Chapter 4

Author’s Note: This story is a collaboration with my friend and editor, Harvey. We both contributed equally to its content and we hope you enjoy it. Additionally we’d like to thank Jim (Mojavejoe420) for his contributions to this chapter.

“Hi, sweetheart!”

I’d barely stepped out of my car when my Dad wrapped me up in a big bear hug in the driveway. I closed my eyes and melted into his strong arms.

It was a long drive from Las Vegas to my childhood home in Glendale, California, right outside of Los Angeles. I’d been working steadily for Dana for the last month, going on one and sometimes two dates a weekend. Even though I could’ve used the money, I’d decided to take this weekend off and spend it with my father. I knew he needed me and there was always next weekend to work and add to my growing bank account.

“Daddy, mmm, you feel so good!”

“You do too,” and he squeezed me again. We walked into the house with his arm around me and he asked about the drive, my car, and my classes.

The house seemed too big, though, too empty. I noticed some of the artwork was gone, and some of Mom’s crystal collection, too. Daddy saw me looking around as I took in all the new and not-so-good changes. I thought of asking him about it, but decided against it. Perhaps after I get settled in, I thought. We sat down on the couch in the living room after my father got a couple of beers out of the fridge.

“I love when you visit me; how long will you be able to stay?” he said longingly.

“I have to leave Sunday at about noon. I have classes Monday morning that I can’t miss.”

I saw the hurt look in his eyes. I knew he wanted me to stay longer, but it was an impossibility. “I understand, sweetheart, you’re busy with school, and I’ll just enjoy the time that I have you here with me.”

He asked me again about my classes and my ‘part-time job’ at the school bookstore. I hated lying to him but I knew he’d never be able to handle the truth of how I was really paying my bills now that he could no longer assist me. Once we’d caught up a little, I hit him with a serious topic that I hoped he’d be okay talking about.

“So, how are things going with Elaine?”

I knew that she and my Dad had been getting closer lately. I was glad for him; he’d been in quite a dry spell ever since my mother passed away suddenly three years ago. He’d loved her dearly and it took him a couple of years to move past losing her and try to ‘get back out there again’ and meet someone new. Just as things had started to get better for him he’d lost his job, and of course being unemployed wasn’t a big selling point with the ladies. When he met Elaine I thought things had finally started looking up for him.

“I’d planned on you meeting her today, but we had a falling out and that won’t be happening,” he said solemnly.

My heart sank and I reached out, took his hand, and gave it a gentle squeeze. “I’m sorry, Daddy. I thought everything was going well with her.”

“Everything was going great, until ... ummm ... last night.” I waited patiently for him to continue as he collected his thoughts. “This is really difficult to talk about with my daughter. I know you’re a grown woman ... but ... still...” His voice trailed off as the picture became a bit clearer.

“Daddy, you know you can talk to me, right? I’m kinda grown up now. I even know about,” I looked around the room and then whispered, “s-e-x.”

Working for Dana, I’d quickly learned that humor could diffuse any potentially awkward situation with her clients. It always worked with them, and it worked on my Dad as well.

He gave me a big laugh. “Well, all right, then, you asked for it. It was about s-e-x. I wanted it and she didn’t.”

I broke into a little scowl. “You weren’t pressuring her too quickly, were you? I thought you’d been going out a while?”

“Elisa, we’d been going out for four months, but she’s ... you know ... Catholic. After she got divorced she didn’t want to have sex until she got married again, and I guess I wasn’t willing to wait for her.”

This was a complicated situation, more complicated than I’d envisioned. I didn’t blame my Dad for wanting sex without being married. However, I also respected Elaine’s decision to abstain because of her religious convictions.

More than anything, I felt sorry for my Dad. He looked so dejected. Poor guy, I’m sure he really needs to get laid. Again, I tried to use humor to cheer him up. “Well, maybe it’s for the best. She’s probably lousy in bed and wouldn’t give you head.”

He coughed, and when he regained his composure he apologized. “Sorry, I wasn’t expecting that from you and you kind of caught me off guard there. It’s a moot point now, we had a huge fight last night and she was really pissed when she left.”

