Tom's First Time Getting Fucked

Tom scanned the hotel reception then put his head down quickly. There was no one working that he knew, he thanked covid for one thing, the mask he had on that concealed his face. If it wasn't for the mask he probably wouldn't have the balls to go through with this, it quelled his butterflies somewhat.

Thankfully he found the elevator quickly and looked somewhat like he knew where he was going. Having someone ask him if he needed help was the last thing he wanted. Tom pressed the button for the elevator and waited, gripping the strap of his rucksack that hung off his shoulder.

As he waited his thoughts were firing non stops, is this what I want, what if he's unclean, are we doing the right thing, is it safe? Tom pushed the thoughts aside and replied to his mind and affirming to himself, this is correct. A meet like this he has fantasised for many years but never had the guts to follow through with it.

But tonight is different, if a little spontaneous. Tom's girlfriend was out of town and as usual he opened a profile on a hookup site to see who's about and chat. He did this regularly when home alone but never met with anyone. Tonight though an out of town business man was staying in a local hotel, he had nice pictures, looked clean and his cock was a good 6 inches. Perfect for a first time Tom thought when he messaged him, turns out this guy is into cross dressers and liked the pictures he saw on Tom's profile.

A few messages later and here we are. The elevator dings and Tom walks in, thankfully no one else is wanting to use the lift. He presses 3 and waits for the doors to shut before looking in the mirror. He was a tall broad man, not the body of a femboy. Shot black hair and olive skin, he was in a simple black t-shirt and black jeans. In his rucksack was his skirt, thigh high socks, lube and condoms.

The elevator had arrived, this was his last chance to back out, Tom stepped out into the hallway and hesitated but thought to himself it's now or never, he was alone in the hallway and forced himself to walk and find the door, it happened to be not far from the elevator, he knocked twice and removed his mask while he waited.

The sound of footsteps getting closer to the door made his heart beat twice as fast, the door opened slightly with a head popping round the gap.

"Hello," said the man.

"Eh, are you SilverFox70?" whispered Tom, unable to hide the nerves in his voice, he checked up and down the hallway as he waited for a reply.

"Yes, yes, please come in." said SilverFox70 opening the door wide.

Tom stepped in, the room was standard size, double bed in the middle, an arm chair in the corner draped in shirts and trousers and a ensuite bathroom. Tom scanned the room quickly, the bed looked clean and appeared untouched.

His eyes fell upon the man, he was in his early 50s had short greying hair and a round protruding beer belly but not overly fat, a towel was round his middrift. Excellent, so he has showered thought Tom who stood awkwardly at the door entrance heart beating out of his chest and mouth going dry.

"Are you coming in? or," said SilverFox70 gesturing with his hand waving Tom in while his other hand leant on the door handle. Tom nodded and stepped in, the door closed behind him.

"Mind if I use your bathroom?" asked Tom, not looking at the man and already walking towards it.

"Of course," replied SilverFox70.

Tom closed the door and put his rucksack down, and quickly took his trainers and trousers off then grabbed his girlfriends black thigh high socks from his bag, he put his foot in and pulled them up to his thigh, they were dark black nylon socks with red bows at the top, he repeated for the other leg and then stepped into his girlfriends black skirt it was short and slutty just covering his round bubble butt and giving a nice sexy thigh gap between skirt and nylon socks.

He kept the black t-shirt on, it went well with the skirt and this was him dressed, not a convincing crossdresser but he figured it didn't matter if he was head down and bent over downward dog on the bed, he should be a good enough fuck. He was smooth all over, not from shaving but naturally not hairy at all. His cock was semi erect and lifted the front of the skirt slightly.

Tom douched before arriving so hoped he was still clean as he grabbed his lube and condoms and opened the door. The main light was off and the room had a cosy dim glow from a side lamp by the bed. Perched on the end of the bed was SilverFox70 his towel was gone and he sat stark naked, legs spread wide facing the bathroom, he stroked his erect cock as he looked up.

"Bloody hell, your legs are gorgeous, is this really your first time?" he asked

Tom nodded as he walked slowly towards the naked man, placing one tiptoed foot outstretched then leading with the other, doing his best catwalk style walk. "Yeah, first time with a real cock, but no need to go easy on me." said Tom

"Give us a twirl, darling."

Tom grimaced slightly at being called darling but spun around so his black pleated skirt lifted.

"What's your name?" asked SilverFox70

"Tom."

"No I mean your, girly name, what do you call yourself?"

"Oh I don't have one," Tom shrugged and dropped to his knees and covered the short distance moving on his knees to sit between the man's legs.

"Tom, Tom, hmm, what about Tommie, Tomisha, nah Tracy, yeah you're Tracy now." The man shook his cock at Tom.

"Now suck it Tracy."

There was no backing out now, the thigh high socks and skirt was like a mask, a different character. He guessed he's Tracy now, he took the cock by the head with one hand and pulled the foreskin back then lent forward with an open mouth, the tip of the cock slid over his tongue, he closed eyes then his mouth and flicked his tongue around the tip while sucking back n forth. His hand on the cock twisted up and down in time with his head bobbing up and down.

The man moaned, "Good girl."

This was the first cock Tom has ever sucked and he loved the feeling of it and loved that he was giving pleasure. To his surprise he felt the cock grow thicker and larger than it already was. Tom gagged as the enlarged cock hit the back of his throat.

He had practiced deep throating a dildo before but was too scared to really push it but now with this large cock In his mouth he wanted it all, he wanted to fuck his throat like a slut. He pulled the cock out of his mouth and took a deep breath, trying to relax then he plunged his mouth down the cock, his cheeks puffed out as he gaged and spluttered but he held the cock as deep as he could go, his gag reflex squeezing the cock forcing it out.

