(Author's notes: This is Chapter 2 of a continuous story. It will make the most sense if you read Chapter 1 first.)
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We began doing some weekends where both nights were trio. One Friday night, we were all extra-tired from work, so we abandoned our plans for going out, had a pizza delivered, and retired to bed. No one was too tired for sex, though. As we morphed from position to position, I noticed that several times, as one of them cupped my ass, or stroked my vaj, a fingertip would "happen" to brush across my brown star. Neither of them actually tried to penetrate my ass, but they were definitely checking out how I would react. I didn't brush them off or twist away from them, but I did, of course, notice.
Saturday morning, I awoke first, and as they slept on either side of me, I made a decision. I didn't know if I would ever be able to enjoy having a cock in my ass – it had never worked for me before – but I decided it would not be from lack of trying.
That night we had a party to go to, and it was a good one, so we were out late. We got home, took quick showers, and settled into bed. Jeremy was the first to flick his finger across my asshole. He immediately said "Whoa!"
Chad said, "What?"
"Check this out!"
Chad put his finger in the same place, and said, "Whoa!"
What they were whoa-ing about was, after my shower, I lubed my ass. Heavily. I concentrated on depth, but some lube accumulated around the pucker. That's what they noticed.
They had huge grins on their faces. "Hold it right there," I said – I definitely had their undivided attention.
"The key word here is SLOW. I'm willing to try it back there, but I'm a little freaked out about it. Only a few of my friends have ever admitted doing this, and they hated it. HATED it. As in, won't try it again." I paused for effect. "Ever."
I let that sink in. "I've been reading about it online. The key seems to be working up to it. Slow. Gentle. If I say stop, you have to promise you'll stop."
I looked up to see two extremely earnest nods.
Chad was on his back, and I straddled him, but stopped short of guiding him into my pussy. I glanced over my shoulder at Jeremy, said "One finger, gently," and kissed Chad. Jeremy slid his finger between my cheeks. I spread my knees further to grant him easier access.
He found my rosebud and teased it, then settled into the center. Ever so gently, he pushed in, just up to the first knuckle. He lingered a few seconds, slowly wiggling it in a circle, and withdrew. He pushed back in, wiggled another few circles, and withdrew again. He massaged the outside, caressing the wrinkles around the opening. I was amazed - no one had ever played with my ass so gently before, so I never knew how sensitive it is, how erotic, how HOT it could feel.
Chad kissed me deeply, massaging my bum-cheeks, keeping them spread for Jeremy. Jeremy slowly painted the inside of my ass, gently stretching the sensitive flesh. Waves of pleasure rippled outward from his finger. I sighed in pleasure.
Jeremy pushed his finger to the second knuckle. I gasped, and concentrated on accepting the intrusion. He withdrew it to the first knuckle, and pushed it back in to the second, leaving it in a bit longer before withdrawing to the first knuckle. He repeated that several times, that timeless motion, in and out. Chad continued massaging my ass, also rubbing my back, kneading the length of my spine, keeping me relaxed.
Jeremy picked up the pace of his two-knuckle fucking. Pleasure radiated from his finger throughout my body. He pulled out, stroking around the edges, caressing the sensitive wrinkles. He re-entered, in and out, around the rim, in and out.
By now I was anticipating what he did, and began pushing back against his hand, accepting the penetration, aiding it. He stopped and slowly pushed it the rest of the way in, a fraction of an inch at a time. I knew it was just one finger, but I felt filled to capacity back there.
He remained patient, at first only stroking from his palm out to the second knuckle, then holding it all the way in and caressing my insides in slow circles.
I was still straddling Chad, my slit massaging his erection. Although I hadn't taken him inside me, as I thrust back on Jeremy's finger, my clit traced the base of Chad's cock. As Jeremy increased how deep he finger-fucked my ass, I rubbed more across Chad. Jeremy penetrated my ass faster, Chad kneaded my butt, my clit slid over his hard-on, Jeremy stroked faster and deeper, all the way out to the nail now, and I came.
I never expected that, never felt it building. I ground my clit down on Chad's dick, Jeremy kept his finger buried in my ass, vibrating the palm of his hand against my butt. I fell into a deep abyss of pleasure, every nerve in my body singing with warm, glowing delight.
