Jenny Plays with the Big Girls Ch. 02

This is the second part of my first entry, "Jenny Plays With the Big Girls." I want to thank everyone for their kind words of support and desire for this story's continuation - it has been heartwarming, to say the least. I can only hope that kind of welcome will only continue.

*

"Jimmy," I explained. "It's only for tomorrow, because the game is so soon upon us. If we win tomorrow, we'll have two weeks to find a suitable replacement for the next game and even more time for the remaining games."

"But...but Lori," Jimmy stammered. "You've gotta be crazy. I mean, there's no way this idea of yours will work. There's no way I could wear a girl's swimsuit or even look convincingly like a girl. Everyone will know right off that I'm a boy pretending to be a girl."

"Look shrimp," I said comfortingly. "Don't get all freaked out over this. I'm not going to force you to do this. We girls are only asking you to do this as a favor for us because we know that you are skilled enough as a volleyball player to pull it off. As for the rest, why don't you at least just try the suit on? Julie is your size and was kind enough to bring over some of her things for you to change into. If you don't look as convincing a little girl as we all think you will, then we'll drop the subject and never bring it up again. However, if you look as nice as we think you're going to look, then at least think about helping out our team and your school in it's time of need, OK?"

"Well, OK Lori," Jimmy agreed reluctantly. "But I still think it's a stupid idea that will never work. But for you and the team, I'll give it the old college try."

"That's my girl," I said with a wink. "I'll go in and give you a hand."

Taking the clothes from Julie, I led Jimmy into the bathroom while telling the rest of the girls to wait in the living room for our return. In the bathroom I had Jimmy strip naked.

"What? Naked?" Jimmy cried out. "Sis, you haven't seen me naked in at least ten years!"

"That's because you were a boy, Jenny," I explained. "And so it wasn't proper. Now we're all just sisters here so we have nothing to hide from each other. Besides, I need to apply this depilatory to your skin to get rid of all that ugly hair you've got."

"Did you just call me Jenny?" Jimmy asked.

"Yes I did, sweetheart," I answered. "Look, sit down for a minute, OK?"

Once Jimmy was seated on the lowered lid of the toilet, I continued. "Look here, sis. We've all got to get our heads wrapped around this change we're making here, and pronto, right? You don't want us calling you Jimmy when you're all dressed up in your feminine finery, do you? You'd be discovered for sure, don't you think?"

"Uh, yeah," he muttered blushingly. "I guess I wasn't thinking."

"For that same reason we need to get rid of this hair," I continued. "No normal teenage girl lets her arms and legs get overgrown with follicle growth like you've got. People see this and it just shouts, THAT'S A BOY IN GIRLS CLOTHES! We wouldn't want that now, would we?"

"Gosh no!" Jimmy said, imagining the sight of him in a bikini being chased down the beach by an angry mob of irate townsfolk. "Oh sis, are you sure we can get away with this?"

"Yes Jenny, I'm sure," I assured my brother. "Remember what I said, if it looks like it won't work, if you aren't 100% convinced you won't be discovered when I'm finished with you, then we'll just forget all about it. But remember this, girl. If you agree to this and it works out, it can only help you in the long run. Think of the field experience you'll get by actually playing in a tournament match instead of just a practice scrimmage. The confidence this experience will build in you will only help you later in life when you try out for bigger and better things."

"Thanks Lori," Jimmy said. "Putting things into that kind of perspective makes me feel better about the whole thing now. I think I'm ready to proceed."

"Good girl, Jenny," I said smilingly, giving my new sister a hug. "I knew you had it in you. Now, stand up here and let me lather this cream around your arms, legs and stuff."

I started spreading the depilatory up Jimmy's left leg from his calf to his thigh. Stopping there I did the same to his right leg. Then I covered his back and buttocks, going so far as to slide my finger between the crack that separated his bottom cheeks into two perfect half moons, sexily goosing his tight butt-hole in the process.

"Hey, hey, watch it Lori," Jimmy squealed. "That's kind of sensitive there!"

"Really girl?" Lori teased. "Have you been giving the boys some back-door action already, sweetie?"

"Aw, cut it out, Lori," he said with a deep blush.

"OK sis, I apologize," I said. "I was only joshing with you anyway. Here, now you take some of this cream and rub it over your groin, all over your cock and balls to get rid of the hair there. I'd do it, but I figure you might think I was getting a bit too personal if I grabbed at your private parts like that, being your sister and all. Yeah, like that, just like you were jerking off to me. Oh, I bet that feels nice, doesn't it, boy?"

As Jimmy began jerking himself off using the depilatory cream as a lubricant, he got more and more lost in the erotic sensations of his hand-job and leaned back into my shoulders, his head laying back into the crook between my neck and shoulders. As he did so, I began to gently kiss his cheek and whisper sweet nothings in his ear as I brought my arms around his slim frame and began applying the last of the smelly cream on his arms, underarms, and then finally around his chest and stomach, smoothing and fondling his chest and nipples as if he had real breasts to caress.

