A Drunken Evening with Mom

Sally was sitting on the couch in the darkened apartment when Nathan tried to sneak in through the fire escape. The only light in the room was the dim glow of her phone. He didn't seem to notice this as he tried to creep to his room, thinking he'd gotten away with it.

"It's 2 AM." Sally's voice calm but stern voice suddenly filled the room. Nathan was startled and bumped into a wall.

He cried out in pain, swearing a little, before turning around to face his mother. Sally turned on the lamp sitting on the side table next to her, filling the room with soft, warm light.

"You okay?" she asked him, sipping on her drink.

"Yeah, just my shoulder... am I in trouble?" he asked her, looking apprehensive.

She sighed. "I'll decide tomorrow, too tired now," she responded in an exasperated tone, pouring the remaining contents of her wine bottle into her glass and having a long drink.

That's when Nathan noticed what she was wearing, the short, tight black dress that showed off a lot of cleavage. Her long red hair looked great too, she'd gotten it done especially for tonight. "Oh yeah... what happened with your date?" he asked, awkwardly, he'd forgotten all about it though he'd been the one to see her off and then capitalize on the opportunity by sneaking out to go to a party on a school night.

"He stood me up," she said simply, finishing her glass of wine. "And that's the last of it." She grunted. "It's fine, it's happened before... a lot of times." Not a lot of good guys wanted to date single moms and it had gotten harder as she got older. A lot of them seemed okay with it one minute then chickened out the next. Didn't matter if her son was basically an adult now, it was if they all saw her as 'used goods' or something, she supposed. She'd thought she'd find some luck with single dads, only to find there was a reason most of them were single.

"I'm sorry," Nathan said, genuinely empathetic. "Anything... I can do?" He asked, though unsure how he could help.

Sally smiled warmly at her son. She supposed as long as she had him around the house she really didn't need someone else that much... though of course there were certain needs Nathan couldn't fulfil. She pointed to a cabinet. "In there, tequila, two glasses, bring them here." she commanded.

Nathan went to grab the drink. "Two glasses?" he asked, just to make sure.

Sally smirked. "I know you've been drinking and getting high all night, one more won't kill you. Hell you're 18 now, I was drinking much earlier," she smirked.

Nathan felt a little pleased. He'd never had a drink with his Mom before, he'd never known her to be this... cool. He placed the bottle and the glasses onto the coffee table in front of Sally, who poured for each of them. "Sit down." She told him, scooching over on the couch for him to sit down next to her.

Nathan already quite tipsy from earlier that evening, sat perhaps a little too close to his Mom than he would normally, their thighs pressed against each others, but neither seemed to mind or care. They took their glasses in hand and threw back the alcohol. Nathan coughed a little. Sally giggled. "Sorry, probably stronger stuff than you're used to." She sighed again but smiled at her sweet boy, pushing the hair out of his face and stroking his cheek gently.

"You have fun at your party at least?" she asked him. He turned red. "Oh?" she laughed. "I know what that means. What's her name?"

"Chloe, and we uh just kissed... a bit... but I mean... she has a boyfriend so."

"Kissing a girl who was already dating someone else?" she stated with a smirk, shaking her head.

"Well she suddenly remembered when I tried to do a little more with her than just kiss..." His face felt very warm when he realized who he was telling this to. "Sorry I shouldn't... not with you."

Sally laughed. "Why not with me?" she asked, reclining back on the couch. "It's not like I've never done anything like that. Kissed a guy when I had a boyfriend, check. Kissed a guy when he had a girlfriend, check. We've all be young once, learn from my experiences," she giggled.

Nathan laughed with her though still unsure whether to feel uncomfortable or not. He swallowed more tequila, it went down easier this time. "Do you, uh... I mean..."

"What?" Sally asked encouragingly.

"Well I mean all these guys, I know you've been on more dates lately. Were any of them any good. I mean like I know you haven't brought any of them home... uh..." His face was burning again. "Sorry, what I meant was... uh..."

Sally laughed, her own face turning a little red. "I mean, you're right, I haven't. None of them were very successful, no. I haven't 'brought a man home' in a long time... and none of them have taken me home either..." she said, draining her glass and pouring more, topping up her son's as well.

