Jiraya's Personal Make-Out Tactic

The legendary ninja Jiraiya was known for many things. His great strength. His charisma. His unbridled libido. The last thing was probably what he was known for the most. He could never stop himself from leering at women and writing erotic novels based on his sexual misadventures.

He was a bestselling author by far and his series always flew off the shelves the second they were released. There was just one thing he felt that was missing. His novels were always told from the perspective of a man so the readers couldn't truly understand how the women felt. It was a shortcoming he grappled with in the past but now it was really eating away at him. As a straight man, he had never experienced anal sex even though he did question the appeal of it a few times in the past.

He needed to do further research if he truly wanted to write more accurate sex scenes in his novels. The task seemed challenging but it was a hurdle he must overcome. The plan was simple. Enter a gay brothel in disguise and order and a man with moderate dick size to fuck him. That shouldn't be too hard, right?

Jiraiya was in a hot springs inn pacing back and forth in his room. A mixture of curiosity and anxiety welled In his stomach. Part of him wanted to back down from the self-imposed challenge and his other half wanted to understand what exactly was it about anal that women loved so much. His perverted mind was dying to seek the truth. While mustering up all the courage he had, he slicked down his hair, wore a pair of shades, and exited the building. He hopped from roof to roof In pursuit of a brothel that would suit his needs.

The cold night air brushed against his rosy cheeks as his eyes honed in on a building that caught his eyes. The banners on the side advertised itself as a men's only club with very discreet men. Sounded like it would do the job. He knocked on the door and a gentleman in butler's attire opened the door for him.

" Greetings sir. Have you made a reservation?" The well-groomed man asked.

" Ugh no. I just had this spontaneous urge for sex and I just kinda wound up here. It's like my dick has a mind of its own sometimes. " Jiraiya used comedy to help ease his tension and calm himself a bit.

" I know.the feeling quite well. Please sit on the sofa and the next available worker will service you as soon as possible. " the butler replied with a grin.

Jiraiya nodded and had a seat. It was too late to get cold feet now. He had come this far so the only thing left to do was to finish the job. This was his last day as an anal virgin. Roughly 15 minutes passed until he was told a room was available. He followed the directions the butler gave him and walked down a long corridor until he stood in front of the room number assigned to him. With one big gulp, his hand cupped on the knob and opened the door.

The room was lavishly designed with black lace curtains and immaculate rugs. On the king size bed was a man with a slender figure but rather plump thighs. His body was only covered in white lingerie and he wore a mask to conceal his mouth but his right eye and spiky silver hair were exposed. Any anxiety Jiraiya felt before was replaced with pure shock.

" Kakashi is that you!?" There was no mistaking the man's identity. His body frame and hairstyle were exactly like that of his most devoted fan. Kakashi recognized the familiar voice and analyzed his stature.

"Jiraiya!? What on earth are you doing here?" Kakashi's sole visible eye widened to the size of a saucer.

" I could ask you the same thing. I'm here for research purposes. For my novel, of course" the pervy sage cleared his throat and tried to regain his composure.

" Hate to break it to you, but this brothel is for gay men. You won't find any women here that will suit your needs. I'm surprised you made it this far without knowing that".

" I know exactly what this place is about. It’s just that I've always written sex scenes where the heroine falls head over heels for the Male lead due to how good anal sex is but I can't even wrap my mind around what that feels like. The anus is a lot different from a vagina. It’s tight and small so I can't see how stuffing a large dick up there could feel good. I wanted to experiment so I could write something more authentic." Jiraiya explained his reasoning to Kakashi and sat by him on the bed. His eyes lingered on the plus-sized body wrapped in white lace. He had gained quite a bit of weight since they last met. The man smelt of fine perfume with hints of rose lotion.

" I see. That's a fine reason to experiment with the same sex if I ever heard one. I suppose you're wondering why I'm here myself. The job of being a ninja brings a lot of unwanted stress with it and everyone needs a way to calm down after long missions. Some people meditate; I prefer having my hole destroyed by random men. I call it a hobby of mine." The silver ninja inched closer to Jiraiya and firmly caressed his crotch.

Jiraiya was more than a little intrigued. This was a side of Kakashi most people never saw. " Color me surprised. You're always such a serious killjoy with your students. It's nice knowing there's a side of you that knows how to have fun. Then again, it's only natural for a fan of my marvelous novels to be sexually liberated. So, how about you help me with the research I came for?"

" I'd love to, but I'm much more of a receiver than a giver. Bottoming Is how I get most of my pleasure. Sorry, I can't be any help. If you’re looking for good dick, talk to Asuma. He's the one who got me into this lifestyle in the first place. "

" And how on earth did that happen?" Jiraiya asked while scratching his chin.