I tried to put a positive spin on the deterioration of his sexual prospects. “Daddy, maybe it’s for the best. Good sex is important in a relationship.” Trust me, I know. Most of the men I see every weekend pay me to do things for them that their wives won’t.

“Yeah, I guess that’s true.” He paused for a moment to collect his thoughts. “Since I’m being so forthright with you about the shitty state of my love life, how about you tell me what you’ve been up to. Are you seeing anybody? Having good sex? Giving good–” He stopped suddenly. I think he shocked himself with what he almost said.

Yes, Daddy, I’ve given good head every weekend for the last month. And I swallow, too. What’s the point of doing all the work and not enjoying the taste?

Of course, I couldn’t admit any of that to my father, so I just smiled for a few moments before formulating my usual lie about what I’d been doing for the past few weekends. “I’m too busy with my school work, but every now and then I’ll go out on a date.”

What I was also discovering, working for Dana, that I couldn’t share with my Dad was that I liked being with men, not boys that were my age. They were more mature, more respectful, and more willing to return the pleasure that I gave them. Of course, there were some exceptions. A couple of them had been way past their prime and a lot more work to please, but overall I’d learned through my weekend experiences that guys my age were now of little interest to me.

The next few hours were great. We talked and laughed about some of his brothers and sisters, and we reminisced about my mother and some of my childhood experiences. Then we talked politics in relation to one of my classes. I always appreciated his take on things and he really understood that there usually wasn’t just a black or white definition or solution to a problem. He liked to consider all sides of a situation and he wanted to make sure that I always did, too. He’s one of the smartest people I know.

We had a great weekend together, and when I left on Sunday I promised to come back as soon as I could. My weekend with him also caused me to feel a bit conflicted. He’d said he was getting by just fine, but the insides of the cabinets and fridge were pretty barren. He’d already sold off the BMW, and he’d talked about selling the Infiniti next.

I had extra money that I was more than willing to give him, but I knew he’d never accept it from me. Additionally, it would blow apart my lie about working in the college bookstore for minimum wage, and it would force me to be truthful about what I was really doing on the weekends. His little girl seeing men on the weekends for money, that was information that I knew he was in no way ready to handle.

His lack of a love life also concerned me. He’s very good-looking and quite a catch; he’s kept himself in great shape despite the unemployment. He wasn’t one to just sit around and feel sorry for himself. Pretty women would be flocking to him if he could just find another job. Maybe I could get an escort for him? Would that even be good for him?

That was kind of weird, thinking about my Dad with one of Dana’s girls. I’ve seen all their pictures; I wonder which one he’d like. And would they be good to him like I’m good to my clients? I’d want him to have somebody who wouldn’t just go through the motions. I’d want him to feel passion again, and she’d have to put in the work with him just like I did when I saw my clients. It was an interesting thought, but one that I was in no way ready to act on.

I’d just filled my gas tank in Barstow and gotten back on the freeway when my phone chirped me out of my reverie. I was surprised to see it was Dana on the caller ID. Normally we only texted and rarely spoke on the phone.

“Hello?”

“Hello, Elisa, it’s Dana. Is this a good time?”

“Sure, I’m in my car by myself. What can I do for you?”

“In your car, well, can you pull over somewhere for a few minutes? Or maybe call me later?”

“Give me just a second.” Luckily I was a quarter of a mile from a rest area. I took the exit and parked my car.

“Okay, I’m off the freeway and I can talk. Is anything wrong?”

“Oh, gosh, no. Quite the opposite, in fact. Somebody is getting quite popular!”

“Really ... ummm ... I guess that’s a good thing, right?

“It’s a very good thing for both of us.”

I know it’s a good thing for you, you’ve been getting a large share of my earnings. Of course, I kept that snide little thought to myself.

“So what’s new?”

“Well, two things, actually two clients, and they’re both pretty interesting and potentially lucrative. I’ll start with the shorter date. We have Steven, a thirty-nine-year-old accountant who would like to book you for four hours on Saturday night. It sounds nice, actually. Dancing and drinks at the Tao nightclub, then a few hours of sex afterwards. He’s checked most of the normal boxes, but he has a request we don’t actually have a box for.”

