This story is in the same setting as my earlier works "Gaming the System" and "Games People Play" but no real relation other than some cameos.
Content is straight and lesbian sex with relatively simple transformations including breast enlargement and age progression.
All characters are 18+ and this is my original work.
—
Seeing a tiny doll-like fairy standing on the foot of his bed somehow seemed like a perfect end for the day Dennis had been having. He'd spent the day working grumbling as he watched the pretty college girls ignore him while he worked at the counter of the small book store. After work he'd pedaled his bicycle to a sandwich shop near home, texting his mother as he didn't feel right letting her cook dinner for him. He was twenty, after all, and would love to move out of the home he'd grown up in if only he could afford it. He remembered rolling his eyes as a few couples met for dates. He found himself despairing at his own long-term single status.
The night had gotten worse as he'd tossed his trash into the receptacle and he'd walked outside towards the rack where he'd locked up his bicycle. He saw a pretty blond girl who lived nearby being hassled by two guys. One, wearing a knit cap, had her cornered against the brick wall and was loudly asking for a date in an obviously unwanted way. His associate, shaved head revealing pale flesh dotted with small pimples and scars, egged him on, making comments about the woman's tits.
Dennis was no hero that would jump in and fight the two thugs, but he also couldn't ignore the whole thing. He snapped his phone's camera on and began recording, while loudly yelling, "Hey! Assholes! Hey! Hey!"
Amazingly it worked. Knit-cap had pulled away, a snarl on his face at his fun being interrupted. Shaved-head pushed Dennis, causing him to step back a bit. The two ran as a police car cruised by.
The girl was shaking and introduced herself as Andrea. Dennis was amazed as he'd somehow actually gotten a girl's number for once in his life, albeit under unusual circumstances. She thanked him profusely, holding his hand in both of hers, then she ran to her car, keys in hand.
So Dennis had found himself at home. He'd greeted his mother as he walked past the living room, carrying his backpack to his room. By rote he pulled a sketchbook free, putting it on the desk on top of another three books filled with his attempts at art.
An hour later as he was laying in bed the fairy had appeared. She was a bit less than a foot tall, dressed in a pale blue dress. Her wings extended from her back, rising above her head. She was perhaps a foot tall, with short-cut blue hair and a tiny beret-like hat that somehow stayed on. He couldn't remember how she'd gotten in: He thought she'd flown in front he window, but it was closed. The thing spoke, in a surprisingly loud voice that had a musical British accent, reminiscent of Mary Poppins.
"Dennis! I'm glad to finally meet you! You've been a very good boy."
He looked around, afraid his mother would hear the woman in his room.
"So we need to talk!"
Dennis stammered a response, "Uh, sure. Talk? What?"
"You can call me Fairy Belinda. I'm, er, a Fairy. Sorry. Not great at this part. Anyway, my job is giving out rewards to people who earn them. You did a good thing this evening, and you're getting three wishes!"
"Three wishes?"
She smiled, then continued, "Yes! Yes! Three wishes and you already made them earlier today. Don't worry: Satisfaction is guaranteed so we'll review them in a few days after they've taken effect, one per day. Here, let's have a reminder..."
The fairy waved a wand with one tiny hand and Dennis remembered three brief moments from earlier in the day.
...He was working at the book store as the girls giggled and joked. He'd thought, "I wish I knew how women thought."
...At the sandwich shop watching the happy couples, an inner voice had said, "I wish I was someone's idea of a fun date."
...While reaching for his phone to tape the two toughs harassing Andrea, his mind had been filled with the thought, "I wish I was a real adult and knew how to handle things like this."
Dumbfounded, Dennis' mouth was open in an 'o' of surprise as Belinda waved her wand and sparkles of light filled his vision.
—
Dennis awoke, tasting the remnants of his dinner in his mouth. He'd forgotten to brush last night and still tasted a bit of onion from his sandwich. He grabbed for his glasses then reached for a pair of of sweatpants from the floor of the messy room. Something about his room felt off, but he couldn't place it. He pulled the sweatpants over his legs, sensing another strange sense of wrongness he couldn't place as he sleepily wandered down the hall. He stood before the toilet, noticing for the first time that the underwear under his sweatpants had changed from his normal boxers to more feminine panties that stretched across a flat span of skin.
He pulled the panties down, practically ripping them in sudden panic. The expected cock was gone, replaced by an obviously feminine slit fringed by a sparse ring of pubic hair. Dennis spun around, expecting this was some strange dream, but remembered the Fairy from last night and the first wish she'd promised to grant.
"I wish I knew how women thought."
Returning to the toilet, Dennis sat and willed urine to flow, shivering at the oddly different feeling. That complete, she stripped to examine her change body. She grunted, the sound incredibly 'girly' in her ears, as she realized she'd lost several inches of height. She'd been short before, but seemed even shorter now.
That aside, she was almost disappointed at how similar she looked to her old male self. She remained chubby, with a layer of fat covering giving her thick legs and a hint of a rounded belly. Her pale skin is smooth and rounded, but her breasts were barely visible rising from her chest despite larger nipples she traced with her painted fingernails. She suddenly noticed her nails had been painted in a crazy mix of green and purple. Her face could almost pass for her previous self, but as she studied her appearance she found countless tiny changes. Her lips looked a little thicker, her nose perhaps a tiny bit smaller. She grabbed at one earlobe and realized she had pierced ears now.
She saw her cheeks reddening, framed by longer hair in a straight cut that desperately needed to be brushed. Dennis was a virgin, and this was his first time touching a woman's body even if not in the way he'd expected or hoped for. Hands pulled back as if her new form was red-hot: She couldn't grope herself in the bathroom, especially if her mom was home!