Story Notes:
The following story takes place after Ash as completed the Sinnoh League. Categories: male/FEMALE
Chapter 19 - Agent Jessie
Everyone slept well that night having spent the day swimming and having sex. When morning arrived, everyone was feeling refreshed and ready continue their journey to their first gym leader, Sabrina. Brock and Misty had both said they would be the like to be last people Ash would battle with. Being in the Cerulean Gym brought back memories for all of them, but these recent events were about to become a memory as well.
"Good morning everyone" Misty said as everyone dropped their stuff at the entrance lobby.
"Hi Misty. Sleep well?" Dawn she asked the boys as she put her backpack on the ground.
"Yeah, slept solid the entire time." Ash replied.
Moments later, Misty's sisters arrived at the front lobby to see them off. Each of them had a gift in their hand. Everyone turned to watch them approach.
"Well everyone, I guess this is goodbye." Lily said with a bit of sadness in her voice.
"It's been fun while you guys were here." Violet said right after Lily.
"We wish you could stay longer and visit with us some more, but I guess you're all eager to continue on your new journey." Daisy said.
"Thanks you guys. Were going to miss you too." Ash said as he starred at the boxes they were each holding.
"Goodbye, Lily! Goodbye, Violet! Goodbye, Daisy! Next time I visit I will make sure we have some private fun of our own!" Brock said somewhat disappointed he didn't get to do any of Misty's older sisters while he was here.
"Will be waiting for you Brock." Violet said as she winked at him.
"Guess will just have to wait a bit longer to get some action with Brock." Lily said with a smile on her face.
"Hey, at least you two got some action. All I got was a sunburn." Daisy said as she looked at her red skin as everyone laughed at Daisy's remarks realizing she was left out from their fun yesterday.
"Well before you go, we have a present for you girls from us." Lily said as the three of them all gave gifts to Misty, May and Dawn.
"Now don't open them for a couple days. We want you to think about what's inside for a few days before you open it." Daisy said.
"That way, you'll all be thinking of all the strange and wonderful things that are in those boxes!" Violet exclaimed with a bit of a chuckle in her voice.
"I wonder what's inside" Dawn said as Violet gave her the gift.
"You'll just have to wait and find out! It's a surprise. But we're sure you'll like it!" Lily told her.
"I hate surprises. I want to know what it is now..." Ash said as he tried to grab the box from May to shake it around a bit.
"Hey Ash! You'll find out in a few days just like us." May told him as she put the gift in her backpack safely.
"Thanks for the gifts you guys." Misty said as she hugged her sisters.
"You're welcome! We're going to miss you Misty." Daisy said as she rubbed Misty's back as she hugged Violet.
"Take care! Okay?" Violet said as she let go of Misty.
"You too." Misty replied as she picked up her stuff off the floor.
"So where are you off to?" Lily asked wondering where their next stop would be.
"Were off to Saffron City's Gym to visit Sabrina." Ash told them.
"Saffron City, huh? We haven't been there in a while girls. We should go shopping there one day." Daisy said as she was thinking to herself as she replied.
"Well we better get going. It's going to take us a few days to get there and we need to get to a Pokemon Center before dark." Brock told everyone as he started out he front door.
"See you later everyone! Take care!" Misty's sisters said as the group began their journey to Saffron City.
After a bit of walking, the group was almost out of Cerulean City. Just a few days earlier, they were on their way here and now they were leaving the city behind.
"Sad to leave your home town again?" May asked Misty as they looked back at the city that was slowly disappearing into the distance.
"Not really. I've been running the Gym for ages now. It's time my sisters watched it while I went on a journey of my own. It's only fair." Misty told her.
"I wonder what it's like being a Gym Leader. It must be quite a hard job. All those trainers coming to battle. You'de need to make sure your Pokemon were always in top fighting shape." Dawn asked everyone as they continued walking.
"It can be quite tough, but its also quite fun. I enjoyed being a Gym Leader" Brock said as he turned to talk to Dawn while he walked.
"I enjoyed it too, but it's time I had a break from it. It gets stressful after awhile." Misty explain to her.
The group continued on walking on the path to Saffron City, enjoying the time together. Ash and his friends hadn't heard or seen from Team Rocket in day and their mistimely appearances every day had Ash a bit worried.
"You know, we haven't seen Team Rocket in a few days. I wonder what they are up to?" Ash asked pondering what their next scheme might be.
"Well we are on their home turf. The one thing I don't miss about traveling with you Ash is Team Rocket. We need to make sure were on high alert at all times." Misty said as she was back to her serious self again.
"Maybe they have finally given up trying to get our Pokemon and are going after someone else instead." May wondered.
"Maybe, but I find it unlikely that they would stop after all this time." Brock concluded as he too wondered where they might be.
In another area of the Kanto Region, Jessie, James and Meowth were on their way to the Team Rocket Headquarters. Since they had returned to the Kanto Region, they decided that it was time to check in with the boss to report on their mission in the Sinnoh Region.
"Are we almost there?" James asked as he was walking slowly trying to catch his breath.
"It seems further than last time." Meowth replied.
"I think were almost there. It's just around the bend." Jessie said as she started looking over the rocks to see if they could find their destination.
After a minute or so of walking, Jessie, James and Meowth could see the Team Rocket Headquarters in front of them. It was set in a mountain for protection and as usual, there were two Team Rocket henchmen at the front gate making sure no unauthorized visitors tried to enter the complex. Jessie, James and Meowth walked up to the gate and identified themselves.
"Agents Jessie, James and Meowth reporting as order." Jessie told them as they stood at attention.
"The boss is waiting for us to report on our activities in the Sinnoh Region." James continued.
"Don't stand there all day. The boss is expecting us now." Meowth told them as they looked suspiciously at the three of them.
"I remember you three." One of the guards said as he looked at the other guard.
"You're the three that were here on po-go sticks last time." the other guard said recalling their previous experience with Jessie, James and Meowth.
"Were going to have to double check that the boss really wants to see you." the guard said as he went into the guard booth to contact the boss inside while the other guard stood in front of the gate.
"Boss, we have 3 agents from the Sinnoh Region that say they are here to see you. Should I let them in?" the agent asked as he waited for Giovanni's response.
"Yes, let them in. I've been waiting for them to report on their activities there." Giovanni said as he cut off the transmission to the guard.
The guard walked out of the booth and pressed the gate button to raise the gate. The other guard obviously knew what the boss's decision was and moved out of the way.
"The boss will see you now." the guard said as he motioned for Jessie, James and Meowth to enter the headquarters.
"It's about time!" Jessie said as she began walking past the guards.
"We told you he was waiting for us!" James said as he also started walking.
"You're glad the boss isn't mad with you for making him wait!" Meowth said with he head held high as he walked by the guards without looking at them.
Seconds later the group entered the headquarters for Team Rocket. They had been here quite a few times and knew the way to the boss's office. They walked into the elevator and took it to the top level. As the doors of the elevator opened, they could see right into the boss's office at the end of the hall. He was sitting at his desk looking outside.
Jessie, James and Meowth walked into his office and stood at attention.
"Jessie, James and Meowth reporting as ordered." Jessie said to Giovanni as they awaited his response.
"Ah, I've been expecting you." Giovanni said as he turned his chair around to face them.
"So, let's hear you report on your activities in the Sinnoh region." he continued.
For the next 20 minutes or so, Jessie, James and Meowth explained all their activities in the Sinnoh region. As the only group of Team Rocket agents in that region, they had a lot of explaining to do about Team Galatic and their activities.
It had been a few years since Giovanni had seen this group of agents in real life and his eye kept focusing on a more mature looking Jessie. This wasn't the young girl he originally remembered joining Team Rocket and he couldn't help but stare at her as they continued explaining everything that had happened to them. After a while, they talk began to blur and Giovanni sat there staring at her.
Jessie didn't notice Giovanni starring at her as she, James and Meowth had almost got to the point of arguing as they continued their report. Jessie was in her prime and Giovanni couldn't believe how beautiful she looked. He was so mesmerized by her that he didn't care that the three of them were arguing.
Jessie, James and Meowth continued arguing back and forth for a few minutes not realizing that Giovanni had stopped paying attention to them and was more concerned about Jessie's looks. Finally Giovanni had enough and decided it was time to end this.
"Okay that's enough. You can explain the rest in your written report." Giovanni said as he cut them off in mid sentence.
Jessie, James and Meowth quickly turned to look at the boss and they all tried to compose themselves realizing that the boss might be angry which was something they didn't want.
"Will do boss." Meowth replied.
"Now go. I'll expect your report by tomorrow. Agent 363 will arrange quarters for you while you stay here. You can talk to him at the front desk." Giovanni told them as he motioned them to leave.
Jessie, James and Meowth saluted as they turned around and started heading out of Giovanni's office. Giovanni watched Jessie begin walking. Her tight skirt practically form fitted around her ass giving him a great view of the shape of her ass. It looked firm and tight and it was driving him crazy.
"Agent Jessie, stay here for a few minutes. There is something I wish to discuss with you. The rest of you go." Giovanni finally spoke up as Jessie turned and quickly returned towards Giovanni's desk.
"Close the doors when you leave." Giovanni instructed James and Meowth who were a bit confused as to why Jessie was called back into his office.
James and Meowth entered the hall and closed the doors behind them. They watched as their vision of Jessie vanished with the closing of the doors.
