Painful Hotel Surprise

Blair arrived at the hotel room in a short denim miniskirt and pink tube top. She knocked on the door and a surprisingly handsome young man swung it open. He surveyed her with a satisfied look and beckoned her inside. Her black stilettos clicked against the ground as she placed her small bag on the counter next to the television with a nervous smile. She wasn't sure what to expect, as she was quite new to this field.

"I'm Chet, nice to meet you," they shook hands. "My buddy gave you a glowing recommendation, I'm curious as to what you can do for me."

"Um... I guess whatever," she shrugged sheepishly, admiring his chiseled jaw and piercing green eyes. He gave her a warm grin, showing off his vibrantly white teeth and smoothed his short brown hair down , obviously in habit.

"You're new at this I can tell." Chet grinned. "Two thousand right?"

"Yes, and a condom if you're fucking me." Her slight shame mixed with excitement as he pulled a condom out of his wallet and tossed it on the bed.

"How do you feel about a little bondage?"

"Eh..." Blair looked around, pushing her long blonde hair out of the way to scratch the back of her neck. She was already prepared to have sex with the guy, what could he do, rape her? "I guess a little is okay." Her nervousness grew. She had been asked before by boyfriends, but never consented to any bondage. She wasn't kinky at all and would never have been doing this if she didn't have tens of thousands of dollars in student loans to pay off.

"Awesome." He walked to the bedside table and pulled out the money and a bit of rope. As she counted it he began rubbing her thighs, noticing her breathing get heavier. She slid the money into her purse and turned towards him with an especially deep breath. He turned her back around and tied her wrists. Smelling her neck and hair, he spanked her ass, enjoying the sound of a painful grunt. She closed her eyes as he nuzzled her neck affectionately, trying to imagine this being as romantic as possible, though it didn't feel that way to her. She decided to pretend they were a couple. Maybe we're on our honeymoon, she thought.

She hadn't experienced being tied up before and wasn't sure how she felt about it as he pushed her face up onto the bed. Struggling to see if she could escape if she wanted to, she suddenly realized her wrists were tied too tightly to move. As she was about to ask him to loosen them, he reached under one of the pillows and pulled out a red ball gag, which he stuffed into her mouth before she could finish the word 'can'.

'What the fuck does he think he's doing?' She grunted and struggled as he lifted her head and buckled the gag behind her neck. 'Oh my God this was such a mistake! He's going to fucking kill me!'

She kicked and struggled while he kissed her neck and cheeks. She was beautiful, he thought, and grabbed her hair to keep her head in place. Fat tears swelled up in her eyes and for a moment he pitied her, until he felt her breasts and regained control of the sexual fantasies he was about to force on her. She looked up at him with tears that smudged the pretty blue in her large, horrified pupils. He backed off of her chest, grabbing her writhing ankles. He wrestled them together and pinned them under his arm while his other hand pulled a snap tie out of his suit pants pocket. Beginning to sweat and pant, it took several minutes to wrap the thin plastic around her ankles and zip it tightly snug. He let go of her bound legs and they immediately shot up, knocking him in the chin. Biting his tongue, he fell off the bed with a loud curse.

She couldn't help but feel the smallest bit aroused. Here she was, struggling on a bed, bound and gagged for the first time in her life. There was an undeniable wetness in her crotch and she felt a mixture of shame and excitement.

'Oh shit was that a good idea?' She asked herself. 'Now he's gonna be pissed, and I don't want to make this harder on myself than it has to be. I mean he's obviously got something unpleasant planned. Wait... fuck that, I don't want to make it easy on this asshole scumbag!' Certain her situation couldn't get any worse as she slid towards the head of the bed trying to keep her short skirt down, she heard Chet correct her.

"Come on out guys," he rubbed his chin gingerly as two men in similar business suits entered from the bathroom. Blair emitted a muffled shriek, barely loud enough, it seemed to her, to wake a person sleeping on the other side of the room. Tears flowed down her face as she openly sobbed, gasping for breath through the ball gag. She hated the solid rubber jammed so far in her mouth she could barely swallow. Uselessly trying to squirm away from her approaching attackers, she began to plead with facial expressions and a rapid shaking of her head.

'What the hell are they going to do to me?' She unnecessarily asked herself. It was an instinctive question that she knew the answer to. She could admit a slight turn on a minute ago with only Chet, but three attackers? She was horrified and more than overwhelmed, panting through her ball gag as adrenaline surged through her body.

"Fucking bitch," Chet dragged her off the side of the bed by her hair and she hit the floor with a painful thud, choking on all the saliva in her mouth that was beginning to ooze down her chin. Her shirt and bra were ripped open with one powerful yank, exposing her full perky breasts. She found no part of this enjoyable as she was propped up on her knees and blindfolded. She heard three zips and felt the smooth delicate skin of three penises slapping her cheeks and lips. She grunted and moaned in protest. With every slap she felt more disgraced and violated. Tears dripped from the silky blindfold as she choked on the ball gag with disgust. 'Two fucking minutes ago I was just here to suck some dick and get fucked for some badly needed money. How in the hell did I wind up in this terrible situation? Prostitution is wrong, but do I deserve this?'

