Head First

The wig shop occupied a storefront on the business loop. It was
next to a nail salon on one side and a muffler repair shop on the
other. Dennis sat in his car for a long couple of minutes as he
looked at it. It didn't look like much. He could hear the
equipment from the muffler shop and he knew that every eye would
be on him as he entered the wig shop. He believed so, anyway. He
had never been shopping before. Not for girl stuff.

He took a deep breath, opened the door to his car, and stepped
out.

The door to the shop was hung with cowbells that clanged dully
behind him as it swung shut. Shelves lined the walls of the shop,
on which stood a dizzying array of hairstyles, each perched on a
Styrofoam head. The center aisles were stocked with cosmetics in
colors and shades from mild to wild. The register sat on a glass
counter that displayed a multitude of false nails and related
products in a bewildering riot of polychromatic styles. Two
smiling Korean women stood behind the counter.

His heart was beating in his throat as he walked up and down the
aisles, looking at wigs. He fingered the tags on styles he liked,
but he was afraid to pick one up for fear that he would betray
his intentions. He came back to one or two styles that he liked.
The one that appealed to him most was a long, full style in dark
auburn with blunt cut bangs. It was made of real human hair, so
it was one of the most expensive styles in the store.

One of the shopkeepers came up behind him and asked: "Would you
like to try it on?" Dennis felt a constriction in his chest when
the question was asked.

"Oh, no... I couldn't," he stammered.

"Go ahead," came another voice to his left. It was another
customer. A man. Dennis had been so wrapped up in himself and his
fears that he hadn't even noticed other customers. The man was
thin--willowy, even--and slightly taller than Dennis. He had
short cropped hair that was dyed blond. He had a pair of studs in
each ear. "That style will look good on you," the man continued.

Dennis looked from the man to the wig to the sales lady and back
again to the wig. He took a deep breath. "What the heck." He took
the wig down, smoothed his hair back, and put it on. When he
looked in the mirror behind the counter, he didn't like what he
saw.

The other customer stifled a laugh. "That will never do. Let me
adjust that for you." Dennis acquiesced and allowed the man to
tug the wig into place. "Do you think this would look better with
the bangs trimmed, Tomiko?" he asked the sales lady.

"Yes," the woman said, adding a bow for emphasis. She retrieved a
pair of scissors from behind the counter and proceeded to trim
the wig just above Dennis's eyes.

"Perfect," the man said. Tomiko, the sales lady nodded in
agreement. Dennis saw the results in the mirror and was struck
dumb. It DID look good on him. He knew that he had to have it. He
reached for his wallet.

As he removed the wig from his head, and handed it to the sales
lady to bag for him, the other customer introduced himself,
offering him his hand to shake. "I'm James," he said. He leaned
towards Dennis and whispered conspiratorially: "This is your
first time out shopping, isn't it?"

Dennis laughed nervously. "Pretty obvious, isn't it?"

James grinned broadly. "Yes. I made you a mile away. Of course,
not many men come in here." James grabbed a wig from the shelf.
"What do you think of this one?" It was a short, blonde, gamine
wig feathered around the face. "Is it me? Oh! You'll need some
wig caps with that. Get the fishnet ones with the open top.
They're the best ones." He turned to the sales lady. "Bag this
one up for me, Tomiko. And some of that champagne-colored nail
polish, too."

Dennis finished making his purchases. "I'm Dennis," he said to
James. "Pleased to meet you."

"Pleasure. Do you go out at all?"

"No, never."

"Too bad. I'm going to be at About Face tonight. I was hoping you
might come see me."

"I don't know where that is."

"Oh, it's a gay bar out off Academy Road. It's two lights past
McDonald's. You can't miss it. Tonight is their weekly drag show.
Will you come?"

"You're performing?"

James smiled enigmatically. "I'm not performing personally, but
my alter-ego is. Come out and meet her, if you like."

Dennis nodded. "Okay," he agreed, his voice and posture meek.

"Great! I'll see you there."

---

What the hell am I doing, Dennis asked himself. He asked it in
his mind over and over as he drove out to About Face. Dennis had
never been to a gay bar. He rarely went out at all. He spent most
of his evenings at home with his cat, reading or watching
television. He was terrified and exhilarated at the same time.
The day had started as a harmless adventure to indulge his secret
crossdressing, but now it was escalating. He hadn't dressed to go
out. He wasn't ready for that yet. But he had on a pair of black
French cut panties and a matching silk camisole under his jeans
and chambray shirt.

As he had done at the wig shop, he sat in his car for several
long minutes to get up his courage. It was an effort of will to
open the car door and step out. He walked slowly to the front
door of the bar.

