The Advisor - 2

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The Advisor -- 2
By Katherine Day
(Copyright 2016)
(My name is Pernod, but everyone knows me as Perry. They say I’m really good at giving advice to teenage girls. But I’m a boy, or am I?)

(From the previous chapter) We hugged and I began crying. When I dried my tears, I told her how mom had caught me in one of my sister Kelly’s nightgowns, and had occasionally let me dress up around the house, even helping me learn how to put on makeup, even though I had picked up the basics through watching her and following some clips on You Tube.

“I’m happy you’re not disgusted with me, Cindy,” I said when I finished my story.

“Why should I be? Now, I’ll be friends with the prettiest girl around,” she said.

2 – Enraptured Boys

While I kept my hair fairly long so that it reached my collar, I had never tried to fashion it, merely being content to brush it and to let it hang a bit loosely. I had gotten into the habit of continually brushing it back from my face, and I guess that added to the perception that I might be a girl. My hair was brown and fairly full, but I never thought my hair could be as pretty as Cindy’s blonde tresses or Sylvia Perez’s jet black hair.

“Perry, I think I can fix your hair so that you’ll look really sweet,” Cindy said as we prepped ourselves to take our pictures for the site.

“OK, go for it, but I still need to have it look like a boy’s hair after this is over,” I said.

“Don’t worry,” she said.

I wasn’t too sure, but I accepted her assurances; she was my best friend and I didn’t think she’d do anything to shame me. I worried a bit as she fussed with it, even trimming it a bit with scissors. She worked some hair across my forehead, smiling and looking pleased with herself as she worked. Oh no, this is going to be awful, I thought.

“There it’s done,” she said fifteen minutes later. “Let’s see how you look.”

“Wow. That’s me?”

“Yes, young lady, that’s you,” she said. She was standing behind me as we looked into the mirror and we both smiled into the glass. She leaned over and kissed me lightly on the cheek.

“We’re the bestest of girlfriends now, Perry,” she said.

“I like that,” I said. We kissed again, this time a bit longer.

“Could we borrow a blouse or some type of top from your sister, Perry?” she asked. We were only going to do headshots, but it was apparent I’d probably need to wear something girlish, since my shoulders would probably show.

“I don’t think Kelly will care,” I volunteered. “She’s off to college and won’t be back now ’til Thanksgiving.”

As the two of us entered Kelly’s bedroom I tried not to betray how well I knew how to navigate her closets and dresser drawers. I let her blunder through the outfits.

“How’s this?” she asked pulling a sleeveless blouse from the closet. I almost gagged; the blouse she grabbed was one of my favorites and I had worn it several times during my moments as a teen girl. It was a light orange satiny pullover that fit tightly against my body and was highlighted with blue curlicue trim. It looked so feminine.

“It’s OK, I guess,” I said, trying to hide my enthusiasm.

“Maybe it’s not right for you, Perry,” Cindy said. “I think the top should be worn by a girl with breasts and you’re pretty flat.”

“I’ll wear it, Cindy. I like it, since the color will go good with my hair,” I said. “We won’t be showing my chest anyway in the picture, will we?”

Nonetheless, Cindy felt I should show some shape to my chest, so we searched through drawers until we found several old training bras that Kelly had stashed away. Cindy helped me put on the bra, and after stuffing some socks in each cup, I magically had breasts. I liked the feeling.

*****
The posting of our pictures brought an almost immediate growth in the number of hits that our site got. Unexpectedly, we found more and more boys writing in, and not all the messages included questions; some of the boys had other ideas. Here’s just a sample:

“Wow, Perry, you’re hot. Have you got a boyfriend? If not, I’m six feet tall, blonde and starting tight end on our football team. Write me at [email protected].”

“Perry. I have a juiced-up ’67 Ford Fairlane convertible. Come ride with me. Hotrod [email protected].”

“I’d like to bring you home to mom. [email protected].”

Virtually all of the boys sent along pictures of themselves, and I must say I found myself imagining how sweet it might be to be dancing, hugging and maybe even kissing some of them. Some, however, were truly embarrassing and, I guess, you’d call them x-rated. I found pictures of boy crotches to be disgusting. Needless to say, I didn’t respond to any of these nasty messages and trashed them all.

