On the first night of their trek through the forest of Vulcan Island, Ash had had trouble going to sleep. His mind was simply too busy thinking about all sorts of things, from Misty’s weird, clingy behavior, to Max’s announcement that he would enter the Battle of the Champions as well. The thing that occupied him the most though, was how good it had felt to him to see his old travelling partner May again.

During their first journey together, May had been a complete rookie when it came to training Pokemon. Ash had offered to help her and under his tutelage he had watched her blossom, both in- and outside of her contests. Back then, he had never considered her to be more than a travelling companion and a student, but his years in isolation after the Unova League had led him to realize that he liked May more than just a friend.

And now, after more than 5 years, she was travelling with him again. She had pulled him, almost single-handedly if you didn’t count Cynthia’s taunting challenge, out of his isolation. This was the first night of their journey through Vulcan Island’s forest and when Ash had turned over to her, he had noticed that May was not in her sleeping bag anymore. Following her light footprints in the grass, Ash had followed in pursuit, both out of curiosity and out of a strange sense of duty, as if he was supposed to keep her safe.

May’s trail of footprints led him quite far away from their campsite; Ash estimated he had been walking 5 minutes at the very least when he finally discovered the wandering brunette. When he saw her, Ash discovered she had led him to a big open clearing in the forest, measuring at least 20 meters in diameter. Not a single tree sat in the open space of the clearing, only a single tree stump, measuring about a meter wide, occupied the middle. On that tree sat May, barefoot and cross-legged, wearing nothing but her slightly washed out pink pajamas. She just sat there like a statue, a faint smile on her lips and a sparkle in her eyes as she looked at the star-filled sky above them.

Ash was relieved to see she was okay, but he also felt uncomfortable intruding a scene as serene as the one before him. Still, he hadn’t made it this far only to turn around and leave. Taking a couple of deep breathes of the surprisingly heavy forest air; he forced himself to calm down before he slowly walked into the clearing towards May. His mind was a whirlwind of questions and emotions and he wasn’t sure what to do with any of them. Excitement, unease, a feeling he could only describe as love, fear and even quite a bit of lust in the back of his mind all twirled around in the depths of his thoughts. He forced them all down though, finally coming to a calm state of mind by the time he reached May and stood beside her.

He looked up to the sky and he understood why May had been so mesmerized. The sky above Vulcan Island truly was beautiful.

“Beautiful, isn’t it?” he asked, turning to the star-gazing coordinator. With a gasp and a curse, May was jolted from her stare and she promptly fell backward, off of the tree stump and on to her shoulder, making her legs stick out at odd angles. “Oh my god, May! I’m so sorry!” Ash apologized frantically and he crouched down besides the girl and tried to help her up to her feet.

“Ash! W-… What the hell are YOU doing here?!” she cried as she got her footing again as she leaned on the tree stump with her shoulders. “I thought you were sleeping!”

“And I thought YOU were sleeping!” Ash threw back at here as he felt his face flush with embarrassment over the awkward situation he had gotten himself in.

“So, when you discovered I wasn’t at the camp anymore…” May continued in a low voice, “you just decided to go out and stalk me? I could’ve been taking a leak for all you’d know!”

“But-.. I saw-…  I wouldn’t…” Ash muttered, utterly embarrassed by May’s forwardness, “I-I’ll just leave… I’m sorry to interrupt…” he muttered on as he turned around and started to jog away from the girl he had wanted to talk to so much.

May gasped, seemingly giving herself a mental punch to the head and cried out:

“Ash! Wait!”

He walked on…

“Please…”

Her plead was soft, yet it carried all the way to him with such a force that he had no choice but to stop. He could detect a hint of desperation in her voice and he slowly turned around. She was on the verge of tears and a single silver drop was already making its way down her left cheek.

“I didn’t mean to sound like… I didn’t mean to... please Ash, stay with me…” she said as she choked back the rest of her tears. The trainer from Pallet Town slowly walked towards her again, before he sat down beside on the tree stump as May looked down to the ground.

“S-sorry about that…” May hiccupped as she rubbed away her single tear, “you just scared me witless for a second there.”

“Yeah, sorry about that… I guess I should’ve made myself known a bit earlier” he laughed a bit uncertain. He gingerly brought his hand up to May’s face and, when she made no move to interrupt him, wiped away the rest of her tear with his thumb. He couldn’t help but notice how soft her skin felt.

“So…” he continued, “you couldn’t sleep either, huh?”

“Nope!” she answered with a small smile, “Too much on my mind I guess. I haven’t been this excited since I participated in the Johto Grand Festival!”

“Yeah, I heard about that. Congratulations on winning by the way, sorry I wasn’t there to cheer you on” he apologized.

“Don’t, Ash. It doesn’t matter…” May cut him off. “You had your own problems to take care of. Remember? The Johto Grand Festival was held just 2 months after you went into isolation. You had a lot more things on your mind than just little old May and her festival.”

Ash sighed, feeling only slightly better from her encouragement. “No, that’s no excuse. I’ve been so selfish, tore myself from everyone’s lives just because I couldn’t cope with yet another lost Pokemon league” he pounded his fist into the tree stump, leaving a small dent and gaining a pair of sore knuckles.

May turned her head slightly to the side and observed him. So much regret was unhealthy for a person, she considered, and of all people it certainly didn’t suit Ash. She wondered what had happened to the carefree, determined and slightly thick-headed boy she remembered.

“If that’s how you feel about everything… Why didn’t you come back earlier?” she asked as she laid her hand in his, squeezing it slightly in encouragement.

“Pride, mostly” came the answer, accompanied by a sarcastic laugh. “I had already failed my goal of becoming a champion in every major League I ever entered…” he continued, staring straight to the ground while squeezing May’s hand in return.

