Under Her Wing

"I can't get at your clit from this angle," he said.

"Then move lower," she commanded. He scooched down on the bed until the top of her pussy was level with his tongue. He moved two fingers in, stroking up along her lips and quickly locating her clitoris. "There it is," she said, trying to hide the catch in her voice as he stimulated her. Philip began flicking his tongue, just like she had shown him, against her little bud.

"Mmmmmmm," purred Margot. "That's good. You remember." She bent down now, giving him a better angle and spreading her body across his own. He realized that her face must be level with his cock now, just as he felt her tongue against his shaft. She licked upward, toward the tip, before taking the head of his penis into her mouth. He could feel her wet lips against him and her tongue swirling around his knob. He started to buck his hips, gently, against her mouth movements. After a while, he became so concentrated on how good the blowjob felt that he was struggling to keep up the rhythm of tonguing her. Margot noticed this, and drew him out of her mouth, pushing her ass and pussy down harder into his face.

"You see the problem with sixty-nine now," she said. "It's a great way to get started, but after a while it's hard to concentrate. That's usually when it's best to transition to proper fucking. Do you understand?" He tried to reply, but his words were muffled by her pussy. "I said, do you understand? Say 'yes, Miss Blumstein.'" She eased up now, moving off his mouth so he could speak.

"Yes, Miss Blumstein," he gasped. For a moment, her strict teacher aspect vanished and she looked genuinely concerned as she turned around and sat on the bed.

"This isn't too intense for you, is it? I can slow down if you want. Are you okay?"

"Never better, Margot. Is this what roleplay is?"

She smiled. It was a tender smile, the real Margot. "This is light roleplay. Usually about as into character as I like to get. If you want to try a different dynamic, we can. It's important that you're comfortable with all this and that we communicate. You're so young and inexperienced."

He smiled back. "I am young and inexperienced. That's why I'm grateful for your lessons, Miss Blumstein."

He thought she might smile, but she didn't. Her face went stern again, and she gave an exaggerated little "hmph!" She crossed her arms under her large breasts. He could see her nipples were firm again, standing up at attention. "Pile up the pillows," she commanded. "I wish to lean against them. Then fetch a condom from the drawer." Her gathered up the pillows, as she had instructed, around the headboard of the bed, and then moved to the bedside table. The drawer she had taken a condom from the night before was still open, and he took out another packet and hurriedly ripped it open, pulling out the condom. He held his penis in his hand and was about to roll the condom on, just as she had done, when she slapped his hand. "Don't touch yourself," she said. "There will be no masturbation under my roof. Give me the condom." She took his cock in her own hand now, and rolled the condom on, herself. "That's better. Now, Mr. Santos, I'm going to teach you about missionary position. Some say it's a cliche, but it's a cliche for a reason, and an excellent foundational point." She leaned back onto the pillows, spreading her legs wide. She reached a hand down and, without breaking eye contact with him, began to rub her clitoris. She raised an eyebrow, daring him to say something, to call out her no-masturbation hypocrisy, but Philip was silent. She pushed a second finger right into her pussy, then pulled it out, with a soft squelching sound. The finger was shining wet, and she beckoned to him with it. Philip climbed, carefully, over her reclining body, and she moved the wet finger to his face now, pushing it, gently but insistently, into his mouth. Philip had no objections, happily sucking down her love juices as he felt her body under his. She was so soft, with her wide hips and pillowy ass and heavy breasts. "Put your hands on my hips," she said, and he did, resting his elbows on her propped-up knees. She grabbed his penis at the base, between two fingers, and pulled him, slowly, into her. She gave a low, dragging moan as he entered her, the cry fading out as he finally had no more length to give. "You're in my cunt now, Mr. Santos," she panted. "How does it feel?"

"It's the best feeling in the world, Miss Blumstein," he said. He noticed a momentary, out-of-character smile flicker across her face.

"I'm going to let you take over for the time being, Mr. Santos. I'll issue pointers and corrections as needed, but I want to get a sense of your instincts in a situation like this. What comes naturally to you? Do you understand, Mr. Santos?"

"Yes, Miss Blumstein," he said, and slowly pulled back out of her before pushing, rapidly, in. He started to slam, rapidly, in and out of her now, pounding her tight, wet cunt.

