Pre Story Context
UK readers and some places in Europe will likely be familiar with what a 'Holiday Rep' is. For anyone in the US, Canada, Australia or based anywhere else, I don't think there is an equivalent job that you will be aware of. It was a job that many young British people did for an opportunity to work abroad, without having to speak another language, and for the chance to be promiscuous in the environment of Sun, Sea and Sex. We represented the Tour Operators who arranged package holidays from the UK to Spain, Portugal, Greece, Türkiye, etc. Guests would book a package holiday for a week (sometimes 2 weeks) that included their flights, their hotel and on arrival, a bus transfer to their hotel, with their Holiday Rep meeting them at the airport and escorting them on their journey. For the duration of their holiday, we were on hand at their hotel (or at least meant to be!) to be their point of contact, if they had any problems, if they wanted to arrange excursions, etc. We booked tickets for tours, and we also arranged evening entertainment, normally involving copious amounts of drinking and partying. We took them on bar crawls in the town; we arranged nightclub tickets; we hosted parties on boats out on the sea. Most of us were very sexually active as well, with the customers, with the bar staff, and often, with each other. Lots of holiday makers, for some reason, wanted to fuck their holiday rep, and we were normally happy to oblige. We played drinking games in the bars that encouraged promiscuous behaviour....think of it as a frat house party that took place every night, all summer season long! We frequently hooked up with each other if we didn't fancy any of that week's arrivals much!
Some companies were marketed towards the young, free and single crowd, companies such as 'Club 18-30' (Google them, and the reputation they used to have!). Groups of Guys or Groups of girls, on holiday together, sometimes on bachelor/bachelorette parties, were our main clientele.
Whereas some other companies were marketed more toward family package holidays...the reps who worked for them didn't so much hook up with guests, but they did with each other!
I worked for a company similar to Club 18-30. (For the purpose of this story, the company name has been changed to a fictional one)
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I had worked as a Holiday Rep for Hedonism Holidays for several years. My first two summer seasons in Ibiza were a blur of non-stop parties, plenty of drinking, days I would never forget, and some days I couldn't remember. After being a not-so-confident guy in my youth, this job had changed me, and I had slept with more women than I ever thought possible, and done some pretty wild things that I would never be able to tell some of my family about! In my 3rd season, I had been moved to Crete in the Greek Islands, and that was just as wild as Ibiza. By my 4th season, I had been promoted to Team Manager and assigned back to Ibiza. As I was experienced there, I knew the bars, the clubs, and their owners, so I would be a good manager to negotiate with the owners when we wanted to use their venues for our parties and events. I also knew the Island back to front.
My crew of Holiday Reps for Hedonism Holidays were a great mixed bunch, which was ideal for the company. It was good to have a mix of personalities to deal with the multitude of different types of customers we got. Some boisterous groups of guys responded well to a young, pretty and sassy female rep to rein them in when they got drunk and disorderly round the pool. A handsome young male rep could persuade a group of girls to buy tickets for all of the events we sold tickets for. I had a team of 3 guys and 3 girls, some of them on their first season, and some were a few seasons experienced.
This was around 2010, and we were not paid a great deal for the job we did and relied heavily on commissions from tickets sold. But also, we didn't need to worry about paying rent on the apartments we lived in; the company arranged our accommodations and paid for them, so our salary reflected that. It also meant that, to save money, we often shared apartments with other staff. I was lucky; as a Manager, I still shared, but it was a two-bedroom apartment, so at least I had my own room. It wasn't uncommon for the Holiday Reps to live in small, cramped studio apartments, or even share a bedroom in some cases. I was assigned to live with another Manager, Sabrina. She worked for the Parent company’s family holiday brand, rather than directly for Hedonism. So Sabrina didn't attend our parties or bar crawls, at least not on a professional basis...she often turned up out of uniform after she had finished her duties. But she was equally as promiscuous as the rest of us. She was a fun person to have to share an apartment with. She was a similar age to me, around 26 or 27 and was blonde-haired. She was a fuller-figured girl, but she was a filthy bitch. She was very vocal when having sex, and I once heard her getting taken from both ends by two guys when I came home one evening. Sabrina and I had also fucked a few times, after getting home after a night out. But we both knew it was what it was, and had no issue with the other coming home with someone whenever we did.
One morning, I was sat on our balcony, completing some paperwork alongside Sabrina. Paperwork and form-filling were the more tedious side of the job that they didn't advertise at the recruitment events in the UK. Sabrina looked out over the balcony, down the street.
"Isn’t that Aimee over there?" she asked, prompting me to look up.
Aimee was one of my Hedonism Reps. A first-year rep, she was 18, from Liverpool, with a broad Scouse accent, and only 4 ft 9 in tall. She was loud, confident and very pretty, and because of her small stature, guys loved her; they hoped to throw her around the bedroom like a ragdoll, given how petite she was. She also had developed a reputation in the short few months she had been in Ibiza. I was fully aware that she had been fucking the night porter at one of the hotels she represented, and I knew that she had been fingered on the dance floor of one of the clubs by a young guy on holiday, because I had seen that happen!
