No Monkey Business: Week 01

Mom calmly reached down and grabbed her pyjama bottoms, then pressed them against her pussy to stop my cum dribbling everywhere. "Well then," she said, as if we'd just finished watching the news, "night night, Steven."

"Night, mom," I said, feeling a bit surreal, then watched her ass sashay upstairs. I contemplated falling asleep right there on the couch but knew I'd regret it in the morning. Instead I forced myself upstairs, stripped off the rest of my clothes, and fell into bed, grateful with my last waking thought that mom had changed my sheets since the morning.

--

I don't know what I was dreaming about the next morning, I only know it couldn't compare to what I woke up to.

I was laying on my back, naked, and with my bed covers nowhere to be found. Of more immediate note was the hand I could feel stroking up and down my cock with a purpose. I raised my head to look down and saw mom crouched by the side of the bed, the bottle of lube in one hand, my hard dick in the other.

"Oh, hi, Steven," she said when she noticed me looking down. "I thought I'd help get you ready for this morning's session. I hope that's okay."

"That's fine, mom," I gasped, laying my head back on the bed so I didn't have to watch her face as she jerked me off.

"I know this is difficult for you," she went on as she stroked. I assumed she meant the situation as a whole, since being jacked off was not high on my list of things that were difficult for me. "And I really do appreciate you doing this for me."

"It's nothing, mom, really," I croaked, feeling my cock start to twitch with an impending orgasm. I'd only been awake for a minute, which led me to wonder just how long mom had been jerking me off as I slept. "I'm getting close," I said, wondering what position she'd want me in today.

"Okay, honey," she said. "You just stay there, I'll take care of this." I wasn't entirely sure what she meant, until she stood up, threw one leg over me and knelt on the bed, her pussy hovering directly above my cock and - praise be! - her ass facing me. She grabbed my cock again then slowly lowered her pussy over the cock head protruding from her hand. "Ready?" she asked, and I realised that in this position she would be the one fucking me rather than vice versa.

"Go for it," I said, gazing hungrily at my mom's ass.

And go for it she did. She immediately started bouncing her hips up and down apace, thrusting down onto her hand and the cock within. I was still waking up but quickly realised there were some added benefits to this position. First, mom was putting her whole body weight down with each thrust, not just using the power she could muster from her hips like I had been. Her hand was doing its utmost to stop my cock penetrating her pussy, but it was clearly struggling under the onslaught. As a result much more of my cock was pushing inside mom with each of her thrusts. I was still a long way from actually fucking her, but the feeling was divine nonetheless. Another benefit was, predictably, her ass. I'd thought it looked good when still, but the sight of it shaking up and down in time with her thrusts made me wish I was a poet so I could pen an ode to it then and there.

"Oh fuck, mom, that feels good," I said. It occurred to me that wasn't the kind of thing I was probably supposed to say during our arrangement, but after mom's dirty talk the previous night I was feeling a bit freer.

"Oh, Steven!" my mom cried, apparently agreeing with my evaluation. "Fuck me, Steven! Fuck me right now!"

Despite mom's words she kept her hand tight around my cock, preventing any actual fuckery from taking place. But, spurred on, I did start thrusting my hips upwards in time with her downward pushes. The result was electrifying and after only a few more thrusts I felt my cock race past the point of no return. "I'm cumming, mom!" I yelled, at just the same time as mom whimpered "I'm cumming, Steven!"

She pulled her hand away and thrust down hard at the same moment as I bucked my hips upward. Our hips met in the middle and my cock exploded with cum, showering the inside of her pussy. I grunted with lust as I came, while mom made incredibly sexy little moans. Finally my orgasm abated and I lay my head back down on the bed, gasping for air.

I assumed that mom would get off me then, but she seemed in no rush to. After another minute of laying there, my cock still inside her, I found out why.

"Steven," she said.

"Mom," I replied.

"I need to lay down," she said.

I let out a little laugh. "I know, right? That was pretty intense."

"No no," she said, then gave a little laugh herself. "Well yes. But that's not what I mean. If I get up like this then your cum is going to go everywhere. I need it inside me, remember?"

