The Catch-Up Ch. 05

"What?" I said hurriedly and wordlessly, she handed it to me.

GIGI: I guessss that you're hard right now

"Ohhh, man. This is getting serious." I took a deep breath, staring at that text on my phone screen, all too aware that I did have a hard-on in my chino shorts.

"I'm, uh... guessing you have to take another pic?" Bridget mumbled.

"I mean, yeah, but... should I?" I cleared my throat.

"Oh, come on, you can't pussy out now. This is like a once-in-a-lifetime thing. You think Gigi would send you nudes if she knew it was you?"

"Okay, first off, fuck you." But I knew she was right. "Shit. Okay. Maybe just another, um... bulge pic... I don't know why I'm telling you this," I stammered quickly. "Do you want to like... look way for a sec?"

"...Sure." Before things could get more awkward, Bridget turned around. I swallowed, unzipped my shorts and as quickly as I could, snapped a photo of my underwear, complete with the bulging outline of my hard cock against the thin cotton.

Fumbling to zip myself back up, I typed out a caption and sent the photo, holding my breath the entire time.

UNKNOWN: That was an easy one

We sat there in silence, waiting for a response, Bridget hovering so close to me I could smell pot, men's deodorant, and the citrus air freshener she used to try to cover up the pot.

It was a photo, a close-up of Gigi's sharp chin, the bottom of her slim nose, her full lips parted, and her pink tongue stuck all the way out.

I suddenly remembered the sensation of that tongue brushing my earlobe teasingly during truth or dare, and shivered.

GIGI: Finally, this game is getting fun

Bridget let out a long breath that tickled my neck.

"...What are you gonna guess?"

"Got anything good? If I'm gonna show you the next picture, you have to work for it." My voice was hoarse.

"She knows you've met and she's seen your skin tone. If you're gonna stay covert, it has to be something she doesn't know you know." Bridget adjusted her cap as she thought. "What do you think her favourite position is?"

"I don't know. Like... you wanna actually guess?" It seemed almost inconceivable to stop cheating at this point.

"What position were you in with Sadie? That obviously made a big impression."

"Um... from behind, like... doggy, I guess." I rubbed my eyebrow. This was really getting into the nitty-gritty.

"Could go with that. She's got that whole killer sex vixen thing happening though, she seems like she'd like something a bit more active." Bridget chewed her lip.

"Yeah, I was gonna say... Should we guess cowgirl?" I asked.

"Sure, just do it, we don't want her leave her hanging," Bridget said quickly.

GIGI: lol incorrect... and you were doing so well

Bridget and I groaned. "I said to do doggy!" Bridget smacked me in the shoulder.

"Yeah, and then you changed your mind, genius!" I pulled her hat down over her eyes. My phone vibrated.

GIGI: I guess that you're over 6 inches

"Dick pic, dick pic alert!" Bridget dug her fingers into my arm. "She's practically begging for it, oh my god."

"Jesus Christ." I swiped my hand down my flushed face. This was hell on my nerves.

"What? Are you not..." Bridget trailed off with a snort of nervous laughter.

"I don't know!" I threw myself back on the carpet, covering my eyes.

"What, like you haven't measured it?"

"No! I was going to, but then I felt stupid and I couldn't find the measuring tape..."

Bridget cackled with laughter. "Well, I guess we better find it."

"We?" I muttered.

"I mean... you said if I wanted to see the pics I had to work for it, so... Anyways, you'd probably fuck it up by yourself," She said quickly, snickering. I narrowed my eyes, but seeing as there were very little boundaries left between Bridget and I at this point, I shrugged.

We hunted around downstairs for the plastic tape measure, grabbed it as quick as we could and hurried back upstairs.

"All right—let's get this over with," Bridget held out the tape measure aggressively, like she was going to throttle me with it.

"I'm, uh... I'm not ready..." After all that anxious running around downstairs, my hard-on had retreated into a semi.

"Oh. Maybe just, uh, look at the pics she already sent and..." Bridget mumbled and I nodded.

"Sure." I paused, sitting down on my bed and gesturing nervously to my fly. "Do you mind if I..."

"No, no, uh... you do you..." Bridget ran a hand through her tangled hair, plopping down on the other end of the bed. "Not sure how else we're going to, uh, measure it."

Swallowing, I unzipped my shorts and started to rub myself, just through my underwear at first. I looked down at my phone, flipping through the photos of Gigi's waiting tongue, of her nipples poking through her dress, of her ass curving out from beneath it.

