On my first day at work, I was supposed to be at the office by 9 AM. This gave me the chance to stop by for a quick styling session with Brianna at her friend’s place beforehand.
She did a beautiful everyday look that wouldn’t make me stand out negatively at work.
I had put on a thin sweater and dark blue jeans, and for shoes, I slipped into comfortable white sneakers.
Brianna came along too, but she didn’t like my outfit choice at all. To make sure I wouldn’t wear it anymore, she simply cut up my sweater right there during the styling.
Now, I had nothing to wear on top except my bra.
She laid out a shoulder-baring wine-red satin dress for me, which barely covered my thighs and was open at the navel area.
She also packed matching underwear and strappy pumps.
I told her that I wasn’t going to a party, just to work.
She just replied that if anyone asked, I could say I had a birthday party to attend right after.
Once the styling was done, I reluctantly changed. The stylist then gave me a black over-the-knee stocking.
Once I had everything on, I had to hurry so I wouldn’t be late for work. Brianna apparently didn’t have time to drive me, so I was forced to take public transportation.
I couldn’t take my large bag with me on the elevator, of course. Brianna gave me a small crossbody bag that just fit my phone and keys.
She handed me my white sneakers in a plastic bag.
So, I set off. On the subway, I felt a bit uneasy in my outfit; I constantly felt like the guys were staring at me.
I was relieved when I finally got off and headed to the office.
There, my boss greeted me with a wide smile on his face. Obviously, he liked what I was wearing.
He assigned Susan, a good-looking woman around 25, to show me around and shadow me for the day.
Susan was always heavily made up and had long, painted nails. By the time I arrived, she was already changed into white pants and a white smock.
She greeted me and offered to use first names, which I happily accepted.
Susan took me to the uniform room, where I got my first set of work clothes.
Then we went to the women’s locker room, which I already knew well from before.
My boss had already given me all the necessary keys, including one for my new locker.
Susan said goodbye briefly and told me we’d meet next door in the break room soon.
I took off my dress and slipped into my work pants and smock. On the way out, I checked my makeup one more time and headed to the break room.
Susan was already waiting for me. Besides us, no one else was in the break room.
She came right over and asked if I had other underwear with me. I asked what she meant. She just said that while my underwear matched my pretty dress, it didn’t work under the white work clothes.
Darn, I hadn’t thought of that—I suspected Brianna had set this up on purpose again.
The few hours I was scheduled to work that day flew by, and none of my colleagues really approached me. An hour before the end of the shift, Susan told me she’d gotten word that I should change and then go see the boss.
I hurried and was soon back in my dress, arriving at my boss’s office.
He was already waiting outside the door and invited me into his office on the second floor. The building was an old one with pretty steep stairs. He let me go first.
I think he got a good look up my dress. But I didn’t let on.
Once upstairs, he asked me to sit and questioned me about my impressions of the day.
After a little chat, he said he was calling it a day too and would be happy to give me a ride partway home in his car. His apartment was near a transfer point for me—I knew that from my previous job with him as “Mike.”
Without thinking much about it, I gladly accepted, and a few minutes later, we were in his car.
He kept chatting with me, wanting to know more about me. While shifting gears, his hand “accidentally” brushed over my stockinged legs repeatedly.
Just before we reached the stop where he was supposed to drop me off, he asked if I’d join him at his favorite restaurant since he hadn’t eaten yet and he’d treat me.
Since I hadn’t eaten much either—I’d left it in my big bag at Brianna’s—I gladly accepted the invitation.
Instead of eating nearby as I assumed, we drove a few neighborhoods away to Fisherman’s Wharf in San Francisco—no, wait, let’s adapt: to a seafood spot on the Upper East Side in New York City.
He opened the passenger door for me like a gentleman and helped me out.
At the restaurant, he ordered a large beer first; I just got a small still water. He recommended all sorts of dishes that he ordered for himself (escargot as an appetizer and shrimp as the main course). I settled for a small pizza, since I was having trouble fitting into my dress—I must have overindulged in the last few days.
