Chapter 14: Out of the Blue

“Nnnngggghhhh...” I groaned in rapturous relief at finally, finally, finally sinking my aching cock into the warm, wet confines of a supremely tight teenage twat.

Once the girls had decided to see how far they could “push all of the boundaries just short of having sex”, Sam had made a new rule for tonight that I couldn’t penetrate any of them until they told me I could. I figured it was no big deal since I’d actually gotten into both Naimh and Sam already, and in all honesty we’d been messing around and having fun in ways that were reasonably pleasurable.

But I still wasn’t allowed to actually put my P into someone’s V, if you know what I mean. It was as if we’d been reset back to the days in high school when the girls would tease me and titillate me right up to the brink, trusting that I’d never simply take anything they didn’t explicitly give me. And with that thought in mind, it felt like they’d been teasing me for decades.

Up until now, at least.

And it felt soooo gooooood.

I could feel my face contorting in agony and ecstasy as I drove deeper and deeper until there was nowhere left to drive.

And from beneath my heaving body, lovely Lily smiled up at me with sparkles in her eyes and a delighted look on her face as she watched my face contorting in agony and ecstasy as I drove deeper and deeper until there was nowhere left to drive.

My cute ku’uipo clutched my arms and panted shallowly, carefully observing every millimeter of my face as I pushed every millimeter of my dick deep inside. And as soon as I had completed my journey to the point where man and woman were joined together as intimately as two human beings can ever be, she reached up to grab my head and yank it down so that our mouths could join together as intimately as two human beings can ever be.

Perhaps I should explain.

As I already told you, the girls and I spent all evening exploring all the different ways we could find pleasure without ever putting my P into someone’s V (or someone’s A, for that matter). But through trial and error, the girls certainly seemed determined to at least try to find whatever other places they could put my P.

What made the entire situation wholly unfair was that each of the girls (except Lily) still got to get her V stuffed with P – just not my P. The very first thing Sam did was buckle on Matty Junior and proceed to start demonstrating to Lily how it worked. Naimh was more than happy to lie back across my bed and grab her legs behind her knees to pull them apart. The platinum-blonde proceeded to plow her temporary prick into the redhead’s pink pussy and then pound away at her while the pair of pretty maidens made out with each other with marvelous moans and sexy sighs, much to Lily’s viewing delight.

And mine.

Fuck, watching my Head Girlfriend’s bubble butt rising and falling and pumping and pounding while Naimh squealed and moaned and ... yeah.

Meanwhile, Belle wanted to try out some of the “alternative” methods for masturbating my rod. We’d done plenty of blowjobs and titfucks, of course, and even the occasional hotdogging of her buns. But my little pixie wanted to try out the whole “fucking her thighs from behind” thing that Sam had described and also see where else she could fit my cock.

Our first problem was the one-foot height difference. There was no way I could stand behind Belle and slot my dick between her thighs without squatting rather uncomfortably in a position I’d never be able to maintain for very long. Belle’s solution was to run downstairs and swipe the stepstool from the kitchen for her to stand on. And while the whole situation was quite novel, “novel” wasn’t very good for maintaining an erection (plus, the next day Belle forgot where she’d left the stepstool when she needed to retrieve some spices from one of the top shelves).

Anyways, Belle was of course quite happy to drop down and blow me hard again. After that she parked the stepstool right behind one of the armchairs in the sitting area, braced herself atop its backrest, and had me slide my dick between her thighs that way while cupping her hand to keep it angled through the furrow of her pussy.

It felt ... novel.

But nowhere near as good as being inside a pussy.

Still, Belle seemed to be getting a kick watching my mushroom head push forward through the gap of her thighs and into her cupped hand while she tried to keep the top of my rod pressed up against her clit. I was happy she was having fun, but at the same time, I really wasn’t getting enough direct stimulation to feel satisfied.

On the bright side, I still had a great view of Sam pounding Naimh into the mattress with Matty Junior, which was both sexy and stimulating. I found myself quite jealous of the faux phallus, but forced myself to try not to think about that aspect too hard. Lily was certainly entranced, however, so when Sam came to a stop and asked if Lily wanted to try it out, the little Hawaiian girl nodded quite eagerly.

