Holli Earns Her Wings ? by: Nova
If you are less than eighteen years old or offended by material of a
sexual nature, read no further. Although this story is autobiographically
based, all names and situations have been fictionalized and any
resemblance to any real person or event is purely coincidental.
ONE
Early in my career as a design-builder I decided to take on a housemate
to help keep myself financially comfortable while my client list grew. I
had started my business about three years earlier with a partner after
generating some contacts while I interned at an architect and then
construction firm during graduate school.
After several weeks of running ads and interviewing prospects, I finally
found someone whose lifestyle was compatible with mine. Jenni called
about my ad and after answering a few basic questions we made an
appointment for her to come over and see the place later that same Sunday
afternoon. She explained over the phone that she was tired of sharing a
three bedroom house with three other flight attendants whose boyfriends
often spent days at a time under the same roof. My offer turned out to be
a great situation for both of us. I spent most of my time at the house
because I work out of my home studio, and because Jenni worked as a
flight attendant, she was out of town for many days at a time. This was a
great arrangement but not the foremost reason I chose her to move-in.
A knock at the front door signaled her punctuality. I peered through the
peep-hole and spontaneously grinned like a maniac. She was beautiful
resembling a brunette Gweneth Paltrow but with larger breasts. At first
glimpse, I knew I wanted her to move in. I took a moment to compose
myself then opened the door, introduced myself, and invited her in for a
tour.
"Hi, you must be Jenni," I said reaching out to shake her hand, "I'm
Harry, please come in and let me show you around"
Beginning with the main floor of the house, I first showed her the living
room, dining room, kitchen, and media room, before moving upstairs to the
bedrooms and terraces. Returning downstairs, we headed out to the
backyard as I pointed out, among other things, the property's voice
controls and security system. We then walked around the pool to the
studio at the rear of the property that also serves as my business
office.
She asked, "So you're an artist?"
"Well, actually," I replied as we walked in, "I'm a design-builder, sort
of like an architect, but in my spare time I do like to paint and have
been lucky enough to sell a few pieces." I went on to say that the studio
is a working office on weekdays for myself, my business partner and our
one employee. "The neighborhood is zoned for mixed use; some of the
buildings along the street are homes, some are small offices, and some,
like mine are both," I explained.
The studio is a single large room, about 20' by 35', with a series of
sliding glass doors serving as the wall facing the pool, plus floor to
ceiling windows in the two side walls for maximum daylight. The back wall
is normal sheetrock covered with working designs plus photos, awards,
licenses, diplomas and other mementos. My business partner Jeff and I
each have a work area at opposite ends of the room while our assistant
Carie has a desk in the center facing the pool.
Decorated with a sofa, a pair of club chairs and a large low table. the
space behind Caries desk serves as the reception area. I handle the
design side of the business and Jeff handles the actual construction side
of the business.
While I rambled on about a current project, Jenni paced across the floor
checking out some of the paintings, designs and photos on the back wall.
She stopped abruptly, motioning to a particular photo and asked, "Isn't
this Holli Harryson?"
Surpised by her recognition, I stammered, "Oh, uh.. yes it is."
"She's beautiful," Jenni said. "I used to hang out with some other flight
attendants at the club where she worked. How do you know her?"
"Well," I replied while taking a deep breath, "she's me."
Jenni's face widened in surprise as she exclaimed, "No way!"
Jenni reminisced aloud about her experiences at Candi's, a local club and
showbar that featured drag and gender illusionist shows, and then asked
me if I still performed. I explained to her that I worked a while at
Candi's because of encouragement from my ex-girlfriend Kim who knew some
of the performers through her business. Kim thought I could make some
easy money there because of my looks and build.
"Her business?" Jenni asked puzzled.
"Yea," I replied, "Kim owns a salon where a few of the 'girls' are
regular customers."
"Is she a hairdresser?"
"Actually, hair, makeup, nails, everything," I said, "and she use to
practice on me. Anyway," I sighed, "I guess that's how I got started.
She'd spend an hour or two doing this and that to my face and hair and
then tell me I looked at least as good as anyone working at Candi's.
Things just progressed from there."
Staring at my portrait I said, "She was right ya know. On a busy weekend,
I could easily make $500 a night if I waited tables and worked on stage.
All I really needed to do was look pretty and be a little flirty and the
tips would get bigger and bigger. Guys and girls alike were constantly
propositioning me."
"So you don't do it anymore, I mean female-impersonate or whatever you
call it?" Jenni asked.
"No," I said, "not at a club, but at the time I made enough money to put
myself through graduate school. Just before getting my master's degree, I
came into a small inheritance and used it plus my Candi's money to
remodel this house."
"Wow.. so how long have you lived here?" she asked.
"I've lived here for about four years and me, Jeff, and Carie moved the
office into this studio a little over a year or so. Moving in here saved
us the rent and utilities we paid at our old office downtown, plus I get
a pretty good break on my personal income taxes"
Feeling comfortable with her I smiled, changed the subject, and asked,
"Jenni, do you have time to sit down for a cup of coffee? I think we'd
make great housemates and I'd like to figure out a price and a date you
could move in if your interested."
She smiled back and said, "Sure."
Returning to the main house, I brewed some coffee as we began to chat. We
quickly agreed on a price and date and soon thereafter the conversation
returned to my 'Holli' protrait. She said she thought I resembled
Nicolette Sheridan. I wasn't quite sure who that was at the time, but I
took it as a compliment. I elaborated on what I had told her in the
studio explaining that I have been crossdressing since childhood and
still did so regularly.
She said she was 'cool' with that and added it would be really neat to
have a guy roommate with whom she could talk about 'girl-stuff.' She
began to indirectly raise the subject of my sexuality, but before she
could thoroughly embarrass herself, I rescued her by saying, "I'm a
straight guy and a lesbian girl!" going on to explain that when I'm
dressed as a man, which is most of the time, I'm only attracted to women,
but when I'm dressed as a woman, anything goes. At work, I'm just my
ordinary regular male self, although Jeff and Carie both know I
crossdress and are aware of my past.
She laughed as I further explained that in most of my everyday life,
being only 5'7" and a thin 130 lbs, with long wavy blonde hair and no
muscle tone, has made dating women a challenge. "In high school, I was
the guy who had lots of female friends and always the last one picked for
any team sport," I said. "As a guy," I continued, "I don't have much luck
at all, but as Holli I am constantly being hit on."
Jenni squealed, "You should go out with me to a gay bar then! The guys
there aren't looking for anything other than the occassional dance," and
continued, "I love it whenever I'm crewed together with a male flight
attendant because, like you may have guessed, most of the guys are gay
and know some really cool clubs to go to. And the best part is the pilots
never go to the same bar as the guy flight attendants."
I asked what the problem was with pilots and she told me about how
horrible it would be for her and for some other girls whenever they were
crewed together with particular pilots who thought of themselves as hot
studs. Some constantly hit on the better looking female flight attendants
while treating the less attractive females and all the males like dirt.
