First Time Gay Crossdressing Bbc

Author's notes: This story contains hetero and gay sex, plus crossdressing and interracial love. Feel free to bail out now if any of that is not what you like.

It's a complete rewrite of my most read story, "First Time With My Best Friend", with over two million views between the three chapters. I read through all 250+ comments, and fixed problems pointed out in that constructive criticism. In particular, I completely rethought that awful original third chapter that so many commentators justifiably hated -- in the rewrite the POV character remains a good friend, instead of acting like a reprehensible jerk.

I originally posted this rewrite in the Interracial Love category, because the plot and characters focus primarily on interracial relationships. But after mulling it over, I felt that I needed to repost it, under a different title in the Gay Male category, to reach the majority of its intended audience.

XXX

How did a married straight man like me wind up bent over a couch with my best friend grunting, grabbing my hips, and sliding his huge black cock painfully deep into my ass?

***

Ben and his wife, Janelle, first met me and my wife, Ciara, when they were contemplating buying a house in our upscale neighborhood. Well, upscale except for the dust and jackhammer noise and whatnot as construction workers finished building out the housing development. The realtor who had sold us our house asked us to let Ben and Janelle tour it, since it was the same two story model as the house under construction that were thinking about buying. They were concerned that in a upscale neighborhood like ours the only minorities might be the Latino construction crews building the place.

Our realtor overcame that objection without saying a word, by choosing a house to show them that was lived in by an ostensibly interracial couple. I tease my wife about identifying as black, despite loving Starbucks, Barry Manilow, and country music. We were the inverse of each other, couplewise. Ben was a handsome muscular black man, a former professional athlete who after he got 'sports-old' (aka mid-20s) and lost a step, switched to studying for the bar exam. He'd married a beautiful slender dark-eyed white woman. While I was what my bootylicious and deliciously curvy wife described as "nerdy hot", a slim bookish looking artist with glasses and long dark brown hair tied in a ponytail.

The four of us hit it off immediately, chatting and laughing and touring our house. They viewed my colorful abstract paintings on the walls, which Janelle said made it look like a contemporary art museum. Our realtor hung back, happy to let us do her job.

Ben and Janelle signed the sales contract the next day, for the house diagonally across the street from us. Over the course of the next year Ben and I became best friends. OK, best MALE friends. Our wives were our best friends ever. Obviously.

***

Ben and I were hanging out on his black leather couch. We were drinking cold Shiner beer, and watching interracial blowjob porn he had streaming from his laptop to his 85" TV. I was helping him do the faux bachelor thing since Janelle was on the second day of a four day business trip. In the course of a rambling discussion, we wound up debating how to spell 'black':

"So," I said, "how do you feel about writers using 'black' with a small 'b' versus 'Black' with a capital 'B'?

"First off, people can -- usually -- call their own ethnicity whatever the hell they want. I wanna refer to a bruddah as 'niggah', I can. But, what would happen if some white person wrote articles using capital-W 'White'?"

"That's racist as fuck. Lotta bad history behind that."

"Sooo... how about a white person using capital-B 'Black' in writing?"

"Hmmm. Virtue signaling, oblivious to the flip side of the capital-W 'White' racial supremacist thing?"

Ben nodded, maybe 'yes', maybe 'hey, look at that!' The TV was showing a secretary kneeling on a wide-armed black leather couch, remarkably similar to the one we were sitting on. She was bent down, sucking off an improbably muscled black guy with almost no body fat and a surreally long dick. "Weird segue, but whattah ya think 'bout that scene?"

"Fucking hot."

"Now THAT's how you blow a guy," Ben said. "I mean, deepthroat is fine for a change of pace. But the way she's concentrating on the head, softly bobbing and using her tongue - so hot."

"Day-ahm," I said. "She's got her back arched and her butt in the air. She's making great eye contact. Lips covering her teeth and her tongue licking the frenulum - perfect."

"There you go again, using big ol' fiddy-cent words - the fuck is a frenulum?"

"The sensitive underside of the cockhead."

"Coulda just said that."

"Don't hate on me 'cause I have a large vocabulary. Speaking of large... vocabularies... he's got a really huge one."

"Nah. Somewhat bigger than your median bruthuh, sure. Not nearly as big as mine, if you take into account width as well as length."

"No fucking way. He's gotta be, like, 98th percentile in size."

Ben shrugged. "You're using a lotta words to say you literally don't know dick." He pointed at the actress, who was gently kneading the guy's balls. She was also rubbing his frenulum against the inside of her cheek, causing her cheek to bulge out sexily. "Hey, she kinda looks like you, you know?"

