9 to 5 Pt. 04

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Brenda starts work, and has a night out with the girls.
3.3k words
4.71
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Part 4 of the 5 part series

Updated 03/15/2024
Created 01/30/2024
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I gave Stacy a little twirl when I met her in the kitchen, and she said there would not be a soft cock in my department.

We took the tube together and headed into the city.

Part 4

I left Stacy at the tube station, so we did not walk into the office together. Sally was the same offish self, when I told her I had arrived. 10 minutes later, Todd arrived.

"Ah, Brenda, you are here," he said with a snide smile. God, I felt like punching him, but I thought better of it.

He led me up to HR, and I had to sit through the same boring induction videos I had already seen the last time I was employed here.

Finally, Granger took me up to the 15th floor and showed me to my desk; ironically, it was my old desk, and I had to smile to myself.

There were several faces I knew, but it looked like the department had undergone a massive shake-up since my forced departure. I was not the best pleased when one of the brown nosers, Greg Lowmax, was assigned as my mentor. I used to run rings around this twat, and now he is my mentor. It did not help that he was leering at me as he showed me around the department.

"This is Brenda; she is starting today under me." He introduced me as we went, smirking at the innuendo he was making about me being under him.

I smiled, keen to be the fresh, naïve girl that I was supposed to be. After I was left alone, I logged on to my terminal and paused, letting out a long, deep breath. I just hoped that when I was working here as Bryan, I was not as lecherous as Greg and his boys club. Stacy always referred to him as a prick, so hopefully that went in my favour.

A couple of girls came over to introduce themselves. I recognised Karen and Tara, but the new girl was a stranger to me. I pretended not to show any recognition as they introduced themselves, even though I had fucked Tara more than once in the stationary cupboard.

Soon I was focused on my work, and though I knew this system inside out, I called Greg over to show me stuff I pretended to be unsure of. The cunt leaned over me and rested a hand on my shoulder. Clearly, the me-too movement was not practiced here.

After lunch, I just put my head down and started trading stocks and shares. I was careful not to outshine anyone else on my first day, but I knew Brenda was a natural at this job and would be the big account winner in no time. But for now, I kept my powder dry.

Greg asked me if I wanted to go with him for a drink. I politely declined, saying I was off to meet my boyfriend. I could tell he saw this as a challenge rather than a rebuttal.

I met Stacy at the Wine Room, and I filled her in on my first day.

"I'd rather sleep with a hobo than that tosser, Greg," Stacy said with disdain.

"Well, my disguise is clearly working; I had shagged Tara Knight more than once, and she just smiled at me," I said.

"To be fair, Tara is not the sharpest tool in the workshop; it is her luscious cock, sucking lips that have kept her career progressing," Stacy commented.

I laughed, "I can vouch for that personally."

The next few days flew by, and I pretended to get to know the systems. I had run into most of the people I used to work with, and none of them clocked me as Bryan. Greg was still trying his luck to get into my knickers, but he was in a losing battle.

I had been welcomed into the office sisterhood and now took my lunches with Karen, Tara, and Sam, the new girl. I was starting to get into my role as a woman, and sometimes I forgot that I was a man in disguise.

Stacy mocked me for reading gossip magazines like OK and Hello. I just told her, "I need to research this shit so I can hold my own when gossiping with the girls."

But part of me was really enjoying the comradery of the sisterhood, as they called themselves. It helped break up the constant unwanted male attention.

That Friday night, the girls invited me out on the town with them, and I accepted. Stacy told me to be careful as I finished getting dolled up in my new emerald green, off-the-shoulder cocktail dress. I had to admit, I looked damn hot in a frock. I French plaited my hair (YouTube is a crossdressors invaluable resource for tutorials). I completed my ensemble with a pair of 4-inch black fuck me stilettos and a sequined clutch bag for my phone and money.

I took the tube over to Camden and met the girls in the bar next to the lock.

