Uncle Bob - Work from Home Ch. 01

I popped my eyebrows at the reference to her own teen pregnancy.

Jess raised her glass again, a contemplative look on her face. "Like I've said before, maybe it's Fate that brought us together at a time like this."

I chuckled and deadpanned, "Fate sent Coronavirus to stop Mandy from getting knocked up. Got it."

Jess set down her wine glass and leaned a little closer to me. "Actually, I meant that Fate brought me you at a time when I needed you the most."

I blinked, a little surprised to see her amazingly gorgeous face only inches away from mine. "I'm, uh... glad to be here too."

"Uh-huh," she agreed. "REALLY glad." And then she softly pressed her lips to mine.

I didn't kiss back at first, scared shitless at what was happening to be honest. I'd spent so many years stopping myself from letting these feelings for her take control, spent so much time convincing myself it was never gonna happen and SHOULD never happen to make myself feel better about the idea that it was never gonna happen. And yet here we were, and the object of my desire was kissing me.

Jess didn't take my initial inaction personally. She just kissed me a little harder, with a little more passion, until I moaned and instinct kicked in and I started to kiss her back. I wrapped my arm around her back and held her close, she got excited by my positive response, and suddenly she was in my lap while the pair of us made out like love-struck teenagers.

Once, just once, I thought about Brian and pulled my head back. I gasped for breath as Jess stared into my eyes, a question in hers as to why I'd stopped. She suddenly looked nervous, scared that she'd done something wrong. "This is a bad idea, isn't it," she asked quietly.

"Probably," I agreed, but I wanted her too much so I grabbed her head and stuck my tongue right back into her mouth.

My hands had slipped beneath the back of her shirt so I could feel her naked skin against my palms. I took care not to push the pace any faster than she wanted lest I scare her off, so I never tried to unsnap her bra or even grab her ass outside of her shorts. I simply held her and stroked her and told myself that if we never moved past this one kiss, and if our lips never again met in this manner for the rest of my life, it would be alright. At least I got to feel her in my arms like this just once. It would have to be enough.

But it was not enough for her.

First, she grabbed my hands and planted them on her ass. Now with explicit permission, I went ahead and started kneading those buns to my heart's content, even slipping my palms beneath the hems so I could feel her pliant cheeks skin-to-skin. She dry humped my erection, but only for a little bit. A minute later, Jess pulled back with a wicked gleam in her eye, and with one final peck on my nose, she slithered off my lap and onto the floor in front of me.

I held my breath, not daring to let myself believe what was about to happen next. But I didn't have to wait in limbo long. Jess grabbed the waistband of my shorts and tugged while telling me out loud to lift my butt up so she could get them off me. I was happy to hop on the couch cushion while she yanked my shorts and boxers all the way down to the floor and off my feet. And before I could even blink she had the first five inches of my dick in her mouth.

"Mmm..." Jess moaned and stared up at me as if savoring the most delicious meal imaginable. She hummed and bobbed her head up and down, sucking me expertly and snaking out her tongue to lick up my sensitive underside.

"Holy crap, Jess," I groaned. "You're so fucking good at that."

Shaking her head as if in disbelief, she popped off my prick and jacked it in her right hand, muttering, "This is the first dick I've had in my mouth since Brian died, so I may be a little rusty. I could never bring myself to take another lover. But it's only fitting that heaven sent me his little brother to take care of me. Seriously, you two are even about the same size."

I'd have to take her word for it. I couldn't remember ever checking out my brother's dick, especially not erect, not that it really mattered. All that mattered to me in this moment was the way the most gorgeous girl I'd ever met gave me the blowjob of a lifetime. It was as if she'd kept all of her love and lust pent-up for years and years and only unleashed them all right now on me.

I lasted as long as I could for two reasons. One, I didn't want her to think I was some two-minute chump who'd lose my load so easily. But two, the sight of the one woman I'd always wanted more than anyone in the world bobbing her beautiful face up and down my dick was something I wanted to last forever. The feeling of her doing so was pretty damn incredible as well.

Alas, all good things must come to an end, and despite all my best efforts to hold out, eventually she started jacking my shaft with her hand in a rapid motion while licking my mushroom head and gaping her mouth open just past my tip.

"Cum for me, Bobby. Spurt all your creamy seed into my mouth. I've been dying to taste you since the day you moved in here. Cum for me, Bobby! I'm so hungry for your sperm. Cum, Bobby, cum!"