Breath growing heavy, I pulled down my waistband and took out my rapidly swelling cock. I had seen Bridget's pussy, I had tasted it, for god's sake—it wasn't so strange that she was seeing my hard, naked dick.

I stroked myself firmly, feeling my shaft continue to stiffen and grow taut. Out of the corner of my eye, I saw Bridget, who was casually averting her eyes, glance over.

"Okay, we should, uh... measure—" She turned towards me, lifting the measuring tape awkwardly.

"Wait, um... it gets bigger..." I mumbled. "If you just—give me a sec."

Bridget froze. "—Oh. Really—Okay." She gave a soft huff of laughter. "Sorry, this isn't exactly my area of expertise..."

I snorted, giving her a quick smile. "I know, it's all good."

"Do you want... uh, do you want some lube or something?" She asked.

"Oh, uh... do you have some?" I asked. It might help—normally I could get to full mast in a few seconds, but the strangeness and anxiety of the situation was slowing me down a little.

"Always—" Bridget climbed down from the bed and went to her backpack. She had a small tube in her hand when she returned, sitting next to me on the bed and uncapping it. I went to hold out my hand, but she just reached over and squirted the translucent gel directly onto the head of my cock.

I gasped as the cool lubricant splashed onto my flushed skin, and we made awkward eye contact, before she quickly pulled back. But Bridget stayed close, watching me spread the lube along my length, giving a slick sheen to my cock and my strokes a slippery smoothness.

"It's so... angry-looking," Bridget said, sounding like she was observing an alien species. How had I forgotten that she'd never seen a cock before in real life?

I laughed in spite of myself. "...Thanks?"

"I'm serious, dude. It looks painful." She was frowning, mouth slightly open, an expression of wonder, confusion and slight alarm. "And your foreskin... truly wild."

"Shut up..." I snorted, trying to focus on the photos. One last look at Gigi's butt and I grunted. "Okay, I think I'm ready."

"Okay—hold still." Bridget shifted closer, lowering the tape measure. "I Googled how to do it properly—you have to bone press it."

"What does that mean?"

"Here—" Again, surprising me, Bridget reached down and placed the end of the tape measure against the skin just above the base of my dick, and pressed down until she hit bone. Her knuckle was just barely brushing the base of my cock. "Like that."

Brow furrowed, tongue at the corner of her mouth, she carefully stretched the tape measure out to the tip of my cockhead, laying it flat against my shaft. I'd seen a similar expression on her face when we were dissecting a frog in Bio class—keen focus and morbid curiosity.

"Call it like—6.6...6.7 inches." Hearing Bridget calmly report the exact length of my erect cock was certainly one of the strangest moments of my life, but I wasn't complaining about the results--I knew how rare (and inconvenient) the 8 and 9-inch monsters that porn stars boasted were.

She removed the tape measure and then quickly wrapped it around the thickest part of my shaft. I stood as still as I could, the tips of Bridget's fingers again, millimeters from my cock. "And like... 5.8 inch girth."

"Cool..." I said, throat dry, not expecting this much thoroughness. "Should we take the—"

"Yeah—" Bridget slid away the measuring tape and grabbed my phone. "Just sit there like that—you can hold it if you want."

To get the angle she wanted, she crouched down on her haunches on the floor in front of me, and automatically my cock flexed at the sight of her basically kneeling between my legs. Thankfully, she didn't seem to notice. Eyes on the screen, she nodded, looking satisfied. "I feel like that's good. Not that I would really know."

"This is so weird," I murmured as I took my phone. The photo was honestly really good. Sun was streaming in from the skylight, bathing my tawny brown skin, and my cock looked about as thick and hard as it ever did, especially from the angle Bridget had chosen.

"It's all for the nudes, AJ..." She plopped herself on the bed beside me. I awkwardly tucked myself back into my underwear, still uncomfortably hard.

UNKNOWN: Good guess

I typed out simply along with the photo, taking a deep breath before hitting send. It was away, and there was nothing I could do about it.

Bridget and I settled ourselves on our stomachs across my bed, side by side like a couple of schoolgirls at a sleepover as we waited for a reply.

"She did want a dick pic, right?" I said after a few moments of nothing. "I didn't just sexually harass her?

"She literally guessed your dick size, dude. I'm pretty sure that's what she was going for."

Bzz. Bridget crowded into me to look.

GIGI: So that's why Sadie screamed

GIGI: God damn that thing is fat

A rush of excitement filled my chest.