"I wonder what the boss wants with Jessie." Meowth asked James.
"I dunno. Usually we do everything together as a group. Seems like that might change now though." James said with a hint of disappointment in his voice.
"He can't split us up even if he is the boss!" Meowth said starting to get a bit of anger in his voice.
"Well it's not like we can barge back in there now. He'd kick us out faster than we could get in the room." James said in a depressed voice.
"Yeah, I guess your right. Best we just wait till Jessie gets out and we can find out from her whats going on." Meowth said as he began to walk towards the elevator.
James followed him as they both went down to the front desk to get their room sorted out. They both continued to wonder what the boss wanted with Jessie.
"So Jessie, you've been a member of Team Rocket for many years now and you're still a field agent, is that correct?" Giovanni said as he continued to scan her body with his eyes.
"Yes, that's correct sir." Jessie thought as she was now hoping a promotion was coming.
Giovanni already knew the answer to his question and was just making small talk to make Jessie a bit more comfortable. He could tell that she was a bit nervous, but who wouldn't be when talking to their boss.
"How would you like to join a special branch of Team Rocket that only a few members are a part of?" Giovanni finally asked her with a bit of a smirk on his face.
"The special agent group?" Jessie eagerly replied hoping that it was going to be that.
Jessie remember her last encounter with Domino and she hoped that she could become part of the group, that way Domino couldn't bug her about being a lowly grunt in Team Rocket anymore.
"Yes, the special agent group..." Giovanni replied realizing that Jessie was to incompetent to be a member of his personal elite agent core.
"...but this division is a bit more specialized. You see, this group reports directly to me in person." Giovanni continued to explain to Jessie as she was getting a bit more excited by the minute.
"The group is secret and you should not tell anyone including other agents about it. Once you join, you can never leave the group. You will always be a part of it. Are you willing to accept these terms Agent Jessie?" Giovanni asked her without telling her the full details he had in store for her.
"Yes sir!" Jessie quickly replied.
"Good, you'll start immediately then." Giovanni said with a smirk on his face.
"W-what do I have to do, sir..?" Jessie asked as she gently tugged on the end of her skirt as she saw Giovanni starring at it.
"Why don't you come sit on my lap and I will explain to you a bit more what your duties will be." Giovanni told her with a sly smile and Jessie could see the erection in his pants already as she began to walk behind his desk.
Jessie was starting to get a bit scared as it now seemed the the boss had other ideas for her than what she originally thought. The erection in Giovanni's pants was quite large and the fact that he wanted her to come sit on her lap would make it very awkward to avoid. Jessie was hesitant to sit on his lap as she walked to the side of his desk.
"Come and sit here." Giovanni said as he patted his legs with his hands motioning for Jessie to come sit down.
Jessie took a big gulp and slowly moved towards the boss. She began to sit down on his lap as Giovanni sneered at her, please that she was obeying him.
"There we go. Now I can further explain your duties now that your a member of this special division of Team Rocket." Giovanni said as he began to explain.
"So what exactly will I be doing?" Jessie said a bit curious as she could now feel his erect penis pushing his pants against her leg.
"We're just gonna have a little fun together." Giovanni said as his left hand was now rubbing against herlegs, slowly stroking her soft skin.
Wrapping his right hand around the back of her neck, Giovanni pulled Jessie into his lips. She did not resist whatsoever and almost immediately her tongue was at the back of his throat. They kissed passionately and her hands found their way to either side of his face. Jessie was starting to relax a bit now and was actually liking the attention that the boss was giving her. There were plenty of girls in Team Rocket and the fact that he found her attractive made her feel special. After a few seconds kissing, Giovanni pulled away sharply and stared at her with a devilish smile.
"On your knees!" Giovanni ordered and without hesitation, Jessie dropped to her knees as he undid his belt and pulled his zipper down.
"Pull it out." he told her.
Jessie slid her right hand over his bulge to catch his zipper and slowly pulled it down before sliding her hand into his fly. Giovanni's erection flew out his pants with only the tiniest tug from her hand. Her hands were surprisingly cool as she gently clasped Giovanni's penis. She pulled his balls out with her left hand before beginning to slowly stroke him up and down.
Giovanni's penis was hot and hard. It was also the biggest penis Jessie had ever seen. It looked to be about a foot long and over an inch wide. Jessie wasn't too experienced in sex, but she had had her fair share of men and she knew this was a very large penis for any man. The size of his penis seemed to fit Giovanni's body as he was quite a large man. Jessie's small hands could feel blood rushing through the huge veins.
Jessie started to slowly jerk Giovanni off with both hands. Almost immediately, a large droplet of precum emerged and Jessie instinctively licked it. She closed her eyes and savored its taste.
"Mmmm. Tastes so good." Jessie said as she licked the tip of his penis's swollen head.
Giovanni couldn't take her teasing anymore and he grabbed her head and forced his rock hard penis into her mouth. Jessie felt a little bit of resentment at the rough treatment the boss was giving her but his penis tasted so good that she quickly forgot about his treatment and began to play along. Jessie willingly and eagerly moved her mouth up and down along his penis, barely able to get much of it in her mouth as it was so big.
"My god. You're penis is so big! I bet you can't wait to shoot your load inside my mouth! Or would would you rather come all over me, or inside me?" Jessie said as she was now getting turned on herself.
"Less talking, more sucking." Giovanni ordered.
Jessie sucked on just the head of his penis before taking more into her mouth, slowly sliding her lips further up his penis. Giovanni began to pump his hips he began fucking her mouth now, holding her in place while he pistoned his hardon in and out of her lips. His penis pounded deep into her mouth and it wasn't long beforre it started gagging her. After a few more thrusts he pulled out, allowing her a chance to catch her breath.
Jessie had never experienced anything like that. Giovanni, her boss of many years, was thrusting his huge penis inside her mouth and down part of her throat. He managed to enter half of his twelve inch penis into her mouth, but deep-throating the other half proved to be beyond her abilities.
"So are you enjoying your first mission as the newest member of Team Rocket's elite?" Giovanni asked Jessie as she was regaining her breath as she knelt in front of his desk chair.
Suddenly, there was a knock at the door and quickly Giovanni pushed Jessie out of sight under his desk. Jessie could hear Giovanni fumbling with the things on his desk as he moved his chair closer to the desk as the door opened.
"Uh, I'm sorry to boss, but we just had word that a new gang in on the move and is beginning to overtake some of our territory." a Team Rocket grunt said as he reported the findings to Giovanni.
The two talked for a few minutes as Jessie tried to stay as quiet as she could. Giovanni's pants were still undone and his erection was still as hard as ever.
"Thank you for the report. Close the door on your way out." Giovanni told the grunt as he seemed a bit angry now.
Moments later, Jessie heard the door close and Giovanni moved his chair out to allow her to get out from under the desk.
"There is a new gang attempting to take control of come of our vital areas." Giovanni angrily said as Jessie could see that he was trying to devise plans to counter this new threat.
"This sounds bad." Jessie replied as she tried to sympathize with her boss.
"They must be stopped." Giovanni said as he banged his fist against the arm rest.
Jessie could see that Giovanni was quite stressed out now after this news. It kind of killed the mood that was in the room before the news. Giovanni's fly was still open and his penis seemed more erect that before. It seemed to Jessie that Giovanni got turned on even more when he was angry.
"Well, I know something that can help you out right now." Jessie said as she moved up towards his penis and began to lick and suck it again.
Jessie pulled down Giovanni's pants so she could access his penis and balls better. While she did that, Giovanni began to take her white vest uniform top off revealing her skin tight black shirt underneath.
"Would you like me to take my skirt off too?" Jessie asked cheerily.
"Oh, fuck, yes," Giovanni replied loving the attention he was getting.
Jessie began to take her top off with a teasing smile on her face as she did so. She pulled it off to reveal an elegant black full-cupped bra, the upper half made of floral lace. Giovanni could see parts of her aerolas through the lace. Giovanni's eyes froze at the spot where her nipples were thrusting against the fabric of her bra and he licked his lips in excitement seeing her aerolas through the bra.
"Why don't you go lock the door, while I slip out of these clothes completely." Giovanni instructed as Jessie got up and began walking toward the door.
Giovanni quickly took off the rest of his suit and threw it on the ground as Jessie locked the door making sure they wouldn't have any more interruptions. Giovanni eye Jessie's every move as she began to walk back towards him at the desk. She stood in front of him and cupped her breasts.
"Do you like what you see?" she asked enticingly.
"Yes, but I'de like to see more now." Giovanni told her.
"That can be arranged." Jessie said as she smiled seductively.
Jessie started working her hips, dancing slowly and seductively in front of Giovanni who had returned to his seat. Jessie's hands played with the bra straps on her shoulders as she slipped one and then the other off her shoulders. Her breasts were almost free, but they were still held within the bra cups. She reached up to the cups and pretended to pull the cups down to expose them, but instead she pushed her breast up a bit revealing her cleavage to him as she bent down a bit in front of him.
The anticipation was killing Giovanni and he couldn't resist any longer. He began stroking his penis up and down in front of Jessie as she slid the bra straps back up onto her shoulders and turned away from him. She released the bra clasp at her back and let the two pieces fall away to expose her back. Jessie then turned around again, holding the cups of her bra against her breasts.
