Chapter 2

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.

“I want to apologize again to you, honey. I know I always promised to help pay for your education and I know what a disappointment this is.”

I absentmindedly listened to my father on the other end of the line while scrolling through my profile page on Dana’s secure website. “No, Daddy, it’s okay, I totally understand. I know unemployment isn’t much money and you need to use it to take care of yourself.”

“Are you going to have to quit school like you thought?”

I could hear the concern in his voice and I tried to keep my tone light and upbeat. “No, I got a job and it should take care of the expenses that you’re not going to be able to cover,” I said confidently.

“That’s great that you found a job so quickly; what will you be doing?”

Time for a lie ... a huge lie. “I got a part-time job through the student work-study program.”

“Will you make enough to cover everything you need?”

“Yes, Daddy, more than enough. Please just concentrate on you and take care of yourself, don’t worry about me, okay?”

“You know I always worry about you, honey, but okay,” he said reluctantly.

“I have to get going, Dad, and get my homework done, but I’ll call you next week.”

“Okay, honey, I love you.”

“I love you too, Daddy, bye bye for now.”

I felt horrible lying to my father, but I knew I didn’t really have any other option. It would break his heart if he ever discovered what I was doing for money now that he couldn’t help me anymore. Thankfully, I knew he’d never find out and my secret would be safe.

I set out for my Friday-evening date in a good mood. I’d talked with Dana earlier in the week, and she’d reminded me that not all my dates would be as easy and enjoyable as my first one with Henry. She knew about the date I’d accepted for tonight and she’d cautioned me to be prepared for a bit of a challenge with an even older man. But I figured a one-hour quickie couldn’t be that bad, and the 475 dollars I would earn for bareback sex with no extras would be easy money. Because this was our first meeting, I chose to wear the same little black cocktail dress and heels I’d worn the previous week with Henry.

It was 6:30 when I pulled into the parking lot of the Palms casino and made my way to the Coffee Bean and Tea Leaf coffee shop. When I arrived, I noticed an older gentleman sitting at one of the tables near the counter. Since there was no one else near him, I couldn’t help but assume he was my date. He was an older gentleman, much older, and I guessed his age to be about 75 or maybe even pushing 80. Unlike my previous date, Henry, he looked frail and weak, and I noticed a walking cane leaning up against his chair. When our eyes met, he gave me a polite smile and I was fairly certain he was my date for the evening, so I approached him.

“You’re quite striking, just like your picture,” he stated confidently, “I’m Peter.”

“Thank you so much,” I said shyly. “I’m Elisa, may I join you?”

“Of course, can I get you a coffee or tea?” he asked.

“I’d love a latte, but I’ll get it.”

Since he was using a cane, I wasn’t sure how well he got around, and because I was standing up anyway it seemed like a good way to build rapport. He reached into his pocket and pulled out a 20-dollar bill and handed it to me. “I’d also take a refill on my Earl Grey tea.”

It already felt like a much different date than my first experience. We were meeting earlier than my previous date last week, and drinking non-alcoholic beverages just seemed to add to my uneasiness somehow. Nonetheless, I vowed to make his experience the best I possibly could and I desperately tried to shake off any negative feelings I was having towards him. After I placed our order and got our drinks, I sat down at the table beside him.

“So, have you been doing this long?” he asked.

My first instinct was to lie, but being truthful with Henry last week seemed to work out well and I decided to employ the same strategy. “I have been an escort only a couple of weeks,” I admitted. “You’re only my second date.”

He gave me a little smile. “I’m glad you’re new at it. I always have a much more enjoyable experience with the newer girls.”

“I’m glad and I’ll definitely take care of you,” I said seductively.

He took a sip of his tea. “So, your profile says you’re a student; why did you get into this line of work?”

“I needed some extra money to help pay for some of my expenses, and this seemed like a good way to earn it.”

“You’ll do just fine in this line of work.” He reached across the table and took my hand in his. It felt cold and almost clammy, which gave me an uneasy, unsettling feeling. However, I didn’t let it show and I romantically gave his hand a little squeeze before he released mine.