Of course, Belle insisted on being the first to get fucked by Lily’s strap-on, so my impish pixie left me to go join the others on the bed after Sam pulled out of Naimh.

My gorgeous redhead looked absolutely ravishing: flat on her back with her legs spread to the sides and her red-worn pussy gaping open and soaking wet. It was quite the inviting sight and I wanted nothing more than to drive my dick deep into her inner depths and just give my Irish girlfriend a royal pounding. But I hadn’t forgotten the whole point of tonight’s activities and so held myself back with a sigh.

On the other hand, I recognized that my horny girlfriend had not actually gotten off from Sam’s strap-on shafting. The whole thing had been more “toy demonstration” than “orgasm induction” for Lily’s sake. So when Naimh stared down the length of her body at me with an expression of lustful need, I was quick to park my face in her pussy, ram two fingers into her twat, and start eating as if her life depended on her climaxing in less than two minutes flat.

I’m proud to say that if that had actually been the case, I would’ve saved my girlfriend’s life with plenty of time to spare. Yay me.

But as great as it was to feel my personal redhead boxing my ears with her thighs as she squealed and screamed in ecstasy, I still couldn’t plant my prick into her puffy pink pussy. I then got distracted by the über-sexy sight beside me: the promised one about watching two short-but-stacked little hotties rolling around completely naked, their pouty lips crashing together while their big titties mashed together at the same time, all with Lily’s ‘lovely arse’ pumping up and down in rhythm with the way she thrust her fake dong in and out of Belle’s tight twat. Well “semi-rhythmic”, at least. Lily had never actually felt anyone else thrusting a cock into her, and she’d certainly never done the thrusting before either (nor even been born with the instinct), so she was having trouble coordinating her abdominal and leg muscles to perform the process.

Who’d have ever thought Lily would wind up fucking Belle with a strap-on before losing her virginity?

In any case, my real-deal dong didn’t suffer from disuse for long. Sam was more than happy to roll me onto my back and put her original suggestion into practice: that of riding my rod like a rail in a cowgirl position, trapping my steel-hard shaft against my belly and scooting herself forward and back across it while grinding her clit down on my cock and leaking pussy juice all over me. It probably brought back some fond memories for her, because it brought back some fond memories for me too.

At first she bent over so we could make out like bandits while I grabbed her juicy ass and helped yank her back and forth. Then she shifted up a bit to crush my face beneath her heaving bosom, threatening to suffocate me within her lush titflesh while I felt oh so freaking tempted to adjust the angle of my prick so that it speared into her saturated snatch the next time she scooted backwards. But I held off on that temptation and instead snared one of her tasty, turgid teats within my mouth and suckled on it powerfully until my hands helped grind her clit against my bone to the point where she finally stiffened up and came.

“Gawd I love you...” Sam wheezed as she came down from her high, holding my cheeks in her hands before giving me a quick kiss.

“I know,” I panted right back, grinning before tugging her down to me for another kiss.

Meanwhile, the two shorties giggled as Belle switched positions to let Lily discover the joy of blasting away from behind while enjoying the view of a shapely booty. In her enthusiasm, Lily set aside her inner Disney Princess and embraced her inner cowgirl by reaching up to pull Belle’s hair into a makeshift bridle, sending the little pixie into overdrive. Unfortunately, that fun quickly ended with Lily losing her connection when both girls gave ground in anticipation of an epic thrust only for the phallus to bounce harmlessly off Belle’s thigh.

Lily fumbled trying to get P back into V like, well ... a fumbling virgin. Belle wasn’t making it any easier by wiggling her tushy as an enticing - yet moving - target and eventually took matters into her own hands by swinging back around and sitting her friend down so she could notch herself on top (Who’s the cowgirl now?) with her boobies shoved into Lily’s face. Of course, from that position, there really wasn’t much Lily could do other than kiss, nibble, bite, and hold on as Belle undulated on top of her.

Belle took Lily’s hands and placed them on her butt to show her how to guide her up and down even if she hadn’t yet discovered the hidden art of the Sitting Upward Thrust, but the Hawaiian ku’uipo let her hands roam back up her little lover’s back to pull her into a soft kiss. Belle pulled back with a grin that she found mirrored on her bestie’s face as the two burst into giggles. Belle carved herself around and bounced up-and-down on Lily’s borrowed equipment a few more times, but soon disengaged as both girls turned their attention to what the three of us were up to.

