Wing Night at Stingers
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In high school, my best friend, Dave, was a stud. He dated so many hot
girls I couldn't keep count. On the other hand, I couldn't get to
first base with girls. I was awkward and shy. I felt silly, I looked
silly. I was silly. I would have been a totally isolated, outcast nerd,
had it not been for Dave.
We had a lot of fun hanging around, cruising in his Camaro. I was his
wing man. I felt cool as hell riding around town in that car. We'd go
to a drive in, where Dave inevitably knew the car hops. We'd go to the
rec hall, where Dave would shoot pool. I wasn't much good at pool, so I
mostly just hung out at the lunch counter, or around the pool tables
watching Dave shoot. They weren't supposed to bet money at the rec hall,
but they always did. Dave would have me hold the money, and most of the
time we left with an extra 20 or 30 dollars.
"Cruising money," Dave would say with a confident smile.
"Great," I'd say, "let's cruise!"
I truly did feel special riding around with Dave. He was the coolest
guy I knew, and he was my best friend.
Senior year, at Halloween, I was still just 17, and the legal drinking
age then was 18, and some of the rec hall guys were planning to go bar
hopping. I thought Dave was going to go with them, taking a date, like
he usually did, so I figured I would just be staying at home watching
TV. Then Dave surprised me saying there was a house party we should go
to. "There's a girl I'm hoping will be there," Dave explained.
"Sounds cool!" I said. "Yeah, I'd like to go, if that's what you want,
great!" I was thrilled beyond words that I'd be going to a party, and
not be stuck alone at home.
"It's a costume party," Dave said. "So we'll have to come up with
something cool to wear."
"Great," I said. I hadn't worn a costume for Halloween since grade
school, I was thinking.
"It's gotta be something cool," Dave said. "We don't want to just drag
out our old devil or ghost outfits."
"Right," I said, "we'll come up with something."
A couple days later, Dave stopped by my house. "I've got it," he said,
and handed me a rolled up magazine. I took the magazine and unrolled it.
It was an Esquire, and there was a picture of that supermodel Claudia
Schiffer, and her boyfriend the magician David Copperfield on the cover.
"Cool," I said. "So...what's your idea?"
"Well, look through there; don't just go by the cover," Dave started to
explain. "Check out the pictures inside."
Dave took the magazine out of my hands. "Claudia Schiffer; oh man, she's
hot!" he said, showing me again the cover.
"Yeah, she's hot," I said, looking at the picture of the tall, ultra
pretty blonde model.
"And David Copperfield, he's a magician like me," Dave said, "I do
tricks, right?"
Dave was good with card tricks, and he'd do that thing of pulling
quarters from behind my ears. "Yeah, sleight of hand. Right, you're
good at that," I said.
Dave flipped through the pages, then showed me the article from the
cover. "Here," he said, sitting down and showing it to me, "take a look
at these pictures."
The article had 4 or 5 pictures of Schiffer and Copperfield together. I
looked at each picture, trying to figure out what he wanted me to see.
"There!" Dave said, pointing to a picture with Copperfield dressed in a
black suit with a magician top hat and a wand. "Look at Claudia," Dave
told me.
Schiffer was sitting in a red sleeveless dress, with white strap heels.
She was posed as if Copperfield's wand was putting her into a trance. I
stared at the picture.
"Do ya see it?" Dave asked.
I looked up at him.
"It struck me as soon as I saw it," he said.
I looked back at the picture.
"That's us," he explained. "For Halloween, we're going as David
Copperfield and Claudia Schiffer."
I looked at him, and back at the magazine, back and forth, my eyes
squinting.
"I know you see it," he said, "I look a bit like Copperfield, and you
could easily be Schiffer."
A strange feeling rushing over me, I looked at Dave. "You want me to
dress up like a woman?"
"Well, like that woman," he went on. "See, I'll be in my magician
outfit, and you'll be dressed like a fashion model; I think everybody
will get it, the connection."
Dave went on, "I've already talked to my sister about it, and she thinks
it's a great idea; she says she can help you with makeup, and she can
get us a great deal on your clothes at her store. I've got a lot of
money I've been saying from shooting pool, so I can spend a little on my
wing man's outfit. If you want to do it, that is."
I was overwhelmed. I secretly loved the idea, but I was afraid of
showing it. I could easily see what Dave was talking about. Looking at
looking at the pictures of Claudia my mind was flashing in and out on it
being me. Not that I'm supermodel material, or anything, but I am tall,
thin, and blonde. On top of that, I could relate to Schiffer's
expressions, her eyes and smile, like a mental link.
