Gender: Male Age: 20 Location: Manhattan
It started in the shower.
The kids slept until it was light out, their internal clocks finely tuned to the sun, but Jack and I had to roll out of bed long before then. He always hit the snooze button at least twice, and I usually snuggled up to his broad, strong back until he rolled me over to reverse spoon and pulled my hips in to him so I could feel how hard he was for me. There wasn’t a day on earth that Jack didn’t wake up hard. It made me smile and wiggle back against him, all sleepy eyes and long limbs.
It was a very rare occasion when we had time for morning sex in our rush to get everything ready and everyone out the door on time. Still, he loved it when I reached back and squeezed and tugged on him in those drifting moments still caught between sleeping and awake. I liked to imagine what he’d been dreaming about as I reached back to stroke him against my ass— what new flavor of the feminine had entered his unconscious during the night—a dark, exotic beauty; a long, slender blonde, some cool drink of water; or maybe a curvy, fiery redhead like me?
It was an awkward angle for me to do for very long, and sometimes he took his cock in his hand and rubbed it up and down the crack of my ass, or just moved the head against the soft skin of my cheek. Once in a while, if I’d forgotten and worn panties to bed, I’d curl my arm behind my back and pull my panties up tight. He loved to see me “bound” that way, even just the suggestion, my wrist twisted in the material and resting against my lower back, my bikini panties pulled taut and thin as a thong between my cheeks.
There were mornings when he felt more urgent, when he grabbed my hips and shoved his cock between my ass cheeks, rubbing it there, hard. Those mornings he’d press into me and stroke his cock against my ass, his breath coming faster against my neck, his cock an iron bar, hand pistoning up and down his shaft. I loved listening to the sweet flesh music of his hand on his cock. It made me moan and wiggle against him as I reached back to spread my ass for him—god, he loved that!—and arch my back so he could aim his cock at the tender little rosebud of my asshole. That usually sent him over the edge, my hands opening myself to him that way, and he would grunt and thrust and spill his cum deep into the crack of my ass.
Those were the days I really needed a shower.
I was the queen of fast showers, with a litany of things to do that day already running through my head. He was a shower lingerer, just standing for long moments under the water, soap in hand, while I was all-business, scrubbing and rinsing and shaving in record time.
Sometimes he could get me to linger with him, distract me from the endless lists of stuff to accomplish in my head. That’s where it really started, although I recognize it now as a progression from our early morning ass-stroking sessions. It happened more on mornings when he was still excited, those mornings he didn’t masturbate to completion in our bed, those mornings when his cock revived the minute soap and water were applied.
Those mornings he would take my hand and put it on his cock as he washed it, slick and hard and throbbing, something he knew never failed to interest me. I couldn’t
often resist a hard cock thrusting into my hand, even when there were other things to do.
Still, I would protest. “Jack, we can’t. I forgot to make lunches last night.”
“How about a little breakfast first?” He’d kiss me and then rub his fingers over my lips and I would know immediately what he wanted.
I loved sucking him off in the shower, although I didn’t often get the opportunity. I loved kneeling in the needling spray, gulping down his cock and his cum, nearly drowning in the cascade of water over my head as he shoved himself into my mouth. My pussy got wet just thinking about it.
“Jack, we can’t, really,” I’d tell him, finishing rinsing my hair.
“Then just let me stroke myself against your ass.”
And that’s how it started, me bent over in the shower, my hands braced against the tile, my legs spread, the hot water running over my ass as he kneaded my flesh, spreading my cheeks open and rubbing his cock up and down my slit, teasing my pussy and my clit, before he began stroking himself right against my asshole.
But it didn’t end there. Oh, no. That’s just where it started. One morning, he put his finger there, a gentle probing, a tickling tease. I shied away at first, embarrassed. For me, there was a grave difference between his cock, too enormous to gain purchase against that tiny hole when he stroked it there, and his finger, which seemed to have a sly intention. Of course, I was right.
