The First Time Out: lunch with Shelly

The First Time Out: lunch with Shelly Fantasy/Fiction ©2025 Amanda_Cd_Slut This is a work of fiction. Names, characters, businesses, places, and incidents are either the product of the author's imagination or are used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental.

Monday and Tuesday were pretty brutal at work, lots of deliveries to make before the expected rain on Wednesday and we put in some long days to get everything done. I arrived home at dark Tuesday evening and work had been called off for the next two days already. Happy for the time off, but exhausted from the long hard days, I grabbed a bottle of beer and headed for the tub. No real plans, but I wanted to let Amanda out on my days off. I shook my hair out and poured the other half bottle of bubble bath into the running water. Sinking down and sipping on the beer to relax for a bit. After a good cleaning out and shaved completely smooth from head to toe, I went to Amanda's bedroom with another beer in hand to curl my hair and put on a little makeup. Just my breastplate with bra and panty set, I pulled on another silky smooth gown and crawled in her bed to sleep for the night. Before I fell asleep I got a message from Shelly, asking if I was off tomorrow and when I said that I was, she said to meet her for lunch at a local restaurant that was usually busy. I said I would be there and she messaged back saying "no, I want Amanda there", laughing emoji sent back with the message "I don't think she's ready for that". A couple of minutes later I got another message from her with video attached. I clicked on it and nearly fainted as I saw me giving Greg head while sitting on the toilet dressed as Amanda.

The next message asked if she was ready now, I responded with "Amanda said she will be there" the last thing I got from her was, "make sure she is dressed pretty!" I just said "ok" before going to sleep in the exquisite feeling pink satin sheets. I had to get up early in order to get "Amanda" ready for lunch at noon with Shelly. Shower, shave my face and fix my hair again, the painstakingly hard makeup to try and fool people without the comfort of a mask to hide behind. Black lingerie set since it was raining and would show less if I got wet. The breastplate smoothed out perfectly so nobody could tell it was on and the flat inverted chastity device to keep my secret hidden. This time I used the black straps instead of the pink ones to match my panties. I chose an emerald green dress with long sleeves to hide my dry elbows and scratched up from work arms. Choosing some low heel emerald green pumps that matched the dress, pink press on nails and lipstick this time and I was ready to go. Looking at my reflection in the full length mirror I kept thinking something was missing, finally realizing that I needed some jewelry to break up the patches of exposed skin, I chose a fake pearl necklace and bracelet combo that looked good but not too fancy for a lunch date with a friend.

A message from Shelly said "forty five minutes dear" and I grabbed a pair of ladies sunglasses and my regular purse with identification, cigarettes, phone and a pink raincoat over my dress. Umbrella was in the car already and I had to get going or risk being late and whatever she decided to do with that damn video. Shelly was already in the restaurant and had a booth in a back corner, I hung my raincoat and umbrella in the entryway and with my sunglasses still on I strode through the crowded eating place to find her. There was so many people there that I know and I was sweating bullets that someone would recognize me and call me out. Fortunately nobody did and I found Shelly in a corner booth waiting for my arrival. She jumped up and hugged me before insisting that I set beside her and started grilling me about my weekend with Greg. Not just the regular "we hooked up yeah" she wanted details and wouldn't stop until I was spewing them like a woman. We would get quiet when someone was close to us and whispered a lot, but it was followed by loud giggling from us both.

I asked her for the video and she told me no way, it had become her girlfriends favorite porn to get in the mood with and plus she wanted some leverage on me for a while. I blushed and pleaded with her for the video or at least to destroy it. The kind of work things I done would be horrible if it got out. She told me she had an idea about that, but would tell me about it later. I knew she was scheming up something but had no idea what yet. Going on to ask if I was going to see Greg again, I said I hoped so but hadn't heard from him yet. She insisted that I message him and see if he wanted to come over since I was already fixed up and off work the next day. Insistant that I do it where she could see the message. Reluctantly I sent him a message saying hello and asked how he was doing. He replied "good but missing you babygurl", that got Shelly fired up and she made me take a selfie with her and send it to him saying that I missed him too and I was off work the next day if he wanted to do something later this evening. He sent a pic back of him shirtless and working out in a gym somewhere, with the message asking "your place at seven?" Answering on my own for once I said "that's perfect sexy, looking good lover" and sent it without thinking about it. Shelly was tickled pink with my response.

We finished lunch and she wanted me to go to the mall with her and wasn't taking no for an answer. I finally agreed to her seemingly whimsical demands and we headed there in her car leaving mine at the restaurant. First stop was a clothing store and we browsed through several racks of all kinds of clothes. I was mesmerized however when I spotted a gorgeous baby blue dress with a high ruffled neckline and crystal bow, it had four layer, sheer long sleeves with ruffles, and an embroidered sequin bodice with shoulder frills. Shelly saw how I was transfixed on the gorgeous dress and decided I needed to try it on. I tried, but there was no use arguing with her as she had already called a sales lady over. Pulling me along towards a changing room she went in with me and started helping unzip the dress I had on just like we had been girlfriends our whole life or something. I wasn't comfortable with it at first but quickly realized it was futile to resist her. The first one was much too tight and she asked for another size, the second one was a perfect fit and I felt like a princess wearing it. Shelly wasn't pleased however and made me sit down until she got back. Leaving me alone for what seemed like forever, I was beginning to think she had left me.

