No Monkey Business:
I know how these stories start. I'm supposed to tell you that my mom is the hottest person I know. That all my friends come over whenever they get the chance just to ogle her. I should say that I get mad at them for thinking of my mom in that way, but really I'm just mad because I think of her that way but could never do anything about it.
Unfortunately that's not how this story starts.
My mom is not a hot woman. She's forty years old and has a face that only a son could love. She's the kind of woman who didn't so much get hit with the ugly stick as she did fall out of the ugly tree, hitting every branch on her way down. With her face. Her hair is a dull brown and hangs lankly from her head. Her eyes are too small and too close together. Her nose and teeth all manage to be crooked, but not in the same direction.
The rest of her? That's where the cliché might be true. But that's getting ahead of myself. When this story starts I was as clueless as anyone else as to the charms that lay below my mother's neck. I had never seen her in a bikini. Nor a swimming costume. Not even a tight t-shirt. Hell, whatever the weather she only ever seemed to wear baggy jumpers and jeans that just didn't fit. Her choice of clothes didn't accentuate her curves, it hid them under folds of spare fabric.
From what I could tell, she'd always been this way. She hadn't been ravaged by the years. If anything, she looked the same now as she had since she had turned eighteen. You're probably thinking that she can't be that ugly, she has a son after all! Yeah, well. My mom may be ugly, but at least she's here. My father, on the other hand, has been conspicuous by his absence for my entire life. Part of me can't really blame him. My mother isn't unaware of how she looks and has become seriously introverted because of it. She's not exactly a bundle of joy to be around unless you really get to know her. I couldn't name a single friend of hers. She works from home, avoids family parties, and as far as I know has never dated anyone in her life. We've never discussed my father or my conception, thank God, but I assume it was a drunken one night stand, or a masquerade party where my mom's mask never came off. At least, not until it was too late.
With all that, it's fair to say that I'm about the only good thing in my mom's life. I try to be a good son, and I think I succeed. For eighteen years I've been my mom's constant companion, best friend, and the only person who's really loved her.
All good things must come to an end, though. Soon I'd be leaving for college. I'd got a scholarship to the state University. It was about a four hour drive away so I'd promised my mom I'd drive back to visit her as often as possible, but she wasn't convinced and she wasn't happy. I'd foreseen that reaction. The reaction I hadn't foreseen was her suddenly becoming broody.
"A baby?" I asked, certain I'd misheard my mother.
"That's right," she said. She was in the middle of washing up the dishes from breakfast. I was sat at the kitchen table behind her, orange juice in hand, and mouth agape.
"A baby," I said again. Not really a question this time. Just an attempt to make my brain understand the words. It didn't.
"Yes, Steven, a baby." My mother sighed. "You know what a baby is, don't you?"
"Yeah, mom," I said, shifting uncomfortably. "It's just... You want a baby? Now?"
"Well not right this minute, but yes. You're leaving me, Steven. I don't want you to feel guilty about it, you have your life to live, I know. But when you're gone, what will I do?"
"Geez, mom," I said. I wanted to say 'You'll be able to see your friends more' or 'You can start dating again', as if she wasn't doing those things because of me. But we both knew it had nothing to do with me. "A baby. Huh."
"You leave for college in two months, right?" she said, glancing over at the calendar on the kitchen wall. "Ideally I'd like to be pregnant by then. Then I won't be alone, not really." She absentmindedly touched her stomach, getting bubbles on her jumper.
"Okay," I said. "I guess it would be pretty amazing to have a little brother or sister."
Mom looked over her shoulder at me and smiled. I wasn't sure I really wanted to go into the details, but part of me was morbidly curious, so I asked anyway.
"So, uh, mom. How're you... you know?" Mom had turned back to the washing up but I could see her neck start to turn red with embarrassment. I suspected mine was too. "Will the hospital, you know, artificially... you know." I really wished I hadn't started that sentence.
Mom shook her head. "No, hon. My insurance won't cover that sort of procedure, especially if I'm, ah, that is to say. Not if I can conceive... naturally."
Now my face was definitely red. "Oh." I managed to say. "Well then. I'm sure you'll find... can't be that difficult... yep." I finished lamely.