I took a sip of my latte. I could tell he liked me and we were building rapport with each other, but I wanted to keep him talking. “So, what do you do for work?”

“I sold my plumbing supply business 15 years ago and I’m comfortably retired now. Having a little extra money allows me to spend an evening with a pretty young girl like you a couple of times a month.”

I shot him another sexy, seductive smile. “I’m glad you found my profile; I’m having a great time already and I know it will only get better.”

“To be honest, I look for the new girls, and once we meet, if there’s a connection, they become my regulars.”

“I look forward to being one of your girls,” I said sexily.

“Speaking of which, my time is kinda limited, my wife thinks I’m at bingo, so if you’re ready we can retire to my room.”

“I’d love that,” I said enthusiastically. In reality, I wished he would have not mentioned his wife. His statement reminded me that Dana had said most of her clients were married. It was so much easier for me to have sex with a guy who was single. Fucking a married guy was a hangup that I was still struggling with and working through.

When we both stood up, he reached for his cane. He put his arm in mine and we very slowly made our way to the large bank of elevators that would take us to the upper floors. On our way there we received many knowing looks from the gamblers. Last week with Henry we somehow passed as a plausible couple, but not tonight. It felt as if I was holding a large sign above my head that read, “I’m an escort.” I wanted to walk faster to escape the knowing looks and glares we were receiving from everyone we encountered, but of course I had to walk at a snail’s pace so Peter could keep up with me. It was a truly mortifying experience.

After what felt like an hour we finally reached the elevators, which took us up to the 45th floor. He must have requested a room by the elevator, because we only took a few more steps before we reached the door. He reached into his pocket, pulled out a keycard, opened the door, and held it open for me, which gave me a chance to take in my surroundings. The walls were painted an off-white and there was a king-size bed to my right as I entered the room. There was a dark brown hardwood floor underneath the bed and a small living-room area with a brown shag carpet that was complete with a couch and chair. There was also a brown accent wall behind the couch that gave the room a small pop of color. I also noticed a large mirror behind the bed, which I thought was an interesting decorative touch.

Peter walked past me and then sat on the edge of the bed. “Would you take off your clothes for me?” he asked.

He obviously wasn’t into wasting time. “Yes, of course,” I said demurely.

As I unzipped the back of my little dress, he quickly began removing his clothes. I let the little black dress fall to the floor and I felt his eyes move up and down my long, lean frame. “You have a beautiful body,” he said huskily.

“Thank you,” I said shyly. When he removed his boxers, my eyes traveled down and I noticed that he had a very small penis. Only a couple of inches of it was visible and it was not very thick. I’d been with quite a few guys but I couldn’t remember any of them being this small. However, I ensured that my expression remained calm and even despite my inner disappointment at his obvious shortcoming.

“Take off your panties, but leave your heels on,” he said while his eyes continued to drink me in.

Slowly, I slid my fingers through the waistband of the little thong and casually moved them down my tan thighs and then stepped out of them. He seemed to like to be in control of everything that was taking place so I decided to let him make the next move.

“None of you girls seem to have any pubic hair these days,” he stated matter-of-factly. “It’s so much different than the young women that I was used to growing up.”

“I hope it’s okay that I shaved for you,” I purred sexily. I actually had been getting it waxed off because I got really bad razor bumps when I shaved, but I reasoned that wasn’t something he needed to know.

“I love it, come over here and join me on the bed.”

I took a couple of steps forward and slid onto the bed beside him, and he leaned in and we shared a soft kiss. His lips were as cold and clammy as his hands were earlier, but again I acted like I didn’t notice or mind. “I want to feel your mouth on me,” he said after he broke our little embrace.

