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The Halloween That Changed My Life (mm-trans/f, UA-teens, ETOH)

CDAshleyFoxx · 355

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Offline CDAshleyFoxx

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This is a fictional story about a group of teen boys who have a wild night one Halloween eve. Little did they know that their friend was hiding something under his costume. This fictional story deals with young teens and transgender topics along with some alcohol consumption. Avoid if you must.


Offline CDAshleyFoxx

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Reply #1 on: October 28, 2022, 06:37:04 AM
Chapter 1

I just turned eighteen, so I’m officially an adult, but I feel like I’m just getting started like I’m about to be reborn. I guess that is a little confusing without some context, so I guess I should go back five years, so like 2017ish. That is when my life took a dramatic change from the path I was on to where I am today.

It was Halloween, and I was being dropped off at my friend’s house. My parents were really religious, so we didn’t celebrate Halloween, along with several other holidays in the typical way most people celebrate them. If we weren’t going to mass then we were abstaining. Halloween was “satan’s holiday,” my mother said, so I wasn’t allowed to participate, but she did let me stay over at my friend’s house under the agreement that his parents were home. When my mom pulled up, Tim and his mom came out to greet us, and as the parents talked, we ran in the house to put my sleeping bag and bag of clothes in Tim’s room. Shortly after my mother left, Josh, our other friend showed up.

Before I go further, I guess I should describe myself and our group dynamic. We were all middle school nerds. We weren’t popular in school and just socialized with each other. We played video games and not sports. We played Dungeons and Dragons and World of Warcraft, if that says anything. Tim and Josh were my age, but I kind of looked up to them like they were my big brothers and role models. Even among us, they were more confident and more outgoing. They would make decisions for me, and I think they knew they had to because my mom made me such a push over sheltering me from the world.

I was kind of the runt of the litter. Part of being smaller than my peers also had to do with the fact that I had just started puberty at thirteen, and it was slow going, so my voice hadn’t changed, and I was still a softy, even though I was normally weighted. While the rest of my peers were getting muscles, chiseled faces and growing taller, I still looked young and androgynous. I didn’t know it then, but the surge in testosterone in my body was peaking and dropping abruptly with less sensitivity, and it was causing a feedback, rebound effect or something that spiked my estrogen, which actually lingered longer in my system for some reason, or I was likely more sensitive to estrogens. My doctor tried to explain it to me later in life that it is not entirely uncommon and that these hormone deficiencies or fluctuations, if more extreme, can be treated with aromatase blockers and growth hormone injections had my parents taken me to doctors, but they believed everything was in God’s hands and for a reason, and I guess I believe that too now, but I digress. Anyways, it was leading to changes that made me gain fat on my rear and hips and made my skin soft, and it left me with bad gynecomastia, which is breast growth in males. At first I just had puffy nipples with soft and slightly enlarged areolas, but those progressed to small breast buds. Eventually, the breast buds softened and spread out, and I started to get some curvature and shape to my chest. In short time, I almost reached Tanner Stage 4, my doc later said, where I hadn’t developed full adult breasts—that would be Stage 5—but I had the volume of Stage 3-4 with a secondary height of puffy tip to my areolas still. Nothing was dramatic like I didn’t have double-Ds—more like a B cup—but it made my androgynous body look even more feminine than some of my female peers that were still flat chested, and I was really self-conscious about it. If I had been overweight then I’m sure the fat deposits wouldn’t be as noticeable, but I was still petite and fairly lean like I had a flat stomach and my ribs showed, so the unusually fat distribution was kind of noticeable when I was naked. I did my best to hide them with baggy shirts, and I just hunched over looking timid and pathetic, and I never went to pools or places with my shirt off. In fact, my parents hadn’t even seen them, and I was all too afraid to bring it up. Yeah, so my clothes never fit well, and they were cheap, plain crap from Target, so yeah, I looked pretty pathetic. What else? Oh, and I’m very nearsighted, and back then, I wore thick glasses instead of contacts, which made my eyes look super small, so yeah, I was a total dork.

Anyways, we were planning on just staying in that night and watching scary movies while we played Dungeons and Dragons, but as fate would have it, those plans rapidly changed. Tim’s mom was a lead nurse in the ER, and she was being called in because the other lead got sick. She told Tim’s older sister that she had to watch us, which his sister adamantly objected to because she had plans to meet up with her boyfriend and go to a Halloween party, but Tim’s mom made her swear. Well, the second Tim’s mom left for work, Tim’s sister changed into her costume and bailed on us. She told us to keep our mouths shut, or she would make Tim’s life a living hell, and we believed her. She drove off and left us alone in the house. This wasn’t a big deal to me, and I figured nothing would change, but then Tim had a face like he was looking mischievous. He looked over at us, as we sat in front of the TV around our board game, and said, “You guys want a drink? My mom’s liquor cabinet isn’t locked.”

I didn’t know what to say, but I was scared of being caught, scared of actually drinking alcohol, and I was scared of dying, being super brainwashed by my mother. Josh answered for me, “Of course we do, don’t you Casey? Yeah, he wants some.” Tim and Josh went into the kitchen and left me to drudge after them. Tim pulled a bottle of Malibu rum from the top cupboard and poured us each a drink. I had a taste and immediately recoiled. In fact, we all did, but they were trying to be macho, so they restrained their faces, as they laughed and took another swig. “It tastes like coconut,” Josh said. Then Tim suggested we chase it with some root beer. We were laughing and giggling, as we drank the liquor, acting so adult with our adult drinks, but we didn’t have much because Tim was afraid his mother would notice it missing. We really only had like two shots each, but two shots was enough to make us feel pretty tipsy and start to act stupid. We were being silly when Tim suggested that we go Trick or Treating, so we could get some candy. They knew I wasn’t allowed, so they were pushing me to go out with them. I pointed out that we didn’t have any costumes, but Tim interjected. He said we could wear his costumes.

