A couple weeks had passed and everything seemed to be going great! Obviously Mel didn’t have much time during the week, due to class, but the weekends were ours. We were having a lot of fun together. On this particular weekend, Mel kept her promise from our first date and we went shopping together. Since neither of us had much money, we settled on a local thrift store for the trip. I was extremely nervous, I didn’t want anyone seeing me like this! But she reassured me, no one would care. It was just a thrift shop, all second hand stuff. No one paid attention to places like this, let alone the people who worked there.

Still, I was apprehensive. This was my first time ever buying girl’s clothes for myself after all. Mel on the other hand, seemed excited at this! A bit too excited if you ask me. Together, we went through the racks of clothing. She grabbed anything that was feminine and looked like it might fit me, much to my embarrassment.

“Mel,” I said quietly. “I don’t have a ton of money here. I can’t buy all of this!”

“Oh relax, would you?” she said, dismissively. “We’re not buying everything. We need to figure out your size, and that means trying things on. Plus, this gives you options. You don’t know your style yet, so let’s figure it out together.”

I blushed, but she had a point. It seemed I had no choice but to try these things on. Once we finished picking out what felt like half the store, we went over to the changing area. Nothing amazing here, just a couple of small rooms with, thankfully, full doors covering them. I carried the mountain of clothes inside one of the open rooms. Mel would wait for me just outside the door. I took a deep breath as I set everything down. This was it, the big moment. I was about to wear women’s clothes for the first time in six years. Question was, where to start?

I looked over the gigantic pile to try and find something reasonable to start with. Yeah, that was it. Start small and work my way up. No use in stressing myself out over this. I found a white shirt that was fairly androgynous, if you ignored the pink, glittery letters that spelled out “Princess” across the chest. I took off my shirt and tried it on. It was a tad snug, but otherwise not a terrible fit. I grabbed a pair of jeans she picked out and tried to put those on. Were they supposed to be this tight? I just barely managed to get them on and buttoned up. 

Alright, moment of truth. Time to see how I looked. I went over to the mirror on the wall there and saw myself. My face turned a deep red. I was actually doing it, I was wearing girls’ clothes again! This time, no one could yell at me or freak out. Mel had made sure I was safe. The shirt was actually pretty nice, though the jeans didn’t leave much to the imagination. Not that there was anything to see really. They were difficult to move in and were extremely tight around my lower extremities as well. I took another breath, as best I could, and walked out to show Mel.

“So, um, what do you think?” I managed to ask, my face a deep shade of crimson.

“Oh my gosh! Look at you!!! You’re adorable!” she squeed. “I love that shirt, it really suits you! Those skinny jeans may not be the best look on you though. Some guys can rock them but you don’t really have the body for them. Oh well, it was worth a shot. Go ahead and take those off, there should be better fitting ones in there.”

Relieved, I went back into the changing room and practically tore the jeans off. Finally I could breathe again! I threw them aside, starting what became a reject pile. I fished out another pair of jeans from the pile, which looked like they would fit better. Still a women’s cut though. I got them on and looked into the mirror once more. Not a bad fit! Between the jeans and the shirt, I was starting to look cute! 

But one look at my face ruined that instantly. Same old guy face, even the mustache I had shaved off was growing back in. I sighed. Why couldn’t I be pretty, like all those guys I’d seen online? Granted, most of those were anime characters and created by artists, they weren’t real people. Still, I couldn’t help but feel a twinge of jealousy at it. Damn it, the feelings were starting to come back. I had been able to suppress them, more or less, by not actively dressing up and trying to focus on other things. Now that I was back and wearing the clothes again, they were returning in full force. I had to push them down so I could just enjoy the moment. I went back out again.

“Oh yes, much better!” she nodded. “You look really cute. How do you like that shirt? You haven’t taken it off”

“Um yea, it’s a nice fit and well, cute too. But I don’t know if I wanna buy it. Kind of difficult to pass it off as something a guy could wear.” 

