Chapter 6: Chapter 6: Generosity

-Chapter 6: Generosity-

I was nervous when we got to the mall. Aside from not having been there in years, this would be my first time in public as a woman. Sure, there was the hospital and the drive-thru, but those didn't count. This was the real deal. Not to mention, I'd never enjoyed clothes shopping in the past, only adding to my apprehension. I realized as Anna parked the car, that I'd spent most of the ride with my teeth clenched. This was the moment of truth, and I could feel myself starting to panic. As things were beginning to get bad, I felt a firm but gentle hand on my shoulder;

"Hey, come on. You've got this! When you go out there, all anyone's gonna see is an ordinary woman."

"That's what I'm afraid of!"

Anna sighed quietly;

"Look, I don't know what you're feeling right now. What you're going through is totally beyond my experience. But, I do know you. I know you can sometimes have a hard time dealing with new stress, but once you learn something, it becomes second nature to you. I know you're a lot braver and stronger than you give yourself credit for. And, I'm gonna be with you the whole time. There's nothing weird about a couple girls going shopping together. So, trust me, this is gonna go fine. You ready?"

I took a deep breath;

"Yeah, as ready as I'll ever be. And… thanks, Anna."

She smiled and gave my shoulder a bit of a squeeze before getting out of the car. As we walked into the mall, I noticed a couple of people glancing our way, but nothing out of the ordinary. So far so good. We settled on shopping at JCPenny's. They should have pretty much everything I needed, and it wasn't like I had never shopped there before, so it would be less of a culture shock. The Forever 21's and Victoria's Secret's of the world could wait a while. I definitely wasn't there yet. What did come as a bit of a shock when we arrived was just how vast the women's section was. I'd passed by it plenty of times when I had been there in the past, so I knew it was bigger than the men's selection, but I'd never really taken stock of just how much larger it actually was.

We made a wide sweep. I thought it would be a good idea to start out light so I could get a sense of my size before picking out more. We went through tops, bottoms, shoes, underwear, and just about everything else you could imagine. By the time we'd gone through the store once, I think my head might have been spinning. Then, it came time for me to try things on. I'd been dreading that bit, mostly because I always hated doing it as a guy. You shut yourself in a stall that's either just a bit too small, or way too big, strip off your clothes, and hope the articles you've brought in both a) fit, and b) look good on you. Failing either of those categories means changing back, finding something else, and repeating the process as many times as it takes for you to find the right clothes in the right size. And, well, I've been over how I used to feel about my reflection. As a guy, having to stare at myself in the mirror over and over again might as well have been some kind of psychological torture. Okay, maybe that's a bit extreme, but the point is, it was never a good time!

As much as I'd been dreading it, however, the process of trying on outfits wasn't nearly as bad as I had remembered it being. Maybe part of that was the fact that my reflection, while still new and strange to me, didn't feel as alien as it used to, though I still couldn't figure out why that was. The other reason why it wasn't so unpleasant was that it was almost… fun. I really didn't have much reference for what my style would be as a woman, so I was really experimenting. I would put together an outfit, and if I thought it looked okay, I'd show Anna, who would, in no uncertain terms, tell me if it looked great or like an absolute nightmare (At least I could trust her to be honest.) Sure, the constant dressing and undressing was still a bit of a pain, but I wasn't unhappy. I might have even been enjoying myself. At the time, I chalked that enjoyment to the fact that I had been with Anna. I always had a good time when I was with her, and shopping with your best friend is genuinely fun. I didn't really consider that there may have been more to it than that.

The bras were a bit of a struggle. I fumbled hopelessly with the hooks before I finally got them figured out. Anna had told me how to put one on, but it sounded so much easier when she said it. The feeling wasn't all that unpleasant. The straps dug into my shoulders a little bit, but the cups felt great! It was a nice relief to have the support under my breasts, and they jiggled about a lot less once they'd been contained. It might take me a while to get used to wearing them, but having a bra there to keep the girls under control would definitely be worth it.

