Katie-the-Angel-Witch

Yes this is an older piece that's much lower stakes than the previous tale in this anthology but come on, it's cute, and what trans person HASN'T used Tabletop RPGs to play characters of their gender, before they know their gender or before they're ready to come out.

Okay I didn't, but in my defense I was the DM in that group once it got too big and we had to split it into two parties, and I was still very much closeted and afraid of showing my femininity whatsoever. Anyways, enjoy this tale of a fateful DnD session.

“Wow did I actually do it? Did I actually manage to get a full party a month in a row all on time?” Our DM, Sarah, laughed. It was a bright laugh. When the DM laughs you should usually be scared. But Sarah’s I’m-about-to-do-some-bullshit DM laugh was much different from that one. 

“Well that’s what happens when your party is college kids from the same course without part time jobs.” Matt shrugged and took a sip of his ice tea. He was the half-orc wizard. He made it work. It was amazing to witness. 

“Right right, so what’s on today’s agenda kiddos?” Sarah stretched and went to check her notes from the last session. “Oh okay we left off at a delicious point where you were about to enter a haunted mansion.” She rubbed her hands together. “Alright y’all ten minutes before we start, go grab some drinks in the sports bottles that don’t spill. Snacks are to be left on the side table. I’m gonna finish setting up.” She made her way over to her cupboard and started taking out a box of miniatures for ghost scenarios. I gulped and walked over to her nervously. 

“H-hey Sarah, I was wondering, since it’s like a haunted mansion, what if… what if my character got possessed by a female ghost that changed his body, but he managed to push her out while his body remained female?” I twiddled my thumbs nervously, as Sarah looked at me.

“You keep asking for Damian the Tiefling Fighter to get turned into a girl every session. You can just make a new character that’s a girl, you know, I don’t have a problem with that.” She sighed as she looked through her collection, picking out a couple of specific shapes. 

“I don’t want to make a new character, though, I… I like Damian. I just think it’d be neat if he was a girl for a while, you know?” Sarah faced me and looked me over. 

“Riley, is there something you’re too afraid to share?” Sarah grabbed my shoulder gently in that moment, my eyes darted around the room.

“N-no definitely not there’s nothing I fear would ruin any friendships I have or destroy a safe space I have with a group of friends definitely nothing like that.” I gulped, and she let go of my shoulder. 

“Alright Riley. Just hold on a minute while I have a talk with the other three. Nothing you need to be there for.” I saw her walk off and grab the rest of my group, going into the adjacent room as I stood there awkwardly. The conversation they were having something I wouldn’t be privy to. 

Sarah meanwhile, in the other room with Matt, Lily and Constanze (Connie for short), took a deep breath and turned towards them. “I think Riley is trans.” Her party looked between each other. Looks of yeah duh on all their faces. 

“Riley does keep asking you for TG/TF opportunities. Which to be fair doesn’t have to mean anything, I enjoy it for fap material.” Matt scratched his face, chuckling. 

“Ugh Matt no TMI, Tee Em Fucking I, I still haven’t forgiven you for the tentacles.” Connie made a gagging sound. 

“You told me you were into them.” Matt crossed his arms.

“I was in class! YOU were in class! We all were in class!” Connie threw her arms up into the air in frustration, as Sarah clapped to get their attention. 

“Hey y’all chill I wouldn’t have brought it up if I had the one thing. Riley’s response to me asking if he has something to share is what made it click.” Sarah gestured to the group.

“What was the response?” Lily asked, tucking a stray strand of hair behind her ear. 

“Nervous laughter and denial of having anything that, I quote, makes him fear he’d lose friends.” Lily nodded at Sarah’s reply. “I’m going to offer the option of wearing a dress tonight to Riley. I’m going to need you to affirm Riley. We’re gonna do his request of Damian getting possessed and turned into a girl. I’m going to make it permanent.” Sarah gestured to the group again. “And you’re going to roleplay the most supportive party members a tiefling fighter could have, got it?” Everyone nodded at her, as she made her way back to the main room, turning to them before crossing the threshold “You stay here for a second while I ask Riley.” 