Mom finished the washing up during my dazzling soliloquy and stared at the floor as she dried her hands. "Yes, I'm sure I'll manage." With that she almost ran from the room and I heard her bedroom door shut. I went up to my own room and tried to think of anything apart from that morning's conversation. Eventually, I succeeded.
--
The next month was a flurry of activity for me. I hadn't quite foreseen how much preparation was involved in leaving home for the first time. I also had my friends to see as much as possible before we scattered across the land. Unlike my mother I did manage to have a group of close friends, and intended to stay in touch with them.
I should also probably point out that I didn't inherit my mother's looks. Thank you, dad! I'd even landed myself a girlfriend, Cassie, during my final year of high school. We'd done quite a lot of heavy petting in my car, and I'd even gone down on her a few times, but my cherry remained thoroughly intact. When she asked to meet me a month before college started I let myself believe that this was the night. It turned out she didn't want to fuck me, she actually wanted to break up with me. There would be lots of girls at college, she told me, and she didn't want me to feel beholden to a girl on the other side of the country. I suspected it wasn't my freedom to fuck around that she was trying to ensure, but I decided not to pursue it. I smiled, nodded, said the right things and got out of there. It was probably for the best. Cassie and I got on just fine but I'd never really felt anything for her other than a teenage desire to get off.
My preparations for college may have been going apace, but my mom's attempts to find a willing sperm donor were going nowhere. We hadn't discussed it since that first chat in the kitchen, but I knew mom hadn't left home for anything more than grocery shopping since then, and I was pretty sure no one had been around while I was out with my friends or my now ex-girlfriend.
I'd wondered how my mom was trying to find someone willing to get her pregnant, and with about three weeks to go before I left I stumbled upon the answer. I'd been on Craigslist, trying to sell some stuff I'd no longer need and buy a couple of items that I was lacking. I'd arranged most of what I needed when, on a whim, I decided to check out the personals section for my town. Hell, maybe Suzie from high school was on there begging for a one night stand. I'd always had a thing for Suzie.
Suzie was not on Craigslist. My mother was.
"Unattractive 40 year old woman seeks man to impregnate her" was the title. The entry itself didn't give much more than that, other than to say the man would not be expected to be involved with the baby when it was born, and to provide a link to a photo. If my mother was trying to entice men then the photo was perfectly chosen to have the exact opposite effect. It was a close up of just my mom's face in all its glory. To be honest the whole entry looked like a joke. In a town the size of ours I doubted that many people would even see it, and those that did would not be tempted. I did not hold out much hope for my mom's success.
--
It turned out I was right not to expect much. With just two weeks before I started college my mom was still carrying as many babies as she had been for the last eighteen years. Namely none. I thought she might give up on the idea and buy a cat, or maybe just persevere beyond those two weeks. The deadline was self imposed and I didn't think it would really matter if she didn't get pregnant for a while longer. My mom had other ideas.
"Can I ask you something, Steven?" she asked.
"Sure, mom," I said. I was sat at the kitchen table drinking an orange juice while my mom washed up the dishes from breakfast. It was eerily familiar.
"Do you think I'm unattractive?"
I nearly choked on my orange juice, but managed to turn it into a small cough. "No, mom!" I said, perhaps too enthusiastically. I tried to dial it back a bit. "You're my mom, you'll always be beautiful to me." It was a lame answer I know. It was precisely the kind of thing parents say to their ugly kids. But what else could I say?
"Thank you, that means a lot," said my mom. She finished the last bit of washing up and turned around to dry her hands. I could see tears in her eyes. "I wonder, could you do me a favor?"
"Sure, mom, anything at all," I said.
She smiled at that. "Let's talk about it upstairs," she said, and headed off.
I followed, wondering what this could be about. When we got upstairs we headed into my mom's room. She sat on the bed and I sat facing her on the small chair she kept by her dressing table. "So..." I prompted.
"There's no easy way to ask this, Steven," she said. A long pause followed, probably because there was no easy way to ask what she wanted to. Finally she continued. "I've not had any luck finding a man to help me with... what we discussed before."
I nodded, having guessed as much. "Sorry, mom," I said. "I'm sure you'll find one eventually."
My mom shook her head. "I'm not so sure. Besides, you're leaving in two weeks, I don't have long."