He had a thing for DC comics and more specifically, he really liked Batman, so he had a Batman consume from two years back that he wore, and he had a Joker costume from last year that fit Josh. I was afraid someone would see me and recognize me and tell my mom, so I was super paranoid about going out, telling the guys I didn’t want to go. “Plus, you don’t have anymore costumes,” I pointed out. 

Tim thought about it for a second, and then made a half-hearted suggestion that I could go as Harley Quinn, saying that I could wear his sister’s costume from last year, as Josh and he laughed. But then he snapped out of the laugh and was serious. “Dude, you should totally do it! No one will recognize you,” he said with enthusiasm, but then he laughed saying, “They’ll probably just think you are my sister or…my girlfriend,” then snickering, as Josh and he laughed some more.

“Like you would have a girlfriend,” Josh teased.

“Shut up,” Tim said, as he pushed Josh on the shoulder before turning his attention back to me. “But if you don’t want to then we could just leave you here for a little while. We will be right back once we score some candy.”

I was feeling the effects of the alcohol, and it was making me feel braver or stupider than normal and full of energy. The last thing I wanted was to be left at Tim’s house alone, so I acquiesced. My older cousin would dress me up in her dresses, so we could play tea together, so I wasn’t exactly unfamiliar with playing dress up. Tim led me to his sister’s room and opened her closet and found the costume tucked in the back. “Here it is,” he said. “This is going to be hilarious. Alright, put this on Casey,” he said, as he threw the costume on her bed. He went in her bathroom and began rummaging through her drawers. “Here it is,” he said, as he pulled out her daily makeup bag, as well as, a box of costume makeup. “I think that is everything you’ll need. All her shoes are in that box. Hurry up,” he said, as he quickly left to his bathroom to get ready with Josh.

I stared at the outfit for a second and couldn’t believe I agreed to their terms. I wanted to back out, but I was more afraid of being left behind like a social outcast that I gave in to peer pressure. I separated everything out on the bed, so I could assess the costume. It was much more older-teen or adult than something worn by girls my age. There was a blonde wig with pigtails, black fishnet thigh-high stockings, one red and one white arm sleeves, there was a black and white puffy skirt, there was a white crop top that read, ‘Daddy’s Little Monster,’ and there was a little black and red sleeveless jacket with poker symbols on it. When I say little, it was shorter than the white shirt. I was really second guessing this whole thing, but I didn’t want to look like a punk who was too afraid, so I started removing my clothes. I got down to my boxers and began putting on the shirt and skirt. Looking in the mirror to see how it fit, I realized that my breasts were clearly outlined in the shirt, and the bottom of my boxers were showing. I realized I had little choice, but to find some undergarments in his sister’s drawers. Outside of some period granny panties, everything in there was thongs or g-strings. I begrudgingly dropped my boxers and pulled up one of her red thongs over my hips and between my cheeks. This was the first time I had ever worn woman’s underwear, but I actually didn’t mind it. In fact, it felt kind of good and naughty. I lifted the skirt and looked at my full bubble butt in the mirror, and I saw a very feminine reflection that turned me on, as if I was staring at a real girl and not just some picture on my phone. I reached down and grabbed my own ass, watching in the mirror, as if I was watching my hand grab a real girl’s ass, but I snapped myself out of my self-indulgence; I didn’t have time to linger. I found a matching red bra, and I put that on, and then I put the shirt and jacket on. Tim’s sister wasn’t large chested, so the padded bra fit snuggly and lifted my small breasts, resulting in two full-looking mounds on my chest that actually looked like I had adult boobs, but most importantly, it masked the fact that under the shape of the bra was actual breast tissue, and that is all that mattered. I didn’t really know what to think, as I stared at my reflection, but it made me imagine what it would be like having real breasts that I could show off like the well-developed girls did at my school, and it made me imagine what it would be like to be a girl having access to my boobs and getting to touch them all the time, as if all girls just want to touch and look at their tits incessantly.

I shook it off and went into her bathroom. My face was pretty pale, but I added some white powder to my face, and then I put some red and blue on my eyes followed by some black on my eyelids, and then I smeared it in with my finger to look messy. I found some of her mascara and put that on with haste before drawling red diamonds and hearts on my cheeks and splashing my cheeks with some blush and my lips with her red lipstick. I found some of her perfume and sprayed some on my neck.

I went back in the room and put on the wig. She had some bobby pins on her nightstand that kept it secured to my hair. I even tossed my head around to make sure it wasn’t going anywhere. I put on the fishnet stockings and arm covers, and then I rummaged through her shoes and found some black tall Converse that were a little tight, but fit enough that I wouldn’t be miserable. As I looked in the mirror through my glasses, I put my hands in the jacket pocket to pose, and I felt something, so I pulled it out, and it was a black neck choker, so I put that on. Looking in the mirror, I couldn’t believe it; I was super cute and totally passable like there was no way anyone would know it was me, but despite the alcohol, I was a little freaked out to step out of the room, but then Tim came barging in and practically died laughing when he saw me. “Dude, Josh! You got to see this,” he laughed. “Dude, you gotta leave these glasses at home,” he said, as he walked over and ripped them off my face just as Josh came charging into the room.

“No fucking way! Oh shit! He looks like he could be your sister, dude,” Josh said. “There is no way anyone will recognize you man.”

Josh and Tim was eyeing me up and down, and for a moment, I couldn’t tell what they were thinking. “What is it? Did I mess up the makeup? Come on guys, what is it?”

“Naw man,” Tim said. “I just didn’t know your eyes were so big and blue, you know. I don’t think I’ve seen you without your glasses. You just look different.”

Josh was staring at my navel and legs. “Yeah, the eyes. Never knew you had such a shape to your eyes.”

