Fancy Dress, Booze and a Sore Ass!

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Jim and Charlotte were walking home from a nice lunch at a local restaurant when they spotted a flyer for a costume party that night.

It was going to be at a club just a few blocks from their apartment and Charlotte was keen on going.

“Wouldn’t it be fun Jim? We could get dressed up like we did in college and have a wild night! We haven’t cut loose since we got married and I think it would be great to go out and get crazy, don’t you?”

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Jim was hesitant just because he didn’t know anything about the party. How could they tell what would be going on at this place based on a flyer? What if it was some kind of gang party or something (which didn’t really make sense but Jim tended to be a bit of a worrier, something that his wife was trying to work on)?

“Okay, let’s do it,” he said after careful consideration.

His lovely wife planted a kiss on his cheek and hooked her arm in his so they could rush home to get their costumes. He went into his closet looking for the things he had worn in college but his James Bond outfit was way too tight and his lumberjack outfit from high school was the same. He had filled out a little bit since his college years when he was incredibly skinny. He was actually surprised that a woman as hot as Charlotte had even gone out with him in the first place because he was pretty scrawny when they met. That worked out pretty well for him, though.

He turned to his wife as she was putting on her dog costume and informed her that they wouldn’t be able to go because he didn’t have a costume. Ever the fun-loving beauty Charlotte immediately figured something out for her young and somewhat insecure husband.

“Here, you can wear something of mine,” she said, handing him a tiny waitress uniform that she had worn to a party during their junior year.

He remembered how incredibly hot she looked in it and how she had teased him all night long by bending over and flashing her ass at him when no one else could see. They had some of the best sex of their lives that night because by the time they got home his dick was rock hard and practically spilling out of his pants. Maybe it would have the same effect if he was wearing the costume.

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He wasn’t sure about leaping crossdressing like this. He didn’t think he’d look very good dressed as a woman but his wife didn’t even bat an eye when she handed him the costume. She didn’t have a problem with him dressing like a woman so if she was okay with the cross-dressing then he wasn’t going to put up a fight. He always looked to Charlotte to guide him in matters like this one and she had never led him astray so he figured it was fine.

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He put on the dress and it felt surprisingly good. It was a pretty stereotypical sexy waitress look with a short skirt, a black tank-style top half and surprisingly sexy white ruffle sleeves that went just a little bit past his shoulders. There was a red doo-rag that went over his head and even though it kind of reminded him of what a pirate would wear he put it on. He was pretty much doing what his wife told him to because, once again, she had never led him astray.

They made their way to the party and found that it was already well underway when they arrived. The music was pumping and there were people in costumes of all kinds inside. The drinks were cheap and both Jim and Charlotte ordered enough to get pretty well buzzed. They weren’t interested in having just a little bit of fun that night. If they were going to go out and party it was going to be a wild, wild night and they were going to make sure they had no inhibitions so they could enjoy it as much as possible.

Charlotte had been a party girl in college and she had quieted that instinct after they got married. Tonight she was letting it out again which is why Jim found himself standing alone less than an hour after they arrived. His wife wasn’t going to cheat on him but she was going to enjoy the attentions of the men at the party who liked her naughty costume, which was essentially a tight body stocking with a dog’s head at the top. She was playing the part of a dog but she was showing off her hot body and the men loved it.

While Jim was watching her fade into the mass of bodies at the party he heard a sensual voice behind him, “Hey cutie.”

He turned around to see a very beautiful woman in a long green dress and matching green opera gloves. He had always had a thing for girls in gloves and her dress was slinky and sexy so she was pretty much perfect. He wondered briefly what her costume was but didn’t think about it much because she started groping his dick through his skirt and he could think of little more than how good it felt and how nervous he was that his wife would see.

Jim and Charlotte enjoyed a very healthy sex life but that didn’t stop him from dreaming about other women. Plus, the last he had seen of his wife she was dancing very closely with another man so he figured there wouldn’t be any harm in indulging in a little fun with this sexy girl. The fact that he was a crossdressing boy that night and that he had downed four drinks already made it pretty difficult to decide anything with a sound mind so he was just going by the seat of his pants. It was a fun ride so far though and he wasn’t about to get off.

