Summer with a Young Domme - Part 10

Click here to read the previous parts of the story.

“It’s a beautiful night, isn’t it?” Anna asked as she leaned into Derek while they looked out at the moonlit ocean from the deck of a fabulous house that rested right at the edge of the beach.

Derek put his arm around his girlfriend and pulled her closer. “It is,” he said. “It feels like a perfect night, too.”

“Yeah?” Anna asked.

“Yeah,” he said. “Any night spent with you is a great night, but this night, at this party, at this house, this feels pretty perfect.”

Derek didn’t actually know whose house it was or who was hosting the party – it was someone Anna knew – and it didn’t really matter. All that mattered was that he’d gotten an invite, he’d accepted, and he’d spent most of the night – up to that point, at least – hanging out with his girlfriend.

As Derek was about to say something else, the sliding glass door opened and Cooper stepped out, joining the dozen other people situated on the deck’s exceedingly comfortable – and voluminous – furniture. Cooper’s gaze moved over the deck until he settled on Anna. He approached with a confident smile on his face and Derek wondered if the tenor of his evening was about to change.

“Hey there,” Anna said as she looked up at the man she’d been fucking for the past two weeks.

“Hey,” Cooper replied as he glanced at Anna’s cleavage, which was subtle but still spectacular in a v-neck t-shirt. “Since it’s my last night in town, I was hoping you’d join me for a walk on the beach.”

Derek was tempted to step in and insist that Cooper fuck off, but he resisted the urge for fear of annoying Anna, who’d made the rules of their relationship clear time and time again.

“That sounds nice,” Anna said.

Cooper glanced at Derek and smiled in the way any man would in that moment and held out his hand. Anna took it and they headed towards the staircase leading down to the sandy, moonlit beach as Derek remained on the couch with a dumbfounded look on his face.

Anna looked over her shoulder and said, “Be good while I’m gone. And don’t leave.”

Derek nodded and watched his girlfriend and the guy she’d fucked countless times over the past two weeks walk down the stairs and step onto the beach. They held hands as they walked towards the water and Derek hopped off the couch and followed before stopping at the edge of the deck and putting his hands on the smooth wooden railing. He watched Cooper put his arm around Anna and pull her close as they turned and walked parallel to the water, moving away from the house, presumably in search of a little bit of privacy.

“Tough break,” a familiar voice said.

Derek turned to see Melanie standing next to him with a borderline giddy smile on her face, like she was taking pleasure in what she must have thought was a fairly miserable moment for him.

“I’m not here to cause trouble,” Melanie added. “To be honest, I find you fascinating. Not in a way that makes me want to keep trying to steal you from Anna, but fascinating nonetheless. Like, why did you just sit there while he took your girlfriend? Why aren’t you running out into the sand to try and kick his ass?”

“Because Anna wouldn’t want that,” Derek answered as he kept his eyes on Anna and Cooper as they slowly strolled down the beach like a couple.

“What about what you want?” Melanie asked.

Anna and Cooper stopped and turned towards each other. The moonlight was more than enough to illuminate them and Derek watched as his girlfriend kissed another man, and with remarkable passion. Derek watched Cooper’s hands move down Anna’s back and slip into her shorts to grasp her ass. He watched Anna stand on her toes, and while he wasn’t close enough to tell if their kiss had evolved to include tongues, Derek was certain it had. It was the sort of kiss that acted as foreplay, for there was little point in touching each other in the way they were doing if they didn’t intend on following it up with sex.

“I don’t understand me, Melanie,” Derek said. “I’m not sure I can explain myself to you in a way that will make any sense at all.”

“Maybe it’s not that complicated,” she replied. “Still fascinating, but not terribly complicated. Maybe standing here and watching Anna kiss another guy on the beach turns you on. Maybe thinking about what they’re going to do when they’re done kissing turns you on. Maybe that’s all there is to it.”

Derek was fairly certain that one of Cooper’s hands had made it under Anna’s shirt and to her chest. The angle wasn’t perfect so he couldn’t entirely tell, but it seemed that his girlfriend was letting another man play with her breasts right there on the beach. She wasn’t wearing a bra, either, which meant that Cooper was touching her soft, smooth, utterly perfect flesh and no doubt playing with her nipples.

“If you were alone right now, would you masturbate?” Melanie asked.

“No,” Derek replied. “Anna told me to be good.”

Melanie chuckled. “And that means no masturbating?”

Derek nodded as his gaze remained focused on the foreplay unfolding on the beach. “She likes…she likes to tease me, I guess. She likes that it…well, that I’m turned on by different things than most guys. She likes being in control.”

“And you like giving her control,” Melanie said.