I sat and looked up at Dave. He was standing over me pointing at the
picture of Schiffer and Copperfield, and it was like we slipped into the
pose of him, like Copperfield, putting me, like Schiffer, into a trance.
"So, do ya want to do it?" Dave asked.
"Yeah, okay, let's do it," I agreed.
"So, it's decided then," Dave said, "we'll do it!"
Dave went over his plan of taking me to the department store where his
sister works, saying she'd help me with the clothes and makeup and
stuff. I was just looking at him and nodding. I was sort of embarrassed
at how easily I was talked in to this, and at how excited I was about
it. It didn't seem to bother Dave, though; he was like the ultimate
macho guy, doing macho things, but he was always okay with me being shy
and quiet, and not very macho. I figured that was what made me a good
wingman for him; we were never in competition.
The next day Dave picked me up to go see his sister. "Diane said early
afternoon was the best time for her to help you. Something about not
being so busy, so you could use the dressing rooms."
"Okay," not arguing, I got in the Camaro, and we left.
"How ya doing?" Dave asked, probably noticing I was unusually quiet.
"Nervous," I said, glancing at Dave, "and a little embarrassed."
"Aw, don't worry; you'll look great!" Dave assured me.
"So, I'm going to have a makeover?" I asked.
"Yeah, makeup and styling, I guess that it," Dave said. "But today I
think it's more of a consultation, and you'll pick out some clothes,
shoes and stuff. The party isn't till next Saturday, I think you'll get
the makeover that afternoon."
I nodded, agreeing to everything. "Oh, okay, wow," I said, trying not to
sound too excited.
When we got to the store, Dave stopped at the customer service desk to
ask for Diane. "She's a manager here now," Dave told me. They paged
her, and we waited. I looked around at all the racks of classy looking
clothes, sexy mannequins, and the display areas with jewelry and
cosmetics. I was lost in it, when I heard Diane say "hi Danny!"
"Oh, hi Diane," I said, smiling. Dave's sister, who was a junior in
college, was very pretty and friendly. I admired her a lot.
"So, you're going to a costume party! It sounds so exciting and fun,
you must be excited!"
"Yeah," I said, "I'm a little nervous, but it does sound like fun."
"You're a cute guy, Danny," Diane said, capturing me with her eyes.
"You're blessed with nice features. I think you'll be surprised how much
you can look like Schiffer.
I was mesmerized by her positive energy. Diane and I smiled and chuckled
at each other. It occurred to both of us that we were having a girl
moment. Diane touched my arm. "This is going to be fun!" We both
looked over at Dave, I was relieved that he was distracted by girls
shopping, and didn't seem to notice the girl moment with me and his
sister. Diane said, "David, let me have Danny for a while."
"Yeah, sure," Dave said. He glanced at me. "Have fun," he said, "I'll
be back in a bit." With so many hot girls around, I was sure Dave would
make use of his time, but I still looked at him as he walked away.
Diana showed me around the store, non-stop chatting all the way. I was
feeling strangely giddy, and I felt I was starting to match Diane's
bounce as we walked.
"Here we are," Diane said, "club wear. This is what you want." I
looked around at the mannequins in short, tight dresses. "Club wear
tends to be figure-enhancing, and at the same time revealing." She
explained. "You want to be sexy when you're out, so people will notice
you and accept you" She looked at me with the slyest of grins, and we
had another girl moment, almost giggling about being sexy for attention.
Diane introduced me to a salesgirl, who measured me and showed me
several she thought would work for me,holding them up to me to gauge fit
and color. "I like this one," I said, holding up a red sleeveless
dress. I explained to her that I was trying to look for a costume party
like Claudia Schiffer from a picture in Esquire. "Oh, yeah, I get it!"
she said, looking at my face, and scanning up and down my body, with an
approving nod.
Just then Diane came back. "How's it going?" she asked. I showed her
my red dress, and explained how it looked like the one Schiffer wore in
that picture. "Oh, yeah, Dave showed me that picture," Diane said, "I
agree, yeah, that's the dress!" Then Diane handed me a new portable
shaver. "Here," she said, "I'm assuming you haven't shaved your legs
yet. You can't wear a dress like this with hairy gams. You can use
this in the dressing room."
Just then, Dave walked up. "Hey, how's it going?" he asked, looking at
Diane and me. He noticed the dressed I was holding and smiled. "Oh, we
have things to do yet," Diane said, "we need another hour or so." Diane
put her hands up to me like she was presenting me in a show. "You want
Danny to look good, don't you?" she asked rhetorically. "Yeah, sure,"
Dave said, I'll see ya in a couple hours then." He turned to walk away,
then looked at me. "See ya later, Danny," he said. "See ya, Dave," I
said, watching him walk away.
