Summer Break - Part 3

Click here to read the previous parts of the story.

 “Whose house is this?”

“Who cares?”

That was the brief exchange Tim and his best friend Bryan had as they walked towards the expansive beach front house that was hosting the party. Bryan made a very good point – it didn’t matter whose house it was because all that mattered was that they’d been invited – and the moment they were and among the mass of people nothing really mattered other than getting a drink and having a damn good time.

Tim recognized at least half the people at the party – former classmates – and just about everybody was friendly. He wondered if that’s what happened once you’d gone off to college, if you came back caring very little about the kind of social status bullshit that you cared about before graduation.

After dark Tim found his way onto the back deck, where he admired the remarkably large bonfire someone had lit and was still tending to. He watched and threw back the last of the punch-like concoction he’d scooped out of a massive bowl in the kitchen and smiled at the rather pleasant sense of warmth and buzziness coursing through him as a result of whatever was in the drink.

Seeking more of that, Tim turned to head back into the kitchen and found himself staring at a girl he recognized.

“Hey, Tim,” she said with a surprisingly sweet smile.

“Hey, Kara.”

“You look good. Really good, actually.”

Kara was out of Tim’s league. Or at least she’d seemed out of his league while they were in school together. Now, though, she was coming up to him and telling him that he looked good. He couldn’t quite make sense of it, which was why he said nothing in response and instead stared at her beautiful, symmetrical face.

“Aren’t you going to tell me I look good?” she asked playfully.

“Right, yeah, shit, well, you do. I mean, you’ve always looked good, though, so, you know. I guess I’ve thought it hundreds of times, but you can’t read my mind, so yeah, you look good. Beautiful.”

Tim was certain she’d walk away after he’d stumbled his way through complimenting her, but instead Kara smiled and stepped closer.

“Yeah? Did you have a crush on me?”

Tim wasn’t sure that ‘crush’ was the right way to describe it, mostly because Kara genuinely seemed out of his league so he’d never really entertained the idea of going out with her. He knew that wasn’t the way to answer her question though.

“I did. I mean, how could I not?”

She laughed softly and Tim couldn’t help but wonder why she was talking to him. Half the guys at the party would have been thrilled to talk to her, including some that were far better looking than Tim.

“How was your freshman year?” he asked.

For just a moment her lips curled into a frown and she looked down at her drink. “Not great, honestly. I got paired with two bitches for roommates and…I don’t know, it just wasn’t quite what I was hoping for. I’m thinking about transferring, actually.”

“Oh, shit, I’m sorry to hear that.”

She looked up and smiled. “How was your freshman year?”

He felt bad for telling the truth, but there was no point in lying. “It was good. Really good, actually.”

Kara studied him for a few seconds, tilted her head as if she was deepening her study, and said, “You had sex, didn’t you?”

It was such a direct, abrupt question that Tim struggled to offer a response.

“That’s what it is. That’s what’s different about you. You’ve been having sex.”

“Do I really seem different?” he asked.

She nodded and approached the deck’s railing. Tim turned and they both looked at the bonfire, which had somehow gotten bigger.

“You were…well, I don’t mean to be offensive or anything, but you were shy and just a little bit dorky. Now, though, you have way more confidence. I mean, you were always pretty good looking and really, really nice, but you just seemed…well, kind of scared.”

“I never really thought of it that way, but I guess I was.”

Kara looked up at him and smiled. “And now you’re not. I mean, here you are talking to a girl you were too nervous to talk to just a year ago.” She leaned over and nudged him a little before asking, "You never actually answered me. Was I right that you found your confidence thanks to a girl?"

Tim smiled and nodded. "I did meet a girl at college. I have had sex and if I seem more confident then there's a good chance that's exactly why."

"It was more than sex, wasn't it?"

Kara looked genuinely happy and again Tim nodded. This time, though, he thought of Alexis. Of all the dates they'd been on. Of the many times they'd had sex. Of the intense pleasures and joys he'd experienced both with and because of her.

Then he thought of her all the way across the country, of her on a beach a lot like the one he was on, of her walking hand-in-hand down the beach with a guy, of her kissing that guy. A little less than a week had passed since they'd first masturbated together while talking about Alexis indulging in that very pleasure - and more like it - and they'd visited that topic once again just a few days ago.

