Halloween at Work

By Laura Ellis

Published on Oct 27, 2023

Transgender

Halloween at Work: Part II The saga continues By Laura Ellis

This is a continuation of Halloween at Work, which, by the way, was my first published work, and very vanilla compared to my later offerings. So if you haven't read it yet, take a few minutes and take a look at it first. It is a quick read and will help you understand this better. Again, please remember that this work is mine, and do not re-post without my permission. You can email me at girly_girl_laura_69@yahoo.com with any suggestions, thoughts, or secret little fantasies this story might bring up. So enough chatter, on with the story.

Part II:

I got a sudden uneasy feeling when I hurt Stacey ask me about doing her a favor. Sentences that start out that way never seem to end up good. So I braced myself for the worst. She took me in the office so we could speak privately. What she asked, for some, may have been bad, but for me I secretly loved it.

"Carla isn't going to be back for a few days, possibly a week. This kind of causes a problem for us. You know that meeting of the mall managers Saturday, well she was supposed to go with me, and we are booked as 2 women. Seeing as how the housing is set, and everything, I can't change that now. But the main problem is, the only person I could spare to go with me would be you. I need to ask you a question, Jeff. I saw you here yesterday, and saw how comfortable you were in the role of a woman. You can feel safe telling me the truth since I have known you for a long time. Is that the first time you have dressed as a woman?"

Needless to say, I was a little shocked. I tried to think about how to answer her without revealing my secret. But after a few minutes of stalling, something in my brain told me to just let it all out finally. So, for the next half hour, I related the story of my life to Stacey. I told her of how my sister used to dress me up when we were little. Of sneaking into her room when she was away to try on her things. I told her all about the secret wardrobe I had accumulated over the years. All about the purges, the purchases, and everything else. I also told her how much I really enjoyed dressing like I did yesterday, and feeling accepted for being someone I liked being, with no consequences either way, even making the comment that I happened to be wearing a pair of the panties she bought for me right now, which gave way to a little grin from Stacey.

Well, after all that Stacey said that if I was willing, she would love it if I would go with her to the meeting. It would be our secret for now, but if I wanted others to know, that was up to me. We decided to hold off on that. "Well Jeff, or should I say Laura, I need to get used to that. For being so honest with me, and doing me this favor, I think I owe you. Tonight, when we close, you and I will stay after and get you a wardrobe suitable for an entire weekend entirely as a girl. And just to say thanks, it is all on me. My daddy pays the credit card bill anyway, and he has decided that any purchase made at this store he won't even look at, so that is no problem." After telling her how thankful I was, but avoiding groveling and kissing her feet, I went back to go to work. Needless to say I was rather distracted.

Once closing time rolled around, it was time to go have our fun. Stacey had already let everyone go home, so it was just she and I. It was a little strange being there knowing what we were there for, but I was quite excited. I had been making mental notes all day of things I wanted to try on.

"You ready to get started hot stuff?" Stacey said with a grin and a wink. All I could do was nod my head yes, and try not to faint. After all, this is every TV's dream. Being alone, in a woman's clothing store, with a beautiful woman acting as your personal shopper, and anything you want is free.

"Well, if I am to see you dressed as a girl all weekend, we may as well start now. So there missy, strip to those panties." She said it with force, but in a way that I could tell she was trying to put me at ease, and it was working. I slowly removed my shirt, and pants to reveal the cute purple bikini style panties she had bought for me. "She grinned when she saw them. "Those are very cute on you, but they don't do much to hide your, um, womanhood." I looked down to see I was more aroused by this than I ever knew possible. "You really should take care of that before we get started. Go in the bathroom and do your business. Let me know if you need any help." Again with a wink and a grin.

Well, after what seemed like about 3 seconds I was cleaning myself up. I tucked my now tired self back between my legs, pulled up my panties, and walked back out to meet Stacey. She had already gatherer a bunch of stuff up and had a dressing room full and waiting.

"Feel better now?" she asked. She looked down to see that I had tucked myself back. "Looks good, is it still there?" she said, as she reached out and patted my new little mound. This kind of took me by surprise, but I was definitely not complaining. I had always had a bit of a crush on Stacey, and I think she did a little on me too, but neither of us ever acted upon it. "Yeah, it's still there, just put away for now. Maybe we will have to let "her" out later." I said with a wink. I figured two could play at that little sexual innuendo game. Besides, she started it. Stacey just smiled, "Perhaps we will missy, but you better behave now. Don't make me get all bossy on you." I just looked at her straight faced and said, "Maybe I like it that way." Again, she grinned. Our little verbal joust went on for a few more minutes before we started back to the task at hand.

