Sharing Lily with Will

AUTHOR'S NOTE

This is a follow up of the story "Sharing Lily with Louis" which I highly recommend you read first.

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We didn't try anything again for a couple of months after that. For the first week or so I moped around the apartment but Lily and I have a strong relationship, and we talked it out. In the end I came to the conclusion that I would like to try it again, but this time didn't intend to be sidelined quite as much; because I had been so nervous about our first threesome, I'd assumed that Lily was going to be just as shy, though I suppose I should have known she would get wild once she was into it. Now that I knew the procedures a little better, I was ready to have my voice heard, and my cock felt. I knew, of course, that despite feeling guilty, Lily would be very, very willing to go for round two with Louis, so after some deliberating, we decided to make it happen again.

The plan was for him to come over the following Friday, for some late night fun. That evening we were having a small party with a few friends (which Louis couldn't make, being the busy man that he was) and the idea was to loosen up with a few drinks before Louis joined us and we got down to business. He was arriving quite late, leaving Lily and me some time between the party and his arrival to fool around and warm up. Since my rather negative reaction during the first threesome, I had warmed up to the idea of seeing Lily fucked by another man, especially in the ass, which she took like a champ, and I got horny just thinking about other men checking her out. None the less it still made me jealous to actually witness her doing something with someone else. So, when Lily asked me if it was okay that she wore a low-cut top to the party and flirted a little extra, in preparation for Louis, I was hesitant to consent, though of course I did. It was, after all, pretty hot to see her in action.

Despite my apprehension, I enjoyed her performance thoroughly, especially when it came to Will, my best friend, who was always the most flirtatious guy in the room, and this evening enjoyed her attention a lot. I watched on, jealous despite myself, as she rested her hand on his knee when they talked and laughed at his every joke.

By the end of the evening everyone had left except Will, as was usual since we started our tradition to end every party with a few beers, just me and him, though Lily had not gone to bed yet. She was sitting on his knee, straddling it as she occasionally caught my eye and smiled sexily. I smiled back and tried to continue the conversation as best I could with Will, but every now and then I could see her actually grinding her pussy against his knee, as she pretended to shift her weight. I'm sure he noticed it as well, but he took it in stride, bless him, and kept up the conversation with gusto, resting his hands inconspicuously on his own legs, a beer in one of them. We were all drinking, and aside from being incredibly horny at Lily's show, we were all also slowly and surely getting drunk. Finally, Lily stood up, grinding her pussy hard against Will's leg one last time, and leaning on it with both arms to push her tits together for me as she made to get up.

"I think it's time I went to bed, guys, don't stay up too late, now."

She walked over to me, bending over to kiss me. Our lips met briefly and she paused as we parted to give me her 'look,' meaning she wanted me to join her in bed as soon as possible. Walking away, she let her hand linger on my shoulder, and she put a little extra swing in her hips, which worked for Will's benefit as much as it did mine.

"What, no kiss for me?" Will called after her. He always had been a cheeky guy, and this was one of his most common goodbyes to her.

I played along and called after, "yeah that doesn't seem fair!"

I knew she found him attractive, we had talked about it before. He is quite tall and has strong arms, ending in equally strong hands, with big fingers, which Lily loved to point out would feel amazing, to my slight chagrin. None the less, I didn't expect her to do what she did next: she came back around the corner, and walked towards Will. My heart started beating faster as she approached him, coming to a halt in front of him with her stance wide and her arms akimbo. He leaned back on the couch, a little confused as to where his joke was taking him, and smiled nervously at me. I managed a smile as Lily looked back at me, and then sat down and straddled his lap, her hands gripping the back of the couch behind him as she leaned in, tilting her head sideways as if she was about to kiss him. Will spread his arms, in defeat, or as a football player proving innocence in a foul, but Lily pulled back before her lips touched his and smiled triumphantly, "can't handle it, huh?"

"Well I can," he scoffed, trying to recover, "but I don't know if Sam can."

I laughed, "oh, I can."

She looked back over her shoulder, still straddling him, and winked. I bit my bottom lip at the sight, and smiled back. She got up, kissed her two fingers and placed them on his lips, and left the room.

