It was a beautiful day at the beach and Chuck figured since no one else was around that he would strip everything off and go for a swim in the nude. It can be freeing to remove all impediments between you and the natural world and the good-looking young man was revelling in that as he swam around the salty water.
When he returned to his spot on the beach he noticed that his clothes were gone, which presented a problem. He would never make it back to his car without exposing himself to multiple people and that was liable to get him in some trouble. He figured there wasn’t any risk in going skinny dipping but it turns out he was wrong.
Someone had stolen his clothes and a quick survey of the beach to both sides showed only a few people and none with a pile of clothing. He was racking his brain for solutions to the problem when he saw a pink blouse and a short red skirt on a towel just a little ways down the beach. He hadn’t considered wearing women’s clothing to get himself out of the jam but nothing else was coming to him so he scampered over to the towel and quickly put on the clothes. He felt like a fool but deep in the recesses of his mind, something woke up and that something really liked being dressed in female attire.
He was pondering that sudden awakening when he heard someone yell at him from the water, “Hey, what the hell do you think you’re doing!”
He turned around to see a beautiful woman coming out of the ocean wearing a red bikini. It’s a shame he had taken her clothes because it would have been nice to flirt with her a little. Maybe he could have gone home with her and had some fun at his beach rental. Maybe if he had just asked her nicely if he could wear her clothes she would have said yes and they would have a great story about how they met under these super cute circumstances. All that was out the window now. To her, Chuck was just a creepy guy who was probably a crossdresser and went around stealing women’s clothing from the beach.
Instead of sticking around to explain that he wasn’t a crossdressing thief but that someone had stolen his clothes, he decided to perpetrate the same crime against her. He turned and ran up the beach, counting on being faster than her so he could make it to safety without getting in any more hot water. He never suspected she would do something like go to the cops but there happened to be a pair of them right there on the beach so she reported the crime and they were on it. It was not going to be Chuck’s lucky day.
One of the cops was a busty redhead with a pretty face and luscious lips. The other was a good-looking guy with dark hair and a strong build. When they found Chuck – it was pretty easy since he was dressed in women’s clothing – they arrested him immediately and put him in the squad car.
“You sure look cute in those clothes,” the male officer remarked as he pulled Chuck’s arms behind him.
Chuck hung his head in shame as he was placed into the back of the squad car with his hands trapped behind him in cuffs that strangled his wrists. He couldn’t have been more embarrassed at being caught dressed in a ruffled pink blouse and a short red skirt. It would have been a little less mortifying if the cop hadn’t insisted on complimenting him but the whole thing was just terrible.
The busty female cop got in the back seat with him and it seemed like she didn’t know he was a man. He was good looking but he did have feminine facial features so it was certainly possible she had made a mistake. After all, the girl had only reported that a thief had stolen her clothes, not what gender the thief was. The female cop sensed there was something not quite right with Chuck and when she slid her hand up his skirt and discovered his dick hanging down she knew. He was just a naughty sex pervert and he deserved to be treated like one. He was going around stealing women’s clothes so he could dress in them and there was nothing more disgusting than that.
At least, that’s what Chuck thought when she took a look at his cock and called him a pervert. Why would he have believed anything else based on her response? When the two cops brought him into the station he found out that she was way kinkier than he had ever thought. She didn’t think he was a piece of shit pervert cross-dressing slut thief. She thought he was kind of sexy and she wanted to have some fun with him.
“Since you obviously want to be a girl we should make you look like a girl. I brought my makeup to work today so we’re going to put you in some of it so you’ll look nice and feminine. Wouldn’t that be nice my little crossdresser?” she asked in as humiliating a way as possible.
Chuck mumbled something under his breath and hoped that she wouldn’t actually put any makeup on him because that would be utterly mortifying. To be treated like a girl and dressed like a girl and made up like a girl would probably be too much for him to handle. Sadly for him, that’s exactly what this lovely babe had planned. She was going to turn him into a cute little sissy for her pleasure.
The lipstick was the first thing she put on him. It was a shade of pink that she said would be perfect for a sissy crossdresser. It would make him feel like a woman to have that sticky, glossy substance all over his lips, one of a woman’s instruments for giving her sexual partners pleasure. The nail polish was the next thing to come out because Chuck’s feet and hands had to look pretty. If a crossdressing boy is going to look like a girl then he has to go all the way and use all the beauty products that are available to him. He must be committed to being a sissy and she was making sure that even if Chuck was a forced sissy that he looked good.