Jessie smiled as she saw Giovanni stroking himself as she watched her strip. Jessie slowly lowered the bra off her breast, replacing the area of her breast that was covered by the bra with her hands. Giovanni saw the bra fall to the ground but was disappointed to see that she was still covering the majority of her breasts with her hands. She pressed her breasts flat and moved her hands in circular motions. Jessie moved her hands slightly and parted her fingers a bit. Giovanni realized that she was revealing her nipples through the part in her fingers and he stared intently.
"Oh, wow!" Giovanni moaned as she Jessie finally removed her hands from her breasts to reveal her 34dd breasts to him.
"So? What do you think? Do you like 'em?" Jessie said as she straightened her back to thrust her chest out more to make her breasts look even bigger.
"They're amazing." Giovanni responded.
"You must really love my boobs, as you can't seem to take your eyes off of them."Jessie said laughing and gave her breasts a shake.
"Are you kidding? I love breasts!" Giovanni told her.
"I love to have my tits fucked." Jessie said running her hands over her sumptuous breasts.
"I love feeling a nice hard penis slide in between my big titties." Jessie continued as she rubbed her breasts together.
Giovanni was in heaven as he watched his sexy young agent turn into his personal dream come true.
"Do you want me to fuck those sexy tits of yours?" he asked her.
"God yes! Fuck my tits!" Jessie replied as she squeezed her breasts and once again knelt down in front of Giovanni.
Giovanni placed his penis in between the cleavage of her breasts as soon as she was in range.
"Oh! I can see you're very eager. Perhaps you'd like to come over my tits?" Jessie exclaimed in excitement as he began sliding his penis all over her breasts.
Giovanni reached down to fondle her magnificent boobs that he had been watching for the past few minutes and he quickly had them wrapped around his penis. He started to pump his penis in between her huge tits as the head of his penis was popping out the top of her cleavage with each thrust. She reached down and began massaging his balls while he thrusted his penis between her breasts.
"Tell me how much you like getting your tits fucked." Giovanni ordered as he continued.
"I love it! You're penis is so big and warm. I cannot wait for you to shoot your hot cum all over them! " she exclaimed squeezing her breasts together even tighter.
Jessie's large boobs were nice and soft and a great cushion for Giovanni's large penis as it stroked in between the cleavage. He continued stroking his penis between her breasts for a few minutes, as he continued to build up to a climax. Jessie could see he was starting to have problems holding his cum back.
"Cum on my big tits! Cum on my big slutty tits!" Jessie taunted him as she awaited him to cum.
Giovanni began stroking in between her breasts as fast as he could. He started to moan as he could feel the cum heading towards the head of his penis. Jessie closed her eyes and felt the hot liquid splash onto her huge breasts. He continued splurting large blasts of his white cum and Jessie though it would never end. Giovanni shuddered as the final drops of cum fell onto her breasts and he wiped the tip of his penis over one of her nipples.
Jessie finally opened her eyes and looked down at all the cum on her breasts. She saw that the head of his penis was covered in cum and she was immediately attracted to it. Not wanting to waste any of his cum, she opened her mouth and put the head of his penis in her mouth.
Jessie started to lick the cum off his penis and it was quickly cleaned off. Jessie then began slurping and sucking like a vacuum trying to suck out any remaining cum. Giovanni groaned in bliss and she smiled up at him as he encouraged her to continue.
Jessie then proceeded to give Giovanni the best blowjob he had ever had in a while. She planted tiny kisses up and down by his penis as she flicked her tongue across balls and then licked up the shaft of his penis. She then put his penis in her mouth and bobbed her head up and down, swallowing his large penis as best as she could.
Giovanni's breathed harder as the sensitive skin of his penis ached from the attention Jessie was giving it. Jessie whimpered softly as she lifted her head, sucking on the penis in her mouth. Jessie loved to give blowjobs. Giovanni continued moaning softly as Jessie sucked his penis. Finally, Jessie believed she had sucked out the remaining cum and she stopped.
Jessie stood up once again and twirled around while raising her short skirt to show Giovanni that she was wearing a black g-string that matched her bra.
"Do you like looking at my pussy through my panties?" she asked him as she got up on the desk and began to spread her legs wide.
"Oh yes! I want to lick your sweet pussy." Giovanni replied as he moved in close towards Jessie.
"Lick your fingers and reach inside your panties. Play with your clit!" Giovanni ordered ass he waited to see if Jessie would obey him.
Jessie's short dress rode high up her hips now and Giovanni was getting a very close view of her round as. He could also see that her labia was quite puffy and her tiny panties were barely able to cover her pussy now. Jessie parted her legs a bit more and Giovanni could now see a damp spot on her panties. She put her hand in her panties and then began to play with her pussy.
Giovanni slid his hands down between her legs and caressed the lips of her vagina through her panties as Jessie continued to rub her clit.
"You're all wet and its soaking through your panties. You like touching yourself, don't you? You like my fingers there too?" Giovanni asked.
"Yes, I love feeling my pussy." Jessie told him.
"Do you want me take over for you now?" Giovanni asked her.
"Please." She responded quickly.
"Now take off your panties for me so I can see what I'm doing." Giovanni instructed her.
Jessie grabbed the side bands of her panties and began to raise it up her legs slowly revealing her pussy to Giovanni. Her pussy lips were completely bare and smooth while there was a patch of pubic hair above her pussy in a triangle shape. Giovanni loved the look of her inviting pussy and he couldn't wait to feel it. Jessie also took off her skirt leaving her completely naked infront of Giovanni on his desk.
Giovanni moved his head up to one of Jessie's breasts and started kissing one nipple and fondling the other breast with his hand. His lips and tongue circled round her nipple causing it to get incredibly hard. His fingers gently rubbed her other breast and nipple producing the same result. She moaned a little as she loved the way he was playing with her breasts.
After a few minutes of playing with her breasts, Giovanni slowly slid down her body as he kissed and licks all the way from her breasts to her stomach. Giovanni relished the feel of her hot, smooth skin as his lips touched her.
Jessie spread her legs as wide open as she could, inviting Giovanni to move down between them. He ran his tongue from her stomach to her hip and then down until he went around her pubic hair and then over to the softness of her cunt lips.
"Oh! Lick me! Lick me, please! I want to feel that hot tongue of yours licking me out! Lick my clit and make me cum!" Jessie said as she could no longer take any more of his teasing.
Giovanni began sucking on her pussy lips in his mouth and used his tongue to play with her clit. Jessie moaned as Giovanni continued eating her pussy.
"Damn, you're good at eating pussy!" Jessie said as she couldn't believe how good he was.
Giovanni's face was buried in Jessie's lovely pussy. He clamped his lips around her clit and started sucking on it, while his tongue probed and licked it at the same time. After only a few minutes of sucking and licking her clit, Jessie climaxed and gave out loud moan.
"Oh my! I came so fast!" Jessie exclaimed.
Giovanni's jaw was getting a little tired so he stopped licking her and looked at her pussy that was now quite red and swollen from all the attention he had given it. He was ready now to move this on to the next stage. He stood up in front of Jessie and slowly stroked his penis. Jessie couldn't believe how big it was and was a bit afraid of something that large going inside her.
Jessie was also somewhat nervous as she lay there naked on the top of Giovanni's desk. She had been in his office many times, but never did she think she would see his office from this angle. Now that moment was about to arrive as Giovanni moved in between Jessie's legs and he looked down at the hotness of her pink pussy lips that were very wet and swollen from the fingering and licking he'd already been giving her.
"You'de better be ready for this!" Giovanni said as he stepped in front of her and aimed his large erect penis at her dripping pussy.
Jessie threw back her head and yelled as Giovanni drove his large penis into her wet pussy. After the first few strokes, Jessie started to push back into him to match his rhythm. At every thrust, she moaned lightly and she began to buck wildly. Giovanni was forced to push her flat against his desktop and hold her there so she wouldn't fall off.
"Fuck me hard!" Jessie squealed as shockwaves of pleasure consumed her causing her to arch her back and make her breasts protrude from her body further.
Giovanni began pounding his large penis into Jessie's pussy. She screamed as he buried his penis in her again and again. Giovanni pushed his thick penis in a few more inches, but he barely had any of his large penis in her yet.
"You like that? Does that feel good?" Jessie said seductively.
"Oh yeah." Giovanni sighed as he pushed another 2 inches inside her.
Govanni could now feel the engorged head of his penis hitting the mouth of her cervix as he thrusted. He retracted his penis almost completely out of her pussy and then drove it back in again. He did this a few time, each time he managed to get another inch of his penis inside her.
"God it's so big!" Jessie cried.
Giovanni's powerful and strong erection plowed through her delicate pink pussy lips right against the entrance to her womb. Jessie could feel Giovanni's big hard penis filling up her entire pussy as he thrusted it in and out of her. She knew that Giovanni was very experienced by the way he was having sex with her as she was quickly building up to yet another climax.
Jessie's pussy muscles clamped tight around Giovanni's penis as he managed to get in about 8 inches of he penis. Jessie couldn't believe how big he was. She had never had sex with someone who had such a big penis. Her pussy was stretched to the max to allow it to fit in her. She knew she couldn't take anymore of it inside her and the constant bashing against her cervix was driving her crazy.
Jessie's orgasm began to build again until finally she climaxed again. Jessie had never had two orgasms this close together and the feeling was overwhelming. She closed her eyes as the feeling rippled through her body. She could still feel Giovanni going at her pussy relentlessly.
