Emily's Escorts

Saturday Evening

I took a deep breath and checked my reflection in the bar window. It was early evening so the glass reflected well enough. Emily and I had decided that my form fitting, white mini was the ideal outfit for tonight's meeting. Emily said it showed off all my curves beautifully and that Leena, my client for the night, would adore it.

A few hours earlier I had checked into the penthouse suite of a luxurious hotel. I'd unpacked my clothes for the night and next day, as well as the toys I'd brought with me. Emily had come over to help me with my hair and makeup. Emily is my boss and best friend. I can always trust her judgement. My long red hair, which normally drops to just above my bum, was now mid back because Emily had applied her magic and ringletted it, gathering it at my neck with a pale green barrette. She'd applied red lipstick, mascara and a subtle glitter eyeshadow, adding a small squirt of Givenchy just below my ears.

She took a step back, appraising my look with her practised eye. She was wearing a stylish trouser suit, her shoulder length dark hair in its perfect bob. She was wearing five inch heels, as much to compensate for her diminutive stature as anything.

"Um, Anna babe... you're going to have to lose the knickers."

I looked at my reflection in the mirror. I could see what she meant. Even though I was only wearing a white thong, the panty line was quite obvious. I unselfconsciously lifted the hem of my dress and dropped the string down my legs and onto the floor. Emily picked it up and placed it on the dresser. I pulled the dress back down, covering up my newly waxed pussy and Emily helped me with my white, four inch stiletto heels.

I steadied myself and Emily looked at her watch and then back at me. "Okay babe, time for your date."

We shared a brief kiss and she patted me on the behind and said, "Have fun, babe."

I smiled, picked up my pink clutch bag which contained my room key, lipstick, perfume, mascara, phone and purse and, before opening the door and walking out said, "I think I will, babe. I always get a little anxious with a new client but I know she's more nervous than me."

I left, knowing that Emily would be tidying up and then leaving before Leena and I came back in an hour or so. The elevator ride and short walk to the bar led me to this moment and I had the door opened for me by a burly looking bouncer who I smiled at and thanked. I scanned the bar which was adorned with tables, chairs and benches around the outside. It wasn't overcrowded and I spotted Leena immediately, sitting on a stool at the long bar with her back to me.

I took a moment to take her in. Her long, dark brown, slightly wavy hair was loose and parted in the middle. She was wearing a one shoulder, dark green dress. From the angle I could see her at, it looked to be about knee length. She was weaning tights or stockings covering her elegantly long legs.

I walked up to her, aware of not a few eyes tracking me, and said, "Leena?"

She turned and got up off her stool. As arranged in our phone call she said, "Jenny!" She nervously hugged me and I returned the hug as she kissed my cheek.

Of course I use a pseudonym. I don't want some client finding out who I really am and stalking me.

"Lovely to see you, Leena." We had arranged a cover story that we were old friends so that it wouldn't look like what it actually was. Appearances must be maintained, after all.

She let go of me and asked me if I'd like a drink. I could see she had a glass of white wine so I just said I'd have whatever she was drinking and she duly ordered and paid for it. Picking up my glass I said, "So lovely to see you again. Perhaps we can go to a quiet corner and catch up?"

She nodded nervously and said, "Yes, yes. Let's do that. Um, over in that corner? It looks kind of private."

I smiled and nodded. "Lead the way, hun."

We walked over to the table and each took one of the comfy leather-look chairs, sitting at right angles to each other. I could see she was very nervous, which always gives me a thrill. It meant I would have to be a little assertive.

"So, are you okay? Want to talk about anything in particular?"

She swallowed and looked at me and then down at her drink. "I... I don't know. This is the first time I've... I mean. What do we do?"

I put a reassuring hand over hers and said, "We will do whatever you want to... within reason, of course." I laughed a little and she laughed with me, her tension dropping slightly. "So this really is your first time? I don't mean with an escort, I mean with a woman."

She nodded. "Other than fooling around in uni, but that was just drunken snogging and the occasional boob grope, nothing more."

I smiled and lifted my glass. "Let's not have too many of these then. Don't want there to be any drunken snogging later."

She giggled and we both took a sip of our drinks.

She looked back up and said, "You're very beautiful Jenny. Your picture doesn't do you justice."

I actually blushed a little. "Thank you, Leena. You are also beautiful and I'm envious of you."