I took a deep breath and was almost afraid to ask my next question. “Okay, and what would that be?”

“It’s his wife’s birthday and he’d like you to be his present to her.”

My jaw dropped open and I was thankful we were on the phone instead of talking face-to-face. “I ... ummm ... I don’t know.”

The hesitancy in my voice was quite evident and she quickly stepped in. “Before you say no, just hear me out.”

“Okay,” I said cautiously.

“He will be there, but mostly as an observer. He wants you to have a few drinks, dance with her, pursue her, and then have sex with her. He wants to help her relive her college days, something along those lines.”

“How old is she?”

I could hear her typing on her computer, looking up the information I’d requested. “You’d be meeting them on her 30th birthday.”

My mind was running wild with possibilities. Seeing ... being with ... taking care of older men, that was something I could handle, something I was getting good at and growing accustomed to. But this ... what she was asking of me ... this request was on a whole other level.

“I know you’re apprehensive, Elisa, but let’s talk about it, okay?”

“Okay,” I said in a voice barely above a whisper.

“During your interview we never talked about this type of date because, frankly, our clients rarely request it.”

“Okay, but why me?”

“She loves your pictures and he loves your glowing reviews. Especially your ‘willingness to ensure your clients leave satisfied,’ as your last date put it.”

“I ... ummm ... I’m just ... ummm ... not sure.” My head was still spinning, and it was as if my brain refused to form a coherent thought.

“Tell me what you’re thinking,” she said.

I took a deep breath, cleared my head, and willed myself to respond to my boss with a cogent answer. “You’ve always expected a lot from me and I’ve always delivered for you and our clients, I think we can agree on that, right?”

“I completely agree with that.”

“What if I agreed to this and wasn’t able to meet her expectations?”

“Have you had many experiences with women?”

“I’ve had a few, but let’s just say that it’s been limited.”

That was the understatement of the year. During my freshman year I met a girl who lived in my dorm. We became friends and went out together. When our night of hard partying was over, we went back to her room and her libido was in overdrive. She hit on me, which led to us making out, me going down on her, and me getting her off multiple times. Unfortunately, she fell asleep before she could reciprocate, which left me turned on and incredibly frustrated.

To make matters worse, when I saw her the following day she pretended nothing had happened. I was actually dumb enough to let it happen again, hoping for a different outcome. Finally, I put my foot down and rebuffed her advances, which led to the end of our friendship. I was fairly certain she’d loved what I did to her, because I just mimicked what guys always did to me. Since then I’ve always been into guys and never considered myself to be anything other than heterosexual.

Which brought me back to the question. Would my ... ummm ... very limited skill-set even come close to meeting an experienced bisexual woman’s expectations or that of her rich husband? Dana’s voice broke me out of my thoughts and back to the now.

“Listen, Elisa, out of all my employees they specifically requested you. If you say no they’ll look elsewhere. But I believe in you, and like you said you’ve never let me down. I know this time won’t be any different.”

Now she’s handling me. For better or worse, her kind words and her faith in me won me over. “Okay, I’ll do this.”

“Excellent, I know you’ll have a great evening with them. His name is Steven and his wife’s name is Lynn, and they have a couple of kids. While I have you on the phone I’ll send you a picture of them.”

“Okay, but let me ask you, she’s had a lot of experiences with women?” I tried to sound confident, but I was afraid my inquiry might betray my lingering self-doubt. A couple of seconds later my phone chirped and I looked at the picture while Dana answered me.

“Steven told me that she’d been with quite a few girls during college but once they’d married and had children her opportunities dried up. Lynn’s greatest fantasy is to be with a hot young college girl and have, what did I write down here ... oh, yes. She wants crazy and wild and romantic love-sex. I guess it’d be up to you to interpret what that means.”

Dana was talking but I was only half-listening; I was staring at the photo she’d sent me. They were on a beach, under a palm tree, and his arm was securely around her, holding her tight against his body. He was wearing long surfer-type board shorts and she was in a little blue bikini.