“Of course, I’d love that,” I whispered. He leaned back and propped himself against the headboard, and I slid between his legs. Without using my hands, I took his flaccid little penis into my mouth and began to gently suck. He moved his hands to my long dark hair and began to gently weave them through it. I was hearing little moans and grunts of appreciation from above me, but nothing seemed to be happening in the erection department. Even though I was keeping my mouth warm and wet, I let a long string of saliva drip out of my mouth and onto his cock before taking him back inside. A couple of minutes went by as I continued to fellate him. Unfortunately, despite my best efforts, I was unable to get him hard, and my jaw was beginning to get sore.

“Your mouth feels so good,” he moaned from above me. “Keep going. I took my Cialis about an hour and a half ago and it should be kicking in at any time.”

Now I understood the problem. It wasn’t me or my lack of skills at giving head. Instead, it was him and his erectile dysfunction. Like everything else, I pretended that it didn’t bother me because I wanted to please him and make him happy. “I know a little trick that might help, if you’re okay with me trying it.”

“Sure, I’ll let you try whatever you want,” he said appreciatively.

I slipped out of bed and grabbed my clutch purse, which I’d placed on the bedside table. I dug around inside and retrieved a small bottle of Astroglide. I slid back into bed between his legs and coated my middle finger with a generous amount of lube. “Okay, let me know if it becomes uncomfortable, okay?”

“I will.”

Slowly, I eased the tip of my middle finger inside him. I could feel his body tense up when I reached the tight ring of his sphincter and my progress was momentarily thwarted. “Are you okay, do you want me to stop?” I asked.

“No, don’t stop, it feels amazing.”

“Okay, Daddy,” I cooed sexily. I slowly worked my finger in deeper and moved it until I could feel the front wall of his rectum. He let out a low, deep moan, and it was as if the tension was leaving his body as he began to relax.

“Oh, yeah, right there,” he grunted.

I took him back into my mouth and began to gently suck while continuing to rub his prostate, and gradually he started to get hard. I concentrated my efforts on the head of his penis, ensuring my mouth remained warm and wet. After about a minute or so, I realized he was fully erect and I let his cock slip out of my mouth.

“How do you want me, baby?” I asked. He wasn’t very steady on his feet so I was pretty sure I knew the answer to my question, but I still wanted to give him the choice.

“I want you on top of me, I want you to ride me.”

“Oh yeah, I’d love that.” In reality, nothing we’d done was turning me on and I wasn’t even wet. I guessed that even fully erect he wasn’t even four inches, and to make matters worse he was pencil-thin. Regardless, I was faking being aroused really well and he seemed to be ecstatic that he was actually hard enough to penetrate me. Before he lost his erection, I quickly grabbed the Astroglide, poured a large dollop onto my fingers, and worked them into my pussy to create some artificial moisture. Then I slid on top of him, sitting on his stomach. I scooted down until I felt his cock rest at my aperture, then I reached behind and guided him inside me.

“Oh yeah, your pussy feels so good,” he moaned.

I began to slowly grind on him, squeezing the muscles in my vagina as tight as I could. “Your cock feels so good inside me, Daddy,” I moaned. Another lie. In all honesty I could barely feel him inside me, but it didn’t seem to matter. His heavy moans and pants told me that he was enjoying the experience much more than I was, and that was all I really cared about.

Taking me by surprise, he reached up and roughly squeezed my breasts, pawing at them very aggressively. Normally, a little bit of rough play turned me on, but nothing about him was arousing to me so it just seemed to add to the sexual frustration I was feeling. I continued to squeeze him tight inside me, milking him, and I heard his breathing change and he began to stiffen up. Even though he’d only been inside me for one or maybe two minutes, he was close to orgasm.

“Yeah, fuck me hard and deep, just like that,” I moaned, continuing to play it up and making him think I loved everything he was doing when the reality of the situation was the exact opposite. I was moaning and grinding on top of him when he stiffened up for the final time. I faked my orgasm perfectly, just in time with his real one. Just as he began to open his eyes, I collapsed on top of him and pretended to catch my breath. I couldn’t remember anyone who’d ever come so fast, but in total honesty I was just glad my date with him was almost over.

“God, you were great, that was just amazing,” he gushed as I rolled off of him and slid to his side.