She looked puzzled. "You are?"

I nodded and smiled. "Much bigger tits and shapely hips," I said as I took my hands and grabbed my braless, barely b cup boobs and pushed them up.

She let out a genuine laugh and said, "Well, they're not always a blessing, particularly when I go running, and I have to wear a strapless bra in this dress."

"Well, you look fabulous and I do love that dress, by the way."

"Thanks. I really love yours. How on earth do you have no VPL?"

I winked at her and just said, "Nothing to make a panty line visible, hun."

She blushed and then whispered. "Wow. Just knowing that sent a little tingle downstairs. So you're like, totally naked under that dress?"

Under the table I placed a hand on her knee and gave her a gentle squeeze of reassurance. I was about to bring it back up when she placed her hand over mine.

"We're all naked under our clothes, Leena. So... I suppose I should wish you a happy birthday."

Three days earlier

I was out doing a little shopping. No particular purchases in mind, I just like going and trying on clothes and making random purchases. My phone rang and I reached into my shoulder bag to get it out. It was Emily.

I swiped to answer and said, "Hi babe!"

"Anna, darling. How are you?"

"I'm great. Out shopping."

"Are you somewhere you can talk?"

I spied a bench ahead of me and said, "Sure. Give me a sec."

I walked over and sat down. "Okay babe, shoot. You found me a client?"

"Mhm. Yes. Quite an unusual one."

"Unusual? How?"

"Well, she's a married, bi-curious woman who's husband is paying for her to spend a night with a woman. As a birthday present."

I giggled. "Seriously? Okay. That is a new one.... Oh god, he doesn't want to be there and watch, does he?"

Emily giggled and said, "No babe. Apparently it's her thirty fifth birthday," which made her eight years older than me, "and she's apparently been telling him for some years that she wants to explore her les side so he found us."

I was quite stunned. "Really? He doesn't want us to film it or anything like that?"

"Apparently not, although if you want to film anything that's up to you."

I giggled. "If I do it will be on my phone. Okay, so send me the details. Let me talk to her to see if we want to go ahead."

"I'll text them to you now. Her name's Leena, by the way."

"Leena. Okay. I'll call her when I get home."

"Thanks, darling. Love you! Mwah!"

"Love you too, babe. Mwah!"

I disconnected, put my phone in my bag and stood up. An unusual one indeed.

I aborted my shopping trip and decided to head home to make this call. I was intrigued. I heard the beep of a text coming in and when I got back to my apartment I checked and there was Leena's number. I dialled her, ensuring beforehand I'd blocked my caller ID. She picked up on the third ring.

A pleasant, educated, light voice answered. "Hello?"

"Is that Leena?"

"Yes. Yes it is. Who is this?"

"Hi Leena. I'm Jenny. From Emily's Escorts?"

There was a pause followed by, "Oh my. That was quick. Eric only called a couple of hours ago."

"We like to be prompt," I said, "so I gather from Emily that you want a birthday present."

Another pause. "Um. Yes... I... think so."

"You're not sure?"

"I... I am. Sure. I've just never..."

"It's okay, Leena. I understand. Would you like to see a picture of me so you can decide whether you want to go ahead?"

"Um... sure. I can send one of me if you like as well."

"Okay. Great. Have you got a pen and paper? Great. Here's my email address."

I spent a minute spelling out my Escort's email and then she asked me, "Um... this picture? Does it have to be, like, naughty?"

I laughed. "No, Just a selfie of your face at least. That way, when we meet we'll know each other."

I could hear the relief in her voice, "Okay. Great."

"If I hang up now, send me an email and I'll send one in reply. Then I'll call you back."

"Great. Thanks Jenny. Talk soon."

I hung up and checked my email.

A few minutes later I got one from Leena. It just said:

'Hi Jenny - hope you like. Leena.'

Despite our conversation she had picked a photo of herself, sitting on a bed in a pale blue, translucent baby doll negligee, her long legs curled up beneath her, her long hair arrayed around her shoulders, her generous breasts filling the nightie. She looked gorgeous.

I thought hard about what I would send and picked one of the snaps from my agency portfolio. It was me in a white basque, stockings and lace panties with red stilettos.

I sent it in reply just saying, "Calling you back now. X"

I dialled her number once more and she picked up almost immediately.

"Oh, Jenny. My word. Is that what you'll be wearing when we meet?"

