The night could not have been going worse for Subaru. Well, that was not entirely true, no one died or had any lasting injuries or lost anything truly important yet, but it was still pretty bad. He offered to go pick up taxes from one of the Mather's domains villages which went fine on his own and he was even able to find some nice gifts for Emilia and Beatrice, and Rem when she woke up. The problem started when he tried to go back. He had been about halfway back to the mansion but was ambushed by bandits. They were not even really that tough so if he brought literally anyone else, he would have been fine. But since Patrasche was sick he had to have a more scared ground dragon, Patrasche would give him and the replacement an earful when they got back.
The only problem was getting back. He'd lost the carriage when the bandits arrived and lost pretty much all of the money that was in there. He was thankful they were dumb enough to let down their guard so he could slip away. Subaru was not thankful they'd made him dress up in the women's clothing he'd had in the carriage and took his clothes. They got their laughter in from him dressing up, more so when they even made him dress in women's underwear. At least he looked good in the "Natsumi" outfit. A silver lining, he supposed.
Subaru and the ground dragon were tired after the long trip to and from the village and the attack did not help with the nerves, luckily there was a tavern at the last bit of the trip. Pulling the ground dragon into the stable he found a familiar face. Frufoo, Otto's personal ground dragon! He tied up his ground dragon and gave Frufoo and scratch on the bottom of the neck and while Frufoo was confused after a few cautious sniffs they found out it was their master's friend.
Subaru hurried inside but careful not to get his dress dirty from the stable, it was the only clothes he had right now. Inside the tavern was dank, dark, smelled of foul alcohol and smoke, and was full of people drowning their sorrows in their cups. So, all in all a pretty average tavern. At the bar though he found who he was looking for, Otto was engaging the bartender with some banter as he was chugging down some of the local beer. Pushing past the people Subaru made it to the bar and behind Otto. He put his hand on Otto's shoulder and sat down next to him.
"Otto, I know what this looks like but," Subaru was interrupted.
"Well, hey pretty," hic "pretty lady." Otto slurred his speech, "what can I do for you."
Subaru's hopes were dashed in that instant, he knew Otto was a lightweight, but he had thought he was gonna be sober enough to get them home at least. "Otto when we get home, I am so gonna kick your ass," sighed Subaru.
The drunken Otto laughed, "I do love a lady who can kick my ass."
"Otto, you drunk it's me, Subaru."
Otto got huffy as he swayed back and forth in his chair, "Hey I'm not dru-" he put his hand to his mouth to prevent either a burp or barf. "Nope, I'm drunk." He smiled happily.
Subaru shook his head, Plan B it was then. "Hey barkeep, did Otto here have a room here tonight?" Subaru thought he was gonna have to stay here anyway, it wouldn't be the worst thing to put up with Otto. Heck he could even steal the bed for himself.
The bartender was polishing a glass. "Yeah, he got one about two drinks ago. Good thing too because he was about to get cut off. Can't have people falling asleep at the bar, bad for business." Subaru supposed he was right. "But uh, it was a room designed for two. Especially not for a lady of the night such as yourself."
"A lady of the night..." Subaru caught on faster than he would have liked, "I'm a guy, his friend! Look the clothes are because of-"
The bartender put his hands up defensively, "Hey I'm not gonna judge, I just own the place. It's just don't do anything to kinky or rob him. I'm running a tavern not a brothel here."
Subaru's temper was flaring but he knew he could not do anything about it now. He clenched a fist under the bar, "just tell me which room it is so I can put Otto here to sleep. The bartender did and so Subaru took the drunk and rambling Otto to the room across the bar all the while getting looks from about half the patrons. Subaru felt humiliated, frustrated, and ready for the night to end.
The room was considerably smaller than the rooms at the mansion only having enough space for an uncomfortable looking bed and a small nightstand with a lit candle. Subaru prepared to toss Otto onto the floor after closing the door when Otto spoke up. "Oh, my bed, a pretty lady and an open bed can only mean one thing."
Subaru groaned, "Otto stop thinking with your dick and start thinking with your head. It's me, Subaru."
Otto looked him dead in the eyes, "I have a friend named Subaru, but he's a guy."
Subaru did not know if he wanted to slap some sense into Otto or slap himself for thinking he'd even understand. He closed his eyes and took a deep breath to calm down. In that instant Otto took that as his chance to pin Subaru to the wall and give him a kiss on the lips. Subaru eyes opened in an instant and he began struggling. "Otto what in the hell are you doing!"
"What? Drinking and then spending the night with a lady is what I used to do on hard worked weeks." The kiss may have sobered him up some, but Otto could still not make out that it was just Subaru in a dress.
