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Hitting a home run with the rookie (Charliesweb7 & Crusade)

Sure, she could go and sleep with him right then and there. But...why? She knew they would eventually have sex. And it is not like she was asking him to wait years. She just wanted to take things slow. They could experience this together. They were both rather innocent so it was kind of nice. Tara was glad that she didn't get a guy that was super experienced and pushed her way too far.

Tara smiled again, nodding her head. "I want to do this. I want to please you." She mentioned. Within her boundaries though. Tara propped herself on her elbows, her green eyes looking over his body. Well, she certainly couldn't complain there. He wasn't a complete swimsuit model but he was rather fit. She didn't care though, he still looked great. When he finally shifted the shorts off, her eyes widened slightly. It looked so big! Even if it was just in the boxers. It seemed to be a large bulge. Not that she knew any different but still.

"I think you should lay down." She suggested. Once he did, she moved onto her side and propped herself up on one elbow. The other arm moved over his chest slowly before trailing down his abdomen. Tara made sure to look up at him with a smile. "I hope I do well." She added, her fingers just ghosting along the edge of his boxers now.
 
Evan loved hearing Tara say she wanted to please him. He wanted to do the same for her, but he knew they were taking things slow and he didn't want to push the matter. He would let her dictate the speed of everything and when the time came, he would be ready for anything.

When she caught a glimpse of his cock through his boxers, Evan couldn't help but smile at those widening eyes. He knew he was well-endowed, just from those same looks he'd gotten in gym locker rooms and the fact that well...it just seemed really big.

Laying down per her instruction, Evan reached back to prop his head up with a pillow, glancing over at Tara. He took a deep breath, feeling like his heart was going to beat right out of his chest. Even though he was only going to get touched above the boxers, it was still going to the first really overtly sexual experience he'd ever had.

"You're going to do incredible," he said softly, reassuring her. He placed his hand on hers and gave it a reassuring squeeze before drawing it back, letting her do whatever she wanted.
 
Their fingers interlocked and he gave a gentle squeeze. They weren't having sex at the moment...so she wasn't as nervous. Well, she was afraid of squeezing too much and all of a sudden she hurts him. She had to make sure that she wasn't too hard. Tara smiled at him and nodded her head. "I hope I will.." She whispered to him.

Her hand slowly moved down, now finally resting over his package. Her rings lightly curled, cupping gently to cover is package. She gave a smile again before lightly started to add slight press. She started lightly rubbing up and down, then looking to him. "How does that feel?" She asked him gently. She wanted to make sure what she was doing was pleasurable to him.
 
Evan longed for Tara's touch. The two of them had flirted with the notion of sex before and even though they weren't technically going all the way, any type of release was welcome. However Tara wanted to get him off, he was going to be perfectly alright with it.

He tried staying as relaxed as possible, not wanting to seem tense or uncomfortable even though he was slightly nervous at the prospect. He didn't want to cum too soon and embarrass himself or make Tara feel obligated that she had to get him off. He was okay with whatever. He liked to think he was easy to please. After all, he was new to all of this, too.

When Evan finally watched Tara's hand move to his package through the boxers, Evan relaxed, feeling the tenseness in his shoulders subside as she moved her hand. He let out a groan, letting her know just how great it felt. "That's awesome, Tara. Feels really good," he told her, licking his lips.
 
"Good." She whispered, then continuing to rub him. She wanted to make sure that anything she did was good for him. She adjusted on the bed, her eyes looking over him. She was rather glad they turned out like this. In this way. Better than him hating her forever.

Tara leaned down, moving her lips to his neck and tenderly kissing his neck. Her lips traveled along, moving in tandem with her hand. She moved over to his jaw, kissing more before finally finding his lips and giving him a deep kiss.
 
It was good seeing Tara look fairly comfortable giving him the handjob. Seeing her break out of her shell a little bit and seem intent on pleasing him was nice. He let out another groan as her lips found his neck and he let his eyes fall closed. There was something about the combination of her kisses and the movement of her hand that was perfect.

When her lips found his own, Evan placed his hand on the back of her head as he kissed her back, the passion-filled kiss incredible. It was the kind he could get really lost in and if it hadn't been for her hand working his cock, he was sure he would have. He ended up groaning against her lips, feeling his cock throbbing inside his boxers. She was impressing him in every way imaginable and his body was responding accordingly.
 
As their kisses intensified, the corners of her lips turned into a smile. She kissed back, making sure to put more passion in as well. Her hand moved faster, rubbing a little bit harder and faster. She was getting turned on herself! Was it bad that she was thinking about them going further? She didn't want to regret it but she was thinking about a steamy sex session...

