Uncle Bob - Work from Home Ch. 02

"It's not safe."

"YOU kept fucking him when it wasn't safe."

"Because I couldn't get pregnant as long as he kept cumming in my ass."

"So FINE then, he can cum in MY ass! I won't get pregnant that way, right?"

Jess gave her daughter a serious look. "Are you sure that's what you want? Anal isn't for everyone."

"I know rubbing myself while giving him a blowjob isn't cutting it anymore. I've SEEN the look of utter and complete satisfaction on your face when he's buried all the way deep inside your ass. We can at least TRY, right? I NEED his dick INSIDE me, one way or another."

Jess pursed her lips, winced, and muttered reluctantly, "What if...?". She hesitated before finishing, "What if we let him go down on you?"

Mandy blinked. "Well, yeah, totally. But then I still want his dick in my ass."

"You won't want his dick in your ass after he's gone down on you," Jess disagreed. "You just said masturbating yourself while giving him a blowjob isn't cutting it anymore, but once you've got his tongue in your twat, you'll be satisfied for sure."

"You think so?"

Jess hesitated again, biting her lip. But after a pregnant pause, she finally replied, "Yes, I think so."

"Then let's go."

****

"Are we really doing this?" I muttered in amazement, staring down at Mandy's gorgeous naked body laid out before me.

This was actually only the third time I'd ever seen her completely naked. That first time she had an "oops" with her towel had been such a success that she repeated it a few days later, with diminishing results. She figured that teasing me and showing a little bit of skin at a time, like a nipple slip here or a flash of her pussy there worked better for giving me an erection than just baring it all.

But the hot teenage vixen didn't have a stitch of clothing on for this.

"We're really doing this," Mandy replied enthusiastically while looking down at me between her upraised knees, even though my question had actually been directed at her mother.

Still, I waited for Jess's signal. She had that same hesitation, biting her lip. I was a little bit confused. After all, Mandy was already giving me oral. Returning the favor, as it was, shouldn't be this big of a deal, right? But apparently it was, and I was about to call the whole thing off when Jess finally nodded and gestured for me to go ahead.

I bent my head down slowly, with Mandy watching me the whole way. I extended my tongue and took a long lick at her sweet slit from bottom to top. She shivered, moaned, and then suddenly crushed my head between her thighs.

Jess snorted. "Yep. Same thing happened to me the first time a boy licked me."

I managed to hook my hands around Mandy's thighs, holding them apart just enough for her to box my ears but not quite crush my skull. I actually had to keep my hands there pretty much the whole time because every five seconds she wanted to try crushing my skull again. I didn't even do anything fancy -- I pretty much just licked her clit and maybe sucked on it a bit. Every little thing I did gave her a screaming orgasm.

At last, her legs separated and she went limp beneath me. My face was soaked, so I got up and wiped her girlcum off my face with some tissues. I was breathing hard and tired, but Mandy was breathing a lot harder and looked a lot more tired. I figured my work was done, but the horny teenager picked her head up, stared straight at me, and growled, "Now I fucking NEED him inside of me."

"Mandy... we talked about this," Jess warned.

"You said I can't put him in my pussy," she challenged.

"Mandy..."

"You said that once I got his tongue in my twat, I'd be satisfied for sure. Didn't work out that way. I need him MORE. I need him INSIDE ME, one way or another."

"Shit," Jess sighed, rubbing her forehead.

Arching an eyebrow, I glanced over at her. "You look like you were expecting this."

She exhaled slowly and explained, "When I was her age, I let a boy go down on me."

"And?"

She sighed. "And the exact same thing happened. Getting a few oral orgasms didn't take the edge off, they just made me want his dick in me even more. Lucky you."

"I NEED it, Mommyyyyy. I NEED him... Put it in me, Uncle Bob. Fuck me... Now... I NEEEEED you in me," Mandy whined, rubbing her clit and wriggling her naked body on the bed before me.

"You're NOT putting it in her pussy," Jess scolded me, waggling her index finger in my face.

I held my hands up defensively. "Nuh-uh."

"Mommmmmyyyyyy!!!" Mandy whined.

"Fine!" Jess finally barked and then sighed wearily. "Roll over. Stick your butt in the air. I'll get the lube."

