Halloween Crossdressing [mf] [bi] [anal] [oral] [cum play]

The first time i cross dressed was Halloween of my freshman year of college. I have my friend Kylee to thank for pressuring me into it with her constant comments about how cute i’d look in a dress and heels. Now i’ve known Kylee since high school, and she is what most would consider a nymphomaniac. Some of her high school escapades include waiting around in the locker room naked after our basketball team’s practice, sitting in the back of the bus on school trips with a butt plug and letting jocks “discretely” fuck her with it, incessantly teasing the (private catholic) school’s priest, getting kicked off the cheer squad for flashing the crowd, and countless other stories. I could write a damn novel about Kylee’s sex drive but before i talk about the Halloween party, i’ll regale you with the time she dolled me up in her dorm and things escalated ;)

***SHOPPING***

The story starts with myself and a group of my girlfriends (including Kylee) shopping downtown in our college town. It was October so they accompanied their uggs and pumpkin spice drinks with tight leggings that hugged their asses like it was a soldier coming back from 3 tours in Ass-ghanistan. To my resentment, they all treated me like a gbf despite me being bi, however I did get to witness all the playful touches and gropes that are expected in friendships that include someone like Kylee. I’m not a complete creep so I didn’t join in all the time, but every once in a while i’d get a “feel my new bra” or “guys touch my butt.” Kylee was always different, though, she was much more flirty with me since high school, but I never thought much of it because she constantly had a boyfriend (read: boy toy). But back to the shopping: we were in Kohl’s and Kylee pulled a mini-skirt off the rack and thrust it in front of me saying “Here you go Charlie! Found your halloween costume, you can go as Sarah!” I laughed and looked at Sarah as she adjusted her own miniskirt. “Come on guys it’s still warm out,” objected Sarah, “i mean Ky you literally wore one yesterday.” I put the miniskirt back on the rack, saying I didn’t have anything to go with it and even then I wouldn’t make a very pretty girl. The others were walking away and Kylee said quietly “You’d make a sexy girl.” I blushed and shook my head dismissively. “You should wear one of my sundresses, I’ll do your hair and makeup!” She seemed really eager to see me as a woman. I suggested we should catch up with the others when she pulled my hand and whispered in my ear “I can get you fucked by anyone you want at my Halloween party. I know how much you want to choke on Sean’s dick, right Charlie?” She must have noticed how my ears were bright red because she giggled and told me to come to her dorm tonight to try everything on.

***THE DRESS***

I looked at myself in Kylee’s mirror, partly turned on at the sight of myself in a dress, but mostly impressed that the top wasn’t sagging to my stomach. Kylee has big tits (DD i think, idk i’ve never asked) which made the sundress resemble a sail when i wore it and after struggling with safety pins and a sewing needle for an hour she finally got the dress to fit me right. It caressed my body like a dream and felt so soft I never wanted to take it off. I’d never realized how good it felt to wear a sundress; my shoulders free, my legs free, my back exposed. The way the dress fell on my ass made it feel as big as Kylee’s, and I know she picked it to show me off to the boys. The thought of one of them (or better yet all of them) bending me over and taking me from behind right there on the spot was all that filled my mind and my dick responded accordingly, pitching a noticeable tent in the dress. I quickly did the ol’ band tuck with my boxers, unsure if I hid it in time or if I was too slow for Kylee. “Hey Charlie i can see your boxers underneath, you need something smaller.” The way she said it made it clear that she definitely noticed, and now she was just messing with me. “Here put these on.” I turned to see her throw a pair of black lace panties at me. She must have seen the hesitation on my face because she walked up behind me in her pj pants and oversized t-shirt and gently wrapped her arms around my waist. “You’re already grade-A fuck meat, these are just going to seal the deal. But remember those are my lucky pair, so make sure Sean doesn’t rip them.” She winked and playfully fucked me with her imaginary cock once before pushing me into the bathroom to put on the underwear. This did little to help my erection, and so my attempts to put on the tight black panties proved futile. I pulled the dress over my cock to see the head bulging and covered in precum. Everything Kylee was doing had driven me wild, and the sundress didn’t help either. Acting through my groin, I quickly locked the door and sat on the closed toilet lid, dick in hand. Her bathroom smelled overwhelmingly like her favorite perfume, which only made me harder. I stroked my dick as quietly as possible, knowing that the walls were thin and Kylee was waiting for me, which only made it hotter. I took the panties off, held them to my face, and took a deep sniff. I felt like one of those gross weabs in a hentai, but it didn’t stop me. Knowing that Kylee had gotten fucked countless times in them made me feel even dirtier, and the sensation of the soft dress fabric caressing my whole body meant I was edging in probably less than a minute. I stopped for a second to listen for movement from Kylee, and in that silence i had a perverted thought. I stepped over to her sink and opened up the cabinet drawers one at a time slowly and quietly. Three drawers down I found them: Kylee’s sex toys. I knew I had to be quick or else Kylee would come knocking, so I grabbed a bright blue dildo and a small bottle of lube. I started back towards the toilet when I heard the clicking of metal and the bathroom door flew open to reveal Kylee with an amused face.

