***Author's note: Anyone in this story who indulges in any sexual activity is eighteen or older.***
1
This was by no means Jackie's first gang-bang, and she couldn't imagine for a second that it would be her last, but it was most definitely the first gang-bang where her teenage son happened to be in attendance.
Stavros, her usual contact from the escort agency, had phoned her that afternoon; a last minute booking had come up, suddenly, out of the blue.
"We're talking multiple clients." He had said, in that disinterested, matter-of-fact tone he always used. As if pimping out women for sex was no more exciting than doing some minor clerical work.
"Define
multiple
clients,
Stav?" She had responded.
"Five guys. College boys, out for a good time."
"I see. And you want me to show them a
good
time
all by myself? That's a lot of cock for me to suck on my own. I could do with some help, to take the strain." She said. "Hell, if we're talking about a
party,
wouldn't they like to see a couple of us girls put on a show?"
"What kind of show?"
"Eat each other out. Fuck each other with strap-ons. That sort of thing." She looked around for a moment, suddenly aware of what this conversation might sound like to disinterested passers-by.
"You definitely paint a picture with words, that is your gift. Well,
one
of them." Stavros replied, with a dry tone. "But no one else is around. You're the only lady available. Come on, Jacks, you know you're just the girl for the occasion."
Jackie stood there for a moment, pondering her course of action. She could feel a familiar tingle growing inside her. A sense of excitement and anticipation.
Five guys.
Five college guys.
Jocks,
probably. Young men with hard bodies and, hopefully, big dicks.
Oh fuck, who are you trying to kid?
She thought to herself.
You know you want to do it.
"Okay, I'm in." She said.
"Cool." Stavros replied. "I'll email you the details. There's a two-hundred dollar bonus in it for you."
"Great."
"Oh, one more thing. You might want to attend to certain hygiene matters; they paid extra to do you in the ass."
"Yippee!" She muttered, wanting to sound sarcastic and jaundiced, but her excitement still seeped through.
She hung up, and a few seconds later her phone pinged, telling her she'd received a message. Stav's email informed her of where to go, what time to be there, and who her contact was. The
party
wasn't for a few hours, so she had plenty of time to get ready.
Jackie took a quick shower, administered a couple enemas and then shaved herself all over, paying special attention to her crotch. The vast majority of clients these days had an almost pathological aversion to female pubic hair - college boys especially - and so, in a 21st century consumer-capitalist society, like the good ol' US-of-A, Jackie understood that she had to cater to her patrons' desires. If that meant
no bush
, then no bush it was.
She thought it was a bit of a shame, to be honest. Jackie was a natural redhead - well, she had been; she'd been dying her hair for years now - and, if she let it grow, she had a fiery patch of coppery ginger pubes, that she was rather proud of. But hey, in the world of classy, high-end prostitution, the customer was
always
right.
Jackie then got dressed. She opted for a very casual look. Jeans, knee-high boots and a dark, modest top. She looked like a common-or-garden soccer mom. If you saw her, you might not give her a second look. And that was
exactly
the point. The way it usually worked, especially if she was heading to a hotel, she would dress like a
civilian
. The management at those types of establishment knew exactly what went on under their roofs. Call-girls came and went. It was part and parcel of every hotel's daily routine.
If you were a hooker, looking for
business
in the bar or lobby, you dressed appropriately - some varying degree of sluttiness - and you hoped you wouldn't be asked to leave. If you already had a
date
arranged in one of the rooms, however, you tried to look inconspicuous. Once you arrived, and received your customary
donation
, you could head to the bathroom and whore yourself up.
Then the fun would begin.
Sometimes you had to play cat and mouse with the hotel employees, depending on how uptight they were. The best places, with the best lobby staff, worked
with
the girls. They understood that some of their guests had certain
needs
, and someone like Jackie was exactly the sort of person who could cater to those needs. Anonymously and discreetly. Her agency's number was in the personal phonebook of plenty of
concierges
in town. There would usually be a little kickback for them, if they helped arrange a meet up. Some preferred payment
in
kind
, and Jackie had been known to blow a few guys in the front office when she had to.
Her current destination was a hotel downtown, called The Mallard. It wasn't the classiest of joints, not anymore, but she'd been fucked in plenty of worse places. In its heyday it had been pretty smart, but now it looked a little worse for wear. Past its prime. Jackie knew the feeling.
She'd arrived ten minutes early and made her way to the room number she'd been given. She was carrying a large bag, that contained all the things your modern sex worker might need to provide some sensual pleasure. There was a change of clothes, including stockings and slutty lingerie, plenty of condoms, Viagra, lube, handcuffs, and even some dildos (which Jackie doubted she'd have any need for tonight). There was also a can of mace and a telescopic baton.
You could never be too careful.
She took a moment to compose herself, put on her
game-face
as it were, then she knocked on the door. After a few moments, it opened and a young, blond-haired man was stood opposite her.
"Uh...hello?" He stammered, nervously.
"Hello, sweetie." Jackie said, with the confidence bred by years of meeting clients in situations exactly like this. "Are you Paul?"
"Yeah."
"Well, hello Paul. I'm Glory. Are you going to invite me in?"
"Sure."
He opened the door wider and Jackie sauntered past, putting on the best hip-swaying moves she could muster. She always knew how to make an
entrance
. Paul closed the door behind them.
Glory was her
professional
name, the name she used when she fucked and sucked her clients. It was a terrible pun really. Jackie was christened Jacqueline Louise Blaze. Jackie Blaze would have been a great name for a prostitute, but she had been advised to take up a
pseudonym
and, after much consideration, Glory seemed a reasonable
moniker
to adopt. In truth, she didn't like it that much, but she'd been using it for the best part of twenty years, so she wasn't going to change it now.
She made her way into the room, which was in fact a suite. There was a short hallway, going through to the main bedroom, with a couple of other doors, presumably leading off to a bathroom and perhaps another bedroom. Paul led the way, nervously looking back over his shoulder from time to time. Jackie wondered if he might be a virgin. He was quite handsome, tall and with a fine physique, but he didn't seem all that confident. The thought both amused and aroused her. Taking a teenage boy's
cherry
was one of Jackie's specialities.
In the main bedroom, she found two other young men, sat casually on the edge of the bed. They looked a lot more relaxed than their friend. She smiled at them all, with a dazzling insincere sincerity.
"Well, gentlemen, are we all going to have ourselves a good time tonight?" She asked.
"Sure thing, ma'am." One of the other boys replied, eyeing her up and down with an almost carnivorous leer.
He's no virgin,
she thought to herself.
He is going to be someone I'll have to keep my eye on.
"So, I was told there were going to be five of you strapping young men. I was never too hot at math, but I can only count three."
"Uh...yeah...there are two other guys but they are running a bit late. They should be here soon." Paul stammered.