Julia, Ben and Lisa Ch. 03

Ch 03: WEDNESDAY

A few quick notes:

1. this is the third 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

I made it to Julia's house around 9 AM the following morning, timed for when her parents would be off to work. We hugged and she gave me a nice kiss on the cheek. We had the place to ourselves, Julia's Mom having dropped Bobo for the day at the Doggie Depot (a grooming salon) on her way in to work.

We had breakfast out in the yard, just coffee and toast. When I reached for the butter Julia slapped my hand away, "Now, now. We're watching our figures." We broke up — it's well known in our family that each of us can eat like a truck-driver without gaining an ounce. But her point was made.

We cleaned up our dishes and she said, "Time to begin. Back to the internet for starters. The bra? The boobs? I'm a little worried about your tits."

"C'mon! Give me a break. It's early."

"Your tits. I stand by it. Now move."

We sat side by side as she began to search. In no more than 10 minutes we were both overwhelmed by the choices we would need to make. Self-stickers? Glue-ons? Bra pouches? Color, size, weight, density, nipple size and color. Hard nips? Soft nips? Bra styles and support? Material? Well, at least that one was clear. Everyone who commented said the silicon could not be beat. And the cost seemed to go from about $30 to like $1,000 or more if you wanted a custom fitting.

"Fuck," I said. "Who knew tits were so complicated?"

"Yeah, they really are. Why I told you I was nervous about it."

We ended up on a site called Titania Bleu. After ten minutes of reading side by side coach felt we were on to something. Julia said, "good value" and Julia said, "good on skin color and tone." They did breast forms designed specifically by and for guys. Julia said, "might cut both ways" but which, who woulda known such a thing existed? I said, "Go Big Bleu!" and coach loved it. We were both into it. Coach decided I needed to start with smaller boobs. A bigger bust would be harder to fake. I wanted small pinkish areola and soft (just slightly extended) nipples. Coach was down with that. Customer reviewers raved about their cute bras (mmmm me, dressing!), the realistic look in cute tops and blouses (mmmmm me, pretty!) and feel (mmmm me, felt up!) and I began to chub up a bit.

Julia measured and said that I should be a 34 small-B. We bought three specialty bras to go with the inserts, the kind with pouches. The company said their forms could be used with normal support bras, but it seemed simpler to start this way. The bras looked nice and had good structure, while also looking pretty girly, with some cute lace and a bow under the cleavage. The main thing was to have the support of a bra that would keep the tits from wandering around my chest.

The whole package was $239. Julia thought it was a good price given inclusion of the bras. That it was right for a starter set. That we could upgrade my tits later if something more dramatic was needed. Mmmmmm. Me. With tits. We paused over shipping. Should we wait till her parents were safely gone on their trip? Julia said she'd be sure to intercept the package. We were eager to get going. So I kicked in an extra $39 for two day shipping in her name.

I was starting to be a little worried about the money. I'd received a part of my inheritance from Gramps and Grandma when I turned 18, but only the first $30,000. Already I was into being a girl for about $1,200 of that.

The boobs and bra done, we were ready, or at least Julia was, for round two.

"Now strip and shave dude. I want every one of those gnarly hairs gone when you come out of the bathroom."

"Everything?"

"Everything. Arms, legs, pits, dick, ball sack, ass..." She peeked down the shirt I wore by pulling it out with one finger. "Your chest and belly look fine, nothing there. But double check. Get it smooth."

"My pubes? For real?"

"Duh! That especially. I told you we don't want any bumps there. If I know you, you've let yourself go and have a mini-forrest of guy stuff down there. Gross!"

"But..."

"No buts. We're doing this. What do you think girls do anyhow? We shave it up for our man, that's what. And bonus! It feels great in panties."

"But I'm not trying to get a man." Was certainly the right thing to say.

"No, but you are trying to be a realistic girl. And girls shave their pussies. Period."

Pussy. If only. Period. Made me think of her "period emergency" the day before and how far into her cycle she was. I wondered briefly, what does a tampon feel like when it's like, you know, inside you? But I couldn't go there.

Julia slapped me in the ass, saying, "I have shaving cream and a brand new razor in the shower waiting for you. Your head is fine, just keep growing it out, but you can redo it with my shampoo if you like, has a nice scent. Plus there's a scented body wash. Now go." And off to the bath I went.

