Holly's First Night

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She joins her friend in a charged group sex session.
7.8k words
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Part 1 of the 5 part series

Updated 06/09/2023
Created 07/17/2018
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This is kind of a taster of what will expand into my autobiography, if you wish to make a comment please do.

Holly

*****

I was in my second year at University College London, studying PPE. I'd found the first year hard, struggling to keep up with the course and the expense of living in London. As the end of the first semester of the second year approached, I was really in trouble, academically and financially.

My flatmate Zoe always seemed to have plenty of cash, and some very nice clothes. One day, just after the first Christmas adverts had finished before yet another anodyne yet artistically gritty Northern soap opera started on the TV, I asked her how she managed.

"It's simple," she replied "I accompany men to events for a fee." It took a few moments for the penny to drop.

"You mean, you're an escort?" I was genuinely shocked, she was, my flatmate was, a...a prostitute! She knew exactly what I had thought, her eyes narrowed.

"Shame on you Holly Eliza Jordan, I do not," and she really emphasised the 'not', "fuck men for money."

"I'm sorry Zoe, but you just told me..."

"Holl, you stupid cow, I said I go to events; dances, dinners, gala dinners even sometimes. I do lunches, but I sure as fuck, do not, do breakfast."

Her passionate response shamed me, and I quickly back-pedalled.

"I'm sorry, Zo, but y'know, it does happen."

"Not to me you stupid bitch, what do you think I am?" She went into her room, slamming the door behind her.

I watched Netflix; Pretty Woman. Richard Gere looking devastatingly handsome and Julia Roberts as the hapless whore.

It didn't help.

Next morning Zoe was still angry with me. This wasn't good, normally we'd have a disagreement, about the cleaning rota, or who should put the bins out, or who'd had the last of the Ben and Jerry's ice cream. It would be followed by a bottle of cheap wine and everything would be forgotten. But this had hit a raw nerve it seemed. I didn't know what to do to heal the wound I'd opened. When Friday came around and the atmosphere was still colder than an outside toilet in Antarctica, I tried again.

"Zo, I'm sorry, I shouldn't have said that."

"You didn't say anything, you thought it." was her only response.

"Yeah, okay, but..." I let the next words hang, dangerously.

"Look, I have a hard enough time as it is, these men thinking I'm an easy lay, without you betraying me too."

I didn't have to try hard to look totally confused because I really was.

Confused, that is.

Zoe was pretty, that was undeniable; she was a tall, willowy, coffee coloured vision, possessing a self-confidence I could only dream of, backed up by real physical, I don't know... hotness?

I guessed she didn't like the chasm that had opened between us any more than I did.

"Look, Holl," she said, it was early Friday morning, I had a tutorial at ten but my estrangement from her was far more important.

"Zo?" was my rather pathetic response.

"The guys I go with, I mean... escort. Look we don't have sex, y'know? If they look like they can afford it, I might give them a hand-job, or...or even give them a blowjob." She flushed red.

It still seemed bizarre to me, but I clutched at getting my Zoe back. She took a deep breath sitting at the table, a bowl of cornflakes in front of her, dressed in her pyjamas and told me about the agency that put her in touch with businessmen looking for company.

"Basically they provide arm-candy for rich visitors, mainly Chinese, but some Russian and Africans too." She told me the fee she got from the agency, which would have paid the rent several month's over for an evening of being pleasant to some guy, and that her clients could be generous too; buying her things she desired. Apparently she now had quite a substantial nest egg.

I genuinely didn't know what to say to her. Was she a whore, or just a girl who made the best of her assets?

"Come and meet Alexandra, she runs the agency." Zoe said.

So, later that afternoon I stood in front of a woman who had more than a passing resemblance to one of my dad's favourite aunties. Her plump face had little laughter lines at the creases of her eyes, she had her blond her tied back into a severe ponytail and wore a black scoop-necked top, under a dark grey cardigan, hardly how I'd imagined the owner of an escort agency would dress. Alexandra looked at me dispassionately,

"Miss Jordan, do you know why you are here?"

"You're looking for girls to accompany visitors to the city."

"Yes in part, the girls must be bright, intelligent and good company, but there is often...more expected of them."

I nodded, nervously.

"Stand up straight now, let me see you."

