The Babysitter Did It Ch. 05

Story Info
Dad does babysitter a "favour".
5.5k words
4.57
75.7k
29

Part 5 of the 7 part series

Updated 06/07/2023
Created 05/29/2012
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Disclaimer: All characters in the following story involved in any sexual activity are 18 years old or older.

Request: Take 2 seconds to vote on the story or better yet, 2 minutes and leave a comment - Thanks!

Thursday morning, 11am. Sitting at my desk. Like some coke addict I was starting to tremble a little from withdrawal. My drug of choice wasn't some white powder though. It was a beautiful, sexy eighteen year old sex goddess that fate had thrown into my lap and as of yesterday, for the first time, onto my dick!

It had been worth the wait. I now marked time as BK and AK (Before Krissy and After Krissy). I used to fantasize BK but those fantasies were nowhere near to the amazing reality of the last few weeks.

At 11:30am on the dot I was on my way out the door to see how my Bold Blonde Beauty was going to top yesterday. She somehow managed to constantly raise the stakes.

I entered the garage with a foolish grin on my face like a kid going into a candy store. The door was opened for me.

"Hi Ruby," I said not surprised this time by the presence of our lookout.

"No Mr. A. I like when you call me 'Red'. Your nickname for me makes me feel special."

As I closed the door behind me I said, "You are special Red, very special. And not just because you're our 'watchful watcher'." I winked at her. Like all of Krissy's gang, as she called them, Red was a knock-out. Dressed in a white sheer blouse and a tartan red mini skirt, her killer legs looked ready to be licked from bottom to top, especially with their just-below-the-knee high sheer white stockings.

She blushed which was cute but I couldn't see how anything could embarrass her. After all, yesterday I'd seen her naked writhing on the floor from masturbating while I came inside Krissy.

Just like last time she yelled, "Krissy, Mr. A is hitting on me again!"

"Is he now Scarlett? Last time I checked, you were the one saying how sexy my Mr. Adams was!" said Krissy, walking in to the room.

My turn to blush again. This was becoming a habit.

There was certainly nothing frumpy about Krissy today. She wore a red bustier, red high cut semi-see through panties and six inch stilettos. I inhaled sharply at the sight of her. Krissy smiled at my reaction and her face shone.

"I see you like, Mr. A?" said Krissy.

"Oh I like babe, I like," I answered.

"Babe? That the best you got Mr. Adams?" This last came through the adjacent doorway. I spun my head in that direction. "Jen?" I said confusedly.

It was cute Jen who I assumed was Chinese Canadian. Seems I was always getting surprised by her. The last time I saw her was in the cinema when I opened my eyes as I started to explode and had quite a pleasant shock.

Jen was smartly dressed, almost business like.

"Yes, Jen is still my name. Hope that's not a problem. But seriously, I'm sure you can come up with a better way to refer to your dream girl."

"Umm," was all I could manage.

Krissy came to my rescue.

"Lay off Jen. Mr. A, could I speak to you privately a moment?"

She took my arm and led me into my study and closed the door behind us.

The curve of her bustier just barely covered her areolas. My eyes were stuck there hoping to catch a glimpse of something more. Krissy put her finger under my chin and lifted my head a bit. She was smiling. "Glad you like it so much Mr. A, but I have something serious to talk about."

"Okay," I said, "but you must admit that your fab outfit doesn't make it easy." I had no idea where this was going.

"I asked Jen over because...well...to put it bluntly, Ruby sucked at being a lookout. A train could have ploughed through the house and she wouldn't have noticed in the state that she was in."

"Yeah, I guess we were lucky," I said.

"Well, this time I don't want to depend on luck. Which is why Jen is here. Any concerns?"

"Nope. I'm fine with Jen. Sounds like you're confident she will focus on her job."

"No questions about it. Jen will keep her commitment and not get distracted. That's how she rolls."

"So..."

"So, about Ruby still being here. Well, I owe Ruby a huge favour. Last year I got in over my head at a bar and Ruby saved my ass, figuratively and literally. It's because of the 'bad stuff' she's been through that she knows how to kick some serious butt -- I'm talking 2 two hundred pound baddies."

"Wow. Who would have thought. Guess I better stay on her good side."

"No need to worry. With good guys and even minor bad ones, she's got a tongue on her but physically a kitten. With real baddies though she loses it...let's just say if one of them wasn't so embarrassed he might have been able to press charges."

"All interesting, but...," and I reached out to caress her butt.

