tagTranssexuals & CrossdressersFinding A New Purpose Ch. 05

Finding A New Purpose Ch. 05


** Note: This story is purely fictional. All characters and actions they perform are fictional as well.

Also, this is a slightly longer chapter. The reason why is because it's leading up to a rather intense scene in the next one that could qualify for several different categories, but I'll leave it in this one so it's easy to find.


I woke up in my own bed, rubbing the sleep out of my eyes before making my way to my bathroom to get ready for the day like I normally did. Quick shower, shave my legs and face, brush my teeth, get dressed (if you could call it that), and started walking down the hall towards the master bedroom, yawning most of the way. The door creaked open as I quietly slipped inside, trying not to wake Mike.

Obviously I was out of it, because when I got into his bed and reached for him, I found my hand stuck in a pillow. It took me a second to realize he'd stuffed his bed to make it look like someone was there. Throwing the sheets off of me, I shuffled my way out of the room and down the hallway in my slippers and a skimpy nightie.

"THAT'S what you're wearing to shop in?" Mike said as I walked into the dining room.

I gazed around confused, "Huh? Why are you up already? And why did you stuff pillows in the bed?"

"I decided to make breakfast," He motioned towards the table. There was a bowl of cut up fruit, a box of cereal, and milk. Not much in terms for breakfast, but then again he didn't cook like I did.

"Thank you," I said, taking my seat across from him. "Wait, shop? I did the grocery shopping yesterday."

"You can be quite dense sometimes. Or forgetful. One of the two." He shook his head and picked up the paper. "Birthday. Ringing any bells?"

"Why do I keep forgetting? I thought I was in the wrong condo when I saw food on the table that I hadn't prepared."

"Glad to know I'm appreciated around here," he said under his breath.

"Oh come on, you know what I meant. It's just unexpected! You do more than enough for me around here." I winked when he bent the paper down to look at me.

"You just like me for my body," he teased.

"That's my line, mister," I said as I got up from the table with my bowl and walked over to grab his so I could put them in the sink. "You know I'm right," I said as I slowly turned around in circles next to him. The paper folded down again so he could look at me.

"Ehh... Yeah, I keep you around for that sexy butt of yours." He pinched my behind through the nightie, as I headed off into the kitchen, giggling.

"Seriously though, you need to go put something on and do your hair up because I want to leave sometime this century. You're the one that has to go to all these different shops. You realize one of them his halfway across the city, right?" Mike said as I came back for the milk.

"It's not socially acceptable to walk around hanging off your arm while wearing this?" I replied sarcastically.

"Sometime this century, please?" he said again, going back to his paper.

I went back into my room to get dressed for a second time. The nightie I had been wearing was folded and put back in its place in my dresser before I sorted through what 'regular' clothing I had left. I decided on a pair of tight, low-cut jeans and a white tank top. It was about all I had in terms of feminine clothes, though hopefully not for long. I considered not wearing any panties but since I was going to be trying clothes on all day, I pulled a white thong up around my waist. It was shaped to look like a large butterfly (or small butterfly rather, since the crotch of the panties was quite meager) in the front. They were one of the first things I'd taken from my sister.

I put a simple white bra on. The bra was only an A-cup, but it was padded to make me appear more like a B. It was nice that Mike enjoyed more petite breasts, but I wanted to make myself look a bit more shapely up top since I was going out into public with him. I put the rest of my normal clothes on and went to the mirror in my bathroom to fix my hair.

Over the past several months, I had let my hair grow longer, until it had come down to about the length of my chin. It was just short enough that I could pass it off well enough when I had to go into the office or visit my family. No one seemed to notice it as being odd or anything, which made my life a lot easier. When I wanted to though, I could do it up in this nice, tousled look that most women wished they had. It looked good with my dark brown hair that I'd streaked with red highlights. I sprayed my hair after I was done to help it keep its shape as I took clothes on and off during my shopping.

The hairspray made me cough. I could never understand why most hairsprays smelled horrid, and this one was no different. I stuck my tongue out in disgust and decided to mask it with a light perfume I wore occasionally. Mike always said he loved the way it made me smell.

"I'm ready, and it's still the twenty-first century!" I yelled down the hall as I grabbed my phone and keys off of the table by my door and set them in my bag that I put on my shoulder. It was small and unassuming. Large purses just bothered me. Not to mention they looked like suitcases, in my opinion.

