The Model
by Alyssa Davis
At last! Summer vacation...At 16 years old, I'm finally working on my first
real job earning my own money. OK, so I'm only working for my aunt who
owns a small dressmaker shop. But, it is a full time job, for the summer, and
I'll probably continue part-time after that. I had spent a lot of time here
playing when I was younger; now she's given me the opportunity of earning
some spending money. She's taken care of me since I was born...said I was
so tiny I could fit into a shoe box. I've always been small and kind of frail,
guess I always will be.
I had just finished sweeping the floor of her workroom and, using a magnet,
picked the pins out of the debris. Sitting at her kitchen table, (she lives
behind the work area) I was loading pin cushions with the pins I had
salvaged when I heard Aunt Evie's voice talking angrily in the workroom.
"This darn old thing! Of all times..."
I peeked around the corner and saw her standing over the dress form. The
center pole was broken off from the weighted base, and there was no way to
keep it upright.
"Oh, Al dear, I'm sorry if you heard my outburst, but I'm having a terrible
problem with this dress form. It broke on me again, and I don't think it can
be repaired. On top of that, I have four bridesmaids dresses to hem before
Saturday, and even if I order a new form it'll take a month to come. I'll
never get these dresses finished in time."
She looked over at me standing in the doorway with my hand on one hip. A
smile came over her face as the idea struck her,
" Could I talk you into being my dress form model for a while? All you'd
have to do is stand there, and with you turning, I wouldn't have to move
around and I could be finished in no time."
She stood smiling expectantly, the broken dress form lying like a dead body
between us. Me? In a dress? The mere thought of it sent a shiver down my
spine. How could she know? For as long as I can remember I'd wondered
what it would be like to be a girl, to dress in these wondrous fabrics and
styles. Shame at the thoughts that had come to me as I'd run my fingers over
the sleek satin and lace revisited me now. Goose bumps raised the hackles of
my neck as I tried to be casual about this wondrous opportunity. "I'd like to
help you Auntie, but what if someone comes in and sees me, a boy in a
dress?"
She stood in thought for a moment and then brightened,
"Oh, I don't think that's much of a problem, with your long curly hair, in a
dress, you'll look like a girl. Nobody will recognize you or pay attention to
you. They'll just think you're a girl that works here."
She forged ahead rather than give me a chance to back out.
" It sure would be a big help for me if I'm going to meet my deadline."
My answer came slow, as if she had convinced me,
"OK," I said in a hesitant voice, "let's do it, this should be a laugh!"
I dutifully followed Evie back into the back area of her shop where the
dresses were neatly hung on hangers. Four beautiful dresses in a dusty rose
color. She had me strip to my jockey shorts. It felt funny as we pulled the
first one down over my head, my uplifted arms inserted into the sleeves. It
slid down easily and fit perfectly. It was odd, but I knew that I liked it
already. She zipped up the back of the dress and we both looked at it in the
mirror. The bust area of the dress was empty and looked silly, even to me.
She brushed my naturally curly hair up and back into a reasonably feminine
hairstyle, bringing a few strands down over my forehead....Amazing, I
thought, as she completely changed my appearance with a few strokes of a
hairbrush. Watching in the mirror, I realized that I looked exactly like my
sister! In fact, Aunt Evie said the same thing as if reading my mind.
"Al, you look like you're a twin to your sister in that dress and hairstyle."
My sister is older but we're the same physical size.
In the fitting room, Evie had me stand on a box-like stage in the center of the
room, the mirrored walls reflecting my new image while she sat on the floor
and began to take measurements, setting the hem line, placing pins as I
turned. I could see this girl in the long dress looking back at me from every
angle, the re-styled hair and feminine dress creating a fetching creature that
called out to me. I felt something happen inside me...a change... a thrill...an
exciting sensation.. The feel of the dress brushing against my bare legs was
new and different, the tight feel of the dress bodice on my chest reminding
me that I was under her control.
"Aren't the ladies going to be wearing high heels?" I asked.
"Yes, of course, why?"
"Won't that affect the length of the skirt? I know that that's a question they
ask when I get my pants tailored...what kind of shoes will you be wearing?
I noticed that you're measuring from the floor with me in my sox. When
they wear heels, the skirt could be too short, right?"
Her eyes smiled,
"That's an excellent point. How clever of you to notice. I'd better call and
ask what size heels they'll be wearing"
While Evie was making the call, I twirled and danced around in the pretty
gown, admiring myself in the mirrors, striking various poses as I had seen
models do on TV. I was unaware that she was watching me from another
room while talking on the phone. She returned with several boxes of shoes.
"You were right. They want the skirt shortened to take into account the heels
they will be wearing. They reminded me that I have the shoes here, they had
me send them out to be dyed to match the dresses. I hope we can find a pair
that fits you."
With an outward casualness that didn't match my feeling inside, I began to
try them on. A flash of fear spread through me as I worried that they may be
the wrong size for me. For some reason now I desperately wanted to see how
high heeled shoes would feel and look on me. Fortunately the last pair just
barely fit once I had taken off my heavy sox.
Evie handed me a pair of nylon stockings.
"Here, you need these. We can't have you wearing their shoes in your
bare feet."
Without thinking, I rolled the hose into a little donut and hooked it over my
toes, working it over my foot and unrolled it up my leg. At the top I folded
it over so it would stay in place. I had seen my mother do this and never
thought about what I was doing. After the second stocking was in place Evie
smiled at me. She was impressed.
Thoughts ran through her head, 'You never cease to amaze me, Al....Your
awareness of women's fashions caught my mistake with the hem
measurements, and you put on stockings like a woman. I wonder what other
surprises you have for me? Have you ever done this before? You haven't
been wearing your sister's clothes have you?'...But she said nothing,
keeping it all inside her ...she was beginning to surmise....
I finished with the stockings and slipped the shoes on. I had to be careful
with the added height of the heels, holding the front of the long gown up so I
wouldn't trip. I took several turns around the shop but in minutes I seemed
to have gotten the hang of it and moved back up onto the pinning area. As I
looked at her we both smiled, but said nothing.
We returned to the measurements, this time with me looking more regal in my
bridesmaid gown. The stockings and high heeled shoes gave me a feeling I
can't describe; all I know is that I felt more comfortable this way, my
excitement internal, a buzz that wouldn't go away...it was neat!. I couldn't
tell Evie, but in helping her I was really enjoying myself; secretly I think she
knew.
When the first dress was complete, Evie unzipped the back of the dress and
I tried to remove it but in the warmth of the back of the shop I had gotten a bit
sweaty, and my damp skin made it very difficult to slide off. With extreme
care, and the effort of both of us, we got it off. She hung it up on it's hanger
again, shaking her head,
"It's kind of warm today, I'd like you to wear a slip so we don't ruin these
dresses with perspiration. We almost tore the dress."
