Lily's Cosplay Show

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Hey, you said there were three costumes, right?" Ryan replied cheekily.

Lily just groaned in reluctant assent as she rose from the table.

"Fair enough, fair enough," she muttered as she shakily made her way to the closet across the room. "One more!"

Ryan re-seated himself on the couch. The sexy moans of pleasure from his girlfriend had brought forth his erection again and he casually played with himself as he pondered the possibilities--both for the outfit that Lily might come out wearing as well as the potential sex positions they might explore.

This costume change took a bit longer than the last, but not too long.

"I hope you're ready for this," Lily called out enticingly, still hidden behind the door.

"Oh, I'm ready," Ryan answered back eagerly.

As she stepped out, Ryan noted that she had definitely saved the best for last. Or, at least, the one that he would think of as the "best". She was dressed in the white-bloused, orange-skirted costume of one of the sailor scouts from Sailor Moon. Ryan had never been deeply into that particular anime, but he was reasonably sure it was Sailor Venus. Not that it mattered--the dark orange skirt was tantalizingly short, showing off basically all of the sexy long legs that he loved so much. Additionally, unlike the other two outfits, this one came with shoes--orange high heels with an ankle strap. He had never seen Lily in heels before and it made her legs look even better than he thought possible.

"Holy fucking shit!" he exclaimed, greedily looking her up and down.

Lily giggled shyly at his reaction and slowly made her way across the room. She was clearly inexperienced in wearing heels and had to walk very deliberately.

"I hate heels," she explained with frustration, still taking it one step at a time. "But Ingrid lent them to me so I could match the color to the skirt, so I figured I'd put them on."

"Ingrid?" Ryan sniggered. "An old lady from the quilting group is doing Sailor Moon cosplay?"

"She's our age," Lily shot back. "She's in my calc class."

"Well, she has great taste in shoes," Ryan replied, rising to his feet as Lily made the last few steps to approach him. "Although I doubt she'd look half as good as you in them."

Lily brushed off the compliment as she finally finished crossing the room. Wrapping her arms around Ryan, he did the same and their lips met in a long, slow kiss that gave way to another, then another, then another.

Still naked from the waist down, Ryan's erection pressed against the fabric of her skirt. It was somewhat rough, but he also didn't want to get any precum on the outfit, so he deftly lifted the skirt and tucked his cock inside. Lily had not put her panties back on and her own small erection brushed against his.

Their kisses grew shorter and faster.

"Do you like being taller than me?" Ryan asked with a chuckle, slouching slightly. He was normally several inches taller than his girlfriend but in these heels the roles were reversed.

"No," she replied flatly.

Fearing that he had struck a nerve, Ryan laughed it off and stiffened his posture, standing on his tiptoes to, barely, rise above her.

She smiled at his attempt to make things more comfortable and suggested a better way.

"I want you inside me. While I sit on the edge of the table," she whispered in his ear. "I'm already lubed up and ready to go."

In a flurry of kisses, they shuffled together to the large table in the center of the room. They paused briefly as Lily hopped up on the edge and spread her legs. She wrapped her arms around the back of his neck, pulling him toward her.

Ryan lifted up her skirt and tucked it behind her penis, small but stiff and excited. Before dating Lily, he never would have guessed that this would excite him, but there was something about seeing his big, hard cock beside a much smaller, more feminine penis that turned him on immensely.

She had indeed lubed herself up. Ryan swirled the head of his cock around her pussy, slicking it up too. He then slowly pushed himself in.

Lily's breath caught as he entered her. In their current position, she felt even tighter than normal.

He only made it an inch or so before pulling back and gently pushing forward again. Slow, deliberate thrusts went slightly deeper each time, until Lily's breathing became less labored and more relaxed.

No longer having to concentrate on not going in too fast, Ryan was free to focus on other things. He leaned forward and began kissing again, back to slow, steady kisses, in time with his thrusts. His arms wrapped around her but only brushed the rough fabric of the sailor scout outfit. He noted that this was just one of the downsides of costumed sex--not being able to feel all of her smooth, bare skin.

Of course, she wasn't entirely covered up, he realized. His hands moved from her back and shoulders down to her legs. He wasn't in the best position to feel all of her, but he was able to caress the warm flesh of her thighs as they pressed against his hips. He really didn't want to finish so quickly, but at the rate he was going, it wasn't far off.

