Caught in the Storm Chapter 5 Prelude to a New Game
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Caught In The Storm - Chapter 2 A Whole New Level free porn video
Caught in the Storm
Chapter Two - A Whole New Level
Billy sat there stunned silent. April's hands gripping his upper thigh
felt intoxicating. He looked at her painted nails, a soft lavender which
contrasted with both the denim of his skirt and the brown leggings they
were holding so firmly. He was still in shock at her question, her impish
grin, the mere notion. Could he?
"Hello, Earth to Billy." April waved a hand in front of his face, the
other still holding his leg. "Are you there? Did I break you?"
He grinned. "No. You just caught me off guard. It's not something I'd
ever thought about." He shook his head as if trying to toss the thought
from inside it, again feeling his pigtails playfully bouncing around. "I
don't know I could."
"Of course you COULD," she said emphatically. "Put one leg in each leg
hole, pull up."
April, too, had a way of disarming him. That had done it. "That's not
what I meant," he said chuckling.
"But it's true."
"I know, but it's different."
"No different than wearing a dress and tights, or leggings and a cute
skirt," she said, flipping his skirt up. He reacted exactly as a girl
would, gasping and reactively trying to stop it from coming up too far.
He blushed deeply when his hands crashed onto his thigh, rushing the
skirt down, on top of her hand.
"I... uh..." He was too flustered by his reaction to even get his
thoughts together to speak.
"You're a natural at this." She teased, gripping his leg, again. She
extended her fingers just a little, up his leg a little more as guys had
flirtatiously tried to do with her. "So? Are you game?" She winked again
as she asked, using a far more flirtatiously playful near whisper tone of
voice. "I promise, it'll be fun."
"YEAH!" Tess jumped up from the floor, grabbing one of his hands and
jumping up and down holding it. "Let's play more dress up! Mommy can
play, too! We can all play! It will be sooooooo much fun!"
Billy looked at the two girls, mother and daughter, both with 'that
look'. He sighed, nodded, and said, "Why not?"
So, for the third time within the hour Billy found himself following Tess
down the hall to find something to play dress-up in, this time both of
them behind April. They followed April into her own room this time, which
had a modest walk-in closet that dwarfed the smaller accordion-doored
closet in the guest room Tess had gotten the earlier outfits from.
As they passed Tess's room April said to her daughter, "Sweetie, why
don't you change into something warmer that you can wear outside?"
"Okay, Mommy!" Tess skipped into her room and shut the door.
"Now, for you," April said, making the 'follow me' finger motion to
Billy. "Let's get you into something a little more practical, but damn if
you don't make that work!" She smirked, watching him almost stumble
shortening his stride and pressing his skirt down shyly- an almost
girlish reaction that amused her to no end.
She walked into her modest walk-in closet, which was not particularly
large but did make the small accordion-doored closet in the guest room
seem small by comparison. "So where did you learn to walk in heels so
well?" she said from inside the closet.
"Uh, nowhere," Billy said coming to the door to watch her perusing her
overwhelmingly large wardrobe. "Oh wow."
"What?" April looked over her shoulder. "Checking me out again?"
"What?! No!" Billy waved his hands in protest.
"Turn for me." She spun her finger to indicate she wanted him to turn.
"On your heels, sharply." He did. "Ok, again, slowly."
"What? Why?" he asked as he started the second turn.
"Well the first was fun just to see you working those heels and that
skirt so well, and it flirtatiously lifted up." She grinned impishly
again. "This time is so I can get a sense for what would fit you
alright."
"Are you serious?"
"Well, you COULD wear that out, but those capris leggings are not
insulated and that skirt is short, so you'll be cold."
"Well, I can understand that. I don't know about wearing heels going..."
The words trailed off as he realized he was talking about going out.
"Wait. Cold? Are we GOING somewhere?!"
"Dinner," April said digging through a section of dresses. "Unless you
want to sit around hungry."
"It's starting to snow."
"So we're going to dress warmer." April still seemed so nonchalant it was
confusing Billy.