Derek had never really thought about it in such a clear, concise way, but it struck him as the truth. “Yes, I do.”

“But you are turned on right now,” Melanie said.

Derek nodded. There seemed to be little point in trying to deny it. Even if Melanie ran through the party talking about what a weirdo Derek was, it wouldn’t really matter. He’d be off to college before long and there was a good chance he’d never seen anyone at the party ever again.

“See, fascinating,” Melanie added. “Oh, wow, it looks like he’s headed right into her shorts.”

Derek was fairly certain she was right. Cooper appeared to have pushed a hand down the front of Anna’s shorts. They were no longer kissing, but only because it seemed like she was too busy moaning from the pleasure of being fingered on the beach to kiss.

“Have you ever been fingered on the beach?” Derek asked.

“I have,” Melanie replied. “I’m pretty sure most girls in this town experience that at some point. Even you’ve gone down on Anna on the beach, haven’t you?”

“I have,” Derek answered as he thought of the times Anna had granted him the pleasure of tasting her pussy while they were at the beach.

“Do you wish you were the one out there with her?” Melanie asked.

“Desperately,” Derek replied.

“Do you wish she’d let you fuck her?” she asked.

“Yes,” Derek said with a nod. “I really, really do.” He laughed, mostly at his own sense of desperation for the one thing he wasn’t sure he’d ever get from his girlfriend.

“There are lots of girls that don’t mind taking a guy’s virginity,” Melanie said. “So if you make it to college without Anna having popped your cherry, you don’t need to worry. In fact, it sounds like you’ve developed skills that most girls are going to be very grateful for.”

Derek looked away from the entrancing foreplay unfolding on the beach, studied Melanie’s face for a moment to make sure she was being serious, and asked, “Really?”

Melanie laughed and put a hand on Derek’s arm. He felt a small-but-noticeable pulse of desire work its way through his body as she said, “If a guy knows how to use something other than his dick to make a girl feel good he’s an outlier. I promise, if you show your first college girlfriend that you can make her cum with your tongue and your fingers – and that you’re willing and eager to do so – she will be very appreciative and she will absolutely be more willing to have sex with you.”

“Well, that’s good to know,” Derek said as he glanced down at Melanie’s hand on his arm. He wanted her to take it away, and yet he felt unwilling to actually move his arm away.

Melanie smiled, pulled her hand away, and said, “Enjoy the rest of the party, Derek. I have a feeling things might get a little more interesting for you.”

Melanie nodded towards the beach and Derek looked to see that Anna and Cooper were headed back to the house. They were holding hands and they kept looking at each other, like the lust they’d built up while fooling around on the beach had left them utterly enchanted with each other.

As they approached the deck, Cooper let go of Anna’s hand and walked towards the side of the house while Anna ascended the staircase and moved next to Derek. “We’re going to my truck. Cooper’s leaving tomorrow morning and he wants to fuck me one last time before he goes. I want him too, of course.”

“I know. I could tell,” Derek replied.

Anna smiled, leaned in, and kissed him on the cheek. Her lips lingered until he felt bold enough to turn his head. Their lips met and Anna’s tongue slipped into his mouth in an instant. Derek couldn’t help but find it arousing to kiss her so soon after another man had done the same thing and it left his cock in a powerfully erect state.

“I want you to watch,” Anna said softly. “Not from inside the truck and not from right next to it, but I want you to watch. Find a spot a handful of cars away. Somewhere where you can be a little bit hidden.”

“Does Cooper know I’m going to be watching?” Derek asked.

“No,” Anna replied. “I don’t think he’d mind if he did know, but I didn’t tell him. You won’t be able to see much, but I still want you to watch. Will you do that for me, Derek? Will you watch Cooper fuck me?”

Derek’s knees wobbled for a moment as her question left him feeling a deep sense of longing. “Yes,” he answered. “I’d love to.”

Anna smiled, kissed him on the cheek, and said, “I know. You know where I parked. Wait a few minutes and then come. Okay?”

Derek nodded and Anna walked away. He turned to watch her go and then looked out at the beach again. He tried his best not to think about Anna – he needed his erection to deflate a little before he left – but it was hard not to. He wasn’t sure why, but he was thrilled at the idea of watching her and he couldn’t help but picture it.

Once his erection had faded, Derek made his way through the house – Melanie caught his eye and offered a knowing smile – and out the front door. He walked down the dark, car-lined street and took a left on a side street and headed towards Anna’s truck.

