Babysitting Fiasco

Mrs. Anderson greeted me at the door wearing just a towel. Her huge boobs spilling over the top.

"Hi Josh. Come in, come in. I have to finish getting ready. I'm so late. Jessie's going to kill me."

"Gee, I hope not, Mrs. Anderson, who would I babysit for?"

I replied.

"Ha ha Mr. Funnyman," she said poking me in the ribs. I jumped back and gasped.

"Oh, is someone ticklish? Don't worry, I'm just joshing you," She joked, poking me in the ribs again. I laughed.

"Very," I replied, reaching out to grab her hand as she tried to poke me for a third time, however at the same time her towel slipped off her and she reached down to grab it, my hand accidentally grabbed her breast.

"Hey, you're here to babysit, nothing more," she said in mock sternness.

"Oh, my God, I'm so sorry, Mrs. Anderson. I did not mean to do that," I stammered, turning beet red.

"Then do you mind letting go?" She asked, looking down.

I followed her gaze and realized I was still holding her breast.

I promptly let go, but couldn't help watching as it bounced.

"Well, at least I know you're not gay," she said, looking at my crotch.

I looked down at my cock trying to burst through my jeans. I turned ever more red, if that was possible.

"The kids are outside playing. Why don't you go to the bathroom and calm down before you join them," she said, reaching out and patting my crotch a couple of times.

With that she turned and started walking down the hall to her bedroom, not bothering to cover up with the towel.

"Mrs. Anderson, I really am sorry."

"Josh, you've seen me naked and touched my breast, I think we can be on a first name bases now. Call me Amber," she called over her shoulder.

I know there aren't that many guys who babysit, especially while in college, but I had know this family a long time. Well, I've known Mrs. Anderson, a/k/a Amber for years, but not her 2nd husband Mike. He was older and traveled a lot. He was gone now. Amber's first husband died when the kids were pretty young, then she met Mike, he was divorced and his kids were older. His daughter, Carley and I had some of the same classes. I knew of her, but didn't really know her. Different circles. I was more bookish, she was more popular.

Anyway, babysitting was great, the money was good, also after the kids went to bed I could study. Plus I thought it'd be good practice for when I had kids someday. You know, if I met someone like Amber. All I needed was a few billion dollars, a masters degree from an ivy league school, and the looks of George Clooney. All of which Mike had, I on the other hand possessed none of these things. But I had personality and personality goes a long way - at least according to Samuel L. Jackson in Pulp Fiction.

After wearing the kids out from playing outside, part of the time I was their captive and they tied me up to the jungle gym outside. When we came in I casually dropped the ropes by the couch and forgot about them. Then I gave them a bath, fed them, put them to bed and read them a story.

After studying, I must have nodded off, because I woke up to the front door being opened.

"Owe! Damn, Carley that hurt!"

"Ha! That's what you get bitch!"

"Would you two keep it down, you're going to wake up Carley's brother and sister."

"Trust me, those two could sleep through a tornado," Carley said.

"Hey, if your step mom isn't home, who's watching the munchkins?"

"Probably that creepy weirdo, Josh," Carley said.

"Ewww, you mean that guy in your English class?" One of her friends asked.

Creepy weirdo? I mean I know we're not exactly friends, but creepy weirdo, really? I decided to teach these haughty girls a lesson. I hid behind the couch and waited. As soon as they sat down I jumped out and yelled, "Boo!"

"Shit!" Faith said and jumped off the couch like she'd been poked with a cattle prod.

"Oh my God!" Said Lexi, covering her head and ducking in the couch.

"Josh! What the fuck?!" Carley asked, grabbing her heart. "I think I just peed a little bit."

"Ewww," Lexi and Faith said simultaneously, looking at her crotch.

"Stop looking at my crotch. I said I think and only a litrle."

"Well go check, I think I smell it," Faith said.

"Ewwww!" Lexi said.