“I doubt I could’ve lived with myself had I given up on yet another goal I had set myself. So I pressed on…  Tuned out to the people who meant the most to me… Numbed to everything except my training.”

He looked up to the sky again and this time it was his eyes that were filled to the brim.

“I missed so much… Let so many people down. Yet here you all are, welcoming me back as though nothing ever happened!” he choked back the tears, desperate not to burst into crying in front of May. “Thank you, May. For everything”

May smiled and rested her head on his shoulder as they continued to watch the stars together. “Any time Ash… Any time…”

They continued to gaze at the heavens like this for what seemed like hours, but might as well have been just minutes, sat in complete silence, just basking in each other’s presence. 

“The stars sure are pretty out here…” May spoke breathlessly as hundreds of stars reflected in her eyes.

“They’re not the only pretty ones out here…” Ash said in a low voice.

May snickered, more out of a sudden nervousness than anything else. “Wow, Ash! Where did THAT come from all of a sudden?”

“Are you trying to flirt with me?” she giggled.

Ash remained firm though, he did not relinquish their eye contact as he raised their intertwined hands to their chests. “So what if I am?” he asked, his voice sincere.

“So what?” May shot back quickly, “I haven’t seen you in more than 5 years! Now you’re back, we’re travelling together again, and you’re trying to flirt with me?”

Ash took hold of both her arms and looked her straight in the eyes. “Yes, May! Yes I am! I haven’t been idle these last 5 years May, this thick skull has done some thinking!” he released her, instead taking both her hands into his again. “I’m going to do something I should’ve done back when you left for Johto after our Hoenn journey…” he vowed as he gathered a final charge of courage. “May, I love you” he could not feel his lips forming the words, but he heard himself say it. It just felt right to say it, as though a piece of the puzzle that was his life had just been put into place.

May, in the meantime, had not answered him immediately. Instead, she stared at him, eyes wide and mouth hanging open slightly, complete amazement clearly displayed in her eyes. Suddenly, she blinked twice and shook her head slightly. “Well…” she said, her emotions unreadable, “I guess that makes this a lot easier” she finished flatly.

She didn’t give Ash the time to raise his eyebrow, the next thing he knew, May had crashed into him, pressing their lips together in what was their first kiss as a couple. Their kiss did not last long; May soon retreated, though she kept his face in her hand. “I love you too, you knucklehead” she confirmed and she gave him a beautiful smile as her eyes filled with water once again.

Surprise made way for relieve and love as Ash smiled widely. She felt the same way! The girl, who started out as a friend, then progressed into a student, before she slowly but surely turned into his secret affection, that girl returned his feelings. He couldn’t believe his luck. Almost as if to make sure he wasn’t dreaming he enveloped her in a strong hug and kissed her again. What started as a gentle kiss soon transformed into an all-out make-out session as they traded heated kisses while their hands were exploring all over their bodies. A gentle caress here, a heated kiss there, neither of them relented as the air around them grew thicker and they both felt every restraint in them disappear as they breathed in the musky forest air. Ash groaned as he felt May’s hand stroke the inside of his thighs. May, in return, rewarded his heated kisses with a high-pitched moan.

It didn’t take long before Ash could feel himself harden as  his pajama pants got uncomfortably tight as he continued to cover May’s neck in kisses. He held his right hand in the small of her back, while his left hand went up and gently took hold of her right breast. It felt so soft; Ash couldn’t suppress a shudder as he gently started to massage her mound. With a satisfied smirk, he noticed May’s nipples were hardening under his treatment as her breasts now sported two sharp points, clearly visible through her shirt. In the meantime, May hadn’t failed to notice her own effects on Ash’s body. She could clearly feel the arousal in his pants poking her thigh. She loved the way he gently handled her breasts and she could feel a burning sensation take hold between her thighs.

She gently took hold of the bulge in his pants, causing Ash to hiss and break off their kiss.

“Is that a Slowpoketail in your pants, or are you just happy to see me, Ash?” she joked as she looked down. She noticed his bulge was quite big and it gave her a weird sense of pride, knowing that she was the one who caused him to grow this big.

“Nothing in my pockets, so I guess I’m just very happy indeed” Ash grinned. He let out another moan when May gave his pajama-covered rod an experimental squeeze.

“Careful, May!” he groaned, “if you keep that up, I might not be able to hold back!”  He was already straining to keep himself under control and the longer May continued her work, the harder it became for him to not just jump on her and fuck her brains out.

No! – He mentally berated himself. That was not how he was going to let it happen. He wanted their first time to be happen out of love, love from both sides. He wanted her to be ready…

“Hold back, huh?” he heard May say, which snapped him back to the situation at hand. He hadn’t even realized she had gotten down on her knees in the grass. She was still holding on to his bulge and she was showing him a wicked grin in which he could read all the lust and love he himself experienced. “Good!” she said, “because I don’t want you holding back anything tonight!” and with that, she hooked her fingers behind the bands of his pajama pants and started to pull them down.

Ash let out a gasp and took hold of her face, gently nudging her to look him in the eyes. “A-… Are you sure about this, May?” he asked with a look of concern, “we’ve only just started this, isn’t it a bit too soon to take it to the next level already?”

“Don’t get me wrong May,” he continued, “I love you, and I want to do this with you… But only if you want it too May.” He could see May’s eyes brimming with water again.

“I don’t want to rush this May… Are you sure you’re ready?” he finished and wiped away the fresh tears that had started to drip from his girlfriend’s eyes.

May hastily wiped her eyes with her arm before she hooked on to his pants again. “Thank you Ash, for being so considerate… But I waited for this for more than 5 years, I’m more than ready!” and with that, she jerked her hands down, lowering Ash’s pajama pants to his ankles and releasing his growing erection to the world. Ash let out an approving hiss as he felt the cool forest air gently caress his member. He wasn’t quite fully erect just yet, but he had no doubt May was going to change that pretty soon…

May, meanwhile, was quite stunned with what she had found. Ash was simply huge!

