No Monkey Business Week 01

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.