Chapter Ten: Jude
“Okay, I’m going to lie down at the foot of the bed and you get on top of me,” Wynn said, talking with his hands. Since his cock was the longer of the two, it was decided that he should be in my pussy while Holden slid inside my ass—or attempted to.
I won’t lie. I was nervous as fuck at the prospect of having both their cocks inside of me at once. I mean, I’d had one in my mouth and one in my pussy several times already. And I’d had anal sex lots of times. I loved anal. In fact, it was right up there with vaginal and oral sex in my book. Sure, it was a little uncomfortable a little at first, but when things got lubed up really good and everyone took their time, it could feel incredible. I could orgasm just from anal. No lie. I had done so many times.
But now…
My heart was beating faster than normal. I could feel it pounding in my chest. Adrenaline was coursing through my veins. I wondered if this was what it felt like the first time you stood at the open doorway getting ready to jump out a plane. It was both exciting and a little scary. At least I wasn’t in danger of splattering all over the ground, I told myself. I mean, there was that, right?
I loved anal, but now I was looking at having Wynn’s twelve-inch cock in my pussy, or however many inches I could take in. And Holden’s ten-inch cock in my ass, or however much. Nervous or not, just the anticipation of it was making my juices flow like a raging river. Yes, I was a little nervous, but I think the guys were even more nervous than I was.
Wynn lay back on the bed with his ass at the edge and his big cock sticking up like a branchless tree. His cock was not only long, but girthy and thick, mapped with veins. It was a beautiful thing to behold. And to hold. I wrapped my fingers around it and gave it a few strokes as I climbed on top to straddle him.
“Okay, you know how this part works,” Wynn said, putting his hands on my hips to slowly lower my pussy onto him. I paused for a moment when I felt the bulbous head press against my hole, but I was already super wet, so he slid in without a problem.
“Ohh… that’s so… nice…” I said, lowering myself onto him until I felt the tip of his cock hit my inner wall. I moved up and down on him a few times to get us both good and wet. Already, I was gushing like a leaky pipe.
“Now, me,” Holden said from behind. He moved to the edge of the bed, and with Wynn’s cock inside me, I pushed my ass out and invited Holden to join our little party.
Holden had brought a tube of KY from the bathroom and stood now slathering his cock with it. With enough KY, you could drive a Buick through the eye of a needle. In this scenario, my pussy was the eye...
“Let me grease you up, my dear,” Holden said with a grin. He squirted a glob of KY on his fingers and lubed up my ass good, rubbing the jelly around my hole and dipping in his finger a few times for good measure. I grunted and moaned each time his finger slid inside. When he decided I was ready, Holden put his hands on my ass and positioned the head of his cock at my anus.
“Just breathe,” Wynn said, looking up into my eyes. “And yell stop if you need to.”
“Yes,” Holden said, giving my ass a playful squeeze. “Do not let us hurt you.”
“I’m fine,” I said, forcing a smile for their benefit, trying to hide my nerves. The feeling of Wynn’s cock inside my pussy was overriding my fear. As I slowly slid up and down on Wynn’s pole, I gave Holden a nod to proceed.
I closed my eyes and breathed slowly in and out, focusing on the pleasure Wynn’s cock was already giving me. I knew from experience that gritting my teeth and holding my breath was not the right thing to do. Anal sex is about muscle control, relaxation, breathing, going slowly. Holden had done this many times. He knew what he was doing. I trusted him completely.
When the head of Holden’s cock slid into my ass, I gasped a little. Not because it hurt, but because it felt really crowded back there with Wynn’s cock already in my vagina. Holden asked if I was okay and I said yes. Keep going. Proceed. Please…
Holden slid in a little more, then a little more. When he was just at the right spot, I said, “There… right… there… oh… wow… do I feel… full…”
“Are you okay?” Wynn asked.
“Yes, just go slowly…” I said.
We started slowly at first, moving as one. As Wynn moved his hips up and down to fuck my pussy, Holden moved his hips in and out to fuck my ass. It didn’t take long. Soon, we were all in rhythm and I was convinced that if my heart didn’t stop, I was going to have the best orgasm of my life.
“Jeez… you’re so… fucking… tight…” Wynn said, his fingers digging into my hips. “Damn… Holden… gimme some room…”
Holden was trying not to laugh and not to cum. I knew my pussy was tight, but my ass was super tight, clenched around his shaft. And it had to feel incredible when the head of his cock slid in and out of my ass. His fingers pressed into my ass and he sped up a little, still being careful not to go to deep.
“Fuck… I can’t… fuck… hold it… anymore…” Holden said, his motion becoming erratic as the orgasm started to build. “Fuck… I’m gonna… cum…”
“Me… too…” Wynn said. I smiled. I was making them both cum at the same time. There had to be some kind of merit badge for such an auspicious accomplishment. I could only imagine what that little graphic would look like.
“I’m… oh… shit… shit… cumming… yes… yes… yes…” I moaned and forced myself not to jerk too quickly. I had two very large cocks inside of me. One wrong move on my part and we’d all end up in the emergency room trying to explain what happened.
Luckily, all three orgasms hit at once.
Our bodies twitched and jerked in unison.
Two seconds… three… four…
After a moment, we all blew out the breath we had been holding and collapsed in a sweaty, goopy heap on the bed.
A few minutes later, without saying a word, we all fell fast asleep.
For a very long time, I would remember this as the best Saturday night of my life.