(Exclusive Jan 2025)

(All characters are consenting adults)

I Shouldn’t Have Worn Her Clothes II (Good Ending)

After a prank backfired, I was left sitting in my room, trapped as a busty woman trapped in a very tight and very hot latex suit, that was rubbing against my new vagina more with each moment that passed.

My only options were to masturbate and orgasm as a woman, which was incredibly embarrassing, emasculating, and something I don’t I’ll ever forget, or apologize to my sister, promise in writing to leave her alone, and lastly replace all her clothes that I stretched out.

“Dammit, this sucks. No matter what, I'll be humiliated and she wins…” I drop backward onto my bed, which causes my breasts to bounce, while also rubbing my erect nipples. “OoOOOhh!” the sensation caused me to moan.

I quickly cover my mouth but then hear laughter coming from outside my room. I take a deep breath. “Get the hell out of here Cali!” I yell from my bed. “Fine, fine. You’re a young woman having her first experience. I’ll give you privacy.” She yells back through my bedroom door.

I take a deep breath and sit back up. “It seems I have to make a choice. Masturbate and get out of this body. Or put up with it, swallow my pride, and go shopping in it, which while a lot will leave my manhood intact.” I take one more deep breath as I decide.

I placed my hand on my crotch and the sensation of it was too much for me. “I… I can’t do it…” I feel incredibly embarrassed. “It seems I have to give in… Which honestly might be for the better. Maybe it’s time to stop fighting with Cali all the time.”

I stand up, doing my best to ignore the sensations and slight desperations to relieve my frustration and open the door. I then walked over to Cali’s bedroom and knocked on the door. “Hey, Cali,” I said while knocking on the door.

I hear her get up and walk over to the door, then as she opens it. In her hand was her phone, almost like she had it ready and waiting for something. “Yeah? What’s up, sis.” She says looking quite surprised and slightly disappointed.

“I’m sorry… I really am, and I think it’ll be a good thing to stop fighting and pranking each other.” I said clearly defeated. Cali again seemed surprised. “Re… Really? I didn’t think you’d actually apologize.” Cali said as she put her phone in her pocket.

“Yeah, I wasn’t sure I would either. So, do you have a paper ready for me to sign or do we need to get one?” I ask hoping to get most of this out of the way, get out of this suit, and never think about being a woman again.

“Uh, no actually, but I can tell you’re sincere, so let’s just skip that and go shopping,” Cali said as she clapped her hands excitedly. “Alright, I’m ready whenever you are,” I said, not sure that I was actually ready to go outside as a busty woman in tight latex.

Cali smiled and grabbed her purse, while I grabbed my wallet. I just ended up giving it to her to put in her purse since I don’t have pockets. After that Cali drives us to the mall and we head to her favorite store, Tailored Girl’s.

As we walked through the mall I noticed nearly everyone staring at me. I sighed. “What’s wrong sis?” Cali asked, seemingly genuinely concerned. “Don’t call me sis…” I said slightly annoyed, but then decided to tell her. “It’s just… everyone is staring at me…”

I then look down at the suit. “They must love seeing a woman wearing this thing while walking around.” Cali shook her head. “I hate to break it to you sis, but while that does add to it, they’d be looking at you no matter what.”

I raised an eyebrow. “Really why?” Cali then laughed. “Because you’re a beautiful young girl. Even more so than me.” Cali wasn't looking at me when she said that, which was good because my face turned bright red from being embarrassed, but I also smiled for some reason.

I put my hands behind my head. “I mean I guess I’m hot, but more beautiful than you? I’m not sure about that. I mean you look exactly like mom.” I looked away when I said that, though I’m not entirely sure why, perhaps because I didn’t want her to know I meant it.

Cali laughed. “Yeah I’m told that a lot, and she sure was beautiful, but you know… You now look a lot like her as well.” We both got silent after that. Perhaps because we knew it was true, or merely wanted to give a moment of silence for our lost mother.

The silence made me think. We used to be so close before losing her. It seemed like our mother was the glue that held us together and without her we became enemies. I may not be exactly thrilled to have been turned into a woman, but perhaps this was what we needed in order to repair things.

We arrive at the store and head inside. “Alright time to do some shopping. Tell you what Tracy. We’re about the same size, so go around finding things that fit you and then bring them to me please.” Cali said in a genuinely nice way.

I sighed. “Don’t call me Tracy. But yeah, that seems okay. It’ll get us out of here quicker.” I said to Cali as I walked off. I go around looking for clothes similar to what Cali would wear. Some black punk t-shirts, a few tight dresses, fishnet leggings, and even a lace bra and panty set.

Once I had a nice pile I went and found Cali. “Here we go, a nice pile of things that looked like what you had in the closet,” I say to Cali as I place them on the changing table in the changing room she was about to enter.

