Under Her Wing Ch. 02

Over the rest of the summer, Philip's thoughts were constantly in Toronto, and Margot was doing everything she could to build up the anticipation. First she texted him a photo that looked professionally taken, a boudoir shot of her and Emily in frilly lingerie, sitting on a bed making come-hither eyes at the camera.

When he texted back the simple word "beautiful", she sent him a winky face emoji and a whole barrage of photos from the same session.

He'd seen porn before, but this was hotter even though there was no actual nudity, in part because of context. He knew these two ladies, had made love to one and was soon to make love to the other, and these photos had been taken with him, personally, as the target audience. He realized now how much he was looking forward, not just to fucking Margot again, but to fucking Emily. She was truly beautiful, in her way. She looked great in that sexy lingerie, anyway, her blonde hair done up in a bun and her truly massive tits barely contained by the bra. She reminded him of the plus-size lingerie models he saw on billboards at stores, and any society that said her body type couldn't be attractive, he realized, must be mad.

Margot, by contrast, was his every adolescent dream come true. Her brown hair was up in rollers in these photos, her lips painted an aggressive crimson that perfectly matched the red polka dots on the white silk of her camisole. And, of course, she still had those glasses on.

These photos, he knew, would be his primary masturbation fodder for the next month.

He got a friend request on Facebook from an Emily Shipton. Yes, he confirmed, the very same Emily. It occurred to her that he hadn't known to last name up to that point.

"enjoying the pictures?" she texted him.

"very much," he responded. "Can't wait to be there in person."

"Send me a dick pic," she wrote. "show me how much you're enjoying them"

"I don't know if I'm allowed," he replied. Wow. He'd never sent one of those before.

"Margot says its ok ;)" she wrote, followed by several eggplant emojis.

"I dunno I should probably get her permission directly," he said. He sent Margot a message. "Emily is asking for a dick pic can I send her one?"

While he was typing, he got another message from Emily. "Awww you're so obedient what a sweetie."

Margot replied a moment later. It was just a smiley face emoji and a thumbs up.

"Okay," Philip muttered to himself. He looked at the pictures again, stroking his cock to improve his erection. He was paying particular attention to one of Emily, bent over, hands against the bed frame, ass sticking out toward the camera, obscured from view by nothing but soft pink lace. She had turned her head back, giving the camera a very naughty smile indeed.

Philip looked at her fat ass, imagining he was on his knees behind her, her hands - or maybe Margot's - imperiously pushing his face between those big white buttocks.

He snapped a picture on his phone and texted it to her, and to Margot as well.

"mmmm" came Emily's response. "im really wet. Thats a nice big one i cant wait to suck it while ur girlfriend watches".

Margot replied a moment later with "I miss you."

Over the next few weeks, he'd get texts from them now and then. Margot sent him a picture of a massage table she'd bought after he finished up the massage course she'd instructed him to sign up for. Emily asked if he wanted to see a picture of her pussy, but then sent him a picture of an actual literal cat.

"this is Hazelnut i am fostering her for Toronto cat rescue."

Finally, and perhaps most concerningly, there was the picture Margot sent him of herself one morning. She was topless, those big beautiful tits he had grown to love on full display. She had a terminal case of bedhead and no makeup. It looked like she'd taken this moments after waking up. All she seemed to be wearing was a big blue strap-on, about the size of his own penis, that projected from her crotch.

The caption was "It's getting to be time, baby."

In late August, Philip rented a van and got a few friends to help him load his things into it. He'd arranged for some friends who already lived in Toronto to help him unload everything when he got there, too. It was a long, stressful drive after a long, stressful packing process, and he knew the unpacking process wouldn't be much better. The one bright spot on the horizon was that both Margot and Emily had offered to help out.

Finally he pulled the van onto Major Street. He'd been able to arrange with his new landlady to move in a few days before the first of September, giving him time to get set up before classes started, and also meaning that the street wasn't crowded with other people who were also moving. He parked the van, locked it, and sent everyone who had offered to help a group text.

"Just pulled in. I'm going to go get dinner right now but I'll see you all in about an hour?"

