Ron Ch. 06: With Courtney and Jenni

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Ron and Courtney are joined by David and Jennifer and two more.
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Part 6 of the 11 part series

Updated 06/07/2023
Created 03/22/2016
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Since he was 12 David Whipple had kept a journal of each day's activities. He sometimes missed days, as much as two weeks, and sometimes filled in nothing but a date with no content, but he often filled in gaps and always kept it up. He had filled almost two dozen composition books and a couple of thicker hard bound blank books he had received as gifts.

Extract from Journal of David Whipple

Sunday Evening

So much sex. Such a brief time. Eight girls. Sally said "women" and surely Marlene Malone was a woman as well as Eva and Dahlia. Hard to think of the girls I went to high school with as women tho. And all within the last three days.

What girls! The absolute best looking girl in the entire high school, Jennifer Young. Every guy I know lusted after her. And I got a whole evening with her. And she wanted me. And then a foursome with her and Courtney Summers and a sixsome (is that a word) with a couple of other cheerleaders. I wrote about her back in Junior year. Thought she was a freshman. Lusted after her too. Smallish, looked young but an early bloomer kind of young. Both Jennifer and Courtney were cheerleaders and ran with a fast crowd. Always rumors about one or the other fucking some guy. Never one of the nerds though. Eddie Keegan once claimed he had fucked Courtney but he was a well known liar.

I had seen a couple sexted pics of each of them. There were supposed to be some full blown sex videos. Never looked on line hard enough to find them. Didn't know any of the right guys to have them shown to me. But who needs pics or videos. Anyway Ron has plenty of video on his camera. Part of it I shot myself, complete with close-ups of all the girls vulva. And I've actually fucked them. Not just the few minutes of genital contact from the party but actual full on sex with "O" boy! Ate 'em both out. Both sucked me off too.

Maybe I'll describe the party later but since I'm on the topic of the girls. There was also Sarah Malone and her mom, Marlene. Sarah's another cheerleader from school. Really cute, short, voluptuous and totally built. Her mom is just an older version. Ron says they strip at a nudie place up the freeway. I'll have to check it out. Sally (yeah, THE Sally) says Sarah is her good friend.

Kate O'Reilly is also from school. She's a cute girl. I remember her from a couple of classes as real shy but sure wasn't shy at the party, Ron has taken a shine to her.

That leaves Eva and Dahlia. Hooter's girls. Need I say more?

So Ron, a virgin only a week ago, gets every one of the girls numbers and makes a date with Courtney. He could hardly talk to girls a week ago. And Jennifer invites herself along. Says she came to keep me company while Ron is out with Courtney. That's what I mean when I said she wanted me.

Company is an understatement. No sooner than they are out the door and she starts stroking at my penis! Asks if I have any porno. On my computer I tell her. I hook up the HDMI and she takes the mouse, pushing me on the couch. I have maybe a hundred free clips and things from the internet and she rummages through them. Settles on one that starts with a girl pulling down a guy's pants and sucking on his penis.

Before I know it she's doing the same to me! I gotta rub her crotch and she takes my hand and shoves it inside her panties so I can feel her skin and hair and even push my finger inside her. I find her G spot and rub that with my thumb at her clit. Well she leaves of her sucking and pulls her pants off. We're both naked from the waist down. I don't like that and pull her top up. She cooperates and lets me unhook her bra. God she has great breasts! They feel nice and soft but firm too with hard nipples. She lets me suck 'em like I was a baby. And she strokes my penis all the time.

I think what the hell and go down to taste her vagina. Sally tastes real fishy like but Jennifer is kind of soapy a little astringent and flowery like maybe she's put on a lot of perfume or something. Also there's a sour flavor. I love it! Use my finger to get her excited and more sour flavor flows out. Licking at her clit she comes like an out of tune motor that needs oil. Squealing and vibrating. I just lap up the juice and keep on working her cunt.

When she calms down she attacked me. Jumps on top. Pulls off my shirt. Pushes me on my back. Next thing I know she's got my penis inside her and she's bouncing on me like I'm a trampoline.

Before I come, she's off me and runs upstairs. I chase after her into my parent's bedroom. She ignores my objections and pulls me on top of her. I know she wants me inside her and I oblige. Anyway, I'm pumping into her. Then she's on top and riding me. Then I'm on top pumping away. Then she's sucking me. Then doggy style. Then we're 69. Then I'm pumping inside her. Never seems to me that either of us if in charge. One of us decides to change position and we do it. No words exchanged but a lot of moaning and groaning and squealing and laughing.

