Under Her Wing Ch. 02

"You drive me crazy, Margot."

She came now, explosively, screaming up at his bedroom ceiling. He felt her nails digging into his back, her legs wrapping around him so hard he could barely breathe.

"I'm gonna come," he whispered.

"Come inside me," Margot cried, still in the depths of orgasm. "Fill me with it!" She brushed his hand away from her clit now, and he moved back into his previous position, holding her tight against him. He bucked frantically, sticking her with his hard rod before finally erupting in her still-spasming cunt.

As his thrusts slowed, she gave a long, purring sigh, feeling his hot semen spread through her. She put her arms around him, squeezing him tight, and kissing him, deeply, on the lips. Philip squeezed back, kissing her, reveling in the moment and their reunion.

That afternoon, Margot showed Philip the nearest grocery store, and he bought his first load of food in Toronto. They went back to her place for the night, him bringing a change of clothes, and she showed him the new massage table.

"I have a long day ahead of me tomorrow," she said, "so maybe after work I can lie on this and you can show me what you've learned."

"Sounds great," said Philip. "When is the thing with Emily happening?"

"I don't know," said Margot. "I'll text her and see when she wants to do it. I'm really looking forward to seeing you two together."

"I'm looking forward to it, too," said Philip.

"Of course you are, you pervert," said Margot, giving him a teasing slap. "More pussy can't possibly hurt, can it?"

"Nope," said Philip, smiling. "I'm an obedient boy. I do what Miss Blumstein commands, even if that's to fuck her friend."

"Oh, you're going to fuck her, alright," said Margot. She had slid a hand down Philip's pants now, and was grasping his stiffening cock. "Cute boy like you, she'll just eat you up. You're going to fuck her on my bed, and I'm going to sit in that chair right there and I'm going to watch. I'm going to watch you push your gorgeous cock up her her fat cunt."

Philip started to thrust his hips slightly against her hand, and he put his own arm around her waist. "Will we need to use condoms with her?"

"I don't think so," said Margot. "I'll ask her when she last got checked, but it should be okay."

"Are you going to fuck her?" Philip asked.

"No," said Margot. "I'm only into guys. But I like to share with my friends." Margot unzipped his fly now and pulled out his cock. "Oh, she's going to love this. And I have a few other friends who might enjoy your services as well..."

"You're the boss," said Philip.

"Yes I am," said Margot, grinning. She dropped down onto her knees, putting her mouth over him, forming a tight seal with her lips. She bobbed her head back and forth along his length, and he felt her tongue running along the underside of his helmet.

"Holy fuck," he gasped. His hand fell to the back of her head, his fingers running through her brown curls. She looked up at him, warmly, lovingly, as she sucked him. It reminded him of that first blowjob she'd given him, months ago, in this very room.

But just as he was getting into it, she pulled away and sat on the edge of the bed. "Come here, little boy," she whispered, beckoning to him. "On your knees."

As he knelt in front of her, she wiggled out of her shorts and panties, pussy on display once again. She put her hand on the back of his head and pulled him, firmly, to her clit. Philip stuck out his tongue, lightly flicking her little button with it as she had taught him, and she gave little, gasping cries of pleasure every time he touched her. She was starting to get very wet indeed now, and he felt her juices pooling around his chin.

"Give me a finger," she whispered, and Philip slid his index finger up her wet cunt. It moved smoothly, with no resistance, along her slick box, stroking her insides the way she liked as he moved in and out. "You... you remember what I taught you," Margot gasped. "You're doing very well, Mr. Santos. Make me come and I'll let you fuck me. Would you like that, Mr. Santos? To fuck your teacher?" The roleplay was back.

"I'd like that so much," Philip whispered. "What red-blooded boy doesn't want to fuck the teacher?" Margot gave a squeal of delight at that, and within a few minutes, she came in a gasping mess all over his face. Without wasting a moment, she stood up now, putting her hands against the wall.

"Get behind me," she commanded. Philip hastened to obey. She started to slowly grind her ass against his crotch, arcing it now to give him access to her pussy. "Fuck your pretty teacher up against the wall."

It was an unfamiliar position, and Philip had a bit of trouble feeding his dick up into her, but they soon got the angle right. He put his hands on her waist and thrusted into her, drawing a deep, satisfied moan from her. Before long, he'd found a good rhythm and balance, and he moved his hands up, under her shirt. He undid her bra but it didn't fall down, just sat loose under her shirt, letting him move his hands around front to cup her breasts himself. She was shimmying her shoulders, pushing her tits against his palms, and her felt her arousal in the stiffness of her nipples, the wetness of her pussy.

