Urban
patreon
They Think I am a Woman! - Part 1
🕑 Added 2025-05-15 14:51:44 +0000 UTC'I'll have to ring them. Let them know about the mistake.
'What job were you going after, hun?' said Sheila.
I went a bit red.
'Erm, secretary.'
I hurriedly explained. 'The job didn't say anything about being male or female, and anyway, they can't discriminate anymore. There are laws against it.'
Sheila looked at me with an amused expression on her face.
'Sure, Tony, do you really believe what you are saying?' There are a few male secretaries, but that is normally in big companies that need to be careful about discrimination. I'm betting that, as you are going to be interviewed by the director, it's a small company without a human resources department.
I knew in my heart that she was right. They would want a woman, not a man.
'Why did you go for a job like that anyway?'
'I can type.'
'When did you learn that?'
'Well, my dad was a software engineer; he got me interested in computers. I learned how to use a computer keyboard when I was knee-high to a grasshopper. I got to be very good before he died. I used to help write up his notes.
I screwed up the letter and threw it in the bin.
Sheila was looking at me oddly.
'How much does the job pay?'
16K a year with bonuses.'
'Wow, that's good money. You could afford to live on that, couldn't you?
'Sure, but it's academic; I can't go to an interview. It's a waste of time. I'll ring them tomorrow to cancel.
Sheila gave me another strange look.
'Tony, have you got any other jobs in the pipeline, say, brain surgeon, pop singer, judge, anything at all?'
'No, you know I haven't.'
'Stand up a minute.'
'What?'
'Just do as Auntie Sheila asks, please.'
I stood up. 'What is wrong with Sheila?' I thought. She needs to go to bed. This night work is getting to her.
'Turn around.'
'What!'
'I said turn around, silly, do a twirl, go on, just for little me.'
I shook my head, thinking that she had flipped or something, but I slowly turned around until I was facing her again.
'You are a skinny little runt for a boy of 18, aren't you?'
'PARDON.'
'Oh, sorry, Tony. I know you have a thing about your size and shape, but don't you see, it could work.
'WHAT COULD WORK!'
'Don't shout, you'll wake up the rats in the walls.'
I calmed down a bit.
'Sorry, but I get upset when people call me names and don't explain themselves.'
'I apologize, Tony; look, I'll lay it on the line. One, you have no money; two, you have no job; and three, you are about to be thrown out on your ear. Am I right so far?'
I nodded, still not knowing where this was going.
'OK, point four, you are quite small; in fact, you could be called petite, am I right?'
'Yes, I can't help that, though, can I?'
'No, but you can use it to your advantage. Now we are realistic enough to know that you won't get that job if you go to the interview as you are.
'Yes, but I can't go any other way, can I!'
'Yes, you can.'
'No, I can't, silly!'
'What if you went as a girl?'
'A GIRL.'
'Yup, I think it would work.'
I sat down heavily on my creaky bed.
'Sheila, are you nuts? How can I go as a girl when it's obvious to anyone with eyes that I am a boy?'
'Not when I'm finished with you, hun. Look, I know you sort of look like a boy now, but let's face it, you are no hunk. You are thin and small; you are about an inch shorter than I. You have a nice face. Do you shave much?
I felt my face go red. What with being blond and a little underdeveloped in the he-man department, I only needed to shave a couple of times a week, if that. I somehow never did have my fair share of hair.
'Sometimes,' I said in a small voice.
All this was embarrassing and more than a little bit personal. Remember, I was painfully shy, and I was very immature where the opposite sex was concerned. I didn't know how to deal with a feisty, outgoing girl like Sheila, and now she was calmly suggesting that I turn myself into a girl, get a job, and live happily ever after!
Sheila grabbed my hand and said. 'Look, Tony, as the song says, I think that you can do it if you really try. I will help you. We have a few days to get things right. Let's go to my apartment and try to see if I can turn you into the ideal secretary.'
'What about your boyfriend Steve? Won't he be there?'
'No, he's on call at the hospital till tomorrow. Come on, don't wimp out on me now.'
In a daze, I let her lead me to her apartment, and as I went in, all I could think of was what my mom would think of her little boy now.
So there I was, sitting on Sheila's bed, being shown all manner of girly things.
