Julia, Ben and Lisa Ch. 09

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We meet Josh and Harry.
15.5k words
4.77
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Part 9 of the 20 part series

Updated 06/09/2023
Created 02/04/2020
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Ch 09: Wednesday

A few quick notes:

1. this is the ninth chapter of a longish story, a novel in many chapters

2. everyone is 18+

3. there is no safe sex here - cause it's a fantasy, not an instruction manual

4. crossdressing and gender bending, not everyone's cuppa tea - be forewarned

We were both quiet and shy the next morning. How do you start after an experience like that?

Julia was up first and had coffee, grapefruit, juice and Cheerios on the table when I went down. I had dressed cautiously, guy shorts over my soiled panties and a boy-tee. Julia wore an oversized Minnesota Vikings shirt that came almost to her knees. Knowing she was probably nude under it gave my cock the first nice jolt of the day. Her messy hair was tied back in a pony tail.

We hugged and 'morninged and began to eat. Her parents had texted success in getting to the Bahamas. My Mom had texted about me needing to be home Friday morning to let in the A/C repair man. Damn. We weren't happy about the Lakers draft. I invited her to a touring company's Evita, but that wouldn't till August. Her college roommate had Instagrammed pictures from Yosemite. She was texting with Alicia, and then with Amanda, saying goodbye before the Spain trip.

Julia put down her phone and looked over at me slurping the grapefruit. "I don't think we should fuck." She got right to the point I guess.

"Oh, aaah, I never thought..."

"Yeah, you did. Me too. Both of us. I mean we thought about it, not saying either of us..."

"I know. It's OK. You don't have to explain."

"But I do. We need to get this out in the open now. I don't want either one of us hurt by this. OK?"

"Yes. OK." I was reluctant to get into it for all sorts of reasons, starting with embarrassment at her knowing how bad I would want it, and ending with me being a jerk for even imagining it. But there would be no stopping her now.

"Well, then, first. We start fucking and where does it end? I mean we fuck in my bedroom when Beth and Roger aren't around. We fuck in your bedroom when Uncle Ed and Aunt Jane aren't around. We fuck in the car when they are, or out in the woods. Like hobos. We fuck and fuck and fuck and where does it end?"

"Ummm, hopefully with even more fucking?" I needed to be a wise guy here to lighten things. It kind of worked. Julia gave me her nice smile.

"Yeah. exactly. And where does that lead us? There's no way our parents aren't going to find out, no way at all. I'm still not sure Mom didn't actually think we were fucking the day she almost caught us. Who knows? They'd find out, maybe in the first day or the first month, but they'd find out. We're not the sorts who would hide it well, are we?"

She never paused here. "Now we've got four parents going berserk. Your family is a mess, mine is a mess, we are a mess. Our Moms fighting, our Dads blaming each other and blaming us. No way a relationship would survive this, no way either of us would survive."

"You're right, I know..."

But she went on, "Then there's what we have now. I love you. You love me. Everyone knows. Everyone approves. Everyone loves us more because of how we love each other. Do you think that would last through a sexual relationship? Not even talking about the others, just us. We're the best friends that could ever be. I can't see us throwing that away. Not for sex, nice as it is. Not when we can both have all the sex we need with other people and still love each other like we always have."

"Well, you can at least..." Feeling a bit sorry for myself I guess.

"No, dipshit. You too. Just need to build up that manly confidence, girly confidence too. You're going to see. I know it."

"OK. Maybe."

"Which brings me to the third point. Bi. You're bi. I'm not. What are we supposed to do? Share a boyfriend? Or I get to sit at home while you're off blowing some hot college guy next year? How could that ever work? I mean I 100% support your thing. I loved, loved, loved watching you suck and cum, love seeing you in panties. But I'm not your girlfriend, not your lover. I'm not sure how I could handle it."

Made me think of Donnie and Dolores, how lucky they were to have each other.

"OK. OK. OK. Let's not beat it to death. Please."

Secretly inside I was pretty flattered. Julia had so many reasons we shouldn't fuck. She must really have thought about it as some sort of weird possibility. Me? Fucking Julia? Her? Fucking me? Incredible. I guess I must have been at least somewhat manly in her eyes.

"Yeah. Sorry. I know. I just needed to get it all out. And please! Please, please know I love you to death and more than anything in this world." She looked over at me seriously and took my hand above the Cheerios bowl. We waited, her rubbing my hand gently. Her eyes were big and became wet. I was choked up too. She loved me so much. I loved her so much. "More than you can imagine... more than anything in the world...anything...except possibly for my new Kate Spade bag, which makes me cum harder than any man ever could."