" One day he won two free trips to the hot springs during a raffle so he invited me along. I normally go to the hot springs alone so most of my comrades don't know about my not so little secret"

Kakashi shifted his position on the bed to arch his back with his ass up in the air. Jiraiya caught full sight of all the curves and plumpness Kakashi kept hidden. His ass was much larger than one would expect. It was like a giant ripe peach ready to be plucked and devoured. The panties he wore looked ready to tear at any second.

" My pants are pretty loose so you can't notice how big my ass is unless you get up close and personal. Once Asuma caught sight of this beauty, he went wild. He's already dating Kurenai but even he couldn't resist this body. He ate my ass out and smashed my hole right there in the bathing area of the springs. It was the best dick I ever had and he made me lose my bladder several times. He's fucked me several more times after that and encouraged me to put my talents to good use. Nowadays, I work at this brothel whenever I have the time."

Jiraiya was marveled by the story. He had always known Kakashi and Asuma, but he would've never figured they would be friends with benefits. The two made an attractive pair and it was good they had healthy sex lives. Sex was the best way to cope with being a ninja.

" It looks like Asuma has the sex drive I'm looking for to complete my research. I'll be sure to chat with him soon. Until then, I need to explore that big ass and see if it's worth all the Ryo I paid." Jiraiya's huge hands slapped Kakashi’s juicy booty and watched the mounds of flesh jiggle. The masked ninja out a high pitched moaned and trembled from the force.

" Oh, that was a nice moan. I'll have to make you scream even louder than that " His hands grabbed the soft silky panties and roughly yanked them off. The bare ass was right before his very eyes and it looked phenomenal. The skin was perfectly smooth and had the right amount of fat. His hands moved from the ass to the underside of the belly. It seemed that Kakashi gained more than a couple of pounds to get his ass to such glorious shape.

" Well look at you Kakashi. Have you been stuffing your face just to get this thick?" He teased. The masked ninja bashfully nodded his head and looked away.

"It’s sometimes hard to Increase the size of your butt with exercise. Fattening up my body was the best way to do it. I've lost a few clients because of my fat but I've also gained new ones. I'm not quite sure how to feel about that" he sighed.

Jiraiya placed a firm grip on Kakashi’s head and ruffled up his hair. " If you ask me, you look amazing with the added fat. It gives you more curves and makes your thighs all the more fun to caress. Imagine how great you would look with even more weight. " Kakashi’s face turned a shade of red he never thought possible. Jiraiya made him comfortable with his new body and even encouraged him to continue his weight gain journey.

" I'm so flattered, Jiraiya. Nobody has even complimented me like that before. Perhaps I should stuff my face in a bucket of ice cream after our session. " Kakashi had on a smile so wide and glowing that Jiraiya could notice it even with the mask.

He had his silver-haired comrade lay on his back with his feet pointed to the sky. He was taken back by how abused Kakashi’s anus looked. It was clear that the man had taken a countless amount of dick over the years. Jiraiya would be sure to exchange sex stories with him at some point. The perverted sage grabbed Kakashi by his ankle to bring the foot to his mouth, basking in its scent and flavor. His tongue in between the toes before swirling all around the sole. The ticklish foreplay made the usually stoic ninja giggle uncontrollably. Jiraiya got a good taste of minty essential oil Kakashi soaked his feet in. How was it even possible for a man to be this sexy? Jiraiya never knew that a man could be so soft and plump. He felt like he was missing out on a lot of sex with the other team.

" Enough with the foreplay. Time to see what's it like on the other side " The sage gave Kakashi a firm slap on the stomach before slowly sliding his cock inside and pounding away. He was glad Kakashi already filled his ass with a lubricant because he forgot his own. Fucking a Male's ass was a lot more pleasant than Jiraiya thought it would be. Kakashi's entrance was smooth and juicy due to his lack of body hair and lubricated hole. Jiraiya grunted once he felt the hooker's hole squeeze down tightly on his member, wanting to milk out every drop of sperm he had.

" AH fuck! You certainly know you way around fucking a good ass. I just hope you won't put your all into it just because I'm a guy" Kakashi smirked and rolled his eyes back once the dick went in further.

" Your student doesn't call me the pervy sage for nothing. I never back down from a sex challenge. This ass is mine." He slapped the belly once more and gripped him by the hips to buckle inside him even harder. Fucking his great anus didn't feel too different from fucking a pussy. It was much noisier and it knew how to grip hard onto his tip. Every thrust produces a sound reminiscent of a queef. Jiraiya was amazed by Kakashi’s slutty body.

