Chapter Three – Jack
Chapter Three
Jack
“Is he going to think you died?” Thea asked from beside me on her bed.
“Don’t go,” Thea said, rocking up onto her arms beside me with a slight pout.
I shrugged, mystified. “All right.” I saw enough of Bruce at work and he was a man, he’d understand. I still had another day off here—did she? “What were your plans?”
“I don’t have any. Other than you.” She gave me a mischievous grin.
“You don’t have to work?”
“Not until midnight. I might need a nap between now and then, but….” One of her hands crept under the sheets to encircle my cock.
I chuckled darkly and lay back. “Has anyone ever told you you’re insatiable?”
“You say that like it’s a bad thing.”
I grinned, even as she was making me hard—teenaged Jack would be so proud. “I’m out of condoms. So unless you’ve got some, we’ll have to face daylight.”
She laughed. “I’m a stripper. Strippers burn in the sun, it’s why we use tanning beds.” She crawled over me suggestively to open up a nightstand drawer full of…things. Things with tassels, things with straps, things that looked like rubber swords, and nubbly things—I leaned over to gawk.
“What are all of those?”
“Gifts from admirers. You would be surprised at all the gifts I get. And also sex toys.” Thea gave me a devilish look. “You’ve never played with anything before?”
“I mean I know what a vibrator is and I’ve seen raunchy porn, but—"
“You’ve never seen so many in one space before,” she said, gesturing grandly at the drawer, before digging around in it again, pulling one Trojan up in its shining package and moving to all fours.
“I think this is our last condom, so we’d better make it count.
” She batted her eyelashes, the very picture of innocence as she offered the condom over. “What do you want to do with it, Jack?”
It occurred to me then that there was no way I could’ve possibly explained this exquisite moment to younger-me, to give him hope and something to look forward to. No time capsule, no letter from the future, not even a personal visit would’ve made him—me—believe.
And yet here I was.
“I don’t know.” I said—because I didn’t care. Anything, any way I could get inside her, and make her feel good, make me feel good, was golden.
“Oh, come on Jack—you know.”
“Dealer’s choice,” I said, pushing the condom back. She thoughtfully tapped it against her lips.
“Hmm. It’s been awhile, but….” She darted back down and pulled up a toy, a small buzzy thing, then knelt nearby. “When we were younger…you had to have thought about me, right?”
“Uh huh.” There was no point in lying.
“Did you ever jerk off while thinking about me?”
“Of course.” I snorted. “Just like every other red blooded male in our graduating class.”
She leaned forward and pulled the sheet back. “Did you ever think that someday I’d be jerking you off?” she said, leaning over to stroke my cock.
“No,” I said, with absolute honesty. The second her hand touched my flesh—I wanted to shudder with excitement. She kept stroking as she lowered herself down bodily, crouching beside me.
“Did you ever think that someday I’d be sucking your cock?” she asked, staring up, as her lips parted to take me in.
My cock had to have been bathed in my cum, we’d fucked four times last night and hadn’t showered off—but she didn’t seem concerned, and the thought of her lapping up my cum made me even harder.
“Definitely not.”
“Hmm,” she agreed, swirling her tongue around my head before licking down my shaft to nuzzle at my balls.
“Goddamn,” I whispered, and she made another amused sound.
“Last question then—did you ever jerk off imagining yourself fucking me in the ass?”
I startled from the reverie I was falling into. “Uh—no. Not really.” And that? Was a lie. But admitting that I had seemed uncouth.
“Why not?” She faked being offended.
“It’s, uh, not in my repertoire.”
At that, her face lit up. “You’ve never?”
I hadn’t. Imagined it? Yes. Done it? “No. It just…hasn’t come up.”
“And you’ve never asked?”
“It seemed better not to know what I was missing.”
“Well, you’re wrong—and soon you won’t be missing it anymore.” She dove back into the drawer and pulled out a glove and lube, handing them over to me. “You can’t just jump on in there—not with me at least.”
“Oh—okay?” I said, pulling a glove on my right hand. I was used to that at least, I wore gloves every day at work.
“Get your fingers all warm and lube-y,” she said, and then lay down beside me. I heard her toy turn on, and saw one of her hands dart down beneath her, presumably landing between her thighs.
“And then?” I asked, doing what I was told, rubbing lube between my thumb and two forefingers.
“Go slow,” she said, and angled her pert bottom up.
I reached for her with my ungloved hand first, stroking down her back and up her thighs.
This…was a change for me. And yet how could I not?
Not when she was willing? I trailed my hand back up her leg and then grabbed hold of her left ass cheek, pulling it wide enough for me to see where she wanted me.
I stroked a lubed and gloved finger down her crack carefully, then gently pushed in.
She made a happy moan as I felt her ass take me. It felt just like fingers in a pussy, only the walls were tighter. I pushed deeper, and then started playing my finger in and out, back and forth.
“Oh, that’s good,” she whispered, rocking her ass up to take me, and then back down into her toy, I could hear the intermittent way its buzzing muffled on her skin. “More?” she asked, as I pulled my first finger almost out—and pushed a second one in to join it.
“Ohhhhhhhh,” she moaned.
