Chapter End Notes:The party was starting to wrap up and most of the guest had already left. The remaining guests were saying their goodbyes as it was now just past midnight. Everyone seemed to have enjoyed themselves that night. May and her friends had a really good day and the party that topped it off was really fun.

Some of the PlayPoke staff were starting to clean up and stack the chairs and tables from the event. Cynthia was still at the party and now that it was coming to a close she decided to go and talk to May about her experiences that day.

"So did you enjoy the party?" Cynthia said as she walked over to May.

"I sure did. It turned out a lot better than I thought it would. I still can't believe that I won the competition." May said as Cynthia could tell that May was genuinely surprised that she had won the competition.

"You did great and you definitely picked outfits that suited you which the crowd and judges also thought were good." Cythina said as she explained to May why she had won.

"Thanks. I'm glad people thought that I looked that good." May said as she was grateful for the complement.

"You're definitely a beautify woman and winning that contest shows that people definitely like you. Have you thought about the PlayPoke photoshoot offer at all? It's an amazing offer and I'm sure that a lot of people would want to buy the issue." Cynthia said as she wanted to see if May had considered doing it or not yet.

May recalled the earlier conversation she had with Mr. Contesta and Cynthia about an extra photoshoot that would be featured in the upcoming PlayPoke magazine Miss Aopulco special issue if she chose to do it. The extra photoshoot would feature her naked and possibly having sexual intercourse. May was still a shocked by the prospect of doing a photoshoot naked for a publication that would be seen by a lot of people and even more concerned about people seeing her having sex even if it was with people she liked and trusted.

"I haven't really thought about it too much yet." May finally responded as she needed to say something to Cynthia.

"Well continue to think about it because its an amazing opportunity to become even more popular. Who knows what other opportunities will be given to you and other job offers will be offered as you become more known to the public. I know from experience that it's a good opportunity." Cynthia said as she knew from experience that it would make May a more popular person.

"From experience?" May said as she knew Cynthia had done some PlayPoke photoshoot before but she didn't realize she had also done explicit ones too.

By this time, Ash had noticed that May and Cynthia were talking together. Cynthia happened to glance over to see Ash and their eyes locked for a second. Ash decided to walk over to the girls to see what they were talking about and to join in on the conversation.

"Yeah, I've actually done a few explicit photoshoots for PlayPoke magazine recently. I really enjoyed doing them and it definitely opened other opportunities for me, like judging today's Bikini contest." Cynthia said as she made sure that Ash had heard her reply to May's question as a bit of a tease for him.

Cynthia had always found Ash to be quite an amazing individual and now that he was in the Master League, he had really proven himself to be a challenging opponent for her. She had watched him grow over the years since the time they first met in the Sinnoh region. Ash had matured and Cynthia could tell that he was now a very responsible and likable person. Cynthia found those qualities to be very attractive traits and she could see why Ash had a few girlfriends traveling with him on his journey. Cynthia also liked younger guys and Ash fit all of her criteria for guys she liked.

"You've done explicit photoshoots?" Ash said as he was shocked and intrigued at the same time as he overheard May and Cynthia talking.

"Yes. I've done a few. I was just telling May that she should consider the offer that PlayPoke offered her today." Cynthia said as she could tell that the little tease for Ash had worked as it had implanted a little thought into Ash's mind to think about now.

"What offer?" Ash said as he wanted to know more about the offer that May had been given.

"I was offered a photoshoot with PlayPoke to do shoot naked and possibly having sexual intercourse." May said to Ash as he was yet again surprised in this short conversation that he'd just joined.

"Oh so that's what you're thinking about. We'll we know from when you signed up that you might be offered other jobs. You don't have to do it though. Your obligations are done with PlayPoke." Ash said as he reassured May that it wasn't something she had to do.

"Yeah, I definitely haven't decided but Cynthia was saying since I won the Bikini contest today, I have the opportunity to become even more popular with this photoshoot which could unlock even more job opportunities in the future." May said as she explained the situation to Ash.

"You should seriously think about doing it May, besides Ash here would be a great candidate to join you in the photoshoot. He's already very popular as he's in the Master League now and the issue could appeal to both guys and girls." Cynthia said as she saw Ash's eyes bulge open wide when he heard the suggestion.

"What me in the photoshoot too?" Ash said as he couldn't believe what he was hearing.

"Well yeah, the offer was to May and any of her friends that she chose to join her in the shoot. I assume you to are close friends and are having sex together from the way you act around each other I assumed as much." Cynthia said as both May and Ash didn't think their interactions with each other were that obvious or Cynthia just made a wild assumption.

"Uh... yeah I guess that makes sense." May finally said as Ash and May traded glances back and forth as both of them didn't want to say anything.

"I thought as much. It's something you should think about though as it really is a once in a lifetime opportunity. Not many people are offered a photoshoot with PlayPoke magazine. I know I was surprised when I was offered it." Cynthia said as she recalled some of the feelings she had when she was offered the job.

"Were you scared or nervous when you did the photoshoot?" May asked Cynthia as she wanted to know a bit more about her experience.

"Not really. The photographer was really good about making me feel comfortable in front to the camera and I had some of my friends with me that I loved and trusted so I ended up being a really good experience." Cynthia explained to May as she hoped it helped convince her.

"Actually we do have a bit of experience in front of the camera..." Ash said as he remembered the video his mom had made.

"You do? Well then you should feel a lot more comfortable about doing it already." Cynthia said as she was now a bit curious what they had actually been doing sexually together.

"Ash! She doesn't need to know everything in our personal lives." May said as she scolded Ash for saying that they had experience in front of the camera.

"It's fine. I won't ask if you don't want to tell." Cynthia said as she noticed that Ash's other friends were now coming over to join the conversation.

"Well guys its starting to get late and most people have left now, I guess its time we head back to Iris's room for the night." Brock said as he suggested that everyone turned in for the night.

