Author's Note: This story is a prequel to "Don't make it weird", but I'm treating it as a stand-alone entry. It shouldn't matter if you read it before or after.
By the time I realized I hadn't disconnected from my call with my best friend, Tom's hand was already sliding underneath my panties, and I was too preoccupied with how his fingers massaged my clit to really worry about taking my earpiece out.
My hands were busy clutching at his broad shoulders, pulling on his longish hair as our mouths melded together. He tasted minty and fresh, mostly because he was a bit neurotic about bad breath so he brushed around ten times a day.
"Damn, Isa, you're so fucking hot," he breathed as he broke our kiss to all but rip my shirt off. He was towering over me, more muscular than I usually went for, but that was because he'd proven to be a gentleman and not the usual brainless gym rat I ran into.
There was nothing gentlemanly about how he was looking at me, though. I felt my insides flutter as his eyes roamed over my body.
It might not be fair that he was standing there in that tailored suit and I was pressed up against the wall in nothing but a pair of panties, but working from home ever since this pandemic had begun, my usual office attire consisted of a comfy, loose shirt I'd once stolen from my best friend and my underwear. I didn't even have to wear a bra unless I had a videoconference, and the feeling of Poe's old t-shirt rubbing against my nipples all day usually had me prepped and ready for when my boyfriend came by.
Boyfriend might be pushing it if I really thought about it. Tom was more of a force of nature, hard to pin down and put in a marked area under one definition. As he calmly took off his jacket and folded it over my office chair, I couldn't stop looking at his hands while he rolled up the sleeves of his crisp white shirt. The silk tie was also removed before sexy times because it had been a gift from his mom—I thought it was super sweet that he was so careful with it—and I tended to get grabby when he was ravishing me.
He kept that fucking smirk on his face, but I'd known him long enough now to know that it was just his resting face, not necessarily that he was a dick. Okay, he was a bit of a dick, but not towards me, and sometimes that really works for a girl.
My apartment was a bit chilly because I liked it that way, but I was beginning to sweat. Standing in my rapidly soaking panties as this older guy who'd picked me up at the gym six months earlier undid his belt, I was already remembering the orgasms he'd drawn from my flesh the last time he'd been over.
Tom worked at the District Attorney's office, some big, important role he never wanted to talk about because he aimed to disconnect when he was with me, so he was still going about his regular work routine, except he wore double masks. His germaphobia demanded it. I didn't really mind his not giving me the details of his job, since it wasn't as if I wanted to be regaling him with the exciting world of computer network security and cloud storage. We had better ways to spend our time.
Fucking. We spent our time fucking.
What are our mid-twenties for, if not for experimentation? I'd never been with someone so much older than me, and not to shit on guys my age or anything, but Tom had skills that I was sure only came with the mileage. Regardless of what our official relationship status was, fling, fuckbuddies, going somewhere, I wasn't exactly too concerned picturing a white picket fence anyway. Tom was a lot of fun, and that's what I needed, particularly in this new weird place the world was in.
My contemplation was cut short as he grabbed my hands and pinned them above my head, kissing me again hard enough to make me see stars. Every inch of my skin felt electric as he drew his belt across it, from my tummy up along my exposed breasts and neck, until he wrapped it in a tight knot across my wrists, picked me up, and put me on my bed.
"Hey, Baby, I missed you." Erika's voice in my ear jarred me, to say the least.
What the fuck?
The earpod was still in place because I had a little plastic hook that kept it there, but I had assumed that the call I'd been on with Poe had dropped by now. My phone was on my desk next to my computer, and it looked like my childhood friend, confidant, and all-around favorite person had also assumed that I'd be hanging up. Erika, his current girlfriend, had come around to see him after work, much like Tom had shown up at my place.
I was going to say something, but then I saw Tom taking his pants off, his big cock straining at his jockeys, and my words dried up in my mouth. Just remembering what he felt like inside me distracted me enough that I missed whatever exchange Poe and Erika were having because then Tom was taking his sweet time undoing the buttons on his shirt and I was mesmerized. He was hot, and he knew it.
