Under Her Wing

Under Her Wing 3

It was Monday. Labour Day.

Philip woke up a good half hour before his alarm would go off. He'd been looking forward to today all weekend. He'd had to fight to keep himself from jerking off in all that time, thinking about what today would bring.

Today was the day he would fuck Emily, and Margot would watch.

He took a long shower, making sure to clean under his foreskin in particular. His penis was becoming aroused at his touch, and he had to will it back down, flexing muscles in his arms to draw the blood away.

He got dressed quickly, ate breakfast, brushed his teeth. He sent Margot and Emily each a text, asking when would be a good time to start. It was 7:00 AM.

"super cute that you are so eager" replied Emily, "but you will have to wait until a reasonable hour bucko"

Margot didn't seem to have even seen his text. Maybe she was still asleep. He sat and waited. Played a few turns of

Civilization VI

. Finally, Emily texted back.

"how is 10 for you?"

"Works for me," he replied.

"Can't wait!" chimed in Margot. "Philip, want to meet outside your place at 9:15? Then we can ride over together"

He replied with a thumbs up emoji.

Margot met him in a very cute brown sweater and a pair of blue jeans, both of which hugged her body in all the right ways.

"Fuck, you look good," he said to her before she pulled him to her for a deep kiss.

"Likewise," she grinned, coming up for air. "I want to thank you for doing this, today. It really means a lot to me, being able to share you like this."

"I'm actually looking forward to it," he said. "I've been learning a lot lately. Not just, like, sex in general, but kinks and trust and all that. It's exciting."

They caught a streetcar up to the subway, and then made their way north to York Mills Station. Emily, Margot explained, lived in an apartment near there, and close to her work at the Landlord Tenant Board.

"Will we need to use condoms?" he asked, quietly.

"No," said Margot. "Turns out, Emily has an IUD so no worries about pregnancy. And she's clean, so no problem there either."

"Awesome," said Philip. "Is there... Are you okay? You look like you're walking a little strangely."

Margot smiled, nervously, and leaned in to whisper in his ear. "I have a butt plug in," she told him. "And I'm still getting used to it. I've brought a few toys in my purse, to keep myself entertained while you two have fun."

"Damn," said Philip. "That is maybe the hottest thing anyone has ever said to me." She grinned mischievously, and kissed him.

Philip's heart was pounding as they rode the elevator up to Emily's floor, walked down the corridor to her door, which she'd left unlocked. They entered the apartment, quietly, locking the door behind them. Philip took a moment to look around.

It was a very nice apartment, clearly, with big windows offering a great view of the city. The place seemed to be decorated fairly starkly, with modern white streamlined furniture and a few large bookcases, but not much adorning the walls beyond a basic wall clock; a far cry from Margot's plush apartment and its kitschy cat clock.

"Is that you?" came Emily's voice from the bedroom.

"It's us," said Margot. "I've brought you a present. Let me just get him ready."

She dropped to her knees, unzipping Philip's pants as he, taking the hint, squirmed out of his shirt. Very quickly, he was completely nude, and very erect. Margot took Philip's hand and led him into Emily's room.

Emily was lying, naked but for a pair of sheer white stockings, on a grey-sheeted king-size bed, flipping through a paperback romance novel, and the sight took Philip's breath away. She was a big woman, but not obese or unsightly. She was curvy, with smooth skin, wide hips, and massive breasts. When she moved to put the book on her bedside table, Philip saw a tangle of blonde pubic hair over a very pink vagina. She was gorgeous.

Emily stood up and walked to the door, putting her arms around Philip and pulling his naked body into a tight embrace. "He's beautiful," she said to Margot. "Thank you." Before he even realized what was happening, her tongue was in his mouth and she pulled him onto the bed with her.

Philip's hands fell to her waist, returning her embrace and she kissed him. Finally, she came up for air. "I've been looking forward to this ever since I saw you, cutie," she hissed into his ear, her own hand caressing his ass.

Across the room, Margot sat down in a chair that Emily had set up, facing the bed. Her jeans were already off and she was hurriedly unbuttoning her shirt, stripping down to her underwear as she watched them.

"I want to eat you out," Philip said to Emily.

"No hurry, baby," she cooed. "We have the whole day ahead of us. You'll get your chance. Kiss me." He did, in a tangle of tongues, lips, hands moving up and down each other's bodies as they became better acquainted.

