First Time Fucking My Best Friend

"Hey, baby," I said, kissing my wife, Carina, and squeezing her ample sexy booty. "Enjoy your girl's night out."

"Hey!" she said, laughing. "Hands off mister!"

"It's time for an inappropriate hug," I said, poker-faced. Then I squeezed the other cheek.

"That's not a hug!"

"Mmmmmm," I said, still squeezing.

Carina repo'd her butt from my hand, then she and Harry's wife Dakota waved goodbye and left through the back door into the garage. I heard the sound of our car's engine starting up. The garage door squeaked up and back down.

Harry came out of the kitchen with two opened IPA beers. He was my best friend since we were little kids poking at anthills with sticks and daring each other to climb further up onto dangerously thin branches at the top of trees. He had grown into a tall slim man with masculine features except for his long shaggy black hair, which tumbled luxuriously below his shoulders, making him look like a rock star or maybe a modern day Jesus. We sat on his leather couch and each took a swig. Buddy the Corgi, being the horny bastard that he is, wagged his stub of a tail and started the festivities by humping Harry's leg.

"The fuck?" Harry said.

"He really likes you. He's making you his bitch."

Harry waved his leg around, trying to shake Buddy off, but that only got Buddy more excited about his best friend at that moment, and he shot his load on Harry's leg.

"Well," Harry said, the sarcasm barely detectable. "That was great."

I laughed and spun the box of tissues across the coffee table to him. "Buddy's getting more tail than me."

Harry wiped off the cum. Perhaps he should have been pissed about it, but he's a pretty chill zen guy. "Seriously? How often do you and Carina fuck?" he asked.

"Lately, not so much. Down to maybe once a week. You?"

"I wish it was that often. Dakota's just not in the mood lately. I've been getting hard all week long, but every time I start touching her and trying to get her turned on, she tells me she's got work to do or some such bullshit. I'm horny all the time. Driving me crazy."

I nodded. "Yeah, feel you on that. I'm horned up all the time too."

We sipped beer in companionable silence, then Harry said, "Whatta you feel like doing tonight?"

"Dunno. Maybe a few rounds of Truth or Dare?"

"Sure."

"So, what do you think your number is now?"

"Number?"

"How many women have you fucked?"

"Counting blowjobs and handjobs, or just fucking fucks?"

"However you keep score."

"Counting blowjobs, but not fingering and handjobs, maybe thirty, forty chicks. Then just the wife since." I took a swig of beer, and decided to up the ante. "So how many men did you have sex with?"

"What?"

"'Zero? One? Ten? ... I'll accept the nearest order of magnitude if you were such a slut you lost track."

"None," he said quickly, but then he got a guilty look on his face and averted his eyes.

"C'mon," I said. "Spit it out."

He played nervously with his long shiny hair. "Well, maybe technically one."

"The fuck you mean, 'technically'?"

"Well, there was this guy on the track team in high school who kind of hit on me once in the locker room after track practice, waiting around until it was just the two of us toweling off after the shower. I thought he was just joking around, but then he bent over and started sucking on me, took me by surprise. Not sure it really counts, though, since it wasn't like I came or anything."

"Are you seriously trying to invoke the Five Second Rule for blowjobs?"

"Well, it was longer than that. I mean, who doesn't like a nice blowjob? But eventually I pushed him off cause I'm not gay. OK, my turn. You ever receive a blowjob from a guy?"

"Nah. Not even your Five Second Rule kind. I mean, I've had a few gay guys offer, squeeze my junk at a party or tell me they'd like to get on their knees and open their mouth for me and lick my pole, stuff like that. You know, cause I'm good looking."

"Sounds more like gay looking."

"You wish." I glanced at Harry's crotch. Hunh. Is he getting a little hard at the thought? "You're blushing, dude. So, if I took out my dick, would you want to get on your knees and suck it like a good little bitch?"

He laughed, playing along. "Not if you call me bitch, big boy. Maybe if you were nice to me and called me 'your sexy girlfriend', I might be persuaded."

I decided to act like he'd just offered the Dare part of Truth or Dare. I stood up from the couch and walked in front of where he was seated, then slowly unzipped my shorts. Since I wasn't wearing any underwear, my stiffening dick sprang free as the zipper slid down. "OK, dare accepted. Would my sexy girlfriend like to suck my cock?"

He looked at me like maybe I was carrying a joke a bit too far.

"OK, just touch it."

Harry stared at my cock, transfixed.

"I can see you want to touch it. I dare you."

