Mike and his new bride Carla were not a typical couple. It was rare to find two people that were still virgins when they got married but these two had been dating since high school and they had pledged that they wouldn't have sex until they were joined in holy matrimony. It was obviously difficult for the both of them but especially for Mike since Carla was such a hottie. She had long blonde hair, big perky tits, a tight tummy, a wicked hot ass and plump dick sucking lips that would someday coax multiple loads of cum out of his cock. He had made a promise though and he was pretty sure the two of them being virgins was going to make their honeymoon sex way, way hotter.
The two of them got married in May and took a week off to go on a beautiful, romantic honeymoon. They were planning on having sex the first night, obviously, and they were on an after dinner walk in the park when their lives changed forever. They had just eaten at the fanciest restaurant in town and one of the patrons had paid for their dinner because it came out that they were on their honeymoon. So they had eaten what was probably a $400 meal (with the wine) and paid nothing for it. It should come as no surprise that they were on cloud nine and deeply in love as they strolled arm in arm through the park.
Carla was wearing a short red dress with long sleeves and a scoop neck and a pair of fishnet stockings on her long and sexy legs. She knew it was a little bit racy to be wearing something like that to a fancy restaurant but they made her feel really sexy and a little bit slutty and she really liked that. Mike had his arm around her waist and he was thinking about how badly he wanted to fuck her as soon as they got back to the hotel room.
He stopped and turned to face her, "I love you Carla. You're so beautiful and perfect and I can't believe that you and I are going to be together for the rest of our lives."
With that he planted a passionate kiss on her lips and their tongues intertwined. As they kissed they were completely lost in the pleasure of it so they didn't notice the burly bald dude peering at them from behind a tree. If they had they probably would have seen his hand furiously stroking his dick and they almost certainly would have run at the sight of it. They would not have been interested in sticking around so some pervert could enjoy the site of them being in love.
They were too caught up in their newlywed passion though and that meant they didn't spot him until it was too late. He stepped out from behind the tree, an imposingly tall man with incredibly broad shoulders and a whole lot of muscles, and asked them if they liked what they saw. That's when they finally spotted his alarmingly large cock protruding from his pelvis.
"If you do what I tell you no one will get hurt. Otherwise I'm going to mess up your bride's pretty face and I know you don't want that, do you boy?" he growled at them.
Looking at the grown Ian could barely get the words out, "No sir, I don't want that. I swear, we'll do whatever you want."
Carla was too terrified to be upset that her husband was being such a pushover. Instead she was worried about this man's threat of breaking her face with his fists. She knew that he had the power to do something terrible to her and she suspected that he had the drive to do it too. It would take a seriously broken man to abuse a woman like that and he seemed like just the type.
"I want you two to switch clothes. I want the boy wearing your pretty red dress and your fishnet stockings and to be honest I want you wearing only your panties little slut girl. He can just throw his clothes on the ground. That's it, take your clothes off."
They looked at each other with fear in their eyes and when he barked at them to do it quickly they started stripping with the kind of speed that would have happened if they had made it back to their hotel room. This time they were stripping for sex with someone else though. What neither of them could figure was why this scary looking man would want Mike to become a crossdresser. What use could he possibly have for a man in women's clothing? Maybe he just wanted Mike in a dress so he would be less inclined to run for help or try and fight back while his wife was being raped.
As it turned out they were wrong. He wanted Mike in the women's clothing because he intended on raping him, not Carla.
"You look so pretty in that dress boy. You've got a great, tight ass and a nice set of little balls there. Is this the first time you've dressed as a woman?"
Again Mike looked at the ground and answered meekly, "Yes sir it is. I'm not a crossdresser."
With a smile on his face the scarily big man said, "Well, you should be. You're a natural and I know that you could have lots of hot hardcore fun with guys like me. You see, I've got a thing for sissy boys. I love to fuck pussy too but nothing turns me on like seeing a man in women's clothing and getting to fuck him hard. That's right, this throbbing cock is going to slide into that asshole of yours. I assume you're a virgin?"