Tara pulled away from the kisses, inhaling deeply. "You....close?" She asked, swallowing.
 
There was an intensity in the kiss and the way Tara's hand movements changed. He could almost sense that she was becoming more comfortable and it showed. It only felt natural to feel more enjoyment knowing Tara was enjoying it as well and the throbbing of his cock was a clear indication of that enjoyment.

When she pulled back from his lips and asked him if he was close, Evan nodded quickly. "Very close, baby," he said, keeping his answer short and sweet. He knew it was only a matter of time before he came and he wasn't sure what route Tara was going to take, but he felt it best to leave that up to her. He didn't want to overburden her by suggesting something too brash.
 
It did feel natural between them. The way their lips meshed together, and the way her hands on his body felt. It felt... right to her. Tara watched his eyes, noticing the more shallow breathing on him. She now realized she was unsure of what she was going to do. "So...what should I do?" She asked. She wasn't exactly going to but him into her mouth or something like that. But would he just cum in his boxers?
 
He wasn't sure what she was going to be comfortable with, but he also knew he wouldn't be looking forward to cumming inside of his boxers, either. When she asked him, he thought about it for a moment. She hadn't mentioned being comfortable actually stroking his cock in the flesh, but they really didn't have much choice. He was on the verge of cumming and to make it a little more natural, he knew it was the only option.

Reaching down, Evan took the initiative and hooked his thumbs into his boxers. He tugged them down to his knees, exposing her to the sight of his bare cock for the first time. He glanced down at it and then into Tara's eyes. "Just jerk me off. It won't take long. I promise," he told her, feeling bad since he didn't know if she was comfortable doing so, but he was so close. He just really wanted to cum for her.
 
He didn't give her any warning before his thumbs hooked into his boxers and then...yeah. Her eyes widened slightly, looking into his eyes. He was...wow... Her mouth was slightly ajar as she looked at the cock. Sure, she had seen them on like...porn before. Or in drawings in health class. But well, this was the first one ever. She was unsure of what to say...

But with his instruction, she wrapped her apparently small hands around the thick rod. She looked to him, then pausing before slowly starting to stroke up and down. This was not exactly what she had planned...but she would just go with it. She adjusted on the bed, almost getting onto her knees to work better.
 
He could see the same look of surprise when he exposed his cock to her as he'd seen when she caught a glimpse of his manhood through his boxers the first time. Seeing one of those small hands wrap around his cock was almost surreal. Another groan escaped Evan's lips as his shaft throbbed against her palm.

As she adjusted herself and stroked his cock, Evan set up on his elbows for a better look. He watched her hand move over his shaft as if it were something she'd done plenty of times. It was only a matter of time before he could take no more.

"Fuck, I'm going to cum," he called out and with her hand leading the way, Evan groaned as he shot his load. His eyes widened as he watched the first thick rope shoot powerfully upward and land on Tara's cheek. The thick shot managed to cover her lips as well. The last few spurts weren't nearly as powerful. A few landed atop his thighs and the last bits trickled down his shaft and Tara's hand.

He looked into her eyes, wanting to apologize, but all he managed to mutter was, "Fuck." He didn't want to tell her how sexy it was to see his cum on her face. He just hoped she handled it in stride and wasn't weirded out.
 
This is what she was supposed to do right? Stroke up...and down...up...and down. It was really a nice rhythm. She didn't want to squeeze too hard or just go too fast. She had to do something right. But the way he groaned, she had a feeling she was doing a good job.

Well he at least let her know. There was a warning before the rope hit her cheek. Of course, she was not expecting that at all. A gasp fell from her lips as she stopped stroking but left her hand around his shaft. When he seemed to be done cumming, she looked up to him. Her hand and face were painted with his cum now. Tara swallowed, looking into his eyes. There was only one thing she could do or that she thought of doing and that was to lick it up. She parted her lips, licking her lips of his cum. It was salty...kind of weird. Not something she wanted to eat but didn't that make guys happy?
 
Evan felt bad. Had he known he was going to cum so powerfully, he may have taken some precautionary steps in order to prevent the facial he'd just given Tara. Nevertheless, he was extremely turned on by the sight and watching her lick her lips gave him a feeling in the pit of his stomach he couldn't readily describe.

"I'm sorry. I mean, I didn't know that that was going to...sorry," he said, stammering as he tried articulating the fact that he hadn't intentionally cum on her face. It wasn't as if he'd ever experienced something like that before and when he came while jerking himself off, he ordinarily did it in a tissue, so he was unaware of the power of his cum shot.
 