She carefully took his hardening member in her hand and marveled at the feel of it, somehow it was a lot warmer than she had expected it to be. She tried to measure its length, guessing it to be about 16 centimeters from tip to base; she noticed it wasn’t done growing yet either. Clenching her hand around it, she wondered just how long Ash would be when fully erect.

Well, only one way to find out…

With a grin, she slowly started to jerk her clenched fist up and down his rod. Although she had had no previous sexual experience, her mother did instruct her in the basics of sex when she started having her period. Of course, she had focused on the birds and the beedrills mostly, with special attention given to the subject of birth control. Curious by nature, May had done some research into the subject of her own, so she wasn’t completely clueless when it came to satisfying a boy. But actually doing it out in a public forest? It excited May to no end and she quickly went to work on Ash’s rod.

She continued her slow, short jerks for a while before she changed things up a bit by reverting to longer strokes where she made sure to leave not a single spot on his dick untouched. Ash couldn’t believe what was happening to him and with a loud groan he threw his head back as May started to jerk him off using both of her hands. To think, two weeks ago this situation had been nothing but a wet dream, and now here he was, living it!

May was pleased to see her treatment having such a great effect on Ash. To her, simply stroking the fleshy rod seemed almost silly, but she loved the way she could make Ash moan when she squeezed it. To be honest, simply looking at the thing gave her a strange feeling in the stomach and it intensified the burning desire she felt between her legs.

Experimenting further, May started to slightly knead his member with her left hand while her right hand went down to slowly rub his testicles. If at all possible, this felt even better to Ash and he wondered just how much longer he was going to last if May kept this up. His increased moaning only served as a stimulant to his girlfriend, and she quickly increased her pace until her hands were nearly a blur.

“So, Ash…” she asked as she noticed pearly white pre-cum leaking from his tip, “how am I doing so far? Does this feel good?”

“Argh… May!” he groaned, “it feels- ah, it f-fee-heels, amazing! You’re so good at this!” he gasped as she further increased her speed. She was now making rapid long strokes over his rod while her other hand was swiftly tickling his balls. Ash knew he wasn’t going to last. For all the stamina he had, it just felt too good and he could almost feel his balls tightening in preparation for his release.

“May!” he gasped, putting his hand on her head, “I’m going to c-cum!”

Surprised, May slowed down her strokes before coming to a halt, leaving her boyfriend agonizingly close to release. “W-why did you stop May?” Ash asked as he gasped for breath, he could feel his legs shaking from the effort it took him to hold back his orgasm.

May had a devilish grin on her face as she got up from her knees and enveloped Ash in a hug as she pulled him into a heated kiss. She could feel his erection poking her between the thighs and she noticed she was incredibly wet down there. When she retreated from his face, a thin strand of saliva still connected their tongues as they gasped for breath.

Smoothly, she slid her hand into her pajama pants pocket, retrieving a purple container about the size of a cigarette box.

“What’s that?” Ash asked, his eyes following the container as May got down on her knees again.

“I want to have you inside me when you cum, Ash” she stated in a manner-of-fact tone laced with lust and desire. “But, I don’t want to get pregnant just yet and this little guy is going to help us make sure that won’t happen” she finished and she showed him the blue latex circle in between her thumb and her forefinger. A condom, Ash realized with shock!

She came prepared! She must've been planning this from the start!

“S-should I-…” he offered, but he was met with a confident shake of her head. “No Ash, I’ve got this. I want to do it this time…” she refused and placed the latex on his tip. Making sure to keep the end closed between her thumb and forefinger, she unrolled the condom until his entire member was covered in a thin protective layer of blue latex. Then May lied down on the grass before him and she lowered her pants to her ankles, finally exposing her bald pussy to the outside world. Ash could see that the handjob she had given him had not left her unaffected; the insides of her thighs were soaked with a clear, sweet smelling liquid.

“What are you waiting for?” she giggled nervously, “a written invitation?”

Shaking with nerves, Ash discarded his pajama shirt and stepped out of his pajama pants which still clung to his ankles. Now completely naked, he crouched down on his knees between her legs. He noticed her chest rising and falling rapidly in tune with her breathing and her face was flushed red with desire.

“May?” he asked one final time as he hovered above her, “are you sure about this?”

“Yes Ash,” she breathed, “I love you and I want to make love with you. Please, be my first” she finished with a small smile.

“All right May… just… This is going to hurt a bit” he warned her with care in his voice as he took his rod in his hand and guided it towards her needy entrance. “I’ll try to be gentle.”

“I know you will Ash…” she replied before she braced herself. Ash placed the tip of his rod near her entrance and slowly started to push. Applying a little bit of pressure, he felt her lower lips slowly give way to his member as he saw the head disappear within May. Immediately, she let out a low groan as she felt her inner walls being separated by the unknown invader. The new sensation was amazing to Ash and he had to do everything within his power to stop himself from going too fast. Clenching his teeth, he continued pushing in until he felt something within her resist him, causing May to let out a high-pitched squeal. He had only just fit about a third of his member in and Ash knew the strange resistance was May’s hymen as he looked her in the eye one last time. She bit her lip as she gave a shaky nod, giving Ash permission to continue.

He lowered himself on to her, pressing his chest to her still-clothed upper body and placing his mouth next to her ear. “I’ll try to make it quick…” he whispered and placed his hand under her head. Then, using all the speed he could muster, he pushed in deeper, tearing May’s hymen and pushing another third of his length into her. May let out a cry of pain as she felt a sharp stab in her lower stomach. Almost instinctively, she wrapped her arms around Ash and locked her legs behind his back, stopping him from retreating. Ash pulled her into another kiss as tears streamed from her eyes. He hated having to put her through this pain, but he knew the reward would be worth it, and he knew she was aware of that as well.