"You saying I look like a chick?"

"Slim, those glasses, long wavy dark hair? Swap out your Y chromosomes for X's, that could be you. Take the compliment, for fuck's sake."

A long silence. "Uh... thanks?"

"And you've got her soft cocksucking lips, too. You'd be a natural."

"Jesus, Ben. Your wife's been gone all of two days, and you're acting like you haven't been laid in weeks."

"Course I'm horny. Janelle and I fuck, what, two or three times a day?"

"Seriously?"

"Sure. How often do you and Ciara fuck?"

"Been four days. She's been stressed from work, not in the mood."

"You poor bastard."

"I'm probably hornier than you right now."

Ben raised his left eyebrow. "If we weren't both happily married, I'd say we could both use a temporary side chick. Entirely theoretically speaking, of course. I love Janelle so much. I'd never cheat on her with another woman."

"Umm... that sounds like an overly specific denial. Cheating with a woman -- bad. Cheating with a gu--"

"What? No. Fuck's sake, I'm not gay." He looked at the screen, where the guy had his hand on top of the woman's head. Shoving her deeper into his mouth, face fucking her, while his other hand leisurely spanked her firm butt. "Damn. Look at that. If I found myself with a guy who looked like her, offering to do that to me, I'd be tempted. Not that I would succumb." He looked at me, overly speculatively.

"Oh, hell no. I'm not gay."

"I wasn't offering." But he kept looking at me.

"Jesus. You need to go jack off already."

"You know, you're right." He pushed off the couch and stood up.

Guess that's my cue to give him some privacy.

I stood up too.

Ben stepped uncomfortably closer to me. "Theoretically speaking..."

"Yeah?"

"Would it be cheating if, instead of jacking themselves off, guys took turns jacking it for the other guy? Just masturbation either way, so the wives should be OK with it, yeah?"

I stared at him a moment, then burst out laughing. "You almost had me for a moment there, thought you were serious. Yeah, go run that logic by your wife - she'll be, 'of course, honey, go for it'." I waited a moment. "Said no Janelle, ever."

He grinned. "Yeah. Admit it - you totally bought that for a second."

Time to tease him back.

"So, speaking entirely theoretically, how would they go about it? Deciding how to take turns?" I grabbed his hand and hovered it an inch away from my crotch, trying to make him super uncomfortable. Make him back down first. "Like, rock paper scissors? Whoever loses has to touch first?"

He stared into my eyes, like he was wondering how far to take it, to try to make me the bitch who caves first.

He put his hands on my shoulders. "The more feminine one - the one who wants it more - would go first.

He pushed down. "The one who looks like the chick in that video."

Taken by surprise, my legs gave way, and I found myself on my knees looking up at him.

I thought, He pushed down pretty hard, right? So I didn't choose to sink to my knees. Did I?

I tried to stand up, but he kept his hands on my shoulders, gently squeezing them. In a husky voice he said, "Take it out. Touch it."

I looked into my best friend's eyes. He was smiling, with this smirk like he was waiting for me to surrender. To admit I was a pussy, afraid to keep escalating the joke.

To ask - or worse yet, beg - for permission to quit kneeling before him. With that large bulge in his jeans at eye level.

Fuck it. I'll make him flinch first. Make him the bitch.

I put my hand on the zipper of his jeans, not breaking eye contact. I slooowly pulled it down, waiting for him to concede by slapping my hand away. Undid the button above the zipper.

No objection. Nada.

He wasn't wearing any underwear, or a belt either. When I finished undoing the button, his jeans dropped down and his semi-hard cock sprang free. It was already bigger than mine ever got, and growing. Most of the shaft was a dark brown umber, not quite black, with large veins showing under the skin. The circumcised head and the foreskin below his large mushroom was lighter, a reddish-brown. But the most memorable feature was how thick it was. As thick as my slim feminine-looking wrists.

"We're gonna take turns, right?" I whispered. Not sure if we were still joking.

"Mmmm-hmmm," he said, shoving his jeans down to his ankles. "Squeeze my cockhead. Run your other fingertips across my balls. Gently."

"I shouldn't," I said. But my hands ignored my mental dithering and moved of their own accord, like it was just a dream.

Or perhaps I wanted to do this, and my mind was desperately trying to rationalize me touching his dick?

