No Monkey Business: Week 01

"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.