He slowly reached out and lightly brushed his fingertips against the head, causing my cock to rise up a bit as blood rushed into it.

"Now squeeze it. Make it harder."

Harry tentatively squeezed the shaft.

I sighed a bit from pleasure. Damn. He's really doing it. "Now take your other hand and knead the head." When he paused, like that was somehow a bit too gay, I said, "C'mon. Doesn't it feel good in your hand?"

He looked up shyly. "Ummm, honestly? Yeah." He began kneading the head. "Please don't tell anyone."

"It's our secret." I moaned as his hands expertly kneaded my cockhead, jacking me off, but way hotter than when I masturbated, due to the warmth of someone else's hand and using a different technique, kinda rolling it between his palms.

"Mmm," I said. "Now lick it."

"No way."

"You said you would if I called you my girlfriend," I said, using a bit of revisionist history.

He kept kneading my hardness, thinking it over, with a look in his eyes like he really wanted to but needed coaxing. Needed me to boss him around.

I reached down and caressed one of his cheeks, then slowly slid a finger across his lips. "Come on. I know you want to do it. Take the dare. Don't you want to please your boyfriend?" My cock was almost touching his lips.

He swallowed, which made my cock jump up, thinking of how sexy it is to get my load swallowed. Then he whispered, "OK."

I gently put a hand on the back of Harry's head and pushed. His lips tightened, barring entry. "Just lick the tip," I said. He looked up at me, questioning, then gave a tentative lick. "That's good," I said in my smokiest bedroom voice. "Now kiss it." He complied. "I'm gonna put just the head inside now." His lips parted slightly, and I slowly eased my cockhead between his lips, then paused with his warm mouth enveloping the head, letting him get used to it. He looked at me, startled, like he couldn't believe he was really doing this. I stroked his wavy soft hair. "That's a good girlfriend. Now use your tongue." I gazed into his brown eyes with their wide open pupils, and saw a look of soft acceptance ease into his expression. He ran his tongue along the sensitive underside of my cockhead, accepting my command.

I moaned. "Ohh. It's been so long. Damn, that feels good. Keep licking me with your tongue, baby. Please your man. Come on, run your tongue down the shaft." I reached down and took his right hand, and brought it up so it cupped my balls. "Easy," I whispered. "Squeeze them gently." He took the hint, kneading them while he slid his tongue down my stiff cock. Then he put his lips on my cockhead and took a bit of the shaft into his mouth.

I put my hands on his shoulders and gave a slight push downward. "Mmmmm. I want my girlfriend on her knees. I want you looking up at me, and telling me how much you love to suck your boyfriend's cock."

He gave me a look like maybe being on his knees was a bit too submissive, but then slid off the leather couch, my cock still in his mouth, and got on his knees.

"Say it."

He pulled his mouth off my cockhead, then whispered, "I'd love to suck my boyfriend's cock. Please?" I grabbed a handful of his long feminine hair and slid my prick back into his warm wet mouth. He looked up at me, accepting his submission, as my shaft slid deeper inside his mouth. I grunted with pleasure, trying to go all the way inside, but his hands pushed against my thighs to stop me halfway in. I pulled out until his lips were kissing the tip of my cock, then forced myself back inside. His tongue slid along the underside on the downstroke. I put a hand on the back of his neck and pushed deeper inside, then began slowly facefucking him, trying to go a bit deeper with each stroke, trying to hit the back of his throat. He resisted as I got close, gagging on the length, so I used the distraction to drop my shorts down to my ankles and kick them free, leaving me naked from the waist down.

I caressed his face, a hand stroking his cheeks, then I laced my fingers at the back of his neck and wrapped my thumbs above his Adam's apple. I lightly squeezed, completing my domination by symbolically choking him and fucking his throat deeper and deeper. Harry looked at me like he couldn't quite believe I was doing this.

"Want me to stop?"

Harry shook his head no.

I pulled out. "You gotta say it out loud. Say 'Choke me.'"

A pause, then in a small voice, "Choke me, Robert. Please."

I tightened my grip a bit more and slowly forced my cock deep inside, waiting for Harry to object. Instead, his tongue licked at the descending shaft and his warm hands massaged the load in my balls. I could feel his throat swell slightly as my cockhead pushed past my encircling hands. I grunted and bucked my hips, watching him gag and his eyes water, taking it like a girl as I forced entry, until the back of his throat yielded to my hard cock and I pushed the shaft all the way inside, my balls touching his chin. That must have reminded him that he was being remiss in his duties, since he resumed kneading my balls, the soft warmth of his hand bringing me near the edge.