Cindy got a few such messages, too, but I got maybe three or four times more than she did. It was embarrassing and I began feeling so bad for Cindy; she was the sweetest, dearest of friends and I hated to see her hurt.

Cindy sensed my feelings and volunteered: “See I told you that you were the prettier of the two of us, didn’t I?”

“But it’s not right, Cindy. I’m a boy.”

“Not that I can see,” she said. We both giggled.

*****
It brought back memories: A year earlier, mother caught me in my sister’s nightgown one warm summer afternoon when she arrived home early from work. I had raided Kelly’s dresser and found a light almost translucent gown with thin straps over the shoulders and paraded in front of my mirror feeling totally girlish. Underneath, I wore panties (also taken from her). I had laid down on my bed after a while and day-dreamed over how sweet it was to be a soft, lovely girl; it was true, I had the fleshy, unmuscular body of a still to mature teen girl.

I had fallen asleep in my reverie. I awoke with a start when I felt someone nudge me. It was mother; I panicked. I bolted upright into a sitting position, feeling exposed and violated.

"Oh mom, I'm sorry," I screamed, beginning to cry.

She stood there for a moment, her puzzled expression turning into a smile.

"Mom, I'll never do it again," I said, blubbering through my sobs.

Mom continued to be silent. She studied me, still smiling and then reached to find a tissue from the nightstand. She handed it to me, "Here, wipe your eyes, my pretty girl."

She sat next to me and hugged me tightly.

"That's OK honey," she said gently. "I've suspected you might be borrowing Kelly’s clothes for some time now."

"Are you mad at me, mother?"

"Yes, because you sneaked into Kelly’s room. That's being a thief and being dishonest," she said, her voice growing stern.

"I was afraid of what you'd say."

“That’s exactly why shouldn’t lie to me, Perry, and also you can imagine what your father would say if he saw you like this.”

I hung my head; my father, who was naturally athletic, would be furious, I felt. Dad had been gone for over a month to erect a giant excavator at a mine in Brazil, but was to return within a few days. After such prolonged trips, he’d be home for several weeks at a time, before he’d be sent out again. Dad was really pretty nice to me, except for his constant nagging that I keep my hair trimmed. To satisfy him, I was always careful not to let it get too long.

“Don’t tell daddy,” I said.

“I won’t, but you must tell mother about your feelings," she continued her voice softer now. "Do you like wearing Kelly’s clothes?"

"Yes, mother, but I know I shouldn't 'cause I'm a boy."

"Hmmm, yes you are, but you're also a very pretty girl, darling."

"I am?" I asked, clearly flattered by her comment.

"But if you're going to dress up like a girl, I guess you’d better do it properly," she said smiling.

“Mother, you really don’t mind?”

She paused before replying. “Yes, I do mind a bit because we thought we were raising a son and not a girl as pretty as you. It’s just such a shock. Do you really like posing as a girl?”

“Yes, mother,” I replied sheepishly. “And, mother, when I’m all dressed up I feel I am not posing. I feel I am a girl. In fact, I like being a girl.”

“Well, for now, Perry, get out of your sister’s things and get into your boy clothes,” she ordered.

I wanted to cry. I thought mom might understand, but I’m not sure she did. I knew my dad wouldn’t understand.

*****
On Saturday, two days after mom
caught me in Kelly’s nightgown, she said to me as she served me pancakes for breakfast, “I still can’t believe that you’d sneak into Kelly’s room and put on her clothes, even her panties.”

“Mom, I told you I won’t wear any of her stuff again,” I repeated, even though I wasn’t sure I could live up to my words.

“That’s a promise I’ll hold you to, Perry.”

“OK.”

She returned to the stove to scoop up several of the pancakes, placing them on my plate. She looked at me quizzically, “Are you truly serious that you like dressing as a girl? And that sometimes you even think you’re a girl?”

I looked down at the plate of pancakes before me. I was afraid to answer the question; I felt I was serious about the desire, but I had no idea what the consequences would be should I admit it. After all, I was a boy, everyone expected me to be a boy.

“Well?” she pressed the question.

I nodded.

“Is that a yes? You wish you were a girl?”

“Yes, mother.”

