When I woke up the next morning I rolled over to find that the Rich was already gone. That was not too surprising since he was often up way before me. I rolled back over and stayed up to get out of bed and I stumbled my way downstairs for some coffee. When I got down stairs I saw Jack sitting at the counter eating a bowl of cereal. Me not being a morning person gave him an unintelligible groan and grumble that could have been a 'good morning.'
"Good morning Naomi!" Jack's chipper voice rang out.
I hated that he was such a morning person. Just like his father. I got my cup of coffee and delighted in the sweet warmth of hot caffeine. Already feeling much better, I sat down across from jack.
"Good morning sweetie," I said, much more articulate. "What are you up to today? Got everything ready for school tomorrow?"
"Yeah mostly I have one thing left to do but it won't take long. I, um, actually had something to ask you."
I took another sip of my coffee before I answered.
"Yeah of course what's up?"
"Well I uh I know you don't want me to use socks anymore for...for when I...well you know and using a cup is more a two person job...." he trailed off leaving me hanging on what he was trying to ask me.
I was definitely not awake enough to be interrupting this conversation. I just stared at him blankly.
"I was going to this morning but...."
Then it dawned on me. He was asking me to help him masturbate again.
"Oh my gosh sweetie I am so sorry I didn't even realize I guess you would have had some morning wood or something right?"
He chuckled and seemed to relax when I finally understood what he was saying.
"Yeah, kind of. I didn't know what I should do about it so I figured I'd have to wait until you were up."
"Yeah yeah of course I'll have to go to the store today to get some groceries. I can pick you up some magnum condoms so you can take care of it yourself next time."
I thought I was being completely reasonable but I was confused when I saw Jack's shoulders seem to slump.
"What's wrong sweetie?" I asked.
"It's nothing, I just dont think jerking off into a condom will be the same as you holding a cup."
"Sweetie, I can't hold a cup for you everytime you want to jerk....masturbate. Especially as often as you seem to do it."
"I guess that's true," he admitted but didn't seem happy about it.
"Well how about you head down and I will get the cup and change and head on down."
"You don't have to change...." he trailed off looking into his bowl.
"What do you mean? I'm in my PJs. I can't wear this all day."
"I mean not to the store, sure but I don't mind."
Confused, I looked down at my normal sleep attire. I was in a tight white tank top and some loose booty covering thin shorts. It took me a second but I realized what he was saying. I really was not a morning person at all. I blushed because my horny step son basically just told me not to change because what I was wearing would help him masturbate. I bit my lip and gave him alittle smirk.
"You likey what I wearing. What if I wear something special?" I said this in my fakest thick asian accent.
The effect was instantaneous as Jack froze and just hung there with his mouth gaped open. I rolled my eyes and clapped my hands to snap him out of it.
"You are too easy. Go downstairs, I'll be down in a minute." I chuckled as I walked past him. I could feel his eyes on my backside.
When I got up to my room I grabbed the cup that was still on my nightstand and before I left I looked at my dresser. I mean what would be the harm if I did slip something on? If anything it would help the situation.
Tapping my hand on the cup I sighed and sat it down and pulled out my lingerie drawer. Being married to another man I had no shortage of sexy clothing. I settled on one that I think Jack would enjoy particularly.
As I walked downstairs in just my lingerie I became self conscious once I hit the main floor. It felt like I was sneaking around. I became aware that we really had too many windows. I mean we really didn't have neighbors but I still got paranoid until I came to the basement stairs.
I knocked on Jack's door and he called me to enter. I let the door swing open and he was laying on his bed, pants already off working a semi stiff cock to life. When he saw me leaning on the doorframe he stopped and his jaw dropped so much I thought it was going to fall off. I was wearing a black lace corset onesie that wasn't quite sheer.
"Cum bucket reporting for duty sir," I said in a deep sultry voice as I held up the cup.
"Oh my god Naomi! You look amazing!" Jack said prettified with awe.
I noticed his semi erection was now fully erect. I always enjoyed being able to make men hard. I knew I was attractive and I knew how easy men were to a petite Asian woman.
I bit my lip and winked at Jack, "start stroking, big boy."
Without need for further incentive Jack grasped his big hard cock and started stroking slowly. That little shit was going to draw this out as long as he could.
"Now, now you can do better than that. We got a job to do, don't exploit the situation."
He hung his head and started stroking faster. I came over and sat next to him on the bed.
"You didn't want to have any porn open?" I asked when I sat down.
"I um didn't think I needed it," he said, eyeing me up and down as she continued to stroke his massive cock.
"Are you expecting me to put on alittle shoe for you?" I said in mock disapproval.
Jack tried to hide a face that said that's exactly what he was hoping for but he shook his head.
"Good because I'm not here to hold the cup and look pretty," I paused for dramatic effect before speaking in that thick broken accent, "me likey chu stroking big big cock."
