Jenny Plays with the Big Girls Ch. 07

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Jimmy shines as Jenny struts her stuff - on and off court.
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Part 7 of the 10 part series

Updated 10/19/2022
Created 09/30/2009
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Johnboy9
Johnboy9
434 Followers

The following is chapter 7 in the ongoing saga of our poor, hapless Jimmy's deeper indoctrination into the world of femininity, that lucky guy! :-)

Again, thanks to all who have supported this minor effort with their kind words and votes of support, as well as wishes for this story's continuation. This story is slowly coming to a conclusion, perhaps in 1 or 2 more chapters, so I have started another story you may wish to keep your eyes open for. I hope it is half as well received as "Jenny" has been. Again, I do hope you enjoy this submission as much as I have enjoyed writing it.


Just beyond where Helen was waiting was the parking space into which Julie pulled. This lot was reserved for the players, family, judges and referees of today's game. By the looks of all the cars here, it seemed that a number of family members had come to see the results of this match.

Once out of the vehicle, we all raced up to greet Helen and thank her for not only offering to play for our injured Laurie, but for, once again, deciding to join our sorority.

Helen was immediately taken aback when she spotted Jenny, as she'd never seen her before amongst us girls and thought she was another new pledge.

"My goodness, Lori," she started. "Who is this sweet thing? I don't remember her being being here before. Have you been pledging more recruits that I've been unaware of?"

"Oh my," I said. "I guess it's been awhile since you've been around, Helen. This is my sister, my real sister, Jenny. She'll be a sophomore next year and will be pledging with us then, as well. She's our team mascot. Jenny, I want you to meet Helen Strunk, a new pledge like yourself."

Jenny put out her hand very demurely and said, "I'm very pleased to meet you, Helen. I hope you enjoy being with us at Lambda Lambda Psi. "

"I'm sure I will, Jenny," she said. "I already know most of the girls here already and get along with them famously. But lets not keep gabbing like this now, we can save that for after the game. Let's get some practice in while there's still time."

"Good idea," Cindi said. "I'll grab a ball and meet you all at the practice net."

With that, we all headed to the net as Cindi ran to grab a ball. When she returned, we started to slap the ball around while Jenny stood by watching excitedly.

As expected, Helen's performance in today's practice was as excellent as any I'd remembered seeing in the past, and also, as anticipated, the boys soon gathered around the watching Jenny like bees to honey, all the while feigning an interest in the practice going on around them.

Jenny didn't seem any the wiser and came to accept their camaraderie as they kept asking questions about the game and the girls going about their play.

Even the hands brushing about her shoulders and back seemed only friendly at most as they seemed not to be pushing her into any untoward sexual positions or shenanigans.

Suddenly I noticed Jenny getting red-faced and saw that she was beginning to breathe faster, more irregular. Then I saw that two of the boys had been able to ward off all the others – alpha males, I assumed – and watched as they placed their hands quite possessively on her ass and began rubbing it in nice, long caresses.

Then, as the boy on Jenny's right started caressing her shoulders, I noticed he leaned over to whisper something in her ear.

At the moment he did so, I saw her nearly squeal in surprise. Then I saw that the boy on her left had stopped rubbing her ass and it looked like he was now fucking her ass with his finger as the other boy spoke to her. A moment later I watched the three of them disappear behind the bleachers.

Suddenly I realized this was going too fast too soon. I mean, sure, I was expecting something like this to happen, but in a more controlled atmosphere, and in the presence of her teammates. And after the game, not before it even got started.

Jesus, what kind of slut had I created, anyway? But then, I thought, what kind of sister had I become? Here I was, following them so I could watch because it excited the hell out of me, instead of trying to stop it, even though I knew that was what I should be doing.

I got close enough to hear what was going on, and close enough to intervene in case there was trouble, but far enough away so that I was unseen by those upon whom I was spying.

"OK bitch," the one boy, whom I would later learn was named Bob, insisted, once they reached the shelter of the bleachers. "You come here all by your lonesome, dressed like that? You can only want one thing, bitch!"

"Yeah, girl," the other one, named George, added. "And Bob and I are the ones to give you just what your looking for, ain't that right, Bob?"

"Right as rain, George," Bob sneered. "Right as rain."

"Oh God," Jenny whimpered. "Please don't hurt me. Please don't..."

"Oh crap, bitch," Bob said menacingly. "Don't start pleading! I hate that, I really do!"

