420'd Accidental Bi Sex

Story Info
Accidental mispost of personal ad leads to first time w/ man.
4.2k words
4.7
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174

Part 1 of the 2 part series

Updated 06/09/2023
Created 11/28/2018
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The personal ad I wrote while stoned and horny:

I'm looking for someone with a bit of a kinky streak. I'm tall, smart, funny -- you be that too. Here's what I like:

(attached picture from the waist down of what I like -- a woman with a booty wearing black lacy panties)

***

I posted the ad, not expecting much -- this site was a sausagefest, perhaps ten men for every woman. I finished the bowl I was smoking, then checked email.

Holy shit. Five responses already?

***

"Wanna fuck that little ass"

What? Must be some gay dude being creepy.

Delete.

***

"u down to fuck, baby?"

Gotta be spam. No woman answers an ad like that.

Delete.

***

"Your a hot gurl. Wanna hook up?"

The fuck? Did I ...

I pulled up the ad. Dammit. Posted in Guys For Guys, not Guys For Women. Gotta back off the weed before posting. I reread it to the part where it said, "Here's what I like ...", followed by a somewhat androgynous woman's body in lacy panties.

I rolled my eyes.

No wonder. They think that's me wearing those panties.

I sighed and hit the delete button to shut down the post, then went to delete the rest of the emails, which due to incoming responses was now up to seven waiting in the queue.

***

"Top here. You a bottom?"

Delete.

***

i'm DTF. u 2?

Delete.

***

"No bs, no expectations, no diseases...

"6'5", 32 y/o, 215 lb, brn/brn, 6" cut/thick, dom, verbal top would love to spend some time with a sexy panty boy like yourself and live out some of our mutual fantasies. Looking for something casual we can build upon.

Love a panty boy that wants to model some lingerie and assume many sexy poses while changing outfits, give me a sexy lap dance and demonstrate what a slut you are then perhaps drop to your knees to worship me while i feel your sexy ass. Like to have a finger inserted in you while you work my cock in your mouth so i can feel you clenching while stretching you out. then take and fuck your panty ass-pussy, pumping it like there's no tomorrow and cumming hard all over that ass, backside or face. Lots of pre-cum and a multi cummer here.

Most definitely like to photograph you in your sexy outfits. Love scrunchy butt thongs/bathing suits. Love a sexy ass in a thong/t-back (can't emphasize that enough) and stockings! Even better slightly hidden thongs and/or visible above jeans, booty shorts, boy shorts, under semi see through lingerie, etc.

Forgot to mention that i eat some mean ass-pussy!"

My finger hovered over the delete button as I read ... and read ... and felt my cock start to stiffen.

The fuck? I'm not gay. Maybe I'm turned on imagining doing this to some girl ... that must be it.

Delete.

Then I mass deleted all the remaining emails.

And sat there, my heart pounding. Just out of curiosity, wonder what those pics in that erotic email looked like ...

So I undeleted the one email, pulled it back into my inbox. Can't hurt just to look, yeah?

Pic 1: A face shot of a ruggedly handsome man with a muscular bare chest hinting of many hours at the gym.

Pic 2: A firm set of abs, strong legs ... and a large erect cock.

I should delete this, I thought, as I kept staring at that cock, lingering. I really should ... do that.

Pic 3: A POV picture looking down at a beautiful dark haired woman with green eyes wearing skimpy black lingerie, on her knees, making eye contact like she was mesmerized, her mouth open and two strings of sticky cum bridging her lips and the stiff cock she was grasping at the base ...

I kept staring at this picture. Holy fuck, that's hot. That would be hot to ... get ... such a blowjob.

I emailed the guy back: "Sorry dude, I posted in the wrong section, meant to post in Men For Women. That was a sexy fantasy you described, but I'm straight. Best of luck! Harry."

I was about to close my laptop when another email popped up, from the same address:

"Were you turned on? Did it get you hard, thinking about doing that? I'm Jamie, btw."

I emailed back: "Ummm, yeah. Kinda. Especially that straight pic of the girl on her knees."

Another email popped up: "Hey, let's chat. No harm in that, yes? Call me at [number redacted]."

I looked the number for maybe 30 seconds, which can seem like an eternity, then shrugged and dialed the number on my cell.

A growly, sexy masculine voice answered. "Jamie. Is this Harry?"

"Yeah."

"You wanna come to my house? We can look at porn together, stuff like that blowjob pic that turned you on so much."

"What?"

"C'mon, it'll be fun."

"I -- I shouldn't ..."