"That's it, Jenny girl," I whispered. "Go for it, girl. Be all that you can be. Imagine your tits are as big as mine, Jenny. Don't you wish you had tit's as big as mine? You know, Jenny, if you were a girl, you wouldn't have to try and compete against the boys anymore. You'd have to compete against the girls for the boys' favors. Just imagine being lucky enough to get a ten-inch cock to suck on or, even better, to get one like that shoved deep into your butt-hole like this!"

At that I slammed my middle finger right up my brother's butt-hole, thrusting it in and out as if it were a cock, giving him the greatest pleasure possible. His knees buckled, and suddenly, he came.

"Aaahh! Ohh, sis, I never..." Jimmy moaned. "Gosh, that feels so good! I'm going to shoot! I'm coming! I'm coming so good!"

Suddenly struck by the entire erotic nature of the situation , I couldn't believe how wet I'd become at the notion of turning my brother Jimmy into a girl and not just how, in a singular swoop swoop of fate, I came up with the idea to do it to him but also how, with very little objection or resistance, Jimmy's simple-minded decision to so willingly allow me to feminize him to the nth degree possible now seemed to give me near complete mastery over the fate of my gullible brother's destiny. Thus, my mind was now turning over thousands of lewd, lurid, and quite vivid images as I envisioned untold paths my new sister could be made to walk, being as I was now in a position to force him to go wherever I chose to lead him, er, I mean her. Wild, unchecked visions of Jenny ran through my mind as I imagined, through the use of dildoes and vibrators, sharing her ass with the teammates, passing her around for sexual favors from one girl to another. Then, on some nights, letting their boyfriends get involved as well. These thoughts and more overwhelmed me so much that I reacted without thinking. Before I realized it, I had inserted a second finger into Jimmy's rear passageway and began thrusting both in and out several times. While I raped his butt-hole with my plunging fingers, Jimmy continued to smear his groin with the depilatory cream and jerk himself off with it until he came a second time. Oh god, I'm such a slut, I thought to myself, as I let these fantasies run through my imagination unchecked. Why am I thinking such thoughts? I really do love Jimmy, and he has always been such a nice brother. But damn, this is such a heady feeling, this sense of power that's overtaken me ever since I'd realized the control I now held over Jimmy. Well, I don't care, they're just fancy musings anyway. Nothing will ever come of them, not in real life anyway. Playing these games may be fun to fantasize about, but I would never really do that to my little brother, not for real, no matter how much fun it might seem to be. Still, I need to finish this little game I started with my little chickadee. The depilatory needs to be rinsed off soon anyway.

"So, Jenny," I whispered into Jimmy's ear as he slowly regained his strength. "How does it feel being treated like a girl? It's not all bad, is it? If you agree to wear the clothes like I asked, that is if you agree you look OK in them, we could have fun and games like this lots of times. Wouldn't you like that? Eh?"

"Jeez, Lori," Jimmy complained, rubbing his butt. "You just fucked me up the ass!"

"Yes? So?" I asked, a bit perplexed. "Don't try to tell me you didn't like it?"

"That's not the point, sis," Jimmy went on. "I'm not queer. I don't do things like that."

"I know that, Jenny," I said. "You didn't have your orgasm when I rammed my fingers up your butt because you're gay even if you one day might find out that you are. You had it because you're accepting your girlish state of mind, and are beginning to believe you should be a girl, for the sake of the team."

"Uh, um," Jimmy muttered, completely done in by his sister's twisted logic.

"Don't worry, little girl," I said. "I understand. You are not gay. You are just a horny little boy who will be dressing up like a girl -- a girl who likes a cock up her ass when she's not busy sucking every cock that's offered her and swallowing down all the hot, juicy come into her cute little tummy. See, I know you better than you think, right?"

"Uh, yeah sis," Jimmy said, still too confused to think straight. "I guess, I think."

"Now, Jenny," I said. "Let's get you in the shower and wash off the depilatory cream."

As the cream washed away, the hair went to the drain with the flow of water, leaving a completely hair-free Jimmy standing there. I toweled him dry, instructing him to pat himself down from now on so as not to aggravate his now hairless skin by rubbing it dry like he usually did. Jimmy's hair nearly came to his shoulders so I then feathered his bangs and curled them slightly with my curling iron to give him a quick girlish look. Then I plucked his eyebrows a bit until they were at least passable and applied some light makeup. Then I gave him one of the swimsuits Julie brought over and helped him put it on, again making sure he put his cock between his legs to give him a more feminine front. It was a simple one piece violet, spandex outfit, cut high on his butt and revealing a lot of cheek, but otherwise it was cute, in a traditional sort of way. I had some more, rather exotic and risqué outfits that I really wanted to get my new sister into, but felt that it was a bit too soon to take such a step. Best to start out slowly, I figured.

When I stood him up and turned him to face me, I was amazed and stared in open-mouthed wonder. As much as I thought it could be done, I still could not believe this was my little brother! He, no SHE, was adorable! Taking him to the full-length mirror on the bathroom door, I let him view his image for the first time.