"Yeah," George said. "He does, girl, so you'd best listen to him."

"Now," he added, pulling down his swimming trunks. "Why don't you just get down on your knees and take my dick into that nice, hot mouth of yours? And just keep remembering that you do as we say, and nobody will get hurt. All we want is a little sex, a little relief from a long, tiring day, got it?"

"Yeah, bitch," Bob said. "After all, you seemed mighty cooperative just a little while ago."

"OK, OK," Jenny agreed. "If that's all you want, and you promise you won't hurt me, I'll give you what you want."

At that she sank to her knees and took George's slowly hardening cock into her soft hands, watching it slowly get ever harder and longer until it was about eight to nine inches long and two inches in diameter.

Remembering her pleasures from the night before, she then slowly began to pull his cock into her mouth until it reached her gag reflex and then began to swallow, pulling the cock even deeper into her throat.

Finally she felt his cock hairs nestled against her nose. She held it there for a while until she could no longer breathe and finally was forced to let it out or suffocate.

"Sheeeiit!" George shouted excitedly. "I ain't never had any broad deep-throat me before in my life! Bitch, you got talent in your mouth, let me tell you! You could go professional if you ever get a mind to. Hot damn! Now, finish me up!"

With that George pulled Jenny's mouth back onto his cock but this time held on to her face, controlling his in-and-out piston-like fucking motions.

This action excited the both of them as Jenny started to feel a wetness leaking down the insides of her thighs as she grabbed the naked cheeks of George's muscular ass and sucked his cock harder and harder, looking for that baby-making juice she had so recently come to enjoy.

I myself had started to get excited just watching this whole scene play out. Seeing Jenny turn-on to these two guys just totally blew my mind and I started playing with my tits as I stood there taking this all in. At first, I was worried that these guys would hurt her – knife her or worse.

But when I realized their real intentions and remembered the size of the train Jenny had pulled last night, then I was sure that, as long as this remained a sex play thing, Jenny would be alright, maybe in her element, even though the timing was still not just the best. Suddenly, George began crying out.

"Oh shit, girl," he shouted. "Oh god yes, I'm coming. Ah yes, yes! Fuck, I'm shooting! Take it, bitch, swallow it down, slut, drink it, drink it!"

But Jenny had other plans. After drinking some of it, she pulled back, letting his spurting cock slip from her mouth.

She then held it up to her face and began jerking it off, shooting the rest of his jizz onto her face and then, when he was finished, she spread it all around her eyes, nose, chin and mouth, using his cock like a paint brush and her face as though a canvas.

Once he was done, Bob said, "My turn now, slut."

Jenny was so drained, she wasn't even aware that Bob had spoken. She just lay collapsed at George's feet, her thong-covered (or rather, uncovered) ass pointed up at Bob, which was just the way he was wanting it.

Pulling aside the strap that slipped between Jenny's ass cheeks, Bob applied some spit to her ass hole and shocked her to her senses by slipping first one finger then another up Jenny's ass and pumping them in and out.

"No, no," Jenny cried. "What...what?"

"Yeah, bitch," Bob laughed, giving Jenny's ass a playful slap. "That got you motivated again, didn't it?"

Then, Bob spit on his palm and rubbed it onto his cock. Then he pulled his fingers from her ass and placed the head of his cock at the entrance of her ass and pressed.

"Ohhh, Ohhh, that hurts," Jenny cried.

"Look, bitch," Bob said. "Just make like you're taking a dump. Push out, and it won't hurt so much. I won't guarantee no pain, 'cause my cock's bigger than most – even bigger than George's over there, and he's bigger than average.

But once I'm hard, hell, I've got eleven inches here and I'm three inches wide. But you do as I say, and it will help a lot."

Yes, yes, sis, I wanted to shout, as I fingered my wet, dripping pussy, watching Bob attempt to fuck little Jenny's ass. Listed to the dumb ox, he knows what he's talking about. Oh god, is he hung. I wished I'd had him reaming out my cunt. I'd have felt like I'd died and gone to Heaven! Go, sis, go!

"That's it, girl!" Bob said, as his huge rod slipped slowly into Jenny's ass hole. Jenny's face showed the pain of the ages as she winced and grit her teeth while George, inch by excruciating inch, finally sank his cock in until it was completely into Jenny's ass.