Tim wondered if Alexis would find pleasure in the notion of him fooling around with someone. If he texted her and said that he'd just kissed a girl - perhaps Kara - would she find that thrilling, or would she experience only pure jealousy?

"It was," Tim answered. "She's amazing."

Kara turned her attention back to the bonfire and Tim did the same, though she was so beautiful that he couldn't help but sneak a few looks her way to appreciate the contours of her face and how lovely her arms looked in the sleeveless top she had on.

"How would you feel about a walk on the beach?" she asked before looking up at him.

"I'd love that," he answered.

Kara smiled, finished her drink, and set the cup on the deck's railing before heading down the stairs. Tim followed and quickly caught up to her as they walked away from the party and towards the empty party of the beach.

"Is she pretty?" Kara asked.

"Who?"

She laughed. "The girl. From college. The one that gave you such confidence."

Tim pulled out his phone and brought up a picture Alexis had sent him just a few days ago. She'd gone bikini shopping with her friends and had sent him a shot from the fitting room. He showed Kara the picture and he was almost certain her eyes went a bit wide, like she was surprised at just how good looking Alexis was.

"Wow, yeah, she really is pretty."

Tim wasn't great at reading women, but he thought he detected something akin to insecurity in Kara's voice. "She is. I'm lucky."

"You're still together?" Kara asked.

He nodded. "We are. Everyone keeps telling us that staying together through the summer is going to be hard - if not impossible - but we're going to try."

"I can see why you'd want to stay with her," she said before almost immediately adding, "I didn't mean that in a bad way. Like, you can obviously land a girl like her, I just meant that you clearly like her and she's clearly beautiful so of course you'd want to stay with her."

Tim was fascinated that Kara was now the one getting a bit tongue twisted, so much so that she handed him his phone and looked away for a few moments before pointing towards a sizable piece of driftwood.

"Let's sit," she said.

Kara sat on the smooth wood and Tim sat next to her with a fair amount of space between them. She looked at him and at the gap between them and immediately closed most of it by scooting towards him.

"Do you get lonely?" Kara asked. "Without her, I mean?"

Tim felt like he was in uncharted waters. He wasn't the kind of guy that girls flirted with, and yet it seemed like Kara was pushing hard to make something happen. Under normal circumstances he wouldn't have walked down the beach with her and he wouldn't have been sitting on the driftwood with her. His circumstances weren't entirely normal, though.

"I do. It's hard to go from seeing her almost every day to knowing that I'm not going to see her for a long, long time."

Kara looked up at him and rested her hand on his knee. She reached up and brushed her hair behind her ear before leaning a little closer. She was signaling that she wanted to kiss him.

Tim leaned down and they kissed. He closed his eyes and marveled at the softness of her lips as he reached up to caress her face. Her mouth opened and the tip of her tongue brushed against his lips and teeth. Her hand moved up his leg, stopping mid thigh and moving in slow circles.

The kiss continued as she offered more of her tongue, signaling for Tim to do the same. His hand moved to her leg and he caressed the bare, impossibly smooth-feeling skin his fingers found. She moaned into his mouth and scooted a little closer. She got a little more aggressive with her kissing, too, pushing her tongue deep into his mouth for a moment as her hand inched closer to his crotch.

"You're a good kisser," Kara said softly.

Tim smiled. "I learned a lot this year."

She studied his face, smiled, and then stood up and straddled him with such swiftness and confidence that Tim's cock almost immediately began to throb. She rested her hands on his shoulders for a moment before they moved to the back of his neck. She leaned in and they kissed once more, this time with Kara slowly grinding in his lap and no doubt feeling Tim's excitement for her.

He slipped his fingers under her shirt and ran them up her back until he reached her bra strap. Their tongues mingled as his hands traveled down her back and he grabbed her ass, confidently squeezing it and eliciting a moan into his mouth that filled him with confidence.

"It seems like you had a good teacher," Kara said.

"Yeah?"

She nodded. "You've got me more turned on than I was at any point during my freshman year, so it's safe to say that your girlfriend taught you very well."

