Follows after the events of 'Being the Night Shift Guy. Chapter 7' but can be read as a stand alone story. Jessica has been hired by a hotel heir who has paid for the privilege of being the first to enter her bottom.
Suite Penetration with Jessica Thot
After leaving her night shift guy in safe hands Jessica made her way up to the room Lee had booked for the night. Tapping her card against the door she made her way in to find that Lee was already waiting for her.
He sat casually in one of the antique chairs, absent mindedly scrolling through his phone and wearing only an expensive pair of boxer shorts. Laid out on the bed was a maid's outfit, an interesting choice for someone who had grown up in the hotel industry, and no doubt had already had sex with several real maids.
He said nothing as she slipped out of her dress and began putting on the small uniform. It was clearly a costume maid's outfit and not something worn by actual staff members. However, he had paid extra to have the Tipton Hotel logo embroidered onto it. The white uniform contrasted beautifully with her dark skin, and she took a moment to admire her thicc thighs beneath fabric that she guessed was covering only half her arse. Easy access, she thought to herself and smiled.
Once dressed she stood quietly at attention, waiting for him to come over and inspect her. He stood up slowly and she could see that he was partially erect. A little disappointing as most men should be fully hard seeing her in such a short dress. Of course Lee could have almost any woman, unlike the men who followed her on Only Fans. Maybe he would let her take some photos afterwards or even keep the outfit. She felt turned on imagining her night shift guy making love to her as she pretended to be his maid.
"Not bad" Lee mused "you fill that dress out well."
"Thank you master" she responded as she had been instructed to earlier.
He took his boxer shorts off and looked down expectantly at her. His brown cock stood at half mast and she could tell already that he was larger than average. Was that natural or did he use supplements? A rich man like him could afford the best, if such a product was real and not just an online scam.
"As you can see" he began "I am not yet ready to fill in your back hole."
"Of course master" she knelt down in front of him. Her poor knees, no pillow would be provided for her tonight.
She gently took his member into her hand and began slowly stroking, moving from top to bottom and back up again. This wasn't having much effect so she opened her mouth and licked the underside of his shaft. Things felt a bit harder now. Good, she thought to herself, progress.
She opened wide and took his entire cock into her mouth. She didn't need to work much after that as he immediately began roughly thrusting into her throat. Thank goodness for her lack of gag reflex, she thought, as he fucked her mouth.
Once he was fully erect he removed himself from her mouth. Jessica let out a few loud breaths before regaining her composure.
"Prepare for me on the bed" he instructed.
"Yes master" she replied obediently.
She walked over to the bed while massaging her jaw. Assuming the position she leaned over the bed. No need to pull her dress up as she could feel that her bum was fully revealed to her client. While she waited she could hear that he had gone over to the night stand to apply some lube.
"Is your ass ready for me?"
"That's a good little whore" he sounded turned on by his own words "at least you saved something for a nobleman like me. It almost makes up for giving away your other holes to less deserving men."
"Thank you master."
She could feel his strong hands separating her cheeks as his cock started to make its way inside. He is big, she thought, and she could feel every centimetre.
"You're so big master."
"All the better to fuck you with my dear" he laughed joyfully as he began thrusting, slowly at first, but soon picking up speed.
"Oh my, oh oh" she moaned loudly, only slightly acting to encourage him. This was a new experience for her, but she already knew she would like to try it out with other men. Or maybe Susan and one of her dildos. She was getting moist just imagining it.
"What an amazing little slut you are" he seemed to get off on degrading her, not that she cared at the moment. "Worth the money, that's for sure." As he said this he playfully slapped her arse. She reacted with a high pitched squeal, which resulted in him slapping even harder.
He was clearly enjoying himself and it wasn't long before he came loudly. She could feel his cum filling her anal cavity and suddenly wondered what it would feel like as it slid out of her. After cumming he soon removed his cock and began wiping himself clean on the back of her uniform.
"You were good" he said while catching his breath.
"Thank you master."
"I need to shower now. You should go, I have another girl arriving later tonight. Keep the uniform, I have no doubt you will want to remember this night."
"You are too kind master" she stayed still and listened for the shower to start. Once she could hear the water running she picked up her dress and started making for the special bathroom.
Once there she draped her dress over one of the stalls and took a seat, letting the events of tonight sink into her mind. As tired as she was she still noticed how quiet it was. The Dorian Grey type and his two Euro girls must have left for the night. A pity, she thought, she was hoping for another sexual encounter.
After emptying herself as much as possible she washed her hands and splashed some water onto her face. Not ready to go home yet, she walked around to where the couches were.
"Oh" she was startled when she saw an older man sitting on one of the couches. Short grey hair, dark suit with a bolo tie.
"Sorry to startle ya" he said politely in a southern US accent "I jus' needed somewhere quiet to rest up."
"Don't worry about it" she replied, then had a thought "were you hoping for some of tonight's entertainment?"
"It seems everyone's gone home" he looked her up and down, then started to reach for his wallet.
"No no" she interrupted "this is on the house, I've been bought and paid for by Leopold Tipton." Not technically a lie, she thought to herself.
"Now that's a bit of luck" he gave her a big smile as she slowly walked over, revealing her trimmed bush with each exaggerated step. She motioned for him to stand up as she took a seat on the arm rest, putting her face at the ideal height. She could already see that he was rock hard. Reaching forward she carefully unzipped his trousers. "You're a good girl, aren't ya darlin'?"
"That's right mister" she said cheerfully. Smaller than her last endeavour it wasn't long before his cock was in her mouth. Being a gentleman he seemed content to let her show off her skills as she did her best to give a nice sloppy blow job.
After a while she released his member, resulting in a satisfying 'pop' sound. "So, what brings a southern gentleman like yourself to Australia?"
"Business" he replied as she was jerking him off.
"And is there a Mrs back home waiting for this?" she squeezed gently as she spoke.
"I've been divorced now for a few years" he said sadly.
"No" he began "we couldn't, I..."
"It's okay, I was just hoping you might be a DILF."
"Oh" he perked up a bit "y'all one of them daddy issues kind a girls?"
She looked up at him, cock in hand "oh daddy, we all are."
"In that case darlin' you better put that back in your mouth, 'cause daddy's got a present and it ain't far away."
She quickly obeyed and took his cock into her mouth. He was very turned on and began desperately thrusting into her. It wasn't long before he came inside her, probably more than he had cum in a while. Her mouth was so full and she could feel semen running onto her chin.
When she was sure he had finished she looked up and opened her mouth, revealing a large load of cum on her tongue. He was staring down at her, looking both tired and enamoured. After Lee's almost disinterest, it was nice to see a man who could worship her. She closed her mouth and made a show of swallowing his load.
"What's yer name darlin'?"
"Jessica, that was the best orgasm I have had in a very long time."
Looking into his eyes she could see that he was being completely honest. These were the moments that made her love her job. These moments were why she became a sex worker. Now, there was nothing left to say, except "thank you daddy."