Under Her Wing

"I love it," he said to the landlady. "If there's a bank around here, I can go get the deposit right now."

"Sounds fine. I'd like to get this finalized as soon as possible," she said. "It would just be yourself living here, then? No roommate?"

"That's right. I just have one question. Suppose for whatever reason, I can't make rent payments any more. What happens?" Philip didn't want to jinx his relationship - whatever it was - with Margot, but he also had to consider what might happen if things ended between them and he couldn't afford to live here anymore. He hoped it wouldn't happen, and felt guilty for even considering the possibility, but you never knew.

"Well, Toronto's a pretty good city for renters," said the landlady. "If you need to break a lease, just give me two months' notice, and that's pretty much it."

She told him where the nearest branch was, and before long, they had everything signed and finalized.

He and Margot walked down to Caplansky's after. Caplansky's is a Jewish deli, probably the best of its kind in Toronto. Margot ordered them both smoked meat sandwiches, fries, and pickles on the side.

"What am I going to do with that extra room?" he said.

"Up to you," said Margot. "Don't get a sublet, though. I don't want to have to worry about disturbing a roommate when I come over." She winked at him. "You know how loud I get."

"I do."

"But you could make a little guest bedroom like I've got. Or you could turn it into a study. There are lots of uses for an extra room. Tonight, though, we should do something to celebrate," said Margot. "You've got a new apartment, signed and sealed! I'm so proud of you!"

"I owe you so much," he said to her. "Anything I can do for you, I'll do."

Margot's hand slipped to his knee. "You want to have anal sex when we get back to my place?"

"Seriously?" he asked.

Margot nodded. "I've tried it before but I could never get relaxed enough. With you, I don't think it'll be a problem," she said, and gave him a light, public-appropriate kiss, though under the table, her hand had migrated to his rapidly-stiffening crotch. "But I trust my handsome sugar-baby," she whispered. "You'd never hurt me. You're a patient boy and a good student, aren't you?"

They had a hard time keeping their hands off each other for the rest of dinner and the walk back to her place. When they finally made it, Margot pinned Philip to the wall and forced her tongue down his throat, taking him as her own. He didn't resist. "Such a good little boy-toy," she hissed. "You're going to bring me so much pleasure." She turned around now, rubbing her wide ass against his crotch, still pressing him against the wall, and he kissed her from behind, put his arms around her, caressed her breasts. "Yes," she moaned. "Hold me." She could feel his stiffness pushing up between her buttocks through the fabric of his pants and her dress. "Yes," she moaned again, her tone darker, smouldering. He kissed the side of her neck, showering her neck and ear with kisses. "Nibble my earlobe a little bit," she suggested. "Oh fuck, exactly like that!" She craned her neck around and kissed him fully on the lips again, in a tangle of tongues. "You really turn me on, Philip Santos," she hissed. "Now take my jacket off and hang it up."

He quickly obeyed, removing her jacket and hanging it on the coatrack. "Good boy," she said. "Let's go into my room. March!"

Philip was surprised how much he liked being ordered around by her. He liked the sense of submission, of not having to worry, of trusting her to take care of everything, but he also found it all peculiarly flattering; to be her fuck-toy made him feel wanted. He was done with games and hard-to-get and coldness and all the abstinence bullshit. He wanted honesty, openness, unashamed lust, and Margot had it all. She wanted him and wasn't afraid to admit it.

By the time they got into her bedroom, she had pulled off her green dress and discarded it onto the floor, leaving her in a lacy white bra and panties of a strangely frumpy cut that might have been unappealing on another woman, but were so deeply Margot that Philip could feel his mouth watering at the sight of them. She took hold of his necktie and pulled him onto the bed with her, into an intense embrace and kiss. He felt her soft body under his, until she rolled over on top of him. Now he felt her heavy tits pressing against him. She rained butterfly kisses on his neck and ears now, and his hands moved down onto her wide, fat ass.

"Mmm, that feels nice," she whispered. "But you're a little overdressed." She started to unbutton his shirt.

"Do you want me to take off my tie?" he asked.

"No, leave the tie on. You look very sexy with the tie on." She had his shirt completely unbuttoned now, his chest on display, but she left it and the tie on him, running her hands up and down his chest. He felt an involuntary spasming in his loins as she grazed his stomach, and he gave out a groan as he continued to caress and knead her plump buttocks. "Take my bra off," she said. "I want to see if you can."

