A couple of weeks after Halloween I thought it'd be funny to scare my mom. Her and my asshole father had just finalized their divorce. Even though he was an asshole, mom was still sad, not really about losing him, but more about being alone and having to raise my twin sister and me. We were both 19 and in college, but it was still a struggle for mom, so we tried to make it easy on her. Honestly my intention was to scare her yes, but to make her laugh. I thought she'd get a kick out of it. What happened though changed the dynamic of our family forever.
My mother's name is Judy. She is really pretty but since dad left, she has put on some weight. She used to have long black silky hair, but when she got divorced, she seemed to want a change and cut it really short so that it's spiky now. She also dyed the front part pink. Before the weight gain, she had a nice body. I'd say average for a mother of two kids. Her boobs were always big, but with the added weight they were huge. But she has a pretty face and a great laugh.
Melanie, my twin sister, is a cheerleader, and has a great body. I know you're not supposed to think that about your sister, but it's true. She also has big boobs -- must run in the family -- and is also very pretty. By the way, it was really her idea for this little scare, but since I had the mask left over from a Halloween party, I was the scarer.
My name is Tom. I'm tall and skinny. Not really athletic but obviously a practical joker. Whereas my mom and sister are pretty, I'm just average.
So, even though my dad is as asshole, he made great money, so my mom's bedroom is huge. I was hiding in the walk-in closet wearing a really scaring mask. Melanie, doing her part, was talking to my mom, distracting her. Mom had been planning to go out with her friends and walked into the closet to look for something to wear.
"Trick or treat!" I shouted, jumping out of my hiding spot.
To say Mom was not expecting that was an understatement. She cried out and jumped about a foot in the air.
Melanie and I burst out laughing. Mom, not seeing the humor, lunged at me. "Tomas!" she screamed. You know you're in trouble when your mom uses your full name.
In an effort to get away, I scrambled on the bed. I was promptly tackled by Mom. She then proceeded to sit on me and spank my bottom. Melanie thought this was funny too. Traitor. I'd remember this.
"So, instead of having a nice night out with my friends, I'm stuck home with you two brats," Mom said.
"You can still go out," I said.
"Sure, and I'd be jumping at every sound I heard. Thanks to you!" Smack. Her hand came down on my butt. "Melanie. Are you going to help or just stand there and laugh?" Mom asked.
"Help? It was her idea!" I said.
"Liar," Melanie said. "Sure mom, I'll help." And with that, Melanie pulled down my sweats, exposing my bare butt to her and my mom. "Naughty, naughty!" Melanie said spanking my ass along with Judy.
Then one of them, either mom or Melanie, ran their fingernails across my butt. I jumped because it tickled.
"Oh, is my little boy ticklish?" Mom asked, poking me in the side. I barked out a laugh and jumped again.
Mom laughed and started tickling my sides, while Melanie poked and pinched my ass.
Then I felt a fingernail run across my asshole. I bounced on the bed. "Mom, Tom's butthole is ticklish," Melanie said, tickling it again. I felt my legs being pulled apart and heard Mom's throaty laugh as she too tickled my asshole. Then I felt her bend over and before I knew it, something wet hit my asshole. Melanie laughed. My cock started to get hard as I realized my mom had just drooled spit on my asshole while tickling it. Melanie added her own spit and I felt two fingernails on my asshole.
"I wonder if his armpits and feet are ticklish?" Mom asked. "Flip him over!" She instructed.
Before I knew what was happening, I was flipped over and my shirt was removed. I barely had time to pull my sweats up.
"Sit on his face, Mom," Melanie said.
"Good idea," Mom said. "Let me get more comfortable first." She then took off her pants. Before I even thought about trying to get away, Mom had climbed onto my face, facing my feet. Then her and Melanie started tickling my ribs and bellybutton. Then Melanie moved down and started tickling my inner thighs through my sweats.
With Mom's butt in my face and Melanie tickling my inner thighs my cock once again grew stiff. Mom was laughing and tickling the shit out of me.
"Mom," Melanie said. "Mom!" Melanie tried again. "Judy!" Melanie shouted.
"What?" Mom asked.
Melanie pointed to my crotch. "Look." Mom looked. It was obvious I had an erection.
Mom reached down and grabbed my stiff cock. "Really Tom, a boner?" She asked.
Suddenly, Melanie tugged my sweats and pulled them off, revealing my hard, throbbing cock.
"Oh my God!" Melanie gasped.
"Holy shit!" Mom said.
Judging by their reactions, I guess I wasn't so average after all.
Mom climbed off my face and was still looking at and now slowly stroking my cock. Melanie had disappeared then popped up right by my head, wearing the mask. "Boo!" she shouted. I screamed and jumped.
