Helping friends with their sexual bucket list... [MF] [FF] [PART 3]

Aubrey's pussy felt grippy even though she was sopping wet from a long night of fucking and getting fucked. So I knew this quickie would be, well, quick—which was a must, since Tess was taking a bathroom break somewhere behind the door that separated this outer room from the bedroom half of the suite.

Not that she'd be upset at Aubrey for getting some side action—on the contrary, when she found out later (as you'll see…) she was turned on by it—but there was a risk, in the moment, that she might discover it was me who'd just cum inside of her. Which would shatter the whole "anonymous" part and potentially ruin her night of bucket list fantasies.

So, still inside of Aubrey in an awkward standing position, I pulled out and took her by the hips, spinning her around and bending her over the arm of the couch by the desk. Shifting my weight forward, I got on top of her in basically a pronebone position, sinking my thick cock down into my good friend.

Holding myself inside for a long second, I marveled at the silky feeling of her deepest depths, savoring again that I was the first and only person ever to feel her raw, since she'd only ever fucked her husband, and never without a condom.

"You feel so fucking good," I growled in her ear, feeling the cool air on my wet shaft as I drew all the way out of her and then the searing heat of her insides as I plunged in again.

"S-so do you," she moaned. "I didn't know it c-could b-be like… th-this… oh fuuuuck…"

As I was building up my rhythm, I felt her fingers brush the underside of my cock as she started to frantically rub her clit.

"You feel that?" I growled. In response Aubrey stopped rubbing her clit and ran her fingers across my balls, my shaft, her lips.

"W-wha… ?"

"There's nothing between us."

She inhaled sharply and then moaned again, her fingers frantically playing across the place where our sexual organs came together.

"I'm gonna fill your pussy with my cum," I growled in her ear. "Right now."

A horny gasp, almost a howl, escaped her lips and she craned around to look at me pleadingly, her fingertips playing across my thrusting shaft right at her entrance, feeling my raw, veiny cock working in and out of her swollen lips.

"I w-want… it…" Aubrey moaned raggedly. I was using her pussy now, getting myself off inside of her, and it was driving her wild.

"What do you want." It wasn't a question.

"I w-want…"

With my free hand I reached around to grope her breast, pinching her nipple lightly, and then I ran my fingers down Aubrey's body with agonizing slowness, feeling every inch of her until I got to her pussy, where I reveled in pulling lightly at her lips and pressing my fingertips against her slick opening alongside my dick—not sticking a finger inside, which would be impossible in this position, but feeling and playing and teasing.

"Tell me what you want," I growled again.

"Y-your c-cum," she blurted, almost like a guilty admission. "Your s-seed… d-deep inside of m—"

I gritted my teeth, railing into her harder and harder. Leaning on one hand and using my weight to drive into her as deep as I could, Aubrey began to yelp in pleasure every time I bottomed out, arching her back with each thrust, opening herself up to me—and pushing me right to the edge.

"F-fuck, I'm gonna—" I sputtered.

"I'm ready for y-you…" Aubrey moaned.

My vision went almost black as a wave of pleasure crested across my body, building up to a white-hot feeling at the end of my cock as it spurted the first thick gob of cum into the deepest part of my friend's eager pussy. She reached back with both hands to pull her ass cheeks apart, her eyes wide, just as I grunted and slammed down my hips again, unloading a second thick rope and then another, my dick pumping and spasming deep into her even after my reserves were drained.

I slumped on top of Aubrey, still buried inside all the way, savoring what (I assumed) was the last time I'd ever feel the back of her pussy and her walls gripping around me. She breathed deeply—I could feel her breath heaving from inside her—and I noticed she seemed to be doing the same, just savoring what it was like to be fully filled and stretched out by a longer, girthier dick.

(Not that I'm some porn star or anything, but Aubrey later confided that her husband Thomas did genuinely have a small penis—though she said he knew how to use it)

After a sweetly intimate moment, I picked myself up and pushed with both hands against Aubrey's ass cheeks, making her pussy gape wide open as I withdrew my cum-covered dick. I could see my semen streaked against her pink walls and relished that I'd gotten to be the first person ever to inseminate her—minutes after becoming the first to cum inside our mutual friend Tess.

