tagGay MaleHalloween Kink

Halloween Kink

bytoddstop©

"Hurry up, babe, we have to get going," Jared called through the door. I had to grit my teeth and tear my eyes away from the mirror to answer with, "Just a minute."

The matching costumes had seemed like such a good idea when I came up with the concept. Now, staring at my reflection, I wasn't so sure. Too late now, I told myself. It was our first Halloween party as a couple and we had matching costumes. I'd been so excited for the night and I tried to stop worrying and get some of that feeling back.

I gave myself once last glance. I made a really unattractive woman but that wasn't the point. My sister had come and helped me with the finishing touches and gone to her own party plans. The dark mascara and red, red lipstick were in place, as was the wig. Still, there was no disguising my man face. Or the big lump of cock and balls under the satiny dress. Hell, if I tipped my hips forward you could practically see my circumcision scar under the silky panties and dress. Oh well, nothing to be done now. We were already late for the party. I'd have to remember to sit with my legs crossed.

I opened the bathroom door and Jared's eyes swept over me, taking it all in. He looked hot in his old-fashioned gangster suit, a fake tommy gun in his hand. His fedora was tilted at an angle that made his handsome face look mysterious. He looked really good.

"You look good, Ty, real good." I didn't think he was seeing the same thing I had. I smoothed my hands down the sides of my flapper dress. It was tight around my chest and stomach, not so much around my hips and legs. The thins straps of the dress and bra rested right between the groove of my traps and delts. I tucked a little toy gun into the garter just below the hem of the dress.

"I look stupid but you look hot." I tried not to pout about. What had I been thinking?

"Seriously, you look good," he tried to placate me. I just rolled my eyes at him and slid my feet into the low heels I had waiting by the bed. They'd been nearly impossible to find with my size thirteen feet. In the end me and my sister, Kathy, had found them at a store for trannies and drag queens downtown.

"Let's go," I said and walked toward the door. I wondered how anyone walked in heels, even little ones like mine. I had to concentrate on each step. Worse, I had to keep a hand on Jared's shoulder just to make it to the car. Luckily it wasn't too cold and I didn't need a jacket.

On the ride over we talked about my friends and I gave Jared the latest gossip on who was doing who and what to expect at the party. My nerves eased a bit until we got to my friend Mike's house. We had to park a block away and I found myself leaning on Jared again.

I hate to admit I was vain but I liked guys to stare at me. The drag made me feel foolish and undesirable. I steeled my nerves as we approached the house and plastered a big smile on my face. Had I really thought this was a clever idea to go as a gangster and his moll?

Jared opened the door for me and the thumping bass assaulted my ears. There seemed to be hundreds of people inside. I recognized a few right off and Mike was there. He surged over to me and Jared.

"You made it!" he all but screamed at us. I kept my hand in Jared's and air-kissed Mike's cheeks. "You both look amazing," he gushed. He was wearing a cowboy outfit and I complimented him in kind. His current boyfriend, Jeffery, came up behind him dressed as an Indian. He wore a loincloth, moccasins and some body paint. I wished I'd gone with the go-go boy costumes. I even bought the matching neon green g-strings and the rhinestone pasties to put on our chests. Too bad Jared would never be comfortable showing that much skin. I gave Jeffery a fake smile and pulled Jared further into the house.

Eventually I got over myself and began to enjoy the party. Jared and I split up at one point. I felt bad that he didn't know many of the people at the party but every time I looked over the crowd to find him he was talking to someone. And every time his eyes were already on me. There was a strange kind of intensity in his eyes each time they found mine.

My shoes stayed on for about five minutes before I ditched them. I caught up with a bunch of friends I hadn't seen much of since Jared and I started living together. A few times I wished he was by my side but I wasn't insecure enough to need him there. And if I had been all I had to do was look over at him where he was half paying attention to whatever conversation was going on around him and half watching me.

I had a few drinks, enough to take the edge off, and started having fun. It wasn't long before I was in the backyard dancing. The temperature had dropped but the heat from all the bodies and the strings of paper lanterns kept the area warm. For awhile I mostly forgot all about my costume, except to fix the Cleopatra wig when it started slipping.

"You ready to get out of here?" Jared asked sometime later when he'd found me.

"Are you?" I worried that he'd been having less fun than me. I glanced around and realized a lot of people had left the party. It was later than I'd thought.