"There, girl," Bob said smugly. "It's in."

"It is, isn't it?!" Jenny said, a bit surprisingly, though sure because she felt his hairy groin pressed up against her silky, smooth ass cheeks.

"How does it feel," he asked.

"Ugh," she answered, with a small laugh. "Full!"

"Ready to go for a ride," he asked.

After thinking for a moment, Jenny replied, "Oh hell! As ready as I'll ever be. Give me all eight cylinders, Bob."

"You got it, honey," Bob said with an accompanying laugh. For the first time he used a term of endearment on this girl he had picked up at the volleyball tournament.

Indeed, anyone who could take what he had thrown at this girl deserved his respect, and he was certainly going to show it to her from now on.

At that, Bob reared back, pulling his cock out about seven inches, and then slammed it all the way in again. He repeated this action again and again, pulling Jenny back and forth on the sand, starting to rub her knees raw from the chafing friction.

"Oh, oh god," Jenny began moaning. "Oh, it's great, Oh, I love it! Please, please, fuck me, fuck me harder! Oh yes, yes, god, I love it!"

"God bitch, you're a fantastic fuck," Bob panted out. "I've never had anyone with your endurance, your stamina. Listen, when we're done here, you gotta give me your number.

"I mean, I know the way I came onto you wasn't the nicest way for a guy to meet a chick and all, but I really have come to dig you, and I'd really like to get to know you, if you wouldn't mind. I could really get to like you in a big way, and I can tell you at least like the sex. What do you say, honey?"

"OK, OK, you big, handsome stud, you," Jenny cried out deliriously. "For now, just keep fuckin' the hell out of me. At least wait till I come before you get all sanctimonious on me. Jeez!"

I had to laugh at this sight of almost hillbilly courtship going on not 5 feet in front of my nose, and yet it made me wonder what this would do to Cindi's chances to acquire Jenny as a potential bride.

One thing was certain – our Jenny was growing up and branching out. She was fast becoming a woman in her own right.

"Oh yes,"Bob shouted. "Oh Jenny, oh fuck, I'm coming! I'm coming, Jenny. Please, come with me, honey. Aaahh, I'm shooting."

And the moment Jenny felt Bob's come pouring into her ass, it triggered her own orgasm.

"Yes, yes, Bob," she shouted. "That's it, yes, I'm coming too! Oh god, that's so great a feeling! Oh, it the best – no, honey, you're the best! Oh god, that was the greatest!"

Then they both slumped down to the ground and lay there for two to three minutes. I heard Jenny give Bob her phone number. Not the Sorority number, but the number to his own house.

Just then, the two minute warning whistle sounded, announcing the time for the teams to ready themselves for match play.

It was therefore definitely time to break up this little tete- a-tete, as it was time for us to start and time for Jenny and I to clean up and get the heck out of Dodge.

I left my hiding place, surprising all, and didn't bother trying to explain.

"Come on, Jenny," I said, walking out of my hiding place. "That whistle means the game is about to start, and even though you aren't playing, you are still a representative of the team and need to be on the court.

Me too, for that matter, so let's get cleaned up and out of here. Nice to meet you boys, it's been a pleasure, I assure you."

Getting cleaned up, I pulled a stunned Jenny back to the practice court.

On the way there I asked Jenny why she gave Bob her home number and not the Sorority number where she'll be staying.

"Are you kidding," she said. "Do you think I want to share that hunk with those girls at the sorority? Hell, no!

"At least at my place I'll have him all to myself – Him and any friends he wants to bring over," she added with a twinkling laugh.

Once back to the court, I spoke up to the girls who obviously wondered where the hell Jenny and I had been. Not explaining, I simply said,

"OK, ladies, practice is over. It's time for the real thing now. Remember, girls. This is what we've waited for, the first game of three we need to play and win to be the State Champs.

Remember, play your best, play your hearts out, and, win or lose, we will walk away proud. Never forget, girls, this is, after all, just a game.

"And Cindi, before we go up there, please show Jenny where she's allowed to sit and watch the match as one of our extra teammates, OK?"

"Sure, no problem," Cindi said, a wondering look crossing her brow as she hurriedly led Jenny aside, to the court-side area reserved for injured and extra teammates.

********************

As the two teams took the court, our team, the Battling Bitches won the coin toss and chose to serve. Denise was our server, while Cindi and I played the front line and Julie, Helen and Denise (after she served the ball), played the rear guard.