"You came again already?" Giovanni asked her as he continued thrusting in and out of her.
"Oh yeah! You're really good at this. I've never felt this good before." Jessie said as she looked down at her pussy to see Giovanni's large penis still spreading her pussy lips out wide.
"I cannot get my penis all the way inside you. I'm going to have to try something a bit longer. Flip over and raise you're ass." Giovanni told her.
Giovanni pulled his penis out of Jessie's pussy and she did as she was told. She turned over on her stomach and lay on the desk. She was able to touch the ground now with her feet to help balance herself. Giovanni moved in close to Jessie again and aimed his penis at her ass hole.
"Oh yes. Fuck me in the ass with that big cock!" Jessie told him as she turned her head around to watch Giovanni stick his penis inside her ass.
Jessie gasped loudly as she feel his penis slip past the tight outer opening to her ass.
"You ok?" Giovanni quickly asked not really concerned about her that much.
"Yes. Don't stop. Just go really slow," Jessie replied with her eyes tightly closed.
"Relax. It will make it easier for me to get it all in!" Giovanni told her.
Giovanni applied more pressure as Jessie felt him go deeper into her bowels. She had never felt anything like this before. Inch by inch his penis pushed into her ass and as soon as she thought he had managed to finally get his entire penis inside her, another inch went in.
"How much more do you have?" Jessie asked as she felt like she had a mile inside her.
"Just another two inches and then you will have all 12 inches of my penis inside you!" Giovanni laughed as he pushed another inch inside her.
Giovanni loved feeling the insides of Jessie's ass and comparing to her pussy that he was just in. Both were very tight, but her ass was even tighter than her pussy. Finally he managed to get his entire penis inside her, something he wasn't able to do with her pussy. Jessie's muscles tightened around him, causing him to groan with pleasure.
Jessie then grabbed her ass and squeezed her cheeks together tight.
"You like it when I squeeze you with my ass?" Jessie asked.
"Oh yeah! Keep doing that. It's nice and tight!" Giovanni said as he started thrusting in and out of her ass.
Jessie closed her eyes and clenched her fists as Giovanni began moving faster and faster in and out of her ass. Giovanni felt amazing as he thrusted deeper into her.
"Fuck me, fuck my tight little ass. Faster, please, faster." Jessie said as she was trying her best to pleasure Giovanni.
"You are so tight! It feels so good. I have my entire penis in your hot little asshole now." Giovanni told her.
"I'm glad! I didn't think it would fit!" Jessie moaned as she felt like she was being split apart.
Giovanni continued his thrusting, marveling at the reactions of the beautiful woman beneath him. He loved looking at the entrance of her ass and seeing it spread wide to accommodate his penis.
"Oh god, I'm coming again!" Jessie exclaimed as her whole body tensed up and she climaxed for the third time in such a brief amount of time.
"I seem to do that to girls a lot." Giovanni told her as he was proud that she had already orgasmed three times before he'd even cummed once.
The excitement of the moment of hearing Jessie orgasm and then her muscles tightening because of it, proved to be finally too much for Giovanni to withstand.
"I'm going to cum!" Giovanni groaned as he started to explode inside her ass.
"Yes, come for me! Cum in my ass!" Jessie cried as she could start to feel his hot cum filling her insides.
Giovanni was thrusting hard fast and deep as each blast of cum spewed inside of her. Giovanni's desk began to shake as Jessie attempted to balance herself as Giovanni came. Tons of hot cum was now inside Jessie as Giovanni opened his eyes after a powerful climax. His penis though, was still rock hard and erect.
"That felt good." Giovanni said as he slowly pulled his penis out of Jessie's ass.
"It sure did." Jessie replied as she tried to catch her breath.
Finally Giovanni's penis was out of her ass and Jessie turned around to see that his penis was covered in his cum. He sat back down on his chair and rested for a few moments. Jessie also rested on Giovanni's desk as she knew he'd be wanting more action any second.
"Come sit on top of me and will continue were we left off." Giovanni told Jessie as she turned around and moved towards him.
Jessie slid on top of him on his chair and straddling him. Giovanni felt her hands grab his penis as she guided it to the entrance of her pussy. He could tell she was wetter than ever as the head of his penis was now rubbing against her pussy lips.
Jessie was straddling the head of Giovanni's penis teasing it for a few seconds before she proceeded to mount herself on his erection. Jessie slowly slid his penis into her pussy as it entered her with ease. The combination of Jessie's juices and Giovanni's cum covered penis made it easier for Giovanni to slide his penis deep into Jessie's pussy.
Giovanni could feel his swollen penis head slam against Jessie's cervix as the tip of his penis penetrated that tight little inner hole more and more. Jessie started to bounce up and down on Giovanni's penis which caused her breasts to begin bouncing around. Giovanni watched Jessie's breasts bounce on every thrust as her slippery young pussy gripped his penis with incredible force.
Jessie started to wonder when or if she would be able to get to the base of his shaft and get him fully inside her pussy this time. Jessie moaned as she impaled herself on Giovanni's large penis. She forced herself down onto his penis and then raised up a little then forcing herself down again trying to get his entire penis in her.
Jessie bent over and lay her breasts on Giovanni's chest as she moved her hips up and down on his shaft. Jessie's tits were laying on his chest, moving around and her nipples sometimes rubbed up against his sending a chill down both of them every time they touched. Giovanni grabbed her hips to help keep her balance and started thrusting up into her knowing she would need some help to finally get his full penis all the way inside her pussy.
Finally, Giovanni gathered all his strength and with one last thrust he pushed his penis up into Jessie. Giovanni moaned as he rammed his penis all the way into Jessie's pussy.
Jessie's tits were bouncing up and down to his thrusts and her moans were high pitched as she began to lose it again. Giovanni also couldn't last and longer as well and he let loose at the same time.
"I'm cumming!" Giovanni grunted.
"Cum inside me!" Jessie cried.
With one last thrust, Giovanni slid his penis all the way inside her hungry pussy and held it there as he began spurting load after load of his hot cum inside her pussy.
Jessie's pussy convulsed around him in orgasm as his penis jerked inside her. A wad of cum shot out the end of his penis and splattered off the back of her womb. More of his cum flooded into her pussy as Giovanni began emptying his cum inside her.
A few minutes later Giovanni and Jessie had recovered. Giovanni's large erection had shrunk but his penis was still inside her pussy. Jessie stood up and once again knelt down in front of Giovanni.
"Let me clean you up." Jessie said as she took his penis in her mouth.
Giovanni groaned as his still sensitive penis reacted to Jessie's hungry tongue. Jessie licked clean the combined juices of her pussy and his cum until he was all cleaned up.
"Mmm, I just love the taste of your cum," Jessie said in between licks.
"You did well for you're first assignment Agent Jessie. I think I could use some rest now." Giovanni said.
"Agent 363 will also arrange quarters for you while you stay here. You can talk to him at the front desk as well. I'll contact you when I have another assignment for you." Giovanni said as he picked up come of Jessie's clothes and gave them to her.
"Yes sir." Jessie replied as she got the hint and began putting on her clothes.
"Welcome to the team agent." Giovanni said as he walked toward the side door of his office and closed the door behind him.
Jessie was now left in his office all by herself. She sat there for a few minutes trying to comprehend what had just happened in the last hour. She had just had sex with her boss and was now a member of his private sex group that he had personally chosen. She didn't know if she should feel honored or ashamed. What she did know was it was the best sex she had ever had. She could still feel his hot cum inside her pussy and ass.
Jessie gathered the rest of her clothes and began to get dressed. She knew by this time that James and Meowth would be wondering what was going on. She had to think of something to tell them as the truth was something she wasn't fully comfortable telling even her closest friends. She didn't know what they'de think of her if she told them why the boss wanted a private meeting with her.
Once Jessie was dressed, she opened the door and walked down the hall to the elevator. She pressed the button for the main floor and waited for the elevator to go down. Moments later she arrived at the main floor and she walked over to the main desk.
"Are you Agent 363?" Jessie asked the agent at the desk.
"Yes I am. What can I do for you?" he asked.
"The boss said that I was to talk to you about setting up quarters for me while I stay here." Jessie explained to him.
"And you're name is?" Agent 363 asked.
"Agent Jessie. My friends Agent James and Meowth were probably here earlier." She told him.
"Ah yes. Your quarters are setup with them. They are in room 35 in the residential wing. Level 7." He told her.
"Thank you." Jessie replied as she walked back to the elevator.
Jessie still didn't know what she was going to tell James and Meowth as they were probably anxiously awaiting her arrival. She needed to think of something quick as the elevator began to go up to the 7th floor. The elevator doors opened as Jessie walked out and began searching for her room. A few minutes went by and she managed to fine the room.
Jessie opened the door and walked in to see Meowth and James pacing around. They were obviously waiting for her to return.
"Jessie!" James said as he heard the door open.
"What did the boss want? Are you getting a promotion?" Meowth asked.
Jessie didn't know what to say. She still hadn't thought of what she should tell them.
"Uh.. Yeah... Sorta." Jessie said as she stumbled for words.
Jessie needed a shower and she didn't feel like really discussing it with her friends at the moment. She was hot and sweaty from her time with Giovanni and she needed to clean herself off.
"I need to have a shower. I'll explain after I get out." Jessie told them as she walked over to the bathroom and closed the door behind her.