Derek was a dozen cars away when he first spotted Anna and Cooper. He was sitting on the passenger side and she was in his lap. Derek considered waiting from that spot, but he was too far away to pick up any details of what was happening between his girlfriend and the guy she was fucking and that just wouldn’t do, so he moved closer until he was half a dozen cars away from Anna’s truck. He moved behind an SUV with tinted windows to offer as much cover as possible and peered out from behind the rear of the car to admire the perfect view of his girlfriend having sex with someone else in her truck.

Anna’s shirt was off – a detail that hadn’t been the case when Derek had first spotted them – and Derek felt certain she was riding Cooper’s cock. It was the look of pleasure on the other man’s face that made him certain of it. Derek didn’t know what sex felt like, but he recognized that look from the handjobs and blowjobs Anna had given him. That was the look of a man enjoying serious stimulation of his cock.

Derek couldn’t help but find beauty in watching Anna fuck someone else in her truck. In the moment, everything about it struck him as beautiful as he watched through the windshield. There was beauty in watching Cooper’s hands move up and down Anna’s back before gently moving around front to no doubt play with her breasts as they fucked. There was beauty in watching Anna lean forward to kiss him while his cock filled her pussy at the pace she chose. There was such beauty in all of it that Derek found himself sporting an erection as he hid behind the SUV.

Anna seemed to cum first. She leaned back, rolled her head towards the car’s roof, and stopped moving on Cooper’s cock. Derek wasn’t close enough to hear anything, but her moans must have reverberated around the car in the most beautiful way imaginable.

After a short break, Anna resumed riding Cooper’s cock and she did so with renewed vigor, as if making him cum was the only thing that really mattered in that moment. She bounced gleefully on his dick, doing so with a level of eagerness and speed that Derek imagined must have felt incredible for the man lucky enough to be inside her.

It wasn’t long before the intense pleasure of an orgasm washed over Cooper’s face. Derek first experienced a wave of jealousy as he watched someone else cum inside his girlfriend. It was quickly followed by a surprising level of arousal as he vividly imagined Cooper’s cum unleashing inside Anna.

She remained on top of Cooper and they shared a handful of soft kisses and seemed to engage in a little bit of post-coital talk before eventually disengaging. There was another kiss and then Cooper got out of the truck and headed back towards the house, leaving Anna alone behind the driver’s seat.

Derek waited until Cooper was well out of sight and then rushed towards the truck. As he approached the door he saw that Anna was in a pair of panties but that she’d kindly left the rest of her clothes on the dashboard.

“Come in,” she said with a smile.

Derek opened the door and climbed into the front seat that he suspected had been host to a great deal of sexual interaction long before he’d met Anna.

“Is it safe to assume you enjoyed watching?” Anna asked as he nodded towards the erection still present between Derek’s legs.

He nodded and she scooted towards him and helped Derek out of his shorts, leaving him bottomless and stiff in her front seat. He moaned when Anna wrapped her fingers around his cock and leaned over to kiss his neck.

“Did you wish it was you fucking me?” she asked softly. “Did you wish it was your cock inside my tight, wet pussy?”

“Yes,” Derek answered before an involuntary moan escaped his lips. “Oh, fuck, Anna, that feels so good.”

“I know it does,” she said. “But wouldn’t my pussy feel better?”

Derek leaned back to study her face and see if there was any chance she was being serious. All he saw was a giddy smile, though. “Yes, your pussy would feel better.”

“Even though it’s full of Cooper’s hot cum?” she asked.

Derek’s cock throbbed in her soft, warm hand and he moaned again. For some reason the idea of fucking her while she was full of Cooper’s cum felt even hotter.

Anna released Derek’s cock and straddled him. They kissed as he reached up to play with her breasts just like Cooper had. She moved her panty-clad pussy over his crotch, stimulating his stiffness with the warmth and wetness of her loins.

“Do you want me, Derek?” Anna asked. “Do you want to fuck me even though another man just had his way with me?”

“Yes, desperately,” Derek replied despite knowing there was almost no chance Anna would let him inside her.

Anna leaned forward and Derek took her nipple in his mouth and flicked his tongue back and forth over the stiff flesh. She reached back and grasped his cock to stroke him while the tip continued to rub against her cum-soaked panties.

Then, Anna sat back and Derek looked down to watch as she slowly, delicately pulled aside her panties and exposed her pussy lips. “Is this what you want?” she asked.

Derek looked up and nodded at his beautiful girlfriend. She smiled and took his cock in her hand. Her hips moved forward and she rubbed the head over her exceedingly slippery pussy lips. Derek’s body twitched from the pleasure of coming so close to what he’d come to crave most in the world.

“Cooper wouldn’t let me tease him like this,” Anna said. “He would have pulled me down on his cock. He would have filled my pussy. He would have taken it. He’s not the kind of man that can take being teased. But you are, and I love that about you.”