She stood up from the swivel chair behind the desk, she wore a dark grey woollen skirt, knee length, expensively tailored, as was the matching jacket on a hanger behind her. Unexpectedly I noticed she had thick tights on. As she walked around the desk to come closer, I saw she wore flats. She walked around me a couple of times, like a judge at Cruft's, assessing whether I was a possible champion, or a mongrel. I felt as though I was under the microscope of a researcher. Standing in front of me she said

"Open your mouth."

I did, out of sheer surprise, as she obviously examined my teeth. She went behind her desk again, sat down, picked up a golden coloured pen and watched me for a few seconds. She seemed to make a decision.

"Take your clothes off."

"What?" I asked, stunned.

"Take your clothes off, child. I wish to see you, not your... awful taste in cheap student clothes, so take them off."

I was feeling totally insulted, degraded even, but I did as she said, bending down to unlace my trainers, I heeled them off before undoing my skinny jeans and stepping out of them. Finally I straightened and pulled the UCL sweatshirt off over my head. I stood in front of her, defiantly resisting the instinct to cover myself, in my plain white sports bra and unmatching Minnie Mouse logo'd panties, painfully aware that this was not a good look.

"Hmm, turn around," she directed me, asking me to stand on one leg, bend over touching my toes, stretching my arms above my head, clasping my hands behind my back, and even kneeling on the carpet.

"Good, you may dress and be seated."

I put my clothes on as quickly as possible, sitting on a hard plastic chair to finish tying my laces.

"Miss Jordan, you are a handsome young woman, you have no visible tattoos, which is good. Do you have any that I couldn't see?"

"No." I confirmed shaking my head.

"Good, I do not like my girls to have tattoos; so common. Do you have any piercings, apart from your ears? I can see those." Again I shook my head.

"One or two body piercings are acceptable to our clientele, bear this in mind." she said.

"Good bone structure, pretty good skin, flexible, nice long neck and well proportioned limbs and breasts. But you need to be more precise in removing your body hair, especially your pubic hair." she seemed to be reading a mental checklist of my faults and I was getting pretty angry, then she dropped the bombshell;

"Now, we have to be a little intimate; to explore your sexual preferences and limits."

This was totally unreal, I thought, but she continued inexorably.

"You are not a virgin?"

I shook my head, wondering just how far she would go.

"That's a shame, how many sexual partners have you had?"

I thought, carefully.

"Four"

She raised an eyebrow.

"Were they long-term relationships, or one-night stands?"

"Two boyfriends, one, one-night stand, as you put it and one that didn't last more than a couple of weeks." I replied, trying to sound confident. Her next question shocked me.

"Any girls?"

I thought back to last New Year's Eve, I'd broken up with my last proper boyfriend just before Christmas, and Zoe and I had gone down to the Embankment to watch the fireworks. We'd done the countdown and everybody was hugging and cheering, and Zo had kissed me, full on the lips, giving my boobs a squeeze at the same time. I hadn't known what to do, other than kiss her back, pulling her in close to me. As the crowd surged around us we seemed to be in a cocoon of intimate silence, then somebody had jostled us and the moment was gone.

"No." I said as firmly as I could.

"But you have thought of it, yes?" She seemed to know me better than I did.

"Maybe." That seemed to satisfy her for now.

"Have you ever had more than one partner at a time, hmm? that'll be a no." she said answering her own question.

"How do you masturbate?" I wanted to be out of this room.

"We all masturbate Holly, do you use your hands, or do you have any toys?" She looked me directly in the eyes. I could feel an unbidden flush of embarrassment heating my cheeks.

"No toys." I whispered softly, too scared to admit I had a special hairbrush. She smiled gently.

"Holly, I need to know these things so I can match you to the right client, you can see I'm not taking any notes, I just need to judge what is best for you and this agency." I kind of understood, so I took a deep breath and sat upright, waiting for the next question.

"Do you enjoy sex?"

I nodded affirmatively.

"Okay, good, it is a sweet gift. So you've been in straight relationships, what are your views on oral sex?" She was going to force me to speak about sex, to see what I knew, or more likely, didn't know. I thought about it, I couldn't blush any redder, and I kind of trusted this woman, though god knows why.