After ranting for a few minutes she finished and said, "I'm sorry, it's
just that I wish there were a way to humiliate one of those pilots the
way they humiliate some flight attendants."
TWO
Shortly after Jenni moved in, she fell into a routine of sorts leaving on
trips of three to four days then staying home for two or three days
straight. She loved to cook so when she was off she would insist on
making dinner every night. I didn't have any objections because it turned
out she was great in the kitchen. I did, however, insist on buying the
groceries and doing the dishes. Since her trips back home usually ended
late in the day, I would make dinner those particular nights.
Besides dinner, we started doing other things together including going to
movies, shopping, and eventually to clubs. Mostly we'd go as a guy and a
girl, but every once in a long while, I'd dress up and we'd go as a
couple of girls. I particularly enjoyed our shopping trips because we
wore the same sizes except for shoes and bra. One night, over dinner,
Jenni said, "Can I ask you what may be a very personal question?"
"Well," I replied, "that depends on what it is, but go ahead."
She put her fork down, folded her hands in her lap, and then leaned
forward to me a bit. "Over the past couple of months I could't help but
notice, ...how should I say this? You're always wearing baggy sweats or a
coat and tie, and mornings you're always wrapped in have that big fluffy
robe; there's a beautiful pool out back you never seem to use..."
"Don't worry, just get it out," I interjected.
She strained trying no to offend me and stammered, "What I'm trying to
say is, and any answer is okay with me, but do you have, ...um, I mean,
are you trying to hide your body or something?"
I burst into laughter. "Hey, don't laugh. I'm sorry I brought it up,"
Jenni frowned.
"No, no, no," I said, "it's just that you looked so serious I thought you
were gonna ask me if I ate babies or something else as ridiculous. But to
answer your question, let me show you." I pulled the zipper down my
fleece warm-up then tugged the sleeves from my arms. I pulled loose the
knot on my sweatpants and let them fall to the floor. I was wearing
nothing but a pair of high cut underpants as I turned around then back to
give her a look at me from all angles. I could see Jenni's eyes widen as
she stared at my my girlish figure.
"Wow," Jenni whispered, "How in the world could.."
I cut her off finishing her question, "How in the world could a twenty-
six year old guy have a body like an eighteen year old girl?"
She smiled and added, "If you had breast implants you could be a swimsuit
model!"
"Remember when I told you I how horrible it was for me growing up? I
wasn't kidding," I said, "In fact, the first girl I had sex with later
realized she was a lesbian." I expected Jenni to laugh at this
revelation, but all she did was express a compassionate sigh.
"Body shape notwithstanding, I think you're a beautiful person inside and
out," she added warmly.
"Thanks, don't get me wrong," I said, "I love my body now. I hated it for
years, but it turned out to be a blessing in disguise," I continued on to
explain how, after years of shame in high school and part of college, I
took advantage of my appearance with the help of my ex-girlfriend Kim.
I got my job at Candi's because of Kim. One of the showgirls, Toni,
happened to come to the salon one afternoon and saw me after Kim had
given me a makeover. Toni, who was actually the hostess who ran the shows
at Candi's, told me and Kim that I was a natural and would fit right in
with the line-up of performers at the club. I was hesitant at first, but
a couple of weekends later I was waiting tables and lip-synching to
Spice-Girl songs. I always seemed to have to play women who had a little
baby fat like Baby Spice, Marilynn Monroe, Heather Graham as Roller Girl,
and eventually the one I became most popular for, Britney Spears..
Jenni giggled. "I guess that's around the first time I saw you perform."
I said, "Maybe not, I didn't do my own show until a few months after I
started." I continued my explanation telling her about what goes on
backstage at such a club. A lot of the girls didn't like me because I
wasn't gay, dated real genetic women, and had lots of fans. Except for my
boobs, I didn't rely on padding for the curves of my body, and most of
'em couldn't believe that I wasn't on hormones. See, I have a 26 inch
waist to go with my 38A inch bust and," I added as I twirled around to
show her my rear-end, "I've got 36 inch hips and a nice ass too! Even my
own mother once remarked to me that I had 'womanly hips'. I didn't need
to torture myself with hormones 'cause I was already tortured enough
growing up in this body."
Laughing, Jenni said, "That is one hot bod you've got there girlfriend!"
"You probably saw me perform solo after I had a routine of my own finally
put together. Because of my body shape, I was the obvious choice to
become the house Britney Spears when she became popular. With Kim's help
I put together the right look and for the first time got a proper fitting
for a pair of attachable breast forms and started electrolysis to thin
what litttle facial and body hair I did have. To this day I can't stand
the song 'Baby One More Time', but I still love the schoolgirl look. Once
I started doing Britney, I could easily make $500 a night dancing and
doing shows. I'd get propositioned by men and women alike for all kinds
of money to do all kinds of things with them, but the only thing I did
outside of Candi's were bachelor parties.
They were really fun, but I'll tell you about them some other time. I
quit working there after one of the more jealous drag queens stole one of
my breast forms. The cat-fights backstage could get nasty so I left just
after I finished my master's degree.
I sat down and poured us both another glass of merlot. We stayed up late
that night and watched a couple of old movies together while Jen would
occassionaly ask silly questions like, "Do you wish you had real
breasts?" Things between us grew from there.
THREE
Other than Jeff's and Carie's company, I worked in relative social
isolation at home while Jenni experienced the complete opposite in her
job. Every day she said 'hello' and 'bye-bye' to at least 800 people.
She'd once told me that she'd completely given up meeting a guy while
working explaining that in her experience of the thousands of men she'd
met, the very few she felt attracted to were either married or were just
looking to join the mile high club.
Because of our respective situations, it wasn't surprising that only
about six months after Jenni moved in we became intimate and have
subsequently been together ever since. A while back, I prepared a nice
dinner while waiting on Jenni to get in from the airport. About two hours
after I expected her home, I heard the front door open then slam shut
followed by the sound of bags hitting the floor. Jenni bounded into the
kitchen.
"Everyhing okay?" I asked wondering about the slamming door.
"It was one of those trips I've told you about," she started, "with an
asshole captain and even worse co-pilot."
I poured some wine and motioned for to sit down as I passed her the
glass. "So what happened?" I inquired.
She went on to explain how these two pilots were a pair of real
chauvinist assholes who constantly hit on the all female flight
attendants for the duration of a three-day trip. Not just onboard the
plane, but in the hotel and in the airport shuttle each girl had been
felt-up in one way or another by one or both of the pilots. One morning
when a rookie flight attendant brought coffee to flight deck, these two
jerks thought it would be a funny joke if they had their pants down and
dicks out. "I overheard the copilot Jim say as Mindy walked up 'That's
why it's called the cockpit honey' and then they laughed like a couple of
jackasses," Jenni added disgusted, "They're lucky they didn't try any
shit like that on me!"
