A SUGAR DADDY and HIS SWEET TART
Chapter 5

(Mf, exhib, voy, oral, anal, toys)

by Art Martin

Jeff and Bill get frisky with the girls in Jeff's pool. Later, while babysitting for the "Bates", Brenda is taught some new some new tricks...

Chapters | 1 | 2 | 3 | 4 | 5 | 6 | 7 |

Pursuant to the Berne Convention, this work is copyrighted 2021 with all rights expressly reserved by its author unless explicitly granted.



Standard Disclaimer: This story contains sexually graphic and explicit material and as such it is not suitable for minors. If you are a minor, please leave now as it is illegal for you to be here. If it is illegal for you to read or view sexually explicit material in the community you view such material, please leave now. This story and characters are purely fictional and any resemblance to events or persons (living or dead) is purely coincidental. If you are offended by sexually explicit stories, please read no further. If you are offended by stories featuring group sex, bisexual situations, incest, sex between minors and adults, or any other situation, please check the story code before reading the text. These stories are just that, stories, and do not promote or condone the activities described herein, especially when it comes to unsafe sexual practices or sex between adults and minors.





At Jenny's the next night, I was so excited that I couldn't wait to tell her about my "babysitting" job and how easy it was to put one over my mom.  Of course I didn't tell her it was Bill I was going to be with, but my fictitious college squeeze, Billy.  She made me promise to tell her every little detail of our night of fornicating. 

Saturday morning, Tracy had to go on trip, so Jenny and I moved over to her dad's.  It was still quite warm, so we went swimming.  It just being Jenny, me and Jeff, we wore the thong bikinis he'd bought for us.  Jenny was oblivious to her dad, but I didn't miss the fact that Jeff couldn't keep his eyes off me.  It was just so much fun being nearly naked and having him so obviously interested in me.  I was, unfortunately, perfectly safe, as I was his daughter's best friend and all.  Still, I couldn't help but wonder what it would be like having sex with him, especially since I'd had a crush on him for like, forever.

So we're out there by the pool when Bill shows up.  Jenny nearly freaked.  I thought Jeff would have a cow, but Jeff seemed indifferent to Bill's presence, like it was no big deal that Jenny was nearly naked.  He didn't seem to mind that Bill was getting an eyeful, nor the fact that Bill was ogling Jenny and me.

He didn't get to ogle for long as Jenny wrapped herself in a towel and made her way inside.  I wanted to stay, but with Jenny's retreat, I couldn't.

"Gawd!  I'm so embarrassed," Jenny insisted once inside.

"Why?" I asked.

"Why?  You know why! Bill saw my bare butt!"

"So what? Jeff didn't seem to mind showing us off," I pointed out.  "So, let's go back, show off and have some fun!"

"Are you serious?"

"Yes."

She grabbed my hand and excitedly said, "Yeah!  Let's do it! That'll show Daddy!" So we went back outside. 

Jenny strode up directly in front of her dad and Bill, and with her back to them, unwrapped her towel.  She stood there a good long moment, then strode away with her best runway model stride.  I was so miffed!  Nobody was looking at me! Annoyed at both Bill and Jeff, I went into the water.  Jenny followed close behind. 

Out of the corner of my eye, I saw the two men rise from their chairs.  Jeff took two steps forward and dove in.  Bill, who was dressed, kicked off his sandals and stripped off his shirt and shorts.  "Oh, my god!" I gasped as I realized that he was commando.  He too took two steps forward and dove in.

Jenny, who was doing her best to ignore the guys, squealed as Jeff surfaced, picking her up as he came up tossing her.  A moment or so later, Bill surfaced next to me.

"You're naked!" I fussed.

"Hey, I didn't bring my swim suit," he replied.

"Oh, my god," I lamented.  "What will Jeff say?"

"He'll get over it."

"But Jenny..."

"I really don't think she's offended.  Are you?"

"No, I'm not, but..."

"If Jeff has a problem with my lack of dress, he'll run my ass off.  But, he hasn't, has he?"

"I don't think he's seen you yet," I replied.

"He knows... I told him, so relax.  Jeff's okay with it.

"You know, he fucks her..."

"Who fucks who?"

"You don't know?  Then I'm not going to tell you."

Changing the subject and leaving me wondering who he was talking about, he said, "Look, we're still on for tonight, but Jeff really has the hots for you.  So, I'm going to go flirt with Jenny; and Jeff... Jeff's going to try and score with you.  And just to let you know, if he does, it's alright by me."

