The Retreat Pt. 01

"Where will life take you?"

The words rippled across the page, surrounded by impossibly gorgeous women draped in equally gorgeous clothes.

Stewart had been staring at the ad for five minutes now. Admiring the models, their elegance and the luxury of it all.

A sudden jolt brought him right back to reality, sat on the forty six bus on a rainy Tuesday morning. The prospect of an eight hour shift loomed before him and the only colour in the day was coming from the copy of Conde Nast Travller in his hands.

Stewart didn't think life was taking him anywhere to be honest. He was a newly minted thirty year old, with a dead end job, crappy rental flat and no girlfriend. Or any real friends for that matter. He had mates of course but none that he truly had connected with.

Why was he being so down this morning? Turning thirty hasn't helped at all. He stared at his reflection on the bus window for a moment. Close cropped short brown hair he trimmed himself to save money. A sparse beard hiding a weak chin. Nose too big as well he thought glumly. His saving grace was big bright blue eyes and long eyelashes. Great when he was a kid and looked "adorable" but a bit weird on a grown man perhaps.

He didn't need to look down to be reminded of the rest of the picture. He was slim, always had been, a bit gangly but only 5' 11" so it didn't show too much. He had tried to put on some more masculine muscle before but without any really success. Stewart didn't really mind how he looked, he was as vanilla a looking guy as you could imagine. A face among the multitudes.

Fifteen minutes still to go before he got to work. He dived back into his magazine. Stewart was sure he was made for something a bit more than this. Despite his beige existence he had a real fondness for life's luxuries. He loved nothing more than disappearing into a world of high fashion, travel, luxury hotels and spas, expensive cars and fine dining. Of course it was only ever theoretical, on his fast food chain minimum wage, luxuries in Stewarts life were few and far between.

That didn't mean they didn't exist. The advantage of his simple life was that he spent very little day to day. This meant, once in a while, Stewart would splurge on something fancy. A luxury hotel break, a gourmet meal or a fancy piece of clothing. He also loved driving around in his cheap Porsche Boxter, even though his mates mocked it as a hairdressers car. What did that even really mean anyway? Not that is mattered, on sunny days Stewart could imagine he was flying down the French Riviera rather than the outskirts of Reading.

Finally the bus arrived at work and Stewart got off ready to sell his soul for another day. He changed into his fry cooks outfit and took his place in the line. He was next to Gail today, a gift for sure.

Gail was nineteen, fresh from college and everything Stewart wasn't. She was going places. Taking a gap year before heading to uni in London to study fashion. Tall, gorgeous and far too intelligent to be working in fast food. She was just passing through Stewarts world, earning some pocket money before jetting off somewhere exotic.

"What did you think of the Chanel shoot in Vogue?" Stewart asked. He often tried to talk fashion with Gail. He wasn't sure if she found it endearing or a bit creepy.

"Not for me." She replied, humouring him at least. " It was trying too hard, I don't think Chanel should be sexy, these days they should stay classy. Let the younger brands take care of sexy."

Stewart could feel a blush starting. Just hearing the word "sexy" come out of Gails mouth was enough for him. He involuntarily glanced down and caught sight of Gail's pert butt curving away beneath her apron. Even in a shapeless cooks uniform she shone.

"What sort of look will your brand have when you're a fashion big shot?" He asked quickly to hide his embarrassment and hopefully distract Gail from his glance.

She side eyed him knowingly. "Oh, it would be sexy Stew, you know that!" She followed with a hair flick and an over the top air kiss, and could see Stewart was hooked.

She sees right through me he thought. But, at least she plays along. He hated being called Stew, everyone did it but he couldn't stand it. It sounds dull and rank at the same time. He could give Gail a pass though. As far as he was concerned she could call him whatever she liked.

The pair chatted on and off while to drudgery of the day pushed on. Eventually the shift ended and Stewart clocked out with barely a word. Another dull bus ride followed until finally he was home.

Stewart rented a studio flat above a Sainsbury's Local on the high street. It was poorly furnished and bleak but it was home. After a bowl of packet ramen noodles Stewart collapsed onto his bed ready for the highlight of his day. A long edging session.

This has been his method of unwinding for as long as he could remember. He put on a kimono style robe and pulled his bottle of lube out from the bedside draw. Popping open his laptop it was already on his favourite porn tube site and Stewart felt his cock twitch on anticipation. He wasn't the most well endowed man but it wasn't small. He was much more of a grower and he got nice and hard. When fully erect he could bounce his manhood around like a spring. Something he always found oddly erotic.

Without a second thought Stewart floated away into a sea of porn. He always started with some nice glamorous stripteases. He loved a gorgeous curvy body wrapped in sensual underwear. The power of the woman as she slowly teased her figure and femininity. The glimmer in her eyes that said she knew how sexy she was and loved being watched. Stewart's cock was throbbing now, it was oiled and slick to touch. He grinned knowing it would be like this for hours now.

But, it didn't take long for Stewart to make his way to the transgender category, he knew this is where he would spend most of the night. Stewart had always thought of himself as straight. His porn viewing habits aside. But, more and more these days his mind was filled with gorgeous transgender women and cute sissy sluts. They made his cock much harder for much longer than straight porn ever did. He had ceased analysing it a long time ago and now just embraced it. It's not like anyone was around to find out.

As the session came to an end Stewart was watching a video of one of his favourite Trans performers. It was an intimate solo video and Stewart couldn't take his eyes off her hard meat. It was perfect. Long and stiff with a smooth head. The shaft was bulging, thick with veins and looked like it could burst any minute. Stewarts mouth was watering involuntarily, he imagined having such a gorgeous piece in his mouth. Filling him and enjoying his tongue.

He erupted immediately, just the image in his head was enough. A powerful orgasm flowed through him and hot cum covered his belly. He ached to taste it but his post orgasm come down kicked in fast. Suddenly that didn't seem sexy at all. Cleaning himself up Stewart felt the usual quiet self loathing that came from these experiences. He wished either he didn't have these urges or that he could at least feel at peace with them.

As he drifted off to sleep his subconscious got to work on that request. Stewart's life was about to take a turn for the interesting. He just didn't know it yet.