As I fiddled my thumbs and sighed, I was worried what Sarah would do. I mean, it is just a DnD campaign, I could make a new character, forge bonds with the rest of the party, but. I didn’t want that. Killing off Damian like that would feel like killing off part of me. Sure, he was a male character I picked because I was scared of outing myself. Sarah came out of the other room, went straight for me and grabbed my shoulders. 

“Do you want to wear one of my dresses tonight?” She smiled. Fuck. Oh fuck. How’d she figure it out.

“N-nooo I… I definitely don’t… really really really want to… do that.” I gulped, she patted my head. Her smile was still there. 

“Riley. You keep rolling 1s on bluffing. We’re not even playing Pathfinder, and you keep rolling 1s on bluffing.” She grabbed my hand and started leading me to her bedroom, locking the door behind herself once we were in, before she opened her wardrobe. “Pick one. Put it on. You’re wearing it for the whole session. I’m gonna transform Damian into a girl. And you’re going to cry happy tears because your friends are there for you.” I could only stare at her in awe. 

“S-Sarah…”

“Oh right yeah that reminds me, got a new name picked for yourself you want us to call  you?” 

“Riley is… Riley is okay. It’s neutral. And I think… kind of cute.” I scratched the back of my head, as she grabbed my hand and nudged me towards the closet. I looked through and found the cosplay dress she wore for a con one year. I was really envious of how it looked on her. So I grabbed it. “U-uhm are you… are you gonna be watching?” 

“Duh I’m gonna be watching, I need to make sure you put it on right. But that one, huh, iiiiinteresting.” I could see the :3c in her tone of voice. I sighed and got to undressing, before I slipped the dress on, Sarah helping me zip it up. “I know I sewed it for myself, but sheesh girl, I haven’t realised how similarly shaped we were until now.” Being called girl left butterflies in my stomach as I blushed. “Alright, come downstairs, you’ll be surprised by the response.” She unlocked the door and lead me out and down the stairs again. The dress had a very poofy skirt, was sleeves and had these lace covered straps, and little devil wings on the back along with a tail. “Oh wait just a second.” Sarah ran back into the room before we made it down, coming back down and putting the headband with horns on my head. “Not enough time for me to dig out and style the wig, maybe next session.” She patted my head again and we made our way downstairs. 

“I can’t believe Damian turned into a girl and popped out of the game before we reached that bit in-game.” Matt joked and stuck his tongue out, as Connie punched him in the shoulder. 

“Jackass.” She shook her head and turned to me. “It suits you… Riley still good?” 

“Yeah, Riley still good. So you’re… really all okay with me being trans?” I grabbed my shoulder hopefully, as Matt made an exaggerated gesture. 

“Why who wouldn’t want to be surrounded by a bunch of pretty girls.” He grinned. 

“Your gay ass.” Lily was chewing on bubblegum now, blowing and popping a bubble. 

“That’s pan ass thank you very much. I’m simply more picky about girls than I am about men.” Matt huffed, and I smiled at the group. 

“Everyone… thank you so so much.” I made my way to my seat and sat down, waiting for the game to start. 

“Damian finds himself separated from the group, the door to the room closing behind him suddenly, not letting the rest of the party in.” Sarah’s narration was great. 

“I try to open the door!” Connie reached her hand out to mime opening the door. 

“It does not budge. Holding the doorknob feels extremely, extremely cold. Damian, as you stand in the room, the unlit candle holders come to life with a blue flame. An apparition appears on the bed. Looking like a sickly young woman, about your age, she turns to you.” Sarah cleared her throat preparing to do a voice. “Yooouuuu… You shall be my new body… strong and healthy, unlike the one I had in life.” She dropped the voice for the ghost. “The ghost lunges at you, disappearing within your body, as a chill spreads throughout your bones. Roll me a charisma save.” I rolled the dice, gasping at the result. 

“Nat20.” I gulped. She promised. God I hope she doesn’t do anything bad now. My back felt itchy as did my scalp, but I paid it no mind. 