"Shit Brenda, you scrub up well." Karen complimented me.

I gave the group a twirl and said, "Thanks, ladies."

They had already purchased a bottle of prosecco, and Sam thrust a glass into my hand. I felt at ease with the girls, an ease I never felt with a group of lads. That was mostly a dick-swinging competition, and though I freely admit that I participated in the competition at the time, I am now more than happy to shoot the shit with these girls.

I had a minor panic when Karen teased Tara about Bryan, "Remember that guy Bryan you used to shag? Poor fucker got shit canned. Those cunts upstairs royally screwed him over."

"Yeah, poor bastard," Tara mused. "He had a lovely cock, and he knew what he was doing with it. I wonder what happened to him."

I thought this was a ruse to out me, but after a couple of long seconds, I relaxed when the subject was changed to some other former colleagues who lost their jobs in the wake of the scandal.

The night progressed, and we had moved onto a club, where we started dancing between shots and prosecco. Sam and Karen drew the attention of a couple of guys, and they were clearly receptive to their attention.

Tara and I gave them space but kept on boogying the night away. At first, I did not notice his approach, but soon a guy was dancing with me. A combination of the large amounts of alcohol and the buzz I was on for the fab night, I was actually dancing back to him.

After a couple of songs, he was getting bolder, so he slipped his hand on my hip and pulled me towards him. Even in my heels, I was still shorter than him, and it felt like he towered over me. My heart started to race as I felt the heat of his body next to mine.

In a daze, I hardly noticed the music had switched gears to the slow songs. My new suitor pulled me closer, wrapping his arms around my waist. I instinctively put my arms around his neck, locking my eyes on his.

Lost in the moment, I was receptive to his first kiss and his second. My lips parted, and his tongue entered my mouth. We snogged for what felt like hours; his hands found their way to my arse, and he was happily squeezing my satin-covered butt.

Then, I realised that my cock was rock hard within my knickers; this snapped me out of my first female sexual encounter.

I panicked. What the fuck was I doing? I pulled myself free from his embrace.

"Sorry, I've got to go," I said as I rushed out of the club.

He tried to follow me, but I lost him in the crowd, and soon I was outside in the fresh night air, almost hyperventilating. My cock was still sporting a semi, and I needed release. I headed to the red-light district. There were a couple of prostitutes touting for business.

One said to me as I approached, "Fuck off, bitch, there are too many of us here already."

"Fuck off; I'm looking for some action." I snapped back.

She scoffed at me, then turned to the tart to her right and said, "Becky, there is a lezzy here; do you want to take it?"

Becky looked like she was in her early 30s and clearly had a hard life. She looked me over and said, "£50 for oral."

"Fine," I said, and I followed her down a back alley.

"So, am I eating you, or are you eating me?" she said as she spat out her gum.

I leaned back against a wall and lifted my dress, pulled my panties aside, and let my cock flop out. "I need this taken care of."

"Shit." She said as she lowered herself to her knees in front of me, "A fucking tranny, I would never have guessed."

The hooker lifted my cock to her lips and, without ceremony, took me into her mouth. I leaned my head back against the wall and let out a satisfying moan. I thought from my state of arousal that I would not last long, but after 5 minutes I was edging, but not enough to cum.

I sensed the prostitute was starting to get annoyed with me, which did not help.

"What the fuck!" I screamed as I felt her push a finger into my arse.

She wiggled it around until she found my prostate. I swear my cock grew in her mouth as a new wave of pleasure washed over me.

"Fuck!" I cried as I blasted five hot ropes of man juice into her mouth.

My knees were like jelly, and if I was not supported by the wall, I would have fallen to the floor. The hooker pulled her finger out of me as she freed my cock from her mouth. She stood up and spat my seed on the ground. Part of me regretted the waste of cum; what was wrong with me?

"£50 then." She said, putting a fresh stick of gum into her mouth.

