A Sissy's Halloween

Disclaimer/authors not: All characters in this story are over the age of eighteen. This is my first story so criticism is wanted as long as its constructive. I make these stories based on what I want and my own sexual fantasies. Thank you 😊 .

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To tell this story right I need to start at the very beginning, the time where I first started to question my sexuality. In high school I had had always watched a lot of porn, since I had the house all to myself normally I had ample time to satisfy my lust. Though there came a point where normal guy on girl porn just wasn't enough for me.

In high school I was very short for my age, had long black hair that went below my ears, and had somewhat of a feminine frame and hairless other than a little patch above my crotch. I never had that huge growth spirt, or that voice drop, and not to mention my dick barely even grew, by the end of high school I was 4 inches at my hardest. Around sophomore year is when I discovered sissy porn. At first, I found it kind of weird but there were a lot of things about it that just made me hard. It was mostly captioned gifs of hot girls with cum over there faces or sucking cock or taking it up the ass, but there'd always be a caption that said "accept your true self sissy" or something along those lines.

The more I touched myself to it, the more I wanted it. I wanted to be that girl in that picture, to suck that big delicious cock or have that hot stick cum all over my face. Then senior year came, a year where I took it to the next level. During the summer before it started, I got so horny and said, "fuck it" and started searching in my mom's room, I don't know what for until I found it, a nice big dildo. At first, I was shocked, and didn't know what to do, standing there naked until I picked it up and brought it to my room. I laid across my bed and started feeling it up, it had veins all over and a suction cup on it, my cock was throbbing like crazy. I ended up jerking my little cock as I felt it up, and then put the toy back in my mom's drawer. This continued for weeks and weeks until I got the nerve to put it on a wall and suck it, just like how I saw in the sissy gifs. It was so satisfying but I was missing something.

That something was women's clothes. One day as I was fetching the toy, I saw my mom's underwear laying out in the open, I got the naughty idea of maybe trying some on. I had a similar figure to my mom, so I thought they would fit easily, only difference was her breasts. I did some digging and found a nice soft pair of lace panties that felt amazing as it hugged my big ass and had a strange feeling on my cock as well as a corset, tightening it up all the way, I looked in a mirror and adjusted my hair and I believed I could pass for a girl. A nice hourglass figure with the corset, small breasts, and a sexy butt to match, with short hair and bangs. I could not describe how I felt, it was like sexual freedom for the first time and I loved every minute of it.

From then on, I always sucked the toy cock in that outfit, getting to the point where I started using my fingers to play with my ass as I listened to sissy hypno or bimbo hypno as I sucked cock. And I loved ever minute of it.

Then came the point where I wanted more than just fingers up my ass, and one day I decided to bring that feeling to light. After lubing up the cock with my mouth I lowered it enough and took off my panties. Slowly and surely, I backed my ass up spreading my cheeks until I felt the cool plastic wet tip against my hole. I was nervous, scared, and overall, I was horny. I pressed against it lightly, teasing myself as I pictured a big strong man with a big meaty hot cock pressed against my hole until I begged for it. And I wanted to beg so badly, I pushed on it until I felt it slide inside with a plopping sound. I moaned like a woman and was so happy nobody else heard it. My cock hard and throbbing as I held it there for a few minutes, shaking my butt side to side feeling it out until I back up more and more, gasping as it slid inside. I refused to touch my cock wanting to reach the sissygasm I had heard so much about. Rocking back and forth, arching my back as I moaned in ecstasy. The feeling of my ass being filled by that cock was more than bliss, it was heaven itself, that feeling was my god and I wanted to feel it every day. It took a long time, probably two hours of me sweating, moaning, and re lubing the cock with my mouth until I was able to cum with my slutty little ass. And when I did, I felt the pressure rising as a small little stream dribbled out onto the floor, making a little puddle beneath me as I moaned.

My legs were weak and shaking as I slid off that cock with a resounding plop. Biting my lip as the cool air filled my asshole. I loved the feeling that came after, the feeling of your ass staying open for at least an hour. I walked around in those panties and corset with my ass gaping all giggly, putting away the toy once I was done cleaning it just in case.