“Wow. Okay then. The moment the chill spread throughout your body, you hear the ghost’s voice in your head. As if your own thoughts. You hear her gasp in surprise.” Voice switching. “O-oh, I haven’t expected this. Your will is so strong, and I want to feel alive again, but this… There’s something I can help you with. Something you crave deep down.” The itch got stronger on my back, I hope it wasn’t the dress material, it was really soft and comfortable to wear. Sarah cleared her throat. “Instead of the chill you felt as the ghost entered your body, you now feel a warmth spread through you-” When did it get this hot in here. “You gaze down on your arms, and see the hair on them go light and soft, almost completely invisible, unless you run your hand over it. And even then, your skin is feeling smooth all over, all your body hair receding and shifting.” Fuck, it was hot, I tugged at my collar and noticed my hand. Was it always this smooth and… pink? “Your breathing gets heavy, as you feel your bones crack and shift, you shoulders more feminine, your waist pinching in, your hips expanding. You keep your height as before, and your strength, but underneath your armor-” I felt light headed, and heard cracks “your figure is much more feminine than before, which you notice only for a second, before you feel a pressure built.” Fuck now my chest is itchy. “As two small breasts blossom underneath your armor, and your privates shift inwards.” F-fuck my crotch 

“A-ah aaah AAAAH.” I curled back and screamed, the scream escaping me sounding nothing like me, the stretching and curling going past my spine and into my… tail… I caught my breathing, and looked down at myself, everyone else staring at me. “I… what… h-how, I’m… I…” I ran a hand through my hair and hit the horns, brushing away the headband by accident. 

“Jesus, Riley, I know you really get into character, but I wasn’t expecting you to get into it THIS much.” Matt laughed, and I blushed. And stood up and rushed to the bathroom to look at myself. I was a demon girl. I looked like my in-game character did. Sarah let Damian have little useless wings for the aesthetic, but I could feel them now, see them, see the tail as well. My face soft and adorable and gentle, my teeth sporting small fangs now, my tongue forked, my skin a soft pink shade that went into my horns before they turned a glossy black as they curved. The nails on my hands sharing the hue. 

“My name is Riley, I’m a girl. Riley is a girl. Riley is a cute demon girl.” 

“Hell yeah she is” Sarah was standing in the door frame, looking me over. “You doing alright? I really wasn’t expecting it to get that intense for you. We got one more bit left to finish in-game and I think it’ll be about time to wrap up the session.” I nodded at her, flashing her a grin. 

“Nobody can deny I’m a girl now.” I giggled and returned to the table. Sarah went back to the DM chair and cleared her throat.

“Your transformation finished, the door unlocks and opens to the outside as you fall back, looking up at your party. They all see a cute tiefling girl on the ground. What do you do.” Sarah did the Shinji’s Dad Crossed Hands Pose. You know the pose. Somehow she had the glowing glasses look despite not needing to wear glasses. Matt was the first one to talk. 

“So do you want to stay a girl or get this sorted? I ask, extending my hand down to my party member.” 

“S-stay a girl, I stutter out, taking the hand.” I managed to say. 

“So what name should we use now, Damian doesn’t really fit now.” Connie said aloud as her character.

“Lucy.” I blushed a bit. 

“Alright and I’m calling the session there!” Sarah clapped to announce it. “Holy shit, good game, but also holy fuck? Riley? RILEY? YOU TURNED INTO YOUR CHARACTER HOW THE FUCK!!!” 

“I DON’T KNOW!!! BUT I LOVE IT!!!” I was just smiling while yelling, as Sarah walked over and gave me a hug. 

“Fuck it. Keep the dress. You can stay overnight. We’re dealing with the change in the morning.” She petted my head and I melted at her touch. 

“Alright we’re gonna go home now I think, see you in class.” Lily stood up and the rest of the group followed her out. 

“See ya. Do I have a little tiefling to pet now?” Sarah giggled and kept petting me.

“Yeah. A cute little tiefling girl to pet. That melts at your touch.” I somehow managed to make purring noises. I slept the most comfortable sleep I ever had that night.

Katie-the-Angel-Witch

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