Helping friends with their sexual bucket list… [MFF] [PART 1]

"OK, OK, sworn to secrecy or whatever. Now what's this insane request?"

A few minutes into catching up over drinks one night, my good friend Aubrey had gotten weirdly quiet and fidgety. I'd known her for almost a decade—we'd met as coworkers, become work friends, and then got different jobs but stayed in touch and become even closer—so I could read her like a book and immediately asked what was up.

That was when she blushed and sort of averted her eyes and said she had a crazy request she had to run by me—one from a mutual friend, not from her—but that, no matter what my answer was, I had to swear I'd never tell a soul.

"Seriously, Scott—this is a huge deal. Sacred trust. Friendship on the line." 



"I honestly could not be more confused, but I promise—I will not share whatever you're about to ask me with anyone else, ever."

(Except, obviously, with strangers on reddit years later… )

"OK," Aubrey said, taking a deep breath. "So, I know you've always found Tess, like, unimaginably hot…"

Tess was another former coworker from the same office where Aubrey and I had met, years back. She was a couple of years younger and more junior than us, but we'd all become friends—and I had, indeed, confided in Aubrey that I thought Tess was drop-dead gorgeous: with long, slender legs, wide hips, a slim torso with small but proportional breasts, and back-length blonde hair, she wasn't just my "type"—she was one of the most stunning people you could ever hope to meet. I'd never pursued her purely because she was out of my league and I was sure she'd never be interested. We were still in touch occasionally, but had never been as close as me and Aubrey.

"Y-yes?" I said, raising an eyebrow at her. "But now I'm even more confused."

"This request is from her. Or I guess on her behalf, but not from her."

My heart started to beat a little faster. I still had no idea where this was going, but "this person you find hot has a question for you" wasn't a terrible start…

"Still confused."

Aubrey took a long drink of her cocktail and then another deep breath.

"She's turning 30 in two weeks, and she asked me to set something up for her."

My heart sank. I already had the e-vite: a Friday night beer garden get-together with a bunch of friends.

"The beer garden thing? I'm already planning to—"

"Not that," Aubrey shook her head. "After that. She asked me to help her with something a little more discreet, and a little more… adult."

I raised my eyebrows.

"Oh?"

"She wants to close out her 20s by checking some things off her bucket list she never got to experience—like, before she hits 30 and has to act like a grownup and probably meets her future husband or whatever."

"Sure."

"Specifically, sexual things."

Now my heart started to beat faster.

I wasn't totally shocked that "check stuff off her sexual bucket list" was something Tess would do—back when we'd worked together, in our early 20s, she often talked pretty frankly about how much casual sex she was having. So I knew she was a confident, sexually adventurous person.

"And her sexual bucket list obviously includes… me?" I said with a cartoonish pause for effect. Aubrey snorted and smacked my arm, the tension finally broken.

"Obviously NOT, you idiot," she laughed. "But. One of the things that's on it is… completely anonymous sex. As in, being with someone while blindfolded and never seeing their face, hearing their voice, finding out a name, learning who it was."

Obviously by now I was rock hard. (Thank goodness we were seated side by side at the bar.)

Tess's only other "guidance" had been to pick someone that she, Aubrey, knew and trusted, regardless of whether Tess knew them.

"So I thought of you—you're single, trustworthy, a good guy, will be a grownup and not a creep about it, and also happen to find her super hot, right?" Aubrey said. "So. Everybody wins."

"You're right. I will not need time to think about this," I said.

At this, Aubrey bit her lip and grinned, looking a little embarrassed.

"I'll, um… I'll also be there."

My eyes went wide. She blushed and took another long drink.

"As in… ?"

"I'll be focused on her, but…"

"Threesome was another item on the bucket list?"

"Yep," she nodded. "And another reason I thought of you."

We'd been friends for like a decade, so of course we'd talked about everything under the sun and she knew I'd had a few threesomes, etc. Even though she'd been married for most of that time.

Which begged a question…

"Wait, why not Thomas—and how does he feel about all this?"

Thomas was Aubrey's husband. A great guy—I'd become friends with him through her over the years.