He was really loving her tits; they were bigger than his head, pillowy, and simply enormous. Margot was no slouch in that department either, but Emily was truly something special.

He stole a glance back at Margot. She was watching them eagerly, a hand lazily slid down the front of her panties. She caught his eye and winked at him, signaling him to return his attention to the voluptuous blonde beneath him.

Philip ran a hand through Emily's platinum hair. If it was dyed, it had been done recently; there were no visible roots. He cradled her head in his hands, staring deep into her beautiful blue eyes, her radiant smile, her wide, open face.

"You're beautiful," he whispered to her, and kissed her again, intensely. His kisses moved down her chin, along her neck, and toward her spectacular breasts. She rolled her shoulders, pushing her tits up into his face as he showered them with kisses, caressing them with his hands, licking and sucking at her gorgeous nipples. Her hands were on the back of his head, stroking his dark hair, holding him to her.

She looked across the room, locking eyes with Margot. Margot tried to look away, intimidated by her friend, but couldn't; that gaze was magnetic.

"He's good, isn't he?" ventured Margot.

"No complaints so far," grinned Emily. Slowly, she began to guide Philip down her body. He knew what she was intending. He trailed kisses down her stomach, to her hips, before finding his face in her moistening crotch. "Go ahead, baby," cooed Emily. "Eat me out."

As Philip's eager tongue lapped at her clit, Margot's fingers began to hasten, frantically moving against her own clit. Her other hand was squeezing her breasts through the thin material of her bra.

"Mmmmmm," moaned Emily. "You've never eaten out a fat girl, have you, baby?" Philip began to protest, but Emily shushed him. "It's okay. It doesn't need to be a bad word. Now answer the question." He shook his head, moving his tongue horizontally back and forth across her. Emily shivered. "Ooooh... he's good. You did a good job teaching him, Margot," she cried. Before long, she couldn't say much at all, reveling in the sensation of Philip's tongue.

He kept at it, encouraged by her cries of pleasure. Her juices were flowing into his mouth, that slightly sour vagina taste he had grown to love, her thick legs rubbing gently against his sides as if she wanted as much skin-on-skin contact as possible. He slid his hands slowly down her thighs, caressing the smooth skin as he went, rubbing her all the way down to her ankles as he studiously ate her pussy.

He heard a cry of orgasm from across the room. Margot. He felt Emily's hold on the back of his head tighten, as if to tell him not to turn his head to see her, but he already knew not to stop. He just smiled to himself, happy in the knowledge that even the sight of his oral technique was enough to get her off.

This must be how porn stars feel,

he thought.

He continued moving his tongue across Emily's engorged clitoris, back and forth, occasionally rolling it between his lips to give his tongue a rest, or occasionally dipping into her pussy itself to taste her, varying the rhythm.

Finally, he began to feel her hold on him tightening again, the tension building inside her. Her breathing was becoming faster, and he knew she was close. He kept going, resisting the urge to speed up, doing everything Margot had taught him about consistent, light movement of his tongue.

Emily squealed in delight, squeezing him gently between her thighs. She squealed again, and again, her climax building, and Philip continued to work his tongue, until she reached the very top of the mountain.

"FuckfuckfuckfuckFUCK!" she screamed, and he felt a rush of vaginal fluid pour down his chin. He felt her shivering and shaking around him as the orgasm wracked through her body. He kept licking, with increased urgency but not speed. He could hear Margot moaning again, watching the pleasure he was giving to her friend, until he brought Emily to a second peak and she screamed again.

The hand on the back of his head loosened, inviting him to rest his tongue. He looked up at Emily's beaming face, a trickle of sweat running down her forehead. "Wow," she whispered. "You're really gifted."

"He really is," squeaked Margot. He looked over to her now. She looked so happy in this moment, the happiest he'd seen her since the first time the two of them had made love. He winked at her and blew her a kiss, and she simply smiled back, her eyes soft and full of affection.

Emily's steering hand now dropped to Philip's chin, guiding his gaze back to her. "Stand up, baby," she cooed. He did, standing proud before her, fully erect. Emily climbed off the bed and dropped to her knees in front of him, her face only a few centimeters from his dick. She took it in her hands, examining it. "Look at this big pretty cock," she said. "Margot's a lucky gal." And without another word, she opened her mouth and fully engulfed his cock, sucking him all the way down to his balls until he could practically feel her uvula batting at his head.