“Well, let’s just get going. The sooner we go the sooner we can get back,” I interjected. “But I can’t see for shit without my glasses, so don’t go running off on me. I’ll probably need to hang on to one of you!”

Offline CDAshleyFoxx

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Reply #2 on: October 28, 2022, 06:37:31 AM
Chapter 2

We took a final swig of our drinks and headed out. They say that form follows function, and that is exactly what happened to me. For some reason, I quickly took to being a girl. I was skipping along the side walk and hanging like a needy girlfriend on Tim and Josh, so I didn’t get lost being so blind. I had a strong imagination, so I really took on the roll of Harley Quinn, changing my attitude to being a little ditsy and sassy. In some ways, I was feeling more confident and comfortable in my costume and in her character than in my own body as Casey. When Tim would say my name, I told him to “Call me Harley bitch.” I’m sure the alcohol had something to do with it. Tim and Josh only made fun of me, tugging on my bra strap and trying to flip up my skirt or poke my belly button. Even with their toying around, our ruse worked, and we went unnoticed. I even had some complements on my costume where some adults and other girls said I was cute or had the best costume among all the girls they had seen…girl! An hour later, and we had plenty of candy and headed back to the house to assess our hoard of sucrose. We kicked off our shoes and dumped our bags in the center of the carpet in front of the TV, so we could divvy out the candy evenly. After we divided up the candy, we turned off the lights and put on a scary movie, as we ate the candy.

I was so comfortable in my outfit at this point that I hardly remembered that I was wearing a thong under my skirt, and as it happened, I was entirely unaware that my skirt had ridden up my legs, as I laid on my stomach on the carpet facing the TV. The glow of the TV was highlighting the edges of my body, and Tim was laying on the couch in prime position to see the outline of the bottom curve of my cheeks peeking from under the skirt. Little did I know he had gestured to Josh to come take a look, so I was entirely surprised when the two of them suddenly started laughing. Then I felt my skirt flip up over my rear exposing my bare butt. “Hey! What the fuck guys?!”

“Casey, man, you didn’t have to wear ALL of my sister’s clothes,” Tim chuckled.

“Shut up,” I clapped back, as I covered back up and flipped over! “My boxers were too long!”

That’s when Josh had a laugh, “Well you definitely went shorter!” Then he changed his tone, “But hey, at least you could pull them off. What do you say Tim? He probably has a better ass than your sister.” Then Josh chuckled again, “She’s got a back crack, right? She’s got no right owning thongs,” he said laughing!

“Hey! Shut up about my sister,” Tim clapped back, pushing Josh. “No way Casey has a better ass than my sister.” Tim really looked up to his sister. She was hot and popular, unlike him, so he had her honor to defend, or maybe it was an excuse, but he jumped down on me and wrestled me over. He was bigger than me and more developed, so despite my objections, barely putting up a fight, he was able to easily push me back down on my stomach and pull my skirt over my ass, exposing it again. “Dude, maybe you are right,” he chuckled. “You got a girly ass Casey,” he proclaimed.

“Dude, I told you. Casey probably has a better ass than Jenna Jameson,” Josh declared, as he joined Tim on the carpet. She was the hottest girl in our middle school, so this was saying a lot.

“Come on guys,” I objected. “Let me up. Get off!” But they only ignored me.

“No fucking way he has a better ass than Jenna Jameson,” Tim said, as they studied the shape and volume of my ass, “But I bet it is pretty close; I’ll give you that,” Tim agreed.

“I bet it feels like Jenna Jameson’s ass…” Josh claimed, as if locked in a hypnotic trance. “…all squishy and bouncy.” Josh reached forward and poked my cheek, pushing it into my other cheek and quickly releasing his finger, so my ass recoiled with a small jiggle back into position.

“Josh! What the fuck? Come on guys. Get off of me,” I begged, but Tim kept me pinned, and then I felt Tim poke me a few times in my butt, pushing on my butt and making it jiggle some more. I was super embarrassed, but I was also afraid to defy them, as they were my only friends.  Then I felt the warmth of his entire hand grip my cheek and squeeze it.

“Yeah man, I bet this is what Jenna’s ass feels like,” Tim agreed, kneading and molesting it in his hand. I tried to squirm away, but it only made it worse, and for good reason. With each attempt to twist free, I only was making my butt toss and jiggle some more, which unbeknownst to me, was putting dirty ideas in their head. “Dude, give it a squeeze. It is hella nice,” Tim said to Josh. Josh squeezed the other cheek and eagerly began kneading it in his fingers.

This was all too much for me. I just hid my face between my hands and the carpet and stopped putting up a fight, as they continued molested me. At first I was feeling so exposed and embarrassed and terrified of being caught in his sister’s thong, scared this would get around school, but as they continued, the horror was passing and being replaced by the relaxing sensations of them massaging my ass. There was a part of me that was repulsed at the thought of being touched in a familiar way by a boy; I had always been attracted to girls. At least, I thought I was interested in girls, but then, as Harley Quinn, dressed as a girl, my imagination allowed me to accept the situation, and I began enjoying the attention from my two perverted friends, but I didn’t let them know that. “Come on guys. You’ve had your fun. Haven’t you touched it enough?”

Tim had other ideas, looking over at Josh. “I wonder if he kisses like Jenna Jameson too.” Josh made a confused face that made Tim quickly followup. “Here me out dude. Casey looks like a girl right now, right?” Josh nodded, while I just listened with horror. “Soooo, like, don’t you want to know what it is like to kiss a girl? Like, don’t you at least want to practice, so you don’t fuck it up when you actually kiss a girl?”

“You mean if we ever kiss girls,” Josh said jokingly, mocking himself even, as he laughed.

“Dude, I’m serious! You want to be a complete, fumbling amateur the first time? I don’t,” Tim declared! “We’ve got to practice! It’s now or never!”

He crawled off of me, and I immediately turned over. “I don’t know about this guys,” I said. “I’m feeling weird.”