They remained like that for a couple of minutes as May slowly but surely recovered from the pain of her broken virginity. To be honest, Ash was kind of thankful for the short break. Now, he was nowhere near the limit of his endurance anymore and he couldn’t wait to shove the remainder of his member into her. But waiting was exactly what he did. He owed it to May, he felt. He wanted her to feel just as good as he was feeling, and he knew that wasn’t going to happen if she was in pain when he started.

Then, he felt May relax considerably as she laid her arms out on the grass and unlocked her legs from behind his back.

“I-… I think I feel better now…” she choked back a sob, “you can s-start going in and out now!” Needing no more encouragement, Ash raised himself up again as he slowly pulled out of her until only his head remained in. He moaned deeply as he felt the girl’s inner walls hug his penis tightly, sending waves of pleasure up his spine. He hooked his arms under her legs and bucked his pelvis experimentally. Trying to create some momentum, Ash slowly started to push in and out of May.  Her inner walls were slick with her juices which allowed Ash to smoothly pump his rod in and out of her and with each push he would force just a little bit more of his member inside her. Every couple of thrusts he would change things up a bit by switching to faster, shallow thrusts which May seemed to love, judging from the way she moaned loudly every time he did it.

Ash unhooked his arms from her legs and lowered himself down, using his elbows to support himself, all the while keeping up a steady rhythm of thrusts.

“How does it feel now, May?” he asked between groans as he continued to rhythmically shove his dick into her, “was it worth the pain?”

“Oh Ash, YES!” she moaned after a particularly powerful thrust, “it feels amazing, whatever you do don’t stop!”

He looked down at her pretty face and he could see the pleasure radiating from her eyes. She was enjoying this as much as he was and that made it feel even better! Looking down, he noticed that May had rolled up her pajama shirt above her breasts, releasing them into the chilly night air. Ash had always imagined May having a big set of breasts and he was pleased to see his fantasies hadn’t been far off the mark. May had a pair of extremely nice C cup breasts and right now, her nipples were erect and she was pinching them while she kneaded her breasts firmly. All in all Ash was definitely getting turned on even more seeing May play with herself.

As he continued his own work of pounding away in her pussy, he lowered himself down on her chest and took her right nipple in his mouth. May reacted instantly, letting out a high-pitched shriek of pleasure. The feeling of his tongue on her nipple, combined with his dick filling her up was almost too much for her to cope with and she felt an amazing orgasm build up deep inside her. With a voice husky with pleasure she encouraged Ash to keep going as she rubbed her fingers through his messy hair, something Ash considered to be quite erotic and he increased his speed once again. He could feel his balls tightening with every thrust as his orgasm was building up deep inside him. He knew he wasn’t going to last long anymore and he wondered how close May was by now.

The answer came to him only two minutes later, or rather, it came to May. She suddenly started to moan in quick bursts, increasing in pitch with every moan and Ash could feel her inner muscles spasming, squeezing his member in ways he hadn’t thought possible. May felt every muscle in her body tightening and she locked her legs behind Ash’s back again. She screamed loudly.

“Ash… ASH! I’m CUMMING!” she cried as she felt wave after wave of pleasure burst through body and her juices streamed out of her, coating Ash’s condom-covered dick even more.

Meanwhile, Ash was filled with pride, knowing that he had made his girlfriend cum before he himself experienced release. Just then, as May’s spasming inner walls were milking his member with all their might, he hit his limit. With a final loud grunt he slammed his member in one last time, remaining inside as he finally felt release. He could feel his balls spasm and he knew that with each twitch, another strand of his seed would burst from his tip and into the condom’s reservoir. May could feel him cumming, through the haze of her own orgasm she felt each burst of his potent seed filling the latex shell, and she loved every second of it.

And with a loud groan, it was over. Gasping for breath, Ash pulled his member out before it softened too much. With eyes that wouldn’t properly focus anymore, he peeled off the condom and he noticed the reservoir had been quite full before he threw the rubber protector away to his side. Still gasping loudly he fell on his back besides his girlfriend. May immediately took the opportunity to cuddle up to him, draping one of her legs over his and resting her head on his chest. They remained like this for minutes and the only sound that broke the silence was the sound of their ragged breathing as they were both enveloped in the afterglow of their first time making love. Hundreds of tiny beads of sweat covered their entire bodies and their lower bodies were covered in their bodily fluids. They were a mess, but Arceus was it worth it…

“That was amazing May,” Ash murmured into her hair as he wrapped an arm around her slender body, “I love you…”

“I love you too, Ash” May crooned and as she rubbed her head in the crook of his shoulder, “I always imagined my first time to be a lot more painful and awkward. But your gentleness and your love really made everything just… right!”

“Glad to hear it” Ash smiled down on her lovingly as wrapped his fingers in her long brown hair, “I hope I didn’t hurt you too bad there. You looked really hurt for a while when I, uhm… ‘entered’” he spoke slightly awkwardly.

“Yes Ash, it hurt, but we both knew it would and trust me, the pleasure you gave me afterwards more than made up for it.”

“In fact…” she continued, a shrewd look on her face, “are you up for round number 2?” she asked. Slowly she lowered her hand down his body towards his limp penis and Ash could see the fires of lust in her eyes had flared up again. Again, May felt a blazing heat coming up between her thighs.

She hadn’t been completely satisfied yet, and until she was, she wasn’t going to let Ash go.  As for Ash, well… he kind of liked the idea of having an extremely horny girlfriend.

“Round 2 eh?” he snickered before letting out a low groan as May started to slowly rub his rod again, “What did you have in mind?” he groaned with a smirk. May’s eyes seemed to shine and she pressed a kiss to his lips. She slowly broke the kiss and looked him in the eyes lovingly.