"Fuck, Jess! UNNNGGGHH!" I roared right at the end of her little soliloquy, and she quickly fastened her lips around my knob. I grunted and thrust my hips off the couch, bouncing my cockhead off the back of her mouth while she absorbed my lunge and started drinking down everything I had to give her.

Over and over she swallowed, taking every last drop like a pro. I twitched and shuddered and eventually collapsed, gasping for breath as my head fell across the top of the couch's backrest. I set my head down atop Jess's head, stroking her fine hair lovingly while she continue to nurse my slowly-deflating prick well past the point when there was nothing left to slurp. And only then did she pull me out of her mouth and set her cheek down on my thigh to sigh rapturously.

"Was that good for you?" she asked seductively.

"That was incredible," I assured her. "And you call that rusty? I can't imagine what you could do once you shook off the rust. Thank you."

She waggled her eyebrows at me. "Interested in returning the favor?"

I looked down at the gorgeous young woman on her knees before me, still dressed in casual clothes. I imagined her naked and writhing on a bed with her legs splayed out to the sides while I made love to her pussy with my mouth, tongue, and fingers, and in less than a second I nodded and said, "Absolutely."

Five minutes later I made that imagination a reality. It would have been sooner, but once we got to the Master Bedroom and Jess started taking her clothes off, it took me five minutes to make out with her and kiss my way down her fantastic nude body to finally get my head between her thighs. I mean, a world-class rack like that deserved some special oral attention, right? And her body was a brand-new wonderland that I'd long fantasized about but only now got the chance to explore. So explore I did.

But yeah, I eventually got down between her thighs and started giving her a tongue-lashing. Mine was the first tongue on her clit since my brother's, and the sensations were apparently so overwhelming that she squealed and came in less than two minutes. That was far too short a time to eat a woman out, so I stayed put and promptly gave her another one, and then another.

Jess screamed at the top of her lungs four separate times while drumming my back with her heels before she finally shoved my head away and curled over onto her side, pleading, "No more... No more... I can't take it."

I wiped my face off with some tissues from her nightstand and then spooned myself up behind her fetal-positioned naked body. I rubbed her ass, kissed her shoulder, and nibbled my way up her neck. Her chest was heaving from the exertion of cumming so many times, but as she caught her breath, she reached one hand back to hold my head and craned hers around to kiss me tenderly.

"I wanna feel you inside me," she moaned softly. "Will you please fuck me, Bobby?"

"I've wanted to do that since the day I met you."

"I know." Jess giggled. "I could tell."

Twisting around, Jess opened up her legs and helped move me on top of her in a missionary position. She raised her knees out to the sides while I fisted my cock and nudged it into the entrance of her folds. Her puffy pink labia were wide open and inviting after so many climaxes, and when I started to push my way in, she exhaled and then groaned as I slowly filled her up.

She was exquisitely tight, even tighter than I would have expected, perhaps because it had been so many years since she'd had a real cock inside her. She clutched at my shoulders and crooned in my ear until I reached full depth and then stopped, savoring the sensations.

"I've wanted this for so long," I muttered.

"Now you finally get to have me," she replied warmly.

"I feel so guilty that I'm doing this to my brother's wife," I moaned.

"It's meant to be," she assured me. "You're here to take care of me. And I'll love you as much as I loved him."

I blinked and stared deep into Jess's eyes, reading the truth in them.

"It's meant to be, Bobby. We're meant to be. It's why I could never find another lover after Brian died."

"It's why I could never stay with a girlfriend who couldn't measure up to you," I said in response.

Jess definitely seemed to like that idea, and she grinned even wider. "See? We're meant to be. Now make love to me. Hold me. Kiss me. Fuck me. I'm yours, Bobby. Yes, I dearly loved your brother. I missed him for a long time. But he's gone now and left you to take care of me. From now on, I'm yours. I'm ONLY yours."

I didn't respond except to kiss her once more. And then we started to move.

Over and over I stroked into and out of her. She raised her knees, planted her feet, and fucked me back as hard as I fucked her. She really liked it when I pressed my pelvic bone down on her clit and grinded away at it with short circular motions. But then she also really liked it when I withdrew until just my mushroom head was still inside her and then I slammed all the way back in.

I didn't yet know exactly how she liked to be fucked, but damn I was looking forward to learning. In the meantime, I experimented with just about everything and made her cum twice more, once in a missionary position and once more while I was banging her from behind. In fact, I was so focused on figuring out her buttons that I was never in any real danger of cumming myself. Plus, having busted in her mouth a little earlier, I had the staying power to really ensure I had satisfied my lover before myself.