"Miss Blumstein," he hissed into her ear, "you're my favourite teacher."

Margot gave a shriek of pleasure before replying. "And you're my favourite little teacher's pet. You've learned all this so quickly! You're my prize student!" she gasped. "My beautiful boy!"

They both lost track of time as Philip pumped his young dick into Margot's cunt. It felt like hours to Margot, an endless afternoon of pure bliss. She felt his hot breath on the back of her neck, his wet kisses against her ears. He heard her cries of pleasure, her sighs and moans. Finally he felt his orgasm approaching.

"I'm gonna cum soon," he whispered.

"Oh, me too," purred Margot. "Let's try to cum together." She moved her arms now, her right arm steady against the wall with the entire forearm, rather than simply the palm, while her left arm fell to her crotch, her fingers desperately working at her clitoris. She started to count down. "Ten..." she whispered. "Nine..."

Philip got the idea now, and began counting down along with her, his pace building to the frantic climax.

"Eight... seven... six... five... four... three...

"Two..."

"One," Philip whispered into her ear. He came now, his knees going weak as burst after burst of semen shot out of his cock and into her. He felt her cunt twitch around him, tightening and growing slack, juices running like a waterfall, as Margot came too. She screamed, almost deafeningly, into his ear.

"A Plus," she moaned, with the last of her breath.

Philip spent the night at Margot's place. They didn't have sex again that night, both too exhausted from their almost nonstop fucking since he'd gotten back into town, but they knew the next time wouldn't be far off.

He woke up when her alarm went off.

"Do you want to sleep in a bit?" mumbled Margot as she got out of bed.

"Yeah, if that's okay," Philip said.

"That's fine. I have to go to work, but you have a key, right? You can let yourself out and lock up?"

"Yeah." Before long, he was asleep again.

When Philip woke up again, it was about 8:00. He took a shower, changed into his new clothes, and walked home, careful to lock Margot's front door on his way out. On the way over, he decided that today would be a good day to explore the campus a bit and buy his textbooks.

At about 4 in the afternoon, he got a text from Margot. "Come over at 7 tonight. I need that massage badly."

"Rough day at work?" he texted back.

"Could have been worse i guess. Just very stressful"

"Np i'll be there"

She texted back a smiley face.

He let himself in at 7. He could hear Margot's voice, talking to someone, but the other party seemed muffled.

As he followed her voice, he saw her spread out on the massage table all ready for him, completely nude and lying on her stomach. He loved the way, as always, her ample breasts crushed up beneath her, against the table, and the plump cheeks of her ass on full display, unashamed.

"Hang on, Emily," said Margot. "My massage is here." Philip realized she'd been talking to Emily on her phone, which was on speaker.

"Can you still talk?" asked Emily.

"Yeah, it's okay. I've got it on speaker." She looked up at him, a distant look in her eyes, as though she didn't know him, as if he were simply a nameless masseur, and Philip realized her game right away. More roleplay. "I carry most of my tension in my shoulders and lower back," she instructed him. "Really get in there, too. Be aggressive." She smiled politely.

Philip moved up behind her as her conversation with Emily resumed.

"No, I can't tell you about today," she said. "It's a doctor-patient confidentiality thing. Just a long day, I guess."

"Sounds like you could use the massage then," said Emily.

Philip noticed that Margot had left out a number of massage oils on the table's tray. Good. He picked one and rubbed it into his hands. Standing alongside Margot, he set to work on her shoulders, using all the skills he'd learned over the summer.

She gave out a low, pleased moan. "Just like that," she said. "They didn't tell me what your name was at the agency."

"Oh, it's Philip," he said, playing along.

"Well, do me just like that, Philip," she said. "So Emily, how did your date the other night go?"

"Just fine," said Emily. "He bought me dinner, and then we went back to my place."

"Then what? Details, girl."

"Let's see. First we made out on the couch a bit. Then I rode his face for a while, and he fucked me doggy-style on the rug. Then I kicked him out and he went home." Philip was getting a little hot and bothered listening to all this. He knew Emily must realize he was listening, and wondered how much of this was for his benefit, was the two women teasing him.

"Was it any good?" asked Margot.