Evie went into her apartment and came back with a full nylon slip with wide
lace straps and lace trim. "Here..." she said, handing it to me.
I put it on without objection, actually delighted at this addition. But this too,
had a noticeably empty bodice. I almost said something but then Evie came
with the second dress and it was back up the stand again for me. I stood in
my finery, holding my posture and poses as I knew a young girl would do.
The girl in the glass looked back at me and smiled. I smiled back at her all
afternoon. We finished all four gowns by the end of the day. All marked
and pinned, ready for sewing.
"Al dear, I cant tell you how much I appreciated your help. And you've
been such a good sport about it...not many boys would have been so helpful
and agreeable to do what you did."
I stood there in my slip, stockings, and high heels as if it were the most
normal thing in the world for me. Deep down I knew I was comfortable this
way.
"That's OK, Auntie. It was actually kind of fun. I'd always wondered how
I'd look if I was a girl, and now I know."
I twirled on my toes before her,
"and I'm not half bad. Do you want me to model any more dresses? It
seems to make your work easier and I kinda enjoy doing it."
Confirmation of her suspicions echoed in her head, 'Yes, I really think you
do, my little girl.' Her smile gave nothing of her thoughts away,
"As a matter of fact, there are several outfits you can help me with. If you
don't mind, I'd prefer to use you rather than a dressmaker's form, and " she
paused, "Maybe I can even ask you to model some finished outfits from
time to time. The clothes show off better if someone is wearing them, and I
certainly can't get into these styles anymore."
She looked me over, the form fitting slip displaying my slim build, hiding
nothing.
"You, however, have a model's figure and will look great. Do you mind?"
My heart was in my throat, the thought of wearing these exotic garments
again was something I would kill for. Yet, I'm not sure why. A shoulder
shrug for casualness, then a
"Sure...anything to help you, Auntie."
The next day I approached the shop with rapt anticipation. What would
happen? Would Evie dress me up as she had yesterday? The feeling came
back to me as strong as if I were still wearing them. I needed their touch, the
feeling of constraint, the gentle swish of skirts about my legs, the regal height
of the high heeled shoes. I opened the door and started in.
"Al...? Come on back. I've got those outfits ready for us to work on."
As promised, Evie had it all ready for me. I had to hide my excitement as I
quickly changed out of my clothes and into another slip, but one with more
lace, and a pair of her high heeled shoes. I put it all on without her direction.
She smiled approvingly when she came back and I was all dressed...dressed
as a nice girl, that is. Most of the day, between phone calls and customers, I
put on skirts while she marked and fitted them for alterations. The silky
blouse she had me wear as a top was soft and slippery against my skin. I
stayed that way all day long. Even people popping in to drop off things and
such didn't bother me. They seemed to accept me as part of the shop. In
fact, people seeing me in the skirt and blouse gave no indication of anything
unusual, and some actually complimented me. I appeared to be just another
girl being fitted for a new outfit...a girl being fitted. I liked the idea.
We seemed to fall into a routine, each day dressing me in my now familiar
working outfit of slip, stockings and heels, and then progressing through the
almost never ending pile of clothes to be hemmed and fitted. Even after we
had finished , sometimes early in the day, I would continue to effect my role
of a girl. After a week of modeling skirts and dresses, I was pretty well
adjusted to putting them on and taking them off without assistance from Evie.
She noticed how at ease I was while wearing them. I could tell she was
impressed while watching me as I would smooth my skirt when sitting down
and cross my legs. I found myself doing it almost instinctively. Wearing
these clothes in such a feminine environment made me want to act like a
lady...I felt like I belonged in them. I was all mixed up...why did I, a boy,
enjoy wearing girl's clothes? I should have been embarrassed, but instead, I
felt so natural.
Monday morning of the third week, entering her apartment as usual, I found
a surprise. Along with the usual lace trimmed slip, there was a new pair of
panties, a garter belt, and a matching bra with foam inserts. Next to them
was a shoe box with a cellophane package on top with a new pair of white
stockings. I opened the shoe box and held my breath. Black patent leather
pumps with two inch heels glistened in the morning light.
Evie said nothing, but I knew for sure she was testing me. I stood there for a
while, and finally the voice inside me broke through. This is what I really
wanted. I wanted to feel the silky fabrics against my skin and the precarious
tilt of the high heels. I couldn't disappoint her (or myself), so I eagerly
exchanged my jockey shorts for the panties and hose, bra, slip, and shoes
and with a confidence born of my weeks in them, joined Evie in the
workroom, ready for duty.
She watched me come in and pause to show off for her. Now the bodice of
my slip was full with the simulated breasts of the padded bra. The form
fitting slip showed my narrow shoulders, slim waist, and broad hips. It's
shortness also showed off the shapeliness of my stocking clad and curvy
legs. A girl's figure was reflected back at me from the mirror! No wonder I
felt so confident wearing women's clothes.
"I see you found my gift, dear. Just a token of my appreciation. I thought
you'd enjoy having some of your own things. I felt it's what you wanted."
Tears came to my eyes as I realized how well Evie knew me, perhaps better
than I knew myself. I had hidden nothing from her, and instead of being
upset with me she was actually promoting this new lifestyle.
"Oh thank you, Auntie. This is wonderful." I paused and looked into her
eyes, " you knew that I was enjoying myself, didn't you? That I liked
wearing this stuff."
Her smile brightened the room as she came close and gave me a motherly
hug,
"Yes, I've noticed for a while that you've taken to it...it really makes you
happy and I actually like seeing you dressed that way. I've always thought
that you'd make a better looking girl than a boy. You have such petite
features, you should have been a girl. You're too pretty to be boy. In fact,
your mother always said she wanted another girl. Oh, and there's something
else."
She reached behind her to bring out a dress on a hanger.
"I made you a dress in my spare time. Here, try this on. It's all yours,
along with the lingerie you're wearing. You've earned it."
She handed me a floral printed dress with short sleeves, a straight skirt, and
back zipper. She helped me to immediately put it on, and naturally found it to
be a perfect fit. When Evie zipped it up, the front formed around my padded
breasts proudly. I loved my new look and I now especially loved the feel of
wearing my own clothes. While Evie was taking a phone call, I sat at her
dressing table and looked over the array of cosmetics that covered the
surface. I contemplated applying some of her lipstick to my lips and a little
blush to my cheeks, but hesitated. I brushed my hair a bit for a little touch
up. When Evie returned and saw me, she was still smiling and pleased with
my look.
"Might I suggest a little makeup for you? We can make you into a lovely
young lady if you want to be, OK?"