I quickly came to the conclusion that Lynn was gorgeous. Not the ‘she passes for cute’ variety, but she could be a model, type gorgeous. She had long blonde hair, high cheekbones, and puffy, pouty, sexy lips. He looked every bit his almost forty years, but she could pass for one of the girls I went to class with every day. And her body... This woman has had children? Bullshit, I wouldn’t believe it until I saw them. My eyes slowly gravitated towards him. He was handsome enough, but I’d be willing to bet he had rich parents to land a stunner like her.

“So, did you get the pic? What do you think?” she said.

Any notion of this date not being a complete and utter disaster had evaporated after seeing that picture. Of course, like always, I hid my true feelings from my boss. “They’re a cute couple.”

“I know, right?” She’s really pretty, isn’t she?”

“She is.” She’s Miss-Fucking-America, Boss; how do I even begin to sexually please a woman like that?

“Steven said she also likes playing with toys. He really didn’t elaborate, so just be ready for it, okay?”

Of course she likes toys ... what blonde supermodel goddess doesn’t? I thought sarcastically. “If she likes that, it’s no problem.”

“I knew you wouldn’t have a problem with it,” she said gleefully.

“And you said this would be a four-hour date?”

“Yes, Steven would like to watch and then join in at some point.”

Pleasing a forty-year-old man, finally something I can actually handle. “Him joining us is fine.”

“This will be a great night for you. Your take will be $4,900.”

“I like the sound of that. But you said you have a second date to tell me about?”

“Yes, I do. You remember Edward from a couple weeks ago, right?”

I thought for a moment. Edward ... yeah ... the guy who’d wanted me to see his son and ... ummm ... teach him a few things. As Dana said, that had been a few weeks ago, and I had thought he’d forgotten about it or had changed his mind.

“Yeah, I remember him, what’s he up to?” I asked, hoping he’d agreed to go forward with his plans.

“He wants to book his son for a twenty-four hour-date in five weeks. Will you be available then?”

I couldn’t answer fast enough. “Yes! I’m available.” I couldn’t think straight; how much money would that be? “Wait, my period is when?” Dana tracked all of our periods on her computer. I was on the pill, of course, which gave me regular cycles of shorter duration.

“I already checked, and you’re in the clear. He said he’d already discussed this with you and you’re actually going to be his son’s birthday present, is that right?”

“Yes, I’m supposed to turn his boy into a man. It should be kinda fun, the kid is an honest-to-God virgin, unless something’s happened since I saw Edward, and from what he told me that probably hasn’t changed.”

“Interesting. Well, he’s checked all your boxes for that date, and I was willing to negotiate a discount on the usual fees because of how long the date would be, so it would come to ... let me click to that screen again ... yes. Seventeen thousand five hundred for you.”

I shivered for a moment. “Se-seventeen?” I asked with an unsteady voice. It was actually difficult to imagine someone paying me that much for twenty-four hours of my time.

“Seventeen five, Elisa.”

I took a deep breath. “I think I can live with that,” I gushed.

Dana chuckled into the phone. “I thought you’d be okay with that figure. Can I tell you something, Elisa?”

“Of course.”

“Well, it’s just that I’m very proud of you, dear. I had a feeling about you, and look at how well you’re doing. I’m kicking around the idea of raising your rates to keep up with the demand.”

I giggled. “I’ll leave that up to you, Boss.”

What she’d said was true, though. I had about fifteen requests for dates in my in-box. When I originally agreed to work for her, I told her I could work one night a week so I’d have plenty of time to study and keep up with my classes. However, because of all of the glowing reviews I’d received, I did seem to be in high demand, and that was a little disconcerting. Dana had promised she’d never pressure me into taking on more than I could handle, and I hoped that wouldn’t change.

We chatted a little more about the particulars of the upcoming couple-date and then disconnected. I did some math in my head.

Seventeen-five for the all-day date and almost five for the other is exactly twenty-two four for me, and maybe a raise after that. This could really set me up well.

When I got back into Las Vegas I found that my small two-bedroom apartment was empty. Then I remembered that my roommate, Lexi, was having dinner with her folks in Mesquite, about an hour and a half up the road. It was only about four in the afternoon, so I figured I had a two-to-three-hour window of privacy. I went to my bedroom and sat at my little desk that was normally reserved for doing my school-work.

