Hotel Pink Flamingo - Chapter 1 free porn video

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Sammy sat on the edge of his sisters bed. The chill air of the slightly ajar window prickling his naked skin. Nervous at what he was about to do. His heart lept as the curtain fluttered in the breeze. He sat frozen and motionless. His heart pounded in his ears. He listened to the sounds outside, a nervous twitch in his hands and joints. He sat perched and ready to flee. It was quiet and still, the night air oppressing with it’s heavy silence. Hiking up his right leg to the edge of the bed he gently began to unroll one of his sisters nylon stockings. Smoothly it stretched over his foot, his toes stretching the thin nylon material to it’s max. Shivering slightly, feeling more sensual than he ever had in the past. He repeated the process with his other leg, then laid back on the bed, settling in to the comforter. He touched one foot to the other, hands roaming his thighs and upper legs where the stockings both started and ended. The rhythmic thumping in his chest a testament of his excitement.

He felt his manhood, wrapping his fingers around it, squeezing it tight. He squeezed as hard as he could, it ached with excitement and pleasure. It was rigid yet soft, his circumcised shovel like head extruding from the top of his fist, glistening with precum. His freshly shaved body felt oddly chill and foreign. He stood up, moving quiet and silent to his sisters dresser. He gently moved things aside. Careful not to mess up, either the folding, or the order in which they been placed into her drawers. Delicately, fingering each piece, he carefully remembered how it had been folded. Intending to leave no trace of his violations. He removed a pair of black satin panties. Broader than some of the others he had found, they called to him wistfully, desperately. He held them to his cheek they felt cool to the touch. Bending over he stepped through each leg hole. Nearly losing his balance in his excitement to pull them on. They folded into the cleft of his rear so perfectly, that shivers reverberated up his spine. Walking to the full length mirror he did a pirouette as best as he could. Feeling silly and awkward. He extended his butt towards the mirror, admiring it with an almost painful longing. He stood there chewing on his lower lip a sudden sadness overtaking him. They looked better on him than most women he had seen online. Their lips pushed out like they had just ingested something sour, their all to common poses to show off their asses. He was jealous. He wondered if such simple things made his sister feel as sexy as he did at this moment. He was the same size and height as his sister even though she was 25 and he was just a senior in highschool. His frame was delicate, supple, and thin, just like hers. He admired himself, sadly. Squinting hard into the mirror he could almost imagine he was her standing there. He could feel his pre cum, sticky and hot on the taut skin of his belly. Running a finger through it he lightly massaged the head of his manhood, pressing the satin panties against his shaft sending shivers up his back once again. Milking more pre cum onto his finger he tentatively raised his finger to his lips. The taste was enough to make him yearn to cum. But he was far from ready.

On the bed behind him laid a dress. The very dress that his sister had been wearing the night before. The very dress she had unceremoniously peeled off over her head this morning and tossed in the dirty laundry. He had laid there pretending to be asleep, and admired her half naked body. The dress was a dark maroon, and so stretchy that it showed every curve and crevice of her body. It had left very little to the imagination. Now laying across the middle of her bed, no more than two hand spans wide. It looked more like a scarf than a dress. Walking over, his fingers trailing the dresses length causing him to nearly gasp. The thought of it clinging tightly to his bare skin more than enough to give him goose pimples. Lifting it up, with some struggle, he wriggled it down over his arms and head, trying not to stretch it out. Unrolling and unbunching it as best as he could, he stretched it over his waist and lower half as it clung tightly to him everywhere. The sensuality of the material, causing him to break into a sweat. Caressing his body he felt, exhilarated. The thigh highs, panties, and dress, all elevating his arousal to a height he had never thought possible. Heart pounding and his mouth dry he lay face forward across the foot of the bed. His legs spread slightly and knees against the foot board. In the mirror his backside turned up he looked every much a woman. Hiking the dress up around his hips baring his ass he began to rock slightly. His arms stretched back behind him cupping his butt, spreading it. Feeling the material against him as he spread his cheeks. Feeling the pressure of the seam in her panties touching his asshole. Feeling the pressure of his manhood pressed against his stomach. He rocked and moaned. And felt his orgasm begin to build like the pressure in a balloon as it starts to inflate. With little imagination he had visions of being mounted from behind. Gripping the bed his breath became gasps. The release was unlike any before it. Washing over him like waves on a beach. Causing him to slide down the bed and collapse onto his knees. His hands still gripping the comforter, he knelt there shaking, quivering. This was new, exciting and, well embarrassing! Out loud he muttered under his breath. " what the fuck Sammy what were you even thinking?"

Embarrassment flush on his face, his ears on fire. His face had never felt so hot. He put everything back the way it was in her bedroom before his exploration. Except for the soiled panties, those he kept, though he could not think of why. He left the door half cracked as it had been before. And ashamed walked across the small living room to the couch where he slept. Laid out his blankets, dressed in his pajamas. And went to bed. Still wearing his sisters panties. The thrill still pumping through his veins.