I laughed. "No hun. We'll meet in a bar or something first. I can always put that on later if you wish?"

"Oh god. I don't know. What should I wear?"

"Whatever you feel comfortable in. Do you have a preference for what you want me to wear?"

"Mmmm. Sexy but sophisticated?"

I chuckled. "Okay. I'll do my best."

"So... are we going to dinner first or something?"

"Um. Not a great idea to be honest, Leena. In my experience you and I will both want to be leaving as soon as possible. Make sure you eat before you come out."

"So you want to meet me?"

I smiled and said, "Yes, I do. Are you okay with meeting me?"

"Yes. Yes! Should I do anything to prepare? Like shave down there?"

"How are you normally 'down there'," I asked.

"I... have a triangle and I keep everything else waxed."

"If that's what you like, keep it that way. This is all about you, Leena. Do you have any requests for me? I'm actually bare 'down there' if that's okay. Not sure I've got time to get a merkin." I laughed to let her know I was joking.

She laughed back. "No, that's fine. I like the idea. So can we do this on Saturday? That's my actual birthday."

I was surprised. "Really? You don't want to spend it with your husband?"

She paused. "No. He told me he wants it to be special and this is his way of making it special. We'll celebrate on Sunday."

"Well, if you're sure, yes. We can do Saturday. Let me make a few calls and I'll send you the details. Okay?"

"Yes. Um..."

"What is it? You can say or ask me anything," I reassured her.

"What will we do?"

I laughed. "Do you plan your lovemaking with your husband like this?"

She said, "No. No. I didn't mean it like that. It's just... I'm a complete novice."

"Don't worry Leena. We will take it at whatever speed you want. Okay?"

"Yes. Yes. Thank you, Jenny. Okay. I'll look forward to your email and meeting you on Saturday."

"Me too, Leena. Have a wonderful rest of the day. See you soon."

We disconnected and I called Emily. I gave a report and she said, "Great! Sounds like you're going to have fun. Okay, let me just check bookings."

I heard some typing and then she said, "Perfect. I've booked the penthouse for Saturday. There's a lovely bar just round the corner so it won't be too far to walk in your heels."

I smiled. She's always looking out for me.

She sent me the details and I sent them on to Leena who responded almost immediately with:

'Wonderful. Can't wait to meet you. Very excited and nervous.

Leena x'

---------------------------------

You may be wondering how a twenty seven year old drama graduate ended up as a lesbian escort. Well, it turns out that not everyone who graduates from drama school ends up on the red carpet in Hollywood. I know! It shocked me too. After a couple of years of doing rep and the occasional bit of TV work I'd just attended an audition for a role which I failed to get, by the way, when one of the other auditioners approached me. She'd also been turned down.

We were just walking out of the audition room when this very short, very cute woman stopped me and said, "Anna, isn't it?"

I looked down at her and smiled. "Yes. You're Emily, right? I thought you should have got the part."

She smiled and said, "No darling. They usually cast me as a munchkin."

I laughed. "You're much cuter than any munchkin."

She blushed prettily and said, "So... I'm wondering if you might be interested in some extra work. Maybe once or twice a week?"

I was living on scraps at the time and so I said, "I'd do almost anything for money right now. What sort of work is it?"

She stalled for a moment and said, "Fancy a coffee? I'll explain."

So we went for a coffee at the nearest artisan coffee shop that had popped up. Emily treated me because I was so broke.

As we sat and sipped, Emily explained. "Right. Now. Please don't be shocked and please don't say no immediately. Hear me out?"

I was wary but so in need of work I decided to give her a chance. "Go on," I said.

"Right, well, I have a side line that I'm building up. I run a small escort agency..."

"Stop right there," I said, "I might be desperate but I am not becoming a hooker."

Emily said, "Please Anna. Hear me out?"

I sighed. "Okay. Carry on."

"I'm going to make a guess based on the way I saw you interacting with people. Anna... are you gay?"

That was very perceptive because I try to mask my sexuality as much as possible.

I nodded. "Yes. How on earth did you know?"

"I watched you. You were always warmer with the girls there than you were with the guys. I've even seen it here, with the way you interact with the staff."

I swallowed. "What, so this is a lesbian escort agency you run? It still sounds like the same thing to me, Emily."

She smiled and said, "Well, we have lesbian and bisexual girls on the books. Sometimes couples want a girl to share."