The skin was velvety soft and hot to my touch, with an underlying hard core. His cock stiffened in my hands and rose up, closer and closer to my face. Soon it was sticking straight up, almost touching my lips. Hard, it had to be seven and half, maybe eight inches long. Which by itself wouldn't make it massive, but the incredible girth made it look huge.

How the hell did Janelle take that monster in her pussy?

"Fuuuck," I whispered. "It's so big. Like a horse's cock."

"You like it?"

"Oh, yeah." I immediately regretted the enthusiasm in my voice. Jesus, I'm not gay. Why the hell did I just sound like an excited little bitch?

A drop of precum oozed out of the tip. "Go ahead," Ben murmured. "Still your turn to do it." His large rough hand caressed my cheek. "You know you want to, baby."

Calling me 'baby'? The fuck?

I shouldn't, I thought, as my hand began sliding cautiously down his shaft. Then up again. Squeezing and twisting my hand around the head.

Ben groaned. "Oh yeah. Like that. Faster." He put his other hand on the back of my head, his fingers wrapped around my ponytail. He caressed my scalp while lightly tugging on my hair. Sending jolts of pleasure deep into my head.

Ben pulling my hair made me feel weirdly submissive and turned on. My cock was stiffening in my pants. I felt like my cheeks must be blushing from my shameful arousal.

His hand then slid down to my neck and massaged it with strong hands.

"Uuuuhh," I moaned, involuntarily.

"Feeling good, yeah?"

I answered by twisting my hand on his cockhead while my thumb rubbed around the rim and along the underside.

Ben groaned. "Fuck. Squeeze it, baby. Knead it."

I felt his hand on my neck apply the barest of pressure downward. Or was that wishful thinking?

Is he really coaxing my face toward his cock? No. No. I shouldn't, I thought, as my head slowly bent, my lips almost touching his cockhead. A drop of precum oozed out of his slit, glistening.

His hand kneaded my neck, then squeezed affectionately.

I'll do it, I thought. Then it'll be my turn to nudge my best friend's head onto my cock. That's fair, right?

God, I'm so fucking horny. I'd love to have my cock licked and sucked while I guide his head...

I kissed the tip of his cockhead, smearing precum on the center of my lips.

Ben made a strangling sound of pleasure.

I licked the slit as precum continued to slowly ooze out. It tasted salty and a bit bitter. Oddly similar to yeasty pancake batter, forever sullying pancakes for breakfast for me.

"Jesus," Ben said. "Quit fucking teasing. Either stop, or take my cockhead between those big full lips."

"It's too thick. It won't fit." I belatedly realized this wasn't a 'no'.

"It'll fit." Ben pushed firmly on the back of my neck. This time there wasn't any ambiguity about whether he was pushing.

I felt my lips parting as the dark reddish brown mushroom head pushed inside. My jaws opening wider and wider. Trying to not scratch the invading flesh with my teeth, covering them with my lips. The rim of his cockhead stretched my lips impossibly wide and finally popped inside my slutty mouth.

I looked up into my friend's warm brown eyes, my mouth stuffed wide open with cock. Feeling panicky that he would try to stuff that thick black shaft into my throat and choke me. Could you asphyxiate and die from having something so big stuffed down your throat? I frantically wrapped both hands around his shaft so he couldn't go any deeper.

"Good girl!" he said, stopping his descent inside me and gazing lovingly into my panicked eyes. "See, it fit. I'll stop for now, let you get used to having my head inside you. Would it be weird if I called you Janelle, help me imagine she's doing this?"

A straight guy voluntarily getting on his knees, letting a giant black cock get stuffed inside his mouth, and he thinks roleplaying by calling me his wife's name would be the weird part?

"Mo," I mumbled as best I could around the massive meat in my mouth. I pressed my lips tighter so I could swallow the spit mixed with a bit of precum that was threatening to drown me. "Thah naw uh whurr eng urhh. Eh ahhh ot uh aww uck uhr." Translated from Blowjobese: 'No. That's not the weird thing here. And I'm not a cocksucker.'

Ben softly stroked my cheek with his hands, an amused look in his eyes. In a rumbly bedroom voice he said, "My wife's got a cock in her mouth, which she's sucking, but she's not a cocksucker?"

I decided not to argue the point.

"Lick it with your tongue, Janelle. Slide it around the underside."

It occurred to me that I should try to make my husb - uh, I mean my friend - cum as quickly as possible. Get it over with so I could have my turn.

So I complied enthusiastically, licking and sucking and squeezing the top of his shaft with my lips. My tongue flicking over his frenulum and his pee slit. I bobbed my head in short strokes so his cockhead would slid halfway out and then be fully engulfed again. Imitating everything my wife lovingly did for me when she gave me head, striving to make me feel incredibly good.