****

"Are we really doing this?" I muttered in amazement, feeling a sense of déjà vu. Only this time, I was staring down at Mandy's gorgeous naked body curled up before me.

"Looks like," Jess sighed, pulling her lubricated fingers out of her daughter's stretched butthole. "She's ready."

"Come fuck my ass, Uncle Bobby," Mandy crooned with a siren's call. "I wanna feel your dick inside me for the first time."

"You sure about this?" I asked one last time.

"Yes!" Mandy yelped at the exact same time Jess muttered, "No." I listened to Jess's 'no' more and raised my eyebrows, but a moment later she sighed and gestured for me to go forward, muttering finally, "Yes."

Shaking my head at the absurdity of the situation, I nevertheless leaned forward and notched my dick at the teenaged girl's winking anus.

Mandy shivered and clenched up immediately, closing her asshole to my entrance.

"You need to reLAX, Mandy..." her mom soothed, stroking her daughter's spine. "Relax and open up."

Taking a deep breath, the teenaged virgin set her forehead down and tried to relax. I felt her sphincter loosen and pressed my weight forward. Meanwhile, Jess reached down to spread her daughter's asscheeks for me, and a moment later, my mushroom head popped in.

"AAAAAHHHH!!!" Mandy's head shot up straight, and I could only imagine the way her eyes went saucer-shaped at my invasion. She clamped up tight, with only two inches of cock inside her rectum, and for a moment I was seized with concern.

"We can stop if I'm hurting you," I urged.

"No, no... I can take it..." Mandy insisted, her voice tight. She was hyperventilating a bit though.

"ReLAX," Jess urged. "Calm your breathing. Let your muscles unwind."

Mandy started taking deep breaths, set her forehead back down on the mattress, and moaned gutturally. As she exhaled, her asshole unclenched, and a moment later, she muttered, "Okay, keep going."

I slid forward another few inches.

She tightened up on me again, but a second later she exhaled and relaxed once more. We repeated this two more times until I finally was balls-deep up the hot teenager's butt. And she finally turned her sweaty cheek to the mattress and closed her eyes to sigh in relief.

"I'm so proud of you!" Jess enthused happily for her daughter. "How does it feel?"

"Feels fucking full," Mandy muttered.

"Full good or full bad?"

"I don't know yet. It's not BAD... but... Uncle Bob? Can you start pumping?"

Nodding even though she couldn't see me, I finally said, "In a second." Then I bent over to gently kiss her cheek. "You're gorgeous, you know that?"

"I'll never get tired of you saying it." Mandy grinned. A look of curiosity crossed her face just then, and with furrowed eyebrows, she asked, "Does this mean I'm not a virgin anymore?"

"Uhhh..."

Her mom muttered dryly. "Well you're certainly no longer innocent."

"But you still have a virgin pussy," I put in. "So technically, yes you're a virgin."

Mandy grinned. "I think so too. Do you like that idea, Uncle Bob? Would you like fucking a teenage virgin up her ass anytime you want?"

My dick jumping inside her would've been answer enough, but I swallowed and muttered, "Uh, yeah. I'd like that a lot."

"Then do it. Fuck this little virgin up her ass, Uncle Bob."

I shivered and felt the urge to just start POUNDING her, but I took a deep breath to calm myself and leaned forward to kiss her cheek again, saying gently, "Thank you for this."

"Thank me by filling my ass with your cum."

"I don't think that'll be a problem."

She giggled, and instead of waiting for me to start fucking her, she began to rock her hips and fuck her own ass back and forth along my shaft. Taking her cue, I withdrew myself but kept my hands on her hips to ensure I didn't pop out, and we soon settled into a comfortable rhythm that worked for both of us.

"Fuck yeah, Uncle Bob," Mandy breathed. "Hey Mom? You wanted to know? This is 'full GOOD'. I can see why you like it."

"Glad to know," Jess replied, and she suddenly grabbed my head and kissed me. "Fuck my little girl's ass, Bobby. Fuck her and give her an orgasm. Make it good for her."

"I'll definitely try."

"Unnnngggghhh!" Mandy groaned, now bracing herself on all fours and really pumping her body back and forth. "Fuck... me... Uncle... Bob... Fuck... My... Ass... Ohmigawd... Fuck... My... Ass... You're gonna make me cum... Fuck... My... Ass..."

