Babysitter with Benefits Ch. 04

"Oh!" she exclaimed. I pulled back, squirted some more lube on my finger, then pushed it back in. "Oh! Oh!" she groaned. "Fuck me, that's the first time ever anything has ENTERED that way..."

I giggled. "Really? Have you never..." She shook her head, her reddish hair brushing back and forth over her back.

"Never, I've been quite occupied simply enjoying my pussy, thank you very much!" she smirked. "Not that your finger feels at all unpleasant, mind!"

Encouraged, I probed deeper in her, reaching past the second knuckle before starting to wiggle my finger a little about. I was rewarded with a groan.

"Oh my! Keep at it, please, don't stop!" Ella let her right hand sink from the headboard and soon it cupped her sex, another moan as she no doubt let a finger rub along her slit, feeling how wet she was. "Let's just do this for a while, huh?" She said, eagerly fingering herself with my pointer finger buried in her ass. "Just play a little with me, then get that plug in me and we'll fuck, OK?"

Gently probing her ass, I felt dizzy with excitement. Surely, if she found it so pleasurable to have a finger in her, a small plug - surely she'd want to graduate to my cock, eventually? I hoped so, but was bright enough to decide against pushing for it. If she wanted to, she'd let me know.

Fingering herelf, Ella giggled. "I hope you don't mind me getting all the pleasure at the moment, huh?" She said, breaking into a laugh. "It'll be your turn soon enough, I promise - but this, it just felt so new, so good..."

"Oh, I'm good", I murmured. "The pleasure of giving you pleasure aside, don't forget I already have a toy in me..."

I rewarded her enthusiasm by pulling out of her, then lubing up another finger before gently, very gently pushing back in. She yelped again, increasing the pace of her fingering. "Ooooh, fuu-uuck!" She exclaimed. "That's like, two fingers? Three?" My GOD!!!"

I smiled. I'd be buried in her ass to the hilt before the day was over, of that I was almost certain. "Two fingers. Ready for the purple plug, Ella?"

She groaned. "Yeah, slip it inside me, please..."

Pulling out of her, I reached for the buttplug, glistening with lube. Pressing the tip against her anus, it wasted no time slipping past her sphincter. I let it rest there for a few seconds, before gently pushing it home; it was rather small - some 3" long and probably no more than three quarters of an inch across - so as she'd been probed a little before the plug entered the picture, she took it all in one go, moaning as it came to rest in her.

"Mhm, you mentioned something about a vibrator..." Ella said, voice dripping with lust. Pressing firmly against the base, I gave the plug a second to figure out its services were requested, and a soft hum emanated from it, Ella jolting as if she'd had an electric shock. "Oh. My. God!" She grunted, turning over on her back. "Come here, lover!"

As she pulled up her legs and spread them, I wasted no time kneeling between her thighs, letting my tongue taste her soaked slit again. Another moan. "Oh, another few seconds of that and I'll..."

I greedily lapped away at her, tickling the clit which had already peeked out from under its hood to see what the fuss was all about.

"Another few seconds and I'll cu-uuu-uuhHHMM!!!!!" she squealed, bucking her hips against me - and, indeed, cumming.

Pulling back from her pussy, I eased myself up until I could lay down over her, my cock resting against her belly; she was just coming to again, eyes blinking, before she smiled at me and giggled. "Wow, that was intense," she mused. "I never thought such a small vibrator would make itself felt as much as it did - does. She smiled. "It... Wow, it throbs so, I can feel it in my ass, my pussy, all the way down to my toes..." She laughed. "Not that it can hold a candle to the real thing. Do your thing, please."

I did my thing. Bucking my hips a little, I managed to wiggle a hand in between us, grabbing the base of my cock and pointing it towards the slit I'd just tasted; with my swollen glans resting against her lips, I leaned down, kissed her full on the lips - and sank to the bottom in one smooth stroke. Ella whimpered while eagerly making out, bucking towards me, urging me deeper. Every wiggle she made caressed my cock almost beyond belief, and also made me feel the presence of the hefty plug in my own ass.

I gasped as her velvety snugness welcomed me. No matter how familiar the feel, nothing could ever prepare me fully for how wonderful it felt to push inside her. Slowly, I began to thrust in her, locking eyes with her as I did so. "So," I began. "Does it live up to expectations, being double-teamed by a silicone plug and a neighbour?"