“Don’t you worry Ash, I’ve got everything under control” she breathed huskily before she slowly inched her way down towards his already hardening member.

When she got down, she took off her pajama shirt, finally getting completely naked. She used the pink piece of cotton to clean Ash’s member of any remaining cum. She had considered using her mouth to do the job, but in the end she had decided against it, not feeling very comfortable with the idea of having his penis in her mouth just yet. Besides, her pajama shirt got the job done as well, although in a less erotic manner. That didn’t seem to matter though, because Ash’s member was now not only free of the white stickiness that had covered it, it was also rock hard and standing at attention. May could almost feel her juices dripping just looking at it and she wasted no time in retrieving another condom from her container. Using her teeth to open the package she took out the red latex circle and hastily rolled it over her boyfriend’s penis.

Checking the condom’s reservoir one last time, she rose up to her knees and smiled as she looked at Ash. So far, the Pokemon trainer from Pallet hadn’t said a word as he let May take charge for the round. The look in his eyes took her breath away, a nearly unlimited supply of love, care and trust burned in his brown eyes and May felt her heart fill with love at the sight of him.

Smiling confidently, she took his stiff member in her right hand and positioned herself above his tip. Before Ash had well and truly realized what was about to happen May had already lowered herself onto his dick, finally taking his whole length inside her as his balls slapped against her bottom. May cried out a high-pitched cry as she felt herself being filled up completely. She could clearly feel the tip of Ash’s dick hitting the entrance of her womb and, while a little uncomfortable, it was a feeling she could definitely get used to.

Meanwhile, Ash let out a deep moan as he watched May’s hairless pussy devour his entire dick. He could feel her inner muscles contract around his member and it felt so good he realized he wasn’t going to hang on for very long if May kept this up.

“This time, I’m the one in charge!” May said with a wicked grin on her face as she started to experimentally move her pelvis around. The effect of her movement was obvious as they both gasped at the sudden burst of pleasure it gave them. Determined to keep up the pace, May placed both of her hands on Ash’s chest before slowly moving her pussy up and down on his dick. As she set up a basic rhythm, the night was soon filled once again with the chorus of their moans, cries and hisses as they made love a second time. This time around, Ash reckoned, they were going at it a lot harder than the first time. May was bouncing up and down his dick so fast he had trouble keeping up with it and she continuously let out the strangest noises, almost like an animal. He, in turn, felt the same and he used all the strength he had left to pound his meat into her heated core, all the while growling like an animal himself too.

He loved this new aggressive May and this was definitely a position they were going to use often from now on. Having May on top let him penetrate her a lot deeper than he had been able to do in the missionary position and as a result his member was being squeezed in ways he hadn’t dreamed possible before. This position also had the advantage of a brilliant view of May’s breasts. Each time she bounced up and down his dick, her sizeable mounds would swing up and down and Ash couldn’t resist reaching out for them and taking them into his strong hands. He roughly massaged her tits, pushing, pulling and pinching the nipples from time to time, he even raised himself up once to take her nipple into his mouth to lightly bite it, adding even more ecstasy for May. Needless to say, the girl from Petalburg was in heaven, she absolutely loved to be filled so much by her lover and each time she sank down on his rod it would send new waves of pleasure from her core all to the rest of her body. His dick literally touched every nook and cranny on its way in and out of her heated core.

It had been clear to Ash from the start that they would not be able to keep up this position for long, not at this rate. This theory would soon be proven, because after a few minutes of going at it at top speed, both lovers had reached their limit. May raised herself up one last time, almost letting the tip of his dick escape her folds, before she crashed down on it again, taking it all inside her up to his balls. She was rewarded, as her building orgasm exploded, sending wave after wave of pleasure through her body. With a loud cry she threw her head in her neck and clenched her legs together, giving Ash an even tighter entry. This proofed too much for the young trainer from Pallet and as he felt May’s muscles milking his dick he threw his head back and shouted his pleasure to the heavens. With the strength of a Blastoise’s cannon he unleashed wave after wave of his seed deep inside her, the only thing protecting her womb being a thin veil of latex as Ash rapidly filled the condom with his sperm every time he felt his balls clench.

Completely exhausted, May fell down on his chest. His dick was still firmly clenched within her walls, even after her earth-shattering orgasm.

“That’s-,” Ash gasped with a ragged breath, “that position’s definitely a keeper…” he finished and wrapped his arms around his girlfriend.

“Glad you-… liked it” she replied, her voice raw and hoarse from the screaming she had done. She cuddled up to him and rested her head under his chin. Almost lazily, she slowly raised her pelvis a bit, allowing Ash’s rapidly shrinking member to flop out of her wet folds, its head still covered by the red condom. Looking down at the red piece of protection, Ash started to wonder.

“May, I’ve been wondering…” he mumbled, “why the condoms? I thought girls were put on the pill when they started their periods while on their Pokemon journey?” he asked, stroking her hair absent-mindedly. “Not that it matters, mind you” he added, “for you, I’d wear a thousand condoms!” he joked, pressing a kiss on her head.

May giggled before answering. “Yeah, you’re right about the pill thing. We do get those when we get our first period while we travel” she confirmed, using her index finger to draw small circles around his left nipple.

“I just had a bad reaction when I took my first, when I travelled through Johto. Turns out I’m highly allergic to one of the key ingredients of those things. Makes me swell up like a Snorlax!”

“I see why you’re not using them” Ash jokingly agreed. “So, that’s why you’ve been carrying the condoms around then?”

“Yeah, they were a gift from my mother…” she admitted in a soft voice, blushing madly. “Back then, I was travelling with Drew and my mother thought we were… involved. So, to be certain, she sent me an XL-sized pack of the things, including some premium specials.”

“Premium specials, eh? We’ll have to try those out some time” Ash chuckled; pulling May in closer to him.

“You and Drew…?”

