I was still trying to wrap my head around how horny it was with mom on our last sexploration. Letting someone watch us was even better than we could have possibly imagined. And even though we were sure our chosen voyeur was only going to watch us, in the hot excitement of it all, we ended up letting him take things much further. Mom had not only given him a blowjob, but she'd also let him shoot his entire load in her mouth, all while I fucked her from behind. Boy was that the craziest wildest sex we'd ever had.
So now we realised we were ready to let another guy go all the way and join us in a full-on threesome. That meant, of course, mom would need to get trained in anal, so I would have to prepare her for everything that lay ahead. Mom had never done anal before so it was going to take some time to break her in and then get her ready to take two guys at once. But we knew for sure, at the end of it all, it would be well worth the wait. Watching another guy with his cock inside her, while my cock was inside her too, was gonna blow both our minds. And later, when my dad returned - hoping to return everything to how it was before he had left - having mom trained in anal, oddly prove to be a very fulfilling skill to have!
"Did you get everything hun?" Mom asked.
"Sure," I said, opening up the bag and preceding to spill the contents onto the table. It was gonna be painful for her at first to get used to anal sex, so we really needed to buy the right equipment to build-up to the pain as painlessly as possible. And hell, we were both sure gonna have a ton of fun doing it.
"What's this?" Mom asked pointing to a fluffy, bushy thing on the table.
"It's called a tail butt-plug," I smiled back at her. "When you get used to having something in you this will look really cute and hot, it will make you look like you have a tail. This one is a fox's tail, I thought it was the hottest one they had."
"Oh really!" Mom said in surprise. "Will that make you hotter for me honey, seeing me like a fox?" She laughed.
"Hmm! Yeah, I think so. Guess we'll have to wait and find out. Of course, the butt plug is still pretty big, so it'll take a while for you to get used to anal before you can take something so big," I assured her.
"Oh, you're so caring, hun. I guess most guys would just be thinking about themselves and just shove that up my ass without even thinking about how I felt," she said.
"Yeah, I want to ease you in as slowly as possible mom. I heard a lot of girls hate anal because it's so painful the first time. But the girls who ease into it end up loving it in the end. I want you to love it too, mom," I smiled.
"Oh baby, you're so sweet. I'm sure I'll love having your hard pulsing cock in my ass," she winked, "and it'll be so much better if I know you're loving fucking my ass with it," she smiled. Kissing me deeply, she slipped one hand down the back of my loose shorts to grab hold of my ass, while the other slipped down the front to grab my already hard wet cock." Hell, all these sex toys had got me thinking, and I couldn't wait to use them all on her.
"This is a heart-shaped butt-plug. See how the hearts get bigger and bigger all the way to the top of the shaft," I said, showing her the pink butt-plug. "When you start out you'll only be able to take the smaller ones, but slowly I can insert more and more until even the biggest one is inside you. I guess we won't be able to put them all in the first few times. It might even take a week or more before you can handle them all. I heard it's because some girls find it so painful, but I don't want you to suffer mom," I assured her.
"Oh honey, don't worry, I know you'll take good care of me. Plus, I'm not a girl, I'm a woman," she said, kissing me again on the lips. "I can't promise anything yet, but if I can, I want to let you get them all in me within a few days, I want to try my best for you baby," she said. My cock now out of my shorts and in her hand, her thumb rubbing the pre-cum all over its head, the veins of my cock filled with blood.
"But I think it might be more than a week before I can handle this huge beast," she said, looking down at my wanton cock.
"It's ok mom, I'll give it to you whenever you're ready. I don't wanna rush you. When your ass is loose enough to take me, I'll be ready to fill it up with your favourite sex toy," I said, winking and glancing down to my dripping wet cock.
"Then let the sex games begin," mom smiled, taking a smaller black ball-plug with only 3 small-sized balls on it in her hand, and passing it to me. "This one seems like a safe place to start."
Taking the black ball-plug from her, I took some lubricant and squeezed some along the balls before rubbing it in. As I did so mom took her hands back and undressed herself. Now completely naked except for the pretty black choker she wore around her neck and matching black ankle bracelets and black high heeled shoes to help her reach closer to my height. Turning around, bent over the kitchen table, her ample breasts resting on the surface beneath, her ass jutting out, ready for insertion.