His finger, slippery with the soap he was using to lubricate his cock, slid into my asshole. When I hissed at him and told him no, he didn’t take it out. Instead, he slid in another, increasing the pressure.
“Shh, Charlie, it’s ok,” he murmured to me, using the diminutive form of my name as a comfort measure as his fingers moved, slow, in and out.
“Jack!” I squealed as his fingers moved a little deeper. My face was flushed, and not just from the heat of the water in the shower. “That’s…that’s nasty!”
He chuckled, sliding his other hand between my legs, teasing my clit with one finger just the way he knew I loved. I moaned and arched my back, forgetting about what he was doing in my asshole for the moment.
“Does it feel nasty?” he asked me, rubbing my clit and fucking—yes, he was fucking my asshole—in a slow, easy motion and I was caught wiggling between shame and pleasure.
That first time, shame won out. I pulled away from him and got right out of the shower, drying off and not answering his calls, even when he stuck his head around the curtain.
When we talked about it later that night, as we were falling asleep, I blushed red again, telling him I didn’t want to do anything like it, and that if he insisted on pushing it, we could just shower alone—but the threat sounded hollow, even to me.
And it was. It was only a week or so before he did it again, slipping his finger into my asshole as I was bent over in the shower. This time he’d waited, getting me fully aroused before beginning his gentle inquiry. That time, I didn’t get out of the shower, and he came all over me with his fingers buried deep inside my ass.
The next time, I came so hard my ears were ringing, rubbing my own clit as he fingered my ass and pussy all at once. That time I turned around and sucked him off, as eager to have his cum as he was to give it to me.
The time after that, we crossed into entirely new and frightening territory. I was used to his fingers now, two, sometimes three of them fucking me at once. I liked rocking against him as he fingered my pussy and my ass together, filling me completely.
When he pressed the head of his cock against the tight ring of my asshole, however, that’s where I drew the line. Again, I hurried out of the shower right away, dried off and ignored him for the rest of the morning, no matter what he said. It wasn’t until late that night, the darkness providing enough cover for my shame, that I told him how scared I was, and he held me and rocked me and told me how much he loved me.
And that’s how I got here—my ass in the air, my cheek resting against the cool sheet, two bottles of K-Y on the bed and Jack kneeling behind me, his cock slick and aimed toward a place I never would have believed I could let him enter.
“Wait, wait, wait!” My hands pressed his thighs, my eyes closed tight. The head of his cock positioned right there. I was tense and couldn’t seem to let go.
“It’s ok, baby.” He just rubbed me there, a familiar feeling. I let myself relax a little, enjoying the feel of his KY-slick fingers stroking my tender flesh.
“Ok, ok.” I arched my back, taking a deep breath. I felt him press the head of his cock there again. The tip of him was easy at first as it met my soft, puckered opening, but then his engorged flesh stiffened and strengthened, coming up against a tight band of resistance. “Ohhhh wait, wait!”
He stopped, but he didn’t pull back this time. I felt my own refusal, my whole body a bright red, flashing neon “No!”
“Play with yourself.” His hands gripped my hips, cock pressed tight against my asshole. He wasn’t giving up an inch now.
I reached between my legs, my fingers parting my lips. In spite of my fear, my pussy was swollen, wet, my fingers sliding easily among the delicate folds.
“God, you have such a beautiful cunt.” His voice was full of lust and I knew he was watching me finger myself. I circled my clit with my index finger, large circles growing smaller, zeroing in at a slow, steady pace. A familiar tingling began between my legs and I lost myself in the sensation, working my fingers faster now, my breath hot against the sheet.
Jack pushed in a little further and I gasped and moaned. “Ohhhh no, honey! Wait, wait, please!” I begged him.
“Don’t stop touching yourself.” He pushed in a little harder.
I writhed beneath him. “Ohhh baby, honey, god, I can’t take it! I can’t take that much, please!” His cock felt three times its normal size. I felt my body rejecting him, wanting to expel him, find a way out of this. “Ohh Jack, oh my god, please!”