I burst out laughing. Then got up and started walking away.

"Hey, where do you think you're going?" Carley asked me.

"Some of us actually use the bathroom to pee," I replied, laughing again.

Faith and Lexi snickered at this remark.

When I got back the girls were trying to hide behind the couch to jump out at me, but I easily spotted them. I went to the other side and snuck up behind them, scaring them again.

"I told you that wouldn't work," Lexi said.

"Plan B?" Carley asked. The other two nodded. Then Faith said, "Get him!"

Before I knew it, all three were on me, pulling off my clothes.

"Hey, what are you doing?"

"Oh, your punishment for scaring us, twice, is we're going to strip you and tie you up with these ropes we found convenient by the couch, until my step mom comes home," Carley said.

Before I knew it I was naked and tied up good. These girls either had experience in removing men's clothes, were highly motivated or both. Probably both.

"That's it?" Lexi asked.

"Well, we can't beat the shit out of him, although I'd like to," Carley replied.

"We could tickle him," Faith suggested.

"Yeah!" The other two said.

"No!" I said before I could stop myself.

"Awww, is little Joshy washy ticklish?" Carley asked digging her finger under my armpit.

"Aaaaa!" I screamed writhing on the floor.

Carley sat behind my head and dug into my arm pits.

Faith sat on my chest and tickled my side's and stomach.

Lexi was at my feet, but they weren't very ticklish. "Hey, no fair. His feet aren't ticklish," she pouted.

"Try the back of his knees," Rosey suggested.

That did it. I couldn't get away from thirty fingers tickling me. My face was red and it was getting hard to breathe.

Carley must have noticed, because she called time out.

"Oh my God! Look," Faith said pointing to my crotch.

My cock was rock hard.

"Fuck Josh, if I'd known you were that big I wouldn't have called you names," Carley said.

My cock is actually about average size, but really thick, especially the head.

"Come on girls I have an idea," Carley said jumping up.

"I'll just wait here," I retorted. This got me a laugh from Lexi and Faith.

"Really?" Carley asked.

"It was funny," Lexi and Faith said simultaneously again.

A few minutes later they came back. They had a basket and I had a sinking feeling, this was about to get a lot worse.

And I was right. The girls tickled my cock with everything from a feather duster to makeup brushes to an electric toothbrush. My cock twitched and jumped. The girls thought this was the funniest thing ever. My balls and asshole were tickled and played with too. Soon precome was leaking out of my cock.

"Ewww!" Lexi said pointing it out to the others.

"What it's just precome," Carley replied, then wiped the head of my cock, so the precome was on her finger. She acted like she was going to taste it, then shoved her finger in Lexi's open mouth.

"Carley! Come on, I don't know where that fingers been."

"On Josh's cock," she said laughing.

"I meant before that," Lexi said.

"Oh, my asshole."

"Knowing you, I wouldn't doubt it."

"How does it taste?" Faith asked.

"Pretty good actually."

Carley stuck her finger in her own mouth. "Yep, real good. Want some?" She asked holding out her finger towards Faith.

"I'll get it myself," Faith said, then bent down and took Josh's cock in her mouth.

"Hey, what's going on?" Carley asked. "We are supposed to be punishing him for scaring us. Now we're eating his come and sucking his cock."

"Well, I'm sure he knows how to use this cock, let's see if he knows how to use his tongue...on our assholes," Faith said.

In no time all 3 girls were naked and Carley was sitting on Josh's face with his tongue in her ass.

Well, this isn't what I thought would happen when I decided to scare three 19 year olds, but I'm not going to complain.

"You two play with his balls and asshole while I suck his cock. We'll give him a set of blue balls like he's never had before," Carley ordered.

Faith and Lexi complied laughing. Every five minutes they would switch.

They were so involved that they didn't hear Amber, Jessie and Rosey come in. Jessie was Faith's mom and Rosey was Lexi's mom.

"Having a good time girls?" Amber asked.

