Julia, Ben and Lisa Ch. 02

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Readers: sorry for the delay. I had a little editing problem.

A few quick notes:

1. this is the second 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

Time for girl clothes. I sat on the swing bench out on our side porch waiting for Julia to pick me up. We both had cars and mine was actually nicer, but somehow it was always her car, with her behind the wheel. Not that I minded. I was so excited about what we were about to do that I was almost panting with anticipation. Girl shopping! For me! With the prettiest girl in the world!

I reminded myself that I needed to tone it down, and began to relax and swing and daydream.

I told you Julia was a knockout. Gorgeous smooth white skin without a single blemish, straight even white teeth, a glorious smile complete with dimples, perfect cheekbones, a lovely, softly rounded chin, arched dark eyebrows, sexy full red lips. Her eyes were some kind of blue-green that went right through you. She had thick jet black hair cut in a dramatic bob ending at her chin. Her boobs were these amazingly shapely upturned C-cups (I’d handled her bras of course), set off by slender arms, a tiny waist, shapely legs and completely flat belly. They looked perfect on her 5 foot 6 frame. I’d seen her tight, pear shaped ass in a bikini often enough to know what perfection was.

Her skin had no blemish, but she did have one lonely soft brown freckle on the inside of her left tit. I lusted to touch or kiss it, so gently, so respectfully, so thankfully, even just once. The bikinis showed that off, and showed off her pretty thigh gap too. Those tiny bathing suit panties could only be worn by a girl who shaved her pussy. She called herself skinny, but the rest of the world saw a perfectly proportioned girl.

I was a little taller, but she’d been right about my weight being no more than 10 pounds over hers. 135 pounds. Me. I was pretty skinny for a guy. No contact sports for this dude, but I was hot stuff in the drama club.

And drama is where my dress up thing had started. As a freshman they’d put a gown on me and declared me the school Julia – no, not my Julia, the other one who got in some trouble with Romeo. Actually Juliet, but close enough for me to think I was playing Julia dress-up.

It wasn’t as weird as it sounds. I’d been a day student then at a fancy boy’s boarding school and our sister school was under a measles quarantine the entire 10 weeks of rehearsal. The one eligible faculty daughter broke her ankle skateboarding on the 2nd day, not to mention she was U-G-L-Y. And the sisters of the students all seemed to live out of state.

Someone had to be Juliet. So it had to be a boy. My voice hadn’t broken then and they knew I had the right body type.

Something about the dresses got to me. How beautiful they were, how lovely they felt and smelled. How soft and sexy. How happy they would make Romeo. How natural it all seemed, how feminine and delightful. Something about the way the moms on the dressing team would primp me, tug at me, tuck me, flatter me, fix my hair and do my makeup. How they would worry over my little fake bosom. How happy they were to teach me to speak as a girl and act as a girl.

I mean it was just drama club. But they all said it: I was beautiful in the role — and I killed.

Naturally, since she was so good looking, Julia had lots of dates and boyfriends. She was never the flirty type, just someone with a normal interest in boys. That was her one life, and I wasn’t part of it. The other life, the one with me and her family and close girlfriends, was different. She was goofy-shy, slightly nerdy, funny as hell, a singer in the school’s acapella group and whip-smart, an A student. Julia had finished her senior year of high school with an average of 104.2%, just .3% points behind the class valedictorian. Goodness sakes, she sang in the church choir too. She could also be passionate and fiery and demanding when she needed to be. She was a good daughter, polite, considerate, warm, loving and fun, and an amazing cousin.

All of this was playing out in my head as I stood waiting to see her beat-up Toyota roll up to my house. As I waited to go shopping for girl clothes.

The prior evening when I got home I alternated between insane fear and thinking this was going to be the hottest thing I’d ever experienced. I’d get one of those steel beam hard-ons, and then I’d panic again. I took out the panties she’d been wearing. Panicked. Tried them on. Looked at my ass in the mirror. Smiled. Tucked the family jewels. Panicked. Tucked the front a bit more to see if I could smooth away the lump. Panicked. Wore the panties to bed and loved them. I didn’t even masturbate because I wanted the panties to Anadolu Yakası Grup Escort stay fresh with her scent for as long as possible. In the middle of the night I woke up with a throbbing dick, stripped off the panties and came twice in about three minutes.