"Not so fast," she chided. "You can't just go off like a wild horse right out the gate. Give it to me slow, but hard. Make me moan. Speed up gradually, when the time is right."

"How will I know?"

"How will you know, Miss Blumstein," she corrected. "I'll let you know, Mr. Santos." He started fucking her, slowly but forcefully, driving his fat cock into her as far as it will go. "As you withdraw," she said, "try to push upward a little bit. Stroke the ceiling of my vagina, Mr. Santos." Her impassive, instructional manner was maddening. He wanted now, more than anything else, to impress her, to see that smile again, to hear her scream. He had a pretty good idea what was going on behind the mask, though; Margot knew precisely what she was doing to him. That was the fun of it. He found a rhythm that felt right, and was careful to obey her instructions on angles. She wasn't moaning out loud, but her could feel her nails digging into his back, feel the passion in her fingers.

"Am I doing well, Miss Blumstein?"

"You're doing very well," she said. "It feels very nice." She smiled now, just a little, controlled smile. "Mmmmmm. I want you to suck on my nipples now, Mr. Santos, while you fuck me. Will you do that?"

"Yes, Miss Blumstein," he said, and lowered his head to her left breast, taking her fat, pencil-eraser nipple into his mouth. He sucked exactly as she'd shown him the night before, while continuing to thrust into her. She gave an audible cry of pleasure now, one that she failed to stifle. A couple of loud gasps followed. "You do drive me wild, Mr. Santos," she said. "Let's pick up the pace. Make me come, and then we'll have breakfast." He sped up in his thrusting, and moved his mouth to her right breast now. He found a new rhythm, one that felt natural and rapid without being frantic. "That's a good speed," she purred. "Give me that young cock." He felt like he could keep fucking her for hours at this point. His penis was big and hard, the pace was comfortable, and she was clearly enjoying his ministrations, however much she played the ice princess. Her eyes were shining with delight and her breathing was coming in ragged grunts. "I'm so close," she whispered. "Make me come, Mr. Santos. Make me come and I'll give you an A."

"I want an A," he whispered back. "I want to make you proud, Miss Blumstein."

"You're my prize student, Mr. Santos," she said. "Wait until I show the other teachers what you can do." With that, her pussy started to spasm on his cock, and her words stopped. She was coming, not with a scream or a moan but a storm of grunts and gulps and swallows, like she trying to hold her breath, to stifle a scream. He saw her eyes roll back, and her neck craned back along the pillow, so she was facing the wall. Philip sped up even further now, his lips around her right nipple and his hands on her hips as he pounded her twitching cunt. Finally, Margot couldn't contain her scream any longer. It ripped out of her all at once, ear-piercing.

As her orgasm began to subside, she noticed that Philip was still pounding away just like before. "Did you come yet?" she asked.

"No."

"Are you close?"

"Not really," he admitted.

"Holy shit," she moaned, dropping the teacher character. "Oh, Philip," she breathed. "You're one in a million."

"Maybe I can make you come again?" he suggested.

"Maybe. Oh you're so fucking cute!" she cried. "Give me a kiss."

He made her come once more, in another screaming outburst, before he finally started to feel his own orgasm coming. "I'm close," he told her.

"Where do you want to come?" she asked him. "My mouth? My tits? Or right where you are?"

"Coming on your tits? I didn't even know people did that."

She took her breasts in her hands. "Wow, you are innocent," she said. "Pull out of me and get that condom off. I'll show you what I mean." He did, dropping the condom onto the sheet. She guided him up higher along her body until his dick was level with her sizable breasts and those glorious, sensitive nipples. She took his seven inches in her hand and started to wank him toward the space right between her tits. "Come on me, baby. Come on Miss Blumstein's tits. I want to watch you come. I want to see it shoot out of your young cock."

She gave him a smile now, that same radiant smile that had always melted his heart even in his youth, and he finally shot out a blast of sticky, hot semen onto her chest. She squealed with delight and kept working him with her hand. "Any more for me?" He shot out more and more. She'd been surprised by how much come he had to give the previous night when she was sucking him off, but now that she saw it all at once, pooling on her chest, she was surprised again, despite herself. His come felt warm and beautiful against her skin. She smeared a finger in it and brought it to her mouth to taste. "Mmmmm. What a good boy you are," she said. "Let me clean you up." She took his penis into her mouth now, swirling her tongue along it, licking up any stray cum, then she pulled him out with a pop and gave him a big cummy grin. "Okay, now I need to get cleaned up. Pass me the tissue paper."