"You're passing me around?"

"No, but if you want to fuck Jeff, go ahead and have fun."  With that Bill swam over to Jenny and Jeff.  A moment later Jeff was by me. 

"Bill's naked," I told him.

"He is?" he replied without any concern.  "She's a big girl, just like you are." 

He slid his hands onto the sides of my waist and lifted me out of the water and sat me back down, then launched me in the air squealing.  I hadn't even come up out of the water to catch my breath and he had me.  I surfaced just inches from his face and to my surprise, he kissed me.  And not just a plutonic peck!  He had one hand on my back and the other was filled with my bare buttocks.  Before I knew it, my top, what little there was to it, was undone in the back.  A moment later, the halter around my neck was untied and a moment after that, my top was floating away!

I heard Jenny squeak, "You're naked!"  Then she squealed again laughing as she tried to get away.  "Not my top!  Not my top!" she protested followed by, "Oh, my god!  My top!"

With my top as his trophy, Jeff swam away from me, joining Bill at the side of the pool displaying his trophy.  Flustered, but excited, Jenny and I huddled together.  "Can you believe?" she asked feigning indignation while stifling the urge to giggle and giving herself away. 

"Hey, Brenda!"  I turned to look and Jeff tossed me something. 

It splashed down in front of me and I picked it up.  "It's your dad's swim suit!" I exclaimed with a giggle.

"Daddy!" Jenny whined in surprise. 

She didn't have much time to posture as the guys were coming at us in a churning spray, scattering us like we were deer.  Bill caught Jenny first and lifted her from the water which exposed her tits.  If her dad was going to offer a modicum of protection, he failed miserably, as he let Bill have his way with his daughter and went after me.

Okay, let me be clear right now.  We didn't get molested or even felt up.  They were just playing and more or less kept their hands to themselves... more or less, as Bill didn't hesitate to cop a feel from me whenever he had a chance.  They were like two teenage boys showing off to the girls, getting out of the pool and diving off the diving board, doing flips and jack knives in the buff, giving us girls an eyeful for ourselves.  We too went off the diving board, and pretty soon, we were quite comfortable being topless with them and comfortable with them being totally native. 

I must admit, to me Jenny's dad looked even better nude than in just his Speedo.  Nice cock... not as big as Bill's, but I found it very beautiful.  I just had to think of a way to play with it some without angering Jenny.  As for Bill, from what he said earlier, Jeff didn't care.  

Late in the afternoon, I heard my phone ring.  From the ring tone, I knew it was my mother.  Jenny and I were by then just sunning ourselves while the guys sat to the side and chatted about this and that.  I picked up, but was too late, so I called her back.

"You need to come home and get ready for your babysitting job," she said.  "Do you want me to come and pick you up?"

"Uh, no, Mom.  We're at Jeff's and he'll take me home."

"Okay, but hurry along, dear.  You still need to eat and get ready."

"Yes, Mama."

I hung up and turning to Jeff said, "That was my mom.  I need to go home and get ready for my babysitting job tonight."

"Bummer!" Jenny exclaimed.  "Wouldn't you rather just stay here?"

"Yes, I would, but I need to go home.

"Jeff, would you give me a ride?"

"You go ahead, Jeff," Bill told him.  "I'll stay here with Jenny."

"Not a chance!" laughed Jeff.

"Oh, Daddy, I'll be okay," Jenny interjected.

"Uh, no you won't, sweetheart," Jeff replied. 

"Bill, you take her," Jeff said.

"Jenny?" Bill asked naughtily.

"No, Brenda," replied Jeff with a laugh.

"Don't mind if I do," replied Bill.

Not wanting my mom to get a good look at Bill's car just before "Mr. Bates" picked me up to sit for his kids, I nixed the idea.  "No, she's expecting you to bring me home, Jeff."

"Well, okay," he conceded. "We all need to grab a bite to eat, so we'll all go. 

"Jenny, get your ass dressed, girl.  You too, Bill."

Jenny was clearly annoyed that the party was busting up, but she did as her daddy asked.  Back in her room, we dressed. 

"My daddy has the hots for you, Brenda," she observed.

"Your daddy is a hunk," I replied.

"It's okay by me if you two, you know..."

"Really?"

"Yes!  He's single and so are you."

"I think he just likes to look," I replied.  "I like to look too."

"Me too!" giggled Jenny.  "And Bill, oh my god!  I pity the girl he sticks that thing in.  God, I've never seen a cock that big, except on the internet."

