Boy to Bride Pt. 01 Ch. 01

Part 1: Adam MacDonald

Chapter 1: Ms. Alice the Widow

Adam carefully shifted the wooden board back in to its place. If only people knew what I kept up there, Adam thought, and smirked to himself. Before he was down from the stepping stool, he looked up at the ceiling 2'x2' entry leading to the attic—an artifact left for insulation and electrical, but Adam found other purposes for the musky space. Once his foot touched the floor, Adam felt the pleasurable, tickling feeling on his bare feet. He had been cross-dressing so regularly, that he had forgotten to remove his transparent nylon stockings. They just felt natural to him.

He admired how effeminate hosiery made his slender legs look even more feminine, and he caught a reflection of himself in the corner of his eyes. He walked to the mirror to get a better look of himself. He posed like any teenage girl would, and he did it on command by telling himself these three little rules that he came up with on his own: chest out, stomach in, ass out.

An irresistible itch would always be scratched whenever Adam recognized his feminine side. And he hated when his eyes would inevitably be drawn again to his birthed gender. His wig was already in the attic, along with the rest of his sissy clothes, and he was wearing an old t-shirt (and not the cute over-sized, boyfriend kind of shirt either). He ran his hand through his medium-length, shaggy, brown hair. One day, I won't have to hide who I really am, he thought as his eyes were again drawn to his hosiery.

"Adam would you come down here already? I've been waiting for you for the past fifteen minutes" Adam's mom hollered from downstairs.

"Just a second!" he shouted back, and took one last look at himself. Still a boy. He quickly removed the stockings and scrunched it up in a ball and hid it in the back of his bottom drawer.

Crossdressing was Adam's best kept secret. For years, he took every measure he could to guard this sexy, little passion of his. He learned early on the consequences of dressing up as a girl, and the importance of keeping it a secret, after his parents would routinely humiliate Adam by reminding of a VHS they had of him. Adam was five in the video and he stood in front of a mirror, dressed in one of his mother's black dresses and wearing a pearl necklace, applying cherry red lipstick to his lips liberally.

Throughout the years, the family thought nothing more of this video than just an excuse to tease Adam. They had no clue that he crossdressed to this day, and he found a certain thrill by prancing around in soft panties on some nights behind his closed door while his parents were still in the house.

He was just a little feminine.

Just a bored boy having a little fun with mommy's wardrobe.

He'll grow out of it.

...were all things his family members thought about the video.

They were not as compassionate as these thoughts made them out to be. They relentlessly teased him at home, thus developing a deep shame in Adam, one that he could, strangely, only find relief from dressing up as a girl—he forget about all his problems when he was feminized.

What solidified Adam's secrecy about his crossdressing was a story his father told one night during dinner. Apparently, some of the men in the town set up a sting and lured a crossdresser to a darker part of town and... disappeared. There had been gossip the months following this of men from our block who had been seen with a "tranny". Adam's dad made a joke that the closeted men were responsible for this, and they were trying to shut a loud mouth up. I think that he was only half-joking.

Sally MacDonald was Adam's older sister by two years. She was a blonde, blue-eyed beauty that could make any guy swoon at her feet without her even trying. Absolute perfection on the outside. A manipulative whore on the inside. When her looks get what she wanted, she had other ways to control men. From as far back as Adam could remember and up until high school, Sally used the VHS tape to blackmail Adam to do chores, take blame if she were to be in trouble in some way, or do any of her homework (Adam was a slightly gifted to do more senior work).

Adam entered the dining room and his mother and Ms. Alice were sitting on the same plastic-covered sofa, slightly turned to one another. Ms. Alice was an older widowed lady from across the street. After Ms. Alice's husband passed, she developed a bond with Adam's mother, and now she visited often on Sundays to gossip or play bridge.

"Adam," his mother turned at the sound of his footsteps, "It's about time, we've been waiting for you for a while. Ms. Alice has something to tell you."

She turned to Ms. Alice and smiled, then looked back at Adam, "Have a seat here now, I'll go get us some biscuits and tea."

"Hello Adam." Ms. Alice said and smiled.

Adam didn't know Ms. Alice much. He had helped out with outdoor chores, mostly mowing the lawn, cleaning the pool, and repaving the driveway, around the time her husband passed, but he never really had much conversation with her. She was nice from what he could remember—the cool sodas and ice cold water bottles were always a welcomed blessing to Adam.

"Oh, how you've aged. Already eighteen years young. How have you been, son? Your mother tells me you decided to not go to college this year." Ms. Alice said.

"Well, yeah, I haven't really made my mind up on college yet so I'm taking a year off." he said.

"And how have you been keeping busy?" she said, unnoticed by Adam, her eyes sharpened.

"I've been, uhh—" he began.

You've been dressing up as a sissy boy and prancing around your room in dresses and wigs from what I've seen. You ought to be more consistent with shutting your blinds, thought the nice old lady Ms. Alice.

"Aside from my job at the gas station, not very much. I've been reading a little bit." he said.

"Are you getting enough sun?" she reached over and pushed his bangs back. Adam had no time to react as this lady was, unwittingly to him, assessing him. For the first time in his life, he was glad when he heard the sound of his mother's footsteps and turned his head to the entryway. Ms. Alice noticed one long strand of blonde hair on the back of the boy's black shirt and smiled to herself.

"Just butter biscuits and refreshments today Alice, nothing fancy until Herald goes to the market."