I'll be honest, I'd actually kind of forgotten why we were having these mind blowing sessions. The pleasure I was getting from them was my reward, I'd let slip from my mind the fact that there was a point to them. I was supposed to be getting mom pregnant. I had two weeks to do it. Given how much cum I was pouring into her I didn't think failure was likely. But what if mom didn't get pregnant? Would these sessions continue? Would I come back home for the weekend, fill mom with my cum, then wave goodbye and go back to college? Or what if mom did get pregnant. I'd have a little brother or sister. And a son or daughter. Christ, it was too much to think about, so I focused back on the matter at hand.

"Okay, mom," I said. "How do you want to do this?"

"Just sit up then help me lay on my front," she said. "And don't pull out!"

My cock had yet to go down too much, so it was still being effective at plugging my mom's pussy, but I didn't know how long that would last. I pushed myself into a sitting position and pondered how to get mom flat without pulling out. I settled on wrapping my arms around her jumper-covered torso, then awkwardly pulling my legs back until I was sat on my calves. This little manoeuvre didn't go perfectly, and my cock slipped back and forth, threatening to fall from my mom's pussy on a few occasions and forcing me to jerk my hips forward to keep it in place. The fucking motion was not lost on my cock, which didn't exactly become fully erect again but certainly stopped flagging. Finally I was in position behind mom and ready to lower her down onto the bed. "Okay," I said, "down you go."

Mom nodded and started to lean her weight forward. I'd meant to gently lower her but as I leaned forward with her, gravity got in on the action. I let out a little yelp as our center of gravity passed some critical point and we both fell forward, her face first onto the bed and me on top of her. The motion pushed my cock into depths of mom's pussy that I hadn't been to before, and both mom and I let out grunts, while my cock gave a half-hearted little spurt of cum that it had been saving.

After getting her breath back, mom said "Thanks, Steven. You can pull out now, and maybe go shower." I nodded, then grunted agreement having realised she couldn't see my face. I wasn't as sweaty as I had been after previous encounters, but my crotch was damp with our combined juices. I slipped my cock from mom, entranced by the sight of it bobbing over her ass, then hopped off the bed, heading for the bathroom.

--

After a start like that, the rest of the day was always going to be mundane in comparison. I realised I had a bunch of paperwork that I had to fill out before I started college, and with only twelve days until I went there I couldn't put it off any longer. I stayed holed up in my room for most of the day, printing out forms and filling them in. Half of them needed to be scanned and emailed to various people, while the other half needed to be sent in hard copy. I wondered why they couldn't all be filled in online. Whatever the reason, they needed doing, and so do them I did.

Aside from toilet breaks I only left my room a couple of times, once to grab something for lunch and later for dinner. The first time I went downstairs mom was sat on the couch, working on her laptop. The second time she was still on the couch with a book in hand, but she looked like she was ready to nod off. I guess she hadn't had much sleep the previous night.

I finally fired off the last email and sealed the last envelope at about 11pm. It was way later than I'd anticipated, and I had to stifle a sudden yawn. It occurred to me that I hadn't heard my mom come upstairs, and nor had she come to ask me for my evening sperm donation. It was possible she'd decided to skip a session. Possible, but unlikely. I went to investigate.

I found mom where I'd last seen her, on the couch in the living room. She was laid on her front, her head resting on a small cushion, and her face towards the back of the couch. Based on her steady breathing I figured she was asleep. I could have just left her there. I could have been a noble son, laid a blanket over her, and tiptoed back upstairs. I told myself that I was only waking her up because she'd be more comfortable in bed, and because she was the one who was desperate to get pregnant. It was bullshit of course. I wanted to cum, and cumming inside mom's pussy felt amazing.

I knelt down beside the couch and gently rocked mom's shoulder. "Mom?" I said, quietly. "It's late, mom."

She stirred and her breathing changed slightly as she woke up, or at least became a bit less asleep. "Mmm, okay hon," she said. "I'll head to bed in a minute. Good night." I thought she was going to leave it at that, and that I'd have to go upstairs and jerk off by myself. It suddenly didn't seem as appealing as it had used to. But mom apparently remembered herself at that point. "Oh," she said, groggily. "Be a darling and just cum inside me before you go to bed, okay?" The way she asked it she could have been asking me to take the trash out. I matched her tone as I responded.

"Sure thing, mom."