“Dude, we all feel weird. It is the alcohol and sugar,” Tim explained, as if he was giving us an excuse for our actions. “Come here,” he said, as he lifted me up under my armpits from the floor onto my knees, and then kneeled down right in front of me. My knees spread, as my bare butt sank between my heels until I was sitting on the carpet, hunched over, feeling pathetic and sorry for myself. “Dude, sit up,” Tim said, as he lifted me from my shoulders into an erect posture. “Just close your eyes. This is no big deal.”

There was little I could do to get out of this situation without risking social isolation for the rest of my life, or at least, that is what I thought. I closed my eyes and just waited, as my heart beat out of my chest. It felt like an eternity in that moment, but then I felt Tim’s firm lips press against mine. I didn’t really move, and I just let him press against my lips, and then he pecked along the tips of my mouth. At first I was disgusted that a boy was kissing me, but then I remembered that Tim was, for all intensive purposes, kissing Harley Quinn, and as Harley Quinn, I made a convincing female. I remembered my character, and once I did, I found myself relaxing enough to take in the sensations of his lips against mine, and when I did, I realized it felt good. I began kissing him back, trying to match his pressure and complimenting the tilt of his head, so our heads didn’t hit. My heart was pounding, which was taking my breath away, so my lips naturally parted, and no sooner had they parted than I felt Tim’s tongue slide between my lips. At first, I was too afraid to stick out my tongue. I had kissed my mom and grandma on the lips, so while this was different, the child in me was slightly repulsed at the idea of touching tongues. That didn’t stop Tim, and when he found my tongue, he drew it out, as we slid our tongues between our lips, stroking them across each other. It felt like an eternity, but it only last a few seconds before Tim released my lips, leaving me in an euphoric daze with my eyes closed. I slowly opened my blue eyes to see my red lipstick smeared on Tim’s mouth looking so sensual and adult.

Josh saw this, and immediately pushed Tim out of the way, coming down to his knees right next to him. “It’s my turn!”

“Hold your horses, you horn dog,” Tim clapped back. “She isn’t going anywhere. Shit, I mean he isn’t. Sorry Casey, you got me all confused with those soft lips,” he said, as he smiled. As I shrugged my shoulders to blow it off, Josh leaned in and began kissing my lips aggressively, and it overwhelmed me causing me to stretch open my eyes and pull back. “Dude, not so fast,” Tim instructed. “Haven’t you ever seen a movie or porn? Slow down.” Immediately Josh slowed down and began kissing me super soft, almost going too far in the other direction, but it allowed me to relax and lean back forward into him. I slowly closed my eyes and focused on the sensation of his lips, which were fuller than Tim’s. Josh was eager to French kiss me, so in short time, we were into a heavy kiss with our tongues tangling in our mouths. “Okay, okay,” Tim interrupted, as Josh began holding my legs and pulling me closer to him. “It’s my turn again.” I opened my eyes just as Josh ripped his lips from mine, and I could see the lust in his eyes. It pierced straight into my soul. As Tim pushed him aside, my eyes tracked his, trying to read his thoughts, but I all too well could tell what he was feeling because I was feeling hot and bothered too. I became keenly aware of the erection buried beneath my skirt, feeling trapped in Tim’s sister’s tight thong. And then Tim’s face was in front of mine, so I closed my eyes and felt him kiss me.

We practiced kissing for another five minutes with the two boys taking turns with me, each time, they were getting braver and braver with pulling on my arms to move me closer to them or rubbing on my fish-net-covered legs, even passing their hands up my thighs and under my skirt to the bare skin at the swell of my soft hips. As I was kissing Tim, I felt his hand around my  waist, creep up along my back and under my jacket and shirt. He was pulling on my torso, pulling me into him, but then he moved up to my bra strap. I had my hands on the large, fake, muscular, shoulders of his Batman suit, bracing myself again his lustful kisses when I felt him successfully free the clasp, causing the bra to release its tight grip around my torso. He ripped his lips from me, so he could declare, “I did it with one hand! Dude, you need to practice this, but you have to do it with one hand, or it doesn’t count,” as if there were rules.

I played along, reaching behind my back to clasp the bra. Josh moved Tim aside and assumed a position right in front me looking really excited. I could see the obvious bulge in his pants, so I smirked back up at him, as our eyes met. He leaned forward and pulled me to him, planting a lustful kiss on my lips, while I could feel him fumbling with my strap. I wanted him to be successful, so I held as still as possible, as I continued to make out with him. Eventually, he got it, releasing my bra from my torso, so it was loose against my chest again, but he didn’t declare victory like Tim had. He continued to lustfully kiss me, and his hand gripping my ribs slowly worked up until I felt his thumb near the bottom curve of my breast tissue. There was a part of me that wanted to push his hand away, but I was feeling super horny from all of the making out, so my mind wasn’t sharp, and my guard was down. His warm touch felt good, and I could tell my nipples were feeling hard and sensitive. After only a few seconds that felt like eternity, I moved my hand to his wrist and slowly moved his hand up to my bare breast. The second his hand gripped my chest, his lips stopped moving causing me to open my large eyes to see him staring back at me in disbelief. He quickly stood up. “What,” I asked him, playing coy?

“Dude, you have breasts. Casey’s got breasts,” Josh declared to Tim.