Forty-five minutes later I emerged in the big fluffy robe Julia had provided.

"How'd you do?"

"OK...I guess. It's hard to reach all those...you know, spots and I was afraid of cutting myself. But I think it's OK."

"All right then. Strip and let me see what we are working with."

"Now? Here?" We were in Julia's bedroom.

"Of course. Where else? I'm not gonna let your naked ass touch the living room couch for God's sake. My bedroom is the safest place for us, especially if one of them were to come home. So yeah, right here."

She gave me her nicest, warmest smile to encourage me and said, "And remember, I'm just the coach. I'm pretty sure your high school basketball team isn't hung up about being naked in front of their coach. The same goes for you." She looked at me more sternly. "Now strip."

I was so embarrassed. "But I can't. I mean I will. But not yet. I have...you know, ... I have a problem."

And I did. I was worried but sort of OK coming out of the bath. But then seeing her, realizing what was about to happen, hearing her talk to me like that! Well, it gave me a super hard-on. I was keeping the sides of the robe together, with my penis running straight up along my body to hide it.

"A problem?" She snickered, looking down at my crotch area. "I thought this might happen. I know exactly what to do about it."

Julia walked over to the desk where she studied and rummaged around the draw. I was afraid of what I'd see, but when she turned back to me the only thing she had in her hand was a standard, wooden ruler she used for homework. That and a big goofy smile.

"See we need to train him. There's no way you can tuck with a hard-on. And even when you do tuck him soft you cannot allow yourself to get a stiffy. They say in the videos I watched that it really hurts. So training is for your own good. OK?"

What could I say? A meek "OK" is what squeaked out. "But what's the ruler for?"

"Just strip."

I pulled the edges of the robe apart and my male apparatus sprang loose — standing up now, not touching me, maybe 60 degrees elevated and sporting a little circle of wet at the tip.

"Hmmmm," she said. "Lovely! Nicer than you ever let on. It's cute!" She bent at the waist slightly to get a better look.

I didn't know whether to be offended. Do guys want their dicks to be cute? Did I? But she said "nicer," which was sweet.

"Thank you," I said blushing. Julia was the first girl ever to see my adult cock, and certainly the first ever to study my hard-on this intently. Her words brought an additional blush to my face, and an additional surge of blood to my penis. It made him stand up even higher along my abdomen.

"Thing is we don't need him now. Don't want him now. Watch as my magic wand makes him disappear." She swirled the ruler around and over her head like a magician. Her crazy-ass smile told me she was enjoying our play time.

Julia advanced towards me waving the ruler and then smacking it into her open hand. The robe had fallen to the floor around my ankles and I was totally nude and clean shaven. She smacked the ruler twice more and took aim with it at the cock.

"Wait!! Don't!"

She looked at me and backed up a bit with that devilish smile on her face.

"What the fuck are you doing Julia? That would really hurt."

"Just something I picked when my roommate showed me this pervy blog she found. We were laughing our asses off. All dick stories. You'd be amazed what guys will write about their dicks,...or maybe not..." Her cute grin widened at that. "Anyway, this one story, a college guy sneaks out of the shower into his sister's bedroom on the day of her wedding. Just a towel 'round his waist. Gets a super hard-on looking at his sister's bridal undies, all laid out for her on the bed. Sort of like you with my panties. His dick is poking out from under the towel, he's grooving on how it looks next to the pure white silk. The sister and her Maid-of-Honor are downstairs. He hears them making noises about coming up to dress. He panics. Dude has to soften up his little pirate fast. He looks around, finds her heavy hairbrush, and smacks the flat side against his dick a bunch of times. Said he was so hard that he didn't feel any pain. But he taught that dick a lesson: play time was over and it goes small and soft. The girls come in, he makes some stupid excuse for being there, but looks OK. The sister never realizes he'd been about five seconds from splooging on her bridal panties, but the girlfriend, the Maid-of-Honor girl, she knows. Naturally, the end of the story is the guy fucks the Maid-of-Honor later that night after the reception. Anyway, now we're going to do the same for you — train the little bugger to know when this," pointing to my hard dick, "is and is not allowed."

"Ugggh. I don't know, I..."

Thwack! But not very hard. It didn't really hurt at all. I looked down and the head of my cock was still pointing up to me, the juicy bead had grown a bit.

