Under Her Wing

"Thanks, he said.

Margot was finding herself very much attracted to Philip, but it was more than that. She felt very comfortable around him, like she'd known him all her life, like she could tell him anything. She had told him the most painful facts in her life right now, and he'd listened without judgement. Even their more mundane conversations, over ice cream, over dinner at the fusion place, over The Fox and the Hound had fostered, she thought, a deep connection, and it had been a long time before she felt so close to someone so quickly. He was still the same sweet boy who'd made her the goodbye card when she went off to university.

When they got back to her place, he saw a Facebook message waiting for him. "Oh shit, it's Steven," he said. He'd almost forgotten about Steven.

"Hey man im so sorry i never got back to you but something came up yesterday. u can stay over tonight if you want though," he read out loud.

"'Something came up'", she repeated. "That's fucking shitty of him. I'm sorry, but he made a commitment to you and let you down when you needed him."

"Yeah," Philip said. He didn't think he'd ever heard her swear before. "Still, I don't want to impose on your hospitality any longer."

Margot swallowed, hard. She didn't want him to go, but maybe hearing back from Steven was for the best. "It's been a pleasure having you here, Philip Santos. Believe me. You're welcome to stay here the rest of the week." She screwed up the courage to make her next move. "But... now that you have an alternative and aren't stuck here with me, I feel comfortable asking you this."

"Asking what?"

She looked him straight in the eye now. "I don't want to put any pressure on you, but... instead of sleeping in the guest bedroom tonight, would you like to... come and sleep in my room? We could... keep each other company."

Philip couldn't believe what he was hearing. He'd imagined this possibility, but that had made it seem all the less likely. He stood up and put his arms around her, slowly, just as nervously as she was. A hopeful smile crept across her face, and she fell into his arms. She could feel his hard, lean body through the hug, and smell his scent. It enthralled her. "Kiss me, Philip Santos," she said. She held up her long, swan-like neck, and he moved in for a deep, slow kiss. The kiss gradually intensified. She moved her hands now, from his shoulders slowly down his muscled arms and to his wrists, pulling him along through the apartment and she walked back into her bedroom. She broke the kiss only now. "I want you right now," she said. "Please. Make love to me."

"Okay," he said. "Remember, it's my first time though."

"I won't hurt you."

"I know you won't. But... just don't expect too much."

She smiled. "You could never disappoint me. I want to be your first. Take your shirt off." He pulled his t-shirt up over his head, and she got her first look at his bare, lean chest. "Yesss," she whispered. She caressed him, slowly. "I could get used to this. Sarah must have been crazy, turning this down." Philip put his hand on her chin, tilting her head up for another kiss. Her fingers slowly worked at her own shirt, unbuttoning the blouse dexterously and letting it fall to the floor. Philip's hands rose up to cup her lacy bra, and Margot moaned softly. She reached a hand behind her and unclasped the bra, and it joined the shirt on the floor.

Philip took a knee in front of her now, caressing and kissing her heavy breasts. She had big pink nipples that stuck out the size of the tip of his thumb. He cupped her breasts with his hands, squeezing gently.

"Not quite so hard," she whispered, and he eased up a little. "That's good." He ran his tongue between her breasts, and she gave a shiver as he moved slowly back along her right breast, taking the nipple wholly into his mouth. She felt it harden under the suction. "Oh, Philip Santos," she purred. "I'm going to show you all the ways I like to be touched. All the ways I like to be caressed, licked, and fucked. And we're going to find out together what you like. Would you enjoy that?"

He nodded, frantically, giving an "uh-huh" sound as he moved to her left nipple.

Margot gasped. "That's right, baby, pay attention to both of them. Oh yes!" she cried, as he pinched the right gently between thumb and forefinger. "Give it a little twist. Just the tiniest. Oh keep doing that! Exactly like that!" Both of her arms were wrapped around his head now, holding him to her as he worked at her nipples, her fingers running through his black hair. She could feel an orgasm building already. Only once before had she come from just having her breasts stimulated, although her nipples in particular had always been very sensitive. She gave out a low wail of pleasure now, letting the orgasm wash over her gently, before collapsing backward onto the bed, letting go of him as she softly fell.

"Fuck, that was amazing," she said.

"Did I make you come?" he asked, dumbfounded.

"I think so," she said.