"Uh, ok," he said, sounding befuddled.
"Here, hold this dress up." She handed him a skirtall made of burgundy
corduroy. "That'll work, but you need warmer leggings. Back up." She
shooed him out of the closet and went to her dresser.
"This is a dress," Billy said as she was getting stuff out of her
dresser, from at least two drawers he noted.
"Of course it is, silly." April turned and handed him some folded
clothing, and pointed to the door. "It wouldn't be 'dressup' if you wore
something you'd normally wear." She pushed him gently towards the door.
"But you said we're going out?" he said backing up into the hall.
"Yes, dinner. Remember?" she said plainly. "Now go into the guest room
and put all that on. ALL of it. Just take off what you replace." Before
he could ask what she meant her door closed.
Billy sighed and walked to the guest room, hearing Tess singing in her
room. He shut the door and put the clothes on the bed and sat down,
taking the heels off first. "So a dress, and leggings," he said to
himself. He took his leggings off, then the skirt, looking at how tiny it
seemed in his hands, yet oddly comfortably modest when he was wearing it
moments ago.
He chased THAT thought out of his mind quickly and picked up the leggings
he was given. They were black. As he picked them up something fell to the
floor. He did a double take looking at what it was- panties. His heart
stopped a second. Did April put those there on purpose? Were they
accidentally stuck to the leggings? Surely she didn't... Did she? He
picked them up, almost as if they intimidated him. They were briefs, like
he wore, but different. They looked so small, so delicate, and felt so
soft. They were almost the same color as the dress she'd given him.
That settled it, it was intentional. This must be what she meant by
"taking it to the next level." He sighed, testing their stretch a little.
He wasn't much bigger than April, but this would be different. He could
always just not wear them, what's the worst that would happen? Would she
be disappointed?
"Screw it, who's going to be seeing up my dress?" he said aloud to
himself. He took a deep breath like he was leaping into a pool and pulled
his underwear off and the panties up. He caught himself holding his
breath and exhaled. The terror passed quickly, realizing there was no
reason to be scared, and felt silly that it made him feel scared at all.
"Ok, leggings."
They were tighter, thicker, and had stretchy straps that he immediately
understood were to keep them down around his ankles. They hugged his
legs. He looked in the mirror and realized he was checking out his own
legs and ass, blushed in self-deficating amusement and looked to pick up
the dress. Next to it, with the socks that didn't quite fall off the bed
with the panties... a bra!
"In for a penny..." He sighed and began to take off the sweater.
He'd barely gotten it off when a knock at the door got his attention.
"Need help Billy?" April asked from the hallway.
He looked at the bra. He'd never put one on before. In high school he'd
tried to flirt and unhook them with girls he'd dated, but never could
manage it easily. "Yeah, I guess it would make this faster."
April came in the room and smiled seeing his underwear on the floor. "I'm
proud of you."
"For what?" he said, turning to face her.
"For being this brave, for amusing Tess with this, for amusing me, with
THESE." She traced the pantyline on his left hip to his ass. She felt his
leg and butt tense with surprise. Again, the almost girlish response
amused her. For a second she wanted to experiment more, really really
wanted to. She brushed those thoughts aside and told him to get his shirt
off.
"Ok, turn around and slip your arms in the arm holes and pull it back.
I'll clasp it for you," April instructed, and he did so. "Does that feel
ok?" she asked as it clasped shut.
"A little tight and like it's pulling my chest up."
"So, basically what it should feel like," she said, putting her fingers
in the band here or there testing to ensure it wasn't too tight. "Turn."
"Don't laugh, please. This is a little weird for me," he said as he faced
her, she looked at him and grinned.
"That's a little empty, but all I can do for that..." She paused and
opened the closet, pulling some socks out of a tupperware dresser.
"Here." She stuffed a pair in each cup of the bra. "It won't be a
realistic feeling but it'll fill it out alright under your shirt and
sweater.
"Um, ok," Billy said looking down at 'his chest'.
"Wishing you had these?" April teased her chest up a little, not that he
could see anything under her shirt. That's when he noticed.
