Story: Pretty Pokegirls

“Hilbert… Hilbert your hand feels so good.” Nate whimpered as his friend pumped away at his shaft.

“That’s not right, silly! Remember, I’m Hilda!” Hilbert replied “And you’re Rosa, remember?”

A-aah… yeah…” Nate replied.

There was no better way to spend an afternoon for Hilbert and Nate than indulging in their deepest, darkest secret. The two were crossdressers. Not the “I want to feel pretty” or “I like wearing drag” kinds, the “I want to be a little slutty faggot who wears short skirts and gets fucked by stronger men” kind. They sat on Hilbert’s bed, lovingly stroking one another in their newest crossdressing outfits.

Nate or “Rosa” as he wished to be called was dressed in his friend Rosa’s clothes while Hilbert or “Hilda” as dressed in Hilda’s. Nate had on a tight long sleeved shirt ending in a short yellow skirt and long black tights, complete with a nice hole ripped in the middle for Hilbert to access his cock. Hilbert was wearing a black jacket, white top, and ultra-short jean shorts with his own dick poking through the zippered opening. The two were so excited to have finally gotten enough of their female friend’s clothes to dress as them, with their ongoing mutual masturbation session proving just how enthusiastic they were.

For 20 minutes the two sat there, gently stroking the other, kissing, and occasionally breaking into ridiculous conversations about how girly the other was. Both of them were hard as iron from so thoroughly indulging their fetish.

“I love being a girl! Do you think I look cute in this, Hilda?” Nate asked.

“You’re so cuuute!” Hilbert replied. You look so good in tights!”

“H-haaa, thanks…” Nate replied, growing a quieter as Hilbert’s stroking continued.  Hilbert started to pick up on this.

“Oh gosh, is my pretty little girl okay? Is she gonna cum~?” Hilbert teased.

“Y-yea…” Nate replied.

“Gosh, are you really gonna cum? Dressed in girl’s clothing like this… you really love being a pervert, don’t you?

“Mhm…” Nate replied.

“Now, what do we say if we want to cum again Rosa?” Hilbert asked.

“Please…” Nate responded.

“Please what, princess?” Hilda retorted.

“Please let me cum!” Nate whimpered.

“I don’t think you want it~ Be a big girl and tell me that you reeeally want it1” Hilbert teased.

“P-please let me cum like the perverted girl I am! I’ve g-gotta cum so bad!” Nate shouted.

“Good girl~” Hilbert replied, increasing his stroking to a brisk pace and making Nate huff in excitement at the sudden overstimulous.

“Haaa…AAAaahh~! Oooh Hilda! I’m going to cum! I can’t stop it, I’m going to jizz in my sk-skiiiirt~” Nate moaned. Both of his hands gripped the yellow skirt he was wearing and tried to conceal his throbbing erection as if there was any way to hide he was about to cum. Fantasies about breaking down in public and simply being unable to hold on rushed into his head as that sweet climax finally hit.

“O-OOOOOOooohhh~!” Nate cooed as his cum splattered a dark stain against the bright yellow dress. Several more jets collided with the garment, making Nate’s crotch a sticky mess of hot white love. Nate lay back on the bed, panting in exhaustion and enjoying his delicious post orgasmic glow.

Hilbert became a bit too excited seeing his best friend give into his fantasies and cum from their crossdressing session. The scent of Nate’s hot cum tainted the air instantly, making Hilbert lick his lips in anticipation. He shifted his position, placing his legs between Nate’s head so that his ass, wrapped in tight daisy dukes, was inches away from the other boy’s face. His head dove for his twinky friend’s crotch, peeling back the yellow skirt to thoroughly inspect the damage. It was heavenly. A thin white film coated his entire cock.

Hilbert placed his face right up against his friend’s cock, licking and kissing at the sides in delightful anticipation, savoring his friend’s salty taste. It wasn’t long before Nate was ready for round two, groaning at the sensation of his cock being so lovingly savored. His hands pried at Hilbert’s shorts, completely freeing them from the tight garment. His tantalizing hard cock and puckered asshole were inches away. What a lovely array of options.

Hilbert shuddered in delight as he felt a cold wet tongue piece his anus and slither around his insides. Nate knew far too well how to get Hilbert going with his tongue flicks, so delicately tickling his needy prostate. All the while Nate’s hands pumped at that impressive meaty shaft of Hilbert’s.  It was intoxicating. Slowly, Hilbert’s cleaning of Nate’s cock stopped. The sensation of Nate pleasing him was growing too intense. He pressed his face against the boy’s crotch, taking in the delicious smell of stinking cock as the boy’s lower half was worked on like magic.

“Yes… oooh yes… O-oooh my god Rosa, that feels s-so gooood!” Hilbert moaned into the other boy’s crotch muffling the sentence. Nate gave no response, hypnotized by the sheer depravity of what he was doing. He felt so deliciously submissive with his friend pinning him below his fat ass, working his tongue and stroking him off so feverishly fast just to have him get off to being the girl he craved to be. Hilbert fell silent as things hit a fever pace, shifting his weight against slightly and outright sitting on the boy’s face as he savored the tonguing of his life.

“Aah.. Aaaaahaa~!” Hilbert cooed in delight as orgasm struck. His hard cock flung its inaugural spurt against their bed spread before weaker bursts pattered onto Nate’s clothes below, covering the stomach completely. Hilbert sat there for a moment as the last of his load was drained by Nate’s hands, letting out a chorus of shudders before standing up to readjust his position on the bed.

Hilbert smiled at the sight of his little slutty partner in crime spent and covered in both of their cum. Hilbert scooped up a large blob of his own cum resting on Nate’s chest with his index finger, promptly bringing it to his mouth to savor the taste and join whatever was left of Nate’s semen in his mouth. He sat back down on the bed, pressing against Nate and locking between them in a face to face embrace. Their bodies wrapped together, locking them in a sweet white embrace.

As they looked into each other’s eyes, both still mad with desire but too exhausted to act much further, they locked lips. Back and forth their tongues swapped the taste of their combined loads, coating the insides of their mouths. The two laid there for hours, giggling and kissing one another as they both enjoyed being the horny slutty girls they were deep down.