Jack's head shot up and looked at me. I ran a hand up and down his thigh while my other hand caressed my breast. He took a shuddering breath and I smiled wryly.
"You want bad mom dancy-dance?" I asked.
He nodded breathlessly as he changed hands on his raging erection. I smiled and stood up. I stood a couple feet from the bed and cupped my breasts and slowly saved my hips seductively. Jack looked on in total amazement. He was stroking so fast now. I ran my hands down my body and met at my crotch. I felt my wetness through the thinnest material. I spun around and bent over to present my shapely butt at him. I bent over to touch my toes and I looked back at him and winked. He was stroking so fast I thought he was going to start a fire.
I spun back around and giggled. He smiled and waved his arm before changing back to his other hand.
"What's the matter?" I asked, standing straight.
"My arms are getting tired. It happens sometimes."
"Do you want to find some porn?" I asked for the laptop.
"No, it would take too much time to find something good."
"You mean like 'hot Asian milf gets fucked up the ass by horny stepsons big hard cock'?" I chastised with a hand on my hip.
Jack nodded and switched hands. I sighed and stepped up to the bed and sat back down next to him.
"Okay look I'll do this just this one time okay..." I said as I shooed his hand away and I wrapped my tiny fingers around his big hard cock.
His cocness so big I could even wrap my fingers all the way around it. Jack put his hands on the bed and stared down at my hand as I began to slowly stroke his cock.
I couldn't believe my own eyes actually. There I was, my small hands wrapped around the biggest cock I have ever seen and I was stroking it up and down. I looked at Jack and he looked back at me. I gave him a nervous smile and he returned it.
"Not a word about this to anyone young man." I pointed at him with my other hand.
"Yes I mean no," he chuckled.
"What's so funny?"
"It's like a happy ending massage," he chuckled again.
I chuckled too, "Only that I'm not giving you the 'sucky sucky massage."
We both laughed and I saw him grimace a couple of times.
"Am I doing this wrong?" I asked loosening my grip.
"No it's just a couple times you pull the skin too far and it hurts. Here... " he reached a hand down to guide mine. He pulled my hand up and down to the spots that wouldn't hurt him.
"It would help if we had lube," I said but figured he wouldn't have any and I knew I didn't.
"I don't normally need it," he said.
I bit my tongue. And leaned over his cock. I produced a good amount of saliva and spit it onto the head of his cock. Jack moaned as I worked the saliva all over his cock.
"That's better there isn't?" I asked him now able to pick up speed.
"Much better oh my god. I think I'm going to cum soon."
"Here, sit on the edge again and let me grab the cup."
We changed positions and I knelt down on the floor between his legs and I spit in my other hand now. My first arm was getting tired as well. I looked up at Jack and smiled. It was awkward with my other hand but I got the rhythm back and in no time Jack was breathing hard and rolling his hand back.
"Just let me know when you are about to cum we can't have another accident like last time."
He nodded silently and I kept pumping away at his big cock. Before long this arm was starting to get tired and I was slowing.
"I didn't think it would be this much work. Next time, have some porn set up."
"Next time?" He asked, looking down at me.
I shifted realizing I spoke without thinking. I was already thinking about doing this again. I didn't say anything, just continued to stroke my stepsons big hard cock. I was starting to switch hands and work it in circles.
"It might help if you uh maybe... " he trailed off clearly not knowing how to say it without sounding like he was taking advantage.
"You want me to beg?" I asked in what has become my sexy accent, "cum for me, cum for mommy," I begged, remembering the porno from yesterday.
I leaned up and smacked his cock against my face trying to be olayful sexy. What it did accomplish was reinforce the burning wetness between my legs. I so badly wanted to start running by myself but I couldn't do that Infront of my stepson. That would be wrong. I mean more wrong than giving him a handjob of course.
"You want cum all over my face? You like happy ending massage?"
I could see Jack's balls begin to tighten and he was nodding while he was moaning.
"I'm gonna cum mommy!" Jack nearly yelled at me. I fumbled with the cup and brought it to the base of his cock as I stroked him as fast as I could. I really felt the burn in my arms.
"That's it sweetie cum for mommy! Me love you long time."
At that Jack grunted and he started to shoot his load into the cup. I kept stroking but much slower and more exaggerated. I could feel the force of his cum shooting out of the base of his cock. I licked my lips remembering how good Jack's cum tasted yesterday. A part of me wanted to down the whole cup the moment he was done filling it up but I knew I could possibly do that.
Jack finished cumming and unreleased his cock and looked inside the cup. It was easily twice as full as yesterday's. It would probably take me two gulps to swallow it all. At that thought I shook my head to shake that thought loose.
"What?" Jack asked, seeing my head shake.
"It's just... how can you cum this much??" I asked incredulously.
He shrugged and pulled himself back to lean up on the wall. I stood up feeling the soreness in my knees as I did.
"I should uh go take care of this," I raised the cup of cum.