As it happened, Sam and Naimh had gotten back in the groove of shoving my dick into unconventional crevices. Sam wanted me to try fucking her armpit of all things (novel, not sexy). Belle bounced over and tried to give me a footjob with both feet (awkward and not my personal fetish). Then Naimh attempted to get my dick between her toes (didn’t fit) before deciding to try the between-the-thighs thing. By that point, my dick felt like it was getting such weak stimulation that it started to deflate.

Recognizing the problem on her hands (between her thighs?), Naimh got me to adjust my aim upwards and hotdog her buns, which was marginally more stimulating. The view of sliding my shaft between her bubblicious buttcheeks was great, but could never be as good as the real thing. I guess I started whining a bit, knowing that I wasn’t allowed to shift my angle and spear my schlong through the sexy girl’s sphincter. But then Lily wanted a turn, and the excitement of hotdogging the Hawaiian hottie’s buns was actually quite ... invigorating. I got some fresh starch into my shaft as I mashed Lily’s supple buttcheeks around my big dick (I felt like I could do that one all day). And Sam bent over beside Lily, fondling the petite girl’s big tits while whispering really naughty words about what my big dick was doing between her buttcheeks that seemed to get Lily hotter and hotter with every passing minute.

Meanwhile, Belle had donned Matty Junior before lying flat on her back while Sam left Lily’s side and mounted up cowgirl and went for a ride. When my platinum-blonde beauty bent over to make out with my Baby Belle, I had an excellent view of my Tight-Ass Slut’s tight ass, and I couldn’t help but imagine the Sam sandwich we’d get if I sauntered over to slide the real Matty’s Dick in-between the bountiful buttocks of the buxom blonde bombshell’s booty, bludgeoning open the beautiful babe’s backdoor entrance with my big dick, and then burrowing every last inch into the depths of the buxom blonde bombshell’s bunghole while her wet box was still bayoneted on my Baby Belle’s borrowed dick at the same time.

Nnnngggghhhh.

But I couldn’t. Not yet, at least. Because Sam had made “The Rule”.

For those of you counting at home: Matty Junior had gotten into all three of Naimh’s, Belle’s, and Sam’s pussies while my real thing was still at zero.

Totally unfair.

(Okay fine, I got into both Naimh and Sam before we got started. Ignore me: I’m just whining. I still haven’t cum yet gawddammit!)

I consoled myself with the knowledge that the girls were having fun and that they certainly wouldn’t leave me high and dry for the entire night. Sam’s eyes had sparkled when she’d made that rule, but they’d sparkled with a playful glee that promised me she’d make it worth the wait.

But sometimes waiting can be so hard, you know?

Fortunately, they didn’t make me wait much longer. Naimh was right next to us the whole time I was hotdogging Lily’s buns, reaching down with her right hand to rub the Hawaiian girl’s clit while Sam did the honors of playing with Lily’s tits. And when my gorgeous Irish girlfriend recognized my need, her eyes glittered and she stood up straight in such a way that I felt like I could actually see the lightbulb blinking on above her head.

“I’ve got the best idea!”

“Nnnngggghhhh...” I groaned in rapturous relief at finally, finally, finally sinking my aching cock into the warm, wet confines of a supremely tight teenage twat. It had felt like decades of messing around in ways that “pushed the boundaries just short of having sex” that had been pleasurable but in no way got me close to popping off. But now that the moment was here and I crammed inch after inch into the comely coed’s clasping cunt, it took all the self-control I had to NOT abruptly lose my load.

Because it felt soooo gooooood.

I could feel my face contorting in agony and ecstasy as I drove deeper and deeper until there was nowhere left to drive.

And from beneath my heaving body, lovely Lily smiled up at me with sparkles in her eyes and a delighted look on her face as she watched my face contorting in agony and ecstasy as I drove deeper and deeper until there was nowhere left to drive.