"Oh c'mon, mom," I said, "you don't have to rush it."
Mom just shook her head. "I'm sorry but I need that child before you're gone. I need to feel loved even when you're not around."
"Oh, mom," I said, feeling a rush of love and sympathy for her. "I do love you, no matter where I am. And I always will."
"Thank you, Steven, that means so much to me. And it's why I know I can ask you this." I noticed a flush creeping up my mom's cheeks. And then it came. The favor. "Will you help me get pregnant?"
Now, you may call me dumb, but if your mom propositioned you out of the blue, I suspect you would be as confused as I was. "Um, sure," I said, shifting uncomfortably in my seat.
"You will?" said mom, looking up at me and grinning. "I didn't think you would say yes so quickly, oh thank you, Steven!"
"No worries," I said. "So, you want me to find a guy for you, right? I assume you've already tried-"
My mom cut me off. "No, Steven." Her grin had faded as quickly as it had arrived. "I want you to help me get pregnant." When my face still didn't show any sign of understanding she tried again. "I want you to help me get pregnant."
Finally the clouds parted and a ray of understanding reached me. "Oh!" I said. And then "Oh." If the blush on my mom's cheeks had been creeping then the one that appeared on my face was taking part in a 100 meter sprint.
"Yes," said my mom.
"Oh," I said. We both shut up then and took a sudden interest in the floor. Part of me wanted to say 'Whoops, sorry, big misunderstanding, I'm not fucking you, okay bye' and leave that room. Maybe leave the house. Maybe leave the country and never come back. I'll be honest, that was a big part of me. But some habits die hard. For eighteen years I'd been this woman's closest friend and I really did love her. I'd done everything to make her happy, and the thought of making her so miserable now just killed me a little inside. I wasn't sure I could go through with it, but I also didn't want to flat out say no just yet. I told myself I could always stop things later. Hell, I figured when it came to it my mom would realise how weird the whole thing was and stop it before we actually fucked. "So," I said, trying to move the conversation along. "You want me to... to... to have sex with you?"
My mom looked momentarily horrified. "Oh god! No, Steven! No no no. Nothing like that."
I let out a sigh of relief. Either I'd misunderstood my mom's insinuation - which was horribly embarrassing but probably not as bad as fucking my own mom - or else she'd realised as soon as I'd said the words out loud that the entire situation was ridiculous. Alas, it turned out neither of those was the case.
"No, obviously we can't have sex," my mom continued. "I figure you could just..." she made some vague hand gesture that it took me a moment to decipher.
"Masturbate?" I said.
"Right," she said, nodding furiously and turning an alarming shade of puce. "Until you're ready to..." she made another hand gesture, this one even more abstract.
"Cum?" I offered.
"Ejaculate," she said, giving me a stern glance before staring back down at the carpet. "Then you could just stick it in, inside me, at the last second. Until you're finished. No actual, you know, sexing required."
If I'd been concerned that having sex with my mom would be weird then I needn't have worried. The way she described it made it sound like the least sexual thing imaginable. I didn't really want to go through with it, but nor did I want to break my mom's heart. I decided the best thing to do would be to agree. By the time we actually got around to doing it I figured she'd have had a chance to change her mind.
"Okay," I said. "For you, mom, I guess I'm willing to do it."
"Oh, Steven, you have no idea how much this means to me," said my mom, looking back up at me with tears of happiness in her eyes.
I stood up, brushing some imaginary dust off my lap. "Well, let me know when you want to, you know, do it, and I'll, you know, do it." I made for the door but then my mom spoke up.
"Oh right now," she said. "I should be pretty fertile at the moment, but regardless we should probably do it as much as possible before you go to college. It might take a few tries to get me pregnant."
I stumbled and looked at her. All the blood that had been so keen to rush to my face now fled it, leaving me pale and nervous. "Now?" I said, or at least tried to say. Only a croak came out. I cleared my throat and tried again. "Now?"