"Jessie seems a bit depressed." Meowth said to James.
"Maybe she didn't get the promotion. Wonder what happened." James replied.
"Guess will find out after she gets out of the shower." Meowth said.
"Good morning everyone" Misty said as everyone dropped their stuff at the entrance lobby.
"Hi Misty. Sleep well?" Dawn she asked the boys as she put her backpack on the ground.
"Yeah, slept solid the entire time." Ash replied.
Moments later, Misty's sisters arrived at the front lobby to see them off. Each of them had a gift in their hand. Everyone turned to watch them approach.
"Well everyone, I guess this is goodbye." Lily said with a bit of sadness in her voice.
"It's been fun while you guys were here." Violet said right after Lily.
"We wish you could stay longer and visit with us some more, but I guess you're all eager to continue on your new journey." Daisy said.
"Thanks you guys. Were going to miss you too." Ash said as he starred at the boxes they were each holding.
"Goodbye, Lily! Goodbye, Violet! Goodbye, Daisy! Next time I visit I will make sure we have some private fun of our own!" Brock said somewhat disappointed he didn't get to do any of Misty's older sisters while he was here.
"Will be waiting for you Brock." Violet said as she winked at him.
"Guess will just have to wait a bit longer to get some action with Brock." Lily said with a smile on her face.
"Hey, at least you two got some action. All I got was a sunburn." Daisy said as she looked at her red skin as everyone laughed at Daisy's remarks realizing she was left out from their fun yesterday.
"Well before you go, we have a present for you girls from us." Lily said as the three of them all gave gifts to Misty, May and Dawn.
"Now don't open them for a couple days. We want you to think about what's inside for a few days before you open it." Daisy said.
"That way, you'll all be thinking of all the strange and wonderful things that are in those boxes!" Violet exclaimed with a bit of a chuckle in her voice.
"I wonder what's inside" Dawn said as Violet gave her the gift.
"You'll just have to wait and find out! It's a surprise. But we're sure you'll like it!" Lily told her.
"I hate surprises. I want to know what it is now..." Ash said as he tried to grab the box from May to shake it around a bit.
"Hey Ash! You'll find out in a few days just like us." May told him as she put the gift in her backpack safely.
"Thanks for the gifts you guys." Misty said as she hugged her sisters.
"You're welcome! We're going to miss you Misty." Daisy said as she rubbed Misty's back as she hugged Violet.
"Take care! Okay?" Violet said as she let go of Misty.
"You too." Misty replied as she picked up her stuff off the floor.
"So where are you off to?" Lily asked wondering where their next stop would be.
"Were off to Saffron City's Gym to visit Sabrina." Ash told them.
"Saffron City, huh? We haven't been there in a while girls. We should go shopping there one day." Daisy said as she was thinking to herself as she replied.
"Well we better get going. It's going to take us a few days to get there and we need to get to a Pokemon Center before dark." Brock told everyone as he started out he front door.
"See you later everyone! Take care!" Misty's sisters said as the group began their journey to Saffron City.
After a bit of walking, the group was almost out of Cerulean City. Just a few days earlier, they were on their way here and now they were leaving the city behind.
"Sad to leave your home town again?" May asked Misty as they looked back at the city that was slowly disappearing into the distance.
"Not really. I've been running the Gym for ages now. It's time my sisters watched it while I went on a journey of my own. It's only fair." Misty told her.
"I wonder what it's like being a Gym Leader. It must be quite a hard job. All those trainers coming to battle. You'de need to make sure your Pokemon were always in top fighting shape." Dawn asked everyone as they continued walking.
"It can be quite tough, but its also quite fun. I enjoyed being a Gym Leader" Brock said as he turned to talk to Dawn while he walked.
"I enjoyed it too, but it's time I had a break from it. It gets stressful after awhile." Misty explain to her.
The group continued on walking on the path to Saffron City, enjoying the time together. Ash and his friends hadn't heard or seen from Team Rocket in day and their mistimely appearances every day had Ash a bit worried.
"You know, we haven't seen Team Rocket in a few days. I wonder what they are up to?" Ash asked pondering what their next scheme might be.
"Well we are on their home turf. The one thing I don't miss about traveling with you Ash is Team Rocket. We need to make sure were on high alert at all times." Misty said as she was back to her serious self again.
"Maybe they have finally given up trying to get our Pokemon and are going after someone else instead." May wondered.
"Maybe, but I find it unlikely that they would stop after all this time." Brock concluded as he too wondered where they might be.
In another area of the Kanto Region, Jessie, James and Meowth were on their way to the Team Rocket Headquarters. Since they had returned to the Kanto Region, they decided that it was time to check in with the boss to report on their mission in the Sinnoh Region.
"Are we almost there?" James asked as he was walking slowly trying to catch his breath.
"It seems further than last time." Meowth replied.
"I think were almost there. It's just around the bend." Jessie said as she started looking over the rocks to see if they could find their destination.
After a minute or so of walking, Jessie, James and Meowth could see the Team Rocket Headquarters in front of them. It was set in a mountain for protection and as usual, there were two Team Rocket henchmen at the front gate making sure no unauthorized visitors tried to enter the complex. Jessie, James and Meowth walked up to the gate and identified themselves.
"Agents Jessie, James and Meowth reporting as order." Jessie told them as they stood at attention.
"The boss is waiting for us to report on our activities in the Sinnoh Region." James continued.
"Don't stand there all day. The boss is expecting us now." Meowth told them as they looked suspiciously at the three of them.
"I remember you three." One of the guards said as he looked at the other guard.
"You're the three that were here on po-go sticks last time." the other guard said recalling their previous experience with Jessie, James and Meowth.
"Were going to have to double check that the boss really wants to see you." the guard said as he went into the guard booth to contact the boss inside while the other guard stood in front of the gate.
"Boss, we have 3 agents from the Sinnoh Region that say they are here to see you. Should I let them in?" the agent asked as he waited for Giovanni's response.
"Yes, let them in. I've been waiting for them to report on their activities there." Giovanni said as he cut off the transmission to the guard.
The guard walked out of the booth and pressed the gate button to raise the gate. The other guard obviously knew what the boss's decision was and moved out of the way.
"The boss will see you now." the guard said as he motioned for Jessie, James and Meowth to enter the headquarters.
"It's about time!" Jessie said as she began walking past the guards.
"We told you he was waiting for us!" James said as he also started walking.
"You're glad the boss isn't mad with you for making him wait!" Meowth said with he head held high as he walked by the guards without looking at them.
Seconds later the group entered the headquarters for Team Rocket. They had been here quite a few times and knew the way to the boss's office. They walked into the elevator and took it to the top level. As the doors of the elevator opened, they could see right into the boss's office at the end of the hall. He was sitting at his desk looking outside.
Jessie, James and Meowth walked into his office and stood at attention.
"Jessie, James and Meowth reporting as ordered." Jessie said to Giovanni as they awaited his response.
"Ah, I've been expecting you." Giovanni said as he turned his chair around to face them.
"So, let's hear you report on your activities in the Sinnoh region." he continued.
For the next 20 minutes or so, Jessie, James and Meowth explained all their activities in the Sinnoh region. As the only group of Team Rocket agents in that region, they had a lot of explaining to do about Team Galatic and their activities.
It had been a few years since Giovanni had seen this group of agents in real life and his eye kept focusing on a more mature looking Jessie. This wasn't the young girl he originally remembered joining Team Rocket and he couldn't help but stare at her as they continued explaining everything that had happened to them. After a while, they talk began to blur and Giovanni sat there staring at her.
Jessie didn't notice Giovanni starring at her as she, James and Meowth had almost got to the point of arguing as they continued their report. Jessie was in her prime and Giovanni couldn't believe how beautiful she looked. He was so mesmerized by her that he didn't care that the three of them were arguing.
Jessie, James and Meowth continued arguing back and forth for a few minutes not realizing that Giovanni had stopped paying attention to them and was more concerned about Jessie's looks. Finally Giovanni had enough and decided it was time to end this.
"Okay that's enough. You can explain the rest in your written report." Giovanni said as he cut them off in mid sentence.
Jessie, James and Meowth quickly turned to look at the boss and they all tried to compose themselves realizing that the boss might be angry which was something they didn't want.
"Will do boss." Meowth replied.
"Now go. I'll expect your report by tomorrow. Agent 363 will arrange quarters for you while you stay here. You can talk to him at the front desk." Giovanni told them as he motioned them to leave.
Jessie, James and Meowth saluted as they turned around and started heading out of Giovanni's office. Giovanni watched Jessie begin walking. Her tight skirt practically form fitted around her ass giving him a great view of the shape of her ass. It looked firm and tight and it was driving him crazy.
"Agent Jessie, stay here for a few minutes. There is something I wish to discuss with you. The rest of you go." Giovanni finally spoke up as Jessie turned and quickly returned towards Giovanni's desk.
"Close the doors when you leave." Giovanni instructed James and Meowth who were a bit confused as to why Jessie was called back into his office.
James and Meowth entered the hall and closed the doors behind them. They watched as their vision of Jessie vanished with the closing of the doors.
"I wonder what the boss wants with Jessie." Meowth asked James.
"I dunno. Usually we do everything together as a group. Seems like that might change now though." James said with a hint of disappointment in his voice.