I sympathized with her, refilled her glass as well as mine then
thoughtfully said, "Something's gotta be done to get that jerk back."
"I wish I knew what," she said and continued, "but at least with the new
crew rotations, I won't have to see him for the next few weeks."
I replied, "Well, whatever you want to do about those assholes, I'll help
out if I can."
"Thanks...cheers!" Jen perked up and we clinked our glasses.
Two weeks later I was working in my studio when my personal line rang. It
was Jenni. "I have an idea on how to screw that pilot the way he's always
messing with us."
"Go on," I said.
"Well, he's always trying to stick his dick in us, so what if one of us
stick's our dick in him!"
"Sounds good, but what exactly do you mean?" I quizzed.
"Well, you know how you've said one of your fantasies involved you being
dressed in one of my uniforms while getting it on with some unsuspecting
horny guy?" she reminded me.
"Yea, I suppose so," I admitted.
Reminding me of the many times I've worn one of her uniforms while role
playing 'slutty stewardess,' she continued, "Don't ya' see, you'd be
doing me a favor and enjoying yourself while your at it!"
She ran down the rest of her plan and asked me to think about my
participation adding that she would be very indebted if I went along. She
said goodbye mentioning that she'd talk about it some more when she got
home tomorrow. Just before she could hang up I interrupted. "Honey, I'll
do it."
"What! You will?" she exclaimed.
"Sure, let's talk about it when you get home."
Once home, Jen fleshed out her plan. I was to masquerade as a new flight
attendant meeting her in the lobby bar of the hotel where the aircrews
stay when they overnight in Atlanta. She would invite Jim along for a
drink, promising to introduce him to her friend Holli who just started
with a rival airline a couple of months ago. When I asked Jenni how she'd
make sure he made a pass at me she said, "Are you kidding? You look like
a model! You're just his type, besides, I'll let it be known on the way
in from the airport that the friend I'm meeting might be a little easy."
If he took the bait, namely me, all I had to do was get him upstairs to
my room, get him in a compromising position, then take photos or video of
the event to use against him if he ever harassed any girl in the future.
Humiliation was easier and better than getting him fired. The plan was
simply to guarantee his good behavior or whatever else we wanted through
blackmail.
An accomplice of ours, Katie, who flew with Jen many times and also said
she couldn't stand Jim, would pick me up the morning the plan went into
effect and get me to Atlanta. I'd fly with Katie as her friend, then get
to the hotel and check-in a few hours before Jen's crew was supposed to
arrive. The day before the big event, I drove Jenni to the airport,
kissed her goodbye, and said, "I'll see you tomorrow in Atlanta!"
She replied, "Remember, I want you to look sexy. I want that asshole to
drool over you!"
"Okay!"
"Bye!"
"Bye-bye!"
FOUR
After leaving the airport I headed to my ex Kim's salon for my private
appointment. Kim has a good body and an average face, but what she lacks
in looks she more than makes up in sexual aggressiveness. She is a
constant flirt who always wears tight clothes and short skirts. It's
probably what attracted me to her in the first place. She's not a bimbo
at all; more like a female Casanova who'd fuck a guy or girl before
knowing their name just because she felt horny. Jen knew that Kim and I
were still close friends and suggested I get my nails and hair done at
Kim's salon for the trip.
I pulled into the salon parking lot about two hours before the normal
opening time so I wheeled around back and parked next to Kim's car. I
assumed the front door would be locked so I proceeded to the rear door
and found it open. The jingle of bells tied above the door announced my
arrival. "Is that you Holli?" Kim called out from the front of the salon.
"It's me!" I returned. I could hear her heels clicking in step with mine
as we made our way toward each other.
"I sometimes forget how pretty you are!" Kim blurted as we came face to
face.
That morning I was wearing a belly shirt, short wrap-around sarong skirt,
a pair of 2" heel sandals and just a little day makeup with my hair
pulled up in a clip. Kim was wearing an overtly sexy outfit as usual
consisting of a tight fuzzy sweater over a little black leather skirt.
Perched on a pair of black five-inch stilletos, her black stockings were
undoubtedly held in place by a lacey black garter belt. And as was her
preference, I guessed she would be wearing a black lace bra and panty set
to go with the leather skirt. Later, I would find all this to be true.
Kim took me by the hand and led me to one of the sinks while I explained
the reason for my visit. To my surprise she said, "I know all about it.
Jenni called me a few days ago and told me what you guys are up to.
Airline pilot, huh? That'll be a first for ya. Oh, and by the way, I see
you gotta new set of boobs." She was referring to a set of C cup
attachable forms I recently purchased to wear with sexy outfits. She
studied my hair for a few moments and then said, "You know, if you're
going for a really sexy, almost slutty look, you should let me put in
some extensions before I add highlights." I smiled, agreed, and she got
busy. I had no idea it would take so long. After a while employees
started to arrive, the salon opened, and customers began to show up, but
all the while Kim kept her attention on me. After what seemed like hours
of hair pulling, gluing, and cutting, Kim spun my chair towards the
mirror and asked, "What do ya think?" My smile said it all. My hair not
only looked fuller, it had gone from shoulder length to ass length.
"Now let's get you cut and colored," she ordered.
As Kim worked her magic, we chatted a bit and then got to talking more
seriously about my relationship with Jenni. I told her that I really
cared for Jen otherwise I wouldn't be doing her this favor and then
wondered aloud why Kim was so interested. She leaned into my ear and
whisper, "I'm not jealous hun, just horny."
I giggled and replied aloud, "Then come over for dinner tonight. It's the
least I can do for all this," as I motioned toward my new tresses.
"It's a date."
When Kim finished, she turned me back facing the mirror and said,
"Opinion, honey?"
She had taken my dirty blonde shoulder length do, and turned it into a
sexy wave of golden blonde locks with platinum highlights cascading down
my back to the top of my ass.
"You gave me 'Playmate of the Month' hair," I happilly gasped.
"Glad you approve," she replied flatly and led me over to a nail station.
In no time I was sporting a new set of long fire-red nails to go with my
new hair. As she was finishing, Kim added, "Since your here, why don't
you let Sammy make you up. He's wondering why you're here so I lied and
told him you were gonna start doing shows again."
"Sure," I replied
When I left Candi's, I would work part-time for Kim whenever Sammy had a
large workload like a fashion show or wedding. He'd been the best make-up
artist in town for years and taught me all I know. I moved over to his
station with my new nails in the air ostensibly to help them dry, but
really to keep Sammy from hugging me. He's on of those touchy feely types
who hugs you at the start and end of any conversation you have with him
while touching you constantly throughout. He might also be the gayest man
in town, but he's a dear friend and the best make-up artist I know.
He immediately started gossiping to me about the recent goings on at the
showbars in town, but I interrupted him and told him that Kim had fibbed
on my behalf and that I was in the salon getting my hair and nails done
for a date. He smiled as he tweezed a few hairs from my arched brows, and
said, "I knew one day you'd change sides! You can't go around looking as
pretty as you and not be into guys."
