Toby stood at my laptop again, naked except for a t-shirt, masturbating. His shorts and underwear were on the floor. This wasn’t the first time and it wouldn’t be the last in these stuck-at-home COVID days. He’d pushed my chair out of the way and positioned himself to the left of my computer. He’d moved everything out of the direct path his cock was pointing to. Toby watched a video and I moved next to him to see what it was.
His cock had appeared to soften slightly when I walked into my bedroom, but hardened up again in seconds. My son was, after all, just sixteen. He stroked it slowly, as though it were just something to do, like skimming TV channels or texting. Neither one of us said anything.
The video showed two people, well, parts of them, and the guy fucked the woman in the ass. This seemed to be a favorite subject of Toby’s since he’d done the same to my friend, Jen, a couple weeks ago. I watched the cock slide in and out of her asshole. A half minute later, they showed the “guy” and she was transgendered. The woman with the cock had nice boobs. I wasn’t too sure how I felt about what I was watching, deciding to think about it later.
Toby was more into it than I was. He masturbated heartily, his hand moving faster now. I looked at his cute little ass, thought for a split second about inserting my finger, went back to watching the video and watched her cum. Toby took a short 60 second break to find another similar video and started it. He resumed jacking off. This one showed a guy fucking a lady in the ass, very much the same thing as before.
I was dressed in a blouse and shorts, like most days here in Southern California. My face and hair were a mess, also much the same as usual. I leaned closer to Toby and put my arm around his waist. My breast pressed into his arm. My hand slipped to his front and I cupped his balls.
He jacked a little faster and I decided to help him out a little more. I did everything from beside him as he’s several inches taller than I am and he’s probably still growing. I put my hand on his cock and stroked it, which prompted him to stop fondling himself to let me do it. At least from this position I could see what I was fondling.
“Do you like this, honey?” I asked. “Me jerking you off?”
“Yeah, mom, I do,” he replied.
“I like it, too,” I said. “Your cock is so hard. So warm. You enjoy watching these videos?”
“Yes, mom.”
“You enjoy watching somebody fucking a nice woman in the ass? His cock sliding in and out? Fucking her all the way until his balls touch her butt?”
“Um,” he said.
“Would you like to do that to me, honey? Fuck your mother in the ass? Push your cock into my asshole until you cum? Would you?”
Without any warning, Toby spurted a line of cum that stretched to the back of my desk. I continued to stroke him and his second burst squirted almost as far. After that, they trailed off, but together I saw a lot of cum on my desk.
“Whew,” I said. “I think you needed that.”
“Yeah,” was all he said.
Dinner that night was chili, something I make fairly often because it’s easy and makes two meals. I make California chili, which has beans in it. We watched The Old Guard on Netflix and it was pretty good, although [spoiler alert] I was disappointed that it looks like Charlize Theron might not survive a sequel.
A couple days later, Toby was back masturbating at my laptop. He was doing this more and more. I viewed the handjob video he was watching for a minute, then suggested that we try something in bed. Toby was always up for getting into my bed. He left the video running on my laptop.
We’d had sex maybe eight times in the past four months (and zero before that). Maybe ten times. We didn’t always fuck and I wasn’t planning to this time. Toby was naked to begin with, but I had to take off my blouse and bra, shorts and panties, which I did a little more slowly than absolutely necessary. We stood and looked at each other, his cock pointing directly at me like an accusation, and I stepped forward and took it in hand.
“I love your cock, Toby,” I said. I also loved his slightly lopsided smile and his big eyes, his broadening shoulders and lean body. My son is beautiful, at least to me. (As for me, just check my pictures on my Lush profile. I am what I am.)
His hand reached out and found my waxed cunt, but he didn’t say anything. We fingered each other for a minute, then climbed into bed. Toby started to climb over me, but I held him off.
“No, not today, at least, not right now,” I said. “Lie face down, your body up against mine.”