"Not bad," she said. He made me come twice, so can't complain there." She giggled. "I'll probably see him again. Maybe I'll let him fuck my ass next time." Philip realized, suddenly, how erect he was, his penis hard and heavy against his jeans.

Margot glanced at his crotch, and laughed. "I think you're upsetting my masseur!" she told Emily.

"No, no problem," said Philip. "I'm a professional."

Margot smiled at him, a little more naughty this time. "Can you go a little lower?" she asked, wiggling her bum just a tiny bit. He moved a bit lower now, trying to focus on making it an actual massage and not just foreplay. He got in there. He found her tension and massaged the knots out of her. But as Emily got more and more into the details of her hook-up, Margot became more clearly aroused. He could see her vagina beneath her, glistening wet, and the fluids flowing down onto the surface of the table, as Emily talked and Philip's hands worked.

"Do my glutes," she instructed.

Philip reached for the oil again and noticed that among them was that tube of lubricant. He grinned, realizing what she had in store for him. All this talk of Emily getting butt-fucked must have been calculated. Even Margot's own body language had all been for the express purpose of drawing his attention to her ass.

But Philip stuck, for now, to ordinary massage techniques, rubbing and caressing Margot's cheeks in as nonsexual a way as he could manage, teasing her. She was becoming increasingly restless as she responded to his skilled hands, her breathing getting shallower and her attention wandering from the conversation with Emily.

"Listen," she said to Philip, "can you really get in there?" She was pushing her ass up against his hands now, tormenting herself with her own arousal, and Philip finally decided to be merciful. He squeezed the lube onto his finger, rubbing it up and down, before poking Margot, slowly, in the anus, sinking his digit all the way into her. Margot gave a low moan of pleasure.

"Are you okay?" asked Emily.

"Yeah," she said. "Just... my massage. This guy's very, very good." He smiled at the compliment, moving his finger very slowly, in and out of Margot's ass, his erection unbearable against his pants. He kept rubbing his finger back and forth until there wasn't even a hint of friction and her anus was coated in the slick lubricant. Now he pulled it out, with a popping sound, and spread her cheeks apart, gently. Margot understood what he was doing, and lifted up her hindquarters for easier access as Philip, crouching behind her, pushed his face down into her ass, licking her hole delicately. She tasted clean, and had probably given herself an enema before he arrived.

"Oh my God, yes," cried Margot. "Lick my asshole, Philip. Philip was your name, right?" she teased.

On the phone, Emily went quiet for a moment, but when he listened, Philip realized he could hear her breathing, heavy and rapid, as she listened. His erection raging, Philip finally unzipped his pants and dropped them to his knees, his underwear falling along with them, and his thick cock whipping free. Margot was giving out little cries of pleasure now, her hand on the back of Philip's head, pushing him up against her ass, but still making a valiant effort to carry on the call with Emily.

"No, it's just the massage," she panted. "I don't know what he's doing back there but it feels incredible." Bullshit. She knew.

"Maybe I should sign up for a massage with this guy," purred Emily. "You said his name is Philip? Philip, how does Monday sound for you? Labour Day?"

Philip tried to lift up his head to reply but Margot held him where he was. "Monday's fine," he tried to say, voice muffled by her ass.

"He says he'd love to see you Monday," laughed Margot. "How about my place at noon?"

"Can't wait," said Emily. Philip could tell she was masturbating over the phone but wasn't entirely sure how. Rubbing her clit? Playing with a dildo? The mystery intrigued him, the idea that his eating Margot's ass not only turned both of them on, but also this beautiful third party.

Margot released her hold on Philip's head now, and he stood up. He took the lube bottle again and poured it over the length of his cock, rubbing it in carefully with his fingers as Margot gasped in anticipation.

"I think I'm about to get fucked," Margot whispered into the phone, a giggle of girlish excitement in her voice.

"Fucked how?" said Emily, her voice husky.

"Anally fucked!" she squeaked.

Philip moved onto the table as well now, straddling her beautiful body. Margot pushed up against him, lifting up her ass to give him access, doggy-style, as he lined himself up with her pretty little hole. He thrust in now, slowly. For a moment, the only sound in the room was their breathing. Then the squelching of the lube. Then a high-pitched squeal of delight from Margot as he pushed all the way into her, unprotected.

It felt different without a condom. He could feel his foreskin moving back and forth inside her, along his cock, as the muscular ring of her anus gripped him gently. There was no friction beyond that, to speak of, she was so relaxed and thoroughly lubricated.