"Yes now, honey. Unless you have somewhere better to be." I considered telling her that I did, but apparently she hadn't meant it as she stood up and started undoing her jeans. "You can put your pants and underwear over there," she said, pointing to the chair I'd just vacated. She slipped off her own jeans and folded them neatly before placing them in the corner. I wasn't surprised to see that she wore huge, brown, unflattering panties that adeptly disguised the shape of her behind. I was surprised to see that my mom had amazing legs. I felt a stirring in my cock and for the briefest moment wondered if this might not be so bad after all. And then my mom turned around and my arousal crawled back under whatever rock it had been hiding beneath.
"Come on, chop chop, honey," said my mom. She opened her bedside drawer and pulled out a small bottle of what looked like lube, then lay down on the bed, letting her legs dangle over the side so her panty-clad pussy was lined up with the edge. Feeling like I was in a daze I unbuttoned my own jeans and pulled them off, one leg at a time, before dumping them on the chair she had pointed to. "And those," said my mom, pointing to my underwear. My hands trembled as I hooked my thumbs into the waistband of my boxer shorts and slowly pushed them down. Gravity soon took over and they landed on the floor. I stepped out of them and placed them on top of my jeans. My cock is, as far as I know, perfectly average when erect. But it wasn't erect at the moment, and it appeared to have shrivelled up into near nothingness.
Apparently happy that I was getting on with it, my mom then sat up enough to push her panties down and let them pool on the floor around her ankles. She then lay back down, lifting the hem of her jumper up so it didn't obstruct her pussy.
I was pleasantly surprised to see that my mom had a pretty good looking vagina. I mean, I had minimal experience with real ones, but the ones I'd seen on the internet made it clear that they could range from things of beauty to horror shows. Mom's was definitely near the beautiful end of that spectrum. The brown hair around it was trimmed short and the folds looked inviting rather than repellent. I noticed mom glance at my cock and for a crazy moment I wondered what she thought of it. It looked pretty woeful at the moment. But then I reminded myself that we weren't having sex, so she probably didn't care what my cock looked like.
"Over here," said my mom, gesturing between her legs. "Stand there and do your thing. Just let me know when you're going to, erm, finish, and stick it in."
I shuffled over to where she'd indicated, trying to make the two meter journey last as long as possible. All too soon I was stood between my mom's open, naked legs, with my cock hanging out and an expectant look on my mom's face. "Off you go then," she said. She then proceeded to ignore me and poured a little lube into her hand. I couldn't help but watch as she smeared some over her pussy before using a finger to slowly start to spread it into the pussy itself. It wasn't lost on me that here I was, a virgin, stood in front of a woman who was essentially masturbating and waiting for me to cum inside her. My main problem should have been not cumming everywhere before I got near her pussy, but instead I wasn't even sure I'd be able to get it up.
"Steven?" said my mom, a note of impatience edging into her voice.
"Yep," I said. "On it." I took a deep breath, closed my eyes, and reached down for my cock. I'd thought the hard part would be masturbating in front of my mom, but a more immediate concern was the simple mechanical problem of jerking off while my cock was attempting to enter the microscopic realm. I awkwardly held it between my thumb and a couple of fingers and began to joggle it around.
With my eyes closed it actually got a little easier. I could hear the wet sounds of my mom lubricating her pussy but couldn't see her face - the face both of my mom and of a woman I really wouldn't want to have sex with anyway. Instead I thought about Cassie, my recently exed girlfriend and the only girl I actually had real sexual experiences with. I thought back to the last time I'd eaten her pussy in the back of my car. My cock grew back to its old self and even stiffened at the memory. In real life I'd made Cassie cum twice before she'd abruptly stopped me and told me she needed to get home. In my mind, though, I imagined things taking a different turn. Instead of stopping things, she wanted to return the favor. I imagined her soft lips wrapped around my cock, her head bobbing up and down as she tried to get me off. And then I imagined her crying that she couldn't stand it anymore and sitting up over my lap before impaling her pussy, still wet from my ministrations, straight down on my cock. I started rocking my hips slightly, imagining that I was fucking Cassie. In reality I'd probably want my first time with someone to last a while, but the Cassie in my head didn't care if I came already.
"Oh, God," I said, before remembering who I was jacking off in front of. "I mean, I'm about to cu- ejaculate, mom!" I cried, feeling the point of no return rapidly approach.
"Okay, get it inside me, quickly!" said my mom, sounding urgent.