Melanie started laughing as did Mom. "Look Mom, Tom's scared stiff."
"Let's tie him to the bed and tickle the shit out of him," Mom said.
"Well, tickling something out of him," Melanie said, giving my cock a few strokes. I tried to get up but Mom grabbed me by the balls and applied enough pressure to keep me there, while Melanie grabbed some of my father's old ties.
I was about to be tied up by my father's old ties while my sister and mom tickled my naked body. All because I wanted to scare my mom and try to cheer her up. Well, it worked. I hadn't seen Mom laugh this hard in a long time.
Once I was secured, Melanie tickled my feet, while Mom tickled my ribs and armpits.
"What's got your dick so hard?" Mom asked. "My panty clad pussy rubbing on it or my big boobs smacking you in the face?"
I couldn't answer because I was laughing too hard. "You want to see Mommy's big boobs?" She asked, then took off her shirt and her braless tits flopped out. They were huge. With big areolas and fat nipples. Her nipples her hard. "Suck on Mommy's titties while she tickles you," she said shoving her boobs in my face. Then she stopped tickling me and made me suck her breasts and nipples. She ground her pussy against my hard cock and moaned while I was sucking on her tits.
"Switch!" she shouted. "Melanie, you sit on his face while I tickle his feet."
Melanie was wearing a skirt, but was not wearing panties. So, mom was topless and Melanie was pantieless. I started licking my sister's pussy, causing her to moan.
"Let's see if you can make your sister cum before you do," Mom said, stroking my cock. She jerked it up and down for a while, then spit on it and used her fingertips to twist the head like she was opening a bottlecap. Each time I was close to coming, Mom would reach down and tickle my balls and inner thighs.
Soon Melanie started moaning and grinding her pussy on my face. I ran my tongue as fast as I could over her clit and soon her thighs squeezed my head as she had an intense orgasm. Then she climbed off and joined Mom in tickling my hairless balls and stroking my cock. They both used their mouths and tongues to get my cock really wet. Then they used their thumbs to rub just under the head and that was all it too. I shouted and exploded in a huge orgasm. After a couple of squirts, Mom and Melanie passed my cock back and forth to taste my cum. Then Mom leaned down and used her big tits to clean up the cum from my stomach. Melanie then licked the cum off of Mom's big breasts, while mom reached down and fingered my sister's pussy.
Melanie did a strip tease for me while Mom played with her boobs and pinched her nipples. Then Mom took off her panties. When Mom was naked, she climbed on my face and Melanie slid on my cock. My sister's pussy was really wet. I guess she got off on tickling her brother. Mom's fat pussy lips were also wet. I licked her lips, then stuck my tongue as far as I could inside Mom's cunt and tongue fucked her. Meanwhile, Melanie leaned over so I could suck on her tits.
Mom then had a huge orgasm on my face. Then she tickled me until Melanie had her own orgasm on my cock. Mom sucked all my sister's juice off my cock, then her and Melanie took turns sucking my cock and tickling my balls. Then Mom climbed on my cock while Melanie continued to tickle my balls. Mom's pussy was super tight. It felt like a velvet glove had wrapped itself around my cock. She started out slow then went faster, then slowed again. Every now and then Melanie would pull out my cock and lick off our mother's pussy juice, then slip my cock back inside Mom's tight cunt.
"Yes, Melanie, lick Mamma's asshole," My mom said. Before I could process what, my mother had just said, I felt a finger, Melanie's presumably, slip into my own asshole and soon I felt my mother's pussy tighten even more on my cock and that's when I started shooting inside her pussy.
Melanie lay beside me on the bed and Mom placed her pussy on her face. My sister licked up the cum from our mother's pussy, then they both licked my cock clean.
Mom and Melanie untied my legs and Melanie once again sat on my face and told me to lick her asshole while she lifted my legs up so Mom could lick my asshole. Melanie's butthole didn't taste as bad as I thought it would. Mom also stroked my cock, keeping me hard. Then they switched. Mom's ass didn't taste bad either, just different. Melanie also stroked my cock. The combination of licking my mom's ass while have my sister lick mine, while stroking my cock sent me over the edge and I came again.
Finally, we all took a shower together. I was able to finally touch Mom and Melanie's big breasts and their pussies too. I pinched and squeezed their breasts and nipples. Licked and bit then too. I also fingered them both to another orgasm each. Then Melanie got behind me to lick my asshole again, while Mom knelt down and took my hard cock into her mouth. Watching my cock slid in and out of my mother's mouth sent me over the edge and I started to shoot my load inside it. She swallowed every drop.