"Wait!" He stepped back, pointing at her chest, then her legs, up and
down a few times, mouth agape.
"Yes, I have boobs, and curves, you idiot." She laughed.
"No!" he objected.
"Yes!" She smirked, knowing he was talking about something else entirely.
"You're in pants!" He sounded indignant. "And a t-shirt!"
"It's nicer than a t-shirt." It was a solid burgundy long-sleeved t-
shirt, slightly more formal than a casual t-shirt, but a t-shirt none-
the-less.
"But you gave me a dress. You're in pants!" He was grinning but
emphatically questioning her decision. "Why don't I get the pants?"
"Are you asking to get into my pants?" The look on Billy's face caused
her to burst into laughter, almost falling over. "Just put your dress on,
princess." April laughed leaving the room.
April found Tess in the living room waiting. She'd put jeans on, and a t-
shirt with Tinker Bell, currently her favorite. She had a long sleeved
dark green long-sleeved shirt under her t-shirt.
"Is Uncle Billy ready?" Tess asked, smiling ear to ear, wondering what he
was wearing.
"Almost," April said as she sat down.
"Some girls take soooooo long to get dressed," Tess said, making herself
laugh.
Billy came out a few minutes later. He was tugging at the dress to pull
it down longer, not that that would actually accomplish anything. He was
in the same heels as before. He tugged at the sweater that didn't cover
his sides entirely where the dress was open. "Does this work?" he asked.
"It's a skirtall, it's ok to show the sides a little," April said.
"Ok, that, too," he said. "But I meant, brown and... purple-red?" He
looked lost for the color name.
"Burgundy," Tess said. "It's burgundy, and it's a skirtall!"
"Skirtall?" He nodded. "A skirt overalls? Ok, that works."
"I DO have another top, but it's pink," April said. "That works great
with both black and burgundy, but you'll have to change those heels."
"Let me guess, because they'll clash?" He smirked, already slipping his
foot out of them.
"Come on, and Tess let's get those pigtails out, too," April said walking
past him.
He'd barely put on the pink sweater, just like the brown one, but a v-
neck, when his hair was being fixed. Instead of pigtails they put a few
barrettes in strategically to give his hair a slightly feminine look.
When April asked, he conceded makeup would be fine. He was already this
far into it, heck he was in panties and a stuffed bra!
She put a little pink on his eyes, mascara on his lashes, pink lipstick,
and a little blush. Nothing extravagant, but enough to be seen. He was
glad he had very light facial hair and that he'd shaved that afternoon.
Soon he was at the front door with April and Tess. He'd changed his
socks, pink as well, and was now in heeled ankle boots. April gave him a
fluffy pink coat, promising he'd be warm enough in the skirtall and
leggings.
"Remind me why we're going out again?" he asked nervously at the door.
"Um, dinner," April said, rolling her eyes. "For the third time."
"But the roads." He tried to think of a reason not to go out and be seen
by the world.
"Dell's is just basically right next to the park," Tess said.
Of course, Dell's. They loved that place. A little 'Mom & Pop' kind of
local-owned place. He had eaten there with them before, several times.
"No one will say a thing," April said. "You look like a girl."
"Really?"
"Enough." April took his arm. "And it's a very progressive neighborhood."
That didn't exactly make him feel better, but he let her lead him out the
door. The snow was pretty, falling gently and without sleet now. He was
glad for her arm, the sleet had made several slick spots and in the
heeled boots he almost fell a few times. He couldn't help but wonder if
this is how girls felt on his arm on dates in years past, grateful for
the support and slightly nervous with each step.
Dell's had just come into view when he looked down. "Why am I the only
girl in heels?!"
Tess giggled. "Mommy won't let me wear heels yet, silly." She stopped and
looked back at him. "You just called yourself a girl!" She laughed
hysterically.
"Tess," April said thoughtfully, "while we're playing dress up with Uncle
Billy, let's pretend she is Aunt Billy, ok?"
