The Story of Beth Ch. 03: Night Out

When Wendy suggested a girls night out I jumped at the idea. Even though the idea of going out in public dressed as Beth terrified me, I was very eager to become Beth again. I did have a bit of a problem however. I didn't actually have any clothes for Beth, at least not clothes that could be worn in public. When I told Wendy she immediately offered to take me shopping. I had no idea about picking out women's clothes and my fashion sense in general was a bit suspect. Having Wendy help lifted a huge weight off my shoulders.

Wendy arranged to pick me up the next day after work. I was excited and nervous as I waited at my front window for her car to pull up. When she finally pulled into my driveway I raced out the door to meet her. I got in her passenger seat and she pulled away from my place.

"So, where do you want to start?" Wendy asked as she drove.

I immediately knew what I wanted to ask about. I had been thinking about it since I met Katie.

"Uhhh, so Katie had inserts in her bra or something right?" I asked timidly.

"Yeah, they're great." Wendy answered with a friendly smile. "We got them at a store here in town. Why don't we stop there first."

"Sure, that sounds great." I replied, trying to hide my excitement.

As Wendy drove I thought about how I looked in the mirror as Beth. The stockings, bra and panties did a great job bringing out the curves of my body and making me look much more feminine. With a bra that wasn't tight against my chest. I was practically buzzing with excitement.

We pulled up to a building that was much bigger than I expected. It looked like a big box store but the mannequin in the front window were dressed in everything from lingerie to extravagant costumes. We parked out front and went inside. I was immediately blown away. The inside was much bigger than it looked from the outside. Half the store had shelves and shelves of sex toys and other adult accessories, while the other half was full of clothes.

We were greeted by a small bald man that smiled as he said hello, and then went back to whatever he was doing behind the counter. Wendy and I smiled at him and then she took me by the hand and walked across the store towards one section of the back wall. I was glad Wendy knew where she was going because I would be lost for hours in a place like this. The thought that I would have to ask a stranger what I was looking for made me feel incredibly shy.

"I think a B cup would be the best size for you." Wendy said as we arrived at a wall covered in different sized inserts.

"You don't think I should go comically large?" I asked with a smirk and we both laughed.

Making jokes cut the tension for me, Wendy however seemed to have no issues with any of this. I was very appreciative on how much support I received from the people around me. I had no idea how I could ever navigate any of this if I was on my own. Wendy grabbed a box that had a big B on it and a picture of a bust.

"I think I am going to need a new bra too." I remembered. "I don't think the one I have will fit those."

Wendy nodded and gestured me to another section of the store where there were racks of bras in every imaginable style and color. I picked out a bright red, lacy one that came with a matching set of panties. I definitely had a preference for the lacy, feminine looking ones.

"You've got to try it on," Wendy said pointing to the bra. "we have to make sure it actually fits."

My face got red and flushed as she led me to the change rooms. Wendy saw my nervousness and tried to re-assure me.

"Don't worry, its just the bra." She said with a wink. "I wont make you try on the panties."

I was relieved when the dressing room area was completely empty besides us. I went into the mirrored little room and took off my t shirt. The bra had clasps in the back so I put it on backwards, did up the clasps and then spun it around on my body before putting my arms through the loops. I had seen girlfriends put on bras this way in the past and it was surprisingly easy. Besides adjusting the shoulder straps a bit the fit was very good. There was extra material at the cups but I figured that would be filled by the inserts. I loved the way the lace looked against my skin.

"Alright, let see it." Wendy called out from behind the door.

Sheepishly, I opened the door. I must have looked totally out of place. I had normal jeans on with no shirt and wearing a bra. I poked my head out of the change room before taking a step out. Luckily no one was around to see me besides Wendy.

"The fit looks really good." Wendy said as she put a finger under the material at various spots, checking the tightness. "You really have the body to rock this. Katie would be so envious."

I turned a little red but really appreciated the compliment. Wendy did a little spinning motion with her fingers and copied it with my body, spinning around. She smiled in approval and I retreated back into the change room to take the bra off and slipped my shirt back on.