He slid his hands up her back to the clasp. He fumbled with it for a second but then he figured it out. Margot smiled at him. "Clever boy." She raised up her shoulders to remove the bra altogether, and pushed her heaving tits into his face. "Let me see that trick of yours again," she said. "Do what you did to me that first night we were together." Philip didn't need telling twice; while his hands went back to massaging and caressing her ass, he took her nipple in his mouth, then the other, sucking them just as she liked, and Margot shuddered with pleasure. "Oh, that feels great, baby. That really helps me!" she cried. She slid a hand down his pants and took hold of his hard, thick cock. She didn't jerk him but simply squeezed.

"Not quite so tight," he said, and she eased off. She was rocking her hips back and forth now, grinding against him, and her breath was getting increasingly ragged. He could tell she was close. He pushed one of his fingers under the band of her panties now, brushing against her damp pussy lips, and then prodding her, gently, in her anus. Margot squealed. He didn't push hard enough to actually enter, but simply to tease.

"Oh, you've got a dirty mind, young man," she purred into his ear. "Can't wait to get on to the main event, eh? Can't wait to stick your fat cock up my little asshole? Oh, Philip, you are a dirty little boy-yeeeeeeeeEEEEEE!" Her words turned into a scream as he continued to suck on her nipples, finally bringing her to orgasm. He could sense it, and her ministrations to his cock slowed, became gentler, as she relaxed in a sort of momentary afterglow. "Oh, Philip," she said again. "Who would have known that sweet Philip Santos could make me scream like that?" Philip just smiled up at her. She put her arms around and gave him a squeeze. "My beautiful boy," she said again. "I'll be right back."

She disentagled herself from him and stumbled into the bathroom, still a little weak at the knees from that orgasm. On her way to meet him on Major Street, she'd stopped by a sex shop and picked up an enema bulb. She wanted to be clean for him, so he could eat her ass. She wanted to hurry, but she took her time, running the soapy water in and out of her anus until she felt as clean as fresh linen. She looked at herself in the bathroom mirror.

Margot was thirty, and starting to feel the earliest onset of age. She got hangovers more easily now, and found grey hairs here and there, and she'd put on weight, mostly around her hips, and after the divorce and miscarriage, she'd been worried that she'd be alone forever. She felt withered up, dead inside. To find a handsome, eager young lover like Philip felt like a godsend. And he wasn't even a stranger. Years had gone by since she'd seen him last, true, but in a way, this almost felt like picking up where she'd left off with him, like she'd always meant, even subconsciously, to one day take Philip Santos into her bed, when he was old enough.

She was fully nude now, except for her glasses, and she felt sexier than ever before. She strode back into the bedroom, where she found him, stripped down to just his necktie, which she took in her hands to pull him into a deep, wet kiss. "I'm going to make your dreams come true, Philip Santos," she said. She pulled him up, off the bed, and then pushed him down into a kneeling position. "Get on your knees," she said to him. Then she turned around, put a hand on either buttock, and lowered her ass into his face.

Philip took to it immediately, cluing into what was expected of him right away. He started eating her ass without a moment's hesitation, moving his tongue around the hole in circles before plunging right in. Margot wailed in pleasure as his tongue penetrated her asshole, and pulled her cheeks apart further to give him better access. "Mmmmmmm," she moaned, running her own tongue along the lips of her mouth. "This is good."

"Have you ever done this before?" he asked.

"No," she said. "My friend Emily swears by it, though. I told her about you and she insisted we try anal sex."

"I like Emily," Philip declared. Margot laughed, but the laugh was cut short as his tongue pushed past her sphincter once again. She felt her hole relaxing more and more as his tongue worked. He moved out, kissing her anus lightly, licking the surrounding area, her crack, her cheeks. He bit her, lightly, running his teeth slowly along the smooth skin of her big round bottom, and Margot cried out in pleasure.

"That feels so good, Philip."

"Do you think you might come again?"

"Not yet," she said. "But it's really helping me relax. I need to be relaxed back there, if you're going to stick that big cock of yours in my ass and buttfuck me."

"Oh, that's what I want, Margot," he said.

She thought about making him call her 'Miss Blumstein', but decided against it. This wasn't a moment for role play and power dynamics. She wasn't his teacher right now; this was as new to her as it was to him, aside from a few instructional videos Emily had sent her. Right now he wasn't her student or her sugar-baby or her boy-toy. They were two lonely people who had found each other.