I opened my eyes, and guided my cock head to my mom's opening, even as I felt the cum boiling for release. I pushed forward, into my first pussy. It felt better than I'd imagined it would. Oh so tight yet the lubrication made my cock slip in like it belonged there. I pushed forward until I was buried inside, my balls nestling against my mom's ass. I could feel the cum ready to explode out of me.
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."
"I'm sorry, mom," I said. "I was losing my balance, I just kind of grabbed the first thing I saw." It was a terrible excuse, but mom waved her hand to dismiss the subject.
"Listen, thanks again, Steven. I really appreciate you doing this for me."
"Oh it's no problem, mom," I said, hoping to sound like it was a necessary chore.
"I'm just going to lay here for a bit," she said. "I'll see you in the morning for our next session, okay?"
My cock jerked slightly at the mention of that, and I realised we had thirteen more days of our 'sessions'. I was starting to think this wouldn't be so bad after all.
--
I'd thought the next morning's session would be after breakfast, like the one we had on day one. But mom was either impatient or had plans, because she didn't wait that long.
"Good morning, sweetheart," I heard as I slowly drifted back into consciousness. I'd been dreaming of Cassie. We were in the car, fucking like we never had in real life. I was taking her from behind, but something was different. In real life Cassie was cute but not exactly blessed when it came to her tits or her ass. But the Cassie in my dream had an incredible ass, the best I'd ever seen. In fact I had seen it. It was my mom's ass! I had a moment to wonder how Cassie got my mom's ass, but then the owner of the car we were fucking in showed up, and he was a gorilla, and he challenged me to a dance-off. Dreams, man. Am I right?
Anyway, the dance-off was interrupted by someone's voice permeating my consciousness. I opened my eyes and saw my mom standing in my room. "Hey, mom," I said, glancing over at the clock. It was nearly 8am. Not exactly early but earlier than I'd grown accustomed to getting up during the holidays. I rubbed my face. "What's up?"
"I thought we could get started a bit earlier today," she said, "rather than taking up the morning with it. I'm sure you've got things you'd rather be doing."
"Oh, okay," I said, still a little groggy. "Shall I come to your room, then?"
"No need, hon. We can just do it here." That woke me up. Of course, when it comes to cumming inside your mom there's no room that's better than any other, but somehow doing it in my own bed seemed far more taboo. I didn't get the chance to voice this out loud as my mom whipped my duvet off. I only wore my boxers to bed, and at that moment they were doing a terrible job of restraining my bulging erection. I guess dream Cassie had me really worked up. I looked over at my mom and realised she was only wearing one of her frumpy jumpers. Her pussy peeked out at me from below the hem. "Up you get," she said, waving at me to get up. I stumbled out of bed and she moved to take my place before she spotted a problem.
Her King size bed gave her ample room to sprawl out as I did the deed. My bedroom was significantly more compact, and my single bed was tight into the corner. She couldn't lay down on it and dangle her legs off like she could on her own bed. I could see her realise this and figured we would be using her room after all. Instead she gave a little shrug and crawled onto the bed, getting into the classic doggy style position. She looked over her shoulder at me. "I guess this'll work too, right?" she asked. I nodded dumbly, staring at her ass held proud and high. I didn't think I'd have to go through the motions of fucking my hand against her pussy this morning. Her ass looked so good like that, that I was sure I could just stick my dick in her and cum right now. I forced myself to turn from her ass and look mom right in the face.
"I think this will be fine, mom," I said, exuding a calm that I did not feel inside. I gave mom a reassuring smile, glad for once of her face's remarkable turning off ability. Once I felt like I could move without cumming I turned back to her ass. I didn't take my eyes off it as I slipped my boxers down and stepped out of them. I'm not even sure I blinked. I then clambered back onto the bed and got behind mom, kneeling between her legs. I realised I was naked with mom for the first time, and also that she hadn't brought any lubrication with her. Presumably she'd applied some before coming through. If not then I didn't think it would matter. Precum was literally dripping from the end of my cock. "Ready, mom?" I asked. I felt like it was a little ritual now, and waited for her answer.
"Go for it," she said, and even gave her ass a little shake. I swallowed, hornier than ever, and moved forward.