There was a well built young man at the door with a close-cropped
black goatee and a blond crewcut. He was wearing a pair of black
latex jeans. "There's a three dollar cover tonight," he said.
Dennis fished three one-dollar bills from his wallet and showed
the man his driver's license. Dennis noticed a couple of men
checking him out as he walked to an empty table set back from the
dance floor and stage. He looked around for James, but didn't see
him. Nor did he see a woman who looked like James. He did notice
a couple of women at the bar who were kissing. Dennis began to
get an erection in spite of himself. He squirmed in his chair in
spite of himself. There were a number of same sex couples engaged
in displays of affection around the bar. A television above the
bar proper played a gay porn film in which two men who looked
like marines sucked each other's cocks.

Dennis had never thought of himself as gay, but in spite of this,
the surroundings were having an effect on him.

A waitress came by and took his drink order, a Michelob, and
eventually, the houselights dimmed and the show began.

The emcee was an elephantine drag queen who billed herself as
Amanda Devore. She was dressed in a sparkly gown that did indeed
make her look like a "full figured" woman and she had the voice
down pat. She sounded a little bit like Kathleen Turner. After a
short routine of dirty jokes, she introduced the first
entertainer. "Put your hands together for Miss Zoe Trollop!"

Miss Zoe Trollop was tall. Very tall. She wore a pair of seven
inch platforms, which made her even taller. She also wore a skin
tight pair of leather pants that curved over feminine hips, a
black leather brassiere, and a sparkling, transparent black cloak
trimmed with marabou. Her make-up was impeccable, featuring
cranberry lip liner that tapered off to a peach highlight on the
round parts of her lips, and eyeliner and eyelashes that made her
eyes the most prominent thing on her face. She wore a red wig in
a Jackie-O style that fit the image to a "T." She glided over the
dance floor in a slinky rendition of En Vogue's "Don't Let Go."
She got a lot of tips and kissed most of the men and all of the
women who tipped her. Dennis caught a glimpse of the flesh of her
breasts as she bent over one lesbian and waved them. Dennis was
sure they were real.

The second performer billed herself as "Little Diva" and was a
short blond in a teal and blue leotard that trailed a train made
of peacock feathers. Even in six inch heels, she was shorter than
Dennis--she couldn't have been more than five foot one in
stocking feet. Her make-up was more obviously "drag" make-up,
with overdone lip liner and blush. She was energetic, climbing
over tables and customers in time with Shania Twain. She mimed
giving head to one man who tipped her, and placed her crotch in
the face of a boy the emcee pointed out as a straight guy. Dennis
was thankful he wasn't sitting near the front.

Dennis watched the first two performers in a daze. He couldn't
take his eyes off their crotches or their hips. He wondered what
they did with their genitals and how they got such feminine
curves.

The third performer was a gorgeous brunette who was billed as
Miss Jasmine. She glided out onto the stage to a torrid Wanda
Jackson blues song wearing a PVC corset over a PVC mermaid hobble
skirt and a velvet cape that attached to her shoulders and
wrists. Dennis didn't recognize the song, but he recognized the
girl. It was James. Only now, instead of being willowy, he--she--
was voluptuous. Dennis's jaw hung, slack, from his face. Miss
Jasmine noticed Dennis in the audience and winked at him. This
prodded Dennis to fish a dollar bill from his pocket and approach
the stage. As Jasmine took the bill, she whispered to him: "I'm
glad you came. I'll come talk to you after the show."

The fourth performer was another tall girl, made taller by
insanely high heels. She wore a sparkling red dress encrusted
with rhinestones and lip-synched to Donna Summer's "I Feel Love."
She moved carefully across the stage, lest she tumble off her
heels, but she was otherwise elegant. The audience liked her.
Dennis missed what her name was, but it didn't matter much to
him.

Each of the performers did two more numbers in ever more
outrageous outfits. When it was finally done, the dance floor
filled up and Dennis made his way to the bar. As he waited for
another drink, he felt a hand on his shoulder. He turned around.
Jasmine was standing behind him.

"What did you think of the show?" she asked.

"It was interesting. You look fantastic."

She had changed into a gold lame miniskirt and a semi-transparent
black blouse that showed her black lace bra underneath. She
towered over him in her five inch heels. She curtsied to him.
"Glad you like it. How come you didn't dress up?"

"I'm not ready for that. I've never been out in public. I can't
believe I had the nerve to come here tonight. I almost chickened
out. I would hate to be seen next to you in drag. I would look
like a frump." Dennis took a swig from his beer.