His dickish personality and confidence stemmed from the effect he knew he had on women, and the joy he got from intimidating other men. The flex he'd made on those two dudes who'd been annoying me the day we met still got me through the lonely nights when he couldn't come over. Call me silly and old-fashioned, but it was fucking nice to be fought over. My empowered self wasn't displaced by his assertiveness, I just thought it was hot.
"Oh, Daddy, your cock is so big."
My mouth dropped open in surprise. Erika was speaking in a squeaky little voice that I knew wasn't her normal tone, and the ramifications of what she'd just said blew my mind.
"Huh," Tom definitely smirked then as he stroked his fat cock, standing over me as he stepped out of his underwear. "Don't mind if I do."
Before I could utter a whole syllable, he'd straddled my chest and shoved his cock in my mouth. The head was large and it immediately poked me in the back of my throat, but I wasn't some rookie dilettante in cock worship. Tom's dick was endowed with all the properties that make up a grade-A penis, and I'd spent hours praying at its altar. I relaxed my jaw and curled my tongue underneath the girth invading my mouth, and he shuddered as he put a hand on the headboard to steady himself.
I really enjoyed giving him head, because while it seemed like he was exerting his dominion over me, I could turn him to absolute putty with a few deft strokes of my tongue and squeezing my lips. Most guys I'd been with liked to be dominant, which I enjoyed playing against, but secretly I knew that as time passed, they realized that I was the one controlling our fucking. It hadn't happened yet with Tom, but it probably would. As much as I liked the guy and his cock, when I was being honest with myself, I didn't think he'd be able to handle me—at least not the entirety of me.
Still, that was shit to worry about another day.
"Oh, fuck, Isa. Your mouth is so amazing." Tom's voice had a sexy rasp to it that I found extremely hot. When he panted his desire in my ear, moaned, and grunted as he thrust inside me, it certainly contributed to me getting off.
What caught me by surprise was how the definite sounds of a cock being sucked coming through the earpod were also suddenly working for me.
Even though I was making similar noises myself as Tom fucked my mouth, the little gasps, slurps, and what were probably Poe's moans of appreciation of Erika's skills were ramping up my excitement.
Well, this is weird.
I couldn't disconnect the call, my earpods were cheap ones that didn't have that feature, and I didn't want to interrupt Tom, as he was looking at me with barely disguised wonder cracking through his tough-guy façade when I took his entire length down my throat. He kept his pubic hair nicely trimmed, not scratchy, so I kind of enjoyed how it felt against the tip of my nose; the way his balls bounced against my spit-covered chin as he thrust in and out was like a beating drum that matched the throbbing in my soaked pussy.
"Oh, yes, Daddy, feed me that big cock," Erika was mumbling, the sounds of her slobbering over Poe's penis mixing with the squelches of Tom's cock between my lips.
I hadn't known my friend was into that kind of roleplay, and it was going to be delicious to figure out a way to give him shit about it without revealing that I'd heard him getting freaky with his girlfriend.
Worry that they might be hearing us, in the same way, reared its ugly head, but I remembered that Poe didn't have discrete earpods like mine, he had a huge-ass headset he used for his calls, and the odds that he hadn't taken it off to get busy were slim.
Tom drove away thoughts of my best friend and his girl having sex when he pushed himself off the wall and grabbed a hold of my hair in his strong fist. It hurt a bit, but it was just a little dance across the edge of pleasure and pain. I liked having my hair pulled, which he knew well.
"Fuck, fuck, fuck..." he muttered as he increased his pace. He also reached back and slipped his hands into my underwear, showcasing some great flexibility and balance as he thrust two of his thick fingers inside me. Those yoga sessions really did pay off.
My own orgasm was still a bit off, but having my pussy played with, in such a rough manner, while getting my mouth fucked was inching me closer and closer. Being used like a little fuck toy made my slick walls tighten around his invading digits.
Tom couldn't last, though. This wasn't an observation to his detriment whatsoever. I took it as a point of pride that he couldn't resist my mouth. He had great stamina elsewhere, but I knew he had to have some sort of oral fixation from how quickly I could squeeze the cum from him with my lips.
