Becoming a Bridesmaid Pt. 02

Story Info
Ashley takes the role of bridesmaid for a wedding.
7.1k words
4.65
52.4k
67

Part 2 of the 2 part series

Updated 06/10/2023
Created 06/24/2021
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Later that evening I was sitting in my corset dress and stockings chatting with Ellie. She couldn't stop asking me questions, she could barely contain herself with excitement.

I was caught up in her excitement too for a while, I mean, I was excited to try all these outfits on. I could have changed out of this dress, but I was loving it every time I glimpsed my reflection, or even just looked down towards my waist.

Though some questions made me pause and worry sometimes. I was mostly enjoying myself, but it had all happened so quickly and in the moment, what about the long term? I didn't have too many friends outside of Ellie and Jessica, and I guess now Lou, and my boss, Miss Julie. But what about the people I saw at the gym? The coffee shop? Would I keep going now? Would they recognise me?

But I played along with Ellie, and we had a fun night. Her enthusiasm always pulled me along.

Once we finished, I returned to bed, and was about to head to sleep after such a hectic day. Though I have to admit, before I fell asleep, I started to think of Miss Julie, my clit started to strain in my cage. I got frustrated, and whilst I tried not to at first, I messaged Lou to see what time I could see her tomorrow. She said she had some toys, so maybe she would let me out for a while.

*

The next day, I started browsing my new clothes, unsure where to start. I pulled open my lingerie drawer, and was overwhelmed by the choice. A red lace thong and matching bra caught my eye, so I pulled them out. They were quite well worn, but Julie did tell me that, so I pulled them on. The thong sat very high on the wait, really accentuating my butt, and the bra fit snug around my chest. The breast forms that Julie placed in my drawer fit perfectly.

Next, I realised I had no 'easy' choices, no jeans or t-shirts were left after Julie cleared them out. I flicked through my dresses, and saw a skirt/blazer combo that stuck out. It was pink chequered, a short skirt and matching blazer ('Clueless' style, but pink). There were no t-shirts to wear under the blazer, but Julie packed me a few strappy vests, I chose a plain cream one, and put the outfit together. I finished off with some white ankle socks with frilly ruffles to go with my black Mary Jane heels. If i'm going out as a girl, why not go for it?!

With my blonde wig on, I headed out to Lou's. I was nervous knocking on the door, but felt amazing as her eyebrows raised when she opened the door.

"Wow! Ashley?!"

"Yeah..." I was blushing, but satisfied.

"Come in, you look amazing!"

I caught Lou up on what had gone on yesterday (conveniently leaving out me pulling down Julie's stockings, or that my lingerie and nightwear were all well worn by her), and she was suitably impressed. She kept praising me and I felt like I was floating on air.

Though, I reminded myself of the main reason for being here.

"But... one thing I have been struggling with..." I danced around the topic.

"Your clit?"

"Yeah..." I looked down and blushed. Doing so I caught sight of the key around Lou's ankle.

"That's okay, don't worry, it must all be so new. I can guide you through, what else are friends for?"

I looked up and smiled at Lou. I instinctively went down towards her ankle to undo the bracelet and grab the key.

"What are you...? Oh! Haha, no, don't be silly. I have much better things for you, you just need to know what it means to have a clit. One sec." as Lou headed out the room.

I was confused for a moment, and then Lou returned with a pink box, around the size of a shoebox.

"Okay, you have a lot to catch up on." as she pulled the lid off the box. "Firstly, okay, this stuff can be amazing, but you have to understand that it won't compare to the real thing. You look amazing though, so you won't struggle, but if you ever need someone, I know some guys who would be totally up for spending some time with you."

"Wha..." my head was rushing.

Lou pulled out a big electronic item, with a large dome at the top, "This is a wand, it's for your clit. Start gentle, but push it up against your clit and it feels amazing," then she pulled out a largely realistic looking dildo, "And this is for your pussy, best thing next to the real thing!"

Finally, she pulled out three smaller items, part of a set, but increasing in size, "These are butt plugs, and they can feel great too, it will help you train your pussy too."

I was shocked, I expected to be released, even just for a short while. I mean, I liked that the chastity helped keep my clit tucked in my panties, but I just wanted that sexual release. "Thanks Lou, but, I think maybe if I could just have the key then..."