But I still had my limits. I was pounding away at Jess's super-hot body doggy-style, my hands on her big swaying tits as I made short thrusts into her sweet snatch with my sliding schlong, when I felt the telltale tightness in my testicles. Automatically, I groaned, "I'm gonna cum soon."

Jess whined, close to another climax but having not lost her head completely. "Wait, I'm not protected."

"Oh, shit," I grunted and immediately stopped thrusting. Of course she wouldn't be protected. She hadn't had sex in years, so why would she be on any kind of birth control? And even when she was married, my brother had been shooting blanks.

"No, don't stop!" she complained, fucking herself back at me. "Just don't cum yet!"

"Jess... I'm gonna... I can't... I gotta pull out."

"Nngh," she groaned, clearly desperate for her next orgasm. "Put it in my ass. You can't knock me up if you cum in my ass."

"Umm, what?!?" I exclaimed in surprise. I'd never actually had anal sex before. None of my previous girlfriends had ever shown an interest.

"Just fucking stick it in my ass!" she yelled, dropping her face down onto the mattress and reaching back with both hands to spread her cheeks wide.

Still pretty drunk and delirious with pleasure, I gawked at her winking sphincter so obviously put on display, but only for a second. Then I swiftly withdrew my dick from her saturated snatch, notched my soaking wet cockhead at her anus, and started pushing.

Jess moaned and groaned as she forced herself to relax, and to my surprise, her tiny butthole opened up and let me in. Oh, she clamped right back down after the first two inches popped through, but she moaned and groaned and spread her cheeks apart even wider as if doing so would help ease my passage up her rear passage, and with a little more pressure and a lot more grunting, I managed to fully bury my dick up Jess's backdoor.

"FUCK you're big. Either you're thicker than Brian was or I'm just not used to this anymore."

"Brian used to fuck you up the ass a lot?"

"All the fucking time. I loved it. I mean, he dumped gallons of cum in my pussy when we were trying to get knocked up. But once we realized he couldn't have kids, he kinda just started spurting in me wherever."

"My first time," I muttered.

"Really? I get your cherry! Aww..." Jess giggled and purposely clenched her colon around my cock. "But less talk. More fucking. I need ONE more cum!"

I nodded and started stroking. It was slow-going at first, with a lot more friction that slowed me down than her pussy. It was also super HOT, in a really intense way. And while the process of switching holes and fitting my dick through her tight sphincter had set my ejaculation back, the more I fucked my way through Jess's exquisite asshole, the closer and closer and closer I got.

Fortunately, she was even closer than me. With one hand between her legs rubbing herself, it didn't take long for Jess to brace her forehead against the bed and scream bloody murder as my dick sawing in and out of her butt while she went to town on her own clit collectively brought her off. And she thrashed and bucked on her bed as one last monster orgasm tore right through her.

And then it was my turn. Finally convinced that I'd satisfied my lover, I relaxed my Kegels and hammered away at her poor anal chute, stretching it wider than it had ever expected to be stretched today.

"Fuck my ass, Bobby... Fuck my ass..." she started chanting. Cum deep inside me. Fill me with your sperm. Fuck my ass..."

"Oh, Jess... Oh, Fuck! You're so tight. It's so good. I'm gonna cum, baby. I'm gonna... I'm gonna... HHHHHNNNNGGGGHHHH!!"

I slammed forward one last time, the force of my thrust driving her face straight into the mattress. Jess groaned and squeezed as my fire hydrant burst, blasting her colon full of creamy cum. Instead of separate spurts, it really felt like I just erupted in a single intense and unending stream, until I had spent every single sperm my balls had manufactured, and I finally slumped straight down over my lover's sweaty body.

It was a slightly odd angle. Jess was face-down/ass-up for that final hammering section, and I had climbed up on to the mattress without really thinking about it, squatting so I could drill her almost straight down. Now, as my energy left me, I collapsed on top of her, my chest angled downward with the blood rushing into my head.

The strange nearly upside-down angle played tricks on my mind. The room was spinning as I struggled to recover from the force of my orgasm, and things just seemed to be out of place in my vision.

For example, I could've sworn the bedroom door was cracked open, the light illuminating Mandy's face outside. But when I blinked, the door was closed shut, exactly the way I was dead certain it had been closed when Jess and I first entered the room.

Drunk and upside-down, I assured myself I was seeing things.

Right?