"Is he in?" asked Emily. "Is he sodomizing you?"

"Oh, Emily, it's so fucking good," Margot panted. "He's such a hot boy and he's sticking his big fat dick up my ass!"

"I bet you feel like a dirty little slut now," Emily moaned. "Letting the massage guy stick it up your ass?"

"Oh, I do! I do!" cried Margot. "But he's so hot, I can't resist it!"

Philip wondered if it would be okay for him to say something. Would it break the scene, so to speak? He decided to stay quiet. Margot and Emily would invite him into the conversation if they wanted to. For now, he was contain to remain in the third person as he moved in and out of Margot's bowels. She turned her head back now, and he saw the frenzied expression in her eyes. She kissed him, roughly, forcefully, her tongue probing into his mouth.

"Such a big fucking cock in my ass!" Margot screamed. He could tell her orgasm was approaching. "He's gonna make me come, Emily!" She was so aroused from the massage that it wasn't taking long at all.

"Come for him, you slut!" cried Emily. It sounded like she was getting pretty close herself. "Fuck her, Philip! Fuck her good! She needs it!"

"You're next, Emily!" hissed Philip, finally invited into the conversation. "I'm gonna make you scream and then I'm gonna come all over your face!" He realized, as it said it, that he was really saying it for Margot's benefit, not Emily's. He leaned into Margot's ear now, and began whispering in the breaks between her cries. "I'm gonna fuck your ass, Miss Blumstein, and then I'm gonna fuck your friend's ass, and you're gonna watch. You're gonna watch me pump it in and out of her ass, and you're gonna watch my cum drip out of her."

"Yes!" screamed Margot. "Yes! Yes! Fuck both of us! Oh, I want to see that so badly!" Her words began to fail, as inarticulate screams took over. Philip kept the fucking steady, though. A laboured scream came from the phone now.

"Oh, Margot," cried Emily, "I'm coming. You and your cute little massage boy... eeeaaaaaaaaahhhh!" she howled, clipping the phone's audio. Margot wasn't far behind, with an ear-piercing scream heralding her climax, bringing Margot to anal heaven.

Her entire body clenched and then relaxed, more relaxed than she'd ever been. Her asshole gaped open around his cock, her cunt yawning open, juices simply pouring out of her. A thread of spittle dropped from her watering mouth.

"He's still going, Emily," she moaned.

And he was. Philip kept fucking her upturned ass, pushing his turgid cock down into her slippery depths. He wasn't tired yet, nor was he speeding up with the frantic energy of his own impending orgasm. He was just still going.

"Lucky you," purred Emily. "The stamina on these young guys..."

Margot gave a low, wordless sigh. "He's so good to me. Because he knows who the boss is. Who's the boss, Philip? Say it."

"You're the boss, Miss Blumstein. You're my boss, you're my teacher, you're everything," he grunted.

"And don't you forget it," Margot panted. "Oh baby, keep pushing that cock up my ass. Give it to me. Make me come again. That's right. In. Out. In. Out." She started chanting the words, rhythmically, guiding the tempo of their sodomy.

After a while, Philip finally started to feel his orgasm coming. Margot was close to coming again, though, he could tell, and he wanted very much to give her another climax.

Emily, too, seemed to sense how close they both were. "Philip, Margot tells me she introduced you to pegging. How did you like letting her be the man?"

"Just fine," said Philip. "Why do you ask? Did you want a piece of my ass?"

"Oh, young man, I'd snap you in half," she breathed.

"Can't fucking wait," said Philip, and Emily gave a cry of pleasure. "You could fuck me and I'd fuck Margot. We could make a nice big butt-fuck sandwich. Would you like that?"

Margot's breathing had gotten frantic by now. "Ten," she announced. "Nine."

When she got to zero, Margot shrieked in pleasure, and Philip released his seed up into her asshole, feeling it spread within her as his cock kept twitching, shooting out more cream into her depths. Margot was screaming, panting, crying, cooing, purring. The room was rank with the smell of sweat, ass, dick, lube, even the juice from her pussy. He kept pushing into her, letting her ride out the last of the orgasm before his dick went soft. Finally, he pulled out and collapsed into the nearby couch, sweaty, out of breath, exhausted. Margot was a gasping mess on the massage table, her asshole gaping wide open and a trickle of jizz dripping out of her. And the phone was silent until finally Emily spoke.

"See you both on Monday then," she said, and hung up.