alsoashley

Part 1: Something’s Different About Ash - We hadn’t been back to Alaska in years. It was just the two of us, like always - me and Ash, best friends for as long as I could remember. So long that I could barely even remember when it was we were catching our first salmon and swearing we’d never grow up. But something was off this time. Ash was quieter, more reserved. The windbreaker he wore looked new - too nice, honestly, like it was hiding something. It also just seemed more... I don't know - girly than usual, if that makes sense. He didn’t want to change in front of me in the cabin we had rented - insisted we get a place with separate rooms this year. It wouldn't have felt like an odd request typically, but he just kept slipping into his room every time we got back from the docks. And he never took the windbreaker off, even when it was hot in the cabin. I should’ve just ignored it all. Should’ve let him have his weird little secret. But after a few drinks and frustration when he turned in so early for the night, I pushed open his door without knocking to finally confront him about it. And there he was. Lavender. Lingerie. Lacy little nightie clinging to him under the windbreaker. A matching thong. I froze. Ash froze. And then he whispered, “Please… don’t freak out.” #trans #tgirl #trap #femboy #feminization #pinup #lingerie #sissy #thicc #mtf #girlnextdoor #cosplay

Published: July 7th 2025, 2:27:36 pm

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Part 1: Something’s Different About Ash - We hadn’t been back to Alaska in years. It was just the two of us, like always - me and Ash, best friends for as long as I could remember. So long that I could barely even remember when it was we were catching our first salmon and swearing we’d never grow up. But something was off this time. Ash was quieter, more reserved. The windbreaker he wore looked new - too nice, honestly, like it was hiding something. It also just seemed more... I don't know - girly than usual, if that makes sense. He didn’t want to change in front of me in the cabin we had rented - insisted we get a place with separate rooms this year. It wouldn't have felt like an odd request typically, but he just kept slipping into his room every time we got back from the docks. And he never took the windbreaker off, even when it was hot in the cabin. I should’ve just ignored it all. Should’ve let him have his weird little secret. But after a few drinks and frustration when he turned in so early for the night, I pushed open his door without knocking to finally confront him about it. And there he was. Lavender. Lingerie. Lacy little nightie clinging to him under the windbreaker. A matching thong. I froze. Ash froze. And then he whispered, “Please… don’t freak out.” #trans #tgirl #trap #femboy #feminization #pinup #lingerie #sissy #thicc #mtf #girlnextdoor #cosplay

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Part 2: "Let Me See" I stood on the edge of the room, head spinning. Ash sat awkwardly in the lavender nightie, hands trying to cover what it barely hid. His face was flushed—humiliated. But there was no denying how hot he looked. He sat , trembling, then finally spoke: “You remember when I said I needed money?” Yeah, I remembered. He’d gone off the grid for a while. No texts, no calls. Just reappeared months later, saying he got ‘a gig.’ Turns out the gig involved agreeing to be feminized for an online subscription site - one that made damn good money if the ‘model’ leaned in. HRT, the clothes, only pushing further as he got hotter, the whole thing was mind blowing to me. And the more convincing he became, the more they seemed to want to pay. He looked me in the eye. “I didn’t think it would change me this much. I didn’t think I’d keep doing it after I made just enough for some bills. But… I kind of have to now.” My mouth was dry. My voice cracked. “…Let me see it again.” He hesitated. Then opened up the windbreaker. Showed me. Turned a little, you could tell he was used to showing himself off now, even if he wasn't trying to show off for me. It seemed so natural to him now. The lavender thong framed his smooth curves like it was made for him. I felt something I wasn’t expecting. #trans #tgirl #trap #femboy #feminization #pinup #lingerie #sissy #thicc #mtf #girlnextdoor #cosplay

Part 2: "Let Me See" I stood on the edge of the room, head spinning. Ash sat awkwardly in the lavender nightie, hands trying to cover what it barely hid. His face was flushed—humiliated. But there was no denying how hot he looked. He sat , trembling, then finally spoke: “You remember when I said I needed money?” Yeah, I remembered. He’d gone off the grid for a while. No texts, no calls. Just reappeared months later, saying he got ‘a gig.’ Turns out the gig involved agreeing to be feminized for an online subscription site - one that made damn good money if the ‘model’ leaned in. HRT, the clothes, only pushing further as he got hotter, the whole thing was mind blowing to me. And the more convincing he became, the more they seemed to want to pay. He looked me in the eye. “I didn’t think it would change me this much. I didn’t think I’d keep doing it after I made just enough for some bills. But… I kind of have to now.” My mouth was dry. My voice cracked. “…Let me see it again.” He hesitated. Then opened up the windbreaker. Showed me. Turned a little, you could tell he was used to showing himself off now, even if he wasn't trying to show off for me. It seemed so natural to him now. The lavender thong framed his smooth curves like it was made for him. I felt something I wasn’t expecting. #trans #tgirl #trap #femboy #feminization #pinup #lingerie #sissy #thicc #mtf #girlnextdoor #cosplay

Part 1: I met this cute boy at a coffee shop one winter nigh..

Part 1: I met this cute boy at a coffee shop one winter nigh..

Part 3: Don’t Pretend You Don’t Like This I didn’t say much at first. Didn’t know what to say. But Ash didn’t stop me when I reached out, tugging at the strap of the nightie. He just bit his lip and looked down, submissive. And that’s when I realized it - I had the power now. Ash used to be the loud one, the cocky one, the guy who always made the plans. But now? Now he looked up at me like he was waiting to be told what to do. I circled him slowly, eyes trailing every inch of his changed body. I couldn’t stop staring. The soft thighs, the smooth front hidden under satin, the delicate curve of his waist. “You like looking like this, don’t you?” I asked. He didn’t answer. “Good,” I said. “Because I like it too.” - and then I pulled him closer by the hips. #trans #tgirl #trap #femboy #feminization #pinup #lingerie #sissy #thicc #mtf #girlnextdoor #cosplay

Part 3: Don’t Pretend You Don’t Like This I didn’t say much at first. Didn’t know what to say. But Ash didn’t stop me when I reached out, tugging at the strap of the nightie. He just bit his lip and looked down, submissive. And that’s when I realized it - I had the power now. Ash used to be the loud one, the cocky one, the guy who always made the plans. But now? Now he looked up at me like he was waiting to be told what to do. I circled him slowly, eyes trailing every inch of his changed body. I couldn’t stop staring. The soft thighs, the smooth front hidden under satin, the delicate curve of his waist. “You like looking like this, don’t you?” I asked. He didn’t answer. “Good,” I said. “Because I like it too.” - and then I pulled him closer by the hips. #trans #tgirl #trap #femboy #feminization #pinup #lingerie #sissy #thicc #mtf #girlnextdoor #cosplay

***PART 2*** WITH VERY FEAR, I BOUGHT A SMALL METAL BUTT P..

***PART 2*** WITH VERY FEAR, I BOUGHT A SMALL METAL BUTT P..