No Monkey Business: Week 01

"Okay," I said. I paused for a moment, and saw that mom was frozen in place too. "I feel like I could cum," I said at last.

"Well then," she said, shuffling back slightly then bending forward at the waist over the sink, pushing her ass out towards me. "What are you waiting for?"

I had no good answer to that, other than to stand up and frantically push my jeans and underwear down and off. I all but ran around the kitchen table towards my mom's ass, my hard cock leading the way, precum welling up from its tip. "Ready?" I asked, even before I got there. Mom only wiggled her ass at me. I unceremoniously yanked down her pyjama bottoms which pooled around her feet. Sure enough she wasn't wearing anything beneath them. Her pussy looked wet already, and the skin around it was red, with arousal I guessed.

I wrapped my hand around my cock and shoved it towards her pussy, the tip sliding easily into her, and I wasted no time in building up a rhythm against her. Mom let out a few soft grunts, but soon they started sounding less aroused and more like she was in pain. I wanted to believe that maybe the tip of my cock felt so good that it was making her painfully aroused, but it soon became clear that she wasn't painfully aroused, just in pain.

"Stop, stop," she said after about a minute of my thrusts. "I'm sorry, Steven, that kind of hurts."

"What's the matter?" I asked, pulling my cock backwards and out of mom.

"I think all that hammering of your hand has taken its toll," she said, sounding equal parts disappointed and frustrated. I looked down at her and realised that the red around her pussy wasn't her being inflamed with arousal. I'd been thrusting my hand (and, occasionally, her hand) aggressively against her for the past few days. It was understandable that she was starting to get sore. Understandable, but really annoying. I stood there for a moment, my cock hovering mere inches from mom's pussy. I wondered what she would do if I just slammed my whole cock inside her and started fucking her there over the kitchen sink. I knew what I would do. I'd last about ten seconds then cum like a fountain. Whether I'd survive those ten seconds was less clear to me. Mom had made it clear she wanted my cum, and just as clear she didn't want us to actually have sex. She sighed, apparently not seeing a solution to our problem. "Could you try jerking off, but not against my pussy?" she asked.

"We tried that, mom, remember?" I said. "It didn't work."

"Oh yeah," she said. "What if... no."

"What, mom?"

Mom seemed to psych herself up for a moment, then offered her suggestion. "What if you masturbate against me still, but not against my, my vagina. Then when you're cumming you can slide it inside. I mean, if your penis is already nearby."

I gulped, not entirely sure what mom was getting at. "So, you want me to...?"

"For fuck's sake," said my mom under her breath. But not quite so softly that I didn't hear it. Then, more loudly, she said, "Rub it on my butt, Steven."

"Right," I said, gazing longingly down at the butt in question. I still wasn't really sure what she wanted me to do. I decided to risk a liberal interpretation of her request, and slid my cock into the crack of her ass. "Like this?" I said, rocking my hips back and forth.

"Uh, sure," she said, not sounding too sure. I went for broke and reached for her ass, pulling her cheeks apart enough for my dick to nestle down, so that when I released her, the cheeks rippled back into place, my cock snug between them. I could tell my mom wasn't sure about this development so decided to hurry up before she changed her mind. With my hands on her hips pulling her back, I started thrusting forward.

It didn't take me long to realise that this felt good on a whole new level. What we'd been doing had felt amazing, but I realised that it was essentially glorified jerking off, with a tantalising tease of being inside my mom's pussy as the grand climax. This was something far more sexual. I was getting an ass job from my mom, and it felt incredible. For me, at least. My mom was far less vocal than she had been on previous occasions, and I realised that unless she had some secret erogenous zone hidden in her butt crack, she wasn't really getting stimulated by this. It might have bothered me if I wasn't seconds away from my own orgasm.

"Close!" I grunted for mom's benefit, slamming my hips forward against her. In fact I was more than close. Before I knew what was happening a wave of pleasure surged through me, and a rope of cum flew from the end of my cock, following a beautiful parabolic arc over my mom's back and landing neatly in her hair. "Shit," I hissed, pulling back just as more cum flew forward and landed on mom's ass. Not sure how much more cum I was going to manage, I rammed my cock into mom's pussy and held it there, trembling with my orgasm. Only a dribble more cum emerged once I was inside mom, meaning that most of my sperm were in places that were unlikely to lead to an encounter with one of mom's eggs.