Now left alone, Will and I went out on the balcony with our half-finished beers. Though initially a little shocked, he played it cool and conversation soon resumed. We sat down and talked about girls (of course) and preferences, etc. There is one thing Will and I have always disagreed on and that is boob-size on girls. I have always been one for a nice, big pair of breasts, but Will prefers them petite, which I have never understood. I finished my beer and opened another.

"Trust me dude, big boobs are nice, when you've got yourself a good handful, with some nice cleavage, mmh," I mimicked fondling a pair and put on a content smile.

He laughed, "well I get that you like cleavage, but it's much better when they're small and perky, with some nice nipples."

"What, big can't be perky? What about Lily's, they're perfect!"

"They're nice, but I dunno, the only big boobs I have seen have weird nipples," he answered.

"Trust me, Lily's are beauties."

"Oh yeah?" he smiled, cracking open his sixth beer of the night, "you got any pictures?" he asked, teeth showing in a wide grin and a glint of mischief in his eyes. This was actually not an uncommon thing for him to request, so I just took another swig, "nope, sorry bud."

Then I started thinking about the folder I had on my laptop of a 'photoshoot' Lily and I had made over webcam one night, and wondered what would happen if I actually showed him them. Though I was slightly uncomfortable with the idea, the thought of seeing him ogle my girlfriend was pretty hot. Bolstered by the beer, he pressed on "you're lying, of course you do," he said matter-of-factly.

I paused for a split second, "nah man, sorry," though admittedly the alcohol was working in his favour, focusing my mind on the turn-on of showing (very sexily posed) naked pictures of my girlfriend to my best friend, rather than the fact that I would be showing naked pictures of my girlfriend to my best friend.

"Awwh, come on, it's tradition!" he said, referencing the fact that a couple of our closest friends had shown us pictures of their exes, though I'd never heard it referred to as a tradition before. I looked at him sideways from where I was sitting next to him and checked if he was serious. He looked like he didn't want anything more in the world, though he tried not to betray it, and I opened my mouth to say no again, but instead, on impulse, got up and fetched my laptop.

Will looked like he couldn't believe his luck as I returned with the laptop and opened it. Without a word, I found the files, and opened them for him.

"Oh wow," was the only thing he could say over and over again as I showed him picture after picture of Lily in a variety of poses on a chair; playing with her tits, pulling her hair, gagging herself on her fingers, hanging her plump, round ass off the edge of the chair to show it off, riding the chair, fingering herself, her head thrown back in pleasure, you name it.

When we had cycled through them all he immediately said, "do you have any more?" a pleading look in his eyes.

I smiled, "weeeelll --"

"Yes!" he said, "show me."

"She's right inside, I'm sure with the right persuasion, she'll be willing to help out," I said. I couldn't believe what I had just suggested, and realized what this meant; another guy was going to get off to my girlfriend; another guy ogling Lily. She'd love it of course, but a pang of regret and pre-emptive jealousy hit me as I realized what I'd done. At least she wouldn't be fucking him; Louis would be taking care of that.

Will laughed, taking it for a joke, and I paused, considering pretending I hadn't meant the offer, but I just smiled, "shall we go see if she's up?"

He still looked dubious. I got up and walked inside, and after a short second, Will followed.

"You okay?" I laughed, nervous myself, "you look a little pale."

"Sam, are you serious?" he asked. Again I paused; again I considered walking away, my stomach already churning at the half-enticing thought of pushing the limits and seeing Lily tease him, but I just smiled and held up a finger for patience. I left him in the kitchen and walked into the bedroom where Lily and I had had our previous sexual adventure with Louis, finding her on the bed. Far from being asleep, Lily was lying across the bed, one arm stretching sensually across to grab a pillow, and her other down, tucked between her legs, arching up in pleasure, as she touched herself. She heard me enter and moaned softly, "has Will gone home?"

"Uhm, no; actually he wanted to let you know that he's ready for that kiss now," I said, my soft voice in the darkness contrasting the strange act of hooking my girlfriend up with my best friend.

She hesitated, confused, "you mean you wanna involve Will?" she asked.

"Well yeah, no, just the kiss --"

"Is this your plan or his?" she asked, but I could tell it didn't really matter anymore; more sanctioned fun with other men was always welcome. She rose from the bed, wearing her long, low-cut top which almost hid her cute, white panties, and a sexy, black push-up bra, which was pushing her tits together for a perfect cleavage.