We had a nice laugh together. I dried my eyes and leaned over to kiss her cheek.

"Does this mean I'll never get to see you nude?" I was feeling cheeky, now it was all being laid out like this.

"Dunno. Could you handle it?" She flashed her wicked grin, her eyes still moist.

"I think I handled it all right last night when your tits were in my face. Do you have any idea how much I wanted to lick and suck that freckle? Fuckin' thing has been driving me crazy ever since you developed boobs. But I didn't."

Julia giggled. "Yes. You were a very good boy right then. I realized right after I did it that my tits were right over your mouth. Must have been a nice view for you. But I was so determined to get that lovely perfume behind your ears. Thanks for not doing it. I might have gone nuts too if you had."

"Now you tell me."

We smiled at each other. "Done?" I asked.

"Done."

I told her about my Friday being kind of ruined cause of he AC man, at least the early part of the day. She told me it was fine, that she could go into the computer lab at school and get some of her summer work done. So that was our plan. And we still had 13 other days. Starting now.

"So what do we do? I mean now," I asked.

"Now?" She looked surprised. "Now? Nothing else has changed. Now you run upstairs and get yourself pretty. You're on your own. Pick out whatever you like." She gave me an ironic look, "I mean what you like of your own things, not mine."

"I'll need help with hair and makeup though."

"Yup. Figured. I'll be up in 20 minutes. You shower in my bathroom, I'll use Mom's. Then you tuck and dress. I want you gorgeous when I get in there. We'll do nails, face and hair. Then I'm taking you out for a ride and maybe a walk. Don't worry, we'll go pretty far away."

"No Charlie this time I hope."

"No Charlie. Just us girls. Maybe do some shopping? You could use another pair of shoes or sandals, maybe another outfit. Me too. Coach needs something pretty if she's gonna keep up with you." She gave me her best smile. "Now go, my lithe lovely lass."

"Yes Sir!" I saluted, and ran upstairs before she could whack me in the butt again.

===========================================

An hour later we were pulling out of the three car garage in Uncle Roger's BMW. I was in the dungaree skirt I'd wanted to wear the day we met Charlie. It came just mid-thigh and I loved how my tanned legs and my butt looked in it. Short and tight enough to show off my best girl-features. Julia made me swap the leather belt for a loopy gold chain of hers that better defined my hips and ass. The skirt had cute brass buttons up the front, right over my pussy space. A soft and feminine polka dot blouse in white and blue tucked in to better define my tits. Julia lent me a strand of faux pearls and matching clip-on earrings that went perfectly.

She even lent me a little clutch bag full of what she called girl-essentials, a comb, some mints, lipstick, a little mirror, and two tampons. Whacked I tell you.

Underneath I wore the blue bra with lace edged blue bikini panties. The blues weren't an exact match but they still looked pretty nice together. Julia had done wonders with my hair, nails and makeup, going just slightly darker this time with the eye-liner.

I was untucked for the drive. Saving it for later when it was needed.

Julia had on a soft purple and white linen Empire dress, just above the knee, that set off her bust perfectly. She wore a gold necklace and earrings set and a gold anklet I found impossibly sexy. Gorgeous, as usual.

As we rolled onto the empty street, Julia stopped and rolled down her window.

"Hey, Mr. Sanders!"

Her ancient neighbor had been out watering the lawn. He looked up, stopped the hose and ambled over to the car window.

It made me a little nervous. I'd met Mr. Sanders a bunch of times at Bettencourt family events and cookouts. Seemed like a nice, friendly and warm guy. But I hadn't known I'd be on stage so quickly.

"Hello there Julia," he said leaning in the driver side window. "How's everything? How're the parents? They get off on that big trip of theirs yet?"

He noticed me and asked, "And who is your friend?"

"Oh, this is Lisa, a girlfriend from college. Mom and Dad just left last night and Lisa is staying over for a while to keep me company."

He looked over at me again and said with a smile, "Well, that is fine. You girls take good care of each other. Yes, take good care of our Julia, Lisa. She's the neighborhood sweetie."

"I sure will, Mr. Sanders," I said doing my first real girl-voice of the day.

He beamed at me with pleasure. "Aah. Good for you. And my, my, my but you two girls look so pretty today. Where are you off to?"

"Oh, just a bit of girl-shopping," Julia said.