As he started applying a light foundation to my smooth skin, I said,
"It's not like that Sammy. I'm here because of my girlfriend." With a
disappointed frown on his face, he busied himself next by applying a
dark, almost black, eyeshadow to my lids before continuing with the other
areas of my face. As he worked, he thanked me for being his guinea pig,
saying that he was trying a look on me that he wanted to use for a photo
shoot next week. Above my dark lids, he applied a light silvery shadow
then used a dark pencil liner in a thick line beneath my lashes.
In addition to a rich black mascara, Sammy glued a couple of false lashes
to the outside corners of my eyes. He lined my lips with a deep cinnamon
lipliner, filled them in with a deep rich red color and then added a bit
of gloss to give them a wet look. After some blush and powder, he finally
took a step back and said, "Honey, you look so good, if I were into girls
I'd do you myself!" as he mockingly rocked his hips back and forth.
"Sorry to disappoint you Sammy, but my girlfriend Jen might not approve."
He turned the chair so that I faced the mirror and could see his
handiwork. Sammy had given me a very dramatic look emphasizing my eyes
with a heavy dark eyeliner and shadow. He used a dark lip liner and a
deep red lip color to match my nails. With my new hair and glamorous new
makeover, I looked like I was made up for a Victoria's Secret fashion
show. This much makeup on my face would ordinarily make me or anyone for
that matter, look slutty, but Sammy's expert technique had made me look
glamorously sexy. My hardening cock agreed with my assessment
I found Kim out by the reception desk. She smiled seeing the combined
results of her and Sammy's expert handiwork. "How can I thank you?" I
asked as I gave her a quick hug. "Just make sure the desert is good
tonight," she replied with a wink. I smiled back knowing a wink from Kim
meant she wanted nothing less than hard sex. "My place at six then?" I
said as I headed for the door.
"See ya later," was her affirmative reply.
Kim has always been a sexual Thomas Edison constantly experimenting and
inventing different how, where, when, and whys to have sex. The kinkier,
the better. Though not the first girlfriend to know I crossdressed, she
was the first to encourage development of my alter-ego Holli and often
used Holli in one sort of sex game or another. I love sex, but just
couldn't keep up with the variety and frequency Kim wanted; it's the
reason we're no longer a couple. To this day we are best friends and
occassionaly we'll have a sexual tryst whenever Kim has an appetite for a
'chick with a dick'.
FIVE
It was already late in the day and I still had not packed for the trip
tomorrow, so I cheated and ordered a delivery from a nearby Thai
restaurant scheduling delivery at 6:30.
After picking out some possible outfits and lingerie for tomorrow, I took
a warm bath instead of my usual shower so I wouldn't ruin my hair and
make-up. Just before bathing, I Naired what little hair had grown on my
legs, underarms, body, and scrotum since last week. I also trimmed the
soft, little heart-shaped patch at the base of my cock. After toweling
off, I prepped my smooth chest before putting on my silicone breast
forms. Laying on my back on the floor, I first attach adhesive strips to
my skin that will hold my boobs securely even without a bra for the next
several days and then carefully place each form in place. My custom C-cup
breasts feel and match my skin tone so closely that it is almost
impossible to tell where the form ends and my living skin begins. After
rising from the floor, my new heavy breasts tugged at the sagging skin of
my chest as I moved to the floor length mirror to admire my feminine
body.
I wanted to wear something sexy for Kim so I picked out a three piece
lingerie set to go under the little mini dress I had decided to wear. I
pulled the pink bra straps over my shoulders, hooked the back, and slid
the lacy cups over my new breasts. The naturally saggy skin on my chest
was pushed up and together by the bra and forms giving my bosom perfect
looking cleavage. I then fastened the matching garter belt around my
waist, sat down on my bed, and pointed my toes into a nude thigh high
stocking as I slid it up my silky smooth leg. After doing the same for my
other leg, I hooked the garters to the stocking tops and pulled the
matching pink lace panties up over my thighs. I bent over pushing my cock
back between my legs as I pulled the panties over the garter straps into
place.
I always wear my panties over my garters so I can pull them off when I
want to fuck without having to take off my stockings. I then stepped into
a pair of four inch stilettos and walked over to the floor length mirror.
I twirled left and right admiring myself as I made sure everything looked
right when I remembered Jenni saying I looked like Nicolette Sheridan. I
faced the mirror, pushed my hand down into my panties, felt my stiffening
cock and said aloud, "Yea, but Nicolette doesn't have one of these!"
By now I was feeling just as horny as Kim had earlier in the day, but
even so I resisted the temptation to bring myself to climax right there
and then. Instead, I finished dressing by slipping into a tight pink
mini-dress. Just to set the right mood, I dabbed a little perfume on my
neck and wrists. I checked myself one last time in the mirror. I couldn't
decide whether I looked more like a life-sized Barbie Doll or one of
those models you see on a phone sex infomercial.
The doorbell rang a few minutes after six. It was Kim. I swung the door
open and before she could say anything I kiddingly blurted out, "Do I
look fat in this?" That got her laughing which was the desired effect.
As she walked past me she replied, "I swear Holli, your getting girlier
all the time!"
"So what's cookin' dear?" she asked as she headed straight for the
kitchen.
"I ordered in; is that okay?" following her lead.
She reached into the fridge for a bottle of chardonnay and responded,
"You mean we're not going out?"
"I told you I didn't have much time tonight," I whined as I pulled out of
pair of glasses from the cupboard.
She smiled and poured us each a glass. "I thought we'd go to Candi's for
old time's sake, but that's okay ...what are we having anyway?"
Pleased, I responded, "Thai food, ...spring rolls and some of your
favorites if that's good with you."
"Sure is."
I glanced over at the clock when a knock at the front door announced
dinner's prompt arrival. I pulled some cash from my purse on the hall
table and opened the door. Even though I ordered Thai food, because this
a college town, the delivery guy looked like he just stepped off the set
of 'Dawson's Creek.' As soon as I opened the door his eyes widened then
went up and down my body from head to toe checking me out before he said
anything.
"Um.. ahh, I have your order here from Thai City, it's ahh, $32.67
altogether," he finally blurted out when he caught himself staring.
Evidently, our dinner was in the big boxy styrofoam cooler he was holding
with both hands so I asked him if he could put it on the kitchen counter
down the hall. As I held the door open for him, Kim called out, "Is the
delivery boy cute Holli?"
He and I gave a quick glance at each other as he passed by and I called
back to Kim with an embarrassed sigh, "Yes dear, he is." I follow him to
the kitchen. As he stepped in, Kim stood up and cooed, "Yes he is
indeed," and added, "Hi, I'm Kim and you've already met my girlfriend
Holli."