Nathan was feeling a little dazed but kept drinking. "Um... I'm sorry..."

"For what?"

"For all those guys..." he said awkwardly, feeling bad for his Mom not having anyone. He'd gotten to go on dates and sneak girls into his room, why couldn't his Mom do the same. It seemed unfair. "I mean you're beautiful, and you're great so I mean, if they don't see that, that's their problem," he heard himself say.

Sally was touched. She took her son's hand in hers. "Thank you sweetie, that means a lot. You're very handsome yourself. Look at you... that physique..." she said as she poked one of his biceps. "...that cherub face... no wonder you're so popular at these parties you go to," she smirked. One hand remained on Nathan's, the other held her glass, her finger rubbing the rim slowly as she looked at him and smiled. "...my Nate..." she murmured as she stared.

Nathan stared right back, noticing, not for the first time, her large bust that was right in his eyeline. He felt his mouth go very dry. It wasn't the first time he'd had sexual thoughts about his mother, something he felt very ashamed of. Once he'd seen older pictures of her in a bikini at some beach somewhere and a younger Sally had entered his mind that night as he lay in bed with his hand on himself. Another time he'd seen her walk out of the shower with just a small towel wrapped around her, squeezing her breasts and ass while showing plenty of both. She'd entered into his thoughts that evening too.

This was the first time Sally had thought of her son sexually before, however. She saw him suddenly as a man, no longer a boy. He was tall and strong, he could hold his liquor which was always a big plus for her. He was a man she'd made and molded, a perfect gentlemen, always looking after her. Why was he out chasing these young girls who didn't know what they were doing? He needed a proper woman. These were the thoughts the tequila was making swirl around in her head. The drink had flushed out the small amount of shame that might have kept her from agreeing with these thoughts and from doing what she did next.

She leaned forward and kissed her son softly on the lips. It was a very unmotherly kiss. It was delicate but sensuous, He sat frozen, glass still in his hand, unsure what to do, how to move, what the hell was going on. "Wha-?" He began, his eyes glazed over.

"Shhh..." his mother said, giggling softly, before kissing him again. It was longer this time, more lusty. It did not take long for Nathan to reciprocate, kissing back. A natural impulse, he found himself placing his hands on his mother's waist. When they finally stopped, Nathan's hands were still on her, Sally's hands were on his face. Nathan was speechless, unsure what to say or what to think. Luckily Sally spoke first. "Better than Chloe?" She asked. Nathan tilted his head.

"I mean... it wasn't bad... it's just... me and her kissed like a lot more and I mean... we were kinda touching as well..." he blurted out, not thinking at all what was coming out of his mouth, stopping suddenly, worried he'd offended her.

Sally smirked. "Okay, a challenge then." She didn't know who this girl was, but she suddenly wanted to compete with her. With her and all the little bimbos her son had been messing around with. Oh she'd heard them occasionally, their pornstar moans through the thin apartment walls, this son of hers was not as stealthy as he thought. She'd do better than them, really show them she still had it. "Maybe we could do a little more than just touching." she suggested in a soft, sultry tone, keeping her face very close to his, her hand slowly stroking his thigh.

Nathan was very confused by all of this and was wondering if there was something a little bit extra in that weed he smoked. "I um..." He had to have a long, hard think... or at least a think that was as long and as hard as his current condition allowed. "I mean... I mean..." A small voice in his head was telling him this was wrong, that it was fucked up, that he should leave now. But a much louder voice between his legs was very excited and making a much more compelling argument. He took his mom's face in his hand and heard himself say: "God you're hot!" He pushed his face forward and kissed his mother, longer than before. With his brain out of action, he listened to a different head instead, and it was hard and throbbing and wanting.

Sally's eyes were wide with surprise when her son kissed her that third time. They quickly closed and she kissed back wantonly. She hadn't been kissed like this in years and her son's clear lust for her was really getting her going. A little while in and Sally felt his large hand on her breast for the first time that evening, squeezing gently through her dress. She sighed at the touch. It had been so long since she'd been groped. Eventually she broke the kiss, and stood up.

"Your room or mine?" she asked, hastily, her heart racing.

"Um..." Nathan felt like he was on some kind of rollercoaster.