We got into position, heads on pillows, shoulder to shoulder, skin to skin. I reached under myself with my right hand and told Toby to do the same. I wasn’t sure that he needed a hand underneath.
We began to masturbate together. My hand was on my pussy and I took it easy. It was minutes before I was wet enough to venture a finger inside. Toby started to masturbate normally, his hand on his cock, but he quickly took his hand away and just rubbed his dick into the mattress. He lifted his ass a little and I could sort of see his cock beneath him.
“Try a pillow,” I suggested.
He took the third pillow (I have three regular sized pillows on my king size bed) and put it under him. I couldn’t see his cock anymore. Toby tried a couple different positions, on top of the pillow, fucking the middle of the pillow, and finally just threw the pillow on the floor and went back to fucking the mattress. Well, it looked like fucking. He arms were straight and I could easily see his hard cock, which was rubbing along the bottom sheet. I moved my fingers to my clit and masturbated faster.
He was sliding back and forth. I watched him and rubbed myself.
“Are you thinking about fucking, honey?” I asked. “Fucking me, maybe? As though your cock were inside my cunt?” I played with my clit.
“Look at me, honey,” I said. My ass was grinding along with my hand now, sliding side to side and up and down. I was bouncing on the bed, not far, but it provided extra pressure on my clit. Toby looked at me briefly, but returned to looking straight ahead and down at himself.
“You like watching your cock?” I asked. “Sliding back and forth on the bed? I’ll bet you’re going to cum soon… “
We had been doing this for about seven minutes and I was a ways from cumming. Toby, apparently, was close enough. He quickly sat up and took hold of his cock. He stroked it just like normal, short, quick strokes, and he came. He came on my back and shoulder, streaks of cum, which slid warmly down my side.
“That was pretty good, mom,” he said. “How’d you think of that?”
“Well, I’d recently masturbated prone, and I thought maybe you’d like it, too.”
Toby got up and left. The handjob video had stopped. I was feeling in-between: some distance from an orgasm, but somewhat on my way. I decided to stop. I changed the sheets, even though not much of Toby’s cum had made it to the sheet.
Four days later, I was masturbating in bed and Toby opened my door and walked in. I’d only been pleasuring myself for about three minutes, just thinking, no laptop videos or anything. I’d been thinking about an old boyfriend, one from several years ago, who had been particularly good in bed. My son had a towel in his hand.
“Toby,” I said, “you’re supposed to knock before entering, you know.”
I turned off my vibrator. It was a wand type that I used on occasion, just about always set to the higher vibration level.
“Uh, sorry, mom, I thought you were downstairs. I was, uh, going to use your laptop. To, you know, do what you’re doing.”
“Well, go ahead, I guess,” I said, “I’m not going to stop.”
I turned the vibrator back on at the lower vibration level, and used it on my tummy and upper body. I was in less of a hurry to orgasm now that Toby was here.
He took off all his clothes this time and put the towel on the chair, sat down, and started to google. He quickly found something he liked, clicked the video, stopped it, tried another… anyway, he found one to his liking. He’d moved the chair to one side so I could see the screen, although it was pretty small when seen from the bed. It looked like a compilation of handjobs again.
I was using the vibrator slowly, while Toby was masturbating fairly actively, watching the laptop screen and not looking at me. I could just make out the squirts of cum on the display. The video switched to another couple. I looked at Toby and figured the towel meant he planned to cum on himself. He wasn’t leaning back in the chair yet, though.
Putting the massager on my clit, I gasped, then settled in. Whichever vibrator I use, resting it against my clit provides an instant surge of electricity in and around my cunt. My rush to orgasm seemed to pick up where I’d left off, maybe halfway there.
“Toby,” I said, “come here a second, would you?”
Another guy ejaculated on the video. Most of the time, they were just shooting into the air, either straight up or straight out, kinda fun to watch. Toby walked to the bed, still rubbing his hard cock, and said, “Yeah?”
“Climb on top of me, missionary-style, and put the end of your cock on the vibrator, please.”