Krissy slapped my hand away and said, "Just a sec Mr. Adams, I need you to listen. As I told you before, I'm not going to tell you why Ruby is the way she is -- that's for her to decide if to -- but what I can tell you is that she has a bit of a phobia about intercourse. She wants it badly but hasn't been able to bring her self to let someone make love to her for a long time."

"Long time?" I thought, "She's only 18. Oh how times have changed". I started to see where this might be going and said, "You don't mean..."

"Yes, I do mean. Ruby asked if she could join us just this one time. She thinks with you, she can overcome her fears and start to lead a normal sex life."

"Holy shit!" I thought. "This nymph is asking if I would be ok with fucking her gorgeous friend -- just this once! Unless this was some kind of test...in which case I was going to fail miserably."

"Look Krissy," I cautiously started.

"Mr. Adams.," interrupted Krissy, "I know you're attracted to her." She placed her hand on my cock and could feel how hard it was.

I caught my breath.

"We may have fucking great sex, but I truly believe we have more and I'm willing to bet on it." She started to rub my penis through my pants.

"Whatever you want Krissy," I managed to get out. "Whatever you want."

Krissy lifted her voice. "He said yes," she said loudly.

The door burst open.

"Seriously?" said Red. Her face showed relief. "And you're sure you're ok with it Krissy?"

"Ruby, come over here."

As Red came over, Krissy took Ruby's hand and replaced hers with it on my crotch.

Red slowly rotated her hand on my hard on and smiled. "At least I know he's telling the truth because erections don't lie."

I couldn't think of a reply. In fact I couldn't really think of anything.

Krissy guided me back until my legs touched the couch and then she pushed me to sit down on it. Red knelt down on my right and Krissy followed suit on my left and started unbuttoning my shirt.

First Red pulled my right arm out of my shirt and then Krissy pulled it completely off. Red unbuckled my belt and Krissy pulled it out.

"Lift that cute tushie of yours," said Krissy.

The each took hold of a side of my pants and pulled it down and off my feet. They were working brilliantly as a team. My penis was seeing if it could burst my underwear. They decided to rescue my underwear by peeling it off.

I remembered seeing something like this on the internet. I think it was called "Clothed Females Naked Males" or something like that. It was hot. Never thought I'd live the fantasy scenario though.

Red and Krissy kissed me me on the cheek. Then they moved down to my shoulders in unison. It was as if they were doing some kind of synchronized dance. "'Synchronized fucking' - now there's an Olympic sport that would get a huge viewing audience," I thought.

They kissed my chest and then down to my ribs and my hips. I was tingling all over. Parallel with my cock they looked up at each other. Krissy winked at Red and they continued down my legs.

"Oh you naughty teasers!" I said. "I'm going to punish each of you with a hard fuck," I said smiling ear to ear.

"Turn over," Krissy said.

I did and leaned over the back of the couch.

"Ouch!" I said as all of a sudden I felt two bites at the same time on my ass cheeks.

"Maybe you'll fuck us, maybe you won't!" said Red. Her voice betrayed which option she really wanted though.

I felt slaps on my bum and heard Krissy say, "Now turn back over."

"Alright," I said, "who's going for the first ride."

"Not so fast."

It was Jen with a tray in her hands and a glass filled with three fingers of a what looked like alcohol. There were two halves of a plastic straw that had been cut in two.

Krissy jumped up and took the tray from her. "Thanks Jen," she said.

"My pleasure, babe," she replied with a smirk at me.

I grinned back at her without the slightest bit of self-consciousness even though I was sitting buck naked with my flag pole at attention.

Krissy came back and Jen leftb presumably to take up her post.

"What's this?" I asked.

Krissy passed the glass beneath my nose and I took a whiff.

"Is that my Courvoisier Extra L'Essence de Courvoisier?"

"It sure is. You said it was only for very special occasions. Can you think of anything more special than this?"

I shook my head slowly from side to side. True it was a three thousand plus bottle of Cognac that I got as a fortieth birthday present from my old man but I couldn't think of anything more special than this. Not that I was really thinking. I wondered what he would think if I told him how it had been used. I think he'd be proud.

"So what's with the straws?"

"Full of questions, isn't he?" asked Red. "I can fix that."

She lifted her right leg onto my right knee. This of course raised her mini-skirt way up and I learned that her panties matched her stockings in both colour and sheerness. There was a wet patch between her legs and I could see a small line of pubic red hair at her crotch.

