Juicy Jolie 01

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Juicy secretly dates Ben, but can't hold her feelings in.
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Juicy Jolie 01

My story doesn't start during the summer of 2020 when everything was basically locked down, but it was the kick off, or maybe I should say the reveal of my fem persona Jolie. And I want to say right up front that I'm not slamming any of the promoters who tried very hard to provide people with different forms of entertainment venues.

Hi, my real name is Joel, which led me to chose my fem name as Jolie. The Juicy nickname came from my early days when I had a "that's juicy" catch phrase. I still say that from time to time, but not as often as I did as I grew through my teen years. In other words, don't put it in your head that anyone calls me Juicy because my thighs are all juicy looking and stuff. LOL, I'm quite the opposite actually.

Getting back to that fateful summer almost two years, here is how that went.

OMFG, it was the most boring summer ever, right? Enter stage right, a handful of promoters who had good intentions and opened up a couple of pop-up or makeshift Drive-In Movie Theaters on empty property lots on the north side of Middleton. Great ideas, but the summer of 2020 didn't go so well. I think we went twice and it just wasn't worth it.

Well, fast forward a year and add a few local News cast interviews where the promoters admitted to all of their shortcomings and their promises of a better 2021 movie viewing season and they we were, LOL, sucked in by a few simple TV interviews!

So, the gang decided to give it a try late last spring and we found it to be much better, but there were still many shortcomings. The guys were about to give up on it, LOL, again. Now, I looked at things a little differently. I accepted the restroom issues (yuck) and I accepted that the concession stand was in the backseat of your car (yummy) with whatever you bought from the "Stop & Rob" convenience store, but it was harder to accept the selection of movies. Nothing really caught my attention, but I was as stir crazy as everyone else, so when Ben called and asked if I wanted to go on a beautiful May evening, I accepted.

It was a Friday night and it was when I developed a second catch phrase. During the first hour of the movie, I must have said "hush and watch the movie" one hundred times. I probably could have given poor ole Ben more advance notice, but I didn't. When he pulled into my driveway, I popped out of the front door dressed as Jolie and acted like he had witnessed that side of my life one hundred times before. LOL, poor Ben, maybe! Oh, and I suppose it's fair to say that my catch phrase started out as "hush and drive" before it became "hush and watch the movie" because Ben couldn't gawk, talk and drive at the same time.

But I think he liked or at least appreciated the Denim skirt that I wore, not to mention my dark hair in a ponytail. I appreciated that he chose a parking spot closer to the tree line because it secured one side of his SUV from prying eyes as it was my first exposure as Jolie. Besides, at that time last spring, my facial makeup skills were far from acceptable if I tried anything other than charcoal or satin black.

Unfortunately, time was on Ben's side. It was the 30 minutes between parking and the start of the movie that I didn't think about and I had to engage with him.

"Look Ben, nobody is going to catch us, so just relax. Besides, my reputation of being the "funny one" is in your favor, right? And you honestly didn't know that I was going to, well, dress in drag for our movie date, so your innocence is secure."

"Oh no Juicy, don't you dare call this a movie date! You just sit way over there and don't draw attention to us. Um, I always thought that legs had more of a shine to them when they are wrapped in nylons."

"Hmmm, I'll be sure to wear nylons next time then, now hush and watch the movie."

Hey, I didn't make a fuss or stir the pot. I sat on my side of his SUV and pretended to enjoy the movie that I wasn't enjoying. I mean, I don't think that Hollywood and I are on the page, but I wanted Ben to get past his mental issues and turn his own page. And that didn't seem to be happening, so I opened the SUV door, traded my spot for the backseat and started to dig around inside of the snacks that he had purchased. OMG, it took him almost 15 minutes to grunt and realize that I wasn't coming back to the front seat anytime soon. It was funny to listen to him grunt and groan as he swung his front door open and join me in the back.

"Candy bar or cream filled cakes?"

"Cupcakes! Just hand them to me from way over there."

"Alright. So, for next time, would you prefer flesh tone or nude tone nylons or would the sheer black style be more of your taste?"

"Hah, your brain is all juicy if you think we're doing this again, Juicy! Do you realize what will happen if our friends find out about this?"

"Are you going to tell anyone? And you can call me Jolie if you want to."