Ella nodded fervently. "Hell, yes, it does!" She closed her eyes, grabbed my butt and pulled me down onto her. "Every time you bottom out in me, I feel the buzz of the butt plug even harder..."

She kissed my chin. "If you're happy with it, I think I'll just lie here and be entertained by the two of you, it's already bordering on too intense... Just fuck me, slowly and gently, please?"

Slowly and gently it was. I surely hoped I wasn't already beginning to take sex with Ella for granted, but to my relief found that the frenzied lovemaking of our first few trysts had - at least for the time being - given way to more relaxed, playful, tender lovemaking, probably in part brought on by the realization that there would be more times like these - so no need to devour her as if it was the last time, every time. Ella, too, seemed content with the lowered pace, smiling lustfully back at me as I held her gaze while - still slowly - pulling out of her and sinking back in. I could do this almost for however long she wanted me to as long as we kept this pace. Good.

Anxious that I was too heavy for comfort lying over her, I placed my hands on the mattress and lifted me off of her, still thrusting in her in the same slow, steady pace, taking in the wonderful sight of her perfectly round breasts jiggling ever so slightly with my every thrust before letting my gaze drift back to her face, painted with bliss, making her even more beautiful than usual - no small feat, that!

Smiling back at me, Ella winked. "So, with regards to going all in... The plug is making a most persuasive argument in favour, just so you know..."

I could not help but laugh. "Oh he is, is he?"

"Mhm. Taking it was a lot easier going than I'd imagined, and while you're bigger..." She smiled. "Make me cum again, then we'll do it, OK?"

I quickened the pace, pulling myself up a little so my shaft slid against her clit with every thrust. Ella groaned and bucked hard against me, urging me on. "Yes, harder, harder!!!" - to which I duly obliged.

"You do realize I may well cum myself, huh?" I grunted at her, only to be rewarded with a giggle. "And? I am sure I'll be able to make you ready for seconds once we've relaxed a little..."

Smile broadening, Ella pursed her lips to an O, then suggested she'd almost forgotten what I tasted like - so if I thought that would suffice to get me hard again, then..."

The mere thought of her blowing me made the base of my cock tingle. Increasing the pace further, I knew I was soon approaching the point of no return.

"You close?" I grunted. I got an angelic smile for my trouble. "Very!" she replied, shut her eyes, hugged my butt - and suggested I take her past the finish line.

The fervour of our first lovemaking was back, and firmly so - I slammed my cock into her, relentlessly chasing my own - and her - orgasm. Ella's eyes remained shut, she smiled and kept pulling me down on her, as if I needed any prodding. Soon, the familiar warmth spread throughout my body; I had seconds to go. Pounding her, I was relieved to feel her tense and then contract around me just as my own orgasm erupted; I came, hard, shooting my load in her and collapsing over her just as she yelped and came, too.

We were a sweaty heap of entangled limbs, but I could live with that. Totally spent, I rolled over on my side to relieve her of my weight, then smiled at her as she faced me, pulling a strand of hair aside, sighing contendedly. "Wow," she muttered. "That was a good one. Ah, would you mind turning the purple wonder off, please?"

Giggling, she turned her back on me and pushed her ass toward me; nabbing the plug at the base, I pulled it out of her and unceremoniously dropped it on the floor before cuddling up to her, brushing her hair aside and kissing her in the nape of the neck, hoping I wasn't being too intimate.

Apparently, I wasn't. Ella softly murmured something I didn't quite catch, then wiggled herself closer to me, suggesting I hold her.

I did, enjoying the shared intimacy, but at the same time feeling a sting of uncertainty - were we just sharing a moment after having had excellent sex, or...

I snuggled closer to her while pondering the thought. Was I beginning to take a romantic interest in her? I'd promised her I wouldn't - heck, I'd pretty much promised myself, too, I wouldn't...

Any lingering unease was immediately lifted when Ella turned around to face me, put on her most impish grin and suggested she wanted to see if she could suck me hard again, though.

Flopping over on my back, I eagerly grinned back at her asking her to do her utmost.

She did. Oh, how she did. With a curious playfulness - this was only the second time she'd blown me, hell, the second time she'd blown anybody - so she basically made it up as she went along, kneeling between my thighs, planting sloppy kisses down my stomach before lightly tracing the underside of my semi-flaccid, cum-glistening cock. It twitched. Ella giggled and cupped my balls, kissing the glans, giving her tongue a quick swirl over it.