Mr. Sanders chuckled. "Women! Why my dear wife Sadie would go through some of those stores like a house-afire. Never enough. Shoes! Hats! Dresses! Scarfs! Scarfs, you know, were her specialty. Anything yellow or bright, anything...but it made her so happy." He paused, looked up to the sky out of my line of sight and seemed to mumble a few words. He came back down, laughed at himself, saying "Now look at me going back again ...I'm just...well, anyway, you two try be good, you hear?" He was grinning ear to ear. "Don't spend all of your Dad's money or we'll never hear the end of it."

"We won't Mr. Sanders. Promise. Thanks and you take care now." Julia gave him her most loving and heartfelt smile. Mr. Sanders had lost his Sadie about two years earlier.

A gardener's truck had pulled up and gave a polite honk to remind us we were blocking the way.

"I'll keep an eye out on the house for you while they're away. You tell 'em I wish them happy holidays when they call. And you girls need anything you come right over to me, hear?"

"We will, Mr. Sanders. Thanks again."

We pulled out and hit the road.

Julia said, "Oh my God, he's such a sweetheart. I just love him to death. You heard him about his Sadie? Where do you find a guy like that?"

I said, "Yeah, true love. It's nice. Nice but sad for him."

"I know. I think he misses her like crazy, poor thing. Now he's the neighborhood oracle. Knows everything about everyone. Says the old biddies who are widowed love to share every story with him. Guess a guy that nice gets hit on even in his 80's." She laughed, glanced over and raised her eyebrows invitingly. "And did you hear him? You two girls look so pretty..."

"Yeah, I heard it and it's nice. He seems like a great guy. Now if only it's that easy to fool some of the guys our age."

She laughed again and said, "Right! Let's go find out."

We drove most of the way with just a playlist on the stereo. We were heading to Franklinville, almost 80 miles down the highway, a small country town that had become popular in the last few years as a tourist and ski site. A new luxury resort, a downtown hotel and a high end mall had come in during that time. In the summer season it wasn't likely to be very crowded.

Julia parked the car and we walked around the historic downtown area, did a little window shopping, not attracting any more attention than what Julia always generated. By then it was approaching 1 p.m. and we headed for an outdoor cafe for lunch.

We both ordered salads with light dressing and iced-tea and sat in the sun.

It was so glorious to be out in the sun as a girl. I was tucked and felt pretty. I stretched my legs out and tilted my face up to work the tan. Course my face was already pretty tanned from the boy work on the fence. But it feels totally different to be in the sun as a girl. I noticed a few pretty girls eyeing me as they walked by the cafe, one or two with looks of appreciation in their eyes. It seemed then that the girls were more interested than their guys, probably appreciating my outfit.

We chatted about this and that. Small things. Girl talk. Amanda got her period just as she was getting on the plane. Yuck! Sally Williams had been expelled from our high school in May for vaping in the girl's room. Did you hear SomeLuck Beezy had a new album out? That sort of thing. So relaxed. So fun to be out with the prettiest girl in the world.

Ten minutes into our salads Julia bumped my arm and whispered, "Those two guys. Over there. They're watching."

I looked out of the corner of my eye. I saw a couple business types who must have been done work for the day, suits on but no ties. Early 30's from their looks. One tall, fair and lean, good looking. The other shorter by a few inches, darker and more muscular.

I was immediately intimidated. The idea of checking out the guys, or that they were checking us out, was sort of unreal. Plus they looked so sophisticated and smart and sharp. Like they knew so much more about the world than I ever would. And like they were rich. I felt dumb and fragile, felt like a target a stronger animal might, or might not, decide to eat.

The guys were laughing and drinking martinis, but definitely keeping an eye on us at the same time. Every once in a while I'd see one of them semi-whisper and sort of indicate in our direction, then smiles and laughs. I think I blushed. I know I squirmed in my seat.

I became more conscious of trying to eat like a girl. Small bites, pauses, frequent use of the napkin trying not to spoil my red lipstick. Julia shifted her seat just a tiny bit in their direction and stretched her long legs towards them. That made me giggle. So this is how it was played? I stretched my legs too and the skirt rose up my thighs. The guys had already had a good angle on me.

Julia whispery asked through the napkin pressed to her lips, "Think they're kinda hot. You? You up for playing?"

"Ummm...not really, I..." I mean why would we push it? We could have fun just like this, being totally girly, letting them look, enjoying that. Plus I was still shaken up by the Charlie fiasco. Not ready for a replay of that.