Thwack! A bit harder. The first one had been to the underside of my hard penis, but this one was for the top side. She was eyes down focused on it, smacking the ruler downward from along my belly. Thwack! The dick. Harder still, and that one hurt a little, maybe more than a little. Thwack! The head. Oh my. Then two more similar Thwacks in rapid succession. I was afraid she was getting into this a little too much.

Her arm was raised again when I looked down and saw my penis retreating. Suddenly it was just semi-hard, and the head was drooping. Thwack! The hardest yet, and it got both the pole and the cap, and it definitely hurt.

Again she prepared to strike. "Wait! Wait, Julia. He's...going...going down I think."

She paused and we stood there staring at my deflating dick. Down, drooped, softer, shrinking, softer and down again. Like the jerky lowering of a flag. We waited another minute. My dick was giving up. Down and down it went till it shrank to normal size and fell to rest between my balls. It was over.

Julia gave me the biggest smile, saying, "Good boy. Now he knows his place. And I think it's even cuter now. That's Lesson 1. I'm betting we'll need more of those in the future to train him properly, but it's a good start."

"Ummm, yeah. I guess." Glad the training was over but missing my hard on immediately. Wishing I could have used it to cum in front of her. A pipe-dream.

She stood me up straight and began her inspection of my work in the shower. She started with my face and chest, which hadn't really needed the razor at all. "Good. Good." She turned me to look at my upper back. "Good here too." Now she moved in front of me in a crouch. She took my penis in her hand and lifted it slightly to peer closely at my crotch, my balls and nether regions, saying again "Good job...get used to this. You're dick and balls are actually very handsome and you did it just right! But remember the ruler is right here on the floor if needed." She released my still soft cock, and wiped her hand on her jeans.

Oh-My-God! I was so afraid of Julia and her ruler that my dick didn't harden at all. But Oh-My-God! The prettiest girl in the world had just held my dick in her hand, and had some of my precum on her jeans. Amazing. It was an out-of-body, or at least out-of-dick, experience. My head was spinning.

Now she moved on to my ass and lower back silently, and then to my legs. "Oops. Missed some here." Her finger was running over my upper calf just under the back of my knee. "And here too." A bit lower on the other calf. "Don't worry. I can fix this with a dry shave. There's not very much, and your hair there is nice and fine. Just like a girl's should be." I could tell she was proud of me, and for a second I was too.

Julia ran into the bathroom and emerged with the razor and shaving cream. She spread a drop of the cream on each of the areas and shaved them to her satisfaction.

"Perfect," she pronounced with a proud beaming grain.

"Now put that robe back on. We've done enough for the morning. It's time to go down for lunch." I looked over at her wall clock and was amazed to see it was already 12:30. I think I'd been in a fog the whole time. She continued, "We'll come back up for one more thing and then call it a day."

"One more...?"

"You know," she smiled. Julia picked up the ruler, smacked her hand again, and said, "And we need to really make him behave for this next part. So remember!" Thwack again — but only on her hand.

"Tuck?"

"You know it," I got into the robe and we went downstairs.

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

At lunch — just salads — we tried to talk normally, the way we had been doing since we were 8 year olds. But it wasn't sticking. Talk about an elephant in the room. This was more like a herd of elephants, or a herd of elephants chasing three rhinos towards a family of hippos.

Finally, I burst it out: "Julia, don't you think this is too weird? I mean maybe we ought to cool it. At least for today? I don't know if I can..."

Julia switched from goofy to supportive in a heartbeat. "Oh my God, my baby boy. Is it too much for you?"

"I don't know, but maybe it's going too fast for me. I mean I never thought I would, you know, be, like..."

She reached her hand over and put it over mine, giving me a tender look. "I know. I really do. Maybe we should knock it off for today. If you think that's best. I mean I'm into it, obviously I am. I'm pretty sure you are too. But we can definitely postpone it. Or cancel the whole thing. Up to you. The last thing I want is for you to be hurt by any of this."

"Oh, no. I don't. I mean its super embarrassing, but I...if I'm honest...I really don't want to cancel. You're being so nice it makes it OK, I guess." I was fumbling around not knowing one way or the other what I did actually want.

"Thank you!"