"It's nice, I feel I'm in charge if I'm giving it, and if I receive it, well, what's not to like?" She smiled again, just a little upturn of her lips, but I found I wanted to see it more.

"Have you ever had anal sex?"

I was wrong, I could go redder. I could feel and hear the rush of blood in my ears as I tried to focus on Alexandra.

"Yes."

"How was it?" Painful the first time, but Simon had been a considerate lover, he coaxed me into trying again, making sure I was ready for that invasion of my most intimate place, It turned out that I actually enjoyed it a lot, probably as a rebellion against my mother's Catholicism and indoctrination that sex was a dirty necessity, not to be enjoyed. Also it helped that Simon hadn't been particularly... big.

"I,... I liked it." I admitted.

"That's good, have you ever rimmed a man?" I didn't understand what she meant.

"Rimmed?" I repeated. She smiled at me like she would at an innocent child, which at that point I guess I was.

"Licked around his anus, his arse dear."

"No, never." but Simon had done it to me often enough, funny how I never knew what it was called.

"Have you taken, or do you take, drugs of any kind?" I didn't even smoke, but I had taken a few drags of weed once at a party; it had made me light-headed and nauseous, which is what I told her.

"Okay, that's alright, some of your clients may offer you drugs, you are advised to politely refuse them."

"Very well, that's all good so far, now look at this picture, and tell me which order you would start in."

I looked at the large A4 sized photograph she held up. It was a picture of a place setting, knives, forks, spoons, four different types of wine glass including a smaller port glass. I'd taken a summer job one year at a country house hotel that often put on formal dinners, weddings and so on, so I'd seen all this before. As i explained this to Alexandra, she nodded happily, and graced me with that little smile again.

"And how would you dress if invited to a function like this?" she asked.

"It depends on the invitation" I responded "Cocktail dress, evening gown if it's a black tie event"

"How often do you wear heels?"

"Not very." I replied, since that last Christmas, apart from an abortive date or two I hadn't had a reason to get all dressed up.

"Very well Holly. You are a very attractive young woman who will fit in well with many of my clients. I can offer you a place on my books, however, first I want you to refine yourself a bit". She looked at me, smiling reassuringly, then opened a drawer in her desk and took out a plain white business card which she handed to me.

"Giles has a small gymnasium here, he will be your personal trainer, you will see him every other day, starting on Monday. You need to lose a few kilos and tone up your muscles, also, you should review your bikini line, stray hairs are so very unattractive these days." There was that hot red flush again.

"Giles will advise you on diet, exercise, deportment and dance. I will review your progress in this office in precisely twenty eight days time." She drew another card out, coloured blush pink.

"Maria will give you a makeover, she really is very good; clothes, make-up and hair are her specialities, she will see you next Friday morning at ten." This was all going way too fast now.

"If the review is satisfactory then the agency will pay you a minimum of one thousand pounds for each introduction we arrange."

"Anything your client wishes to offer you as a gift is between you and your client. Each contract will specify the hours you are working for me, you will not perform any additional services for the client within those hours, other than acting as their companion. Do you understand that?"

I nodded.

"Giles and Maria are employed by the agency, they will not require you to pay them a fee. If, when we meet again, you or I do not wish to proceed I shall ask you to sign a non-disclosure agreement and you will never hear from me or the agency again. Fair?"

I nodded again in assent.

"Good, now I have another appointment shortly, you may leave. Goodbye." I was dismissed.

It was starting to rain as I stepped onto the street. What on earth did you think you were doing Holl? I told myself I was going to get paid to be taken out, Alexandra had made it clear, I didn't have to do anything else other than be arm-candy and provide distracting, witty conversation did I? Some nice clothes like Zoe had, a meal, maybe a show and home for hot chocolate and bed.

But whose bed?

Zoe never brought anyone back to the flat. I'd never even caught her doing the walk of shame, something I had done only a few months ago after a disappointing drunken one night stand with a Med student who, frankly didn't know much advanced biology. I found myself on Oxford Street, all the shops garishly lit in the pre-Christmas frenzy of a retail orgy; tinsel, glitter and gaily wrapped boxes jostling with beautiful things. I stopped and looked in the windows of some clothes shop; gloriously flattering dresses hanging on anonymous white plastic bodies.