My hesitation was nonexistent as I turned to the mirror and smiled. Sitting
beside me she walked me through each item, explaining its purpose and the
best way to apply it. Within minutes she had darkened my lashes with
mascara, accented my eyes with eyeliner, made my cheeks glow with
blusher, and arched my eyebrows into more of a thin arch. The lipstick she
let me put on by myself.
I loved the smell and taste of it and kept licking it with the tip of my tongue.
"Better watch that in public, " she admonished, "it looks kind of sexy and
you might start attracting boys. Let's close up and go have lunch, my treat.
I want to show you off to some friends."
"Outside? You mean go out? Auntie, no! I don't think I can do that. I can't
go out on the street like this! What if someone finds out I'm a boy. I'll die
of embarrassment."
She looked at me sternly,
"Hush! Has anyone noticed in the last couple weeks? NO! Besides, no one
will ever know because you're not really a boy, you're a girl! Think of
yourself that way. You're beautiful and you've gotten so feminine, you
could fool anybody. Be confident, be the person you want to be!"
She gave me the moral boost I needed. I did feel good about how I looked as
I primped in front of the mirror, and I wanted to be seen. I was very aware
of how I moved and acted when I wore a dress and makeup. As if I was
rehearsing for the big performance. I don't know what's come over me, but
I liked it.
So, after checking myself in the mirror one more time, we closed the shop for
the day, and went downtown to lunch and visit a few of Evie's friends,
mostly suppliers, at their stores. I was introduced as her niece, Allisa, and
nobody even guessed I was anything but the young lady I presented. I was
so relaxed, I felt I was a born-again female, and secretly wished I could be.
From that day on, every morning I routinely changed into my lingerie, put on
some makeup, something I got better at doing as I improved my skill,
touched up my hair, which I was letting grow longer, and worked in the shop
wearing a short dressing gown until Evie called for Allisa to model something
for a client. The rest of the day I would wear the dress she had made for me,
and even occasionally borrowed a finished dress for a special treat. I
especially enjoyed modeling bridal gowns. In my mind they were the
epitome of femininity. Trying some on definitely gave me some dreams at
night about being a bride. It set me to thinking about men in a new and
different way. Some time I'll tell you about that.
Most all the garments fit me reasonably well, except for the few things that
were special ordered for large women! And with the aid of my padded bra, I
now have a wonderfully girlish figure. Narrow shoulders, small waist,
larger hips and very smooth skin. My arms aren't very muscular either,
which helps with my feminine image. I now spend all my working time at
Aunt Evie's dressed as a girl, (it's our secret from the family) with her
encouragement.....it's my job. I even run errands as Allisa to Evie's friend's
stores to pick up supplies. They enjoy seeing Evie's niece and often engage
her in small talk. Sometimes they tease her about boyfriends. Allisa has to
be clever about her answers.
One summer afternoon, business was slow so we took a break for some ice
tea. Aunt Evie felt like talking.
"So tell me dear, now that you've experienced what it's like to be a girl for a
while, what do you think? Is it what you expected?" she asked.
"Yes and no, Auntie."
An interesting question, I thought. I might as well be open and honest with
her. She was my ally. She made it happen.
"I love the way I look and feel...I mean, I like the feel of a skirt bouncing
around my legs and my legs touching each other without rough trouser legs
between them...I like the extra attention I get and the little courtesies people
show me as a girl that never happens to a boy, but on the down side, it's a
lot of work to be an attractive girl! I must remember all the ladylike gestures
such as keeping a good posture and keeping my skirt down and my legs
together. And, as a girl, I find people often don't take what I have to say
very seriously. They seem to treat me like a child altho' a pretty one. I don't
feel that as a boy. When Al talks, they'd at least pay me the courtesy of letting
me finish. As Allisa, they talk right over me and usually ignore what I have
to say anyway. I get so frustrated I want to yell, but I remember I'm a lady
and ladies don't do that."
Evie laughed. She reached out and touched my hand warmly.
"My love, good for you. You're beginning to learn the differences between
genders. I know you've worked hard to create and maintain your feminine
appearance, but I also know it's been the labor of love. If you didn't want to
do it, you would stop. That's why I've given you the opportunity to dress
and act like a girl...I think it's something you really want to do. As for how
you're treated, you've discovered one of the difficulties of being a woman in
a man's world. Men always seem to treat us as objects to look at and desire,
but not to be taken seriously. You must work that much harder to prove
yourself. And, when necessary, to use your feminine wiles which you'll
develop in time. Men don't have that problem...they're given the benefit of
doubt. I'm sure you find it especially difficult because now you've seen it
both ways. You know what, next summer, let's you and I take a vacation
trip together with you as a young lady. I want you to spend some
continuous time that way to really see what it's like instead of this on again-
off again dressing. How does that sound?"
"I can hardly wait, Auntie....thanks!"
She was both understanding and consoling. Sometimes I felt closer to her
than to my own mother. I wondered how mother would react if she saw me
dressed as a girl. Would she be so understanding? She wanted me to be a
girl, anyway, but I'm not so how would she react? What about my older
sister? They've got to find out eventually.
Allisa is really looking forward to going on the vacation trip with Aunt Evie.
She's wearing her hair as long as she dares without it being too obvious.
She now shaves her legs and underarms like all the other girls in her age
group and is flirting with boys when out doing errands just for the sport of it.
We're coming closer to the school year, and Allisa will only be working and
dressing weekends. But that's OK, I can go out as Allisa on evenings when
my parents and sister are gone. I'm really enjoying all this. Who knows
where this will go?
It had to happen. Entering the fitting area late one afternoon from an errand
to pick up some thread, I said
"Here's the thread you ordered, Auntie."
My sister was there talking to Evie! I started to break out in a cold sweat.
There was no place for me to hide. Sis had spotted me! I had to face her.
"Al, is that you?" Sis asked, surprised.
Evie smiled, but said nothing.
"I would never have guessed, but I recognized the voice and I thought I was
seeing my double. How long have you been doing this?"
I was speechless...I didn't know how to respond.
Turning to Evie, Sis asked,
"You knew about this and you never said anything?"
"It was our little secret, dear. I figured he would tell you when he was
ready."
I could only stand there blushing like a teenage girl, which is what I looked
like anyway.
"Well, I have to say, you make a very convincing girl, Al, even if you do
look like my twin. I wish I would have known you liked to do this....we
could have had a lot of fun," Sis said, turning back to me.
I got my voice back and trying to explain, I said,
"it started innocently enough, Aunt Evie asked me to do it as a favor to help
her out of a bind, and it just sort of grew. I got caught up into dressing as a
girl more and more."
"You don't have to explain it to me....as long as you're happy doing it, I
don't care. I think you always wanted to wear girl's things. I noticed you
watching me dress whenever you could, and asked a lot of questions boys
don't usually ask. Isn't that so?"