"Well obviously he supports it," she said. "But… he also prefers not to know any details, including which guy is involved. Though he agreed with Tess that it needs to be someone I know and trust—the three of us talked all of this through, including like our boundaries and everything."

"Ah, now I get it—we're dealing with more than one bucket list, aren't we?" I looked at her slyly, and she grinned back at me and smacked my arm.

Aubrey was bisexual, but had come to terms with her sexuality only after getting married to Thomas, who was the first and only person she'd ever slept with. After a few years went by, having never explored her bisexuality, she felt like a part of herself might be missing.

Thomas, after initially being freaked out, had quickly come around and—apparently—expressed a willingness to talk about opening up their marriage, so she could sleep with both women and men, if she wanted to. But Aubrey had never been comfortable with, or interested in, hookups—she always craved some kind of deeper connection.

Aubrey said they'd talked about just having a threesome with someone, but hesitated because they'd both heard horror stories about threesomes going poorly and wrecking marriages. So when her good friend Tess approached her, in confidence, about setting up a crazy birthday sex thing, she and Thomas immediately agreed it was the perfect safe, healthy way for her to experiment with her bisexuality. Aubrey, for her part, was also excited about trying sex with at least one other man in her lifetime—someone she trusted, rather than a random hookup.

We hammered out the logistics. I explained to Aubrey that I was really into creampies/cumming inside, and would love to get tested and go without condoms if they were both comfortable doing so. If not, I'd be more than happy to wear protection, but figured I'd shoot my shot (SO TO SPEAK) as long as we were helping each other fulfill fantasies.

Both were on birth control and Tess had already specified that she wanted to go unprotected—that was part of the thrill of fucking someone anonymously, I guess—but Aubrey was initially reluctant. Even though she was on the pill, she and Thomas always used condoms as a backup. So, in addition to Aubrey having only slept with one person, neither she or Tess had ever had unprotected sex.

I didn't say anything, because I didn't want to pressure her. But then she texted me a day later and said she'd thought about it and discussed it with Thomas and would be OK going without a condom, but wanted to think some more about whether she'd be comfortable allowing me to finish inside of her.

I was—obviously—ecstatic beyond words and told her she could set whatever ground rules she wanted, or it could be a game time decision on her part. She agreed.

The wait, as you can imagine, was hellish, but I tried to distract myself with work. I screenshotted my clean STD panel results, cropped out my name and other info, and sent them to Aubrey, so she could share with Tess totally anonymously. I jerked off into oblivion, wildly horny with anticipation, but then mostly reined it in the week beforehand. Which took willpower, but… was it ever worth it.

Finally, the night arrived. Tess's birthday.

I walked into the bar where she and all of her friends were meeting for drinks. Tess was standing among a gaggle of women in the corner. Her back was to me, and she was wearing skin-tight black jeans that showed off her long, sexy legs, her voluptuous ass and wide hips. Her skinny waist was bare, and she was wearing a black crop top with a sheer lace back, exposing her sexy back.

I was instantly hard. There was something insanely hot about seeing this phenomenally gorgeous woman across the bar, dressed to draw attention and to look and feel sexy on her special day, knowing I would be fucking her in a hotel room above this very bar in just a couple of hours.

What made it even hotter, somehow, was that she had absolutely no idea.

I walked over and she happened to half-turn, spotting me, and turned around.

"Scott!" she said, extending her arms for a hug. It was sincere, and not without affection, but definitely platonic—not the kind of hug you give someone you're about to hook up with. I thrilled again at my secret knowledge. "It's been forever. How are things?"

We caught up for a few minutes like two old work friends, but I was almost dizzy—whether from the blood rushing from my head to my throbbing cock, or from the fact that I kept picturing her naked and blindfolded underneath me, the way I'd see her for real very soon.

Just then she caught someone else's eye over my shoulder, thanked me for coming, and rushed off to greet another guest. I walked up to the bar and ordered a martini, my head spinning.

Almost immediately there was a friendly hand on my shoulder. It was Thomas, Aubrey's husband.