"Well, both, sorta, he also wants to see your tits," I added, as she walked past me smiling into the hall to the kitchen. We entered the kitchen and Will's eyes immediately fell on Lily's boobs.

"Wow," he said, and raised his eyes to hers as she smiled at him playfully.

"I hear you changed your mind about that kiss," she said, softly, as if not to scare him, but with an undertone of power; she had already taken control of the situation and we guys were helpless.

"I, well, uh," he muttered, but I nodded to him and he finished with a "yes!" and his best smile, "and," he added, "I'd like to maybe see those?" pointing at her chest with his big hands. I laughed at his comedic behavior which Lily found so charming, and leaned on the wall, watching the scene unfold. She grabbed his two hands in hers and intertwined their fingers, then, standing on her tip-toes, she leaned in and kissed him, sucking his bottom lip as they parted.

"Well now I'm jealous," I said, jokingly, though in truth I wasn't entirely happy with the kiss; watching her teasing him had been fun but I felt pang of regret now, wondering if I had not better just have sent him home. I pulled her back to me, kissing her deeply as my hands landed on her round ass, pulling up the top slightly to reveal it to Will. He stood there awkwardly until we finished. Letting her go and looking at him, I swallowed, before saying "there, now you two can have some more fun, but let's move into the livingroom, it's more comfortable."

Lily took the lead and grabbed our hands, leading us over to the couch and sitting us down next to each other, our knees touching. She stood there and leaned over us, her hands resting on our inner thighs and squeezing. This was what I loved about her; when she was horny she would take charge and fulfill her desires. This was also what made involving others in our games so unpredictable, but I was willing to 'go with the flow,' as Will always proclaims to do (which he certainly was now), at least for a little bit. Louis would be arriving in an hour, anyway, so she would probably wrap this up soon. She looked at me, gave me a passionate kiss, and then focused on our guest. She got on his lap, straddling him as she had done before, and placing her arms to either side of his head, hanging her tits in front of his face. He looked at me in wonder, and seeing me okay with the proceedings, he raised his hands to cup her boobs. She quickly smacked them away and said "uh-uh, only look."

I smiled; no danger of this going too far. While showing Lily off to Will was hot, seeing my bestfriend fuck my girlfriend would be a little extreme. Lily and Louis didn't know each other well except for meeting at parties every so often, so there was little beyond the sex, but Will was different; they'd hang out alone on occasion, and got along really well. Still, a kiss couldn't hurt; they'd even done it before, though admittedly it had been a dare for a drinking game.

Will looked up at the beautiful girl now straddling him, placing his hands instead on her thighs, as she leaned in and kissed him properly. They made out, lips parting to reveal tongues sliding across each other, his big hands now rubbing her legs as they kissed. She began again to grind against him, slowly humping as her hands moved to his face, caressing his unshaven cheeks, and playfully grabbing a handful of hair. She was enjoying herself, clearly, and I felt myself grow hard at the display, deliciously taboo and tantalizing. As they continued, Will, now emboldened, moved his hands to her ass, despite expecting to be slapped away again and found to his surprise that Lily moaned in response. As he massaged her plump ass, she let go of his lips and raised her head with another moan, grabbing the back of his head as she pushed him down into her cleavage. He caught my eye with a goofy, but nervous smile, and I forced a wink, getting horny at Lily's raunchy behavior despite myself.

"Mmh," she said, letting go of Will and sitting back, "I can feel your dick, Will, nice and hard."

My cock jumped as my stomach vaulted, but he smiled, face reddening slightly, "well who wouldn't be?"

She giggled and said "true, but I think you came for a strip show?"

"Ah, yes I did," he said. She got off his lap again, and stepped back a few steps to give us both a full view. Will, now quite in a daze just stared, not hiding his erection as Lily started swirling her hips, hands pulling her top down to cover her panties, revealing her bra and beautiful cleavage. She closed her eyes and moaned, clawing and pulling at her top as she danced in front of the two of us. Will looked hypnotized and my cock felt harder than ever at my best friend's display of lust for my girlfriend. Finally, she stepped closer, as she started pulling her top over her head, revealing first her beautifully toned stomach, her ribs as she stretched to remove her clothes, and finally, her black bra and big tits Will actually audibly gasped as they were released, and she hadn't even removed her bra yet.