Derek knew he wasn’t the kind of man that would simply push himself into a woman. He knew he’d probably never be that kind of man and that didn’t bother him. After all, Anna loved that about him.

“You deserve a reward for being the way you are,” she said. “Would you like a reward?”

Derek nodded. He didn’t care what that reward was. He just wanted it.

“Let me give you one,” Anna said before sitting up, pressing the head of his cock against her pussy lips, and taking him inside her.

Derek’s eyes went wide and he cried out from the pleasure of being fully immersed in her pussy for the first time. Every inch of him disappeared into the intense heat and wetness of her body and he reached out and grabbed her hips to try and urge her to ride him. It was as if he was incapable of thinking, that his cock had taken over and its only mission was to cum.

Anna grabbed his wrists and pulled them away from her body. “No,” she said. “You’re not in control, Derek. It’s my pussy. I get to do what I want with it.”

She sat perfectly still as Derek grappled with sensations he’d never experienced before. Nothing – not even Anna’s mouth – came close to feeling as good as her pussy. The desire he felt – the need, really – was unlike anything his body had ever experienced. It bordered on overwhelming him and making it impossible to do anything other than pursue an orgasm inside her.

“How does it feel?” Anna asked. “To be inside a woman?”

“It’s the best thing I’ve ever felt,” Derek replied.

“You want more, don’t you?” she asked.

Derek nodded vigorously.

“You can understand why Steve got so mad when I broke up with him, can’t you?” she asked.

Again Derek nodded. Of course Steve was pissed. He’d been cut off from the most wonderful thing in the world.

“And now you want to fuck me, don’t you? You want me to ride your cock with my warm, wet, cum-filled pussy, don’t you?” she asked.

Derek nodded.

“You want me to milk a load from your cock just like I did with Cooper, don’t you? You want to fuck the pussy that he fucked. You want to cum inside the pussy that he filled with his load, the load that’s currently bathing your cock, don’t you?” she asked.

“Anna, please,” Derek said as he nodded once again.

Anna smiled, leaned forward, and kissed him. Her pussy remained still as her tongue explored his mouth and it took all of Derek’s willpower not to grab her ass and start fucking his cock up into her.

“You have no idea how much your desperation turns me on,” she whispered.

Anna lifted her pussy from his cock and Derek’s anticipation reached a fever pitch. She was going to ride him. They were going to fuck. He was going to have sex with his girlfriend. Then Anna lifted her pussy entirely off his cock, pulled her panties back over her labia, and crawled off of him.

“No, please,” Derek said. He’d gotten so close. He’d been inside her. He’d experienced the intense joy of her pussy. She couldn’t stop there.

Anna wrapped her fingers around his cock, collected some of the cum that had leaked out of her, and reached up. “Open up,” she said.

Derek didn’t want to go from the bliss of being inside his girlfriend to eating someone else’s cum from her fingers, but he couldn’t disappoint her, so he opened his mouth. Anna slipped her cum-soaked fingers inside and he sucked them clean as she leaned closer to kiss his neck and moan like they were actually fucking.

“You were absolutely perfect tonight, Derek,” she said. “Keep it up and I’ll let you fuck me before the summer is over. I might even let you fuck me more than once. I might let you have me as many times as you can handle before you go.”

Anna’s fingers left his mouth and found his cock once more. She took a tight grip and stroked him swiftly. A few seconds later Derek came. His loins pulsed with a pleasure unlike any he’d ever experienced. It was, without question, the best orgasm of his life. He couldn’t see straight as he filled her truck with a series of loud, lusty moans while his ass jumped off the seat and his cum likely made a huge mess.

“Holy shit,” Derek said afterwards.

“That seemed good,” Anna replied.

He turned to his girlfriend and saw a sweet smile on her face. “It was better than good. I’ve never cum like that before.”

She smiled and kissed him on the cheek. “Just imagine how good it will feel when you get to cum inside me.”

Derek could only assume it would be an entirely new kind of bliss, unlike anything he’d ever felt before.

“I want to cum again,” Anna said. “And I want you to go down on me. Will you do that for me, Derek?”

“Of course,” he replied.

“It’s messy down there,” she said.

Derek knew, but he didn’t care. He just wanted to make Anna happy. “I know, but I don’t care. I want to make you feel good.”

Anna smiled, turned, and scooted back until she was leaning against the driver’s side door. She spread her legs, pulled her panties aside, and said, “Have at it.”

Derek pulled his shorts up, crawled between her legs, and went to work eating his girlfriend’s messy pussy. He was going to make sure she came hard, so he took his time in tending to her. Eventually she’d have a beautiful, body-shaking orgasm and that was all that mattered.