After that sissygasm, normal orgasms just didn't meet expectations. So, to solve that, I used my first debit card and decided to get some things of my own. When my mom was out I dolled myself up and went outside nervously, wearing black yoga pants, a tank top, and did my makeup so that I was sure to pass as a girl, and pass I did.

It was close to Halloween of my senior year and I didn't have a costume yet. I was invited to a friend's party and decided hell why not try something out for a change and get a girl's outfit. So that I did, along with buying a new corset sized to me, and three new panties and one long black amazingly thick dildo, I decided to browse the women's section of the Halloween store. There were so many outfits to choose from, mostly slutty attire that I couldn't help but get a hard on for, from sexy nurses' outfits to slutty witches. After a while of searching I found a leather cat outfit that could both hide my corset and my dicklette underneath, I tried it on and fell in love instantly. Buying that I started to walk out, and noticed something strange, in the adult shop I bought the dildo I saw something I didn't notice at first, a pink and white chastity cage. My jaw dropped, so tiptoeing inside I snagged it, putting it in my bag and walked out as if nothing happened.

I got home in an ecstatic glee as I went to my room and unpacked everything. It was like Christmas but so much sexier. I laid everything out on my bed, the new dildo, the corset, the panties, the costume, and of course the cage. As well as some new girls' clothes I ordered online previously, with the party in a few days I decided to test out how I looked in the costume, putting on the corset and panties, a perfect fit for me, as I slid into the costume and zipping it up. The costume was tight, especially around my waist and ass. I went to a mirror and checked myself out. I really looked like a slutty girl, a nice hourglass figure, big ass, and a cute face as I put on the ears. I took a few pictures smiling.

"I really look like a slut, and a sexy one at that" I say to myself as I pose some more taking pictures.

I smile as I look over those photos, getting a dirty idea. Using a free msg app I text the person who's hosting the party. I text the following: "hello, I heard you were having a party this week, I'm here with my cousin for the holiday but he cant come, mind if I go?" and send him a picture of me in my costume "ill be wearing this, I heard it's a costume party right?". As I lay on my bed waiting for a response.

It was two hours later when I got my response, the messages between us went like this:

"hello, I heard you were having a party this week, I'm here with my cousin for the holiday but he can't come, mind if I go?

I'll be wearing this, I heard it's a costume party, right?

OFC LOL, id love to have you, what's your name btw

Samantha and ty.

Np, here's the address, see you there sexy

His last comment made me pause blush and smile. I was really doing this, I had made a guy think I was a hot girl. I was thrilled and dumbstruck.

I spent the next few days going to school coming home, and riding that new cock lovingly and passionately, training my ass just in case for the party. My dreams were filled with fantasies of gangbangs and me being fucked and dominated in other rooms, made to be a big slut to all. Cumming hard to these fantasies, wearing my new chastity every day without fail.

On the day of the party I was too excited as I got dressed up, everything looking perfect on me as I text the person who was hosting one last time saying I was on my way now. I walked there on my own, with tricker treaters heading in for the night. I got a few stares from fathers as I went, even catcalled by a passerby, the feeling was amazing. As I arrived it seemed like the party was in full swing, I got a text from the host asking if I was there, and I responded that I'm at the door, just arrived.

As I opened the door I was greeted by a big muscular guy, who I'm guessing was the host as he said "Samantha right? Glad you could make it, let me get you a drink"

"t-thank you, by the way I was never told your name" I said awkwardly. I looked around and the party was filled with guys in burly outfits or funny ones, and girls in the most outrageously slutty outfits, some wearing just underwear. So, this was what a party was like I thought to myself.

"it's Nick, guess I forgot to tell you, I was too caught up looking at you" he says as he gives me a wink. His costume was a half-naked cowboy outfit I'm guessing, as his shirt was covering almost nothing, had a cowboy hat, and some tight ass pants. I couldn't help but stare as I followed him into the kitchen.

"t-thanks" I say blushing as I hop up on the counter sitting across from him as he hands me a drink, I take a sip. Coughing as I taste the alcohol.

"don't drink, much do you?" nick asks as he laughs.

"no first time" I say smiling like a dork, as I take another small sip. Looking at the ground.

"so, what brings a fine ass woman like you to this shitty town" he says as he walks closer, standing in front of my legs.

