Hello there readers, this is my first Pokemon lemon ever so please don't be too harsh in the comments, but I welcome all feedback whether it is negative or positive.

I got the inspiration for the first two chapters afer reading a chapter from KingofTerror's story titled 'Ash and All the Girls'.

Enjoy ;)))

Chapter 1 - Serena's Search and Memories of a Previous Encounter

Lumiose City is home to the couple of Ash and Serena, both 24, who have been in a relationship and living together for over 5 years now. Both felt extremely content with life as they always pictured their future to be like this and felt really close and happy with one another.

However, their relationship was different to that of a normal couple as they both agreed that they can have sex with someone else for one night per month just as long as it is just a casual thing with the sole purpose of the engagement being to keep their sex lives varied and make it more exciting and passionate when they make love to each other.

A second rule in their agreement was that they could never have sex with the same person twice - with the exception being that, Ash and Serena have agreements with Shauna and Clemont respectively as backup to fuck with if they can't find a suitable partner for the month. This is because Ash and Serena trust Clemont and Shauna and know they would never fall in love or get too attached with them or anything like that.

We join our unique couple by their front door with Ash wearing only a shirt which was unbuttoned exposing the wifebeater he was wearing underneath. He was also wearing a pair of grey sweatpants with a backpack.

"Serena I'll be leaving now for my once a month" said Ash, Serena made her way to the door and gave Ash a goodbye hug and took his scent in for one last time before he leaves for the day.

She then gazed in his eyes and stroked his left cheek with her right hand and said "Have fun with Bianca, but please try to be a bit more gentle with her than you were with Penelope - don't want another phone call saying that it still feels sore to walk even after two days of sex."

Ash simply rolled his eyes and said "I wasn't going too rough, she was probably exaggerating. I mean you never seem to have any walking issues afterwards". Serena simply gave a deadpan expression and sweatdropped before replying "Ash I am used to having sex with you on a regular basis, besides I have been having sex for over the last 7 years. And you have been having sex for 8 years. You were only Penelope's third partner… or were you only her second?"

Ash sighed and took Serena's left hand and said "I promise I will be gentle this time. Don't worry about me and my time, shouldn't you be busy trying to find someone? You said last night you still haven't chosen a guy yet." Serena frowned, Ash was right, she still hasn't arranged anything with anyone yet, having been busy with giving showcase lessons for future contestants. Well that wasn't completely true, Serena has had an eye on one of her student's brother who was 16 to have some fun with. She would always make sure to expose her cleavage to him, even going one time as far as having half of one of her breasts hanging out of her top, and dropping things and bending over near him to pick them up when he came to collect his sister whilst wearing a short, tight miniskirt which outlined her ass. She has seen him pop boners all the time but wasn't successful however, and concluded that it must be because her beauty and sexiness was too much for the boy to handle. Since then she has given up on him as a potential partner for her once a month fling.

"Don't worry Ash, it won't be too difficult for me to find someone even at short notice, I mean who can turn someone like me down" declared Serena confidently, standing on her sides, and slightly bending over to stick her ass out to remind Ash of her curves.

Ash simply chuckled and shook his head then kissed Serena whilst fondling her breasts before heading out. Serena continued to wave good-bye until Ash entered his car and drove off to the Airport to pick up Bianca whose flight from Alto Mare should be landing soon. He booked a hotel room for them as it would be awkward to bring Bianca home in case Serena had to host her night at home as well since she hasn't confirmed anything yet.

"Well, Ash is off on his way to mess around with Bianca" Serena said to herself before readjusting her bra after Ash fondled her breasts.

She then headed up to her and Ash's room going to the PC desk and sat on their leather executive chair and went on her favourite fling site, and logged into her account and began searching for potential guys to have sex with. She wasn't too picky, as long as it was someone nice, seemed genuine and acted like a gentleman then Serena was willing to share a night with them. Her only searching criteria was that it shouldn't be someone who would be too old for her, so not over the age of 35 and someone who wasn't into BDSM as she always had a fear the person would not untie her at the end and prevent her from leaving. She never specified a distance range as she and Ash were willing to travel to other regions to get off with people.

She logged into her online profile, her avatar was a pic of her on her knees on her and Ash's bed posing nude whilst wearing a white face mask to hide her identity. She looked through her profile and was smiling whilst reading all the positive reviews she got from all her previous partners - to date, she has not received a single review that was at the slightest negative. She was proud of her 100% recommendation score, and it upped her ego in bed. However the downside of this was that it often meant she was approached by random creeps asking for sex which made her feel uneasy. She then browsed through her email and had one eyebrow raised at some of the weirdest requests and pleads for sex especially the ones asking if she would do drugs during sessions, be willing to have sex with a human as well as a pokemon or take part in incestous orgies. She deleted such emails without responding and was slightly disappointed that none of the attractive guys on her favourites list that she had her eyes on were free tonight. She then resorted to manually search for partner and once the results of her search came up she read some of them aloud.