"Yes, maybe I did" I muttered, blushing again.
"Oh, don't make him blush anymore," Evie interceded. "Now that you
know, will you keep our secret?" she asked Sis.
I didn't know what to do or say. I wanted to cry. If my sister told our
parents or friends, I'd die of shame.
"Sure I will, Evie. In fact, I'll even help him dress whenever he wants. I'd
love to have a little sister. When we were little, I wanted to dress him in my
things at play and he always refused. Now I find out he does it behind my
back. Anyway, it's only fair, I wear his things whenever I want. He never
complains."
Turning to me, Sis said,
"I'll keep your secret, little brother, but you owe me one, OK?"
"Yes, Sis"
"By the way, what name do you use as a girl?" she asked.
"Allisa," I responded, waiting for the laugh.
Sis took my hands into hers and said,
"Allisa, I like that. Hello, Allisa. We're going to be good friends, I know."
Evie and I smiled and breathed a sigh of relief. A big hurdle overcome.
From that time on, my sister's attitude towards me was entirely different. We
became very close instead of the sibling rivals we had always been. She
discussed things with me that were never mentioned before. Girl things.
She asked me when I decided to wear girl's things since I never did when we
were little. I replied that I had nothing more than a curiosity about dressing in
girl's clothes until Aunt Evie asked me to model for her. It was then that I
began to enjoy things feminine....it was a real turn-on for me. I found
myself enjoying being a girl more and more. In the privacy of our bedrooms,
Sis let me try on many of her outfits to model for her. She admired the
lingerie Evie had given me. We even exchanged makeup and hair tips.
I turned 17 that summer, and, in the Fall, started my sophomore year in high
school. Sis had graduated and started full time employment. I was working
part-time for Evie, cross dressing whenever possible.
THE DATE
One day, late in the Fall, Sis came to me with a problem.
"Al, I need a very big favor from you. There's this cute guy at work I'm
interested in. I finally got him to ask me out on date, but he's shy and wants
to double date with his boyfriend if I could get his friend a date."
"So?," I asked.
"So I promised to fix up his friend with Connie for Saturday night."
"So is there a problem? She's your best friend...she'll help you."
"Yes! At first, Connie agreed, and everything was set. Now Connie is sick
and cant make it. I really want to go out with Bill. I worked hard to set this
up and without a date for his friend, it's off. I don't know if he'll ask me
again...at least I don't want to risk it."
"So what can I do to help?" I asked, naively.
"Will you take Connie's place as Allisa? Please? You owe me one,
remember?"
Sis was calling in her mark in a way I never expected.
"You're asking me to date a boy? Come on! I'd never get away with it. I'm
not a real girl. He'd kill me if he found out. Be reasonable!" I responded
frantically.
I had mixed emotions...scared, yet intrigued. Might be kind of fun. A real
challenge. But she has to convince me.
"Allisa is a beautiful girl and very feminine. You have no problem passing
as a girl anywhere. This will be easy. We'll just go to a movie. All you
have to do is be there and act natural as a young lady....you've had plenty of
practice. C'mon, give it a try...please?"
"What if he tries to make a move on me...what do I do?"
"Whatever you want him to do. Consider yourself as the woman you want
to be. That should be easy for you. Please?" Sis continued to plead.
I was convinced...at least, I felt she thought I was. Actually, I wanted to try
it. The supreme test.
"OK, I'll do it for you...I owe you, I know. But consider the debt paid."
I was killing two birds with one stone.
Saturday night, I dressed for my date at Evie's apartment with her help so my
parents wouldn't see me. I wore the pretty dress she had made for me, she
had done my hair up and back into a curly bob, and with extra time spent on
my evening makeup, earrings, and high heels, I looked older than my 17
years. And, oh yes, she advised me to wear a panty girdle I borrowed from
Sis just in case. Sis and her friends picked me up at Evie's and I was
introduced to my date as he got out of the car and opened the door to the rear
seat.
"Jerry, this is Allisa," Sis said as he gently took my hand and helped me
enter the car.
"Hello Jerry," I responded cheerfully.
He was a big guy and very handsome...this was going to be fun as long as
he didn't read me as a boy, and after a final checkout in the mirror, I didn't
think that was going to be a problem. I never felt so much like a woman. He
had a pleased and admiring look on his face as his eyes checked me up and
down. I liked that. My coat was open and the curves of my breasts were
noticeable under the sheer dress. I was aware of his eyes stopping there.
OK, I thought. I would have done the same. Sis introduced me to Burt, her
date, as we started out to the theater. We made small talk en route, and upon
arrival, Jerry opened the door on my side of the car and, taking my hand,
helped me out, a real gentleman. I noticed him looking at my legs as I swung
them out of the car and stood up in a ladylike fashion. This pleased me too.
My dark shaded nylons and the high heels enhanced the shape of my legs, as
intended. During the movie, Jerry made no moves except to put his arm
around me which seemed harmless enough. I snuggled against him as he
would have expected a girl to do, and he held me tighter. It was actually
quite comfortable. I was enjoying my first date, and it was as a girl with a
boy!...all I had to do was look pretty and act natural. Naturally what? I still
was mixed up. am I a boy in girl's clothes, or am I really feeling like a girl?
After the movie, we went for some pizza. I was careful to take the smallest
pieces and take very small bites. I had to be a lady at all times. I felt both
boys looking at me....were they admiring me or did they suspect something?
I'm sure it was the former. Sis kept the conversation going, talking about
work with Burt, her co-worker, and just trivia in general. Jerry was very
quiet, just a good listener, but he couldn't keep his eyes off me. I was
confident of my appearance, so that didn't bother me; in fact, I was flattered.
I tried to be warm and friendly to him, without leading him on too far. He
reached for and held my hand under the table, of which I offered no
resistance. He would expect that too. Finishing eating, Sis and I excused
ourselves to go to the lady's room. As I refreshed my lipstick, we talked
about our dates and how it was progressing. Sis was pleased with Burt, and
happy to see the Jerry and I were getting along so well. She noticed us
holding hands and asked if I was going to let him kiss me, suggesting that I
should. I reminded her that I was not a real girl, to which she smiled and
winked. She treated me like a real girlfriend on a date, not as a brother
helping her out of a bind. I was surprised by that
As we stood up to leave, Jerry helped me with my coat, opened doors for
me, and continued these little gestures of courtesy. It pleased me and made
me feel even more of a woman. Of course, he probably shamed Burt into
doing the same for his date. Arriving back at Evie's, where I planned on
spending the night, Jerry walked me to the door.
"Thank you for a lovely evening," I said to him, looking up into his eyes.