"o-oh um, just family mainly, I'm on a bit of a vacation from school for now", I say looking up with a smile.

"makes sense, do you have a boyfriend from your home town", he asks as he puts his arms on the counter next to me looking right at me. He must have been able to tell how aroused and embarrassed I was, because my cock was hurting in its cage.

"no boyfriend, ha. Guys um... they don't really like me from home" I say awkwardly.

"oh, and whys that, your certainly hotter than all the girls here by a longshot, cute ass, sexy face, and one hell of a body" he says in a tone of voice that almost made me swoon.

For a moment I paused and lean In and whispered, "if you promise not to freak out or tell anyone I promise to show you and maybe give you something else", I say smiling. This was it, really it, I was going through with it, and from what I heard about nick, would fuck anything cute with a pulse, guy or girl.

He smiled and wrapped his hands around my waist and said, "secrets are my specialty' and brought his ear close to my lips.

I leaned in and whispered saying, "w-well... I'm not fully a girl.... I'm sorta maybe a crossdresser" I say awkwardly.

He turned to me and thought for a moment, as if examining me, re looking me over "are you sure, your too hot to be a guy in any shape or form" he says as he gave my ass a hard squeeze. Which made me moan silently, "see, even moan like a girl".

I blush, "I really am a cross dresser... I can prove it if you want, maybe even... give you something for not telling anyone" I say as I look at him wistfully.

He smiled with a cocky grin and lifted me up, carrying me out of the kitchen as others cheered at him, "I think id enjoy that" he said as I wrapped my arms around him, blushing as he carried me up the stairs.

He brought me up to the bedroom, his parents I assumed with how clean it was. The bed was made, sheets in and clean. He put me down on the bed, and at this point I saw in his pants the biggest bulge I've ever seen without a doubt. I gulped and smiled as he pointed to my outfit and said "costume off, I wanna see" he said, and I was more than happy to oblige. I turned around, ass toward him as I unzipped my outfit, letting it fall off to reveal my corset and black panties, as I turn around, my chastity cage visible inside my little panties. He smiled and walked closer to me, hands on my waist feeling me up "your definitely cuter than any girl I've ever seen" he said as I blushed up at him.

"t-thank you... you're not grossed out?" I ask smiling.

"of course not, I've always wanted to fuck a slutty sexy sissy", he said as his hands went down gripping my ass hard, making me moan loudly.

His words made both my heart and cock throb in glee, this is what I always wanted. I looked up at him with puppy dog eyes, pout lips and the faintest smile and said "w-well then fuck me like one". The words came out quiet and slowly, as it was hard to say.

He just gave me a grin and undid his shirt and said "get on your knees" in a sexy dominant voice that made me drop instantly. As he unbuckled his pants, letting them fall, then his boxers. And oh my god what I saw was the most amazing thing in the world. His cock wasn't even fully hard, and it was bigger than my face, it was like eight inches half mast and it looked amazing and delicious. He laughed seeing my reaction and told me "go on sissy, feel it up, taste it, you know you want to". And that I did. Using both hands I wrapped them around his big hot cock, it was a bit flaccid, but I could feel it getting harder as I felt it. It was soft and smooth, and it made my mouth water. Inching my lips closer I planted a big kiss on it. Then giving the tip a tiny lick, giggling a lot. He gave me a warm smile and rubbed my head, holding his hand on the back, as I slid it inside my mouth, he let out a groan as it went inside, I was worried I was doing something wrong, but he said, "fuck that's good". So, with that I slowly slid down, doing what I had practiced with my dildo, bobbing slowly as the taste of that cock filled my mind. My eyes on his as I blushed, my hands rubbing his balls gently as I carefully suck on his cock, not going the full way down as my lipstick smears his cock red, a light ring around the deepest I went.

As I bobbed I felt his hand push me deeper, I looked up nervously. He just told me "don't worry, just some encouragement". Understanding I just went deeper with his help, gagging a bit when it hits the back of my throat. Drool running from my mouth onto my corset. As he forced me deeper my eyes teared up, not used to taking something so big deep into my throat, and it was barely halfway in. I thought I was going to pass out when I felt the tip slide deeper. His cock was so hard I almost couldn't believe it was going down so easily. As soon as he let go of my head I popped my mouth off his cock to cough, giggling a bit. And when I caught my breath I went right back down, but he stopped me "ah ah ah, give me a second and lie down on the bed, on your back" he said demanding.

