tagHumor & SatireFirst Time Blunders

First Time Blunders


Sasha was extremely excited, she and her boyfriend Jordan were about to have sex for the first time! They'd been dating for 7 months, and he was the most wonderful guy she'd ever dated; she knew he was the one she'd been waiting for, to lose her virginity to. They were perfect together, always laughing and playing, all of their friends were completely envious of their great relationship.

The pretty blonde looked at herself in the mirror as she and Jordan walked to her room, holding hands. Her cheeks were flushed pink and her blue eyes were sparkling excitedly. At 18, all of her other friends had already lost their virginity, but she had wanted to find the perfect guy to lose hers with. Now she had Jordan and it was time! They'd been sitting downstairs as usual, as she played with his short blonde hair. He had this one curl next to his ear that never went away no matter how short he cut his hair, she thought it was the cutest thing in the world. Then they'd begun kissing instead of talking, and one thing led to another, and she'd finally made the decision!

"Will you make love to me?" her nervous voice was soft and unsure, but his astounded and excited reaction brought confidence back immediately.

"Really?! You mean it?!" it looked like he was about to start bouncing off the walls with excitement, they were both virgins at 18 and apparently some of his guy friends had been giving him a rough time about it. But he, like her, was a romantic at heart and he'd wanted the perfect girl to have his first time with. That was the only thing that had really made her nervous about asking, most teenage male virgins would jump on the chance to lose their cherry, but she'd been afraid that he might not think she was that perfect girl.

"Yes silly," she giggled a little, "I wouldn't tease you by asking if I didn't mean it." His excited kiss came down hard on their mouth, bumping their noses a little. She giggled at his enthusiasm as he pulled away.

"Let's go upstairs," he said, "We can't do this down here in the living room."

So up the stairs they'd gone, giggling and holding hands, looking at each other out of the corner of their eyes. Finally they reached her bedroom, and she hesitated, unsure of what to do. It didn't matter, immediately Jordan was kissing her, running his hands all over her body with young enthusiasm. They stumbled a little, trying to get to the bed with their mouths locked, and when they did reach the bed they practically fell on it.

"Youch!" they knocked teeth together when they fell, and they had to pull away from each other for a moment, untangling their body parts. Finally, they got themselves in order and began kissing again, unclothing each other as they did so. When they were both naked, Jordan began kissing her neck and down to her small 32-B cup breasts.

"OW!" Sasha's body jerked as Jordan bit down too hard on one of her nipples in his enthusiasm, "Not so hard! That hurt!"

"Sorry," he looked up at her with a sheepish and apologetic grin before lowering his mouth to her nipple again, much more gently this time. After a few moments of nuzzling her breasts, he apparently decided that the foreplay had been accomplished, and he got into position between her legs.

Lying prone on top of her, they kissed, and he began nudging his swollen penis forward. It bumped against her thigh and the outsides of her pussy lips. It continued to bump uselessly against her groin for a few more moments before Jordan finally pulled away from the kiss.

"It won't go in!" he looked at her worriedly, as if she might change her mind.

"Well," she said thinking hard, "Why don't you put your hand on it and watch while you put it in."

"But we're supposed to be kissing when it goes in," he countered, "That's the way it's supposed to happen."

Sasha considered this for a moment. She'd never asked any of her friends about the particulars of entry, but in every movie she and Jordan had ever watched the penis most definitely had gone in while the couple kissed.

"Maybe it's just cuz it's our first time," she offered up, "It doesn't know the way yet. How about you look to get just the tip in, and then we'll kiss while you push the rest in."

This seemed like a reasonable compromise, and he pushed the slippery folds of her pussy around with his fingers and used one hand as a guiding mechanism on his penis until he finally found the entrance to the elusive hole. Even just sliding his penis around her wet pussy felt incredible, and it was making him very excited, he pumped the shaft a few times as he pushed around the wet folds. Finally he found something that seemed like it would open up and placed the tip firmly there while he leaned in to kiss her.

It didn't hurt as much as Sasha expected, her hymen had broken a long time ago, and mostly it just felt like pressure as he slid home.

Is he actually in, she wondered. But as Jordan moaned loudly she concurred that he must be. Unfortunately all the excitement and waiting had been too much for Jordan, not to mention that he'd never felt any thing as incredible as Sasha's tight pussy. Upon sliding all the way into her virgin pussy, he immediately began to ejaculate.

Clinging tightly to her body and moaning his ecstacy, he was experiencing the most incredible bliss as the confused girl he was in wondered what was happening. Finally he lay spent on top of her.

"Jordan," asked Sasha's anxious voice, "are you ok?"

"I'm more than ok, that was incredible!" Jordan avowed passionately. Unsure of what he was talking about, Sasha just nodded and allowed him to nestle his head into her shoulder.

Thinking it over, she remembered her friends saying that the girl often didn't enjoy it the first time. Maybe next time, she thought. After all, she'd had her first time with the perfect guy, but that didn't necessarily follow that everything would be perfect.

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