"Mmm, such a good boy," she said, sounding like she was already falling back to sleep.

I stood up and shucked off my pants and underwear, then shrugged to myself and pulled off my top too. It felt better naked, somehow. I then turned to mom's pyjama bottoms. Given all we'd done it felt weird to be nervous, but this was the first time I felt like I might be the one in charge, and so my hands shook slightly as I slipped my fingers into the waistband of mom's bottoms and slowly pulled them down. Mom lifted her ass ever so slightly to help me, affording me an excellent view of it as her pyjamas slowly descended. Again, she wasn't wearing anything beneath her pyjamas. I wondered if she ever did.

Once her bottoms were off I tossed them on the pile of my clothes. I grabbed a cushion from one of the other seats and slid it under mom's hips, lifting her pussy slightly into the air for easier access. My cock was already pretty stiff in anticipation, and it only took a few strokes to reach full hardness. I then knelt on the couch between mom's legs, spreading them to make room. "Ready, mom?" I asked, guiding my cock towards her waiting pussy.

"Mmm," she murmured, "ready and waiting." I pushed the head of my cock into her pussy as she spoke, noting that she was already getting wet, despite barely being awake. I then started thrusting forward into my hand. Mom sighed contentedly, but I was having trouble with the position. The cushion I'd slipped beneath mom helped matters, but her pussy was still too low to comfortably thrust against while I knelt. I let myself drop forward a bit, supporting myself with my left arm while my right hand held my cock. That was a better position for me to thrust against mom, but with only one arm supporting me I soon had trouble maintaining my balance. It was not exactly erotic, wobbling around trying to stay in place as I bucked against mom. She was apparently too far gone to notice my haphazard thrusts, just letting out small sighs whenever I managed to actually push myself against her. I decided I was never going to cum like that, and so took the next logical step. I dropped down still further until I was all but laying on my mom. My left arm still took a bit of my weight, but I was basically on top of mom. I turned my head to the side, away from my mom's face, not really wanting a close up of that as I tried to get off.

Like Goldilocks, I'd found the perfect position on the third try. Or rather, it would be the perfect position for fucking. Less so for what I was supposed to be doing. With my body laying on mom's, and her ass raised up by the cushion and its own perkiness, there was no way I could reach my hand down between us to hold my cock. There was nothing to stop my cock burrowing inside my mom with each thrust, except maybe some exceptional self control on my part. I do not have exceptional self control. I gave an experimental little push forward and my cock was half way into mom's pussy before I knew it. I hastily pulled back as mom stirred.

"Where's your hand, hon?" she asked, slurring slightly as she hovered somewhere between sleep and wakefulness.

"Just rearranging things," I said quickly. I pushed my hand down between her and the cushion, then made a 'V' with my fingers and positioned them on either side of the entrance to her pussy. "There it is," I said, hoping that in her sleep addled state she wouldn't be able to tell the difference between a few fingers pressed against her and my whole hand.

"Mmm," she groaned. "Such a good boy." Apparently my half baked plan worked. To be fair, in drier times my fingers might have been enough to hold my cock at bay. But between the copious wetness oozing from my mom's pussy and the precum leaking out of my cock, they did nothing to help. My best bet would be to just go for it, cum as quickly as possible, and get out of there before mom realised that rather than holding back a hand's worth of cock, I was holding back just a finger's worth.

I started to thrust. I soon realised that if I angled my humping downwards then mom's prodigious ass actually stopped my thrusts before most of my cock had a chance to penetrate her pussy. True, it was more than just the tip, but not enough to really be considered fucking. At least that's what I told myself. My body didn't seem to mind the distinction, especially as the approach I was taking meant my stomach was bouncing up and down on mom's ass, a truly delicious sensation. I was so distracted by it that I didn't notice my thrusts getting ever deeper. Only my mom cooing "Ooh" near my ear broke my reverie. Half my cock was vanishing into mom with each thrust. The realisation broke some dam inside me and I suddenly started cumming without warning.

"Mom!" I groaned as the cum poured from me. I yanked my hand out from under her and buried my cock up to the hilt in her pussy. My mom murmured meaningless sounds and gyrated her ass, encouraging my cock to fill her with its load. I wasn't sure how aware she'd been of me, whether she knew I'd been going way beyond jerking off against her pussy. If she did know then she decided to keep it to herself.