***THE BATHROOM***

I shouted in surprise and scrambled to hide the dildo behind my back while quickly pulling the dress down over my throbbing dick. “I’m so sorry Kyl-“ I couldn’t finish my sentence before she stepped in and closed the door behind her while gesturing me to stop talking. “You know my bathroom door lock doesn’t work, right?” I started to stutter a reply but she looked down at the small dark stain of precum that had developed on the dress. “Having trouble with my panties? Need some help?” She laughed at my attempt to respond and pulled me towards her as she sat on the closed toilet lid. Her messy bun bobbed to the side as she noticed the toy i was still holding. “God you really are thirsty aren’t you?” She teased as she grabbed the dildo from me. I moved my other hand to show her the bottle of lube but she had already started sucking on the dildo to get it wet. Her soft lips deftly enveloped the blue plastic and i could see drool dripping off onto her hello kitty pants. “Turn around.” She commanded as she made eye contact with me, quickly returning to the dildo. My mind was a frenzied blur, I couldn’t think one coherent thought, all that was going through my head was the sound of my heart thumping and Kylee’s orders. I did as she said and her hand firmly pushed my back to bend me over the sink across from the toilet. I felt the weight of the dress lessen as she threw it up over my bare ass. “Oh so you already shaved, huh? Halloween isn’t for another week so I guess you really wanted me to do this to you.” I was about to speak when i felt pressure against my taint which caused my reply to turn into a moan. I heard Kylee laugh and felt a sharp pain as she spanked me twice. “Tell me you want it, beg like i’m Sean.” She taunted as i felt the wet dildo press against my asshole. “P-please do it.” I said, shaking with excitement. “Do what?” the massaging became harder, the dildo almost slipping into my hungry ass as it pushed again and again. “Please fill me with your cock!” That must have been what Kylee was looking for because I barely finished the word “cock” before i felt the dildo enter my asshole with a *shlick.* I groaned with pure ecstasy as i felt her work the cock in and out, slowly but surely pushing deeper and deeper inside of me. Her one hand was on the dildo, while the other was planted firmly on my sissy ass, squeezing and slapping it like she was kneading dough. Kylee suddenly plunged it to the base before pulling it out, my ass fighting to keep the dildo in. I felt my asshole gape as Kylee suctioned the dildo to the toilet and ordered me to sit on it. I lowered myself onto the plastic cock, pulling my dress out of the way as it fell back down over me. Kylee knelt down in front of the toilet and before I could say anything she whipped the fabric off of my dripping cock and deepthroated me to my balls. I sat all the way down on the dildo in surprise and put my hand at the back of her head. She rolled her tongue around my hot throbbing dick, still pressing her nose against my backboard. I grunted like a caveman and Kylee pulled off coughing, drool and tears making her now-red face messy and wet as she looked up into my eyes and smiled, her hand jerking up and down the shaft like she was playing Yahtzee. She didn’t even take a second to wipe her face before kissing the head of my cock, licking the precum off. I lifted myself up and down, remembering the faux cock squeezing its way up my butt like a python. As I moved my hips up, Kylee sucked further down my member, and as i sat back down the blue dildo rammed my prostate like a bull. I have no idea how I lasted this long, but after a few more heavenly minutes of Kylee gagging on my dick and me riding this dildo, I realized i was close. “Kylee i’m gonna cum-“ She looked up, winked at me, then put both of her hands on my ass and pulled down hard, deepthroating me once again and pushing me all the way onto her dildo so it crashed into my prostate for the last time, turning my brain off with abject pleasure as I felt the jizz shooting out of my dick and deep into Kylee’s throat as her eyes widened. She wasn’t expecting this much cum, and she started to pull back but I pushed her head all the way down as I let out a loud moan. She pulled my hands away and let my dick fall out of her mouth. Her head was filled with cum, so she snapped her fingers and angrily motioned me to get on the ground. I tried to get on all fours but my legs were so weak I fell prone on the ground. I felt Kylee pull my needy ass apart and spit all my cum onto my sore butthole. “Take your cum back, you sissy slut!” I heard her pull the drawer open and felt a smaller toy slam into my surprised- and therefore tightened- ass, using my semen as lube while sending cum dripping down my balls. She licked up any excess and flipped me onto my back as she climbed over me. I didn’t try to speak this time, I just let her kiss me and fill my mouth with my own cum. Kylee pulled her head back and told me to swallow, which I did. She stood up over me and grinned “You’re ready for Halloween.”

**END OF PART 1**

*Thanks for reading! I’ve always loved writing and I’m pretty crass so I thought i’d give erotica the old college try! This is Part 1 of 2(?), I’ll post the next pet as soon as it’s done unless this gets shat on lmao.*

Source: reddit.com/r/Erotica/comments/94sveu/halloween_crossdressing_mf_bi_anal_oral_cum_play

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