Memoir of a Stealth Transition - 7 of 38

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Chapter 7 - The Surprise

Let me introduce you to my grandmother - my mother's mother. I had another one, Dad's mother, that you'll hear about later, but she had died when I was very young.

Grandma Gladys was a tall, slim woman, much like her daughter, only Grandma Gladys had remarkably big boobs. Listen, my thirteen-year-old self didn't go for the more polite 'breasts.' Girls, and by extension women, had 'boobs.' I'd known that before - obviously! - but with my newly heightened awareness having just had 'The Talk' and having found out how delightful wearing a bra could be I had to wonder just how big were they?

Not something a kid can comfortably ask his grandmother, eh? I later found out she was an E cup by looking at the tag of one of her brassieres while they hung out to dry. Pretty sad, huh, a kid checking out his grandmother's boobs. I can only plead that puberty, such that it was, must have been starting around then. I had a well developed fascination with breasts, and it never really went away even when I got a pair of my own.

Then there was Grandpa Dave, but he was off golfing. The man was ga-ga about golf, and had tried to get me interested, too. Didn't work, I found it boring. If he wasn't golfing he was fishing, and I didn't like that much either. Now that I'm an old fart I rather enjoy fishing, that is to say drowning worms and maundering while reading a book. Golf is still boring.

Back to the main thread of the story. Grandma Gladys was a tall woman, 5'10", as was my mother. I was not so lucky, I barely made it to 5'5" if I tried to lift myself up on my toes while the doctor slid that metal thing down the wall when they measured your height. I wasn't the shortest kid in my class, but I came close.

I'm maundering again - that's the third time I've gotten sidetracked since I tried to tell you about Grandma.

Naturally I got hugged, placing those boobs practically in front of my nose, and told how big I had grown. Grandma was a good liar, I hadn't grown at all in the two weeks since I had last seen her.

"You look so much like your mother, Con. You really ought to let your hair grow out. Boys these days don't need to look like they just got scalped after joining the army."

"I've been thinking about that, grandma."

"Well do it, child."

"Yes ma'am!" I gave her a mock army salute.

"You're as much of a wiseacre as your mother."

"We tried to raise him right, Mother."

"Work on that teenage rebellion thing, won't you Con? Your mother deserves as much grief as she gave me growing up."

"Don't encourage him, Mother! He does just fine without any help."

"Can I be a radical when I grow up?" I asked.

"Go ask your father."

Naturally Grandma had cookies and cocoa waiting in the kitchen. We sat around and talked a while I tried to be patient, but I really wanted to see if any of Mom's ice skating stuff was still there. After going through those books on ice skating I thought it would be something pretty interesting. Those little short skirts and flashy tops had nothing to do with my interest. Sorry - I just can't lie as well as my Grandma Gladys. I wanted to wear Sonja Henie's tutu, but I'd happily settle for my mother's tutu if it fit.

Fat chance, right? I already told you she's much bigger than I was at thirteen.

Eventually we went up to grandma's attic. I've always loved her attic, she and grandpa lived in this huge, three story old house and the attic was filled with treasures of every kind. It smelled of old dust and faint perfume, and on sunny summer days could be like an oven. I suppose these days Grandma Gladys would be called a hoarder, because the attic wasn't the only room filled with - to put it kindly - the castoffs of a lifetime. When they passed it took months to clean the place, but once again that's another story.

I discovered another downside to having been born male that afternoon - I got to be the one to shift all the boxes around while the delicate women searched for the box - or was it a trunk - or maybe a big suitcase? - with Mom's skating things in it. I could easily get distracted telling you about the other things we found (including some dresses that just might have fit me) but I'll cut to the chase. Eventually we found the right trunk and between us we managed to get it downstairs into one of the spare bedrooms. Then I had to go and wash the crud-of-ages off my hands before I could touch anything. That attic had a lot of dust collected over the years.

Sure enough, there were three pairs of skates in there, in varying sizes as Mom grew up. The biggest pair still fit her and the smallest pair fit me. I was not allowed off the rug under the chair I was sitting on to try the skates, grandma didn't want her floors ruined. My image of being a beautiful ballerina on the ice, floating along and jumping gracefully into a spin took a beating, I was barely able to stand up balanced on those thin blades. Reality sucks sometimes. Mom assured me she could show me how to skate properly, it was only a matter of practice. I sure hoped she was right.