She insisted he take a shower before breakfast, telling him "You smell like... well, you smell like my twat". When he got out of the shower, shaved and washed, she was now in a bathrobe, making coffee. "What do you want to do for breakfast?" she asked. "Want to go out?"

"Sounds good," he said, shrugging. "Is there a good place around here?"

"Yeah, a few. I'll take my shower and get dressed and then we'll drink this coffee and head out, okay?"

He put his arms around her, and she happily cuddled up to him. "How do I smell?" he asked.

"Better," she giggled. "Like shampoo. I approve. Have some coffee and get dressed."

While he waited for her to finish her shower, he sent Steven a text telling him not to worry, that he was fine where he was. He felt like he maybe should have responded the night before, but Margot had driven all thoughts of Steven from his mind. Besides, Steven had left him high and dry in the first place. He wasn't entitled to a prompt response.

At breakfast, Margot was amazed how natural she felt with Philip in public, now that they had fucked. The server could tell, she was sure, that they were, if not Officially A Couple, then at the very least Had Spent the Night Together. Getting breakfast together was a bit of a giveaway. Part of her was afraid of this at first, that people would judge her for getting involved with a younger man (how old was Philip? 22 or 23, probably). But, she was relieved to see, it looked like people didn't really care. Conversation was light and pleasant. They talked about their fields of study mostly, the program he was starting in the fall, her experiences since finishing her residency. Perhaps unconsciously, they were avoiding the subject of exes. She found conversation with Philip was coming very easily, and she had a renewed confidence that she'd made the right choice in inviting him into her life.

"You want to fuck again when we get back to my place?" she asked him, under her breath. She had that mischievous little smile again.

They had sex three more times that day, twice on her bed and once on the couch. They went for a walk to Trinity Bellwoods Park, which he'd never seen before (Philip was very much impressed by all the parks and trees in Toronto). They printed out his credit check and proof of enrollment, and she loaned him a plastic clipboard to keep them from getting krinkled. They watched a few episodes of It's Always Sunny in Philadelphia. It was the best day Philip could remember, better than the early days with Sarah when things had been going so well. Sarah had been hung-up, distant, even seemed afraid of him at times. He knew most of this was the product of her upbringing and not really her fault, but that didn't make it any easier to deal with. She made him feel like she didn't really want to be around him. Margot, on the other hand, was warm, tender, an eager lover, a patient teacher, and generally excellent company. Above all, she made him feel truly wanted. He felt like even if sex hadn't been a factor, they still could have become good friends.

"So what's the schedule for tomorrow?" he asked her in the evening as they sat on the couch, cuddling. They'd spent most of the day naked, not bothering to get dressed again after their second fuck session, after breakfast. She was spooning him on the couch.

"I have work most of the day," she said. "You'll be on your own, sweetie." She tousled his hair.

"Alright. I've got two apartments to look at. One of them... let's see." He opened up the email in his phone. "The first is at two, and it's on Jarvis Street. A ways east from here. The other is at six, on Major Street."

"I can meet you for six," she said. "I'll be done work by then. If it's on Major Street, I'll take you to Caplansky's for dinner. You've got to try Caplansky's."

Margot's alarm clock went off at six in the morning, and she pulled herself out of bed. "Time to get ready for work," she said to him. "You should sleep in, though. You need your rest," she winked at him. "I'll see you tonight at six, okay?"

"Okay," he said. He watched her hips sway as she walked out of the room. God, she was really something.

Philip slept for another hour. When he woke up, she was gone. He took a shower, dressed himself, and made a quick breakfast. This was his fourth day in Toronto, and he was heading home the following afternoon, so hopefully, by the end of the day he'd have a place finalized, though if he had to come up for a second househunting trip, it wouldn't be the end of the world. Just to be safe, he looked at a few more ads on Padmapper, Craigslist, and Kijiji, but there wasn't much left. He spent most of the morning, once again, watching YouTube videos, before finally moving out the door around 1:00. Margot had given him a couple of transit tokens, and he found a streetcar without difficulty to take him over to Jarvis.

