Heather
I looked into the mirror and began cleaning the makeup from my face for the
third time. What was it about makeup? It seemed that no matter how carefully
I worked with it, I could not make it happen. To start with, I just didn't
have the knack of working in the mirror like this. On top of that, when I was
trying to put the damned eyeliner on, my hand was in the way of my face so I
couldn't see what I was doing. It was frustrating. I took a deep breath and
leaned back from the dresser mirror - trying to relax a bit before I started
again.
After composing myself, I began again, maneuvering the little brush around the
line of my eye. I finished the right eye. It looked pretty good - not
perfect, but my threshold for acceptability was lower than it had been an hour
earlier. I finished the left eye and studied the effect carefully. I decided
to settle for it.
I was putting on the lipstick, trying desperately and unsuccessfully to keep it
on my lips when my sister's voice carried up the stairs. "Jerry! Heather is
here!"
Oh shit. I panicked
I tried desperately to stall. "Uh - okay - I'll be down in a couple of
minutes!"
The sound of someone coming up the stairs made my heart jump into my throat. I
didn't want to be seen like this. I threw my bedroom door closed, wishing it
had a lock. It opened again almost immediately as I had known it would.
Heather.
She took in the sight of me standing in my sister's bra and panties, the
sloppy, half-finished makeup on my face. Her own face surprised and a little
angry? Irritated? Something unpleasant.
"Aren't you ready yet?" She glanced at the pile of makeup littering the table
by my bed. "Honestly, women!" It was the perfect parody of the line repeated
so often in movies and sitcoms, but it didn't strike me as funny. "What are
you doing? Why aren't you ready yet?"
"It's this blasted makeup," I huffed. "I don't know how the hell you girls can
put this stuff on so easily and have it look so good."
Her impatient look became tolerant sympathy. "Poor thing, no one has taught
you to put it on properly, have they?" Her tone was patronizing, but her
attitude was all business. "Well, I guess we'll be a little late to the party,
but I will help you with this. First thing is to scrub all this mess off of
you." She turned my face to the light, picked up a tissue and dabbed it in the
cold cream, then began swabbing my face with it.
"You and your ideas, I complained, as she wiped my face clean. I wanted to go
as a cowboy, but that was too common. No - nothing would do but for us to go
as man and woman - you the man and me the woman." I made a face. "I guess
this proves I'll do anything for you, Heather."
She smiled and kissed my forehead. "That's only part of what I love about you,
Jerry."
"Oh?"
"Well, you do have nice pert breasts," she joked as she caressed one bra cup
with the palm of her hand and giving me a calculated look that let me know that
she knew that I was enjoying this attention.
"Gee thanks." I dissembled. I wasn't about to admit how much it turned me on.
"Now let's make you nice and pretty." Heather crouched in front of me and
began applying the makeup. She cupped my chin in her hand and spoke softly to
me as she worked, telling me what she was doing each step of the way. But her
voice became a pleasant droning background to the new sensations that flooded
me. I reveled in the sensations of the various brushes and pads against my
skin, the firm way she moved my head this way and that.
"Why, I believe you are really enjoying this." The meaning of her words slowly
sunk into my consciousness. I opened my eyes to see her gazing contemplatively
at my arousal, evident through the flimsy fabric of my sister's panties. She
kissed me lightly on the cheek as she lightly brushed the evidence, causing a
new shimmer of pleasure to course through me. I closed my eyes again, waiting
for her to continue with the makeup.
"We're done," she chuckled. I opened my eyes, and saw the strangely excited
light in her eyes. It seemed to match the strange feelings within my self.
She appeared to struggle briefly before she composed herself and led me to the
mirror over my dresser. I was astounded. She had made me look stunning. I
turned my face right, then left, studying the effect. It was a marvel. I was
beautiful!
"Now I'm jealous," Heather chuckled, "My boyfriend is prettier than I am!" She
didn't seem to be terribly upset, though. Her smile was as gentle and loving
as I had ever seen it.
She helped me with the clothes - a cheerleader's skirt and sweater, also
borrowed from my sister. Another trip to the mirror revealed me - now a
convincing teenage girl. I felt a mix of pride and... ...something else I
wasn't sure I wanted to identify. Instead of exploring my feelings, I studied
Heather.
She looked convincing. The slacks and bulky sweater hid her slender beauty,
and the way she had swept her short hair into a ducktail was, if dated, at
least masculine. The little stick-on mustache completed the illusion. I was
convinced that anyone who did not know us would actually believe that she was
the guy and I the girl. We smiled at each other and went downstairs arm in
arm.
As we prepared to leave, Gina spoke from the hallway. "Hang on guys. Don't
want to let you get away before we commit this event to posterity!" We turned
to see her, camera in hand, caught in the flash. "That one's no good," she
frowned. "Jerry, put your arm around Heather's waist, and Heather, put your
arm over Jerry's shoulder." We complied and she took a photo.
That was the beginning of a brief photo session - eight or nine pictures,
probably, before she relented and let us get on our way.
In spite of Heather's fears, we were not particularly late to the party. We
were not late. Several people had arrived before us, and we found ourselves
stopping to talk to several people on the way back to the kitchen where the
drinks had been set up. I found myself falling into my role naturally, and
Heather seemed to have no difficulty either. I was happy when a few people we
didn't know asked why we weren't in costume. I lowered my eyes and smiled
shyly while Heather grinned at them without answering, as she draped her arm
across my shoulders in a possessive attitude that I found myself enjoying.
