A Halloween Story: Sister Tricks Brother for Mom's Treats
By Charlie Flemming
Copyright 2020 Charlie Flemming
Hi, I'm Daniel, a high school graduate but still living at home as I decided what to do with the rest of my life. My mom, Kate, was 35 and the hottest woman I knew. She had blonde hair, blue eyes, an angelic face, sexy skin, a rocking body with the best set of tits, DDs, and a fine ass to boot. God, I wanted to fuck her so bad. I know it's wrong to lust after your mother, but I just couldn't help being around this beautiful goddess on a near-daily basis and not make her the target of my jerk-off fantasies.
It was getting to be too much though. She liked to walk around in just her silk robe that hugged her every curve. My sexual fantasies were getting worse and worse as I watched her every move. I needed to do something, anything, or I felt I was going to go insane. I started thinking up crazy plots of ways I'd get to fuck my mother but they were just fantasies for the most part and nothing felt like I would be able to realistically get my mother to touch my cock or anything else for that matter without her thinking I was some kind of horrible pervert by the end of it.
Then, one day a week before Halloween, my sister Cassie, who was 18 and a senior at the local high school, was talking at the breakfast table like she always was about her bitch friends like she always was. "So, that's when Rachel said-" I had already tuned out, for the most part, as I stared at my mother's sexy legs as she uncrossed and recrossed them over and over again, always hoping she'd cross them in such a way that she'd expose her pussy to me from under her silk robe, even for just a moment, the robe was just long enough to keep her most precious place covered. I still wasn't listening to my sister, who was just as hot as my mom, but she wasn't the object of my lust, so I didn't notice her whenever mom was around.
"You'll be staying the night with friends on Halloween?" Mom asked.
"That's right," Cassie went on, "Rachel wanted to-" I had already tuned out again as I longingly stared at my mother's breasts. But that made me think, Mom usually went out with her friend Sara on Halloween night and sometimes came home quite drunk. If Rachel was gone, and Mom thought I was gone too, maybe I could meet up at Mom's Halloween Party with a costume so she didn't know who I was. It was a ridiculous idea, my I couldn't help starting to fantasize about what could happen....
"Actually," I said, despite knowing what I had planned wasn't very plausible, still I had to do something or I was going to masturbate myself to death, "I'm going over to Tom's house on Halloween for a party with my friends, so I'll be gone too."
"Oh, so I'll be all alone," Mom said, "On Halloween night, how scary." Then she laughed, "actually I was going with Sara and Jane over to the neighborhood party like I usually do. It's probably better that way anyway. I hate coming home drunk when you kids are here."
"Come on Mom, I'm not a kid anymore!" Cassie complained, she was over 18 and wanted everyone to know that she was legally an adult.
"Well, until you move out of here, you'll always be a kid to me," Mom said as she stood up and grabbed our plates. As she leaned over the table her robe fell open and I saw one of her tits in all its glory. It was amazing, better than any porn stars I'd ever seen, full and perky without a hint of age yet. Her areola was the perfect size with a hard pink nipple just longing to be sucked. My 9-inch cock was already hard in my pants from just that brief glimpse at my mother's sexy breast. I excused myself from the table and practically ran to my room.
After jerking myself off 3 times in a row before my lust was sedated for a moment, I lay on my bed thinking about my plan. Mostly I was just going to get a costume no one would recognize me in and then do my best to seduce my mother at the party. I sighed. It seemed ridiculous. I'd never seen her bring someone home or even went on dates after Dad left her nearly 10 years ago. I'd just assumed that she didn't have much of a sex drive anymore, or if she did she just masturbated in private when she was horny. Now that I had calmed down and my brain wasn't coming up with overly complicated ways to trick Mom sexually, I realized the plan was doomed to fail. There had to be something I could do, but I wasn't sure what it could be.
Still, I had to try, and the next day I went out to find a costume to wear. I worked out a lot and had a fairly muscular body, but I also hit it most of the time under baggy clothes because my sister would never stop teasing me about anything she could, and that included my efforts for self-improvement. But, that gave me an advantage that if I showed off my body some, people probably wouldn't be focusing on my face.