I peaked, rolled off Chad, and floated back to earth, with these two incredible guys on either side of me. When I was able, I staggered to the bathroom, applied a fresh thick coat of lube, and moistened a washrag. I cleaned Jeremy's hand, kissed him deeply, and croaked "Good job" with what remained of my voice. I turned and kissed Chad, saying "You too," and collapsed between them.
Before we took my ass to the next level, I blew each of them. I wasn't ready to take a dick back there that night, but I wasn't going to leave my guys high and dry. We relaxed for several minutes afterwards, catching our breath, anticipating what was next.
I rolled Jeremy onto his back, straddled him, but stopped short of guiding his cock into me. I glanced over my shoulder at Chad, and whispered, "Two fingers." We were just getting started...
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Sunday noon we had a cook-out to go to. We were supposed to bring potato salad – we make a wicked version with new potatoes, bleu cheese, and bacon. We hadn't gotten it made on Saturday, and obviously there wasn't anything store-bought that was equivalent, so we had to get up early Sunday morning to prep the food. The party was fantastic – great food, great friends. We got home late in the afternoon.
We had another cook-out to go to that evening, but we weren't committed to bringing a dish. Somehow or other, with what awaited us in bed, we didn't make it. Obviously, the guys were looking forward to it. I was too, although somewhat apprehensively. I mean, there was no doubt that we were going to finish what we started. By "we," of course, I mean me – I was going to take a dick up my butt.
Based on last night, the guys were going to be patient and sensitive. Still, the bottom line (pun intended) was, I was going to have a live cock up my ass, maybe two, and they were going to be as hard as they ever got. I was nervous, but mostly in a positive way, because, again, based on last night, I was definitely going to like it. I was probably going to LOVE it.
I wondered how much bigger than Chad's two fingers a dick was going to feel. One finger was wonderful. I never knew what a pleasure center my asshole could be – obviously it's teeming with sensitive nerve endings. It gave me a deep, sensual glow throughout my body, shimmering over me like a spring breeze blowing across a field of tall grass, except about a bazillion times stronger.
Two fingers, however, were more of a challenge. There was considerable stretching involved. Chad was extremely gentle, he did everything to keep it comfortable, but it was a strain. He stayed patient, though, working gently until I got used to the larger size. The more I relaxed, the more pleasure I felt. The larger intrusion provided a much more deeply sensuous payoff.
So, how much more extreme would it be to take a full, live cock? I was about to find out.
The guys placed me on my side, with my butt hanging slightly off the edge of the bed, my knees drawn up near my chest. Chad lubed his longest finger, and eased it in as deep as it would go. He worked it in and out, massaging me, relaxing me, reminding me of the spectacular sensuality of that part of my body.
Jeremy showed me two lubed fingers, and placed them against the entrance. "I'm going to push in now," he said. "It'll be easier if you push back. I don't mean squeeze shut, that's different, but push, like you're trying to poop them back out." It sounded strange, but he was right, pushing actually helped keep me from tensing up and blocking penetration. Meanwhile, Chad washed his hands, then settled in front of me and gently stroked my face.
While Jeremy went deep and heavy with his fingers, stretching the limits of my comfort back there, Chad kissed my nipples, working them over with his tongue, amplifying the ripples of pleasure emanating from my ass, distracting me from any distress back there.
Jeremy was getting quite intense with his fingers, gripping my hip for leverage, going deeper than Chad went last night. He reached a new depth, stretching me hard, and gripped my ass with both hands. "You're doing great, baby, that's almost half."
I was dumfounded. That wasn't fingers...
I was seriously pissed off, for about a tenth of a second, until I realized he had done an amazing thing. Yes it was deceitful, but by not doing what I thought, he kept me from tensing up, which I would have if I had realized he was going in with the heavy artillery.
He more than made up for the deception by being so completely attuned to me. When he felt me react to the realization that I had more than fingers up my butt, he paused, leaving his cock in, letting me adjust to it. When I relaxed, he resumed stroking, slowly at first, barely half an inch. When I didn't tense up, he slid in a little more. After a minute or so, he was back to slowly pulling it all the way out to the tip, and pressing it back in.
I asked him later, "How did you make it feel so mild? I mean, you were thrusting into me, and you were as hard as I've ever felt you, but you made it feel gentle, not at all invasive."