"I want to take you home," he leaned close and said near my ear. Sounded good to me.

"Let's go," I said and took his hand. I found Mike and thanked him for a good time. We passed by the last of the revelers and through the front door.

I felt good about the party, glad we'd come. I had taken some shit from my friends for dating a guy I met on Grindr. Coming with Jared was proof that it was possible to meet a good guy on there and let it turn into something more.

"You okay to drive?" I asked as we walked down the block.

"Yeah, I didn't drink." He took off his suit jacket and draped it over my shoulders. Jared was obsessive about his diet and working out so I wasn't surprised he hadn't had even a beer. I shrugged his jacket tighter in the cool air and he wrapped an arm around me to keep me steady in my recovered heels.

The drive home went fast while I talked and gossiped some more, filling Jared in on what I'd heard at the party. We got back to our apartment and I sighed happily, it felt good to be home. I stepped out of my shoes but before I could take off the wig Jared stopped me.

"Leave it on for a little bit?" he asked. Suddenly he seemed nervous.

"Sure," I drew the word out with a quirked eyebrow.

"Could we maybe, I don't know, like, uh, play around some?" It was strange to see my self-confident boyfriend so tongue-tied.

"Yeah?" I tried to figure out what was going on in his handsome head.

"Like, you know, um... pretend you're really a, a girl?"

"What?" I asked with a laugh.

"Role-play, you know, like we pretend...," he trailed off and spread his hands.

My first reaction was to say no. If we had any issues as a couple it was the fact that Jared wasn't as 'out' as me. Moving in together after six months of dating had been a huge step for him. Saying he loved me? It still hadn't happened though I said it all the time. My mind instantly went to the thought that his role-play idea was bad. Only, I was still pretty drunk.

"I don't know," I told him. He winced at my words.

"I don't want you to be a girl, I mean, obviously. I just want to pretend for tonight. That's all, I swear." He was so earnest and I could tell he was a little afraid of what I might say.

"Okay, we can do this. I'm not sure what to do, though." Really, I didn't have a choice because I'd do whatever he wanted.

"Just follow my lead," he assured me. He grabbed up the hated heels. With a big smile he took my hand and pulled me behind him towards the bedroom.

I'd role-played before. I knew this one guy who liked to pretend he was my massage therapist. It had been great because I got the massage and a happy ending. That was easy to play along with. As Jared led me back I found myself thinking that pretending to be a woman was much more hardcore than I'd ever considered role-play to be. I was more surprised to find that my type-A, old-fashioned and pretty vanilla boyfriend would be into it.

"Lay down," he urged me, beside our bed. "Just relax, Tyler."

I did my best to please him but found myself slightly worried as he slipped the shoes back onto my feet. He caressed my legs over the thigh-high fishnets and I smiled inanely because the whole thing seemed so silly. He looked up and as our eyes met the smile wilted away to be replaced by a look of determination and slight disappointment in his gaze. Right then I decided to quit over-thinking and let myself be all in for his fantasy.

His hands moved up over the exposed tops of my hairy thighs as he spread my legs wider. The hem of the dress moved over the tops of his hands and slid upwards. As it reached my middle I lifted my ass and he eased the satiny material up to my waist. Jared took the material in his hands and slid it higher while pulling me toward him so I sat up. Gently he lifted the bunched up dress over my head and off. I laid back and let him get an eyeful.

Jared hadn't seen the undergarments that Kathy had helped me pick out. Now he studied the little bra and panty set. He ran an appreciative hand over the pouch of the panties that barely covered my cock and only one of my balls. I still wasn't hard but my cock was filling with interest. He ran his hands over my abs and cupped my bra-covered pecs in his palms. It had been a bitch to find a bra that was wide enough for my chest yet flat enough. He leaned forward as he pulled the cup of the bra down and licked over my nipple. A zing of energy sparked from my chest down to my rapidly swelling cock.

I reached for his dress shirt and started unbuttoning it as he kissed me. His lips were hard and his tongue swept through my mouth in a way that was more domineering than usual. I opened my lips to welcome his hot tongue with mine and tugged at his shirt. He broke the kiss and sat up on his knees. He pulled the shirt free from his trousers and pulled it off, revealing his lightly haired torso. Without pausing he undid the fastening on his pants and pushed them down and off.