My cute ku’uipo clutched my arms and panted shallowly, carefully observing every millimeter of my face as I pushed every millimeter of my dick deep inside. And as soon as I had completed my journey to the point where man and woman were joined together as intimately as two human beings can ever be, she reached up to grab my head and yank it down so that our mouths could join together as intimately as two human beings can ever be.

And now you’re caught up.

Lily and I kissed and kissed and kissed like the affectionate lovers we really were. Any discussion about whether or not she should be formally recognized as my official girlfriend weren’t really important. And yet I felt like that designation was already a foregone conclusion.

Did I love her? Well ... I wasn’t sure yet. Did she love me? She definitely seemed well on her way, if not there already. Did I care about her enough to find out how special we could mean to each other? Absolutely. And with our formal date scheduled for next Saturday, I believed that unless something went terribly wrong between now and then, in seven days I would both be taking Lily’s virginity and declaring her my fourth girlfriend at the same time.

But not just yet.

Eventually Lily and I separated, smiling into each other’s face from only inches away as we panted for breath. A moment later I shifted my gaze only fractionally to the side to smile down at Belle’s face instead.

My girlfriend really had the best ideas.

See, I’d sunk my aching cock into the warm, wet confines of Belle’s supremely tight teenage twat where my ever-adoring “not-girlfriend” had parked herself in one of the armchairs with her legs spread apart and to the sides. Lily quite literally sat in Belle’s lap, although her legs had been flung over the armrests to help relieve some of her weight. So when Naimh helped guide my mushroom head into the moist muff of a comely coed’s clasping cunt, it was my lovely “little sister’s” luscious labia my prick was parting instead of Lily’s, even though I was able to stare down into the Hawaiian hottie’s beaming eyes.

In my head, of course I knew I was fucking Belle and not Lily. And yet to see the nubile newcomer’s pretty face beneath mine while I slowly but steadily pumped my prick and felt the pleasure of a pleasant pussy constricting my cock, it was impossible not to imagine this would be what it would feel like when Lily and I had our actual first time.

Speaking of imagination, Belle smiled up at me before ducking her head back behind Lily’s body, perhaps trying to help the illusion that Lily and I were alone. I grinned and reached around to caress Belle’s cheek in thanks before returning my focus to the Hawaiian girl while simultaneously feeling proud of my Baby Belle. Not everyone would be so willing to offer up her body as a substitute hole to help her friend enjoy this kind of experience. And I swore to myself I would make it up to her later.

In the meantime, I took a deep breath and concentrated on what I was supposed to do. Lily wouldn’t be able to feel the physical pleasure of my rigid rod rubbing against her inner nerves or enjoy the stuffed-up sensations of being stretched by my steel-hard shaft. All she really wanted was to hold me, kiss me, and watch the elation on my face as I enjoyed the act of lovemaking so that she could imagine what her own true experience would be like.

So we made love.

Perhaps it wasn’t PG-13, but I still strove to live up to Lily’s most innocent fantasies about her first time: more intimate kissing and fondling instead of screaming and spanking.

Kissing and fondling, Lily was used to. Despite the fact that my much larger body loomed over her in a dominant position with my thick and throbbing dick only inches away from her undefended pussy, she felt no fear or nervous anxiety about whether or not I would try to actually push myself into her. Everyone in the room was on the same page about preserving her virginity until our big romantic date and there was absolutely no pressure whatsoever for her to put out.

She could relax and enjoy herself. She could wrap both her arms and legs around me and hold on for the ride while I steadily pumped my hips back and forth, up and down, in and out. I got to feel the exquisite pleasure of a supertight twat hugging every inch of my big dick, that pleasure feeding erotic arousal and energy into my body that I poured back into Lily’s mouth with passionate kisses and contented groans.

“Matty ... Matty ... Matty...” the beautiful girl in my arms breathed, chanting my name as if it were a sacred word.

“Lily ... Lily...” I murmured back, making it clear that no matter where my dick was currently buried, in this moment I was focused on her. “My Lily ... My sweetheart ... My ku’uipo.”

“Say it again, hoalauna...”

“My ku’uipo...”

“Again...”

“My ku’uipo...”

“Again!”

“My ku’uipo!”

“Holy FUCK!”