“Shut the fuck up,” Tim said in disbelief. My heart was pounding that much more out of my chest, as I looked up at them, realizing the cat was out of the bag, so I decided to reveal myself. I slowly pulled up my shirt and bra and flashed my shapely tits at them. Their faces were in disbelief, as if a paradigm in their brains was suddenly ripped apart and altered. Maybe it was seeing breasts on a guy or realizing I had breasts this whole time, but there was a moment of silence, as they stared with awe. “Dude, are you a girl like a really, real girl,” Tim asked? I immediately wanted to dispel any notion that I was a girl, not knowing if that would disqualify me from being a friend in their group, so as I shook my head, I immediately lifted my puffy skirt to show the small erection bulging from his sister’s panties. “Dude, what are you doing with tits? This is crazy.” I just shrugged, as Tim knelt down in front of me and reached out to fondle my breasts. I closed my eyes when his hand made contact, as if a huge weight and secrete was being lifted off of my shoulders. “Dude, take this off,” Tim said, pulling on my jacket. I pealed off the jacket, and then I carefully lifted the shirt over my pigtails before releasing the bra off my shoulders. At this point, I had nothing on my torso. I had on my sleeves, my choke color, my skirt and panties, and I had on my fishnet stockings, so I was feeling pretty exposed. Tim went back to groping my chest, causing me to put my hands back on my heels to brace myself, which only opened up my chest more. Josh dropped down to his knees next to Tim and took a breast of his own. “They’re only a handful, but they feel nice Casey. They might even be bigger than Jenna Jameson’s.”

Josh interjected. “Dude, no way. I’ve seen her lean forward and run during PE. She’s got a decent sized chest. Try shaking them Casey,” Josh asked, as I took this to mean that he wanted to assess their size. Tim and him pulled back, and I kind of scrunched my shoulders together, tossing and jiggling them around, and bouncing my butt up and down to get them moving up and down on my chest. “It is pretty close man. I’ll give you that, but I think Jenna has Casey barely beat.”

“You’re missing the point!” Tim was wide eyed. “We practically have our own Jenna Jameson right here!”

Offline CDAshleyFoxx

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Reply #3 on: October 28, 2022, 06:38:00 AM
Chapter 3

The two spent a few minutes playing with my breasts, squeezing the supple tissue and tugging on my thick nipples until their were teasingly hard. All the attention made me feel a little awkward and shy, so I closed my eyes to hide from my blush, as they explored and played with my body. Eventually Josh found my parted lips and began making out with me, as he pulled me up on my knees into him. As we kissed, I felt Tim’s needy lips kissing on my breast before his hot mouth wrapped around the bud on the tip of my breast. He drew my nipple into his mouth and shocked me with strength of his suckle, sending a jolt of overwhelming sensation up my spine. Josh had his hands gripped on the back of my skinny arms, pulling me to him, as he kissed me passionately. I don’t know what it was at the time, but there was more chemistry with our kisses like he wasn’t just using me for practice or for just the lust of it. I felt like he was kissing me like I was his girlfriend, if that makes sense. Anyways, while Josh and I were making out, Tim was making moves. While he was sucking on my tit, his hand worked its way under my skirt, and he was fondling my ass. The tips of his fingers seemed to be working slower and slower between my cheeks, as he tugged on my butt in a needy way. It didn’t take long before his fingers were touching the thick thong covering my asshole. I could feel the pressure pushing down on my sphincter with each of his kneading and squeezing of my ass. With clear intention, his worked his finger to the side of the cotton material and pushed it aside. The second his bare finger stroked along my puckered ring, I gasped against Josh’s mouth and twisted my hips away, but Tim clasped my cheek and pulled me back to him. He immediately returned to my sphincter and circled his finger around the tight, virgin ring. His finger smeared the sweaty moisture coming from the hot core of my pelvis, smearing it around the ring of tender tissue, and it was causing my legs to feel weak, wanting to buckle against his touch. I whimpered against Josh’s kisses. I could tell my sphincter was relaxing, as seconds gave way to minutes. Eventually, my sphincter felt dilated, as Tim’s finger seemed to be caressing past the outer ring and against the softer tissue within, which was causing my hole to clench a little before relaxing again, winking with need. I couldn’t help myself and began pushing back against his digit. I think Tim felt the heat and soft tissue too, and he could tell I was ready for more. Without warning, he moved his finger to the center of my hole and pushed it into my anus. Instantly I gasped against Josh’s mouth, as my sphincter gripped around his finger. I could feel it undulating in quivering spasms like it was trying to figure out what to do. Tim moved his clammy finger back and forth in my sweaty anus, loosening me up and getting me relaxed. There was urgency, but some experience in his movements, as if he had been studying porn for years to prepare himself for this moment. When he felt me relax enough to push back against his digit, so it slid into my rectum, he realized I was ready for him.

He released his mouth from my breast and postured up with his finger still buried in my ass. I took notice and released my mouth from Josh, so I could look Tim in the eyes to discern his intentions. He leaned forward and kissed me, and I could feel the urgency and lust on his lips. Josh had released me and scooted back. Tim pulled himself from my mouth and began kissing my neck, as his finger worked back and forth in my asshole, causing me to whimper under deep breaths. His mouth on my sensitive neck felt amazing, as he was tenderizing my tissue and leaving his mark with a hickey on my neck like he did all over my tits. He moved his mouth up to my ear and whispered. “Bend forward,” he said, as he tugged on my anus to guid my ass up, while he pushed me down to my hands. I was totally in sissy mode at that point, so I just waited there on my hands and knees, as he moved behind me and pulled his finger out of my gaping hole. He lifted my skirt over my hips, exposing my ass to him before smacking my ass and aggressively gripping it. “So fucking nice,” he said, as he pulled the thong over my hips and down to my thighs. He began swiftly undoing the yellow belt around his waste and pulling down the pants of his Bat suit.

“Dude, what the fuck are you doing,” Josh said in my defense?

“Don’t tell me you don’t want to hit this,” Tim said, as he lowered his underwear, exposing his erection before smacking his hard cock against my sphincter. I felt a warm loogie land on my asshole, and then I felt the soft skin of Tim’s cock smearing the slippery saliva all over my sphincter. It felt so good, and it made me instinctively arch my back. “See, she wants it.” Tim pushed his thumb down on the head of his thin, long rod, pushing it against the resistance of my entrance, and within a few seconds, my asshole swallowed the head of his cock. The second the head got in I pushed back, and it slid inside my anus, stretching me to length. I braced myself, as I felt Tim clasp his hands around my hips. He pushed forward, and his cock burst through the grip of my sphincter, which immediately caused me to tense up and clamp down on his cock.

