No Monkey Business: Week 01

And then I looked up.

My mom was looking down at me, an odd look on her face. But it wasn't the odd look that threw me, it was the face. I could say that seeing her face reminded me that I was about to cum inside my own mom, and that's what bothered me. But I'd be lying. My mother was powerfully unattractive, plain and simple. The cum that had been ready to burst from me like an unstoppable force thought better of it and receded back into a holding pattern in my balls. I knew if I stood there much longer I'd lose my erection too. I pulled backwards, my cock slipping out of my mom's pussy with a quiet pop.

"You didn't ejaculate?" said my mom, part question and part statement.

"Uh, no," I said, suddenly bashful. "I guess I wasn't quite as close as I thought I was," I lied.

"Oh, okay," said my mom. "No problem, just carry on."

I nodded and, not knowing what else to do, closed my eyes and returned to Cassie in the back of my car. We picked up where we'd left off, her on top, riding me like her life depended on it. Thinking it might help, I flipped my imagined Cassie onto her back so she was in roughly the same position as my mom was in front of me. I'd been really close to cumming and my body apparently had far fewer qualms about cumming inside an imaginary Cassie compared to a very real mom and so in a couple of minutes I was ready to cum again. I waited even longer this time, sure I was going to wait too long and cum all over my mom's sweater. But I managed to avoid that ignoble fate and warned my mom again. "Gonna cum, mom!" I said.

Once again I opened my eyes and guided myself to my mom's opening. This time I paused for a beat then slammed my hips forward, pushing my cock even deeper until my hips came to a stop with a dull slap against my mom. I'd decided this time I just wouldn't look up at my mom, but when my cock slammed inside her my mom let out a breathy moan. I automatically glanced up at the noise and saw my mom's face, her eyes closed and a look of pained pleasure on her features. I looked away immediately but the damage had been done. My cock hovered on the brink of an orgasm but already I could feel it start to recede. I was so close! I knew that only a little stimulation would suffice, and so I pulled back a few inches then slammed forward again. I was sure that was enough and opened my mouth, intending to moan at the pleasure emanating in my balls. Instead I let out a pained "Agh!" as my mom slapped me.

"Steven!" she yelled, pulling back and away from me. My cock popped free again and I was sure it was going to pick that moment to explode everywhere. Somehow it refrained, instead bobbing slightly in time with my pulse and looking purple and angry. "I said no sex! That means no thrusting, no groping, no monkey business! Just put it in and cum!"

"Sorry, mom," I said, keeping my eyes down in a look of contrition. As an added bonus it meant I didn't have to look her in the face and lose my erection. "It won't happen again."

"See that it doesn't," she said, her tone softening. "What's taking so long, anyway?"

"It's just hard," I said, before adding "difficult, I mean. The timing. I have to stop masturbating to put it in you, and then I don't need to cum any more."

My mom nodded, accepting this reasoning. "I suppose if it gets the job done you could, sort of, have the tip in. While you masturbate, I mean. Then as soon as you start to... finish, you could put the rest inside. That way you won't spill any."

I wasn't sure if that would work but it seemed worth a go. "Okay, I'll give it a try," I said. Mom got back into position and I manoeuvred my cock then pressed the head into my mom. She sighed softly but I resisted the urge to look up. Instead I carefully encircled my exposed cock with my thumb and a finger, making sure not to touch my mom's pussy. I then closed my eyes and got back to Cassie.

It didn't take long for the problems to become clear. Holding just the head of my cock inside mom's pussy while stroking it, but without touching my mom, was a tricky operation. Doing it with my eyes closed was going to be impossible. "Sorry, mom!" I said, having shoved my hand against her pussy twice and accidentally pulled out once in the space of five seconds.

"Okay, stop, stop," said my mom, sitting up slightly. "That's not working," she said. "Why don't you just open your eyes, that might help."

I floundered for an excuse not to other than 'I don't want to risk seeing your face.' I settled for "I don't think that would help. It's just too awkward to avoid touching you."