"Relax. We'll just chill, smoke some weed -- I mean, if you do 420 ... you're not a cop, are you?"

"Fuck no."

"Got some kickass Colorado weed, 30% THC. We can watch porn, talk, maybe jack off together ..."

"What?!"

"Are you telling me you've never looked at straight porn with a guy and masturbated together?"

"Hell no."

"Oookay, no jacking it. No worries. We won't do anything if it feels weird."

I shouldn't, I thought, as I heard my voice say, "Ummm, OK, I guess."

He gave me the address. "How long do you think you'll be?"

Hunh, I thought, looking it up on Waze. Just over a mile away. If it gets weird, it's a short ride back home. Silence on the phone, as he let me think it over. "Umm, maybe five minutes?"

"See ya!"

I drove over slowly, that "mellow no rush cause everything feels awesome" kind of weed driving. The guy, Jamie, lived in a small house on a quiet residential street. I parked by the curb, having second thoughts. As I was on the verge of flaking out on meeting him, the front door opened and he smiled at me and waved as he walked toward my car.

"You Harry?"

What the fuck, I thought. Worst case scenario, I smoke some good weed.

We went inside his spotlessly clean house, almost OCD levels of cleanliness, and sat about a foot apart from each other on his black leather couch by a coffee table. The table had a small black plastic cylinder resting on it, with labeling on top, probably an eighth of an ounce, and a small, cool looking monkey skull grey pipe. It also had a large iMac, freeze framed on a POV porn video of a brunette girl on her knees giving a BJ. Jamie tapped a button and the video resumed playing, the girl expertly sucking and licking the cockhead, in high definition.

"That video good for you?" Jamie asked.

"Yeah."

"Let's get down to it," Jamie said, smiling and plucking a small green nugget from the cylinder and putting it into the bowl. He fired it up with a lighter labeled "Dank" in green letters and inhaled deeply. Holding the smoke in his lungs, he handed the pipe to me, a sweet funky dankness in the air from the smoke curling up from the bowl.

I took a big hit. Oh my fucking god that's good shit. I tried to hold it all in, but coughed a bit. Jamie coolly exhaled a thin plume and patted me on the back as I coughed, an amused look in his handsome dark brown eyes.

"It's strong stuff. Doesn't take much, yeah?" He took another toke, then handed the pipe back. In that sort of choked voice of someone not wanting to lose good smoke, he said, "Finish it."

I took a more cautious hit, inhaling a lot of air with the smoke this time, my lungs getting almost painfully full before the nugget ran out.

Jamie tapped the keyboard, opening his "Other bookmarks" tab, revealing a long list of porn sites. "The straight porn sites are on top," he said. "Pick whatever turns you on."

I scanned down, then opened a subtab labeled "Big Ass | Big tits hd."

Jamie grinned. "Like 'em thick?"

"Mmm-hm."

I scrolled down until I found a promising clip and opened that, then moused along the time bar until I reached a part where the actress was lying on the bed and the guy was straddling her head, facefucking her. I hit Play and then went to full screen.

"Good call," Jamie said.

We sat side by side, watching and listening as the facefucking turned into a rough doggy prone bone. The weed started kicking in hard, my head buzzing and my dick getting hard as the couple switched position on the screen and she started giving the guy head. I glanced over at Jamie, who had a similar bulge in his jeans. "I thought you were gay."

He shrugged. "More like bi. I prefer guys a bit more, but I've fucked plenty of women."

"I'm straight. No interest in guys."

He gave me an amused grin. "I've heard that a lot. Let's test that theory, shall we?" He tugged his jeans down to mid-thigh, revealing a long semi-erect cut cock.

"What the ..."

"Relax, just a scientific experiment, checking which gets your attention -- this, or the straight couple -- oops, they're up to a threesome now -- on the screen?"

I realized I was staring at his stiff prick, and quickly went eyes front to the screen. But, a few seconds later, I went back to looking at his cock.

"Unn-hunh. Thought so."

"I'm not gay," I said, hotly. "Just ... curious. Never seen another guy get hard before."

"Curious about what it looks like when it gets fully stiff?"

I didn't say anything, listening to the two girls on the screen taking turns noisily getting fucked by the guy, but still looking at Jamie's cock.

Jamie must have taken my silence for consent, since he opened the door on the side table by the couch and took out a white hand cloth and a tube of KY Jelly. He smeared some lube on, and started jacking. It quickly got fully stiff, maybe seven, seven and a half inches long. I stared, mesmerized, as his hand expertly twisted and stroked the cockhead. He tossed me the lube. "Go ahead, jack yourself. It feels weird just me doing this." When I hesitated, he said, "Nothing the least bit gay about masturbating to straight porn, dude."

