Straight Crossdresser

Summary: Guy dresses as a girl on Halloween and ends up performing as one.

Note: This is a Halloween 2019 Contest story, so please vote.

Thanks to: Tex Beethoven, and Robert for editing.

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As I draped the sheer pantyhose onto my legs to finish off my Halloween costume, preparing for a night of cock sucking and bottoming at the annual Halloween men's only orgy (my wife Amber going to her own annual girls only Halloween orgy), I couldn't help but reminisce about the day I realized I loved wearing pantyhose, loved sucking cock and was a natural bottom.

It was thirty years ago.

The year was 1989.

I was eighteen.

I was straight.

I was the starting wide receiver on my high school football team.

I was dating a knockout cheerleader, Amber (whom I eventually married), who was a kinky insatiable slut: she liked sucking cock, she loved getting fucked, and was even happy to take it in the ass.

I had it all.

Then... during one wild crazy Halloween night... everything changed, but not for the worse.

First, using Halloween as a cover, I decided to try something I'd always been curious about: I wore pantyhose.

I've always had a thing for pantyhose.

My mom wore them all the time.

All teachers back then wore them every day... they had no idea the impact their dangling heels had on me as they sat at their desks.

The cheerleaders wore them with their outfits.

Oh... the eighties... they were so awesome.

So although my girlfriend thought it was her idea, as I'd manipulated her into thinking it was, she dressed as a football player and I dressed as a cheerleader for the nighttime Halloween party... no way was I wearing that to school, as I would be dress coded for sure.

Simply putting the pantyhose on was a major turn-on. I loved moving my hands up and down Amber's pantyhose-clad legs, I loved when she stroked my cock with her pantyhose feet and I loved sucking on her nylon-clad toes (although she thought that was a little weird). I knew this next was also weird, but I decided not to wear underwear, so I could feel the smooth pantyhose on my cock.

I rubbed my cock over the pantyhose, and it felt so good I had to stop or I would have come in them, which would have been the end before I even got started.

Amber arrived with a wig and did my make-up. She teased, as she looked at her handiwork, "You're kinda hot as a girl, Ben."

"Think so?" I asked, suddenly a little self-conscious.

"Oh yeah," she smiled, as she leaned in for a kiss, "you'd probably fuck yourself."

I laughed, "If only I could."

"Hey," she said, reaching behind me and slapping my ass, "That's my job."

"Wait," I said, realizing that didn't sound right. "I'm supposed to fuck you."

"Play your cards right and you will," she smiled.

"Oh, I'll play them right," I flirted back.

"I bet you will," she smiled, as she lowered herself before me, flipped up my skirt and checked me out. "No underwear," she mused.

"I thought commando was hotter," I answered, as she pulled my pantyhose down and took my cock in her mouth.

"This doesn't count as playing my cards," I moaned as she bobbed.

A few minutes later, my load deposited in her belly, I finally looked in the mirror. With the blonde wig Amber had brought, added to her make-up job, I did look... dare I say it?... kind of hot.

As I stared at myself Amber said, "You really look good, baby."

"Thanks," I said, mentally agreeing with her.

"I guess we should have bought heels for you too," she said, looking me over.

"I'd probably kill myself in those," I laughed, as I was wearing girl's shoes... but they were basic black flats.

"What doesn't kill you makes you stronger," she quipped using my usual truism, as she patted her chest just like I did after I made a big catch.

"Fair enough," I laughed.

We headed to the party as she warned teasingly, "You may get hit on by some guys tonight."

"And you may get hit on by some girls," I countered.

"You'd like that," she laughed. Actually, she'd been teasing me about a threesome for a while. She even listed a few of her friends she'd be willing to go down on while I fucked her. So far she hadn't mentioned my fucking any of her friends, although I wasn't sure I wanted to anyway (just seemed like a bad idea), but the idea of watching her licking a pussy was pretty fucking hot.

"I wouldn't not like it," I countered.

"Perv," she said.

"Just a guy," I shrugged.

"Every guy is a perv," she extrapolated.

"You're just as big of a perv as I am," I pointed out.

"Guilty as charged," she laughed, as we pulled up to the party.

"So you're allowed to fuck any girl you want tonight, and I can fuck any guy," I joked, as I got out of the car.

"Not exactly girly, you can suck any cock or take any dick in that pretty ass of yours, but your own cock is imaginary," she played along as she got out of the car and slapped my ass.