"Please, please don't fuck me sir. Please, I've never had anything back there and I know it's going to hurt so badly. Please!" he pleaded.
"Sorry bitch, I've been waiting all night for a couple just like you two and now that I've found you you're not going anywhere until I've had my fun. That means you need to get fucked."
He stroked his dick while caressing Mike's ass and his fishnet clad legs and the young crossdressing boy could see that the cock that would soon be invading him was dripping precum. At least that would make the entrance a little less painful. No matter what it was going to hurt though.
"Bend over that bench, slut. I'm going to fuck that sissy asshole of yours while your pretty wife watches. She's not going anywhere, right? She knows that I'll break you in half if she even tries to get away."
The time had come for Mike to get fucked in the ass and he was terrified. Taking anything up his ass was a terrifying proposition but taking a dick this long and thick was even scarier. Would the guy tear him open? Would he make his asshole bleed with his big cock? The time to find out was at hand and the fucking was going to start.
Mike's virgin asshole was pink and tight looking as the burly attacker rubbed his slippery cockhead over it. He was looking forward to fucking this bitch boy more than anything and his dick was eager to push in there and give it to him good. With slow and steady pressure he slide every inch of his thick dick meat inside the sissy asshole, fucking his new meat good.
"You're not a virgin anymore bitch. Now you're just a sissy slut that gets fucked by any big cock that wants inside you. Isn't that right bitch boy?"
Mike just groaned at the pressure that was building in his rectum. He was getting fucked like a woman and he was fighting hard not to enjoy it despite the mounting pleasure in his backside. Was it possible that all along he had been a crossdressing sissy and he had never acknowledged it? Was this thing living deep inside him just waiting to be released as his true self? He was really enjoying this crossdressing sex despite the slight pain that was caused by his ass being stretched so wide.
During all of this Carla was standing off to the side with her hands across her big breasts and her panties riding up into her crotch. She was a little chilly but otherwise she was just overwhelmed by the sensations of being forced to strip and watching her husband get fucked in the ass. Was he actually enjoying the sex this burly monster was giving him?
Mike groaned and let his enjoyment slip out, "That feels so good. Fuck me harder!"
"I knew you'd be a perfect little sissy bitch. I could tell from the moment I saw you too that you were the kind of guy that would love a little crossdressing sex. I just had to find a way to get you into a dress and as soon as that soft material slid over your head I knew you were going to be the perfect fuck slut for me. Now take all of my cock you stupid sissy slut!"
He thrust all 10 inches of his big dick meat into Mike's asshole hard and the young man screamed loudly. It hurt getting fucked like that but once again it felt so damn good he could barely contain himself. Now the big cockhead was rubbing against his prostate and it was an entirely new pleasure.
There was another virgin among the three of them and the attacker wasn't about to let her get away with not getting fucked. No, he was going to pop her cherry too and the poor girl was going to have to take everything he had to offer because he was the one in control. Pulling out of Mike's asshole he directed his dick towards the trembling blonde just a few feet away and told her that it was time she lost her cherry too.
"You're not going to be a virgin much longer baby. My big cock is going to make that pussy of yours it's personal fuck hole."
He grabbed the slim slut and while Mike was still bent over the bench lost in the realization that he was a sissy crossdresser he fucked his new wife. He fucked the bitch in her tight pussy, breaking through her hymen and continuing to pump. There was a little bit of blood but that didn't stop him. He was going to screw her until his dick exploded, spilling a hot load of semen all over her.
It hurt like hell at first but in the end she loved it. She couldn't help but moan for him, telling him that it felt good to be filled with cock. Mike had just awoken from his stupor and he was stroking his dick furiously watching her get pounded. Their marriage had changed forever and was not likely to go back to it's innocent, virginal state. They had both lost their virginity but to a man with a huge dick and ropey muscles. It was good though. By the time it was over both guys had shot their loads on Carla's body and she had cum more than a few times. She was now a fuck slut and they were both horny for cock meat. Mike would probably be a crossdressing slut forever.