My mom sighed in exasperation. She'd probably thought getting a horny teenager to jerk off then cum inside her would be easy. "Alright, I guess you can touch me if it's not a sexual thing. Just hold your hand here like this and jerk into it." She reached down for my cock before realising what she was doing and pulling her hand back. Then she seemed to steel herself and reached down again. She grabbed my still hard cock and I jumped slightly from the contact. Before I had the chance to react she pulled my cock towards her. I moved my hips forward to accommodate her as she held her hand against her pussy in such a way that if I rocked my hips I'd be fucking her hand, with my cock's tip only just inside her. "See," she said, as I gave my hips a few experimental thrusts "like that." The feel of her hand around my cock was incredible, but all too soon she took her hand away. "Okay, you do it."

I moved my hand where hers had been, very aware that I was now touching her pussy with my hand. She let out another one of those breathy moans, but I resolutely stared down at her pussy as my cock rocked back and forth between my fingers, the head making obscene sloshing noises as it moved around just inside her pussy.

I heard a whispered "Oh, God," come from my mom and I realised that in our current position I was pushing the knuckle of my thumb right into her clitoris every time I humped my hand. The objective may have been for me to cum inside her, but it occurred to me that my mom hadn't had sex since I was conceived. Would she cum too, I wondered? I started to thrust harder and faster, the bed creaking rhythmically as I fucked my hand over mom's pussy.

"Oh, god, oh, Steven, are you close?" asked my mom, her voice a whimper.

"Yes, mom," I groaned, the cum rising once more and hoping it was third time lucky.

"Oh, oh, oh," sighed my mom. I was no expert on my mom's sex noises but she sounded awfully close to her own orgasm. For some reason I suddenly wanted her to cum too. I held myself back from the edge for a few seconds more, and my willpower paid off as my mom suddenly tensed up and cried "Oh, fuck, Steven! Cum inside me!"

Right on cue my balls gave up the load they'd been trying to get rid of and cum shot from my cock. As soon as I felt the first blast I moved my hand and rammed my cock as far into my mom's pussy as it would go. Maybe it was the fact I'd essentially been edging myself for the last half hour. Maybe it was because it was my first time inside a woman. Maybe it was both. Whatever the reason I came like I'd never cum before. My legs trembled as shot after shot of cum rushed from my cock. I fought to stay still, all too aware of mom's feelings on thrusting. Luckily I didn't need to move as mom's pussy was clenching and trembling around my cock, stimulating it as well as any thrusting would have achieved. Mom's orgasm seemed to be at least as rewarding as mine as she let out shaky whimpers and clasped the bedsheet in her hands.

Finally our orgasms subsided, though my cock stayed relatively hard inside my mom. I was breathing hard, despite not doing much, and my mom sounded like she'd been running for the last half hour, not laying down. "Thanks," she said once she had her breath back, as if I'd just helped her bring in the groceries, not flooded her with cum.

"No problem," I said, finally looking back at her face. If I'd thought about it I might have expected to see my mom in a new light after what had just happened. Maybe realised that she really was beautiful all along, or some shit like that. But no, my mom still looked like the ugly sister's uglier cousin. My cock, hitherto ready for round two, suddenly decided it needed a break, and slipped softly out of my mom.

I wasn't sure how to act then, or what to say. It wasn't the kind of situation you find yourself in often. Fortunately mom took charge, and was all business. "So how often do you normally, ah, masturbate a week?" she asked.

I'd just jerked off in front of her and cum inside her, so it was ridiculous that her question made me embarrassed. And yet it did. "Uh, everyday," I said, before admitting "twice some days."

"Okay," said my mom. "Great!"

That wasn't exactly the response I'd expect after telling my mom I jack off every day (twice some days), but then this wasn't a normal day.

"You're leaving in two weeks," continued my mom. "I reckon you can push yourself to twice a day every day until you go. Right?"

"Uh, sure," I said, momentarily not understanding why my mom wanted me to jack off so much. Like I said, I may be dumb sometimes, but this was all new to me. My brain caught up after a moment and I realised she wanted me to cum inside her twice a day for the next two weeks. I had to admit that the thought of repeating that orgasm I'd just had was an appealing notion. If only I'd been one of those lucky bastards with a hot mom. But then I probably wouldn't be in this position.

"Okay then, why don't you go get cleaned up," said my mom, and I realised she was dismissing me from her room. That was fine with me and I high tailed it to the bathroom for a much needed shower.