"Morning sleepy head" Chrissy announced as she bounced through the front door. Sammy opened his heavy lidded eyes, squinting at the sunligh glaring in through the windows.

"Morning sis" he said. She stood in the entry way her eyes hallow despite the beaming smile on her face.

"I brought breakfast" she said. Sammy rolled off the couch, eyeing the bag hungrily. As he rose he became suddenly aware of her panties that he still wore. Abashed he glanced down, and then back up at her as she leaned against the wall to take her heels off.

"You know , this covid thing has really hurt us. People just aren't going out." Chrissy stood there heels dangling in one hand. Her blonde hair slightly disheveled. Gorgeous and glowing in the morning light, her wrinkled yet elegant blue dress clinging to her. Teasing Sammy's memory of last night. "Can you clean the rooms today?" She asked. "I really need some rest."

"Of course" he replied.

Chrissy smiled wanly, the skin crinkling around her eyes, and padded off, barefoot, to her bedroom. Sammy drug himself out of bed, ate, showered, dressed and stepped out the front door. He paused outside the doorway to look around. They lived in a small hotel and had the only suite with a full kitchen and separate bedroom. The owner graciously provided their room in return for Chrissys maid and management work. It had been a blessing, Chrissy cared for and had raised Sammy. She had been the only mother he remembered. She had taken him in when he was 6. He couldn't remember life before her, or before the hotel. The one room hotel suite was all he had ever known. And ever since Covid had been declared a world wide pandemic, the small hotel was suffering, they had very few guests. Mostly folks on business, as tourism had all but dried up. The gratuities from the guests had been their only source of income and had pretty much disappeared. The room provided, was all the income the hotel owners were willing to provide. Chrissy took to falling back on other "skills" and Sammy filled in cleaning rooms and provided any necessary services the guests might need throughout the day. Sammy felt guilty that Chrissy had to resort to these other sources of income. He felt even more guilty that he actually enjoyed the alone time it gave him at night. Allowing him to pursue, well, things he couldn't before.

Gathering himself, and putting his God forsaken mask on. He pushed open the door to the housekeeping facilities. The thrum and hum of the washers and dryers a familiar and soothing sound. "Hey Sofia" he said loudly over the top of the machines. "How goes it" She looked up from her laundry bins and greeted him with a great big smile. "Hola senor Sammy." And with that promptly went back to laundry.

Entering the small office and sitting behind the desk he sorted some of the papers and went over the to do lists for the day. Only 3 guests, he groaned, hoping the hotel wouldn't go belly up. He made note that two were checking out this morning and the third , had asked to have their room picked up. Leaving a message with the front desk, of an early departure for work and a late afternoon return time. Wishing to have fresh towels and linens. This is where he would start then. He grabbed the cleaning cart and made his way through the single story complex to the guests room. Knocking gently and calling housekeeping several times. He confirmed the room must be empty. So he unlocked the door slipping inside pulling the cart in behind him. It was dark, only a slim glowing line split the room down the middle, wavering slightly as the curtains shifted from the door when it clicked shut behind him. His nostrils flaired, the slight aroma of women's perfume hung in the air. Sammys heart sped up , beating in his ears. To his left was a dresser, a flat screen television perching on it. A queen sized bed separated him from a wall to wall closet with sliding mirrored panels. A room, familiar,and just like every other room in the Hotel. He wound his way around the foot of the bed, trailing the fingers of his left hand over the top of the television, no dust. Just past the bed and on the other side of the closet, the door to the bathroom stood open. A neat pile of used towels sat in the middle of the floor, and various cosmetics were strewn across the vanity.