I tilted my head to gnaw on Lily’s neck while she clutched my head and quivered beneath me with breathy moans. I worked my way lower to nuzzle my nose into her cleavage and playfully nip at her turgid nipples. I suckled at first one teat and then the other, the hungry expression on my face bringing delight to hers. And I held myself above her, gazing deep into her eyes.

Like my ku’uipo was the sexiest, most incredible, most desirable woman on Planet Earth.

And then she came.

I wasn’t even fucking her. My P was not in her V, but she came anyway. She was kind of riding my rod at the time, all of her weight supported in the base of my shaft even though the first six inches or so were buried within Belle. Perhaps she got enough pressure on her clit to trigger her, or maybe the emotional high she felt was enough to send her over the edge. Probably a little of both.

Whatever the reason, one moment Lily was staring back into my eyes as if I was the sexiest, most incredible, most desirable man on Planet Earth. The next moment her eyelids fluttered and her mouth gaped open while she tilted her head back a bit and started screaming, “MATTY! MATTY! AAAAUUUUGGGGHHHH!!!”

And then Belle came, chorusing from underneath, “MATTY! MATTY! MMMAAATTTTTTYYY!!!”

My Baby Belle’s convulsing cunt clutched my cock as if trying to coax out my cum and clamping up so close-fitting that at first I couldn’t move. I kept myself buried deep within her while both Belle and Lily thrashed beneath me, feeling my balls coming to a boil. For a moment I wanted nothing more than to unleash both barrels and blast off deep within one little shorty’s soaking wet snatch while imagining I was firing off into the other one’s. But a split-second later I remembered Lily’s original request, and I groaned and strained and gritted my teeth to hold back the rising tide while struggling to extract myself from Belle’s vagina’s viselike grip.

At the last fucking second Belle’s pussy finally let me go. I jerked myself out and took a big step, planting my left foot on the armrest while leaning forward and bracing my left hand atop the backrest. My right hand aimed while pinching off the tip to prevent an early explosion. But as soon as I got my mushroom head in front of Lily’s still gasping face, I unleashed hell, groaned a sigh of relief, and gushed out a gallon of gooey jism all over the Hawaiian hottie’s comely countenance, starting with a stringy shot straight across her forehead and a little bit into her hair.

“EEEEEE!!!” she squealed in delighted surprise as I continued painting her face. She had to blink when the second shot painted across her left eye and the bridge of her nose. The third hit her in the cheek and down over her upper lip with some of it getting into her mouth. And then she managed to line up her own gaping piehole so that the fourth and then fifth shots also spurted inside, although the fifth one left a trail down her lower lip and chin.

I sagged a bit, my strength leaving me, but Lily kept her face parked beneath my leaking dick so that my sixth and seventh shots splattered onto her forehead and cheeks. She stuck her tongue out and groaned “Ahhh...” as if she were at the doctor’s office with a tongue depressor. After dealing with the girls messing around and pushing boundaries without ever letting me into a pussy for what felt like hours, I had a LOT of cum backed up in me. And my ku’uipo stayed there, soaking up every last droplet onto her skin, until I had nothing left to give.

When I finally dropped my foot off the armrest and took a step back, I found Sam was right behind me and she hooked her hands beneath my armpits to help me stagger over to the opposite armrest. We were both a little off balance, so she dropped down onto the cushion first and I literally fell into my girlfriend’s lap, both of us laughing like idiots.

But the show wasn’t over yet as Lily abruptly twisted in Belle’s lap right in front of us, gathering up the pool of cum on her tongue and swiftly shoving it between Belle’s lips. And then Matty’s Little Cumslut took over, hungrily going after every gooey glob that decorated her new bestie’s pretty face with erotic moans and audible slurps signaling every step of her success.

Naimh suddenly dropped down next to me and Sam on the armchair, her emerald eyes afire as she grinned at Sam. “That was SOOOO hot! Can you and me do that next! Do you wanna be on top making out with him or underneath being the substitute pussy? I’m good with either. Maybe we try both?”

Seriously: I was the luckiest man in the world.

Following the girls’ attempt at killing me through Death By Fucking™ on Saturday night, we took it pretty easy on Sunday. Then on Monday morning, Naimh woke me up with an alarm clock BJ, I wound up filling her cunt with a fresh load of liquid love, and she rather happily held my hand all the way to campus while Belle followed behind us.