I never really watched porn, the real thing was always so much better to me. Before I started working for Dana, I’d occasionally, maybe once a month, pick some lucky random guy from one of my classes and hook up. But now, having sex once and sometimes twice a week more than scratched that itch, and it was almost as if the more I got the more I wanted. On the occasional times when I did touch myself, the image in my head was always of a guy, one who I’d plan to pursue. However, today felt different. I pulled out my phone and pulled up the image Dana had sent me. There she is again ... that beautiful blonde on the beach with her husband’s arm around her. As sexy as that image was, I’d need a little more stimulus if I was going to get myself off.

I flipped my laptop open, searched for Lipstick Lesbian, and checked out the videos on the list.

Well that’s a bust. It was just a bunch of YouTube videos that featured very masculine-looking girls discussing their conquests of Lipstick Lesbians. I needed more than talk, so I tried Romantic Lesbians.

That search produced gorgeous female couples in fairly long clips. I chose one that featured two very pretty girls, Malena Morgan and Mia Malkova. It was about fifteen minutes long and I clicked the full-screen button. I quickly discovered there was no plot, and I was okay with that because I wasn’t looking for one. When the clip began both women were naked, outdoors and by a swimming pool. They were passionately kissing while running their hands up and down each other’s body.

I set the laptop on my bed and tilted the screen so I could easily see it. As the video played, and the girls cooed softly, I shut the blinds, darkening the room. I dug out an opened bottle of Pinot Grigio from my small fridge and emptied the remaining contents into my coffee cup.

Yeah, that’s nice, I thought, savoring the cool, crisp taste. The effect was almost immediate; the cold wine turned warm as I swallowed, and I felt a little glow radiating through my chest. Watching the porn girls slide their tongues in and out of each other’s mouth gave my pussy a little tingle. I set the cup down on my desk next to the bed, slipped out of my clothes, and slid into the bed with my laptop in front of me.

My vagina moistened in anticipation. The video girls weren’t wasting any time. One of them had two of her fingers inside the other while she moaned in appreciation.

Damn, that is so sexy. I pinched and pulled my nipples until they stood proudly off my breasts. You’ll want me to do that to you, won’t you, Lynn? You’ll want me to please you, just like that.

My fingers continued to pinch and pull my nipples, sending little tingles through my stomach. So many guys my age go straight for my pussy. I teased them more, languorously, as I slowly turned myself on. You wouldn’t do that, would you, Lynn? You’d play with my breasts, you’d work me up, have me dripping wet, and have me begging for you to touch my pussy before you ever did.

My pussy felt like it was on fire and I could feel my secretions oozing out of my vagina. As the video continued to play, my thoughts, my fantasies went wild. You’ll be wearing a sexy little thong for me, Lynn, won’t you? What should I do with it? Should I put it in my mouth? Or, better yet, would you make me put it in my mouth?

That thought generated a whole wave of tingles that were reverberating between my legs. One of the girls was moaning now because the other had her tongue buried deep in her vagina. However, that was no longer what I was interested in. I closed my laptop, grabbed my phone, and again stared at the picture. Then I propped the phone up, leaned back on my pillows, and began teasing my pussy.

I just want to fantasize about you, Lynn ... only you ... you and me, together.

My fingers teased my little hood for a few moments, and the warm sensations radiated throughout my body. The lips of my vagina were red, puffy, and engorged, and my juices were gathering on them and making the tips of my fingers nice and slippery. Slowly, I dipped one and then two fingers inside. I couldn’t resist, I slipped my wet fingers inside my mouth.

You’ll want to taste me, Lynn, won’t you? You’ll love how I taste, won’t you? I hope you will.

I was worked up and already very close. I thought of using my fingers to finish myself off but decided against it. I reached into my nightstand and pulled out my favorite vibrator. It was long, about seven inches, and black.

Have you ever had a black man, Lynn? Has a black man run his hands over your flawless porcelain skin or run his fingers through your long, beautiful blonde hair? That was something I’d never experienced ... maybe someday.