She took the lube from the shelf, having deliberately left it in reach, and handed it back to him. "Rub this into me," she said. "And be generous."

Philip squeezed a big dollop of the stuff onto her asshole, and slowly, gently, pushed his finger inside her. Margot cried out as he penetrated her. There was almost no friction at all, like a smooth gliding motion into her body. He moved in and out, back and forth, coating her entire anus and rectum with the stuff. "That's not too cold, is it?" he asked.

"No," she said. Honestly, she'd barely noticed the cold, but now that he pointed it out, it did feel a little cold. "Rub it all around the outside of my hole, too."

He continued to rain kisses all over her ass as he worked, rubbing the lube deep into her and outside her and everywhere. Margot moved a hand almost subconsciously down to her vagina, and began to absent-mindedly masturbate as he worked. "Okay," she said after a moment. "Gonna cum after all. Stick your tongue back inside me." She put her other hand against the wall, steadying herself as his tongue and her finger worked at both her holes, bringing the orgasm ever closer. Philip could feel the pressure of her fingers in her cunt, poking at the membrane between vagina and anus. He had his left hand on her left buttock, holding her open to his exploring tongue, but he moved his right hand up to her back, and slowly ran his fingernail along her spine. Margot almost buckled at the knees at that, and gave out a low groan. She felt her eyes roll back in her head as her orgasm washed over her like a flood. Her cunt spasmed on her fingers and he felt her asshole dilate around his tongue. After a moment of that, she gently pulled him away and turned to face him, her expression positively beatific. "Thank you," she said to him, and hugged him, tight, holding nothing back. She felt his penis, rock hard, batting against her thighs, and rested her hand on him. Philip's own expression, she thought, was one of pure fiery arousal, and she decided it was time. "Lie down on the bed," she said to him. "On your back."

Philip did, propping himself up against the pillows. She could hardly take her eyes off his erect penis, standing up like a flagpole. She licked her lips at the sight of it, and took another condom from the drawer.

Margot moved onto the bed with him, on her hands and knees now, and grabbed his cock and took him into her mouth. She was getting to love his taste, love the feel of him in her mouth. She didn't suck for long - just enough to get him as erect as possible - before rolling the condom along his length. She looked up at him, into his eyes now. Both felt like there was something they should say, perhaps, but in that look, everything that needed to be communicated between them was made clear. Finally, Margot broke the silence. "I want you in me."

She climbed up along him now, pressing her soft body against him, straddling him now, sitting on his lap. He felt his cock pushing up between her round cheeks, while his face was now between her breasts. Margot lifted herself up off him and reached back, taking his condom-wrapped penis in her hands and guiding it to her anus as she lowered herself, slowly, back down on him, never breaking eye contact.

The head of his penis pushed against her asshole for a moment, and then slid, easily, in. Margot couldn't believe how relaxed she felt as her backdoor gladly accepted Philip's throbbing rod. She pushed down harder now, taking him deeper into her bowels. "Fuck," she whispered. "You're all the way in my butt, Philip Santos."

"Oh, Margot, Margot, Margot Blumstein. This feels amazing."

She bit her lower lip, wiggling on his dick. "Yeah, I have to agree. This feels really good," she said, cracking a naughty smile. She slowly started to rock her hips against him, drawing him in and out of her anal depths. His erection was pointing downward, towards his feet rather than his head, while his legs had been pushed apart. "Oh, yeah," she cooed, as she found a rhythm. "Yeah. Fuck me, sweetie. Give Margot the buttfuck she needs." She started to gyrate her shoulders now, pushing her tits into his face, and Philip took the hint, sucking and licking her firm nipples as she took him into her ass. "Mmmmmmm," she moaned. "Just like that. Oh, you're such a good fucking boy!" She lowered a hand to her curls and started to rub her pussy, aggressively. "Talk to me, Philip," she said. "Talk to me while you buttfuck me."

"Oh my gosh, Margot," he whispered. "You're the hottest woman in the world. All I want is to please you."

"How will you do that?" she gasped.

"I'm going to suck your tits," he said. "I'm going to lick your clit and stick my tongue up your ass. I'm going to put my dick everyone on your body it will fit and cover you in my come."

"You are a dirty boy!" she cried.

"I want to be your dirty boy," he said. "I want to be your favourite sex toy. I want you to use me, Margot Blumstein."

