Brooke's Childhood Best Friend

For so many young people, moving out at 18 is their first chance to really explore themselves, discover who they really are.

Brooke had discovered when she moved out that she wanted to be a girl, it was fairly obvious decision. She had always been attracted to boys, but watched straight porn growing up, feeling jealous of the girls who had tits and pussies and could look pretty in make-up.

So when she left home, she started dressing as a girl in her flat. She let her blonde hair grow out long, it was. All the way down her back it was that long. She no longer needed parental consent, so began visiting the doctors and taking hormones, she grew gorgeous little tits, and in just 6 months she was living as a girl.

She had been so influenced by the girls on porn, she actually dressed quite slutty too, though she was still yet to fuck a guy. She was at the moment, just happy to live as the girl she always knew she was.

However her family didn't know. She didn't know how she could tell them, her mom and dad, her old best friend Jeff... what if they wouldn't understand? She'd never even told them she liked men...

So as time had passed she had grown distant from her family, her girly voice stopped her making phone calls, texts were the main form of communication she had with them.

She missed Jeff the most, they'd been so close growing up, he was the best friend anyone could ask for, so sweet and generous, but she wasn't sure he would understand this... so they had spoken less and less as time went on the last few months.

One evening Brooke was just sat in her flat, wearing a pink vest, white booty shorts and black thigh high socks, she was reading an article on her tablet about trans people on university campuses, she briefly looked at the comments section, filled with hate as usual.

She shook her head to no one but herself the closed the tablet, she put it on the coffee table and then she heard a knock at her door.

She walked over and opened it, she was stunned to see Jeff stood there, holding a pack of beer, he looked confused.

"I'm sorry I must have the wrong flat..." he said, but I knew his senses were telling him something wasn't quite right.

"No no come in I'll explain who I am," I said.

He came into Brookes flat, he had been just once before when she first moved in, when she was still a boy.

He sat on the sofa and Brooke sat next to him.

Jeff had clearly come from work, he was wearing his suit still, with a blue tie, Brooke always thought men in suits looked irresistibly sexy when they pulled off.

She sat next to him and looked into his eyes.

"So are you... the girlfriend?" Jeff asked.

"No Jeff..." She looked deeply into his eyes, Brooke wanted him to recognise her soul, who she was deep down, below her body, the sibling she always had been to Jeff.

"i'm just the girl who lives here." She finished.

Jeff's eyes widened, he realised who was there, the person he had come to see.

"Oh my god" he whispered to himself.

They sat in silence for a moment, the tension was unbearable.

Jeff swallowed and said "so this is why I haven't heard from you?"

Brooke nodded.

"And this is who you are... all the time?"

Again she nodded.

Jeff reached forward and opened a beer, and leaned back on the sofa.

"Well then... I suppose I better get to know you again. Because I don't care... I care a lot about you...um..." he struggled to know what to call her.

"Brooke" she finished, realising he had no idea what to call her, they laughed a nervous, but nice laugh. Brooke was relieved.

"I care about you too Jeff."

They hugged on the sofa, and Brooke took a beer.

They spent the next couple of hours catching up and drinking, discussing work, Brooke's new identity and life, boyfriends and girlfriends (or the distinct lack of them).

Jeff asked "so have you been... intimate with a guy?"

Brooke stood up and said "no, can you believe it?" She twirled in front of Jeff as if to ask how could they resist her.

She bent over in front of Jeff and said "I mean... look at my butt! It's a nice ass right?"

Jeff laughed, "yeah it is to be fair..."

"Touch it" Brooke said.

Jeff laughed again, "What?"

"Seriously! Feel how firm it is! I have no idea how I don't have a boyfriend yet."

Jeff placed both his hands on Brooke's ass cheeks, feeling how firm they were, squeezing her ass in his hands.

His cock began growing hard in his trousers.

"It's a nice butt right?" Brooke asked, wiggling it in his face.

Jeff slipped his hands under the bottom of her shorts, squeezing her ass skin to skin underneath. Brooke gasped, and let out a small moan, a moan that told Jeff she was also getting turned on by this.