Things started off okay. I guided the head of my cock into her, as I had before, including making sure her clit was going to be taken care of by my encircling hand. The problems started when I began to thrust forward. When she'd been laid flat, the bed itself held my mom in place. Now, with her pussy up in the air, every time I thrust forward her body rocked forward too. I couldn't get any real traction, and I sensed mom was getting frustrated too. My erection was in no danger of vanishing, so I kept the motion going for a few minutes, but this was clearly not going to work.
"Sorry, mom," I said, pulling back slightly. "I can't make it work like this, I need something to hold you still."
Mom seemed to think for a moment then gave a little shrug. "How about you hold me still," she said. "Just grab my waist with your free hand. That should work."
I figured it was worth a try. And holding mom's waist hardly constituted groping her. I got back into position, entered her with the head of my cock, and grabbed her waist through the material of her jumper. I noticed that she had a slim, firm waist under all that fabric, and I pondered for the first time what she might look like under those jumpers she always wore. I'd been orgasmically surprised by what lay beneath her jeans, it was almost certainly too much to hope for that her top half was just as good. And now certainly wasn't the time to worry about it. I resumed my thrusting motion, this time using my left hand on mom's waist to hold her back as I moved forward.
"It's not working, is it?" said mom after a few minutes of this. To be honest it was working better, and I probably could have gotten off if we'd persevered. But boy am I glad that we didn't.
"Not really, mom. Sorry," I said.
"It's not your fault, honey," she said. We were both silent for a while then. I assumed we'd now have to go back to mom's room and I could finally cum. That's when mom spoke up. "Okay, I reckon if you used both hands on my waist you'd be able to hold me back, right? Then you could cum."
I nodded before realising mom was facing away from me. "I guess so, sure," I said. But I've only got two hands, mom."
"Luckily for us I've got hands too," said my mom. It took me a moment to realise what she was getting at.
"Oh!" I said when comprehension dawned. "So you'll... hold me in place," I said. It sounded more decent than 'jerk me off into your pussy'.
"Yep," she said, reaching her hand up from between her legs in preparation. Holding her weight on one hand was apparently a bit more effort than mom wanted to exert, as she promptly let her front drop down to the bed. The effect on her ass was incredible, lifting it higher than ever. "Ready when you are," she said, holding her hand out ready for my cock.
I moved forward, placing my cock in her hand then taking hold of her waist in both of my hands. She adjusted her grip a few times, essentially giving me a mini handjob and making me wonder if I was going to cum before we even got started. I couldn't help but notice that the position her hand ended up in left her thumb pressed tight against her clit, ready to stroke against it with each of my thrusts. It seemed we were both ready for some release.
Once we were set up I pushed my hips forward. Mom's grip clearly wasn't where she thought it was as my cock slipped almost half way into her pussy before her hand stopped its progress. We both let out surprised grunts of lust. After a momentary pause I spoke up. "Sorry, mom."
"Not your fault" she said, sounding strained. "Just pull back a bit." I did as she asked and she adjusted her grip again. I pushed forward and this time her hand stopped me just after my cock's head penetrated her. "Okay," she said, "go for it."
I started to thrust again. Kneeling there naked, with my hands holding her waist it really did feel like I was fucking my mom. The thought didn't gross me out particularly. From the position I was in she didn't really seem like my mom. She was just a woman with an amazing ass letting me fuck her from behind. As I got into this way of thinking I started to thrust harder and faster. I almost let my hands roam upwards towards her tits, before catching myself. She might not seem like my mom, but that's precisely who she was. It occurred to me that with her head buried in the bed she might be feeling the same way about me. Sure she knew I was her son, but from her position I was just some guy fucking into her hand while she teased her clit.
As my hips crashed forward little shockwaves spread across mom's ass. It was hypnotic and, unthinking, I brought my hands down her body, coming lower than her jumper and holding her hips, skin to skin. I thought mom might protest, but she let out a soft sigh then started to let out louder ones with each of my thrusts until she was grunting with arousal every time I moved forward. Before long she was pushing her hips backwards, meeting my thrusts with her own. If she'd moved her hand we would have been fucking each other senseless. But her hand stayed resolutely in place, perhaps because through it she was teasing her own clit mercilessly.