Sighing. Sammy set to work, in no particular hurry. It was early yet and likely the other two guests hadn't checked out yet. He hung new towels and wash rags, placing the damp ones into the dirty linen bag on the cart. He went about his business with a practiced proficiency that someone gains from having done the same tasks over and over again. When he got to the bed, he straightened the sheets tucking them in and folding them under. Briskly tugging the duvet bed spread and folding it down. Hearing a small thud, followed by a brief whirring sound he looked down at his feet. Kneeling down he picked up the object, while simultaneously realizing it's purpose. When his fingers closed around it , it began its vibratory medley once again. Twisting the lower half of the phallic device he turned it off. Examining it he felt his manhood stir. Looking around he saw the ladies suitcase on the wooden luggage stand. Top closed but not zippered. Sitting on the bed in front of the suitcase, pearly pink vibratory still in one hand. He opened the suitcase peering in at some complete strangers clothing. There were no outer clothes. Just braziers and panties, stockings, and blouses. Sammy ran his fingers through the medley of under garments feeling a thrill rush through him. His own phallic member folded against his leg, half charged and aching to be released from its current position. Ignoring it, he delved deeper into the suit case. Nothing was in any particular order. Definately not an organizational freak like his sister. Rooting around he found another , smaller vibrator and a bottle of lube. His excitement growing and anticipation pumping a rhythm side by side with his heart. He could feel the sticky pre cum wetting a spot on his boxers. Reaching down he squeezed and moved himself. In a more free position he quickly found himself completely erect and completely aroused. One particular garment had caught his eye. A swim suit. It was different than his sisters bikinis, being a one piece, rather than two. It was dark blue and cut high in the hips. Since the pandemic had been declared the governor for the state had shut the swimming pools and restaurants. The idea struck him so quickly he nearly slid off the bed. Whoever this person was, likely she wouldn't miss a bathing suit. Quickly he jumped for the door, locking the deadbolt and safety latch while peering out of the viewing hole. He grabbed a couple of the dirty towels and laid them across the bed. Disrobing he admired his form in the mirrors, lightly stroking his cock. He stepped into the bathing suit and pulled it up over his hips. It was tight. Tighter than his sisters clothes, this woman was a bit smaller. Wriggling it up over his torso he barely managed to get the shoulder straps over his shoulders. On the bright side, in this bathing suit , his total lack of breaststroke didn't leave sagging empty material. It fit snug against his chest. Leaving the firm outline of his erect nipples. The mushroom shape of the head of his manhood clearly visible , pinned to his abdomen. A small wet spot blossoming out from the head. He always generated lots of pre cum. Crawling onto the bed and laying down on his back he began to work his hands up and down his body. Fingering the seams around his thighs, the smoothness of the material against his abdomen. His member throbbed. It beat with a heart of it's own. Rolling over onto his stomach, preparing for the finale, he rolled onto the large phallic vibrator and tube of lube. His heart suddenly stopped beating. Why not he thought. Popping the cap to the lube he squeezed some out onto his finger. While laying on his side he reached behind slipped his hand under the back of the swimsuit and rubbed the lube on his asshole. He nearly came just from that. Tenatively he probed his hole with his finger, his hesitancy almost a tease. One knuckle, two, he slid his index finger inside of himself. He wasn't able to go any further, the angle was just too difficult to reach. Grasping the vibrator he reached behind once again and pressed the blunted tip against himself. Feeling tremendous pressure as it was much larger than his finger. Just about when he was about to give up, it popped inside. He gasped and his legs went straight, his body rigid. The pain a bright flash in the back of his eyes. It quickly subsided however and he began once again to work it in, and back out and back in again, slowly he became adjusted to the girth of the object, his cock throbbing and now releasing ore cum in rhythmic spurts, in beat with his heart. With the vibrator half way in he began to roll on to his back. Once in position his hips pushed out and heels dug into the bed he lowered his rear end towards the bed, slowly he pushed the device fully into him. Where it made contact with something glorious. Pulling the fabric of the swim suit aside and freeing his member he lay that way for some time. He reveled in the feeling of the vibrator inside of him, pressed firmly against the bed. His member oozing pre cum twitching and jumping of its own accord. Gyrating his hips to apply and relax pressure on the device it became enough to twist the end to the on position. The vibrations came of such intensity against his prostate that without hesitation or realization he began to climax. Shooting hot white strands of sticky cum so powerfully that the first couple jettisons hit him in the face. The orgasm finished tland the vibrations becoming too painful, he rolled to his side, grasped the vibrator and pulled it out. The large suction sound that followed came a moment before the pain. His stretched out hole collapsing too fast. He curled up in pain and lay there for a minute. Tears in his eyes, he licked his lips, and tasted his semen that had run down his cheek as it had mixed with tears.

He cleaned up. In a state of shock everything a blur, he finished off the rest of the day, numb.

The next day, he had several rooms to clean, the weekend having arrived, a small numbers of guests were slowly filtering in. Keeping one eye on that fabulous room he had cleaned the day earlier had proven difficult, but in the end it paid off. He caught side of her as she exited her room and headed to the front lobby to check out. She couldn't have been more than five foot tall. Tan skin, much older than his sister who was 25. She had bleach blonde hair and couldn't have weight more than 100 lbs. Inward he chuckled with the thought that she had no idea that the next time she used that vibrator she would be using a tainted toy. The thought brought a heat to the back of his neck. He watched her as she walked away from him. Wondering if he would ever get to be with someone that pretty. Well at least he had something to remember her by. He put his mind to cleaning hoping to finish early.

The weeks went by, turning to months. His birthday had come and gone.. Sammy had found many more opportunities, and slowly amassed a small collection of outfits and negligees. Mostly from guests who came and went. But he still found that he couldn't stay out of his sisters things. From time to time he would keep some of her garments. He had secured a hiding spot, not having much privacy in the small hotel suite. It had been difficult. The couch had turned into a dresser of sorts. Sometime in the evening he would pull it all out and admire it. Trying various outfits on. Examining himself in the mirror. They made him feel pretty, sexual, lustful, more connected to women. He felt more comfortable as each and every day passed. Sometimes wearing women's underwear under his clothes for entire days. Always, he found himself arroused.

Revelations

Graduation was just around the corner. Sammy had been a great student. Diligent and steadfast in his schoolwork. He applied himself well. And finishing school early had always been a goal. Being able to have the freedom to help Chrissy out, was a big priority. With Covid still being such a big concern, there would be no real graduation. Everything was virtual. He didn't mind at all.