"Awe, the room is a bit cramped though and some of us will have to sleep together." Dawn said as she wasn't looking forward to the cramped room.

"It's better than sleeping on the beach again though." Misty said as she was glad to have a bed either way.

"You guys need some extra room tonight? I'm in my own suite that has multiple rooms at a hotel down the street, so there is plenty of room if some of you want to board with me for the night. How many beds are there in your room?" Cynthia said as she asked if they wanted to board with her for the night.

"There are 4 beds in the room." Iris said as she told Cynthia.

"How about if Ash and May stay in my room tonight as thanks for being a last minute judge and for winning the contest?. That should free up the space for your friends to have a restful sleep tonight and we can all meet in the hotel lobby tomorrow for some breakfast." Cynthia suggested as she was already starting to scheme a bit hoping that Ash's friends would agree.

"Sounds good to me. I could use a nice relaxing sleep in my own bed tonight." Misty said as she was really tired and was glad that she could be able to stretch out in the bed.

"Fine with me too. Are you sure its okay Cynthia?" Ash said as he was a bit surprised that Cynthia offered them.

"Sure. Its no problem at all." Cynthia said as she smiled.

"Alright let's head out then. I'm getting tired and its quite late now. Good night guys. See you in the morning." May said as Ash and Cynthia joined her and left the Pokemon Center toward the hotel.

The hotel was only a few minutes walk away from the Pokemon Center and as they walked in Ash and May were very impressed with how fancy the lobby looked. Cynthia walked over to the elevator and Ash and May followed her. Cynthia pressed the button for the top floor and the elevator started going. Most people had already gone to sleep so the elevator car went all the way to the top without stopping.

The doors to the elevator opened and Ash and May followed Cynthia to her room. It was only a few feet down the hall and Cynthia got out her keycard and swiped it through the reader to open the door. Cynthia walked into the room and motioned for Ash and May to join her. They were both amazed when they walked in the room.

The penthouse suite was a very impressive rooms, one of the most expensive rooms Ash or May had ever been in. The floors were all shining dark marble with rugs and expensive looking furniture. There was an immense bay window at the end of the room that overlooked the beach. The walls were high and had vaulted ceilings with skylights that were filled with the nights sky. A large king sized canopy bed with drapes was to the side of the room. There were also two other doors on the left side of the room that led to a walk in closet and what looked to be a bathroom and sauna. On the right side of the room there was three doors, one that led to a guest room, one that led to a kitchen and another looked like a media entertainment room.

"Wow! This room looks amazing!" Ash said as he looked around amazed at how expensive everything was.

"It sure is. I could live in a room like this." May said as she was also impressed with the room.

"Well, if you continue doing what you are doing, you could also be living this life style. I wanted to show you this room because this is the type of room that popular stars stay in regularly. I've gotten accustom to it but I still find it to be very impressive. This is the type of room that PlayPoke uses for their photoshoots too, elegant and expensive looking." Cynthia said as she could tell that both May and Ash were quite impressed with the room's decor. 

"Really? Wow. Look at the size of that bed! It's huge!" May said as she'd never seen a bed that big before.

"If you guys would like to get ready for bed, the bathroom is just to your left. Here, let me show you." Cynthia said as she hoped that she would be able to convince them to do a bit more extra curricular activities that night as she directed May and Ash to the bathroom

Ash, May and Cynthia walked into the large bathroom and were once again stunned by the elegance and style of the room. It was almost as big as a public bathroom in a Pokemon Center. There was a sauna room, a huge shower that had marble walls and a bench seat and what looked to be like multiple shower heads. There was a large whirlpool tub that had a large picture window that allowed bathers to be able to look out as they bathed. There was two sinks and a large mirror.

"This bathroom is incredible. I could spend hours in here." May said as it was pretty much every girls dream bathroom.

"Yeah its really spectacular looking room for a bathroom." Ash said as too could only be impressed with the luxurious room.

"Well feel free to get ready for bed then. I think I'm going to have a relaxing hot steam in the sauna room before I go to bed. Your welcome to join me if you wish." Cynthia said as she walked over to the sauna room door.

"Oh! That sounds like it could be very relaxing. If you don't mind I think I'll join you as soon as I brush my teeth and wash up." May said as she was interested in a relaxing sauna.

"Alright then. How about you Ash? Care to join us?" Cynthia said with a bit of an inviting smile that Ash found very hard to resist as he didn't see Cynthia smile too often as she always seemed very serious.

"Uh.. Okay I guess I'll join you guys." Ash said as May could tell that Cynthia seemed to like Ash by the way she was acting and May knew that Ash now had a hard time saying no when it came to what girls wanted.

May didn't mind the fact that Cynthia seemed to like Ash. Ash was a very likeable person but it seemed odd to May that Cynthia would go after Ash who was quite younger than she was. May gave a little smirk to Cynthia to indicate to her that she knew what she was up to. Cynthia noticed the smirk and smiled back at May hoping that she would get the approval from May to allow her to continue since Ash was her close friend. May nodded back at Cynthia as she knew there really wasn't anything to stop her from doing what she wanted. It wasn't like Ash was going to resist the advances from a supermodel like Cynthia.

"I'm just going to get my bathing suit and I'll be right back." Cynthia said as she walked out of the bathroom to get her bathing suit.

"Alright." May said as she opened up her backpack and got out her toothbrush and began brushing her teeth.

Ash opened his backpack as well and looked for his swimming trunks. He quickly found them and took them out. He then realized there wasn't anywhere to change privately, so he decided to quickly go into the shower area to change. By the time Ash had quickly changed, May was about ready to change into her bathing suit as well.

May realized that Cynthia was actually kind of competing for Ash's attention now, so she decided that she should wear blue her microkini bikini that helped her win the bikini competition. She was a bit more content wearing it now even though it wasn't the most comfortable outfit to wear as it wasn't big enough to cup her breasts to support them and just barely had enough material to cover her nipples and areola.