"So I have permission to slut it up tonight and to do anything a girl can," I continued.

"Yep, you may receive all the dick you can handle," she agreed with a laugh.

"And you can munch on as much cunt as you wish," I offered generously in return.

"I can't fuck them with my big dick?" she asked, as she pulled a strap-on cock out of her oversized purse.

"Wow! Okay, fuck away," I laughed, wondering when she'd bought one of those.

"I'll bang some bitches tonight," she bragged, in a lame attempt to sound like a guy... she just didn't have a deep enough voice for it.

"Bang away," I laughed, the visual of her with a strap-on pounding any one of her hot friends making my cock harden in my pantyhose.

We walked into the party, and I was teased like crazy by my buddies. My ass was slapped. My fake tits were cupped. I wondered if this was what happened to the real girls at these parties.

I had a few drinks.

Amber had a few drinks.

We were very comfortable in our relationship, so it wasn't unusual for us to be apart for most of the night... so long as we ended up going home together.

I was finishing a drink, sitting on a barstool, when a guy I didn't recognize, dressed in a Superman outfit, hit on me. "Hey cutie, you want to be my Supergirl?"

I laughed but played along, assuming he wasn't serious. "I bet you say that to all the girls."

"Only to the girls worthy of a man of steel," he said suavely, something I would have said on the prowl in my pre-Amber days.

I playfully glanced down to his crotch, which unless he had a sock in there, was pretty impressive, "Is that so?"

He smiled as he cupped his dick and sat down beside me, "All steel."

"I hope you're not faster than a speeding bullet," I joked, getting a bit of an odd rush as I flirted with a guy. It was harmless, sure... but it was breaking the usual mundanity of a party: drink, joke, drink, tell stories that aren't even half true, and oh yes... drink.

"More of a marathon runner," he said, his hand going to my knee, "I love a girl in pantyhose."

"I love wearing them," I said, oddly enjoying his hand on my leg. Yes he was a guy, but we were just role playing, so I went with it.

"You look hot in them," he complimented, his hand slowly creeping up.

"Thanks," I replied, beginning to think this was a little more than harmless banter. Did he think I was actually a girl?

"I have a weakness for a sexy girl in nylons," he continued, his hand reaching the bottom of my skirt.

He did think I was a girl. I was kind of flattered. Yet I wasn't sure how long to let this go on. Yet, I couldn't resist the obvious response, "So nylons are your kryptonite?"

He laughed, as his hand ventured beneath my skirt, "Yes, they are."

How far was I going to let this go? I should have stopped it by now. Yet I still didn't. I found this interlude both exciting and stimulating... my six-inch cock hardening underneath my short skirt.

When I didn't say anything to object, his hand disappeared under my skirt. I stammered, partly acting coy and partly paralyzed by indecision, "W-w-what are you doing?"

"Saving a damsel in need," he said, his hand stopping just a few inches from my now completely hard cock.

"Do I look like I need saving?" I asked, part of me annoyed he'd stopped his hand, part of me thankful. These mixed feelings were confusing the hell out of me. What was I hoping would happen here?

"Definitely," he nodded, just as his hand darted forward those final few inches and squeezed my cock. "Nice," he said, revealing he knew I was a guy.

Shocked, I leapt off the barstool and headed to the bathroom. My cock was hard, my head was spinning, but I also needed to pee. I stammered, "S-s-sorry, this girl needs to go to the washroom and freshen up."

I could feel my cock rage and my cheeks burn as I headed to the bathroom to finally break the seal and get some time alone (when drinking, I always held out from pissing until I couldn't any longer... as once I went the first time, I seemed to make constant trips to the bathroom... which at a party could be a pretty lengthy wait each time).

The bathroom door was locked, so I headed upstairs to the ensuite one I knew was off Dave's parents' bedroom, and thankfully both rooms were unoccupied. Usually someone was using the bedroom to get head or get laid, sometimes it was me, so the path being open was a miracle.

I pulled my pantyhose down and instantly began pissing through a hard cock. In spite of the difficulty, it felt almost like an orgasm. I know that sounds strange, but God, it felt good.

As the never-ending gold stream sprayed, I replayed what had just happened. Why did it turn me on? Why did I let it go so far?

I smirked at recalling Amber saying I could suck or get fucked by any guy tonight. She didn't give me permission to get sucked though, since a girl couldn't do that. I guess that also meant she couldn't get licked or fucked, at least not in her pussy, so fair enough.