"Yeah well, it's still getting late. We better get going." He was already standing in the door way holding it open, waiting for me to go past him.


"Should I try the red one on first, or the blue?" I asked from inside the dressing room.

"It doesn't matter, you're going to try both on either way," Mike said, his face buried in his hands. "Remind me not to do this again."

"Hey, bud, you offered to do this for my birthday. Remember? All you," I said, pulling a nice summer dress on. It had pretty red chrysanthemums printed on it. The other dress hanging on the door had some blue-ish lavender flowers on it that I didn't recognized. The color was beautiful, and would match my ocean colored eyes well, so I had grabbed it to before dragging Mike back to a bench designed for suffering men to sit on.

I stepped out and twirled in front of him before asking him what he thought. "It's alright I guess, I liked the blue one more." Mike muttered. I sighed loudly before heading back in to change.

"You could have said that before I put the red one on you know." I hung the dress up on the hook and grabbed the one with the blue flowers. The fabric was softer on my skin than the previous one, not to mention it was shorter.

"You still would have tried it on," he said in an annoyed tone.

I came out again and twirled for him, hoping the dress would gain his approval. "Better," was all he said. I put my hands to my sides and stomped my foot. "What? I just figured you'd be trying on sexier dresses. Don't get mad at me; I'm the one paying for all this stuff, anyway. At least that dress is shorter than the other ones.

"Good, 'cause I want this one," I said from inside the changing room. After putting my bra and top back on, I pulled up these nice khaki capris pants that I'd bought earlier in the day. I carefully hung the blue dress back on its hanger and dragged Mike to the cash register of the fourth store we'd been too. He begrudgingly handed the women behind the register his card before turning around and leaning against the counter.

"Don't mind him," I said to the woman who smiled at me as she placed my new dress in a bag. "He CHOSE to go shopping with me." We both laughed and Mike started heading for the door.

"Don't remind me," he sighed as I caught up.

"No worries," I said as I walked next to him. "We get to do the exciting stuff now."

"Exciting stuff? Shoes again? You already got three pairs." He put his hands in his pockets. I put my arm around his as he said, "Why the hell do heels cost so much?"

"Oh stop it," I said, slapping his arm.

"You aren't the one who's spent like, five hundred dollars in the past three hours."

"But, I'm worth it right?" I asked, trying to sound innocent. "Plus, the next place has this cute little cocktail dress." I emphasized the 'little' part.

"Well, we're definitely getting warmer then."

Mike drove us to my next destination and found a parking garage close by. It was one of those underground ones, that always seemed dark no matter how much lighting they put in. They just felt eerie. I found my self clutching Mike's arm and holding myself next to him closely as we walked back up to the street. He felt safe.

We walked into the clothing store and headed up to the second floor, which was the women's section. I quickly explained to a nearby clerk what I was looking for, and she led me to it as I dragged a more reluctant man behind me. The clerk left after showing me to the section where the dresses that I was looking for were. As I searched for it, Mike looked through the dresses too, pointing out recommendations he liked.

"You can pick one and I'll try it on for you, but that's it," I said, shaking my finger. "Here we go." I'd found the dress I was looking for. It was a sleeveless black cocktail dress. I hadn't been kidding when I'd said it was little. Personally, I thought it qualified more as a miniskirt, but it had been advertised as a cocktail dress. It was open in the back, revealing down to the small of the back where it folded several times, giving it the impression it had fallen down. The front was a bit more modest, though, it revealed a good bit of neckline, but it wasn't meant to show off a bust.

"I only get to pick one? What about two?" He started begging. I shook my head in my hand. Figures I bring him to this section and he's the one that wants to keep picking out things.

"Only one. You can buy me another one later." I grabbed two of the same dress. 'Ha, I'm actually buying myself a little black dress,' I mused whimsically to myself.

"I'm not sure if I should try a size two or just go with the three. The two looks like it might be a bit tight. I'll just try them both I guess." I was talking to myself out loud. Mike overheard me as he walked over carrying another dress.

"Just put on the two, it will show you off better," he whispered behind me, pulling my hair to the side and nibbling at my ear. I responded by pushing him back and grabbing the dress out of his hands.