“Never. Though I do think he fancied me at some point, but he’s not my type” May assured him, planting a tender kiss on his lips. “I told you, you were my first, and you know I wouldn’t lie about something like that.”

“You’re right… I love you May” Ash murmured and he rested his head on the grass again. Looking up to the sky, they stared at the stars as sleep slowly overtook them.

“You see those stars over there?” May asked, pointing towards the sky with a slim finger.

“Look! They look just like two Luvdisc kissing! Can’t you see how their lips meet?” she said with some tired excitement in her voice.

“Really? I think it looks like a Pikachu using Volt Tackle if you ask me…” Ash jokingly responded, his voice thick with sleepiness.

“Way to kill the mood Ash!” May replied in a mock-angry fashion, “if only Max were here, he could pull you away by your ear like he always did with Brock!”

“You sure you’d want your brother to find us here? We’re kind of naked here, remember?”

“Point taken” giggled May, “let’s leave Max out of this picture.”

Just then, right before sleep could overtake them, they both heard a loud rustling, coming from the bushes at the side of the clearing. Jolting awake, both trainers scrambled to their feet and hastily retrieved their pajamas. Before they could properly cover themselves though, the intruder made his presence known. A towering figure appeared from the bushes, revealing red feathers and a large beak. A Blaziken had marched in on their afterglow and not just any Blaziken, but the one May had started her journey with when it had been just a Torchic.

“Blaziken!” May cried out, clutching her pajama shirt to her chest, covering her privates only barely. “W-what are you doing here? Why did you leave your Pokeball?”

Blaziken did not answer. Instead it calmly walked up to them, coming to a halt with about 1,5 meters between them. He looked from May, to Ash and back again, taking his time to sniff the air and give Ash a penetrating stare.

Ash was intimidated to say the least. Here was one of May’s absolute powerhouses, sniffing the air and staring at them while they were naked. He figured the fire Pokemon’s instincts could probably tell him everything about what May and he had done. He considered what could happen if the giant bird did not approve and he didn’t like the idea. If angered, Blaziken could no doubt take him out in a single kick if he so wished.

Finally, after what seemed like an eternity, Blaziken blinked and nodded his head to Ash. With a low grumbling “Blaaaaaaze” he lowered his head into what was clearly a bow.

“What’s he doing?” Ash quietly whispered to May, stunned by the whole scene.

“I don’t know, he’s never done this before!” May answered him, equally stunned. “If I’d have to guess… He’s accepting you as my boyfriend.”

“He’s been protecting me, you see. Ever since I moved to Slateport, he’s been at my side. Maybe this is his way of telling us he accepts you?”

Meanwhile, Blaziken had risen to his feet again and had closed the distance between him and his trainer. He put his right claw on her shoulder and gave her a small, encouraging rub. A smile was evident on his beak, but May could also see something strange in his eyes. Something she hadn’t seen before, but somehow recognized. As if she had seen it before that night.

Ash took in the scene from a small distance and when he looked down he was met with quite a shock.

“May! Look down!” he gasped. “If that bow meant he’s accepting me, then what the hell is this that supposed to mean?!”

Surprised, May looked down and was met with a disturbing sight. Blaziken’s dick was standing out, straight at attention and rock hard. It was completely red and covered in purple veins. Unlike with Ash’s penis, Blaziken did not seem to have any foreskin, rather, it existed as a single unit, slick with juices. May also noticed that Blaziken’s member was shaped much straighter than a human penis. Rather than being rounded, the fire-type’s penis had lots of straight edges, giving it a sharp look, almost like a beak. Finally, she noticed the base of his penis was covered in tiny pointed barb-like lumps.

­

Startled, May jumped back a few steps, shaking off Blaziken’s claw on her shoulder. The big bird looked visibly hurt by her reaction.

“B-Blaziken! What’s the meaning of this?” she asked, completely confused by her Pokemon’s strange behavior. Blaziken replied with a long stream of him repeating various parts of his name, all the while making wild gestures with his claws. May couldn’t make heads or tails of it, but her partner’s throbbing erection had given her the gist of his meaning.

“You… L-love me?” she asked, looking him straight in the eyes. She realized now where she had seen the look in his eyes before. Blaziken had the same feverish lust in his eyes as Ash had had only minutes ago. The fire-type replied with a short nod, confirming May’s suspicion.

“And, f-from your ‘thing’ down there…” she mumbled, eying his massive erection warily, “I take it you want to f-… fuck me?”

Again, Blaziken replied with a short nod, a bright blush appearing under his cheeks. This face was twisted into a strange combination of lust, love and shame.

His confirmation left May stunned. She had always been very fond of Blaziken, partly because he had been her first Pokemon when she started her journey. More recently, his role of bodyguard had definitely intensified their relationship. But she had never considered that Blaziken could develop feelings for her beyond their usual trainer-Pokemon relation. Apparently her starter had a different opinion.

Suddenly, May became aware of a dripping sensation between her thighs. Looking down, she was shocked to see her pussy was once again drenched in her fluids.

Arceus, what’s happening to me? Am I really getting turned on by my own Pokemon?

She looked Blaziken in the eyes, again noticing the strange haze of lust inside them. Then, she looked down again to his throbbing erection and felt a stab of desire below her stomach, the heat between her legs instantly returning in full force.

I guess that’s a yes…

May was at a loss. What was she going to do? Surely, she couldn’t have sex with her Pokemon?

The very thought was so bizarre; it just had to be illegal! Besides, Blaziken was part of an entirely different species!

Looking back into Blaziken’s eyes she knew he recognized her badly-hidden disgust at his request. Right there and then, May could see her Blaziken’s heart breaking into a thousand pieces. He lowered his feathery head as tears leaked from his eyes. Slowly, he turned around and started to walk away.

Seeing her precious Pokemon hurt so bad stunned May even more than his unsettling request had.

