Decisions Decisions Ch. 02

(Author's notes: This is Chapter 2 of a continuous story. It will make the most sense if you read Chapter 1 first.)

: : : : :

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...

: : : : :

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."

"I put all the energy into the out stroke, not the in stroke. It takes a lot of concentration, it's instinctive to put the oomph on the 'in,' but that would have been uncomfortable for you."

He gradually increased the depth. Occasionally I'd flinch, and he'd pause, hold it in place, letting me stretch around it, adapt to the size. My universe had now shrunk to the tiny area between my butt cheeks. His cock radiated a deep warmth, relaxing any part of me that protested the intrusion. He knew exactly when to pause, and when to resume pumping into me. He always started back with tiny strokes. He'd work back to where he had been, and only go deeper when he sensed I was ready.

Something I never expected was that my clit got direct stimulation from being penetrated back there. I was concentrating on the sensation of Jeremy's well-lubed dick entering my butt, with no expectation of cumming. My clit, however, began to notice that my lips pulled tight over it every time he thrust into me. I was amazed to feel that familiar wave of an approaching orgasm. It got nearer, it grew and grew, I was almost there, I was so close, but it stalled. It lurked just out of reach, teasing me, a wave that never quite broke.

I had been holding my knees together, maximizing his access to my ass, but I lifted the top knee slightly, enough to get a fingertip onto the top of my slit and slip it under the hood of my swollen, energized clit. I rubbed slowly across it, and that was all she wrote – I exploded into an all-consuming orgasm. It felt like every muscle in my body tensed, every nerve singing the praises of having a dick in my ass.

Jeremy told me later that he was so focused on keeping me comfortable, he didn't expect to cum at all. "But when you came," he said, "You squeezed my cock so tight, I came at once." I felt him press up into me and hold there, quivering and quaking. I could feel each contraction as he shot his load into me. He collapsed across my back, holding me tight.

I wasn't up for a second dick up my ass, so I blew Chad. I barely remember doing it – all I recall is my ass, glowing in pleasure.

The math was getting more complicated: one dick plus one ass, squared, times one dick plus one mouth, squared, equals the square root of unexpected pleasure.

Sleep came quickly, with my incredible guys snuggled on either side of me.

: : : : :

That was rare, spending Sunday night together. We had never spent Monday night together on a work week. That was a momentous weekend, though, and we had unfinished business. Monday evening after work, they were back. We had a simple, light dinner.

We went straight to the bedroom. Chad proved to be just as attentive, gentle, and patient as Jeremy was. He started with the usual, one finger, then he actually went in with two fingers – I looked. He chuckled and said, "I didn't think that trick would work twice."

Which was fine, I wasn't nearly as tense – already succeeding once, I actually felt rather relaxed. Chad and Jeremy have very similar cocks, and while I've never done anything as crass as measure them, I think Jeremy's is slightly bigger around, while Chad's is a bit longer. Since Jeremy's had fit, I was confident Chad's would.

Chad eased his dick in, slow and gentle. I remembered to push back against him, which helped him get past the muscle ring. He slid in a couple of inches, and paused, making sure I was okay. He pulled out, barely an inch, and eased back in, letting me get comfortable.

Like Jeremy, he was gentle and attentive, pausing when I needed it. I was able to focus on how it felt – absolutely incredible. I loved it. I mean, I'm not saying that I only want to do anal from now on, but if it can always feel this freakin' good, I'm in. Often. Actually, they're in.

Jeremy settled in front of me, caressing my face, massaging my breasts, increasing the sensuality of the moment. I noticed he positioned himself where he could clearly see the cock entering my butt.

Chad did everything for my comfort that Jeremy had done. It was easier this time, less about pausing, more about actual fucking. He was so patient, my ass just glowed in pleasure.

My clit, though, realized from the start that there was opportunity here. From Chad's first stroke I felt the tug of my nether lips stretching across it, exciting it, driving it towards a climax. Chad told me later that he remembered what Jeremy said about putting the major energy into the out stroke rather than the in. He also said that he resisted burying his entire length into me – he found a depth that felt good for him and seemed comfortable for me, and concentrated on rhythm.

And oh, what a rhythm. On my side, I couldn't contribute much to the motion, but I did what I could to meet him half way.

With Chad's cock well established in the back, I pulled Jeremy forward where I could take him into my mouth. I wouldn't be up for a second dick up my ass tonight, and I could have blown him afterward, but I wanted my evening to end with my ass. To get him off as quickly as possible, I made my mouth the ultimate receptacle for his cock. I sucked and swirled, but positioned on my side, I couldn't actively plunge down over him. I pulled his hips forward, hoping he'd understand that I meant that he should thrust. He got it, and began fucking my face, building from gentle to aggressive.