"Hope this is your choice, 'cause this your pick that I'm putting on," I said, heading towards the dressing room. This time, I didn't have to drag him. He followed me eagerly.

Once inside I started undressing myself. After I pulled my tank and jeans off, I folded them and set them in the chair behind me. As I unclasped my bra, I realized the only hook in the room was on the door where I had placed the the dresses. In all of the other stores, I had been putting my underwear on one of the spare hooks. I just shrugged as I hung them over the wall separating my room from the one next to it.

"I'm putting mine on first," I said loudly, making sure Mike heard me.

"Hey, Mike!" The voice sounded familiar. It was coming from outside of the dressing room where Mike was sitting. I continued getting dressed.

"Oh uh. Hey, Jessica." He said her name loudly. "What are you doing here?"

All I really heard was 'Jessica.' I started panicking. 'Oh shit!' I sat down on my clothes and pulled my legs up, hoping she wouldn't notice anyone in the stall just a few feet away from her. I hadn't even thought about what I'd do if I ran into anyone that knew me, and here was my sister, talking to Mike.

"I could ask you the same..." She said, looking at him strangely. "You realize this is the women's dressing room, right?"

"Ha, oops. I get lost in big stores like this." He was trying to get himself out of the awkward situation. Failing miserably at it, too.

"Right... Hey I heard about you and Rachel. You get over it yet?"

"Yeah, I guess. I have been occupying myself with other things." That was for sure.

"Ah. You could have called me you know. I would have gladly helped you get over her." That slut! Had she seriously just said that?

Mike coughed, "Uh, thanks but, I think Alex would be pretty damn pissed about that." I was pissed already!

"Probably would be," She chirped. "You waiting for someone? I heard someone talking in the dressing room but the other stall is empty."

She had gotten Mike. His earlier excuse was pretty pathetic. "Oh right, yeah. Just a friend of mine. She asked me for her opinion on something," He said nervously trying to cover for himself.

"Well, that's nice of you." I heard her make her way into the other stall. Jessica shut the door hard and she started getting undressed. Great. My sister was getting naked right next to me and here I was, wearing a dress. I prayed she had lots of things to try on so I could get out before she finished. Or maybe I could wait long enough for her to leave? No, that wouldn't work, Mike had told her he was helping his friend who was trying on clothes.

I had started getting out of the dress before I came to a horrifying realization. My bra and panties had fallen into her stall when she slammed the door. What could I do? She would notice any second. I couldn't just run off. It would raise suspicions on her part, leaving without my underwear, and I doubted I could get dressed fast enough. And if I left wearing the dress, one of the clerks would stop me from walking off wearing their merchandise. I pulled the dress up.

"Oh, oops. You dropped something over here," I cringed when she said that. She wasn't speaking very loudly, and I doubted Mike could hear. "Oh hey! I used to have panties like these. I really liked them, but they disappeared."

'Shit, shit, shit!' I kept saying to myself. Adrenaline was coursing through me from the panic.

"Yeah, I never found out where they walked off to. I think my brother stole them. Here." I saw her hand holding them over the wall for me.

"Boys will be boys." I forced myself to laugh, and it came out terrible. I snatched MY undergarments from her grasp.

"Still, that's weird," She said as I heard her putting clothes on. "So you know that guy out there?"

'Be cool, she doesn't suspect anything yet.' "Oh, uh, yeah. He's a good friend of mine." I felt my voice shaking. Nerves were making it hard to focus on not letting my natural voice come through.

"Lucky. He's such a hunk! Have you two ever...?" She trailed off, trying not to giggle. I didn't know what to do. The urge to run kept forcing out any other thoughts.

"No. No." I lied to her.

"I bet he's great in the sack." This was my own sister! My little sister! Well, not really little anymore. She was eighteen, but that didn't matter! "Hey, does this look good on me?"

"Huh?" I said.

Oh. Fuck.

Everything felt like it was going slow. I spun around and saw the knob on the stall door slowly turning and begin to open. I froze like a deer in headlights. My legs wouldn't move even though I screamed for them to run. Anywhere. I had to get out. Jessica stepped into the stall with her back to me, shutting the door lightly this time. My eyes widened in fear when she turned around.