"He can't split us up even if he is the boss!" Meowth said starting to get a bit of anger in his voice.
"Well it's not like we can barge back in there now. He'd kick us out faster than we could get in the room." James said in a depressed voice.
"Yeah, I guess your right. Best we just wait till Jessie gets out and we can find out from her whats going on." Meowth said as he began to walk towards the elevator.
James followed him as they both went down to the front desk to get their room sorted out. They both continued to wonder what the boss wanted with Jessie.
"So Jessie, you've been a member of Team Rocket for many years now and you're still a field agent, is that correct?" Giovanni said as he continued to scan her body with his eyes.
"Yes, that's correct sir." Jessie thought as she was now hoping a promotion was coming.
Giovanni already knew the answer to his question and was just making small talk to make Jessie a bit more comfortable. He could tell that she was a bit nervous, but who wouldn't be when talking to their boss.
"How would you like to join a special branch of Team Rocket that only a few members are a part of?" Giovanni finally asked her with a bit of a smirk on his face.
"The special agent group?" Jessie eagerly replied hoping that it was going to be that.
Jessie remember her last encounter with Domino and she hoped that she could become part of the group, that way Domino couldn't bug her about being a lowly grunt in Team Rocket anymore.
"Yes, the special agent group..." Giovanni replied realizing that Jessie was to incompetent to be a member of his personal elite agent core.
"...but this division is a bit more specialized. You see, this group reports directly to me in person." Giovanni continued to explain to Jessie as she was getting a bit more excited by the minute.
"The group is secret and you should not tell anyone including other agents about it. Once you join, you can never leave the group. You will always be a part of it. Are you willing to accept these terms Agent Jessie?" Giovanni asked her without telling her the full details he had in store for her.
"Yes sir!" Jessie quickly replied.
"Good, you'll start immediately then." Giovanni said with a smirk on his face.
"W-what do I have to do, sir..?" Jessie asked as she gently tugged on the end of her skirt as she saw Giovanni starring at it.
"Why don't you come sit on my lap and I will explain to you a bit more what your duties will be." Giovanni told her with a sly smile and Jessie could see the erection in his pants already as she began to walk behind his desk.
Jessie was starting to get a bit scared as it now seemed the the boss had other ideas for her than what she originally thought. The erection in Giovanni's pants was quite large and the fact that he wanted her to come sit on her lap would make it very awkward to avoid. Jessie was hesitant to sit on his lap as she walked to the side of his desk.
"Come and sit here." Giovanni said as he patted his legs with his hands motioning for Jessie to come sit down.
Jessie took a big gulp and slowly moved towards the boss. She began to sit down on his lap as Giovanni sneered at her, please that she was obeying him.
"There we go. Now I can further explain your duties now that your a member of this special division of Team Rocket." Giovanni said as he began to explain.
"So what exactly will I be doing?" Jessie said a bit curious as she could now feel his erect penis pushing his pants against her leg.
"We're just gonna have a little fun together." Giovanni said as his left hand was now rubbing against herlegs, slowly stroking her soft skin.
Wrapping his right hand around the back of her neck, Giovanni pulled Jessie into his lips. She did not resist whatsoever and almost immediately her tongue was at the back of his throat. They kissed passionately and her hands found their way to either side of his face. Jessie was starting to relax a bit now and was actually liking the attention that the boss was giving her. There were plenty of girls in Team Rocket and the fact that he found her attractive made her feel special. After a few seconds kissing, Giovanni pulled away sharply and stared at her with a devilish smile.
"On your knees!" Giovanni ordered and without hesitation, Jessie dropped to her knees as he undid his belt and pulled his zipper down.
"Pull it out." he told her.
Jessie slid her right hand over his bulge to catch his zipper and slowly pulled it down before sliding her hand into his fly. Giovanni's erection flew out his pants with only the tiniest tug from her hand. Her hands were surprisingly cool as she gently clasped Giovanni's penis. She pulled his balls out with her left hand before beginning to slowly stroke him up and down.
Giovanni's penis was hot and hard. It was also the biggest penis Jessie had ever seen. It looked to be about a foot long and over an inch wide. Jessie wasn't too experienced in sex, but she had had her fair share of men and she knew this was a very large penis for any man. The size of his penis seemed to fit Giovanni's body as he was quite a large man. Jessie's small hands could feel blood rushing through the huge veins.
Jessie started to slowly jerk Giovanni off with both hands. Almost immediately, a large droplet of precum emerged and Jessie instinctively licked it. She closed her eyes and savored its taste.
"Mmmm. Tastes so good." Jessie said as she licked the tip of his penis's swollen head.
Giovanni couldn't take her teasing anymore and he grabbed her head and forced his rock hard penis into her mouth. Jessie felt a little bit of resentment at the rough treatment the boss was giving her but his penis tasted so good that she quickly forgot about his treatment and began to play along. Jessie willingly and eagerly moved her mouth up and down along his penis, barely able to get much of it in her mouth as it was so big.
"My god. You're penis is so big! I bet you can't wait to shoot your load inside my mouth! Or would would you rather come all over me, or inside me?" Jessie said as she was now getting turned on herself.
"Less talking, more sucking." Giovanni ordered.
Jessie sucked on just the head of his penis before taking more into her mouth, slowly sliding her lips further up his penis. Giovanni began to pump his hips he began fucking her mouth now, holding her in place while he pistoned his hardon in and out of her lips. His penis pounded deep into her mouth and it wasn't long beforre it started gagging her. After a few more thrusts he pulled out, allowing her a chance to catch her breath.
Jessie had never experienced anything like that. Giovanni, her boss of many years, was thrusting his huge penis inside her mouth and down part of her throat. He managed to enter half of his twelve inch penis into her mouth, but deep-throating the other half proved to be beyond her abilities.
"So are you enjoying your first mission as the newest member of Team Rocket's elite?" Giovanni asked Jessie as she was regaining her breath as she knelt in front of his desk chair.
Suddenly, there was a knock at the door and quickly Giovanni pushed Jessie out of sight under his desk. Jessie could hear Giovanni fumbling with the things on his desk as he moved his chair closer to the desk as the door opened.
"Uh, I'm sorry to boss, but we just had word that a new gang in on the move and is beginning to overtake some of our territory." a Team Rocket grunt said as he reported the findings to Giovanni.
The two talked for a few minutes as Jessie tried to stay as quiet as she could. Giovanni's pants were still undone and his erection was still as hard as ever.
"Thank you for the report. Close the door on your way out." Giovanni told the grunt as he seemed a bit angry now.
Moments later, Jessie heard the door close and Giovanni moved his chair out to allow her to get out from under the desk.
"There is a new gang attempting to take control of come of our vital areas." Giovanni angrily said as Jessie could see that he was trying to devise plans to counter this new threat.
"This sounds bad." Jessie replied as she tried to sympathize with her boss.
"They must be stopped." Giovanni said as he banged his fist against the arm rest.
Jessie could see that Giovanni was quite stressed out now after this news. It kind of killed the mood that was in the room before the news. Giovanni's fly was still open and his penis seemed more erect that before. It seemed to Jessie that Giovanni got turned on even more when he was angry.
"Well, I know something that can help you out right now." Jessie said as she moved up towards his penis and began to lick and suck it again.
Jessie pulled down Giovanni's pants so she could access his penis and balls better. While she did that, Giovanni began to take her white vest uniform top off revealing her skin tight black shirt underneath.
"Would you like me to take my skirt off too?" Jessie asked cheerily.
"Oh, fuck, yes," Giovanni replied loving the attention he was getting.
Jessie began to take her top off with a teasing smile on her face as she did so. She pulled it off to reveal an elegant black full-cupped bra, the upper half made of floral lace. Giovanni could see parts of her aerolas through the lace. Giovanni's eyes froze at the spot where her nipples were thrusting against the fabric of her bra and he licked his lips in excitement seeing her aerolas through the bra.
"Why don't you go lock the door, while I slip out of these clothes completely." Giovanni instructed as Jessie got up and began walking toward the door.
Giovanni quickly took off the rest of his suit and threw it on the ground as Jessie locked the door making sure they wouldn't have any more interruptions. Giovanni eye Jessie's every move as she began to walk back towards him at the desk. She stood in front of him and cupped her breasts.
"Do you like what you see?" she asked enticingly.
"Yes, but I'de like to see more now." Giovanni told her.
"That can be arranged." Jessie said as she smiled seductively.
Jessie started working her hips, dancing slowly and seductively in front of Giovanni who had returned to his seat. Jessie's hands played with the bra straps on her shoulders as she slipped one and then the other off her shoulders. Her breasts were almost free, but they were still held within the bra cups. She reached up to the cups and pretended to pull the cups down to expose them, but instead she pushed her breast up a bit revealing her cleavage to him as she bent down a bit in front of him.
The anticipation was killing Giovanni and he couldn't resist any longer. He began stroking his penis up and down in front of Jessie as she slid the bra straps back up onto her shoulders and turned away from him. She released the bra clasp at her back and let the two pieces fall away to expose her back. Jessie then turned around again, holding the cups of her bra against her breasts.
Jessie smiled as she saw Giovanni stroking himself as she watched her strip. Jessie slowly lowered the bra off her breast, replacing the area of her breast that was covered by the bra with her hands. Giovanni saw the bra fall to the ground but was disappointed to see that she was still covering the majority of her breasts with her hands. She pressed her breasts flat and moved her hands in circular motions. Jessie moved her hands slightly and parted her fingers a bit. Giovanni realized that she was revealing her nipples through the part in her fingers and he stared intently.