He sat down next to her on the bed. She could see the raging hard-on in his pants, tenting the material. She reached out a hand and took hold of it, through the fabric, and gave him a naughty smile. Slowly, lazily, she started to unzip his fly, pulling his pants and boxers down and drawing out his long, hard penis. "I guess the stereotype about Asian guys isn't true after all," she said, before pushing her lips over him and taking his entire length into her mouth. She sucked him enthusiastically, luxuriantly, slowly, running her lips up and down his shaft. Philip put his hands on the back of her head, feeling her hair, still in that same too-formal bun. She hadn't taken her dorky glasses off, either, he realized, but he liked her glasses just fine.

"Leave your glasses on," he said. He thought he saw a smile play around the corners of her mouth. Her eyes caught his, locking their gazes together and she worked with her mouth at his tool. He started thrusting, gently meeting her motions with his. He transitioned now to a standing-up position, fucking her face slowly, and letting his pants and boxers fall down around his ankles. Margot, likewise, reached back to unfasten her skirt, wriggling out of it without ever breaking eye contact, on her hands and knees on the bed. He could see her panties now, white fabric with red lining, and little pictures of Minnie Mouse on them. There were a good few inches of naked thigh on display before the tops of her stockings. He feasted his eyes on every inch of her beautiful body, all its flaws and realities and perfections, as she expertly sucked his cock. He loved her flaws; they were what differentiated her from his sexual fantasies, made her a real woman, not some impossible ideal of eroticism. "You were my first crush, Margot," he said to her. "Did you know that? I always had a bit of a thing for you." He could see the tenderness in her eyes, the warmth. He was being blown, he reminded himself, by Margot Blumstein, and had just brought her to orgasm. It was the proudest moment of his life. "I think I'm going to come now. Is that okay?"

"Mmm-hmmmm," she grunted, continuing to work her head back and forth along his shaft. One of her hands was gently cupping his balls now, not quite squeezing them but holding them with a slightly pulsing tightness, increasing and decreasing as she sucked. It felt nice, honestly. Her other hand was working, slowly, in the front of her panties. As his breathing intensified, and his orgasm got closer, she drew her hand out of his panties and cupped the cheek of his ass. He could feel the wetness of her fingers. Slowly, she poked her index finger against his anus. She caught his eye, her expression questioning now. Should she continue?

Philip had only the barest idea of what was considered normal here, and really, he was willing to try anything for Margot. He wanted to surrender himself entirely to her right now. He nodded, slowly, and she pushed her finger all the way up to the knuckle. He'd never felt anything go up there before, but it wasn't unpleasant. She wiggled her finger, slowly inching it past the muscular ring of his anus and into him. He did his best to relax, to surrender, to open himself up to her.

"Oh my God," he whispered, and came, hard, into her mouth. Margot happily, greedily sucked down his seed. She pulled her finger out of him and he collapsed onto the bed beside her, and she sat up next to him. He was naked except for his socks, and she was stripped down to her panties and stockings and, of course, her glasses. She rested her head on his shoulder and he put an arm around her. "Nobody's ever done that to me before," he said.

"Done what?" she teased.

"You know what," he said.

She chuckled and gave him a mischievous look. "I feel like if most boys weren't scared to try it they might like it," she said.

"Anything you want to do, I'll try," he said. "I surrender to you entirely."

Margot beamed. "My very own boy-toy," she said. "I like you, Philip Santos. You're cute. You turned up on my doorstep, a little lost boy, and I'm so glad I took you in." She reached up and tousled his hair. "Do you want to learn how to eat pussy?"

"I would be delighted," he said. He moved off the bed and knelt on the floor in front of her, as she leaned back, spreading her legs. She grabbed a few of the pillows - big cylindrical ones, like you'd prop up while reading in bed - and made a little pile to lean on. Then she hooked her thumbs in the sides of her panties and pulled down, stepping out of them.