"Ok!" Tess said, not giving it a thought and turning to walk again. She
looked over her shoulder. "With an 'ie'?"
"Sure," Billy said. "Why not?"
"And Billie," April said, "with an 'ie'," grinning, "I wore one and half
inch pumps all day. I did not want to be in heels during dinner, but you
never wear them, so it's a treat for you."
"Oh it's a treat alright," he said dryly as they got to the corner. There
the breeze picked up and he was glad the skirt was straight and not
flighty like the one he'd worn earlier. The leggings were not entirely
preventing him from getting a chill, but they were surprisingly effective
enough. He figured he could walk several blocks in them before he really
got cold, not much different than his jeans.
The three crossed the street to the little diner. It was only about half
full. "April! Tess!" A woman yelled from the counter. She looked like she
was in her late forties or early fifties with greying hair and the lines
of many years. Her smile created the strongest creases on her face and
her eyes sparkled with genuine happiness seeing regular customers that
clearly were more of friends to her than merely business.
"Hi Mama Dell!" Tess said, running behind the counter to hug the woman.
"Hi Dell," April said coming over to the counter. They hugged over the
counter as Tess came back around from behind the counter.
"Who is your pretty friend here?" Dell asked, looking Billy up and down.
"We haven't met sweetheart, I'm Mama Dell, you can call me Dell."
"Uh, Billy," he said nervously as Dell took his hand.
"With an 'ie'!" Tess chimed in proudly, causing Billy to blush a little.
"Well, Billie, with an 'ie', you need to stop biting these nails and
cutting them too short." Dell said with a motherly tone. "Boys," She
paused, "and girls, will find it more attractive if you take better care
of them." She winked and gave an examining look.
Tess took the lead to a corner booth. "We always sit here!" she said
happily bouncing into a spot where she could see the window and watch the
snow.
April brought menus from the counter. "Do you want inside or outside,
Billie, with an 'ie'?" She smirked seeing him blush a little at the
attention that that was causing him already.
"Uh, inside," he said, sliding in first when April motioned for him to.
"Most girls do," she whispered as she sat beside him, putting a hand on
his leg just where his skirtall hem sat. "Enjoy the chance to experience
'the other side'." She smiled warmly.
"Well, we left without my wallet, so I'm enjoying that perk." Billy
smirked back at her.
"You little minx!" April elbowed Billy. "A little flirty dress, heels,
and shaking that tush when we walked, clinging to me for help. 'Oh strong
stable man save me!' All for a free meal?" she teased in that friendly
way best friends can get away with.
"For that, I'm ordering the steak," Billy said with a grin.
Dinner went quicker than expected. Billy found himself far more
comfortable than he would have ever thought possible. Here he was in a
dress, in public, with makeup on, and under it all, panties and a bra.
The walk home was colder because the wind had picked up, and it was more
slippery than before with a thin coat of snow over the now solid iced
over sleet. Billy walked arm in arm with April for stability in the
heeled boots, not just holding her hand as before. Tess happily skipped
along seemingly unfazed by the snow and ice. She chattered non-stop all
the way home about how fun the game was and ideas for other outfits they
could all wear.
By the time they got home the snow was really coming down, already half
an inch was taking hold on the road.
Everyone got in the house and Tess went to her room. April kicked off her
shoes and sat down on the couch. She patted the couch and Billy joined
her. "So, was it so bad?"
"It was... interesting," Billy replied, crossing his legs.
"Oh you're doing that now?" April pushed his leg.
"Just felt like the thing to do," he said, letting her push his leg off.
"If you aren't in love with those heels you can kick them off and put
your feet up on the couch like me." She teased.
He slipped the boots off and folded his legs under him the way he'd seen
girls do before. "Is this right?" He joked.
Tess came in the room and sat between them, eyeing her mom and Billy
suspiciously. "Are you staying for movie time?" she asked him. "Can he
stay, Mommy?" She turned to April.
"Probably a good idea, the roads are going to be dangerous," April said.
"I guess I could, but how will I get home later?"
"Stay the night, we have a guest room," April offered.