I tried to rescue the the poor guy from Kim's advances by quickly asking
again, "How much did you say the check is?" He looked back and forth
between me and Kim as he emptied the contents of the box onto the counter
probably wondering what the heck these two hot chicks were up to. "It's
$32.67, ma'am," he answered. I handed him $40 as Kim interjected, "What's
the best tip you've ever received?"
He replied, "I guess around $50 once on a big order."
"I don't mean money necessarily," Kim cooed as she ran her hand down the
length of his arm and then to his butt. I thought the guy was gonna freak
out at Kim's forwardness, but to my surprise he turned his crotch into
her thigh, grins and said, "Well, ...I once got it on with a couple of
hot chicks for a $32.67 order."
Taking his bold statement as her cue, Kim slid her hand down the front of
his khakis groping for his cock as she said, "Oh really?" as she lifted
an eyebrow. He returned her grope by reaching his hands around her hips
to squeeze her ass. Meanwhile, I slid onto a stool a couple of feet away
just a bit shocked but not surprised at how quickly Kim was making it
with a complete stranger. Secured, but at an uncomfortable angle tucked
between my asscheeks, I could feel my cock coming to life. The delivery
boy's hands found their way to the button and zipper of Kim's skirt and
quickly let it fall to her ankles. With a flick of her 5" stilettto, Kim
freed herself of the skirt and began to pull her blouse from her
shoulders.
As soon as the tops of her breasts showed from the push-up bra she wore,
he pulled her in tight and began kissing her bosom. As her blouse hit the
floor, he reached around and expertly unsnapped her bra and let it fall
as well. He moved like a guy who'd undressed many women in his few years
since puberty.
"Slow down, slow down," she whispered as she gripped the front of his
pants. She stepped backward leading him by the belt toward the den
adjacent to the kitchen. "Coming Holli?" she ordered as she pulled him
toward one of the recliners in the den. Turning to face him as he slid
onto the chair she asked, "So what do you think of Holli?" She stood
between his legs like a stripper about to give a valued customer a lap
dance while she waited for him to come up with the right answer.
"I think she's hot!" he replied as I made my way toward them.
"Hotter than me?" she cooed as she shrank to her knees in front of him.
He didn't want to risk what appeared to be an immanent blowjob by giving
the wrong answer. Recognizing the confusion on his face, Kim soothingly
said, "Go ahead, answer truthfully," as she freed his belt and unzipped
his pants
While Kim tugged his pants down, as diplomatically as possible he said,
"Well, uh, you're more of the pretty girl-next-door type, the kind of
girl every guy likes and wants to get to know." As I came up behind Kim
and rested my hands on her shoulders, he finished, "And Holli, you're
more like the 'Price is Right' game show model."
Kim and I both giggled taking what he said as a pretty good compliment
given the apparent pressure of his situation. As he finished his answer,
Kim began to free his throbbing cock from his underwear. She coyly asked,
"Do you wanna win a prize from the 'Price is Right' girl?"
Immediately I knew she meant for me to go down on this lucky guy. He
answered by cracking a big smile and pulling his golf shirt up over his
head and dropping it to the floor.
We've seduced unsuspecting men together in the past, but only after
talking about it beforehand. This was the first time Kim started
something without first letting me know. Not knowing what she was going
to do next, I took the initiative.
I dropped to my knees and slid my hands from her shoulders around under
her breasts cupping each in my hands while pinching her nipples between
my long red nails. Kim cupped his balls in her left hand while stroking
his member with her right as if milking his head. I ran my nails back
around over her back, over her hip, and pulled her lacy black thong down
her thighs. Like me, she wears her undies over her garters. Kim released
his member and stood up, then with the same motion she used to kick her
skirt away, she discarded her panties.
Still on my knees behind her, I ran my right hand up the inside of her
left thigh as I peeked around her hips and said, "Before we go any
further, we need to be safe." The delivery boy looked bewildered so I
said, "Down the hall on the right, there's some condoms and KY in the
bathroom medicine cabinet." Understanding what I meant, he pulled himself
up and headed down the hall still fully erect.
As he went down the hall, I pulled Kim's arm down, dropping her back on
her knees facing me. I confessed to her, "I'm so horny."
"I knew you'd be when I walked in here and saw you in that pink dress!"
"I guess you know me better than I know myself after all these years."
"So what do ya wanna do, ...maybe a sixty-nine butt fuck?"
In a muffled gasp I let out, "Yes!" and added, "Unzip my dress." I
stepped out of the spandex mini-dress and whispered, "I'm wearing a
plug," as I pulled my panties down and slid a buttplug from my man pussy
tossing it into a candy dish on an end table.
Kim kissed me on the lips and said, "Okay, but when he's gone, it's my
turn."
She pulled her long hair across her shoulders and onto her breasts then
rolled on her back in the center of the shag rug with her head closest to
the hall. I straddled her face with my back to the now returning delivery
boy. I gently twisted my neck side to side causing my long blonde hair to
brush across my heart shaped ass. That motion is Kim's cue to push one
hand up against my cock and balls to conceal them tight across my
stomach.
From this point on, Kim's primary job is to keep my hard-on out of his
sight. All he saw as he walked back in was a pair of hot horny chicks in
a sixty-nine position; the one on top enjoying a good pussy rubbing
courtesy of the one below. This is just one of several positions we've
used to have sex with an otherwise unsuspecting straight guy. They're so
wrapped up in the fantasy of having a three-way with a pair of hotties
that they never have a clue it's actually a two-guy, one girl menage-au-
tois.
I looked over my shoulder and notice he's already slipped a Trojan over
his high hard cock. He held the lube and a wash cloth in one hand while
using the other to keep his balance as he lowered himself to his knees
behind me. His thighs pressed against my smooth stocking clad legs
causing me to go down on all fours. I peeked over my shoulders to give
him instructions, but see he's way ahead of me already about to insert
his lube drenched fingers into my glory hole.
Pleasantly surprised at his familiarity at ass-play, I gently gripped my
lower lip with my teeth and held my breath as his fingers gently slid in.
I took a long deep breath and pulled the white shag rug tightly in my red
nails while he expertly expanded my little ring to accommodate his fat
cock. Having worn a buttplug until a few minutes ago, he found me ready
for his entry after only a few moments of fingering. He gripped my ass
like a bowling ball readying me for his cock to follow.
While holding my hip with his left hand, he guided his love muscle into
my ass-pussy with his right. I arched my back, holding my ass as high in
the air as possible as he first buried his cockhead. I closed my eyes and
took a quick breath as I felt the sudden heat of his shaft. Holding my
hips with both hands, he pushed deeper. With a grunt he jerked forward as
I returned the motion by rocking back into his thighs. I craved the
pressure of his big johnson filling my ass.
He leaned forward and let out a long breath as he ran his nose through my
long hair. I pulled away from his thighs then rocked back hard signaling
my desire to be fucked hard. He straightened his back and once more
pulled my hips back as he thrusted his cock forward. I let out a soft
encouraging, "Yes.." He readied another thrust as I rocked back into his
thighs. Again and again we repeated the same motion but with a little
more speed each time. Below me I felt Kim struggling to keep my own
raging hard-on from exposing itself. He threw his right foot over my calf
when suddenly his strokes became shorter but faster.