"You might want to work on your timing," said mom drily as I pulled my cock out of her. She reached down and pulled up her pyjama bottoms before resuming the washing up. I was surprised she was standing up straight so soon after I'd cum inside her, running the risk of my precious gift leaking straight out again. But then she could probably tell that the load I'd given her wasn't going to make much difference in the grand scheme of things.

"I know, sorry about that," I said.

Mom just shrugged. "It's no big deal, sweetheart. You might want to get washed up a bit." I had worked up quite the sweat during our session, not to mention the usual array of fluids coating my crotch.

"Right," I said, and headed upstairs for a quick shower. The rest of the evening passed with us both sat companionably in front of the TV. It wasn't awkward, per se, but I couldn't shake the feeling that I'd failed in my task. I'd do better next time, I decided.

--

In my dream I was driving, I know not where. A gorilla stood on the road side, thumb outstretched, wanting a ride. I ignored him. He gave me the finger. It was a long drive, and a shame I had to do it alone.

My dream shifted, as they so often do, and I wasn't driving the car alone, I was in the back seat with Cassie. We were making out passionately, a scene that came straight from my memory. In my memory, making out led to some pretty frantic groping, or even my tongue writing love poems on her clit. My dream had other things in mind, and it shifted again from a make out session to me pounding into her pussy from behind. The car in my dream helpfully expanded in size to make this more possible. It wasn't the only thing that had grown. I ran my hands over Cassie's ass, which had gone from what might politely be called petite to an ass to die for. Once again I realised that dream Cassie had somehow gotten hold of my mom's ass. And then Cassie moaned out "I'm going to cum" and the voice no more belonged to my ex girlfriend than the ass did. I was fucking my mom, I realised, with a jolt.

The jolt carried through from my dream into the real world and woke me up. For a moment I lay there, confusion reigning supreme. But a very pressing feeling below the covers woke me up in a hurry. My cock was hard, an orgasm so close that I was surprised I hadn't cum already. I froze in place, sure that even that wouldn't be enough to stop the impending eruption. If a butterfly flapped its wings in Kansas I was pretty sure there would be a tornado in Tokyo and a huge sticky mess in my bed. I could hear the clock ticking on the wall opposite and started counting the seconds, partly to ensure I didn't accidentally have a sexy thought and cum, and partly just to see how long it would take for my cock to calm down.

I was well into the three hundreds before I felt like I could move without having an accident. I immediately flung off the covers and slipped out of my boxers, worried about the stimulation they might provide just by touching me.

It was ridiculous, it really was. I was eighteen and had cum eight times in the past four days. I shouldn't be having wet dreams. It was some kind of sick joke my balls were playing on me. It was also a problem. The immediate threat of an orgasm had passed, but my cock was still just as erect. If I went back to sleep now I would be waking up in a puddle of my own cum. But I couldn't jack off - mom needed all of my cum that she could get. Especially after the fiasco with my last performance. That's when I remembered what she'd said the day before. About cumming in her whenever I needed to, night or day. True, she'd also said we should stick to two sessions a day, but the digital clock by my bed assured me it was after 2am, so technically it was tomorrow.

My logic may have been shaky, but this time I really do have to blame it on how horny I was. I slipped out of bed naked and made my way out of my room, down the hallway, and quietly opened mom's bedroom door. With the lights off I was having to do it all by memory. Fortunately I knew the layout of the house pretty well after eighteen years of living there.

I shuffled over to mom's bed and paused for a second. Through the silence I could hear my mom's steady breathing, she was asleep. Well of course she was asleep, it was the middle of the night.

I reached down and felt for the covers, then slipped into bed. Mom made a small noise but didn't seem to wake up, so I manoeuvred myself across the bed, under the covers, until my exploring fingers made contact with her.

"Mom?" I said, softly.

"Mmm, Steven?" she said, her voice thick with sleep. "Is it morning already?"

"Uh, in a sense," I said. I knew I was on dangerous ground, but I felt like getting my cum inside mom was the main priority, sticking to her twice-a-day notion was more of a guideline.