The occasional glances I'd get from other women as I went in and out of the changing room did make me a little uncomfortable. There wasn't much to their looks, though some of them did seem to be judging me. It was mostly the fact that I wasn't used to being seen as a woman yet. With that in mind, I was really glad Anna had taken my measurements at her place. Having a stranger in some boutique do it, or trying to do it myself would have been way too much for me at that point. After about a half hour of trying on clothes, I'd figured out my general sizing. I seemed to be middle of the road in most respects. Medium size tops, average waistband size, and so on. With that part out of the way, it came time to gather the rest of the clothes I'd be getting. And, at Anna's insistence, it was a lot.

Where to even start? There were a couple t-shirts, some tank-tops, a sweater, three different blouses, a flannel, some long sleeve shirts, and a crop top, if I'd ever feel so bold as to wear one. There were two hoodies, a denim jacket, a raincoat, and a cardigan. We'd picked out six bras and seven pairs of underwear of varying styles. There were three pairs of denim shorts, some athletic shorts, several pairs of jeans, some leggings, a pair of joggers, and multiple skirts of varying lengths. The shoes consisted of two pairs of tennis shoes, some sandals, a pair of boots, some flats, and a pair of heels I didn't even know how to walk in. Anna picked out some accessories; a necklace, a watch, and a bracelet, as well as a couple sets of earrings, even though I hadn't had my ears pierced yet. She also grabbed some scented lotion, perfume, and makeup, which she promised to teach me how to put on tomorrow. And to round it all out, she said I needed to get two sets of pajamas and a dress.

All of this would cost a king's ransom. There was no way on earth it'd be less than $500. I imagined it would be closer to twice that. Every time I'd try to talk Anna out of getting something, she'd grab two more items. I'd agreed to let her help me out, but this was way too much. And yet, whenever I'd try to get her to stop, Anna would insist. This was clearly important to her. Every time I'd start to feel guilty, she would place the responsibility on herself. She was doing this because she wanted to. I struggled to understand. I felt like I didn't deserve any of this, and yet she wouldn't back down. No one had ever done anything this generous for me before, yet she seemed happy to give so much. I was grateful. I was beyond grateful. I couldn't help feeling guilty, but I was truly grateful.

The expression on the cashier's face was one of awe when he saw the veritable mountain of clothes we'd collected. The magnitude of the display made me feel pretty self conscious, yet Anna just smiled as if this was the most mundane of exchanges. She vehemently refused to let me know the full price, but I definitely heard a seven followed by some syllables from the cashier. And, if that wasn't enough, Anna paid debit. Everything was done, then and there. In total, our haul filled eight bags, not including the shoe boxes. It's a small wonder we managed to even carry everything back to the car. By the time we left the store, it was around 6:00 in the evening, and the clouds were dyed a dark shade of purple by the orange glow of the setting sun.

We swung by my house to drop off most of the clothes and pick up my phone charger, a day's worth of my meds, and a toothbrush, before we returned to Anna's apartment. Upon our arrival, we set down our things, and took off our shoes. No sooner had had Anna left her bedroom than she began sifting through her pantry;

"I'm gonna make us dinner. You should go shower in the meantime."

"I don't suppose you'd let me help with the cooking, or pay you for the food, would you?"

"No, and no! I'm pampering you, and you're gonna like it, young lady!"

"I just feel guilty is all. You've been taking care of me all day today and yesterday. Plus, you just spent god knows how much money on me. It feels like I'm taking advantage of you."

"It's not taking advantage if I offered to do it!" she announced, waving a wooden spoon in my general direction. She turned to face me; "So just make this easy for me, and just let me spoil you, alright?" 

I hadn't really considered that trying to get Anna to cut back would be making things harder for her. If it were someone else, trying to get them to stop giving so much may have actually gotten them to ease up a bit, but when Anna set her mind to something, no force in heaven or on earth could stop her. Arguing was an uphill battle that would just waste both of our energy. So I relented.