He watched the plump booty tremble on command and try its hardest to suck all his seed out. It was a giant mass of flesh that was designed to pleasure his dick to the best of his capability. Jiraiya put all of his energy into holding back his nut. Kakashi had the kind of ass a man could fuck for whole month straight and never grow tired of it. Kakashi held a similar opinion of Jiraiya's dick since moaning and pleading for more was the only thing he was capable of at this point. All of his attention was on throwing his hips back onto the dick and shaking them with all his force. Dear god was Jiraiya the goods. Every slam into his ass pussy was creaming him out and making his tip leak with pre-cum. He needed to feel Jiraiya’s hot seed flood the insides of his walls. “ AH AH FUUUCKKK! DAMN DADDY!!!!” Kakashi bellowed loud enough for even men outside the room to hear them. His bladder had given out from under all the pressure he was put through. His stiff cock was nothing more than a hydrant of piss soaking up the previously stainless white sheets. He hoped that wouldn’t come out his paycheck. Kakashi felt like a shameless dirty whore for wallowing in his own piss like that. He preferred to keep himself clean, but there were times where accidents were inevitable. Some men took pride in forcing their conquest to lose control of their body and others were so revolted they never came back.

Sometimes they didn’t even tip. They’d just pin all the blame on Kakashi for not living up to their unrealistic sex fantasies. Kakashi couldn’t keep track of the number of clients who expected him to be a perfect sex machine who didn’t so much as moan without their permission. His gluttonous diet combined with the physically demanding nature of his job meant that sperm wasn’t going to be the only fluid spraying from his hole. Before his weight gain journey, he used to starve himself for most of the day to keep his system clean. His first session with Asuma completely changed that. The bearded man taught him that if a man couldn’t embrace his natural body for all its faults, he wasn’t worth getting piped down by. Jiraiya certainly didn’t seem to mind the waterworks display going on in front of him. He simply continued fucking the daylights out of his masked friend while he emptied his bladder. His strokes into the hole were as long and sensual as Kakashi’s best clients. Jiraiya didn’t need to be bi-curious that a sweet piece of ass was not female exclusive. The booty was enough to make even the strongest men weak in the knees; such is what the sage thought when he felt the stamina drain from his cock.

“ Take my seed, Kakashi! I’m giving your ass all of my nut! Take it all!” he shouted right before his mighty manhood fired an unrepenting stream on sperm into the bottom. It was much more semen than the average male could produce at once; a sure sign of his vitality. The force of the ejaculate was so great it could only be described as a semen enema. The slutty moans and grunts of two sex addicts in heat intermingled into a sublime symphony. The two white-haired perverts laid side by side on the piss and sperm-soaked bed.

“ What was it like fucking male pussy for a change? Was it as good as fucking a woman?” Kakashi looked at his client with a smirk as he awaited his answer.

“ It was…. Let’s not compare apples to oranges. Sex with females is wonderful and sex with you was fucking fantastic. Don’t think I ever fucked a girl until she pissed herself so that's a plus. I guess gender doesn’t matter as much during sex as much as I thought it did. All you need is a partner that knows what they’re doing. You’re a phenomenal sex worker who deserves every bit of money you get. Maybe this is your true calling.” He caressed Kakashi's folds of fat while gazing at the beautiful star-filled night sky from beyond the window.
“ Who knows. Being a ninja and a prostitute have their perks. I’m not sure if I would give one up for the other. Though, if I keep gaining weight like this, I may not be able to fulfill my ninja duties. Now wouldn’t that be a shame? I take that you’re planning on visiting Asuma right about now. Tell him I said he has some fierce competition. Both of you really know how to gut a bitch out.”

“ I’m honored, but that’s something you can tell him for yourself. You’re coming along for the ride.” With the youthful vigor of a spry ninja, Jiraiya leaped out of bed while carrying Kakashi like a bride on wedding day. He hopped out of the window and used the walls of the adjacent building to propel himself to the roof. Kakashi flailed his arms around as he tried to free himself from the larger man's tight grip. He couldn’t tell if it was the cold night air or his own embarrassment that caused the shivers to run down his spine. His body was completely bare besides the mask and people were filling up the streets as they returned home from work.

“ What the hell are you doing?! Someone could see us up here and we’d be the talk of the town. Let’s get our clothes at least” He pleaded with the man and hoped he would let him go.

“ Nope. I’m feeling risky tonight. Good sex waits for no one. You and Asuma and going fuck me from both ends so I can complete my research. Asuma’s going to have one hell of a surprise when he sees us. Let’s go!!” Jiraiya leaped from roof to roof in pursuit of the hung dick belonging to Asuma. A true pervert is always eager for adventure.

Notes:

In case you don't know, this is a fanfiction for the Naruto series. I've always imagined Kakashi making a perfect big booty bottom and being even more perfect if he had a chubby body. It just seems to suit him so well. I could also see Jiraiya being hedonistic enough to experiment with men to see how it feels. It'll be fun writing chapter 2 where he gets in a threeway with Asuma and Kakashi.