Red peeled off her stocking and put it over my eyes. It felt like silk.

"Aww," I whined like a kid but then I realized that Red, possibly intentionally, had pulled the stocking taught so that after she tied it behind my head, I could still kind of see.

Red repeated the same thing with her left leg. This time she took the stocking and wrapped it around my cock and used it to gently massage it.

"Hmm," I said.

I lost track of Krissy but she came into view holding a straw with her finger covering the top of it. She brought it to my chest and removed her finger. It ran down my chest and pooled in my belly button.

Krissy gently pushed my cock out of the way and sucked the cognac from my belly button and licked all the way up my chest where it had run down.

I shivered. "Ok, it's definite now. This is probably the best usage of this spirit in it's history."

Krissy smiled. "We're just getting started Mr. A."

Krissy put her straw into the glass and sipped some of it.

"Do you like it?" I asked.

Krissy didn't answer. She leaned in close to me and kissed me on the mouth. I opened my lips to receive her tongue and was surprised to find the fine cognac filling my mouth. Luckily it didn't make me cough. I held it in my mouth and Krissy's tongue came in to swish it around. With our kissing, some dribbled out onto my chin but Red was quick to lick it up.

I sucked on Krissy's tongue and was sorry when she pulled away. We each swallowed some of the cognac.

"My turn," said Red.

I saw her peel off her panties. She lifted them under my nose and said, "Smell what you do to me Mr. A."

I have a good memory when it comes to smell and I remembered this lovely nectar from the last time I smelled her panties in the cinema.

She tossed them onto my clothes and said, "You can keep them if you'd like."

"Yes, please."

Red mounted the couch and stood astraddle me.

"Oh yeah, pussy time!" I said.

"Yes and no," said Red.

Krissy held up the glass and Red put her straw into it, sucked a bit up and then covered it with her finger. She then pushed my head back and lifted her right foot next to my left ear.

"Open up but don't swallow," she said.

I smiled. "I expect to be saying the exact opposite to you in the very near future."

Red chuckled. "I can't wait Mr. A., now open wide."

I opened my mouth. Red's pussy was hovering over me. She brought the straw to the top of her pussy and lifted her finger. The cognac ran down her pussy and into my mouth. She repeated this a couple times and then came down to kiss me the way Krissy had done."

Red pulled away and said, "Okay, you can swallow now."

"Mmm...girls I didn't think $3000 cognac could be made better...I think you've spoiled it for me. From now on I want Courvoisier Extra L'Essence de Krissy et Red."

"He's so adorable Krissy," said Red. "Ok, for that I'll reward you with the gift of sight." She removed the stocking covering my eyes.

I made a show of blinking my eyes as if I was getting accustomed to the light again.

They kissed me on either side of my cheek and then moved to my lips where we managed a three-way kiss. The girls pulled away from me slightly so that they were just kissing each other.

I took the opportunity to caress their asses -- Red's bare one and Krissy's panty covered one. I continued up Red's back under her top but ran into Krissy's bustier.

"Enough Krissy, come here," I said and pulled her into my lap facing away from me. I started unzipping her bustier and she started slowly moving her ass around which was pushing my dick onto my stomach.

"Now that's better," I said as I pushed the bustier forward so that it fell to the floor. I pulled her back and reached around to cup her breasts. I squeezed her nipples and started massaging them. Krissy leaned her head backwards onto my shoulder and closed her eyes. "Mmm hmm," she mumbled and still managed to move her ass ever so slightly so that it drove me crazy.

Red came around to the front and leaned in. I squeezed Krissy's left breast and felt Red's lips close over the nipple.

Krissy inhaled sharply. Red let go and started circling Krissy's nipple with her tongue. She moved on to sucking it with the intensity of someone starving. Krissy groaned into my ear.

Red bit down gently on Krissy's nipple. As an accomplished breast-man, I appreciated Red's skill. "You're quite good at this," I said to her.

Red smiled. "I like to think so," she said and moved over to Krissy's right breast and repeated what she had done to similar effect.

Red pulled away slightly so that she could push my legs and Krissy's wide apart. She knelt between our legs and gently cupped my balls for a moment. Then she placed her fingernails on either side of them and lightly scraped them down the length of my thighs to me knees. She did the same to Krissy and repeated a couple times switching between us.

Red lifted up. "It's been a while since I tasted your pussy Krissy," she said. She leaned forward and licked Krissy's pussy through the panties. Krissy squirmed and I went back to caressing her breasts.