When I winced aloud in pain, Josh sprung to my rescue. “See man! You’re going to hurt her!”

I didn’t know how I felt, as they kept using female pronouns. I mean, I looked like a girl. I had just as much ass and tits of any middle school girl. I was practically dressed in lingerie. I was wearing makeup. I was on my hands and knees with my best friend’s cock in my ass. It clicked then and there that this was totally me. It wasn’t some fluke that I was in this position. The sissy female inside me was totally acquiescing to the realization that I was totally a girl, as if everything in my life suddenly made sense in light of the situation.

I could feel the tension in my body giving way, as my glutes relaxed, allowing my back to arch once again. My anus was quivering around his cock, but it was acclimating quickly. Tim wasn’t very thick, but he had decent length—maybe five and a half to six straight inches. Tim could feel me relax too. He pulled on my hips, while pushing forward, slowly sliding his cock all the way inside me until my ass was pressed fulling to his hips. “See bro. You were tripping for nothing. She’s good, and she is so fucking hot in there. You have no idea. ” He slowly pulled his rod back out, guiding me away before pulling on my hips and sliding his cock back in my ass. He slowly moved it back and forth, spitting more saliva to lubricate my anus, as he went. I heavy breathing turned into soft moans. “See bro,” Tim said, still seeing the look of concern on Josh’s face, as his slow strokes turned into more forceful plunges into my ass. “Casey, tell him you like it.”

For some reason, it was hard to look Josh in the eye like I was cheating on him or something, as if he was cockolding me to his friend, but I did as Tim said, and I looked up at him with my big blue eyes smitten with lust. “I like it.”

“See bro,” Tim said, as he crashed his hips into my ass harder, making it clap against his pelvis. “She loves getting fucked.” My moans got a little louder. I never knew why girls moaned so much, but it just comes out like a combination of pleasure, pain and the labor of working a dick in and out of your body. It is taxing, but I was loving the sensation. “Tell him Casey. Tell him how much you love getting fucked.”

“I love it!” I was totally simping to him. I was his bitch. My whole body was getting hot and sweaty now.

“Casey,” Tim continued. “Tell Josh how much you love having a cock in your ass.”

“I love…oh fuck, shit,” I said, as Tim kicked it up a gear.

“Dude, that’s too fast,” Josh said, but I interrupted him, reaching out to grab his thigh, as I braced myself.

Tim slowed down to a crawl from pounding my ass, having sent my tits jolting about from his furious thrusts. I let out a breath of air I was holding in tension, as my body broke out in a sweat, glistened with dewy moisture. “Dude, Casey is loving this. Look at her.” Josh looked down at my face, as I looked up at him and nodded with a weak and euphoric expression. “See! Man, just pull out your cock, and I bet Casey will be all too happy take care of you.” I bit my lip and blushed, looking up at the bulge in his pants, as I was sure Tim was reading my mind. “Casey, just tell him how you want to give him his first blowjob, so he can chill.” My hand was still on his thigh. I couldn’t speak the words. I just bit my lip, as I nodded and tugged on his pants. “Awww come on man.”

Josh stepped back and unclasped his pants, lowering them to his ankles. I could feel my mouth getting dry with nervous anticipation. He took off his jacket and shirt, exposing his chiseled body. He wasn’t muscular like a jock, but he was naturally lean and defined. He lowered his boxers, exposing his gorgeous erection. He stepped out of his clothes and sat back on the couch. Before he could fully get himself situated, I had crawled forward between his legs, causing Tim’s cock to fall out of my ass. I knelt up with my arms on Josh’s thighs and grasped his cock. I only looked at it for a moment before I closed my eyes and lowered my mouth around his meat, trying to swallow it all in one big gulp, which only made me gag a little. I collected myself after the reflex reaction and tried controlled my enthusiasm. I slowly worked his cock back and forth in my wet mouth, quickly salivating all over his meat.

I could instantly tell that it was much bigger than Tim’s cock, yet both were much larger and more developed than mine, which was barely longer than my finger and tapered to a small, undeveloped tip. Tim had a cut, straight cock with a large mushroom-tipped head that was slightly bigger than the shaft, and Tim had a tuft of black curls at the base of his cock. I recall how the soft, velvet head of his cock worked through my virgin anus and then my muscles clenched around the head, pulling it into my rectum, as my anus gripped his smaller shaft. Josh was uncut, slightly curved and sitting more upright. The thick, amber-brown curls sitting above his more developed cock was easily hiding a few inches. I could tell from the size of his hairy balls that he was a few years ahead of us in his development. With my hand around his shaft and my mouth around the head of his cock, I could also tell that his cock had significantly more girth than Tim’s, so much so, that I questioned if I could fit such a thing in my ass. He was probably only seven to seven and a half inches, but back then, that seemed huge.

As I slowly worked my mouth up and down Josh’s cock, Tim moved behind me and lifted me from my hips to get my ass in the air. I spread my legs and arched my back, as he crawled between my legs. Once again, I felt his saliva splat against my asshole before feeling his cock slipping around my entrance. With little resistance, he pressed his mushroom tip back into my rectum and began humping me. As he fucked me, I suckled on Josh’s delicious rod. I don’t know what I liked more: a cock in my ass or one in my mouth, but I was surprisingly enjoying myself. I was feeling like I was getting all this amazing attention like they both needed me to please them, needing my body to fulfill their desires. I had never been the center of attention, even in our group, so this proved to be my way, and I was loving it. I came off his cock for some fresh air and looked up into his eyes before blushing and closing them again; he had a way of looking right through me. I ran my tongue along his shaft and then dove back onto the head of his cock. I wasn’t very skilled or fancy then, so I don’t know if he was enjoying it, as much as I was enjoying the process.