"Come on, at least try it, until the wedding? For me?"

"I..."

"Look, I have to head out for a bit now. Take this and just give it a try. I'll make sure I knock before I come back." Lou said as she thrust the box into my hands.

I decided I couldn't say no to Lou, and just sat still as she left, cradling the box in my arms. She dashed around, grabbing her bag, ready to leave.

"Oh, I almost forgot, here." Lou quickly passed me a magazine, on the front it had a ripped guy in just tight boxers, a huge bulge on display. Before I could protest, Lou had gone.

I was confused, but also desperate. I started with the wand, and tried how it felt. Not bothering even taking my skirt or panties off, I placed the head of the wand against my caged clit and turned it on. The feeling was definitely there, I felt a real tingle, it was so different.

Those initial tingles made me crave more, so I started trying everything Lou suggested. Before I knew it, I had my panties down, and was applying lube to the realistic dildo. I even admit, whilst I found myself starting by thinking of Miss Julie, I did end up flicking curiously through the magazine to see what worked for me.

The next thing I knew, there was a knocking on the door, how long had it been?! I looked at my phone, it had been nearly two hours. I was completely consumed, I snapped myself out of it and pulled up my skirt and panties. As I was making myself presentable, I noticed a wet patch in the red panties, I guess I had some success!

"How was it?" Lou greeted me.

"Well... actually..."

"See!"

"No, it was good, I admit, but, still, it isn't the same. I don't feel... finished."

"Haha, well, you'll get there. It's different for everyone, some find it harder than others. But remember what I said, the real thing is the next level, I can make it happen for you."

Lou winked at me. I was about to tell her that I wouldn't be interested, but then my mind flicked to those magazine pictures, and I paused for a second, I just let out a non-committal laugh and blushed a little.

***

Before I talk about the wedding day, I have to share how I was feeling and what I went through in the build up.

After the visit to Lou's, I ended up spending a lot of time in my bedroom with her toys, trying and failing to feel a true 'release'. As I sat there, using all combinations of the wand and dildo, I have to say it felt amazing, but I never got that 'finish' that I felt before my clit was locked up. Whilst I tried watching a lot of videos, and thinking about a lot of things as well, I have to admit that my eyes did fall upon the magazine Lou provided quite frequently. There was a centre-fold image of a guy that I found myself a little obsessed by, he was in tight white boxers with a clearly large package barely concealed, ripped abs glistening above. What was happening to me?!

At the same time as these frustrations, I also had my first weekend working for Miss Julie in her store. On the Friday evening I received a text message: Black studded thong, matching bra and garter with sheer stockings. Tight red bodycon miniskirt with slit, leopard print blouse, thin black stilettos. 8am.

I woke at 6am the following morning, wanting to spend 90 minutes making sure I looked my best for Miss Julie. I went through my daily morning shower, shaving and moisturising routine, then put on the lingerie set before applying my make-up. The thong rose high at the backs and had metallic studs on the thick strap around my hips, the bra also had the same studs on the straps over the shoulders. It took me a while to work out exactly how to get the garter on, and then attach the straps to my stockings, but I managed to work it out.

I was conscious of the time, but before I dashed off, I had to spend a while admiring myself in the mirror. I loved how I looked, both sexy and professional, with the feeling of the garter hidden beneath my tight red skirt only adding to the feeling. I noticed as I turned to admire the way my butt stuck out, tightly hugged by my red skirt, that the studded straps around my hips were slightly visible, as were the bra straps beneath my leopard print blouse despite the ruffles around the collar, plunging towards my cleavage.

I arrived 5 minutes early, just about managing to totter on my heels to the door, and Miss Julie greeted me at the entrance. She ran me through what I needed to do for the opening, cleaning the floors, putting out new stock and telling me the other things I would need to do on my own in future weeks. As I was moving around the store, getting more confident but still shaky in my stilettos, I started to feel the nerves hit me about dealing with customers all day. Would they notice me? Would they say something?

Thankfully I had an easy first couple of hours after the store opened. We only had a couple of customers, one was a regular who Miss Julie dealt with, another browsed for a while and left. Into the afternoon it got a little more busy, but everybody was really nice, thanking me if I went to check some other sizes for them or for helping them at the checkout. One customer even complimented me on my outfit, I was really starting to feel at home.

