9 to 5

My name is Bryan Rogers. I'm 26, 5`8", and slim built for a guy due to the swimming I did at university. I graduated with honors in business management and financial market management. I had at uni built a nice little portfolio of stocks and managed to clear my student debt just after I graduated.

Armed with my degrees, I soon found employment at Jackson and Wright, a top London powerhouse in the city. My savvy skills soon led me to rise to a team leader role, and I was pulling in 50K a year. I was living the yuppy dream: a river-side apartment in Docklands, an Aston Martin in the parking garage, and expensive suits( though I avoid the stereotypical red braces). I also had a steady stream of sexual partners. Girls like me who were career-minded and just wanted a fuck to scratch an itch. I had a couple of regular friends with benefits, but it was all very casual.

So, like I said, I was living the Gordan Gecko dream until one day my world imploded.

Josh Jackson, son of CEO Denny Jackson, fucked me over royally. He was my department head and had shorted several stocks that ended up collapsing, costing the firm a few million pounds in losses. On top of that, the Omi busman fined the company another million for mismanagement of customer funds.

As is usual for such a cluster fuck, the word came down that heads would roll. Little did I know I was number one on the chopping block. Josh the cunt had put my name on all the dodgy stocks he was trading, so I got the blame, and there was little I could do about it!

My head was spinning as the security guard left me holding my little cardboard box with my few personal items. So, in the space of an hour, I went from a high-flying executive with a 50k salary to unemployed.

Back in my flat, I drowned my sorrows with a 30-year-old bottle of scotch before passing out on the couch.

I awoke with an almighty hangover, but I fought away the pain and hit my contacts at other firms in the city. Two hours later, I cut off the last call. Shit, word had gotten around, and I had been blackballed.

My so-called friends also stopped returning my calls, all but Stacy from my old firm. She was one of the few women I slept with who oozed sex appeal when wearing a power suit in the office.

Stacy took me out for a drink to commiserate about my fallen career.

"That bastard Josh got away scot-free," Stacy said, sipping her cocktail. "Rumor has it, his father had the documents changed to put your name on the trades; he did not care who it was as long as Josh was in the clear."

I lowered my head in my hands and said, "So it was blind fucking luck that I was picked; well, at least it was not personal!"

Stacy put a consoling arm on my shoulder. "They also made sure the other firms knew it was you as well. Sorry, Bryan, but you are finished in this city.

I felt a tear escape the corner of my eye but managed to wipe it away before anyone noticed.

Stacy and I had a few more drinks before we went back to her flat for what I assumed was a pity fuck. Not that I'm complaining; she gives a great head and fucks like an animal. Usually, I'd just get up and leave, but I was in no hurry; it was not like I had to go into the office in the morning.

As we lay there, Stacy looked over at me with a look in her eye that suggested she was seeing me for the first time.

"You know, Bryan, you are not average for a bloke; in fact, if you were wearing a dress and a wig, you would pass as a woman without question," she said as a matter of fact.

"Gee, you know how to kick a guy when he is down," I replied.

She smiled as she playfully punched me in the arm. "I have no complaints about that lovely cock of yours, but the rest of your body is very effeminate."

She let those words hang in the air before she delivered her devious plan.

"Look, as Bryan, you are unemployable; you are toxic," Stacy said in a serious tone. "I have a friend, Brenda; we graduated together, and shortly after, she went on a gap year to Africa and fell in love with a fella who is a missionary. She has fallen off the face of the earth as far as everyone is concerned, and some think she may even be dead."

"That is a sweet story, but what has that got to do with anything?" I said.

"Look, Duffus, she has all the qualifications you have; she is not using them, and with a little work, I can re-invent you as Brenda Chaplin hi flying executive," Stacy said, pleased with her plan.

My eyes widened. "You want me to dress as a woman to get a job? That is insane."

"We could pull it off; we can apply for her birth certificate; and from there, we can get you all the ID you will need to become her," she said as if it were a rational plan. "I can give you a makeover, and no one will ever recognise you; it is foolproof."

"Yeah, and I'm the fool!" I scoffed!

Stacy paused for a moment as she considered her next words: "OK, if you let me dress you up as Brenda and we go out to a club, I bet if you do not get outed, you would consider my plan, and if you are outed, I'll drop the whole idea."