"Uhhh. UNNHHH. Oh god. So close to cumming," I said and then, because he seemed to like being called a girl, I added, "... in my sexy girlfriend's mouth. Don't move. I don't want to cum yet. Look at me. Look up at me."

He looked up, his eyes still teary from the cock jammed down his throat, but taking it. He pulled off the shaft, gasped for air, then said, "Please don't cum in my mouth."

I gave a noncommital shrug while still gripping his neck, applying forward pressure, trying to get inside his hot wet mouth that felt almost as good as a cunt, but he pursed his lips closed and shook his head no.

I quit pressing. "What?"

"Please? Promise me?"

"I promise," I said, and sealed the deal before he could change his mind by pushing back inside and facefucking him slowly, trying not to cum just yet, just the head pressing in and out. Harry's lips were squeezing and releasing like a pussy would, teasing me, and his tongue was licking rapidly all over the sensitive underside and lip of the helmet, like he was using his mouth and tongue to silently apologize for his rebellion.

"Ohmygod," I said. "You're a great cocksucker. Such a good girl."

Harry was apparently turned on by this praise, his recent reluctance forgotten, since he quit kneading my balls so he could tug on his shorts and slide them and his black underwear to his knees. He began rubbing his hard dick. His lips slid down my shaft, teasing me with his tongue all the way. Oh fuck, that felt good. I was groaning, trying not to cum yet as he deepthroated me. When his lips touched my pubic hair and my balls touched his chin, I looked into his gentle green eyes and groaned. "I'm gonna cum."

He got a worried look in his eyes.

I pulled almost all the shaft out and did short strokes, my cockhead rapidly pushing in and out of his light brown lips. "It's OK. I won't cum in your mouth. Oh fuck, here it cums ... unh ... unh ..." I pulled out and started jacking my cockhead, then shot rope after rope of cum onto his startled face, almost getting one cumshot in his left eye before he blinked shut and took that burst on his eyelid and eyelash. "Aaaah, fuuuck. That was hot," I said, panting for air.

"The fuck!?" he said, wiping at his face.

"You said not to cum in your mouth."

"But on my FACE?"

I shrugged. "You don't have any tits to come on." I wiped some of the cum off his face with a finger, then gently smeared it on his lips. "C'mon, taste it."

"What?!"

I wiped most of the remaining cum off his face and extended a gooey finger. "Please. Be a good girlfriend, give it a taste."

His face looked like he was thinking of saying no, but his lips parted as my finger nudged for entry and I slid it inside.

"Aaah, yeah. Suck the cum off."

He complied as I fingerfucked his face gently. His tongue licked and flicked the underside, like he hadn't gotten quite enough cock.

"SUCH a good girl."

His eyes lit up. He gave my finger a leisurely blowjob, then pulled off. "I gotta shower, get this cum off my face."

"Sure you don't want to leave it? Looks kinda hot."

He rolled his eyes. "Yeah, that'll go over well when Carina and Dakota get home."

We both pulled up our shorts. Harry looked toward the bathroom, then at me. He hesitated, then reached out with his hand, a finger pointing towards me like that homoerotic Adam and God scene on the ceiling of the Sistine Chapel, a shy awkward look in his green eyes like offering to hold my hand was somehow more intimate than sucking my dick. I reached out and slowly slid my hand into his soft palm onto and squeezed softly. It was a weirdly erotic moment.

"You ready?" Harry said.

I nodded, and he tugged on my hand as he walked toward the bathroom, leaving me about a half step behind. I watched his slender hips sway as he walked. I'd never noticed before how feminine he looked in motion, with his long wavy hair cascading partway down his back and his curvy round butt and slim hips moving almost hypnotically.

My bathroom had a white and gray granite countertop with double sinks and a full length mirror behind it, and a glass encased shower with brushed nickel rods at the corners and top. I pulled out a couple fluffy white towels from the cabinet and handed one to Harry. "I'm gonna wash off my Johnson in the sink," I said.

Harry nodded, then turned on the water in the shower and started undressing. Naked, he had a slim but muscular body, and a curiously feminine looking bubble butt. I pulled off my shorts and got the water running in the sink while Harry stepped into the shower, giving me a shy look over his shoulder. I washed off my dick, then watched Harry, his back to me, soap up and rinse off his face as the water cascaded onto his hair and ran down his body along with the soap bubbles, leaving his skin glistening.

