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- May 27, 2017
Jessie wasn't from a particularly well off family, but they got by well enough to survive without exactly being in poverty. Still, it meant that they didn't really have the money for him to have the things he wanted. Jessie never had the latest cell phone, he never had the latest console or newest computer games and almost certainly wouldn't be able to attend college. They didn't have the money and he wasn't an A+ student to get a scholarship. He'd looked for part time jobs in all of the usual places, but none of them were hiring, or the ones that were hiring generally gave the jobs to the cooler, more popular students, the ones who'd bring in business rather than turn it away with a 'lameness factor'.
Just when he had been about to give up though, when Jessie was ready to resign himself to a life of just 'getting by' he had come across a rather odd flyer. He had just been walking through town one day and one of the usual people on the street handing out flyers had shoved it into his hands before he could turn it down. Rather than being an ad trying to sell something it seemed to have been a job advertisement, a job advertisement for...well...'escorts', but not just any escorts, it seemed the agency specialised in Traps. Jessie had always had something of a feminine appearance, so it was understandable why the person handing out the flyers had chosen to give him in particular one.
At first he just shoved the flyer in his pocket and dismissed the idea, but the more he thought on it the more he started to consider it. The money would be good, way more than he'd get working part time at a store. He could afford all the latest stuff and save for college all at the same time, no need to pick and choose.
The next few days had been something of a whirlwind, Jessie had called the number on the flyer, gone to meet with a rep from the agency and been treated to a nice meal at a nice restaurant, then before he could really realise what was going on he had signed himself up, being given a bag containing everything he would need. Clothes, a wig, glasses, makeup, enough to ensure he wouldn't be recognised by the clients.
Now Jessie was arriving for his first job. The details had been texted to his phone, the address of a hotel and the room number. There hadn't been an outfit preference included in the assignment, so Jessie had opted for the schoolgirl uniform, complete with even bra and panties. His normally short blonde hair was completely hidden by the wig, the glasses and lightly applied makeup enhancing his already feminine appearance. He was nervous, incredibly nervous, this wasn't just his first job as an escort, it was his first sexual experience with another person. Still, too late to back out now, and he had to focus on not screwing this up if he hoped to ever make some decent money from this.
With one final deep breath, Jessie looked up at the door, checking the room number for perhaps the 5th time, then tucked his phone away in his bag, reaching out and knocking on the door firmly.
Just when he had been about to give up though, when Jessie was ready to resign himself to a life of just 'getting by' he had come across a rather odd flyer. He had just been walking through town one day and one of the usual people on the street handing out flyers had shoved it into his hands before he could turn it down. Rather than being an ad trying to sell something it seemed to have been a job advertisement, a job advertisement for...well...'escorts', but not just any escorts, it seemed the agency specialised in Traps. Jessie had always had something of a feminine appearance, so it was understandable why the person handing out the flyers had chosen to give him in particular one.
At first he just shoved the flyer in his pocket and dismissed the idea, but the more he thought on it the more he started to consider it. The money would be good, way more than he'd get working part time at a store. He could afford all the latest stuff and save for college all at the same time, no need to pick and choose.
The next few days had been something of a whirlwind, Jessie had called the number on the flyer, gone to meet with a rep from the agency and been treated to a nice meal at a nice restaurant, then before he could really realise what was going on he had signed himself up, being given a bag containing everything he would need. Clothes, a wig, glasses, makeup, enough to ensure he wouldn't be recognised by the clients.
Now Jessie was arriving for his first job. The details had been texted to his phone, the address of a hotel and the room number. There hadn't been an outfit preference included in the assignment, so Jessie had opted for the schoolgirl uniform, complete with even bra and panties. His normally short blonde hair was completely hidden by the wig, the glasses and lightly applied makeup enhancing his already feminine appearance. He was nervous, incredibly nervous, this wasn't just his first job as an escort, it was his first sexual experience with another person. Still, too late to back out now, and he had to focus on not screwing this up if he hoped to ever make some decent money from this.
With one final deep breath, Jessie looked up at the door, checking the room number for perhaps the 5th time, then tucked his phone away in his bag, reaching out and knocking on the door firmly.