"Your room is probably messy," Sally considered. "My room then. Come quickly." She smirked before unzipping the back of her dress and letting it fall to the ground. She stepped out of it, completely naked and enjoyed the look of her son's hungry eyes running up and down her body. She snatched up the bottle of tequila and moved quickly to her room, Nathan's eyes fixed on her ass as made her leave.

Nathan took a minute to even somewhat comprehend everything. He stood up, finished his drink and rushed off to his Mom's room, tearing off his shirt in the process. What he was doing and who he was doing it with were far from his mind. All he knew was there was a very attractive naked woman who wanted to sleep with him and he owed it to himself to make sure that happened.

He found her laying on the bed, drinking right from the bottle. He stood in the doorway, just taking her in. She looked amazing. Her long hair fanned out underneath her. Though there were some lines under those blue eyes and her face had a few more freckles than the year before, it still seemed quite youthful. But Nathan had seen all that before. New to him were the large, perfectly round breasts. These too had a smattering of freckles on the top of them. They were sagging a little but Nathan didn't care about that. And above his mother's pussy was a large tuft of hair as orange as the hair on her head.

His body was shaking as his eyes ran over her. He wanted to go to her, to place his hands all over her, to put his mouth on every inch, but something was holding him back. He definitely wanted her, his cock was hard and pulsing in his tight jeans, but he was also scared. This was his Mom, he suddenly realized. But it wasn't the blood that bothered him, it was the expectation. She wasn't just some girl from school who'd never done more than held hands. This was a woman with some life experience. Would he be good enough for his mother? Would he be able to satisfy her. In that moment he suddenly felt very overwhelmed by the situation.

"Are you just gonna stand there and stare at me Nathan, or are you go going to come over here and fuck me?" She asked with a grin. That just appeared to terrify him more. Noticing this, Sally chuckled, placing the half-empty bottle on the side and rolling off the bed. "Come here baby," she said, holding him. "You don't have to if you don't want to," she said, doing her best to hide her disappointment. "I'm asking a lot of you." He was still her little boy deep down, she realized. Maybe this was all a mistake, she considered, though in the here and now, its what she wanted.

"It's not that I..." began Nathan, "...it's not that I don't... want to it's just that... I'm not sure if I will be able to... I dunno..."

Sally reached down to feel him, finding something much larger than she expected. "Feels like you'll be able to, to me." She smirked. "Let's just take it slow?" She suggested, though deep down she was still second guessing herself, her libido had quickly taken over again.

She kissed him again and at the sensation of his mother's lips on his, Nathan quickly began to forget his anxieties. Time seemed to slow down again. Their tongues met once more and they were both lost in each other.

Sally's deft hands reached down and fiddled with her son's belt, unfastening it and then his pants. They felt to his ankles. His cock pushed out through the opening on the front of his boxers. Sally wrapped her fingers around it gently. God it was girthy, and quite long too. It was her turn to feel a little apprehensive. Had she had one this big before? Probably, but it had been a while. She kept the kiss going, her palm stroking the base of his shaft.

The sensation of his mother's touch felt strangely wonderful. Her hands were warm and gentle. It was more of a caress than the yanking he was used to. He groaned into her kiss and wrapped his arms more tightly around her. Sally's lips moved from his, gliding up to his cheek and then pressing close to his ear. "Get me onto the bed, honey," she whispered. Nathan nodded slowly and they moved towards the bed together.

Sally ungripped her son's cock as she lay back on the bed, Nathan suddenly feeling an ache at the loss of her touch. He discarded his underwear and lay atop of her, their lips meeting once more as his hard, throbbing member rubbed gently against her inner thigh. Sally sighed softly at the feel of it. Both of their hearts were pounding now, both of them recognizing they were inches away from the point of no return.

They both reached for Nathan's cock at the same time, their fingers touching. They had stopped kissing now, their eyes met, locked onto one another's. Slowly, their hands moved together as one. Both wanted this, both needed this. As soon as his tip entered her, Sally let out a large moan. "Fuck..." she cried out, smiling up at her boy. Nathan grinned back as he pushed himself all of the way in.

