Becoming Samantha

All characters in this story are over the age of 18.

I live for feedback! Please feel free to comment or reach out to me. Thank you for reading Sammy's story.

Chapter 1

Explorations

Sammy sat on the edge of his sisters bed, chill air from the open window prickled his naked skin. Nervous at what he was about to do, he sat frozen, heart pounding in his ears and listened to the sounds outside the narrowly opened window. A nervous twitch haunted his muscles.

It was quiet and still, the night air oppressive with its heavy silence. Hiking up his right leg, he unrolled one of his sisters nylon stockings over his foot. It stretched smoothly as he rolled it up his legs. Shivering slightly, he felt a burst of arousal, more than he had ever felt in the past.

With both nylon stockings gripping his upper thighs, he laid back on the bed and settled into the comforter. He touched one foot to the other, while his hands roamed across the odd material. As he examined his long slender legs in the moonlight, he felt pretty. The rhythmic thumping in his chest was a testament to his excitement.

He moved his hands to his cock and wrapped his fingers around it. Squeezing it as hard as he could, it ached with excitement. Completely rigid, his circumcised cock glistened with precum. .

Sammy stood up, moving quietly. Feeling like a car burglar, he opened his sister's dresser. Moving things aside, careful not to mess anything up, he went through her underwear. Delicately, he fingered each piece, enjoying the textures of the fabric. A pair of black satin panties stood out to him. They were broader than the thongs and seemed sturdier.

He held the panties to his cheek, the cool and silky texture excited him. Bending over, he stepped through each leg hole, nearly losing his balance. Pulling them up, they folded into the cleft of his ass perfectly, sending shivers reverberating up his spine. Anxiously, he walked to the full length mirror and examined himself as best as he could. An awful feeling of awkwardness and longing came over him

Sammy stood there chewing on his lower lip sadness overtaking him. They looked better on him than he had ever hoped. He wondered if such simple things made his sister feel as sexy as he did at this moment. Sammy was the same size and height as his sister, even though she was older. His younger frame was delicate and slender, they were a perfect match. He admired himself and squinted hard into the mirror. Almost, he could imagine it was his sister, standing there, in front of the mirror. The feeling of his precum, sticky and hot, reminded him that he wasn't his sister. Running a finger through his precum, he lightly massaged the head of his cock. Pessing the satin panties against his shaft, Sent 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 squirm with the desire to cum. Closing his eyes, he imagined it was the taste of a strange man in his mouth.

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 it laid 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 trailed along its length, causing his breathing to become ragged. The thought of it clinging tightly to his bare skin, more than enough to give him goosebumps. Lifting it up and over his head and with some struggle, he wriggled it down over his body, 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. The sensuality of the material, causing him to break into a sweat. He caressed his body, smoothing the material to his abdomen.

He felt exhilarated, excited and sexy. 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. Spreading his legs slightly and knees against the footboard he turned his backside up. He looked at himself in the mirror, all curves and feminine and wondered what it would be like to be a woman getting fucked from behind.

Hiking the dress up around his hips, baring his ass, he began to rock slightly. His arms stretched back behind him, cupping his ass cheeks, spreading himself wide. The feeling of the material against him, all bunched up around his hips, made his imagination go wild. The pressure of the seam in his sisters panties, touching his asshole and the pressure of his manhood pinned between stomach and bed, became his entire focus. He rocked and moaned. And felt his orgasm begin to build like the pressure in a balloon as it starts to inflate. With a little imagination, he had visions of being mounted from behind. Gripping the bed his breath became gasps.

The release was unlike any before. It washed over him like waves on a beach. Crashing together like oceans colliding, his blood roared in his ears like a jet engine. His climax far larger than imaginable, began to retreat, he began to slide down the bed and collapsed onto his knees. His hands still gripped the comforter, he knelt there shaking, quivering. This was new. Both excited, and embarrassed he began to overflow with shame.

He whispered under his breath. "What the fuck Sammy what were you even thinking?"

Embarrassment made his ears burn and his cheeks bright red. He had never felt so humiliated. Putting everything back the way it had been, except for the soiled panties, he made sure everything was, as before. He left the door half cracked and ashamed, walked across the small living room to the couch where he slept. He laid out his blankets and dressed in his pajamas. Sammy went to bed that night still wearing his sisters panties. The thrill, still pumped through his veins.

"Morning sleepy head" Chrissy announced as she bounced through the front door.

Sammy opened his heavy lidded eyes, squinting at the sunlight that glared at him through the windows.

"Morning sis" Sammy said.

Chrissy stood in the entryway, her eyes hallow, despite the beaming smile on her face.

"I brought breakfast" she said.

Sammy smiled, and rolled off the couch, he eyed the bag hungrily. As he rose he tried not to think about Chrissys panties that he still wore. Abashed he glanced down at his pajama bottoms and then back up at her. 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 said, She stood there heels dangling in one hand. Blonde hair slightly disheveled, Chrissy looked gorgeous and glowed in the morning light. Her wrinkled yet elegant blue dress clung to her, contouring her slender frame. It teased Sammy's memories of himself 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. Turning, she padded off, barefoot, to her bedroom.