"So good, Mandy. You're so fucking tight. Your ass is amazing."

"Better than my Mom's ass?" she giggled.

"I'm not answering trap questions," I assured them both. "They're both amazing."

Mandy and Jess both laughed. Jess held my head and kissed me again. "You realize you're gonna have to put a load in my ass as soon as you're done with her, right? Watching this is giving me a CRAVING."

"Poor me," I grunted, kissing her back.

"Hey, focus! Ex-virgin asshole needs attention here!" Mandy complained. I laughed and went to work, getting a fresh grip on her hips and really laying down the lumber. And soon enough I had her quivering in anticipation of an amazing orgasm.

"Fuck... me! Fuck... me! Fuck me, Uncle Bob! I'm gonna cum! I'm cumming on your cock! It's so good! You feel so good! I'm cumming, Uncle Bob! I'm cumming! AAAAAAHHHHH!!!!"

Mandy's colon clenched down around my cock, squeezing my shaft tight and sucking the sperm out of me. I powered my way through her climax, plundering that tight asshole as she quaked and came. And three seconds she screamed her delirious ecstasy, I slammed forward one final time and roared my own release.

"AAAAARRRRRRGGGGGHHHH!!!" I growled, firing away as I bathed Mandy's butthole with billions of sperm seeking an egg they would never find. But no matter, I reveled in the ecstasy of my orgasm while laughing giddily to hear my teenaged lover howling her own.

Eventually, I found myself slumped over Mandy's prostrate body beneath me. She chuckled, interlaced her fingers through mine, and sighed. "We are SOOO doing that again."

"Get in line," Jess drawled. "My ass is next."

****

"Just to be clear, you don't put him in your pussy until we get you on birth control. I don't want you becoming a teen mom like I was."

The three of us had just finished up ensuring Jess was as completely satisfied as her daughter had been, and Mandy had even rubbed herself to another orgasm watching us.

Mandy frowned. "But you always said I was the best thing that ever happened to you."

"You are, and I don't regret a thing. But at the same time, your life will be much easier if you wait until you've graduated college at least."

"I know, I know."

"It's only a few more weeks. You can handle a few more weeks."

"Fine, fine," the teenager grumped, agreeing reluctantly. She came forward and gave her mom a quick peck on the cheek and then me as well. She then headed off to her own room to clean up while Jess and I remained cuddled together in the afterglow.

My lover and I made out a bit, kissing gently, but after a while, our bodies started to cool and she started tugging me off the bed. "C'mon, let's go take a shower together."

My eyes sparkled. Showering with Jess and rubbing soap all over her fantastic naked body was always fun.

"And then," she added, "maybe you'd like to spend the night with me?"

I arched an eyebrow. "Are you sure?" Thus far, Jess had always sent me back to my own room after sex, as part of maintaining our boundaries.

"You passed the test," she replied warmly. "You've proven your commitment. So now that I've chosen my mate, I'm welcoming you into my bed to entice you to remain."

I blinked. "Consider me 'enticed'."

She leaned forward and nuzzled my nose. "Besides, I really want to feel your arms wrapped around me when I fall asleep tonight," she murmured from an inch away.

"I've wanted to hold you in my arms when I fell asleep for a lot longer than that," I replied.

Jess grinned, pecked my lips, and sighed. "I love you, Bobby."

I blinked and brushed hair back from her eyes and tucked it behind her cheek. I could tell how much it had taken from her to say those words. "I love you, too," I told her sincerely. "I've loved you for years."

We started kissing again, and probably could have started another round right then and there. But Jess pulled me off the bed and into the shower, where we cleaned up from the night's exertions.

Five minutes later, I slid my fresh erection into her sweet pussy.

Seven minutes after that, Jess looked deep into my eyes, gave me a little smile, and asked, "What would you say if I said I was thinking about starting a family with you, the family I never quite got to have with Brian?"

I didn't respond verbally, at least not right away. Her words filled my mind with the idea of spurting my sperm into her fertile womb, and as soon as that thought popped into my mind, I held her as close as a man and a woman could ever be, and I came.