The thrusting was slow at first, but steady. Nathan had done this several times before but this time felt especially different, somehow. It was as if he was still testing the water, still uncertain of what he was doing here. It was strange, he hadn't even felt this nervous during his first time. His then girlfriend Paula had been and he'd taken it slow for her sake, but he felt a higher level of confidence in what he was doing. Right here, right now, however, it was different feeling entirely. And he was sure that it was because of who he was inside right now that was causing it.

Sally enjoyed the pace however. She liked that someone was finally taking the time with her. As she lay on her back, gazing up at her son as he slid in and out of her, nervous mixed with determination on his face, she evaluated this performance with a disappointing sexual past. She remembered the night Nathan had been conceived, that was over far too quickly for her, she was surprised it had even resulted in pregnancy. Her last date, her last date to actually take her home, had been excessively rough. This was the pace she preferred, really feeling Nathan's cock inside of her. Her sighs became subtly louder with each thrust. She reached up with her hand to caress his face. "Good job so far." She said softly, trying to give him encouragement. He smiled back awkwardly. Sally's breath was becoming heavier from both the drink and the stimulation. "Okay, just speed it up a little... that's it... fuck..." she groaned, as Nathan followed her instructions.

He was gradually gaining confidence, really allowing himself to enjoy the feeling of himself inside of Sally. "...fuck..." he murmured, echoing his mom. He pressed his face into her neck and placed a hand on her breast, squeezing and groping as he continued to thrust inside her. He found himself steadily increasing his speed. Sally moaned loudly.

"Oh... Nathan..." she heard herself say. Her fingers gripped the bedsheets and her bare legs wrapped tightly around his body, as if trying to pull him in deeper. "Nathan..." she said again, this time a little louder. "Faster... faster..." Nathan nodded and pumped himself into her faster and faster.

It felt so good to have someone inside her like this again, and there was something so perverse about these specific circumstances, for some reason it was really working for her. Her moans were becoming louder and louder. She reached up and pulled her son's face to her own as she came, pressing their lips together roughly as he continued to fuck her.

Nathan's breath was getting heavy. His cock throbbed violently inside of his mother. He'd pushed all his worries out of his mind now. He was doing it, fulfilling his fantasy of really giving it to a gorgeous MILF, making her moan and cry out his name, so he must have been doing a good job. And the fact that it was his actual Mom too... "Ah... fuck... Mom... ah shit..." He came hard inside of her. "Shit, shit, shit, shit..." He pulled out, realizing in his drunken stupidity he'd forgotten to wear protection.

Sally laid back, dazed from all the drink and the sex. She had felt her son fill her with his load, she was unperturbed. It had been a long while since she'd felt that. As she felt it drip out of her, a small amount of the warm sticky stuff pooling between her thighs she simply giggled. Then she noticed her son siting on the edge of the bed, panicking. "Hey sweetie, what's wrong?" She asked, feeling so light-headed. She got up on her knees and moved over to him, holding him and kissing him tenderly on the cheek. "We were having such a good time."

"But I came... inside you and I...."

She laughed gently. "Oh is that it. Oh honey, it's fine, it's just cum. Get over here." She took his face in her hands once more and kissed him lovingly on the mouth. "You know it's not every man I let do that... but you're not just any man, are you." She smiled, touching him on the nose.

"So you're not mad.... you... you like it..." he asked, finding himself grinning again, his cock stiffening at the thought of his mom being into his 'creampie'.

She smirked and lifted up a small amount of the cum leaking out of her onto the tip of her finger. Her eyes locked with Nathan's, as she swallowed the morsel. "I love it." She responded, grinning. "You have to stop freaking out hun, your Mommy just needs to have some sex, okay. Can you do that for her?" Nathan nodded slowly.

"Good." She said, reaching over to lightly touch his sticky and quickly re-stiffening cock. It was very sensitive. "And I hope there was more in you than that," she giggled, gripping the base of his shaft with delicate fingers, before bending down and taking his tip into her mouth.

It wasn't long before her son was nice and hard again. Nathan stared down in awe, not quite sure what to do with his hands. He opted to stroke her bare back gently and occasionally push the hair out of her face, his as his eyes fixated on her head as it went up and down, his mom's lips tight around him as she sucked, taking as much of him in as she could, while her hand stroked the rest. It was a strange visual but one which made him pulse in her mouth.