Never had so much fun as that. She comes a couple of times. In the middle of one of her orgasms while I'm on top her vagina sucks the semen out of me. I'm pretty sure I screamed. It was intense!

She pushes my head to her crotch and tells me to clean her off. It's clear she means with my tongue. She pulls my hips around and cleans me off with her mouth while I do my best between her legs. There's a pool of the stuff on my parent's bedspread. I hope I'll be able to get it out.

We get between the sheets and I fall asleep her back to with my arms around her and my penis in her butt crack.

I keep one hand on a breast and another cupped over her genitals.

Sunday Night

I am startled awake by a loud wail. The sexy body next to me is already awake and listening. I ask her what it is. I really knew the answer. It's Ron and Courtney going at it. We get up and sneak over to the guest bedroom where Ron is staying and watch as Ron fucks the bejeezus out of Courtney. Ron's expensive camera is on a tripod facing them. I can see the red recording light blinking to show it is recording video.

As soon as the two separate, Jennifer rushes in and starts sucking Ron's penis. I took the camera off the tripod and did what I could to capture both vaginal close-ups and full figure shots of the two beauties. Suddenly Ron was inside Jennifer and the two of them were off to the side of the bed fucking. Courtney asked me to fuck her and I didn't wait. She was tied to the bedposts legs spread. Her pussy, with its dangling cherry jewelry, was completely exposed. She was amazingly tight and squealed with laughter as I drove in. I kissed her and her sweet little titties as I fucked.

The bed shook as both Ron and I worked them over. I watched Ron's big dick sliding in and out of Jennifer. Recorded that and my own cock driving in and out of Courtney. I put the camera aside and watched Ron's cock doing Jennifer while feeling my own in Courtney. What a turn on.

Jennifer said we should move to the king sized bed in the master bedroom. Courtney was tied down and Jennifer released her legs. I undid her wrists. Courtney immediately wrapped her legs around me and dug her heels into my butt forcing my penis hard inside. She pulled me to her and told me to stay and keep on fucking.

When you have your penis in the tight fitting, wet vagina of a cute and beautiful girl and you can feel her soft breasts with their hard nipples pushing against your chest because she's hugging you tight and she has her legs wrapped around you and she says to stay and keep fucking what do you do? You stay and keep fucking, that's what you do. Anyway it's what I do. It's what I did, kept fucking.

At some point Jennifer yelled from the master bedroom asking where we were and Courtney yelled back that we were staying put. I pounded her harder than I've ever pounded. Not that I've had a lot of experience at it. She came hard or did a great job of pretending. She rode me to my climax. I hadn't realized I had no condom on until I felt my semen running down my butt crack. She put her dripping pussy over my mouth and I licked up the combined juices. They tasted better than just my semen. There was more of it than I thought I would have in me after having fucked Jennifer.

I was wiped out and fell asleep with her still astride me.

Monday Morning

I was awakened by furry dampness on my face, Jennifer's pussy. Someone was sucking my cock. I knew it had to be Courtney. What else could I do? I licked at the pussy and Jennifer announced I was awake. She got up right away but Courtney impaled herself on my penis and told me it was time for breakfast. Ron was recording the whole thing off to the side. I tried to get Courtney to stay but she jumped off and pulled me out of bed. I will say that having two beautiful, naked girls wake you up does get the blood flowing.

Everybody helped with the breakfast. Jennifer made some great pancakes using a bunch of spices she found. Throughout breakfast the girls jabbered about last night and how they wanted to continue in the hot tub so we went to the hot tub. Ron said that there was room for at least two more and convinced the girls to call up a couple cheerleader friends, Diane and Felicity. Ron had never been like this before.

The two friends arrived wearing shorts over bikinis. Ron and Courtney answered the door naked while I recorded the arrival on Ron's camera. The two girls just stared, especially at Ron's penis. Courtney made some remark about skinny dipping and seeing the rest of us naked they immediately stripped.