"Hey man, good to see ya," he said. We shook hands and he ordered a beer. Again, my libido was raging at the thought that my friend had no idea I was going to have sex with his wife that very evening.

As we chatted, I glanced back and saw Tess in conspiratorial conversation with Aubrey—evidently, she and Thomas had just walked in, but Tess had held her up. From across the bar it looked like just two friends having an intimate conversation, but I suspected it was about something else.

A couple of minutes later Aubrey came over and joined Thomas and me at the bar. At first, there was the subtlest hint of awkwardness about her—conscious, no doubt, that she was here with the birthday girl and her oblivious husband, neither of whom knew she'd arranged for me, of all people, to take part in what was to come. But we soon settled into our usual rhythm, as friends, and I think I even caught a flash of excitement in Aubrey's eyes at one point. Maybe it was starting to turn her on as much as me.

The happy hour wore on—at one point, some friend of Tess's I'd never met offered a toast—and as it started to thin out, I checked my watch and realized it was time for me to get moving, too. I said a quick but warm goodbye to the oblivious Thomas and to Aubrey, knowing I'd be seeing her very soon… and then went to hug Tess goodbye.

She was half-distracted, since I'd tried to say a quick goodbye while she was in conversation with somebody.

"Ah, we barely caught up," she said disappointedly. "But thank you so much for coming out—let's see more of each other soon!"

"Very soon," I agreed.

She gave me a quick hug. I felt her pert breasts up against me, her strong, sexy back under my hand as I pulled her in. Then she turned back to her friends.

I left, walked down the block and, instead of getting an Uber, ducked into the bar on the corner to kill time. About an hour later, my phone buzzed—the text I'd been waiting for, from Aubrey:

"ready"

Heart pounding, I downed the rest of my beer and settled up.

Walking past the bar where Tess had had her birthday happy hour, I went to the hotel lobby, showed my ID to pick up the keycard Aubrey had left for me, and then headed to the elevators. The room was a suite, so I let myself in quietly to the empty outer room and then went straight to the bathroom. Then I stepped out and sat on the couch and texted Aubrey back:

"ready"

There were two purses and a suitcase under the desk, but the door to the bedroom was shut and there was no sound. Then the door opened briefly and I heard soft music and saw light, and Aubrey shut it behind her and came walking toward me in a plush hotel bathrobe, her hair mussed.

The plan had been for the two of them to get started before I arrived… and, clearly, they had. I smirked as Aubrey walked up to me and started to say something sarcastic.

"Well, it looks like you didn't need any—"

But she cut me off, as she walked up to me, by planting a lust-fueled kiss on my lips and wrapping her arms around me. She tasted strongly like freshly-eaten pussy—Tess's pussy.

Instantly the energy changed. I kissed my friend back ravenously as she pulled my shirt off and then we both fumbled with my belt. As she pulled my pants down, I yanked on the knot of her robe and it came open, revealing Aubrey's ample breasts with large areolas, a neatly trimmed patch of brown pubic hair below.

I wrapped my arms around her inside the robe, kissing her again and pulling her naked body against mine, groping her breast and feeling her nipple harden under my hand, grabbing her ass, flicking a hand up her inner thigh…

Aubrey gasped and pulled away.

"Holy shit," she said. "I've never been so turned on in my fucking life."

"Honestly, same?" I said, going back in for a kiss but stopping when she pulled away again.

"But… Tess is waiting for us both, and this is supposed to be her night..."

She looked at me with the thrill of anticipation in her eyes. I took off my boxer briefs and she looked down at my hard cock hungrily—only the second one she'd ever even seen, after her husband's, and only the second that would ever go inside of her.

"Let's go."

We tiptoed as we got close to the door and then she held a finger to her lips, opened it, and we entered.

The room was warm and one of the lamps beside the bed was on, so there was plenty of light. A Bluetooth speaker played some kind of unmemorable playlist at the level of white noise. On the bed, Tess was lying naked on top of the white comforter, her long, tan legs spread open to reveal a tight pink pussy, framed by the sexiest bikini tan lines, against which she was holding a loudly buzzing vibrator. Grinding it against her clit with one hand, Tess squeezed one of her tits with the other—her nipples hard and perfect and pink, like pencil erasers—bucking her hips and writhing against the bed. Her long blonde hair splayed against the pillow, but her beautiful face was partly obscured by an eye mask which Aubrey had helped her secure with a bit of medical tape at the top and bottom, so she genuinely couldn't see a thing.