"Holy shit," he gasped. She looked up at him, eyes dancing with mischief, before sliding her lips back down his shaft, until nothing but the tip remained in her mouth. She pressed her lips down on the soft head, a little bit of pressure with no teeth. Then she took his entire length again, faster this time. In and out, slowly increasing the speed. Her mouth felt amazing; if anything, she was even better at this than Margot was. Philip began to slowly pump his hips, gently, not wanting to choke her, but wanting to feel every inch of her wet mouth on him. His hands fell down to the back of her head, stroking her blonde hair as she sucked him. Without looking, she grabbed a tube of lube off the bedside table and smeared a finger in it, and he felt one of her hands creeping around behind him, her slippery finger tentatively rubbing at his asshole. He didn't resist, and she slowly poked into him, just up to the first knuckle, but enough that he could definitely feel it.

"Fuuuuuck," he moaned, as she worked. He stole a glance back at Margot, who was watching, enraptured. At some point, she had shed her bra and panties, and was now fully naked.

"Is she taking good care of you?" Margot asked, her voice dripping with exaggerated tenderness. All Philip could do was nod.

Emily took him to the very edge of coming, before abruptly pulling back, taking him out of her mouth, her fingertip sliding out of his ass. Philip groaned in frustration as Emily smiled up at him, before elegantly standing up and lying back down on the bed. She was on her back now, her legs spread wide, the position she had been when he entered, the length and breadth of her curvy, incredible body displayed in front of him. She grinned again, and beckoned.

This was it. He swallowed, nervous, but his penis, dripping with her thick saliva, remained at full mast. He climbed into the bed with her, climbed on top of her, felt her appreciative hands sliding down his sides, guiding him into position, his hands on her hips, the tip of his cock just brushing against her pussy lips. He pushed forward ever so slightly, feeling her part around him. She gasped in pleasure, but he pulled back, teasing her. He slid forward again, just a few centimeters, feeling her wetness again, and then pulled back again, leaving her gasping in frustration. He smiled down at her, doing his best to recapture the mischievous glint in her own eyes a second ago. Her expression was pleading.

"Please," she whispered. "Give me this young cock. Fill me up, Philip."

That was all the encouragement he needed. He thrust forward, into her wet cunt, and she gasped again at the feeling of him. "Oooooh," Emily moaned. "You're a big boy, Philip. Did you know that?"

"I guess so," he said, half-joking. "I don't have much of a frame of reference. I assumed I was average size."

"Mmmmmm," she moaned. "Baby doesn't know what a treasure he is." She rolled her hips, encouragingly, and Philip pulled back out before pushing back in, moving to the rhythm she was setting. He gripped her hips, pulling himself into her body with every thrust. Emily was crying out in pleasure at every movement he made; she felt it all through his cock. He pushed his head between her breasts, dragging his tongue along her skin, exploring the valley between and then climbing back up one of the hills, taking her puffy nipple in his mouth and swirling his tongue around it. Emily's fingers dug into his back, squeezing him, her curvy body almost enveloping him, and he loved it.

Gradually, he started to increase his speed, setting a faster tempo. Emily followed, with the movement of her hips and the frequency of her gasps of pleasure. But there was another sound, a buzzing. Philip stole a glance toward Margot and saw that she had produced a vibrator from her purse and was frantically pushing it to her excited clit. Philip grinned at her, a moment of eye contact, before returning his attention to Emily. He kissed her, passionately and deeply, a tangle of tongues, the taste of dick on her lips, but he didn't care. He felt so sexy right now, so wanted by both of these amazing women; this was no time to be a prude. This was the moment for him to be the dirty boytoy Margot wanted him to be. He would do whatever she wanted him to.

Emily's pussy was as wet as her kiss, and he knew his orgasm was approaching. One of Emily's hands was still on his back, but the other had migrated to the back of his head, stroking his dark hair as they kissed. The buzzing of the vibrator was getting more insistent, and he could hear Margot's cries of pleasure as her own orgasm built. His eyes were closed now, but he could feel hers, boring into him from across the room, and he loved it. He loved the feel of Emily's yielding body under him, her responsiveness to his every movement.

"Oh shit," grunted Emily, breaking the kiss. "You're gonna make me come again."