"Okay," she said. And then nothing. I decided to take that as permission and reached down until I found the waistband of her pyjamas. Mom was laying on her side but she lifted her hips slightly as I pushed down, helping me get her bottoms off, and even cycled her legs lazily to kick them off once they got past her knees. I then returned my hands to her waistline but got somewhat distracted en route by her ass. Even in the pitch black her ass was a thing of wonder to me. I stroked it with my hand, feeling how soft it was, the exceptional curve. I could have lay there all night just stroking it. Mom had other ideas.

She let out a low growl, it sounded more like lust than annoyance, but when she said "Behave" there was definitely some annoyance there too. She reached behind herself, I thought to move my hand from her ass. Instead, she fumbled around until she found my cock, and made an appreciative noise at how hard it was already. She then scooted backwards towards me until we were spooning, making sure she lined my cock up along my ass crack as she did so. She then released my cock and took my hand, moving it around so I was holding her around her middle, and finally gave her ass a little wiggle up and down.

If that was her way of signalling that I should begin then she wouldn't have to ask twice. I immediately started thrusting up, her ass feeling astonishing around my cock. My arousal was already in full swing and precum started oozing out from my cock, making the sensation even more delicious and letting my cock slide higher and lower along mom's ass with each thrust.

The eroticism of doing all this while essentially blind was not lost on me, and I had a sudden twinge of guilt that, as with our session in the kitchen earlier, mom was presumably not getting so much out of this.

With only a half-baked, horniness inspired plan in mind I started to make sure my thrusts into mom's ass crack went a little lower each stroke. Before long I started to feel the outline of mom's asshole with the head of my cock at the bottom end of each stroke. Mom shifted uncomfortably then, perhaps worried I was going to accidentally start fucking her ass. But that wasn't my plan.

After a few more thrusts I pulled back just slightly further on one of my backstrokes. When I pushed forward again my cock took the path of least resistance and rather than sliding back up mom's ass crack it headed straight between her legs. Mom gasped and reached down, perhaps planning to move my cock back again. But I was rock solid and fully erect, and as I resumed thrusting I could feel my cock rubbing over mom's clitoris with each pass. She started letting out gaspy little moans and she seemed to think better of moving me.

After a few minutes of this mom started moving her hips slightly, probably trying to maximise her own stimulation. While this new position was clearly doing it for mom, I had to admit that sliding my cock over the entrance to mom's pussy was not as stimulating for me as her snug ass crack had been. I was far from in danger of going soft, but nor did my orgasm seem to be getting any closer. I was stuck in a highly pleasurable sexual limbo.

Not quite sure what else to do, I decided to use the same tactic I had a few days earlier. In the dark I didn't know what mom was wearing on her top half. It didn't feel like one of her jumpers, so it was probably the top half of one of those pyjama sets she liked. Whatever it was, I moved my hand down from her tummy where she'd placed it and quickly slid it back up under her top till I reached the swell of her breasts. I grabbed one unceremoniously and started squeezing it between my fingers.

Mom let out a surprised coo and started bucking her hips harder against me, before grabbing my hand through the material of her top and squeezing it even harder than I had been squeezing her breast.

It was a delicious sensation, and I thought I might finally cum. And that's when mom stopped moving and pulled away.

"Wha...?" I managed to say as my hand was yanked from mom's top and my cock fell from between her legs. But mom didn't have stopping in mind. Instead she rolled over to face me and reached down to grab my cock, shoving it awkwardly back between her legs to slide against her pussy.

"Fuck me," she whispered, more to herself than to me. I knew enough to know this was her lust fuelled dirty talk rather than an explicit request, but damn did it make my cock twitch just hearing it.

I started thrusting like a man possessed, the base of my cock sliding over mom's clit and making her gasp, moan, and reach around me to claw at my back. I reached around too and grabbed mom's ass. I squeezed it and pulled it, using it to pull mom against me, using mom to get myself off. It all felt way too good to last, and I didn't.

"Mom," I managed to croak out. "Cum... uh." It wasn't exactly poetry and I wasn't even sure if mom heard me as she never stopped rubbing herself against me.