"Yes, it is...what time is it?" I asked.
"10:00," Sabrina said, looking at her watch. "Shouldn't she already be at work?"
"Yes, and she is clearly just coming home!" I said, looking at the state of Aimee. She was wearing next to nothing. What appeared to be a Trilby-style hat, a black corset, barely containing her tits, which were impressively sized for her height, and a skirt that covered her ass, but only just. Fishnet stockings and idiotically high-heeled stilettos, making her seem taller than she realistically was. She was stumbling back to the building, as we all lived in the same apartment block. She looked like she had been up all night.
"To be honest, I have seen her coming back after being out all night a few times, but wasn't sure what her hotel visiting hours are, so was never sure if she was late or not," Sabrina confessed.
"Yes, I am aware that she has not turned up for work a few times in the mornings. I think she needs to have her first written warning. She has had a few verbal ones, but she is taking the piss a bit now."
"We were young first year reps once ourselves, Jamie," Sabrina reminded me.
"I know, and we all missed duties once or twice, and we took the punishment that came with it. The company needn't bother paying for an apartment for Aimee if the little slapper isn't going to ever sleep in the fucking thing! Where the fuck has she been all night!?" I asked rhetorically.
"Well," Sabrina said, "I guess you will have to intercept her before she gets to her apartment, and we can find out what the situation is."
I nodded and went to the hallway. Aimee's apartment was on the same floor as mine and Sabrina's. She stepped out of the lift.
"Good morning, Aimee," I said, startling her a little.
"What the Fuck!" Aimee squealed, turning to face me. "Oh, hiya Jamie," she said sheepishly, knowing she had been caught.
"With me, please," I said, beckoning her towards me and had her follow me to my apartment. She followed, her heels clicking on the tiled floor of the corridor to my door. I led her through to the main room of the apartment, where Sabrina was waiting as well.
"Morning, Aimee," Sabrina said, raising her eyes at her.
"Hi Sabrina," Aimee said back. "Look, if I am in for a bollocking, then just get on with it, because I am knackered," she snapped.
"Aimee, you are in no position to make demands. Yes, you will be getting a written warning this time, and yes, you are already an hour late for work; you should be at the Don Carlos Hotel already, in case any of your punters need you. Why the fuck are you only just getting home now, and why are you dressed like that?" I asked her.
"It was Luke's birthday last night."
"Yes, I know it was. So?"
"He had a party at the Q Bar; it was a 'Pimps and Hoes' theme costume party," Aimee explained.
I understood her attire now; she looked every inch the little Hoe. "Ok, and you are only just getting back now?"
"I went to an after-party," she said, beginning to get visibly annoyed with the interrogation.
"You stayed there all night then?" Sabrina asked. "You look like you have barely slept, almost like you have been through an ordeal!"
"If you must know, I got fucked by four guys!" Aimee said brashly, thinking it would shock us into wrapping up the impromptu disciplinary hearing, clearly not aware that Sabrina and I, in our careers, had behaved just as badly, if not worse than Aimee.
That confession did get my attention, though. "Oh? And who were they? You thought you would live up to what you were dressed as?" I asked.
She sniggered and tried to hide her grin. "Yeah, I was up all night being a good little Hoe! I don't know who they were...some Spanish lads at the bar asked me if I wanted to go back to their apartment after the bar shut, for more drinks and a bit of a party, so I did." She was still trying to shock us. "I got fucked and spanked all night," she bragged.
"Spanked?" Sabrina said, slightly taken aback.
"Yeah, hard. Does it still show?" Aimee said, arrogantly lifting her skirt, which didn't need to be lifted much to show her bare buttocks.
Sabrina stepped off her chair, approached Aimee, turned her to face the table, and inspected her bottom, which was indeed still a bit red and raw from very clearly having been spanked. "Oooh, that looks sore?" She said, and without thinking, started to gently run her thumb over the red flesh.
"It is a bit," Aimee admitted, and turned to look at me, and saw that I was starting to get aroused at the sight of her bending over the dining room table, and Sabrina absentmindedly stroking Aimee's bottom.
I looked at Sabrina, who smiled at me. We silently acknowledged what the other was thinking. Then I continued questioning Aimee. "Tell us what happened, every detail," I said, joining Sabrina in soothing Aimee's other buttock.
Aimee realised what we were getting at and started to tell us what happened. "I went back to their place, and we had some drinks. One of them put some music on, and I was dancing with him. He started groping my tits as he did, and I put my arms round his shoulders and kissed him. I felt my knickers getting pulled down."
"And you let him?" I asked.
"I didn't mind; I wanted to fuck him. He unzipped himself and shoved it in me as we were standing, dancing. But it was awkward because of the height difference, so he got on his back, and I got on top of him and started riding his cock," she continued, clearly loving the audience hearing about her night.