Chrissy and Sammy lived in a small hotel, called the pink flamingo. They lived in a small apartment, reserved for the on-site manager. Just a single bedroom unit that the owner graciously provided. Chrissy was the on site manager, and often filled in for cleaning duties. Since the pandemic, Chrissy had let go the cleaning staff because business was too slow. The one or two guests they had a night were easy enough to clean up after themselves.

Chrissy cared for and had raised Sammy. She had been the only mother he remembered. She had taken him in when he was just little. He couldn't remember life before her, or before the hotel. The one room hotel suite was all he had ever known. 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 owner was 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. Sammy made his way to housekeeping and grabbed the cleaning cart. Making his way through the single story complex, he began checking rooms. Knocking gently and calling housekeeping several times, he confirmed the room must be empty, he unlocked the door and slipped inside, pulling the cart in behind him.

It was dark, only a slim, glowing line, split the room down the middle. The line wavered slightly as the curtains shifted from the doors draft. His nostrils flared, the slight aroma of women's perfume hung in the air. Sammy's heart sped up and began pounding 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. The room was familiar, being identical to all the others in the Pink Flamingo.

Walking around the foot of the bed, he trailing the fingers of his left hand over the top of the television. 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. 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 and folding it down, he heard a small thud. It was 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 vibrator still in one hand. He opened the suitcase peering in at the ladies clothing within. It was full of braziers, panties, stockings, and blouses. Sammy ran his fingers through the medley of under garments feeling a thrill rush through him. His cock, folded against his leg, throbbed and ached to be released from its current position. Ignoring it, he delved deeper into the suitcase. Nothing was in any particular order. This lady was definitely not an organizational freak like his sister. Rooting around he found another smaller vibrator and a bottle of lube. His excitement grew beyond anything he'd ever felt. Anticipation pumped a familiar rhythm in his veins. He could feel the sticky precum wetting a spot in his boxers. Reaching down he squeezed and moved himself into a more comfortable position. Quickly, he found himself erect. One particular garment had caught his eye, a swim suit. It was a one piece, which was different than his sisters two piece bikinis. Dark blue and cut high in the hips, it looked snug. 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. Removing his clothing, he admired his form in the mirrors while lightly stroking himself.

Stepping into the bathing suit and pulling it up over his hips, he marveled over how tightly it hugged him. 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 breasts didn't leave sagging empty material. It fit snug against his chest. Leaving the firm outline of his erect nipples. The mushroom shape of his cock was clearly visible , pinned to his abdomen. A small wet spot blossoming out from the head.

He always generated a lot of pre cum. Crawling onto the bed and laying on his back, he began to work his hands all over his body. Fingering the seams around his thighs, the smoothness of the material against his abdomen. His cock ached, beating with a heart of its own. Rolling over onto his stomach, writhing around, he prepared for the finale. Hesitating, remembering the vibrator and the lube, he made a quick decision. Popping the cap to the lube he squeezed some out onto his finger, it was cold. While laying on his side he reached behind and slipped his hand under the back of the swimsuit. Rubbing the lube onto his asshole, he nearly orgasmed. Tentatively he probed his hole with his finger, his hesitancy almost a tease. One knuckle, then two, he slid his middle 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 his opening. Feeling tremendous pressure, as it was much larger than his finger, he almost chickened out. 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 out, and back in again. Slowly he became adjusted to the girth of the object, his cock throbbed and released pre cum in rhythmic spurts. 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 himself back onto the bed. Slowly he pushed the device fully into his asshole, where it made contact with his prostate. He had never known such a pleasurable feeling. Desparately he pulled the fabric of the swimduit aside and freed his throbbung cock. He lay that way for some time, watching his dick wag around under its own volition. He reveled in the feeling of the vibrator inside of him, pinned firmly between him and the bed.

His cock oozed pre cum, strings of it dripping onto his covered abdomen. Gyrating his hips to mimic the forceful give and take action of intercourse, he managed to unexpectedly swith the device on. The vibrations came with such intensity that without hesitation or effort, he began to climax. He exploded. Hot, white, strings of sticky cum, blasted out so powerfully that the first couple jettisons hit him in the face.

He moaned out loud almost crying out, his cum ran down the side of his nose and onto his upper lip. He licked his lips instinctively, the taste of his cum rocketed him into a second round of orgasmic spasms. He cried out in pain as the vibrations became far too painful. He rolled to his side and grasped the vibrator desparately pulling it out. The large suction sound that followed came just a moment before the pain.

"Y-y-yoooooow" this time he cried out.

He felt his asshole spasm and slowly close. Curled up in pain, he lay there for a minute, tears in his eyes. Gathering his strength, he began to cleaned up. In a state of shock, everything a blur, he finished off the rest of the day, numb to the world.

The next day, he had several rooms to clean, the weekend having arrived, a small number 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 finally caught sight of the occupant. 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 25 year old sister. She had bleach blonde hair and couldn't have weighed more than 100 lbs. Inwardly he chuckled, the thought that she had no idea where her vibrator had been, amused him. The image of her using it herself 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, he had her swimsuit to remember her by. With that thought, he put his mind to cleaning hoping to finish early.