There are very few women who are better looking than Jennifer and Courtney has a fabulous body. These two were right up there. In some ways they were identical. Similar heights, kind of tall, maybe 5 foot 8. The same slim figure with a gently tapering waist, slim waist, flat tummy and small, tight butt. They both had round faces, round eyes, dyed black hair and page-boy cuts. They both had shaved pussies, except for a small triangle of trimmed hair pointing at their crotch.

But the similarities ended once the clothes were off. They were almost opposites in breasts and gentiles. Felicity had smaller breasts with huge, puffy aureoles and dimples instead of nipples. Diane's were good sized breasts, which I discovered were soft as marshmallow except for hard tiny aureoles that seemed to be almost all nipple.

Felicity had almost no major labia. Her minor labia seemed large and puffy. Diane had prominent but thin labia that covered her minor labia flaps. Her large clit hood and the clit itself were exposed between them.

Diane's pussy especially fascinated me. I took a long video close-up of it. I handed the camera to Jennifer and jumped in next to Diane in the hot tub. My hand was immediately at her crotch. I thought she'd push it away or say something. But she smiled and pushed against my hand. I pinched her labia and rolled the flexible lips between my thumb and forefinger. Her vagina was amazingly tight. I had trouble getting even one finger inside past what seemed like a small O-ring. I wondered if a cock would even be able to get in. Mine was hard with the desire to try.

As I attempted to get a second finger inside and rubbed my thumb on her huge clit, she grabbed my cock with one hand and my head with the other. She kissed me hard with plenty of tongue while gently stroking my cock. Something about kissing really gets the adrenaline going. She told me my cock was hard as a rock. She made it sound like something fabulous. I only knew it was so anxious to get inside her that it was getting painful.

My second finger managed to slide into her wet cavity and she was soon writhing in orgasm. She made no sound but intensified her kiss and maintained a firm grip on my cock.

When she calmed, she stood and had me sit on the side of the tub. She sucked my cock in her mouth and began expertly stimulating it while massaging my balls. Next to me, Felicity was churning the already bubbling water while sitting on Ron's lap. Jennifer and Courtney recorded the action from the opposite side of the tub. They passed the camera between them. The one without the camera would massage the others breasts or cunt. That did nothing to calm my hard-on. Sometimes they walked around to where the action was for close-ups. They kept shouting encouragement.

I desperately wanted my cock inside the woman working my cock. She kept looking at me with her round, smiling, and shining eyes. I decided and stood. "Come on," I said, taking her hand from my penis.

I grabbed a mattress off a patio chaise and threw it on the lawn. Diane knew what was going on. There was a bowl of condoms from the party on the patio table and she grabbed one. She lay back on the mattress, her legs spread. She handed me the condom and I saw she had also grabbed one of the KY tubes. She jammed it up her tight cunt and squeezed. The gel spread over her crotch. She smiled and giggled slightly as I anxiously fumbled with the condom, finally managing to get it unrolled over me.

I didn't hesitate and drove it into the tight cavity. My fears of it not getting in were unfounded. "Like it?" she asked me. God, yes, I liked it. "Made it slippery for you," she said. She had these smiling, happy eyes. They seemed to shine with even more happiness as I began thrusting in and out. I guess she knows how tight she is and likes the lube. Lucky we had the KY still out. I was reminded that we'd need to do a sweep of the whole house before my parents got home. Even with her vagina filled with gel I felt the way it grasped me and pulled the foreskin, all the skin of my cock and the condom over the hard shaft. I couldn't resist driving hard and fast. She pulled my head to her and kissed like she had done in the spa. She used her breasts to massage my chest. Maybe she was using my chest to massage her breasts. Her hips were driving up into me with as much vigor as I was driving into her. Courtney was filming and kept saying, "harder, faster." I knew I wouldn't last much longer.

Ron tapped me on the shoulder and suggested we trade. I didn't want to give up a tight cunt. Who would? But knew I'd soon explode and I wanted a chance at Felicity. So I traded. Like Diane, Felicity lay on her back, legs spread. Her labia were spread to each side like butterfly wings, a dark, round hole between. I guessed it was left by Ron's big cock. I thought I could see her cervix inside. My cock needed a rest much as it wanted inside that hole. Anyway, I started by eating her out. I should get a will power award. I found I could get almost my whole hand into her. Another difference between the two. Her vagina was shallow but stretched as deep as I could push in.

I got up and drove my cock inside her. She might not have been as tight but fucking her was great. Easier on the cock and her smooth slippery vagina was perfect for a leisurely fuck.