"Nonsense," Jasmine said. "You would look fine. You've got good
features. Your beard is a little heavy, but I've seen worse.
You're in good shape, so you shouldn't have any problems finding
clothes."

"I have clothes. I've been buying stuff mail order for years.
Nothing fancy, though. Not like what you wore tonight."

She smiled. "Well, you can't go grocery shopping in a get-up like
this one." She paused. "Care to dance?"

"Uh... sure. But I dance like a white guy." She took his hand and
led him to the dance floor.

They danced for about an hour before last call. Jasmine had a few
drinks between songs and was flushed with alcohol and exercise
before the night ended. She was slightly drunk by then and asked
Dennis to give her a ride home.

"I had a great time," Dennis told her as they pulled up to her
house.

She smiled. "You'll have a better time if you get dressed up next
time." They traded phone numbers. She gave him a kiss on the
cheek before she opened the door and stepped out. "Give me a hand
with my stuff?" she asked.

"Sure." he said. He stepped out after her.

She had a garment bag with her show outfits and a make-up case.
He carried them both as she fished in her purse for her keys. She
opened the door and turned on a lamp. After she set down her
purse, she took her things from him and carried them into a back
room. As he waited for her to return, he looked around at her
home. It was tidy, with a beige suede couch and chairs, glass and
chrome tables and bookshelves, and abstract art on the walls. He
wandered over to one of her paintings and came to the startling
realization that it was an original Mondrian, not a print.

"Wow," he said aloud.

She returned from the back and asked him if he wanted a nightcap.

"I shouldn't," he said. "I have to drive home."

She pouted in disappointment. "I understand," she said. She
walked over to him, closer than he was comfortable with. She
draped her arms over his shoulders and kissed him on the lips.
"Well, if you're sure..." She kissed him again, with her tongue
this time. "I guess this is good night."

Dennis's face was burning as he disentangled himself from her.
"I... I have to go," he said, fumbling at the doorknob."

Jasmine let him go, realizing that she had gone too far. "Okay.
Drive safe, hon. Call me tomorrow and we'll go shopping." She
smiled at him.

It was all Dennis could do to close the door behind him and walk
back to his car.

"I'm not gay," he said aloud to himself. He repeated it several
times as he drove home, but once there, he stripped to his
camisole and panties and masturbated himself silly with thoughts
of the evening.

---

"How did you get such a flat... well... you know?" Dennis asked
James over lunch.

James smiled broadly. He was noticeably femme today, as if his
feminine self hadn't quite shaken herself out of his body while
he slept. His eyes were still made up, too. His clothes, jeans
and a white blouse, were girl's clothes, even though they were
masculine cuts.

"Duct tape," he said.

"And the hips?"

"Sofa cushion I took a kitchen knife to." James took a bite from
his sandwich as Dennis mulled over his responses.

"Doesn't duct tape hurt?"

"It hurts like a motherfucker if you put it directly on the skin
of your wee wee. That's why I put a pair panties on first, then
tape over the panties."

"I see..."

James winked at him, then smiled around the straw of his soda.

"Where are we going shopping?"

"I don't know. A dress shop I know that will let us try things
on, probably. Raven's Lingerie Shop. Probably the MAC store."

"The MAC store? What's that?"

"Make-up, honey! Best stuff out there! We'll get you a color
analysis while we are at it."

At the end of the trip, Dennis had an armful of bags. He had put
a strain on his credit card, especially after James had suggested
that he get a Victorian corset. "You'll love the look," he said
as the girl at the lingerie shop took his measurements. The
garment she sold him was dark green velvet. He bought a pair of
matching stockings and some marabou mules with five inch heels.

It was disturbing getting a color analysis at the make-up shop.
The woman who attended him, began daubing his cheeks with
foundation and blush right in the middle of the store, amid the
Saturday afternoon customer traffic. Dennis was shocked that no
one even batted an eye. He ended up with a personalized make-up
kit that cost more than Dennis even dreamed was possible. When
Dennis balked at paying such an extravagant amount, James handed
the girl his platinum card.

"You need this, hon," he whispered to him.

Dennis was sure the girl thought that he and James were gay
lovers. He wanted to die of embarrassment. Dennis also wound up
with two dresses (including a red pvc mini dress he wasn't sure
he could ever bring himself to wear outside), a couple of skirts
(including a scandalously short leather mini), and a few tops.

That evening, they returned to James's house. Dennis sat heavily
on the couch as James picked up the phone and ordered Chinese
food. As they waited for it to be delivered, they talked.

"Did you have fun?" James asked.

'Oh, yeah," Dennis said. "Had a blast, even when I wanted to
crawl into a hole and die from embarrassment. I can't believe how
much stuff we got."