May knew Ash liked seeing her in the bikini so she took it and changed in the shower area just like Ash had moments earlier. By this time, Cynthia had changed into her sheer black bikini that was semi transparent that she had warn earlier in the day. She had caught Ash looking at her breasts earlier in the day and she thought it would be fun to let him have another look. Once again Ash took quick peak and he could sort of see the outline of her areola's through the material before forcing himself to look away as May had changed into her bathing suit which caused Ash to gulp a bit.

"So you two look like your read for the sauna now. After you two." Cynthia said as the three of them entered the sauna room and Cynthia closed the door behind them.



Cynthia and May sat down on the opposite side of the sauna room from Ash. He couldn't help admire the girl's bodies as both of the girls looked really sexy in their bathing suits and he smiled as he felt his penis twitch a bit from the sight. Ash didn't try to hide the fact that he was looking at their bodies as it just seemed natural to do so when they were in their bikini's.

"What do you think of the sauna?" Cynthia said as she decided she'd say something.

"It's pretty nice and warm." Ash said as he tried to look at Cynthia's face and into her eyes and not at her body.

"Yeah it is. I like how the steam opens my pours." May said as she was starting to sweat a bit from the heat.



"Thanks for letting us stay here tonight Cynthia. We really appreciate it. This hotel room certainly is quite luxurious." Ash said as he looked around at the sauna room as steam started to build around them making it a bit harder for Ash to see the girls now.

"Don't mention it. It's really too big for one person anyhow. I'm glad you guys came. So what are your upcoming plans?" Cynthia said as she was interested in knowing what they were going to be up to next.

"I think I am going to battle against Lt. Surge next. I've actually been looking forward to this rematch for awhile as I am sure his Raichu has got a lot stronger since the first time we battled, but so has my Pikachu." Ash said as he realized that he'd have to go get Pikachu in Pallet Town before he challenged Surge because Professor Oak just couldn't transfer him in his Poke ball.

"Lt. Surge is a tough guy. By the time you get to battle me to challenge for Champion Master, you'll have become even stronger. I'll have to make sure I start training my Pokemon soon so they are ready for you." Cynthia said as she realized that Ash would be a very formidable opponent for her.

May, Cynthia and Ash all small talked for about 20 minutes or so. It was starting to get really hot in the sauna and all three of them were sweating quite a lot. Ash had just about enough of the heat and needed to cool down.

"Wow! It's really getting hot in here. Do you mind if I use the shower real quick to cool off?" Ash asked Cynthia as he hoped she would agree.

"Sure. That actually sounds like a good idea. I think I've had just about enough of the sauna for tonight too." Cynthia said as she decided she'd get out of the sauna with Ash.

"We'll I don't want to stay in here alone, so I'll wait till Ash has had his shower." May said as she didn't want to be left in the sauna alone even though she was still enjoying it.

"Ah don't worry May, I think the shower room is big enough as well for all of us to have a shower at once. It's almost the same size as this sauna." Cynthia said as Ash was kind of surprised that Cynthia would suggest that they shower all at the same time.

"Uh wouldn't that limit our privacy a bit?" Ash said as he was surprised that she would suggest that they group shower together.

"We'll just have a by the pool shower and keep our swimsuits on while we shower." Cynthia said as she hoped that it would actually go a bit further than that.

"Okay then." Ash said as he found the thought of showering with May and Cynthia even with their bathing suits on a bit sexy and he knew he'd have to be sure to watch himself so that neither of the girls noticed his erection that was starting to build.



The three of them got out of the sauna and walked over to the shower room and they went in the shower room together. As Cynthia had said, it was quite a big shower. The shower only had one control which Cynthia turned on. Multiple heads began to pour cold water on Ash, May and Cynthia as the three of them began to cool off under the water.

Ash had a great view of some amazing wet cleavage from both May and Cynthia as both their swimsuits were now wet. Cynthia noticed that Ash was looking at her breast which made Ash instantly blush and his face turned to a nice shade of red. 

"Uh... I'm sorry I didn't mean to..." Ash quickly said as he knew Cynthia caught him starring at her.

"It's okay Ash. You don't have to turn away. If you want to look at my breasts while you shower, I don't mind, in fact I want you too. I like it when guys think I look good." Cynthia said as she finally got Ash's attention.

May kind of rolled her eyes as she realized this was coming but at least now it was in the open and the cat and mouse game could finally end. Ash couldn't pull my eyes away from Cynthia's wet breasts not matter how hard he tried as he watched her shower.



Ash watched as the small drops of water splashed onto Cynthia and flowed down her body. Ash was reminded of the first time he and his mom had had a shower together and he was now starting to get more turned on as Cynthia was older than he was and Ash realized that liked looking at older girls too. By this time, May and Cynthia could both see the erection forming under Ash's swimming trunks. Realizing that Ash was turned on also turned on May and Cynthia as all three of them were starting to get horny.

Ash couldn't believe this was happening to him, two bikini contest winners were in the shower with him and it seemed like it would be going a bit more past just showering at this point. Cynthia grabbed a bar of soap and began creating a thick white foam. She walked over to Ash and began soaping up his young smooth chest. Ash didn't have big muscles like Brock but his body was shaped well. 

Ash now got the best view of Cynthia's cleavage that he'd ever got and he admired her gorgeous breasts as the water ran down between them. Cynthia knew Ash was starring at her cleavage and that turned her on and she felt her nipples growing hard and press against the fabric of her bikini. Ash actually watched as he saw Cynthia's nipples get erect under her bikini top and that also caused Ash's penis to become fully erect as well. Cynthia massaged Ash's shoulders with her hands a bit and she wiggled her shoulders back and forth a bit which made her wet breast jiggle a bit.