During and after the meal, he kept ordering more large beers, and I noticed his eyes getting glassier and his voice slurring more and more. Then he ordered a second shrimp platter, and I saw it getting later and later.
I really wanted to leave, but eventually it was so late that no buses were running, and I didn’t know how I’d get home.
At some point, he said I’d have to drive him home in his car because he wasn’t capable anymore. I had to agree.
I don’t know how he managed, but he paid the hefty bill, and we went to his car. I had to support him a lot, or he would have fallen a few times.
Curiously, he could tell me exactly the fastest way to his place.
Since he had his own parking spot at his building, we didn’t have to hunt for one. But he said I’d have to help him into his apartment.
So, I dragged him up to the fourth floor in the old building. He had an apartment that spanned the entire floor. The floors below had three doors each, but up there, just one. Above that was the attic.
Once I got him into his apartment, he said I could stay in his guest suite in the attic, since I couldn’t get home from here without a car anyway.
With some unease, I accepted anyway, since I wouldn’t have to stay directly with him.
I left him alone in his apartment and went up one floor to the attic.
There was only one door there too, and after unlocking it, a huge long hallway opened up with many doors off it. For a guest suite, it was massive. Most doors off the hall were locked. Only the bathroom, kitchen, and a small living room were open. I thought I’d have to sleep on the couch, but luckily, I tried the apartment key on the locked doors. Sure enough, it fit another lock. Behind it was a very feminine bedroom.
You’d think a young woman lived here. The closets were full of women’s clothes. It was all pretty weird.
But ultimately, I was glad to have a bed to crawl into after stripping down to my underwear. What bothered me were the windows that wouldn’t open. But next to the door, I found a thermostat I could turn down to cool. I noticed the room getting cooler right away, so it must have had air conditioning.
Snuggled in bed, I fell asleep almost immediately.
I don’t know how long I’d slept or what time it was when I suddenly woke up.
As soon as I opened my eyes, I was staring into my boss’s face. He was sitting on me and had just handcuffed my arms. I wanted to scream my lungs out, but he’d already stuffed a gag in my mouth and inflated it.
He said that if I was pretending to be a woman, I shouldn’t be surprised if a man wanted sex with me. Plus, he was into sissy shemales.
He put cuffs on my legs and used ropes to pull them up and apart, fixing them somewhere. Now I couldn’t close my legs.
My butt was no longer on the bed.
He pulled down my panties, took my tiny dick, and started blowing it.
Just before I came, he stopped and pulled the satin panties back over it, letting me cum into them. Then he ripped them at the sides, removed my gag, and stuffed the cum-soaked panties into my mouth. After that, he taped my mouth shut.
Then he slipped a clear plastic bag over my head and sealed it with tape around my neck. He poked a small hole in the bag at mouth level.
Now I couldn’t get fresh air. At first, I tried to stay calm, but the less air I could breathe, the more panicked I got.
I tried to scream, but the panties in my mouth prevented it.
He let me struggle for a long time until I was almost passing out. Only then did he remove the bag from my head.
Then he lowered my legs back onto the bed, turned my body so I was on my stomach, briefly freed my arms, but only to cuff them behind my back again.
He left me like that until early morning.
In the morning, he came back into the room with all sorts of items.
He freed me and said I had to put on everything he’d laid out. Without it, he wouldn’t let me leave the room. Plus, I should hurry because my shift at the hospital was starting soon, and I wouldn’t want to be late.
I looked at what he’d laid out:
- Pink satin bra
- Pink high-waisted panties
- Very loose long-sleeved shirt
- Short white tennis skirt
- Lovense anal vibrator
- Lovense vibrating nipple clamps
- Lovense cock ring
- Way too small white sneakers
- Green tights
- Green handbag
- Green glasses
I refused to put it on, but my boss made it clear he’d expose my secret publicly.