"Shut the fuck up," she grunted, but she was still smiling. "Sex toys don't talk. Give me that young cock up my ass. Make me come."

She continued rocking her hips. He could feel the tightness of her ass, even through the lube and the condom. The muscles gripping him, the shape of her tailbone. Whenever she leaned back on him, he could see the base of his cock disappearing up her hot little anus, and he was amazed by how far she could take him. She pushed a nipple back into his mouth, and he was keen to oblige.

"Good boy," she said, stroking his hair as she fucked him. "I love feeling you, moving in and out of my body like that." She had gotten bored with the silence and wanted to talk again.

"Can you come this way?" he asked.

She nodded. "I think so." He wasn't in her cunt but he was close enough, and she was feeling all the same kind of stimulation. Coupled with his oral ministrations to her puffy, sensitive nipples, and her own fingers at her vagina, an orgasm should be within reach and triply intense. "Just think. Soon you'll live within walking distance of me and we can do this whenever we want. When I get home from a long, stressful day at work, I can just call you over for a nice relaxing round of buttsex to help me unwind."

"Whenever you want," he said. "I'll be at your beck and call."

"Oh, Philip. My cute little boy-toy. You really are one in a million." She meant it. She couldn't remember ever feeling so comfortable with a guy. He wasn't judging her, didn't blame her for anything, made her feel young and alive again, got her so physically relaxed she was able to open herself up for anal, and she was truly loving it. She felt a rush of affection and tenderness for him. She kissed him on the forehead, and then gently angled her head down, their noses nuzzling together, to kiss him on the lips. He kissed back, gently but intensely, and when the kiss finally broke, she saw the same warmth in his eyes that she felt.

Her orgasm was building up now, in her bowels, rectum, cunt, her entire lower body, her every nerve ending. She could feel his heart beating alongside her own, conducted through his chest and the blood in his cock and he moved in and out of her sensitive anal ring, but now she wasn't sure which heartbeat was whose, wasn't sure where his body stopped and hers began.

"Oh, my sweet baby boy," she whispered to him, and then she came.

Margot came with a more intense orgasm she'd ever felt, an electric jolt arcing between her asshole and her pussy. She moved her fingers faster over her clit now, her throat engulfed in a low, wordless moan right into Philip's ear, her ankles straight and her toes curled so hard it was almost painful. She squeezed him tight to her, never wanting to let go of him. To her amazement, she felt a steady squirt of wetness at her pussy and onto his stomach as she ejaculated onto him. She didn't even know she could do that.

Now Philip came. She felt it in her ass, the sudden surge of fluid heat in the condom, saw it in his eyes, the absolute overwhelm of physical stimuli as her every anal muscle squeezed his penis, milked it for every last drop of seed.

Neither of them could speak. They lay, trying to catch their breaths, panting heavily into each other's faces. He held her tight, tighter than he had ever held anyone before. To his delight, she squeezed back. She had a look in her eyes of wildness, abandon, surprise, like she was impressed not just with him but with herself, like she hadn't known it was possible to come so hard.

"Oh, Philip," she finally moaned, running a hand through his hair. "I feel alive again when I'm with you."

His penis, now flaccid, fell out of her with a wet sound, and she gave a long, loud fart. "Excuse me," she giggled, and Philip laughed too.

"Why do you have to go away tomorrow?" she said. "I wish you could just stay here with me. We'd never get out of bed and we'd live on delivery pizza."

"Sounds like my idea of heaven," said Philip. "This whole week has been... well, life changing."

"For me too. I'm so glad you're here, you have no idea. What time is your train tomorrow?"

"Bus. It's at 2:30."

"Okay. I work tomorrow but I have a bit of time between appointments around then. I'm meeting my friend Emily for lunch. Why don't you join us, and then I'll put you on your bus?"

"Sounds goods. This is the Emily who recommended... this?"

"That's her. You'll like her."

"I already owe her a big favour, I think."

Margot smiled mysteriously. He would have asked her why but he was already falling asleep.

When Philip woke up, Margot was already gone and their clothes were still scattered at the foot of the bed and the surrounding hallway. He got his last set of clothes out of his suitcase and got dressed. He checked his phone. It was only about 9. He texted Margot asking if it was okay if he gave all of his worn clothes a run in her laundry machine, and she replied that it was fine and she'd have the lunch details to him soon.