We'll be back for you. If you're lucky we'll be allowed to have some fun with you before we get rid of you." He pulled down on my bra, exposing my breasts then ran his hand along the inside of my thigh.

My spine tingled with the intimate touching, and my breath quickened. Satisfied, he left me in the chair. I listened for the sound of the car starting before struggling in vain against my bonds. I had to move fast as I certainly didn't want to stick around to find out what would happen to me. Looking around the room, I searched for something I could do to break free. I tried the ropes, but they were tied down tight, and there was nothing I could do.

I was starting to grow hard from the bondage, being tied up and exposed turned me. I moaned softly under the gag in frustration. Just as I was about to give up and accept my fate, I spied a loose nail jutting out of the desk. It might be enough to get my ropes undone. It was awkward to move, but I was able to inch the chair over to the nail, trying to catch the ropes on it. With a lot of effort and frustration, I was able to reach it.

It must have taken fifteen minutes, but I was able to get the knots on my wrists undone. Breathing a sigh of relief, I untied the ropes from my ankles and ripped the gag off. I had to move quick. Luckily, the door was unlocked. I ran out as fast as I could, fighting through my dizziness. I stumbled down the stairs to the first floor and found my car. I was almost at the hotel when I realized my crop top was still pulled up. In the hotel parking lot, I took a deep breath to calm myself and fix my clothes before I went inside.