"You're going to be leaking out of us both all night," Aubrey said, obviously thinking exactly the same thing I was (another perk of fucking a good friend).

"That's so fucking hot," I said.

Reluctantly I let the moment pass and then helped her up, watching as a few dribbles of semen made it from her lips down her inner thigh and then to her knee. I carefully redid my pants, eager to get out of there before Tess came looking for Aubrey and saw her "anonymous stranger" had just been her old work friend.

"Sorry you didn't cum, but I figured we should be quick…"

"No, this was perfect," Aubrey said, giving me a quick kiss as we moved toward the door. "I got what I needed from you… and now I just want Tess to eat it out of me."

If I hadn't had to leave, right then, I swear to god…

But we said a quick goodbye and I did finally leave, reeling from a couple of surreal and intense hours. It was some of the most alive and in command of myself and my sexuality that I've ever felt.

Aubrey later told me what had happened next: she went back inside to find Tess unmaking the bed and rearranging pillows and getting comfortable, having emerged from the bathroom just a brief moment earlier. Relieved that she and I hadn't been caught in the act, Aubrey then described to a completely shocked Tess how she'd chased after The Stranger and had a quickie just now in the other room.

She showed Tess my cum dribbling out of her pussy, and they started touching one another as Aubrey shared more detail. But the storytelling trailed off as she and Tess got more and more revved up and started eating each other out. She told me there had been a lot of dirty talk about the taste of my cum inside one another, what it feels like to have sperm in your pussy for the first time, etc.

They'd fallen asleep and then had sex again at least one more time the next morning—and then the two of them had gone to a fancy brunch at a popular downtown restaurant, where a beat-by-beat recap of the night was the sole topic of conversation: how hot it had been, what it had felt like to fuck raw versus with condoms in previous encounters, how much they'd enjoyed eating pussy and getting each other off, how weird it was to feel the sensation of cum dripping out of them while at a fancy restaurant.

About a month later I was at work downtown and ran out for a cup of coffee. Walking into the coffee shop a couple of blocks away, I thrilled to see that Tess, of all people, happened to be near the front of the line. Her back was to me, and she was wearing dark gray yoga pants that showed off her incredible, sexy legs and every contour of the supple, pear-shaped ass I'd been all over just a few weeks prior. I got immediately rock hard and fought to suppress the flashes of memory that kept coming back, adjusting my pants so my erection wouldn't be obvious while I stood in line.

Tess got her coffee and turned around in my direction but took out her phone. She was wearing a loose linen top that was mostly open, showing off a blue sports bra that cupped the pert breasts I'd sucked on. The gray yoga pants showed off some cameltoe, the not-so-faint outline of those gorgeous pussy lips I'd tasted and parted with my dick the last time I'd seen her.

And. She. Had. NO. IDEA.

My head was swimming as Tess kept walking in my direction and then happened to look up, making brief passing eye contact. I gave a tiny wave but she looked away blank-faced, without recognition—and then stopped in her tracks a couple of steps later and wheeled around, breaking into a beautiful smile.

"Scott! I walked right past you!" she laughed, opening her arms for a hug. I pulled her against me amiably, the smell of her long blonde hair bringing me back vividly to that night. Her lithe body in my arms felt so familiar to me—I'd touched and tasted almost literally every inch of her, inside and out—even though she didn't know it.

"It's been too long!" I said with a smile. The manner between us was relaxed and normal without any hint of any weirdness—just two old work friends running into each other. Except I couldn't stop thinking about the taste of her pussy.

"Yeah, oh man… when was the last time I even saw you? Krista's going away party?" She was racking her brain. The party in question had been maybe three months ago. I was screaming inside, loving that I had ravished Tess's stunning body, given her more than one orgasm, helped Aubrey fulfill her wildest sexual fantasies only a month ago—and she didn't even remember seeing me in passing that night.