He was tall, burly, and handsome, and very gentle. I had never looked at a
man like this before, nor had I ever felt so vulnerable, but the combination of
his behavior towards me and the way I felt with my transformation had a
strange effect on me. I felt more feminine than ever before, a feeling I did not
dislike 'tho I knew it was wrong.
"Will you go out with me again?" he asked, holding my relatively small
hands gently in his large hands.
"Yes, that would be fun," I immediately responded, without thinking.
Then it hit me....What did I just say? What did I do! I'm a boy...I'm not
supposed to be dating a man in the first place! And a second date? But I said
yes, and now I'm committed.
With that, Jerry pulled me close, put his arms around me, and softly kissed
me on the lips. I was totally surprised by the move, but, I submitted to his
kiss. I relaxed my lips and returned his kiss until he released his hold on me.
I cant say I didn't enjoy it, but I'd never admit it. It was a man kissing a
woman. The only words spoken were, "I'll phone you, Allisa" as he
returned to the car and departed into the night. I could like Jerry as a boy, but
I liked him as a girl too. He's such a gentleman. I was swept off my feet on
my first date. Really my first date...I had never even dated a girl and now I
was dating a boy! Wait till I tell Sis. Dare I tell Evie? I let myself in,
changed into a nightgown, removed my makeup, and slept good that night in
the guest room, completely confused by the events of the evening. 'If I'm a
boy, why did I enjoy myself so much as a girl dating a boy? If I'm a girl,
why shouldn't I enjoy myself with a boy? If I'm a boy, why do I want to be
a girl? If I'm a girl, why am I being raised as a boy? What will we do on the
next date? Why did I enjoy his kiss? What if he wants more than a kiss?'
On and On...................Sleep came slowly.
The next day, I said little to Evie except that we went to a movie and pizza
and it was fun dating as a girl. She was pleased that I enjoyed myself. But,
Sis and I did a total recall of the date. I told her I was kissed and I confided
that I liked it, which pleased but didn't surprise her. She really considered
me to be a sister. When I said I had accepted another date with Jerry, she
was in awe. I admitted it slipped out without thinking, but what's done is
done. I have to follow thru. She was delighted and agreed to help me any
way she could. My friendship with Jerry would enhance her relationship
with Burt. All I could ask for was her panty girdle again. She offered to buy
me my own.
Jerry called and set the date up for the following Saturday night. He took me
bowling and out to eat afterwards. On the way home, we parked and talked
for a while. I now completely forgot I was a boy. It was a typical boy-girl
conversation. We eventually embraced and I snuggled into his arms where I
felt most comfortable, even as his hand gently caressed my breast. After a
while, he kissed me softly, followed by more passionate kisses. I enjoyed
his kisses but somehow I felt it was wrong...I should not be enjoying them! I
was completely submissive, allowing his advances up to the point of heavy
petting. His hands were on my legs under my skirt, sliding on the smooth
nylon of my hose. His touch was slow and gentle but, I couldn't let his
hands go too far what with my foam filled breasts and hidden treasure in my
panty girdle, namely my hard, throbbing penis, straining to be released from
it's nylon containment. How I wished my bra was filled with my own flesh.
If I now had any feelings of guilt about my gender, they were diminished by
my feelings toward Jerry. When we kissed, it felt so right. I just relaxed and
enjoyed the moment....I could fall in love with this man. Later, when talking
to Sis, I felt ashamed of my reaction to Jerry's advances, but she told me not
be. What I did was natural for a girl and that's what I had considered myself
to be. I told her the jury was still out on that subject, altho at times, I did
agree with her. Jerry and I dated a few more times until I felt it was going
too far. I was enjoying his advances too much and felt it had to end before
we got too close and we both would be hurt badly. It's what I would have
wanted if I were in his position.. I was having thoughts and feelings about
him that worried me. In my dreams, we were having sex together; I wanted
him to take me and I was enjoying it! This could not be. We had to break up
so I told him I was leaving town for a job in New York. I had to end this
foolishness before it went too far. Sis reluctantly agreed. I think she would
have preferred I stay with Jerry and be his girl but, I think she was being
selfish.
I continued to work for Evie through my senior year of high school as Allisa
as much as possible. No more dates, not even with girls. As a boy, I wasn't
too popular with the girls socially as I was very quiet, shy, and small, but
those qualities were probably useful in attracting girls to associate with me for
help with schoolwork being I was a good student and always got good
grades. I was never a sports jock, so socially, I blended in with the
wallflowers. I had no boyfriends either, for the same reasons. They avoided
me completely. But I enjoyed being Allisa, because she made friends easily.
She wasn't shy but instead, playful and outgoing. She brought out a
different side of my personality. She allowed me to be the person I wanted
to be. Through Sis, I met new friends as Allisa and was accepted by them as
Sis's younger sister. Allisa was developing her own social life.
Eventually, my parents discovered my cross dressing. Mother spotted me
wearing Sis's dress one day while I was helping her hem it. Strange, that's
how this all got started. Anyway, Mom exclaimed that I could be a twin to
Sis, we looked so much alike. One thing led to another, and I wound up
modeling some other of Sis's dresses for Mom. She was impressed at my
appearance, my long hair, and how feminine I acted while cross dressed. I
finally admitted what I had been doing. That explained why I had let my hair
grow so long and shaved my legs and underarms. She also had seen a
gradual change in my personality over a period of time. I hadn't noticed until
she mentioned it but I had become more passive and less argumentative than a
normal teenage boy. In retrospect, I was becoming more
feminine....probably due to all the time I spent as Allisa. I had figured it was
just maturity, but she knew better, having raised two other boys, my older
brothers who were considerably older and were already living away from
home. She agreed that as long as I was happy with my cross dressing,
that's all that mattered. She would love me no matter what I did. She had
no problem selling Dad on what I was doing....he wasn't too disturbed
either. My parents originally preferred to have two boys and two girls
anyway, so it was fine if I wanted to be a girl. As mentioned earlier, they
had hoped for a girl when I was born. Maybe I should fulfill their wish.
VACATION
The time came for Aunt Evie to fulfill her promise of a vacation trip. We
settled for a trip to New Orleans, traveling as two women. I was to spend
two weeks totally as a woman. I packed only women's clothes...the only
male article was my shaver, and I hardly needed that since I mostly used hair
remover on my face. We flew to our destination and rented a car with Evie as
the designated driver. Al's license wouldn't work for Allisa. Checking in at
the hotel, Evie had reserved a single room for us to share. That seemed
harmless enough, but we discovered the room had only a single king size
bed. And no other rooms were available. Not unusual for two women to
share a bed, but our case was a little different. I think it bothered me more
than Evie because I'd never shared a bed with anyone.