Ash's hair was all wet and his bangs were flopping in front of his eyes and he'd have to push it to the side ever few minutes. Cynthia noticed this and the next time Ash needed to move his hair to the side, she reached her hand out and brushed his hair to the side. She then smiled at him and leaned forward as she moved forward and began gently kissing Ash on the lips. Ash was now backed up against the shower wall and May was wishing it was her kissing Ash as she watched the two of them.

Ash was a bit stunned by Cynthia's forthright approach towards him and he felt her tongue trying to find a way inside his mouth. Ash parted his lips to allow her tongue to enter and tongues met and they began to move around in each other mouths as Ash started returning Cynthia's affectionate kiss. Cynthia was now enjoying the kiss even more as she realized he was now returning her kiss. This made her even more excited and horny and she pressed her breasts against his chest as they kissed.

"Wow! I'm surprised how good a kisser you are! Usually guys your age aren't very good. It seems like you've had a lot of practice." Cynthia said as she looked over at May who kind of smiled in an embarrassing way. 

Cynthia then kissed Ash on his forehead and pulled his head down toward her cleavage which he had been looking at earlier. His face was now in between her large breasts and Ash couldn't believe it.

"I noticed you liked looking at my breasts earlier, so I've decided to let you have a closer look." Cynthia said as Ash wasn't protesting at all.

Ash realized now that she had caught him starring at her but obviously she didn't mind as he was now face first between her beautiful breasts. She let him rest there for a few moments before she noticed that his erection was getting larger in his wet trunks.

"Take your shorts off Ash." Cynthia said as she looked down at Ash's swimming trunks which were soaking wet now from the shower.

Ash didn't need to hear her say it a second time and he did as he was told and quickly took off his swimming trunks and tossed them to the other side of the shower. Ash was completely naked now in front of Cynthia and May. His penis stood erect in front as Cynthia and May both looked down lustfully at it.

"Impressive young man! There are many guys that would love to have a penis that is big and a sexy as yours is." Cynthia said as she was pleasantly surprised to see that despite Ash's height, he had an impressive penis for his age.

Ash was speechless as he didn't know how to respond to Cynthia's complement. He didn't have to as Cynthia picked up a bottle of liquid soap and began pouring it over her tits. She used up almost the entire bottle as her breasts and bikini top were now completely covered in the soap. Her body was now glistening and shining with all the liquid soap and Ash thought her body looked incredible as looked her over.

"Would you like me to give you a boobjob?" Cynthia asked as Ash couldn't believe she was asking him that.

"Of course he does! Look at him, he's almost ready to explode as it is." May said as she knew Ash was going to enjoy every second of it.

"Is May telling the truth? Do you really want me to do it? I want to hear you say it before I do." Cynthia said as she teased Ash.

"I do want you to!" Ash said as he was looking forward to it.

"That's what I wanted to hear. Now let's see what I can do to help make that penis of your's feel better." Cynthia said as she got down on her knees in the shower and raised her breasts up so that they slid between Ash's penis.

Cynthia left her bikini on but there was still plenty of cleavage for her to give Ash an amazing boobjob. Her breasts were so slippery and soapy that Ash penis slipped right on the cleavage of her breasts fine. Ash's first feeling of Cynthia's breasts were of his penis touching her wet and soapy breasts. It felt amazing but the texture of her skin was lost with all the soap on her breasts.

Cynthia grabbed her breasts and began moving them back and forth. Ash's penis often slipped out of her cleavage as it was slow slippery but she did her best to keep Ash's penis between her breasts. Ash was starting to enjoy the boobjob he was getting from Cynthia as her gorgeous breasts stroked his penis.



Ash had never seen breasts as big as Cynthia's up close, even his own mom and Dawn's mom who were older women didn't have breasts this big. Ash felt like he was very lucky that he was able to behold them and to have his penis being stroked by them.

"Ash you seem to be a bit tense and uncomfortable. Aren't you enjoying this?" Cynthia asked as she could tell that Ash wasn't fully enjoying his boobjob.

"Uh no, I'm enjoying it, it's just I never expected to be doing something like this with you." Ash said as he still felt a bit shy.

"What he means is he's a bit shy when it comes to doing things like this with girls. He really does want you to continue but being the proper gentlemen that he is, he didn't want to make it seem like he's taking advantage of you." May said as she knew Ash all too well.

"Is that so Ash? If that's the case, then don't worry about it. I want to do this with you because I like you and I want you to like me too so we both can feel good together and love each other just like you love May here." Cynthia said as she had stopped giving Ash a boobjob to talk with him.

"Yeah. I'm always a bit shy and uncomfortable around girls I like." Ash said as he subconsciously spurted out that he liked Cynthia.

"Oh so you like me do you?" Cynthia said as she was glad that Ash felt the same way and admitted it now.

"Uh what?! I mean... Uh yeah I guess I do like you." Ash said as he blushed a bit and he was glad that the cool water from the shower masked his hot red face a bit.

"Well since I like you and you like me, let's keep going shall we?" Cynthia said as she began stroking Ash's penis with her breasts again as they bounced around and her erect nipples that were pressing against the fabric of her bikini looked like they no longer wanted to be covered. 

Even though Cynthia still had her bikini on, her breasts were big enough to still get some movement going around Ash's penis. It would have been a bit easier for her to give him the boobjob with it off but she didn't feel like stripping it off right away.

"You're starting to get comfortable now and like this, aren't you, Ash?" Cynthia asked as she could tell by his moaning he was enjoying it now.

"Oh, yes, Cynthia I like it a lot!" Ash said as he was really enjoying himself now.

"Good, I love feeling your big hard penis against my breasts. It feels so good against them. Here try doing it yourself for a bit." Cynthia said as she grabbed Ash's wrists and placed is hands on her bikini covered breasts.

Ash was getting more horny by the second and he was now touching Cynthia's magnificent breasts for the very first time. Ash straddled her breasts and pushed his penis between them and squeezed her cleavage tight like she had been moments earlier.

