Theo and I had gotten more and more daring this last summer before he headed off to college. Little teases and flirts between us had started years ago, as we both hit puberty right around the same time. Each of our curiosity about the opposite sex had grown, and we’d learned so much just from “tell me – tell you”, and then ‘peek for peek’.
This year, though, for a sort of graduation present I’d contrived to flash him full-on naked strolling the hall from the shower to my room right in front of his door, having ‘forgotten’ a towel. He found a way to reciprocate, giving me an eyeful of him as he stripped from sweaty yard work – though I’m pretty sure lawn mowing wasn’t what had turned him on.
The summer simmered hotter as we got bolder with each other, always aware of where Mom and Dad were so we never got too far.
And then, on a hot July night, Mom and Dad were out late. And Theo and I had just finished dinner. I made sure to bend over too far loading the dishwasher in my short shorts, and he pinched me on my ass, hard, as he passed to the sink. I chased him to his room – even though he’s 50 pounds heavier than me. He turned on me then with a look of ‘what now’?
I’d stopped short when he turned, and stared at him a moment. Then slowly, deliberately, I walked past him – not pinching his ass – and sat on his bed.
“Know what I did here last time you slept over at Rick’s?”
He shook his head no.
I hesitated only a second, biting my lip, then stripped off my shorts and panties and peeled my tank top off before I could think too much about it. Watching Theo, who stared at me slack-jawed, I opened my legs and started playing with myself. I was already wet, and my fingers slid easily along and into my slit.
Theo looked like a man in a trance, his eyes tracing down my body to fix between my legs, watching as I fingered myself. I don’t think he was conscious of stripping himself, and taking his hardening cock in his own hand to start jerking it.
Oh, god, he was beautiful, and hot. I think I moaned then – not just from my own pleasuring, but from appreciation of him. His cock was bigger than I’d remembered, and it was all hard – for me.
We watched each other masturbate, breathing louder, moving faster until I gave a little cry and came with my fingers sliding over my clit. I stared at Theo until I had to close my eyes and arch into the pleasure.
Coming down from my peak, I stretched languidly, sliding my hands up my sides just because it felt good. I watched Theo, whose stare remained fixed on me. He was so close, pumping his shaft hard.
And then he let loose. I’d never truly seen him jerk off before, other than quick peeks, and I’d certainly never seen him cum. The white stream shot from him, and even though he was a good few feet from me, to my surprise it splattered right on my tummy, almost to my belly button. As he gasped and made the sexiest grunting sounds, stream after stream arced and splattered hot against my skin, maybe 6 or 7 times. I wouldn’t have believed it if I hadn’t seen and felt it.
And I felt more, too. I’d just cum, and had just watched him do the same, but inside, something dark and molten wanted, needed, more. My gaze shifted slowly up from his twitching, still-hard cock, to Theo’s face. The look in his eyes… matched how I felt.
He took a step toward me and butterflies danced in my stomach as his cum dripped down my skin. Our eyes met as he took another step, the hand that wasn’t gripping the base of his shaft reaching for my hip.
I opened my mouth as if to speak, but I didn’t have any words as his eyes moved down my body. I followed his gaze, and watched my legs open wider as he guided his cock to me. A glob of his cum slid down my slit, and I shivered. Was this going to happen? Was this happening?
I don’t know what I was going to say, but I didn’t get past his name before his cock nosed into my slit and pushed inside me. And before I could catch my breath, Theo was lowering on top of me, his hand letting go of his cock to palm my breast. His lips against mine muffled my moan as his cock stretched me open and sank into me.
I kissed him fiercely, reaching my arms around his broad shoulders, raising my legs, heels against his muscled ass to pull him to me.
Until his cock nudged my hymen and I jerked a little and winced. Theo froze, then broke our kiss and raised his head, looking down at me, lustful, concerned, uncertain. I felt my love for him double in that moment, and my own lust triple.
I looked him in the eyes, and nodded.
“Yes.” I almost didn’t recognize my own voice.
I pulled his head down to kiss me again, and moaned “Yes” into his lips as he pulled partway out of me.
“Ye-” I screamed as he jerked his hips forward and pierced my virginity. But his lips were on me, and I was full, oh, God, so full of him. And Theo was fucking me. Fucking me! And it hurt, and then it hurt less, and then not at all, and then…
“Oh, God, Theo…”
“Don’t stop. Don’t ever stop.”
He didn’t. We didn’t. Not until I’d cum under him twice more. Not until he roared and buried himself all the way in me, cumming so hard I felt every pulse of his cock and jet of his semen deep inside.
After every last ounce of pleasure was wrung from both of us, he collapsed beside me and we lay panting and dazed for a long time. Then we looked at each other. I started with the giggles, and after he stared at me for a moment he started laughing too. We hugged each other close, sticky and messy, and laughed and kissed over and over, as if some great dam had broken and life was finally flowing strong and fast.
Clean-up was easier than you might have thought. Theo’s sheets needed a wash anyway, and a hot shower erased all outward signs of what we’d done. Inside, however, things were different. And when Theo came out of his shower, towel around his waist, I could see he felt the same.
“I gotta get the day-after pill tomorrow.” I told him.
“Oh fuck! Yes. I’m s-”
“Stop right there,” I put my hand over his lips. “I’m not sorry, you’re not sorry. I’ll take care of this, and I’m going to tell Mom I want to get on the Pill. We had The Talk a long time ago, and she told me that safe is better than sorry, so if I wanted it, she would say yes, no questions asked.
“Ok, but… right now you could be… we could’ve…” Theo’s expression was troubled, but also… desirous. It made me quiver.
“Maybe. Maybe, but I’m not ready. We’re not ready.”
Something was pushing his towel out from below his waist. I grabbed at where he’d tucked the towel in and pulled it away to watch his cock spring up and finish stiffening.
“Not ready for that, maybe. But ready for something,” I said.
“Mom and Dad should be home soon,” Theo said.
“Not for a while, I bet.” I took hold of his shaft with one hand – God it was hot, and hard – and turned back to my room, pulling him behind me. My sheets needed changing, too. And the thought that we could’ve, that we might have already… I was more than slick, near dripping by the time I’d thrown him on my bed and straddled him.
The rest of the summer, well, what do you expect? Theo and I have been fucking at every single opportunity. As the new school year approaches, we’re still not sure what we’re going to do.
But we’re planning.