I ended up buying a pair of mailman shorts with suspenders, I figured I'd wear that and would be able to show off my muscular body at least, but I still needed a mask. I checked through, but most were the Zorro-type masks in that they only covered the eyes and probably wouldn't be enough to keep my identity hidden from my mom. I looked for full-faced masks but they didn't match the outfit I had, not that much would go with "sexy mailman." In the end, I settled on a "Flash" mask, you know the superhero with super speed. The mask went over my hair and my nose, leaving the eyes mostly open, and my face was exposed below my nose. It seemed good enough and I could maybe just say I'm "a sexy superhero" or something similar without any issues. Yep, my poorly thought-out plan was coming together.
On the day of Halloween, I decided to try on my outfit just to make sure I thought my identity would be properly concealed before I tried again later that evening.
I got it on and looked at myself in the mirror. The Flash mask was perfect and though it did show my mouth, much like it would for the Flash, it also perfectly hid my identity. The short-shorts made me nervous though. They did show off my muscles, but they also hugged my bulbous cock so much that there was an obviously veiny and thick dick in my pants. Something my sister saw immediately when she just barged into my room a moment later.
"Hey Bro," she was saying as she just walked in, scaring the shit out of me as I stood in front of my mirror mostly naked save for the shorts and my mask. "I talked to your dorky friends and they said they aren't doing anything on Halloween..." She trailed off as she saw me, I just stood there with my mouth open looking like the cat who was caught while eating your pet canary.
Sis looked me up and down, then chuckled, "Damn Danny, you've definitely been hitting the gym in your spare time. Nice bod." She laughed again when she looked at my crotch, "Dan, you really don't have to shove a salami down your pants though. Your muscles are good enough to seduce a girl if that's what your plan is." And before I realized what she was doing, my sister Cassie reached down the front of my shorts and took out my huge cock. It was still soft but was starting to get hard as my sister felt it.
She didn't take her hand off it, she seemed downright confused as she started slowly jerking my cock to full hardness. She looked down at it and her other hand joined her first a moment later as she started feeling the fullness of my cock from the tip of the head down to the bottom of my shaft. I moaned softly, not sure if I wanted this to stop.
"Oh wow," Cassie said, she seemed to have forgotten who she was doing this to as she started jerking me off even more, "I can't believe how big you are. Do you mind if I suck it?"
This was a total shock to me, I never knew my sister was such a size queen, "Um, I mean..." I started to say but I shut up when my blonde buxom sister got on the floor in front of me and started licking the pre-cum leaking out of the tip of my cockhead, "Wow, Bro, you taste delicious," Cassie told me as she swallowed my semen, "I'm going to enjoy this," And with that, she engulfed my cock about halfway down the shaft, I don't think she could get much more than that in her mouth. My dick was too large for my sister's small mouth.
"Oh fuck Cassie, I can't believe this is happening," I said dumbly as she sucked me into her horny mouth. "I think I'm about to cum!" I shouted as the familiar feeling of semen rushing up my shaft to explode out my cockhead. My legs were shaking as I felt my body getting ready to cum. My sister just kept sucking though as I exploded into her mouth.
It felt like I could cum forever as my balls unloaded into my sister's mouth. She just kept up and managed to swallow all of it. God, I never thought my sister could give such an amazing blowjob before.
She stood up and laughed at me again as she looked at the stunned expression on my face, "Looks like I'm the one who got the drop on the Flash. Come on Bro, I want to show you something." She then grabbed me by my still hard cock and, after making sure the coast was clear, dragged me into her room across the hall. In the process, I stepped out of my shorts, which had fallen around my ankles during my sister's blowjob anyway.
Once in my sister's room, she pushed me onto her bed. "Okay brother, I'm going to do something for you but it has to be on my terms." She told me as she looked around in her closet for something, she seemed to find it and held up a few objects, two pairs of handcuffs, and a ball gag that went in one's mouth.