Having made a mile long hike to the grocery store. Sammy was just returning, a sack of groceries in each hand. With a little difficulty he managed to muscle the door open without putting the groceries down. What he walked into, made his blood go cold. He dropped both bags of groceries. The paper bags busting open. An onion rolled across the floor towards his sister. It happily hopped, oblivious, bouncing and tumbling. It came to a rest at her feet. She stood in front of the couch, his couch. His precious worn out bed. The only real personal area he had ever had. She stood there facing him. There were tears running down her face, streaking her mascara, marring her perfect angelic face. A knot of concern, worry and a look of despair all mixed into one. In each hand, her fingers balled into fists. She held fitfulls of lingerie. His bedding a mess, it lay jumbled at her bare feet. Her light grey robe, slightly hung open at the neck. He could see the tops of her small breasts heaving with her deep breaths.

"Sammy, oh Sammy what is this." It came out sounding rushed. She sounded so sad. So disappointed. A lump in the back of his throat threatened to choke him to death on the spot. Tears welled up in his eyes and he bit his lower lip. She went as if tonsay something , but instead gasped between trembling lips. He half expected her to wail, like a mother does at the loss of their child. "God, I'm going to wail" he thought to himself. He stepped back bumping into the door, causing it to whip shit behind him with a loud slam.

"Oh Sammy, dear sweet brother." Trembling, she did not seem to know how to put her words together. Leaving her speaking in broken sentences with long uncomfortable pauses between them.

"Some of these are mine…." A breath. "A lot of them aren't" another breath. "Have you been stealing these ?" Her accusation hung in the air like a gloomy cloud. Sammy stood breathless in stark fear and embarassment. Tears of shame streamed down his face. His legs felt weak.

Her face softened, she saw the stark terror in his face. She dropped her burden and rushed up to him. Embracing him. An act that only moments ago, he had thought to be lost to him forever. He wrapped his arms around her as they sank to the floor. She held him for what seemed like forever. "Its okay little brother, I love you. I love you more than you could ever know, whatever it is we will get through it." She cleared her throat, kissing his forehead. "You and me bud, always."

The days ticked by after the events of that afternoon, uneventful, quiet, and just a little awkward. Every time his eyes met hers he'd glance away and blush. They went nearly a week without talking about it further. After 6 days she broke the silence.

"You wear them?" She blurted out, glancing at him, her cheeks turning red. Blushing furiously, he looked at her and nodded. "I see" she said. "No… no i don't really see. I can't quite wrap my head around it." She paused a moment as if to collect her thoughts, then she went on. " Stealing and hiding things, that is wrong. You have to understand that." Taking a deep breath she continued. "If this is who you are, then its who you are. I accept that. But you can't steal and live some secretive life." Sammy looked into her deep blue eyes.

"I understand.."

"Do you ?" She said. "If you get caught stealing from our guests, we will both be out on the street. This is all we have." She spread her arms exaggeratedly.

Tears started to well up in his eyes, she noticed, and her face grew softer. "Do you wish you were a woman?" She asked. He shook his head no, and with a resigned sigh he said. "Sometimes, it just feels right. But not all the time." He had no desire to explain to her the revulsion he felt after he had orgasmed. Or the thrill of coming closer to his femininity through dress. She nodded as if she understood. Moving closer she embraced him. Pulling him in almost conspiratorially. "Well" she said. "I guess it can be like having a little sister , sometimes, when you feel like it." Letting go of him she moved back to the stove. Spinnin lightly on her feet a mischievous look on her face. "We can even go shopping for clothes together! Like sisters…" she added "If you wanted to" turning away he tried to hide his embarassment over the topic. But the thrill was boiling up in him at the prospect of shopping for womens outfits.

Sisterhood

The first time they went shopping it had been a bit awkward. Sammy would help pick out various articles of clothing, and Chrissy would go into the dressing room and try them on. Model them for him. Some moments more awkward than others. He was careful to avoid the intimates sections and focused more on outfits. Dresses primarily. The cute feminine ones. They even found a couple pairs of heels. The entire day had been such a rush. And images of his sister in each outfit cycled through his head. His manhood ached for release and his boxers were sopping wet with pre cum.

Returning to their small domainand with the door firmly shut. Chrissy drew the blinds. And looked inquisitively at Sammy. "Well, are you going to put an outfit on or what ?"

His heart leapt into his throat. He tried to swallow it back. Could he do this ? What if she laughed at him. He looked at her, really looked at her. He saw nothing but caring, love, and concern there. He took a deep breath and gathered his favorite outfit from the bags and headed for the bathroom. "You can use my room to change" She said quietly. He shut her bedroom door behind him and leaned back against it. This was hard, very hard. He didn't even understand why it was so hard.

Chrissy stood outside her room, hearing Sammy lean against the door. She sighed, quietly, fighting off the tears that welled up in her eyes. She was so frightened. Her poor little Sammy. All these questions blazed through her mind like lightening, branching off and forking from one question to another. Was he Gay? Trans? Bi? She stifled a small moan before it could escape her lips. Oh God would he be okay? Would he be alright? He was so fragile, she could tell he was so near to breaking that her heart seemed to palpate.