"30, lives alone (in the garage of his mum's house) in Lumiose with his pokemons… heck no, could be a creep" Serena said shuddering. "27 from Cerulean city, prefers males and pokemon of any gender, O...K...then, 100% no and craves BDSM, no way. "Two "gentlemen" double team, Anistar City, here to stretch you to the max. Nope, never again with double penetration. Darn, is there anyone good available tonight"?

"Oooh Trevor from Vaniville. Wait already fucked him, so that's a no." "Tierno… a bit on the large side. Not too bad though… but wait, says he's currently not in the region and unavailable until January, well that's not going to help me. Next." "Sycamore, Lumiose, looks attractive, 49! He's old enough to be my dad, maybe next time or when I am more in the mood for that sort of thing." "Ramos, Coumarine,… 65! what the f… how does HE have a profile on here?" Then she remembered her promiscuous night with Professor Oak who was the only exception for the age requirement as she completely trusts him and has done so since she was 5 years old, back at the summer camp.

"Tracy, 26 years old currently residing in Pallet Town. Mmmm… looks nice and saw him when I was with Prof Oak but wait, only has protected sex… not a yes from me then" sighed Serena. She knows the importance of staying healthy and free of STDs but can't stand the feeling of condoms as it makes sex less pleasurable in her opinion so only has sex with reputable bareback boys with official medical certificates that prove they are clean. Serena and Ash also have regular monthly STD checks to monitor their own health.

She then viewed a guy called Red's profile and immediately noted that he looked a lot like Ash which upped his position on Serena's list before she realised that it would be creepy to sleep with someone who looks like her boyfriend and may cause problems later on. Also she remembered some of her friends saying that Red never talks during meet-ups and just goes straight to the main event. Serena quickly crossed him off her list also taking into account how difficult and desperate it must be to climb Mt. Silver just for sex.

Getting frustrated, she whined and shouted "I want to get laid tonight, it can't be that difficult!". She then used her left hand to masturbate, whilst still browsing the site for a guy. The profile of Brock, from Pewter, caught her eyes but it took only one glance at his reviews before she abandoned his profile - it appears almost all the girls have complained about having contracted STDs from encounters with Brock even though he claimed he was clean.

Serena was getting disheartened and was about to speed dial Clemont to come over this time to her place for sex especially after what happened last time. Whilst deciding whether to call him or not, she remembered their previous encounter. It was 5 months ago, the last time she was unsuccessful with arranging an appointment with a guy, she went over to Clemont's dressed in her favourite red high-waist skirt and black top and after they shared a quick french kiss and gropes at the door, entered his living room where Chespin and Bunnelby where watching TV. Clemont and Serena sat down and had a casual chat and drank some Cola to relax. Serena then remembered and fetched from her handbag a small food bag filled with macaroons for Chespin who gladly took it and ate it all in one go. Serena giggled at this and when she noticed that Bunnelby was occupied with saving Chespin who was now choking from eating too many macaroons at once, glanced at Clemont and when he made eye contact with her, she spread her legs to show him her panty-less crotch, exposing her vagina to him. Clemont immediately popped a boner and his glasses became foggy.

Serena didn't want to wait any longer and then grabbed his arm and whispered "Come on, let's play" before taking him into his room. In their rush, they forgot to lock the door and 15 minutes into their sexual romp, Chespin entered to try and find Serena in the hope of getting more macaroons. But what he saw made his eyes open wide - on his master's bed was his master and his female friend, both naked and sweating with the duvet only covering them from the waist down. From what Chespin could make out, Serena was sitting on top of Clemont who was facing her and appeared to be jumping up and down on him with a smile whilst her hands were on his stomach. Clemont had his eyes closed and was gasping whenever Serena was coming down on him. Chespin immediately felt weird and moved past all the clothes that were scattered on the floor and climbed, unbeknown to the pair, onto the bed and tapped Clemont. Clemont was in utter bliss and mindlessly said "Not now Chespin, can't you see I'm busy. We can play later, I promi…" He suddenly opened his eyes and shouted "Chespin what are you doing here!" His outburst bought Serena back down to Earth, as she stopped impaling herself on Clemont's cock and became wide-eyed when she realised Chespin was there and quickly covered herself with the duvet.

Chespin was just innocently looking back and forth between the two not knowing what they were up to. Serena didn't know what to do but when she realised Chespin was sporting a good sized boner, for his size, she quickly gave him a handjob (to this day she doesn't know why she did that) and after Chespin experienced his first ever orgasm, he was on the verge of collapsing but before he did, was picked up by Serena who pressed him against her breasts and kissed him on his lips. Chespin then passed out with a smile. The sight of the erotic interaction caused Clemont to lose it and ejaculate and shoot his load into Serena's pussy, who was caught by surprise by the warmth flooding through her and caused her to drench Clemont's 6 inch cock in her fluids. So Serena was determined not have such a scenario playing out again (despite the enjoyable ending) and decided along with Clemont and Ash (after he stopped laughing at the story when Serena told him) that if she and Clemont were to have sex, it would be at her and Ash's place.

Well how was chapter 1 guys? Don't worry folks Serena will have a rocking time in chapter 2, rest assured.