It was an apartment building, but a much nicer one than he'd seen on Spadina. Just a studio apartment, with no separate bedroom, but the room itself was of a decent size, and the kitchen seemed okay, and there was laundry in the basement. He asked when the last time was they'd sprayed for bugs.

"Last year," said the landlord. "We've had a few problems with roaches, and we take them very seriously. If you see one, let us know, and we'll have an exterminator up within the week." Sounded good. He filled in an application and gave her copies of his paperwork.

"Look, if you want the place," said the landlord, "it's yours. You seem fine, and I'm trying to get the place filled as soon as possible."

"I have one more place to look at today," Philip said. "So I should have an answer for you by this evening. Is that soon enough?"

The landlord nodded. "Should be. Can't guarantee I'll hold it for you, though, if someone else makes an offer."

Philip had a late lunch at a taco place on Bloor. He liked the Jarvis apartment, honestly. It was a good distance from school, and the neighbourhood seemed to be of pretty reasonable value for what you paid. He spent most of the rest of the afternoon exploring the U of T campus, which reminded him of the Harry Potter movies.

At 5:00, he got a text from Margot. "Leaving work now. What's Major address again?" He sent it to her. "I hope you get this place. Very short walk from me!"

He hadn't thought of that. What a plus that would be!

Philip liked Major Street, even though the name was a bit of a misnomer, since it was a fairly quiet side street. It reminded him of Margot's own Euclid. Plenty of trees, and old brick houses in place of big apartment buildings. He wondered if he could afford it here. Before long, Margot arrived on the corner. She was wearing a beautiful green dress with a brown tweed jacket over it; probably a little glamourous for work but he didn't know how she was expected to dress. "Hey, you," she said, giving him a light kiss. He kissed her back, a little more intensely. "Not in public," she whispered. "That kind of kissing is only for when we're alone, okay?"

"Sorry," he said.

"It's okay. I forget you've never done this before," she said. "Oh, it's exciting!" She squeezed his hand. "So which house is it?"

"That one." He pointed to a very nice, old-fashioned brick building.

"I love it," she said.

"I've texted the landlady," said Philip. "She should be out in a minute."

Just as he was saying that, the front door opened. The landlady was a handsome South Asian woman, of about forty. "You're here to see the two-bedroom?" she asked.

"No," Philip said. "The one-bedroom. For 1250$?"

"I'm sorry," said the landlady. "We just signed someone for that this morning. I guess you didn't get the text I sent out?"

"I guess not," said Philip, disappointed. Oh, well. The place on Jarvis would be fine.

"How much is the two-bedroom?" asked Margot.

"1850$ a month. That includes utilities."

"We'll have a look at it," said Margot.

"Great! Come on in," said the landlady. Philip gave Margot a questioning look. He couldn't afford 1850 a month. She smiled at him, as if to say not to worry.

It was the second floor of three. "You'd have the entire floor to yourselves," said the landlady. "Laundry's ensuite, right here," she showed him the machines, next to the stairs. "Good sized kitchen. The living room is really something, I think." She was right. The living room alone was bigger than the entire apartment at Jarvis, he was certain, with a big bay window, the kind you could sit in, facing out to the street. There was a sizable master bedroom and even the smaller bedroom was decent. Philip loved it, but he wasn't sure what Margot had in mind.

"Can we have a moment to discuss it?" he said to the landlady.

"Sure. I'll leave you two alone," she said, and did.

"I can't afford this," he said to Margot. "And you've already got a place of your own."

"Don't worry," she said. "I can afford it. Let me take care of you, Philip Santos."

"You mean you'd pay part of the rent, just so I could live closer to you?"

She nodded. "Let me take care of you, Philip Santos," she said again. "You could be my sugar-baby. That's what I want you to be," she said. "Please. I want to take care of you, very badly."

Philip had never even thought about this. He knew such arrangements existed, usually with the genders reversed, but the idea of being a party to such a thing had never occurred to him. True, in bed with her, at the height of passion, the idea of surrendering himself to her entirely had been all he wanted, but in the waking world... well, why not?

"If you're sure this is what you want," he said. "And that you can afford it."

"I'm sure." He put her arms around his waist and pulled him in for a deep, passionate kiss. Apparently this counted as 'in private'. When they finally broke the kiss, her eyes were shining.