Squeezing some lubricant onto my middle finger I then gently rubbed it around the hole of moms ass. Gently teasing her, I pushed down on her asshole at which she sizzled with pleasure. Not daring yet to break her open and push inside her, I continued to ease her, all the while stroking and patting her ass cheeks with my free hand. As I stroked her asshole. Spread out on the table, she seemed to purr like a kitty, enjoying the gentle sensation on her sensitive asshole.
All three balls were pretty tiny and only the last one equalled the side of my thickest finger. Now, I was ready to finally penetrate her asshole with the smallest. Gentle pushing it inside her, I watched her breasts heave a little under her, squashed into the table, showing her satisfaction clearly. Now, the first tiny ball fully inside her, it almost seemed like a gentle relaxing massage to her. Confident of the non-existent pain yet, I slowly slid the second, slightly larger ball into her ass. Again, mom just lay on the table, enjoying the gentle sensation presented by the small balls as they entered her ass.
Teasing the two balls in and out of her ass, I could see how much she enjoyed the sexual sensation in her anus, and was happy to see that it wasn't at all painful to her yet. Quite the opposite, instead it seemed to be a very relaxing, relieving, pleasant experience for her.
Pleasuring her ass for a while, I was ready to try the last, slightly larger ball, this one about the same size as the width of my biggest finger, and when this one was in, I could really start to have fun too by inserting my own finger and gently teasing her ass with it.
As the final ball slid inside her asshole, I could finally see a tiny twinge of the pain to come, as she let out a slight and shallow gasp as the ball fully filled her ass. Leaning down to kiss her and comfort her I asked her how she felt.
"Oh honey, it's good. It feels so relaxing and soothing, but that last one definitely brought on a whole new sensation. I could feel that one gentle cross over the barrier from pleasure to pain hun. I guess you should get me used to that one for a while. Maybe I won't be able to go any bigger than that today babe," she whispered from her comfortable relaxation.
"Sure mom," I agreed, proceeding to gently pleaser her by slowly pulling out and then pushing in all three balls to gently massage her ass. As I slowly started to increase the speed, mom started to really enjoy the sexual sensation more and more and her breathing and panting started to rev up in unison.
"Do you want me to fuck you harder with it?" I asked, leaning down again and whispering in her ear.
"Oh yes please baby, I think I can take more hun, but only with this one. I don't think I'm ready for anything bigger yet," she admitted.
"Sure!" I said, kissing her cheek, neck and ears from behind as I slowly ramped up the speed and really started to fuck her ass hard and fast with the anal-plug.
Now, mom was really starting to feel the intensely hot sensation of anal sex and I could see she was really enjoying it. To be honest, I hadn't actually thought I would be able to get all three beads in her on our first try, but of course, I was her son, so I knew she had been through a hell of lot more pain when she had given birth to me. In fact, thinking about it now made me realise, maybe mom would be able to handle anything I could possibly throw at her, unlike an inexperienced teenager who might have found it too painful already.
Soon I was slamming moms ass without mercy and she was taking, and even loving every moment of it! Whispering in her ear as I widened her ass with the anal-plug, I suggested inserting my finger into her instead. Finally feeling inside her ass with my own finger would give me a kind of sensation far superior to the just seeing what the plug fuck her ass. Nodding her head in agreement, I gently slid the balls out of her as I lubed up my finger and slowly slid it into her ass.
Now I could see mom let out a slight sigh of pain and pleasure combined yet immediately reassuring me, telling me how much she wanted me. Gently pushing my finger into her ass, slowly moving deeper and deeper while fingering her at less shallow levels and gradually increasing until finally, my finger was the entire way inside her.
Now, deep inside her, I again started to increase my motions and fingered her deep then shallow, deep, then shallow. To my excitement, mom was clearly excited and ready for me to finger fuck her with all my strength. My hard wet cock dangling beneath me, I let it bounce on the cheek of her ass.
I was shocked that she had let me finger fuck her with all my force, but it made me realise again, that maybe we would be able to do so much more on this first time around because she had already experienced so much pain.
"Baby, try the cute pink heart-shaped one. I think I can take at least some of it," she said, lost in the moment and again wanting me, much the same as she had done when Daniel had cum in her mouth and face-fucked her, even though her own rules had initially strictly prevented it.
"Ok," I said, eager to move up to the next level snd see how far we could go this first time around.
Sliding my finger out of her ass, I lubed up the much longer pink heart-shaped ball-plug, the first of its seven heart-shaped nodes, being already around the size of the biggest ball on the smaller black one. Gently easing it into moms ass, I proceeded straight away to slip the second slightly larger one in her too. Larger even than my finger, she made little sign that the swap up in size was causing her any pain at all and simply urged me to have my fun.