"I wouldn't be embarrassed, hon. Your money is as good as
anyone's. Besides, nobody cares. The clerks work on commission,
so if you spend a lot of money with them, they love to have us.
As for the rest of the customers, they don't know you and you
don't know them, so who cares what they think."

"What if I ran into a client?"

"Did you?"

"No, but..."

"Trust me, they wouldn't have cared. I doubt that they would have
realized why you were even in the store... except when we were in
the MAC store, and if they were there, chances are that they
wouldn't have batted an eyelash."

The Chinese food got there and they ate. James warned Dennis not
to eat too much if he wanted to get into his new corset. He
winked at him. After they finished eating, James went out to the
car and brought in all the bags, including Dennis's.

"Wanna play dress-up?" he asked.

A mild look of panic crossed Dennis's face. "Oh, I couldn't
really..."

"Sure you could. I don't think it's fair that you know what I
look like as a girl, but I don't know what you look like. C'mon,
it'll be fun."

"Well..."

James smiled and pulled Dennis up from the couch. He marched him
to the bathroom. "There are razors and shave cream in the shower
stall if you want to shave your legs or any other part. Let me
know if you want help." He winked at Dennis.

Dennis didn't need to shave his legs. He shaved them every other
day at home. He kept his body completely free from hair below the
waist. He did need to shave his face though. It took him twenty
minutes to get a really close shave. He was careful not to cut
himself.

When he emerged, James had begun changing into Jasmine. It
occurred to Dennis that Jasmine had no beard shadow at all. He
wondered about that. Maybe he shaved in another part of the
house.

"Ditch that lumberjack drag, hon and put this on," Jasmine said
to him, holding out a light silk dressing robe. Dennis returned
to the bathroom, closed the door, took off his clothes down to
his camisole and panties, put on the dressing robe and came out
into the bedroom.

"Very definite potential," Jasmine said. "Come sit at my vanity
and we'll do your make-up."

Jasmine took his hand and sat him in front of the mirror. She
gave his face a long look before she reached for any cosmetics.
She stroked his eyebrows with her index finger to see how they
lay. A smile flashed across her lips, apparently satisfied with
the brows. She began with a stick foundation and a dusting of
loose powder. She had an old fashioned powder puff for this last
operation. It tickled Dennis and he had a hard time suppressing a
giggle as she dusted him. Eyeliner was next. She manhandled his
eyelids during this operation, but she was careful not to poke
his eyes. She took an inordinate amount of time with his eye
shadow, using at least three or four different colors of shadow.

As she coated his lashes with mascara, Jasmine said, "We need to
get you some false eyelashes, hon. This will just have to do for
now." She also shaped his eyebrows with the mascara wand. She
saved his lips for last, meticulously lining them and working
inward with rose lipstick.

Meanwhile, Dennis was squirming in his seat. His crossed legs
concealed a raging erection. He didn't move much during the whole
procedure. He was afraid that Jasmine would notice just how
excited he was and he wasn't ready to face the consequences.

Jasmine finally placed a brunette wig in a Gibson Girl-style on
his head and arranged the hair carefully. After a light spritzing
of wig spray, she pronounced him "finished," then shooed him into
the living room and closed the door behind her. Dennis shrugged,
then began sorting through the bags of stuff they had purchased.
He was going to wear the corset, he decided. He put on the
matching thong. It bulged dramatically, and he closed his eyes
and did some multiplication tables in his head to make his
erection detumesce, then he tucked his privates between his legs
and pulled the thong tight to hold it in place. He followed it
with the green stockings that matched the corset. They were stay-
ups, but he would attach them to the corset 's garters once he
was laced in.

That was the big problem. He didn't know how to get into the
corset by himself. He fumbled the busk of the corset so that it
was on him and he attempted to pull the laces closed. It was a
struggle and he wasn't satisfied with the results. Suddenly, he
had an inspiration. He looped the laces over the knobs of the
door to Jasmine's hall closet and let his own weight pull the
corset closed. It constricted around his midsection, reducing his
waistline severely and shaping his torso into a feminine
hourglass. He wrapped the laces around his midsection and tied
them at his front. He wasn't dexterous enough to tie them behind
him.

He then slid his feet into the mules. He had never dared heels so
high before. It took a second for him to get his balance, then he
took a few tentative steps to see if he could walk in them. He
realized that he had to walk from his hips in heels that high. He
felt feminine. He felt delicious. He wished there was a mirror in
the front room so he could see what he looked like. He fished a
diaphanous green robe that matched the corset and stockings out
of his bag, bit the price tag off of it, and slid into it. He sat
on the couch to wait for Jasmine.