It was funny. The instant I admitted to it, I felt like a weight had been lifted from me, that I was exposing my true self and that somehow everything would work out in the end.

“OK, Perry, I guess I understand,” mother said. “Maybe we ought to give you a chance to try it out, but we’ll have to do it properly. No more raiding Kelly’s room and no more lying to me.”

“You mean it mom? Thank you, thank you.”

“Finish your pancakes and sausage, darling, and then we’ll go shopping for your own lingerie, so get dressed when you’re done with your pancakes.”

“You mean we’ll buy my own panties and bras and gowns?”

“Every girl needs her own things, doesn’t she?”

I gulped down the rest of my food and rushed upstairs to dress.

“Today, honey, and only today, you can wear some of Kelly’s stuff,” she said. “You can wear a pair of her jeans and pick out a cute top. I’ll be up in a few minutes to fix your hair.”

“But, mother, you mean go outside as a girl? I can’t do that. People will know.”

“Just do it. You want to be a girl. Now you’ll have to see what it’s like.”

“But, I might meet someone from school,” I protested.

“Don’t be such a ninny. Believe me, you’ll just look like a typical teen girl.”

*****
From that day on and whenever my dad was gone on one of his long trips, mother occasionally let me wear my girl clothes. She even helped me to look pretty. We had already created a modest wardrobe, including a nice plaid skirt, a white blouse with a collar and a fluffy sweater. I even had a half dozen panties, ballet flats, panty hose and simple faux pearl necklace. A few days earlier, we picked up two size 34-A bras and cheap breast forms. She taught me to apply light color to my face, a neutral shade of lipgloss to fluff up my lips and a modest bit of eye shadow.

From that time on mother took me to the Uptown Salon to have my hair trimmed and styled. At first I resisted going there, but the ladies there treated me with great attention and respect. They styled my hair into a page boy that could be considered to be quite androgynous. "Your classmates will still see you as a boy, but others might see you as a girl," Beatrice, the salon's owner and a friend of mom's, said. "Is that OK?"

"I guess, Miss Beatrice."

"You are a very pretty boy, Perry," the salon owner said, smiling.

After my hair styling began, it turned out that I was usually called "miss" or "young lady" by strangers; for a while, I wondered whether I should correct them, but then thought the better of it. If they thought I was a girl, so what? I even began feeding into the image by walking more erect and taking shorter steps, bringing about a natural feminine sway to my motion. Mother and I went shopping for clothing that might be considered androgynous; I took to wearing girls’ jeans that actually fit me more comfortably than boy jeans due to their taper and wider hip size.

We restricted my girlish moments to those periods of time when dad was gone. During his weeks at home, I chose my boy clothes and tried to dress in a more masculine manner; we went so far as to have my hair cut and put into a more boyish style a few days before he returned home. Of course, we hid my stash of feminine clothes.

It surprised me how easily I slipped into the life as a teenaged girl; though I had yet to venture out in public in a skirt or dress — still choosing the androgynous look — I found boys looking at me, often smiling and sometimes sensed their eyes following me as a walked by. I was apparently a pretty girl in their eyes. What a great feeling! And a scary one, too!

(To be continued)
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Comments

Perhaps the real her is now

Perhaps the real her is now coming out of him with the help of Cindy and their new website.

memories...

Looks like Perry is starting to come to terms with suppressed feelings. Perry's feelings of unease are more about enjoying the experience rather than going against her nature. Hopefully Cindy saw the same thing Perry's mom saw and is trying to help her rather accept herself.

I'm told STFU more times in a day than most people get told in a lifetime

Thank you Katherine,

So true for a lot of us but so wonderful when you have a Mum who realizes who you
are and accepts you .A lovely story and I look forward to more .

ALISON

Neat Story!

Thank you - can't wait to read part 3. It's really nice that his (her) mom accepts it and helps out.

Coming of gender

Jamie Lee's picture

A very nice story about a boy coming to terms with his hidden gender.

Mom is accepting, will dad? Will Perry and Cindy continue with their blog? Who else will discover a girl named Perry?

Others have feelings too.

A scary one ? Perhaps, but

A scary one ? Perhaps, but you should be excited for your mother's support.

Karen