"That's it, Ash! Fuck my titties. I see that my teasing you finally paid off." Cynthia said as she loved watched Ash's penis appear and disappear in the cleavage of her breasts.

"You were purposely teasing me?!" Ash said as he never liked being teased by anyone.

"Of course she was Ash. That's what girls do when they put their breasts on display like she had been. You still got a lot to learn. Girls like to tease guys!" May said as she couldn't believe Ash still couldn't understand girls sexual signals.

"So you were teasing me all this time and I felt ashamed for looking." Ash said as he was glad now that it was on purpose and that his earlier being caught peaking wasn't so bad now.

"I was hoping you were interested in me too, so I guess I was right about that! Girls notice when guys check us out. Guys don't think we notice, but we do. Sometimes though, girls what guys to check them out." Cynthia said as she smiled at Ash.

"How big are your breasts Cynthia?" May asked as she was curious so see how they compared against hers. 

"They are 38dd. They are quite big aren't they? They are natural too. I'm quite proud of them especially when guys like Ash here seem to enjoy them. I like when they look at them as it makes me feel good about myself that guys want to look at me. You know May, you have pretty big breasts for your age too. I guess that's one of the reasons you won this years bikini contest. How big are your breasts?" Cythina said as she had always found her breasts to be one of her most defining features.

"I'm a 34c. Not quite as big as your's though. My mom has 36dd, so hopefully I'll grow to about her size." May said as she told Cynthia her breast size.

"I'm sure you will. I'm sure Ash loves playing with your breasts just like he seems to be liking my breasts now." Cynthia said as Ash was slowly stroking his penis between her breasts still.

"He does. I've given him a few myself. He always likes them." May said as she recalled doing them for Ash a few times in the past.

"You know, I'd like to see you give Ash a titfuck so I can watch you two." Cynthia said as May looked a bit shocked by Cynthia's proposal.

"Right here, right now?" May said as she was quite content just watching Ash and Cynthia do it.

"Sure. Watching other people do sexual stuff is a turnon for me." Cynthia said as she backed off to Ash's dismay.

"Uh alright." May said as she got down on the shower floor in the same position that Cynthia was just in.

May's sling bikini made is really easy for her to give Ash access to her breast to the boobjob. She left the bikini on and wrapped her large firm breasts around his penis. May's breasts felt wet like Cynthia's breasts but not quite as slippery as it was just water on May's skin and not soap as well. May pushed her breasts together and Ash groaned aloud at the sensation of May beginning to stroke her breasts against his penis.

"Oh May this feels so good!" Ash said as he closed his eyes and let May do her job.

"Well May it seems you are talented at that as well. I love watching your foreskin goes back and forth as it strokes between her breasts." Cynthia said as she watched May give Ash a boobjob now.

Ash started leaking pre-cum as the stroking of his penis between May and Cynthia's breasts was almost too much for him. Each time May pushed her breasts down, the head of Ash's penis came out the top of May's cleavage and Cynthia could see the head and the hole of his penis. Cynthia wanted him to cum all over May right then and there but they needed to pace Ash.

"Do it a bit faster May. Ash really likes your breasts." Cynthia encouraged May.

May was starting to enjoy pleasuring Ash with her breasts. May also found it strangely erotic having Cynthia watch them do it. The exhibitionist feeling made May more horny as she stroked her breasts against Ash's penis faster now. 

"Oh Ash, blushing again. You certainly blush easily. Why are you blushing now for? I thought you were more comfortable doing this with me."

"It's a bit embarrassing when you have an audience watching you do sexual stuff." Ash said as he was still a bit shy.

"Well, for what it's worth, I like looking at you naked, so you should find that as complement and it should increase your self esteem. Now stop being so shy and embarrassed. May and I aren't embarrassed, so neither should you. Just relax and don't worry about it. Keep in mind that this will only end up being pleasurable for all of us." Cynthia said as she tried to reassure Ash a bit.

"Alright, I'll do my best not too." Ash said as May stopped giving Ash a boobjob and stood up as the tiles on the floor were hard to kneel on for too long.

"I can't kneel too long on the tile floor without it hurting my knees. I needed to get up." May said as Cynthia and Ash both wondered why she stopped.

"Why don't we dry off then and go over to the bed." Cynthia suggested.

"Alright anything beats this hard floor." May said as she was glad to get up.

Cynthia, Ash and May exited the shower and each took a towel and began to dry their bodies off. Ash quickly wrapped the towel around his shivering body to warm him up a bit. The girls still had their bikini's on so they had some clothing unlike Ash who was completely naked. Cynthia and May both wrapped towels around themselves after drying off.

The three of them walked into the main room and over to the large king size bed which dominated the entire room. Cynthia and May finished drying themselves off and dropped the towel on the floor in front of the bed, revealing their semi dried bathing suits again. Ash's attention was immediately focused on them. Cynthia got on the bed and lay down as she crossed her legs a bit and stretched out on her bed in her bathing suit.

"Wow this almost feels like a fantasy!" Ash said as he couldn't believe how sexy Cynthia looked on her bed.

"A fantasy huh? I guess you've have a fantasy about me? Huh?" Cynthia said as she pressed Ash for more information about his fantasy.

"Oh erm... It's nothing really. Seeing you on the bed like that is amazing. You look really sexy right now. I..." Ash said as May and Cynthia were both impressed that Ash was willing to finally express some of his feeling with them having to pull his teeth to get him to admit it.

"Why thank you for the complement Ash. But you what? You stopped saying what your were thinking. What were you going to say? You can tell us." Cynthia said as she wanted to hear what Ash was thinking.

"I... I was imagining what you look like naked." Ash said as he told her what he was fantasying about.

"Oh is that all of your fantasy just wanted to see me naked? You never thought getting blowjob or us fucking?" Cynthia said as she was a bit disappointed with Ash's imagination. 