She looked at me, confused, like she couldn't place me. I was pleading with God to not let her recognize me. My eyes looked away from her, as if she couldn't see me if I didn't see her.

"You... YOU!" she hissed under her breath. "I knew something was up! What. The FUCK?!" I was so busted. That was it. My life was completely over.

"Look at you! Dammit, I just knew it had to be you who stole my things!" I was breaking apart inside. She'd tell my parents. They would disown me. People would talk.

"I... uh... I..." I couldn't get anything out. My mind couldn't even piece together a pointless excuse.

"My own brother. Right in front of me wearing a dress!" I heard her start laughing. It felt so... belittling. I looked down, but all I saw was her body in a pink and black miniskirt. To say it was revealing was an understatement. I tried not to, but the dress forced my eyes to her large breasts. The skirt was completely open down past her belly button, and the only thing keeping her tits from coming out was the thin piece of fabric holding the sides of the dress together under her bust line. Her tits were still very exposed. She looked like some slut that belonged in a club grinding against all sorts of guys in rhythm to the music.

I closed my eyes, shutting the image out of my mind, but I just came back to the thoughts about how my life was all over. Tears started forming in my eyes as I fought the urge to break down.

"Hahaha, aww, I didn't mean to make you cry." Her hands reached up to my face and wiped the tears out of my eyes. I braced myself for more ridicules. She put her hands around me and embraced me. I didn't know what she planned to do to me next. "Don't cry, you're alright."

"What?" I said, sniffling. What was going on?

"If I didn't know your face so well, I would have thought you were pretty sexy looking in that dress, if I do say so myself. Too bad you don't have much to fill out the rest of it," she laughed a bit as she leaned back and shook her tits a bit. I wasn't laughing.

"Don't mock me, I know what you're doing." I responded, bitterly.

"I don't think you do. You think I'm going to tell everyone that you dress up in girly things, right?" My eyes glared at her. Of course that's what she was going to do. My little sister always loved getting me in trouble and there probably wasn't anything worse than what she'd just discovered.

"Just knock it off and get a hold of yourself," she snapped. "I'm not going to do that, not to my own brother... er sister?"

"Don't mess around, it's not funny," I said, trying not to start crying again.

"I'm not! Look, here, I'll prove it. I slept with Meredith." She sounded serious.

"Meredith? Your best friend?" It was shocking news.

"Yeah, see? We all have secrets. Now you have something you could tell Mom and Dad, too. Please, don't though. Dad would be quite upset if he found out his little girl wasn't such a goody-goody."

"I've known that since you were fifteen," I said, trying not to smile. It seemed things might be okay after all.

"Oh really now? Well, no surprise you went snooping in my closet and found something years ago. I just can't believe you stole my lingerie!"

"I'm sorry," I apologized. "I can buy you new things. I have more than enough money."

"No, it's alright. Though I am upset that you stole my favorite panties. What all did you take out of my closet?" That made me feel guilty. Not only had I messed with her things, I'd taken her favorite thong without even thinking twice.

"I only took a few things," I told her about the garter belt and other things, but not what I had used them for.

"Oh, I didn't even notice. But these I sure did." She held up the white, butterfly shaped thong.

"You can have them back if you want. Oh, and I also..." I stopped myself. 'Stop digging the hole deeper!' my mind yelled .

"You also what?" She waited for a response, putting the panties back.

"I also, umm." I didn't want to say it. "I used some of your... things."

"Some of my things? What thi-... No you didn't. Seriously!? You know what those are for right?!" She sounded horrified.

"Well, I... yeah. I'm sorry! I was curious!"

"I put those... inside of me! Ah! What did you do with them?!" Was she being rhetorical?

"Uhh." I didn't know if she actually wanted the answer. "I uhh... I don't know?! The same things you do!"

"Gross! Did you even clean them off?!"

"Yes! Don't be dumb. I cleaned them off every time." I felt insulted.

"Every... time? How often would you do that?!" She sounded like she was getting mad.

"Look, I'm sorry okay? I didn't do it all that much, only before I would go over to Mike's." Wait, had I just said that?

"Before you went over to Mike's?" Jessica said it slowly, making sure she had heard me right. I was afraid she was putting two and two together. "Wait a minute. Why are you here with your roommate?"

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