The first splash of his warm jizz went straight down my throat, so I barely tasted it, but the subsequent spurts filled me to overflowing, and since he kept thrusting against me, all that sticky cum got pushed out past my lips, dripping over my cheeks and chin. Drops ran down my neck, and my comforter was soaked from all the saliva that had pooled around me. The smell of his essence drove me a little wild, I admit, and I bucked my hips as he continued finger fucking me, timed perfectly with the final spurts against my tonsils.
Just a regular Wednesday for us, really.
One other thing that made me appreciate Tom was how he took it as a point of pride to make me cum. Maybe it wasn't exactly healthy that he saw it as a competition, but I didn't see it as a bad thing, since he knew what he was doing. Jerkily withdrawing himself from my mouth, he kissed me on my forehead and traced his way down to my panties using his tongue.
"Are you going to cum for me, Daddy?" Erika still used that little girl voice that jarred me, but the feeling of Tom's tongue as he pulled my panties to the side and began making love to me with his tongue was keeping me in a strange place.
I heard Poe grunt and Erika coo, which made me glad that my best friend didn't seem to be very vocal because I didn't want to be hearing his voice right then. Tom's flicking and swirling around my clit was getting me up that mountain quickly, but the image that popped in my head of Erika on her knees, slobber and spit on her chin, jerking Poe's up-until-then-imaginary-cock as it spewed all over her face was also contributing to the rising crescendo of lust.
For a split second, I wondered if there was something wrong with me. I'd never thought of Poe as a guy in that way before. We'd grown up together, as close as siblings, and we'd talked about sex enough that nothing was really taboo between us, but it had never led to any sexual overtones in my vision of him. Going off of Erika's enthusiastic compliments, he packed something nice in his pants. It wasn't as if I was curious now, really, but I rationalized it away as being similar to finding out your brother was having sex. You knew he was, but it just wasn't something you dwelled on.
Tom drove his fingers back inside me and all thoughts of my best friend fled for the moment. I was so close. He was clean-shaven, but a bit of stubble was already showing this late in the day, and the slight scraping against my inner thighs as he moved his head back and forth sent shivers shooting up my spine.
I tried getting out of the knot his belt held my wrists in, so I could focus on what Tom was doing to me instead of getting thoughts of other people fucking in my head, but there was no give for me to work my hands loose.
Tom saw me struggling and shot me a devious look, the lower half of his face dripping with my juices as he quit thrusting his fingers inside me and only started giving me long, slow licks over my lips.
"What's the matter? Are you close?"
Bastard. He knew I was. Sometimes he really was a dick.
He didn't usually make me beg for it, so he must've had a win at court today. He was extra cocky with his ministrations.
"Daddy, I need your cock inside me," Erika pleaded in my ear. "I need it, Daddy, please."
Shit. That was actually kind of hot. I'd never done that before with a guy, but I had an evil thought, inspired by my best friend's perversions.
Adopting what I pictured was an air of innocence, I batted my eyes at Tom and bit my lip.
"Daddy, I need your cock inside me so bad, please..." I drew the words out slowly.
Tom froze in place comically. His eyes widened a fraction and his slow teasing of my clit faltered. A little rush of hilarity mixed with excitement pulsed through me.
"Please Daddy," I emphasized the suddenly filthy word. I saw him swallow as he stared at me, and I knew he was suddenly picturing everything in a new scenario. How much older he was than me. How we looked together. How I could technically be his daughter if he'd knocked a girl up in his teens.
I don't think I have any Daddy issues, my father's a saint, and as soon as I thought about it I realized it had nothing to do with that. At least not that I could see. It was the naughtiness of it. The implied taboo. The entire wrongness of the concept was what made it so enticing.
The temperature in the room seemed to change as Tom raised himself above me, his swinging dick hovering above my dripping pussy. The corded muscles of his arms, chest, and neck kept him in place effortlessly. His eyes roamed my face, a bit confused and a lot turned on.
He was so into it, I realized. He'd been struck mute. Maybe it was something he'd been afraid to explore with me or was waiting until more time had passed, but we were there now.
"Oh yeah, Daddy, you like my tight little pussy wrapped around that big, fat cock?"