Jenny was standing on the sidelines, and, as she was a member of the team, she would be kept away from the spectators for the duration of the game, who would be watching from the bleachers.

Our team had done well over the regular season, ending with a 27/3 record, putting us in second place. We were playing the Queen's Guards, a slightly lesser team, who ended their season with a 23/7 record, or fourth place.

I found it amusing, and in a sense, for Helen, a time for retribution, because the girls making up the Queen's Guards were from the Alpha Omicron Pi sorority, her old pledge. Helping us beat them would be a fine parting shot for her to show them just how she really felt about their sorority.

We'd done well against them in the past, and I had no reason not to be able to have the same success against them this time as well. But ever since I'd been able to get my brother into a dress with pasted on tits and a faux-pussy, I have learned to expect the unexpected lately.

Upon the first serve, all of us lobbed the ball back and forth a number of times until a team member from the 'Guards' hit the net and caused an error which gave us a point, the first of the game.

Denise again served, this time nicking the net, letting a player on the other team spike the ball back to us. We were unable to get to it in time. The Guards received no point for that, but they did garner the serve.

This sort of play bandied back and forth most of the game until the referee called a water break after a half hour's play, when our team had a slight lead, 14 to 12. The first team to reach 21 won the match.

"Oh God," I said. "This heat is something!"

"You're not kidding," Denise added, passing me a cold bottle of Gatorade.

"How're you holding up, Helen," Cindi asked. "Everything OK?"

"Yeah," she answered. "Everything's fine here. You guys holding up OK?"

"I guess we're OK," I said. "I just wish this game had been a little more one-sided – in our favor! It's too damn hot to be playing such a close, drawn-out game today."

Just then the ref blew the whistle, calling an end to the time-out. The two teams returned to the court to once again face of in the field of battle.

This time something strange seemed to happen, at least it appeared so to me. The Guards had the serve. Their server slapped the first three volleys to Helen – who missed every one of them.

Now, I'll admit, one of them was so difficult I think even I would have missed it, so I couldn't blame her for that one, and maybe she was still shaking that one off when the next volley came at her, but three in a row was starting to make me a bit nervous, especially when Cindi whispered the same concerns to me.

"Hey, Lori," she said. "What's up with Helen? That's three points she's practically given away!"

"I have no idea," I said. "I was wondering the same thing. Let's give it a couple more plays and see what happens."

I could see Jenny, sitting on the sidelines, frowning with concern as well. We'd all seen Helen play today. She'd been near faultless. In fact, she'd been one of the Guards' best players. As such, these blatant errors made our wariness that much more worrisome.

Their server's next shot was a net ball, thus giving us the serve again. I decided to put Helen to the test. When Denise got the ball, I walked back to her and instructed her to lob the ball to me and do nothing else.

At the serve, she did just that. I hit the ball straight up and back into Helen's zone for her to hit over the net. When she got to it, she spiked it into the ground on our side of the net.

At that point, with the score now 14-16, I realized she had conned me, had conned us all. She was not here to play for us, or even to pledge our sorority, but was here to ruin our game and help her sorority win through deception.

At this point I called for a time out and walked over to the sidelines. There I approached Jenny.

"Jenny," I said. "Helen is trying to make us lose. She never wanted to help us win. I need you now, sis. I need you to take over for Helen and play for us now. Please, Jenny, we need your help."

"But Lori,"Jenny asked. "What about my all-important role of team mascot? I thought you girls really needed me to fill that position for you."

"Oh Jenny," I said, almost in tears now, realizing what I'd actually nearly made of my sweet, dear brother. "God, I'm so very sorry for what I did to you, for what I let the others do to you."

And now I was crying, finally coming to terms with all that I had done to Jenny...no, Jimmy, and even worse, all that I had even planned to continue doing to him, even as I worried about what Mother might say once she found out, even knowing that sometime, someday, she would, indeed, find out.

"Look, Lori" Jenny said reassuringly. "I was only joking, well, sort of. Look, if you're apologizing for putting me into a dress, taking me out on the town and fucking my brains out, among other things, then, after getting me home, doping me up and gluing some tits and a fake pussy on me, please don't.

"Didn't I tell you before that I had a ball when I was doing those things? Look, didn't you just see me take on two guys there behind the bleachers? Did it look like I was complaining then?

Johnboy9
Johnboy9
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