"He's going to love the way you look," Diane told me. I smiled
hopefully. Then Diane walked me back into the dressing rooms. She
checked each stall to make sure other women weren't using them. Diane
ushered me into a stall. "Hear ya go!" she said, and tapping the
shaver, "first your legs," then touching the dress, "then the dress." I
stood motionless inside the dressing stall for a moment, starting to
have a sense of what was happening to me. "I can see why Dave likes
you," Diane told me, with a comforting smile. Then she pulled the door
shut, and left me to get dressed.
I hung the dress on a hook, feeling the fabric with my fingers. Then I
took off my shoes and my jeans, and sat down on the bench. I took the
shaver out of the package, turned it on, and shaved my right leg, then
my left, till I was hairless from ankle to crotch. I was amazed at how
well the shaver worked, and at how great my legs felt. I rubbed my
hands over my skin, so smooth! I sat looking at my legs, moving them
around to catch the light from different angles. Then I looked in the
mirror and unbuttoned my shirt, slipping it off one shoulder at a time.
I used the shaver to remove the little bit of hair on my chest, then I
went ahead and shaved my arms. Standing up, seeing my smooth shaved body
in my white male briefs, I knew this would never work. I tapped on the
door, calling for Diana. Realizing I was in a woman's dressing room, I
consciously tried to feminize my voice, and was a bit shocked at how
well it sounded. I tapped on the door again, and called for Diane
again, half just to hear my own voice.
"Danny?" I heard Diana outside. I opened the door a crack and peeked
out. "We forgot something," I said. "You mean this?" Diana said,
handing me a bag. "It's panties and a bra," she said, "you absolutely
will need that!" "Yes!" I said, not able to hide my excitement. We
girl smiled each other through the crack in the door.
I took the panties and bra from the bag and carefully laid them on the
bench. They were beige, and the material felt fabulous. I pulled off
the coarse cotton boy briefs, folded them and put them on the bench. It
was pure thrill putting on my first pair of panties. I slid them up my
shaved legs, marveling at how they felt. I tucked around at my balls and
penis until they just looked like just a nice little bush under my
panties. Satisfied, I picked up the bra. It was strapless underwire, and
don't ask me how, but I seemed to intuitively know how to reach behind
myself to loop the hooks, and to work the cups up under and over my
breasts, lifting them to a nice little cleavage. The sensations going
through me now were like lightning. I was aglow and on fire as I looked
at myself in the mirror.
I took the red dress from the hanger, and looked it over. It was so
tiny, it was hard to believe it could get into it, or that it would
cover any amount of me. Diana called the dress a "bodycon," saying it
would hug and enhance my figure. I held the dress up over my head, and
standing straight and tall, pulled it down over my body, bra and
panties. I adjusted the straps on my shoulders, and the tugged gently
shifting the stretch waist till it felt right. I stood looking at
myself in the mirror, turning side to side, pose to pose. I looked as
amazing as I felt, I thought! Then I opened the door and stepped into
the hallway. Diana was at the cashier's desk, but came back to the
dressing area when she heard me open the door.
"Oh, my gawd, girl!" she said. "You look amazing!"
I instinctively turned and stood in different poses. My smile was
glowing.
"Girl, you are so pretty!" Diana said. "I see why David wanted to get
you dressed up. He does like pretty girls!"
Hearing Dave's name got my heart beating. And the way Diana mentioned
him, I wondered if more planning had gone into this than I'd realized.
Had Dave asked me to the party just to see me dressed up?
"You need shoes, Dani," Diana said. "Come on!" she said, and taking my
arm and leading me out into the store. She stopped at the cashier's
desk, took a brush from her purse, and did a quick styling of my long
hair. Then she took out some red lipstick and an eyebrow pencil and did
a quick job on my lips and eyes. "You'll learn how to do this for
yourself, Dani," she said. "Makeup is easy when your structure is so
naturally pretty!"
Satisfied, she headed over to the shoe aisle, me following her barefoot.
I couldn't help smiling at everyone who looked at me, and they all
smiled back. We got to the shoe section, and Diana told me to sit down,
then she talked to the salesperson there, who came over to measure my
feet. I was suddenly embarrassed that my nails weren't filed and
polished; the sales girl obviously noticed. "You're going to get a
pedicure, too," Diana broke in, "along with your manicure." I looked at
my sad looking nails, and nodded.