It felt heavenly. I pondered for a moment how her inexperience made it feel even better - she curiously tried soon this, soon that, developing her technique as she went along rather than, as perhaps would have been the case had she had a few men under her belt, going for what she knew would work and be done with it.

Her tongue swirled over the purplish glans, and I could feel myself starting to swell again, to amused giggles from Ella. "What, I thought you'd cum and then it would be a CHALLENGE to get you hard again, but this..." she glanced up at me, smiling - "This hardly counts, does it?" She kissed the tip of my cock softly, then let her lips slowly slide down it until the head was fully inside her mouth. She then started sucking, ever so gently. Softly stroking her hair, I could feel myself growing harder by the second - her mouth was everything a man could hope for and more, and the prize when I was fully erect again... I moaned.

A few more seconds of this, and I'd be ready. She apparently sensed it, too, and pulled off of me. "That was easier than I'd thought", she quipped. "I'll keep that in mind for future use!"

She then laid over on her side, slowly stroking me in case I'd need reminding that staying hard was in my own interest. "So, how do we do this," she asked, suddenly serious. "Would I be on all fours, or will something else work better?"

I smiled, then got up, a drop of saliva - or maybe precum - dribbling from my cock as I rose. "I thought, maybe if you lie down on your back, ass on the edge of the bed here..." - I motioned for the foot end - "...then I can be on my knees on the floor, should be about the right height, then we can have eye contact. Will make for better communication, methinks. So you can keep me from getting carried away - plus it will be simpler for you to masturbate if need be."

Ella nodded. "Sounds like a plan!" - and with that, she arched herself, planted her feet on the floor and eased her ass forward until it rested on the very edge of the bed. Crunch time.

I grabbed the lube from the nightstand, then took a condom from the package in the top drawer. Glancing back at Ella, lying there on the bed and staring at me with eyes sparkling with excitement, I had to really concentrate to keep myself from shaking my head in meek disbelief. Tearing open the foil, I swiftly rolled it on, squirted a generous helping of lube in the palm of my hand, then started applying it to her anus. She squirmed and moaned as I gently probed her, finding I slipped in almost unhindered.

Repeatedly dipping my finger in the lube, I ensured she got lots in her, before closing my palm around the shaft of my cock, covering it in lube with a couple of soft strokes. I was ready. She was ready.

Taking a pillow from the bed, I knelt on it and there I was, cock swaying as I nudged closer to her ass. Locking eyes with her, I could see hers were almost glazed over with lust, mixed with a little bit of anxiety. I smiled, suggesting that I'd be very, very careful - and, of course, that if she asked me to stop, I'd pull out instantly and that'd be the end of it until - or even if - she felt ready to try again. She nodded. "I am sure you'll be careful, now, just... Do it before I lose my nerve, huh?"

Resting the glans against her puckered hole, I took a deep breath, then, while still holding her gaze, I started pushing my hips forward. The pressure built. Ella stared back, not averting her gaze for an instant. Seconds later, she eased up a little, and my glans slipped past the sphincter, causing her to grunt a drawn-out "Ooo-oooh!" before smiling faintly at me. "Oh, you're much, much... Well, you FEEL much, much bigger like this!"

She giggled uncertainly. "Not that I've any complaints, mind. Just... Go real slow, huh?" I nodded. I had no intent of scaring her off anal, seeing as being in her was every bit as tight, warm and wonderful as I'd hoped it would be. Reaching for first one ankle and raising it until it rested over my shoulder, then the other, I had a perfect starting point for entering her to the hilt, grabbing her thighs and slowly, oh-so-slowly pulling her towards me. Her eyes were wide open, but her gaze seemed turned inward as she focused all her attention on the new and unfamiliar - though I hoped not unpleasant - feeling of my cock in her ass.

I was almost halfway there when she, panting, asked me to pause a little. "Sure thing, you want me to pull out?" I asked, hoping any tinge of anxiety in my voice would be interpreted as concern for her well-being, rather than concern that the show would be over. To my shame, I had to admit to myself that I had both thoughts in mind, despite really wanting the first one to govern my mind alone.

She shook her head. "No, just stay, I need some time to adjust, is all." Lazily, she dragged a finger along her slit, then started rubbing her mound. "It feels so good, I just... Well, I don't want it to be too much, too soon."

I looked at her, mesmerised, as she deftly fingerfucked herself, taking the occasional detour to rub her clit before returning her attention to the soaked slit.

She nodded at me. "Please. Do it."