"Hell no, I'm not telling anyone about this and I think I'll stick with Juicy for now. Maybe we should call it a night and leave before we end up like that couple over there."

Again, I wasn't interested in shaking up the pot, so I handed him a napkin to wipe the chocolate cake from his mouth and pointed towards the makeshift exit. I felt that my first outing went alright and I was hoping to be forced to come up with another catch phrase for the ride home, but it was pretty silent. But at least he didn't leave me standing on the side of the road.

"Alright Ben, I can't say that I enjoyed the movie, but I did enjoy being with you as Jolie or as my fem Juicy character because you seem to prefer that. So, good night?"

"Ugh, I'm not mad, but I'm not happy either! Maybe we can do this again, but we don't tell anyone!"

And that was that. I left him with a few parting comments trying to let him know that he could post on Chang that he went out on a movie date without naming names and that I would never put him in a situation that he felt all that uncomfortable in meaning that no, I was telling anyone about our date. And notice that I'm not saying anything about what may or may not have been going on in his pants. It was dark and I didn't look, so I didn't know anything about that.

LOL, his parting comment was that I should wear shinny flesh tone pantyhose next time and I made it clear to him that pantyhose had a place, a time and a purpose, but they were like wearing a suit of armor. I didn't say anything, but I assumed that he would appreciate a nude tone.

Well, not much happened for the next two weeks. I mean, there were the normal back and forth texting going on, but nothing about the next drive-in movie night. And best of all, nothing from anyone else, so Ben did keep his mouth shut.

And then, about a week later, I gave Ben the business! I mean, he finally suggested one more try at the drive-in, but it was a late request, so I gave him the business about how important advance notice is for a part time cross dresser. Up to that point, I hadn't had enough practice yet to just "whip out" a decent Jolie at the drop of a dime. I mean, maybe a trashy Juicy, but not a nice Jolie. LOL, he said that it was dark at the drive-in and that a trashy Juicy would be fine. I frowned and told him to take his time at the convenience store and that I would be ready just before sundown. I mean, guys, right? They must think that people just walk around the house in nylons or fishnets.

Well, he got trashy Juicy because I just so happened to be prancing around in fishnets and all I had to do was to slip on a Denim mini skirt, pull my hair back and find a logo pullover that I had laid out on the bed. I know if asked for shinny nylons, but hey, give a CD advance warning, right?

Anyways, as the sun was going down and I knew he would be in my driveway soon, I knew two things. One, hey, I wasn't all that mad about trashy Juicy, which I labelled as goth Juicy in my head and two, oh snap, I was going to have to let him ask questions or talk about it or something, right? I mean, LOL, I'm trashy, not mean!

Hmmm, the first thing I noticed was that there was a folded blanket in the center of the backseat. Hmmm, right?

"Onward Ben to another terrible movie. By the way, ah, I know I said it was OK to post stuff, but you should actually get a piece of ass if you're going to post that you got a piece of ass."

"Oh, sure and be the only truthful person on Chang? Yeah, right. Besides, I believe it was you that tagged my post with a row of emojis. Listen, I'm not going to go all bat crazy about this, but just exactly what are you? A sissy? A faggot or what? And I'm not trying to be mean, I'm just confused."

"Oh, I suppose quirky or queer is long behind me and my cross dressing is sort of new, so maybe a CD in training? By the way, if you think we need that blanket in back, well, then you're the faggot."

"Ah, well, I didn't expect, ah, hey, I don't know how that new blanket got back there. Oh, hey, let's talk about how you look like we could go to Club Deep Star after the movie."

"Hah, says the guy who has a lot to learn about telling his date that she looks nice and who is also the same guy who has never been to Club Deep Star. I mean, the fishnets fit in with that, but I doubt if we're cool enough to even get into the parking lot. And I was only teasing you about the blanket."

"Ah, alright, well, maybe we should snack on something, you know, from the snack bag in the back seat."

"OMG, seriously Ben, practice in the mirror."

Well, my reaction seemed natural enough as I opened the door and jumped into the back, but he really had me thinking about hanging out with the cool kids over at the underground club. I mean, that would be cool as hell, even if we never made it through the entrance line. Which, as I understand it, is a place to be seen. Hah, I knew immediately that my clothing choices and makeup skills were about to get an upgrade.