I was excited about staying en femme for two full weeks, keeping my
makeup on, keeping my hair looking nice, not having to change back to
boy's things every day. I seemed to be in a constant state of arousal,
something Evie noticed the first night in bed. Dressed in our silky
nightgowns, we took our places in the large bed on opposite sides of the
huge bed. I fell asleep easily and must have dreamed of being in Jerry's
arms, because suddenly I woke up in Evie's arms, tightly pressed against her
body and my hands caressing her breasts under her gown which had drifted
up to her waist. My manhood was hard and poised against her legs. She did
not move me away, but instead held me tightly and comforted me. She said I
was moaning and kissing her. She rather enjoyed it. Being a young widow,
she hadn't been with a man for a long time. I apologized for disturbing her
and gave her a long tender kiss on the lips and fell asleep in her arms since
she didn't want to release me.
In the morning, we showered and dressed for a day of sightseeing. I chose a
bright, flowery, summer dress with a half slip and a lace camisole, white
pantyhose, and low heeled shoes, good for walking. I freshened my makeup
which I had not removed from last night, and brushed my long curly hair into
place. Evie, likewise put on her makeup, and I helped her with her hair,
putting it into a bun. She said nothing about last night and I didn't mention it
either. We set off to see the town. Most of the day was spent in the French
Quarter, dining in famous restaurants and visiting museums. Evie not only
constantly referred to me as Allisa...she treated me totally as a woman.
Once, when I thanked her for that, she replied,
"No need for that,. this is what you wanted and I'm only trying to make you
happy. When we go home in two weeks, you can thank me then, if you still
want to."
I knew I would.
Going to bed, the second night, I turned off the light and rolled over to kiss
Evie goodnight. I kissed her lightly on her cheek and thanked her for a
lovely day. She pulled me to her and our lips met in a long wet kiss. I
sensed the passion of a lonely woman. I reached down and touched her
warm, soft breast through her gown. She held my hand on her breast and
fondled my soft stem with her other hand until it got hard and hot. Saying
nothing, she turned onto her back and pulled up her gown as an invitation. I
lifted my nightgown up to my waist and assumed the male dominant
position, and my rigid shaft easily slid into her wet, waiting love canal. It
was heaven. She brought her legs tightly together and clamped my center
inside her, consuming me. So soft, so warm, so wet. She had exchanged
my virginity with the ultimate gift of love. I was having sex with my
aunt....but then, she's not my real aunt. She's the woman who has nurtured
me since I was born and now I was repaying her in her time of need. I was
the young, innocent...she, older, experienced. The fulfillment of every
young boy's dream. I alternately kissed and sucked the nipples of her supple
breasts until they became erect, while fondling the luscious mounds with both
hands. I was fixated by those beautiful mammary's. Oh, how I wanted my
own! I then worked my way to her lips where our tongues met and licked at
each other's lipstick. Being my first sexual encounter with a woman, this
whole experience was new to me and I climaxed too quickly. She accepted
my charge graciously, with a low pleasureful moan of ecstasy, and didn't
wait for her own climax but rather, relaxed and let me withdraw. Her only
comment to me was,
"Forgive me, my love...it's been so long since I've been with a man."
I hugged her and kissed her again. We embraced and went to sleep. I was
thinking, 'Ah, those beautiful breasts...how I wished they were mine. But, I
must settle for foam rubber.'
When we awoke in the morning, Evie's only comment was,
"Well, young lady, did you sleep well?"
I could only reply blushingly, "Yes, thank you," and headed for the shower.
She had given me a gift I'll never forget.
Another day of sightseeing as we joined a group and toured some of the ante-
bellum mansions. I felt so naturally female, I was chattering like a teenage
girl, talking to our tour companions. I was like a bride on her honeymoon
after her first sexual encounter. Everyone was so nice and treated me like the
young lady I appeared to be, and I loved it. I was the youngest girl on the
bus, and the driver made sure to look after me. Of course, the tight, low
neck, jersey Tee shirt and the short skirt I was wearing with nude pantyhose
may have helped. Evie enjoyed the attention I got and my reaction.
The third night was another new experience. This time, in the dark, Evie
delicately lifted up my gown, rolled me onto my back, gently fondled my
genitals to get me hard and, straddling my body, mounted me, her in the
traditional male position, guiding my throbbing, hot shaft into her receptive,
wet opening. She said, "Tonight, I'll be the man and you're the woman you
want to be....see how you enjoy it, my love." She worked her body slowly
up and down, kissing my lips, my nipples, my neck, holding me tightly,
touching me all over, definitely dominating me. I was completely submissive
to her and enjoyed it immensely. I knew this was my place, where I truly
belonged. I fantasized that she was Jerry and he was making love to me. I
was his woman. His body was on mine, his manhood was inside of me! She
picked up the pace until I could wait no longer and climaxed, shooting my
generous wad into her. Shortly thereafter, she reached orgasm with a loud
moan and a sigh....the first time I'd seen her climax. I'm sure she preferred
to be on top where she could be in control for the best sensation. She rolled
over and we both fell asleep. This time, I had no guilt feelings about my
fantasy.
While taking my morning shower, the curtain opened and Evie joined me!
"Let's pretend I'm your husband and you're my wife?" she asked, soaping
my back.
"How did you like sex from the woman's position?"
"It was wonderful....I think that's where I belong," I replied with no
hesitation, "and I think you enjoyed being the man."
I didn't want to tell her of my fantasy, but I couldn't stop thinking about
Jerry either.
"Well, I certainly do enjoy the man's position, that's why I want to be your
pretend husband. Is that OK?"
"Yes, dear," I responded, girlishly.
She turned me around to soap my front and noticing my erect penis, she
washed that first, making it firmer. I wanted her to finish it, but she stopped
rubbing. I took some soap and lathered her chest and delicious breasts. She
willingly let me touch all of her body which confused me even more...at this
moment, am I a man enjoying a woman, or am I a lesbian with another
woman? In my feminine frame of mind, I feel like a lesbian, but I have no
remorse.
"You're going to need a panty girdle for that thing if you cant control it,"
rinsing the soap off my still rigid member.
I could only smile, but by now, I wasn't the least bit shy. She looked at my
boy's chest with only a little flab for a bosom and shook her head.
"I wish I had your breasts," I offered.
"I wish I could help you there, my love, but until you decide what you want
to do, we'll leave that alone. A padded bra will have to do."
She rubbed soap on my nipples, saying
"my poor dear, if only these would grow for you."
Her rubbing made my nipples hard.
I asked her what my options were to get female breasts. She said I could get
breast implants or try hormones, but I had to very sure I wanted enlarged
breasts because they would be difficult to conceal as a man so I would have
to commit to being a woman and I was not ready for that. Maybe she was
wrong. I left her alone in the shower and went to get dressed. The first
thing I put on was my bra, padded with the well formed foam inserts and
looked at myself in the mirror, wishing they were real. I loved the look they
imparted to my body.