"Yeah, he's a big boy, alright."

*****

Mr. Bates picked me up promptly at 6:30 PM.  I thought he might just stay in his car and honk the horn, but he got out and went to the door. My dad answered the door.

"Bates.  Bob Bates," I heard him introduce himself.  "My wife and I will be out rather late tonight, but I'll try my best to get Brenda home by 2 AM."

"That's fine," I heard my dad say.

Then Dad called out, "Brenda!  Mr. Bates is here to pick you up!"

"I'm coming," I called back. 

I bounded for the door, kissing my dad goodbye on the way out.  Bill was close behind.  Being a gentleman, he got my door for me.  Then he waved to my dad as he entered the car, with the express purpose of fucking me cross-eyed that night, my dad none the wiser.  I must admit, Bill was convincing.  He'd changed into some nice khaki slacks, nice polished shoes, a nice open shirt and was wearing a navy sports jacket, just the attire a successful man might wear to take his wife out for the evening. 

We made a beeline to his place.  Not surprisingly, he undressed me right away, then he undressed and had me blow him while he stood looking down at me.  He blew his wad, pulling out at the last second and squirting me in the face and tits.  Before I could figure out what to do, he had his phone out and took several pictures of me.  I got mad, but he said that they were just for him, so it wasn't a big deal.  He left me to clean myself up and went to get us something to drink. 

With drinks in hand (I had a Coke and he had his scotch) we retired to the big sofa and ottoman.  On the ottoman, he had his bag with everything he would need.  Finishing our drinks, it was my turn to be orally pleasured.  I was shocked, however, when he wanted to do it orally from behind while I was on my hands and knees, but not nearly as shocked as when he licked across my anus.

"Gawd, that so dirty!" I whined looking back over my shoulder.  He paid no attention to my "objection" and just included my anus with his oral pleasuring and fingering of my pussy and clit. Soon I didn't care either, as it all felt so good.

He got me climbing the mountain toward the pinnacle of pure pleasure.  I was almost there when he slid his fat cock deep into my juicing pussy. Bottoming out on my cervix, he ground his hips, stirring his cock inside me for a moment, before pulling back in preparation to sink back into me.  It only took a few strokes and I was cumming on his wonderful dick.

My pussy was squeezing his dick as my orgasm swept over me.  Suddenly I became aware of his finger up my butt, which only increased the intensity of my orgasm. My orgasm peaked, then began to fade, still he slowly fucked me with both his cock and his thick finger, adding  lube to the finger deep in my ass.  Another orgasm burst upon me and I was left breathless, my arms collapsing under me, and still he slowly fucked me.  Bill always demonstrated great stamina and having already cum in my mouth once (and on my face), he wasn't going to be ready to cum again for quite some time.  Meanwhile, he fucked me, and fucked me and my orgasms continued to roll over me.  I was truly fucked senseless, not that he hadn't fucked me senseless before. 

Suddenly he pulled out of my cunt and my ass, leaving me feeling empty.  I stayed with my head on the ottoman and my butt raised for fucking.  After a long minute, I felt something pressing into my asshole.  It wasn't his dick, as I could see him behind me and his groin wasn't pressing into me.  Whatever it was began to enter me.

"Owww!" I cried out while lifting myself up, then it popped into me and the discomfort eased. 

"What did you do?" I asked as my asshole was spread open around the object. 

"It's an anal trainer," he informed.  "A butt plug. It doesn't hurt does it?"

"No.  Not really."

"We'll leave it in for a while, then replace it with a larger one."

"Larger one?  Why?"

"Why?  Because I don't want to hurt you."

"Are you going to..."

"Fuck you in the ass?" he said completing my question.  "Yes, I am."   

Bill then flipped me onto my back, spread my legs apart and went down on me, which completely distracted me from the object up my butt.  He only sucked on my clit for a few delicious moments before spinning me around on the ottoman with my head partially hanging off the edge.  Straddling my head, he dragged his ball sack over my face several times, then leaning over me, presented his big cock to my lips.  There was no hesitation on my part to take his cock into my mouth. 

For me, all this was fine and good with the world just sucking on his fat knob, and it didn't bother me that he pushed several inches of his eight inch prick into my mouth, but he kept pressing more and more of it into my mouth.  It hit the back of my throat, I gagged and he withdrew a little ways giving me time to swallow and catch my breath before he drove it against the back of my throat again.  I gagged again and he repeated the motion.  Let me tell you, at that point the last thing on my mind was the butt plug. I knew that he wanted to shove that thing down my throat and it scared me... What if I choked on it? 