I finished pissing.

I tapped an extra few times... didn't want any afterthought leakage into the pantyhose.

I pulled my pantyhose back up and rubbed my cock against the sheer nylon. It felt good. I considered jerking off, but resisted.

I washed up, always disgusted by how many guys don't wash their hands after going the washroom, and headed out.

I froze.

Superman was in the bedroom sitting on the bed.

"Come here, beautiful," he ordered.

That's something else I would say. It would be followed by Amber dropping to her knees, or my guiding her to her knees and her sucking my cock.

Oddly, I felt myself walking towards him.

Why?

I reached him and began to protest, "Look bud, I'm straight."

He reached his hand under my skirt and directly to my cock. "You sure about that? Then why are you hard?"

"I don't know," I answered, as I allowed him slowly to rub my cock through the pantyhose.

"You like this, don't you?" he asked.

"I-I-I don't know," I stammered with an undeniable moan.

"You're dressed as a girl for only one reason," he said, slowly rubbing my cock.

"To wear pantyhose," I clarified.

"That's what you think consciously," he said but added, as he put his hands on my shoulders and did what I'd done at least a dozen times in my life from his point of view, and firmly pushed me down, "but unconsciously you want to be a girl."

I was physically strong enough to resist. I was a little taller than he, and he was likely a little wider, but I definitely could have resisted: legs are stronger than arms.

Yet I didn't.

I felt myself suddenly on my knees.

My face near his crotch.

As I pondered his claim, I let him treat me like I was the girl. What he said wasn't true. I'd never imagined being a girl. I'd imagined dressing like a girl, but to be one? Never.

"Take out my cock," he ordered as I knelt before him.

"I have a girlfriend," I stressed, realizing I was really getting myself into a surreal predicament.

"So do I," he said as he suddenly pulled his cock out, "but I bet you'll be a better cock sucker than she is."

I literally gasped.

Not at the size... although it was big... seven plus inches and with a unique upwards curve.

But at the audacity just to pull out his cock in front of me.

I stared.

"Go ahead, just stroke it," he ordered.

"But I'm not gay," I said.

"Me neither," he said, "but tonight you're a girl. A cute little cock sucking slut."

I couldn't believe he'd just called me a cock sucking slut. I should have wanted to beat the shit out of him. Yet my knees felt glued to the floor.

When I didn't protest his shocking name calling he repeated the order, "Go ahead and stroke it, we both know you want to."

And I couldn't explain it; I'd seen a lot of cocks in the change room and never been intrigued by one, never pondered sucking one, never considered myself even slightly curious, but at this moment I was intrigued... I was definitely curious.

"You don't have to suck it if you don't want to," he said. "But you got me hard as steel in that sexy outfit, so the least you can do is jerk me off."

To my muddled brain, this seemed like a logical compromise. I didn't have to suck him; and it was my fault he was hard.

I mindlessly reached up and wrapped my hand around his hard-as-steel cock.

"There you go," he said approvingly, as I began to slowly stroke it.

"That feels really good," he said.

I stared at his cock in awe.

It felt so weird in my hand, but weird in a good way.

"Good girl," he moaned, as I continued stroking his cock.

Being called a good girl, like everything else since I'd met him, should have sent me into a rage... but it didn't. No, I was intoxicated by his cock, by the act I was performing.

So I wasn't at all surprised when he pushed the envelope by saying, "Go ahead, pretty girl. Take my big cock between those cute cock sucking lips."

Like everything else so far, I should have said no.

I should have stood up and walked away.

Yet I didn't.

I was dressed as a girl, I felt like a girl and, during this surreal moment, for all intents and purposes I'd become a girl.

I didn't think. I reacted. Just like I did on the football field.

I opened my mouth, leaned forward and took his cock between my lips.

"Good girl," he groaned, as I secured the head of his cock in my mouth.

I had a cock in my mouth.

A stranger's cock in my mouth.

I moved my head forward past the ridge and began slowly bobbing.

I couldn't explain it... but this felt so right. Yes, I ate Amber's pussy, although I can't say I enjoyed it all that much. I always found it awkward and kind of confusing. I didn't know where exactly to lick. When to start flicking the clit. Yet sucking a cock was pretty simplistic.

Just bob.

Well, there was some variety. You could suck on the balls, you could swirl your tongue around the cock, or you could create extra saliva.