"You have very long, narrow feet," the salesgirl said. "Luckily, we are
one of the few stores that carry your size." She got up, "here, let me
show you what we've got." I got up and followed the sales girl to look
at the shoes. "Your best fit will be size 10, B width," the salesgirl
said. "Most of the shoes on this rack, and this table, come in that
size."
I picked out a nice looking pair of white strap heels, and the girl went
in back to get my size. I sat down, the girl came back and fitted me in
my new shoes, then she offered her hand to help me stand. I stood for a
moment, gauging the feel, then took one step, then another. I felt
quite fine, and walked a few steps down the carpet, turned and walked
back.
"They feel great!" I said. "They look great!" Diana said.
Diana told the salesgirl she'd get the credit, but that we would be
ringing all of my purchases at another register. Then we walked back to
the dressing room.
"You walk well in heels," Diana commented, "is this really your first
time?" "Except for when I was little, playing in my mom's shoes," I
admitted. "Ah," Diana said, "so you knew then already." I looked at
her, and I knew what she was saying, but I was kind of stunned by it
anyway.
"Okay, girl!" Diana said when we were back in the dress department,
"it's a shame, I know, but you're going to have to bag all this stuff
and get back in your drab jeans and shirt. You don't want David to see
you looking like this just yet." The implication of what she said
stunning me even more than I was already stunned.
So I went back to the dressing room, reluctantly took off my wonderful
new clothes and shoes, putting my dress back on it's hanger, my bra and
panties back in their bag, and my fabulous shoes back in their box. I
put back on my guy white briefs, my jeans, shirt and tennis shoes. As
much as I dreaded switching back to drab, oddly, I still felt like a
girl wearing it. Hmm, I thought, dresses are powerful!
When I went back to the counter, Dave was there. "Hey," I said. "Hey,
Danny," he said back, smiling at me.
Diana said she'd write my things up on her employee discount. I said I
could pay for it, but Dave jumped in right away saying "No way! This
treat's on me!" I smiled, and Diana smiled, and we looked at each other
and had one more secret girl moment.
"Oh, wait!" Diana said. "Let me wipe your lipstick off."
Embarrassed a little, having forgotten about it, I glanced at Dave.
"Looks good," Dave said casually, "you can leave it on if ya want."
Diana and I shrugged. "Okay," I said, maybe a little too happily. I
thanked Diana and started to walk out with Dave.
"Oh, wait!" Diana stopped me, coming over to whisper in my ear. "If
you're wearing makeup, you really ought to put this back on." And she
pointed to the bag with my panties and bra. "Oh, yeah!" I said, and
told Dave I needed another minute.
Back in the dressing room, I quickly took off my jeans, put my panties
back on, readjusting my works, then slid the bra up under my shirt,
working it around my boobs. Jeans back on, I walked out smiling at
Diana, puffing up my cleavage while David was looking away.
"Okay, ready," I said.
"Wow," David said, looking at me. I waved bye to Diana, and David and I
walked slowly out of the store, bumping shoulders along the way. I felt
like I still had some of Diana's bounce in my step.
Back at the Camaro, Dave opened my door. "There ya go!" he said. I
looked at him and slid in.
We cruised around just like always. I turned on the radio. "So, it was
great, wasn't it?" he asked. "Yeah," I answered, "it was really great."
"So, I guess you're really up for this," Dave said, "I mean, for
dressing up and going to the party."
"Yeah, it's a great idea," I said. "Diana convinced me. It will be
fun, I'm looking forward to it" Dave looked at me and smiled. I smiled
and leaned back in my seat, noticing my breasts raising up a bit as I
did.
"Can I ask you something?" I said, looking over at Dave.
"Sure," Dave said, "what ya want to know?"
"Is this about me dressing up so we can go to that party, or is it about
we're going to that party because you wanted to see me dressed up?" I
asked daringly.
"Hmm, good question," Dave said. "Which one do you think it is?"
He snickered, and I think we both blushed.
"Another question: is there really a girl you're hoping to see there?
"Yeah, there is," Dave said, "you!" and he poked my arm.
"When I'm a girl, I want to call you David, instead of Dave. Is that
alright?" I asked.
"Sure," David said. "I like that." Then he added, "And I can still
call you Danny, except we both know it will be the girl Dani, right?"
I giggled and smiled. "Right, David."
"I like you, Dani," he said, "you're fun to be with, and you look great
now, too!"
"Thank you, David," I said. "You're wonderful."
"I think Dani will be my new wing girl," David said, giving me a very
nice look.
"She is already," I said. Leaning back smiling dreamily.
David revved up the Camaro and got on it a bit. I loved the feel of the
power carrying me down the road.
Ofelia
- 13.06.2020
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