"Ok...ok that's enough" Brooke said, but Jeffs hands keep rubbing her ass, and then he took them out and hooked his fingers in her shorts waistband, and pulled them down.

He knew it was wrong, she knew it was wrong, after all they'd grown up together, people used to say they seemed like siblings... but fuck it felt good.

Her pale fat ass was revealed to Jeff, it was smooth and completely hairless, including her butthole which he could now see.

She continued acting defiant, gasping "Jeff... I was only joking, isn't this too far... oh god" she moaned as she Jeff sucked his finger and started teasing her asshole with it.

He could tell she fucked herself a lot, her asshole was ready to accept his finger easily.

She moaned louder despite herself as Jeffs finger slid into her butt, her own cock was growing unashamedly hard.

She slowly stood up, forcing Jeff to pull his finger out Brooke's ass.

She turned around to face him, Brooke pulled her t-shirt over her head, revealing her small tits and hard nipples.

She wiggled her hips so her shorts fell to the floor, she stepped one foot at a time out of them, the thigh-high socks now the only things left on her body.

He could see her erect cock, her nipples also just as hard.

He could see the lust in her eyes.

She climbed on top of Jeff, her legs either side of him, her butt sat on his erect cock, it sat so right on him.

She leaned forward and kissed him deeply, her tongue entered his mouth. He still couldn't believe his little brother was now a sexy little sister, with soft feminine lips that felt like so many of the women he had kissed before.

A little better than a lot of them.

His hands grabbed her ass as they made-out on the sofa, squeezing it harder and spanking it occasionally, making her moan into his mouth.

Brooke unbuttoned Jeffs shirt and kissed his neck, then down to his chest, she licked his nipples and he moaned, no one had ever done that to him before.

Brooke sat on his lap and placed her small tits at his face "your turn" she said, Jeff happily obliged, sucked her nipples in turn.

Brooke moaned softly and he again started spanking her ass as she grinded against his cock and he sucked on her little tits.

She got off him and took him by the hand into her bedroom.

Brooke dropped to her knees and unbuckled Jeffs belt, before pulling down his trousers and boxers and revealing his large cock.

Brooke took it into her mouth and began to suck it, Jeff moaned and placed his hands on her head guiding the speed, he didn't want to cum yet.

Brooke swirled her tongue around Jeffs cock as she sucked it, then licked and sucked his balls as well.

He couldn't take much more, she could tell. So she grabbed the lube and lay on the bed, she squirted lube into her hand and rubbed it into her waiting asshole.

Jeff watched and rubbed his cock slowly in excitement, now totally naked, he climbed on top of Brooke and placed his cock at her asshole entrance.

Brooke moaned as Jeff slid his cock into her ass. They kissed as he fully penetrated her.

Jeff slowly started fucking her, her blonde hair looked amazing the way it went follow onto her tits, which jiggled as Jeff fucked Brooke harder.

Brooke screamed in ecstasy, he was hitting her G spot, her cock was rock hard as he fucked her, her legs wrapped around his back as he held her and fucked her.

Jeff picked up the speed, fucking Brooke harder and faster. She squealed in delight as her childhood best friend pounded her, really making her a woman.

Jeff grunted and she knew he was getting close, she reached a hand up and gently rubbed one of his nipples and looked at him with pleading eyes.

"Cum baby, I want you to cum on my tits" she cooed.

Jeff pulled out, and stood up. Brooke quickly got in front of him on her knees, and started rubbing his cock rapidly.

It didn't take long, Jeff moaned and came, shooting his load all over Brooke's tits.

White streams of cum shot all over her tits, some hit her stomach, one stream hit her arm.

She kissed Jeffs cock and looked up at him.

Her own cock was still rock hard.

"Round 2?" She asked, winking at Jeff.

Jeff smiled at Brooke.

She had really grown into quite the woman, and he liked it.

Brooke got into the bed in doggy, and pulled her ass cheeks apart with both hands.

"Come get it baby" she cooed, her asshole gaping and inviting him in.

Jeff decided to really make her feel like she had lost her virginity, the next fuck would need to end in a creampie...