"Well... I guess when you put it that way I could fantasize about doing that too." Ash said as he liked how straightforward Cynthia had become.

"The truth is Ash, I have been fantasizing about you for years, since we first met in the Sinnoh region. I have never lost those feeling and seeing you here again today, I realized I needed to make a move. You are a very special guy Ash and I don't meet guys like you very often." Cynthia said as she told Ash how she really felt about him.

"Really? You've liked me for that long?" Ash said as he was surprised to hear Cynthia say that.

"I know it sounds a bit weird me telling you after all this time and that it's not exactly normal for an older woman like me to like a younger guy but I wanted you to know that I actually like you." Cynthia said as she continued to explain to them how she felt.

"Your not the only older women that has found Ash attractive, so it's not that odd." May said as she lead Cynthia on a bit.

"Oh Ash has had relationships with women older than him before? Do tell!" Cynthia said as she sat up on the bed wanting to hear all about it.

"Ash has had sex with quite a few older girls before including Dawn's mom and his own mom!" May told Cynthia as she was shocked to hear that Ash had had sex with his own mom.

"You had sex with your own mom? That sounds exciting! How did that happen?" Cynthia said as she wanted to hear more.

"Ash's mom decided to teach him about sex and she figured the best way to teach him was to do it with him. She's been giving him sex lessons ever since." May said as Ash was blushing a bit as Cynthia listened to the story.

"Sex lessons eh? That certainly sounds like a lot of fun." Cynthia said as she was

"We have actually all been doing the lessons with Ash's mom. We've really learned a lot from her over the sessions." May said as she finished explaining their sexual life to Cynthia.

"I'm surprised after hearing that, that you haven't already decided to do the PlayPoke photoshoot May. It sounds like you already have the necessary experience." Cynthia said as she was learning more about Ash and May every second.

"Well it's a lot different doing it in private than it is doing it in public for all to see." May said as Cynthia understood May's position.

"I want to make you an offer Ash. If you convince May to do the PlayPoke photoshoot right now, I'll strip naked in front of you. You wanted to see me naked and I want to get May to do this photoshoot, so we all get what we want. What do you say?" Cynthia said as May was surprised that she would try to get Ash to convince her to do the photoshoot.

"I can't believe I'm hearing this. You're trying to bribe Ash to convince me to do the photoshoot now?" May said as she couldn't believe Cynthia would stoop this low in her tactics.

"Why not? I know you May, you'll do anything that will make you more popular. I'm pretty sure you've already thought about doing the photoshoot and you are just trying to make it seem like you aren't a prude." Ash said as he also knew how May thought and reacted since he'd known her so long as well.

"You just want to convince me now so you can see Cynthia naked. Fine, I'll agree to do the photoshoot but you have to be in it with me, so your not getting out of this situation that easily." May said as she wanted to make sure Ash was with her if she was going to do the photoshoot.

"Fine I'll do it too. I don't mind." Ash said as he really didn't think about what he was getting into here by agreeing to do the photoshoot.

"So your both going to do the photoshoot now? Amazing, that will be a really good photoshoot. You two don't realize how popular it will be when it's released. I know and I'm sure you'll both do fine." Cynthia said as her plan to get Ash to get May to agree to do the photoshoot had worked.

"Well it seems like you two both got what you wanted." May said as she realized that she had just spontaneously agreed to something that could be life altering.

"Believe me May, it's the right choice. You'll thank me for making you do it. Now I guess I have to live up to my part of this bargain huh?" Cynthia said as she realized she'd have to strip naked her in a second.

"That's right. I want to watch you strip naked. I want to see you take off that bikini you have been teasing me with all day and show me your tits and pussy." Ash said as he was really getting horny and Cynthia liked how Ash finally was acting more forthright.

"So you want to see my tits and pussy that badly huh? You know you could have asked me a lot earlier and I would have obliged. I've wanted undress myself in front of you so you could admire me and I guess that moment has finally arrived." Cynthia said as she got up off the bed and stood in the middle of the room in preparation for a small strip tease for Ash.



Ash was trembling in anticipation as he knew that Cynthia was going to be naked in a few seconds and he'd finally get to see what she looked like. Cynthia took a deep breath and reached around her back and slowly untied the straps of her bikini top and then lifted the cups that covered her 38dd breasts. Cynthia's breasts were now revealed and a jolt of excitement went through Ash's body right to his throbbing erect penis under his towel. Her tits were gorgeous tits and seeing both of her bare breasts in their entirety for the first time was mesmerizing. They were well shaped and her light pink/brown areolas much have been around 2 inches wide, the biggest aerolas Ash had ever seen. Her erect nipples stood out for nearly half an inch from her breasts as Ash knew her nipples must have been big after seeing them erect under her bikini.

"Like what you see?" Cynthia asked Ash as she knew he did.

"Amazing! Your breasts are beautiful. I thought I'd never had a chance to see your breasts naked and now that I have they're more than perfect that I had imagined. I love the size of your nipples, your large aerolas and the shape of your breasts. They're amazing." Ash said as Cynthia enjoyed getting the complement from him.

All the was left now was her bikini thong bottoms. Ash began thinking about if Cynthia shaved her pussy completely or if some hair would be there. Ash's attention changed from Cynthia's breasts to the small triangular shaped thong that hugged her pussy so tight from being wet that Ash could already see the outline her mount with an indented gash in the middle. Cynthia grabbed the sizes of her thong and slowly eased her bikini bottom down her long legs.

Cynthia's pussy was now completely visible and her pussy lips were shaved hairless. The only pubic hair she had was a little strip above her slit that looked quite sexy as it was neatly trimmed. Cynthia opened her legs to give Ash and May a better view of her pussy. She had a very beautiful pussy and reminded Ash of his mom's pussy by the way it was shaped. Cynthia moved her hands in between her legs and spread her lips open so that they could see the pink opening of her vagina. Ash couldn't stand it any longer and he threw off his towel and slowly began stroking his penis. Cynthia then came and sat down on the bed beside Ash.