He didn't have to wait long. She opened the bedroom door and
emerged wearing a black satin corset of her own, with a pair of
seven inch platforms on her feet, fishnets on her legs, and a
riot of black chiffon black feather around her shoulders and
trailing behind her behind and legs. She wore a blonde wig with
blunt-cut bangs and a mound of hair in back that trailed down to
the middle of her back. She had a single diamond hung from a
slender silver chain around her neck and two diamond pendants in
her ears. She was immaculately made up.

"Wow," was all Dennis could say. This brought an immediate smile
to Jasmine's face.

"Glad you like it," she said. "I had this old thing lying around
and I thought I would see if I still like it." She sauntered over
to Dennis and pulled him to his feet. "Let's have a look," she
said.

Dennis did a slow walk to the center of the room, then turned
around to show her the whole outfit.

"Verrry nice," Jasmine said. "Wait right there! I want to get my
camera." She minced to the hall closet and pulled a digital
camera from the top shelf.

"Show me some cheesecake, sweetie," she said as she aimed the
camera. Dennis tried his best to strike a sexy, feminine pose.
This was made fairly easy for him by the corset, which seriously
restricted his movement. Jasmine continued to take photos as she
goaded Dennis into more and more provocative poses.

"These will look fabulous!" Jasmine said, closing the lens cap.
"Let me get something to drink and then you can take some of me."
She fetched two glasses of wine and handed one to Dennis.

Jasmine was a natural in front of the camera. The feminine grace
that made her an electrifying stage performer translated to her
poses and Dennis was sure that she practices posing as part of
her act. After Dennis finished shooting her, she popped the disc
out and loaded another.

"Let's see what you look like in that PVC number!" she said.

Dennis was game, so he changed into the red PVC mini dress,
changed into a black thong and a garter belt, and changed his
stocking for black fishnets. Jasmine gave him some red sandals
with a six inch heel to wear. They took more pictures and drank
more wine and giggled like schoolgirls well into the night. When
at last they ran out of outfits to shoot, Dennis collapsed onto
the couch and rubbed his aching feet. He'd never worn heels that
high for that long before. He was wearing a white babydoll with
marabou trim by this time, with a white satin thong and white
stockings. He had removed the shoes, though.

Jasmine, sat next to him and poured him another glass of wine.
She was wearing a bustier in burgundy velvet by now, with
matching g-string and stockings.

She smiled at him. "Did you have fun today?" she asked him.

"Oh, God yes," he replied. "Today was fantastic! I had a blast."

"I'm glad," she said, looking into his eyes.

Then she leaned over and kissed him on the lips. Dennis had lost
some of his inhibitions from the other night and between the wine
and the sexy outfits Jasmine had been wearing all night, he was
aroused. Jasmine took his acceptance as a sign to go further and
she kissed him again, probing his lips with her tongue this time.
Dennis closed his eyes and let her kiss him. He was barely aware
of her probing hand, when it released his manhood from the thong
that had kept it confined. He didn't object when she began to
stroke him slowly. He returned her kiss passionately and drew her
to him.

Eventually, she broke for air. Smiling sweetly at him, she said,
"The night's still young, darling. What shall I call my beautiful
girlfriend?"

"Diana," he--now she after giving herself a name--said without thinking.

"Kiss me again, Diana."

She complied with a vengeance. They embraced in a deep soul kiss
as Jasmine continued to stroke Diana's erection.

She finally pushed her away and said, "We can't let this go to
waste."

She slid to the floor and positioned herself between Diana's
legs, smiled up at her, and then went down on her with a purr of
hunger. Diana closed her eyes and enjoyed it. Jasmine was
obviously experienced. She fluttered her tongue on the tip
several time before taking it deep into her mouth and throat. It
didn't take her long to come. She had been excited all evening
and this brought things to mind-blowing climax.

Jasmine swallowed everything that erupted from Diana, then
licked her clean. This sent aftershocks of pleasure through her
body. Then she slid back up the couch and snuggled in close to
Diana, kissing her bare flesh everywhere she found it on the way
back to her crimson lips.

"Mmmm..." Jasmine cooed in her ear. "I think you liked that,
too."

"Gawd, that was fantastic," Diana sighed.

"Would you like to do that to me?"

Diana opened her eyes and gazed at Jasmine's lovely face. She
realized that she DID want to do that for her. "Yes," she agreed.
"But I've never done anything like this before... I don't know
how."

Jasmine stood before her, took her by the hand and pulled her to
her feet. She led him to the bedroom. Looking back over her
shoulder, she said: "Don't worry, darling. I'll teach you. I have
so many things to teach you..."