As for girls, I think I was half in love with almost every girl in our class at one time or another. But my love life was pretty blah despite that. I tried to send a vibe to the girls. I asked a few out. They were all nice girls, and we generally had fun, but somehow we never got past a little kissing. It bothered me and it didn’t bother me. I couldn’t really tell which. I figured that it might come together for me in college. I hoped so. Now that I was 18 I was determined to be a bit more aggressive trying to have some kind of love life.

Thinking about girls however sort of had the opposite of the intended effect. I mean I’d look at them, see how cute their outfits were, and end up wondering more about the beautiful clothing and how the girl was wearing it than about the girl herself. I had started doing a bit of dress up. Of course I thought of me as Juliet. I wanted to be as pretty as I had been as Romeo’s lover. I really didn’t feel gay at all, just someone who wanted to be pretty. Or maybe to be pretty plus loved and held as a girl. Just once even. The few times I’d fantasized about guys it was about sucking their dicks — but fantasies about girls far outnumbered that. So, no, not all that gay.

But the cocksucking fantasy was pretty hot. I felt it in the pit of my stomach once I got into touching panties and bras and cute blouses or skirts. I dreamt of looking cute, on my knees, with a thick cock in my mouth, looking up at some hot guy who knew how to control and use my mouth for his pleasure. That I wanted him to know I would suck his dick better than any girl, that I would swallow his cum and be thankful for the opportunity. Which is possibly a little gay.

On my knees. I would be so proud to be there for him, to lap along his upright cock and lick away a cute little bead of precum, to meet his eyes, mine open wide in awe and appreciation, to smile up in submission, to let him know I knew my place, to have him plunge that cock deep in my mouth as I gently cradled his balls, to see if I could take him in my throat, to be fully a girl, soft, sexy and submissive, to be cute for him in a little strappy tee and soft pink panties, to gracefully accept the blast of his hot cum in my mouth, to be filled up with him, to make my tongue a pretty cup for display, to swallow happily, greedily, gratefully, to lick him clean after. To be the girl of his dreams, an eager and obedient cocksucker, to have the other girls envy me.

When I pictured myself as that girl I felt lighter, gigglier, happier and sexier. Content and desired.

Not that I would ever admit this to Julia, or anyone else for that matter. I didn’t have to tell her about every hangnail, or every pimple on my ass. And I didn’t need to tell her about this either.

Where was she?

I’d been outside for 15 minutes waiting. Remembering and fantasizing, but waiting too. Now I panicked. Maybe it was all a big joke. Maybe she never thought I would take it seriously. Maybe she was sitting at home laughing her ass off. The day was only a little warm, but I was definitely starting to perspire. I felt like an idiot.

I shook myself. That’s not Julia. I let the negative thoughts go, and my mind wandered off again.

A few weeks earlier Julia and I had laid on her bed watching Breaking Bad, and when she paused the show to go downstairs to get us drinks, it seemed like the most natural thing in the world just to go over and peek in her lingerie drawer. Just, you know, to see.

And then to touch. And touch some others. To touch the crotch, run my fingers inside along the band, touch where her hips would be, where her pussy or ass would be, touch the cute little bows, and touch her Hello Kitty thong. To lick the kitty.

There were so many, all jumbled together in that drawer. In so many colors and patterns and cuts. Red, blue, black, yellow, peach, cream, white, pink, striped, swirled, paisleyed and polka-dotted, plain, bold, sheer, transparent, logo-ed and cartooned. Pretty bows, lace, silk and soft cotton. Briefs, hipsters, thongs, bikinis, boy-shorts, boxers and g-strings. Each seemed lovelier than the last.

The bras were there too of course, right next to the panties. But for that one night I only had time for the below kind of undies.

Images of Julia with her boyfriends at college, and of their fingers and hands being were mine now were, of her raising her ass to let them slide down over her thighs and knees and ankles raced through me, and of panties tossed casually into the front seat of a car, or on the floor beside her dorm room bed, and of seed that would spill into them later when it was time for Anadolu Yakası Manken Escort him to leave. Fuck! I was super hard in an instant.

I think she almost caught me that night. My mind had followed my dick, and so my mind was elsewhere when I heard her curse on the stairway. She’d spilled some of the drinks. In a flash I recovered, but not before taking a pair of horizontal red-striped bikinis and stashing them deep in my pocket. I breathed deep a few times and ran out to help her with the spill, remembering to untuck the shirt to hide my crotch. Thankfully, she hadn’t noticed. That was the first time.