So, I put on all the clothes first, leaving out the vibrators.
After inspecting, he reminded me that I had to wear everything—including the sex toys.
So, I put those on too.
Now I knew at least one of the devices from before and that they could be remote-controlled.
Once I was fully dressed again, he took a smartphone and stuck it into the side pocket under my shirt, which he then zipped shut and locked with a small padlock. He did the same with the panties, so I couldn’t reach the vibrators. Then he fiddled with my long-sleeved shirt. It had hidden loops on the inside—I hadn’t noticed when putting it on. He threaded a belt through those and the skirt’s loops, connecting the shirt and skirt. He locked that too. Now I couldn’t take off my clothes, reach any vibrators, or change myself.
Then he took his smartphone and tested each of the three devices one by one to check they worked properly.
The nipple clamps worried me a bit because I thought they’d show through the shirt. But since the bra had firm cups, surprisingly, they weren’t visible at all.
Now he sent me off, telling me to take public transportation. Since it was pouring rain outside, he handed me a bright green but transparent rain jacket.
Then I had to head out. I felt really uncomfortable in my skin, especially since he kept turning on one or more vibrators during the ride.
When I finally arrived at work, he was already there and greeted me with a malicious grin that the others couldn’t see.
He said he was glad I’d agreed over the phone to take a double shift today to help relieve the evening crew due to the high workload right now.
The staff in central dispatch were thrilled about my supposed agreement, which I knew nothing about until then, and they didn’t even notice it was only my second day and I couldn’t find my way around alone yet. Unlike my boss, they hadn’t recognized me as their former male colleague.
I asked my boss if I could speak to him alone briefly, which he allowed. When we were alone, I asked how I was supposed to change now.
He just said I wouldn’t change; I’d work in my outfit. The only thing I could and was allowed to take off was the tights. They weren’t affected by all the locking.
If anyone asked, I just needed to say I didn’t have a laundry locker yet, and since it was Saturday, the uniform distribution was closed. I’d thrown my clothes from yesterday into the cleaning bin.
So, I had to do my work in the short white skirt, which of course everyone noticed right away.
Luckily, no one noticed the “tech” I was wearing inside…
Surprisingly, it stayed completely quiet for the first few hours, so I didn’t even think about it during work.
I was more focused on remembering to sit or bend in ways so no one could look up my skirt, which didn’t always work. It actually led to my “new” colleagues chatting with me a lot.
After the morning shift ended and the evening crew took over, things got quieter in terms of workload.
Central dispatch called me and said I had to go with a colleague to pick up from another hospital.
I met the colleague at our vehicles. He said he’d gotten word that I should drive. He asked if I’d ever driven these vehicles before. I said no, even though as a “man” before, I’d driven them all the time.
He quickly explained the vehicle’s tech, and we set off. The drive to the destination was about 45 minutes.
The vehicle wasn’t the newest, so it rattled and shook everywhere.
We hadn’t been driving long when all the vibrators inside me started up. At first relatively weak, but gradually getting stronger.
Initially, it didn’t bother me; I even found it quite pleasant. Only the nipple clamps were uncomfortable from the start. What I found worst was that they didn’t just vibrate—they gave me electric shocks too.
Eventually, the vibrations got so strong that I couldn’t concentrate properly anymore, couldn’t keep the vehicle steady in the lane. Then I couldn’t hold back moaning anymore. Plus, I had to cry out from the electric shocks on the nipple clamps.
My colleague asked if everything was okay with me.
On the spot, all I could think of was to say I was on my period and sorry, but it always started really bad for me.
I was glad when we finally arrived at the hospital where we were picking up a patient.
I could barely get out; I had to double over from the discomfort.
My colleague said he’d quickly get the patient alone. His bad mood toward me was written all over his face.
I said I’d come along, but as we went right through the ER, all the devices jumped back to max vibration, and I collapsed.
Staff from the ER came right over to help me.
I just said everything was fine and I didn’t need help.