Red pulled away and grabbed the small sheer material covering Krissy's snatch. She pulled to the side and easily ripped Krissy's panties.

Krissy's eyes flew open and she raised her head. "Hey! Those cost a...," she stared with. She broke off and took a sharp intake of breath as Red attacked her bare pussy and sucked her clitoris into her mouth.

Krissy tensed up and pushed her head back into my shoulders.

"You were saying?" I whispered into her ear.

"Never...," she managed as Red let go of her clit. "...Mind," she finished with as Red started licking the full lengthy of her pussy.

Krissy opened her legs wider and placed them over my legs. I was surprised at how wide apart she could open them up.

"Gymnastics. They teach such great life skills," said Red.

Red went to town licking Krissy's pussy. She had good technique. She flicked her tongue on Krissy's asshole and ran her tongue on the area between it and Krissy's pussy. She then went up the full length of Krissy's cleft and sucked her clit again. She brought her right hand up which was in a fist with her index finger sticking out. She placed it at the mouth of Krissy's box and then shoved her finger in.

"Ooh!" Krissy managed and her reflex was to pull her legs together to squeeze Red's head and she grabbed Red's hair with both her hands.

The tip of Red's elbow came briefly into sight and disappeared again so I knew Red was finger fucking Krissy.

I squeezed Krissy's breasts with my hands and then the nipples between my fingers.

"Yeah," Krissy said. "No, no, don't stop," she said, presumably to Red as I had diligently continued to play with Krissy's boobs.

"Oh!" Krissy managed and her mouth stayed open and her fingers pulled Red's hair even tighter. As Red's elbow continued to pop in and out of view I guessed that Red had increased the number of fingers she was using to fuck Krissy.

Krissy's breathing became more erratic and she she started to move her hips. I stuck one of my fingers in her mouth and she sucked it tightly.

Red picked up the pace and Krissy let my finger go.

"I'm gonna...," Krissy said.

I started to squeeze Krissy's nipples very hard, probably slightly painfully.

"I'm gonna..."

I thought Krissy was going to rip out some of Red's beautiful hair.

"Ahh!" Krissy yelled and started bucking her hips. I held her upper body in place with my hands on her breasts.

"Ahh!" she said again and then bit down on my ear lobe. It hurt but in a distant way as I held onto my beauty as she powerfully came into Red's mouth.

Krissy's grip on my ear gradually lessened. "I didn't want to come so fast," she mumbled.

"May that be your biggest sex problem sis," said Red. "Now make way," she continued with a gentle slap to Krissy's hip.

Krissy turned to me and I gave her a kiss on her lips.

"Hey, hey, stop being greedy. Another pussy waiting."

Krissy pulled away smiling. "Ok, ok, you'll get yours!" said Krissy and got up.

"Ahem...actually, I need to be getting back to work," I said.

"What!?" they said in unison. They both looked alarmed.

"Just kidding!" I said.

"Ha ha, not funny," said Red as she grabbed my balls in her right hand. She looked down at me, into my eyes, and started to increase the pressure of her squeezing.

I looked down and back up at her and saw that her eyes were starting to glaze over. She was no longer here.

"Red?" I said.

The pressure increased.

"Stop Red!" I said with some urgency in my voice and I went to try to get her hands off.

She slapped my face hard with her left hand.

"Ruby!" shouted Krissy.

Red blinked and let go of my balls. "What? Oh my god Mr. A. I'm so sorry!"

She gently caressed my face which I was sure still had a handprint on it.

"Sorry, sorry, sorry. I got lost for a moment. I promise it won't happen again."

"Better not," said Krissy menacingly.

Red's eyes looked like they might be filling up.

"It's ok," I said and kissed each eye. "I've always been curious about light S&M".

She smiled and visibly relaxed. "Thanks Mr. A. Krissy note that one down. Ok, now I think I remember you saying something about swallowing..." And with that she knelt between my legs and put the head of my penis into her mouth.

Some far off part of my brain hoped she didn't get lost again as teeth clamping down would be so much worse than a hand. That part of the brain however was the back seat non-driver in this case.

"Yes, Red. That's it," I said as she swirled her tongue around the tip.

Krissy came over and kissed me.

"Still having fun?" she asked.

"Miserable time," I answered just as Red decided to deep throat me and slowly pull her lips back up the full length of my dick.

"I can see that," said Krissy smiling as I put my head back.

12