We're all breathing hard when at once the delivery boy's body went rigid.
He sounded like a man trying to lift a two-ton weight as I felt his
steamy cum explode from his cock into the Trojan buried deep within my
rectum. After a few moments, he pulled out and slumped to the floor on
his ass sweating and breathing hard.
I pulled my legs together as Kim rose from between my legs onto her
knees. She walked on her knees around me being sure to obscure his view
of my crotch as I pivoted behind her. Now positioned between he and I,
she leaned back into me resting the back of her head between my breasts
while my erect cock hid between the small of her back and my stomach.
Meanwhile, the delivery boy was cleaning himself with the washcloth
trying to wipe the scent of sex from his body before returning to work.
Kim and I remained in a sitting spoon position as he stood and began to
dress. Kim looked up at him and said, "So, tell me again, what's the best
tip you've ever received?"
As he pulled his polo over his head he replied, "Not only was that the
best tip I've ever been given, I'm so late now, I don't care if it's my
last."
I added, "If you keep this to yourself, next time we order, we'll ask for
you."
He grinned and said, "No one's gonna belive me anyway, besides, I'm a
gentleman."
Dismissing him, Kim said, "Okay Gentleman, you know the way out."
He grabbed his cooler from the kitchen counter, said a quick good-bye,
and headed out the front door. As the sound of his car faded from the
driveway, I said, "Hungry for some cold Thai?"
To which Kim replied, "Oh no! It's my turn now."
Kim rose to her feet and turned toward me pushing her soft close-trimmed
beaver just a few inches from my face. She placed her hands on her hips
and inhaled slowly. Her five inch spiked heels gave her just enough
height to position her clit level with my glistening red lips. I knew
what she wanted.
Sitting on my knees with my ass touching the spikes of my own heels, I
ran my hands up and behind her silky thighs. I cocked my head to one side
tossing my long golden hair over one shoulder, looked up into her pretty
eyes, and slowly lowered my jaw. Keeping my eyes locked on hers, I slid
my tongue out over my bottom lip and teased her swelling berry. Her wispy
eyelashes fluttered as she let out a long shallow breath. I pressed my
face in closer pushing my nose against her shaved pussy.
Alternating between flat and deep licks, I teased her swollen clit as my
mouth became wet with her flowing love juices. By now, all eye contact
had broken and Kim had grabbed a handful of my hair at the top of my
head. I pushed my chin in harder between her thighs when she started
thrusting her hips forward. She began to moan softly in several
disconnected words, "Good ...yes ...aha ..mmmm ...yess.."
I grabbed onto her asscheeks in much the same way Superman grabs his suit
lapels in a phone booth. She pushed harder bending a bit at the knees
while squeezing the tufts of my hair she held with her hands. She held
and bucked my face like a cowboy on an angry bronco. I felt I was
suffocating when at last she suddenly released me, and gently slumped to
hers knees beside me.
"That was sooo good," she cooed as she nibbled at the tops of my
man-breasts.
She leaned against me, arms around my waist and mine around her hers, as
she slowly regained her composure. After a few minutes, she teased,
"You're the only one who didn't get there 'O'," then continued, "Let's
see what we can do about that."
Kim ran her long fingernails through my hair in an attempt to fluff out
what tresses she had earlier crunched in her hand. She continued primping
me for a few moments more until satisfied, then started caressing my
breastforms through my lace bra admitting, "I think you'd look better if
these were a little bigger and real."
I replied, "Remember, you kinda helped talk me into these in the first
place."
She added, "Maybe, ...but I think you sometimes wish they were real too."
I stroked her long hair as she worked her tongue from my sensitive ear,
across my neck and chest, down my flat stomach, and then along my
throbbing cock. She moved herself between my legs and carefully cupped my
sack with her left hand while holding the base of my cock steady with her
right. She knew how to give me my favorite blowjob because she'd seen me
give it to other guys many times. I leaned back on my elbows, holding my
chest and head up while assuming a missionary position. Our stillettos
and stockings rubbed against each others as she moved to a kneeling
position while lowering her head toward my raging hard-on.
I jerked my head from side to side in order to keep my long hair from
obscuring my view. She looked up into my eyes as she pushed her pouty,
glistening red lips onto my cockhead. My eyes closed reflexively as the
pleasure welled up from my crotch. She relaxed her lower jaw and pushed
down the length of my shaft while holding it in place with her right
hand. I gnawed my lower lip to counter this overwhelming pleasure with a
little pain. As she pulled her mouth back up the shaft, she pressed
her soft wet tongue against the sensitive underside of my member.
I shook my head in ecstasy and dropped on my back when she started back
down my shaft adding a little suction with her cheeks as she went. She
repeated the motion over a few more times before adding some movement
with her right hand. While holding my cockhead steady in her mouth, she
adjusted her grip on the base of my shaft and began to slide her hand up
and down synchronized with the bobbing of her head. Together, the
quickening motion of her hand, her tongue, her cheeks, and her lips
brought me closer and closer to climax when agonizingly she ripped away
from my overheated dick, gasped for air, and blurted, "Fuck me!"
Before I could think, she pulled me up toward her exchanging missionary
positions so now I was kneeling over her as she spread her legs. She
reached out and pulled me down onto her, my bra pressing against her
breasts as she kissed me hard and deep. I slid my nylon clad legs into
position and with my ruby-nailed fingers, guided my cock onto her bald
beaver. She was steaming wet inside. My six inches easily slid in all the
way to the hilt on first stroke. We let out a simultaneous purr of
pleasure. I pulled my hips back and she arched her back as I readied to
thrust again.
My blonde hair cascaded down my back and over my shoulders tickling her
erect nipples. Our lacey garters rubbed against our bare flesh as I bore
down on her once more. Again and again and faster and harder we bucked
until at last my load exploded within her hot body covering her insides
with my steaming love juice. Panting like junk yard dogs we lay there
quietly savoring the evening's experience.
After a long while, Kim broke the sleepy silence. "Hungry now?" she
kidded.
SIX
My alarmclock went off much too soon. The night before with Kim had been
spectacular, but for Jenni's sake, I had to perform at least as well
today. Kim had spent the night in the guestroom, and the smell of coffee
wafting through the house made it plain she had already risen. I wandered
downstairs wearing a only a pair of boxer short forgetting the heavy
breast forms were still securely fastened to my chest. I found her in the
kitchen breakfasting over the morning paper. Looking up from her paper,
she said, "Well, you look like a well-fucked shemale this morning," and
added, "it's a good thing I'm here to help you get ready."
"And good-morning to you too," I responded still half sleep.
"Look, didn't you say you had to be ready by ten-thirty?"
"Yea, so?"
