💾 Archived View for tilde.pink › ~nifty › tv › the-beginning-of-womanhood.gmi captured on 2024-05-10 at 13:32:04. Gemini links have been rewritten to link to archived content

View Raw

More Information

-=-=-=-=-=-=-

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

out in drag. ��She did my eyes and then proceeded to finish hers.

"You're lucky in a way, Barbara, not having to work." "Do you think

I wanted to lose my job?" I replied. "No, I'm not saying that. It's

just that you have time to explore the far reaches of your

personality. You are not hindered by time as I am. You look great,

by the way," she said. "Thanks" I replied as I was blow drying my

hair.�

Carol asked me to stop at a jeweler and get my ears pierced this

morning at the mall and to get som small diamond studs. After a

look in the mirror and checking out the reflection, I was more than

glad to say yes to her and to ask where she suggested I go. She

told me of a little shop on the second level of the mall which was

run by a girlfriend of hers.

She put a pair of clip-ons on and said they were for now and new

ones would come tonight. I wasn't sure what she meant and she

touched my lips with her finger when I was about to ask. "You'll

find out," she said. "Now move the car, I have to get to work. You

might as well get Peggy now so I can get out of the driveway." I

looked at the clock and it was seven fifteen. I was nervous about

going out in my new outfit but Carol grabbed me by the arm and said

"Let's go, I'm going to be late." So I went.

While walking, I looked down at my "breasts" under my long sweater

and got a charge. I loved the way they proudly stood out. I

generally liked my look. "Baby, I'm going to be late tonight," said

Carol. She explained that she had a client coming in from

California who was showing a new line of fashions (Carol is a buyer

for a large department store) and had to bring him out to dinner.

She told me to have fun with Peggy this afternoon when we went

shopping and suggested we go out to dinner ourselves.

She offered to let me wear a new dress that she had bought and only

worn once. I was a black sleeveless cocktail dress that fell mid

thigh and looked great with pumps (the higher the better). I told

her that I thought things were going a bit fast and that maybe we

should slow it down a bit. She looked at me and said, "Who are you

kidding? You were born to be doing this and you know it." I giggled

a bit and she laughed. "Go get your girl friend and get her to work

Barbara. And behave yourself today." I kissed her, careful not to,

mess her makeup or mine and went off to get Peggy.

On the way over I got quite scared since I had no wallet, no

identification, just the clothes on my back and the car keys. I

pulled up in her driveway and got out. I walked up the front stairs

and rang the bell. She met me in a bathrobe and curlers. Her eyes

lit up when she realized who I was after she gave me a double take.

"Bobby?" she said. "Yes," I said, "can I come in?" "Oh, sure,sure,

I'm sorry. I just wasn't sure it was you. You look gorgeous. Oh,

you're blushing. It's okay, it looks cute on you." I was waiting to

come up for air.

Peggy was racing around the house screaming about how late she was

for work, running and holding her curlers in her hair. She was

wearing only a shortie kimono silk bathrobe that kept opening as she

ran around exposing various body parts. I was really enjoying the

show and she knew it. During a sprint with a comb in one hand and an

uncurled curler in the other, she finally stopped short about six

feet from me. She turned to me and laughed. Her robe was wide open

and she was naked underneath.

I could see the tuft of hair between her legs and her well formed

breasts. She quickly marched over to where I was on the couch and

sat next to me. She kissed me on the cheek and said, "I'm not going

to work today, Barbara, we're going to play, okay?" Her breasts

were fully exposed now as she sat there next to me and I looked at

them, rather than her, and said okay. She took my chin in her

fingers and lifted my head up so I was looking her in the eye. "Are

you talking to them or me?" she asked. "Oh, you of course," I

replied. "Good," she said, "I thought I lost you for a minute." I

laughed hard and so did she.

She picked up the phone and called into work and told them she was

not coming in all the while smiling at me. She explained about her

car and how she wasn't feeling well and how she just couldn't do it

while she winked at me. She hung it up and put her hand out for me

to give her "five" which I did and she said' "let's party."

I was game but didn't know what to expect. "First Barbara, we have

to get you some clothes and lingerie. We can do that this morning.

Then we go out to lunch. We'll stop at the hotel for the four to six

crowd and then go bar-hopping. Are you game?" I stood there with my

mouth open. "That's a big step for me Peggy," I said. She assured me

I looked great and would have no problems. She was really charged

up about blowing off some steam and needed an accomplice. I was that

accomplice.

"Peggy, I don't have my ID or credit cards or anything," I said,

"how can I go shopping?" She told me not to worry, that she would

charge everything on her cards and I could reimburse her. She

started to pull the curlers out and dropped her robe to the floor.

She stood in front of a full length mirror and combed her hair our.

She turned to look at me and said, "Since you're one of us now, I

don't have to worry about walking around in various states of

undress with you anymore. Come her and help me get dressed." ��I

helped her clasp her black bra and matching garters to a sheer set

of sandletoe thigh highs. She pulled up a black string bikini panty

and finished with a black leather mini and a white see-through

blouse. She put on a wide belt with a gold buckle and a pair of

three inch spike pumps.

A touch of makeup and she turned around and asked "How do I look,

Barb?" I could have dropped to my knees. She looked gorgeous. I

stared at the pumps especially. She asked if I wanted to borrow a

pair and that she could match the red color of my flats to which I

said, "Oh, yes might I?" (I couldn't believe I said it but I was

completely spellbound by the figure before me and the costume and

aura that surrounded me.) I wanted to go further and further with

this and wasn't quite sure when or where to stop.

Peggy handed me a pair of red spike pumps. I tried them on and they

were a bit tight but they fit and I pranced around the room in

them. I swung my butt and hips for Peggy and she laughed. She

remarked that I appeared to be getting off on the experience. One

look in my starry eyes told the whole story. I was. I loved it. She

held a hand out and motioned me to come with her into the bedroom.

She held my hand and led me to her large closet. "Is there anything

that you want to wear today that's in here, Barbara? I have a lot

of things that will fit you. Carol says you're a ten just like me."

I gazed in wonder at the many dresses, skirts, blazers and blouses

that were hanging in front of me.

Peggy told me to remove my sweater and my pants which I did. "You

can put the pumps back on if you want," she said. I did. I stood

there and tried dress after dress on. I was having a ball and so was

Peggy. She and I finally settled on a black mini with a flame red

low cut blouse with a black camisole showing underneath. I wore

garters and stockings underneath and a pair of four inch patent

leather heels finished off the look. Peggy teased and sprayed my

hair, used additional eye shadow and mascara and finished me off in

a black biker jacket with studs. I looked in the mirror and almost

fainted. Between the punk hairdo, the tough looking jacket, the low

cut blouse and the "knock me down and fuck me" pumps, I was in a

state of shock. "Is that really me?" I sad. "Sure is," replied

Peggy.

"It's fun being a girl, isn't it?" "Yes," I said, "if I ever live

through it. My pulse must be about two hundred right now Peggy."

Peggy looked at her watch. It was twelve o'clock. "Time for lunch,

hon. Let's go to the Homestead." "But that's a pick up joint," I

said. "I know, silly, why do you think I recommended it?" She gave

me a shiny black leather pocketbook with a long shoulder strap and

put some hankies, makeup and an old wallet in. She then opened a

drawer in her night table and took a tampon and a rubber and

dropped them into the purse too. "You want to look real don't you?"

I laughed and we scurried out to the car and to our lunch date.�

>>>>>>>> to be continued (soon) >>>>>>>>>