"Need anything else here?" Wendy asks as I came out of the change room again.

"Ummmm, Katie had that pink thing on the other night..." I said nervously. Too embarrassed to actually call the chastity device by name.

"Oh, you mean her little cage." Wendy said smiling. "Yeah, those are great. You don't want a huge bulge in front of your dress."

We walked to the end of the store with shelves of sex toys into the section with various bondage related things. I was impressed with the huge selection of chastity devices. They had all kinds of styles and colors.

"Does anything jump out at you?" Wendy asked as she browsed the selection.

"I would like to get something cute and pink." I answered, still a bit embarrassed about the whole thing. "How do the sizes work?"

Wendy handed me a package that had a hot pink one on it.

"You don't want any extra room in there to grow, but if you are going to wear it for a while maybe don't get one that is too tight."

I had a mini struggle in my mind. My masculine side wanted me to exaggerate my own size so that it seemed like I need a larger one to contain me. On the other hand I wanted Beth to have something tiny so that is was small and feminine looking. Truthfully though I was only modestly endowed so I picked one of the smaller sizes.

"That will look so cute on you." Wendy beamed and I couldn't help but smile back at her. "Need anything else?"

"No, I think that's it from here." I answered and started walking towards the checkout to pay.

"Wait, I know." Wendy said suddenly and darted into another aisle.

I was already at the checkout when she caught up to me and I saw what she had. It was a clear plastic container with a fairly large metal plug in it. At the base there was a shiny red jewel that matched the color of the underwear set I was paying for.

"This is the same one me and Katie have." Wendy said enthusiastically. "We'll be matching. It'll be my treat."

I turned red and looked at the cashier. I have never bought toys in person and the idea that he knew that the plug was for me filled me with embarrassment. He didn't even flinch and just rang up my stuff and put them in a bag. In retrospect it was a silly thing to be embarrassed about. I'm sure he has seen way more wild stuff than some dude buying a few toys and lingerie. We both paid and made out way back to the car. As I left the store I was already thinking about coming back and spending hours browsing the various shelves like a kid in a candy store.

"So what kind of outfit should we get you?" Wendy asked as we both got in the car.

"I would love a nice dress." I replied as I imagined myself in different outfits. "Something short and flirty."

It felt surprisingly natural describing things I wanted to wear. I didn't think I would ever have described my own clothes as 'short and flirty' before, and I really liked it.

"I know a great little shop." Wendy exclaimed as she pulled out of the parking spot.

We pulled up to a store barely 5 minutes later and parked out front. It looked like a trendy boutique store that had everything from clothes and shoes to accessories and purses. Again, I was glad I had Wendy with me as I would have been way to anxious to shop for anything myself. We went in and Wendy began slowly walking through the store between different displays and racks of clothes. I followed her like a puppy dog, eyes wide as I imagined myself in various outfits.

I stopped in front of a mannequin wearing a bright red, tight fitting cocktail dress. I reached out an ran the material between my fingers. It was smooth and soft, and I imagined it against my skin. Wendy noticed I was no longer following and came back to meet me.

"That dress would look amazing on you." She beamed while I looked around to see if anyone heard her. I was definitely not comfortable other people knowing we were shopping for me. Luckily the place was completely empty except for one saleswoman at the opposite end of the store.

Wendy looked me up and down and then started flipping through the rack of identical dresses in slightly different sizes. She pulled one out and held it up against me, trying to visualize how it would fit. I saw the young lady walking towards us and took a quick step away from Wendy so the dress wouldn't be against me when she got there.

"Can I get a dressing room started for you?" She asked once she was a few feet away.

"Sure please." Wendy answered and handed her the dress.

"Perfect, let me know if you need help finding anything." The lady said and walked towards back of the shop. I followed her with my eyes until she disappeared down a side hallway where I assumed the dressing rooms were.

"You're probably going to need matching shoes right?" Wendy asked turning back to me.

"Haha, Yeah. I guess my dress shoes wouldn't go with that dress." I joked, again trying to easy my own anxiety.