Shallowly fucking her with the first two hearts, it was clear she was ready for more already and without even contemplating it I slipped, not only the third but the second one into her ass. Her response was to simply gasp in excitement for more, which I eagerly gave her. Pounding on her ass for minutes on end, she was totally lost on sexually exploration and the intensifying pleasures she was feeling in her previously virgin ass. Watching the cute pink hearts slip in and out of her ass was a super erotic adventure I would never forget. Now, all I could think about was inserted the cute fox tail plug in her so that I could fuck her vagina at the same time that her ass was filled with its huge balls.
"I wanna try the fox plug and fuck you mom," I said, pounding on her as hard as I could with the heart-shaped anal-plug.
"Don't you wanna wait until you've tried all of the heart-shaped ones first?" She asked almost breathless.
"Mom, I've been fucking you with them for a few minutes already and you didn't even notice I'd gone all the way up. It seems like you can take anything," I said. My cock bulging and brimming with cum, ready to spew in her pussy.
"Oh baby, I didn't know!" She exclaimed. "Then sure, have your fun honey, I think I'm already ready to be double teamed baby."
Before she had even finished speaking, I had yanked the heart-shaped but-plug all the way out of her ass, to which she let out a massive gasp, and was luring up the fix tail one ready for insertion. Slowly inserting it into her now ripe ass, and as the final ball split her ass even further open, she let out her first real scream of pain. Yet, before I could even try to comfort her, she assured me she was okay and almost demanded that I fuck her now while she was at the height of the new sensations she was feeling.
Ramming the foxtail butt-plug up her ass and seeing my mom with a fluffy fox tail hanging out of her pretty ass and knowing inside it she had its three balls stretching her ass wide, made me feel incredibly horny. My wet cock almost gushing with pre-cum already, I slid it quickly inside her so that now, finally, she was double penetrated for the first time.
"Oh god!" I thought, looking down at her ass and seeing the tail sticking out from one hole and my thick cock buried in another of her holes made immediately rev up the gears all the way to power fucking her pussy as hard and fast as I could.
Fucking mom like this was pure ecstasy and every few minutes I would pull out of her and slide around to her face so she could suck me off while I played with her ass, fucking it with the tail plug. Returning my cock once more to her vagina I enjoyed her as much as I could, only imagining how amazing it must feel for her to have not one, but two shafts, penetrating her at the same time. As I started to rev up to cum she begged me to do something I still didn't think she was ready for!
"Baby, I want you to fuck me in the ass and fill it up with your hot sticky cum baby, I don't want you to wait anymore," she said, "I'm ready now. I want you now," she demanded.
Shocked by her eagerness, there was no time for questions, I already knew when mom got super horny, she was liable to do and allow anything. I knew that from watching Daniel cum in her mouth then face fuck her when she had strictly forbidden it. So for her now to jump from possible weeks of anal training to having me fuck her in the ass right now, shouldn't really have shocked me. Yet as a lubed up my cock and squeezed it into her still tight cock-virgin asshole, stretching her wider than I'd ever thought it possible to stretch, she almost begged me with her every action, movement, and sound, to fuck her in the ass with all the force I had.
The foxtail on the table beside us, I powered deep and hard into moms ass, eagerly trying to bring us both to the point of climax as soon as possible. Her ass cheeks smashing into my thighs with every thrust, I pleasured her to the extreme. Now her moans revealed the mix of pleasure and pain like never before. My huge cock filling such a tiny hole was something I still didn't think was possible, even though my hard cock was rammed deep inside it, splitting it open with every powerful thrust of my pelvis.
Within minutes of entering her, I was ready to cum in her. Her body quivering, she too, was ready to explode. The final thrusts delivering the payload to her wanton asshole, I filled her up. Still pounding on her without easing up even after I'd ejected my cum in her, its frothy whiteness began to spill out over the rim of her ass, covering my thick hard shaft with its stickiness.
Taking mom from zero to hero in such a short space of time was just the first shock of our anal adventure together. Finding the right guy to join us in pursuing our wanton lusts to the next level, and to truly double penetrate her, not only in two holes but from two cocks, was our next goal. Yet the surprise of who would fill that role was something neither of us could have ever contemplated in our wildest dreams! Just a few weeks later, and out of the blue, not only would I discover I had a half brother, but my moms love for her sons would lead to our wildest most shocking sexual experience yet!