I thought about it, then shrugged and pulled my jeans down a bit until my prick popped free, by now almost hard, and started stroking. My prick quickly reached full mast. The video ended, and some suggested clips filled the center of the screen. I clicked on a link showing a pretty brunette sucking a black cock, a close up shot filmed from the underside of the action. I moused along the time bar til I got the matching scene, and let er rip. She started not quite deepthroating the large black cock with each of his forward thrusts, her head bobbing to meet the incoming shaft.

"You like that, yeah?" Jamie said, softly.

"Uh-hunh." I stroked a little faster.

"You imagining you're the one fucking that pretty face? Or the one taking it?"

I felt maybe I should take umbrage to that, but the high from the weed urged candor. "Honestly?"

"Yeah."

"Kinda switching back and forth."

"Me too. Hey, would you like it to feel more like her mouth on your johnson? When you're not imagining taking it, that is."

"How?"

Jamie scooted over so his hip barely touched mine, then quickly reached over when my hand was on the downstroke and grasped my cockhead. I opened my mouth to protest, but he started twisting and squeezing and rubbing in ways I had never thought of, and yeah, it did feel like a real blowjob. I closed my eyes and moaned softly. I took my hand off my dick so he could have full access to the shaft. He did something with his thumb, pressing with it on the underside of the cockhead and wiggling it. I moaned louder.

"Good, yeah?"

"Don't stop. Fuuuuck." I could feel an orgasm starting to build, but tamped it down, wanting this lovely moment to go on and on.

Jamie leaned in and whispered in my ear, his breath hot, "Practice what I'm doing on me."

I hesitated for a heartbeat, then grasped his cock, which was surprisingly hot, and gave it a tentative squeeze. I felt it twitch in my hand. It felt kinda weird, holding another man's stiff dick for the first time. It felt really good. I stroked down the shaft.

"Yeah," Jamie said. "Do it."

We jacked each other and watched the porn clip a while. Jamie leaned forward and did a quick search, then called up a clip of a busty blond girl on a white couch leaning down and deepthroating the actor's long cock.

I watched it and growled with lust while Jamie brought me to the brink of orgasm and backed off.

Out of the corner of my eye I watched Jamie observing where my eyes were tracking on the screen. "Imagining right now you're the girl deepthroating?" Jamie said, except it came out sounding more like a statement than a question.

I nodded, not trusting my voice.

Jamie reached over with his unlubed hand and rubbed and kneaded the back of my neck, matching the rhythm of his hand on my cock. I sighed with pleasure. Jamie placed gentle pressure on my neck, pushing down, while using his free hand to remove my hand from his cock, then grabbing the hand towel and cleaning the lube off his prick.

I watched, mesmerized, as my head was slowly pushed toward his cockhead, which grew bigger and bigger in my field of view as I bent toward his stiff prick. I felt I maybe should object or something, resist the pressure on the back of my neck, but the weed was saying otherwise. Jamie stopped pushing when my lips were not quite touching.

"Lick the tip."

I hesitated, then did, tasting salty precum, listening to the sound of the blond on the screen giving a sloppy wet blowjob. The light pressure resumed, and his helmet slid between my lips and across my tongue. I waited for him to stop, but he kept pressing and his shaft started to descend inside me. I finally resisted when his cockhead hit the back of my throat and made me gag a bit.

Jamie took his hand off my neck and started stroking my hair. "You like it?"

I came up for air and looked up into his soft brown eyes.

When I said nothing, he softly asked, "Do you want to stop?"

It felt so good, his hands running through my hair. I realized I didn't want to stop. So I started bobbing on his cockhead, and Jamie gave me tips on how to lick and suck and please him. I imagined I was the blond in the video. At his suggestion, I took his shaft in one hand and squeezed it, and took his balls in the other, warming them, as he groaned with pleasure and lightly grabbed my hair and took control. I imagined how it must look and feel to Jamie with my head in his lap, getting facefucked. Part of me resisted in my head, feeling this was too gay. I pulled off his shaft and looked in his eyes again.

Jamie must have read my thoughts, or my expression. "It's OK," he whispered in my ear. "It's OK to be a little bit bi. Doesn't make you not straight, just curious. It's just us." When I kept looking, he whispered in my ear, "Do you want to stop? You can, you know."

I replied by enveloping his cockhead with my lips and pressing down, taking more and more of his shaft, suppressing the gag reflex until I had the entire length inside me. I came up gasping for air, and Jamie stroked my hair some more and gazed at me with what might have been a loving look in his eyes. Or maybe just loving doing it.

