Not a Man Ch. 03

My alarm rang at 7:30 am, and for the second morning in a row, I woke up with my head pounding like someone took a hammer to it. I sat up, and looked around in confusion. I was still dressed from the night before, back in my own bed, with no idea how I got there.

The memories slowly came back to me, while I turned on the coffee maker, drank some water, and poured cereal into a bowl. Jay, showing his tender side. Me, touching his cock. Tess, laughing at my dick. Tess, applying lipstick.

I checked my face in the bathroom mirror. Red lipstick was smeared all over my mouth, and cheeks. That changed the order of things, and I decided to take a shower first, spending several minutes scrubbing my face clean. I remembered the way I had looked last night, right after Tess applied it. Like a girl.

No, that had probably just been the alcohol. I must have drunk so much that I couldn't see straight anymore. That's the only reason I did all those things. The hot water helped clear the fog of my hangover, and by the end, I felt like a halfway decent human again. A cup of coffee, and bowl of cereal later, and I was a hundred percent human again. I wasn't so sure about being a hundred percent man, though.

I couldn't find my phone anywhere, and realized I must have left it on Mr. Table. That was definitely the last time I would ever drink that much, I promised to myself. I'd have to actually talk to Jay to get my phone back. For just a brief moment, I considered just letting him have the phone, but it had been eight hundred bucks. Besides, chances were pretty damn good that Jay would talk to me anyway. At least I wasn't under any obligation to wear women's underwear anymore. Although, that part in itself wasn't too bad. People seeing me wear them was the real problem.

Even better, it was the last day of the week. Just one more day, and I'd have the weekend all to myself. I could just stay at home, drink beer, and play videogames all day. No touching of penises, other than my own, of course, and nobody there to call me girl names.

When I got into the car, it still smelled of booze and perfume, and I rolled down a window to air it out. I did not want to think about Tess that moment, especially because I remembered her words the moment I sat down behind the wheel. "Jay is going to slide his entire cock in your little boy-pussy, and you're gonna moan, and beg for more."

A shiver ran down my spine, and I wasn't sure if it was fear or excitement. I had held Jay's cock in my own hand, and wondered if it was even possible to fit it in me. I hoped I never found out.

As I drove down Washington, I made sure to drive just under the speed limit, and managed to avoid another encounter with the grumpy cop. The morning was actually going pretty well, and not even Darla managed to find anything to whine about when I walked into the office a whole ten minutes early.

Without my phone to distract me, I even managed to get a lot of work done. Friday was the usual end of week server backup day at Lifelast, which I could have done in my sleep. Except, Darla insisted that she was the only one important enough in the office to handle such a responsibility. The only problem was, she had no idea how to do it.

Every week, like clockwork, Darla shambles over to my desk, stinks up my cubicle, and starts chatting all friendly. It always ends the same way.

"Henry, I'm gonna need you write another one of the programs for me. I'd do it myself, but I have so much on my plate already, you know how it is, and you've done it once or twice already."

She then shambles back into her office, and I send her an email with an attached batch file that starts the backup process. I've tried explaining to her that I just send her the same damn file every week, but she didn't seem to understand. She just expects an email to pop up in her inbox that has an attachment she can just double click, and do everything for her.

All so she can be the one to report back to the main office in San Diego that she "took care of the job." If I did ever get fired at Lifelast, I'd always have a backdoor, if I wanted it.

I was in the middle of responding to a ticket of a Lifelast employee who, I have no idea how, managed to spill coffee on his keyboard for the third time that week, when I heard a knock on the wall of my cubicle. It was Tess.

"Hey Henry, whatcha doing?"

"Just work," I replied tersely, with incredibly mixed feelings.

Tess was still the same person, on the outside at least. Incredibly gorgeous, with a body to match. My feelings for her never really went away, despite the fact I now knew more about who she really was.

"You left this at Jay's," Tess said, and handed me my phone.

"Thanks!" That meant I might not have to see Jay after all. The morning kept getting better.

"He left you a little surprise, too. Actually, I should call it a big surprise," she giggled.

I tapped the screen, and was greeted by a closeup picture of Jay's erect cock as my new background image. Before that day, I didn't think it was possible to identify someone just based on their dick alone, but I had seen more than I wanted of Jay's. God, it really was perfect, in pretty much every way. If Tess was the height of female beauty, then Jay's cock would be the essence of masculinity.