GIGI: Ask me

Bridget snatched my phone.

UNKNOWN: I guess you're thinking about sucking that fat cock

"Bridget..." I sputtered, and she flashed me a mischievous smile.

GIGI: Fuck...... guilty

Gigi's mouth and chest filled the frame of the photo. Two of her fingers were between her parted lips, wet and shiny. But below, her bodycon dress was rolled down to her ribcage, and her full, tanned tits were completely exposed. They were perky and squeezed tight together even without a bra, more than a comfortable handful, with fat, wine-dark nipples, one pierced, of course, with a silver barbell.

"Holy shit..." Automatically, I reached down and pressed my palm against my cock, straining against my underwear again.

"Yesss..." Bridget whispered, mouth opening. "Finally." She still had my phone in her hand and typed out another text.

UNKNOWN: Holy shit those are unreal

GIGI: I guess you're jerking off to that pic

I breathed in sharply. Bridget immediately sat up on her knees and turned the phone towards me. "Take it out. We're gonna send her a video."

"Are you sure—"

"I'll be quiet. Come on..." She was breathing hard. "Jerk it."

"Okay, okay..." I said nervously, fishing my cock back out of my underwear and starting to pump. With Bridget holding my phone, I didn't have the image of Gigi's tits to look at, but as the first nude I'd ever gotten, it was pretty much burned into my mind.

And there was also Bridget.

As I started to stroke, lying on my back, my tomboyish friend hunkered down on all fours, leaning on her elbows to her face and the phone was on a level with my dick. Her butt was raised just a little above the rest of her, one ankle crossed over the other like Gigi's had been in the pic from last night, though she was wearing a lot more clothing, obviously.

Her hazel eyes were fixed on the screen, narrowed in concentration. I swallowed—it was honestly bizarre how hot it was to see her staring with such rapt attention at a video of me jerking off.

"Hh," I breathed softly, my fist sliding up and down my cock.

"Okay... got it," She said softly and I saw her type out a message and hit send. I just lay there, still casually touching myself. Bridget glanced over at me and our eyes met. I saw her gaze run briefly up and down my body. Her breath was shallow and her cheeks were a little red. That photo of Gigi must have turned her on as much as it did me.

When an answering buzz came back, Bridget scooted over and lay down next to me on her back, our shoulders touching, holding the phone above both of us so we could both see.

GIGI: Good boy

GIGI: Fuckit's soo juicy

The next two texts were accompanied by a photo.

GIGI: Game over

GIGI: You win

It was a photo of Gigi from the neck down, her back facing the camera, kneeling on her bed with her thighs spread in a V, completely naked except for her black thigh-highs. The smooth arch of her bronzed, toned back curved down to the thrust of her hips and the round swell of her bare, sun-kissed ass, cheeks firm and squeezable.

Bridget and I said variations of the word "Fuck" at the same time. As my fingers wrapped back around my cock, hers fumbled the button on her loose shorts, unzipping them, yanking them over her hips and down her legs. Her eyes stayed on the photo as she thrust a hand into her boyshorts.

With the other hand, she texted back.

UNKNOWN: Oh my fucking god

UNKNOWN: Your body is insane

UNKNOWN: Video?

Then she opened the photo again, and while we waited impatiently for Gigi's response, Bridget and I lay there touching ourselves to the sight of Gigi's naked body, side by side. Bridget's breathing grew steadily heavier, and I could hear how wet she was under her fingers, hand moving urgently inside her panties.

"Fuck, it's hot," Bridget bit out.

"I know. She's killing me," I panted.

"No, like—It's really hot in here—" Bridget huffed. Being in the attic, my room often was in the summer. "I'm getting sweaty. Fuck it, I'm just gonna get naked, okay?"

"Uh, yeah, I don't care—" I tried to say as casually as someone could while jerking off and watching one of my best friends hurriedly strip off her shirt, sports bra and finally, underwear.

My phone buzzed and Bridget flopped down on her back next to me again, only now she was completely naked, bare leg pressing against mine, bare tits swaying slightly as she settled. This was definitely the closest I'd ever been to a naked girl I wasn't about to have sex with.

"Come on, play it—" Bridget hissed, reaching out and tapping the video Gigi had just sent.

The video opened on the same frame as her last photo, kneeling with her back and ass to the camera. But then, like the photo was coming to life, Bridget slid her hand back, running her fingers over her naked curves before sinking her acrylic nails into her thick ass cheek, grabbing a big handful and squeezing, shaking gently to show off the ripples through the full globe.