I twisted the bottom of the big vibe, powering it on, and I felt it pulse on my hand. I let the tip slide over each of my erect nipples and I let out a low, deep moan. When I looked down, there was a large wet spot between my legs, soiling the sheets.

We’re going to get each other off, aren’t we, Lynn? Right in front of your husband. I’m going to show him what his wife’s body is capable of. I’m going to show him that I can make you come over and over, like only another woman can.

Okay, let’s make this happen.

I moved the vibe down and used the tip to split my wet lips open. With one long hard thrust I slid nearly all of it inside me. “Fuck, yesss,” I moaned. I worked it in and out of my pussy harder and faster, picking up the pace. Then I adjusted the angle so it perfectly pulsated against my clit while I continued to slam it and out of my vagina.

My orgasm hit me hard and fast. The sudden build-up of pressure and the intense, explosive climax took my breath away. Wave after wave hit me and it felt as if I couldn’t keep air in my lungs. My head lolled from side to side and I sank deep into my bed. Almost involuntarily, I withdrew the buzzing vibrator from my vagina so it would no longer make contact with my now-very-sensitive clit.

It took another minute or so before I was able to catch my breath. That was kinda hot, I thought to myself, but nowhere near as good as the real thing. After my senses were back about me, all my anxiety and self-doubt once again flooded my mind. Can I pull this off? Is it even possible for me to please this experienced, sophisticated woman, in front of her husband, no less? Dana had always demanded so much from me, and somehow I’d always been able to meet her, and her clients’, high expectations. Will this be the first time I let her down? Will the evening I spend with this couple even come close to my fantasies?

I wished I was meeting them that night so I could get this anxiety-ridden date over with and put it behind me. Unfortunately, I had an entire week to wait before I’d find out if I was up to this task.

It was Saturday night and my knees were knocking together. My stomach was queasy and I was not entirely sure that the small Cobb salad I’d eaten for dinner would remain there. Steven had requested a late start time for our date, ten o’clock. That made sense, because most clubs don’t really fill up and get going until later in the evening. I didn’t know how much we’d be drinking so I’d booked an Uber to take me to the Venetian instead of driving my car.

I must have tried on ten different outfits once I got out of the shower. What the hell do I wear when I’m going on a date and meeting an older couple for the first time? After what felt like hours in front of the mirror, I finally settled on a black, strappy-back, sleeveless cocktail dress. I also chose to wear two-inch kitten heels that went perfectly with the short little frock. Normally, I wore tall high heels when I met clients, but Dana had told me that Lynn loved to dance so I knew we’d be spending at least part of the evening out on the dance floor. The shorter heels didn’t give my legs the long-and-leggy, well-defined look that my clients always appreciated, but I always found it difficult dancing in four-inch heels and I hoped my couple would let it slide. To complete the look I selected a black silk thong, and because most of my back was exposed I didn’t wear a bra.

I’d spent the entire week trying to keep this evening off of my mind as I attended my classes and did my homework. Steven was an older man and exactly what I was now growing accustomed to. However, his wife was a completely different situation, and I was filled with anxiety, apprehension, and self-doubt about my abilities to please an older, experienced bisexual woman.

It was 9:45 and I was waiting about a hundred feet from the entrance of the Tao nightclub. I was sitting at a large bank of slot machines, nursing my watered-down drink and attempting to blend in with the other gamblers. I resisted the almost overwhelming temptation to look at my watch for the tenth time. Will they be the first client to actually stand me up? That would be difficult to envision, but maybe ... just maybe ... if nothing else, it would get me out of this potentially precarious situation. Then my hopes were dashed.

I saw a couple walking towards the entrance of Tao and quickly recognized Steven and Lynn from their picture. She was wearing a little black miniskirt with a cute white lace top, a brown cardigan sweater, and black ankle boots with two-inch heels. Her flowing blonde hair was actually a little longer than in the picture Dana had sent me. It was styled in gentle loose curls that fell perfectly around her ample breasts; she truly looked stunning. Seeing her in person also made me realize how tall she was. She had to be at least 5’9” and combined with the added height of her boots she had to be close to six feet. She reminded me of a mythical amazon goddess that would devour anyone or anything in her sight, and that only added to the butterflies that were nervously churning in my stomach.