Men were fewer and further between in the store, and normally just casually browsed the vintage section or quickly grabbed something in the store. However later in the afternoon one did call me over. He was tall, probably early 40s, with dark hair and a thick but well maintained beard. The store was quieter at that point, and he asked me if I could find a pair of shoes in a larger size. I found this strange as the shoes were all on display on the bottom shelf, but I didn't want to cause a fuss, I tried to get between him to bend down and look through the other shoes, but he didn't give me much space. After shuffling around for a moment, I could sense he wasn't going to move and decided to bend down for the shoes anyway, careful to make sure my miniskirt didn't ride up. As I bent down, he moved in closer and I felt him rub up against my butt. I was shocked and felt my face go red, I quickly found the right size and handed it to him. Thankfully, the situation calmed down and he bought the pair of shoes, thanking me, and even saying to Miss Julie how helpful I was at the checkout. I thought that I should feel uncomfortable, but I couldn't help my mind flashing to my toys and the magazine... did I like that?

The rest of my first day was much less eventful, but Miss Julie gave me a lot of praise. I felt really accomplished and proud of myself, growing more and more confident in my new life.

One thing that I did not expect was my orders for the following day. I wasn't surprised by Miss Julie's list for my outfit the next day (pink gingham mini-pinafore dress, white crop-top underneath, white knee-high socks with pink bows and pink kitten heels, with my white cotton bra and panties set). However, she did tell me to arrive at the same time (8am) even though we opened later on a Sunday.

"Your old clothes will make back a bit of money, but I gave you a lot of expensive items, I think it's only fair you do a bit extra. Come straight up to the flat tomorrow morning, and you can clean up in there before we open." Julie told me.

Especially after feeling so good about my day, I felt I couldn't argue with that, I wouldn't have the amazing outfits that I had without Miss Julie...

"Yes Miss Julie." was my only response before heading home.

*

I was again 5 minutes early the following day, and buzzed for Miss Julie's flat above the store. She took a while before opening the door to her flat, and I blushed as I was greeted by her in an incredibly short and revealing sheer nightgown. She ushered me in, I followed trying to avert my eyes.

I followed, heading to the bedroom, and then felt my face grow searing hot as a man exited the bedroom in just tight boxer shorts. As with Miss Julie, I tried to avert my gaze, but I couldn't help seeing his large package barely contained in the boxers.

I felt embarrassed and out of place in my pink gingham outfit, the man just smiled at me. He must have been in his late 40s, messy short hair, dark stubble and a hairy chest. Thankfully I was quickly escorted through to the bedroom and Miss Julie closed the door.

"Don't worry about David, he's leaving soon anyway," clearly seeing my awkwardness.

"The outfit looks great cutie, but didn't you bring something to clean in?"

"No... I..."

Miss Julie sighed.

"As cute as you look in gingham, we need to save that for the customers today. Who knows, your gentleman might be back for some more shoes... Look, I went to the gym last night, my clothes are somewhere over there in the corner, you can wear that stuff this morning to keep you clean. Or just clean in your panties... David might recognise those though." she laughed.

"Okay, i'm going to have some breakfast with David, you get this room cleaned up then move onto the bathroom. I'll see you later."

I started to calm down a little once I was alone in the bedroom, door closed, keeping me apart from the two of them in the next room, even though I immediately heard laughing and giggling.

My eyes panned across the room, it was a real mess. Bedsheets everywhere, clothes strewn across the floor, I didn't know where to start. Feeling conscious of myself, I started feeling through some of the the clothes and sheets on the floor for Miss Julie's gym clothes. The sheets were warm and damp, clearly used just before I arrived. As I was rifling through, I caught some stickiness on my hand, I wiped it off and tried not to think of it, and then found the gym clothes.

I carefully took off my pink gingham outfit, finishing with the slightly discoloured white cotton bra and panties, thinking of their previous use. I then grabbed the black lululemon leggings, still with black cotton lace-trim panties on the inside (clearly quickly ripped off), they were still damp with sweat having been bundled up. I pulled them on, realising the fairly strong, but not unpleasant smell coming from the crotch as I also put on the similarly damp matching sports bra.