“We’ll call it a maybe for now. Try on a different shirt and this time, put on a skirt. I wanna see those pretty legs of yours,” she grinned.

“You mean my hairy ass legs that I’ve never shaved?” I quipped.

With that, I went back into the changing room once more. It was time to try on more outfits. A pink graphic tee featuring Sailor Moon characters, with a black, pleated skirt, cute! Definitely a keeper! White crop top with a black miniskirt and belt, too punk. Into the reject pile it went. A lavender gingham dress with a ruffled hem, extremely cute! Buying that for sure! An anime themed hoodie and women’s jeans, a nice combo. Good for the cooler weather coming soon. A red, long coat to go along with that, definitely keeping me warm in the winter. A purple tunic, with matching skirt and some leggings, not bad. Those went in the “maybe” pile.

On and on it went until we arrived at the last outfit, this beautiful pink dress. It reminded me so much of the dress that started all of this, with its puffy sleeves and ruffles. Whomever donated this was either an idiot, or a godsend. My hands shook nervously as I pulled the garment over my head and placed my arms inside the sleeves. I was having flashbacks to my first time crossdressing, the memories were so vivid! Tears started flowing down my face, I couldn’t tell if they were because I was so happy to wear this or if it was the memories messing with my head. No matter, this feeling was incredible!

After a minute or so, I pulled myself together and went out. Mel gasped at the sight. “Oh my gosh!” she exclaimed. “You have got to buy that! You look so adorable!”

I checked the price tag, fifteen dollars. Not bad, considering something like this could easily retail for over a hundred! By now, the “keep” pile had gotten a bit big. I considered maybe giving something else up in exchange for the dress. I picked an outfit I had been rather iffy with anyways and moved it to the “reject” pile. Anything left in the “maybe” pile was moved there as well. With that, my shopping expedition was complete! I now had a good selection of girl clothes! I came out with the clothes I had chosen, though I would need help carrying all of them. Plus I really didn’t want anyone to think I was buying them for myself.

The lady at the checkout counter was pretty nice, she seemed to accept the excuse that these were all for Mel. In the end, the price came out to just over $100. Not bad for this many clothes! Still, that was just barely within my budget. We paid and loaded everything into my car, before hitting the road back to her dorm. I was so excited! Finally, my own clothes! I could dress up whenever I wanted! At least when I was with Mel. I looked over at her, then at the pile of clothes in the back seat. I couldn’t wait to get them back to the dorm!

When we finally got to the dorm, Mel ran in real quick to get one of her moving boxes. It would be so much easier to bring in the clothes and store them this way. Hopefully Liz wouldn’t mind too much! I was still keeping this private for now, our little secret. I was too embarrassed to let others know in real life, besides Mel of course. What we had here felt special. She was the first girl to accept me for who I really was! How could I not love her? She was perfect for me! Ok, maybe not perfect. A little rough around the edges. I could handle that though, I could easily fix what was wrong. I took a psychology course at college and everything, I knew plenty on this stuff.

Suddenly, I was snapped back to reality by Mel’s voice. “Michael? Are you listening?”

“H-huh? What?” I stammered. “Uh, sorry. I kinda spaced out for a minute there. What were you saying?”

She sighed and shook her head. “Pay attention, would you? I said Liz isn’t in the dorm right now. We can get everything up there and stored away before she gets back.”

“Oh, right. Uh, let’s go then.” I said, as the two of us started packing everything up.

Once we had it all up in the room and safely stored away, we sat on the bed together. She smiled at me and rested her head on my shoulder.

“This is nice, just the two of us. I wish you hadn’t cut your hair though, it’s too short to do anything with. I can’t even play with it properly. You need a wig if you want this to look right.”

“Hey now,” I said defensively. “I just spent a hundred bucks at the thrift shop! I can’t afford to get a wig too! This is getting too expensive, Mel! I need to actually save some money here. I barely make anything as is, this stupid job barely gives me any hours and the pay is shit. That was basically everything I had for right now!”