As I reached for a beer glass, Heather touched my hand, caught my eyes with
hers and gave me a very small shake of the head. Instead, she began assembling
a cocktail for me - something elegant and feminine looking. I sipped it and
found it a little sweet, but quite tasty. When I saw the trace of my lipstick
on the edge of the glass, I felt a subtle twinge in my groin. I sipped again
while I looked into Heather's eyes. She leaned forward and embraced me softly
as she kissed the side of my neck. A sexual charge surged through me, and my
knees grew a little weak. Recalling the phrase I had heard so often from her
in similar situations, I whispered, "not here."
Separating, we found our way back through the growing crowd to the living room
to find friends we could hang with.
The crowd grew larger. Most of the people here were folks I had never met
before. I was apprehensive at first - afraid that someone would mistake my
costume for evidence of a less than macho attitude, but I found my concerns
baseless for more than one reason. Most of the people did not know I was a
guy, even some of my friends did not recognize me at first. And even those who
did know did not seem concerned - this was, after all, a costume party.
Everyone was expected to be in the guise of someone they were not. There was a
moment with William, one of the football team who got belligerent when he
figured out who I was. He made some kind of crack about faggots and his
girlfriend snapped at him to stop being stupid.
But it did give me pause. Although I had started the evening in the guise of
someone I was not, I found myself enjoying the costume - finding a certain
comfort as if I were at home in this guise. William's crack made me begin to
think about it, and what I realized about myself made me concerned. I enjoyed
being a girl - I enjoyed Heather, as a boy, making little loving gestures as a
boy to a girl. But there was a little hollowness in the pit of my stomach as I
wondered what I had become.
Heather, my friend for years before we had started dating each other, was
sensitive to my moods. She sensed right away that something was bothering me,
and guessed what it might be. Summoning her role as the man, she steered me
through the back door into the garden. There were little lights strung among
the trees and bushes and a path that led a short way from the house to a bench
by a small fish pond. We sat on the bench. Heather turned to me, took both of
my hands in hers and looked into my eyes with sympathy.
"Are you disturbed about what William said?" she asked softly.
I was hesitant at first, not sure I understood my feelings thoroughly - not
sure if I wanted to risk our relationship by revealing what I suspected my
feelings might be. Slowly, I began to tell her, and she to draw me out until
finally, I revealed to both of us what I already knew unconsciously - that I
enjoyed the roles we were in, that I wanted to do this again. I watched her
face for the disgust I feared, but instead her face softened. "I want it,
too," her voice was husky with emotion.
Her arms found their way around me, embracing me. I found tears in my eyes,
could not see clearly, but my lips found her lips, clung to her lips in a soft
and lingering kiss that promised so much.
I giggled nervously as I wiped the lipstick from her lips, the tears from my
eyes. "Can we go home now?" I asked.
"My house is closer, and no one is home," she responded, squeezing me, giving
me a peck on the cheek. The implied promise made me giddy with anticipation.
I don't really remember leaving the party. I do recall arriving at her home,
entering the front door and embracing in the front hall. I remember clearly
the kiss, her tongue exploring my mouth, her hands exploring my body. I recall
going limp with desire before she relented. I know that I caught my breath as
she led me up the stairs to her bedroom, then lost it as she closed the door
and caught me in another embrace.
Without being aware of moving, I found the edge of her bed touching the back of
my knees, and I sank down, pulling her down on top of me. Her lips never left
my mouth as her hands found the hem of my cheerleader's sweater. We broke the
kiss as she lifted the garment over my head, and resumed it immediately.
She unfastened my skirt, and slipped it down my body as I raised my bottom for
her. I caught at her as she stood, but relented and watched as she slipped the
sweater and slacks off, returning to me unclothed. Her hands explored my soft
skin while her lips explored my mouth, my face, my neck, my shoulders.
She slipped down my body and drew the panties away from my quivering cock,
kissing it lightly on the tip before she engulfed it softly with her mouth.
Before I lost control, I pulled at her shoulders, urging her up on top of me,
and she complied, kissing my lips again before she reached down to fit my
hardness into her wet sex. "Oh, sweetheart," she whispered, "I want to make
love to you always like this."
"I will always be your girl," I promised. "But fuck me now, boyfriend, fuck me
and make me come like I never came before!"
And she did. Slowly and sweetly at first, then wildly. At the end, she was
gasping and sweating as I was gasping and sweating. I watched her boyish face
as she fucked me, her eyes sometimes closed in concentration, sometimes open
and drinking in my own pretty face. And when I felt my orgasm building, I told
her, urging her to make me cum, urging her to cum with me, and she did,
shuddering sweetly as my spunk pumped into her. This was completeness - she
and I together, loving, straining to be one. The warmth that had built in us
so urgently blossomed and settled like a slow bubble around us and we drifted
sleepily in each other's arms, still joined, unable to find enough energy to do
much more than look into each other's eyes.
---
That was last night. I awoke this morning, still in her arms, the dried
evidence of our passion crusting skin and sheets. Her face is so beautiful in
repose, but my arm is under her, and I have to go pee. I worry that my parents
might be worried that I didn't come home last night. The makeup on my face is
itchy and I want to get it off. But I know, as I watch her smile in her sleep,
that I will want her to put it on me again - soon.
