Caught By My Assistant Emily Ch. 02

CAUGHT BY MY ASSISTANT EMILY -- chapter 2

by: cdCindy1

What happens after my assistant finds out about my secret gay sissy CD life.

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Author's Note: A couple of months ago, my assistant Emily confronted me about my secret sexual activities after hearing me say my "Daily Affirmations". Read Chapter 1 for all the details of what happened when she confronted me and I confessed to her about my secret sissy life. As I said about the first chapter, this story is almost 100% true with only some minor details different (names have been changed to protect the girls). If the readers want me to, I will write a third chapter to let you know what happened next.

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After my beautiful young assistant Emily found out about my secret sissy life, she left me mostly alone for a week, just smiling at me when seeing me at the office. Her best friend and co-worker, Shelly, also had a big smile on her face when she saw me and said "Hi Dave" very flirtatious-like. I assumed that Emily had already told her my secret. Emily had said that she would only tell Shelly and no one else about my secret. They are best friends and Emily knew that she wouldn't be able to keep such a fabulous interesting secret from her best friend. She assured me that no one else in the office would find out and she would make sure that my wife never knew about my secret sissy life. It would only be Emily and Shelly. That's the way she wanted it and we had agreed that we would get together -- the 3 of us -- and have some fun with my secret. What exactly she had in mind, I didn't know, but I was certainly looking forward to finding out.

A week later, on Friday afternoon when everyone had left the office early (as they do every Friday), I was alone in my office and was able to masturbate to my various porn videos without interruption. This is something I do regularly on Fridays, which is something Emily found out when she caught me. I had a wonderful session, in private, jerking off to my favorite CD and sissy videos. The following Monday, Emily came into my office and told me that we are going to have a session (me & her) the next Friday after everyone had left work. She wanted me to wear all my lingerie to work under my male clothes -- panties, nylons and bra. She suggested a dark color bra underneath a black t-shirt and a dark dress shirt, so that no one else in the office would be able to see it. I found myself with an erection when she told me this because I knew it was something I wanted to happen. Emily is such a beautiful sexy woman and I couldn't wait to have a "session" with her. She noticed my erection and said "I hope your pink panties can keep that down so no one else will know what's happening." Frankly, since she and Shelly already knew about my secret sissy life, I didn't mind a bit of exhibitionism but I did agree with her that no one else should find out about our secret sessions.

That Friday morning I was careful to put on my black fishnet nylons, pink panties and black lacy bra underneath my dark male clothes, without my wife watching. When I looked in the mirror I got an erection thinking that no one in the office, except Emily and Shelly, would know what I was wearing underneath my male clothes. I was thinking how exciting it is to be a secret sissy crossdresser, as some Literotica readers already know. At 4:15 pm that day, after everyone had already left the office, Emily buzzed me and told me that I had better be ready for her. She was just outside my office door and I was to open it wearing only my sexy lingerie. I did as she instructed me to do.

Previously, I had only taken off my male clothes while sitting behind my desk jerking off to CD and sissy porn. But that day, opening the door to my work assistant, not knowing for sure 100% that she was the only person left at the office, was nerve-racking but also very exciting. It turns out that she was the only person standing there, in her low cut tight top which showcased her fantastic boobs and her short tight skirt which accentuated her sexy legs. In that moment I was actually a little bit disappointed that no one else was there. I guess my secret exhibitionism was making me wish the entire office knew that I'm a sissy faggot crossdresser. Oh well, maybe another day. I know that right now I can't let anyone else find out about my secret life (other than Emily and Shelly) but that week I had started having dreams of everyone finding out, including my wife. When I opened the door to see just Emily standing there, I realized that I was in the best situation at this time. I know that she and Shelly will keep my sissy life secret and I was looking forward to finding out what they had in store for me, as the 3 of us would together explore the boundaries of my secret sissy life.

Emily walked into my office with a big smile on her face. "Good sissy, you wore your sexy fishnet nylons, the pink panties I like and the black bra I suggested. Did anyone at the office figure out what you were wearing under your male clothes today?"

I responded, "No, I don't think anyone could tell -- except for Shelly. She gave me a big sexy smile every time I passed her in the hallway today. It was a wonderful feeling realizing that she knew what I was wearing underneath my male clothes. By the way, since you've obviously already told her about me, why is she not here today?"

"She couldn't change an appointment she had scheduled this afternoon but she did say that she's very much looking forward to the 3 of us having another 'after-work session' next Friday." That got me hard -- Emily noticed and I immediately became embarrassed at the small bulge in the front of my panties. "Don't worry about that. I think it's cute that you get hard in front of me. Now, let's get started, shall we?"

I went behind my desk and showed her the sissy porn video I had been watching and she said that hopefully one day we can make me look as pretty as the sissy in the video. That made me feel so good knowing that Emily was interested in helping me become the best sissy I can be.

I was beginning to think that her finding out about my secret might be the best thing that could ever happen to me.