I started to pick up the tell tale noises that signalled my mom's imminent orgasm. It was weird how quickly I'd gone from not contemplating my mom as a sexual being to knowing what she sounded like when she was about to cum. But I didn't have time for such musings as my own orgasm wasn't far behind.
"Steven," she gasped out between grunts. "Close?" she asked.
"So close!" I replied and redoubled my efforts to pound into her hand. The extra stimulation on her clit triggered her own orgasm and she responded by pushing her face into my bed and letting out a muffled scream. Caught up in her own pleasure she moved her hand from my cock and started rubbing her clit furiously. I wasn't prepared for the sudden removal of the only thing standing between me and my mom's pussy and my next thrust carried me forward all the way inside her. I tried to stop there, I really did, but my hips were on auto pilot and before I could contemplate what I was doing I'd pulled my cock back until only the head remained inside her, then crashed forward again. I don't know how many thrusts constitute a fuck, but I was at most a technicality away from fucking my mom.
Left to my own devices I probably would have kept thrusting into my mom until I came, an ending that was, admittedly, only seconds away. But my mom had regained enough composure to stop me doing anything we might regret, and when I pulled out for a second time her hand wrapped back around my cock. I groaned something indecipherable and stilled my hips, not sure if mom was stopping things because I'd crossed a line. But no, she really wanted that cum inside her, and when I stopped moving my hips she decided to take matters into her own hands.
She pushed her hips back so that a good third of my cock was once more within her pussy, and then she started to stroke me. It was an awkward position, and she couldn't get to a lot of my cock. Fortunately I was so lubricated with our combined juices, and so turned on, that she just had to rub frantically at my cock for a few moments to trigger the orgasm she wanted.
"Cumming!" I yelled and thrust forwards as mom pulled her hand away. I dug my fingers into her hips, trembling as the orgasm tore through me. My mom stroked my balls as I came, perhaps trying to encourage every sperm I had to make the trip. Based on the amount of cum I felt flowing out I think she succeeded.
Finally my orgasm subsided and I knelt there for a moment longer, shaking. Sweat was dripping from me, mixing with the other bodily fluids pooled around me on the bed. I unceremoniously sat backwards onto my calves, my rapidly deflating dick dribbling a final bit of cum onto my leg. "Shower," I said, when I could say anything. And with that I rolled off the bed and made my way to the bathroom on wobbly legs.
--
It turned out that mom's suggestion that we free up the morning by getting business out of the way first thing was a good one. I managed to meet up with Alex after breakfast (not at the bowling alley) and we ended up spending most of the day together. We reminisced about school and made the usual promises about staying in touch in the future. Whether that were true or not, time would tell, but if that was our last day hanging out together than it was a good day.
I got home close to bedtime and encountered mom reading on the living room couch. "Hey, mom," I said, sitting down on the couch.
"Hi, Steven," she said, then ignored me for a minute until she finished the page. That done she put the book down and turned to me. "How was Alex?"
"He was good, thanks," I said. "He's off to college the day after tomorrow, so it was good to see him."
"You're all leaving so soon," said mom. I thought she was going to tear up, maybe try to guilt trip me into not going to college after all. Instead she gave me a naughty smile. "We don't have much time. Ready to cum inside me?"
I tried to remember when it had become cumming inside her and not ejaculating. But mom cut off my thoughts by standing up and dropping her pyjama bottoms to the floor. She wasn't wearing any underwear beneath them. I wondered what she was wearing beneath her baggy jumper, but couldn't think of even a lame excuse for her to take it off. 'Hey, mom, I heard your chance of conceiving goes up if you let me see your tits' probably wouldn't cut it. I had almost two weeks to think of a reason. For now I had other things to think about. Mom knelt on the couch, ass facing out, and held onto the back of the couch with one hand. She reached her other hand between her legs and held it out, as if waiting to be given something. In a sense I suppose she was.
I stood up and dropped my own trousers and underwear before stepping over to behind mom. Her ass was every bit as incredible as I remembered it and I absentmindedly reached out to touch it before remembering the rules. Still, as awe inspiring as mom's ass was, I'd had three big orgasms in the past two days and was pretty tired after hanging out with Alex all day. My dick was far from being the shrivelled mess it had been when we'd started this endeavor, but nor was it ready to cut diamonds with.