Tess was also wearing noise canceling earbuds, so she hadn't heard us enter the room, though she'd known that Aubrey would be leaving to get someone at some point.

Holding a finger to her lips, Aubrey dropped her robe and crept back to Tess on the bed and kissed the inside of her knee. Tess started and gasped, her mouth breaking into a breathless, pleasurable smile as she reached down to take Aubrey's head in her hands and pull it toward her pussy. Aubrey kissed her way up Tess's inner thigh and then started to lap tentatively at Tess's clit, drawing a lusty moan from Tess.

I crept up closer, watching as Tess pulled her lips apart for Aubrey's tongue, seeing it dip inside the glistening folds of Tess's pink insides and then linger on her exposed clit, savoring the fact that I was watching my good friend eat pussy for more or less the first time—until they got started a few minutes before I arrived, it had just been a fantasy to Aubrey—and my other friend experience having her pussy eaten by a woman.

After lingering for a long moment in silence I stepped back a bit, stroking my cock and taking in the scene. Aubrey's ass was practically in my face as she crouched over Tess on the bed, devouring her. I drank in the sight of her asshole, her pink pussy lips swollen and slightly parted, knowing I'd get to feel every inch of her soon.

But first, the birthday girl.

Gingerly, I tiptoed to the side of the bed, near Tess's head. I tried to be gentle as I got onto the mattress on my knees, but of course Tess immediately felt my weight on the bed and snapped her blindfolded face around in my direction, her nipples hard and her chest heaving. I could see her entire body shuddering in horny anticipation, knowing some other anonymous stranger had entered the room and was about to have his way with her.

Leaning on one hand and aiming my diamond-hard cock with the other, I placed my tip, glistening with precum, gently against her cheek—and she instantly turned her blindfolded head and took the tip of my cock in her mouth, swirling her tongue around it and moaning in horny excitement and bringing one hand up from Aubrey's head to stroke me.

I looked down as one of the most gorgeous women I'd ever met moaned onto my cock, wrapping her lips around it and grabbing my ass to pull me deeper into her mouth. Looking down, I saw Aubrey eagerly watching Tess suck my dick while she continued to lap hungrily at her pussy. I grabbed Tess's breast and pinched her nipple and she writhed in pleasure toward me, utterly possessed by the sheer hedonistic thrill of what we were doing.

This was getting me more and more revved up. On the verge of losing control already, I laid on my side and pulled Tess's legs up over my shoulders, so we were side by side on the bed in a 69 position. Aubrey slightly shifted positions but kept licking Tess's pussy as I brought my face down to join her. Pulling back just a little, she held Tess's pussy lips open and I took a moment to admire how gorgeously pink and wet her insides were, glistening in the warmly-lit hotel room. I heard Tess's breath catch in her throat as it turned her on to realize The Stranger was peeling her open to peer inside her.

Then I plunged my tongue into Tess's pink folds, tasting her briny musk along with Aubrey's saliva and feeling Tess quiver as we ate her out, her mouth still on my cock. As I pulled my face back, Aubrey leaned in and kissed me hard, both of us now tasting strongly like Tess's pussy, and then we took turns eating Tess out and trying, awkwardly but hotly, to do so at the same time.

Tess was a total wreck. Isolated from Aubrey and me by the blindfold and noise canceling earbuds, she was lost in a world of Tess-centric pleasure, bombarded by waves of stimulation and unexpected sensations as our hands and mouths explored and caressed and serviced her. She was squirming and moaning, flexing and unflexing her toes, spouting gibberish around my cock and breathing hard into my pubic hair.

But all of a sudden Aubrey and I felt her hands pulling us away, so we stopped and looked up. Tess rolled onto her back, letting my cock spring from her mouth. She took a second to catch her breath, but then she let her lithe body relax into the mattress again.