"Jeez, you're really staring at that thing, huh?" remarked Tess, and I realized I had been. "Don't worry, little slut, you'll get your chance soon."

I put the phone in my pocket, but not before a shiver of excitement ran up my spine, and my dick twitched in my pants. "Is that all?" I snapped at her, feeling guilty about my body's unwanted reaction.

"No, silly. You and I are gonna have such a great time," she bubbled.

"We are?"

"Yeah. We're going shopping!"

"Why?" I asked, suspiciously.

"You're gonna need a lot of new clothes, silly."

"I have clothes."

"You have guy clothes, yeah."

"But—"

"No arguments, Henrietta," she interrupted, emphasizing the nickname. "Jay's orders."

I sighed. "When?"

"Now."

"I got lunch in half an hour, we can go then," I offered.

"We're going now, come on."

Tess grabbed my hand, and started pulling. With my free hand, I quickly locked my computer, and got up. I could have refused, if I wanted to, but as pathetic as it sounds, I would have given up a lot just for her to touch me. Two days earlier, if she had come up to me, and held my hand, I would have masturbated over the memory for a long time. Things were slightly different now, but I let her lead me on like a little puppy with only a little bit of hesitation, anyway.

Darla shot me a nasty glare as we passed her office, but I could tell she was in the middle of composing one of her "Very Important Emails," and only had a glance to spare for me. Or maybe she didn't expect me to walk out of the office hand in hand with a beautiful woman half an hour before lunch, but that's what I did.

Tess held out her hand for the keys, and I handed them to her. We got in my little Toyota, and started driving. It didn't occur to me until after we were already underway that she didn't even bother asking if it was okay to let her drive. She just naturally assumed control, and, just like the pussy Jay told me I was, I let her.

"Where are we going?" I asked

"The mall," she replied, turning left on 8th.

"Really?"

"Is that so surprising?"

"I don't know," I explained, "I expected some sort of deviant sex store, or something."

Tess laughed. "I don't think you're ready for those yet."

"So no kinky leather outfits, then, huh?"

"Nope. Just regular off the rack chick stuff."

"Just underwear, right?"

"No, silly," she said, as if she were tired of explaining the same thing over and over to a child. "Skirts, and tank tops, and some nice blouses, and yes, some panties too. And bras."

"But... why?" I pleaded once again.

"It's fun, you know. I never had a little sister growing up, but I always wanted one."

"But I'm not a girl," I protested.

"Henry, please. You might as well be one. We've known each other like what, two years now? In all that time, do you know how many guys at the office have hit on me? At least one a week. Hell, I've even fucked a bunch of them, and I have to say, some of them had pretty small dicks. Not as tiny as yours, of course, but still. And you know what? Some of them were alright. At least they took a shot at it. Not you, though. For two years, you never even talked about women. I was pretty sure you were gay for the first couple of months, before you started to get embarrassed whenever I wore a low cut top. You were just fucking jerking off by yourself, fantasizing about getting with me, and then when Jay and I start hooking up, you try to blackmail him so he leaves me alone?

"Henry, I don't want to be left alone. It's really fucking awesome being with a guy who actually wants to fuck you, rather than just dreaming about it. Now that I think about it, it actually really pisses me off just how pathetic you are."

Tears rolled down my cheeks, and my entire chest hurt, as if she had just stabbed me. Worst of all, I knew she was right. I wanted to try and argue with her, but I couldn't come up with anything that didn't sound pathetic.

We drove the rest of the short trip in silence, until Tess came to a halt at the Port Annabel Mall. She pulled the handbrake, but neither of us moved. Tess pulled a kleenex out of her purse, grabbed my chin, and started dabbing at my cheeks.

"I'm sorry, Henry. I didn't mean to yell at you like that. It's just... I have a lot on my mind right now, and I guess I took it out on you."

"What you... what you said... you're right," I stammered. "I am pathetic."

"I know, but I could have been nicer about it. Guess I'm not that good at being a big sister, yet." Tess stuck the kleenex back in her purse, gave me a quick peck on the lips, and said, "Come on, let's get you some clothes. It's gonna be fun!"

She got out of the car, and I was left confused, hurt, and even more confused. I could still taste her lip balm on my lips, and desperately tried not to forget what her mouth had felt like. Soft, and warm, mostly. Apparently it was possible to feel like shit, and have an erection at the same time.