"Come on bitch," a voice growled as she was violently yanked to her feet by several hands and bent over the bed. She heard the men's pants being taken off and a pair of legs straddled her back and tied arms. Her head was forced up by her hair and the ball gag was removed, immediately replaced by a hand. She tried to bite the sweaty skin of his fingers but couldn't grab any with her teeth. She heard a clanking of metal as her mouth was ripped wide open by too many fingers to count. She tried to scream but her open throat could only expel gargles as her shoulders and arms began to go numb under the weight of the man. The fingers forced a large cold ring into her mouth with string ties that were quickly fastened behind her head. The man dismounted her and she was rolled onto her side, his hard cock thrusted deep down her throat. The sounds of her gags mixed with the loud slaps against her ass. Her thong was snapped with a painful tug against her thighs, and her shirt and bra remnants were also forcefully removed. The man on the bed hopped off, replaced by a different attacker, who began pumping her throat. The wet dick that had just left her mouth now proceeded to attempt to enter her asshole. She tried to pinch her cheeks together to prevent entry without success. She tasted the sweat of the throbbing cock in her mouth and felt the painful stretching in her butt. After a minute, the dick was completely inside her, thrusting in and out. She moaned in pain as she felt the cock in her mouth pull out. Burst after burst of warm cum was sprayed on her cheeks, blindfold, and tongue. It tasted terribly sour, but with her mouth held open she had no choice but to swallow it when it dripped to the back of her throat.

'Wow he came quickly. I must have really turned him on. What a nice compliment from this asshole rapist.'

"How's that taste you stupid slut?" She heard Chet ask as he slapped her across the face. A third dick was stuck in her mouth as her ass continued to be pummeled violently. This one wasn't hard yet, and it flopped between her tongue and the roof of her mouth.

She had never had a dick in her ass before and it was hurting her immensely. She groaned in pain as the man pumped in and out with force. As the minutes dragged on his dick was getting dry so he lubricated it with spit. As the now slimy dick continued to pound away at her helpless butt she realized it wasn't as terrible as she had always thought it would be.

The man inside her asshole groaned loudly as she felt his dick shoved as far as it would go, pulsating with powerful shakes, and she knew he was cumming inside of her. He pulled her skirt back down, as though that suddenly made her decent, while the penis in her mouth hardened. The still flowing tears met the spots of cum on her face, feeling sticky with every facial movement as the man in her mouth jerked her head back and forth. Her skirt was lifted and a penis was again inserted into her ass, this time to her enjoyment. She knew it was Chets, noticing the slight curve at the tip after a minute. She struggled for breath between her choking sobs and the milliseconds that the penis in her mouth was removed before reentering.

"Deep breath bitch," the cock was completely removed for a second. She gasped before her nose was held shut and her mouth was filled with the slimy rock hard penis. It hit the back of her throat and her very mild gag reflex was violently triggered. He didn't move his cock from her throat, commanding her to hold it. Silently begging for a breath as her ass throbbed from the large dick fucking it, she felt her stomach turn. The man pulled out of her mouth and she vomited on the blankets of the bed. The man sprayed squirts of jizz on her face with a satisfied moan. Some was shot up her nose, and she winced as it burned her nostrils.

"Fucking whore puked," the man chuckled, then grabbed her by the hair and rubbed her face in it. She choked on the disgusting smell as Chet pulled out of her ass, pulled her skirt down, and shot his second load of warm semen on her back.

'Please let it end! Please let them leave me alone'. She couldn't imagine what she had done to deserve this. As exciting and somewhat enjoyable as it had been, she still felt ashamed and violated. Her legs were swung up onto the bed and she sobbed face down, still smelling her own vomit, still tasting the salty sour semen, still tortured by the pain in her asshole. She heard dressing and she felt one of her legs scratch against something small. She realized with a depressed choke that it was the condom she had told Chet to use. The men, laughing and slapping five, stood at the end of the bed surveying their handiwork.

"Stupid bitch."

"Dumb slut."

She heard the two other men wash up in the bathroom as Chet stroked her thighs and called her beautiful. The others bade goodbye to Chet and left the room. Chet went to the bathroom to wash his own penis off. He came back and forced her into doggy position.

She gasped in ecstasy as he grazed her pussy lips with his fingertips. He slid one, then two fingers inside, massaging with tender circles. She laid on the bed enjoying this as her tears finally stopped. She moaned softly and began rocking back and forth against his sturdy fingers. After a few minutes he replaced his fingers with his hard cock. He began thrusting powerfully in and out of her pussy. Her ashamed feelings slowly melted away , transforming into a repetitive chant of 'Oh my God' in her head. She forgot about the condom concern, thinking of nothing but the fat cock savagely invading her vagina. Over and over he thrusted into her, until she felt herself about to cum. With a long, loud moan she felt her pussy throb with pleasure as her open mouth tried to cry out to her higher power.

Chet pulled out of her pussy and sank his dick into her ass as he came. He got off of her and she collapsed onto her side, trying to steady her panting breath as her heart pounded. She had never cum that hard in her life, and she couldn't understand how she now felt. Chet went back to the bathroom while Blair lay in confusion. After a minute she heard him come back and dress.

"Enjoy your awkward conversation with housekeeping," he laughed, and then left the room. As wonderful as her orgasm had felt, she snapped back to reality. Blair lay horrified on the bed, wondering how long it would be until she would have to have that dreadful conversation, and hoping that they had at least left the money in her bag.