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When the girl whispered into his ear that she wanted him to follow her to the bathroom he had to stop and think. If he followed her then he would almost certainly end up cheating on his wife. However, he was wearing a slutty women’s and a little bit of cross-dressing sex might have been okay with his wife. He couldn’t see her ask so he just went along with the beautiful girl, following the commands of his dick over the protests of his brain.

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She locked the door behind them and sauntered over to the last stall in the way that only a truly sexy, sensual woman could manage and spoke, “Well, what are you waiting for?”

She was asking him to join her in the stall so they could have sex and by that point, he was so aroused he couldn’t have stopped himself if he wanted to. He walked in, she shut the door behind him and pulled up the bottom of his skirt to reveal his dick with no panties. That’s exactly how his wife had worn the outfit years earlier and she thought it would be fun if he copied her. She probably didn’t imagine that he’d end up getting a blowjob from some slut in the bathroom though.

The girl gave her new cross-dressing lover a great head, slurping and sucking on his cock until it was rock hard. She had sucked lots of dick before because he had never been gobbled so lovingly. Even his wife, who was an enthusiastic woman in the bedroom, had never given him such a great blowjob. The beautiful girl even licked his asshole a little bit. Jim thought that was pretty wild at the time she was doing it but in just a few minutes he would understand her purpose.

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At the time he thought she was just being a kinky slut but it turned out she was getting his asshole ready for a deep sissy fucking. The girl in the blue dress and the sexy blue gloves was not a girl at all. Her costume was a girl; she was a cross-dressing man just like Jim and she was about to fuck his ass with her big sissy cock. The two of them were going to have hot crossdressing sex and because she had given him such a good head and gotten him so turned on he couldn’t even bring himself to ask her to stop even though he knew it was going to hurt.

When she pulled her dress up over her waist and revealed an enormous and rock-hard cock Jim’s eyes went wide. He knew that dick was going to be in his asshole soon and he was scared. He opened his mouth to object to her intentions but the beautiful crossdresser stuck her tongue down his throat and guided her cock to the opening of his asshole. With one quick thrust, she managed to get half the length inside him, fucking him like the sissy bitch he knew he was becoming. A man can’t get fucked up the ass and not become something else. He certainly wasn’t a genuine man anymore, not after letting this beautiful woman fuck him so hard and so deep.

Her crossdresser cock was balls deep inside him and even though he was moaning in pain and begging her to take it out she kept on thrusting. He was drunk and the truth is he was pretty aroused so he didn’t want her to take it out. He just thought it was the thing he should be saying with a dick in his formerly very manly ass. He kind of felt like a slut getting fucked so hard and he was a little embarrassed to be enjoying it so much.

He was sitting on the toilet when she had first slipped her sissy cock into his newly minted sissy asshole and after a few minutes fucking him like that she wanted something new. The girl with the big cock deftly spun him over and pushed his head onto the lid of the toilet while she slipped her dick into his asshole from behind. It was a lusty, sensual doggy style crossdresser fuck and it finally started to feel amazing. That position allowed her to get really deep in his asshole and she was massaging his prostate with her cock. Every thrust made his dick jump and despite a deep sense of shame at being fucked like a woman he could feel an orgasm approaching.

The sissy sex was powerful and Jim was beginning to wish that he could have sex like that all the time. He liked being taken like a woman and it occurred to him that costume parties were going to be his favourite. He would be going to any around the city looking to meet up with this girl again so he could get fucked hard.

After ten minutes of pure hardcore bliss, the girl with the big cock unleashed her cum into Jim’s asshole. She officially made him into a sissy bitch when she filled his rectum with jizz and he was in heaven. After she was done she pulled her panties up, fixed her dress and simply walked out. She didn’t have much to say to the man she had just turned into her bitch and that was fine by him.

Later that night Jim and his wife were sleeping peacefully when he awoke with his asshole burning. He had never been fucked before and he was hurting. He liked the pain though because it reminded him of the pleasure he had experienced with the beautiful girl in the blue dress and the blue gloves. It was a pleasure he knew he had to experience again sometime.

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