He got a small chorus of responses and confirmations. Then a private message from Margot. "I'm free right now if you want to get dinner together. My treat"

They arranged to return to the taco fusion place they'd gone to on his first night in Toronto over the summer. When Philip arrived there, Margot was already waiting outside, and his heart leaped to see her. Perhaps he was partly expecting to see her all dressed up for him, but no, she was wearing blue jeans, a slightly-worn t-shirt, and no makeup. Which made sense, really, since there would be heavy lifting involved. But as he approached, her face lit up and she put her arms around him, pulling him in for a passionate kiss, almost the kind of kiss she'd normally reserve for when they were in private.

"I fucking missed you," she said.

"Missed you too!"

They went in and got a table with menus.

"So I was thinking," said Margot, "we probably won't have time to set your place up as well as move everything in. If you'd like to come over and sleep at my place again, I'd love to have you."

"That sounds nice," he said. "But I should warn you right now, I've been either on my feet or driving all day. I'm already pretty tired and by tonight I'll be utterly exhausted, so don't expect much of me."

Margot smiled. "Don't worry, Philip. I'm a reasonable woman. We'll have plenty of time, now that we're going to be neighbours." She slid a hand to his knee, but it was more of a gesture of affection than a sexual advance. "When does school start? Not til September?"

"Yeah, next Tuesday," he said. "I need to get set up in my new place first. I could certainly use a guide, though. Someone who knows this neighbourhood?"

"Well, I'll be working during the day, of course, but I could certainly show you a few things. Grocery stores, things like that. And I think Emily had something she wanted to show you, of course." She winked at him.

Dinner was excellent, and the rest of the move-in went very well. Margot caught a few of Philip's friends checking her and Emily out, wondering who these beautiful older women were and how Philip knew them. Emily, at least, seemed to be loving the attention, and was a shameless flirt all evening.

"Don't worry," she said, when Margot took her aside. "I'm not going to fuck one of his friends. I know how young guys get about these things."

"Okay," said Margot. "Look, I really like Philip, and I don't mind sharing him with you, but I don't think it's a good idea to drag his friends into this. I don't want to mess this up."

"Don't worry," Emily said again. "I've got a hook-up lined up for tonight already. Guy I met at the club the other night."

"Is he hot?"

"Fuck yes," said Emily. "I'm going to be riding that boy's face until morning. I'm just teasing these kids to get myself warmed up."

After a few hours, everything was moved out of the truck and into Philip's new apartment. They returned the van to the rental agency's Toronto location, and Philip bought everyone a round of beer at a nearby bar. It was a good time, but everyone was very tired and it wasn't long before his friends began to trickle out. Philip, for his part, was exhausted, and barely remembered even walking back to Margot's house afterwards.

When he woke up, he was on the pink sheets of Margot's bed. She wasn't next to him, but the living room light seemed to be on, so he assumed she was already up and active. He began to sit up but something pulled him back to the bed, and he realized he had been hand-cuffed to the bed frame. There were manacles around both his wrists, and his heels, holding him spread-eagled over the mattress.

"Margot?" he called.

After a moment, the door opened. Margot was there, her hair up in rollers like in the boudoir shots, her clunky glasses on, but other than that, she was completely nude. No, not nude. She had the strap-on.

"Good morning, baby boy," she whispered to him. "Are you ready for this?" She reached down, grasping the prosthetic phallus and jerking it like a real penis.

"I hope so," Philip said. He wasn't in love with the idea of getting pegged, but couldn't deny a certain curiosity. Seeing Margot so transparently aroused was sexy enough in its own right, after all.

She slowly walked toward him, wiggling her hips with every step, and taking the same tube of lubricant from her shelf that he had used on her over the summer. "Good. Because it's time to show me that you're mine."

She squeezed the lube onto her index finger and slid it, quickly, up his ass. He was amazed how easily it went in. With her other hand, she took a hold of his penis and moved it to her mouth as she knelt over his crotch. She licked and kissed at his shaft, never quite taking it into her mouth entirely. He wanted to put a hand on the back of her head, run his fingers through her hair and push her onto his cock, but the manacles prevented that. She squeezed his balls and licked his knob, while poking her finger deep into his butt, getting his insides slippery with lubricant. Finally, she pulled her finger out, a bubble of lube making a popping sound.