“Beauty isn’t cheap Michael,” she scoffed. “Do you wanna look like a guy while wearing those clothes or do you wanna be pretty? I’m the one storing them for you here! I don’t have to do that, I’m being nice. Least you could do is get a cheap wig to go with it. Halloween is coming up, I think I saw one of those costume stores open up at the mall. We can go there and get you one.”

She made a good point, surely a costume wig wouldn’t be too expensive. But that would have to wait for another time, I didn’t have a lot of money left and my parents were expecting me home for dinner. So I had to get going. We hugged and shared a kiss, then I got into my car to leave. This had been an amazing day! So much fun! I sighed contently before starting it up and headed for home.

The drive home was fine at first, just listening to music and doing the typical half hour trip back. However, as I went along, my mind began to wander. I started off thinking about everything we had just done and how fun it was, but then my mind suddenly turned back to “it”. The promise I had made to Tara all those years ago. What did I just do? Not only had I broken that very promise I made, but I did so blatantly! I vigorously tried on so many women’s clothes, even purchased a bunch of them! What was I thinking?! How could I betray her like this? I was so pathetic! What the hell was wrong with me? Why couldn’t I just be normal for once in my stupid life?!

By now, I was sobbing so hard that I had to pull over. I was in no shape to drive, not like this. Fuck me, why now? I just had such an amazing time and yet, all I could feel was guilt and shame over it. What could I do? Should I apologize? But she had no way of knowing that I did this, not unless I told her. Maybe I could keep it a secret? Yea, cause that worked out SO well the last time! I was just so confused at this point, there didn’t seem to be any right answer. So I just sat there, crying for a bit.

Once I managed to compose myself a little, I started to make my way home again. My parents were probably wondering why I was late, I could just make up an excuse about traffic or an accident on the way back. Not like they would know any better. When I finally reached the house, I had to do a double take. There was an extra car in the driveway! It looked familiar, but I couldn’t place it. I figured Mom and Dad must have company over. No big deal, that wasn’t completely unusual. So I parked my car and headed inside to see who it was.

“Mom, Dad, I’m home!” I said as I walked in.

“Heya Mikey!” A familiar, yet unexpected voice greeted me.

I froze dead in my tracks. I knew that voice, but there was no way, right? How could she be here? Now, of all times! My fears were confirmed as she rounded the corner.

“Nice to see you again little bro,” Tara said as she approached. 

No, this couldn’t be happening, why now?! Just like that, I was a kid again. Standing there, mouth agape and looking like a deer caught in headlights, just like the time she caught me in her clothes. My throat was dry, I couldn’t move or speak. Why was she here? Did she know? How? There was no way! Then why? My mind was racing a mile a minute while my body just stood there, frozen. Finally, she spoke up.

“Hello? Michael? Everything ok?” she said, waving her hand in front of my face. That made me snap back to reality. I had to push my feelings down for now and act cool.

“Oh uh, h-hey Tara,” I managed to spit out finally. “What are you doing here? I mean, um, not that you’re not welcome here, just, uh, wasn’t expecting to see you is all.”

She looked at me with concern for a moment, before coming over and giving me a hug. “It’s good to see you again little bro. I was feeling a bit homesick and I got nothing going on this weekend. Plus Samantha is out of town for some big concert thing. So, I figured I could come home for the weekend. We can catch up, have some sibling bonding time and stuff! How does that sound?”

I was, obviously, a bit hesitant. The whole weekend? With the last person I wanted to see right now? Yea, that sounded wonderful!

“Oh sure Tara, sounds like fun. I’d be happy to catch up with you and stuff.” I said, plastering a fake smile on my face. “I, uh, just came back from visiting my girlfriend. You know, just the two of us, hanging out at the mall and stuff. It was a nice time.” I really hoped she would buy it.

“Oh yea! You said something about having a girlfriend now! Look at you, all grown up and going on dates! You’d better be treating her right, like a proper lady. Come on, let's go in the living room and you can tell me all about her!”