"Alright, I get your point. And thank you. Seriously, there aren't enough words for me to express how grateful I am toward you."

She smiled, folding her arms and nodding triumphantly;

"Much better! Now be a good girl and go get cleaned up!"

"What about you?"

"I'll shower after we eat. Now off with ya!"

"Yes ma'am…"

So I did as I was ordered, and headed to the bathroom. I shut the door with a sigh. I was very tired. It would be a gross understatement to say that today had been a long day. And, while Anna is my favorite person in the whole world, I needed a few minutes to myself by that point. A relaxing hot shower sounded very nice. Her bathroom had a bathtub with a separate walk-in shower, which was a bit of a pleasant change from the shower in the guest bathroom I used at home. I stripped off the outfit Anna had given me earlier (no point in dirtying up the new clothes I'd gotten if we were just hanging out,) and turned on the water, waiting a few moments for it to warm up. Satisfied with the temperature, I stepped in and got to washing away the day's grime.

Showering my new body wasn't as strange as I had thought it would be. It definitely felt different, but not in a bad way. The soap and water ran over my skin a lot more easily now. I had always been fairly hairy as a guy. I never really liked it, but I didn't see much point in doing anything about it. The absence of body hair made everything a lot more slippery, but it was almost kinda nice. Shaving wasn't nearly as bad as I had feared it might be, either. I managed to run the razor Anna had lent me up my legs, and over my armpits without cutting myself. This might not sound like much of an achievement, but when you're as uncoordinated as I am, every small victory counts. 

I did, however, once again find myself distracted by my breasts. Like I said, my smooth skin made everything kinda slippery, and they were no exception. As I washed them, they shook and squished together, and I found myself becoming quite entertained. I don't even want to imagine how silly and immature I must have looked, but, you know what? Boobs are fun. I was having fun. I saw a post on some board once asking men and women to mention little things they enjoyed that the other sex missed out on, and I definitely remember 'playing with your boobs in the shower' being on there more than once. And, yeah, it was pretty great. I don't care how ridiculous I looked, I was by myself, having a good time. When life gives you lemons, right?

So I spent a couple minutes playing with myself. I giggled quietly, and fondled myself, and it felt good. It did feel good. And my mind got to wandering. People masturbate in the shower all the time. I hadn't ever really done it before, but what was the harm? I was alone. I was feeling pretty good. I had had a long day. I was in the mood. Why not? I was very curious about what my body had in store for me on that front, and, if nothing else, I wanted to start heading down that path. So I started slowly. I massaged my breasts, gently at first, then a bit more firmly. A warm feeling spread throughout my body, starting in the pit of my stomach, then gradually radiating outward. I could feel my breasts starting to swell, and my nipples hardened, aching ever so much. I gently squeezed my right nipple between my index finger and thumb, and,

"Mmmmm~"

It felt good. It felt really good, and I couldn't stop myself from moaning ever so quietly. There was a throbbing in my crotch. I felt flushed, and my knees were getting a little weak. This was… intense, and I could tell I had only just scratched the surface. I was beginning to feel a little apprehensive. If this was how it felt just starting out, what would it feel like to finish? I didn't know if I was ready for that, but I wanted to press on. I reached down, timidly running my finger across my labia. They were so, so sensitive, and I could feel a dampness that wasn't just the water. I pressed a little harder, rubbing both lips in a clockwise circle. I rubbed my vagina, and played with my breasts, and the sensations kept getting more and more intense. I went one step further, and stuck two fingers in myself.

"Ahh-haah!"

My knees knocked together, and I clasped my hand over my mouth to stifle my moans. Everything felt like it had been dialed up to eleven by that point. Even the drops of water hitting my skin were sending out little ripples of stimulation. Closing my eyes, I envisioned a fantasy. I was with another woman. Our nude forms pressed together and our legs tangled. I could almost feel the warmth of her body; her hot breath against my skin; her soft lips pressed against mine in a passionate kiss. I pressed a little deeper, and curled my fingers, and gasped into my palm. My heart was hammering in my chest. My breathing was fast and ragged. My legs felt like putty, and I had to brace myself against the wall to hold myself upright. 