"Oooh! Sleepover!" Tess got excited again.
A few hours later, well into the second Princess Diaries movie, Tess was
fast asleep on the floor. April got up and carried Tess to bed. She was
gone for several minutes before Billy got up and stretched his legs. He
turned to see April coming back, in her pajamas.
She wore a long sleeved flannel shirt that hung to her mid-thighs.
"I left some pajamas in the guest room for you," April said. "Probably a
little more comfortable to sleep in than that." Billy started to head to
the room, picking up the boots on the way. "Oh, and there's some stuff to
clean up the makeup in the guest bath, let me know if you need help."
Billy walked into the bedroom. He couldn't miss the pajamas. A long grey
shirt with short pink sleeves. On the front, Tinker Bell below the text
"#FEISTY". Beside the shirt a pair of pink cotton stretch shorts.
"Seriously?" Billy said, leaning out the door holding the shirt. "This?"
"Tinker Bell is one of Tess's favorites. She'll love it when she sees it
in the morning." April rounded the couch and looked back. "Hurry up and
get changed, we can watch something more interesting." She turned and sat
down.
Billy took off the dress, looking at himself in the mirror in the close
fitting shirt and leggings. He could almost pass as a girl like this he
thought. Heck, he'd done it this evening at the diner, hadn't he? He
slowly took off the clothing. Finally he got down to just bra and
panties. He struggled, but eventually got the bra off. Looking around he
didn't see his underwear, or any of his clothes.
"April?" he poked his head out whispering trying to get her attention.
She didn't react. He tried a few times before giving up. He couldn't tell
if she wasn't able to hear him or if she was playing coy and ignoring
him. He took a deep breath and went to the bed. He put the shirt on, it
was very short, even shorter than the skirt he'd worn earlier, by a good
measure. Now he understood why the shorts. He put them on then went to
the bathroom to clean up.
Several minutes later he came out to the living room. April was sitting
on the couch, her half-bared legs stretched out across most of the couch.
She was watching the snow out the window. "Well it's about time. Sheesh,
some girls take forever," she teased.
"Alright, alright." Billy waved his hand to shut her up. "So, my
underwear?"
"They would clash with that cute nightie." She grinned, moving her legs a
little. "Come sit down."
Billy sat on the opposite end of the couch. "What are we watching?"
"Serendipity," she said, pulling a blanket off the back of the couch.
"And showing that much leg, you're going to get cold. Come on, cuddle
with me."
They sat and watched the movie, making small talk and snide jokes
periodically, just like old times. Soon they closer than he'd been to her
in years, her legs folded in among his. He was surprised to feel her hand
on his leg. He started to move, but she put an arm around him and pulled
on his shoulder, he let himself be pulled towards her. He was surprised
when he felt her legs slide down his, she laid down behind him, his head
on her folded arm just in front of her, a leg between his.
Billy fell asleep first. April held him close to her, playing with his
hair gently until she realized he was out. She looked down at her nearly
life-long friend, and felt a stirring she never felt for him before. Sure
she'd always loved how gentle, kind, and protective he was of her, and
even more so of Tess. But that almost felt like a sibling sort of
relationship, but this... this was different.
She looked out the window, the snow was coming down still, and would most
of the night. What a strange turn of events that this snow would come in
today, unexpected as it was until hours before it hit, arriving earlier
than forecast. What a delightfully unexpected sight to see Billy in a
skirt when she walked in the house. April still didn't know what
possessed her to push his buttons to get him into panties, a dress, and
to go out to dinner in heeled boots, while she wore pants and sneakers.
She didn't know why she chose the pajamas for him that she had. Her
flannel shirt was longer, it even had matching pants she could have given
him. Something about all this captivated her, almost as much as the
confusion she was feeling looking at him sleeping peacefully in her arms
now.
She looked out the window in contemplation. It was still snowing. It
would most of the night. April didn't think much more that night. Soon
she, too, was sleeping peacefully, content that he was there, caught in
this storm, and this weird string of events, with her.
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