Tim smiled and they kissed again. He kept one hand on Kara's ass while the other moved under her t-shirt and over her stomach. He inched his way towards her breasts and noted that she moved her hips faster the closer he got. He surmised that she was urging him to explore as he desired, so Tim ran his fingers over the soft material of her bra. He figured she might be in a bikini top and found himself awash in a deeper level of arousal as he touched the far sexier fabric.

"That feels so good," she whispered before kissing his neck.

Tim was gentle as he played with her breasts. That was how Alexis liked it, except in rare cases when they were having particularly vigorous sex. She always preferred a gentle touch during foreplay, though, so he applied that lesson to Kara and it seemed to be working wonders as she was moving her hips even more vigorously while showering his neck in soft, seductive kisses.

"Tim...I think I'm...I think I'm gonna cum," she said.

"Cum for me," he replied.

She held his head in her hands and looked into his eyes while grinding her hips over his crotch and undoubtedly generating the friction that was guiding her towards an orgasm.

"Cum for me, Kara."

She did just that. She stopped grinding, closed her eyes, and let out a beautiful moan before kissing him. She moaned into his mouth while their tongues mingled and he pulled his hand from her t-shirt, wrapped his arms around her, and held her close.

After her body had finished trembling, Kara leaned back, smiled, and then kissed Tim deeply. "That was the best orgasm I've had in a long, long time. Thank you."

"It was my pleasure. Really."

She kissed him on the cheek, stood up, and dropped to her knees in front of him. Kara reached for his zipper but Tim grabbed her wrist. She looked up with genuine surprise on her face and what he thought was a bit of hurt.

"I know this probably sounds crazy - and it has nothing to do with you - but I'd actually rather not do that."

"Really?"

He nodded and Kara got up and sat next to him on the driftwood.

"I wasn't going to say anything because I think maybe other people might think it's pretty weird, but my girlfriend and I have this...agreement. Basically, we're allowed to fool around with other people and we agreed that we'd tell each other about it when it happened."

"How very progressive."

"Well, I don't know about that - it might end up being incredibly stupid - but the thing is, she was the first one to do something and when we talked about it we both got really turned on. I don't know if that's going to happen this time, but I sort of feel like I want to save myself - just this time - just in case we both get really turned on again."

"So, basically, you might have found yourself the best girlfriend ever," Kara said with a smile.

"It's entirely possible," Tim replied.

Her fingers entwined with his and she rested her head against his shoulder. "Well, I don't want to sound like a total slut or anything, but I think I'd really enjoy being the girl you hook up with, and I think I'd be pretty good at making you feel good if, you know, there's ever a point where you want that. If not, well, I'd also really enjoy doing what we just did because, you know, I had a really good orgasm and most guys our age are not good at making a girl cum, at least in my experience."

Tim looked at her and leaned in for a kiss. She was so beautiful and he was still so horny, so of course he kissed her. To his delight she was more than willing to let that kiss go on for quite some time.

"Can I get your number?" he asked.

She looked gleeful. "Of course. Give me yours, too."

They exchanged phones and numbers and spent the rest of the party talking and occasionally making out. Tim left feeling massively horny and eager to talk to his girlfriend, so he called Alexis the moment he got home and locked himself in his room. It was a little past midnight his time, which meant she would almost certainly still be awake.

"Hey, baby," Alexis said softly.

"Hey. It's so good to hear your voice."

"Yeah? Have you been thinking about me?"

"I have. Constantly. Though, I guess, in a weird way, maybe."

"Hmm. Intriguing. How so?"

Tim was suddenly nervous. He'd been turned on by Alexis almost kissing a guy at a party, but there was no guarantee she'd feel the same way about him fooling around with another girl.

"I...I met someone tonight."

"Met someone?"

"Someone I knew before college. We were in the same graduating class, though she never really paid attention to me in school."

"But she paid attention to you tonight?"

His cock stirred as he thought of the kissing, of the dry humping on the beach, of the orgasm he'd given Kara. "She did. She said I seemed different. Much more confident. She actually guessed that it was because I'd been having sex."

"So she was into you?" Alexis asked.

