Careful What You Wish For

My name is Kyle, I'm 18 and a senior in high school. My friend Ben and I had planned on going on a school trip to New York, but because my grades weren't good, I couldn't go. So, I went over to see him off. Also, my grandmother was in town visiting my mom (her daughter), so this was an excuse to not be bored listening to them talk about me as a baby and looking at pictures of me as a baby. He'd be gone a week. There were college chaperons and we were hoping to get laid during the trip. We were both virgins. Ben lived with his mom, two sisters 19 and 20 and his grandmother because his parents were divorced. His mom worked from home so she was there all the time and I was over there all the time. Mainly because Ben and I were friends, but also because his mom Diane, had really big tits.

The first time I saw them (and by them, I mean her tits) was at the community pool. She was laying on a chair and her tits were spilling out the side of her bathing suit. Her massive cleavage showed too. She was sort of okay looking, but she never wore makeup, so maybe that would improve her looks. Then I saw Ben come over and talk to her. Here was my opportunity. I saw him around school, but never talked to him. So, I went up and introduced myself. I forced myself to look at Ben and not stare at him mom's boobs, but it was really hard. And so was my cock.

We had to be quiet because Ben's grandmother was sleeping and his sisters were studying in their room. Eventually, the bus came and Ben left. I stayed behind and "innocently" ask Ben's mom, Diane if she needed me to do anything while Ben is gone. She said, perhaps mow the lawn if I wouldn't mind. I said sure.

"Let me know if I can do anything for you too," she replied.

"You can show me those huge ta ta's of yours," I said under my breath as I walked to the bathroom.

I came back to finish my drink before I left. But before I could grab my glass, she grabbed me and pulled my arms back. "So, you want to look at my ta ta's huh?" she asked. "Well, how about if I have a look at yours first." Then I felt my shirt being pulled up. "Hmmm. Not much in the titty department, are you?" she asked, tickling and pinching my nipples. "Answer me!" she said, poking me under the arms.

I burst out laughing.

"Oh, is someone ticklish?" she asked. Digger her fingers into my armpits. I was thrashing and laughing and almost crying.

Then I saw Ben's sisters walk into the room. Katie and Carrie. "Mom, what are you doing? You'll wake up Grandma." Katy said.

"I'm punishing this pervert. Quik help me. Take off his shoes and tickle his feet."

Both girls jumped into action. If anything, my feet were more ticklish than my pits.

They had to move me to the floor, because I was thrashing around too much. Ben's sisters each sat on one leg and tickled my feet, while their mom sat on my arms and tickled my armpits, ribs and stomach.

Finally, the noise was too much and Diane's mom came to investigate.

"Oh, my what's going on here?" She asked.

"Were punishing a pervert, mom. Take off his pants, I'll bet his knees are really ticklish," Diane instructed her mother.

The other's stopped tickling me, while Carol, Diane's mother unfastened my belt, unbuttoned my jeans, tugged down the zipper and with the help of Katie and Carrie, pulled off my jeans. Now I was only clad in my underwear in front of my friend's mom, his sisters and his grandmother. I felt myself turn beet red.

"Get him!" Carol shouted and attacked my knees. Diane was right, my knees were ticklish. Apparently, my whole body was. They tickled me non-stop for about twenty minutes. Katie left and came back with two hair brushes and handed one to Carrie. This really drove me crazy. They were tired of holding me down and decided to tie me to a massage table, Diane's side business.

Then they all really started tickling me. Then I noticed something. At some point they all took off their bras. I could easily see their tits bouncing under their shirts. That's when I got an erection.

"Diane, you're right. He is a pervert. Look at that thing," Carol said, slapping my cock through my underwear.

"Sick pervert," Diane said, and she too slapped my cock. Then her daughters joined in. Soon all four women took turns slapping my cock. "Okay. That's enough. Go back to tickling him. I'll be right back."

The others reluctantly returned to tickling me, though each would "accidently" brush against my hard cock, then say sorry.

Diane returned with a feather duster and a pair of scissors. With a couple of snips, my underwear was cut off. Now my cock sprang free. Throbbing and swaying. All the women laughed at the state I was in.

"You're in a pretty venerable state right now," Diane said, grabbing my cock at the base and squeezing. "You're tied up naked with four fully dressed women. You're at our mercy. We can do anything we want with you. What do you think ladies?"

"Tickle him!" Carol shouted and soon all four women were tickling my cock and balls with a feather from the feather duster Diane had given them.

Then the doorbell rang. "Oohh, that's our surprise guest. Be right back," Diane said.

That's when I saw to my horror my mom and grandmother walk into the room.

"Mom. What are you doing..." I said in between laughter.

"You're right. I guess something did come up," my mom said, walking over and looking at my hard cock, then into my eyes.

"Mom. Thank God. Help me. This crazy family stripped me naked, tied me up and tickled me for no reason," I said.

"Oh, so you didn't say you wanted to look at Diane's Ta ta's as you call them?" Mom asked.