I glanced at the Mac's screen. Jamie must have set the porn to auto roll over to the next video while I was sucking him, since there was now a sexy thick Latina getting pounded doggystyle on a black couch similar to the one we were sitting on, making awesome noises while the guy grabbed her hair and pulled her onto his thrusts.

I leaned back down and resumed my cocksucking and ball kneading. A bit later, I felt my jeans being yanked further down. I pulled off the cock just as Jamie slid a finger with cool lube between my cheeks and onto my hole.

"Hey! What are you doing?"

"What I said I wanted to do, in my email to you." He started applying pressure on my hole.

"What?!"

He stopped pushing, but kept his finger resting on my hole. He picked up his cell phone off the table with his spare hand and read from his email:

"Like to have a finger inserted in you while you work my cock in your mouth so i can feel you clenching while stretching you out."

I stared at him, speechless.

"Not like I made a secret of what I wanted. And yet you still came here, knowing what I'd like to do. So maybe deep down you wanted it too. But, if you don't, well, you can leave anytime." A long pause, which he filled by dropping another weed nugget in the pipe. "Do you want to leave?" He held out the pipe. "Or do you want to suck on this some more?"

I slowly put my lips on the pipe, looking up into his mischievous dark eyes. He flicked the lighter, and I sucked in a huge lungful of smoke. I yelped and coughed when he started pressing his finger into my ass, pushing through the ring. It hurt a little, but it also felt really hot.

"Want it deeper?"

I nodded yes.

He started sliding it in, a millimeter at a time, while I exhaled the smoke and embraced the high and took his cock in my mouth, slowly sliding it into my mouth in time with his descending finger, until his finger bottomed deep inside my ass just before his cock did deep inside my mouth, his black pubic hair scratchy against my lips and nose.

"Now clench it," he said. Not being sure which he meant, I clenched both my lips and my assring. That must have been the right answer, since he groaned and grabbed my head and started facefucking and fingerfucking me in rhythm. I couldn't quite believe how quickly things had escalated, from regarding myself as entirely straight to having two holes penetrated at once.

While I was still processing this, and sucking his cockhead, and clenching the finger in my ass, horny and incredibly stoned and giving in to the moment, Jamie said, "Look at the screen now."

Another video was rolling, this time of a beautiful Latina with a sexy booty laying on her back, her legs spread apart, while a cock pressed into her butthole, then pushed deep inside in a series of thrusts.

"Do you think that's hot?" Jamie asked.

I lifted my head off his cock. "Yeah," I grunted as his finger slid deep inside me.

"Are you imagining being the guy there?"

"Unh. Oh wow," I said, as his finger hit my prostate, causing me to shudder with pleasure. " Uh, no. Her."

"Lay back."

I stared, not sure I could go there, but his eyes were so sexy and full of lust for me, so I leaned back and put my head on the armrest. Jamie yanked my jeans off, then climbed between my legs, nudging them a bit apart. I turned my head and looked at the screen, with the Latina spreading her legs wide open for his thrusts. Jamie looked at it too, then grabbed my ankles and raised my legs in the air, put one over his right shoulder, and spread the other leg wide apart like hers. He grabbed his phone and read from his email earlier, "Forgot to mention that i eat some mean ass-pussy!"

He kissed his way down my neck, my chest, and my stomach.

And started licking my butthole.

OHMYGOD, I thought. Oh fuck. Oh fuckfuckfuck this feels sooo good.

I started breathing hard, and moaning, and thrusting my hips toward his tongue as the weed and the tongue caused my head to fill with indescribable pleasure, writhing under his lapping.

Jamie was stroking his hard prick with more lube. He kissed his way back up toward my face. I averted my lips because of where that tongue had been, so he kissed my neck instead and rubbed his cockhead up and down against my hole. He glanced at the phone he'd just picked up and read another line from earlier: "then take and fuck your panty ass-pussy, pumping it like there's no tomorrow and cumming hard all over that ass, backside or face."

He waited, and I waited, and when I looked at him with perhaps a bit of fear in my eyes, or reluctance, or maybe just a hint of uncertainty, poised on the cusp, he quickly slid back down and started licking my hole again.

I bucked my hips up into his face. "Fuck, yes. Ooooh ..."

To my surprise, I started cumming without him touching my cock at all.

Jamie looked at the cum spurting out, startled, then climbed back up and positioned his cockhead against my hole. "I'm gonna fuck you right now, baby, while you're still riding the wave."

12