"Well it's after eight and you should just see yourself."
I helped myself to a cup of coffee and slunk down in a chair beside her.
After a few tentative sips I said, "I do appreciate your help Kim,"
before getting back up and heading to my bedroom. Over my shoulder I
added, "I'm heading for the shower."
As I turned off the water after a quick shower, I heard Kim call from the
adjacent dressing room, "Don't do anything to your hair; I'll take care
of it."
"Okay!" came my reply. After wrapping my long hair up in a towel, I dried
the rest of my body before dabbing my ass and cock and balls with
scented powder. I moved out to the vanity in my dressing room and began
applying my make-up while Kim busied herself with my hair. As usual, I
started with a concealer before applying a light foundation to even out
my skin tone.
"Aren't you glad you went through with all that electrolysis?"
Kim observed of my smooth facial skin. Once satisfied that I had an
unblemished canvas to start with, I added a taupe eye shadow with silvery
highlights, and used a dark pencil liner and mascara to give my eyes a
sensual look. Kim continued to comb and roll my hair as I tried to work
on my face while she bobbed my head back and forth. I decided to wait for
her to finish before I continued.
"Am I gonna be late?" I wondered aloud.
"No, I'll be done in a few minutes, and you can finish you face under the
dryer," Kim reassured me.
I hate the dryer, but it's the best way to set the body and flowing curls
in my hair. I started applying my lip liner just after Kim switched on
the dryer. I added a glistening ruby-red lipstick and then pinkish blush
to finish the professional but flirty look I wanted. Since I was immobile
while the dryer hummed along, Kim laid my clothes out on the dressing
table behind me. She finally released me from the dryer and I began to
dress with rollers still in my hair.
I began with a black lace garter belt and matching see through mesh bra.
My attachable forms jiggle, look, and feel indistinguishable from the
real thing underneath a bra whether the material is see through or not. I
then slid a pair of black nylon thigh-highs up my smooth legs and
attached then to the garters with a little help from Kim. She'd spent
time in the dressing room at Candi's and knew how to help me tuck and
hide my cock when I pulled on my lacey panties. Kim decided it was
time to brush out my hair at this point so we went back over to the
vanity.
Her experience fingers quickly dispensed with the rollers and soon she
was brushing and spraying my hair into what I affectionately started
calling my 'Playboy Bunny' hairstyle. My platinum highlighted blonde hair
cascaded in curly waves over my shoulders across my tits and down my back
to my ass crack. It looked as good as yesterday.
Puzzled, I said, "Don't flight attendants have to wear their hair up or
something?"
Kim replied, "Honey, you're not a flight attendant, your just pretending
to be one so you can fuck some guy. Remember? Besides, that uniform she
gave you has a skirt I'm sure would violate some FAA rule."
"Sorry, dumb blonde syndrome I guess."
Once Kim finished my hair I returned to the dressing table and slipped
into my sexy uniform. I first slipped into the bone colored silk blouse
ignoring the usual camisole worn underneath such a see-through garment. I
wanted anyone who peeked to see the outline of my black lace bra
underneath the blouse. Next I stepped into the black wool blend skirt.
Kim was right, it has been altered to be a little tighter and much
shorter than any skirt I've ever seen on an aircraft.
She zipped me up from behind as I looked down to notice the bottom hem
half way up my thigh. "You're right," I said as she fastened the
waistband. Kim moved around in front of me, pulled up the collar of my
blouse, and slipped the little red flouncy tie around my neck. As she
pulled my collar back down, I stepped into a pair of four inch pumps.
"These might be a little high," I said, "but I'm only pretending, right?"
Kim snickered. Finally, Kim helped me into the form-fitting black wool
blend blazer brushing it with her fingers here and there to smooth it
over my curves.
"Wow," she complimented. I spritzed on some Chanel No.5, added a pair of
gold hoop earings, a matching thin wristwatch and bracelet, and finally
slid a couple of rings on my fingers. With an excited sigh, I announced,
"I'm ready."
Kim helped me pack my makeup, garments, and other items I'd need on the
trip. Holding a tube of lube she teased, "Do ya think one's enough."
"Very funny," I said flatly. As I latched my bag, we heard the double
beep of a car horn outside. "That's my cue," I said. I grabbed my purse
and pulled my wheeled suitcase toward the front door as we said our
goodbyes.
SEVEN
Katie's mouth and eyes widened as I strutted toward her car. "You look
amazing!" she said enthusiastically as she popped the trunk lid for me.
"I still get kinda freaked out whenever I see you in dressed up; you look
better than any flight attendant I know!" she added.
"Well," I said, "let's hope this asshole Jim thinks I look good too."
We bypassed the terminal at the airport and went straight to the
airline's operations center where Katie picked up an employee pass to get
us on a company training aircraft departing for Atlanta shortly. On
board, the plane was empty except for five pilots, two of which
apparently were trainees, a couple of company executives who flirted with
Jamie and I during the short flight, and another off-duty flight
attendant hitching a ride to Atlanta like us. On the ground we were given
a ride to the main terminal by a company car and from there we took a cab
to the hotel arriving just after three in the afternoon.
Jamie checked me into the hotel so I'd have a suite on the same floor as
the airline crews. We then went upstairs unpacked our bags and prepared
the room. While I put some condoms, lube, and a washcloth in the
nightstand next to the bed, Jamie hid digital video camera in a black
patent leather purse on a dresser at the foot of the bed. She said it had
an unobstructed view the room from under the flap of the purse without
itself being seen. Lastly, I opened my jacket and blouse and attached a
pair of perky nipples to my breastforms under my bra.
"What on earth are you doing?" Katie giggled.
"Guys like perky nipples, right?" I responded, "I should know, I'm one
of them." She shook her head still unsure how I could look like such an
attractive woman, but actually be a man. I tried to help her understand.
"Some guys are born genetics that help make them a world champion body-
builder, like Arnold Swartzenegger. I'm the exact opposite. I was born
with genetics that gave me a woman's curves and a pretty face." She
relaxed a bit using my explanation to help come to some inner
understanding of my outward appearance.
The phone rang. I picked it up. "Hello?" I said in a soft sultry voice.
"We're at the airport waiting for the shuttle," the voice on the other
end said. I put my hand over the phone and whispered to Jamie, "It's
Jen."
"We're ready here if everything's still on," I said.
"Great! I already told him I'm meeting an old girlfriend who just started
as a flight attendant and I'll try to embellish a little more on the ride
over," Jenni responded.
"So I'll see you in the lobby bar in about 45 minutes?"
"Yes, and remember, everything I've told him about you is true except
your real gender. He knows you worked in a showbar, but he thinks you
were a dancer or stripper or something like that. He kinda fixated on
that aspect, anyway gotta run ... oh yeah, make sure Jamie gives you a
nametag and insignia." The line went dead before I could say anything.
"Jamie, Jen says you have a nametage and insignia for me?"