She pulled him into her again with an almighty heave. Philip gave her every millimeter of his cock, desperate to please her, and she gasped in delight before screaming out an intense orgasm. He kept fucking, riding it out with her, taking her to a pitch of ecstasy with his throbbing cock. But he wasn't quite ready to come quite yet.

Behind him, he heard Margot give out that same low moan he had come to know and love. "You like watching this, Margot?" he asked, not breaking eye contact with Emily.

"It's sooooo hot," she groaned.

"I like it too," he panted. "Emily's got a really nice pussy."

And then he felt himself release into her, that incredible, almost-numb feeling of ejaculating. Emily gave a tiny little squeal at the sensation of it, still moving her hips in time with his last few thrusts, her arms and legs squeezing him tight into her. He felt another hand on the top of his head.

Margot. He had never felt so much affection in his life.

Carefully, he withdrew his shrinking cock from Emily's dripping pussy, as Margot handed her friend a box of tissues. Emily grinned and took a few pieces, wiping herself down.

"Wow," panted Emily. "That was really good. You're a talented boy, Philip." She pulled him in for another kiss, deep and loving, breaking it finally to hand him off back to Margot. Philip felt himself passed between the two women, Margot's affectionate tongue sliding into his mouth. He wondered if she could taste Emily on his breath. He wondered if that bothered her. Apparently not that much.

"How was that?" she asked him, finally.

"Good," he said. "I thought at first it might feel weird, like I was cheating on you or something, but it never did. The fact that you were watching and enjoying it was what made it okay, I think."

"That's good. Because if it ever starts to feel uncomfortable, you can tell me. I don't want to push you into something you don't want to do."

"I wanted to do it," he assured her, gazing deeply into her eyes, and she knew he was telling the truth. "I think I really like being shared and passed around like a toy. It makes me feel... wanted. And, you know, Emily's really hot and I liked fucking her."

Margot chuckled at this. "Of course you did, you dirty little boy. This is a pretty sweet deal for you, isn't it?"

"It's an amazing deal," confessed Philip.

He felt Emily behind him now, her arms wrapping themselves around his shoulders, pulling him away from Margo. One hand traveled all the way down to his already-stiffening cock.

"You're hard again already?" she gasped.

"Of course," he said. "I'm in my early 20s. I could do this all day."

"Fuuuuuck," groaned Emily. "We may hold you to that." She turned him around, so that he was facing her, as she fell back onto the bed. "Margo can have a turn after this if she wants, but right now..." she turned over on the bed, lying on her belly, resting her hands on the cheeks of her curvaceous ass. "...I hope you like eating ass, baby."

Philip eagerly followed her. As he went, Margo gave him a light, encouraging pat on his own ass. Without hesitation, he dove into Emily's cheeks, sliding his tongue up her open, willing hole, swirling it around, relishing the sounds of her cries of delight. He slapped her cheeks, pulling them apart, kneading her voluptuous flesh as he worked. When his tongue got tired and he needed a break, he dragged his teeth along her wide asscheeks, raining kisses and little bites onto her.

"Mmmmmmm," Emily purred. "Nothing like a boy who knows how to eat ass."

Finally, she reached onto the bedside table and grabbed a tube of lubricant and a shockingly large butt plug. "Time for step two," she said.

Philip did as Margot had taught him, squeezing a blob of the lube onto Emily's asshole and pushing it in with his index finger. He heard Emily's breath catch as his finger slid all the way up to the knuckle inside her ready, excited hole. He pulled in and out, caressing her insides, loving the smooth, tight grip she had on him.

"Oh, fuck, that feels amazing," Emily grunted. "Just like that, baby."

He stole a glance back over at Margot. She was rubbing her pussy again, and her other hand was underneath her, tugging at her own butt plug. She winked at him again, and he returned his attention to Emily, sliding his finger in and out, faster and faster, just like Margot had taught him.

"Fuck," moaned Emily again. "You're... going to make me... cum... so fucking haaaaaaaaaaaaa..." Her words were swallowed up by her scream as the anal orgasm tore through her, rippling out from her ample ass cheeks down her legs, up her body. He let her ride it out, continuing the motion of his finger, until her cries died away and he felt the last bit of tension relax in her. Now, he knew, it was time for the plug.

He had never used one of these before with Margot, but it looked pretty self-explanatory. He smeared a blob of lube across its surface, and slowly pushed the tip of the plug into Emily's relaxed ass, watching her open wider and wider around it.