“Great job sis! This stuff is great. I can’t wait until we try them on.” Cali said as she grabbed my hand and pulled me inside the changing room. She then locked the door and undressed in front of me. “Cali, come on! That’s gross.”

She rolled her eyes. “We’re both girls right now so it’s not weird. Just hand me some clothes and you won’t have to look long.” I nod and start hanging her things. She starts with the underwear. “Wow these are great, but I think I need another view of them.”

She says as she turns toward me. I immediately realized what she meant. “Do.. Do I have to?” She nodded and I feel it’s not even worth the protest. So she took the bra and panties off and helped me get into them, which wasn't so easy since I was stuck in the latex suit.

Once they were on she walked around me inspecting them. “Wow. I didn’t think they looked good on me, but on you, they look great.” Cali said before suddenly turning around and grabbing more clothes. I felt myself blushing from the compliment so I didn’t realize she was grabbing more.

“Here put this on as well,” Cali said as she handed me a dress. I was still gushing over the compliment that I didn't even think before putting it on. So I ended up wearing a very short, tight black dress, though not as tight as the latex.

“Yup, definitely buying that. Alright take it off and try this one.” Cali said as she began to throw more clothes at me. I didn’t protest, perhaps because I was slightly enjoying it. After trying on what felt like half the store, we finally left the changing room with a bunch of clothes we agreed were the best.

We brought them to checkout. “Hey, sis. Can I have my wallet so I can pay?” I said as I reached my hand out. Cali looked at me, opened her purse, and then pulled out her own credit card. “I thought you wanted me to pay for it?” I asked confused as she swiped her card to pay.

“I did too, but today was fun, and I’m no longer mad. So let’s just say you paid me back by being my beautiful model and lovely sister for the day.” Cali said, smiling at me. I blushed and couldn't help but smile back. “If you’re sure… Thank you, Cali today ended up being fun.”

“Yeah, it was,” Cali said as she grabbed the bags of clothes. The two of us then slowly made our way out of the mall, but Cali suddenly stopped. “Hey, can you hold these bags and stay here for a moment? I need to go get something real quick.”

I nod, take the bags, and watch her run off like a kid in a candy store. She ends up coming back several minutes later holding a bag. I wanted to ask her what was in it, but she was clearly trying to hide it, and the last thing I wanted to do was start a fight now that we were seemingly friends again.

Once we were back home I helped Cali put the new clothes in the wash. After that, she told me to wait in the room and she’d come in and unlock the suit. I sat on my bed and waited a few minutes. “Sorry for the wait, sis,” Cali said as she came into my room.

“It’s not a big deal. I’m sort of getting used to being like this. Though I’d still prefer to get out of this suit soon. It really is hot.” I said before we both started laughing. Cali then pulled out a small device. “Here you go. Press this on the suit and it’ll unlock.”

She placed it on the bed next to me, then pulled out the bag she got last minute earlier. “Or you could use this and masturbate.” She pulled out a small magic wand. “If you do… Your transformation will become permanent, and you’ll stay as my sister.”

Cali seemed nervous while saying that, and when I tried to ask her about it, she stopped me. “You don’t need to say anything. Choose whichever one you want. No matter what, I hope afterward, we can still be as close as we are today.”

Cali then turned around and left my room, closing the door on the way out. “If I would have masturbated… I would have gotten stuck as a girl. That’s crazy. I’d probably be very angry and want revenge, but now I…”

I gulped as the thought entered my mind. “I might actually want to stay like this…” My face heated up again and I felt so conflicted. I spent the next several hours holding the device that would turn me back into a man, and the one that would seal me as a woman.

I thought about how things have been, and how today was. Someone, today was better than every other day combined. We were both happy, we connected, had fun, and got cute clothes… Would that go away if I was a guy again? I didn’t know, and I couldn’t make a real decision.

So I decided to let fate choose. I put both devices in the bag and shook it around. “Alright, the first one I touch will be what I pick.” I close my eyes and stick my hand into the bag. I touch one of the devices and pull it out. I then open my eyes and see the magic wand.

“So It’s a life as a woman… and as a sister,” I say feeling a bit relieved. It seemed this was the outcome my heart really wanted. I toss the bag on the floor, sit back, and press the magic wand to my crotch. I then turn it on and not long after I’m moaning.

Then not long after that, I had my first orgasm as a woman, and with it, I sealed myself inside this female body. As soon as I was done and catching my breath I heard my sister cheering in her bedroom. I smiled and got up.

I checked the suit and it came right off. I then head to the shower to clean the cum off of myself, and while I’m inside my sister sneaked in and left me another present. When I got out, I found one of the cute outfits I helped pick out waiting for me, panties and bra included.

“I think things will be better this way, and I’m really glad to have this chance.” I then take the clothes and get dressed, before stepping out and greeting my sister as her sister for the first time. I know things are going to be better, and from now on we’ll be there for each other.