Shelby and Johnny, PT4 Riding Jackie

Shelby and Johnny, PT4 Riding Jackie
By Discustingperv

Authors note: This is part 4 of a continuing story that was originally
titled, “It All Started Innocently Enough.”

Starting with the original title, then Part 2 “Taking
Shelby,” Part 3 “Shelby’s Secret.” I go back and forth in time.
So if one story doesn’t make sense, check out the others so you’re caught up.
I will continue writing this series so long as the feedback is good. I will also add other stories as the mood moves me.
I thank you in advance for your support.

Somewhere in my slumber, I went back to another time. Shelby and I had just started out. Shelby had two sisters, Jackie and Kelly.
This is where our story begins.

When I met Shelby the three girls were a mess.
They all had esteem issues and very little self worth.

I found out that the father was verbally abusive to thegirls.
Basically telling them how useless they were and they would amount to
nothing in life other than becoming whores. He told them repeatedly how they would have to sell their bodies just to buy underwear.

They weren’t the boys he wanted so, he treated them like shit.
Their mom, Irene, took the brunt of the abuse until she wised up and throw the worthless fuck out. I had a run in with him and totally kicked his fat ass, but that’s for another story.

I had brought Shelby out of her shell. I treated her like gold. I respected her and always kept my word with her.
She was dressing better and had more self-confidence, especially after I popped her cherry.

I had about a week before I was to go away to the Army and we were in Shelby’s room doing what we usually did when the feeling hit. What we enjoyed!

FUCKING!!!

I was doing a slow pile drive in and out of her tight gash. Just feeling her hotpussy around my rock hard cock.
I thought I heard an additional moan in the room with us. I looked around, still keeping my pace, when I noticed Jackie in the closet.

Her eyes were closed and she had one hand down her sweat pants and another under her shirt. I was embarrassed and flattered at the same time. I stopped my pile driving and whispered in Shelby’s ear,

“Shelby baby, don’t freak out, but Jackie is watching us!
She’s Jilling herself in the closet.”

Shelby’s eyes went wide and she turned beet red. She was about to say something when I put my finger to her lips and said,
“SHHH!!”

My upper head went to work and I whispered to Shelby,
“Baby, if she wants a show, why don’t we give her one?”

Shelby whispered back, “It’s embarrassing!
Doing it with my sister watching us?”

I said, “Babe, it’ll be fine. Trust me?”

(We had a thing, when she wasn’t sure of soething I would ask if she trusted me and her response was always, “with my very life!”)

She thought for a moment, then said,

“With my very life!”

I said, “Ok, let’s make us and the headboard make some noise!!”

I pulled out of Shelby’s dripping pussy and pulled her to the edge of the bed and spread her legs wide, I had my arms under her knees.
Her legs looked like a big M.

This was also an angle where Jackie could see almost everything. Jackie obviously heard us moving and opened her eyes. What she was looking at made her go wide eyed and she started working herself good!
Shelby reached down and started Jilling her clip and I started ramming.

The headboard was banging the wall and Shelby was moaning and screaming,

“OOOHHH!!!

YEAHHHH!!!

AAAHHHH!!!

GIVEITTOME!!!

JOHNNNYYY!!!

OHYES!!!

YES!!!

YESSSSS!!!

YYYEEESSS!!!

OOHHHYYYY!!!

YYYYEEESSS!!!

IIIMMMMM!!!

CCCUUMMMM!!!

IINNNGG!!!

UUHHHH!!!”

I came hard too yelling,

“OOOHHH!!!

YEAH!!!!!!

BABBBYYYY!!!

HHERE I GOO!!!

AAAHH!!!!!!”

And with each spurt.

“OOHHHH YEAH!!!!!!

OOHHH!!!

YYEAAHHH!!!”

I collapsed on top of Shelby, then rolled her over on top of me.
We were kissing and trying to catch our breath when we heard muffled moans coming from the closet.

We both looked up to see Jackie Jilling herself to orgasm.
She had her eyes closed and her head back and was shaking it side to side. Her legs were apart and slightly bent and she was leaning kinda forward. She was biting her lip but the moans were still pretty loud.

We hear a loud, “OOOOOHHH!!!