Philip had never seen a vagina before in person, and Margot's did not disappoint. She had a well-kempt bush of dark brown pubic hair over it, trimmed, springy to the touch. "See this? This is my clitoris," she said. "Never lose track of it. Flick it with your tongue, very gently. As light as you can make it. He did, as well as he could. She gave a purr of pleasure. "That's good. The most important thing, though, sweetie, is consistency. Don't speed up unless I tell you to. Don't slow down. Keep up that exact pace. I know boys like to speed up and go faster to climax, but for women it's different. Just keep up that exact rhythm. Mmmmmm, that's nice. Just like that, baby." He kept going. She put one hand on the back of his head, feeling his hair, and with the other, she caressed her own breast, flicking the nipple slowly. "Okay, now I want you to slide a pointer finger up into my pussy-hole. Go slow and gentle, and be very careful of your fingernail." She gave a squeal of delight as she obeyed. "Nice and slow. In and out. In and out. Follow the rhythm of my voice. Good boy. Just like that. Oh, you're a natural. Ohhhhhh..." Her words began to fade into inarticulate moans. Philip was tempted to speed up the pace. Just like she said, that was how he would reach his own orgasm, but he remembered what she had said and kept it slow, gentle, even as her moans became more urgent, intense, frantic. He became aware of his penis now, which was hard and erect again, and batting against her shin as he ate her pussy.

"Oh, Philip," she moaned, finding words again. "You're such a sweet boy. My sweet baby boy. I'm glad you told me you always had a crush on me. I'm glad you told me you wanted to surrender to me. I will make your dreams come true, baby boy. Oh, Philip! Philip!" WIth that, Margot gave a shudder, and felt herself come apart in a beautiful orgasm. She gave a long, high-pitched squeal, and her pussy spasmed on his finger. She reached down and put her own finger to his chin, lifting him up, telling him it was done.

"Did you come?" he asked.

"Did I come?" she repeated. "About as hard as I have in years, sweetie. You've got a real talent. You know that?" Philip blushed. He didn't know that. "Awww. My sweet innocent Philip is blushing! Come here." She drew him up toward her for a deep kiss. She reached a hand out to take a hold of his erect cock and finally broke the kiss. "Lie down on the bed," she said. "On your back." He hastened to comply. Was he finally about to lose his virginity?

Margot opened up a drawer in her bedside table and pulled out a small foil packet. Oh shit. This was the moment. "Your lesson's done for tonight," she said. "We'll go over fine details tomorrow. For now, let's just fuck." She unwrapped the condom and took his penis in her hand again. She gave it a quick suck one more time, and then rolled the condom down along his length.

"Oh, Margot," Philip whimpered, "that feels so good. I love it when you touch me."

"I love touching you too," she said. The condom now firmly in place, she swung a leg over him, straddling his groin. "I'm going to have a hard time keeping my hands off you over the next few days." She took his penis in her hand and guided it, gently, into her very wet pussy. She moaned, loudly, as he filled her up. "Don't worry about technique," she said again. "Just enjoy this. Enjoy me, Philip Santos." She started, slowly, to move her hips up and down on him, running his cock into and out of her. Philip looked up into her face; she was smiling down at him with an expression of such kindness, such joy in this moment, like neither of them could believe their luck that it was really happening. He put his arms around her shoulders, feeling her warmth and she slowly, gently fucked him. "I'm so glad you're here," she said. "Not just that somebody's here but that you're here. You, Philip."

His cock felt bigger, harder than it had ever felt before as he felt her wetness moving, gently but firmly, over it. In and out of her pussy. In an out. "I'm glad it's you too," he said. "This is a dream come true." Margot's smile grew bigger. He thought he saw tears in her eyes.

His hands slowly moved around her sides to her breasts, caressing them again. He pinched her nipples gently, like she had shown him, and she moaned loudly. "You're a good student, Philip."

"I want to be a good student," he said, gazing up into her eyes. "I want to make you proud, Margot Blumstein. I'm proud to be here with you." He was really getting into the talk. She leaned down and kissed him, deeply, uncharacteristically aggressively, like her life depended on it. Maybe it did. She pushed her tongue deep into his mouth, almost down his throat, frantically. She was gyrating her hips faster now. She broke the kiss, roughly. "Don't stop what you're doing," she said. She moved her shoulders to grind her breasts against his hands. "Fuck me, Philip Santos. Fuck Margot Blumstein. Give me what I need."

"Anything you need," he whispered. He could feel his orgasm coming. "Let me be yours. Your student, your toy, your lover, anything you need me to be."

"Are you close?" she whispered. He nodded. "Come for me."

"But what about you?"

"You've already made me come twice tonight," she said. "It's okay. You don't need to make me come every time. Not yet. We'll get there." The idea of getting there, of spending more time with Margot, of learning from her over many fuck sessions, pushed him over the edge now. He felt the pressure in his balls finally break, and he came, a warm flow into the condom. She felt it through the latex, and moved her body faster and faster now, to make this as enjoyable for him as possible, and it felt so good, Philip cried out her name. Margot beamed with pride.