“It was so good, I loved it.” At this point, another lie couldn’t hurt, right?

He reached over and pulled his wallet out of his pants. “Here’s a couple of C-notes for you, I loved this and I can’t wait to do it again.”

“Thank you so much,” I said as I accepted his tip. But I’d have to think long and hard before accepting another date request from him. The only thing good about my evening with him was that it was over, I’d made some money, I’d made him happy, and I knew he’d give me a good review.

“I’m going to grab a quick shower while you’re getting dressed, okay?”

“Sure, no problem.”

I collected my clothes and got into the shower. As I was rinsing off, I noticed that he’d barely come inside me, which made me wonder if I was the only one who’d faked it. I got dressed, and when I opened the bathroom door I saw that he was already gone and didn’t even tell me good-bye. It was all for the best, because I’d actually dreaded the thought of walking through the casino again with him under the judgemental stares of the players.

All told, it was an interesting second experience. Dana had told me that there would be dates like this where I’d have to concentrate on giving pleasure to my partner while knowing that there’d be none for myself. The date had gone smoothly and I knew I’d made Peter happy. I reasoned that sometimes that would be the best outcome I could hope for.

After the sexual disappointment of the previous evening I was hoping for a much better time on tonight’s date, and I drove towards South Las Vegas Boulevard, the legendary Strip, in high spirits and high heels that looked good with my shapely legs and my new two-piece spaghetti-strap white lace cocktail dress. The hem of the sexy little frock came just above my knees and featured a modified bikini top. It was actually the other dress that Dana had helped me choose during my interview. I knew I was going to have to perform all kinds of sexual acts, but the money would be fantastic; I would be earning over 4,000 dollars for the three-hour date. The man I was to meet was in his late 40s, around my father’s age and a few years younger than Henry, so I was already excited about the possibilities.

I arrived at the Mandalay Bay, left my car with the valet attendant, and walked briskly through the casino to the Eyecandy lounge to meet my date. But when I got there my excitement died and turned to dread; there was a man there that I knew, and I was sure he’d recognize me. I’d known my date’s name was Brian, but I’d never dreamt that I’d actually know the man approaching me when I accepted the date. He was a long-time friend of my father who’d known me since I was a small child.

He stood before me with a twinkle in his eyes, and I knew what the situation was. He was my date for the evening and I was going to have to perform for him sexually. I was totally mortified. My knees were shaking and I thought I might actually faint.

“Hello, Elisa,” he said with a bright smile. “How nice to see you.”

“Hello, Mr. Anderson,” I managed to whisper.

“Under the circumstances, I think it’s okay for you to call me Brian. Let’s sit down,” he suggested. “You look a little unsteady.”

There’s an understatement, I thought. It’s more like totally screwed, and not in a good way.

He led me to a table near the back of the room and a server immediately approached us. I requested a Cosmopolitan and Brian ordered a scotch and water. I was shaking both inside and out; I couldn’t keep my hands still in my lap.

“Relax, Elisa,” he said in an effort to calm me down. “This won’t be bad.”

“I’m so embarrassed,” I said in a low, horrified tone.

“I understand, but it’s okay. I couldn’t believe it when I saw your pictures on the website. I watched you grow up and I thought you’d turned into a beautiful woman, so I was extremely excited about the prospect of being on a date with you.”

“That’s very flattering,” I replied, “but this is so...”

“I know, it’s kind of strange, but it’s also very intriguing for me.”

Our drinks arrived, and I immediately gulped down half of mine in an effort to settle my nerves. Brian sipped from his, then asked, “Why are you doing this, Elisa?”

“I think you know my father lost his job,” I answered, “and I need money to stay in school.”

“I do know, and I’m sorry about that for both you and your family. I’m very sympathetic about your problem, and I’m happy to help you out financially.” He paused, then continued, “But you’ll have to earn the money.”

“I know,” I whispered. “I hope you won’t tell anyone about me, about this...”