Kind of high pitched, almost a cry.
We saw Jackie’s knees buckle and a VERY wet spot appeared on the front of her sweat pants.
Then she lost her balance and fell backwards among the stuffed animals in the closet.

She was played out on her back breathing very heavily. One hand down her pants and the other up her shirt. Shelby and I couldn’t help but laugh out loud. Jackie turned red and buried her face into the pile of stuffed animals.

She said, “I’m soo embarrassed!!! I didn’t mean to watch you too!! It looked soo hot!!” And she started to cry.

Shelby got up and went to her side and put her arms around her sister, telling her it was ok and not to cry. I saw Shelby kiss Jackie tenderly.

That WASN’T a sisterly kiss.

They’ve obviously done THAT before.

I just watched, getting turned on all over again.

It was SO HOT!!!!!!

They kissed and cuddled then Shelby whispered something into Jackie’s ear. They had a short, whispered conversation.
Giggled like a couple of little girls.

Then Shelby said to me,
“Johnny, could you cover your cock babe?”

Jackie had already seen it, but I said, “Ok.”

So I covered myself up and Shelby grabbed a robe and put it on and took Jackie by the hand and brought her over. Then we sat and talked awhile. About Shelby and me, Jackie and sex.

I found out that the girls had been kissing and fondling each other for years. It started from comforting each other after the times of verbal abuse. Then turned into pretending they were with boys as they got older.

Now Jackie was A MESS!

She had the lowest self worth of the three girls. She was the weakest emotionally. Her hair was always unkempt. She wore clothes only to cover her body.

She was tall and skinny for her age. She had lemon sized tits, (they were nicely shaped and had potential), and she had no ass.

I mean just back of the legs, then back.

NO ASS!!

I found this out by looking at her with and without clothes.
She had “puppy breath” and she smelled funny. Shelby asked me to teach Jackie what to do. I asked how far she wanted me to go and she told me to go all the way if Jackie wanted me to.

I asked, “What about us?
This IS your sister! It’ll be like I’m cheating on you!”

Shelby said, “It’s ok. I’ll share you with my sisters, BUT NO ONE ELSE!!!”

I said, “Are you absolutely sure about this? You get other women involved and it could get ugly real quick!”

Shelby replied, “You trust me?”

Looking into those beautiful, pleading, green eyes. How COULD I resist?!

I could only answer with,
“With my very life!”

She smacked my arm and said,

“Hey, that’s my line!!
Now get your ass over there and make that cock work on my sis!”

“COOL!!!” I replied with a BIG smile.

I brought Jackie next to me and put my arm around her waist.
I looked at her. At first glance you didn’t see that Shelby and Jackie were sisters.
Now Shelby’s younger sister was like a mini Shelby. But that’s for another story.
Jackie had wait length aburn hair and ice blue eyes. Her body form was just straight, except for the two little lumps on her chest. When I looked into her eyes, I saw the real beauty within.

Now it was time to work.

I took her face into my hands and gently kissed her lips. They were nice and soft. I used my tongue to spread her lips, then, she opened her mouth.

There was no action she just opened her mouth like we were practicing artistic respiration. As much as they had kissed, Shelby and Jackie hadn’t French kissed.

So, I teach her how to French kiss. How to roll her tongue and get a pleasant kiss. She was a fast learner and pretty soon she was going at it pretty good.

There was still something amiss. Usually when I kissed Shelby this way I would have a raging hard on. I just had a partial.
I chose it up to Shelby sitting next to us and Jackie’s body odors.

We got going pretty good and I ran my hand under her sweat shirt and felt her little tits. They were firm like two well filled water balloons.

I took her nipples between my fingers and started squeeze and fondling.
She gasped a little. I reached for the hem of her shirt and started to pull it up. I got it half way up when she stopped me.

Shelby told her,
“It’s ok. I want you to learn from him.”

Jackie just let go.

I took off her sweat shirt and started to kiss her down. Lips to chin, to her neck, shoulders and breasts.I tasted, licked and suckled each title.

Jackie tasted funny.

I ran my hand down between her legs and found a that of pussy hair. Jackie put her hand down but Shelby took it off and said, “It’s ok, pay attention, Jackie!”

So I took Jackie’s sweat pants and underwear off. As soon as I did I could smell her pussy. It wasn’t pleasant.