--

If you've never jerked off in front of your mom then cum inside her as she has an orgasm you accidentally gave her (and I'm going to go out on a limb here and assume you haven't) then you might think the most awkward part about it is actually doing it. Standing there, with your cock in hand, doing that most private of activities right in front of your own mother. Pretty awkward, right? Actually, not so much. I don't know about you but when I'm jacking it I don't really worry about mundane things like that. I mean, when you're jerking off do you get fixated on the fact that your parents are in the next room, or that you're using the hand that you used to shake hands with your grandpa a few hours earlier? Of course not. Masturbation is the great mind cleanser. When you're doing it, nothing else really matters.

So if not the actual act, then the most awkward part has to be the immediate aftermath, right? We've all had that post-masturbation come down. Oh god, we think. My parents are in the next room! I just used that hand to give grandpa a handshake! Why was I watching midget elephant porn! Everything that seemed unimportant in the face of impending orgasm suddenly comes back into focus. Cumming inside your mom seems like the kind of thing that might feel good at the time but send you straight into therapy afterwards. Well, not for me at least. As you probably gathered, I didn't do it because the haze of horniness descended and I just had to cum, no matter where nor with who. No, I did it because my mom guilt tripped me into it. And apparently I was going to do it again.

No, for me, the really awkward part was a few hours later as I sat down for lunch at the kitchen table with my mom. Or as she would now forever be known, the first woman I came inside.

"So what've you got planned for the rest of the day?" asked the first woman I came inside, or as she will be known for the rest of the story: mom.

"Oh not much," I said, wondering if mom was acting cool or was genuinely unfazed by that morning's activities. I considered adding 'Gonna cum inside you again later' to see if she'd react to that, but figured hell hadn't quite frozen over yet. Instead I said "Alex invited me to go bowling, but I said I couldn't go."

"Oh, honey," said my mom, "you don't need to cancel your plans for me."

I opened my mouth to tell her that I hadn't. That I was avoiding the bowling alley because Cassie's brother worked there and he seemed to think I'd cheated on her, or something, and was just waiting for an excuse to kick my ass. In fact I'd begged Alex to change his plans so we could hang out, but he'd said it was too late. So unless I went out for a drive by myself I was stuck at home with mom. I thought about saying all that but realised how mean it sounded. If I could cum inside my mom to make her happy then I could tell a little lie about why I was at home.

"Pfft," I said, "it's no problem. It'll be nice to spend some time with you before college."

My mom's face split into a grin. Her happiness made the white lie worth it. And if I was honest then it would be nice to spend some time with her. I'd been so caught up in preparing for college and seeing my friends that I had been neglecting her a little.

"Well then," said my mom, "how about we finish up in here then watch something truly awful on TV?"

Now it was my turn to grin. "You're on!"

The afternoon passed in a pleasant blur of oversized sharks and unlikely weather events. Sometimes simultaneously. We paused briefly to rustle up some burgers for dinner before collapsing back in front of the TV. By the time the last film finished I'd almost forgotten the little task I had in stall. Almost.

I was hoping that mom had forgotten, or at least changed her mind. Then I could go to my room and jack off, just me and the mental image of Cassie, without mom's actual image intruding. But no such luck.

"So, Steven," she said, as she flicked off the TV. "Ready to go again?"

I gulped, suddenly feeling nervous, and nodded. "Your room again?"

"Yep," she said. "Let's go." We traipsed upstairs and back into her room. My jeans were still laid on her chair and I realised I'd left them there this morning, changing into new ones after my shower. By the time I'd noted this my mom already had her own jeans and underwear off. She turned to her bedside drawer to grab the lube, affording me my first view of her ass. It was love at first sight.

I'd never really considered myself an ass man, but if any ass could convert me to that path then it was the one before me. Two large, round, eminently grabbable globes faced me. The skin looked soft and I felt my cock stirring immediately in my pants. I quickly shed my jeans and underwear and tossed them on top of my other pairs. I couldn't take my eyes off my mom's ass, and I wondered why she always covered it up so. Maybe she didn't realise what a thing of beauty she had behind her.

My cock reached full attention just as my mom turned back around, lube in hand. I automatically looked up at her face and my erection started to wilt just as quickly as it had arrived. She was looking down at my cock, a wry grin turning into a frown in unison with my cock's descent. "Everything alright?" she asked, cocking an eyebrow.

"Yeah, fine," I said unconvincingly.