But I understood a cock.

I, from the inside out, understood what felt good on mine.

I understood how to enhance the pleasure.

So I did to this guy what I liked being done to me.

I loved having my head pleasured at first, so I did exactly that to his cock. I pulled back and swirled my tongue around his cock head.

"Oh yes, I knew you'd be a great cock sucker," he said as I focused on his cock head.

I forgot I was a guy.

I forgot I was straight.

I forgot I had a girlfriend. A girlfriend who was somewhere in this house.

I just focused on the cock.

I slid my tongue down his shaft... just like Amber did to me.

I moved my mouth to his balls... just like Amber did to me.

"Oh yes, you eager little slut," he said, impressed. "Suck on my balls."

I should have felt anger or shame at such derogatory words, yet instead I felt exhilaration.

I took one of his balls in my mouth and sucked on it.

After a few seconds I did the same thing to his other ball.

He said, "You're a natural cock sucker."

I moaned in response as I slithered my tongue up and down his shaft and took it back into my mouth.

Then I started bobbing.

Taking a little more into my mouth with each downward bob.

"Oh yeah, suck my cock, slut," he moaned, giving me the encouragement I needed.

After a couple minutes, where by now I was taking over half in my mouth with ease, he pulled his cock out.

"Tell me what you want," he ordered, tapping his cock on my lips.

"To suck your cock," I answered, wanting his cock back in my mouth so badly.

"Because you're my cock sucker," he said.

"Yes, I'm your cock sucker," I agreed.

"My slutty girl," he continued, as he traced my lips with his cock... teasing me relentlessly.

"Yes, I'm your slutty girl," I agreed again, desperate to have his cock back in my mouth.

I liked getting head, I liked fucking pussy and I liked fucking ass, yet somehow all those experiences paled compared to the pleasure I was experiencing now. My cock pulsed, my body was on fire, and my mouth watered.

I couldn't explain it, but I knew, just like I knew when I had a defender bested during a play, this was who I was.

"Show me," he said.

"Thank you," I replied absurdly, as I took his cock back in my mouth and shifted to my brand new porn star slut persona.

I bobbed hungrily.

He began to moan louder, and I realized that he was going to come soon.

Amber swallowed, but she didn't like it.

Amber took facials, and she did seem to enjoy it.

As I took almost all his cock in my mouth, I wondered what cum would taste like for the first time.

I didn't have much time to think about it as he warned, "I'm about to come in your hungry mouth, slut."

I kept bobbing, deciding I wanted to feel his cum shoot into my mouth.

"Oh fuck, here it comes, slut," he grunted a few seconds later as his warm cum spewed into my mouth.

I didn't slow down. I just kept bobbing as the cum swept down my throat.

Once he was done he pulled out and said, "That was amazing, slut."

"Thank you," I replied, knowing my grateful response only added to the absurdity of the situation.

"If you want another load later tonight," he said, as he put his cock away, "meet me at one o'clock behind the shed."

"Okay," I said, glancing to the clock and seeing it was 11:30.

"I expect you to be there, my little slut," he said.

"I'll be there," I committed, wanting to have that cock back in my mouth.

"I know you will," he said as he headed to the door.

I quickly got up as he exited the room.

"Our turn," a guy and a girl walked in, barely looking at me.

I quickly got out of there and headed back downstairs to the party.

"There you are," Amber spotted me, obviously quite tipsy.

"Here I am," I said, completely sober after my cock sucking adventure.

"Where have you been?" she asked.

"Sucking a cock," I answered, knowing she'd think I was kidding.

"A big one I hope," she said, playing along, as her hand went under my skirt to my still hard cock.

"Seven plus inches of hard steel," I continued telling the truth, the whole truth and nothing but the truth.

"Bigger than yours, then," she smiled, rubbing my cock right there in the middle of a crowded room.

"Don't size shame me," I pouted.

"Size doesn't matter," she assured me, as she took my hand and led me outside.

"It's how I use it," I said.

"Exactly," she said.

Once outside, she led me to our fuck spot, behind some trees (we often ended up there, as she liked outdoor sex) and got out of her football pants.

"Fuck me, baby," she said once she was half naked, "for some reason I'm really horny right now."

"Did you get any pussy?" I asked, as I pulled down my pantyhose.

"Not yet," she said, "but you're about to."

"After all that cock I just had, I could use some pussy," I said, enjoying telling her the truth even if she didn't know it.