There must have been two dozen outfits in there, Mom must have really been into skating. Mom couldn't resist seeing if she still fit into the one she used for her last competition, so she disappeared into the bathroom to change. Grandma had this enigmatic smile on her face while we waited, a smile I now know after reaching the age where nostalgia looms large in your life. She was obviously remembering the little girl who once was.

Mom came back and it seemed that fifteen years and one pregnancy had not affected her figure. The outfit still fit. Now those skating costumes are made to be a close fit, there isn't much room for growth allowed. I could see Mom's bosom (thinking boobs in front of my Mom and Grandma was really too much) was a bit tight - something she blamed on me using them as a baby. I think that's the first time I started to appreciate my mother as a woman, that skating outfit displayed her figure very well.

"I never would have believed it, Beverly," Grandma enthused. "You always looked wonderful in those outfits and you still do. I just wish I could still wear things from fifteen years back."

"Fishing for compliments, Mother?"

"Your father does the fishing in this family. I do the wishing. Look here, this is the first one you wore when you were eight years old. You looked so adorable."

"And I got eliminated when I blew the last jump and Shelly Wilson got the first place."

"Still got that competitive streak, eh daughter?"

"I guess I do."

"What was this one for, Mom?"

I couldn't help it. The outfit was a creamy white with gorgeous embroidery around the neckline and the edge of the very short skirt. The material was very stretchy and it was all in one piece, with the panties as part of the dress. I instinctively held it up and measured it to my body.

"My god, Bev. If it wasn't for the brush cut I'd swear you were a teen again."

"Well, Mom said I'd look cute in at tutu just the other day," I offered.

"It looks like it would even fit you, Con." Mom said.

"So, should I wear it when you teach me to skate, Mom?"

I just hoped the light bantering of the morning would let me get away with that.

"Your hair would give you away, I'm afraid."

"Now that shouldn't be a problem. Just wait here a minute," Grandma said.

She left the room and a few minutes later came back with a wig, one that was practically the same color as my mother's hair.

"I can't wear this any more since I let myself go gray. Let's see what you look like with long hair, child."

So grandma fussed and tugged and brushed and when I looked in the mirror the mother-daughter resemblance was very apparent. The wig was much like how my mother wore her hair, enhancing the effect. A lot of girls in those days were wearing jeans and a t-shirt much like what I was wearing (although the girls usually had flowers or puppies on them), so even the clothing wasn't too out-of-place.

"I can't believe it!" my mother said in wonder. "I knew you took after my side of the family, but that's… that's… spooky!"

"Should I try on the outfit?" I asked hopefully.

"Do you want to?"

"I think I do."

Oh boy, I had to take the chance. I just had to.

"Then go ahead. It ought to be interesting."

It never occurred to me back then to wonder just what my mother and grandmother were discussing while I was gone. Like I said, my parents were pretty unusual, but they were the only parents I had. I was blissfully ignorant that they had noticed I was unusually interested in girl's things for a normal boy. Self-centered little brat, wasn't I?

So I went into the bathroom and took off all my clothes and tried on the outfit. Other than being a bit loose in the bust and tight in the crotch, it fit pretty well - at least after I took it off again to remove my tightie-whities, which just didn't work with those built-in panties that kept people from seeing too much when the skirt went flying. I took off my shoes and socks, too. That looked much better.

I was a bit nervous going back to show them how I looked, but I was simply too high with being able to wear a dress and feel like a girl that I was oblivious.

"I think I'm going to have to start believing in reincarnation, Beverly," Grandma said with a huge grin.

"There's no doubt that she's my daughter, is there Mom?

Daughter?

DAUGHTER???

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Comments

Love the story

Dee Sylvan's picture

perhaps this isn't as 'stealthy' as Con thinks. Telling his mother and grandmother he wants to wear his mom's skating outfit just let the cat out of the bag. Con has started the proverbial ball rolling downhill and there will be havoc. Dee

DeeDee

Grabbing the chance

Podracer's picture

with both little paws, is Connie. How different to most, even those who would have liked to take it too - and dare not. I hope all three of them enjoy the result.

Teri Ann
"Reach for the sun."

Remarkable!

What an amazing family! My family would have given me the lecture of a lifetime, my father would have beat my butt, and I would have been grounded for months.


"Life is not measured by the breaths you take, but by the moments that take your breath away.”
George Carlin

I just wish

that my mother seeing me in girl's clothing had gone well. Instead, I ended up in the hospital with a concussion, broken ribs and a punctured lung.