I was at a crossroads. My body wanted me to keep going. To race across that finish line and claim that sweet release I had been chasing. But I was scared. I felt like I could collapse. I wanted to finish; to know what it felt like. But there was some part of me that felt like I shouldn't be doing this. A part that feared those fantasies were rooted in feelings I knew I wasn't supposed to have. The sensations and desires were so intense, and I had never felt anything like this before. But it was just… too much.

I tried to calm down. I focused on my breathing, placing a hand against my chest. I listened to the sound of the running water, and concentrated on the feeling of the droplets hitting the top of my head. And, gradually, I came down from that high. My heartbeat slowed. My breathing became more regular. My muscles relaxed. I let out a sigh of relief. On some level, I was glad to have enough control over my body and my urges to stop myself. I did want to venture down that road. I did want to find out what it felt like. But… not now. I wasn't ready, and it wasn't the time.

I returned to the task at hand. All that I needed to do was wash my hair. I'd kept it pretty short throughout high school and college, so getting it all clean would take some doing. I grabbed the shampoo, and stopped for a moment, when I realized that it smelled like Anna. Or, rather, Anna smelled like it, and now I was going to smell like Anna. Using someone's shampoo might not have been as high on my imaginary 'best friends checklist' as her giving me her underwear but it made me feel a bit closer, in a strange way. Like it was another personal thing we could share. Maybe that's weird, but it made me kinda happy, at least. And I could use a little pick-me-up after getting myself so worked up. Washing my hair took a good bit more scrubbing than I was used to, but once I was satisfied, I rinsed and felt content with a job well done.

Turning off the water, I stopped for a moment. I noticed, with some surprise, the distinctive feeling of individual beads of water running down my body and over my legs. With the body hair I'd had as a man, I hadn't experienced that sensation in as long as I could possibly remember. It was strange. It was such a small thing, but it was different. And I liked it. I stood there for a while, just letting the water run off me. I found myself smiling. I didn't understand why, but, for some reason, this tiny little experience was making me happy.

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After most of the water had rolled off me, I dried myself, and wrapped the towel around my hair. I put on some deodorant (also borrowed), and dressed myself again. Feeling dry enough, I hung my towel on the rack, my still damp hair sticking to the back of my neck, and opened the bathroom door to be greeted by the pleasant aroma of herbs and spices. Following my nose, of course, led me to the kitchen, where I saw Anna stirring a pot over the stovetop.

"Hey, that smells really good!"

She peeked over her shoulder, smiling my way;

"It's just curry with some chicken and a side of veggies. Nothing special, but hopefully it comes out alright! Should be done in just a minute."

"You want any help setting the table and stuff?"

"Sure, there are plates in that cabinet over there," she said, gesturing with her elbow. "There should be some glasses in the box in the corner by the fridge, too. You want anything to drink?"

"Water's fine, thanks," I replied as I grabbed a couple plates, having to stretch to reach them. 

I set the plates on the counter as Anna turned off one burner once the rice finished steaming. Collecting the glasses, I filled mine with ice and water from the fridge, and did the same when Anna asked for some, herself. As I set them at the dining room table, Anna turned, leaning on the counter and asked;

"So, Sophie, when you were in the shower, did you do any… exploring?"

I felt my cheeks grow hot even before I whipped around to face her;

"H-huh?!"

She grinned cheekily;

"I'll take that reaction as a yes."

"Wh-what?! No! I mean… I thought about- No!"

"Why not? Nothing wrong with taking a little me-time."

"I-I mean, it's not even my shower!" I stammered, looking away bashfully.

"Hey, I do it in the shower all the time."

"And you're just telling me that?!"