When she finally came back to the dressing room and I let her in, she was carrying a bag from another shop whose name I didn't recognize. In her usual hurried manner she tells me to strip, I waited for her to turn around or something but she just said it again more firmly "I said strip!" I took the dress off thinking that is what she meant, hanging it carefully on the hanger. But I quickly discovered she meant completely strip as she started unsnapping things and helping me take everything off, including the flat chastity device. I was bright red with embarrassment but she didn't even blink as she told me to sit back with my legs spread wide. By now I was just doing what she told me to without argument. Down on her knees between my legs she pulled the catheter out of my shriveled penis and stretched it out by grasping the head. I felt something smooth and silky wrapped around it and then it snapped suddenly like a rubber band. Not painful, but definitely uncomfortable for a few seconds, next she pulled out a tube of something and smeared it on whatever she had in her hand that I couldn't see. Tucking my testicles inside the soft contraption before pushing it tightly against my pelvis and adjusted it slightly before holding it perfectly still for a couple of minutes.

When she was done holding it I felt her finger tickling my sensitive head and gasped sharply as my penis decided to get a little erect, but it couldn't find room to grow. Looking down between my legs I saw what looked like an actual vagina, but it was some kind of synthetic almost silicone material, very realistic feeling to the touch. Dragging my finger between the smooth lips I could feel the tip of my penis at the top where a clitoris would normally be located. Shelly was pleased with the results and smiled as I discovered my new "pussy". I told her how nice it looked, much better than the flat device with straps everywhere. She wasn't finished yet and with my corset top removed, she brought two super realistic breasts from the bag before smearing the same adhesive on them and sticking them on my bare chest and holding them tightly for a few minutes. I asked about the adhesive and how long before it would need replacement, she had a mischievous grin on her face and told me that it wouldn't come off under any circumstances for a week.

I panicked and exclaimed rather loudly "A Week? But I have to go to work before then Shelly!" She didn't like my tone and grabbed my face and told me not to talk to her that way again and I could miss work for a week at least. I nodded yes and apologized for snapping at her, she said it was alright just this one time, but I needed to trust her from now on. I knew she would never put me in harms way and I did trust her, so I agreed to behave and let her have her way. That made her smile and she stuck her head out the dressing room door and spoke to the sales lady. The lady returned a few minutes later with a gorgeous strapless bra and panty set in a sort of dusty rose, almost pink color and some chunky heeled shoes the same color with ankle straps. The bra and panty set were silk with a little lace around the top edge. They both felt amazing against my smooth skin and it excited me to the point I almost got an erection, but it was thwarted by the chastity device I was wearing between my legs. The best part was looking down to see that smooth mound filling the crotch of the panties.

Next came the chunky heeled shoes that she strapped around my ankles and made me stand up in. Walking around the small dressing room they felt very comfortable. Shelly made a comment about my toenails needing worked on as they stuck through the open toe designed shoes. She helped me put the dress back on and stood back to inspect her handywork. Pleased with herself she threw all my stuff in the bag and opened the door telling me to follow her. Suddenly turning back around she pushed me back inside the small room and locked the door. I was confused to why until she told me to turn around and bend over the seat. I was definitely confused now but did as I was told without question again. I heard her rummage through the bag before leaning over to show me what she forgot. Telling me to be quiet while she puts it in, and scolded me for not already wearing one. It was a stainless steel butt plug with a heart shaped stopper that had a baby blue stone inside, but the plug part was bigger than the big vibrating one I had and I knew it was going to stretch my tight sissy hole a lot. She stuck it in her mouth to warm it before applying just a dab of lube, with my panties pulled down she held my cheeks apart and slowly pushed the huge steel wedge shaped head in my ass. Twisting it around to straighten it she pulled my panties up and we walked out of the dressing room.

To be truthful, Shelly walked and I waddled with the huge plug stretching my ass out uncomfortably. She slapped my butt and told me to walk like a lady as we went to the cashier's station with the sales lady. Shelly thought as we were checking out and had the lady get three more of the bra and panty sets, same size but in white, light pink and baby blue as well as a clutch that matched the dress. Transferring my license, credit card that she used to pay for everything, phone and cigarettes right there on the counter before throwing my purse in the bag as well. I felt extremely vulnerable walking out of the dress shop with the huge plug in my butt and my legs bare for the whole world to see. The dress was short as well and showed my panties when I would move certain ways. The chunky heeled open toe shoes felt fantastic on my feet though, better than anything I had at home in my collection. I thought we were probably done until she started dragging me towards another shop I didn't recognize. I was mortified when she pulled the door open and I saw it was a salon for women and there were several ladies in there already.