Her ultimatum hung in the air. I was in stunned silence before Stacy broke the tension: "I take the fact that you have not dismissed the idea out of hand that you are considering it?"

Was I? She had the wheels turning in my head; I had no real friends other than Stacy, it seems. I have no family after my folks were killed in a plane crash when I was 19. Who would miss Bryan Rogers? Could this work? Could I pull it off? I might be, by Stacy's observation, slightly built as a man, but I was a man's man when it came to my mannerisms.

I looked her in the eye and said, "You think you can polish a turd like me into a lady?"

"A lady might be pushing it, but I can make you passable enough," she said convincingly. "What have you to lose, except a little macho bravado?"

"Fuck it, I need to try something; I bet those cunts have gotten me blacklisted globally," I said, resigned to her plan.

Stacy hugged me tight and giggled like a schoolgirl. "This is going to be so much fun."

Her hand slipped to my cock, and within minutes I was balls-deep in her again. The thought of femininizing me must be a real turn-on for her, as I fucked her through four orgasms before I dumped my load into her.

After we fucked, I fell into a deep sleep, the first time I had stayed over at Stacy's. When I awoke, I was alone. Looking at the bedside clock, it was 10 a.m., so I assumed Stacy had gone to work.

I helped myself to some breakfast before hitting the shower. Standing in her bedroom, I looked at myself in her full-length mirror. I tucked my cock between my legs like Buffalo Bill from Silence of the Lambs. Stacy was right from the neck down; except for my cock, I had a feminine figure.

"Fuck, I never really noticed till now," I said to myself as I took the view in.

I practically jumped out of my skin as my mobile phone rang, jolting me back to reality.

The caller ID showed it was Stacy: "Bryan, I hope you slept well. You looked so peaceful this morning that I decided to leave you be."

"Thanks; it was the best sleep I've had since I was canned," I replied.

"Well, tonight is the night we get to see if you can pull off Brenda," Stacy told me, and my heart pounded in my chest.

"Stacy, I'm not so sure..." I meekly said.

"Don't you fucking dare back out on me!" She bit my head off. "I already planned this to the letter; I'll be home early, and you had better be there."

Stunned, I could only muster a simple "Okay."

Stacy hung up on me, and I felt a flood of emotions as I started to weep at how pathetic my situation had become.

Around 3, the door to the flat opened, and Stacy came in carrying several bags. She walked straight past me, went into the bedroom, and dumped the backs on her bed.

"Bryan!" she called to me.

As I entered the bedroom, she was just hanging up her suit jacket. "Okay, mister, I have booked a cab to take us to Camden at 6 p.m. I have that long to work my magic; now strip."

I now knew better and started to take off my shirt and jeans. As I stripped, Stacy went and turned on the shower, and as she re-entered the room, she was unbuttoning her shirt. Seeing the lacy bra and her fabulous tits come into view caused my cock to grow.

Stacy tossed the shirt into a hamper and then turned to me and said, "You'd better get that under control if you want to have a chance at passing tonight."

Soon we were both standing there naked as the day we were born. I so wanted to take her there and then, but I could feel a frosty reception coming my way if I did.

She led me to the shower, and we both stepped in. Stacy was all business as she rubbed cream all over my body.

After a few seconds, I yelled, "Fuck Stacy, that is burning my skin off."

"Stop being a baby; it is only a little hair remover. It will be off in a minute," she replied.

She was right; as she rinsed me off, the little body hair I had went down the drain. Stacy shut off the shower and handed me a silky robe, and she put one on herself. My whole body tingled as the silky robe engulfed my new sensitive skin, and again, my cock rose to full erection.

"Fuck Brenda, you need to get that thing under control," Stacy teased me.

I stared blankly at her as she addressed me as Brenda for the first time. Now, like a deer caught in some headlights, I was led to her makeup table, where I sat in stony silence as she went to work on my face.

First, she plucked and shaped my eyebrows, then glued on some false eyelashes.

"God, I'm jealous of your skin, Brenda; you won't need much foundation," Stacy complimented me as she started to apply the contouring makeup.

I felt a moment of pride from her compliment, but the bubble burst when my inner macho man told me to stop acting like a poof. Again, I was back to my silent self as Stacy finished making up my face, with the red lipstick being the final touch.