They showed me to the staff restroom, and I went in.
My colleague headed off to the patient meanwhile.
I locked myself in a stall first and checked if I could somehow reach the devices or the smartphone, but nothing worked. I was really well secured.
I went back to the vehicle, where my colleague was already waiting, ready to go.
He said I should take it easy and stay in the back with the patient. He’d drive on the way back.
Unfortunately, the vibrations were just as strong on the return trip, making me double over in pain several times.
To my luck, our passenger didn’t seem to notice or ignored it skillfully.
Once we were back and had completed the task, I dragged myself to central dispatch, where my boss was also hanging out, and complained of severe abdominal pain.
My boss came right over and told the colleagues they should send me home immediately. He’d drive me in his car.
I didn’t have to change, of course—I was still all locked up.
He took me to his vehicle, and we drove—not to my place as I suspected, but back toward his apartment. The vibrators kept going during the drive, and I had to double over again and again.
He said he’d take me tennis playing first—and he did.
We stopped at a tennis club’s parking lot.
He changed into appropriate clothes; I kept everything on.
Then he gave me a tennis racket, and we went to a free court.
A real game didn’t happen with the vibrators running, of course.
He said I was too dumb for everything.
He called off the tennis and pulled me into the locker room.
There, I had to sit in the men’s changing area while he changed.
But instead of changing further, he came over and shoved his dick in my mouth.
Automatically, I started blowing him. With my fingers, I gently played with his balls, and soon his cock was at full mast.
But apparently, my rhythm didn’t match his idea, so he grabbed my head with both hands and sped it up.
He shoved his tool so deep that I felt his pubes on my nose.
He repeated that several times until he finally shot his cum down my throat.
After I’d licked his cock nice and clean,
Once he was satisfied with my work, I had to stay seated and look up at him.
Then suddenly, my face got wet again. It wasn’t cum—it was his piss, which he sprayed right in my face.
The stuff ran down me and stained all my clothes yellow.
Then he slapped me a few times for the dirty, stinking clothes I was wearing now.
After that, he unlocked all the locks, took the smartphone, and told me to shower here. I could remove the nipple clamps and cock ring, but not the vibrator in my ass.
After showering, he tossed me a thong and a tight short dress to put on. No bra, so I had no bust support in the dress.
Matching ankle boots were lying in the locker room, which I had to put on.
Dressed like that, he went with me to the car and drove me to Brooklyn.
There, he stopped in front of an unassuming house and went with me to the front door. After a short wait, it opened, and we entered.
He just said this is where I’d get my temporary tits. I didn’t know exactly what he meant, but I’d find out soon.
I had to lie on a table; first, I took off my dress.
The person who’d let us in shaved any tiny hairs off my upper body and fetched large breasts and a kind of short pants from the next room.
First, I had to put on the pants. For that, I stood up. I pulled them on—it was latex pants that gave me a beautiful vagina. My penis went into a sort of condom, so I could do my business with the pants on.
Then I had to lie back on the table. Initially on my stomach.
I felt him fiddling with the pants in the back. In between, he spread a pretty cold mass, like lube, between my skin and the pants. Then I saw him working with an airbrush gun on me.
After that, I had to turn onto my back, and the same procedure started on the front.
Finally, he coated the breasts on the skin-facing side with the liquid stuff and placed them on my chest. He finished with the airbrush gun there too.
When he was done, I had to stand up again. I just said I needed a bra, or the things would fall off.
Both laughed, and my boss said they’d stay on even without a bra. The tits were glued fast to me, and I couldn’t get them off without special solvent.
The same went for the artificial vagina. I could even do my big business with it.
I had to stand in front of a mirror and saw that everything was airbrushed so color-matched that you couldn’t see any transition from my skin to the latex.
Now I had to put the dress back on. Then my boss pulled me to the car, drove me back to his place, and immediately tried out the artificial vagina.
By the time he left me lying there exhausted, it had been another relatively long and hard sex session at the end of the day.
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