The floor looked as if a bomb had hit it. There were skirts, blouses, panties, nylons, dresses, and other things that I was not sure of, all over the place.
'Ooh, look, this would be lovely.' Exclaimed Sheila, holding up a black blouse.
'Err, nice blouse' was all I could think of saying.
'Don't be silly, this is my LBD.'
'LB, what?' I asked innocently.
'God, you haven't lived much, have you, hun? It's my little black dress. What do you think?
I went as red as a beetroot and just sort of squeaked.
'Sorry, Tony, I didn't get that.'
I cleared my strangely constricted throat and said, 'I can't wear that; it's far too short. Do you want to get me into trouble or something?'!
Sheila looked at the dress critically and sighed, 'Ah, well, a girl has to try. OK, what about this then?'
She pulled a longer dress out of the pile in front of her. It was a cream color and looked like a sort of cottony fabric with straps. (Hey, don't ask for detailed descriptions; it's not as if I am a fashion expert or something !)
'Can't I wear a top and a pair of slacks?' I asked, more in hope than expectation.
'No, you need to wear something that oozes efficient secretary. Let's try it on, shall we?
'OK,' I said with a certain amount of natural reluctance.
I grabbed the dress and started to put it on.
'What are you doing, Tony?' You have to take your clothes off first, dummy.'
'Is that really necessary? We only want to see if it fits.'
'You won't know if it fits unless you strip down properly and try the dress on like a real girl. Look, we are going about this the wrong way. Let's do it as if it were me getting ready to go out for the evening, OK?
'OK.'
'Right, first things first. Go and take a shower. I don't want any BO on my nice, clean clothes. Wash your hair, and don't forget to use the conditioner. When you've finished, put on the robe that's hanging on the back of the shower room door. While you are doing that, I will tidy up here and get your undies and things sorted out.'
I scooted into the bathroom and shut the door, locking it, just to make sure that Sheila didn't rush in and take me by surprise.
I stripped down to my birthday suit and got into the shower. I found some shower gel. It was pink and smelled nice. As I showered, I was thinking all the time that I was silly to think that I could pull this off. My self-esteem was not great. I had no confidence in myself, and no way would I be able to fool anyone that I was a girl and that I could hold down a job as a secretary. I washed my hair, remembering to use the conditioner on my rather long locks. Finally, I was finished. I switched off the shower, grabbed a big towel, and dried myself as quickly as I could.
I stepped out of the shower and saw the robe on the back of the door. It just had to be pink and silky, didn't it!
I put it on and tied it using the silky belt. I must admit that it did feel nice, sort of soft and slippery. Anyway, enough of these pervy thoughts. I went back into the bedroom to find Sheila putting a few things on the bed that looked decidedly feminine.
'All clean then?' she had in that bright, nursery sort of way.
''Yes, I think so.'
'OK, take the robe off, and let's have a good look at you.'
I did my red beetroot face again.
'Look, Tony, I have seen more bare men than you have had hot dinners. Just think of it as if you are in the hospital and are undergoing treatment. I need to see you without your clothes on so that I can work out what size undies and things we need, OK?
'OK. But promise you won't laugh.'
'What at? There is nothing under that robe that I haven't seen a million times.'
I slowly took off the robe and let it fall, holding my hand in front of my rather small and shrunken manhood.
'Well, you're skinnier than I thought. No hair except a few pubes. Quite a nice shape, though. I think we can do something with you that will convince your interviewer that you are worth employing.'
She ran her fingers through my hair.
'Put the robe back on while I sort your hair out. It's long enough for me to do something with it.'
I quickly did as she asked; better the robe than in the nude!
Sheila put some large rollers in my hair and then blow-dried it. She then pulled the rollers out, dried some more, and then attacked my shocked locks with a large hairbrush. She seemed to take ages. Pulling my hair one way and then another. I was getting a headache by the time she was satisfied.
'That will do for now, but I think we will have to visit the salon before you go to the interview.'
Salon! That sounded ominous.
'Can I see what you've done?' I asked.
'Not yet, wait until we've finished. Now let's do some makeup.
Do I need makeup? We're only trying on some clothes!
'Remember, hun, we said that we were getting ready to go out for the evening. No way would I go out without some war paint on. Just trust me, I won't make you look stupid, OK?'