"What style do you want?" Wendy asked as she led me to the shoe section. "Heels... Flats... Maybe stilettos?"

"I have never walked in heels so maybe something lower." I answered, not noticing she said stilettos as a joke.

"Definitely don't want heels then, for your first time going dancing." She said handing me a shoe off the wall of shoes in front of us. "These flats would be super cute with that dress. What size are you?"

I was immediately grateful that all the boxes of shoes were stacked right beside the display and we didn't have to ask the lady working there for a men's size 10. I grabbed the box with the right size and let Wendy guide me past the cashier desk towards the hall of change rooms.

"Number 3 is open for you." The lady said with a polite smile as we walked by.

I was grateful both that the store was empty besides us and that the change rooms were in a secluded little hallway, out of sight from anyone that just walked into the store.

I walked into the change room and saw the dress handing against the far wall. Wendy sat down on a large padded bench just across from the door. She smiled at me as I closed the change room door behind me. My hands shook a little with a combination of excitement and nervousness. I slipped off my shirt and pants, unzipped the back of the dress and stepped into it. I felt a rush of blood as I pulled it up my body and felt the soft, smooth material slid up against my skin. I felt myself getting hard from the combination of the feeling of the dress and my appearance in the mirror. The dress hung on my shoulders and the cut was high enough that the inserts couldn't be seen. It ran partway up my thigh and hugged my ass tightly. As I was unboxing the shoes to try them on at the same time I heard someone come into the hallways of change rooms.

"Everything fitting ok?" I heard the saleswoman ask. "Do you need me to get you any other sizes?"

I froze and panic started to set in. I just realized that if Wendy was sitting outside the change room, the saleswoman knew it was me trying on the dress. I couldn't bring myself to answer but luckily Wendy answered for me.

"I think we're ok. Thanks for checking."

"No problem, just call me if you need anything." I heard from the saleswoman and her footsteps faded as she walked back out of the hall.

My panic subsided and I finished putting the shoes on to complete the outfit. I stood there staring at myself in the mirror and felt my pulse slow down to a reasonable level again. Wendy, guessing I was done by the lack of movement in the stall, spoke up.

"Are you ready. Let's have a look."

Nervously, I opened the door to the small change room. I was relieved when Wendy's eyes lit up and she smiled.

"That looks amazing on you. Do you need me to zip you up?"

I slowly turned around, still not wanting to leave the stall. Wendy zipped up the back of the dress and I reveled in it tightening up around my chest.

"Let's get a good look at you." Wendy said, and I stepped back and did a slow spin, letting her see me and checking myself out in the mirror at the same time.

"You look sexy as hell, but you may need to do something about those legs." She said with a giggle. "And uhhh, something about that too."

Wendy gestured at the front of my dress. I looked in the mirror and realized my legs were pretty hairy. I would have to shave, that's for sure. I looked down at myself and my face turned red. I had a very noticeable bulge on the front of my dress where my hard-on strained against the tight fabric.

"I think we have that covered." I answered and we both laughed.

I paused there for a long moment, staring at my curves, until I was satisfied and turned my back to Wendy. She unzipped me without prompting and gave me a playful smack on the ass before exiting the change room. I slipped the shoes back off and let the dress slid down my body. Taking it off felt as sexy as putting it on. I hung it back on the hanger before putting my own clothes back on. It felt incredibly satisfying to be buying this dress for myself.

I got dressed and walked out of the change room, back towards the sales desk with the dress and shoes in hand. I stopped in front of the desk and was glad that no one else had entered the store.

"Have everything you need?" The saleswoman asked with a polite smile.

I smiled back and nodded silently. I'm sure my face was bright red and I was glad she didn't have any look of judgment on hers. She rung up the items and put them in a large bag. I paid and we left the store quietly. I loved the dress and had a notion like I shouldn't have it or something. I walked hurriedly to the car before anyone noticed and took it away from me. This was completely silly of course, and in retrospect I realized it stemmed from my insecurities regarding exploring this new side of me.