She poured more lube over the strap-on, streaming a line of the stuff onto the shaft, and smearing it along the length of the thing. She ran a lube-stained hand along his chest, towards his stomach, where he felt that involuntary fluttering of the muscles he'd felt before with her. He laughed, uncontrollably, and perhaps a little uncomfortably.

Margot, concerned, instantly dropped her facade. "I won't hurt you," she reassured him. "It'll feel really good. I promise."

"I know."

"Look, if you don't want to do this, we don't have to."

"I don't mind. I want to do it. For you." Margot smiled. "There are so many things I would do for you, Margot." It looked like she was fighting back tears now, but the moment quickly passed, as sentiment gave way to lust.

She moved her hips between his legs now, getting underneath him. He could feel the big dildo between his cheeks.

"Fuck me, Margot," he hissed to her. "Fuck me, you filthy thing." She smiled widely now, and took the dildo in her hand, lining it up with his anus, before pushing in with an almighty thrust.

"Like that?" she said.

Philip couldn't say a word. It was an overpowering sensation, though not entirely an unpleasant one. He'd never felt anything like this before.

Margot laughed now. "Aww, poor baby can't talk." She reached down toward his face and slapped him, hard. "Welcome to Toronto, fucker," she hissed.

She took his dick in her other hand and started to jerk him off. They locked eyes now, his expression wary, like a deer in the headlights. He was panting, hard, as she drove the dildo up his ass.

"I'm going to fuck you," she said, "until you come. You're going to come all over my stomach and tits. Then, if you're good, I'll undo these cuffs and let you go."

Philip finally found the breath to speak. "I don't want to go," he moaned.

Margot grinned. "How does it feel, getting fucked up the ass?"

"I don't know," he said truthfully. "I... I don't mind it. I like that you like it."

"This is just something I really, really want to do," she whispered.

"Do it," he said. "Make me yours, Miss Blumstein. I want to be your little teacher's pet. Slap me again."

She did, hard. She was getting more and more excited now, driving the toy into him faster and faster. Philip was getting to enjoy it, honestly, letting go of his masculinity, even just in play.

Margot's breath was getting heavier now. He realized that the other end of the dildo was rubbing against her clitoris, bringing her closer to an orgasm of her own. And suddenly, he started to feel what she was talking about as the strap-on hit his prostate. There was a feeling like a giant air bubble in his ass, and he ejaculated quickly, hard, in her hand, Margot angling him toward her stomach. His seed arced high, speckling the undersides of her breasts with sticky whiteness. But even as his orgasm subsided, she kept humping, driving into him.

"I'm so close," she moaned. "Just a little longer."

"As long as you need," he gasped.

Margot grinned, biting the knuckle of the hand that had been on his ass. Her other hand, the clean one, she stuck up toward his face, sticking her index and middle fingers into Philip's mouth. He sucked them, gently. Margot gasped, and stopped thrusting, collapsing across his body. He could feel his own cum squishing up between their stomachs. Her body was shuddering. So was his, now that he thought about it.

He craned his neck down as far as he could and kissed her hair. "That was fantastic," he said. "Thank you for introducing me to it."

Margot looked up at him, tears of happiness rolling down her face. "Thank you for letting me do that," she said. "Oh God, I missed you, Philip Santos." She kissed him now, not hard but soft, a tangle of tongues, lips, and tender affection.

They lay like that for a few minutes, catching their breath, before she finally undid his cuffs. Even then, they stayed on the bed, her lying across him, his arms around her.

"My ex-husband would never let me do that," she said. "He thought it would turn him gay or something. Kept trying to stick his up my ass, whenever he got a chance."

"I thought you'd never had anal before," he said.

"You were the first guy I could relax enough with," she said. "I was never opposed to the idea. I liked it, in fact. But I guess subconsciously, I never really trusted him."

"Well, he's gone now," said Philip. "And speaking of exes, I heard from Sarah recently."

"Oh yeah?"

"Yeah. She's a lesbian, it turns out. She moved to Vancouver and is much happier."

Margot laughed, which was exactly what Philip had hoped for. He'd wanted to cheer her up. "Okay. Good for her. Good for everyone who got out of that town." Margot reached a hand up and started to idly stroke Philip's hair. "I think we both need to shower," she said. "We're covered in your cum. Then we'll have breakfast and head over to your place to set things up. Deal?"