With one hand, Tess reached up and removed one of her noise canceling earbuds, leaving it on the bed beside her. I'd have to try to be quiet, or at least not recognizable.

"Whoever you are," she said, her breasts still heaving, her voice quivering with horniness. "I need you to put that dick inside me right now."

Seized by something primal, an animalistic growl escaped my lips—so much for "quiet"—and I rolled off the bed, onto my feet, and then spun around and grabbed Tess by the hips, pulling her to the edge of the bed. At the same time Aubrey climbed fully up onto the bed, her eyes glued to Tess's pussy as I lined myself up with it.

"Holy fuck," Aubrey said under her breath. I looked up at her and we exchanged "I can't believe this is happening" eye contact, and then she reached down to spread Tess's pussy lips as I pressed my cockhead against them.

"Oh fuck, fuck… oh yes… oh my god…" Tess was moaning softly, almost weeping, in anticipation as I slowly, slowly pushed forward, feeling the wetness and then the white-hot heat of her slick, inviting hole open up for me as my tip penetrated deeper and deeper, her walls quivering as they stretched around me—her breath ragged as she felt some anonymous stranger bottom out, as deep inside of her as anyone could be, throbbing and leaking precum against the entrance to her empty womb.

"Oh my god," Aubrey whispered huskily, starting to rub Tess's clit. "This is so fucking hot… I've never watched people fuck before…"

Tess could only whimper in response.

"You have no idea whose dick is inside you right now, do you?" Aubrey moaned.

"N-no idea…" Tess was breathlessly turned on by this—gasping, desperate, in the throes of experiencing a longtime fantasy fulfilled. I slowly drew my cock out of her, inducing another whimper, and then plunged in again, making her moan.

"I can't believe I'm watching him fuck you raw," Aubrey whispered. "A total stranger."

Tess squirmed and reached down to wrap her hand around my dick where it was splitting her open, her mouth agape as she felt me draw it out and then thrust back in, gradually building up a rhythm as we savored feeling one another for the first time.

"He's so deep inside of you," Aubrey moaned.

"S-so… d-deep…" Tess echoed faintly in between thrusts. I was working her pussy harder, now, and seemed to be hitting a place that was leaving her more and more breathless, making her body tense up. My balls slapped against her ass and I felt her walls quivering, the heat and wetness emanating from her driving me wild. Her pussy felt so perfectly tight and wet and inviting.

"Eat my pussy while I watch him stroke in and out of you," Aubrey whispered, swinging her leg over Tess's face and positioning her own swollen lips above her friend's mouth. Tess reached up to grab Aubrey's hips and I watched Aubrey's eyes roll back in her head as Tess's tongue contacted her clit.

Then she brought her face down to where my dick was pumping in and out of Tess's pussy, her eyes wide.

"Fuck it looks so good," Aubrey groaned, causing Tess to moan into her pussy. "You're creaming on his cock. You always let people fuck you raw?"

"N-no…" Tess gasped, between licks of Aubrey's clit. "N-never…"

"Not once?"

"N-never…" Tess moaned. This was driving her beyond wild.

"And you don't even know his name…"

"Nnnngghuuuh…"

With that, Aubrey took us both by surprise and lowered her head to Tess's pussy, starting to voraciously lick not just her clit, but her lips and my glistening shaft as I worked it in and out of her. Aubrey's tongue was everywhere, and felt amazing… and then an almost-scream escaped from Tess's lips and we felt her body tense up, so both Aubrey and I kept doing exactly what we were doing.

Not five seconds later, Tess cried out almost like she was in pain and her body writhed and I felt her pussy start clenching and unclenching uncontrollably around me. As her earth-shattering orgasm washed over her and began to subside, I slowed my thrusts and Aubrey pulled her head back, looking up at me in satisfaction as she wiped Tess's juices from her chin.

But I did not greet her satisfied smile as an old friend from work.

I saw a flicker of surprise as she read the look on my face: hunger, primal and animalistic.

In an instant, her smile was replaced by something primal, too, as the reality of what was about to happen struck us both.