I heard her before I saw her, jerked out of my panty-reverie. Julia pulled up with a screech of tires and old breaks. “Sorry,” she smiled out of the window, “Period emergency. Get in.”

That was Julia to a tee. She had never been shy about her periods and even told me about the time she bled through white shorts during a history test in the 8th grade.

An hour later we were standing in front of a large panty display at Victoria’s Secret, Julia oohing and aahing over the ones she found cutest for me. She’d hold them up for me to check, then hold them over her skirt to give me an idea of what they might look like on a girl, or at least a girl with her kind of body. She was as animated as ever, and collected every third or fourth pair she considered into our small shopping basket.

Me? I was trying to be invisible, or, if not invisible then some kind of imitation of a guy accompanying his girl friend shopping, maybe sort of interested but not too interested?

“Hi! Can I help you guys?”

A soft, sweet, feminine voice, with maybe a hint of Southern twang? We turned around, Julia with a roll of her eyes and me with my mouth probably hanging open. She was a really pretty sales girl, maybe early 20’s, with frizzy, bold red hair to her shoulders and a faint spray of freckles beneath her eyes. She wore a simple black pencil skirt accented with a gold waist chain, a classic white blouse (2 buttons undone) and flat shoes. Her legs were bare and tanned. The outfit covered what looked like small or medium sized boobs, a nice waist and flaring hips. Sexy! She had a pretty matching-shade-of-red lipstick grin. Her green eyes shone as if delighted to see us.

“I just love it when couples shop here together. It’s so cute that your man is here with you.” Definitely some southern in there.

Julia deadpanned, “Oh, yeah. He’s super into my panties.” Which, I realized could be read in one of three ways: he loves the way I look in panties (the adoring boyfriend reading), or yes, we do fuck like crazy (the sexy, naughty girlfriend reading) or he wishes he could look like me in them (the accurate reading). It made my head snap. I knew Julia. She had meant all three at once to confuse the girl and to confuse me too.

The salesgirl registered the innuendo and smiled. “Well,” she said beaming, “I can see why. Y’all’s gorgeous.” She moved in between us and picked up a pair of midnight blue bikinis with little white bows above the crotch and at the sides. The salesgirl held them up towards Julia and said, “This would be a great color for you, your dark features. Or, maybe,” she shuffled around and found a black g-string, “these if you’re wearing a nice little dress. No panty lines, very sexy on a girl like you.”

She reached over to hand Julia the undergarments, and as she did used her other hand to casually touch Julia’s forearm. She did it with a small bite down on her lower lip, as if nervous about Julia’s response, or as if hoping for something. I thought, “F-me! What is this?”

The redhead rounded back, facing us both now, found some lacy white boy-shorts, stretched them over the hips of her skirt to model what the panty would look like on her. She gave us a big blushing smile. “Or these? Every girl needs…” She came in to touch Julia’s arm again.

She twisted her neck awkwardly towards me, still touching Julia but searching me out, as if wondering about my vote. Or wondering whether I knew. I could see Julia give another roll of her eyes and pull back from the touch, turning her face away. “No thanks, we have this covered but we’ll call if we need you.” Dismissing her.

The sales girl backed her hand off quick and said, “OK then. Yeah, of course. My name is Mona, so y’all feel free if you need anything at all.” She waited, looked at Julia, then looked back at me, nervous and flushed, looked like there was something more she wanted to say. I wondered if she was missing the hint. “Anything,” she repeated hopefully. She turned back once more to Julia and said, “Oh, and we have some nice panty-bra sets that are on sale up front. Thirty percent off and really cute. I can find some in your size. Let’s see, a B cup? Or are they C? Yes, of course, maybe 32-C? I can measure for you, Anadolu Yakası Masöz Escort if you like. So important to get the bra fitted correctly. So many girls…” She paused, looking a bit dazed, then went on, “…you know, but let me help if you want to see them. I’d love to…” She let is fade out as she walked backwards away from us, her eyes still glued to Julia. She had got the hint after all, but kept the beam as if it were glued to her mouth. Finally she turned and sped away to the sales counter.