She was so, so tight. But I not only pulled in and out, I spun wider, testing the boundaries of this new place, feeling her asshole soften for me.
“Yeah, Jack,” she said, with another appreciative moan. And when she felt wide enough, when I thought I could fit inside—I pulled my hand out, snapped the glove off, and pulled the last condom on.
I was surprised when she rose up to all fours in front of me. “I want you to see it,” she said, twisting back as I slicked the condom with lube. “I want you to watch yourself go into me.”
What I wanted to tell her was that I’d been going into her ever since I’d first seen her last night—in less than a day, I’d gone into her so hard I might’ve lost track of myself and fallen in.
“I don’t want to watch me, Thea” I said, lining myself up behind her. “I want to watch you,” I said, and pushed forward.
She groaned at the same time I did—the sensation of her ass was unlike any I’d experienced before.
I could feel the tight band of muscle there pressing against me, and waited for it to relax so I could push further.
As it did, I did, my hands spreading her cheeks wide, feeling myself sliding into her, falling anew.
“Oh Jack—just like that,” she whispered softly. I moved forward bodily until I was right behind her, my cock settled deep.
She made a whining sound and started to move, catching herself between her and her toy again, me watching her ride on and off of my cock, feeling how my cock spread her wide.
Then I started to thrust, slowly at first, and she stopped for me to find my own rhythm, pulling myself almost out, then watching-feeling myself slide back in.
“That’s so good,” she purred, darting her hand back to buzz her clit again.
“Give me that,” I said, reaching under her to follow her hand, pinning her with my body. She gave it over and I touched it to her, still buzzing. “Here?” I asked, missing on purpose.
She shook her head. “Nuh-uh.”
“Here?”
She laughed and shook her head again.
“Here?” I said, winding it up through her folds against her clit.
She whined instead of answering me.
I caught my other arm around her chest and leaned into her, forcing us to fall forward together, me still fucking her, my chest pressed against her back, covering her bodily against her bed.
“I like you here, trapped,” I said, kissing her neck as her hips kept pulsing between my cock and where I held her toy.
It was like I was taking her from the front and behind both at once.
She reached a hand back to run through my hair and started to writhe beneath me, to give me more of her ass, and then grind against the vibrator, back and forth, back and forth.
“I want to feel your ass come around me, Thea,” I said, catching her earlobe to suck. “I want you to fuck yourself with my cock until you can’t help but come,” I whispered. I wanted to do anything, everything, to feel her lose herself again around me.
“I want that too,” she whispered—and underneath her my hand found a breast and pinched its nipple and she gasped, as my lips found her neck again. “Jack.” Her free hand wound in the sheet beside me, as her other hand reached back to clench in my hair. “This is so good,” she moaned.
I utterly agreed with her, and hoped to hell she realized how amazing we were together. I knew I’d be dreaming about the past twenty-four hours for the rest of my life—I wanted to make sure she would, too.
I pulled the toy away from her clit and she made a petulant sound.
“If this is our last condom—I don’t want you to come yet—I don’t want to stop fucking you,” I whispered as I stroked inside her, because it was true.
Her hand in my hair pulled and she twisted to look back at me. “Then don’t,” she whispered back.
I held her tighter, my arms wrapped around her, one hand against the softness of her breast, the other holding the toy as my thrusts ground her against my knuckles.
And I closed my eyes, feeling my cock sink into her, again and again, savoring the delicious tension as it pulled out, the perfect sensation as it pressed back in.
How was some other man not here instead of me?
How was I the man taking this beautiful woman in her glorious ass?
I opened my eyes again and saw her still watching me, knowing that I was only barely still in control, and it was time.
I opened my palm with the toy and planted it against her clit again.
“I’m never going to stop fucking you,” I whispered in her ear, and realized it was true—even without her there, from here on out, I’d always be reliving the last night in my mind.
I took her ass like I owned it, in strong steady strokes, and on each downbeat pressed her clit solidly into the toy in my hand, and I felt her body start to tremble.
“Oh my God—Jack—this time—please—don’t stop—I can’t take it if you stop—"
“Never,” I promised, taking her hard, grinding her into my hand with each thrust until she gasped like she’d been surprised.
“Jack—Jack! Oh!” she shouted, curling into the mattress and into my hand.
She bucked beneath me with the force of her orgasm, and I had to follow her.
I sped my thrusts up, and she arched back to give me more of her ass and that was it, her offering her ass to me, because she wanted me to take it, she wanted all my load—just like I’d always dreamed—
I came with a shout, my whole body lurching forward with the force of my orgasm as I planted my cock inside of her to take it from me. My hips twitched spasmodically against hers, my thrusting mindless, as I could feel my balls lifting and pumping as she drained them again.
I collapsed on top of her, feeling her breathing raggedly beneath me, until I rolled over, my cock sliding out of her to drape against my thigh. “I have never, ever, had sex this good.”
She laughed melodiously, rolling onto her side. “You should never tell a woman that.”
“Why?” I asked in all innocence.
“Because then she knows,” she said and gave me a mysterious smile before snuggling up against me. I didn’t press the matter, and not long after that we were asleep again.