Elaine had been my secretary before her promotion. After a few months when it became obvious to her that I was a closet sissy, she changed. Not in a way that was apparent to other people in the office. Just to me. And once she changed, she made sure that my life changed forever.
I dropped a few hints that I was fascinated with the idea of role reversal and female clothes. Instead of her getting me coffee, I started to get her a tea and muffin each morning. Instead of her making copies of documents for me and running errands for me, I made runs to the drug store downstairs to buy her pantyhose and gum, and I took her stuff to the copy machine and left copies on her desk. A few times I left little notes in red ink, saying it was a pleasure to serve the Mistress. She would read them and smile. And I would almost curtsey to her delight.
Then she started to get kind of brash around me. She got into the habit of going into my office when I went to lunch and closing the door and making personal phone calls to her boyfriend. I would wait for her to get office the phone, sometimes for an hour after I got back. She rarely did the work I asked her to do. I decided that she was taking advantage and it had to stop. I told her that I wanted to have a serious talk with her. I decided not to have any contact with her all morning so that I would not let my sissy weak side get the better of me and talk to her after I came back from lunch. I then would put her in her place, gently.
When I got back from lunch she was nowhere to be found. But there was a pink shopping bag on my chair and a gift-wrapped box inside. I knew she had left it there and I should have taken the bag and gift and put it on her chair unwrapped. That would have been the wise thing to do. But I felt the butterfly flutter in my tummy and my sissy thingy began to throb. So, I locked my door and closed the blinds and opened Elaine's gift.
It was a flowing silky top and tap pants. Sheer chiffon. Lilac and cream colored. And inside the box there were pictures of Elaine wearing the very same outfit kissing and sucking an incredibly sexy, naked guy. Her boyfriend. His hard cock was in clear sight. Five pictures, all showing off the outfit and sexy Elaine serving him.
My hands shook and I touched and explored the tap pants. As I held them, a little note fluttered out into my lap. It said, “Sissy, these are for you. Smell them and then put them on, sis, they are unwashed.” I sat there for 15 minutes touching myself, looking at the clothes, looking at the pictures, looking at the note, looking at his cock, re-reading the note.
I had to put the tap pants on. I had to. My pants thrown under my desk. My boy underwear in my drawer. The soft pants fit snug. I could feel the stickiness of her cum under my balls. Or was it his cum. I was incapable of thinking. I wanted to stay in her soft tap pants all day. Just staring at my computer screen and feeling so totally femmy. I noticed that I had just gotten an email and it was from her.“Do they fit? I bet you look so sexy, don’t you sissy?” It shocked me that she would send that kind of email at the office. Then another --- “Open the door, silly one. You said we needed to talk. I agree. Open up now!!!”
How could I not obey? I unlocked and she hurried in and relocked the door. She smiled when she saw how weak I looked, and she told me to put on the top. And I did. She told me to twirl around for her and I did. She sat down in my chair and pointed to a spot on the floor and I sat. She asked me if I knew that the tap pants were filled with her and her boyfriendÕs cum. I said I thought so. She asked me if I got turned on seeing his cock and I said yes. She told me that she expected me to wear her things and that she knew that I was too weak to fight the feelings.
So once a week, she would leave a gift for me and I would change in my office and she would watch me twirl. Along with each outfit was a set of pictures and a note Ð sometimes from her and sometimes from him. All the while, I slowly drifted into the deep craving --for her, for the clothes, for the sense that he was preparing each outfit by having sex with Elaine the night before. She liked to talk about her career during those moments in my office. She was eager to understand what I did and how to learn how the business operated. We talked about her career and I started to show her how to draw up plans and run calculations and manage projects. She was a fast learner. Sometimes she put lipstick on me to bring out my sissiness even more. Sometimes she made me say I was a pretty little faggot and that I wanted to suck Raul in the worst way.
Last month she got me a little tunic like hairdresser wear and matching white stretch pants. And she convinced me to enroll in a beauty class at Leroi Institute which as a few blocks away from our building. At first I though she was joking but that evening, Sir showed up and Elaine and Sir walked me over to Leroi to make the 6:15 class. I did not want to be seen walking into the beauty studio. But it was not my decision. She explained to me that she and Raul (Sir) had been talking about me for weeks and they both decided that I deserved a little gift from both of them. A semester of evening classes at Leroi, in return for showing Elaine more and more of what I do.
At first the Leroi training was frightening. There were only three others in the class. Two young Philippine girls probably in their late teens, one middle age African American guy, obviously gay. The beauty instructor was a young woman in her 30s with too much make-up. She told us that we had a future as hair and skin stylists. I wanted to run away but Sir grabbed my by my tunic and explained that this was a gift from Elaine. So I stayed for the whole semester. Each week, I found myself slipping into sissy trace, and instead of looking down at the other students, I found myself identifying with them and stated to socialize with the other man in the class Ð Rodney. Yes he was gay, but we like the same things and I found myself admiring his open sexuality. While my sexuality made me feel weak, he seem proud of his sexual preferences and I felt safe being around him. The girls giggled at my outfit and maybe at my new friendship with Rodney, but they were cute and sweet. They wore tiny tee shirts and jeans and looked so sexy and girlish.
We practiced doing hair on each other and Ren, one of the girls, cut my hair in bangs that I could comb back when I was at the office. The other girl, Nina, showed me how I looked in lip gloss and I decide to wear light make-up each time I was in class. No one minded. Rodney was not into feminine outfits but always complimented how I looked. At first, I admit that found him annoying, and I felt superior to him. But when I started to cut his hair and I give his manicures we talked quite a bit. I realized he was an interesting and warm-hearted soul.
By the end of the semester, I was able to do ElaineÕs and SirÕs hair, give them facials and do their nails. It was thrilling and I simply stopped caring about my day job! And on the weekends I found myself running errands for Elaine and meeting Rodney for a movie or dinner. Of course we were simply close friends, but we both knew that there was a sexual attraction, and he was perfectly OK with me dressing feminine when we were at his apartment or mine. I would wear outfits that Elaine bought me and Rodney would rent a movie and buy a bottle of wine and we would stay in on Friday and Saturday evenings. If it was too late to get home safely, he would convince me to sleep over and over time I guess we decided it was kind of a steady thing. I gave up my apartment when the lease was up so we both could save some money.
Well that was months ago. Since then ElaineÕs career has taken off. She got the hang of my job. As she always said, if a weak and femmy guy can do it, then she could do it much better. Last month, Elaine was promoted to a job similar to mine. My job was phased out after management approved a restructure plan that I wrote, with some help from Raul. Elaine and Raul are married and I still do their hair.
Both Rodney and I decided it was OK to work at the same boutique even though we are living together. He does my hair and nails and I guess I am sissy most of the time. He expects it now. I still think of Elaine as my Mistress but I know she is too busy to think of me that way anymore and Rodney and I are saving up for our own shop in Ft Lauderdale one day.