Every day was a new experience with new things to see and do. I was
completely happy being Allisa full time. Evie began to play the role of my
husband and treated me as if I was the wife, escorting me around during the
day and dominating me at night. I was completely submissive to my
"husband" and enjoyed every minute. The sex on this trip was certainly an
unexpected treat. Thank goodness for the error with the hotel room. I lost
my virginity and found happiness as a woman. This vacation was turning
into a honeymoon and I was the bride!
The two weeks went by too quickly, and soon, we headed home. Evie asked
the question:
"Well, Allisa, you've lived as a woman for two full weeks. Do you think
you'd like to make it permanent?"
To which I enthusiastically replied,
"Absolutely yes! And I especially liked being a wife."
"Oh Allisa, you're hopeless," Evie said, with a wink and a kiss, "I thought
you would tire of the novelty and I could change your mind."
"Well Evie, after all, you did start the whole cross dressing thing," I said,
giving her a big hug and whispering "Thank you".
THE BRIDESMAID
After graduation, I left Aunt Evie's employ for a full time job, but I still
helped her out occasionally, especially at night. She continued to help me
cross dress, and I helped her with her "needs" as a good wife would do for
her husband. Yes, the game continued. I secretly hoped to find employment
as Allisa, perhaps as a secretary, but I knew that was going too far. That was
not to be; I wasn't ready to commit. Allisa continued to be only an occasional
but frequent visitor. I joined my sister's group of friends as Allisa, Sis's
younger sister, and was easily accepted. It was the only social life I had. As
Al, I was a dud., besides, I had gotten too effeminate for a boy. I preferred
to be Allisa. Allisa was pretty, and popular. She was invited to party's and
shopping sprees with the girls. I was happy being Allisa, but I knew I had to
make a living as a man. As a compromise, I found a job as a photographer's
assistant with on-the-job training. I was able to keep my hair long, and my
effeminate appearance did not draw unusual attention in the world of art
directors, hairdressers, and cosmetologists. My cross dressing skills came in
useful when helping models dress, applying their makeup, and arranging
their outfits for the photograph. My boss was extremely impressed with my
talent and found it very useful, and the girls were comfortable working with
me. If he only knew how I learned those skills. On occasions such as
Halloween parties, I'd appear in woman's costumes and blow everybody's
minds. They couldn't believe how feminine I looked, yet it was so natural
for me. Many of the clients thought I was a real girl and wanted to date me
until they learned my true identity. My boss loved it.
Delores, a long time friend of Sis and mine, was to be married. We all got
involved with the plans of the large wedding. I was asked to take extra
candid photos of everything, which I willingly agreed to do as my gift to
them. I built up a series, starting with gift selections by the bride and groom,
gown selection, reception hall, etc. I attended the rehearsals with my trusty
camera, and shot many pictures. Two days before the wedding, a minor
disaster struck. One of the bridesmaids fell and broke her leg, requiring a
large cast and the use of a wheelchair. She couldn't be in the ceremony as
planned, upsetting the balance of attendants. This caused a financial ripple
effect all the way down to the groomsman's tux rental. Delores needed a
replacement fast to avoid a lot of embarrassment and hard feelings. Sis
suggested to Dee that maybe Allisa, our "cousin" who was visiting, could fill
in as a replacement. Dee did not know Allisa and that I was she. In
desperation, she begged Sis to ask Allisa. Sis then asked me if I'd do it, to
which I replied that I'd be happy to, but that meant the end of the candid
photos. Sis said she'd cover for me with some excuse that I was called away
by my boss for a location shoot. Allisa was introduced to Dee and was
immediately invited to join the wedding party at the pre-nuptial dinner on the
eve of the wedding. Sis, also a bridesmaid, and I, helping each other,
proceeded to dress in outfits befitting the occasion and attended the dinner
where we were introduced to the out of town guests and other members of
the bridal party. I tried to make myself look different than my sister so we
didn't appear as twins. Her hair was down, I wore mine up. She wore a
skirt, blouse, and jacket, while I put on a pretty dress and my highest heels to
make me taller. My large hoop earrings finished the look. I was introduced
to my escort for the ceremony, a handsome young man who couldn't take his
eyes off of me. He tried to hit on me all evening, but I kept my wits this
time. I was now an experienced woman and didn't want to date another man,
although he was tempting and it was difficult to decline his invitations. So
confident was I as a woman that I no longer had guilt feelings about dating a
man. But, I was attracted to another bridesmaid, a small and very pretty girl
named Elaine. We became friends, instantly, and got better acquainted as the
evening progressed. We both attracted the young men, but we stood our
ground and hung out together as girls do.
Early the next morning, the wedding day, Dee sent over the bridesmaid's
gown I was to wear. Sis and I went to the church to get dressed for the
ceremony, getting an early start. We knew it was going to take time to
transform ourselves. We met the other girls there...a total of four
bridesmaids and the bride. We all helped each other dress in our gowns and
do our hair and makeup. I wore a black bustier with garters and blue
stockings to match the gown.. The garment cinched in my waist and
enhanced my figure to a very feminine shape. My bra was filled with
expensive silicone breast forms glued to my skin, which I had recently
purchased on the advice of a professional makeup artist. With makeup, you
couldn't see where they attached to the skin. They looked very natural and
formed a noticeable cleavage. This was my supreme moment. Presenting
myself to a crowd of people in a gown similar to what I wore the first time I
cross dressed. Only, I was now very experienced at appearing and acting
feminine and no one doubted otherwise. My experience with the
photographer's models and their professional makeup artists came in handy.
I did my makeup with extreme care, and helped the other girls, especially
Elaine to whom I paid extra attention. Although all the girls were running
around in various stages of undress in the dressing room, seeing Elaine in her
bra and panties was a real turn on for me...I considered her "special."
Somehow, with her, I felt like a man.. The bridesmaid's gowns were a light
blue with an off the shoulder d?colletage, and it fit my small body perfectly,
and displayed a little of my breast and cleavage as intended. The hem, just
above the knees and worn with three petticoats for fullness, showed off our
legs. The shoes, colored to match the gowns, had 3" heels and were a
perfect fit. With my past experience, I had no problem walking in the heels.
Having had both ears pierced, I wore dangling earrings matching those of
the other girls. We were all stunning. The ceremony was beautiful. I felt
wonderful walking down the aisle with my tall, handsome, escort and all
eyes upon me, and standing at the alter with the other girls. As usual, I was
confident of my appearance. I kept thinking to myself, 'I look like a
woman, I feel like a woman, I am a woman.' The thought gave me a great
deal of comfort.