Tim tried to discern any jealousy or annoyance in his girlfriend's voice, but he didn't hear it. "She was. I didn't see it at first - I guess because she'd completely ignored me before - but she was into me. I got the feeling...I don't know, like she didn't exactly have good luck with guys at college, that maybe she'd run across some not so good guys. Anyway, she was into me. She did some flirting. I'm pretty sure I did some flirting back."

Alexis was silent for a few seconds before she asked, "Did anything else happen?"

He could hear her breathing. It sounded heavier. "She asked me to go for a walk down the beach. Away from the party and all the people."

"Did you go for that walk?"

"I did. We talked as we walked down the beach. She wanted to see you so I showed her a picture. The one of you modeling the bikini you recently bought."

"What did she think?"

"Actually, I think she was...jealous of you, I guess? Like, she seemed kind of taken aback by how pretty you are."

"Am I prettier than her?"

"You are," he answered immediately. It happened to be the truth, which made it easier to answer in an instant.

Tim was almost certain he heard Alexis unzip whatever bottoms she was wearing. There was definitely movement and he imagined - perhaps because it turned him on - that she was talking off a pair of denim shorts so she could masturbate.

"She's pretty, though?"

"Yeah, she is. Not as pretty as you, but she's good looking, yeah."

"Do you think that seeing the picture of me made her want you, Tim?"

"I...I don't know. We did...we did end up sitting after that. There was this big driftwood log. She sat down. I sat next to her. She moved closer almost immediately. And then...well, not longer after...we kissed."

Alexis moaned and Tim was certain she was masturbating.

"Was she a good kisser?"

"Yes," he answered. "She said I was a good kisser, too."

"You are."

"Because you taught me how to be."

Alexis moaned again. "And did it turn you on to kiss her, baby?"

"It did."

"And are you turned on right now?"

"Yes. Are you?"

Tim heard the sound of Alexis's wet pussy. She must have had the phone between her legs. It was incredible. So much so that he stripped his shorts and boxers off and stroked his cock until he was throbbing with desire.

"I'm turned on," she said. "I like that she was jealous when she saw my picture. I like that she wanted you more because she saw that you could land a girl that looks like me. I like that she got to enjoy that I helped you become a good kisser."

"That wasn't all she got to enjoy," Tim said. "She straddled me after we kissed. She sat in my lap and we kept making out. She liked the way I touched her. It turned her on. She kept moaning into my mouth."

"Fuck...where did you touch her?"

"Her ass. Her back. Her breasts."

"Yeah? You played with her tits?"

"I did."

"Were you gentle?"

"I was. Just like you taught me. Gentle during foreplay."

Alexis moaned louder. "And did you turn her on, Tim? Did playing with her tits and kissing her turn her on?"

"It did more than that. It...she had an orgasm while grinding on me."

Tim heard the wetness of his girlfriend's pussy once more. She was happily letting him know that his tale had gotten her all wet.

"Fuck...Tim...did she make you cum?"

"No. She offered. I think she was going to give me a handjob, but I told her I wanted to wait. I told her I...I told her about our agreement. I told her that we both got turned on when we talked about you almost kissing a guy and that I wanted to...well, that I wanted to cum with you."

"Tim...fuck...I'm gonna cum!"

Tim held off. He listened to Alexis cum. He smiled at the notion that he'd helped two different girls cum that night.

"Wow," Alexis said between heavy breaths. "That was really hot. Is all of that true, by the way?"

"Yes," he replied. "Do you...did it really turn you on?"

"Yeah. It's strange. This whole thing is strange, I guess, but I liked that she got jealous after seeing my picture and I really like that she wanted you more because she saw that you were dating me. It might be really strange that I liked that the stuff I'd taught you led to an orgasm for her, that I turned you into someone that's better able to make a girl feel good, but I don’t care. I mean, if I'm not there to enjoy those skills that I taught you, someone else might as well enjoy them, right?"

"I suppose so."

"Did you cum?" Alexis asked.

"No. My dick is still hard though."

"You know, I like that you didn't let her give you an orgasm. That really turned me on, too. I like that you wanted to wait for me, that you wanted me to be the one to make you cum."

"I did."

"Let's FaceTime."

Tim tapped his screen and saw his beautiful girlfriend in her bed. She had on a cropped t-shirt and she almost immediately offered him a view of her plump, soaking wet pussy lips as she moved her phone between her legs.