"Well Jenny," I asked. "What do you think?

"Gosh Lori," Jimmy gasped. "Is that really me? I look like someone I'd want to date!"

"That's the real you, girl," I said. So, are you convinced yet that you can pull this off? Do you want to give it a try now, for the good of the team and our school?"

"Gee, sis," He said. "If you can make me look this convincing all the time, then not only for the good of the team and the school, but for the experience and confidence I can get from doing this, I'll agree to go ahead and play for you guys. And not just this one game, but if you'll have me, I'd like to play until you guys get disqualified, or you win the whole kitten-caboodle!"

"Oh Jenny," I said, throwing my arms around my new sister in a grateful hug. "You don't know how happy you've made me today. Now let's go and tell everyone else the good news. Plus I'm sure they want to see how great you turned out!"

The rich violet outfit contrasted well with his sun-bleached blond hair, dark blue eyes and tanned skin coloring as together we walked back to the living room. Coming through the doorway, all three of the awaiting girls gasped in awe, jumping up to greet us.

"Welcome to the team, Jenny," Denise blurted out, while running her hands over the material of the suit where it hugged into the curves of Jimmy's body.

"Ditto, chickie," Julie added, pulling teasingly on his nipples. "You look better in my suit than I ever did. I'm jealous!"

"Don't listen to her, Jenny," Cindi said as she patted and caressed Jimmy's ass, pulling his suit even higher on his cheeks, causing Jimmy to wince slightly even as she managed to slide the band into his ass crack, thong-style. "She's just worried that you're going to take all her boyfriends away from her. But don't worry, we'll make sure there's plenty to go around, won't we girls?"

Jimmy couldn't help but blush at all the attention he was receiving from the girls. He had only just started developing an interest in the opposite sex in his senior year of high school, and had only had one girlfriend in his brief foray into the great unknown. They had only had one date which had not gone too well, as he had sexually peaked long before he'd wanted to. She had ridiculed him for his lack of sexual prowess and word soon spread until it was all over school. Thus it was a major reason why he decided to travel 3000 miles to go State, in California, the College his sister went to, in an attempt to make sure he was far enough away from any school his high school mates might choose.

Now, here he was being fondled, caressed, almost literally swooned over by a bunch of College girls, and some of them sophomores and juniors, all because he was dressed up like one of them. A guy could get used to this, Jimmy began thinking. All that wasted time and effort I went through trying to impress the girls back home with my masculine bravado. Now it seems all I ever had to do was put on some of their clothes and I could have had them eating out of my hand! Jeez, go figure!

"OK girls," I announced. "Enough of this love fest. I think now that Jenny's here to stay, we should go out and celebrate her new found femininity while also celebrate her agreeing to play on our team. Who's up for pizza and a movie?"

All the girls agreed wholeheartedly to the notion of a night out on the town, but Jimmy balked a bit. It was one thing to dress up like a girl in their sorority, figuring to get back into his own clothes now and head back now to his own place, but to go out in public like one of the girls was way too scary, and he just wasn't ready for that.

"Uh, Lori," He said. "I figured I'd just head on back to my place now. I can come back tomorrow before the match to get ready..."

"Look Jenny," I told him, before he could get any further. "You're going to have to be seen in public eventually. We'll be playing our next tournament game tomorrow, and anyone just watching from the sidelines will see you playing there. Going out with us tonight, letting others see you as the petite, fragile feminine creature you have become, will give you the practice you need to learn how to act and walk like a girl and go a long ways to help you build confidence in your new persona, allowing you to feel stronger and less nervous in the pretty girly clothes you wear with each passing day. Besides, girl, from now on, you're a member of out Sorority. You're a Lambda Lambda Psi chick for the rest of your college days, honey."

"Lori!" Jimmy replied shamefacedly. "You've gotta be kidding! I mean, well, I guess I really wasn't thinking everything through here. Yes, you're right in that I really do need the practice to get into the right frame of mind for this whole volleyball thing to work. I mean, OK, I can't just put a girl's bathing suit or dress on and leave it at that, expecting everything to fall into place, and "POOF" I'm a girl, or at least girl-like. I imagine I will still walk and talk like a boy and do other things like a boy that I'm going to have to hide or change in order to further develop my masquerade. OK, I'll go with you girls and do whatever you want me to in order to work on so that I might become as girlish as I need to so no one discovers I'm a boy in girl's clothes. But I can't just join your Sorority like that. There are rules and regulations. And just because you put me in girl's clothes doesn't negate the fact that I'm still a boy, and boy's just can't up and join sororities!"

"That's what I wanted to hear, girl," I said, giving my little brother a hug. "And about joining the Sorority? Don't worry about a thing, dearie. I have a friend in the Registrar's office who owes me a favor. Pretty soon nobody will ever remember you were ever a boy. Now, let's get you dressed for a night out with the girls."