The Beginning of Womanhood
by Barbara Montana
I awoke that morning as I had during the previous three
months clad in a nightgown and my hair in curlers. This would
not seem so strange to the average person except for the fact
that people of my sex (male) don't usually wear nightgowns.
My wife Carol had gotten me started on the wearing of
nightgowns and other assorted pieces of female finery. I was
somewhat shocked when she first suggested it but I knew that
she meant business when she would only have sex if I were
dressed as a vixen.
She started one night shortly after we were wed by
leaving a long red floor length nightgown on my side of the
bed before we retired for the evening. We had been out
partying all night and I had a few drinks in me. Carol had
already changed into a long silky black low cut nightgown and
was laying on top of the covers while I was taking off my
cothes and getting ready for bed.
I looked at her and my side of the bed (with only my
bikini briefs on) and asked her why she had the red nightgown
on the bed when she already had one on. She stated that the
red nightgown was for me. I looked at her in disbelief. "For
me?", I said. "Yes" Bob, she replied and stated that I looked
a bit horney and the only way I would get near her was to
wear the nightgown. I figured "what the heck" and put it on.
"Are you ready for me now?", I asked. "Not yet" she stated
"You're not going to leave that underwear on under that
beautiful nightgown are you?" I looked down and pulled my
gown up. Maybe the underwear didn't go with it. She went to
her bureau and pulled out a pair of red tap pants and
instructed me to put them on. I immediately put them on and
asked Carol if that was all. She said it was for now except
that I had to go downstairs for a candle. She said she felt
romantic and that would fit her mood. "By the way, what did
your sister Jill call you?... Barbara? I blushed..
I complied with her wishes and went downstairs in my
new clothes and rummaged through drawers for a candle. While
walking around I felt the silkiness of the long red nightgown
on my body and the weight of the straps on my shoulders. I
enjoyed the swishing of the tap pants on my crotch and
thought back to my younger days when my sisters dressed me up
when my mother was out.
I had been raised as the youngest of five with four
sisters who were older. I was somewhat a toy to them,
something to dress up and play with. My thoughts went to a
little yellow party dress that they had me wear one day. I
resisted but without avail and thay finally got it on me.
When they got me into it, my resistance stopped. I knew I had
been beaten and just took a breather. My oldest sister, Jill,
looked at me and said, "Bobby, I think you look more like a
Barbara." Being twelve, I couldn't think of anything else to
do so I stuck my tongue out at her.
She and my other sisters laughed and said that I looked
like a little sissy with my yellow dress on and my tongue
out. I was humiliated. They comforted me after I started
crying and told me they wouldn't bother me any more if I
completed my outfit. I agreed and put on white anklet socks
with turned down fringe and black patent leather pumps that
had belonged to Jill. Jill also handed me a pair of panties
that had tiers of ruffles on them and told me to put them on.
I was totally embarrassed but did so after shedding my male
undershorts from under my frilly party dress.
My sisters were all giggling at this point and I was
ready to break down and cry. Jill noticed my predicament and
gave me a hug. She told me I looked pretty and not to get so
upset. My other sisters were saying, "What's wrong Barbara?"
(in a mocking tone) as Jill was consoling me. Jill took me
into another room and told me that I really was pretty in my
dress and asked me to turn around in front of her. I did it
and then she asked me to put my arms out as I did my swirl. I
did that for her too. She held me by the arms and said that I
was as pretty, if not prettier, than my other sisters.
I came back to reality and realized that my yellow
dress had been replaced by a red nightgown. Carol was yelling
from upstairs. Where is the candle? I want to have a soft mood
here in the bedroom. "Bring it up here and light it," she dem-
anded. I pulled the nightgown up to my knees with one hand,
rushed up the stairs and complied with her wishes.
"You know Bob," she said "I was talking to Jill the other
night and she told me stories about when you were young and
your sisters used to dress you up." She said that you didn't
like it at first but after a while you really didn't need any
encouragement. As she spoke on about my experiences with my
sisters, I wondered how much Jill had actually told her. It
seemed as she went on that there was very little she didn't
know.
I admitted that I had learned to enjoy wearing girl's
clothes and playing little girl's games including dolls and
jump rope. My sisters had conditioned me at a very young age
and it was a matter of survival in that household. Carol said
that she liked the idea of me having an obvious feminine side.
She said she wanted to explore it more with me and that she
would very much like me to dress up for her and to let her guide
me into the ways of womanhood.
"I'm kind of excited about this Carol," I said nervously "but
I'm kind of scared too." "What are you suggesting?" I asked.
She said that since I had such a slight body and such fine
features that I would have no trouble passing. She also said that
she would like to have a girlfriend to shop and gab with and that
I would be perfect. She also humiliated me when she said that I
was obviously effeminate and her friends had noticed that and
commented to her about it. She said that some were actually
jealous of her because she was always able to talk to me about
clothes and other feminine things in front of them. I was
encouraged by Carole to participate in conversations with her
girlfriends when they came over.