"Mmm, thanks sweetheart," she murmured. "G'night."

"Night, mom," I said, rapidly getting off the couch, grabbing my clothes, and dashing upstairs. I could hear her breaths take on the slow, steady cadence of sleep before I even reached the steps.

--

When I woke up the next morning, something seemed wrong. It took me a moment to figure out what it was. My limbs all seemed to be intact. I hadn't broken an eighteen year streak and wet the bed. The house didn't seem to be on fire.

No, what was wrong was that I was alone in my room. Up until two days ago this wouldn't have surprised me. But in those two days I'd woken up with mom first hovering over me and then jacking me off. Her absence this morning troubled me. What if she'd decided to call off our arrangement? I'd wanted that more than anything when we'd started, now I wasn't sure I'd want to stop even after our two week period was up and I'd, presumably, succeeded in getting mom pregnant.

Still, I was never going to explain mom's absence if I stayed in bed all day. I hopped out and headed downstairs in just my boxers. Mom wasn't down there. If she'd slept on the couch then she must have gotten up by now. That only really left her bedroom, so I returned upstairs and knocked on her door.

"Come in!" I heard her call. She didn't sound mad, which was a good sign. I opened the door and poked my head through.

"Morning, mom," I said. She was sat in bed, her legs under the covers and one of her large green jumpers covering her top. Her laptop sat on her lap and I assumed she was getting on with some work. "Oh, sorry," I said. "I didn't mean to interrupt you if you're working."

Mom waved her hand dismissively and closed the laptop before putting it on her bedside table. "Listen, Steven," she said. I tensed up, pretty sure I knew what was coming. Maybe she wasn't mad about the previous night, but she'd be disappointed, she'd realise this was a bad idea. She'd say that she was probably pregnant by now and if not then it just wasn't meant to be. All I could do now was apologise and try to let her end our arrangement gracefully.

"I'm sorry," she said. My mouth fell open a little, trying to figure out what topsy-turvy universe I'd just fallen into. "About last night, I mean. I must have been pretty tired to fall asleep on the couch like that. To be honest I barely remember you coming downstairs to check on me."

"Oh," I said, relief and guilt flooding through me. "I did, you know..." I made an abstract hand gesture.

Mom nodded. "I know," she said. "I remember asking you to, uh, well, cum inside me. And when I woke up later there was plenty of evidence that you'd done what I asked."

I felt my cheeks redden slightly. "I hope that was okay," I said, and mom nodded.

"Of course, sweetheart! To be honest you could cum in me whenever you felt the urge for the next few weeks and I wouldn't mind, whatever I was doing, wherever I was, awake or asleep. But I don't want you to wear yourself out so we should probably keep our twice a day plan." I nodded as if I was thinking about the merits of what she said rather than the fact I really, really wanted to cum in her pussy again.

"Speaking of which..." I said, hoping she took the hint. It appeared she did as she grinned at me and flung the covers back on her bed, revealing that a jumper was the only thing she was wearing.

"Get over here and cum in your mom," she said, rolling onto her front and spreading her legs. Who was I to say no to that?

--

Mom and I ate together that evening, sitting at the kitchen table like a normal family. We chatted about college and for a while it was easy for me to forget that I'd all but fucked her the previous evening, and would be cumming in her for more than another week.

After food mom took the dishes over to the sink and started washing up. My gaze turned to her ass, as it was wont to do these days. Mom had taken to wearing her pyjama bottoms around the house, and I guessed nothing beneath them. They weren't exactly close fitting but they were much better than the voluminous jeans she had swum around in before. And besides, now I knew what her ass looked like beneath her clothes it was difficult not to imagine it.

I realised with a start that I was hard under the table. Instinctively I thought about heading up to my room to jerk off into a wad of tissues, but then I remembered that wasn't how things worked any more. I also remembered what mom had said that morning.

"Hey mom," I said. "Did you mean what you said earlier, about me cumming in you whenever the urge strikes?"

I saw mom nod, albeit a little hesitantly. "Of course, honey. Like I said, it's probably best if we don't overdo it, but if you feel like you could cum then I don't see any point wasting the opportunity."