After a dozen or more tries, he pulled out of my mouth, only to be manhandled onto my hands and knees once again.  My focus returned to the butt plug as he tugged on it. I yelped when he popped it out of my butthole.  I was thinking, 'He's going to shove his dick up my ass!' and I knew it was too big. 

Within seconds of taking the plug from my ass, I felt something even bigger pressing against me.  The way it speared into my anus, I knew it wasn't his dick, but another, or maybe it was the same butt plug. 

It wasn't the same one he'd put up my ass before, but an even larger one.  Again I yelped as the widest part passed my sphincter muscle and popped in behind it and in the process took my breath away. 

There was no way I could ignore what was in me, but I didn't have time to dwell on it as I was once again flipped onto my back and spun around with my head off the ottoman.  In an instant, he was pressing his cock to my lips and I opened to take him in.  I expected him to go straight for the back of my throat, but he didn't go quite that far. Leaning far over me, he fucked his dick in my mouth and as he did so, his finger found my clit.  Almost immediately he began vibrating his finger on my clit causing me to squirm about.  Suddenly, without warning, he jammed his dick into the back of my throat.  I gagged and he did it again.

"Swallow it, Blondie!" I heard him say just before he jammed it into the back of my throat for the third time.  I swallowed and his big dick went down my throat.  I couldn't breathe as he held it down my throat.  Butt plug?  What butt plug?  There was only his dick and my vibrating clit in my universe. He pulled out, letting me catch my breath and went to the back of my throat again.

He ordered, "Swallow it!" as I gagged.  I swallowed and it went down my throat for the second time and the fireworks began. I came and came hard.  When it passed, my clit was still tingling from the echoing orgasm and his manipulations, but  I could breathe easily. 

His dick went back into my mouth, sliding in until it hit the back of my throat.  I swallowed and it continued in until his balls draped over my eyes and his pubic hair was smashed into my chin.   "That's a good girl," he praised. 

He withdrew all but the head of his cock from my mouth and pressed it back inside my mouth.  I knew what to expect and swallowed at the precise moment before I gagged and took him into my throat once again. 

"You've got the hang of it, baby," I heard him say just before pulling his dick out and letting me breathe before fucking into my throat again.  

Butt plug? Like I said, what butt plug?  At that point I was mostly unaware of it. I say mostly, because you can't totally ignore something stuck up your ass, even if it wasn't hurting you.

He pulled out of my mouth, leaned over and gave me one of his signature kisses with his big tongue filling and exploring my mouth.

He broke the kiss, telling me what a "fine piece of ass" I was, then manhandled me back onto my hands and knees once again.  He tugged on the butt plug, focusing my attention back there once again. 

"Does that hurt?" he asked as he tugged at it.

"No," I answered only to have my eyes crossed, "Oh!"  as he pulled it past my sphincter and out of my ass. 

"It's looking good," he said and as if to emphasize the point, he stuck a finger up my gaping hole and wiggled it around, bouncing it off the walls of my poop chute.  "Just just need a little more," he said, "and you'll be good to go."

A moment later, another, bigger butt plug was introduced to me.  I flinched, but didn't yelp when the widest portion passed behind my anal ring and lodged there. It was however, uncomfortable, at least for the first few minutes it was inside me.  Then like the previous two, I hardly noticed it.  Oh, I noticed it alright, but it wasn't hurting me at all.  Besides he had me on my knees on the floor by the ottoman.  Looking up at him he looked huge! 

Taking his dick in his hand, he began to playfully slap my face with it, then looking down at me with a hungry look stopped and ordered, not asked, "Kiss my balls."  That was always fun for me to do.  I don't know why, but I just love to nuzzle into a guy's ball sack, taking in its feel on my face and taking in his aroma.  So I lifted his heavy tumescent organ to get it out of my way and began nuzzling, kissing and licking on his balls.  

"You really like that.  Don't you, honey pie?" he said while stroking my head and hair.  "Well, so do I.  And you're good at it too." 

I licked, kissed and nuzzled his nuts for another minute or so before he said, "Now be a good girl and suck my dick."  I knew that he expected me to take all of it, but I wasn't so sure I could from this angle, but I tried, I really tried and I swallowed that python like it was a goldfish.  Except it didn't taste fishy, it just tasted like cock, a flavor I rather liked.

"Damn, you're a quick study, Blondie.  Fuck, yeah, what a great cocksucker you've turned out to be."  I think he meant that as a compliment.