I said, “Jackie, we have work to do!
Come on Shelby!”

I took Shelby and Jackie by the hand and we went to the bathroom.
I found a comb, scissors and razor. Soap, shampoo and conditioner.

Now Irene, the mom, had a big roman tub with a shower chair in it and one of those hand held shower heads. Irene was a large woman due to abuse and a medical condition.

I got the shower nice and hot and we had Jackie sit down.
Shelby washed and conditioned Jackie’s hair.
I went to work with the scissors and razor. I don’t know how much hair a girl is supposed to have downtown, but it seemed to me that Jackie had more than her fair share.

I’m partial, still am to this day, to bald pussies.
I don’t know why. I just like em that way. It makes it nicer to eat.

So I held Jackie’s underarms, pussy and legs.
Now she was clean. We had her brush her teeth and use mouthwash. I told her that guys like girls that smell nice and look decent.
Shelby worked on Jackie’s hair. Shelby combined and curled Jackie’s hair then added just a hint of makeup.

What a DIFFERENCE!!!

A half hour ago, I wouldn’t have even given Jackie a second look, but now. Wow! With the right clothes and some self confidence, she would be ok. She still wouldn’t have much of a shape, but me and Shelby could work on her clothes and help her accent what she did have.

We went back into the bedroom. We were all naked. Shelby looked at Jackie and told her,

“This is how you can make a guy happy, by sucking his cock!
Get down here and do what I do.”

Shelby told Jackie that you start with kissing and then work your way down. Shelby did it first, then, told Jackie to do the same.
Like follow the leader Shelby told her.
Jackie started with kissing me. We got pretty password with it, then they started working their way down.

I was rock hard and was doing all I could to maintain control.

In my upper head I was doing adding and subtracting, multiplication, picturing 80 year old grandma in her string bikini, Gilligans’ Island, the Love Boat, anything to keep from shooting.
I was being done by two girls at once.

WAS THAT COOL OR WHAT!!!

Jackie got down to my cock.
She kissed the tip and then put it into her mouth, then,
Nothing!
The lips were around it but no action. I said to Shelby, “Help her!!”
Shelby led Jackie and Said,
“DO what I do.”

Shelby kissed and licked the head and then down my shake to my balls and gently suckled them, then Jackie followed.

I let out a groan and said,

“Ooohhhhh
yeaaaahhhhhh!!!
THAT’S it Jackie!”
It seemed to give Jackie a little more confidence.

I heard Shelby says, “Be careful Jackie, that thing is loaded with cum and when it goes off,
WATCH OUT!!!”

Jackie stopped and said, “This is fun!”

I replied, “You don’t know just how much.”

As Jackie and Shelby were taking turns with the blowjob I started to Jill Jackie’s clip and fingering her hole. She started to lightly moan.
Jackie was really getting into her cock sucking and I was doing all I could to keep from cumming.

I finally said, “Jackie, yougottastop! beforeIcum!
In…Yyyyour…
Mmmmouth”

Shelby said, “You better stop Jackie.
He’s not kidding!!”

Jackie was just moaning,

“MMMMMMMMMM!!
MMHHHmm!!!
Mmmmmmm!!
Mmmmmhhh!!
mmhmhmmmm!!”

Jackie just grabbed my ass cheats and kept on going.

I held on as long as I could. I was squeezing Shelby’s hand hard and squeezing the bed sheets with my other hand. I gritted my teeth.
I tensed every muscle in my body! I held on as long as I could bear.
I managed to say,

“JJAAAKKIIEEEE!!!”

But Jackie just kept it up.

I breathed out,

“HHHHEERE…

IITTTT…

CCUUMMMSSSSS!!!

AAAAHHHH!!!

I squirted jet after jet into Jackie’s mouth.
She cought and gagged a little but just kept on gulping it down.
She kept it up until I went semi-soft.
While Jackie was blowing me I was working her pussy.
I was Jilling her for all it was worth!

I had up to three fingers in her tight gash, but I was going shallow just under the hood of her gash.
I opened my eyes to see Shelby and Jackie’s lips locked together.
Jackie was bucking against my fingers.
I could feel her trembling and hear her sights of pleasure.
I told Jackie,

“Hold on as long as you can,

HOLD IT GIRL!!!