It was kind of cute when he stammered. Honestly, it was really cute. She smiled gently and looked to him. "Don't worry about it. It is not like you meant to." She whispered, removing her hand and rocking back onto her heels. "It is not like it got in my eye. Nor will it hurt me." She told him. Sure, it was clearly not what she expected. She would kiss him but that might freak him out. "So was that good?" She asked him, smiling wider. She hoped it was good! he came right?
 
He was glad Tara didn't hold it against him. After all, it wasn't intentional and his cumming like that was just a product of him really enjoying what she did for him. Evan smiled at her question and then nodded.

"Of course it was. You did see what I just did, didn't you?" he asked, smirking as he lifted himself to his feet. Naked from the waste down, he headed into the bathroom and grabbed a towel, carrying it out to Tara so she could clean up.

"I feel like whenever you're ready, I definitely need to repay you for that. You're incredible," he said, using a separate towel to wipe some excess cum from his cock before pulling on his boxers.
 
Tara laughed a little bit, watching him get up. Well, their first little step was a success. A messy one but surely a success. She looked down at the sheets before looking over to him as he walked back in. Was it weird that she was kind of...staring a bit? It was a little hypnotizing... She lightly grabbed the towel from him, wiping off her hand and then her cheek. At the mention of repaying, she blushed and looked away. "That is alright. You really don't have to." She explained to him. "The point is that you are pleased and happy." She continued. Wasn't that how it was supposed to be?
 
"Very true, Tara. I'm very pleased and very happy, but until you are, I won't be able to sleep at night," he said with a smile. He sat back against the headboard of the bed and looked at Tara. He couldn't believe what had just taken place. The innocent above the boxers handjob had turned into something far less innocent and yet Tara seemed alright with it. Evan was just honestly relieved she'd handled everything so well.

"But that being said, we don't have to rush things. Whatever you're comfortable with," he added.
 
Tara just simply shrugged her shoulders. "It is really not a big deal." She repeated. Tara moved on the bed, up to where he was after setting the towel on the nightstand. "This was a little further than I expected to go right now but it is fine. I feel okay about it. I just don't want to rush things and then feel like we rushed into it too soon." She explained, adjusting so that she was cuddled up with him. "Because I like you." She added. No, she didn't love him but she really did like him.
 
Evan wrapped his arm around Tara, still feeling a slight twinge of guilt at not being able to reciprocate and give her the proper thank you for having given him such an amazing release. At the same time, he didn't want to push things, especially so early in their relationship. "I really like you, too," Evan admitted, giving Tara a kiss on the forehead before letting out a content sigh.

They had only experienced each other for a few days, but already, things just felt right. It was a feeling completely foreign to Evan, but one he could definitely see himself getting used to. After all, the two were going to be spending loads of time together.
 
She didn't want him to feel obligated to. Just like he had felt about her giving him a hand job. She was enjoying her time with him. It was kind of amazing how...right it felt between them. "So how did your first hand job feel?" She asked. She just wanted him to give her feedback. "Was there something that Ic an do better?" She asked. Wait..did that sound weird to ask?
 
Evan really hadn't expected Tara to ask him about the handjob or critique it. After all, he came fast and obviously powerfully. He didn't think she'd even consider that she'd done anything wrong.

He smirked and turned to face her. "You did great. Obviously, it felt better actually feeling your hand on it. You made me cum pretty quick and you saw how much I came, so I'd say, A+, Tara. My cock definitely approves."
 
Tara laughed a bit, blushing at his comment of an A+ and his cock approved. She had a rather wide smile however, then kissing his cheek. "Well I am glad he approves." She teased him. She moved over, lightly crawling on top of him. She hovered over him, brushing her hair back before looking into his eyes. She was seeming to get rather comfortable with him. She leaned down, kissing him softly to start with.
 
Evan was a little surprised seeing her crawl on top of him. He smiled and ran his hands down her sides, letting them come to rest on her hips. When she kissed him, he kissed her back, letting her dictate the flow. It wasn't that he was paranoid about overstepping boundaries, but he figured she would be better suited to guide them in whatever direction she chose.
 
She was glad that he didn't push things. After all, she didn't want to feel like he was pushy and wanted her naked this moment. Knowing that he was willing to wait enabled her to open up a bit more. Also since her secret was out, she felt more free to be herself. She continued the light kisses, slowly pulling away and resting her forehead against his. "You know, you are a great kisser..." She whispered, a smile gracing her face.
 
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