But Julia doesn't take stage direction all that well. She nodded as if in agreement, then wiggled her eyebrows, stuck out her tongue at me and excused herself to go to the ladies. Another thing I wasn't ready for.

She said, "Watch." She had that Julia gleam in her eye.

What was she getting me into now? As if it was unclear. My tummy gave a little flutter and I shifted my bum again, this time to make sure the tuck was still good.

About a minute after she left the tall one got up and headed in her direction, his drink in hand. The shorter one, not that bad looking himself now that I could see him alone, sat glancing in my direction but would look away when I raised my head. It was sooooo cute, and he looked so manly and strong. But I was nervous being alone at the table.

Julia came back 10 minutes later, trailed by the tall one. She was excited and laughing, "Oh my god, Lisa! Guess who I ran into? I mean really ran into. I turned the wrong way coming out of the ladies room and rammed right into him. And he's like holding this drink and it's like, bam! Splashes all over his suit. I'm such a klutz!"

Julia rolled her eyes for us both, exasperated by her own clumsiness.

"Turns out, and it's like, oh-my-god! Turns out this is my Dad's brother's broker. Uncle Frank's broker! Can you imagine? I, like, wrote down my name on this paper, cause, you know, of course I offered to pay for the cleaning, and he's like, 'Bettencourt?' and I was like 'Yeah' and he knew the name immediately. Cause of Uncle Frank I mean. Can you believe it?"

I looked up. "Oh, wow," trying not to get sucked in too fast. Wishing I had some degree of control over the force of nature that was my cousin.

She turned beaming to him. "Josh, this is Lisa. Lisa, Josh." He reached in with a bright confident smile to shake my hand. I was a bit self-conscious of the size of my hands, but I did the grip and pressure just girly-right and he didn't seem to notice anything out of place. Nice! A rush! He held back as Julia rambled on. "And, oh-my-god Lisa, he's so nice, like won't let me pay for the cleaning or anything and he invited us to his table for a drink with his friend, and I thought...well, if Lisa will, then I will."

Putting me on the spot. Freaking me out.

"Um..well..." But I could feel my little pussy wanting to agree.

Now it was Josh's turn to sell. "Come on Lisa. Meet my friend Harry. He's a riot. Smart as hell too, like maybe a genius. But very chill. You'll like him."

"But we're not 21, we can't..."

"Don't worry about that. We're tight with Brad, the owner. And the cops never hassle these tourist spots about drinking age. I bet half the people here aren't 21 yet. Or we can just get you guys soft drinks. Either way."

So we had to go over then. The guys ordered an expensive bottle of Chablis for us all to share, switching off their martinis. The waitress was a cute girl our age and immediately began the drill of asking for ID. Harry intervened and said, "Brad told us it would be OK," and slipped the girl two $20 bills. She backed off, giving us girls a look of surprise and then a pretty smile.

The guys had placed us in the middle of a rounded corner bench, beautiful hedged flowers behind us, the sun at our backs and the view in front across the lovely patio to the mountains. Was nice, really nice. Harry was on my left, then me, then Julia and then Josh to her right. A sensation of being trapped, strange but nice. And they had decided. Who got which girl. You could tell right away that Josh was the more senior guy.

Turned out they were both from Chicago, down to meet what Josh called his "high end clients". Immediately I'm wondering, how do they know Brad so well if they're from out of town? I'm also practicing inside my soft whispery girl voice to get ready for when I needed to say something. I'm also wondering if my makeup is right and if my breasts look real in the blouse.

Harry turned out to be OK. Quieter than Josh, which was good, but intense looking. He told a few funny jokes, nothing offensive or weird. Silly jokes. Otherwise pretty quiet. Which made it awkward because Josh was monopolizing Julia with semi-private conversation, telling her about his condo in Chicago and his ski vacation in Jackson Hole and how he was about to buy a Porsche.

Harry asked about me. College (yes), year (sticking with sophomore), sorority (not yet, pledge next year), boyfriend (stuttering and coy, off and on), ski (no), tennis (yes, but a lie cause I had to admit to something). Then he asked about golf and I admitted that Julia and I had played (poorly) a few times. So we talked about that and he said we should go together some time, which was nice.

We'd been there for about an hour, now well into the 2nd bottle of Chablis. There were no more problems from the waitress about our drinks. I was afraid of getting sloppy, or too silly. My girl voice was working fine. I was settling in, allowing myself to enjoy the pings and girly feelings.