"Otto, I swear to God if you don't stop this right now-"
Subaru's struggle came to a head when Otto planted another forceful kiss on Subaru after lifting up the bottom of the dress and snaking his hand on Subaru's dick stuffed into the panties. Subaru gave another yelp but this time something else was mixed in. A moan from the gentle touch of his friend. "Wow, you really are a guy." Otto's slurring disappeared and with it came a voice of ambivalence. But that quickly disappeared, "well it's not to bad. My best friend is dating a half-elf and I'm in love with a cat girl so guys having sex doesn't really mean much."
"But I am Su-," Subaru's objection was cut off as Otto started stroking him with the palm of his hand through the panties. Subaru had only got a few kisses from Emilia and some not even from this Emilia and here he was moaning because his friend, his guy friend, was playing with his cock. Forceful yet gentle, needing yet pleasuring. Tonight got even worse. Subaru could not resist when Otto went for another kiss this time parting his lips and working his tongue in Subaru's mouth. Subaru wanted to put his mind on Emilia, how they would eventually be like this, but his body fought him to stay in the moment.
Then Otto stopped his stroking assault and pushed Subaru to his knees in front of him as Subaru was still dazed from the moment. Subaru could see the bulge in Otto's pants and his stomach churned. This shouldn't be happening this shouldn't be happening this shouldn't be happening this shouldn't be happening. Otto dropped his pants and his cock was right at eye level. Subaru couldn't make out the size, but he knew it was big and he knew what Otto wanted. "Come on, don't be shy." Subaru shut his mouth, he could feel the wetness from Otto's precum and the smell from it was a bitter sour smell. Almost an intoxicating musk. Subaru let the cock in.
Otto moaned in relief as his member found it's spot. So warm, so wet. Subaru had never been with Emilia let alone seen her naked or got to grope her yet here he was, dressed as a woman in a tavern sucking a man's cock. Otto's cock. His best friend's cock. On instinct alone Subaru started sucking and licking all around the cock. "Oh Frederica." Otto moaned. Oh, great he's thinking about someone else, Subaru caught himself thinking. Why did he care who Otto was thinking about? The sooner this was done the sooner he could forget this night ever happened. Subaru didn't think about guys like that. Not Otto.
Subaru put his hands on Otto hips and gently pushed them back and Otto obliged with the request. The cock was out of his mouth with only a single strand of spit connecting the two. "The name's Natsumi," Subaru gave his crossdressing name while trying to catch his breath. He didn't know why it mattered but Otto calling out someone else really ticked him off. Maybe more than him forcing the cock on him.
"Nat...sumi," Otto muttered.
Subaru gave a nod then took Otto's cock in hand. Instead of Otto thrusting in Subaru took the lead and started bobbing his head on the cock. Back and forth. Back and forth. His tongue swirled along the member feeling every inch he could fit in his mouth. It must have been good enough because soon Otto was moaning heavily and saying "Natsumi." Subaru couldn't help but feel pride at that. And then feel hatred for feeling that pride. He was supposed to be Emilia's. But then Otto gripped Subaru's head and gave one final thrust before shooting a load into Subaru's mouth. It was so thick, so bitter, so creamy, so Otto. Subaru swallowed the load. He even sucked the last drops from Otto.
Releasing the cock from his mouth the two needed to catch their breath and regain some stamina. Subaru thought they were done, he thought Otto had been satisfied but Otto picked him up from the ground like he was a bride and plopped him down on the bed. "Look, Otto, please," was all Subaru was able to get out before Otto pulled the dress up once again and revealed Subaru privates in the girly panties. Otto pulled them down slightly and Subaru's cock sprung forth. Otto took two fingers in his mouth and wetted them. Otto lined up taking Subaru's cock in his mouth with putting the fingers to Subaru's virgin hole.
Subaru moaned as his cock was getting some much-needed sucking and as his asshole was getting opened. The push inside hurt. Playing with his anus, thrusting the fingers in the delicate hole, and widening it. "Otto," Subaru moaned. It felt like Otto stopped blowing him long before he stopped with his fingers. But eventually he did stop. And he positioned himself above Subaru. The only objection this time was Subaru taking a kiss from Otto. A deep, romantic kiss saying he was ready. Subaru stopped think of this being wrong, he still loved Emilia of course and he didn't think he loved Otto in the same way. But in this moment, he was Natsumi, and Natsumi used their ass for pleasure. Right now Otto, later...
Otto thrusted his whole cock in. They moaned each other's names. Subaru opened his mouth and let his tongue out Otto reciprocated and the two fought in a fierce battle over which one kissed better as Subaru was getting his ass pounded. Subaru felt whole as Otto his just the right spots to make his body feel sparks of pleasure. It felt like an eternity as well as too soon as Subaru could feel Otto's cock twitch from inside him. "Inside inside," Subaru moaned wrapping his legs around Otto. After a few more thrusts Otto exploded inside of Subaru sending rope after rope of sticky cum inside Subaru. Subaru gave out and shot cum all over his own chest.
Subaru relaxed his legs and allowed Otto to remove his cock. Slowly and with and audible pop sound Otto removed himself. A small gush of cum dripped from Subaru.