When we reached our usual intersection, my redheaded girlfriend gave me a quick kiss and then bounced away towards the Biology buildings while Belle happily slid her small hand into mine for the journey that remained. We chatted about whatever popped into Belle’s pretty little head for a bit until we got to the Engineering buildings. When we got there, my petite “little sister” jumped up into my arms and wrapped her legs around my waist so she could give me a passionate French kiss. I let her snog me for a minute before relaxing my grip as a signal for her to put her feet down. And then I patted her ass while she flashed me a pixie wink and then spun around to head off towards Chemistry.

I turned around to head inside and noticed a gorgeous honey-blonde babe in a neatly-pressed black suit approaching the building. “Good morning, Skylar,” I greeted affably, still riding the emotional high of that goodbye kiss with Belle, as I put myself on an intercept path with the blonde.

Skylar gave me a pleasant smile as we fell into step side-by-side, replying, “Good morning, Matt.”

Her tone was so casual and polite that it took me a second to realize she’d called me ‘Matt’ instead of ‘Matty’. It occurred to me that her using my more intimate nickname perhaps wasn’t appropriate around my classmates, so I simply smiled back and asked, “How was your weekend?”

“It was quiet, thankfully, after Saturday’s adventures,” she replied with mild relief. “I had a lot of work to catch up on.”

We entered the building together and then walked over to the auditorium-style lecture hall. “Schoolwork?” I asked. “Are graduate classes really so much harder than undergrad?”

“Well, certainly in comparison to a freshman introductory course, they are. When you get to the upper-division courses you’ll know what a real workload looks like.” Skylar pursed her lips and for a moment her eyes tightened. “You’re still quite young, Matt. Sometimes I forget that you’re only a teenager.”

“Age is just a number,” I replied with a shrug. “And everyone was a teenager at one point in their lives.”

“Indeed.” Skylar’s eyes took on a faraway gaze for a moment, as if she was looking back into memory. Meanwhile, we entered the lecture hall and began descending the steps side-by-side. I listened to the rhythmic sounds of her high-heels striking each individual stair tread rather than interrupt her momentary reverie.

Eventually we made it all the way to my regular seat without any further conversation. Skylar did not join me at my seat today. Instead she gave me a prim smile and said politely, “Have a good day, Matt.”

“Have a good day,” I replied in the same tone.

And then she continued down to the lecture floor and went straight to set her bag down at the professor’s desk. Two students immediately approached her, and she spent the next several minutes answering their questions.

Professor D eventually began his lecture and I settled in for class. It was one of his better lectures, all things considered. Immediately following the end of class, both the professor and our T.A. took questions from approaching students. Having felt I already got the basic gist of the lesson, I packed up my bags and headed out of the auditorium.

It was a cloudy day outside and threatening rain, but my world was full of sunshine and rainbows at the sight of the most gorgeous thing I’d ever seen waiting for me. My freckled Irish redhead bounced up to me with a beaming smile and her usual happy exclamation, “Matty!”

She came to a stop, and a split-second later her boobs stopped jiggling as well. She wore an insulated rain jacket unzipped throat to tails and a form-fitting sweater beneath that really hugged “the girls” along with her usual spray-painted jeans. She didn’t dry-hump my leg or anything but we still came together for a sweet kiss.

I smiled and rubbed my girlfriend’s ass. “Hungry for food or do you still have that key to the janitor’s closet?”

Naimh smirked and shook her head. “Sorry. He told me to leave the spare key in the closet. Don’t want to get the poor man in trouble, you know? We can go straight to lunch but ... uhhh...”

When her voice trailed off and she started looking past my shoulder, I chuckled and informed her, “Skylar’s fielding questions from other students. She is a T.A., remember?”

“Right, right,” Naimh muttered with an understanding nod.

“How about we sit down over there and wait for her to come out,” I suggested, gesturing to a table within view of the building entrance.

“Grand.” She wrapped her arm around my lower back and we walked together over to the table. I sat down first on the bench seat, facing away from the table itself and leaning against it like a backrest. But rather than sit down beside me, my gorgeous girlfriend plopped into my lap sideways so that I could wrap my arms around her and start up a fresh snogging session.