All three girls jumped.

"Mom what the he'll?" Carley shouted.

"Geepers creepers, that's the third time we've been scared tonight." Lexi said, then noticed her mom. "Oh shit. I mean hi mommy."

"Oh shit is right," Rosey said.

"I don't mean to break up the family reunion, but could someone please get me off? I'm dying here," I said.

All six women looked at Josh's cock, which was leaking precome again.

Almost absentmindedly Amber reached out and wiped the precome off Josh's cock and promptly licked her finger.

"Like mother like daughter," Faith said.

"What do you mean?" Amber asked.

"She did the same thing earlier," Lexi explained.

"Step mother," Amber said.

"Step daughter," Carley replied.

"Well Josh if I'd known your cock was really that big earlier when you saw me naked I might have stayed home," Amber said.

"Wait so you saw my mom and me both naked today?" Carley asked.

"Yes, her towel slipped off her and I saw her naked," Josh explained.

"Don't forget you also grabbed my breast too."

"I explained that was an accident," I said to clarify for the rest of the women. No one seemed to be buying it though.

"Mother daughter is a lot of men's fantisies," Carley said.

"I thought you were step mother and step daughter," I replied sarcastically.

"That's enough out of you," Carley said and started tickling me again.

I burst out laughing and started jumping around.

"Oh that's right, you're ticklish," Amber remembered. Then started running her hands up and down Josh's side's. Then she noticed the box of supplies.

"What's all this?"

"Items we tickled him with," Carley said smugly.

"Is that my toothbrush?" Amber yelped.

"Maybe?" Carley replied

"Okay girls, time for your punishment. You will use your tongues to make Josh come, while we spank your butts.

"But mom..." Carley pleaded.

"Butt is right," Amber said. "Ass up, head down."

"You two also," Jessie ordered.

I was in a quandary. I was about to get the release I sought, but I would also love to see the girls getting their butts spanked by their mom's. Oh well, you can't have everything. Plus I didn't really think they were getting spanked all that hard. It sounded more like moaning than whimpering or crying.

"Switch," Amber said and now the mom's were spanking their friends daughters. Then they switched again.

"Amber your daughter's pussy is absolutely dripping," Rosey said.

"They all are," Jessie said, after looking at each girls pussy.

"Lets see if we can have a four way simultaneous orgasm," Amber suggested.

"Well, we know they all like having their assholes licked," Rosey said, then started licking Carley's asshole, while sliding two fingers inside her soaking cunt.

That sent me over the edge and I shot a huge come load. The girls playfully fought over who got to suck my cock clean, then were knocking heads trying to lap up any come off my body. Soon though I was forgotten as one by one the girls had huge orgasms themselves.

Spent they collapsed on me. "As much as I am enjoying this, could someone please untie me? I really have to pee."

When I came out the girls were gone, sent to bed I assumed.

"Josh you can sleep downstairs tonight," Amber said.

I often did that as it was a hike back to my apartment.

"Thanks, Mrs. I mean Amber."

I was relaxing watching some TV before going to sleep. The basement is soundproof, so I knew I wouldn't bother anyone. Then Amber, Jessie and Rosey came down. Good grief, what now, I thought.

"We just wanted to apologize for the way our girls behaved," Jessie said.

"Well I did scare them pretty good."

"We know we just watched the tape," Amber said. "It was really funny. I'll show it to you tomorrow."

"Oh yeah. I forgot you have cameras."

"Don't worry, our husband's won't ever see them. I did make a copy for Jessie and Rosey though," Amber explained.

"Oh sure," I said, smiling, not sure if this was good or bad.

"There's also another reason we came down here, Josh. I wanted to show Jessie and Rosey how to give a massage. As you know I'm a professional massuser, and since it would be awkward to use one of my clients, we thought since we're all here it would be a perfect opportunity."

"Plus we've already seen you naked," Rosey supplied.