Wendy drove me back home and I barely said anything the whole way home. I was too preoccupied with thinking about myself getting to wear that dress again. Once she dropped me off I put my new things in the house and walked to the nearby store. I picked up some shaving cream, razors and moisturizer. After my purchase I walked home very quickly with excitement.

At home I ran a bath and soaked for a while before shaving everything from the waist down. My legs took a while as I was not used to shaving them but I was proud that I managed the whole thing without cutting myself once. Once out of the bath I dried off and moisturized everything from the waist down again. I walked around the house naked, letting the moisturizer soak into my skin.

I unboxed and laid all my new purchases on my bed. My heart raced with excitement as I looked at the bra and pantie combo. I decided to try the bra on but not the panties since I didn't want anything to get on them before I had a chance to properly wear them. The bra fit amazing and I was blown away by how much better it looked with the inserts in. It felt incredible to be able to look down and see breasts in the lacy bra on my chest. I pranced around a bit with just the bra, getting looks at myself from different angles in the mirror. Once satisfied I decided to try out the other two purchases.

I started with the metal plug. I had my own butt plugs but this one felt special somehow. Wendy got it for me and it matched the one she and Katie had. I ran it under warm water in the sink so the cold metal wouldn't be such a shock when it was against, and inside me. I saw surprised how little lube the smooth metal needed. I got on my knees on the floor and bent forward, pressing the tip against my hole from behind. I barely needed any pressure before my body opened up and the wide bulb slid in. I closed around the narrow end and all that was left was a sparkly red jewel that I admired in the mirror. I loved the weight and feeling of fullness as I went back to the bed for my other new toy.

Here I had a problem. I picked up the small chastity device and looked down at my rock hard cock. There was no way this was going to work in this state. I decided if I got off I might shrink back small enough to fit it. I got on my hands and knees on my bed and looked at the red dress laid out beside me. I began imagining how I would look and how it would feel on my body and began slowly stroking myself. Between the imagery and sensation in my ass it barely took a minute until my orgasm shook my body.

I tried not to think about Beth as I cleaned up, hoping I would get soft quicker. My situation wasn't helped by the fact that every time I walked around the plug sent little sensations through my whole body. I eventually just sat down and watched the news and applied a cold washcloth to my penis until I was small enough to try the little cage. I followed the directions that came in the box and it wasn't too tough getting it on and secured. It had a small built in latch that kept it closed so I didn't need a lock or something that would rattle or make noise. Once it was on I put on a tight pair of panties to hold it securely against my body. I inspected myself in the mirror and loved how it looked. It made the bulge in my panties, even though it was still noticeable, much smaller. I was very happy I went with the smaller option I picked. Still, it took some getting used to. I was getting turned on again just by looking at it in the mirror but the snug fit prevented my from actually getting hard. It just felt like a bit of dull pressure. I decided I would wear it around the house every day until I got used to it before wearing it out on girls night.

The rest of the week went by without anything significant happening. I came home straight from work every day and put on first the cage, then my new plug and a pair of panties. I got used to peeing sitting down with it on and learned I needed to wipe it very well to prevent any dripping. On Thursday, the day before our night out I gave Jess a call.

"Hey, I have a favor to ask you." I started the call hesitantly.

"Sure, what's up."

"I'm kind of doing a night out as Beth tomorrow and was hoping you would help me with makeup and getting ready."

"Of course. I would love to." And I could hear the excitement in her voice. "Do you have makeup and everything?"

"Ummm, no." I realized. "Can I borrow some of yours?"

"Haha, you know this stuff isn't cheap right?" Jess teased. "I will bring the basics over but you need to buy your own supply."

She offered to help make me a list and I happily agreed and thanked her profusely. I could barely sleep that night due to my excitement for the next day. Work was a blur and ducked out early to go home and get ready. When I got home I ran a warm bath and proceeded to shave everything but my head. After the bath I took a very quick, somewhat cold shower just to rinse any extra residue from the bath off. The cold water also helped calm my libido and I put my cage on immediately after I got out. I figured that once I started turning myself into Beth there was no way I would get it on the whole night. I then moisturized and started putting on my new bra and panties set.