"Before we go any further, I want you to do a lap dance for me. I want you to be the most feminine you can be and put all of your sissy self into it. I want to see how feminine you really are so that I'll know how much work we need to do to get you to be the sissiest faggot crossdresser in town." I wiggled my ass as sexy as I could and I gave Emily the best lap dance I could possiby do. She said I did a good job and my dancing really turned her on. I was down to my panties, nylons and bra when she turned me around, grabbed my ass and then rubbed up & down my asscrack. I started to moan and she giggled, saying "you are such a bottom bitch aren't you". She then told me to masturbate to the porn video. I pulled my panties down and stroked my thin pencil dick while she was standing beside me watching the video. I then noticed that she had started rubbing her nipple on one breast with one hand and had put her other hand inside her pants, deep into her panties. This turned me on so much that I shot my load of cum into my coffee mug. She said "good sissy, now drink all your cum like a good sissy cumslut". I put the coffee mug up to my lips and drank all of my cum; it was delicious. "That was hot, watching you jerk off and then eating your own cum. Wait until Shelly sees this. She's gonna be so horny." Emily said she was going to make sure Shelly joined us the next time we got together. That's going to be so much sexy fun.

The next Friday afternoon Emily left me alone to masturbate to my gay and cuckold porn while dressed in my nylons, panties and bra. The following Friday, however, both Emily and Shelly came to my office after everyone had left. They said that they were in the mood to watch their sissy faggot boss jerk off to sissy porn. First, they wanted me to say my Daily Affirmations, especially "I"m a Sissy Girl". After saying all 3 of my Daily Affirmations out loud, I noticed that Emily and Shelly had started playing with each other. While I had started jerking off to the CD, sissy & gay porn that I was watching, Shelly was rubbing Emily's tits & Emily had her hand under Shelly's skirt rubbing her panties. I think they both had an orgasm while watching me jerk off. I decided to give them an even better show when I shot my sticky cum into my coffee mug and then drank all of it while they watched. They both said it really turned them on to see me drink my own cum. I asked them if this was the 1^st time they've played with each other sexually. Emily responded by telling me that I would find out later but I needed to earn it first. I got another pencil dick hard-on just thinking about what they would tell me. I was also wondering what she meant by "I had to earn it". I'm sure it's going to be fun, whatever it is she orders me to do.

A few days later, Emily told me that she and Shelly were getting things organized, booking off one of the Fridays so they would have the entire day free, and then planning what we're going to do that day. She said that I would have to be able to get away from the office all afternoon. We discussed our work schedules and decided that the next Friday was good. I asked her what she was planning but of course she wouldn't tell me. That made my pencil dick even harder inside my panties. It's such a good feeling when that happens.

A couple of days before the Friday we had scheduled for our 'sissy play date', Emily "ordered" me to make sure I wear my pink panties, my black fishnet nylons and also my red lacy bra. She said I should wear a dark t-shirt and a red long-sleeve shirt over top to hide the red bra. She and Shelly will have the full day off and I am to leave at lunch time, making sure that I have "appointments" outside the office all afternoon. She gave me her address and I'm to go to her place, which is only about a 5 minute drive from our office. She said we would have some sandwiches at her place before we started our "play day" (so I didn't need to bring a lunch to work that day). Again she wouldn't tell me what we're going to do. She just smiled her wicked smile and said "I'm sure you'll enjoy it". I was wondering if we were going to go shopping for shoes & dresses, or do make-up, or maybe just stay at her place and watch sissy, CD and gay videos all afternoon. Maybe I would even get to see Emily and Shelly play with each other again and find out how that came to be. Whatever we were going to do, I was so excited when she was telling me the plans that I had to excuse myself, go to the washroom, and jerk off. I couldn't wait until everyone had left the office.

Later that day, I was sitting in my office watching a sissy porn, saying my 3 Daily Affirmations (I say them every day). I was so looking forward to next Friday and I started to realize that I am now under Emily's complete control. It was such a good feeling.

In case anyone is wondering, my Daily Affirmations are:

DAILY AFFIRMATION (from the Church of Cock)

I will find a cock today and I will worship it.

I will take it into my mouth and feel the warmth on my tongue.

I will feel the cum flow down my throat, over my body, into my mind and my soul.

I will drink the cum freely and experience true bliss.

COCK IS MY UNIVERSE (from the Church of Cock)

Cock is my universe.

To take cock into my mouth or into my body is to let the universe exist within me.

It is my sole purpose in life. I crave cock. I need cock.

I want to be a cum dumpster. I want cum in my mouth. I want cum on my face.

I need to have a cock in my mouth. No matter where I am, I crave the taste of cock.

Being a cocksucker is my purpose in life.

Cum sustains me. Cock is life and cum is bliss.

SISSY AFFIRMATION (inspired by Mistress Constance)

I'm a sissy girl. I love to wear panties and sexy clothes.

I'm a sissy girl. I love to be a girly girl, so soft and sexy and pretty. I love to be dressed in my favorite pink panties, my black fishnet nylons, my favorite red lacy bra, pink babydoll, and sexy high heels.

I'm a sissy girl. I'm not a real man. I want to look and feel like a woman.

I'm a sissy girl. I have a pencil dick -- no, I have a pencil "clitty". Hee hee hee

I'm a sissy girl. My lips were made to be covered in lipstick and my mouth was made to be filled with a big juicy cock.

I'm a sissy girl. I love to give myself to a man, fully & completely. To have a man make love to me.

I'm a sissy girl. My wife needs to know.