She had thought long and hard about this. Forcing herself to be accepting and look at the positives. She had to support him no matter what. "I guess It doesn't matter what he is after all" she thought. "He's still my little brother." She took a step forward calling gently "Sammy? Are you doing alright in there? " "y-yes sis" his muffled stammered reply came through the door.

She breathed a sigh of relief. Placing one hand longingly on her door, wishing she knew how to he more supportive. Nervously she smoothed down the stomach of her blouse, and brushed a few pieces of lint off. She was anxious. "I don't even know what I'm doing. He's going to look fucking rediculous and you, YOU, set him up for this. YOU had to take him shopping, you had to encourage this, this, behavior." The truth was she had suspected for some time that something was amiss. She was incredibly neurotic and almost OCD about things. She had known right away that her drawers had been gone through. Even tried to convince herself that the things gone missing were just her suspicious nature taking the front seat. But she knew. She had convinced herself that he was just curious. But she had been wrong.

She knocked on the door. He replied immediately "Come in, I guess, I might need some help." Her palms sweaty, she ran them across her stomach again. She turned the knob and walked into the poorly lit bedroom.

Her breath caught in her throat. Her eyes began to sting. He was beautiful. Stunning. Gorgeous. The picture perfect image of a young lady. Her dear brother stood there barefooted. He was wearing a summer dress, purple with pink flowers. Fitted around the torso and flaring at the hips. It came down to a couple inches above his knees. His calves were slender and feminine, even his ankles appeared dainty. She stood there in complete shock. Her eyes climbed higher, the dress hung frumpy in the breast, as he had none to fill them out. The straps adorned his shoulders accenting his slender collar bones and narrow neck. "Oh my" she said huskily "Little brother you are beautiful" she cleared her throat. Some of his anxiety visibly melted away. She walked up to him saying. "let's see here turn around" he did as she bade. She pinched the material slightly behind his shoulder blades tugging on it. Seeing that it fit him well, he just had no breasts to fill it out. The soft spun material hung on him better than most women. He had her butt, she thought as she unbunched some of the material around his waist. In fact he was the same spitting image of her. She grabbed him by the shoulders, turning him around, and looked into his deep blue eyes. "What is it you need help with ?" She asked. "I can't figure out these heels they are too small I think" he replied. With a little giggle she backed him up to the bed where he uncerimonoously plopped down on his cute butt. "Silly" she said. "They need to be a bit smaller or else they'd slide around on your foot. The price for beauty …." She trailed off. Locating the shoes, she knelt in front of him. Taking him by the ankle she cupped his foot in her hand. He jumped. "Whats the matter, ticklish? " he jerked away making an annoyed face as she tickled his bare foot. "Stop it!" he said half giggling himself. At the moment he had jerked away, the dress had ridden up. Without meaning to,her eyes rested on the black satin panties, damp, around the bulge of his cock. She tried to hide her embarassment with one more round of tickles. He sighed when she relented and proffered his foot. She held his right foot, his bare skin cool to her touch. With her free hand she slowly worked the stilleto style heel over his cute toes and over his heel and strapped it on. Having done the same with the other foot, she sat back and marveled in her success. Nearly leaping to her feet. She grabbed Sammy by the hands and slowly pulled him to his feet being as gentle as possible. He stood with his toes pointed at odd angles. Looking like a child trying on their first pair of roller skates. She smiled a genuine smile straight from her heart. For the first time in the last few days she felt relieved about all of this. Like she had been carrying lead weights around, and suddenly they were gone. Sammy smiled back abashedly and averted his eyes. Her heart rang like a bell with warmth and love for him. "Come with me!" She said as she took his hand and carefully led him from the room. He walked awkwardly in the heels. She led him to the bathroom, patting the bathroom counter. He almost fell over. "Whoa there" she said trying not to laugh. Grabbing him by the hips she helped him slide his butt onto the counter. She spent the next 45 minutes breathing into his face as she applied all the various tools of female beauty. After applying the last bit of lipstick she leaned back to inspect her work. "Gorgeous darlin" she drawled. Helping him off the counter so he could look in the mirror.

She left him like that. Dolled up and practicing walking in heels. He had been genuinely happy. His embarassment still evident, but no longer overpowering him.

After dressing for her nights work. She had felt guilty leaving him. Though he had some mixed feelings about it all. She would need to be careful not to cross any boundaries. While changing for work, she had found her panties soaked through. Her vision flashed back to seeing his cock outlined in her panties. HER PANTIES. why had that turned her on so much. She fought a shudder. "Eww girl, thats your brother" She shoved the feelings down. This was not the time for her to lose grip on reality. She had to be a rock.