“It’s ok.” He was panting, as if what he was doing required a great deal of effort. I didn’t know if it was the holding back or the pushing in. “Keep rubbing your clit.”
I did, my fingers a sweet distraction from the hot throbbing steel rod pressing into my behind. “Oh please, please, please, please, please.” I was begging him, and I didn’t even know what for. Some sort of release?
“Just a little more,” he whispered and I felt a slight pop as my ass opened to accept the entire head of his cock.
“Ahhhh god!” I was shaking, my face flushed. “No more, I can’t!”
“That was the hardest part.” His hands stroked my ass, my hips.
My body began to adjust to the feeling of his cock stretching me open in places it wasn’t used to being distended. “Go slow. Please. Slow.”
“Ok.” His voice was a whisper, and he pulled on my hips, giving himself some leverage.
“Slow, slow, slow!” I felt him pressing deeper into me—the thin, tight band of flesh that had kept him at bay had now been pushed past, over the swell of him. He had a straight shot toward my center now.
“Jack, ohhhh god, it’s so much!” I couldn’t believe how vast he felt in me.
“Can you take more?” He squeezed my hips, his hands holding me steady.
“Yes.” I breathed it into the bed. “Yes. Go ahead.” He got himself another inch, maybe two. “Wait, wait!”
“Does it hurt?”.
I shook my head, panting with the effort to take him into me. “No. I just… I have to get used to feeling it. So full.”
“More?” His hips rocked a little.
“Yes.” I pressed back against him, aching to feel the saddle of his hips against my ass. “Come on, that’s it. Deeper. Is there more? Yeahhh, I can take it, baby. All the way in me.”
Jack moaned as he sank into my flesh, buried now, to the hilt.
“You’re in my ass.” I was filled with wonder. “Oh my god.”
“I’m gonna fuck your ass.” His voice sent a shiver through me.
“Oh, honey, easy!” My mind had only just gotten wrapped around the idea of penetration—I hadn’t made it to the idea of being fucked yet.
The delicate flesh around my asshole flowered open as he began to pull back, easing almost all the way out of me. I felt the tip of him, the ridge which had felt so impossible, easing out, and then back in.
“Slowwwww.” My thighs shook. “Ohh honey, please, please.”
He was moving now, in and out of my ass. “Oh, it’s so tight. Charlie your ass is so tight!”
“Do you like it?” I pressed back against him, feeling how hard he was inside of me. “Do you like fucking my ass?”
He groaned, driving harder against me, and I met his thrust, rocking back. I loved the feel of him grinding into me, the sound of his grunts and moans. His lust, his pleasure, sent me soaring, and my fingers moving faster and faster over my clit.
“Harder,” I whimpered, my fingers wet and slick with my juices as I circled my clit. “Ohh, please, fuck me harder!”
He did, his balls slapping against my pussy, his fingers using the bones of my pelvis like handle grips, pulling me back to him again and again. I loved feeling him ram into me with such force, with a slick, wild abandon that left me panting and moaning.
“Oh, fuck my ass!” I felt my orgasm building, his cock a driving force against my ass, my fingers working my clit for all I was worth. “I want you to come in my ass!”
He groaned at the words, and I felt him beginning to let go, his movements filled with purpose and longing now, heading toward an ecstatic finish line.
“Oooo baby, you’re gonna make me come!” I arched my back and buried my fingers in my pussy as I shuddered with it, my thumb still rubbing on my clit, sending sweet waves through my body as I bucked and writhed beneath him.
He was just behind me, sliding me forward onto the bed, my knees collapsing as he plunged into my ass with all of his weight. His whole body quivered against the length of mine, his cock a throbbing wet pulse as he spilled waves of his cum into my depths.
When I was later tucked against him, my bottom still throbbing, I didn’t wonder anymore how I got there as he petted me and held me and kissed my forehead, still flushed and sweat-dampened. For once, I didn’t feel rushed or out of time. As I looked back at our journey toward that moment, I knew just how I got there—and I was filled with him and felt complete.
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