"Oh, wow!" Giovanni moaned as she Jessie finally removed her hands from her breasts to reveal her 34dd breasts to him.
"So? What do you think? Do you like 'em?" Jessie said as she straightened her back to thrust her chest out more to make her breasts look even bigger.
"They're amazing." Giovanni responded.
"You must really love my boobs, as you can't seem to take your eyes off of them."Jessie said laughing and gave her breasts a shake.
"Are you kidding? I love breasts!" Giovanni told her.
"I love to have my tits fucked." Jessie said running her hands over her sumptuous breasts.
"I love feeling a nice hard penis slide in between my big titties." Jessie continued as she rubbed her breasts together.
Giovanni was in heaven as he watched his sexy young agent turn into his personal dream come true.
"Do you want me to fuck those sexy tits of yours?" he asked her.
"God yes! Fuck my tits!" Jessie replied as she squeezed her breasts and once again knelt down in front of Giovanni.
Giovanni placed his penis in between the cleavage of her breasts as soon as she was in range.
"Oh! I can see you're very eager. Perhaps you'd like to come over my tits?" Jessie exclaimed in excitement as he began sliding his penis all over her breasts.
Giovanni reached down to fondle her magnificent boobs that he had been watching for the past few minutes and he quickly had them wrapped around his penis. He started to pump his penis in between her huge tits as the head of his penis was popping out the top of her cleavage with each thrust. She reached down and began massaging his balls while he thrusted his penis between her breasts.
"Tell me how much you like getting your tits fucked." Giovanni ordered as he continued.
"I love it! You're penis is so big and warm. I cannot wait for you to shoot your hot cum all over them! " she exclaimed squeezing her breasts together even tighter.
Jessie's large boobs were nice and soft and a great cushion for Giovanni's large penis as it stroked in between the cleavage. He continued stroking his penis between her breasts for a few minutes, as he continued to build up to a climax. Jessie could see he was starting to have problems holding his cum back.
"Cum on my big tits! Cum on my big slutty tits!" Jessie taunted him as she awaited him to cum.
Giovanni began stroking in between her breasts as fast as he could. He started to moan as he could feel the cum heading towards the head of his penis. Jessie closed her eyes and felt the hot liquid splash onto her huge breasts. He continued splurting large blasts of his white cum and Jessie though it would never end. Giovanni shuddered as the final drops of cum fell onto her breasts and he wiped the tip of his penis over one of her nipples.
Jessie finally opened her eyes and looked down at all the cum on her breasts. She saw that the head of his penis was covered in cum and she was immediately attracted to it. Not wanting to waste any of his cum, she opened her mouth and put the head of his penis in her mouth.
Jessie started to lick the cum off his penis and it was quickly cleaned off. Jessie then began slurping and sucking like a vacuum trying to suck out any remaining cum. Giovanni groaned in bliss and she smiled up at him as he encouraged her to continue.
Jessie then proceeded to give Giovanni the best blowjob he had ever had in a while. She planted tiny kisses up and down by his penis as she flicked her tongue across balls and then licked up the shaft of his penis. She then put his penis in her mouth and bobbed her head up and down, swallowing his large penis as best as she could.
Giovanni's breathed harder as the sensitive skin of his penis ached from the attention Jessie was giving it. Jessie whimpered softly as she lifted her head, sucking on the penis in her mouth. Jessie loved to give blowjobs. Giovanni continued moaning softly as Jessie sucked his penis. Finally, Jessie believed she had sucked out the remaining cum and she stopped.
Jessie stood up once again and twirled around while raising her short skirt to show Giovanni that she was wearing a black g-string that matched her bra.
"Do you like looking at my pussy through my panties?" she asked him as she got up on the desk and began to spread her legs wide.
"Oh yes! I want to lick your sweet pussy." Giovanni replied as he moved in close towards Jessie.
"Lick your fingers and reach inside your panties. Play with your clit!" Giovanni ordered ass he waited to see if Jessie would obey him.
Jessie's short dress rode high up her hips now and Giovanni was getting a very close view of her round as. He could also see that her labia was quite puffy and her tiny panties were barely able to cover her pussy now. Jessie parted her legs a bit more and Giovanni could now see a damp spot on her panties. She put her hand in her panties and then began to play with her pussy.
Giovanni slid his hands down between her legs and caressed the lips of her vagina through her panties as Jessie continued to rub her clit.
"You're all wet and its soaking through your panties. You like touching yourself, don't you? You like my fingers there too?" Giovanni asked.
"Yes, I love feeling my pussy." Jessie told him.
"Do you want me take over for you now?" Giovanni asked her.
"Please." She responded quickly.
"Now take off your panties for me so I can see what I'm doing." Giovanni instructed her.
Jessie grabbed the side bands of her panties and began to raise it up her legs slowly revealing her pussy to Giovanni. Her pussy lips were completely bare and smooth while there was a patch of pubic hair above her pussy in a triangle shape. Giovanni loved the look of her inviting pussy and he couldn't wait to feel it. Jessie also took off her skirt leaving her completely naked infront of Giovanni on his desk.
Giovanni moved his head up to one of Jessie's breasts and started kissing one nipple and fondling the other breast with his hand. His lips and tongue circled round her nipple causing it to get incredibly hard. His fingers gently rubbed her other breast and nipple producing the same result. She moaned a little as she loved the way he was playing with her breasts.
After a few minutes of playing with her breasts, Giovanni slowly slid down her body as he kissed and licks all the way from her breasts to her stomach. Giovanni relished the feel of her hot, smooth skin as his lips touched her.
Jessie spread her legs as wide open as she could, inviting Giovanni to move down between them. He ran his tongue from her stomach to her hip and then down until he went around her pubic hair and then over to the softness of her cunt lips.
"Oh! Lick me! Lick me, please! I want to feel that hot tongue of yours licking me out! Lick my clit and make me cum!" Jessie said as she could no longer take any more of his teasing.
Giovanni began sucking on her pussy lips in his mouth and used his tongue to play with her clit. Jessie moaned as Giovanni continued eating her pussy.
"Damn, you're good at eating pussy!" Jessie said as she couldn't believe how good he was.
Giovanni's face was buried in Jessie's lovely pussy. He clamped his lips around her clit and started sucking on it, while his tongue probed and licked it at the same time. After only a few minutes of sucking and licking her clit, Jessie climaxed and gave out loud moan.
"Oh my! I came so fast!" Jessie exclaimed.
Giovanni's jaw was getting a little tired so he stopped licking her and looked at her pussy that was now quite red and swollen from all the attention he had given it. He was ready now to move this on to the next stage. He stood up in front of Jessie and slowly stroked his penis. Jessie couldn't believe how big it was and was a bit afraid of something that large going inside her.
Jessie was also somewhat nervous as she lay there naked on the top of Giovanni's desk. She had been in his office many times, but never did she think she would see his office from this angle. Now that moment was about to arrive as Giovanni moved in between Jessie's legs and he looked down at the hotness of her pink pussy lips that were very wet and swollen from the fingering and licking he'd already been giving her.
"You'de better be ready for this!" Giovanni said as he stepped in front of her and aimed his large erect penis at her dripping pussy.
Jessie threw back her head and yelled as Giovanni drove his large penis into her wet pussy. After the first few strokes, Jessie started to push back into him to match his rhythm. At every thrust, she moaned lightly and she began to buck wildly. Giovanni was forced to push her flat against his desktop and hold her there so she wouldn't fall off.
"Fuck me hard!" Jessie squealed as shockwaves of pleasure consumed her causing her to arch her back and make her breasts protrude from her body further.
Giovanni began pounding his large penis into Jessie's pussy. She screamed as he buried his penis in her again and again. Giovanni pushed his thick penis in a few more inches, but he barely had any of his large penis in her yet.
"You like that? Does that feel good?" Jessie said seductively.
"Oh yeah." Giovanni sighed as he pushed another 2 inches inside her.
Govanni could now feel the engorged head of his penis hitting the mouth of her cervix as he thrusted. He retracted his penis almost completely out of her pussy and then drove it back in again. He did this a few time, each time he managed to get another inch of his penis inside her.
"God it's so big!" Jessie cried.
Giovanni's powerful and strong erection plowed through her delicate pink pussy lips right against the entrance to her womb. Jessie could feel Giovanni's big hard penis filling up her entire pussy as he thrusted it in and out of her. She knew that Giovanni was very experienced by the way he was having sex with her as she was quickly building up to yet another climax.
Jessie's pussy muscles clamped tight around Giovanni's penis as he managed to get in about 8 inches of he penis. Jessie couldn't believe how big he was. She had never had sex with someone who had such a big penis. Her pussy was stretched to the max to allow it to fit in her. She knew she couldn't take anymore of it inside her and the constant bashing against her cervix was driving her crazy.
Jessie's orgasm began to build again until finally she climaxed again. Jessie had never had two orgasms this close together and the feeling was overwhelming. She closed her eyes as the feeling rippled through her body. She could still feel Giovanni going at her pussy relentlessly.
"You came again already?" Giovanni asked her as he continued thrusting in and out of her.
"Oh yeah! You're really good at this. I've never felt this good before." Jessie said as she looked down at her pussy to see Giovanni's large penis still spreading her pussy lips out wide.