Then again… When it comes to love, is species really all that important?

May’s thoughts were racing. Would it really be wrong to love a Pokemon, if that Pokemon loved you in return? She recalled her upbringing, the rules her parents had instilled in her and to her surprise she realized they had never taught her anything about love between humans and Pokemon. In fact, she couldn’t recall the subject ever being raised. It had always been ignored and May had to wonder why…

Surely, Pokemon were intelligent creatures. They could act on their own accord, some of them even mastered the human language, and did Blaziken’s tears not prove the fact that Pokemon had emotions?

Then there was also the fact that Blaziken seemed amazingly well hung. Blushing furiously, May had to admit she felt more than a little curiosity when she regarded her Pokemon’s unusually-shaped tool.

“Blaziken, wait!” she called out to the heartbroken bird. Her voice was surprisingly solid despite the train of emotions she had just experienced. She turned to face Ash and he could see she had a blazing look of determination in her eyes.

“I want to do it, Ash” she stated bluntly. “I want to have sex with Blaziken.”

Ash was floored. It had only been an hour since he and May had confessed their love for one another and now she wanted to have sex with another man already? And not just another man, but a Pokemon?!

“May, are you serious?” he asked, his voice suddenly two octaves higher than usual. “You’ve only been my girlfriend for an hour and you already want to have sex with someone else?!”

The determination in her eyes made way for love as he walked up to him and took his face in her hand. “I love you Ash. I love you and only you!” she murmured.

“Trust me, it’ll be just this once. I feel I need to reward Blaziken for everything he has done for me… Please Ash, I don’t want to hurt either of your feelings!”

“And I suppose, with a dick like that, he’s kind of hard to resist, right?” Ash remarked, careful to keep his tone as light as possible. May lowered her head, blushing furiously as she clutched her pajama shirt even tighter to her still-exposed chest. Ash put his hand on her shoulder.

“I guess I know you too well May” he chuckled as he rubbed her shoulder. “Go on then, make him happy. You have my blessing” he continued, his voice even and a smile on his face. “Just promise me you’ll still be mine afterwards.”

May let out a laugh of relief and she threw herself in Ash’s arms, kissing him full on the lips. “Always! I’ll always be yours Ash!” she laughed.

His mind put at ease, Ash softly pushed her back. “Go on then,” he spoke smoothly, “someone’s waiting for you…”

And with that, May slowly turned around, coming face to face with her Pokemon once again. Confident and more than a little horny, she teasingly dropped her pajama shirt to the ground, fully exposing her nudity. Her nipples had hardened to pointy little raisins again and her womanhood was dripping with her wetness, May was ready for him and Blaziken knew it. Looking up at Ash, he gave a short nod of thanks before he returned his attention to his beautiful trainer.

Closing the distance between them, he engulfed her in a feathery hug. She had always felt safe in his strong arms and tonight was no exception. She gently rubbed her hands all over his chest, ruffling his feathers and causing him to let out a breathy “Blaaaaaaaaaze” of lust. He wanted to kiss her, but given the fact that he had a beak, he instead opted to let his tongue work on her breasts. As one claw took hold of her left buttock and the other claw took hold of her breast he covered her other breast in long, slow licks. May moaned out loudly from the feeling. His tongue was completely different from Ash’s, not quite a sandpaper texture but definitely rougher than a human’s.

Sneakily, Blaziken let go of her buttock before sliding his talon underneath her. With a single digit he rubbed her lower lips, he was amazed by the sheer amount of liquid his trainer was excreting. When his digit was wet enough, he slowly applied pressure before his entire finger sank deep within her folds.

“Oh, Arceus, Blaziken! That feels so good!” May cried out as she wrapped her arms around his torso in an effort to keep standing. Blaziken’s treatment, combined with her already drained stamina was making it harder for her to support herself. When Blaziken started to slowly pump his finger in and out of her folds she screamed out loud as she was overwhelmed by her own pleasure. She had thought Blaziken’s sharp talon would be dangerous. She thought it would hurt. The opposite seemed true though, as all she felt was a roughly textured, wet, scaly finger moving in and out of her.

Wanting to repay him, May tried to focus her attention, pushing the waves of pleasure to the back of her mind. Determined, she took hold of Blaziken’s penis and slowly started to rub up and down his length. The texture of his member was completely different from what she had experienced with Ash. Her Pokemon’s shaft seemed to be permanently slick with juices and it was so hard she felt like she was rubbing a wet piece of steel. Blaziken let out a loud roar as she continued to fondle his throbbing member in her small soft hands.

They looked each other in the eyes and both saw their own fires of lust and desire mirrored in the other’s eyes. With a rough moan Blaziken withdrew his finger from her vagina. He took her in his strong arms and carried her bridal-style towards the tree stump in the middle of the clearing. This confused May greatly, but she was too much under the effect of her own lust to offer any resistance. When the blaze Pokemon reached the stump, he placed her on her knees on top of it. Then, he took both of her ass-cheeks in his strong talons and spread them apart slightly, opening his trainer’s wet slit to the outside world.

May realized what would happen moments before it did. She braced herself, but it was no use and she screamed her pleasure to the starry sky above them as Blaziken lined up his rod with her entrance and pushed in. Her incredible wetness and his already slick dick caused him to immediately push in his full length and he heard his balls connect with her ass in a wet slap. Blaziken instantly began to forcefully buck his hips back and forth, shoving his member in and out of his beloved trainer as they both moaned out in bliss.

May couldn’t believe it. The whole situation just seemed so unreal, yet it felt so good! Unlike Ash, Blaziken’s dick did not touch up to her womb, but what he lacked in length he more than made up for in girth. May felt herself being stretched wider than she’d ever been stretched before and she loved it. She could also clearly feel the hundreds of little barb-like lumps at the base of his penis. Every time he thrust into her she felt them stimulate her lower lips and rub her clit. The sensations it sent through her were beyond anything she had experienced before and she let out a continuous stream of low moans.