I let out a gasp, releasing Josh’s cock from my mouth, as Tim gripped my hips tighter and began pounding my ass hard. I was wincing and moaning, bracing myself on Josh’s legs with his cock still in my hand for those short, few seconds until suddenly Tim began to jerk and jolt hard against my ass, squeezing the flesh of my cheeks so tight, he left bruises of his finger tips in my flesh. I could feel his rod spasming in my ass with jerking throbs, as he unloaded streams of hot cum. “Oh shit,” he said in amazement, after he grunted his last jerk. “I can’t believe it.” For someone with so much to say, I would say he was lost for words in that moment.

His furious tempo in those final seconds took my breath away, so I was breathing hard trying to catch my breath, as my head was swimming with wonderment from the feeling of him cumming inside me, never thinking such a sensation would be so gratifying. “Holy shit! That was hot,” I said! The gratification came from knowing my body was able to give him such pleasure, and it welled up in me, filling me with new confidence and energy. I wanted more!

Offline CDAshleyFoxx

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Reply #4 on: October 28, 2022, 06:38:27 AM
Chapter 4

The second I caught my breath I returned my wet mouth to Josh’s cock. I wanted him to cum too. I moaned with my eagerness, as I sucked on his cock, thinking of my next move. I didn’t want to rush Tim, so I let him stay in me for a little bit, as he smacked and spread my ass, admiring his cock still buried in my hole. Eventually, he slowly withdrew his cock from my ass, and when he did, I could feel my hole gaping wide. It slowly spasmed shut within several contractions, spewing some of Tim’s cum down my bare taint and balls. Tim smacked my ass again, as I postured up to pull my face off of Josh’s cock. I paused for a moment, as Tim sampled the curve and size of my cheeks. Meanwhile, his cum was still oozing from my loose hole. I stood up and stepped out of the thong that fell to my ankles. I quickly climbed up on Josh’s lap and found his mouth with mine, kissing him lustfully. I sat down on his cock, and for a moment, my hard rod and small balls rubbed down the length of his shaft. I picked myself back up, reached around my back and pulled his cock down, so I could sit on it. His cock sat against my taint with the head poking up between my cheeks. He slid his hands along my thighs, under my skirt and up to my ass. As he squeezed my cheeks, my ass spread, and his cock worked between my crack. I worked my hips back and forth, grinding my sphincter against his shaft, lathering the head of his cock in Tim’s slippery cum. I could tell he was trying to angle his hips and catch my sphincter with the head of his cock, so I stopped teasing him. I pulled my lips away from his mouth and reached behind my backside to find his cock beneath my puffy skirt. Then I felt his mouth latch to my nipple, as he aggressively squeezed my other breast, which took my breath away, but then I found his cock and guided it to the entrance of my hole. I slowly pushed the head into my anus and sunk down on his cock. I only got a few inches in when the stretch was too much. I could feel the eagerness of his hips wanting to thrust up into me, but needed a moment. The cum pouring from my sphincter, running down his shaft, helped to ease his cock more and more through my asshole. As I slowly worked my ass up and down, I could feel my body acclimating to his size and his patience waining. I whispered in his ear, “It’s almost in.” After the bulk of his girth worked its way past the tightest point, I was able to sink myself completely down on his crotch.

His cock was flooding my rectum, as if he was poking my belly button from the inside. I couldn’t believe how full I felt. I was a little overwhelming, so much so, that I had to take a moment. I could still feel my asshole stretched around his cock, twitching and quivering, as if it was confused what to do. My body was telling me I needed a moment. “It’s in, but just give me a second,” I whispered to him, and he nodded. He leaned forward and kissed me, as he wrapped his arms around the small of my waist to hold me tight to him. Eventually I was feeling more confident, so I slowly lifted my ass, sliding his cock along the rippling folds of my insides before I lowered myself back down on his cock. The girth and curve of his cock was pressing on my insides giving me a feeling I had never felt before. Each time I lowered myself down on his cock, rocking my hips, so his cock pushed on my insides, I could feel a sensation run up my taint, straight to the tip of my cock making it tingle. “That feels really good,” I said out aloud. I started to get a tempo going, and I was moving much more up and down his cock, and then Josh started matching my motion with small thrusts, twisting his hips, so his cock pushed up against my insides. “Oh shit, that feels really good,” I said, as he gripped my ass, pushing me down on his cock. I was overwhelmed by the girth of his cock stretching me, along with the feeling of his cock sliding back and forth inside my slippery, cum-filled insides, pushing firmly up against the wall of my rectum. I was working my hips in a fast tempo, somewhat losing my control when, with zero warning, my body released my first orgasm ever. The electric sensations running to the tip of my cock from each thrust of his cock suddenly broke free like a dam ripping open. The tension in my pelvis suddenly unloaded, and my hips began to quiver in confusion from the overwhelming wave of sensations passing through my body. My cock twitched spurts of cum inside my skirt and on Josh’s stomach. I was so overwhelmed by the sensation that I moaned deeply, while my anus rhythmically gripped Josh’s cock.

“Dude, she’s cumming,” he said, feeling my anus squeezing his shaft and spurts of cum hitting his stomach.

“Fuck yeah man! I got a front row seat,” Tim exclaimed. It was true. He was laying back on the carpet looking up between Josh’s legs watching Josh’s cock pumping in and out of my ass, all the while, he was jerking off a new erection. He could see my hips jolting and bucking and my asshole gripping down on Josh’s shaft. “That’s hot!”