"This isn't over, mister," Mom said reaching down and grabbing my balls. Melanie reached down also and stroked me to another hard on. Then her and Mom laughed and walked out of the shower leaving me with another boner. I stayed until the water turned cold and by cock went soft. I didn't have any more cum in me anyway.
Last year I scared my mom (with my sister's help), and it turned out pretty good for me. My name is Tom, and I just turned 20. Melanie (my twin sister) was out with friends and had moved to a dorm, so it was just mom and me in the house now. Mom and dad had been divorced for about a year and although mom wasn't sad anymore, she still wasn't dating anyone either. It was a shame because after gaining a little weight and chopping off her hair, she was working out now and had grown her hair out and look really good, I mean for a 40 something woman.
Anyway, it was Halloween and since I still didn't have any close friends, and hadn't been invited to any parties, so I went downtown, dressed in a ghillie suit and stood by the main bars and scared the shit out of everyone walking by. A couple people got mad, but most thought it was funny and I even got a couple girls numbers. I did that for a couple hours then decided to go home.
However, when I got there, I was still wearing the suit, and I saw the Uber my mom and her three friends had taken home from a party they went to. Well, I couldn't pass up the opportunity to scare mom and her friends in this costume, could I? I hid by the side of the house and waited.
They were laughing and talking about all the creepy guys that hit on them. And most of them were married.
"Trick or treat!" I shouted when they were all basically right in front of me.
Mom screamed.
Irene cursed.
Gale jumped back and almost fell.
And Katharine clutched her heart.
"What the fuck!" Irene said.
"Who is that?" Gale asked. "I almost broke my ankle!"
"Thomas!" Mom shouted, ripping off the head piece. "Again!?"
"Again. What do you mean again?" Katharine asked.
"Oh, my son thinks it's funny to scare me. He did it last year, that's why I canceled on you guys."
"Well, he needs to be punished or something!" Gale insisted.
"Oh, he will be and you're all going to help," Mom said and marched me inside.
I was told to remove the ghillie suit. Those things are hot, so I was only in my underwear. I explained this to mom, but she didn't care.
Like mom, I too had been working out some. I was still tall, obviously, but I had gained some muscle and although I wasn't where I wanted to be, I was getting close. Still, it was embarrassing being in just your underwear in front of your mother and her 40-year-old friends.
Mom and Irene sat on the couch while Gale and Kathy (short for Katharine) sat in individual chairs.
Without a word, mom pulled me onto her lap and ripped my underwear down and started spanking me, right in front of the others.
"Oh my," Gale said. "I wasn't expecting this."
"It's what he deserves," Irene said.
"I agree," Kathy said.
After mom spanked me ten times, I started to get up to leave, but she stopped me.
"You're getting a spanking from all of us," Mom said. "You scared all of us, all of us will participate in your punishment."
With that, Irene grabbed me and pulled me onto her lap and spanked me ten times also.
By the time Gale and Kathy were done, I could feel my butt was on fire.
The women all laughed at me as I faced away from them so they could take in their work.
"It's so red," Gale said.
And warm," Kathy said, reaching out to cup my butt. Them all the women had a feel.
"You think that's something, watch this," Mom said and told me to bend over and spread my cheeks apart. I did.
Mom took her finger and tickled my butthole. I jumped and laughed like I did a year ago.
The others laughed at this and Irene said, "I wanna try." Then she reached out and tickled my asshole with her fingernail also. I jumped away.
"He keeps moving!" complained Gale.
"I'll fix that," Mom said and soon I found myself tied face-down on mom's massage table. She put a pillow under my crotch to lift my butt in the air.
Mom said she needed to get somethings and left while her friends tickled, poked and spank my ass and butthole. Laughing every time I jumped, moaned or yelped.
Mom returned and handed everyone a feather. Soon four feathers were being run all over my body, not just my butt. The bottom of my feet and also my cock and balls which had gotten bigger and were poking out beneath me. Mom also used my own electric toothbrush on my asshole. I almost came right then, but she stopped before I could. Exciting? Yes. Gross? Also, yes.
After a few more spanks from everyone I was turned over and retied.
My hard cock stood up like a periscope. Mom grabbed it and said, "Maybe if I jerk you off while my friends tickle you, you'll learn not to scare us or anyone again."
While her friends tickled me, mom stroked my cock up and down. The others wanted a turn, so mom let them all give me a few strokes too. When I was close to coming though they'd stop and squeeze my cock or balls and laugh as I grimaced in pain and frustration.
Then mom, remembering what she did last year, or maybe this is just how she gave hand jobs, rubbed her thumb under the head until I shouted, I was going to come and soon my load flew out of my cock to the delight and laughter of the others.