HOLD IT GIRL!!!

HOLDIT!!!”

I was fingering, she was bucking, Shelby was kissing her hard.

Then Jackie throw her head back opened her mouth and at first nothing came out.
She was panting heavily!!!

That’s when I went down on her and started licking and sucking her clip and tongue fucking her hole.

Then…Sound!!!

A low groan at first building louder and louder,

“OOOHHHH!!!

OHMMYGOODDD!!!

OOOAAAHHH!!!

AAAHHH!!!

IIIMMM!!!

CUMMIIINNGG!!!

OOOH HOH OH OH!!!

HOOOOH!!!

HHa!!

HHHa!!

HHHa!!

HHHa!!

YYYEEAAAHHH!!!”

With that her body convulsed and her orgasm made her body spasm and twitch. Her hands were white on the sheets. She tensed like a spring for about half a minute, then she released as a torrent of pussy juice came out of her gash, she came in waves.

She fell back and just lay there gasping for air and whimpering,

“Ohmygod!!!

OOHHHHmygod!!!

Ohmygod!!!

“That was better than anything I have EVER felt in my LIFE!!!

SO…

SOOOO GOODDD!!!”

Shelby pulled me to her and kissed me passwordately and said,

“Oh, Johnny! That was soooo hot. Thank you for making my sister feel so good.
Now, I want you to show her how to fuck!”

“Ok.” I said.

“But Jackie has to be ready. I told you I won’t do anything you don’t want to do and I’llshow Jackie the same respect.”

When Jackie recovered Shelby started to talk to her.
Jackie thought it would be fun.

I had to ask, “Jackie, Where did you learn to suck cock and swallow cum, it’s like you’ve done it for years.”

She replied, “You’re the first!
I was feeling so good with you rubbing me I didn’t want to stop!
So when you went, I had no choice but to swallow!
You tasted soo good!”

“WOW!! Thanks.” I replied.
Do you want to go to the next step, fucking?
I should say ‘love making.’ There IS a difference.”

Jackie said. “I’d like to do that,
Shelby? Would it would be ok for me to fuck Johnny?”

Shelby said, “Sure, It’ll be so much fun.”

I said, “You know Jackie, it hurts the first time, so you HAVE to be able to relax when it first goes in. After the first time, it’s not so bad.”

Then Shelby said, “That’s right and then you have to practice to get it right. It gets better each time.”

Jackie said, “Ok, what do I have to do?”

I said, “First, get you wet, then get me hard, then we do it!”

Shelby and me started working on Jackie. Kissing her, fondling her, squeeze her nipples. I started kissing the inside of Jackie’s thigh and Shelby started on the other.
We met at Jackie’s pussy and each took turns licking and sucking her clip.

I showed Shelby how to roll her tongue and tongue fuck Jackie. Jackie was moaning and bucking. She was now sopping wet.

I said, “Jackie, sweetheart.
Are you ready to become a woman?”

With a dreamy look on her face she just said,
“K,” and nodded.

I laid down on the bed and had Jackie straddle me.
I told her to lift herself with her legs and then to hold her pussy lips open. I put my hands on her waist to guide her and Shelby pointed my cock to Jackie’s entrance.

She was soaking wet. Pussy juice was dripping on me.
Her gash was soft but very tight.
I held Jackie as she lowered herself down.

I was in up to the head.

Boy! Was this tight! Tighter than Shelby was when we first did it.
I thought to myself, different pussies, different sizes.

I had her raise and lower until her hole adjusted and she gasped when I met her resistance. I was doing a good job of controlling my cum.

Now, the moment of truth. With Jackie impaled on my cock to her hymen I asked,
“Are you sure you want to do this?”

Jackie said, “I’ve never wanted anything more in my life!”

I said “Ok! Just like Shelby and me did it. On the count of three you drop ALL your weight down,
OK?”

Jackie nodded and said, “K.”

I felt like a bull in a rodeo that was about to be ridden and the rider was getting ready for the ride. I guess that about describes it!

I guided her waist down, up 1,
Down, up 2,
Down…
Up…
THREEEE!!!