Julia took me behind a rack of swimsuits and huffed. I spoke first, “What the fuck was that?”

“What? Annoying sales girl? B-cup my ass!”

“Yeah, I know. But she was hitting on you. Right in front of me.” I was actually feeling a little hurt as the pretend boyfriend, but a little turned on too. The girl was smoking hot.

“Oh, fudge! Guys always think there’s a lez angle whenever two girls talk for more than eight seconds. Don’t be a douche.” But she giggled. I knew she had to have seen it too. “It happens,” to which I said mentally “not to me, it don’t.” Julia continued, “Anyway, we’re done here. I have five pair and that’s more than enough to get started. You’re gonna look amazing. So fuck Mona.”

“May I?”

Julia chuckled and said, “Be my guest. I wouldn’t fuck her with Uncle Ed’s dick.”

Was she actually a bit jealous? Could a girl who looked like Julia be jealous of another girl? File that question for later. Her Uncle Ed of course is my Dad, but I had bigger fish to fry.

I gave up on the Mona discussion; it wasn’t going anywhere. But stilI antsy, my eyes wandered over to the aisle of pretty, colorful bras. Julia followed my eyes and smiled. I stammered out, “What about…?”

“Bras? Yeah. I know. But we need research first on the right kind to go with, you know, whatever we get for tits. Maybe we can come back when Mona’s not around. I don’t wanna see you attacking her on the bridal lingerie aisle. B-cup my…twat!”

Reluctantly, at least on my part, we left Vic’s. I saw Mona watching us as we checked out and left. I gave her a friendly wave and a big smile from us both. She gave me a nice smile back.

We spent the rest of the afternoon at three shops: two dresses, one girly-casual and one expensive dress-up (a splurge), four skirts (short, summery, flirty), four blouses, skinny jeans, a bunch of cute little tops, nude panty hose, cream colored shorts, two more tops for the shorts, a pair of (flat) sexy Italian sandals, and then makeup. The makeup took the longest time since Julia was not totally familiar with products for my slightly darker complexion. Finally she was satisfied with the right eyeliner, mascara, blush, three shades of red lipstick, and a nice lip gloss.

The whole thing, VS plus the outfits and makeup, cost me $983 and I was like “F-me! What girls go through for guys!” and Julia was like, “Not the half of it dude, not the half.” She made me feel a little better when she told me we would return a lot of the clothes after she’d had me model. And that girls were dressing at least as much for each other as for their men.

On the ride home Julia called the five pair of panties we’d purchased, plus the bikinis she’d stripped off the night before, my “starter set.” We’d adjust as needed after we began “tuck practice” and bra and boob research the next day while her parents were at work. She took all the clothing back home with her saying she didn’t trust such nice things with me alone overnight.

She pulled up in front of my house. We sat and I breathed deep. “Tuck practice?” I asked stupidly.

“Yeah, that stupid thing, I mean things, there are three of them…”

“Three?” I asked. “What are you talking…?”

“You have two balls don’t you? Those too. And your three guy thingies aren’t going to disappear by themselves when you put on one of those cute dresses. I’m pretty sure you don’t want a bulge there. So we practice.”

“Ah,…OK…I guess…I mean, how do you know all this?” She thought I’d bulge? Cool.

Julia giggled. “A little thing called the internet? I’ll have to show you some time. It’s fascinating. Twenty minutes last night on YouTube and I think I have the idea.”

I paused, uncomfortable with the image. She looked at me and I knew who the boss was. I turned away, almost panting, nervous, gripped my kneecaps and looked straight ahead out the window of the car. “So, ummm… we practice together? Like you’re gonna see me nude?”

“Well yeah. I guess so. I mean I don’t wanna freak you out or anything.” I turned back to her. She made a little sad, grimace face to show me that she cared. “But it’s like, you remember? I told you you’re gonna need a pussy to be a pussy, right? I’m your coach. Just think of me as a coach.”

“But, you? You’re not gonna…?”

“Me?” she seemed surprised. “No, not me. Wish on, dude.” She let out a big laugh at me, then more charitably, “… but who knows? One of the things we’ll do is dress up together some day. You know? Like two girlfriends going out to party. And then, well no promises, but we’ll see.” And it made her blush, which was cute and nice and friendly.

I walked in the house to Mom and Dad with my head spinning. Did I have any idea what I was getting myself into?

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