They were a bit guarded at first when the talk inevitably
turned to men, but after a while they discussed their periods,
affairs, fantasies and other juicy tidbits in front of me and let
me participate fully in the conversation. When the conversation
got around to men I usually clammed up but every once in a while I
would join in on the commentary about how attractive some male
movie or soap star was and the many romantic rumors that
surrounded them.
After a while I was totally accepted in their gossip and they
often substituted me for Carol when they called for her and got me
instead. These gossip calls came especially from two of our
friends, Peggy and Susan. I became as caddy as any of them and
freely talked about the bitches of the neighborhood, gaudy outfits
that were being worn by those women we didn't like and other fun
topics.
Carol said it would be logical for me to express my feminine
side and to dress the part occasionally. She then dropped a bomb
on me. She told me that she had spoken to Peggy about it and that
she had agreed that it would be a good idea.
I was flabbergasted. "How could you embarrass me like this,
Carol," I said, "oh, how am I ever to face her again?" I held my
head in my hands and sobbed. Carol put her hand on my shoulder and
told me not to get so upset because Peggy was a friend and should
be trusted as such. "Sure," I said, "and the next one she'll tell
is Susan." I was filled with a sense of sorrow that my fond
relationship with Peggy and Susan was now touched by my secret
desires and would never be the same again. I felt like I had lost
my best friends in a matter of minutes.
Just then the phone rang. I thought it was odd since it was
almost eleven o'clock and we usually didn't get calls this late.
Carol picked up the receiver, "Oh hi, Peg," she said. I almost
died. There I was sitting on the bed with my nightgown and panties
on, slobbering and Peggy had to call right at this very moment. I
wanted to crawl under the covers and hide.
Peggy obviously had a problem with her car and needed a ride
to work in the morning. Carol told her not to worry that "Bobby
would give her a ride." I held my hands over my mouth and wanted
to scream. It got worse.
I heard Carol say "wait a sec" and then handed the phone to
me. I was in a cold sweat at this point. "How could you do this?"
I whispered to Carol. She handed me the phone and I squeaked a
hello to Peggy. She said "Hi, hon. I got a problem. My car broke
down and Carol said that you can give me a ride to work tomorrow.
Is that okay?" I said sure (my voice was cracking by this time).
She then continued and said that she had a long talk with Carol
about me and that she didn't want me to be embarrassed. I
responded that I was and couldn't help it. She said that I was one
of her sweetest and best friends and that she wanted me to know
that if anything, my desires to dress as a woman could help our
friendship grow. I cried and she tried in vain to console me. I
finished the conversation by saying that I would pick her up in
the morning at eight. She then asked me to put Carol back on.
Carol spoke briefly to her and then hung up the phone. She
disappeared downstairs. I laid on the bed thinking and worrying
about what was next for me. Could things ever be the same with my
good friend Peggy? Or would she look at me as a freak; someone who
should be on the Phil Donahue show?
I went into the bathroom and splashed some water on my
face. My long hair was at my shoulders and contrasted quite a bit
differently with the red nightgown than with my regular attire. I
took a brush and brushed it out so that it fell evenly on my
shoulders. I liked the image that stared back at me and I smiled.
The breast of the nightgown was cut tightly on the bottom
and gave the impression that I had small breasts behind the
blousy top. I stroked the fabric and my nipples hardened and felt
like small pegs. I have large nipples (about the size of half
dolars, quite unmasculine and very sensitive. Carol commented on
this feature when we were dating and compared them to her nipples
which are just a bit larger. She liked and still likes to play
with mine during our lovemaking sessions and takes great pleasure
in making them stick out when I get aroused.
I lowered the spaghetti strap on one side of my nightgown
and played with my now naked breast. I looked at the image before
me in the mirror. There I was with my long blone hair, parted in
the middle (I usually keep it in a ponytail), flowing around my
shoulders. One side of my nightgown was down with my nipple
exposed and my hand was carressing it. My appearance was quite
feminine although I didn't have a great deal of mass in my chest
area. I cupped my breast from underneath and pushed it up so that
it would give the appearance of a more feminine form. I touched
and stroked it with the other hand. I was feeling a tingle in my
crotch and lowered my hand to massage it when I was shocked back
to my senses by Carol's voice.
She was talking to someone right outside! I then heard
Peggy's voice. Carol knocked on the door and asked if I was
inside. I said I was after getting over the initial shock. She
asked me to come out. I pulled my nightgown back up and was
completely confused as to what to do next. I looked around for
something other than the nightgown to put on. I had left the bath
towels in the bedroom after an earlier shower. There were no
clothes in the hamper. I had done a wash this morning. There were
nothing but face towels on the shelf and I was in trouble. There
was no way out and I knew it. I was trapped. I decided to come out
and face the music. I brushed my hair again, fixed the straps on
my nightgown and walked into the bedroom. I saw Peggy and Carol
sitting on the bed talking.