"Hell yeah, I am. You're missing out, sister."

"I, uh… I…!"

I was tripping all over my words, folding my arms indignantly;

"I'll do it, when I do it, alright?!"

"Mmhmm…"

I looked back to see her smiling at me, her smug, mischievous expression rubbing me in decidedly the wrong way.

"Wh-what's that look for?!"

Her grin widened a little more;

"Oh, nothing~"

I found myself whining at her response, my embarrassment rapidly approaching critical mass. Anna suddenly burst out giggling;

"Hehehehe! Oh god, Sophie, you're so cute when you're mad!"

I sighed. It seemed this was my new lot in life. At least Anna was having fun. I knew she wouldn't ever take it too far, but I had a feeling she would be turning her teasing up a notch for the foreseeable future. Mildly perturbed, I kept to myself for the few minutes before it came time to eat. When everything was ready, Anna called me over, and I served myself a plate of the curry and vegetables, sitting across from her at the dinner table. We chatted while we ate, laughing as we realized that neither of us ever really ate at the table, both preferring to eat in front of the computer. 

Much to my surprise, Anna managed to go the whole meal without teasing me. I made a point of praising her self control after the fact. I also praised her cooking, as the meal was delicious. In a rare moment of humility, she admitted she wasn't a great cook, but that she'd learned how to make a few different meals for herself and her roommates in college. She had prepared a bowl of diced fruits for herself to eat later in the week, but she said we ought to share it as a dessert. Grateful for the meal, I asked her;

"So, would you mind if I at least did the dishes? I wanna help out, even if it's just a little bit."

"Yeah, that'd actually be a big help, thanks!" she replied with a smile. "While you do that, I'm gonna take a shower."

"Sounds good!"

"By the way, if you wanna get changed, I left the pajamas you brought in my room. I think I'm gonna stay up and watch YouTube for a bit before bed, but I'll probably start getting ready as soon as I'm done in the shower."

"Gotcha. I'll change after I finish with the dishes."

"Alrighty then!" she announced, leaving for the bathroom. "Now, I'm gonna go enjoy some quality me-time in the shower!"

"Pervert!" I shouted as she shut the door.

I spent the next few minutes cleaning up. Putting the leftovers in a tupperware container, I scrubbed the pots, plates, and glasses. After drying everything, I returned the plates to the cabinet, leaving the rest on the counter, since I didn't know where it went. With that done, I headed to the bedroom and shut the door. I saw the bag with my clothes in it next to the bed, and took out the outfit I planned to sleep in; a set of light pink silk pajamas composed of a tank top and a pair of shorts. I had wanted to get something a bit less… effeminate, but Anna suggested that I ought to try leaning into it, saying it might make things easier. I was still reluctant, but Anna pressed the point and convinced me, as she often did. 

So, I took off my t-shirt and shorts, and slipped into the nightwear. And, oh my, was it comfortable. The material was so light and soft, it felt like I was wearing nothing at all! I couldn't help but marvel at how smooth and cool the silken garment felt against my skin. The shorts were a bit short for my taste. Not quite embarrassingly so, but definitely getting there. I turned to look at myself in the body length mirror Anna kept by her closet. What came as a surprise to me, even though it really shouldn't have been at that point, was how girly I looked in that outfit. The girl looking back at me seemed so dainty and small in those cute, lacy pajamas. The girl who was, as I have already firmly established, me. That connection was getting pretty firmly cemented in my head.

When I saw the girl in the mirror, I didn't see a stranger any more; I saw myself. And, those pajamas looked really cute on me. When I realized that, I felt happy. I was happy without reservation. This was me, and I looked cute, and that felt good. I liked feeling cute. I couldn't deny that feeling if I had wanted to, and by that point, I didn't even feel like fighting it. My appearance had started making me happy for the first time in as long as I could remember, but I couldn't understand the reason why. I was happy enough that I chose not to worry about it. I couldn't hide from the truth. I acknowledged it. I liked my body.

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