Lily smiled and giggled, and said "Will! Are you enjoying yourself?"

At this he seemed to snap out of his trance and smiled his schoolboy-antics-smile, but kept his eyes on her tits, "why yes, yes I am!" Then looking up in her eyes he said, "very much." Their eyes didn't leave each other until she giggled again, dropping her gaze to his crotch.

"Mmmh, good," she said, "but I don't think you guys should be bothered with those jeans, why don't you take them off?" I smiled, happy to be included again, but Will looked a bit hesitant, unsure what to do, and looked over at me.

"Well how about you come over here and help us a little?" I said, reluctantly playing the wingman for both of them. Lily looked at me and rolled her eyes, smiling as she did, and, biting her bottom lip and stepping up to us, got on her knees. She shuffled up to me, and looked into my eyes as she started undoing my belt and pants. I leaned down and kissed her as she pulled my buttons apart, leaving my pants completely open and my boxers -- now tenting like crazy -- showing through.

She smacked me lightly on my thigh as she pulled off, "there, now you can manage the rest by yourself."

I laughed at her mock annoyance and said, "now, don't forget Will."

"How could I ever forget Will," she said, smiling now, "I've been waiting to see what that cock of his looks like."

"Who says you get to see his cock?" I said, both Will and I staring as she crawled over and situated herself between his legs.

"I'm in control of the pants, aren't I?" she said with a wicked smile as she started undoing his belt, her nimble hands grabbing the buckle and unclasping it as she pulled. My cock jumped at the sight of her small hands darting across his crotch, carefully poised to undo and pull down his pants. As she unzipped him, she pulled his shirt up to reveal his toned stomach and big pecs, and leaned down. I craned my neck to make sure there was no funny business and saw her lick his belly up to his navel, then snake around it and land a kiss on his broad chest. Again, he gasped, involuntarily, and my stomach twisted as I heard the sounds of pleasure from a man my girlfriend was pleasing. She continued her work and pulled his pants open, revealing his boxers, straining erection and all. Instead of stopping where she had with me, however, Lily started pulling at his pants, sliding them under his ass and down his legs, where she left them. She moved up again, running her fingers up his hairy leg, past his knee, to the inside of his thigh and even further, passing her hand under the loose-fitting fabric of his boxers to rest it against his balls. He practically squirmed as her fingers brushed inside his boxers. She smiled at the effect and carefully withdrew her hand again, but not before giving his balls a quick pet, her small fingers momentarily tickling him as one of her fingers rubbed softly against his taint, her other hand rested on his knee.

By now I was getting impatient and eager to get back into the game, so I said "whoa, Will gets this and all I get is a 'do it yourself?'" I attempted to sound light-hearted but my jealousy shone through.

"Well, we have to be good hosts," she said, a playful glint in her eye, and I realized she enjoyed my reactions. I had assumed her focus on Louis last time had come from being caught up in the moment, but she was actually enjoying teasing me with Will! I wanted to say something, but bit back a retort to avoid embarrassment while our guest was there. Will, was not completely oblivious to our tension and attempted to lighten the situation.

"Yeah man, it's only proper," he said, showing his teeth and cartoonishly sticking out his tongue. Though his attempt at levity did little to ease my feelings, I smiled politely, and Lily giggled, and slapped him lightly on the knee.

"Will," she laughed, drawing out his name like she did when flirting, leaning back and touching her nipples through the fabric of her bra, "you just want to see these."

And just like that, I was forgotten again, Will's attention required elsewhere. He turned to her and said, "well, yes, I would love to," showing an almost comically shy smile. Whether she found it genuinely charming or if she was putting on a show for me, she giggled again, and got on her feet in front of us. Then, she started her slow-moving dance, touching herself sensually, tracing her fingertips along her stomach and over her soft breasts. Then she came over to me and, taking hold of my hand, bid me rise and led me over to a lounge chair on the other side of the room, across from Will sitting on the couch. Leaving my jeans by the couch and my hard-on clearly showing through my boxers, I sat across from my bestfriend as my girlfriend resumed her strip-tease for us.