To my surprise, I felt my cock hardening again, despite it being early in the refractory period after cumming. It had been a while since Carina's body got me horny again so soon after fucking her - that first year of fucking like rabbits was gone, replaced by a less frantic domesticity.

I grabbed one of the towels and opened the shower door. I squeezed Harry's butt, exploring the soft feminine padding covering the hard muscles underneath. He turned toward me in surprise, his eyes widening fractionally as he saw my stiffening prick.

"C'mon out," I said, handing him the towel. "Your turn. Lemme jack you off."

His dick started rising at the thought as he turned off the water.

I tugged on his bun, guiding him out of the shower and turning him to face the long mirror behind the double sinks. The slightly damp towel I had used was spread out on the space between the sinks. Harry toweled off his hair and his body as I took off my shirt and stepped behind him. Our eyes met in the mirror as I reached around and took his shaft in my hard. It was warm to the touch and still damp, and getting stiff. Harry finished toweling off and carelessly draped the towel over the drying rod on the wall.

I nudged him forward a few inches so the top of his thighs were touching the edge of the countertop, then used the hand that wasn't kneading his by now stiff prick to open one of the counter drawers and take out a small tub of vaseline. I clicked the lid open one handed, then took some of the slick goo and rubbed it onto his cock. A moan escaped his lips as I started expertly jacking him off, my hand slipping up the shaft and onto the head, then squeezing and twisting around the helmet. I pressed up against his hot and moisturized skin, my erect cock nestling between his cheeks like a perverted hot dog in a bun.

I met Harry's startled eyes in the mirror, then began kissing the back of his neck and his shoulder blades. "Aaaaah," he sighed, closing his eyes and arching his head back, his long wet hair brushing erotically against my face.

I kept rubbing and stroking and squeezing his cock, listening to the squishing sounds it made, while my spare hand scooped up a generous dab of vaseline and rubbed it all over my shaft and helmet, then slid it under Harry's feminine round butt and pushed it up between his inviting cleft, while giving a gutteral animal growl.

"What the ..." Harry said. "No."

I froze with my lubed cock partway between his cheeks, then took my hand off his dick.

"Hey!" he said. "Don't stop that."

I whispered in his ear, his wet hair brushing against my lips, "I have a new dare for you."

Our eyes locked in the mirror. "Ummm ... what?"

"I only want to rub it between your cheeks. Nothing more."

"Just rubbing it? That's all?"

I nodded my head yes.

"Promise?"

"I promise."

"Umm ... I guess so."

I resumed jacking him off while nibbling his earlobe, then I planted soft kisses on his neck and shoulder and spine while my cock slid up and down between his cheeks. Harry clenched his butt muscles, like he was trying to limit how deep I could get between them.

"Mmmm, yeah," I said, my eyes grinning at him in the mirror. "Make it nice and tight for me."

He got a chagrined look at his plan backfiring and unclenched his cheeks. I took advantage of that to push my shaft all the way between his cheeks, and then took a big scoop of vaseline and rubbed some more on his cock and then the rest between his butt cheeks.

Harry started fucking my hand, like he was getting closer to cumming, but that also made his butt wiggle and bounce in rhythm to the squishing sounds from my cock sliding between his now well lubed buns. I thrust faster. "You like it?" I asked.

He grunted with pleasure.

"Say it."

"Uh, yeah. It's kinda hot."

"Only kinda hot? Want me to stop?"

"Unnh, shit. Don't stop don't stop. It feels great."

A bit of precum oozed out of my cock, making his cleft even more slippery. I wrapped my arms around Harry and hugged him, pressing my chest against the heat of his back and slowly sliding up and down between his cheeks. A moan escaped his lips.

"You must be feeling something."

He humped back.

I whispered in his ear, "Are you ready to be a good girlfriend now and make this feel even better for you?"

"Uhhh ... what?"

I straightened out the fuzzy white towel on the countertop in front of him, and then pushed gently on the small of his back. "Here's a new dare. Bend over the countertop. Yes, that's a good girl."

He hesitated, so I pushed harder and he leaned down onto the waiting towel, his face pressed against its softness while his eyes nervously watched me in the mirror.

"Oh, you look hot, waiting for your man." He looked so feminine bent over submissively, with his long hair and curvy smooth butt. In the moment it felt she was my girlfriend on the side, one who might do naughty things Carina wouldn't do, so I embraced the role. "Are you ready to take it a little bit further, make your boyfriend feel good?"

I stared at her green sexy eyes gazing back at me in anticipation, seeing maybe a flicker of fear too.