Without realizing it, he had sped up to a frantic pace and felt guilty when Lily gently pushed him back.

"Too hard?" he guessed apologetically.

"No," she replied, slightly out of breath. "I just want to move to a different position."

Ryan looked at her, expectantly. He was up for anything.

"I want you to take me from behind," she whispered.

Not needing to hear it twice, Ryan kissed her gently as he carefully pulled himself out. He then stepped back and allowed her to reposition herself.

All the Overwatch talk from before had probably put it in his head--a phrase in gaming used to describe the best, most awesome part of a match: Play of the Game. POG. Or, less formally, "pog". Or "poggers". And, bent over the table, her long legs bare and toned up by the sexy high heels, her tiny skirt flipped up to show her tight white ass, shaking invitingly for him to plunge himself in as deeply as he could go... well, this was definitely the evening's POG.

Stepping up to position, Ryan adjusted his stance to guide himself back into Lily's awaiting pussy. He entered slowly, but she was still relaxed, so it wasn't long before he was pumping away, burying the whole length of his cock in her.

Back at Lily's apartment, where they usually had sex, they were limited to a loveseat and a bed--her tiny breakfast nook table definitely wouldn't be able to withstand this kind of pounding. The experience of fucking on a table like this was new to Ryan. New and amazing. Just like doggy style, he was able to grip her hips and ass while he pumped away. From a standing position, he had much better control of his movements instead of being on his knees. He pulled out further than he normally would before plunging in deep.

For her part, Lily seemed to be enjoying herself too, moaning softly with each thrust. But, for Ryan, that wasn't enough. He really wanted her to have an amazing orgasm before he allowed himself to finish. So, he slowed his thrusting as he leaned forward.

"Need to change positions, baby?" she asked curiously.

"Not at all," he replied. "I just want to make you moan even louder."

To illustrate his point, he brought one hand up and under her, cupping a petite breast. Her nipples were exquisitely sensitive so, even through the fabric of the blouse and the bra, he was able to take her breath away with well-placed strokes. He then stiffened his hand in a position such that, with each shallow thrust he made, her body moved forward, running her nipple across the ridges between his fingers. His other hand went lower, rubbing her perineum in forceful motions in time with his fucking.

Her moans indeed grew louder, which turned Ryan on even more. It was now a race for him to not come first. His thrusts slowed almost to a stop, which Lily didn't seem to mind, because he continued to pleasure her with his hands.

"Oh, fuck, Ryan!" she exclaimed.

And with this, he resumed his thrusting, at full force. He was so close and when he felt her orgasm--a dual sensation of a clenching around his cock and a dribble of cum from her penis that leaked out onto his wrist--he lost it too, shooting his load deep inside her with powerful thrusts, which gradually slowed to a stop.

They stood coupled together for a time, catching their breath and basking in the post-orgasm afterglow. Ryan eventually broke the silence.

"Hey, it looks like, as long as you keep the skirt lifted up, we'll manage to not get any cum on it at all."

"Poggers," Lily sighed in triumph.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
12 Comments
cmm0cmm08 months ago

I loved it almost as much as the first one. A beautiful story about beautiful people by an awesome writer 🙂

AnonymousAnonymous10 months ago

Loved it just like the first story. I really hope to read more of them in the (near) future.

AnonymousAnonymous11 months ago

Ryan is my hero and lilly my muse. What a beautiful relationship!

damnedfrogdamnedfrogabout 1 year ago

I've loved the first story of Lily and Ryan, and love this too.

I hope you will write other stories of this cute couple.

EdeyEdeyabout 1 year ago

I would love to write more about them and maybe about putting a ring on it ;)

Show More
Share this Story

Similar Stories

Lily in Bloom Ryan's college crush is not like what he had imagined.in Transgender & Crossdressers
Secrets and Surrender High school can be lonely, but shared secrets can help.in Transgender & Crossdressers
My Transgender Neighbor Mike falls for his blonde transgender neighbor, Caroline.in Transgender & Crossdressers
Maybe, It Gets Better Trans teacher Ana spends the night with three teen girls.in Transgender & Crossdressers
Locked Out of Apartment The sexy neighbor girls have a surprise.in Transgender & Crossdressers
More Stories