"And we'll be naked too," Amber said.

"Wait what?" Jessie said.

"Oh don't be such a prude, Jess," Amber scolded.

I looked at Jessie.

"Fine, we'll be naked too."

After I stripped out of my clothes I walked naked into the other room, Amber was the only one there.

"Go ahead and lay down on your stomach, Josh. The other two will be here shortly."

There was a hole cut in the middle of the table. "What's the hole for?" I asked.

"For you penis," Amber replied.

"I figured that part out. Why though."

"Believe it or not, a lot of men get erections during a massage. It's more comfortable this way. I also have one for pregnant women for their belly's to hang down. They all love it."

Soon I felt oil being applied to my back, then Amber was massaging my back. It felt amazing.

I heard the door open and close. That must be Jessie and Rosey, I thought.

"I'm going to do some deep pressure massages to your arms and legs now. It's very important for you to remain still," Amber said in a soothing voice.

After a while I realized something was wrong. I felt three pairs of hands on my back legs and arms, but there was still pressure on my wrists and ankles. It almost felt like, crap I was tied up again. What was it with this family?

"Well lady's, I think, Josh just figured it out," Amber said. She must have felt me tense up.

"Did you really think you could scare our daughters and not be punished for it?" Amber whispered in my ear. "The children are going to a camp for a week, my husbands out of town all week too, and since you're on summer break, guess who's going to be our slave this week?" Amber asked rhetorically.

"I'm guessing me?" I smartly replied.

"That's right, smart ass," Amber said swatting my ass. "Wow check out this hard tight ass girls." Jessie and Rosey came over and started squeezing, pinching and spanking my ass.

"Is your butt ticklish, Josh?" Amber asked and all three started tickling my butt. Then they started licking my butt. One on each cheek and on on my asshole. They made me guess who was licking my asshole. If I got it right, the would each give my cock three strokes, if I guessed wrong, they would each smack my ass three times. Finally Amber asked, "Who wants to go underneath?"

"I will," Jessie volunteered, she picked up a long blue feather and waved it in my face, before slipping under the table.

Rosey showed me the electric toothbrush she had.

"I'll just be using my hands, but just ask our girls and Mike if I know how to use them, I'm sure they'll all agree I do."

"Go!" Jessie shouted.

Amber dug her fingers in my side's, then moved to my arm pits. Rosey had the toothbrush all around my butt and asshole. Meanwhile, my cock was once again hard from Jessie running the feather back and forth on it, around the head and across my balls.

"I bet this would be more sensitive if it was lubricated," Rosey said, then I felt something wet running down my ass crack to my anus. "Bullseye," she said, then I felt her finger spreading her spit around my asshole and slipping inside. "There, how do you like a woman's juices entering your body?"

After a few more minutes they switched places. Amber was tickling my ass, Rosey was using the toothbrush on my cock and Jessie was feathering my arm pits, back and sides.

The toothbrush felt great on my cock. I was sure I was going to come several times, but these women knew what they were doing. Keeping my close to the edge without going over.

Amber's finger was replaced by her tongue. She would lick my asshole and tickle the spot between that and my balls, then switch and lick that part and tickle and finger my asshole. The sensation was amazing.

They changed again. The feather really tickled my ass. The other things was more stimulation. The toothbrush on my upper body made me laugh more than I had all night.

But Amber was right, she sure knew how to use her hands. And her mouth too. She tickled my cock up and down the shaft. Around the head. Underneath the opening. She even tickled it with her tongue when it was in her mouth.

Finally when I was ready to pass out again they stopped and untied me.

"Can I go to sleep now?" I asked.

"Oh Josh honey, you'll be up for a little longer. In more ways than one," Amber said stroking my cock as they simply turned me face up on the table and tied me down again.

And I was going to be here all week? I'll never survive. Maybe babysitting isn't quite the great job I think it is. I mean who ever heard of anyone getting tied up and tickled at McDonald's?