I unbuckled, and followed her inside the large building. I normally did all my shopping online, and it had been a long time since I've actually been to mall. Everything still looked like I was used to, though. A lot of stores, a lot of ads, and a lot of people. Tess navigated the crowds perfectly, leading us to a smaller store titled "Sarah's Boutique" in fancy cursive script. It was located at the end of the one the mall's large wings, and seemed almost deserted from the outside.

"It's one of my favorite stores," Tess commented as we entered.

Inside, the buzz of the crowd was muted, and it felt like a tiny little safe space in an ocean of people. The store seemed to be entirely dedicated to women's fashion, which didn't surprise me, but still fascinated me. The few times I've gone shopping for clothes, it was in the men's department. Suits, shirts, pants, arranged in neat rows, ordered by color, and manufacturer. Sarah's was different. There seemed to be no discernible pattern to the way the clothes were arranged, and no end to the veritable rainbow of colors represented everywhere. In its own special way, it was magical, and I felt strangely comfortable in the place. Two teenaged girls were off to the side, pouring over a bin labelled "30% off."

"I thought that was you! I've missed you so much, Tess," came the cry of an older, brunette, well dressed woman, who rushed over to us, and embraced Tess in a fierce hug.

"Good to see you, Sarah," laughed Tess, and I connected the dots. The woman must have been Sarah, from Sarah's Boutique.

"Who's your friend?" asked Sarah. She pushed her thick, horn rimmed glasses back up her nose, and looked me up and down, with the critical eyes of a professional.

"That's my little sister, Henrietta," explained Tess matter of factly. "Actually, that's why we're here today. People keep confusing her for a guy, so I want to get her some nice clothes."

"I'm not surprised, dressed like that," mused Sarah, with a twinkle in her eye. "Don't worry, we'll find something to make you look adorable," she added, looking at me.

There was no, "But Tess, that's clearly a guy," or "Tess, you're obviously mistaken." No, she didn't even seem to question it.

"What size are you, dear?" inquired Sarah.

"Uh... I don't—" I stammered.

"She's about my size," Tess cut in, and I was grateful she saved me from the embarrassment. "Except up here," she added, gesturing towards my chest.

"Is there anything you're looking for in particular?"

"We need everything. Socks, panties, skirts, shirts, blouses, jackets, bras, maybe even a stylish hat. Hell, even shoes," listed Tess. "Complete makeover, and as cute as you can make it."

Sarah's eyes lit up like christmas had come early, and immediately dashed off deeper into the store, plucking garments from racks here and there, quickly gathering a whole pile of clothes on her arm.

"Tess... how much is this going to cost?" I asked, quietly. I was pretty sure I already knew the answer to, "And who's going to pay for it?"

"Don't worry about it, sis," Tess replied, and playfully dabbed me on the nose. "You're gonna be the cutest little munchkin ever!"

"That's not what I asked!" I protested, but Tess ignored me.

"Come on. I don't think you're gonna be of any help picking out clothes, so you might as well just wait in the cabin."

Tess pushed me into one of the empty rooms in the back of the store. The cabin was surprisingly big, with a bamboo floor, a coat rack, a big bench on one side, and a floor to ceiling mirror on the other. I've seen smaller dorm rooms.

"Start getting undressed, I'm gonna help Sarah," instructed Tess, and closed the door behind her.

I sighed, sat down on the bench, and pulled off my shoes. What the hell had I gotten myself into? Blackmailing me into stripping naked in front of Jay was bad enough already, but now they're also planning on just spending my money. What would come next? Hey, maybe they'd start doing my job, next. That, I could live with.

I pulled out my phone to check the time, and was greeted by Jay's massive cock. A little over an hour, before I'd be expected back at work. How many girls had Jay fucked with that thing? Probably a lot. If you had a tool like that, you'd make sure to use it. He probably didn't even have to masturbate. If he wanted to cum, there'd probably be a line of girls queued up to do it for him.

"It's gorgeous, isn't it?" commented Tess, and I nearly jumped out of my skin.

"I wasn't looking at it, I was just checking the time," I defended myself.

"Sure thing," laughed Tess. "It's cock o'clock."

Behind her, the door opened again, and Sarah barged in carrying a mountain of clothes. She dumped it unceremoniously on the ground, pushed her glasses back up her nose, put her hands on her hips, and looked extremely proud.