I composed myself, putting my cock away and smoothing down my dress. I fished the notes out of my bag and handed them to the prostitute. She stuffed the money in her clutch bag and walked away.

I stayed in the alley for a little longer; that orgasm was one of the most intense ones I've ever had. With the euphoria of the sexual release waning, I was starting to feel the effects of the large amount of alcohol I had consumed.

I suddenly bent over and started to throw up. I felt like I was throwing up my lungs as I expelled several litres of booze.

"Are you OK, love?" I heard it from behind me.

I stood and turned. Standing there were a pair of uniformed policewomen.

"Yeah, sorry, I drank a little too much. I'm going to head home now," I replied, wiping the remaining vomit from the corner of my mouth.

I had sobered enough that the constables let me on my way. I headed straight for the tube station and back to Stacy's.

The rest of the journey home was a bit hazy, but I must have made it back OK.

The next thing I remembered was waking up on Stacy's sofa. I was still fully dressed, and as my eyes started to clear the fog in my head, I saw Stacy standing over me with a cup of coffee.

"It looks like someone had quite the night." She said this as she handed me the cup.

I sniffed the coffee aroma into my nostrils; just the smell helped ease the pounding hangover.

"Yeah, you can say that." I mused before sipping my drink.

Stacy pointed to my crotch and asked, "Are those spunk stains on your knickers?"

I looked down, and my dress had ridden up through the night, exposing my panties. There was a clear white semen stain on the front of them.

"Oh." That is all I could muster.

"No, you cannot just leave it at, oh, spill the beans," Stacy demanded.

"I need a shower first," I said. Truth be told, I needed some time to process the events of the night before.

I stripped off my clothes; the dress had traces of vomit down the front. I hoped a good dry clean would save it; I liked it.

In the shower, emotions overwhelmed me, and I started to sob.

"What is wrong with me? I'm turning into a poof." I cried, tears streaming down my face.

I did not hear Stacy come into the bathroom and say, "Oh Brenda."

Still wearing her pyjamas, Stacy stepped into the shower with me. Under the torrent of water, she embraced me. I buried my face in her shoulder, sobbing uncontrollably.

I was inconsolable for what seemed like ages as my tears flowed. When I finally stopped, Stacy shut the water off and wrapped me in a big fluffy towel. She stripped off her wet clothes and wrapped herself in a large towel too.

We sat on the sofa, and I knew I owed her an explanation, though she was patiently waiting for me to start.

"I kissed a guy last night. And the scary thing is, I enjoyed it." I confessed, not able to meet her gaze.

She hugged me tight. "Brenda, you've made some major changes to your life recently; it is no wonder you are getting confused."

"I've never been attracted to men before. I did not think; I just went with what felt right. But it is not right; I'm a guy." I said, starting to feel my emotions boil up again.

Stacy laughed, "A guy, sorry Brenda, but you have not been acting like a guy recently. I think you are more comfortable as a girl than I've ever seen you as a guy. Perhaps these lifestyle changes have awoken something within you."

I shook my head. "I did not want this to happen to me; I think I need to go back to being Bryan."

"Why, till now, I've never seen you happier. Would it be so bad to let yourself explore this new you? You may like her." Stacy reasoned.

"But I'm a man." I sobbed.

"Stop that now; you've taken a leap to act like a woman. Is it a real surprise that you actually like being a woman?" Stacy snapped at me. "You need to stop beating yourself up about it and go with it."

Silence descended again as her words sank in. Could I, or should I, just explore this new side of myself? I was afraid of where it could lead after last night's encounter on the dancefloor. Could I let myself be picked up by a guy? Could I play the role of a woman sexually?

I had too many questions and no answers. What is the worst that can happen? The feeling of the finger in my butt is what made me come last night. I had no idea the feelings that stirred.

Stacy left me to get dressed, and I threw on a t-shirt and skater skirt.

We headed out to the local café for breakfast, and as we waited for our food, I filled Stacy in on my encounter with the prostitute.

