'Taking Care of Business' With Son

I stepped out of my dress and struggled to find room to pull my shoes off in the tiny hotel bathroom. Didn't matter. I was high on sunshine and ocean breezes after a hard day of vacationing. It was a shame the sun had to set eventually, but a water-side dinner with my brothers and my son had allowed me to maintain a glow throughout the evening, and I was thoroughly exhausted and ready to embrace sleep. And do it all over again the next day. The start of the vacation had been perfect, and my only regret was that finding a few minutes to relax with my massager was going to be difficult before sleep with my son sharing the room.

I remembered my son's words to me earlier in the day as we sat by the pool.

"Mom," he'd said under his breath so that my brothers or nieces who were nearby couldn't have heard. "You might want to set up a spa trip or something for this evening. It looks like I'm going to have to take care of business tonight."

"What is that supposed to mean?" I asked, although I knew exactly what it meant, and took another long sip from my margarita.

"I might have to take care of business," he repeated, and made an extremely subtle jerking off motion with his hand. He smiled at me before taking another drink from his own margarita.

"You do what you need to do on your side of the room," I laughed. His side of the room vs my side of the room was a running joke we'd had since checking in at the resort, because the room was so tiny our queen-sized beds were almost on top of each other. "And just ignore what goes on on my side," I said, making sure he saw me tracking a young man in a speedo walking past our chairs.

Derrick, my son, had stopped coming on family vacations years ago, but after his dad passed away our relationship changed. We got a lot closer, somehow, and even if we still didn't see each other on a day-to-day basis we started getting together a few times a month for a movie or just dinner at my house. I wasn't surprised, frankly, when he expressed interest in coming on this trip, even though he had been only 17 the last time he and I and his father and sister had vacationed as a family. When he mentioned that a trip I'd been planning with my brothers to Florida sounded like it would be fun I'd invited him, and he accepted.

And then we showed up and found out that my brother Ed, who'd booked everything, had put us together in the smallest resort room I'd ever seen. I started feeling self-conscious looking in the mirror at what I'd brought to sleep in - just panties and a breezy pajama top. I had to position my long blonde hair just right in order to obscure my generous cleavage. It wouldn't be so bad once I got into my bed, but I had to parade past him in that get-up in order to get to the bed, and he'd already had a long day of barely-dressed women parading past him.

Which was what made me think of his "take care of business" comment.

"Oh, hey Mom," he said from his bed as I came out of the bathroom. I paused to lay my folded dress and shoes next to my suitcase, but out of the corner of my eye I saw him doing a lot of adjusting of the bedding on his side of the room. I quickly slipped under the covers of my own bed and saw that he'd been watching a movie I'd seen before.

"Do you want a night cap?" he asked, holding up an empty glass. I'd been drinking since we stepped off the plane this morning, although slowly, and saw no reason to stop until I was firmly in dream land.

"Are you having one? Sure, pour one more light one for your mother," I said. After pouring a modest amount of whiskey, he reached over the small nightstand and handed me the glass. "To Florida," I said raising it.

"To the Crawford clan and their family vacations," he said raising his.

"To us," I finished, and then sipped from mine before setting it on the nightstand next to his.

I was finding it hard to pay attention to the movie - I hadn't liked it all that much the first time I'd seen it - and instead started wandering in my mind back to the sun, the drinks, the pool...the men, from earlier.

"I'm not really into this," Derrick said after a scene or two had gone by, "if you want to change it."

"Yeah," I said, thankful that he had read my mind. "Put on whatever you want, Derrick. I'm probably going to fall asleep in a few minutes anyway."

"Actually," he said and then paused.

I looked over at him – even with the lights out it was still pretty light in the room with the TV and the open ocean-view window.

"Actually, I was thinking I might...take care of business? If you remember what I said earlier?"

"Derrick!" I said laughing. "Do you want your mother to take a walk somewhere?"

"Mom, no! I mean, you said earlier I could do what I wanted on my side of the room. I just thought I could do a quick one. I was going to put something on the TV, but I could go in the bathroom or something if you want. Actually, I'll do that."

"No, no," I said and downed the last of my whiskey. "I said you could do what you wanted on your side of the room and I meant it. And the TV is on your side of the room. I'm just going to go to fall asleep so knock yourself out. Just don't...I don't know...be loud or anything. Ed's room is next door - I don't want him to get the wrong idea!"

"Haha, that would be a shock for Uncle Edward, eh? No, Mom, I'll keep it down, I promise."

Unsurprisingly, despite the long day and the alcohol, I had difficulty falling asleep with hotel porn on the TV and my son masturbating on the other bed. For a minute or so I tried to pretend I could just close my eyes and fall asleep, but I found myself listening to the TV, even though Derrick had the volume set to barely-audible, and once I was listening I felt I had to watch, and once I was peaking out of the corner of my eye at the screen I didn't see the difference between that and rolling over and watching.

"Mom, sorry, are you still awake?" Derrick whispered.