"Why is she still dressed?" she asked.

"Off with your clothes, sis," instructed Tess.

Neither of the women made any sort of indication they were going to give me privacy. "Can't she wait outside?" I asked Tess, indicating Sarah.

"Now, now, Henrietta," chided Sarah. "There's no need for false modesty. It's just us girls here."

"But—"

"You heard her. Get naked!" interrupted Tess.

I sighed, got up, and pulled my shirt over my head. No comments about how I didn't have any breasts, or there was a patch of hair on my chest. I unbuckled my belt, and pulled down my pants, revealing my briefs.

"Ready," I announced, hoping it would be enough.

"You should know better by now," replied Tess, as the two women waited expectantly.

"Please..." I begged, even though I knew it was of no use.

"Do you need me to do it for you?" threatened Tess, with a raised eyebrow.

"No," I sighed, and pulled down my briefs.

"Oh my," announced Sarah, and for just a brief moment I hoped that finally someone would question the whole "Henry is a woman" thing. "That is... smaller than I expected."

"I know," chimed in Tess. "I don't think I've ever seen one that tiny."

"And she's quite hairless, too. You're lucky."

I looked down, and thought otherwise. Ever since I was fifteen, and realized that I wasn't like the other boys, I started trimming my pubic hair. I read somewhere online that if you trim, it would make your dick appear bigger, and I needed a lot of help in that department. At first I just used scissors, trying to get as much hair away as possible, and once I got older, I started using an electric razor, touching up once or twice a month. I was by no means hairless, especially on my lower legs.

"How old is she?" inquired Sarah.

"About two days," answered Tess.

"I'm twenty-five," I offered, but neither of them were listening.

"Wow, she's moving along quickly."

"I know. She's a natural." Tess sounded almost proud of that fact. "Anyway, you wanna get started?"

"No," I replied lamely.

"Sure," said Sarah, and picked up the topmost piece of clothing. "Let's start with the panties."

She presented me with a bright pink g-string, and I took a deep breath before accepting it. It was way too thin, and my balls protruded on either side of the thin fabric. Of course, she had plenty of other options available. I didn't even recognize all the different cuts, as Sarah handed me underwear after underwear. My favorite ones were the the regular type, the ones that looked almost like my own briefs. Tess insisted on something "sluttier," though, and of course her opinion was the deciding factor.

Ultimately, she ended up picking out a few briefs, some thongs, and a couple of not-quite-so-thin g-strings in various shades of pink, and black. Her favorite pair was a pink g-string with white frills, and the word "SLUT" in sparkling beads on the front.

"Keep that one on, for now," Tess said. "I think we're good on panties. Did you find a bra?"

"Sort of," replied Sarah. "Most of ours are for bigger women, but I have a small selection of training bras."

The training bras turned out to be nothing like Tess' had been. Their cups were much smaller, and they actually held against my skin. Of course, without actual breasts, no matter how small, they looked off.

"Hmm, they don't fit too well, do they?" Tess echoed my thoughts.

"Figured that might happen. Check these out," offered Sarah, who procured a couple of flesh shaped discs, and handed them to Tess.

"Take a look, Henry." In her excitement, she actually called me by my name.

The discs turned out to be skin-colored breast insets. Tess lifted my bra, and pushed a set of them underneath. They were heavier than expected, and the unfamiliar weight felt strange. I looked in the mirror, and stared at the figure that almost looked like a girl. My "breasts" were tiny, barely an A cup, but they definitely gave my form a feminine quality.

The only thing that disturbed the image was the soft fuzz of hair on my chest. I didn't know why, but at that moment I felt a strong urge to shave it off, just to see what it would look like. I've seen hundreds of porn stars and amateurs that had a similar body type, and I couldn't believe mine was that similar. How had I failed to notice that for so many years?

"Damn," commented Tess.

"Damn is right. She's gonna make one hell of a cute chick. Can you believe I'm actually getting turned on a little? It's been years since Luke... you don't mind if I play with her for a bit?" Sarah asked.

"Go ahead," allowed Tess.

Before I knew what was happening, Sarah stepped up behind me, put her head on my shoulder, and wrapped her arms around me. She smelled of wildflowers, and her breath tickled my neck. One of her hands ran across my stomach, while the other caressed my thigh. I watched the whole thing happen in the mirror, scared, but also excited.