It looked like Erika and Poe were already going at it, from the sloppy sounds in my ear, and I realized that I wanted to be there already. Raising my legs, rubbing them around Tom's thighs, I wrapped them around his waist and lifted my hips so my cunt touched his shaft.
"I need that big, fat cock, Daddy. I want you to take my tight little pussy..." Tom's mouth was hanging open like he was seeing me for the first time, but a fire was coming to life in his eyes. He grabbed my tied wrists and pinned them against the mattress as he kissed me hard.
I screamed even as his tongue pushed mine around my mouth because he'd let himself be drawn by my legs and just plunged inside me in one go. Luckily I was so turned on that it didn't hurt at all, but he was so thick that it was still a violent intrusion in my flesh.
"Fuck me, Daddy, fuck me, Daddy, fuck me, Daddy," Erika was getting reamed, for sure. She was screaming and moaning, and as soon as Tom broke off to bite my neck I fed her words right at him. It might be weird, but it was too fucking good as well.
Hearing me just kept driving him further towards a place I wasn't sure he explored too much. His movements got frantic and his throbbing cock inside me felt the hardest he'd ever been. It was too much for my little pussy, and I told him so, of course. I whispered it in his ear as I sucked on his earlobe.
"FUCK!" Tom swore as he pushed himself away and grabbed my legs, pushing them up onto his shoulders and as soon as he bottomed out inside me in this new position, I came.
"Oh, fuck-fuck-fuck-fuck-yes!" It was the best fucking orgasm I'd had with him, and that was saying a lot. He was out of control. I'm not sure he even knew where he was. He just kept fucking me into the bed as I kept calling him Daddy over and over again.
What a pervert, I laughed in my head. But then again, with sex this good, I was more than happy to stand on that ledge with him.
And Poe. And Erika.
I couldn't make out what was going on halfway across town at Poe's apartment, because my delicious lover was still pumping himself inside me, and I was going to cum for a second time if he kept going. Tom's grunts and heavy breathing had a frantic air to them. I'd never seen him this out of control.
"You feel so fucking good, Daddy, you're going to make me cum again on that big, hard cock, aren't you?" I don't know if I was being too squeaky with the tone, but it was definitely working for him because he somehow increased the pace even further. My bed was creaking, it wasn't built to withstand this much of a pounding on my kitty.
Just as I saw the flush creep up his neck and I knew he was about to shoot his cum inside me, I reached the peak again and we came together.
My pussy was a sopping, aching furnace, but I still felt the jets of his semen coating my insides, and I used all those kegel exercises I'd mastered long ago to squeeze my pussy around his girth, our bodies in perfect rhythm as he bent down and kissed me again, hungrily devouring my lips until he was spent, and my own orgasm ebbed.
He was still unable to speak. He just kept looking at me with wonder and I figured I'd just broken him.
I couldn't help myself. "Oh, Daddy, you filled up my slutty little pussy with so much of your cum." I gave him a little pout.
He finally chuckled and shook his head. "Jesus, where the fuck did that come from?"
"Oh, Daddy, that was so good. I can feel your cum swirling inside me..." From the looks of it Poe and Erika had also finished.
I just smiled at Tom as he untied my hands. I rolled him onto his back, kissing him deeply, feeling his cum leaking onto my thighs as we cuddled. He smelled so good, and the fact that I knew I had him wrapped around my finger did nothing to diminish how much I liked him. Maybe there was something there after all.
I discreetly went to remove the earpod, but I caught one last thing that made me swallow as my blood boiled.
Fucking hell, I chuckled. My best friend was naaaaaasty. It was going to be so much fun teasing him about it.
Still, my secret muses inspired me again.
Shifting against Tom, I pulled his arms around me, facing away from him so he was the much bigger spoon to mine. I could feel his sticky cock rubbing against my butt. He nuzzled my neck, and it felt divine. Lifting one of his hands to my face, the smell confirmed it had been the one he'd been finger-fucking me with.
I sucked two of his fingers into my mouth and moved my ass up against his shaft. He immediately froze and gasped.
"Oh, Daddy. My virgin ass could use some attention. Do you think you could help me with that... Daddy?"