I tried to focus on the cleaning, stripping the bed, gathering the laundry, putting new sheets on and wiping the floor. I tried to keep two piles of laundry, one for Miss Julie's clothes, and one for David. I then moved onto the bathroom, which was similarly messy, especially the spread of pee on the toilet seats which I supposed was from David just before I arrived.

I was wrapped up in the cleaning when I realised the door open behind me. I flushed slightly as I realised it was David standing above me as I was scrubbing the toilet on my knees. He tapped my butt as he asked me "Have you seen some boxer shorts around here babe?"

I felt my clit twitch as his hand touched me, shaken I stuttered as I tried to say yes.

"Don't worry, Jules said you wouldn't mind cleaning them for me. I just wanted to say i'll drop by the store at lunch."

Again, my clit twitched. I couldn't understand what was happening. Then, he left.

I finished up in the bathroom, and grabbed the pile of laundry I gathered for David, and proceeded to clean them by hand in the sink.

Miss Julie thanked me once I had finished, and I put my outfit back on, ready for work.

The rest of the day went well for me, especially after how intense the morning was. Similarly, David's entrance at lunch was less eventful than I expected. He spoke with Miss Julie for a while, and I handed over his freshly dried laundry as he left, though I again felt my clit straining as he said "Thank you" and lightly touched my hip.

I hope all of this shows just the kind of situation I was in, and what my mind was going through before the day of the Wedding. I think it explains how I ended up where I did by the end of the Wedding.

***

We started the day by heading over to Jessica's, the place where it all began for me. As Ellie and I drove over there, I was feeling nervous, but also thinking fondly of those excited moments when we first tried on the dresses. That day, being helped by Lou, was only a few weeks ago, but so much had changed since then.

Both Ellie and myself were wearing casual clothes, as the plan was to do all of our make-up, hair and put on our dresses together. Ellie wore jeans and a plain t-shirt, I was in some denim hotpants and a flowery crop-top. Our bridesmaid dresses were with us in the car.

As we arrived, Lou greeted us with a huge smile. I couldn't help quickly flicking my gaze down to her ankle, where I saw the ankle bracelet and key attached above her bare feet. I tried not to show her I was thinking of it, after all, I only needed to cope with one more day to keep my promise to Lou. She was looking great though, even if she was just in a matching light pink leggings and sports-bra set.

We gathered excited, all heading to Jessica, who we could tell was feeling nervous. She was fussing around, trying to make sure everything had been taken care of at the venue. We tried to calm her down, and focus on getting ready, which was conveniently timed as we heard a knock on the door. Lou headed over, and returned shortly with a tall blonde woman carrying a large metal case, introducing herself as Emily, here to do our hair and make-up.

Jessica went first, followed by Lou. They both looked incredible, which increased my excitement. Though I started to worry if Emily would say anything, did she know about me, had she been warned? When my turn arrived, I was slightly apprehensive as I sat down, but Emily was kind and friendly. I even received compliments on my simple make-up which I had applied that morning, but Emily worked quickly beyond what I was capable of. I couldn't believe it was my face as she progressed, wonderful contours, dark and smokey eyeshadow, bright pink lipstick, some glitter around my cheeks. I looked so good.

Emily then asked if I would like to have my hair done, and before I could fumble a response about how I was wearing a wig, she said that she was amazing with wigs and had some more options in her van. I couldn't say yes quick enough, and took her first suggestion of beautiful wig with long flowing blonde locks. She took her time fixing it carefully in place, and making sure it blended seamlessly, making the overall look something I was astounded by. I had liked the way I looked over the last few weeks, but this was beyond what I could ever have expected, I felt so beautiful, I was so happy.

After thanking Emily, I headed to put on my dress. I headed to the spare bedroom after being shown there by Lou, who also complimented me, further boosting my ego. I pulled out of my handbag the lingerie I packed, some light pink panties which I had been given by Miss Julie, which although had signs of wear on the inside of the gusset, felt so beautiful and delicate as I pulled them on over my butt and clit. I combined the panties with a plain pink strapless bra, and fitted in my breast forms. After that, I pulled the dress up over me, struggling slightly with the pink ruffles, and then making sure the sequinned upper portion of the dress fitted well over my breasts. Finally, I carefully put on my silver high heels on my feet, which showed off my pink-painted nails at the front. I couldn't have been happier with how I looked, I think I admired myself in the mirror for 5 minutes, but it could easily have been a lot longer.

12