"What's taking so long?" asked mom and reached backwards to grab my cock. As soon as she had it she realised the problem. But she didn't seem to think it was anything to worry about. Using a bit of spit as lubrication she started to rub my cock back and forth. I was pretty sure this was something I could do myself but I wasn't going to complain about someone else's hand stroking my cock. Slowly but surely it started to rise up and become truly hard. When it was fully erect my mom pulled me towards her waiting pussy. With the couch for support my mom could hold herself in place while I fucked my hand against her, so I figured we'd be back to that way of doing things. Instead she kept her hand wrapped around me even as my cock head entered her, then she thrust backwards against me, impatient for me to get moving.
Taking my cue I placed my hands on her hips and started thrusting forward. Mom made a purring sound as I began fucking her hand in earnest and she lowered her head. I decided to live life dangerously and slowly moved my hands upwards, going up under her jumper until they rested on her waist. They were back where they'd started that morning, only now there was no bulky jumper between them and my mom's tight waistline. I thought mom might object but if anything she started bucking back against me even harder. I realised that she hadn't used any lubrication on her pussy, yet the sloshing noises being made as my cock head penetrated her told me that lube wasn't an issue. Either she'd predicted my return to the minute and lubed up accordingly, or my mom was getting seriously wet from our encounters. I mean, I knew she was having orgasms but somehow the thought of her getting so turned on before we even started was even more erotic.
As if reading my thoughts, my mom suddenly started making little grunts and I felt her body tense up in orgasm. She managed to keep hold of my cock this time but went pretty limp apart from that. She stopped pushing back against me, leaving me to thrust into her hand and pull her back by the waist.
It took about five minutes but mom finally started to move again, her hips pushing back against me and her fingers massaging my cock with each thrust. After five more minutes I was pretty sure she was approaching another orgasm. My own felt close but I couldn't seem to get there. Maybe I was just too tired.
"Are you going to cum or what?" asked mom after a few more minutes. She didn't sound annoyed, if anything she sounded pleased. But it was getting ever later and I think we both wanted to just cum and go to bed.
"Yes," I said, between thrusts. "Just not quite there."
I decided to go all out and started hammering into my mom, my hips protesting as they were already pretty tired. The effort didn't bring on my own orgasm but my mom suddenly let out a mighty groan. "Oh, god, Steven," she said as her body shook. "I'm cumming!"
I realised it was the first time she'd admitted out loud that she was having orgasms as well, and my dick grew even harder with arousal. Even through her orgasm this wasn't lost on mom, who apparently thought that a bit of dirty talk might speed things along.
"Oh fuck, Steven!" she cried. "You're making me cum! Please, Steven, please! I want your big cock inside me, filling me with your cum!" She leant back then, away from the back of the couch and into me. My hands automatically roamed upwards, my fingers on her torso, before I realised where they were going and stopped them, holding mom's sides tightly. This wasn't lost on my mom. "I want your hands on my tits," said mom, her voice shaking as my hips pistoned up against her. "I want you to feel my tits, I want your cum all over them!"
I didn't know how much of this was dirty talk to get me off and how much was mom lost in her own lust. Whatever the case, I wasn't going to turn down the opportunity to check out mom's tits. I slipped my hands further up inside mom's jumper and finally reached the prize.
I'd been a tits man before meeting mom's ass and deciding to convert. Apparently mom's tits weren't going to take this lying down and were damn well going to convert me back again. In fact I don't think they took anything lying down. Mom's tits were big, there was no getting around that, each one more than my hand could contain. But they were also perky, defying gravity in a way reserved for good bras, surgical enhancement, and anime characters. I was pretty sure none of those applied here. Mom just had perfect tits. I squeezed them between my fingers and ran my fingertips over her nipples. For a moment I thought she had nipple piercings, then I realised that her nipples were just painfully hard with her arousal.
I was so caught up in mom's tits that I didn't realise they'd pushed me over the edge. I felt cum burst out of my dick and quickly yelped "Cumming" to mom. She moved her hand out of the way and thrust down onto my dick as I pushed up. A few more spurts of cum squirted out as I held mom down against me by her tits. All too soon I had to release her beautiful breasts as I collapsed back down onto the couch, gasping for air.
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."