Then I was straight up tickled for 30 minutes with a few seconds of breaks. They used everything from brushes hair and paint, to forks and feathers. Mom even brought her vibrator and used that on me. Since Gale almost broke her ankle, Mom let her hold the vibrator on my cock, while she and the others tickled my balls and shaft until I erupted again. Once again, the women, even mom bent down and licked all the cum from my body. They all had to clean my cock for me too and took it in their mouth, running their tongues around the head and up and down the shaft. They were all good and all had their own way of sucking. I loved seeing their different tongues. Mom and Irene had fat tongues, Gale had a long thin one and Kathy's was forked. Some birth defect she said, but guys all loved it. I did too.
Then mom said since I had my "fun" that being two orgasms, they all deserved some fun too. I watched as they all stripped out of their clothes and soon, they all took turns sitting on my face until I ate them to orgasm.
Mom still had big boobs, but not as big since she'd lost some weight. Her areolas and nipples were still big though and I hoped to suck on them again.
Irene had long brown/gray hair, brown eyes and medium sized boobs, big bumpy areolas and big nipples.
Gale had short sandy blonde hair and really big boobs with small smooth areolas and small nipples.
Kathy had small boobs, small areolas and small nipples, but was the prettiest of all the women (sorry mom) with long red hair and green eyes.
They were all shaved except Kathy who had a very think patch of black pubic hair. So, she was a fake red head. That was fine with me. I'd never been with anyone who had pubic hair. I was curious how she'd taste compared to the others.
The others seemed impressed with Kathy's pubic hair also and they all reached down and ran their fingers through it. A couple must have slipped a finger inside as I heard her moan a couple times.
Irene was first and I went to town on her cunt. In no time I had her squealing like a pig.
She hopped off and Gale climbed on. She took a little longer but soon she came too.
Then mom climbed on. Since I already ate her out, I knew what she liked and I was able to give her a quick orgasm. She stayed on until I gave her a second one. The others were jealous, but it was her house and her rules, she informed them.
Hairy Kathy was last. I didn't know what to expect, but it was so much better than I thought. I found that if I blew on her cunt after a few licks, she'd shiver and push down on my face with her cunt, so she must have liked it. When she came, she squirted all over my face and her pubic hair was soaked along with my face.
After another round of a 30-minute tickle session, I was untied. I got to play with and suck on all the women's boobs while someone else knelt down and sucked my cock.
I came in all their mouths, and they liked the way I played with their tits. Even when I pinched and bit their nipples. They told me to pinch and bite them harder too. Every woman I've been with likes this. Even the ones with very sensitive nipples. I didn't like hurting them, but they really seemed to like it, so I obliged.
Then they all lined up on the couch and bent over, and I was instructed to fuck them all until they came. Since I had just come four times it was a safe bet I wouldn't come in any of them but was still told not to.
I was surprised by how tight they all were. Some tighter than others. Kathy was wetter than the other and of course she squirted when she came.
Irene and Gale moaned when they came. Kathy shouted and Mom cursed.
Then I had them stay that way and rimmed them all out as I fingered their pussies to yet another orgasm. They all liked that, and Kathy and Gale had never had that done to them. I joked and said any time they wanted a rimming to let me know. Mom gave me a (seriously Tom?) look, but Kathy and Gale just smiled.
Also, after rimming them, I spanked them too. They all had nice fat asses. They really liked getting spanked and told me to once again spank them harder. My hand started to hurt after a while. After a few smacks, I reached under and they were all soaking wet, so I fingered them to yet another orgasm. I had also spanked them a couple times as I fucked them and they all told me to fuck them harder. No matter what women say, they all love to be fucked roughly. Young, old it doesn't matter. The couple of girlfriends I had liked it rough too.
Finaly, they wanted to see me fuck and come inside mom. The others played with her tits except Kathy who rimmed me from behind as I fucked mom doggy style. When she shoved her finger in my ass I exploded inside mom, filling her up.
The others took turns licking my cum from mom's twat.
We all just lay on the floor exhausted after that.
"So, what's everyone doing for Thanksgiving?" I asked. They all groaned, rolled their eyes and held me down and tickled me again.
I did hook up with all of them in both separate and group occasions. Both with and without mom.
Kathy had a 20-year-old daughter who had come home to surprise her mom (Kathy's husband was out of town). When she heard laughter coming from her mom's bedroom she walked in and saw her mom (who was naked) tickling a naked guy her own age.
"Mom? What the fuck?"
"Tory, I'll explain later. Help me tickle him. It's so much fun."
Without another word, Tory got undressed and started tickling me too. She was just as hairy as her mom. That was a great afternoon. And that's how Tory became my girlfriend. And for my birthday Tory tied me up naked and she her friends well, perhaps I'll save that story for later.