"No," I said thoughtfully, pretending to rack my brain, too. "Wasn't it… oh! I stopped by your birthday thing."

"Ohhh of course! We barely had a chance to catch up," she said. It turned out she was in the neighborhood for a meeting a couple of blocks from my office.

I remembered just then that Tess had updated her social media profile photo to a shot of her laughing and sipping mimosas—a photo clearly taken by Aubrey at Tess's birthday brunch, when I was still leaking out of both of them. She must think about that every time she sees the photo, I realized. Except she has no clue, to this day, whose semen was seeping out of her as she immortalized the moment with a pic.

Again, maybe other people find this weird?? But to me, there was something almost surreally hot about it.

A couple months after running into Tess, I found myself on the rooftop deck of Aubrey's condo building—a rowhouse with just two units, of which she and Thomas owned the upper floor—celebrating Thomas's 33rd birthday with a bunch of friends. Tess wasn't there, but other old work pals and mutual acquaintances were, and we all had a great time.

Long after most of the guests had left, a thoroughly inebriated Thomas bid goodnight to the handful of us who lingered on the rooftop, then gave Aubrey a weird devilish look, whispered something in her ear, and planted a long, tender kiss on her lips before heading downstairs to their condo to go to bed. Among the few of us who remained, Aubrey became the center of attention now that her husband had left: funny, sexy, and charismatic.

By the end of the night, the crowd had thinned out to just Aubrey, me, a couple I didn't know, and a younger woman named Liza who had worked as an intern for Aubrey a few years back. They had long since become friends, so I'd met Liza in passing a handful of times, at parties or happy hours where Aubrey had invited us both, but I didn't know her well.

Something about the vibe was weird all night. But I only realized later that it was 100% Liza who gave it away. Everybody else, including Aubrey, was pretty relaxed—but I kept getting vaguely nervous vibes from Liza, barely missing her awkward, averted gaze maybe half a dozen times in a couple of hours.

With mousy brown hair, dark-rimmed glasses, and a voluptuous figure, Liza was still in her mid-20s, almost but not quite a decade younger than us. She seemed to prefer going bra-less: tonight, although her personality seemed relatively shy and modest, she was wearing a light sundress made out of some knit material that clung to every contour of her breasts, concealing basically nothing and giving the impression of body paint more than clothing. There was something sarcastic/sardonic but also deeply sensual in her green eyes and long eyelashes.

I was trying hard to make small talk and avoid ogling Liza's breasts when I heard the random couple—friends of Thomas's—say they had to get home. They hugged Aubrey goodbye and made their way out, so I checked my watch and figured I should do the same fairly soon.

But then I looked up to find both Aubrey and Liza staring at me. Liza instantly looked away, seeming a little embarrassed, but Aubrey arched an eyebrow.

I gave her a puzzled look.

"I—uh, yes?" I smirked back at her. "Something I can help you with?"

"Yes, actually," Aubrey replied, standing up. "I can never get the cover back on the stupid outdoor lounge set—mind giving me a hand?"

"Sure," I said, standing up. We'd been sitting around a patio table near the stairs that led down to Aubrey and Thomas's unit. There was a stupid looking fake hedge that semi-divided the roof into two spaces, and the big outdoor couch and lounge chair were on the other side.

I followed her, and as we got out of immediate earshot I walked up alongside and asked in a hushed voice:

"Hey, everything OK? What's with Liza?"

Aubrey laughed, and I noticed a slight edge of nervousness—the first I'd detected in her all night. Something was definitely up.

"Everything's fine—but, yeah, that's why I needed to get you alone over here," she said.

"Okay…"

"I really hate to put you on the spot," she said. Her eyes were shining eagerly. "But. Would you have sex with me again? Tonight?"

Obviously this wasn't totally out of left field, given our history. But the threesome with Tess was supposed to be a one-time thing—sort of a hall pass. And it had been a couple of months with barely another word about it between us.