“Of course not,” he said gently. “Aside from any other reasons, Dana would kill me, and I’d never want to cause a problem between you and your father.”

I let out a little nervous laugh and he smiled at me again.

“I was amazed when Dana told me everything you’re willing to do; you must have had a lot of experience for someone your age.”

Since he already knew what I’d offered to do, there was no point in evading the topic. “Yes, Brian,” I said quietly. “I’m willing to do all those things. I have had some experience and I know what I’m in for.”

“In that case, we’re going to have a very good evening,” he told me, “and I mean we when I say that.”

I can only hope, I thought to myself. But his comment helped me start to relax, and I started thinking about what might happen, and I felt a little tingle. I knew that after last night’s disappointing date I could use some sexual release, and despite my nerves and my embarrassment I was ready for action.

“I’ve always hoped I’d have an opportunity to be with you. I’ve fantasized about this for a long time and I never thought I’d actually have an opportunity to... you know.”

In all honesty, I’d never thought about him in a sexual way. He was always just a friend of my father and someone I’d met sporadically. But under the circumstances he was being quite gracious, and, because I’d be making a lot of money this evening, I hoped we’d have a good time and maybe he’d even want to see me again and it would turn into something more.

“I’m feeling better about this and I’m actually... you know ... looking forward to it now.”

“Do you want another drink?” he asked flirtatiously. “I don’t want to rush you, we have plenty of time.”

I thought another drink might be nice but I decided against it. I figured I might as well let the party get started, because maybe once we got into it I’d be able to enjoy it. “Thank you for offering,” I said sweetly, “but I’m okay for now.”

“Maybe later, then,” he said. “Shall we go upstairs?”

“Yes, I think we should.”

He stood and reached across the table for my hand, and I let him help me rise. We left the lounge and walked to the elevators, then took one to the 42nd floor and walked down the hall to his room. He opened the door and gestured for me to precede him, which gave me a chance to take in my surroundings.

The room was quite large compared to the others I’d been in over the past two weeks and I reasoned it was a junior suite. There was a king-size bed in front of me and two large floor-to-ceiling windows offered magnificent views of the Las Vegas Strip. The room featured a nautical theme with blue carpet and window coverings and a large sand-and-water motif behind the bed. In front of the bed was a sitting area, complete with a couch, two chairs, and a coffee table. He’d obviously pulled out all the stops for this evening, but that wasn’t really surprising. Because of his relationship with my father, I knew he owned a small construction company and could afford such an extravagant room.

After closing the room door behind him he came around and stood in front of me. He looked up and down my body and I waited for him to direct our activities. His eyes roamed up and down my tight lace frock and his eyes lingered at my cleavage.

“Take off the dress,” he directed.

I reached behind me and unzipped the modified bikini top and slid it off my shoulders, then unzipped the back of the tight skirt and wiggled it down past my hips to puddle at my feet. I resisted the urge to wrap my arms across my breasts and form a little hand-bra as I stood in front of him in my tiny thong and heels. I silently waited for his reaction, which came immediately.

“God, you’re beautiful,” he gushed. “I’ve seen you in skimpy bikinis but never like this. Turn around.”

I did a slow pirouette and watched over my shoulder as his gaze fastened on my exposed ass cheeks.

“This is going to be fantastic,” he enthused. “I haven’t been able to do anal for years, and your body is built for it. But first I want you to take the edge off for me.”

I knew what that meant, what he wanted, and my nervousness flared up again. He immediately called me out for my brief hesitation.

“Come on, Elisa,” he said gently. “I’m trying to cut you some slack here, but you’re making that difficult for me. You’re the one who wants to be a high-priced escort, so show me what you can do and get on your knees,” he said somewhat more sternly.

Despite my embarrassment and my nervousness, I knew what I had to do. I really needed the money, and I was worried about getting a bad review that would cut my career as an escort short, so I steeled myself and determined to make the best of this situation. Giving head usually turned me on, and Brian’s semi-dominant tone worked on my mind as well. I slowly sank down onto my knees and reached for his zipper.