"I cannot get my penis all the way inside you. I'm going to have to try something a bit longer. Flip over and raise you're ass." Giovanni told her.
Giovanni pulled his penis out of Jessie's pussy and she did as she was told. She turned over on her stomach and lay on the desk. She was able to touch the ground now with her feet to help balance herself. Giovanni moved in close to Jessie again and aimed his penis at her ass hole.
"Oh yes. Fuck me in the ass with that big cock!" Jessie told him as she turned her head around to watch Giovanni stick his penis inside her ass.
Jessie gasped loudly as she feel his penis slip past the tight outer opening to her ass.
"You ok?" Giovanni quickly asked not really concerned about her that much.
"Yes. Don't stop. Just go really slow," Jessie replied with her eyes tightly closed.
"Relax. It will make it easier for me to get it all in!" Giovanni told her.
Giovanni applied more pressure as Jessie felt him go deeper into her bowels. She had never felt anything like this before. Inch by inch his penis pushed into her ass and as soon as she thought he had managed to finally get his entire penis inside her, another inch went in.
"How much more do you have?" Jessie asked as she felt like she had a mile inside her.
"Just another two inches and then you will have all 12 inches of my penis inside you!" Giovanni laughed as he pushed another inch inside her.
Giovanni loved feeling the insides of Jessie's ass and comparing to her pussy that he was just in. Both were very tight, but her ass was even tighter than her pussy. Finally he managed to get his entire penis inside her, something he wasn't able to do with her pussy. Jessie's muscles tightened around him, causing him to groan with pleasure.
Jessie then grabbed her ass and squeezed her cheeks together tight.
"You like it when I squeeze you with my ass?" Jessie asked.
"Oh yeah! Keep doing that. It's nice and tight!" Giovanni said as he started thrusting in and out of her ass.
Jessie closed her eyes and clenched her fists as Giovanni began moving faster and faster in and out of her ass. Giovanni felt amazing as he thrusted deeper into her.
"Fuck me, fuck my tight little ass. Faster, please, faster." Jessie said as she was trying her best to pleasure Giovanni.
"You are so tight! It feels so good. I have my entire penis in your hot little asshole now." Giovanni told her.
"I'm glad! I didn't think it would fit!" Jessie moaned as she felt like she was being split apart.
Giovanni continued his thrusting, marveling at the reactions of the beautiful woman beneath him. He loved looking at the entrance of her ass and seeing it spread wide to accommodate his penis.
"Oh god, I'm coming again!" Jessie exclaimed as her whole body tensed up and she climaxed for the third time in such a brief amount of time.
"I seem to do that to girls a lot." Giovanni told her as he was proud that she had already orgasmed three times before he'd even cummed once.
The excitement of the moment of hearing Jessie orgasm and then her muscles tightening because of it, proved to be finally too much for Giovanni to withstand.
"I'm going to cum!" Giovanni groaned as he started to explode inside her ass.
"Yes, come for me! Cum in my ass!" Jessie cried as she could start to feel his hot cum filling her insides.
Giovanni was thrusting hard fast and deep as each blast of cum spewed inside of her. Giovanni's desk began to shake as Jessie attempted to balance herself as Giovanni came. Tons of hot cum was now inside Jessie as Giovanni opened his eyes after a powerful climax. His penis though, was still rock hard and erect.
"That felt good." Giovanni said as he slowly pulled his penis out of Jessie's ass.
"It sure did." Jessie replied as she tried to catch her breath.
Finally Giovanni's penis was out of her ass and Jessie turned around to see that his penis was covered in his cum. He sat back down on his chair and rested for a few moments. Jessie also rested on Giovanni's desk as she knew he'd be wanting more action any second.
"Come sit on top of me and will continue were we left off." Giovanni told Jessie as she turned around and moved towards him.
Jessie slid on top of him on his chair and straddling him. Giovanni felt her hands grab his penis as she guided it to the entrance of her pussy. He could tell she was wetter than ever as the head of his penis was now rubbing against her pussy lips.
Jessie was straddling the head of Giovanni's penis teasing it for a few seconds before she proceeded to mount herself on his erection. Jessie slowly slid his penis into her pussy as it entered her with ease. The combination of Jessie's juices and Giovanni's cum covered penis made it easier for Giovanni to slide his penis deep into Jessie's pussy.
Giovanni could feel his swollen penis head slam against Jessie's cervix as the tip of his penis penetrated that tight little inner hole more and more. Jessie started to bounce up and down on Giovanni's penis which caused her breasts to begin bouncing around. Giovanni watched Jessie's breasts bounce on every thrust as her slippery young pussy gripped his penis with incredible force.
Jessie started to wonder when or if she would be able to get to the base of his shaft and get him fully inside her pussy this time. Jessie moaned as she impaled herself on Giovanni's large penis. She forced herself down onto his penis and then raised up a little then forcing herself down again trying to get his entire penis in her.
Jessie bent over and lay her breasts on Giovanni's chest as she moved her hips up and down on his shaft. Jessie's tits were laying on his chest, moving around and her nipples sometimes rubbed up against his sending a chill down both of them every time they touched. Giovanni grabbed her hips to help keep her balance and started thrusting up into her knowing she would need some help to finally get his full penis all the way inside her pussy.
Finally, Giovanni gathered all his strength and with one last thrust he pushed his penis up into Jessie. Giovanni moaned as he rammed his penis all the way into Jessie's pussy.
Jessie's tits were bouncing up and down to his thrusts and her moans were high pitched as she began to lose it again. Giovanni also couldn't last and longer as well and he let loose at the same time.
"I'm cumming!" Giovanni grunted.
"Cum inside me!" Jessie cried.
With one last thrust, Giovanni slid his penis all the way inside her hungry pussy and held it there as he began spurting load after load of his hot cum inside her pussy.
Jessie's pussy convulsed around him in orgasm as his penis jerked inside her. A wad of cum shot out the end of his penis and splattered off the back of her womb. More of his cum flooded into her pussy as Giovanni began emptying his cum inside her.
A few minutes later Giovanni and Jessie had recovered. Giovanni's large erection had shrunk but his penis was still inside her pussy. Jessie stood up and once again knelt down in front of Giovanni.
"Let me clean you up." Jessie said as she took his penis in her mouth.
Giovanni groaned as his still sensitive penis reacted to Jessie's hungry tongue. Jessie licked clean the combined juices of her pussy and his cum until he was all cleaned up.
"Mmm, I just love the taste of your cum," Jessie said in between licks.
"You did well for you're first assignment Agent Jessie. I think I could use some rest now." Giovanni said.
"Agent 363 will also arrange quarters for you while you stay here. You can talk to him at the front desk as well. I'll contact you when I have another assignment for you." Giovanni said as he picked up come of Jessie's clothes and gave them to her.
"Yes sir." Jessie replied as she got the hint and began putting on her clothes.
"Welcome to the team agent." Giovanni said as he walked toward the side door of his office and closed the door behind him.
Jessie was now left in his office all by herself. She sat there for a few minutes trying to comprehend what had just happened in the last hour. She had just had sex with her boss and was now a member of his private sex group that he had personally chosen. She didn't know if she should feel honored or ashamed. What she did know was it was the best sex she had ever had. She could still feel his hot cum inside her pussy and ass.
Jessie gathered the rest of her clothes and began to get dressed. She knew by this time that James and Meowth would be wondering what was going on. She had to think of something to tell them as the truth was something she wasn't fully comfortable telling even her closest friends. She didn't know what they'de think of her if she told them why the boss wanted a private meeting with her.
Once Jessie was dressed, she opened the door and walked down the hall to the elevator. She pressed the button for the main floor and waited for the elevator to go down. Moments later she arrived at the main floor and she walked over to the main desk.
"Are you Agent 363?" Jessie asked the agent at the desk.
"Yes I am. What can I do for you?" he asked.
"The boss said that I was to talk to you about setting up quarters for me while I stay here." Jessie explained to him.
"And you're name is?" Agent 363 asked.
"Agent Jessie. My friends Agent James and Meowth were probably here earlier." She told him.
"Ah yes. Your quarters are setup with them. They are in room 35 in the residential wing. Level 7." He told her.
"Thank you." Jessie replied as she walked back to the elevator.
Jessie still didn't know what she was going to tell James and Meowth as they were probably anxiously awaiting her arrival. She needed to think of something quick as the elevator began to go up to the 7th floor. The elevator doors opened as Jessie walked out and began searching for her room. A few minutes went by and she managed to fine the room.
Jessie opened the door and walked in to see Meowth and James pacing around. They were obviously waiting for her to return.
"Jessie!" James said as he heard the door open.
"What did the boss want? Are you getting a promotion?" Meowth asked.
Jessie didn't know what to say. She still hadn't thought of what she should tell them.
"Uh.. Yeah... Sorta." Jessie said as she stumbled for words.
Jessie needed a shower and she didn't feel like really discussing it with her friends at the moment. She was hot and sweaty from her time with Giovanni and she needed to clean herself off.
"I need to have a shower. I'll explain after I get out." Jessie told them as she walked over to the bathroom and closed the door behind her.
"Jessie seems a bit depressed." Meowth said to James.
"Maybe she didn't get the promotion. Wonder what happened." James replied.
"Guess will find out after she gets out of the shower." Meowth said.