"Uh… is it MY birthday? I thought it was Thomas's…" I said. Aubrey's face crinkled into a smile and we melted into one another's arms, momentarily losing ourselves in a passionate kiss—until Aubrey pulled back.

"Oh my… whew," she said. I realized my hand was cupping her breast and hers was touching my rock-hard cock through my jeans. We peeled ourselves off of one another for a moment and she led me to sit down on the outdoor couch as we caught our breaths.

"I assume Thomas is okay with this?" I asked, just checking in. She nodded enthusiastically.

"So, that's the thing," she said. "It's literally his birthday gift."

"Wait… what?"

"I mean I also got him Lakers tickets for our trip to LA next month," she laughed. "But… seriously. Our sex life has been, like, supercharged since Tess's birthday."

I raised my eyebrows.

"As in, you guys talking about it? Or the fact that you slept with her? Or me? Or what?"

Aubrey just nodded with a vague shrug.

"All of the above," she said. "He loved knowing I was doing it, he loved hearing every detail about it, he loved that it's a total mystery who the guy was. And that he had a bigger dick."

Her eyes smoldered at me.

"So the sexual bucket list continues."

"Exactly." Holy shit. This was going to be fun.

My thoughts drifted to Liza, and I inclined my head back in her direction quizzically.

"Aaaaand tonight… ?"

Aubrey shook her head emphatically.

"Not another threesome, no—something different," she said.

Now that sex was on the table, I won't deny that I was a little disappointed that my too-good-to-be-true fantasy of getting to fuck Liza would not, in fact, be coming true. Still, her nerves betrayed that she must be in on this too, somehow.

Aubrey and I were sitting close, sort of on the verge of making out, and I leaned over and did a stupid little drumroll on her knees.

"Ladies and gentlemen, the next bucket list item is…"

"Sex in public," Aubrey said, her eyes flashing. "While… someone is watching us."

My eyes went wide, thinking of 24-year-old Liza as she sat nervously on the other side of the hedge in her sundress. Aubrey saw me put the pieces together and just nodded, smiling in anticipation.

"So that's the ‘someone'—and by ‘in public,' you mean… "

She pulled me into a kiss, then lay back on the couch and pulled me down on top of her by the collar of my shirt. It was late—maybe 1am—but the rooftop was well lit, and we were in the middle of a dense urban neighborhood with houses all around.

I pulled the straps of Aubrey's dress off of her shoulders and then sat up a little and she helped me work it down to expose her ample breasts. I brought my head down and took her hard nipple in my mouth, eliciting a gasp, then hiked up the bottom of her dress to find that she wasn't wearing panties.

I moved myself up a little so I could see all of her in the light of the patio awning. Her breath caught in her throat, knowing anyone could now see her completely naked underneath me except for the dress fabric bunched around her waist.

"Yesssss," she moaned as I spread her legs, dipping a finger inside of her hot, sopping pussy. Her hands had been frantically working at my belt and fly, but she finally managed to get my pants and boxer briefs halfway down my thighs and started to stroke my thick cock, now diamond-hard and throbbing in her hand.

Aubrey looked up at me, breathlessly horny. I knew I was completely exposed now, too, and found it unexpectedly hot. We both looked down at the two fingers I had buried up to the knuckle in her pussy, then at her two hands working my dick, a drop of precum gathering at the tip.

It was when Aubrey craned her neck up to lick the precum off of my cockhead, running her tongue around it with a sensuous moan, that I heard Liza's footsteps approaching from behind us.

She came around and sat matter-of-factly in the lounge chair opposite the couch, watching us unabashedly. Then, without breaking eye contact with me or changing her expression, she slipped the left side of her sundress down and reached up to knead at her perfect teardrop-shaped breast, pinching her nipple and watching my mouth go wide in reaction—and then she pulled her right knee up on the lounger, spreading her legs and snaking the other hand up under her dress.

My cock throbbed in Aubrey's mouth and I felt her pussy convulse around my fingers. Thomas would be in for one hell of a story tomorrow.

And I assumed this wouldn't be the last item on Aubrey's sexual bucket list.