'OK,' I said reluctantly.
First of all, she put splotches of skin-colored cream all over my face and neck with a sponge and worked it in.
'You have good skin, Tony, but you don't want it to shine in bright lights. Anyway, a girl is naked without foundation. You don't need much, though. Now, some powder, good, you do have nice skin; I'm envious. OK, we need to color those cheeks; you do look a bit anemic. Let's put some nice, mild pink blush on. There, that looks lovely. Right, close your eyes while I put on some eye shadow.
She carried on talking, and I just let it wash over me. A strange feeling came over me as I was worked on by this determined nurse. I suppose it was a mental shrugging of my shoulders. I accepted that she was going to finish what she started, and no amount of whining on my part was going to alter it.
After nearly blinding me with a mascara brush and putting several coats of gloss on my lips, she was finished.
'That wasn't too bad, was it?'
'I suppose not,' I said graciously.
'Right, let's get you some false boobies.'
She rummaged about in some drawers and pulled out a couple of rubber breasts!
'I used these when I went through my Dolly Parton phase. She helped me into a lacy bra and inserted the soft and spongy breasts over my natural, boyish ones. Initially,y they felt cold, and then as they warmed up with the heat of my body, all I could feel was the weight of them on my bra-restricted chest.
'It feels funny,'
You'll get used to them. Now slip these panties on.'
I pulled up the silk and lacy panties; they were very, and I mean very, frilly. They felt smooth and silky, just like the robe.
You had better wear these tights to hide that small bulge that's just appeared.
I blushed as I realized that Mr. Percy was perking up.
'Sit on the bed, and I'll show you the best way of putting them on.'
She rolled up one leg and then the other. I stood up and pulled them up past my belly button. I now knew why they were called tights as Mr. Percy subsided and then disappeared out of the way.
'Put your arms up, hun.'
I was on autopilot now, so I did as I was told.
'This is a slip to make sure that your dress doesn't cling to you; it also feels great.'
As I felt the slip slide over my body, I shivered a bit; it was probably the coldness of the fabric; it couldn't have been anything else.
'OK, now step into the dress, and I will zip it up for you.'
I stepped in, and Sheila helped me to pull it up and zip up the back. I must admit, it didn't feel as bad as I thought it would.
'Sit down and try on a pair of my shoes; you look about the same size.' What are you?
'A small six.'
'My, aren't you a dainty toes?'
She crammed my feet into some cream-colored strappy shoes with long, thin heels.
'That looks good; now stand up.
I tried to stand and immediately fell back down on the bed.
'SHIT.'
'Tut, tut, tut, polite girls do not swear.'
'But Sheila, I can't stand up in these things.'
Most girls love to wear these; they make them taller, walk nicely, and they are considered to be sexy. You soon get used to them.'
'I don't want to be sexy, and I don't want to get used to them,' I said as I struggled to stand up again.
Don't fuss; there are only 3-inch heels. You should see some others I've got. Here, let me help you.'
I finally managed to stand up, my ankles wobbling with the strain of it all.
'Well done, now walk across the floor.'
I took one step and nearly fell over. How can I explain? It was like walking on a tightrope without a long bar to help with the balance.
'Here,' said Sheila, 'hold my arm and try to relax a bit as we walk. Don't take big steps; try small ones. That's it, you're getting the hang of it now.'
It was very hard, but despite the strain on my ankles, I started to get used to the strange shoes and the weird way I felt as I took small steps. I'm probably exaggerating, but my hips felt like a pendulum, swaying from side to side as I walked.
'Can I see myself now?'
'OK, let's go look at you in the full-length mirror in the bathroom. Shut your eyes, and I'll lead you.'
I shut my eyes and held on tight to Sheila's hand, not wanting to fall over again.
'Sheila, I said as I tottered into the bathroom with my eyes still shut, 'I don't think this is going to work.'
'Open your eyes, hun.'
I did as I was told and looked at the mirror.
I didn't recognize the person in the mirror. It wasn't me.
Comments
Brianna Demonet
Toni is jumping in to the deep end of the gender pool.
Brett Schuhkraft
Sheila is a great friend Tony/Toni is hooked and so am I Can’t wait to see how things go