She disengaged from him, gently peeling off the condom and dropping it in a small wastebasket by the bed. "I'm gonna clean you up a little bit," she said, and took his penis into her mouth again, pushing back the foreskin and sucking the remaining semen from the edges. When he was satisfactorily clean, she lay down beside him, resting her head against his shoulder. He put his arm under her waist, and she put an arm over his chest, drawing him in for a cuddle.

"Did you like that?" she asked.

He could only nod.

"As your teacher, I think you show a lot of promise," she said. "And there are so many other things I want to teach you."

"Like what?" he said.

"Oh, you'll find out." Her eyes were shining, fixed on his. "I feel like you might enjoy some light bondage, maybe a bit of roleplay. And I want to teach you a few more positions. Missionary, doggie-style, sixty-nine. Maybe we could try some butt stuff."

"Whose butt?"

She giggled. "Well, whatever you're open to," she whispered, a teasing smile on her face. "I'd love to fuck you in the ass when you're ready for it."

"We could try it," he said, surprised how comfortable he was with the idea.

"I love how fearless you are," she said. "A lot of guys would be scared it would make them not real men anymore or something."

"If it's with a woman as beautiful as you, I don't see the problem."

There was a momentary pause. "I never really thought as myself as beautiful," she said, finally.

"You are, Margot. I've always thought so." She smiled, and kissed him.

"Thank you. And I'd never ask you to do something that I wouldn't do myself, of course." She wiggled her own butt against his arm. "These are options," she said. "Just something to think about. If you're not comfortable with any of it, just let me know and we'll stick to what we've been over so far."

"I want to do it all with you, Margot. Like I said. I surrender myself to you entirely."

Margot cuddled into his neck and shoulder deeper now. "My very own boy-toy," she said. "And it's sweet Philip Santos who made me that goodbye card when I went to college." She reached out an index finger and booped his nose. "Boop Boop Be Doop," she said. "Oh, this is going to be a lot of fun."

Philip's phone went off, waking them both up. It was a text message.

"Put it on silent," groaned Margot.

"I will. Sorry." He got fished the phone out of the pocket of his discarded pants, and opened up the message. "Well, the appointment I had lined up for today is canceled. Someone took the place last night."

"Oh, that's too bad," said Margot. "You'll find somewhere though. Don't worry."

"Thanks," he said.

"Come back to bed."

"It's morning though. Shouldn't you, at least, get up?"

"Today's my day off," she said. "I was thinking maybe we could spend the day together."

He got back under the covers. She put her arms around him and cuddled up to him. "I want to make sure we're on the same page here," she said, looking into his eyes. Her expression was somewhat grave, but also tender. "Was this just a fuck for you? If it was, I won't be upset. You can tell me."

"There's no such thing as just a fuck for me," he said. "First time, remember?"

"Of course," she said. "But... if this is just going to be a single fun week, that's okay with me. That's all it'll be. But when you do move to Toronto... I'd like to keep doing this. You're a really sweet boy, Philip Santos, and I want you in my life."

"Are you asking me to be your boyfriend?" If his eyes weren't so dry and crusty and just-woken-up, there might have been tears in them right now.

"Well, we don't have to be quite so official about it. Let's just see how it goes?"

Philip felt himself getting lost in her eyes. He couldn't stop his mouth from pulling back into a smile, and felt himself on the verge of blubbering, but he tried his best to play it cool. "The twelve year-old me would never forgive myself if I turned down a chance to be Margot Blumstein's... whatever. Whatever I'll be to you."

Margot beamed, and slid her hand down his chest. She grabbed a hold of his stiff morning cock. "Well, I know what I want you to be right now," she purred. "Ready for another lesson, my little student?" Philip nodded. "Good. And maybe not so little after all. Let's start with a review of what we covered last night about eating pussy. Lie down." Her tone was brusque, businesslike, commanding. Teacherly. This was the Margot he remembered from his youth, distant and sassy and unmistakably in charge. He reclined from his sitting position, resting his head firmly on the pillow. Margot turned around now and swung a leg over his face, lowering her dampening pussy toward his mouth, and the wide cheeks of her ass over his eyes.