"No. I won't do that. I like men, I just can't get with them sexually. Sorry."

"So if it was only women you'd consider it?"

She'd trapped me. "I didn't say that."

"Look, Anna, we're a high class operation. It's owned by all of us, although I have the controlling share. If you joined, I would make you an equal partner."

"Equal with the others?"

She shook her head. "No darling. With me."

I was confused. "Why? What's so special about me?"

"You're an actress, darling. A natural one. Imagine what roles you could play in the bedroom. Do you have a current girlfriend by the way? Obviously that could change the situation."

I shook my head and laughed ruefully. "Not only have I got no money, I've got no sex life other than Rosie Palm and some old toys that I can't afford to replace. Hold on, do you have a partner?"

She smiled and nodded. "I do. June. She's one of the girls as well."

I was shocked. "Okay. So how much does this pay?"

"You're considering it?"

"I'm still thinking about it. How much?"

"Three thousand pounds a night."

I was stunned. "My god! What? That's... That's more than I make in a month! It's more than I make in three months sometimes. Women are prepared to pay that much?"

"Women of certain means, darling. Ones who have to hide behind society's conventions because of their status in life."

"And what, I just have to go round their place, make love and then leave?"

"They're paying a lot of money so that they get you for the whole night and next morning. So what do you say? Maybe just try it? Once? I'll pay you five thousand for the first time."

It was a lot to take in. "I need time to think. I can't just say yes."

She reached in her handbag and pulled out a business card. It had 'Emily's Escorts' in an elegant script in silver, with a heart over the "i", below that it had her name and a mobile phone number.

"Call me. Anytime."

I took the card and put it in my bag.

A week later, in which I could only afford baked beans, and another set of auditions had resulted only in some extras work which paid me about two hundred pounds, I called Emily.

Present day - Saturday evening

Leena smiled and said, "Thank you, Jenny. I'm quite excited to receive my present."

I picked up my glass and emptied it. "So, do you want to stay for one more, or shall we forgo the drunken snogging and I'll take you to our suite?"

She lifted her glass and drained it, putting it down and saying, "Um. Yes. Let's go before I lose my nerve."

I rose and picked up my bag. "Come on then, Leena, it's only a five minute walk."

She stood up and we left the bar, the bouncer once more opening the door for us, saying, "Have a good evening ladies." We thanked him and walked along the busy street. We got to the corner of a darkened alley and I decided to take control. Leena obviously was quite timid and I wanted to let her know how she should just let go. I grabbed her hand and pulled her into the alley, pushing her up against the wall and kissing her fiercely. It could have gone one of two ways and I was pleasantly surprised when she not just returned the kiss but put her arms around my waist. The kiss was passionate and I felt her body pushing against mine as I pressed her against the wall. I put my hands up into her hair and, bunching it, pulled a little. I heard her moan as our tongues connected and explored. This had a very warming effect on me and I felt the tingles of passion stirring inside me.

After several minutes of this, almost being caught by a couple passing by, we broke and carried on our walk to the hotel. We crossed the grand, marble lobby to the lifts and, when we got in alone, I once more kissed her, my need rising.

As the lift slowed and the doors started opening we broke apart and walked down to the door at the end of the corridor which led to the penthouse. I fished out my keycard and unlocked the door. We went in and I kicked the door closed as we fell into another kiss in the large drawing room.

I started stroking all over her back and shoulders and I felt her hands stroking up to my bare back. As I dragged my nails over her exposed flesh of her shoulder she moaned once more. We broke and I could see that a lot of the nervousness in her had dissipated.

She swallowed, looking into my eyes. "What do we do now?"

I chuckled a little. "You, madam, will follow me into the bedroom."

I was deliberately acting Domme, having sensed the natural submissiveness in her. She obediently followed me as I took her hand.

When we got into the bedroom I turned and said, "Leena, undress me."

She just nodded and undid the straps at the back of my dress. She slid it slowly, almost reverentially, down my body, slowly exposing my breasts. My nipples by this point were rock hard. My areola are about two inches across, dark pink, with darker nipples.

I commanded her once more, "Leena. Take a nipple in your mouth and suck."

She obeyed instantly. Staring up into my eyes as she did so. I could see the lust and heat in her and smiled inwardly. My nipple to clit connection kicked in immediately.