"Fuck yeah..." Bridget whispered, spreading her thighs next to me, using her own wetness to smear her clit, rubbing quickly with two fingers. And I was right there with her, jacking my cock hard, holding the phone aloft with my other hand.

On the video, Gigi had begun to rock her hips, leaning forward and casually bouncing her ass up and down. Then she swayed it side to side, grinding herself on the bedspread as Bridget and I watched with unblinking fascination.

All I could hear from the video was the music playing in her room, some floaty, girly bedroom pop and faintly, what sounded like a riding mower outside. For some reason it was even hotter that Gigi's dad or knowing her, her gardener, was outside doing the lawn while she was in her room, showing off her naked body for the camera.

Gigi's head turned, so we could just see her chin and lips at the top of the frame over her shoulder, and she spanked her own ass, hard enough that the smack cut through the other noise. I saw her muscles tense and her lips parted gently, but the only sound was a satisfied exhale. Then she reached for the camera and the video ended.

GIGI: Your turn, creeper

"God fucking damn it..." Bridget grabbed the phone. "We have to send her another video." She rolled onto her side, still lying next to me, and pointed the camera at my cock. "Where's the lube? That looked good, before."

"Uhh—" I looked around, feeling a little exposed.

"Ugh, whatever—" Impatiently, Bridget sat up and leaned over until her head was hovering above my cock, holding her tangled, tawny hair back.

I nearly had a fucking heart attack.

But she only let a mouthful of spit drop out of her mouth to land on my fat, purple cockhead, dripping down my length. As she swiped an arm over her lips, our eyes met--mine wide with shock, hers blazing and determined. Then I grunted and started pumping my dick, fast and hard, spreading Bridget's saliva all over my achingly hard shaft until the taut brown skin was shiny and slick.

Bridget whipped up my phone to record. With her naked, leaning over me, face flushed, lips pressed tightly together, the peaks of her breasts stiff and pebbled with goosebumps, I had a lot more to look at then last time. As always her gaze stayed on the phone screen, maybe oblivious to my eyes travelling across her, maybe willfully letting me use her nude body for "inspiration" without making it awkward.

As I watched her, and she filmed me, her free hand strayed between her thighs. With her legs open, I could see her fingers almost absent-mindedly circle her clit, dipping inside her dripping entrance. I felt a ripple of tension run up my cock and my shaft flexed hard, veins throbbing.

Next to me Bridget breathed in sharply and I saw her finger plunge into her pussy. With a slight gasp, I let go to stave off an approaching orgasm and Bridget jabbed stop on the video. As she sent it off, my eyes stayed on her.

"Can I, uh, can I help..." I said, nodding towards her. Bridget looked at me. "...Y'know... practice."

"Practice?" She chewed her lip. "Sure."

"Yeah, just for practice—"

"Yeah..." Bridget breathed, lying back down next to me as I reached between her legs, my hand joining hers. While her fingers moved across her clit, I sank mine inside her, stroking her wet, clasping walls.

My phone lying on the covers, forgotten for the moment, Bridget and I worked in concert to get her off, plying her slick pussy, my free hand on her bare thigh, which was resting on top of mine as we lay side by side.

"Huhh... hh... mmph..." Her heavy breathing turned into shallow, muffled gasps and I shifted so I was leaning over her chest.

"Can I..." Mouth watering, my gaze flicked down to her breasts and she nodded hurriedly, face screwed up with pleasure.

"Mmph..." I closed my lips over Bridget's nipple and sucked, batting it with my tongue, teasing the other one with my fingers.

"Hnngh..." Bridget arched, looking up at the ceiling, rubbing herself faster.

Bzz.

Immediately we both lunged for the phone, clambering awkwardly, our legs getting tangled up with each other. Bridget ended up with it in her hands, falling onto her stomach. I was briefly distracted by the soft curve to her bare ass, but then I huddled in to look at the phone, leaning half-across Bridget's back.

GIGI: It's so fucking hot that I don't even know who you are and your fat cock is making me wet as fuck

The video started on that familiar pose, but Gigi was clearly done messing around, because she immediately leaned forward onto all fours, reached between her thighs and started rubbing her exposed folds, soft and pink in the natural light seeping through her blinds. Bridget and I could hear her panting breaths as she circled her clit, teased it between two of her fingers. She was visibly wet, the shine of moisture catching the light, fingers slick and coated, a strand of arousal connecting one pussy lip to the other.