"You can touch them if you like." Cynthia told him as she noticed Ash was starring at her breasts.

Ash quickly shifted his hands from his penis and cupped Cynthia's naked breasts. He gently squeezed them and they felt a lot different compared to earlier when he felt them with her bikini on and they were wet.

"Your breasts feel so warm and soft. They feel wonderful." Ash said as he massaged her breasts for a couple minutes.

"Ash, would you like to touch my pussy?" Cynthia asked as Ash didn't have to be asked twice and he already was moving his hands between her legs before she finished asking. 

Cynthia felt a quick spike of pleasure jump through her body as Ash's fingers touched her pussy for the first time. Ash lightly ran his hand over her outer labia, stroking and caressing her pussy with his fingers. He than ran his fingers up and down the slit of her pussy as he felt her starting to get wet from his attention. She enjoyed him touching her but she didn't want to orgasm so quickly as the whole situation was making her more horny than normal. Cynthia needed to play this out a bit longer to build to a really satisfying climax and she thought of a great idea how to do that.

"Since you two still seem a bit hesitant about doing the photoshoot, how about I show you guys what a photoshoot is like? I could go setup my camera and I could act like the cameraman would when doing the photoshoot. Perhaps then you two would become more comfortable doing it." Cynthia asked with a hint of nervousness in her voice as she realized that she would soon be having sex with Ash but wanted to prolong it as much as possible to continue building the excitement.

"That actually sounds like a good idea. I'd been wondering exactly what a photoshoot would be like and since you've done it before, it would give us a better understanding." May said as she thought the idea was actually good.

"Excellent, I'll go get my camera and set it up. Why don't you come with me May and we'll dress you in something a bit more appropriate for a photoshoot." Cynthia said as she didn't even bother to ask Ash who was now a bit disappointed that he had to stop playing with her.

May followed Cynthia into her walk-in closet and they closed the door behind them so Ash couldn't watch them. Cynthia had quite a few clothes hung up considering this was her hotel closet and were only the clothes she had brought with her.

"Let's find something a bit more professional looking. Ash is used to seeing you in normal clothes, so lets get you dressed in something a bit more formal." Cynthia said as she looked for an outfit that would first fit May as she was taller than May.

Cynthia's eye caught a nice outfit that she wore sometimes to businesses. It was a white blouse with a skin tight black pencil mini skirt pencil skirt that has a slit down the side of the skirt. Cynthia put the outfit against May's body to see if it would fit her. She moved it around her body to double check that it the style would fit her.

"I think it will fit you. Now we just need to get you some underwear for that outfit." Cynthia said as she handed May the blouse and skirt.

Cynthia opened up a suitcase and started looking through her clothes for some underwear that May could wear. After rummaging through here stuff for a few minutes, Cynthia found a gel padded pushup bra that was a sultry charcoal color that was partially made of spandex. The panties were also the same color and also made of spandex but they were simple but designed to show off a girls natural curves. Cynthia handed May the bra and panties.

"Put these on. I think it will go well with the outfit." Cynthia said as May liked the choice Cynthia made for her and she started taking off her sling bikini that she was still wearing.

May slipped into the panties quickly but found it a bit hard to get into the bra. It was quite tighter than the bra's she was used to so Cynthia gave her a hand clasping the straps together. May looked down at her cleavage which seemed about two full cup sizes larger than normal with the extra gel padding them. 

"I think you need some stocking and a garter belt so go with those. I think I have one that will match." Cynthia said as she bent down to look through her suitcases again and gave May quite the view of her butt and pussy in the process.

May was a bit jealous of Cynthia after seeing her amazing body. It was no wonder guys thought she looked so sexy, even May was attracted to Cynthia. May had had sex with her other girlfriends before but she was a bit turned on seeing Cynthia naked close up in the room with her. It was a strange feeling for May but it soon passed as Cynthia had found the garter belt and stocking she was looking for.

"Put these on as well. You'll look good with them on and they match well." Cynthia said as she thought she did a good job getting an outfit for May all picked out.

May put the garter belt on and then got into the stockings. The garter belt had straps which she connected to the stockings. She then put the white blouse on and got into the skirt and zipped it up.

"You look very professional. Guys love girls that look smart and professional. Now I need to find something to wear too." Cynthia said as May looked a lot different than she normally did.

Cynthia looked through her clothes to find something she thought would excite Ash. She always had a hard time making decisions for herself and after a few minutes of looking, she could tell May was wondering what was taking her so long to make a decision. Her red qipao caught her attention and she decided that she should wear that. Cynthia didn't wear that too often as it was a bit small for her now but she realized since it was small, it would be tight on her and would show off her bodies curves.

She then got a pair of red lacy panties and a matching bra. She put them on pretty fast as to not delay May any longer. She then got into her red qipao which was even tighter than she remembered. She had a hard time closing the front and buttoning it but May gave her a hand as the two of them were finally dressed up.

"You look really sexy in that dress Cynthia." May said as she looked at the form fitting red dress.

"Thank you May. You look good in your dress too. Ash won't know what to do with himself when he sees us." Cynthia said as the two of them had a quick laugh.

Cynthia picked up her camera which was a very expensive looking digital camera with a good lense on it. May realized that Cynthia must be pretty good at photography for owning such a good camera. Cynthia opened the closet door and the two of them walked into the main room again where Ash had been patiently awaiting for them to return. Ash's eyes opened wide when he saw the two of them come out in their sexy looking outfits.

"So what do you think of our outfits Ash?" Cynthia asked as she could tell by the expression on his face that he liked them.

"You both look really sexy!" Ash commented as both the girls stood in front of him modeling off their clothes they were wearing now.