I reluctantly let go of mom's ass and reached frantically between mom's legs from behind, not wanting another cum splattered fiasco like in the kitchen. I positioned my fingers so on my final thrust forward my cock slipped neatly into mom's sopping wet pussy, and I pushed it in to the very hilt.

Mom let out a squeal and I grunted with lust as my orgasm struck. She then let out a less motherly cry of "Fuck!" and rolled onto her back, pulling me with her even as the cum started to jet from my cock. Her hips started going berserk, rolling and bucking against me, and jostling my cock around inside her pussy in a way that would have had me cumming in seconds if I wasn't already. She made a few more noises that might have been words or might have been meaningless, and then her orgasm struck.

If I thought my orgasm felt good then mom's clearly put me to shame. I could feel her whole body shaking beneath me. She was gasping for air and her fingers dug into my back like she needed me to survive. Without warning she grabbed my head in the dark and pulled it down to hers, kissing me frantically on the lips. I kissed back almost on instinct then opened my mouth in surprise. Mom seemed to take this the wrong way and shoved her tongue in my mouth, wrestling with my own even as more whimpers emerged from her throat.

The kiss only lasted a few seconds and then mom flopped her head back onto the bed, breathing hard. Small tremors still passed through her body as her orgasm slowly faded. My own orgasm had come to an end sometime during the kiss, though as I shifted my hips I felt another trickle of cum emerge from my cock.

"Wow," I said when I had enough breath back to say anything. I heard mom chuckle quietly.

"Wow is right," she said. "Sorry if I got a bit carried away at the end there."

"Oh it's okay," I said. I have to admit I was starting to feel a little awkward now that my orgasm had come and gone. That had been way more erotic than our previous sessions. I could see now why mom had wanted to avoid this whole thing taking on any sexual overtones. And that kiss! I felt guilty, but I was a little horrified about the thought of kissing my mom. With the lights on I'd rather go one on one with that gorilla from my dreams than make out with mom. Only the anonymity that the darkness provided had made it happen.

As I was thinking all this mom reached over to her bedside table to turn the digital clock towards us. My cock slipped from mom's pussy as she did so and I moved over the bed until I felt the edge, then sat on it.

"Huh," mom said. "Three thirty. I thought you said it was morning."

I suspected she was looking at me askance, but luckily with the lights off I couldn't see her do it and she, presumably, couldn't see where I was to aim it. "I said 'in a sense'," I reminded her.

"Uh huh," she said. "Then I guess you won't want a session until tomorrow night? Sorry, I mean tonight."

I stammered something unintelligible before realising mom was almost certainly just winding me up. She decided to let me off then. "Good night, Steven," she said. "Thanks for the cum."

I smiled in the dark. "Night, mom. Thanks for having it."

Retracing my steps from earlier I headed back down the hallway and collapsed in bed, falling asleep before I knew it.

--

Mom might not have been entirely serious about our middle-of-the-night encounter being the next day's morning session, but as it turned out that's precisely what it became.

We both woke up late after our exertions, and both found ourselves with a long list of things to get done. I'd agreed to help my friend Claire move some stuff to her boyfriend's house on the other side of town. Neither of them had a car and she wanted to get her most precious belongings safely out of her parent's house before she left for college. I guess she was worried that her mom and dad would sell them, or something. As I had the biggest car amongst her friends left in town I'd agreed to help out. When I'd offered to help a few weeks earlier it had seemed like a good idea, but now I found myself becoming slightly irked at Claire's doll house collection. I could have been at home blasting another load of cum into my mom's waiting pussy. Instead I was wrestling an oversized, undersized house through Claire's boyfriend's front door. He seemed pretty miffed too. Apparently Claire and her boyfriend had different definitions of "a few small items". By the time we all sat down for pizza that evening, the poor guy's house looked like it had more of Claire's belongings in it than his own. I couldn't help but suspect that come the Christmas holidays I'd be helping Claire move all these items back out again following a tragic break up.

When I got home it was already dark. Having had so much sexual release in the past few days I thought my body might appreciate having had the morning off. But if anything I was hornier than ever. I was trembling as I unlocked the front door of the house and went inside. I was going to find mom, wherever she was in the house, whatever she was doing, and I was going to fill her up on the spot.