"I wish I was there," he said. "Holy fuck do I wish I was there."

"I'm sure you do, baby. You'd be in my pussy right now if you were here. You'd be sliding in and out of this tight, wet pussy. You'd be making me feel so good. I'd be moaning and telling you how good your cock felt inside me. I'd be telling you to fuck me harder."

Tim stroked his cock slowly as he was already quite close to cumming. It felt exceptionally good, though, and potentially better than a handjob from Kara would have felt.

"Are you going to see this girl again?"

"Kara. That’s her name, I mean," he said. "Yeah, I'm going to see her again. She gave me her number."

"I want you to tell me when you're going to see her," Alexis said as her fingers moved between her legs. Tim watched them push into her slippery pink flesh and moaned at the sounds of wetness. "I want...I want to be the one to decide if Kara gets to give you an orgasm."

Tim's cock swelled up as a surge of pleasure moved through him. "Oh...fuck...that's so hot, Alexis."

"Mmm, I know," she said as her finger moved over her clit. "I don't know why, but it's so fucking hot. Will you do that for me? Will you tell me when you're going to see her again?"

"I will. I absolutely will."

"And will you let me decide, Tim? Will you let me be the one to decide if she's allowed to give you an orgasm or if you'll have to be satisfied with only making her cum?"

"Yes. I will. You get to decide if she gives me an orgasm."

"Fuck...that's so hot."

Tim stroked his cock as he watched his girlfriend play with her exceedingly wet pussy. He loved that she was turned on by having control over what Kara was allowed to do with him, that she seemed eager to exert that control.

"Let's cum together, baby. I want you to cum while you think about being inside me, about fucking me. Think about how good my pussy feels, about how good it feels to fuck your girlfriend, to cum with me, to cum inside me."

"I'm close," he said.

"Cum for me, Tim. Cum with me. Fuck, Tim, think about cumming inside me! Think about cumming in my tight little pussy!"

Tim came as he thought about being inside the pussy he was staring at on the FaceTime call. He came and his body trembled with delight. He came and spilled a little of it on his sheets before catching the rest with his underwear. He came and it felt so fucking good.

"Wow," he said afterwards. "Wow, Alexis. That was really hot."

She'd cum too, though Tim was so caught up in his orgasm that he'd hardly noticed.

"I know," she said. "I can't believe how quickly I got turned on again."

Tim closed his eyes and smiled.

"Oh, and I didn't mention it, but I have a date tomorrow."

His eyes shot open. "Really? With the guy from the beach party?"

She shook her head. "Someone different. I met him tonight, actually. We hung out at a friend's party. A much smaller party than the one at the beach. There was no kissing or anything. Not like you, lucky boy. We just talked and got to know each other and he asked me out."

Tim was stunned, both because Alexis hadn't mentioned it and because he already felt a twinge of arousal.

"Is that okay?" she asked.

He nodded. "Yeah, of course. In fact, it's pretty crazy, but I'm a little bit turned on from just thinking about it."

"Should I call you after the date?"

"Yes, please."

"Even if it's really late?"

He nodded. "Yes, please."

"And you'll be okay with me fooling around with him? He's really cute."

He was getting more turned on. "Yes, I'll be okay with that."

"And if I let him make me cum, you'll be okay with that?"

Tim nodded. "Yes, absolutely."

"And if I wanted to masturbate again right now while talking about letting this guy make me cum on our date, would you be okay with that?"

"Yes."

Alexis smiled. "I thought you might. I'll bet you'd even be able to masturbate with me."

He nodded.

"We'll save that for tomorrow night. Until then, I love you, Tim."

"I love you too," he said.

"Good night."

Alexis blew him a kiss and ended the call. Tim set his phone down and his mind raced with thoughts of his girlfriend going on an actual date with someone. They'd never talked about actual dates, but it made sense. Tim would probably go on an actual date with Kara at some point. That's what people did, after all.

He considered masturbating again. He was turned on enough that it wouldn't take much effort to cum.

Tim decided against it, though. He'd wait until tomorrow. He'd wait to hear from his girlfriend. He'd wait for her to make him cum.