Every few strokes, I felt a change in the angle of his cock in my mouth. I glanced up to see what it was, and it turned out he was leaning forward to see Chad's cock disappear into my ass. He must have liked what he saw, because in no time he groaned and launched his jizz into my throat. I swallowed, and he settled onto his side, where he had the best angle for watching my ass.

My orgasm was right there, just about to wash over me, when I felt Chad's cock pulsing as he launched his gooch deep inside me. I wanted to cum "naturally," direct from the stimulation of his cock, but I wasn't sure how long he'd keep stroking me after he came, so once again, I reached for my clit. I barely touched it, and exploded, waves of pleasure rippling over me.

The math kept getting more complex: hard dick squared, divided by mouth plus pussy plus asshole, equals unlimited potential for pleasure.

I fell asleep a happy, happy girl.

: : : : :

The following weekend, each night, one guy fucked my pussy, then the other guy fucked my ass, on my side like before. The weekend after that, the same thing, except we did anal first. The third weekend, we did anal in other positions – doggie Friday night, Saturday on my back with my legs pulled up. The weekend after that, we did anal cowgirl, both nights. That became the guys' favorite – apparently it's the tightest and deepest.

It took several more weekends before I could lube up back there without any anxiety. That's when things got really interesting.

One Friday night, we had nothing on our calendar, so we got a pizza, watched a movie, and retired. As usual, I got in the center of the bed, with a guy on each side. We kissed, they massaged my breasts, they took turns fingering my pussy and my ass – already lubed. Chad rolled onto his back, and I straddled him, guiding him into my pussy. We started slow and deep.

Jeremy leaned over me, and whispered into my ear, "You ready for the next step?"

I paused a second, and nodded. I buried my face in Chad's shoulder. Chad raised his knees, giving me lots of room to spread my thighs, and my cheeks. Jeremy inserted one finger, and Chad resumed fucking my pussy, slow and deep. Jeremy added a second finger, matching his motion to what Chad and I were doing.

We did that for several minutes, until I was as relaxed as possible. "Here we go," he said. Chad stopped, fully in. Jeremy lined up his cock, and slowly inserted the tip. He worked it in and out a couple of times, then went for depth.

I groaned, "It's much tighter with another cock in me."

"Mmmm, it sure is," Jeremy grinned. "You're doing good, that's almost half. Start moving over Chad now."

I rolled my hips so that I pulled slowly off of Chad, and Jeremy moved with me so that he neither inserted more nor pulled out. I began slowly fucking Chad, in a little, out a little, while Jeremy held in place. I added depth to my stroking of Chad, and he began to rock with me. We started to get a decent rhythm going, the age-old in and out. Before long, still going slow, we were going deep up front.

"Hold that speed," Jeremy said. Then he began to move, as well. As I took Chad in, Jeremy pulled slightly out. As I pulled off Chad, Jeremy pushed in. It was just a little, he told me later, barely an inch, but the extra friction was amazing for me.

I started to speed up. "Slow, baby, slow," Jeremy cautioned. "We'll get there. It's going great, let's not crash and burn on our first try."

"Okay," I begrudgingly said, "but it feels so amazing."

We rocked along, slow and easy. Chad reached full depth in the front, Jeremy kept gaining a little depth each thrust in back. Occasionally we lost sync, and had to re-establish our combined motion, but overall, it went smoothly. Jeremy said later that he never got more than halfway in, but I have to say, I felt pretty fuckin' full.

Jeremy came first. He trembled and shook, and lost his hold on the arm and knee acrobatics he was doing to support himself. He fell, ramming his cock further up my ass. I hadn't been near cumming – I was probably going to, but it was distant. The unexpected depth, though, combined with Chad's thrusting underneath me, launched me straight into orbit. I came, and came, and bucked and vibrated, and came some more, and that triggered Chad.

We lost our combined rhythm when Jeremy fell. Chad made up the difference by pumping into me fast, while Jeremy held still in my ass, keeping everything up front stretched tight. I came again from Chad's run to the finish.

It took a minute for us to untangle our origami of limbs, and I realized I wasn't sleepy yet. Neither were the guys. We relaxed awhile, cuddling, chatting about how our weeks had gone. I ended up fucking each of them again. Chad took me doggie style, and did his Marathon Man thing, lasting forever. He and I both came huge. Afterward, he rolled me onto my back and kissed me.