She went to her new purchases on the bed and returned with a white box. Opening it, she pulled out a shoulder-length wig that closely matched my hair colour. She slipped it on my head and secured it with some hair grips, so it was firmly in place. A minute or two of fussing with it, and she was done.

Staring back at me was a not-bad-looking girl, a little flat-chested, but a girl for sure, and she was me.

"Fuck Stacy, I don't even recognise myself," I said in stunned amazement.

"I know right," she replied with pride. "Wait till you see yourself in the rest of the outfit."

I knew, being a man, I should have dreaded the thought, but part of me was excited to see where this transformation would end up.

Stacy had me stand and take off the robe. She then went back to her purchases and started to hand me items to put on. First was a pair of lace top stockings, followed by a suspender belt.

"You should always start with your suspenders, as it makes taking your knickers off to pee easier," she advised me.

With a little help, I had the nylons on and clipped to the welts of the belt. The feeling was incredible, and it took all my control to keep my cock in check.

Next, she handed me a pair of lace-edged silk black panties, I slid them up my legs and encased my cock and balls in the soft material.

"I got you boy short panties to keep your manhood held in, not sure you are ready for thongs just yet," Stacy teased me.

The panties were followed by a pair of fake C-cup boobs with straps; the weight on my chest immediately made me change my posture. Stacy then gave me a matching black bra, which she fastened for me.

I looked again in her full-length mirror, and any trace of Bryan was gone. There was a fairly attractive woman looking back at me.

"Come on, you can admire yourself later; I need to get you dressed so I can start on myself," Stacy said, catching me lost in my own reflection.

Stacy produced a black dress and helped me into it. "The LBD, or little black dress, is a must for any girl's wardrobe."

The dress cascaded down my body, and the hem fell halfway between my butt and knees. Stacy zipped the dress up, and it conformed to my new curves, giving me a very sexy silhouette. To finish my outfit, she handed me a pair of black heels with a 3" heel.

"When you walk as a woman, remember to put one foot in front of the other; it will make your arse swing as you walk," Stacy advised me. "Now go grab us a glass of wine while I get ready."

As I walked to the kitchen, I tried to walk as Stacy instructed, and soon it did not feel so alien to walk this way.

I poured us both a glass of pinot gris and headed back to the bedroom, my arse swinging side to side as I strolled.

"Fuck me" was all I could muster when I caught sight of Stacy dolled up.

"You like?" she said, giving me a twirl.

I had seen her naked many times, but when dressed, she was wearing one business suit or another. Now she wore a crimson dress that ended just below her arse and a plunge front that accentuated her breast. She was transformed from a stylish businesswoman to a sexy model.

"I've never seen you in non-work clothes before; you look fucking gorgeous," I replied, picking my jaw off the floor.

Stacy winked, "Why thank you, Brenda; you look beautiful too."

I blushed; for a moment, I forgot I was dressed up to the nines as a woman ready for a night out.

I handed Stacy her wine, and we spent the next hour perfecting my walk, how to sit, and how to reapply my lipstick.

Her phone buzzed with an incoming text message: "Cabs here, oh, one last thing."

Stacy went into a draw and pulled out two rings, one with a simple silver band and the other with a diamond on it. She slipped these onto my wedding finger. I looked at her, confused.

She smiled and said, "It is a tactic I learned a while ago when I want to go out but not draw any unwanted male attention; most will leave a married woman alone."

I felt strangely reassured by this as Stacy slipped another set of rings onto her wedding finger.

Stacy pulled out a little clutch bag and told me to put my phone, cards, and lipstick in it. The bag had a thin gold chain that I slung over my shoulder.

Sensing my nerves, Stacy winked at me and said, "Don't worry, B, you got this."

I took my first tentative steps outside, feeling extremely self-aware of the way I was dressed. We passed a couple in the hallway, and then a guy was in the lift as we descended to the ground floor. Sensing my anxiety, Stacy discreetly reached over and gave my hand a reassuring squeeze.

The guy was a true gentleman and moved aside to allow us to exit the lift first. I was thankful the cab was parked just outside the building, and soon we were safely in the back of the car, headed off into the night.

Stacy burst out laughing. "That guy in the lift was clearly checking you out; I saw his eyes on your arse and legs as we got out of the lift."