He looked a little confused, but submitted to his mother’s will. I suspect it was the first time his cock had ever felt a vibrator. At first, he did exactly what I’d asked and his cock kept falling off the head of the vibrator. He ended up kneeling between my legs, sunk down a little, his hand on his dick to hold it in position.
“Wow, that feels great,” he said.
I turned up the vibration level and his cock jiggled visibly. We could hear the low hum. My clit was constantly shooting energy now. We both just held our positions, neither of us moving much at all, Toby’s hard cock atop the vibrator and my clit below.
“Wow,” he said. He studied his dick more than he looked at my breasts.
I watched Toby’s cock and I watched the screen where guys continued to cum every twenty seconds or so. I was getting close.
“I’m going to cum soon, honey,” I said, “how about you?”
“I think so, I’m not sure,” he replied.
“Do you want to shoot on mommy’s tummy?” I asked. “Mommy’s breasts?” I hardly ever called myself mommy anymore and I liked it.
“I, uh…, “ was as far as he got. He frantically fell to his hands, his legs out, and was just about to push his cock into my cunt when I felt a spurt of cum on the front of my pussy. Then his cock entered my cunt and I felt his cum surge warmly inside me, followed by his dick pushing all the way in and the twitches of my son’s ejaculation.
“Please don’t go,” I said, meaning for him to leave his cock inside me. Which he did and patiently waited another minute until I came. As usual with the vibrator, I came explosively as my orgasm bloomed through my body. I held the vibrator on my clit for maybe forty seconds, long enough for my orgasm to fade and a second orgasm to blossom. The second one wasn’t quite as stomach-crunching as the first, but it curled my toes. I put the vibrator back on my clit for two seconds and had a third little orgasm that simply felt pleasant.
[I almost stopped writing here, but after leaving what I’d already written above to rest for a couple days, one more thing happened that seemed worth writing about. It’s about Toby, of course.]
Two days later, as soon as I walked into my bedroom, I heard the hum even before I saw Toby on my bed. He was flat on his back, his legs spread wide, his balls plainly evident. His hard cock pointed straight at his head. My wand vibrator, the one we’d just used, pressed the head of his cock into his tummy. He didn’t move, he just lay there with a smile on his face, the massager humming.
I stood at the foot of the bed and watched. His eyes were closed. He had stubble on his face from not shaving, his hair disheveled. I could see his cock quivering, but it otherwise wasn’t moving. The head of the vibrator pulsed directly on the underside of the shaft of his dick.
I wondered what he thought about while masturbating, not for the first time. It wouldn’t be like mine, of course, long, hard cocks and wet pussies. Well, maybe wet pussies. Fucking Jen in the ass, just about for sure. And maybe hard cocks, since what were handjobs anyway except for ejaculating cocks? I gave up, realizing that I was putting too much of myself into guessing what Toby fantasized and that I’d just never know. But then, masturbatory fantasies were one of the few things just about everybody kept to themselves, including me.
I’d been standing for about a minute, wondering, when Toby came.
He didn’t shoot large jets of cum up his chest. He didn’t spurt streams on his tummy. Instead, it looked like the cum just leaked out of his cock. There was quite a bit of cum, but it just pooled at the head of his cock and ran down his side. He must have held the vibrator on his dick for twenty seconds after he first started to cum, quite a long time for a guy, really. He let the vibrator fall to his side, still on, and sighed.
“Did you like that, honey?” I asked.
“Yeah, mom, I really did,” he replied.
“How come Katie hasn’t been over in the past week?” I asked. Katie is his girlfriend, someone we’ve both had sex with, stories I’ve already written.
“We’re not together like we were. You know, boyfriend/girlfriend. We’re just friends now and benefits are unlikely.”
I thought about this. It seemed like a big deal to me, but apparently not so much to my son who had just masturbated and cum.
“OK,” I said. I had nothing else to say, so I left, having forgotten why I went into my bedroom in the first place.