I was dripping in sweat, having worked myself up in a feverish pace, but now I was exhausted, collapsing on Josh’s torso, trying desperately to catch my breath and collect myself. It was my first orgasm, but also, it was my first sissy orgasm. The first is always the best. Josh found my gaping mouth and kissed me. I kissed him back with gratitude, but I was feeling light headed, euphoric and weak. All my muscles felt soggy and were quivering, as if I had just finished a marathon. “I need to lye down,” I said, as I tumbled myself off of Josh’s cock. He was kind and lifted me up by my ass, but when his cock fell from my ass, I couldn’t believe how vacuous and empty I felt. I could feel my sphincter trying to spasm shut, but even after five or six contractions, it still wanted to gape open. I tumbled down to the cushion of the couch. Josh was so sweet. He just got up and grabbed some candy from the floor, thinking I needed a sugar pick-me-up. He slid a few gummies in my mouth that I swallowed, while I caught my breath. Then he slid a cherry sucker in my mouth, and I sucked on the sugar, trying to gain back some energy that had been sapped from me. The two boys had really taken a lot out of me.

“Is that better,” Josh asked? I nodded, as I weakly looked up between his legs at his red, hard cock. It looked angry, and I felt bad. He had been so sweet that I just couldn’t leave him like that. As he turned away to fetch more candy, I grabbed his hand, and he looked back. I lifted my skirt over my ass and spread my knee out on the couch. He looked back at my pathetic face. “Are you sure?” I nodded. He moved behind me on the couch and came up between my legs. I felt the head of his cock push my anus back open, and then I felt the sharp stretch of the swell of his cock open me wide. He slid his cock all the way into my rectum until he was balls deep. He worked his cock back and forth in my ass, smooshing his pelvis and balls into my bubble butt, but eventually he leaned over me and laid his weight on my body, breathing in my ear and smelling the perfume on my neck, as he humped my ass. He was causing my breath to get hot again, and I could feel my energy picking up. I moved my hips in unison with his, matching his thrusts with bucks of my hips. Then his temp switch up two notches, and I could tell he was getting close. He was separating off my ass, so he could pound into it. I arched my ass up in the air, giving him access to thrust up into the wall of my rectum; later in life, I learned that it was my prostate that loved to get fucked so much. Anyways, his grunts from his efforts quickly culminated in his unloading in me. When he did, he pressed his hips firmly against my ass and jerked his whole body against mine. I could feel his hot cum filling me up, as well as, the details of his throbbing cock spasming with my asshole stretched around it. I twisted my neck around, so I could kiss him through his orgasm, moaning with satisfaction at the pleasure he was giving me. “Ohhh shit Casey,” Josh said, as he slowly peeled himself off of me, smacking my amazing ass for good measure. “That was nuts.”

“Fuck yeah man,” Tim echoed. “I told you man! I knew you would want to hit it too.” He continued, “Shit, I don’t know man, if Casey’s ass is that good, imagine Jenna Jameson’s pussy. That must be even crazier, but shit, I don’t want to taken anything away from Casey because dam girl, you got an amazing ass. Seriously, first class. I never knew it.”

I looked back up at Josh. “Did you like it?”

“Oh yeah! I can’t believe you let us do that to you. I mean, you are some friend to let us…well, you know,” Josh said. “But yeah, you have a nice body.” He was blushing hard.

“Thanks,” I said, as I smiled back. I had never had anyone say they liked my body, and my body was such a source of embarrassment, so this was a paradigm shift for me, boosting my confidence. “I had a lot of fun too. So…what now?” I was wondering so many things. I almost sounded a little clingy like it was something a girl would say. What did this mean for our friendship? Were they going to be boys and spread the story of their conquest all over school? I figured they wouldn’t, but I just didn’t know. Were they going to tell everyone about my breasts and girly body, embarrassing me and scarring me for life? I had so many concerns, but they weren’t even thinking that far ahead.

“Well, I’m going to shower off,” Tim declared. “We can go in my mom’s bathroom. It is big enough for all of us.”

In the shower, I was without my makeup and girly costume, but that didn’t stop the boys from soaping my ass and tits and getting all excited again. I gave Tim his first blowjob and finished him off in my mouth, while I jerked Josh off and let him cum on my tits.


Things changed a lot after that day. I gained a lot more confidence, and I really started to embrace who I discovered that Halloween. Despite my parents being super religious and conservative, I began growing out my hair and dressing more androgynous. To their distaste, I painted my nails and pierced my ears. I ended up doing counseling through school at first, but eventually, my parents were brought in and told that I identified as transgender. Despite their objections, they followed the advice of the counselors and allowed me to go on hormone blockers and replacement therapy, but they said that they wouldn’t allow me to dress as a girl in their house, and they wouldn’t be using female pronouns.

Tim and Josh kept using me for practice, which really seemed to work because Tim grew to be quite the confident ladies man by the time we reached high school. Still, when he was between girls, if he texted me, I was all too willing to service him. Josh and I actually dated a little on the down low. He moved away after his first year of high school. We stay in touch, and I send him booty pics from time to time, but I can’t really see a long term future. He always liked me, but he was never ready to come out of the closet and declare his interest in trans girls.

High school was some pretty wild times. I’ll leave it at that. I dated a queer girl for a little bit. I would say I find girls attractive, but I’m far more into boys. Now that I am eighteen and out of the house, I feel like I am reborn, a new version of Casey. I am living my best life as who I was meant to be. What’s more, I can dress like a girl, and I can date who I want to date, no longer living by my parents rules. Fortunately, the years were kind to me, and the hormones did the trick to finish what my body naturally started. I have amazing, large, natural breasts without the need for implants, and I have a hot hourglass body with an amazing ass and hips. Most importantly, I kept my soft facial features and large, bold, blue eyes, ditching my thick glasses for contacts. Sometimes I think back on how I got to where I am, confident, happy, dating hot men, having amazing sex, traveling the world and living an amazing life, and I realized it all started that special Halloween night when I agreed to dress up as Harley Quinn. Had I said no, had I not decided to put on that costume and go out, I don’t know if I would be where I am today.

The End