They walked back over to Major Street, Philip still in yesterday's sweaty work clothes. "I want to change into something clean as soon as I can," he said, moving a box off of a suitcase. He found a shirt and pants, and got some socks and underwear out from a duffel bag.

She helped him pick out where to put his furniture, although there was a lot of room left over. It was a space much bigger than he was used to, and it looked strangely hollow, tomblike.

"I'm going to let you unpack these books on your own," said Margot. "I don't know how you want to arrange them on the shelves. You're in charge of that."

"No problem," he said. "Thanks for helping me today."

"I can't think of a better way to spend my day off," Margot said, tousling his hair. Philip turned around and kissed her. What started as a kiss quickly moved into full-body caresses, and it wasn't long before she'd pulled his shirt off.

"Let's go into your room," she said. "I don't want to have sex in the living room until you've got curtains up."

"Fair," Philip agreed.

They moved into his new bedroom, where the bedframe was leaning against the wall, in pieces, along with the mattress. Margot pulled the mattress down onto the floor, where it landed with a loud, dull thump.

"How do you want me?" she said.

"Let's just lie down on the bed and see how it develops," he said.

Margot smiled at him, moving down onto the mattress, lying on her side. Philip lay next to her, facing her. They kissed again, gently, tenderly.

"We've got all day," he said. "Let's take our time."

They made out for a few moments like that, slow and relaxed, but it was not to be. Neither of them could relax, both finding themselves more eager than they had initially anticipated. The kissing, again, became more aggressive, and Philip found his hands migrating up Margot's shirt. She thrilled at his touch, biting her lower lip as his hands moved under her bra, palms flat against her puffy nipples. She arched her back, pushing them harder against his hands. She moved her arms up over her head, pulling off her top quickly, then reaching around her back and unhooking her bra.

Philip brushed it aside now, and moved his head down to her nipples, taking one in his mouth, then the other, sucking, licking, giving just the slightest amount of pressure from his teeth. Margot was already moaning, and she moved a hand down to his crotch, feeling his hardness through the denim of his jeans.

"I'm so glad you're back," she whispered to him. He didn't respond, but just kept working his mouth at her big nipples.

She moved her other hand down now, blindly groping for his zipper. She pulled it down and yanked his jeans down around his knees, pulling his boxers off with them, before grasping his cock and pumping it up and down frantically.

"Fuck me, Philip," she cried. "Fuck me now."

He nodded, and wordlessly reached down to unzip her shorts, helping her quickly out of them and her own panties. She noticed that he had, at some point she hadn't noticed, kicked off his socks, though hers were still on, as well as her glasses.

Margot lay on her back now, her legs wide open, her wet pussy on full display. Her eyes roved hungrily over Philip's muscular young body, his hairless chest and big, thick cock.

"Fuck me," she said again.

Philip moved between her legs, and his erection instantly found its way into her, unburdoned by a condom for the first time. They both gasped in pleasure at the sensation of it.

"I've really missed this feeling," she whispered. "Having you in me."

"These last few weeks have been torture," Philip agreed. He moved his left hand to her hip and his right to her shoulder, taking her entire body in his arms, bracing her, as he moved in and out, pushing her down as he moved up. Margot squealed in pleasure. She was just amazingly wet.

He buried his face in her hair as he pushed himself into her. She clawed at his back, feeling his beautiful erection plunge in and out of her, sliding past the lips of her vagina and stimulating her g-spot perfectly. She took his ear into her mouth, running her tongue through its complex shape.

"Rub my clit," she whispered. "Rub my clit and I'm all yours."

He moved his left hand across to the top of her cunt, moving his chest up to give it some room, and using his right arm to prop himself up on the mattress. In this position, he couldn't thrust as hard or as quickly, but his finger was on her button, flicking lightly, just as she'd shown him before, and he kept his cock moving, slowly but as stiff as ever.

She was so close now. Her cries were becoming screams, his name inarticulately howled against the echoing walls of the apartment. Her eyes were screwed up shut, her neck arching. Philip kissed her chin, moving his lips down her long neck, licking and sucking her soft skin, before moving back up, along her face, and whispering in her ear.