The afternoon of excitement was wearing off as she prepared herself for what she must do. She was dolled up wearing her sexy maroon dress and peep toe pumps. All 5 foot 5 inches of her exuding sexuality. She loved the feeling of power she got over men as she walked down the sidewalk. She checked the app on her phone and saw that her date would arrive at the red lobster, in just a few moments. She picked up her pace to make the last block in time. Arriving, she stood at the corner of the restaurant checking her app once again. There was a message, saying simply, black dodge pickup, searching the parking lot she saw the only black truck, lifted and all jazzed out, idling a couple rows back from her. She made her way between two toyotas that looked like micro machines next to the large pickup, and opened the passenger door. "Figures" she thought to herself "a fucking redneck macho dickhead" she sighed inwardly and at the same time let the corners of her mouth turn up. "Hey there handsome" the words seemed hollow to her, but the beard on his face split to reveal a ear to ear grin. "Well hello there beautiful, you are even more beautiful in person "She climbed up into the ridiculously high truck and shut the door behind her. She settled in, smoothing her dress against her thighs and buckled in. She turned to him about to speak, but he cut her off "$550 for the date right? And…. If I want more.."

"They always want more" she thought, trying not to roll her eyes

"If you want me to spend the night we can arrange that" she stated in a cooing tone. He was a big guy, large in the chest, with a unkempt black beard and greedy eyes. He wore chinos and a polo, that appeared to be clean. "We're going to a company event." He stated matter of factly. "Big hoopla every year, company I work for throws for it's drivers." He turned away from her as he backed out of the parking stall. "Need a pretty young thing on my arm, make the others jealous" he reached over and pawed at her bare leg. "The escort service promised and delivered" his hand climbed higher up her leg. "They'll all wish they had it like me" his hand continued up past her leg, pawing at her tit. She kept a smile on her face belying her disgust, and leaned into him nearly purring. "Except you have to pay for quality pussy" she thought. The service she worked for was a quality one. They set the fees and she got 30%. Tonight would pay $165, well before taxes. Always part of the problem working legit. But there was always the side hustle. Cash paid up at the end of the night, for the full service. Inwardly she sighed, she felt deflated, and drained. Used up. These nights were long and arduous. An act she had to put on simply to survive. Not all nights paid this well. And if she could squeeze another 100 out of this egotistical fuckhead, it would mean she wouldn't have to work for a few more nights. She turned her attention back onto the man. He had been talking the entire time. "What's your name? Oh nevermind, I'm going to call you Jen, no Jennifer. Thats it, Jennifer" They had gotten onto the freeway the lights in the dark left streaks and trails in her peripheral vision. "So…" He talked on. And on. The entire night.

It was an uninteresting date. He showed her off to everyone as Jennifer. And she clung to his arm like the obedient woman he expected her to be. He stood over her and was at least six foot and a couple inches tall. She would swat him and giggle, batting her eyes at him everytime he would grab her ass. Sometimes he was a little rough and she knew his pinches and physical attention to her body would leave their mark on her. After a catered meal and some lavish awards for safety, they left the venue and headed out into the cool night air. Walking arm in arm with him, leaning into him, she looked up at him. "Where to now big guy"

"I have a room, at the Marriott across the street, I wanted to be able to drink and not have to search for a place."

The room was lavishly decorated , had two king sized beds. A suitcase sat on one bed, he had obviously checked in before picking her up. She bent down and removed her shoes, wiggling her toes with delight. "The things I do for beauty" she thought. Arms roughly reached around her, swinging her off her feet, and pulling her into an embrace. His liquor laden breath and coarse beard ground into her face. His tongue searched out her lips.and forced its way inside.

"And so it begins " she thought. When he pulled away, she took a deep breath. "$100 she said, put it on the table over there." She pointed to the stand that the TV rested on. He complied, licking his lips greedily. He nearly ripped his shirt off over his head and unfastened the belt holding his pants up, completely disrobing in a matter of seconds. He was fit, very muscular, and covered in more of that corse black hair from head to toe. His uncut cock stood at full erection, its head glistening in the poor light. In another moment he was upon her, pushing her to her knees. One hand behind her head, fingers intwined in her hair. "Look at me" he said, and so she did. He wasted no time pushing his cock past her lips, the taste of him assaulted her nose and tongue. Pushing past her tongue he went straight for the back of her throat. With practiced effort she accepted his large cock allowing it to pass into her throat. Instantly blocking off her airways. Her eyes began to well up with unwanted tears. "1, 2, 3 , 4" she counted the seconds he held her there with her nose buried in his crotch. "8, 9" he released her, pulling her back by her hair. He stared down at her with a alcoholic glaze in his eyes. " you like that don't you whore!?" and then he impaled her again. "6,7" and again "9,10" tears ran down her face streaking her mascara, his juices and her saliva ran slimy rivulets down her chin. She prayed for him to just cum already , but she knew she wouldn't be that lucky. Still holding her by her hair he pulled her to her feet. He pulled her dress up and over her head. She wore no underwear, a dress like that would just show lines. Her perky tits and erect nipples covered only in her silicon bra. That also was ripped away. She stood there humiliated, forcing herself to maintain her composure. Wiping her face with the back of her hand she smiled up at him, and said "come on handsome show me how gentle you can be" he grinned, that same predator grin from when they first met.

