Isabel's First Time

Sam had been head over heels for her ever since they met. She was only 4'11 with chocolate eyes and fluffy dark hair that tumbled down her shoulders in waves. He found her absolutely adorable and, after getting to know her, he liked her even more. So, after they hung out several more times, he asked her out.

"Um, I... don't think you really want to." Her eyes shifted around his house, as though she was looking for an exit.

"Why not? I really like you- you read the same comics I do and your art is amazing. You're like, one of the coolest chicks I know."

Isabel sighed. "You just... don't."

"But why?" asked Sam, a naturally stubborn person.

When he saw her eyes start to glisten, he felt a pang of worry. "Is it, like, emotional baggage? You don't have to tell me what it is, but I'm a good listener. (Or so I've been told.)"

She chewed on her lip. "If I tell you, can you promise not to tell anyone? You don't have to date me after since it's a deal breaker for most, but... It's dangerous for me if you tell anyone."

Is she in the Witness Protection Program? he guessed.

"Yeah, Belle- lay it on me."

"After I tell you, can you promise we stay friends?"

Sam laughed, nervously. "I mean, as long as you didn't kill anyone or anything like that, yeah."

"Oh, no! Nothing like that. It's... Me. My body's... Not right."

"..."

"I'm sorry I led you on like that. I shouldn't- I know I shouldn't be seeing people like this. Please-" She made a choked sound as a tear rolled down her face.

"Hey, hey, shhhhh..." He made a bold decision to hug her... and was relieved when she hugged him back.

"Tell me if I'm on the wrong track, but I'm straight- and I know a girl when I see one, okay?"

She sniffled against his chest.

"I still really like you- and we've talked about politics already. You know I'm liberal."

She gave a small nod.

"So, I don't care about the way you were born. It's who you are now that I'm attracted to. So," he pulled away to look at her, wiping another tear away from her cheek. "If I accept you, which I do... Would you be willing to give us a shot?"

"Absolutely!"

~~~

The months flew by- they celebrated Sam's nineteenth birthday (he had to repeat a grade in elementary school) and went to parties together. Since Sam never got to give Isabel a birthday gift (she had turned 18 in May, before she moved into town) he'd give her anniversary ones, instead. Sentimental things and one time tickets to see one of Isabel's favorite bands. They taught each other things- and not just about sports and the trans community. Sam taught her how to play video games while she taught him how to salsa dance. In-between doing homework together and talking about current events, they'd also make out for hours at a time until both of them were hard. This made Isabel incredibly nervous, but Sam would pretend not to notice and keep kissing her senseless.

Winter came and went- the two drank hot cocoa together and made snow angels. And when the snow melted in the spring, they'd have picnics out in his large backyard, where he'd collect flowers and put them in her hair.

They didn't know what they were going to do for college, since their campuses were hours apart.

But before they had that conversation, Isabel brought up something else.

"Do you want to have sex?" she asked.

~~~

Isabel figured she had nothing to lose if they were going to break up, anyway. Originally, she never wanted to bring up sex, afraid Sam would be as grossed out as she was with her body. But Sam was as eager as any teenage boy would be to lose his virginity.

"When?"

"What about when we get to my home?" she offered. "My parents are at work."

Sam nodded vigorously, causing her to grin.

~~~

When they got home, Isabel revealed she had lube.

"Nice," he said, his heart pounding.

"We don't have to do this," she said.

"No! I want to." He pulled her in close and kissed her. "I want to be inside you," he said, his voice low and husky.

She blushed. "Inside my ass?"

"No, in your pussy." He grabbed her ass to show that he was talking about the same hole as she was.

"Oh, yes... I'd like that a lot."

"Get on the bed, Belle."

She got on the bed as he popped open the lube. She flipped up her skirt and pulled down her panties, revealing her bare, light brown ass.

"Perfect," he said. "Tell me if I'm going too fast- 'kay, baby girl?"

"Y-yes, I will..."

She gasped as he slid a finger inside her. "You good?" he asked.

"Yes, I've... Fingered myself before."

"Hot," he said, sliding it out and then back in. He did this with a second finger and then a third- her moans music to his ears.

"I'm putting my cock in now," he said, his voice once again low and rumbling.

"Yes! Please..."

He chuckled as he got out his nicely-sized cock. Slowly, he inserted and pushed it inside her lubed ass...

"Your pussy is so tight," he groaned.

Isabel groaned in response.

He fucked her slowly, hitting her prostate about every ten seconds.

"Faster," she whimpered.

"Impatient, much?" Despite this, he kissed her on the back of the neck and picked up the pace.

About five minutes later and he was ready to blow his load. "Baby, you... can touch your... cock- no, clit if... you want to. It's alright." He wanted her to cum with him.

"It hurts so good," she squeaked as she started touching herself. Suddenly he was deeper and she was speaking in tongues, and he easily imagined her eyes rolling back in her head...

With one final thrust, he came inside her, filling her ass with cum. He could tell by her breathing that she came, too.

As he pulled out, he watched his cum trickle out of her hole.

"Beautiful," he said. He left the bedroom and returned with a wet cloth to wipe them down with. "How was that?" he asked, wiping at her ass with the warm cloth.

Isabel shivered beneath him. "Perfect. Thank you..."

And with that, thus concluded Isabel (and Sam's) first time.