A very confusing evening

The rest of the evening rolled on pretty well and the more time I spent with Kate the more I grew to really like her. The feelings of physical attraction that were already in place were complimented by a growing interest in her on a personal level. She was shy at first but once the ice was broken I found her to be very passionate person with a kind of innocent wisdom about her that I found to be endlessly charming.

And more to the point, I could see that the attraction wasn’t one-sided. The whole evening I caught her lingering glances, the way her eyes would roam down my body towards my Trunks when she thought I wasn’t looking. She was clearly too shy to take the initiative, but I could tell that the interest was there and decided to roll the dice and make the first move.

“Hey...”

Kate turned to look at me. “Yeah?”

I leaned in and captured her lips with mine. For a split second I felt her tense up, but it was a fleeting thing and soon I felt her reciprocating the kiss, her tongue wrestling with my own. Instinctively I pulled her closer to me, my hand coming up to cup her breast whilst hers travelled down my trunks to gently take hold of my erection.

“You really want this?” She asked in a breathy whisper, “you really want ...me?”

Even through the haze of lust I could see the uncertainty on her face, the self-doubt that had weighed her down for so long. “Kate,” I said, taking her face in my hands, “You’re funny and smart and crazy hot, I really like you, and I was a fucking idiot for not doing anything about it sooner.”

There was a surge of emotion in her eyes and suddenly we were kissing again with renewed passion. She began to grind on me and my hands caressed every inch of her body. My hands found her ass and I as I palmed her booty, I was reminded of David up in my room and the way his ass had felt under my hands. It was an **** thing, but my dick twitched at the memory and for some reason I felt a greater surge of lust.

What came next was automatic. I lifted Kate off my lap and leant her against the edge of the pool, my cock rubbing against ass insistently, all the while kissing along her neck and gently caressing her tits.

“Alan?” She asked in a daze, “what are you doing?”

“I need you babe,” I breathed, kissing her neck, “I need you right now.”

There was a moment of hesitation. “I’m a virgin...” she paused for a moment, reached up and caressed my face, “be gentle, ok?”

“I promise I won’t hurt you.”

I lined myself up and slowly parted her lips with my cockhead, easing myself in with the utmost of care. I’d never taken someone’s virginity before, but I’d heard enough horror stories to know that I’d have to be gentle and so I kept my movements slow.

It was awkward at first, but as we went on I could feel her easing up, her intakes of breath slowly replaced by outright moans of pleasure. I took that as a sign and picked up the pace, lost in the tight wetness that was hugging my cock.

“Fuck,” Kate cooed, “Oh fuck ... you’re so good!”

“You like it?” I breathed, slamming away, “you like this cock?”

“I need it,” she whined, meeting every thrust with her cushiony ass, drunk on pleasure, “please babe..ugh...keep going!”

Casually I brought a hand to caress her ass as I thrust away, and once again David came to mind. Only this time he was in Kate’s position, bent over in front of me with my cock stabbing into him. It was David who I was fucking, David who was moaning from the onslaught of my dick. I found myself thrusting harder, faster, lost in the fantasy of fucking my friend.

Our groans were a chorus until suddenly it all got too much for me and I found myself unloading deep inside. “Fuck...fuck babe, I think I love you.” We stayed like that for a few moments, breathing heavily until the haze of lust past and I realised I had just cum inside Kate’s unprotected pussy.

About a dozen conflicting emotions went through my mind at once. Primarily it was fear that I had just blown my load inside a girl knowing full well she was very likely to not be on the pill and the fifty million concerns that could bring. But there was also the staggering confusion I had felt about thinking of David. What the actual fuck? I was with Kate, I had been very attracted to Kate, so why did my mind drift back to David? And why had I cum harder than I ever had before?

I was still grappling with these thoughts when Kate pulled herself free of my cock and turned around to regard me. “Did...you mean that?”

“Yeah,” It was an automatic response, and not totally a lie. I certainly liked Kate a lot, perhaps more than I did any other girl. That was close enough, right? “Yeah, I do...I love you.”

Her eyes glistened with tears, but she beamed up at me with a watery smile. “I love you too,” she sucked in a shaky breath, “I... I think I’ve loved you since we were kids and I was always too shy or too stupid to say anything and if only I had-” she caught herself and took my hands within her own. “This...is the best night of my life.”

Eventually as the night wound down Kate went on her way, but not before exchanging numbers and promising to see each other again soon. I was still trying to process everything that happened when I found myself face to face with Amy.

“So you went all in and popped her cherry,” Amy’s eyes were predatory as she looked me up and down, “Honestly I’m surprised, I figured David was more your type.”

I felt my temper flare, “Listen you twisted bitch I’m done playing games with y-”

She took two steps and grasped my dick tightly through my trunks. “Oh babe, you can try and pull the outrage routine all you want, but we both know you love my games,” maintaining her vice grip, she leaned in close to whisper into my ear, “And they’re just beginning.”