I blushed and playfully punched her in the arm. "Not jealous, are we?"

"Get you a couple of hours as a woman, and you are already a prick tease," Stacy retaliated.

We both laughed as my nerves died down just for now. I pulled out my phone and started to browse as the car drove us toward Camden Town.

The car dropped us next to Camden Lock, and Stacy led us to Simmons Bar. Stacy ordered us both a glass of prosecco, and we took a seat at a table.

"Relax; you are going to draw attention to yourself by the way you are acting. Just focus on the moment," Stacy told me.

I smiled and raised my glass to hers. "Here is to not getting beaten up tonight."

We clinked glasses, and the DJ started to play his set. Slowly, with the help of the Dutch courage and the fact that no one had pointed at me and shouted, there was a bloke in a dress sitting there.

After my third glass, I had to pee. I looked at Stacy and said, "I need to pee!"

"So, just go into the ladies; no one will know, so why would they care?" Stacy said.

I tried to hold it, but the urge to go overwhelmed me, and I got up and headed to the bathroom. I almost went into the gents out of habit, but at the last minute, I remembered and went into the ladies. It was as if I had entered an alien planet. Compared to the gents the place was clean, with no piss on the floor.

I took the first empty stall and, after pulling down my panties, grateful for Stacy's advice about wearing them over my suspenders. The relief as I pee'd was magic, and when I was done, I made sure to tuck my cock before smoothing out my dress.

After I exited the stall, I got bold and went to the mirror to touch up my lipstick, as Stacy had taught me.

The girl next to me asked, "Love that lippy; where did you get it?"

My mind raced: "Ah, my mate lent it to me; I'm not sure where she got it."

She smiled, and I made a hasty retreat before she asked me anything else.

When I got back to the table, Stacy was just finishing her drink before standing up.

"The night is young, and I want to dance. Come on, let's go to the Electric Ballroom," Stacy announced.

On the short walk to the ballroom, I did feel some eyes on me, and we even got a wolf whistle from a group of lads headed the other way.

I looked and smiled at them before Stacy leaned into me and said, "Don't forget you're supposed to be married!"

"Oops, I guess I just got carried away in the moment," I replied, a little surprised that I was getting into my new role so easily.

Mild panic set in as the bouncers were doing random ID checks as we approached the ballroom, but thankfully they just waved us through. It was still early, barely 9 p.m. when we got there--but the place was already jumping.

For the next 3 hours, we danced and drank the night away. I was completely relaxed being Brenda, and if I'm honest, I was having the time of my life. My fear of using the lady's loo had passed, and on my last visit, I actually had a brief chat with another girl at the sinks as I freshened my lipstick again.

As I waited at the bar for another round, I felt a pair of eyes on me. I slowly turned around to see a guy in his mid-20s smiling at me.

"Hi, I'm Steve. Can I buy you a drink?" He asked.

Shit, I thought, before I remember Stacy's man repellent on my finger, "Sorry, love, not sure my husband would approve."

I diverted my eyes to the rings on my finger, and his followed. I gave him a little shoulder shrug, and he smiled and disappeared into the crowd.

I sighed in relief as the bartender took my order. Stacy howled with laughter when I told her about my potential suitor.

We left the club around midnight, both a little worse for wear. We managed to hail a cab with little fuss and were soon on our way back to Stacy's Kensington flat.

On the way, we chatted about the evening like a couple of girlfriends would. It turned out Stacy had to rebuff two guys while I managed to attract five unwanted gentleman callers.

Stacy paid for the cab as I waited by the entrance to her building. Soon we were in her flat, and we kicked off our shoes. I had another pee, as Stacy made some coffee.

As she handed me my mug, she said seriously, "So do you believe me now that you could pull this off?"

I swallowed hard. "I find it scary that I managed to pull this off, but to do it day after day in broad daylight, I don't know."

"My only concern is the way you were a cock magnet tonight; you will be fighting off pests in the office," Stacy replied. "But in all seriousness, you can do this, Brenda."

It was strange that even now that we were back at her flat, she was still referring to me as Brenda.

"You really think so?" I asked her now, sobered by the conversation.

"Abso-fucking-lutely," she reassured me.

I smiled at her and said, "Then what is the next step?"