His hard cock strained against the plain white cotton of his boxers. Typical Jared who often made fun of all my brightly colored briefs - though he loved to see me in them. I reached forward and pulled at the waist of his boxers which he helped to remove. He was left naked except for the dark dress socks on his feet that reached mid-calf on his legs.

Jared's big cock reared up out of the dark tangle of his pubic hair. It was one of the things I loved most about Jared, his low-maintenance and regular-guy attitude. He'd laugh if I suggested manscaping to him. He worked out but wasn't at all vain about his looks or body although he had every right to be. I watched him run his hands over my legs while my cock stretched out along my belly well passed the edge of the panties.

I rested my hand over his pec when he leaned forward, the red on my nails was glaring and distracting. He kissed me again and fitted himself between my legs so our cocks could rub together with a minimum of space between our chests. I moaned against his lips and he dominated the kiss with his tongue and teeth. I shivered as he kissed across my jaw.

"Baby, you're so hot," he whispered in my ear before licking around the rim of it. He never called me that. Babe and Ty were the beginning and end of the list of his endearments for me. His 'baby' left me feeling coddled and a little vulnerable.

Jared kissed down to my neck, moving the hair from the wig away with his nose and breath. He bit down on the skin and sucked. It made my balls pull up and my cock lurch. Slowly he released the pleasant suction to kiss and lick down my neck. He found my nipples through the bra and nibbled at one then the other. He pushed the material out of the way and paid more attention to the hard nubs with his mouth until he had me groaning and rutting my hard cock against his. The slick feel of the panties added an extra sensation of pleasure.

"Oh God, Jared," I moaned. I buried my fingers in his short brown hair and messed up the careful part he always had.

"I'm going to make you feel so good, baby," he promised from my chest. He looked up and I met his dark eyes. "You want me to go down on you?" he asked with a hint of uncertainty. "Want me to eat you out?"

I had to remind myself that I was all in, again. "Yeah, please, Jared. Do it."

He ran his hands down my stomach and drew my legs up and open. The heels of the shoes dug into the bedspread. He bent forward and nuzzled against the panties, blew hot air onto my cock and balls. I was tempted to beg him to suck my cock but barely restrained myself from breaking character. I was so hard it hurt.

I dropped my head back and pulled my knees up, holding onto the back of each where the stockings were damp with my sweat. There was a tug at the panties and I looked down to see him with a fold of the material between his teeth. He tore a hole with his fingers and teeth then reached in with more fingers and spread the hole open up the back. The tearing of the fabric seemed so loud and sent a tingle up my spine.

Jared delved into the split and his wet tongue brushed over my asshole and taint. A shuddering moan escaped my lips. "You want me to eat your pussy, baby?" The word pussy was shocking but whether he said pussy or ass I wanted him to do it.

"Oh yeah," I told him. And if my voice was just a little higher pitched than normal I told myself I was just getting into the role for Jared.

He lapped over my opening with broad swipes of his tongue. He sealed his lips around the ring of muscle and sucked before stabbing into it with the tip of his oral muscle. "Please, please...," my voice without my conscious permission. He pushed more of his tongue into me with his hands on the backs of my thighs right where the stockings ended.

Loud slurping and sucking sounds from his mouth echoed out while he used his lips and tongue to fuck my hole open. His teeth scraped over delicate flesh and my head came up off the bed. He was killing me. He speared his tongue inside and unfurled it, spreading my ring. My heart pounded in my chest and I clamped down, forcing his tongue out.

He moved over me again and reached into the drawer of the bedside table, coming back with the lube. He squirted some onto the fingers of his right hand and smeared the lube over my asshole. He pumped more lube out and used it to push a single digit into my ass. His mouth swallowed my gasp and the heaving breaths I couldn't seem to control. I wasn't always the bottom but I'd never wanted him to fuck me quite so badly.

"Your cunt's so wet and hot inside, baby. You want me to fuck you?"

"Yes, Jared, yes. Do it." Not very commanding, more pleading. I might have felt a little embarrassed for myself. He pushed another digit in and fingered me slowly.

"Hand me a condom, baby." I fumbled for the drawer then paused.

"You don't have to," I told him. There was a long pause in which we eyed each other, lifted for a moment from the game we were playing. We'd talked about losing the condoms, had done the math. Nine months together, six of them living together and clean tests for each of us every year. Really, Jared wasn't the one who had to worry. He could count all of his past lovers on two hands and three of the nine had been women. I would've needed a few dozen pairs of hands.