Then he felt a strong hand on the back of his head forcing the cock down his throat further, he violently retched and desperately tried to move his head back but the force of the hand didn't relent as he choked and spluttered on the cock violently. Eventually the hand let him up, Tom's eyes were bloodshot and watery, and as he lifted his mouth off the cock he left a thick strand of drool.

Before he could really catch his breath, both hands grabbed the back of his head forcing him down hard, the cock engulfed his throat once more. He had no control of his head, his mouth was a fuck toy as he was forced back and forth hard and fast. Gagging everytime he was forced down the cock.

The man was moaning each time his cock reached the back of Tom's throat "You're such a slut, letting me fuck your throat like this." He said, not missing a beat.

"You sure this is your first time?" chuckled Silverfox70.

"Get up on the bed, on all fours." he said

Tom wiped his mouth on his arm and stood up, he noticed the man staring at his long toned nylon covered legs.

"Hmm, I love your legs," he said as Tom climbed on to the bed and layed his head down on his arms and left his arse in the air.

He closed his eyes and waited.

"Especially with that skirt and those thick thighs, so sexy." he heard the man say, his voice coming closer. He sensed he was behind him now.

Then Tom felt his skirt lift up slowly, the fabric stroking the back of his legs and arse until it was lifted all the way up on to his back. The sensation and anticipation made his cock hard. Then a smack across his bum cheek startled Tom who grunted.

"You like that, Tracy?" Another but harder spank in the same place elicited the response the man wanted as Tom moaned half in pain.

"I want you to call me Daddy, ok?"

Tom didn't respond for what seemed like an eternity, but was paralysed by fear, he can't back out now. He was uncomfortable with it but eventually replied. "Yes, Daddy."

He felt two hands grab his arse cheeks and pull them apart  then sharp bristles of shaved beard hair rubbing his arse cheeks as a tongue pressed against his tight hole. The tongue

flicked and licked his hole. Tom relaxed and pushed his body back as he enjoyed the sensation of the tongue prodding and licking his bum hole.

"That feels good...Daddy," says Tom turning his head, he notices the mirror and sees himself bent over, head down on the bed and ass up. His nylon covered legs half off the bed and the man old enough to be his Dad crouched down eating his arse.

"hmmm," Tom moans as he loosens his tight hole and feels the tongue do it's best to penetrate. "I'm ready, for your cock."

A muffled "What?" was the reply, the licking not missing a beat, now a hand gripped his cock and tugged up and down.

Tom moaned at the new sensation.

"Please don't, you're going to make me cum, Daddy, stop," begged Tom. The man stopped wanking him and chuckled "You're so sensitive, you're really enjoying this aren't you?"

Tom felt his cheeks go red, "I'm ready for your cock, Daddy."

Tom watched through the mirror as the man got up and rummage through his bag and returned with the Lube.

"I didn't hear you, what did you say?" said the man lubing his cock.

"Fuck me, Daddy." Tom said closing his eyes.

He felt a dollop of cool lube on his arse then a finger moving it around then entering gliding easily in up to the knuckle then out again. Then he felt two fingers doing the same motion of coating themselves in lube then entering, his anus parting easily for the two fingers.

"Ah, you've done this before, you relax so well. Now tighten on my finger," commanded the man.

Tom clenched tightly around the fingers.

"Good slut, this is why anal is better with men. Girls can't clench like that as they don't have one of these." says the man.

Tom feels the fingers in his ass hook and bang into his prostate, he loosens again and moans like a girl for the first time as he's finger fucked hard straight onto his prostate.

The fingers are then ripped out roughly and a large bulbous cock presses against his anus, the man grabs his hips and draws him back as he pushes. Tom's anal splinter struggles to give way, he focuses on relaxing and feels every part of him giving way to the thick cock that inches further and further into his anal cavity as his one tight hole stretches around the cock.

"Oh god, I love it, I feel s..o..ah..ah..aw..." Tom's words are taken away from him as the man pumps his cock in and out

of his arse, Tom moans involuntary with each deep thurst, he's lost for words, he can only moan in pleasure as this man takes his anal virginity, their bodies slapping together with every thrust as he moans.

This better than I imagined he told himself, opening his eyes now to watch the man in the mirror grabbing his hips and pulling himself back on his cock as thrusted deep inside.

"Baby, you've got such a nice pussy,"

Tom felt the cock slide out of his arse and his bum cheeks pulled wide again

"Mmm such a nice gape, roll over."  the man continued.

Tom turned so he was on his back with his legs raised and toes pointed.

"Hmmmn, you have great legs." the man said caressing Tom's thighs and stroking his nylon covered legs, placing them on his shoulder as he leaned over.

Tom grunted as his body folded almost in half under the weight of the man on top, then he gasped in shock and pain as the cock entered him deeper and harder than before, the man was primal, savagely fucking him hard like worthless fuck doll, that's all I am thought Tom, turning his head away from the man's hot cigarette smelling breath as he fucked him relentlessly.

The pain subsided or Tom got used to it and the pleasure of being used like this took over him moaning in pleasure softly and high pitched like the slut he was and the moans only spurred the man on who fucked him even harder.

Tom felt the orgasm inside him building up, "Urgh... fuck," Tom's body tensed, legs tensed, his arse tensed around the cock fucking him as he screamed out as cum spurted from his cock, He felt the cock inside him quiver now and pump, The man kept it in pumping then pulled his now soft cock out, panting.

"Push it out." The last command of the night.

Tom squeezed his stretched anus which farted and squelched as cum pushed out his wrecked hole and continued to dribble out.

"You want to stay tonight?"