I hesitated to arrive at my
I had been contacted by a firm that wanted a talented, experienced secretary. The candidate had to be a crossdresser & willing to work for a female boss. I'd always wanted a high-paying job where I could wear fine ladies' clothes & be appreciated for it.
I entered the office of Ms. Taylor
& was seated for my interview. She was a tall beautiful red-head, 30 years
old & thin and fully shaped. I was jealous. N eedless to say, I went
en femme, in a nice blue skirt suit with an effeminate semi-sheer blouse &
my laciest camisole to show off. I hoped this would tell her I love pretty
clothes & liked fine lingerie.
She was very pleasant & didn't ask anything about my clothes or femininity - strictly my professional skills. No girl talk. After 20 minutes, she asked if I wanted the job. I said, "Of course." 40K per year. Wow.
Finally she said, "You are pretty & quite feminine.. just right. I'd like you to wear nice dresses to work, high heels only. Underneath, I'd like silk stockings only ,with a garter belt. Your lingerie must be high quality and elegant, something pretty enough to show off. You know." She gave me $1,000 to go shopping. I was floored.
Well, I came to work and everything went perfectly for 3 or 4 weeks. I was very busy, but I was so happy to be dressed so well for work each day. Ms. Taylor would look at me in the morning & say, "Quite nice". You're lovely." I would just beam.
Only once did she ask, "What brand of lingerie do you wear?"
I replied, "I try to wear vintage Van Raalte".
"May I see the hem of your slip, Cynthia?", asked Ms. Taylor.
I pulled up my skirt & showed off the 6" lace hem on my light blue Half-slip. She smiled & we went back to work.
At the close of work, after about 4 weeks, she said to me, "Cynthia, there is something I must tell you about. In my bottom right desk drawer is something I'd like you to see & tell me what you think of it. I went & looked & there it was. A black leather harness & 10" dildo. It was a custom strap-on. I took a very deep breath and went to my seat.
"Well? She asked.
"I do enjoy things like that sometimes, but I have to be ready for it. Would you like to use it on me?"
Ms. Taylor then explained, "Cynthia, you are a lovely girl & work hard. It's not very often I have a chance to give my secretary such a treat. We can do it tomorrow at lunch if you'd like. Here in the office. That sofa will be fine. You don't have to - not all my girls enjoy it."
"Think about it tonight & put a note on my desk in the morning with your decision. OK?? Good night Cynthia."
I went home & my head was swimming. Would she fire me if I said no? Finally I told myself I would do it. It would be OK.
I worried over what to wear. I decided on light pink chiffon for the dress. Tiered skirt & lacy bodice. A fine full satin slip and feminine petticoat, with extensive lace & matching lacy tap panties. It was my most feminine outfit for work. Lace thigh-highs as a special touch.
I arrived early & put the note on her desk before she arrived.
It was a full busy morning & she acted like nothing was going on. I was so nervous; but I concentrated on my typing & shorthand. Finally 1pm came. She came out of her office & said, "Cynthia, you are so kind to do this for me. I hope you enjoy it too". She came over & pecked me on the cheek & smiled. "Give me 5 minutes & come in."
I walked in & the lights were down low. She came out of the bathroom ready for action. She was just in her bra, panties and stockings. She had it on, large and quite intimidating. "Don't be afraid, I'll be very gentle. Go lay over the back of the sofa; pull up your dress. I pulled my dress up & exposed my 3-tiered lacy petticoat of satin & chiffon. It was my loveliest petti.
"Cynthia, what a precious petticoat! So delicate in its layers." She lowered it & exposed my tap pants. "Now these are also so sweet." She pulled them slowly down over my bottom & they dropped to my ankles. "You do have nice taste in underthings, Van Raalte is very good."
"I'm going to lubricate you first with my finger. It will go in easier. Do you like french ticklers Cynthia? I have a nice one to put on if you'd like?"
"Yes, please," I said.
"You are a darling sweet
girl," she said.
Needless to say, her session started quickly after she slid my satin panties down to my ankles. It lasted maybe 3 minutes. I was glad when it was over. She pulled up my panties & stood me up.
"Feel better?" she asked. She panted my bottom and said, I" hope you aren't sore!!"
I said, "No, it was just right. I hope I didn't wiggle too much."
She said I could take the rest of the day off as a treat.
Next morning, all was back to normal.
I worked for her for 5 more years & never once did she ask to use it on me again.
I did ask a year later if she'd like to have another session.
"Cynthia," she said, smiling pleasantly, "you really must find a man to do that for you. I've got 3 sissy maids to take care of at home & that is quite enough. That one time showed me that you an obedient & cooperative secretary. Just the perfect working girl.
Back to typing I went, saddened but relieved, it was somewhat uncomfortable, really.
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