"Oh, sure, let me pin them on you," she replied as she rummaged through
her purse finally producing a pin in the logo of the airline I was
supposedly working for, and a name tag that was enscribed 'HOLLY'.
"My name is misspelled," I jokingly complained.
Jamie pinned the nametag and logo to my blazer and said, "Remember, we've
never met before today if he asks."
"Hey," I said, "I, of all people, know how to pretend."
I checked myself in the floor length mirror admiring my long silky legs,
my heart shaped ass in the tight mini-skirt, my beautiful flowing blonde
hair, and big nippley breasts held high in the tight jacket. I strutted a
few steps, twirled, and strutted back and asked Jamie, "Well, what do you
think?"
"You'll eat him up!" she gleefully replied.
I retorted, "I hope so."
EIGHT
A few minutes after I left the suite heading downstairs to the lobby bar,
Jamie would follow. The lobby bar had few customers at this early evening
hour. Besides myself, there was a trio of businessmen together at a
table, a couple of ladies at another table, two single guys at opposite
corners of the sqare-shaped bar, and an attractive thirty something
businesswoman in a smart skirt-suit seated a few stools away from me. I
preached myself at the corner of the bar closest to the front desk, put
my purse up on the bar, and crossed my legs in front of me as I faced out
toward the lobby. Anyone who walked into the hotel would certainly notice
me.
I ordered a vodka martini as I waited for Jenni to arrive. As I fully
expected, just a few minutes after I sat down, one of the two single guys
approached me from their corner of the bar.
"Here for the NBTAA conference?" was his opening line.
"Whatever that is, I'm not. I'm waiting for the rest of my crew who
should be here in any minute now," I said flatly.
"You're crew?" he prodded.
"Yes, my crew. I'm a flight attendant."
"Wow, what airline? and uh, can I buy you a drink while you wait?" was
his next ridiculous line.
I looked him in the eyes, leaned in close to his ear, and whispered in my
most unmistakably male voice, "Look, I'm really a guy in drag waiting for
a couple of other guys in drag before we go out to pick up straight
guys."
He jerked away from me his face knotted in confusion as if he were just
doused with a bucket of icy water. He reeled away towards the elevators
not looking back before he was well out of the lobby bar area. I smirked
thinking to myself that he's gonna think long and hard before trying to
hit on another single lady at a convention.
I took a quick sip of my martini and relaxed. The attractive woman a few
stools away lifted her drink and said, "My compliments, it took me over
fifteen minutes to get that loser to buzz off and you somehow got him
running in just fifteen seconds. What did you say to him anyway?"
In a moment of truth I answered, "I told him I'm really a man."
She looked me up and down and laughed not believing a word of it, "I'll
have to remember to use that line next time. Cheers."
"Cheers," I returned and took a long sip of my martini.
Moments later I heard a familiar voice among many as a crowd stepped into
the hotel from outside. Jenni had arrived.
"Holli, how have you been?" she called out as she approached. I slid off
the barstool while pulling down the hem of my short skirt and replied,
"Jenni, you look great!" We hugged each other like old friends to keep up
appearances. As we embraced Jenni whispered, "Jim can't wait to meet you.
I think he thinks you'd be an easy score." As we separated I replied
confidently, "I think he's right."
To keep our cover, Jenni began to chat about some of the customers at
Kim's salon as if it were an interesting story we shared. As she spoke, I
noticed an attractive looking guy in a pilot's uniform moving toward us
from the lobby. "Is that him?" I whispered. Jenni turned just as the good
looking guy stepped up toward our corner of the bar. He was about 6'2"
tall, broad shouldered, with a trim waistline, short wavy dark hair, and
blue eyes. His uniform was perfectly fitted and pressed. He looked like
the sort of guy you might see on a military recruiting poster or in a
Calvin Klein ad. I was pleasantly shocked.
"Jim!" Jenni opened, "this is my friend Holli; Holli this is one of the
guys I work with, Jim."
"Please to meet you Holli," Jim warmly responded to Jenni's introduction.
"Hi Jim," I sweetly replied.
"Jenni has been talking about you ever since we began this trip Holli. I
feel a bit embarassed that I know so much about you while I'm still a
complete stranger to you," was his charming opening line. It was just as
Jenni predicted; he was already trying to charm my skirt off.
"I guess we'll have to fix that then," was my coy response.
We three began having cocktails and talking about airlines, but Jenni
smartly steered the conversation away from this subject knowing I might
get stuck. Jenni mentioned that I once performed on stage as a showgirl
to which Jim said, "You certainly have the legs and body for it, and I'm
sure you were the prettiest of the bunch as well."
"Oh Jim, you're so sweet," I replied as I brushed the top of his hand
with my long ruby-red fingernails. We all chatted for a few more minutes
as I twirled a lock of my hair in my fingers and occasionally ran my hand
up and down my thigh. I felt he was completely into me so I gave Jenni
the signal for her to depart by crossing and recrossing my legs. She
confirmed she understood me by saying, "I'm gonna go upstairs and take a
cat-nap; wanna meet for dinner in a couple of hours Holli?"
I replied, "Sure, I'll give you a call." Jenni headed toward the
elevators leaving Jim and I alone.
"She's a great lady," Jim said about Jenni once she was out of earshot.
As smooth and innocent as everything he said seemed to sound, I knew from
what Jenni and Jamie had told me, it was just his way of operating. I
decided to take a chance and cut through the chatter saying to Jim, "I've
been sitting in this lobby bar over an hour now so I think I'm gonna head
upstairs too; would you like to join me." He was a player, but my
directness caught him off guard.
He stuttered, "Um, ah, sure, I mean, thank you, that's generous of you."
NINE
He paid our tabs and we headed to the elevators. I took advantage of the
crowded elevator by pressing my soft warm breastforms into his back
making sure he felt my nipples stroke against him all the way to my
floor. When the elevator stopped, he let me exit first so I took the
opportunity to brushed my hand against his crotch as we stepped through
the crowd and onto my floor. No doubt about it, he was aroused. I walked
ahead of him swaying my hips and swishing my long hair across my ass as
we made our way to the door.
We passed a pilot wearing the same type of uniform as Jim who gave him a
smile and nod as we went by. I pulled my keycard from my purse, passed it
through the electronic lock, and opened the door. Stepping through into
the suite I thought I could hardly blame the guy for hitting on me, after
all, I would be constantly hitting on women if I had his good looks. He
had the confidence and looks of a guy who very rarely got turned down.
He closed the door behind us and said, "You really are more attractive in
person than in the photos Jenni showed me."
"Thanks Jim, but you don't have to use anymore lines on me, we're already
in my room," I said as I switched the stereo on tuning it to a smooth
jazz station.
"No line Holli, I mean it," he said as he stepped close to kiss me.
His kiss was passionate. After another brief kiss on the lips, with just
a bit of tongue tip, he kissed his way down my neck beginning just below
my ear while breathing in th