I did. Pulling her towards me, I soon felt her ass keeping the length of my cock like in a vise. A velvety, snug vise, that is. Giving her a mild thrust just as I was in her to the hilt, my balls slapped against her butt cheeks. I was in her as deep as I'd ever be.

Looking down at her, I was relieved to see a somewhat hesitant smile form on her face. She looked amused as she smiled back at me, while picking up the pace she was masturbating at. "Just... Stay there for a while, OK, it feels... Oh, so different, so... So amazing!"

I nodded, taking in the wonderful sight that was Ella, furiously pleasing herself, with me as an, well, I could hardly say innocent bystander, could I, as I was buried balls deep in her?

Just staying in her, the sensation was almost too much - every minute movement she made was instantly transmitted to my cock. I tried to stifle a moan. She giggled. "So, lover, does it feel as good as you had hoped for? Done this before, by the way?"

I blushed. "Last things first - yes, once, almost twenty years ago - but I only, ah, made it an inch or so inside before it was called off, chances are we weren't careful enough. Well, that I wasn't careful enough, I guess, in fairness. As for how I feel now... Yes, it is every bit as wonderful as I had hoped for. So... So different from being in your pussy. Tighter. Much more friction. But still... Somewhat the same, to feel you around me, your every move..."

Ella thrust her ass ever so carefully against me. "OK, can you try fucking me? Like, slowly and carefully? I think I'm ready for it..."

I did. And did it feel amazing. She was well lubed up, so I could pull out of her without much of an effort; when only the glans remained inside her, I thrust forward again, not trusting that her anus would let me right back in if I pulled all the way out. When I tensed my muscles to push my hips forward and sink inside her, I really, really felt the presence of the plug in my own ass. No way in hell I'd turn on the vibrator, I'd need all the help I could get to hold back my own orgasm - definitely not anything to bring it forward!

We fell into a slow, steady rhythm, Ella bucking against my every thrust as I bottomed out in her, groaning as, between her own masturbation and my thrusting, she probably was getting the ride of her life.

"I... I'll be cumming soon," she murmured. "When I do, don't stop, please, just keep thrusting like this, OK?"

Could do. I luckily still had a way to go before cumming again, so with any luck I'd - we'd - be able to get her over the edge and into a massive one before I erupted. Gripping firmly onto her thighs, I took my chances bottoming out in her a little more forcefully. Squeals of delight ensued.

With her free hand, she cupped a breast and pinched her nipple, closing her eyes as orgasm drew near. "Keep looking at me!" I snapped, puzzled as to how assertive I sounded - it had been intended as a plea, but came out more like a command. Ella opened her eyes and met my gaze.

I smiled. "I want to hold your gaze when you cum," I said softly. "You're so, so incredibly beautiful then. Please."

"Tha-aaanks, ah, fuck, FUCK!!!!" she yelped - and there, as if on cue, she clenched down on my cock, shoved her fingers as deep in herself as she could, and came, came hard. There was nothing I could do but hold onto her for dear life, but the look on her face as orgasm rode her... Priceless. I knew it would be etched in my mind for the rest of my days - her focused, intent stare as she desperately tried to hold my gaze, before her eyes glazed over and her focus turned inward...

This was what pure bliss looked like. And it was astonishingly beautiful.

As instructed, I kept fucking her through her orgasm, albeit slowing down a little.

She was riding a big one, frantically fingering herself while in the throes of it; from the looks of it, she was hell-bent on riding on right into the next. Pulling all the way out, I immediately pushed back inside her, getting a loud "Yeee-eeesss!!!" for my trouble - and there, just as her orgasm ebbed, she shook in another. I could feel myself closing in, too, so gave her another couple of thrusts, again pulling all the way out before slipping back inside, providing extra stimulation for the both of us.

Ella whimpered, then softly suggested that she probably could take no more, not now. I was very close. "Please," I begged. "Another couple of seconds will be all I need..."

By way of reply, she pulled herself back a little, then slammed back onto my cock. I erupted, being thrown into an orgasm which made my toes curl; I shot my load deep, deep inside her, then my lights more or less went out - collapsing over her, my still spewiing cock slipping out of her, the last couple of cum spurts filling the condom as my cock slid along her thigh.

I lay over her, still, utterly spent.

Next thing I knew, Ella stirred under me, then exclaimed "Fuck, we fell asleep! What time is it? My parents! Fuck, fuck, FUCK!!!"