The sexy redheaded cop and her partner have a history of taking their more feminine collars and turning them into forced sissies for their pleasure. What they like to do is get them all dressed up and then violate them with a nightstick. The sissy gets boned up the butt while bent over and they get to learn what it feels like to be a real woman. How it feels to be violated by a cock. The redhead with the big tits is the one that always does the fucking while her partner simply watches and plays with his dick. It’s a good thing they have going on and they’ve turned many regular guys into crossdressers with this sexy program.
Chuck is the latest victim and after they put him in makeup it’s time for the truncheon to be forced into his asshole.
“Spread those cheeks nice and wide,” the beautiful redhead commands Chuck after bending him over. “Get ready for some fun.”
She manages to get a little bit of lubrication in there so he doesn’t get completely torn open and then the nightstick slides into his asshole and opens him up like he never thought possible. His day started out so wonderfully with a nice trip to the beach, some sun, some fun and a nice naked swim. That was his big mistake. He thought it would be fine to take a little risk and have some fun in the water without his bathing suit on but clearly someone else thought it would be fun to fuck with him by stealing that suit. A couple of hours later he’s bent over in a seedy back alley with what is effectively a hard cock up his ass.
The busty girl thrusting the toy into his rectum and making him a sissy slut was awfully passionate about her play and hearing all that moaning and groaning was starting to turn Chuck on. She was talking dirty too and it was affecting him in a way he didn’t even know was possible.
In a throaty voice, she purred at him “Do you like that? Does it feel good to have my nightstick shoved up your ass, churning your insides? This is what sissy crossdressers are supposed to take. They’re supposed to be bent over and used like hot sluts. Your asshole is my pleasure zone and I get to use it as I see fit. Today I want you to be my sissy slut, taking cock like you know you were born to do. Tell me that it feels good bitch.”
Chuck was enjoying the deep anal fucking and between thrusts, he panted to her “It feels amazing. It feels so good I don’t ever want you to take it out.”
Getting fucked in the ass was turning out to be the experience that led Chuck to a whole new sexual world. He couldn’t imagine not trying this again because it just felt so great having her fuck his asshole like that. She was actually pretty gentle with her thrusting, pushing it not too deep and not too hard so she didn’t tear him open but instead made him feel like a woman that was being made love to, except by a huge nightstick instead of a dick.
When Chuck turned around at one point he saw the other cop standing just a few feet away stroking his dick. Apparently, his part of the game was to stand around and watch. He was groaning too and moaning under his breath. Chuck assumed he was saying something dirty because his dick kept getting bigger and thicker and it looked like it was going to explode soon. He knew from his own experiences masturbating that when the head expands like he was doing it means that an eruption is coming soon.
The sexy cop pounding his crossdresser ass was giving Chuck a reach around to make him even hotter. She wanted him to feel like getting fucked up the ass was the most pleasurable thing in the world and there’s no better way to do that than to stroke his big dick while the action is going down. She had unbuttoned her top too and her titties eventually came bounding out. She wanted the sissy crossdresser to suck on them to make her pussy wet. She loves having her nipples licked and when he got those plump pink lips around them he didn’t want to let go. He was like a hungry baby yearning for breakfast.
The male cop walked up to Chuck with his dick throbbing and huge and he knew the cock was about to explode and spray thick white semen all over. The guy groaned at the forced crossdresser and then let his load loose, firing it on Chuck’s dick and legs. He gets him a little bit cum stained and that only made the sexy crossdressing boy hotter. He was fully enveloped in the role of the sissy and there was a chance he was never going to get out of it.
When a man discovers a sexual pleasure that he never imagined possible he’s loathed to give it up. He doesn’t ever want it to go away and that’s what happened with Chuck. After fucking him and cumming on him the officers let him walk home of his own volition and as he strolled down the street in his skirt and ruffled pink top he couldn’t help but think he kind of liked being a crossdresser. He also liked all the people looking at him, even if some of them were saying nasty things. The attention was nice. It’s possible Chuck had been transformed into a sissy.
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