Next to me I heard Diane telling Ron to put plenty of lube on "that huge thing." She told him, "slow but steady, push hard." Then she let out a tiny squeal of joy. I guessed that was when his cock got inside.

Jennifer sat on Felicity's face while I was working her crotch and began presenting her breasts to me to lick or suck.

At one point one of the girls said something and all agreed. They had me lay on my back and began what was almost a choreographed routine. They must have done it before it was so regular and seemingly rehearsed. One of them would have my cock inside her, one had her cunt on my face and the others had their cunts at each hand. The one on the cock would lead this raunchy cheer as she bounced to the rhythm. I happily licked and fingered at the others.Once the chant was over, they would change places and do the chant again. Something like:

"Get him hard get him hard, get him hard, girl,

"Fuck that cock, fuck that cock, fuck that cock, girl"

"Fuck it slow, fuck it fast, fuck it til he comes, girl"

You get the picture.

Ron video'd it and then they did the same to Ron while I ran the camera. Watching Diane's tight cunt on Ron's big tool made quite a picture. It almost seemed like his cock was pulling her vagina inside out as she came up. The cock didn't slide all the way out, some of her vaginal wall still clung to him and was pulled out with it.

The girls took complete charge. They knelt in a row and presented their rears to us and said, "What are you waiting for guys, doggy style."

We didn't hesitate and as we fucked them they did more chants, like:

"Fuck us guys, fuck us guys, fuck us til we come."

"Jam it in guys, jam it in, jam it in and out."

And , "That was good, that was good, now its time to SWITCH." was the cue for Ron and I to move to a different girl.

They had a contest. Ron and I lay on our backs and two girls sat on our cocks. One of the others ran the camera and the fourth timed as the girls on our cocks rode us furiously. "Time's up" and they changed positions. The winner was the one who could get one of us to come. Diane won, getting Ron off after a couple of rounds. They continued until I came into Diane myself. The girls were laughing and complaining that Diane always won. I'm not surprised. No guy could last for long inside that tight pussy.

All of us got in the hot tub to wash off.

As I played around with their genitals I asked if they'd done that before. Jennifer winked, Felicity smiled knowingly. Courtney was next to me and squeezed my cock more tightly.

We got out of the tub and lounged around naked on the patio. Well, not exactly lounged. Not really possible to lounge with that naked and beautiful feminine flesh. Especially when they would stoke my penis or use it like a popsicle. Especially not when in the middle of some pointless conversation they'd just hop on and bounce a few times.

Ron started blatantly fucking them and I followed suit. They laughed and encouraged us. Playfully fighting to get one of our cocks.

I fucked Diane to climax again and Ron did them all. The girls left around 1 or 2 in the afternoon leaving Ron and me to clean up the scattered used condoms and packaging. I worried a bit about the neighbors but it had been worth it. What the neighbors saw, they saw.

Ron got Diane and Felicity's numbers. He's turning into a real Don Juan despite (or because of) his youthful appearance.

End Journal entry

Ron's Decision

David counted the pages. Probably his longest journal entry except maybe some long winded boring ones from middle school times.

Ron had been watching David while he was writing and picked up the journal to read when he was done. "Very nice. Better be sure your folks don't see this."

"I don't think they will be looking. There are several explicit pages from sex with Sally. I never got into any trouble over those. But if Matthew or Kimberly, [his brother and sister], ever see it there may be hell to pay. Only three days 'til everyone returns and you'll be heading home."

"Not planning to."

"What?"

"I think I'll stay here and go to your local community college rather than go back home. That is if your parents will have me."

"Oh they'd love to have you. But, really? Why?"

It only took one look from Ron to convey the answer.

"Oh, right, Kate."

"And Jennifer, and Courtney, and Eva, Diane, and ..."

"Okay, I get it."

After his parents returned from their cruise, Ron had only two days before they would be going home. When his mother asked whether he had started packing he told her he didn't want to go back with them and preferred to stay behind. He wanted to attend the local community college college and, if they would let him, stay with his aunt and uncle. His parents quizzed him about the reason and he hemmed and hawed, giving less than adequate answers, all the while thinking about how he should have been prepared for those questions. His mother, being like many mothers, quickly discerned what he was covering. "A girl! You've met a girl?"

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