"You're sure?" His eyes flicked back and forth at mine, judging my sincerity.

"If you are, yes." He grinned and kissed me sweetly on the lips.

I couldn't explain what made me say it. I wanted it, sure. Maybe it was the peek into my straight-laced boyfriend's kinky side. I'd had no reason not to trust him before, I just knew that he was opening up to me in a big way. His trust in me was proof that I could count on him.

"Are you on the pill?" he asked with a goofy grin. "Because I don't want to get you knocked up." It was a joke but it reminded me of the game we'd been playing, probably what he'd meant it to do.

"Yeah, the pill," I agreed and clasped his fingers tightly with my ass.

He looked at me with a pained expression and gently tugged his fingers out. He picked up the lube and this time used it to wet his big cock. Jared pushed it up against my hole and slowly sank the head into my ass. He rose up onto his hands and stared down at me while he fed his length into my body. I bit into my red bottom lip and tried to relax for him.

"You're so tight, baby. Is my big cock hurting your little pussy? Can you take it?" It felt so wrong that his questions should turn me on but they did. I decided to worry about what that meant later.

"Your cock is so big," I told him with a pout. "I... I'm afraid my pussy can't take it." There, I said it and it wasn't as hard as I had thought it would be.

"Just let me in, give it to me. I'll make you scream, it'll feel so good." Jared's voice had gone deep and rusty sounding.

"Promise?" I squeezed around his shaft as he pushed the last little bit in. He was big but I'd had plenty of practice over the last nine months and truthfully it didn't hurt that much. He groaned as I flexed and pulsed my insides around his cock. "Does it feel good when I squeeze your big cock with my pussy?" Was that me who said that?

"Jesus, baby." His cock throbbed.

"Fuck me, Jared."

He slung my legs up onto his shoulders from his elbows. He laid over me and began to hump his cock into me with short strokes that kept him deep in me. I wrapped my arms around his shoulders and moved as much as I could with him. Gradually he withdrew more with each thrust until he was steadily dicking me with long and even strokes.

"Yes, Jared, yes," I chanted. He adjusted the angle of his plunging cock to where he knew I liked it most.

"You love my cock in your pussy?" he asked between gasping breaths.

"Yes, God, yes." I may have been breathing even harder than him. I was sinking into the pleasure of his hard cock plundering my ass.

"Say it!" Jared's voice was deep and commanding.

"Fuck my pussy." I grabbed onto his ass and squeezed the hard globes to encourage him.

"Louder!" I never guessed his voice could sound like that.

"Harder! Fuck my pussy harder!" I screamed it, couldn't stop myself. I'd never wanted to be a woman. Never even wanted to dress in drag but this was too fucking hot. My balls crawled up against the base of my shaft, under the torn panties.

He let my legs fall away and I wrapped them around his waist. He pushed his arms under and around me, pressed our chests together. His flexing hips and ass went into overdrive and he powered his cock into my body until we were bouncing together on the bed in a furious fuck pace.

The need and intensity built quickly as his cock bored me out, rubbed over all those sensitive spots. I felt his hard body all over with my hands and rubbed the sweat from his brow. I felt so good and alive in the moment. I wished it would never end but I could feel him pushing the cum up out of me with his hard fucking. His cock bucked and throbbed so I knew he was close as well.

"Cum in my pussy!" He paused, open-mouthed, and crushed me all the harder against him as I felt the wetness of his cum filling me. I called his name and let loose with my own spray of cum between us. I held him just as tight while he pumped the last of his load into my ass.

After all the buildup and anticipation it felt so good to let go. I melted under Jared and my legs fell onto the bed. My cum filled the space between our bodies and ran down my sides. With a sigh he pulled his cock free of my hole and collapsed onto the bed beside me.

"Holy shit," he said up to the ceiling. "That was so... amazing." He turned onto his side and leaned over to kiss me, slow and deep. "I'm still hard," he said with something like wonder. I nodded because I could feel it pressed up against my side. I rolled onto my side and pressed my sloppy ass up against his arousal. I reached back and moved his cock down. Jared got the hint and slowly pushed it back into my aching chute.

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bytoddstop© 8 comments/ 30308 views/ 19 favorites

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