They looked over to me as I entered the room and Peggy said,
"Hi, hon. (her usual greeting to me) I had to come over after my
call. I couldn't think of sleeping after I knew you were so
upset."
She then got up from the bed and came over and gave me a
hug. I almost melted. She kissed me on the cheek and said that she
wanted me to know that she was and would always be my best friend.
She wanted me to be happy and that she didn't want to lose me. She
said that she understood and appreciated my situation and that she
and Carol wanted me to give in to it and that as wife and friend
they would support me in any way possible. A tear came down her
face as she talked to me.
I looked into her eyes and took both of her hands into mine.
I told her that I loved her and that she was indeed my best
friend. I looked at Carol and told her I loved her too. She got up
from the bed and we all hugged, kissed and cried together.
Peggy held my hand and gave me a small package. I accepted
it and opened it. It was a thin gold chain with a gold heart. On
the back of the heart Peggy's name was inscribed. She told me to
turn around and she fixed the clasp, securing the necklace. She
asked me to turn around so she could see it. I saw Carol looking
on with a teary smile and I walked to the mirror to admire my
friendship pendant. It was pretty and I loved it.
"You really didn't have to do this Peggy," I said. "No, I
wanted to" was her reply. "You are a dear friend and I wanted to
show my feelings toward you. You are going through changes and I
want you to know that you can depend on me if you ever need me. I
want you to be the happiest girl in the world." She said "girl." I
walked over to he and gave her a big hug. I kissed her on the
cheek and thanked her again.
She said that she had to be going and I said that I would
pick her up at eight. She asked if I minded driving her home also.
I said I didn't and then she asked if I wanted to go shopping with
her. She would be getting out early and she was going to buy some
clothes with a recent bonus she had gotten. Carol was smiling and
I said "Sure, that would be fun."
Peggy gave Carol and I a kiss goodnight and gave me a pat on
the butt. "You're going to be fighting the guys off soon, hon.
Maybe we should get you some conservative clothes so you won't be
mauled. That nightgown makes you look delicious." I blushed and
waved her off with a limp wrist.
"See you tomorrow" she said.
I went to bed that night happy with myself, my wife, Carol
and the world. Carol and I hugged each other and fell asleep in
each other's arms, two feminine forms resting before a new
beginning which would be coming soon.
Womanly Part 2
"Coming Out"
By Barbara Montana
Well, six-thirty came around pretty quickly and I was bushed. Carol
patted my rear end and said, "Wake up sleepy-head." "Let me sleep,"
I cried. She said I couldn't, I promised to drive Peggy to work and
I had to keep my promise. Carol pulled me out of bed, helped me off
with my nightgown and pushed me into the bathroom with only my
panties on.
I looked in the mirror. What a mess. My eyes were still puffy from
crying and my hair was in knots. I searched for some cream rinse
for my hair. Ah, yes, here it is. I pulled off my panties, jumped in
the shower, shaved real close, and washed and rinsed my hair (and
of course my other parts). I was starting to come alive again. I
finished up, wrapped myself in a towel and went out to the bedroom
where Carol was fixing her makeup.
I was wrapping my hair in a towel when I looked down at the bed
where some clothes were spread out. I looked at Carol and she was
already dressed for work. "They're for you" she said. I looked
again and saw a white satin bra and matching panties, a pair of
tight flowered stirrup pants with a pink, jewel neck, tunic length
sweater. On the floor was a pair of red ballerina flats.
"I can't wear this out, Carol," I protested. "It's not a question of
can't, Barbara, you can and you will," said Carol. She directed me
to put the clothing on, and threw me a pair of opaque black
pantyhose to wear with the outfit. She said that she had promised
Peggy that I would pick her up "enfemme" and that Peggy was quite
excited.
After drying off I resigned myself to putting on the clothes Carol
had laid out for me. I started with the panties. Thet had a ridge
of lace on the top and legs and felt cool as I put them on. I then
rolled the panty hose on. Carol commented at how well I mastered
the task. She said that I do it faster than her. I was not sure what
to do with the bra so I put the flowered pants on next and then the
red shoes.
Carol looked at me and said, "What are you waiting for? Put your bra
on." I looked back at her and said, "But there's nothing to put in
the cups Carol." She laughed and went to a top drawer in her bureau
and pulled out two small forms. She inserted them into the bra
after I had fastened the front clasp. I slipped the pink sweater
over my head and pulled it down around my hips. Carol motioned me
over and put a bit of lipstick on my lips. She also dabbed a bit of
blush on my cheeks. "Do you want mascara, Barbara?" she asked. I
said why not since I might as well be convincing since I was going