Ash recalled shopping for bikini's with May and the other girls the other day. Initially he found it to be boring and tedious but he had certainly got used to watching they change into sexy clothes pretty fast. Ash couldn't believe that Cynthia was able to get into the qipao she was wearing as it was super skin tight. The top of the dress form fitted around her large breasts and it looked like the buttons would burst any second. Ash looked over at May and noticed that her breasts also seemed bigger than they normally were. Through her white blouse he could sort of see the outlines of a black bra that she was wearing.

"Thanks Ash. It's always good to hear a complement from a guy! I'll just setup this camera and we'll get ready. May why don't you sit on the bed there while I set this up. Ash, if you can turn on the TV and set it to wireless input, you guys will be able to see what the camera is shooting on the big screen." Cynthia said as she started to unfold a portable tripod for the camera.

"Okay!" Ash and May said as they did as Cynthia instructed.

It took Cynthia only a couple minutes to get everything set up the way she wanted and suddenly the camera feed was displayed on the TV. May showed up as everyone turned to the TV to see that it was working.

"Alright. Everything is setup now, so if you're ready May we'll get started taking a few pictures." Cynthia said as she asked May if she was ready.

"I'm all set here. I'm actually a bit nervous but excited at the same time too!" May said as she looked over at herself on the TV.

"There's nothing to worry about. Just focus on the camera and to what I say and it will be fine. The TV shows you what I see in the camera so you can know what's going on and what the picture is going to look like. When we're done, we'll have a lot of great footage. Just wait and see!" Cynthia said as she convince May that it was going to be good.

"Okay then but these pictures are only for us. No one else is to see them or get them." May said as she wanted a bit of reassurance from Cynthia that the pictures would be private.

"I promise. I'll give you the files from the camera to keep once were done, how's that?" Cynthia said as she hoped that if May would have really good pictures to keep from this photoshoot that she would realize just how good she looks.

"Sounds good to me." May said as she crossed her legs a bit.

"Oh that's a great looking pose right there May. Smile a bit." Cynthia said as she took her first picture of May cross legged on the bed.

Cynthia took the first shot and was pleasantly surprised by how well it turned out. May's anxiety lowered a bit as this mock photoshoot began.

"Okay, let's try a different pose. Stand up this time and put your hand on your hip like you mean business." Cynthia said as May did as she was told.

Another price was taken and Ash couldn't believe how stern the pose looked with May's hand on her hip like that.

"Wow May! You look like a work boss that means business with that pose!" Ash said as he was actually a bit frightened by the way May looked currently.

"You think so? You think it's too serious looking a pose?" May said as she loosened up a bit with it and Cynthia quickly took another picture.

"Right there May that's great! Now smile again and put your other hand on your waist." Cynthia said as she clicked the button on the camera.

Cynthia took a few more pictures of May in the next pose before deciding it was time to press onward.

"Now open the top a few buttons on your blouse to give us a glimpse of your bra underneath. Bend forward a bit so that your teasing the camera with your cleavage and showing a bit of your bra." Cynthia said as May undid a few buttons as she was told to reveal some of her cleavage.

May was starting to feel a bit more comfortable doing this since she could see that Ash's was enjoying the stripshow photoshoot. His penis was standing erect and he was having trouble trying not to play with himself to distract May from what she was doing.

"Now undo the buttons just to below your breasts and pull back the blouse to fully expose your pushup bra completely." Cynthia said as the camera flashed a few times as May's sultry charcoal colored gel padded pushup bra was revealed to Ash and the camera.

Ash really liked the bra May was wearing. He'd never seen May wear one like that which pushed up her breasts as well as make them seem bigger. He liked the color of them too but realized the color seemed to suit Cynthia a bit better and then it dawned on him that it must be one of Cynthia's bra's that she was wearing.

"You're doing good May, now completely removed the blouse." Cynthia said as she waited till May took it off before snapping a few more pictures.

May dropped the blouse on the floor and was now fully exposing sultry charcoal color push up bra. Her large breast perfectly fit into the bra's cups which held them firmly up. 

"How does your friend look? Is she doing a good job?" Cynthia asked Ash as she noticed his erection was bigger than ever now.



"She... She looks incredible! That bra is so sexy! Is it your bra Cynthia?" Ash asked as his voice a bit shaky as he as obviously excited and nervous to ask her the question.

"Yes it is. I picked it out because I knew it would also look good on May. It's seems by the look of you down there, that you find it really exciting to look at too." Cynthia said as Ash blushed a bit as he realized Cynthia noticed his hard-on was quite large now.

"Ah well.. It's kinda hard not to be excited watching her strip like this." Ash said as he tried to justify himself a bit.



"Put your hands on your breasts now May and push them together for a picture and to show Ash just how big they are! Tease him and the camera at the same time." Cynthia said as May enjoyed teasing Ash and did that.

May press her large breasts together showing her amble cleavage to Ash and the camera but bending forward a bit again. Normally her breasts would hang down a bit but because the pushup bra was so tight to her body, the shape of her breasts stayed perfectly intact to make them look very sexy and very inviting. The atmosphere in the room was getting heated and the sexual energy was building quickly once again.

"Now turn around and you lift the skirt up to show your lovely stocking covered legs" Cynthia said as May turned around and lifted the skirt a bit as she took a few pictures of May wearing the stockings.

May then decided on her own with a playful and smirky look on her face to unzip her skirt and to slowly strip it off. May pulled the skirt down to reveal her garter belt, panties and stockings. Cynthia had set the camera in rapid mode and was quickly taking pictures. Ash on the other hand was taking mental pictures in his head as he watched May strip. May turned her head towards Ash and moved her fingers in a 'come here motion' all while sticking her butt out to give him a good view of it and her panty covered pussy.

"Ash, I think May is trying to tell us that it's time for you to join the photoshoot." Cynthia said as Ash really didn't need to be told and was already heading over to join May on the bed