"So, you came when she fingered your arse?" Gasped Stacy. "It seems to me that you might need to explore that a bit more; after all, gay guys love to be bummed."

I had a weak smile as I replied, "I'm not sure I'm ready for a cock up there just yet."

Stacy giggled. "That is not what I'm saying; you could try some toys to see if you really do like them."

"Wow." I said, "You mean a dildo?"

"Why not? You have nothing really to lose. I certainly will not judge you for exploring this new side of you." She replied.

"I see," I said.

"Look, I don't want to hit you while you are feeling vulnerable, but I was intending to speak to you this morning." Her tone was shifting to a more serious one. "I think it is time for you to branch out and find your own place."

I just looked at her.

She rested a hand on mine and said, "We both can agree that Brenda is here to stay for the foreseeable future, so it is time for you to get your own space rather than crashing on my sofa."

"I guess you are right." I could not argue with her really; she had put me up for the last month rent-free. "First thing Monday, I'll start looking for a new flat."

As the idea of getting my own place started to sink in, I started to get excited by the prospect of striking out on my own.

Monday morning, I was sitting at my desk, processing trades. I felt good after my chat with Stacy; she was right--it was time to not get hung up on the past and let the new me flourish. Today I wore my charcoal grey suit with a white pussybow blouse underneath. I felt eyes on me on the tube this morning, and for the first time, I swelled with pride that I was starting to have that effect on men.

Tara came up to my desk with a couple of cups of coffee; she placed one down for me. "What happened to you on Friday night? One minute you were sucking face with that hunk, then next you were gone."

I took a sip of my coffee and said, "Sorry, I guess I was not ready yet to be with a guy. I was with my last fella for several years, and though I'm glad I've dumped him, I'm still not ready to let myself go there yet."

"Understandable, that guy, Karen mentioned Bryan; even though he was just into me for sex, I had hoped he would want something more." She said with a look of regret, "He was one of the few guys around here you could have a future with, and now he is gone."

I instantly felt guilty; as Bryan, I was nowhere in the headspace to see her as anything other than a quick bit of relief, but as Brenda, I had gotten to know her, and she was not as shallow as she appeared to be.

"I'm sure there is someone out there for you." I said I was trying to deflect the conversation from Bryan.

We just chatted for the next few minutes before getting back to work.

At lunchtime, I started to browse the ads for a flat. I found one in Hanwell, in the west of London, on the outskirts of Ealing, that was in my current budget. So, I made an appointment for a viewing after work.

I took the tube to Hanwell, and it was clear this part of London was not as affluent as Kensington or Docklands, where I lived as Bryan. But though I had plenty of money squirreled away in off-shore accounts, I had to live within the means of my current salary.

The flat was not a bad 2-bedroom apartment, so I took the lease.

Back at Stacy's, I filled her in on the flat and thanked her for putting me up and helping my transition into Brenda.

"I've got a little housewarming gift for you." Stacy said, handing me a gift-wrapped box, "I hope you like it."

I tore the wrapping paper of the box to reveal a 6-inch vibrator. "What the fuck, Stacy!"

"For those lonely nights in your new flat." Stacy mused.

I could not help but blush.

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4 Comments
AnonymousAnonymousabout 2 months ago

Really enjoying the slow burn of this though wish I had more to read, more often! But that is a good thing. Keeping the transition inevitable but realistic is great to read. The mix of self doubt and sexual exploration with a healthy dose of empowerment/positivity is a good mix rather than instant overwhelming acceptance/unrealistic interactions.

FernVillaFernVillaabout 2 months ago

This is developing into an interesting story. Looking forward to the next episodes

Sister_CageSister_Cageabout 2 months ago

Like how this is not like some other stories, where the woman changes and just starts having sex with men with no thinking about her feelings and fears. Hopefully this story runs and runs

dreamer31adreamer31aabout 2 months ago

Cant wait for the next chapter I bet its exciting

keep it up

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