"What about the other guys?" Sabrina asked, starting to run her hand along Aimee's inner thigh and onto her fishnets.
"Oh!" she groaned slightly at the touch of Sabrina's fingers on her sensitive skin between her legs. "As I was riding the guy on the floor, one of the other guys approached behind me. He said something in Spanish to the other guy, and then I felt him pushing his cock into my arse," she said, starting to breathe heavily, enjoying being touched gently by us, and getting turned on by her own story.
"You got DP'd?" I said, almost proudly. "Did they cum inside you?"
"Yeah, both of them did."
Sabrina hooked her fingers under the elastic of Aimee's underwear and slid them down, running her hands along Aimee's leg as she did. "You filthy little bitch," she whispered as she inspected Aimee's pussy, making her gasp as she touched it. She pushed her fingers inside her with a squelch, which coaxed out some of the cum that was still inside her; it started leaking out.
"And what about the other two guys?" I asked.
"They took me to the sofa, and one of the other guys climbed on top of me and started to fuck me. When he finished, the 4th guy got on. They took turns on me, spanking my arse as they were at it," She breathed as Sabrina fingered her well-used cunt.
"Did you like it?"
"I fucking loved it!"
“Oh, you dirty little hoe!” Sabrina gasped, listening to Aimee’s story. Sabrina could see how hard I was, and she was getting horny listening to Aimee's confession. She reached over and unzipped me, crouched down and took my cock in her mouth, her full lips stretching around me as she brushed her blonde hair away from her face and moaned and hummed around my cock.
Aimee looked back round and became aware of what was going on behind her, Sabrina still probing her pussy as she sucked my cock. She looked up at me, and I looked her in the eye. "Look at the state of you, dressed like a hoe, acting like a hoe and expecting to get away with it. Sounds like you got everything you fucking deserved last night! You like cock, I think we have established that." I told her.
"I fucking love it!" She squealed, knowing what I was getting at. "Please, Jamie, I want it!"
I pulled my cock out of Sabrina's mouth and drove it into Aimee's pussy as she bent over the table.
"Oh fuck!" she cried out as I thrust into her. "Oh god, give it to me!"
I fucked her hard, my thighs slapping against her exposed arse as I did. Sabrina, still crouched, ran one hand along Aimee's fishnet-clad leg and with the other, groped and massaged my balls as I drove into Aimee.
Aimee moaned and panted as we told her what a filthy cunt she was, which she didn't disagree with.
"Oh my fucking god, Aimee!" I cried out as I got close to the edge. “I'm gonna fucking fill you!” I could feel the evidence of the loads from the other guys who had been in there before me, which just made it hotter for how absolutely filthy it was.
"Oh Jesus fucking Christ!" Aimee shouted as I emptied myself inside her. Her Liverpool accent was even more pronounced as she felt the warm fluid flooding her already full and messy cunt, as she herself succumbed to a powerful orgasm.
I pulled myself out of Aimee, and Sabrina took me back in her mouth, sucking the last strings of semen from me, and tasting the cocktail of cum that was on my shaft from Aimee's dirty little hole. Sabrina stuffed her fingers back into Aimee, curling and pumping them, scooping out the collection of semen inside her, bringing her fingers to her mouth to suck clean. Then returning her fingers back in again, and fingered Aimee as she leaned against the table, bringing her to orgasm again. “Oooh..nasty little bitch!” She said as Aimee groaned as she came. “You nasty little bitch!”
We pulled Aimee's knickers back up and turned her to face us. She couldn't hide her smile. "Ok then, Aimee," I said, smirking. "Get back to your apartment and make yourself look presentable, and get back to your duties."
"Yes, Jamie."
"And you will get your written warning officially printed and given to you next time we are in the resort office. Just try to be home in time to go to your duties in the morning; I know you want to keep your job. If you get a second written warning, its the final warning and you will be on a plane home beyond that. So try to be on time."
"Ok, sorry, I don't want to be sent home. I'll try to get back home in good time in future," she said, and I believed her. She headed for the door.
"Oh, and Aimee," I said, and she turned round to me as she stopped at the door. "If you must get filled by so many men, try to make sure they are customers as you persuade them to buy tickets for the reunion party in the UK! Think of the commission!" I said, smiling and raising an eyebrow. Aimee smiled and nodded as she left the apartment.
I turned to Sabrina, and we both laughed as she gathered her things to head out to see some of her team.
"You have a live wire there, Jamie!" she laughed.
"Certainly have....do you think she learned her lesson?"
"No!"
"Me either! I might have to discipline her a few times this season! I don’t know whether to give her the written warning, or promote her to Head Rep!”
“Ha! Well, I’ll leave you to ponder that,” Sabrina said, heading to the door.
……I did have to discipline Aimee plenty of times that season. She never did get sacked, though.