Reluctantly, I went with her. Hopefully, if I left out how I broke my promise, we could keep things relatively normal. So we sat down and I told her about Mel. How we had similar interests, we both loved Pokémon, anime and all that stuff. She was such a sweet girl and even outside of our other activities, we really had a good thing going here. We both really did love each other. 

Though I had to admit, she wasn’t perfect. She was prone to having these fits when things didn’t go her way. Things could be going great and when the smallest thing went wrong, it was like her personality would just shift. She could be happy as a clam and all of a sudden, she’d be completely depressed, thinking everyone hates her. I didn’t get it, but I put up with it. That’s what a good boyfriend does, right? I could help her overcome it. Surely with enough love and support, she could get better.

“Enough about me,” I said. “I wanna hear more about how things are with you! What are you doing for work these days, how’s Samantha doing, stuff like that? You never talk about your life anymore, and I kinda miss that.”

It was true, I did miss talking to her. Even if the timing couldn’t be worse here, it was kinda nice seeing her again. At the same time though, this was a good strategy to get the attention off of me. I could relax a little bit and maybe build up my resolve to keep this a secret. Finally, she spoke up.

“Ah well, things are fine,” she said. “I’m actually a student teacher at our old high school now. Did you forget? I got my bachelor’s degree in teaching. Samantha is fine, we still share an apartment. She actually started a relationship not long ago, nice girl. I hope it works out with them. The two of them are off at a concert together. They offered to bring me along, but I didn’t wanna be a third wheel.”

“Whoa, slow down a second. Did you say she’s dating a girl?” I inquired.

“Oh, yea. Whoops. Probably should have mentioned, she’s a lesbian. She likes girls. Go figure, right?”

“You say that so casually, I’m surprised. You’re ok with that? I mean, I don’t have any problems with it myself. My manager at work is gay, I think. Jarod’s really tough to nail down.”

“Ha! You’re not wrong there.” she laughed. “Jarod’s a bit weird, I still don’t fully understand them myself. But they’re actually pansexual, they’ll date anyone regardless of gender. Pretty cool actually, I only recently learned that term. But yea, I fully accept Samantha. She’s my BFF, that wouldn’t be the case if I didn’t.”

“Wait wait wait! You know Jarod? But how?” I asked, very confused at this point. “They’ve never mentioned you at all, yet you talk like you two are best buds or something. What gives?”

“They haven’t? I’m surprised,” she said. “I’ve known them for a couple years now. We actually met the day you got your appendix out, Samantha introduced me to them and a few others. They were actually a pretty tight knit group, and yet let me in with no hesitation. I’m still surprised, considering I’m so different from all of them.”

“What’s that supposed to mean exactly?” Now she had me curious.

“Ah, I’ve probably said too much already. It’s not my place to talk about these things. If you wanna know more, ask Jarod. Point is, they’re a good friend of mine.”

“Whatever you say sis. So while I was having my appendix out, you were off having fun and making friends?”

“You make it sound so harsh,” she said, sounding slightly annoyed. “I only found out you were in the hospital as we were headed out to get food. I dropped everything the second Mom called, so I could come see you. But it took me a while to get to the hospital and by the time I got there, Mom said you were already being prepped for surgery. I came back the next day, remember?”

“Yeah, yeah, I remember that. Sorry, that was rude. I just meant, I had no idea that’s what you were doing. This is the first time we’ve really talked in a long time,” I said.

“Well there’s no time like the present, right? We’re catching up now, that’s what matters,” she said with a smile, though I noticed a bit of hesitancy in her voice.

It felt like she was hiding something here, something she wanted to talk about but couldn’t. Who was I to judge though? I was doing the exact same thing. It would be hypocritical of me to bring it up, since I was still hiding what happened today. We sat in silence for a minute, both trying to think of what to say next. Luckily, the tension was broken when our dad came downstairs. He was a tall man, dark but graying hair, bald on top and a mustache on his face. He came over and gave Tara a hug and started talking to her. I used this as a chance to slip away for now…

Chapter 6 End