"Still, it's just that it's all about me, ya' know? Me being embarrassed and displayed, me being the douchebag everyone would laugh at. It's hard..." She raised her eyebrows at me. "No pun intended. And really, what about you? What are you thinking about all this? You must think I'm insane or a pervert or ..."

Julia giggled, "Geez! I was afraid you would think I was the pervert. Me, whacking your little soldier with a ruler to get him nice and girly." And laughed again.

"Oh, no. I understood. I needed that. Really. And...aaaahhhh...I kinda like you being in charge like that. It's just...I mean, what are you thinking?"

"Me?" She seemed surprised. "I guess I think it's super-hot, and that you're going to make a really pretty girl. And I guess I just want to support...your thing...your thing with panties. And no, I don't think you're perverted, just kind of naughty and sexy. Both of us. Naughty and sexy. OK?"

Julia paused for that, and went on with a little blush. "Ahhh. Kind of like what I told you, I always wished I had a little sister, you know? Someone to teach...just about being a girl I guess." She paused again and looked at me slightly nervous seeming. "And...aah...you know, to be fair, I guess it's kind of hot for me too. Our project I mean."

Now that was interesting to me. "Whaddaya mean?"

"Ummm. Well. I'm...well, did you know it's like...", she paused to do some math, "like 10 months since I got laid? Like last August? My entire freshman year in college and zero cock. Zero. So it's, you know, just being the coach, creating a brand new girl, it's kind of a turn on."

"Really?" Now this had possibilities.

"Yeah. I'm like some dried up old hag who's grateful just to see and touch a cock again. Even if it's just my cousin's. And even if it's not us, you know, having sex."

We both let this sink in. I knew we weren't going to have sex. That would be plain nuts. But the fact that she was getting a little turned on here seemed really nice too. Down here, safe in the kitchen, with the ruler upstairs, it seemed OK to get at least half hard at what she was saying.

I had to ask, "But what about your feelings? Are you embarrassed or uncomfortable at all? I mean what would embarrass you if not this?"

"Well, I get embarrassed sometimes like everyone else, but not by this. I mean, maybe a little. But I love you and it's a turn-on too, sooo sexy, so not very much."

"Then what? Tell me something, so it's not just me, not just my feelings. Tell me when you have been embarrassed."

"Like in school? Like bombing a test or something? Or wearing the wrong shoes with an outfit?"

"No, not like that. Like this. Like embarrassed about sex. Doesn't that ever happen to you?"

"I knew what you meant." She paused and looked serious. "And, yeah. It happens. Not too often, thank God, but it has happened."

"Then tell me. I don't want this all to be me, about my secrets. You have to tell me one thing. Tell me about one embarrassing sex thing in your life."

Julia put down her fork and sat daintily back in her chair with a serious but neutral look on her face. We waited for her. She was so good to me. And I knew I had her when she turned serious.

She cleared her throat then sipped her iced-tea. "You really need this? Like for real?"

"I do," I said, trying to match her serious look. I did have her.

"OK. I'll tell you. Just one, but it's my biggest one, so no bitching for more after this one OK? After this we're fair and square."

"With details?"

"Oh, what the fuck! With details. Fact, I'm not sure how I could tell it at all without details."

I nodded happily and sat back to enjoy. We waited some more and she cleared her throat a couple more times. Difficult for her to begin I guess — the same as it was for me.

Finally she said, "The Andersons."

"Andersons? Who are they?"

"Our neighbors. About six houses down. In their early 30's I think. George and Louise Anderson. They have these two really nice kids, around ages 2 and 4. I babysit for them. I mean I used to anyway. Last August they were going out to some big company party of his. Weren't supposed to get home till like 1 or 2 in the morning. I think he won some stupid award or something."

She stopped, seemed to be remembering. "Go on" I said.

"Anyway, they left and it was pretty normal at the start. No, totally normal. They left. I fed the kids, we played in the living room. I really loved those kids." She looked distressed at the memory.

"Around 7:30 I got them all cleaned up. Put them to bed. The baby went right down and I read Sally stories till she dropped off. I went downstairs and did what I usually did once the kids were in bed and asleep."

"Which was?"

"I texted James to come over."

"Aaah. I'm getting it. And James was who?"

"Well, just my boyfriend at the time. College dude, graduated two years ahead of me. Didn't last. His loss, the dickwad. But we'd been...you know, intimate for the past few months."