As she lay there, suffering his ministrations, providing sounds of pleasures, she wondered why men always fucked women with their fingers. Did they think women liked that? He crawled on top of her, she lay on her back. The weight of him making her feel like a child. He held each of her wrists at arms length, helpless, stretching her out like a doll. Digging one knee, the size of her torso, in between her legs he spread her wide open. He entered her in one rough push. It was like being ripped in half. She tried to wrap her legs around him in a vain attempt to keep him from pulling out too far. He pulled out and slammed back in, hard, his balls slapping against her ass. Slap , slap , slap she held on feeling like she was going to be knocked off the bed. Abruptly he stopped, withdrew , and ripped the condom off. "God im tired" she thought. "Please cum soon you piece of shit" he rolled her onto her back and slid her backwards across the bed, and began brutalized her throat again. It was like being impaled by a fence post. She lay there on her back. Her head hanging off the bed. Naked and vulnerable. Her sweat mixing with her own saliva and running down her face and into her eyes. His hands roaming all over her entire body. Violating her in every way. His cock sliding in and out of her throat. He raped her face. Her hands pushed against his hips hoping she didn't die here from his horse cock. He finally came. In one final thrust down her throat. He unloaded. "1, 2, 3, 4" she counted as she gagged and snorted strings of cum out her nose, trying to get air. Desperate she clawed at his hips. "5, 6, 7 ,8…..11"

Gasping for air snorting and sobbing. She rolled off her back and onto her knees. Long strings of semen hung from her nose and she crouched wild eyed.

"Clean yourself up" he said. As simple as that. She shuddered. Tears streaming down her face. "Another hundred" she said. "Hell whatever is in your wallet as well, you didn't pay me for your rape fantasy" he laughed " $200 and its yours. I'll pay you $700 if we don't go through the service next time" She cringed, like she'd been slapped. "$700? Cash… So much… oh god help me." She cried out to herself. Her whole world grew large around her, she felt tiny and infinitesimal. Like a tiny dot on a map. "I need to shower" she said, padding naked and humiliated to the bathroom. She stood facing the shower, head bowed and hands against the wall to support her. The steamy air combined with the hot water pouring down her body was almost enough to make her scream in despair. A guttural scream , one of agony and self loathing. She fought it down. It hadn't been that bad, had it? $465? And $700 for the next? She dried off and pulled her dress down over her head, carrying her few belongings and shoes in her hand, she exited the bathroom.

He was asleep on the bed. "Passed out from too much booze." She thought. She hesitated , feeling ashamed, then went for the hotel pad and pen on the dresser. On it she wrote her phone number, "text only no calls." And the name "Jennifer." She left then, in the wee hours of the early morning. Head hung low, ashamed of her weakness. Ashamed of what she had to do to survive, of what she was willing to do.

-->

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Hotel Love

About three years ago my marriage was in deep trouble. We’d been married for nine years; with twin daughters. I’d not long had a promotion at work and my wife was struggling to combine a full-time job with being a good mother and loving spouse. A new job meant that I earned a lot more money but had to work longer hours and stay away from home two or three nights a week. I was too busy to notice any problems until one Friday night when I arrived home to find the kids already in bed. When I...

Erotic
4 years ago
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Hotel Rouge Part 1

Hotel Rouge was everything its website promised - intimate, discreet and luxurious. There was no check-in desk, just a table in the richly decorated hall, where the young woman who materialised as soon as I came in noted my name, took a tasseled key from a drawer and picked up my bag. I couldn't help watching the seductive rotation of her marvellously rounded bottom on the way upstairs - the tight skirt showed it off to perfection, and I got the impression that the woman was more than aware of...

Spanking
3 years ago
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Hotel surprise

It's been awhile since the adult theater incident and I've not stopped hearing about it. My little slut became a full-blown whore in there and her pussy has been dripping with thoughts of me taking her to the theater once more.But she should know that Masters don't give into whims, in fact, we prefer to be creative. Which leads me to our casino getaway. My wife and I often go to the casinos near where we live -- I enjoy the gambling, she enjoys the free hotel room and all the toys I bring...

4 years ago
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Hotel surprise for wife

It's been awhile since the adult theater incident and I've not stopped hearing about it. My little slut became a full-blown whore in there and her pussy has been dripping with thoughts of me taking her to the theater once more.But she should know that Masters don't give into whims, in fact, we prefer to be creative. Which leads me to our casino getaway. My wife and I often go to the casinos near where we live -- I enjoy the gambling, she enjoys the free hotel room and all the toys I bring...

4 years ago
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Hotel Rendezvous I From Her

Way too much time has passed since we last saw each other let alone touched each other. So here I am waiting at the airport for you arrival. This rendezvous is on me, the planning I have done is for your pleasure. My pleasure will come from pleasing you and making you purr like a lion every minute of the next 72, or so, hours. I just hope you enjoy what I have planned for us. For the next 3 days and nights you are mine, I am yours and. . . . . . .best of all WE are together.I arrived a...