"Don't mind me," I whispered back. "Take care of your business. I'm just going to watch for a bit. The TV! I'm just going to watch the TV with you for a little bit." I took care not to look over at him, but even without directly looking at his bed I could see that he was propped up against the headboard with his knees up and the covers up to his chest.

"Okay, Mom," he whispered quietly.

The scene on the TV was a generic one. I wasn't entirely unfamiliar with hotel on-demand porn as I've always had to travel some for work, and the woman and man running through positions on the screen were attractive, but not energetic enough to really get me going. Still, the thought that I was watching porn with my son on the next bed occurred to me... I pulled lazily at a nipple, hoping it wasn't obvious through the covers, and allowed my other hand to gently stroke my pussy over my panties.

Derrick didn't seem to be having any difficulty getting into it, and I could soon hear him jerking himself rhythmically under the sheets. I couldn't help myself. I peaked! He was staring intently at the TV and his stroking was visible against the sheets in his lap. It took all of my effort to stifle a laugh. It was so ridiculous, seeing my son masturbating to the cheesy scene on the television.

I slid my hand inside my panties and found that I was a little wet, and started to use that lubrication to, hopefully, inspire more. In the movie the woman was beginning to reach orgasm, or at least acting as if she were, and for a few moments I successfully imagined I was her, sliding inexorably towards a mind-blowing orgasm at the hands, and fairly well-endowed cock, of her partner. I almost missed the commotion on the bed next to me as Derrick shifted positions, but I was still just present enough in the room to catch it and draw back from abyss with my on-screen stand-in.

The next time I peaked out of the corner of my eye at my son I saw that he was laying down flat on the bed, with the covers down fully to his knees. At first I couldn't understand what I was seeing in his crotch area due to a strange shadow or something, but then it dawned on me that I was looking at his cock - an immense, thick cock, that he was stroking rapidly with one hand, but could have easily used two on without completely obscuring it. He was bigger than the actor in the movie, by a long shot. He was bigger than his father, by a country mile. It was probably the biggest dick I had seen in my entire forty-five years on Earth, and from the quick look I'd gotten, it was smooth and hard as fuck.

I peaked again, allowing myself a longer glance this time. I was in a trance by then, but had I been paying attention I'd have noticed the flood gates had opened between my own legs. Forcibly preventing myself from looking a third time was possibly the most difficult thing I'd ever done in my life, and I could only do it for a few seconds. My eyes snapped to his groin and I took it all in hungrily. His dick was so fucking big I could hardly believe my eyes. His massive, hairless balls traveled up his shaft with every stroke, and then back down again, usually slapping against his own skin. His head was engorged and beautiful. Derrick had always been an attractive man, somewhat muscled, and tall, and dark-haired, but I'd never seen him in this achingly-beautiful light before.

It must have been twenty or thirty seconds that I sat staring slack-jawed at his naked cock, my hand now working furiously at my soaking-wet pussy, my chest heaving and my nipples hard and pointy. It seemed like eternity. I managed to break the spell long enough to glance quickly at his face before locking in on his huge cock again, expecting him to still be staring glassy-eyed at the couple on the television,. But wait. He hadn't been looking at the screen! He had been looking right at me! An unexpected wave of pleasure washed through my body. My son had caught me staring at his erect cock - in fact, was still watching me watching him jerk that fantastic monster.

My face flushed fully red when I met his eyes again, but I didn't care. Actually, I loved it. I wanted him to know that I was embarrassed, but completely enthralled by his body and actions. I wanted him to see his mother, full of desire, staring at his massive dick. I wanted him to know he was loved and cared for and sexy as fuck, and that he was about to push his mom to a gigantic orgasm by allowing her to see him pleasure himself.

Thank god he didn't say anything. He just kept looking at me. Had he said something who knows what I would have said. How could I have explained it? How could I have resisted peeling myself from my own bed and pouring myself into his if there were any words spoken, or any acknowledgment at all of what we were doing? He didn't say anything.

I couldn't help myself, though. Not knowing what else to say, I simply said his name, but midway through the word "Derrick" my body spasmed and turned the second syllable of his name into a catch in my throat and a moan. If there was any doubt about the fact that I was incredibly aroused by the sight of my son jerking off on the bed next to me, it was erased in that moment, and suddenly I knew I was going to cum immediately. I was still riding the crest upwards when Derrick began thrusting his hips up off the bed and shooting streams of cum into the air that smacked down against the taught skin of his stomach and chest.

"Mom," he whispered in the midst of his orgasm. I was lost from there, thrashing against the bed sheets looking frantically for any way to stop myself from screaming out in ecstasy as wave after wave of bliss radiated through my body. Even when I thought I had been cumming for an hour and I must surely come down at some point, my legs jerked and shook with the shockwaves of orgasm.

When I became conscious of the world around me again I found the covers, and my pajama top, had both been yanked down, exposing my tits and swollen nipples. My panties were soaked through, as were the sheets below me. I couldn't remember a time I had taken care of more business with nothing more than my own two hands. The morning was going to be interesting, not to mention the rest of the vacation.

"Night, Derrick," I called happily over my shoulder as I turned into the covers.

"Night, Mom, " came the still-stunned reply.