"Oh don't worry about it dear."

"Your coffee, Alice." she placed the tray on the coffee table then took a seat on the adjacent arm chair, "So, what did I miss?" Mrs. MacDonald said.

Your son dressed up this morning, that's what you missed. And you don't even have a clue what's going on in your own roof, do you? You dumb bimbo, Alice thought.

"Oh nothing, I was just admiring how handsome your son has turned out to be. Is he dating someone right now? I'd always imagine her preferred the blondes."

At the sound of the word blonde, Adam blushed. He reached for a biscuit and kept his gaze away from anyone's eyes. Ms. Alice smiled and thought: Oh, this is going to be easier than I thought.

"Adam? Dating? Hah!" his mom chortled. Adam's awkwardness with girls had caused a bit of resentment from his mother. She had tried to set him up with her friends daughters, and all of those dates ended disastrously. When her friends wouldn't answer her phone calls, she ended up finding out that Adam would say not more than one word to the girls the entire date or even look them in the eye. Her friends thought she abused Adam or something, and since then, their daughters and themselves stayed away from the MacDonald family.

"But he's a very pretty boy."

Adam looked at Ms. Alice and was surprised she described him as pretty. She, of course, pretending she wasn't paying attention to his reaction and kept her eyes on Mrs. MacDonald.

"Call him what you want, doesn't matter if they boy has no courage!"

"I've got something to do." said Adam.

"Do what? You never leave the house!"

Adam frowned at his mother. She always does this, he thought. Indeed, Adam's mother would embarrass him in front of complete strangers. And he could never speak out no matter how much he wanted to. He just couldn't ever open his mouth, he felt it was glued shut. An immense amount of anger, confusion, and shame would always build up in him whenever this happened, and he always had to leave the room whenever this happened.

"If you're going to pout, then go on, go to your room." she waved him away.

Adam left the dining room but stopped in the entryway. He turned around and looked at Ms. Alice who was sitting quite like a lady, modestly drinking her tea. He felt the need to apologize to her, but again, no words could come out so he stormed up the stairs.

Alice put her lips to the china cup.

"I'm sorry, that boy is-" Mrs. MacDonald began.

Ms. Alice painted a smile and nodded her head, she took another sip from her tea.

* * *

Adam's had always been obsessed with Sally's trademark blonde hair. She, or their mother, always seemed to be brushing it. Sally was who Adam had always wanted to be. Her room was completely pink—her walls, bedsheets, curtains, and even desk. Adam always felt invisible to his parents when Sally was in the room—even when she wasn't in the room, they would be talking about her. Any friend Adam thought he had made were really just guys using him to get to his sister.

Strangely, Adam never hated his sister. No, he was envious of her. He wanted to become her. Whenever he was forced to do her laundry, he would have fun putting on a pair of her worn panties and fool around. He'd feel a surge of dopamine whenever he'd slide her panties up his legs, it felt so natural to prance around in them. And when he was finished with his play session, he'd just toss the dirtied panties in the machine wash, and nobody would ever find out.

* * *

I can't believe how mother just embarrassed me. I shut my door, turn the lock, and walk to my nightstand. I crouch, and I shuffle a few books on the bottom shelf and pick out a large red hard cover. I set it on the top of the nightstand and open it. It's a hollowed out book, and inside are a pair of black lace panties. I take them out and ravenously sniff them. They are my mother's panties. She had worn them a few days ago at the charity fundraiser, so the panties are filled with cream from her being near all the wealthy, powerful men.

I close my eyes, and try my hardest to imagine her excusing herself to the bathroom. It is a high-class bathroom with marble walls and vanity mirrors, she walks towards the furthest stall. Another lady flushes the toilet and my mother turns to the mirror and pretends to groom her hair. The lady steps out of the stall, speaks with my mother, then when she exits mother continues with her plan to the furthest stall, enters, and shuts the door. She sits on the lid of the toilet seat, drops her soaked panties to her glossy black heels, and begins rubbing herself. I picture the black dress with one shoulder strap that she wore. I can see her removing the shoulder strap from her arms, and letting the strap dangle by her upper arm. She lifts one of her breasts from the top of her dress, and begins playing with her nipple.

My nose is as close to the dried cream as it can be. I am holding the panties in one hand, sniffing the fragrances deeply, and with my other hand I massage cock my cock through my jogging pants.

My mother's legs begin to convulse as she continues satisfying her urges. She stifles her moans as she now squeezes her breasts, and begins fingering herself. It is difficult for her not to make any noise, so she bites on her tongue and that keeps her quiet. The door to her stall suddenly opens, and one of the gentleman she had been eyeing earlier stands before her. He walks calmly in, and shuts the stall door behind him. He is standing in front of her, her mouth is watering, and he begins to unzip his pants. Finally, he pulls out his cock, and it throbs right in front of mother's face. She is in disbelief of the risk they are taking, but she's too much of a whore to care.

"Well, what are you waiting for?" he says sexy.

Mother turns around, puts one leg on the seat, and pulls up her dress and presents her pussy. The anonymous man spits on his cock. He prods her lips with the head of his cock, teasing her, knowing she had been eyeing him all night. His pulsating dick enters her warm, wet pussy. At the thought of this, I cum intensely. My hips thrust into my jerking hands. Cum squirts all over my night stand. When I open my eyes, I see long lines of my fresh, thick cum all over my table.

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xoxo Sissy Scarlet