In the next 2 hours I think I officially tried on 1 of every item in the store. I tried on business attire, seeing as how the meeting was a formal business affair. I tried on skirt suits, and pants suits, and blouses and skirts, and dresses as well. We settled on 2 different suits. One was a black stretch material. It had a short skirt, with a jacket that had a small belt with a buckle that matched the one on the skirt. I wore a lacy white French cuffed blouse underneath, so the collar and cuffs of the blouse showed out over the jacket. Very feminine, yet extremely business like. We also got a grey tweed suit as well. This one had a long calf length skirt, that had black leather trim up one side and around the waist, with a very high slit. It had a matching longer length belted jacket with the same trim that zipped up instead of buttoned. Very sexy, but still business like. I love suits and women's business attire, so I was in heaven trying these on. Stacey noticed this and asked me if I knew why. "I am not really sure. I think it may be more than one reason. I know I have always been turned on by the secretary look. I used to always surf the net and find pictures of secretaries, and I really liked when I found them tied up. Not sure why, just always did. I also think it's because women's suits are patterned after men's wear. Knowing that guys are always supposed to be in a suit, being in a woman's suit seems like the ultimate form of feminine wear to me. Women wearing suits on the outside looking slightly masculine, but knowing on the inside that they are wearing lacy and silky things underneath, that has always turned me on."

"I know what you mean." Said Stacey. "I love the feeling of power that wearing a power suit has over others. Feeling like I am in control of other peoples actions and they listen to everything I say, just seems to be heightened when I am wearing a suit. But knowing that I am all girl underneath, especially when I wear stockings and garters, or a corset underneath, has always made me feel like women have the best of both worlds in that way."

We also bought some casual clothes. I got 2 pairs of jeans. Both extremely flared, one dark rinse, another stonewashed with cute little studs around the pockets. I got belts to go with both. One studded, the other with one of those rhinestone belt buckles that are so in. I bought 2 skirts, and a couple tops to go with them. I got 2 evening outfits. One was a black sequined sleeveless top, with a long slinky skirt to match, the other was an oh-so-short silver skirt with a black lace overlay. I got the matching top as well.

We bought all kinds of lingerie. We bought bra and panty sets, we bought garters and stockings, a corset, and pantyhose. One of the sets we bought was a very pale pink bra and panty set, with thong panties, and matching garter belt. After I tried it on, Stacey said I should leave it on for now, because she liked the look. Adding some stockings and attaching them to the garters we got back to work. Being that there was a formal dinner on Saturday night, I needed a gown. After trying on about 30 or 40, one of the pleasures I have always wanted to experience, we settled on a very light purple spaghetti strapped dress, that tied in the back, but was mostly backless. "I love the dress Stacey, but...um...won't my bra show in back?" I asked. I know most women would go with out one, and just use those stick up things from Fredrick's, but I didn't have anything to stick up. "Don't worry sweetie, I have a surprise for you." She went into her office and returned with a box. Opening it I found 2 extremely lifelike breasts. "Those are my gift to you for helping me out of a jam. Best part is, they come with this stuff here that attaches them to your chest. So that way the built in bra of the dress will hold your 36C boobies just right." She said with a grin. She put them into the bra I was wearing so I could see how they looked on me.

I was speechless, knowing from looking before for them that these would have cost around $250. I just ran over in my dress and gave her a big hug. As she hugged me back I almost started to cry. She held my face in her hands and wiped away the misty eyes I had. As she did this, she was staring into my eyes, and I was staring back into hers. She slowly stroked my cheek with her hands, and before I knew it, I leaned in and kissed her. She held my face very gently, and kissed me back. We kissed softly for a few minutes, and then the kisses started to get hotter and heavier. I ran my hands across her back, and she was grabbing my thong-clad bottom through my dress. We moved backward into the open dressing room, ad collapsed onto the overstuffed chair in there. She was on top of me. She reached down and moved my skirt aside using the slit in it to her full advantage. She reached down and pulled my thong aside to release me from being tucked back between my legs and wrapped her fingers around me. I was in absolute heaven. I felt Stacey slide down to her knees and take me into her mouth. It felt so wonderful. I opened my eyes to realize that because of all the mirrors in the fitting room I could see us from all angles. It was the most incredibly sexy thing I had ever seen. A cute girl in a formal dress sitting there getting head from a gorgeous woman. It was the stuff of dreams, especially mine.

Stacey stopped after a few minutes, leaving me close, but not having had an orgasm yet. She looked up at me and said, "We should get cleaned up and make these purchases. After that would you like to head back to my place? Remember, I like to be the boss."

The look on my face obviously said yes.

To be continued......

If you liked my story, please drop me a line and let me know. I would greatly appreciate any feedback you could give, and always love hearing about others thoughts on my work.

Email me at girly_girl_laura_69@yahoo.com. I love to hear anyone's suggestions, thoughts, fantasies, etc.

Thanks


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