At the reception following the ceremony, I sat next to Elaine. We had
searched for each other. We chatted throughout the dinner, and stayed
together all evening, even going to the ladies room together multiple times for
makeup repairs. I really liked her. We even danced together, not unusual for
girls to do, until the boys cut in and we had to dance with them. I didn't
mind dancing with the boys, but I preferred to dance with Elaine. This night,
I wasn't in the mood to flirt with the boys....my thoughts were only about
her. Late in the evening, when I could be alone with her, I asked Elaine if
she'd like to go out with me sometime.
"You mean go to lunch and shop together? Yes, I'd love to, Allisa," she
responded with interest.
"Well, not exactly. This may sound strange, but I mean like on a date," I
offered cautiously. Now I was committed...I must follow thru. In my mind,
with her I was Al, overlooking the fact that I presented myself as Allisa.
"Allisa, I don't date girls!" she admonished.
"What if I told you I'm not really a girl...would that make a difference?" I
asked, risking everything. I really wanted to date her but I hoped I wasn't
chasing her away. I had to try. I had very little experience asking a girl for a
date, and here I was, doing it dressed as a girl.
"Oh sure?.and I'm an alien from Venus! Is this some sort of joke? Are we
on Candid Camera or something? What do you mean you're not a
girl....you're as female as I am...why, we've been in the powder room
together..I..I've seen you in your underclothes when we were
dressing....your voice, your figure, you've got breasts! If you're not a girl,
then neither am I," she retorted in disbelief. "You're teasing me...Why are
saying this? I was starting to like you as a friend...now this cruel humor.
Why?" she asked, her eyes filling with tears.
"I want your friendship as a man, Elaine. How can I prove to you that I'm
really a male?" I asked, pleading, searching in desperation.
I couldn't very well ask her to feel my manhood under my dress, nor could I
lift my skirt and expose my male genitals to her. What could I do but try to
explain.
"It's just that I've been cross dressing for a long time and I've developed a
very feminine appearance. I fool everybody. My breasts are silicon rubber
glued to my skin. The rest of what you see is real but a result of hard work
and training. I'm here like this tonight as a favor to Dee because Gail broke
her leg and Dee needed a last minute replacement."
"Then if you are a male, who are you, really? I only know a girl named
Allisa."
Now Elaine, regaining her composure, was curiously interested.
"I'm Sis's brother Al, I'm not really her cousin from out of town as
everyone was told. That was just a cover story. I live and work here. I'm
a genuine male, Elaine, and since I've gotten to know you, I like you very
much, and I want to date you as a male. Does it offend you that I'm a cross
dresser?"
Elaine, by now, was almost speechless. She knew Sis through their
friendship with Delores, but she didn't know Sis had a brother. When she
thought about the situation, she said,
"No, I'm not offended that you're a cross dresser, but I'm a little
embarrassed that I believed you are a real woman. You're very convincing,
to the point that you make me jealous of your appearance. I know, it was
your intention to make everyone think you're a woman, and it wasn't meant
to be a malicious deception....I understand you're only trying to be helpful. I
think you make a beautiful and talented woman even if you are a male.
Yes, I'd love to go out with Allisa; I think having lunch and going shopping
with her would be fun, but I don't know this Al person. I'd like to meet
him, so, yes, I accept his offer of a date. It would be like a blind date....even
tho I'm talking to him, I don't know what he looks like. But, I've met Allisa
and I like her and I don't want to lose her friendship either."
"I can guarantee you, you wont lose Allisa....we're a package deal." I replied
cheerfully.
"Why didn't Dee find a real girl to substitute for Gail?" Elaine asked.
"For several reasons, I guess. I had attended the rehearsals and knew the
procedures, I was available on short notice, and my sister knew I'd fit the
gown and would be willing to wear it. That's a tall order to find anyone else
so quickly," I responded.
Elaine nodded in acceptance of my reasons.
"You're right...it was nice of you to pitch in like that. I don't know of any
other boy who would do that for a friend," she said, winking at me, with a
big smile.
We continued to talk on a more calm basis. A big hurdle had been overcome
for me....I could finally relax.
"Tell me, Al, why do you like wearing women's clothes?" Elaine asked, now
with a genuine curiosity.
"I guess it's a long story, Elaine. As a boy, I've always been sort of a dud.
I'm a little guy, and I always felt inferior. Seems like nobody ever pays any
attention to me. But, I had an opportunity to cross dress and experience
being a woman in public. I found that I was noticed more and treated far
better as a woman than as a man. I enjoy the little courtesies I'm shown. I
sense a personality change too...as a woman, I can climb out of the male
shell I created as a defense mechanism and be myself...be who I want to be.
I can laugh and cry openly and without shame, I can be cheerful and funny,
things girls can get away with that boys can't. I don't have to compete with
the macho guys, and do "guy" things...something I never have been good at.
I've always preferred the softer, gentler, more "womanly" things, I guess
you'd say. So, that's why I enjoy posing as a woman....besides, I like the
way I look and feel as a woman, I've been told I'm better looking than in
men's things."
"Wow, that's some explanation," Elaine responded. "You've got me
worried, I've not seen you as a man. Well, I've never tried to be a boy to see
how the other side behaves, nor do I want to, but I think I can appreciate how
you feel. Of course, if I behaved in a masculine manner, I'd be considered a
Tom Boy, and that's not unacceptable. It's too bad that in our society, you,
as a male, have to resort to impersonating the opposite sex to behave the way
you would like. As a man, you'd be considered a sissy, or as they say now,
a "sensitive" or "new age" man. But, as a woman, of course, you fit right
in. If you enjoy that, I say go for it! You do a great job. I can see you've
had a lot of practice and obviously do enjoy it. I'm not at all offended. I
think it makes you a better person, more sensitive to a woman's needs, what
with first hand experience. In fact, I think it would be fun to get together. I
certainly enjoy Allisa's company, and I'm sure you enjoy being her."
Elaine and I did start to date and continued to see each other regularly. She
was actually my first real girlfriend. Strange, I had dated a boy before I dated
a girl!...and tho I was comfortable as a girl being with the boy, I preferred
being a boy with a girl. Often, I would go as Allisa which Elaine enjoyed
because, as girls, we could do different things than we would as boy-girl
such as shop for and try on clothes in the fitting rooms together. We could
clown around, flirt with men, and generally have a good time. Al's
personality was different and the dates were more of a serious nature. As a
boy, I wasn't comfortable being so outgoing. I think Elaine got a kick out of
the contrast. I filled her in with all the details about Allisa, how I started and
my experiences as a girl, especially my date with a boy, which intrigued her,
especially the part about the kisses and how I enjoyed them. She was
fascinated by my ability to easily transform myself into a woman, with a
corresponding personality, a nicer, warmer one than Al's. I