I worked that dick over as best I could, trying to get him to cum in my mouth, so he'd go soft and not stick that thing up my butt. But... he pushed me away, saying that he needed to let his dick cool off some.

With his dick clear of my mouth, he told me to get up on the ottoman on all fours.  I was a little slow and got a stinging pop to my ass.  I moved real quick then.  He didn't have to tell me to have my knees at the edge, I just did it. 

He tugged on the butt plug, but it was lodged in there.  "Hmmm, it won't come out," he said as he tugged and tugged.  He stopped tugging and added, "Well, I guess you'll just have go home with it like that."

"No! I can't go... Owwww!"

Suddenly my ass felt empty. I must have been wide open as I felt him blow some cool air up inside me.  Weird feeling!  He followed that by squirting something cold up my chute.  I hadn't seen it, but I knew it was AstroGlide and that I was about to have my ass fucked.

Again he surprised me.  I was expecting it doggie style, but he rolled me onto my back, spread my legs and resting them on his shoulders, slid his cock into my pussy.  Maybe he wasn't going to ruin my ass after all.  Sweet Jesus, I just love the feel of his big cock filling up my pussy and the rubbing it did on my clit as he fucked me; it was probably what I thought about most these days. I always got hot really fast, and soon I was almost about to cum when he pulled out completely. 

I saw him squirt AstroGlide onto his glistening prick, then aiming a little lower, he pushed into me.  I grunted, "Uggghhh," at the anal impalement.  Thankfully he didn't just shove it into me, as it was even bigger than the last butt plug he used. 

He paused and let it sit for a moment and then pushed again.  "Uggghhh!" I grunted as I felt his fat glans pop behind my sphincter. The worst was over, I thought, while he remained motionless for a moment allowing me to adjust to his girth.  With his hands, he rubbed my thighs in an attempt to distract me, and I guess it worked.

He pushed again and went in further. Almost immediately I felt my gut cramping at the unaccustomed intrusion and I cried out. Bill continued to rub my thighs.  The cramping eased after a minute or so, and he pushed in a little more. "Uggghhh!" I grunted and the cramping returned. 

Little by little he worked his full eight inches into me. About halfway in, he stopped rubbing one of my thighs and instead began fingering my clit.  That distracted me even more.  When he was all the way in, I felt so full that I thought I might explode. 

I was panting full time by then, like a woman giving birth and that helped a lot.  He slid out and slid back in.  In, out, in, out, big old Bill started to fuck my ass and as each minute passed, it felt better and better.  The frigging of my clit helped immeasurably as he fucked my ass.  He started chanting, "Cum on my dick.  Cum on my dick.  Relax, enjoy it and cum on my fucking dick, you slut.  Cum on my dick.  Cum on my dick." 

The fingering was really getting to me by then and the fucking just felt better and better by the stroke.  I heard myself bark out, "Ah, ah, ah, ah," and then my cunt just exploded, sweeping me away with the most intense climax of the evening.  

By the time Bill got me home that night around 2 AM, I was a changed person. No longer could I think of myself as innocent in any way.  I was a slut, Bill's slut, Bill's ass-fucking,  cock-sucking teen slut.  I didn't want to go home.  I wanted to stay and sleep with Bill.  Sleep with him so that he could fuck his slut first thing in the morning.  Fuck me anyway he wanted.  I was his slut. In my mind, my ass belonged to him.  It's weird, he didn't call me a slut very often, but when he did, it thrilled me

The next day I was reminded of my "babysitting job".  My throat was sore, not to mention my ass.  Still, the slut in me wanted his cock back inside me, where ever he wanted to put it.  I laid low that entire Sunday.  Judy called and wanted me to come over, but I wasn't up to it.  Jenny called and she wanted me to keep her company during her dad's standing Sunday football party.  Mom thought I was sick and I went along with that so that she would dote on me.  Even Daddy seemed concerned.  Bill... I never heard from Bill.  No text messages, no phone calls.  I called him, but he didn't pick up. I texted him, but he didn't text back.  Still, I was convinced that he loved me, even though he never said it.  I hadn't figured out that, "I'm going to fuck you," doesn't translate into, "I love you."  But then again, I was only fifteen and had a lot to learn about boys, men and love.

Of course Jenny and Judy and I chatted it up all through the day and when we weren't talking, we were texting one another. 


To be continued...

In Chapter 6 - After orally servicing Bill, he takes her to a doctor for birth control...

READ Chapter 6



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