"Okay. I did. But Ben and I were supposed to get laid this weekend. So, I was frustrated I couldn't go on the trip and I said something stupid. But this is too far. Don't you think?" I asked.

"I don't know. You're the one with a hard cock in front of six women, four of whom are old enough to be your mother and/or grandmother," mom replied, grabbing my cock and stroking up and down.

My cock got harder and bigger. I let out a moan. I couldn't help it. All the women laughed.

"Pervert," Grandma said, giving me the disappointed look.

"You wanna come this weekend. We can make that happen. Grandma and I'll tickle your feet, while Diane and her family tickle your cock and balls with the feathers.

"But Mom," I protested.

"Shut up, pervert," Mom said, grabbing the hairbrush from Katie.

Soon, Mom and Grandma were scrubbing my feet with hairbrushes, while Diane and her clan ran their feathers over my cock and balls. When I got close to coming, they'd stop and laugh at me as I moaned in frustration.

Finally, they kept tickling me and I warned them I was going to come. Diane and Carol ran their feathers around the head of my cock, while Katie and Carrie tickled my balls. Mom and Grandma used their nails on my feet. After a few seconds of this, I started shooting my load. Spurt after spurt of cum shot from my cock. All the women laughed and applauded.

"I read people are ore ticklish after they come," Katue said and started tickling me in the ribs with her fingers. The others soon joined her.

"How about the cock? Is that more ticklish too?" Grandma asked, reaching out and tickling my cock with her fingernails.

I was laughing and moaning and squirming.

"No not my cock," I shouted. That was all it took. All the women started tickling my cock. Especially the sensitive head.

"I guess we should clean up the mess, " Diane said and leaned down and started licking the come from my body. She was joined by her daughters, my mom and grandmother. Carol popped my cock in her mouth and started "cleaning" that for me. Then she passed it onto her granddaughters, who passed it to Diane, who passed it to my mom who gave it to my grandma.

I thought it was over. They even started to untie me. Then my grandmother of all people asked, "I wonder if his ass is ticklish?"

Soon, I was retied. Bent over a wedge with my ass in the air. My hands were tied again as were my legs. My ass was now exposed to all six women. I was even more vulnerable in this position. I needed to be punished first for my inappropriate remark to Diane. This meant a spanking. Diane was to go first. My cock had softened by this point. However, when she got to swat number five, I was hard again.

"Really, Kyle?" Mom asked, reaching between my legs and grabbing my cock. She gave it a few strokes while she made her point.

All six women gave me ten smacks each. Then came the tickling. I felt feathers, fingers and electric toothbrush and a tongue? Whoa, this was getting serious. Someone, possibly mom or grandmother, just stuck their tongue in my asshole.

My cock was hard, throbbing and dripping precum. I felt four hands tickling my feet. I looked and saw Diane, Carol, Katie and Carrie tickling my feet. Suddenly, my mom reached under and started stroking my cock, while my grandmother used an electric toothbrush on my asshole. That was it, I lost all control and started shooting my second load of the day.

This time, no one cleaned my cum from the table. I was made to lay on it and was retied. Then a blindfold was placed over my eyes. I was instructed to lick all six women to orgasm. The blindfold was so that I didn't know who I was "servicing".

The first pussy was shaved. I doubted it was my grandmother or Carol, but in today's age, you never knew. It took a while, because I didn't have any experience, but finally I got them off. They squealed in a high-pitched voice and I figured it was either Katie or Carrie. Thie next one had pubic hair that touched my nose. I'm guessing landing strip. This time it went better. They came without a sound though. I did feel them shudder a few times. I'm guessing that was good. And so it went. One pussy was hairy and one smelled kind of funky, but as I was tied down, I really didn't have a choice. Besides, six hot (mainly) women just tickled me to two orgasms. My own mother gave me a hand-job, while my own grandmother tickled my asshole with a fucking toothbrush. So, being "forced " to lick a smelly pussy wasn't a big deal. Even if I couldn't see who it was. Then I was tickled some more. It was even more sensational because I couldn't see when it was coming. Of course, my cock was grabbed, stroked, tickled, licked and sucked all the while.

"For your final punishment, you're finally going to see my tit's you're so desperate to see. You're going to stroke yourself off and explode all over them," Diane said. However, when the blindfold came off, I saw all six women standing naked before me. Diane had the biggest and best tits. Both her daughters were nice and big too, just not ass big. Carol's boobs were big but really saggy. The same for my grandmother's tits. Mom had smaller tits, but the best nipples.

"Well, don't just stand there. Stroke it," Mom said.

I grabbed my Johnson and went to town. I looked at all the tits before me, locking them away in my spank bank for later. Soon I felt that old feeling and soon I shot my third load of the day. I aimed at Diane's big hooters, then decided to give everyone some. I pointed my cock like a garden hose and made sure to get some of my come on everyone's tits. They were surprised, but then got into it. Afterwards, I collapsed on the couch, exhausted. Then I watched as everyone licked my come off each other's boobs.

I was kind of bummer I didn't actually get laid. Then I remembered, Ben had a camping trip planned with his dad next month. And I started to think, I wonder...