Blaziken was a much more forceful lover than Ash had been and May could feel his raw feral power as he slammed his cock into her time and time again. With every thrust she nearly lost her balance, how the tree stump was surviving this onslaught she had no idea. She looked back over her shoulder and saw that Blaziken had a fierce smile on his face and his eyes seemed to radiate with a primal lust she had never experienced before. She felt so good; she started to wonder why she had never considered fucking Blaziken before!

Meanwhile, Ash hadn’t sat idly by. How could he? His girlfriend and her Pokemon were going at it like animals and he had to admit, it looked hot as hell! His member had long since risen to full strength again and he was now jacking off furiously as he watched Blaziken nail his girlfriend from behind. Suddenly, he got an idea and he swiftly made his way around to face May. There, he took in a sight that made his dick become painfully hard. May was clenching her eyes shut, her mouth hanging open in an endless stream of moans. She was on her hands and knees and each time Blaziken slammed his penis inside her, her whole body would shift and her breasts would dangle back and forth. Her perfectly hairless pussy was gushing with fluids and with each thrust it was being stretched to its limit. Beads of sweat covered her body; tiny droplets of it fell to the ground every time the fire Pokemon pulled out of her.

He called her name and he saw her focusing her eyes on him, tears of pleasure brimming at the sides.

“Care to lend me a hand here?” he chuckled and he closed the distance between them. His hardened member was hovering right in front of her face.

“Hmmmm, of course!” she managed to groan before another thrust caused her to let out a shriek of pleasure. Coming up, she took Ash’s member in both her hands, only supporting herself with her knees now. She began to rapidly jack him off with short, fast jabs, using both her hands to cover his entire length. Bucking his hips in tune with Blaziken’s thrusts, both males soon formed a rhythm. Slyly, Ash suddenly deviated from their pattern, thrusting at the same time as Blaziken, the tip of his penis bumping into May’s cheek. Secretly, Ash had hoped she’d give him a blowjob, but from the looks of things May wasn’t up for that as she continued her handjob with even more energy. Ash was too tired and her soft hands felt too good on him to keep it going for a long time, but in the end May had a surprise in store for him.

When Ash felt his orgasm building in his balls he let out a loud groan.

“May! I’m-… I’m close!” he cried, clenching his eyes shut in concentration, desperate to delay the inevitable. May on the other hand took her chance and pulled him in even closer before she let his penis slide in between her breasts, giving Ash his very first titfuck. Sliding up and down his dick, she grabbed her breasts and pressed them together, greatly increasing the pressure on Ash’s tool. The sudden shock and the new feeling of her soft breasts were too much for Ash to cope with and he came with a load cry.  For the last time that night he felt his balls contract as he saw 3 thick jets of his sperm hit May in the face and between her breasts, coating large parts of her upper body in his seed. May had anticipated this and she had closed her eyes and mouth when he came, but she was astonished to find herself completely covered when she opened her eyes again. Utterly spent, Ash fell back on his ass and lied spread-eagle on the grass as he rode the last waves of his orgasm.

Just then, May felt something change in Blaziken’s member. It was as though the base of his penis was rapidly thickening as Blaziken increased his speed to maximum. She could feel Blaziken having increasing amounts of trouble getting his entire penis into her as his base kept growing in width. Soon, he couldn’t fit the base in anymore, but that didn’t stop him from trying as he now used even more force in every thrust. Finally, May’s energy was spent and she fell forward as her knees buckled. Blaziken quickly held on to her legs though, supporting her lower body as he kept on pounding into her. May opened her eyes wide as a sudden realization hit her.

Arceus! It’s his knot! He-… He’s trying to knot me!

May did not have to wait long to test her theory. Not a minute had passed when Blaziken used all of his remaining energy to slam into May one last time. This time, the thick barb-covered knot at his base was also slammed inside and May’s lips immediately enveloped it, locking them together as Blaziken finally reached orgasm. Under a loud, thunderous roar Blaziken shot wave after wave of thick, burning hot cum into her pussy. This time, there was no condom to hold it all in and May could feel the hot sticky goo coat her insides and fill her womb.

Overwhelmed by the tingling, burning sensation of being filled with his sperm, May had her final earthshaking orgasm. Her inner walls spasmed and contracted as they tried to milk every last bit of cum out of Blaziken’s member. Shaken by the raw primal pleasure Blaziken had given her, May cried out before she fell forward. Her energy utterly drained, she felt herself being pulled into unconsciousness. Blaziken was not yet spent though, and he spent the next couple of minutes continuing to pour burst after burst of his seed into his beloved trainer’s womb.

By the time his orgasm was finally subdued, May had been filled to the brim and Blaziken reckoned that she was so full her stomach had actually increased a few sizes, showing a small lump in her lower abdomen. His knot had done its job, not a single drop of his seed had escaped her womb. Knowing that their knot would take time to loosen up, Blaziken gently picked May up from the tree stump and walked her over to Ash. The young trainer from Pallet Town had quickly fallen asleep after his last orgasm and he was now snoring peacefully. Gently, Blaziken laid May down on her side, close to Ash. He laid himself down behind her as they were still connected by his knot. He could feel the sleep pulling at him, so he enveloped May in a gentle hug, covering her breasts in his large talons. He pulled her close to him so that his feathers might provide her warmth during the night. Uttering a single, loving “Blaziken”, he closed his eyes and gave in to the night.

Soon, the only sounds that could be heard in the clearing were the soft snores of two lovers and a Pokemon.

Just outside the clearing though, roughly twenty meters from the site where Ash and May had both lost their virginities, things were anything but silent. Here, badly concealed moaning could be heard. Moaning coming from a young red-haired girl from Cerulean City…