Listening, I stood up and laid across the bed, curling up a bit, feeling a tiny bit insecure, he stood over me and parted my legs, putting a finger inside my mouth with one hand and taking my panties off with another, "lube it up sissy, you need to loosen up" he said smiling. I sucked on his finger excitedly and as he pulled it out I spread my legs wide. With one hand he parted my cheeks and with that wet finger, he slid in. the feeling was unlike before, it was different and amazing, I moaned out in surprise. His big meaty finger thrusted in and out gently, my cock hurting in my little cage, wanting freedom as his finger curled inside, "that's it your sissy slut, take it up your ass". His words must have made me tighten up and I don't know why but I felt my asshole shrink around his finger, "wow, you are a tight one" he said as he gave me a light spank.

Minutes passed as he fingered my little hole. With me squirming and moaning, I could feel the blood rushing to my head, it was amazing. It was hard to think of anything else but that feeling of his fingers inside me. I could tell I was sweating, my whole body felt like it was on fire, until he pulled his finger out. I was looking directly at him at the time by I heard him stand up. I turned to see him spit in his hand and slowly stroke his cock, getting it wet once more. "is this what you want you little sissy slut?", he asked as he grabbed my waist pulling me to him, my ass against him with his cock over my caged sissy clit.

I lightly nodded and with a grin he slowly lifted me a bit higher and parted my cheeks. I felt the tip pressed against my asshole, so warm, so inviting. He must have been able to tell how much I needed it, because I heard him laugh and slowly slide that cock in. I gasped and threw my head back, feeling my ass envelop around it. This was not like my dildo at all, this was so much better, it was as if it was something else entirely. I felt every inch as he glided in slowly. He was purposefully going slow, making me remember what every single inch of his cock felt like inside of me, and I love him for it. Once he got to the base, my cheeks were read, my mouth wide open, out of breath, and completely happy. This is the feeling I craved, a sense of being stuffed.

He leaned down and kissed me, whispering afterward "Ready for more", as I felt him slide out. I wasn't even able to say anything, only able to let out a moan. As he got to the tip he slides right back in, keeping a slow steady pace for my own good. Making my first time the most amazing thing I've ever felt. He kept that pace going for a short while, as I felt my orgasm build up more and more, as he aimed for my prostate. Feeling my orgasm about to burst, my legs wrapped around him without thinking as my whole body shook, sending a large shot of cum out of my cage, my moan louder than before. As I came, nick groaned "fuck your too tight" he said as I panted.

"guess I better finish up ass well, hope you like it rough", he said, though I could barely even process it, still feeling my orgasm. He flipped me over on my stomach, raising my butt in the air with his big strong hands, forcefully pulling my hands behind my back, then guiding the tip of his cock back inside my ass. The change in position was completely different. As he slid in, I arched my back gasping for air once more, as suddenly, he started thrusting, hard and fast. Hitting my insides at every point without mercy. My mouth wide open, tongue out as I drooled from the rushes of pleasure he gave to me with each thrust. He was grunting and breathing hard, turning my ass inside out with his huge cock. In no way did I expect that cock was this good.

I felt his cock throbbing inside me, with his pace slowing down he pushed me flat on the bed, putting all his weight on me as he thrusted inside. My body bouncing with each thrust on the bed. I felt his breath against my ear as he wrapped a hand around my throat choking me lightly. The lack of air made the feeling much more enjoyable as suddenly, a felt a rush of something hot inside me. Nick groaned and stayed inside me, shaft buried in my ass to the base as he came. His warm hot cum being shoved deep inside of me was just enough to force out one last tiny orgasm, dribbling out of my cage as I gasped for air when he let go.

After a few seconds he pulled out with a plopping sound and stood up giving me a hard spank, turning me around and planting a huge kiss on my lips. "Damn I could get used to an ass like that", he said as he collected his clothes. Putting on his costume before lying next to me.

For at least five minutes I was breathing hard, barley able to move. After catching me breathe I responded, "and I could get used to a fucking like that" as I gave him a little wink.