And apparently, I had plenty of time to think about my next goal because I wasn't followed into the back seat. I mean, WTF, right? Also, WTF, why was he starting the engine and looking so nervous?

"Ah, are we leaving? Are you that repulsed all of a sudden? Oh, are we going to Club Deep Star to stand in the waiting line?"

"Shut it. Timmy and Suzie are parked just behind us! I'm moving a few rows further back, that's all."

"Oh, so ashamed and scared. Alright, but if you ask me to duck, well, I'll roll down the window and wave at them."

LOL, I'm sure that the promoters caught that and I'm sure there will be a new sign up to clearly state that spinning your tires isn't allowed in the parking area, but at least he didn't ask me to hide. But I let it go because everything went back to normal after he parked "way in the back" of the pop-up drive-in.

"Ah, that's better Ben, now which way are we going to play this? Scared, nervous or down right embarrassing? Oh, I suppose your famous "you sit way over there" is still on option too."

"Well, I'm scared that someone is going to recognize my SUV and I'm nervous that they might walk up on us which would be embarrassing, so all three, maybe?"

"Fair enough, for now. What if I respond with even though I am scared to do anything, the Chang community feels that I should get over being nervous and do my best to not embarrass you by pushing your shorts down? I mean, that's what the blanket is for, right?"

"And what if I respond that I'm not really all that nervous or scared and I'm not embarrassed to be out with you, Juicy?"

"Hmmm, I suppose that I would respond that on the count of three, I will spread out the blanket and you get comfortable, you know, way over there. What would you say to that, Ben?"

"Hah, I'd say that it's a small blanket and that you better get way over here."

Fortunately for Ben, he could be a little more truthful with his next posts on Chang. I mean, we didn't go too far because I was scared to snuggle up to my first guy as Juicy, who also happened to be a friend and he was nervous to return the "hand placement on leg" gesture, but he finally did it. And it wasn't all that bad. I mean, the movie was that bad, but he found his comfort zone and began sticking his fingers in the fishnet weaves with a few minutes.

Oh, I prayed to heavens that he didn't think that was sex, but I did gently move my free hand over his crotch and softly patted his boner. Which immediately brought us to the embarrassing part because he launched! Oh, and I mean he launched. LOL, I would remind him later to again, practice in the mirror, but I gave him his space and let him clean up by using the blanket that I hoped to never see again. I mean, seriously, I know it might be an embarrassing question, but it would be nice to know when the last time he, ah, launched, but that would be for another day.

"It's not embarrassing to honestly say that you lost your wad on a movie date, Ben. Just get over it and let's start thinking about the club in Hillsdale."

"Embarrassing doesn't begin to cover it. Geez. I'm so embarrassed. Did you even touch me?"

"See? See what sex does to a guy's mind? I stroked it like I owned it and I even bent over and licked it like a Lolli Pop, stud. That mess you made on your boxers and OMG, all over the blanket and that was only half of it. I swallowed the rest. You know, while your sex crazed guy brain was all weird and stuff. You can post that."

"You mean that my load was too big for your mouth, so you pointed it like a water hose?"

"Well, it was more like I tried to swing around and sit on it while it was squirting, but I wasn't quick enough. I mean, you were going all "I own you" and "sit on it Juicy" and then you started to squirt it everywhere and then you promised to take me to club next weekend so we could pretend to be one of the cool kids. Also, you promised to pay for new fishnets because you trashed these ones."

"Ugh, do you think we're dating?"

"No, not dating because I know you would totally freak out if anyone caught us together. But you liked what just happened, right? Maybe there is such a thing as close friends with a benefit or two. Also, you need to come up with a story for tomorrow because Timmy did walk up on us, but quickly turned away when you started grunting. Oh, and by grunting, I mean you were screaming as you lost it absolutely everywhere, so come up with a story for half of the city."

"So, what's next?"

"Say you liked having your balls emptied and then slip me a $20 for new fishnets."

Guys, right? No matter much better they feel, they just can't talk about it, but it did slip me a $20 and I took advantage of his distraction and pecked him on the cheek.

"Well, what about going to that club in Hillsdale? I don't know much about that or how to dress. Also, um, am I supposed to pick up anything from the pharmacy?"