4 years ago
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Hotel Handyman gets a surprise TRUE STORY

I was staying in (and escorting from) a ‘mainstream’ hotel in Norwich, Norfolk UK.I checked in (in male mode) and made my way to the room.It was quite a big suite I had booked, as I like bit of freedom and was booked in for a week. The reason I quite like this particular hotel, is the windows open quite a way, and discreet smoking is possible. Anyone who knows me or anything about me will understand that this is of paramount importance for me.As I had a ‘concrete’ booking for 2 hours time I...

3 years ago
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Hotel Window

Hotel chains work very hard to build brand loyalty with their customers. After reading about my hotel adventure you will understand why I am a very loyal and devoted customer for one particular hotel brand. I seek them out whenever I travel. This experience happened about two years ago. I was traveling alone and I was staying at a large suburban hotel. Most of these hotels are multi story with all of the rooms surrounding an enclosed central atrium area. Most rooms have large picture windows...

Voyeur
3 years ago
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Hotel Hardon

I have been staying at the same hotel, every Sunday through Thursday, for over a year.  Work takes me to this place and stresses me every single day.  My nights are my only respites and I try to take every advantage possible. While I always sleep in the nude, unfortunately, there is not any good way for me to take walks outside in the same manner.  The hotel is in a rural area near an airport, surrounded by trees on three sides and a fast food restaurant on the fourth.  Beyond the trees are a...

Exhibitionism
3 years ago
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Hotel Fun

I was on a business trip to a small town in South Carolina. I stayed at the only hotel within 50 miles. When I checked in, the guy behind the counter said that I was the only person staying there. He was about 25 and had a thick southern accent. I noticed his laptop was open and a video was paused. I couldn't see what the picture was but I could make out the title. It said Muscular tops younger stud. Sensing the opportunity, I asked him what there was to do for fun in town. His reply was short...

4 years ago
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Hotel room with Krystal my slut

Two weeks had past since I broke Krystal's anal virginity. She was back at school and I was back at varsity with my studies. Krystal and I exchanged a number of messages as we planned to see each other again. I was still coaching her brother cricket on weekends and the school took me on to help coach some rugby in the afternoons. So thankfully I still had some good money coming in and I could afford to book a hotel room for a Saturday night again. Krystal and I planned this Saturday carefully...

3 years ago
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Hotel Meet

The following events happened as described. As well as I can remember them anyway, lol.A couple of weeks ago I met a guy from here who over the past few weeks had got to know everything about me. I told him about the desires I had about being picked up in a bar then being taken back to a hotel and fucked silly. He knew I was free at the weekend so he organised a night at a hotel and told me he had set up everything for me to live out my fantasy! A day later, a bunch of flowers arrived at my...

4 years ago
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Hotel

It was raining very heavily that night. Tom hated driving in the rain. The thunderstorm roared very loudly and in his car's front screen, he could see lightning blazing itself up on the night sky. On the bright side, the highway wasn't full of that many cars. He was driving from Nevada to Kansas. He grew up in a small little town but his dad took him and the rest of the family away to Las Vegas, being tired of the religious lifestyle. Basically his father and mother ran away together, trying...

4 years ago
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Hotel Adventure

A few months ago, I started a new job. The job took me around the country, often to locations far from home, where I would stay in some easily forgettable hotels, which usually, at least, were blessed with free WiFi. I would generally arrive the night before attending client meetings the next day. This gave me many opportunities to enjoy my old hobby of cross-dressing. Now, I am straight, but - for as long as I can remember - have enjoyed the thrill of dressing as a woman. I have never gone out...

Straight Sex
1 year ago
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Hotel Adventure

A few months ago, I started a new job. The job took me around the country, often to locations far from home, where I would stay in some easily forgettable hotels, which usually, at least, were blessed with free WiFi. I would generally arrive the night before attending client meetings the next day. This gave me many opportunities to enjoy my old hobby of cross dressing. Now, I am straight, but - for as long as I can remember - have enjoyed the thrill of dressing as a woman. I have never gone out...

2 years ago
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Hotel Room Treat

Helen and James had decided to go away to Bath for Valentines day and stop in a hotel for a few nights, while James had got his wife some sexy lingerie to celebrate the special day, Helen was unsure what to get for her husband. Helen enjoyed dressing up for James and he certainly liked to see his wife showing off her sexy body in a number of different outfits and costumes, with this in mind Helen plotted a surprise that would be perfect for their valentines holiday. The lovers awoke on...

3 years ago
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Hotel Rooms

I don’t know what it’s like for other people but I always find hotel rooms a bit of a turn on. Recently I was sent by my company to do some training in the north of the country. The hotel they had booked me into was very plush, the reception was modern looking with a lot of mirrors, it was small but the mirrors gave it a much larger appearance.  The girl at the desk was wearing her uniform tight, showing off very tasty curves. Her blouse was daringly unbuttoned giving a hint of cleavage. My...

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