She let herself down and I pulled her waist down.
I felt the tightest feeling I’ve ever felt envelope my cock.
I felt resistance, rip and pussy on balls!
She was so skinny I could swear I felt her pelvic bone against me, or her cervix. I held her down tight. I was looking right at Jackie’s face when she impaled herself on my cock.

She was looking right at me and when she came down on my cock.
I saw her jaw drop and her eyes went wide. Tears started forming. Every muscle in her body LOCKED!
It was like EVERY ounce of air was taken from her body, then, she dried up!!!

(From the pain I guessed)

Like all the liquid was sucked from her body!
She was trying to breathe or say something but nothing would come out.
This all happened in about two seconds!

Then it started.
It was a little wine that got louder as her breath come back.
It was,

“AAAHHH!!!

OOWWWEEEEE!!!!!!

OWIE!
OWOIE!!
OWIE!!!
TAKEITOUT!!!
TAKEITOUT!!!
ITHURRTS…PLEEEEESE!!
TAKEITOUT!!
OOWWIIIEEEEE!!!”

The sound went from low cry and got louder.
Like an old siren winding up!! It was the wail of a little girl who just smoked her finger.

Both Shelby and me were telling her to relax and that I couldn’t take it out if my life depended on it, even if her mom walked in on us right now.
Her pussy was like a vise on my cock!!
We’re stuck like two dogs fucking until she relaxes.

Looking back, it was kinda funny!

Jackie just put her hands on either side of my chest and hung her head and just waited and sobbed. Her auburn hair ticking my chest as her tears ran down her face and onto my chest.
Poor thing was rEally crying in pain. At the time I felt really bad for hurting her so. But there was NOTHING I could do until she relaxed.

We managed to get her calmed down. I told her to sit up a bit so I could Jill her off some and maybe get some moisture back down there.

Shelby kept kissing Jackie and wiping her tears. I guess because of all the communication my urge to cum subsided.
I wished for a moment that I had cum just to get some lube back down there.
It was SOO fucking tight and it was dry skin to dry skin hurting!!

After about what seemed like forever, she started to relax a little more and started to get some moisture down there.

The Jilling helped.

I then told Jackie to lean back and hold herself up with her arms behind her. This allowed more penetration and better access to her clip. She FINALLY stopped crying and Shelby wiped her tears.
Actually, Shelby teared up abit herself.

Jackie relaxed some more.

In this position I could see some blood leaking out along with some pussy juice. I finally asked Jackie if she was ok. She just nodded (she finally stopped sobbing). As I started to ease myself back and forth, I asked her if she wanted me to pull out.
Jackie just started rocking herself.

THANK GOD her juices started flowing again!!

Now she was getting the idea.
She was starting to moan in pleasure pain.
Saying, “Yeah, NOW it feels good,
Oh yeah!!!
OOhhhhyeah!!!

(And with each trust)

YES…
YES…
YES…

OOOHHH!!!”

I pulled her down to me and rolled her over. I saw Shelby just Jillin’ the HELL out of herself, singing and moaning. I guess because of all the crying and communication I was lasting a good while and going at it real good.

I hooked my arms under Jackie’s knees and spread her open.
She resembled a big M. This opened her more!
I just started thrusting and she was meeting my thrusts.
We were both going.

“YES!!!
YES!!!
YES!!!”

I started first,
“OOOHHHHH!!!

IIIMMMM!!!

CCUMMIINNGG!!!

UUGGGGHH!!!”

Jackie yelled,
“MMMEEE TTOOOO!!!
AAAHHEEEE!!!”

Then Shelby let go,

“AH!!!
AH!!!
AH!!!
AHA!!
AHA!!!!!!!!!
AHAAAA!!!
YYYEEAHHHH!!!”

I saw Shelby squirt.

I squirted buckets into Jackie and Jackie squirted buckets herself!
My cum, her pussy juice and a little blood mixed in oozed from her tight overfilled cunt.
MY GOD we made a mess!!!

What an afternoon.

After we recovered, we all showed together and Shelby assured me that I now had two women to satisfy.

I just said. “Whatever you want, babe.”

WOW!!!!!!!!!!!!!!!!

My little head told my big head,
“Brain?
Yeah penis here!
You know, Shelby DOES have another sister!!!”

Who knows?
Stay tuned.
Damn cum on the keyboard again.
END??????