"Here's what I would suggest. Open your bedroom closet and throw a match in it. And then go to the mall, walk into the store with a flashing skeleton above the door, tell the girl that you're going to Club Deep Star for the first time. And then hand her back the clothes she picks out for you and tell her that you're a newbie and that she needs to dial it down. Also, condoms are not a request, but maybe not unreasonable either."

"Or slip you another $300 and you go to freak store for me?"

"It's not unreasonable for a girlfriend to shop for her boyfriend. And trust me, my homepage will say one beneficial friend shopping for another friend who can't wait for additional benefits."

See? The summer of makeshift drive-in movies during 2021 were so much better than those of the summer of 2020 and the summer was only half over. There were a few more movie dates to follow and Ben loosened up after each drive-in movie date. And it didn't take too long for the word "date" to slip out of his mouth either, not that we were officially dating or anything.

Um, I'm not trying to say anything here, but there was one movie night where things got a little more heated and he fumbled around with the box of condoms. It was nice to know that he wanted a little something, but SOB, I mean, one touch and blast off again, right? I mean, isn't it at least supposed to start at ten and count down to zero?

Anyways, it was a scary moment and neither of us were all that nervous, until embarrassment once again stole the show. Which was actually better for both of us. He didn't have to admit to any gay tendencies and I didn't have to give it up like a T-Girl. I know that explanation is weak, but OMG, it was scary as hell to see such a throbbing member looking for a warm shelter! I mean, damn, it bounced and stuff, you know, just before launch. Also, WTF, right? Besides the ten to zero count down, don't things generally start with a mouth job? I mean, damn Ben, he wanted the gold on the first time!!!!

Anyways, that was the movie summer for us as non-dating friends. But Ben loosened up and caved into the idea of hanging out on the sidewalk in front of Club Deep Star. And I don't mind saying that my selection of his club clothes was on point, just as mine were. I mean, my outfit just oozed sexy, I mean slutty, but his said "SUP? I'm with her" as he tried to get his swagger on. Also, yeah, Ben has very little swagger, but damn, did he look good or what?

And before I go on, please note that I said my outfit oozed sexy. Internally, I do the best that I can, but the book cover is very important for me.

That's where the middle of August comes in. Dear ole shy Ben stepped it up. And no, he wasn't posting or boasting about having a T-Girl girlfriend or anything, but he surprised me in another way just the same. That sneaky SOB showed up to pick me up for our fake trip to the club and SOB, he wasn't alone in the SUV!

As I strutted down the front steps of my Condo, I could clearly see two other heads in the back seat. Hmmm, all without warning, I might add, but it was too late to turn back. Holy Leo and Jake snap, right? Oh, dear ole Ben would pay for that later, believe me, payment was due, but for that night, it was what it was.

Oh, and when I say strutted, I mean in my new fishnets under my black Denim shorts and a crisp new black logo T-shirt that claimed I was from Venus.

And what it turned out to be was a scary moment of what I thought was a medical emergency. The four eye balls in rear seat were in danger of popping out of their sockets, not to mentioned that their jaws were touching the seat.

"Leo, Jake, it's good to see you both. A little surprising, but good. So, shall we go, Ben, the guy who is just full of surprises?"

"Ah, WTF Juicy? Or should I say WTF, Ben? In other words, WTF is happening here?"

"Shut it, Leo and call me Jolie once in a while. Drive Ben. Um, we need some weed to stand in the line. Do you have some hoochie weed sticks Jake?"

"LOL, ah, yeah, I got the sticks, Juicy, I mean Jolie. Say, why don't you ride back here with us? You can, you know, explain things to Leo."

"Hmmm, did you already use a hoochie stick, Jake?"

"Duh, I'm awake, so you know, I took a hoochie stick, I used a hoochie stick or I smoked a hoochie stick. Does that just about cover it all, Jolie? Also, why are you so hoochie tonight? Not that I'm complaining or anything."

"Shut it and don't make trouble tonight as we stand in the line that never moves forward and unzip your jacket. You look like you're going to a dinner party and not to a club where death is statistically possible. Also, I like the word hoochie, just like I like the word woozy, so don't get all woozy tonight either."

"But share my hoochie cigarettes with every stranger?"

"You'll have a chance to get lucky with 1 out of 5 girls. And by lucky, I mean some kissy face action around the side of building. Your odds will increase if you bitch slap Leo out of his trance."

"Hey, I'm alert and listening. But, you know, what do you mean by that?"

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