Could I, would I do it though? The startling response was Yes, if he was handsome, if I fancied him, if he made me laugh and feel comfortable, if he excited me, then yes I might possibly.

At the back of my mind though, a treacherous little worm awoke; if he offered me enough money, then yes, I definitely would.

By the time I got back to the flat the rain had turned into damp, penetrating sleet, the thick heavy clouds advancing dusk even earlier than normal. I climbed the communal staircase, unlocked the door and stepped inside. Zoe wasn't there, probably at a tutorial or something. Hanging my wet coat up over the radiator to dry I went through to my room and switched on my laptop. As it went through its start-up cycle I went to make myself a cup of tea and some toast. When I came back I logged in. I needed to do some research.

Typing in the word 'Escort' into the browser filled my screen with ads, there were even Wiki guides on hiring and being an escort. There were abbreviations, GFE and OWO that had me baffled, until I thought to Google them. All the adverts had glamorous pictures of girls, men and transexuals even. I'd lived in London for nearly eighteen months and hadn't really understood just how big an industry there was out there. I realised that I didn't even know the name of the agency Alexandra ran, so I couldn't look it up.

I went through several, looking to see if I could spot Zoe, but that didn't come to anything. On about the fourth page the videos started to appear; escorts having sex. I clicked on one site; here, there were some obviously amateur films, maybe filmed in secret, and some more professional quality films, more like some of the porn films that I had seen before. I hesitated a moment, then clicked on one.

It showed a slim young blonde girl, dressed in black lingerie slowly gyrating, rather like a striptease act. The camera moved around her as she sat down, playing with herself; squeezing her nipples through her bra, and pulling her panties tight, exposing her sex.

She had a small triangle of hair above her vagina, but none around her lips. After a few minutes, she was joined by a handsome young man, dressed casually. He kissed her from behind as she backed into him, his hands rubbing her exposed breasts, pinching her nipples to hardness.

He was obviously in control of the action as he turned her around, dropping to his knees and nibbling her exposed buttocks before spreading them wide and licking her from her pussy lips all the way up to her arsehole, finally tonguing, rimming I remembered, her arse.

Then the film cut to him lying on his back as she rode his cock, bouncing up and down on it she was definitely providing a soundtrack for the viewer to know she was enjoying it. She seemed to have a couple of orgasms, the she climbed off him. Turning round she started sucking his cock, stroking the shaft and playing with his balls. I noticed then, that he too was hairless down there.

Somewhere along the way his clothes had vanished. With her head bobbing up and down the girl was still making noises of sexual enjoyment. Again the film cut to a different position; she had one hand against a full-length mirror as he took her from behind with her leg hooked up by an arm so the camera could see her being penetrated. She was looking in the mirror, looking him in the eyes, as she had done when giving him the blow-job.

I realised eye contact was going to be an important part of my new career. Again she seemed to orgasm a couple of times, then she was on her knees in front of him as he wanked himself, his sperm leaping the gap between his cock and her face. It looked like she enjoyed having it splash over her. I sat back and thought. Could I really enjoy doing this with a stranger?

I clicked on another film. This was obviously filmed in a hotel, I recognised the group logo on the room service menu on the bedside cabinet. A blonde woman entered the room in a silky red blouse and black miniskirt with fishnet tights. The voice of the man filming welcomed her and asked her to sit on the bed. They made small talk, her accent was foreign, maybe German. He asked her to take her blouse, then her skirt off, then carefully placing the camera down so it caught her on the bed he walked into shot. He had no clothes on, and his head never came into view.

She had a tight, well toned body, and I thought back to what Alexandra had said, maybe I did need to lose a few pounds. His cock was pressed up against her belly as they kissed, then she reached down, running her fingertips lightly over the full length of it as he placed his hand on her mound.

She was completely smooth down there, no hair visible at all. I have to say I was starting to like that look. A cut, and she was sitting on the bed, he was stood very close to her as she squeezed something from a tube onto her hands, then started to stroke his cock. I noticed she used both hands, kind of twisting them as they went up and his length. She too held his gaze, showing off her perfect white teeth in a big smile. As he got closer to cumming she pushed her breasts forward to catch the ejaculate. Finally, he must have picked the camera up as now you could see her leaning back, rubbing his spunk into her body. I heard Zoe call out.