"Ahhhh, yesss, that's a good wife."

I felt a warm glow from the praise. And I was rock hard in my pants, turned on by the surreal stretching of my lips around all that cock. Plus, the taste of his precum was growing on me. And the rubbery smooth texture of his cockhead skin, a thin layer of softness over a wondrously hard core.

I admitted to myself I was enjoying the perverse forbidden-ness of being on my knees, sucking off my best friend. Enjoying trying my best to make him cum. Being called his wife's name, being called a good girl.

In that moment, I embraced and loved being his wife. Being a cocksucker in the best sense of the word. Trying to give my man pleasure and make him cum in my mouth. Even though I suspected the upcoming post-nut clarity might be a rude bitch. But that was a problem for future Bojack Cocksucker to deal with.

"Ah uv muh uuhs buhuhnd!"

He looked at me with soft adoring eyes, like I'd seen him give Janelle so many times in the past. "I love you too, Janelle. You're being such a good wife." Ben grabbed my ponytail, and pushed down firmly. "Can you take some of my shaft, baby? Make your husband feel sooo good?"

I took a hand off his shaft and began gently kneading his large balls, smooth shaven and almost coal black with a trace of dark brown. Leaving the other hand as a backstop to keep him from sinking all the way inside my mouth and throat. I willingly took his big black cock, looking into his lustful eyes as that frighteningly thick shaft slowly sunk deeper into my mouth. Trusting that he wouldn't choke me to death with that horse cock. That he'd had plenty of previous experience doing this to all the women he must have attracted. Women turned on by his muscular body and deep sexy voice, and of course that massive black cock. Heaps of women who were happy to take his dick into their mouth or pussy, and possibly some into their ass.

I gagged as his cock hit the entrance to my throat, perhaps half his shaft inside my hot wet mouth. I pushed my hands against his thick hard thighs. I breathed in the sexy musky scent wafting off his trimmed public hairs. God, he smells really good, a more manly musky version of the incredible fragrance my wife's pussy gave off. A perfume full of an exotic wonderful mix of phermones and other scents that I had fallen in love with the first time I had licked her pussy.

I had a moment of panic as I belatedly realized the danger of taking my hands off his shaft, so I could push against his hard thigh muscles. A symbolic gesture, 'stop', that he could easily overpower with his strong athletic body. I couldn't prevent him from jamming himself all the way inside me. That he might even misread my pushing against his thighs as me wanting to feel and squeeze his powerful muscles. That he might think I was giving consent to shove himself in all the way, instead of trying to halt any deeper entry inside my aching mouth.

"Sorry," he said. "Too deep?"

"Mmmm!" I said, tears running down my cheek, though not in a bad way, just an involuntary reflex of my body.

He slid all the way out of my mouth.

I gasped for breath. "It's OK. I want to make my husband cum. Just... not so deep."

"Sure, baby," he said. "I'll be gentle." He began pushing just his cockhead into and out of my mouth, slowly facefucking me.

I licked and sucked, and flicked my tongue and wrapped my lips lovingly over his cockhead as it thrust into me. My hands were lubricated by my spit and twisting around his shaft, as he thrust faster now. He groaned and grunted and pushed his hips at me. Gripping the back of my head with one hand to push inside. Pulling my hair each time he pulled out so just the tip was inside.

His balls tightened, and he grimaced and said, "I'm gonna cum!"

"Mmmm!"

"Do you want your husband's cum?"

He pulled out for a moment. I gasped for air and said, "Yes! Cum for me, Ben."

He jammed his cockhead back in. "Can I cum in your mouth, baby?"

I nodded 'yes'.

"Do you want this big black cock to shove past your fat cocksucking lips and into your slutty mouth, filling it with dick? Do you want to be a good girl and take my load?"

"Mmmmhh!" I mumbled, nodding my head 'yes'.

He gave me a bit of shaft, just enough to pin me submissively in place, and stopped thrusting. "Oh god. Oh fuuuuck. Here it cums. Uhh, uhhh, arrrrgggghhh!"

I felt my mouth take his hot tasty cum, spurt after spurt, wanting it. Wanting him to give me the gift of his lust. Unlike the unrealistic depictions in smutty stories I've read, he didn't fill my mouth to overflowing. Though he did have an impressive load from just two days without his wife to give him relief.

"Can you swallow for me, Janelle? Can you do that for your husband?"