"Okay," she said, drawing it out into a question. When I didn't say anything else she just shrugged and sat down on the bed. "Same procedure as this morning, okay?" She took some lube and started massaging it into her pussy.

I had to do something to see that ass again. If I was allowed to look at it I'd be able to cum on demand, as many times a day as mom wanted. Faced with her face it was a struggle just to stay hard. "Actually, mom," I started, wondering how the hell I was going to finish this sentence. "I was reading up on this kind of thing and, well, apparently, according to scientists, your chances of conceiving go up if I do you from behind. I mean, if I insert my penis from behind. When I ejaculate, I mean. In that position."

Mom frowned, not exactly believing me but also willing to go along with virtually anything that improved her chances of having a baby. "Huh," she said, "I didn't know that."

"Yep," I said, "it's because of evolution." I was terrible at lying, and this was a terrible lie. But, somehow, mom bought it.

"Okay," she said. "In that case I'll lay on my front, other than that you can do the same as this morning. No thrusting or groping, remember!" she said, waving a finger at me like I was a naughty child.

"Scout's honor," I said, my cock already stirring at the mere thought of such proximity to my mom's ass. Mom just gave me a suspicious look, but she did roll over onto her front, leaving her ass and pussy exposed on the edge of the bed, and her face hidden from view.

I walked over and stood between her outstretched legs. Up close her ass looked even better. I wanted to grab it and squeeze it. I wanted to taste it. I wanted to fuck it. I wasn't allowed to touch it. It was exquisite torture.

"In your own time," said mom, and I realised I'd just been stood there drooling over her ass.

"Right, sorry," I said. I grabbed my cock which was almost painfully hard before I'd even touched it, and pushed the head into my mom's pussy. My mom's clitoris was a hard little nub and I made sure my finger lined up with it as I wrapped my hand around my cock, ready to jerk myself into my mom. "Ready?" I asked, though I wasn't sure what my mom could do at this point to prepare further.

"Yep," she said, "knock yourself out."

I gazed down at her ass and had to catch myself before I got lost staring at it again. Slowly, I began to rock my hips back and forth, making sure my hand moved around enough to stimulate mom's clitoris. If she suspected I was doing it on purpose then she didn't say anything. I thought I'd last longer, having cum already today, but I hadn't counted on my mom's hidden treasure. As I moved my hips back and forth I fantasised about pulling my cock from mom's pussy and slamming it into her ass. In the fantasy she accepted it readily and came as I fucked her ass. In reality I expect she'd kill me as soon as she could sit up straight.

Mom's breath was coming heavier as I continued to thrust my hand against her clit. I adjusted my grip ever so slightly, allowing a little more of my cock into her pussy. I thought she might flip out and slap me again, but instead she let out a low groan and then started to grunt quietly with each of my thrusts. "Fuck," she said in a voice that she probably thought I couldn't hear, and then, more loudly, "are you close, Steven?"

"I'm close, mom," I said. It hadn't been that long but with mom's pussy around the end of my cock and her ass in front of me I was struggling to hold off my orgasm. I briefly considered asking mom to turn around for a second so I could make things last longer, but I didn't want to spoil the moment.

"Oh god, mom," I said, feeling the pressure build up in the base of my cock.

"Steven!" my mom squealed. I felt her whole body tense up and I knew she was only seconds away as well.

"Mom, I'm cumming!" I cried out as the cum surged from my cock. I pulled my hand away and grabbed my mom's ass with it, using it as leverage as I surged my hips forward. I bottomed out as cum flew from my cock and deep into my mom. My balls pressed against my mom's clit, which was apparently the final straw as she let out a breathy scream and started her own orgasm.

"Fuck!" she grunted as her whole body trembled. Her pussy felt like it was massaging my cock, drawing out every last drop of cum. Her trembling had the added benefit of making her ass jiggle in front of me, a sight so erotic that I wasn't sure if I'd go soft even after cumming. Unfortunately even mom's ass couldn't stop the inevitable and my softening cock slipped from mom's pussy, followed by a small trickle of lube and our combined cum.

I stood there still breathing heavily, enraptured by the sight of mom's ass and pussy. As for mom, she sounded out of breath too, but eventually managed to say "I thought we said no groping. Sure felt like your hand on my butt, mister."