Chapter 5

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 walked toward the Old Homestead Steakhouse in Caesars Palace just before five o’clock. I was wearing what was for me a rather conservative knee-length Bodycon dress, with a neckline that showed just a hint of the tops of my breasts, and a pair of four-inch black ankle-strap pumps. I saw a young man standing in the outer corridor. He was tall, just like his father, and quite handsome, but he was underdressed for the occasion in just a polo, a pair of Dockers, and suede loafers. I stopped in front of him and said, “Hello, E.J., I’m Elisa.”

“I hate that nickname, only my father calls me that,” he said disdainfully. “Call me Ed.”

“Okay, Ed, no problem,” I said cheerfully.

He turned and sauntered toward the entrance to the restaurant, obviously expecting me to follow him. All right, I said to myself. I’m going to start this kid’s education right now. He’s got an hour and a half to convince me I can straighten him out. I stood there calmly. When he reached for the door, he noticed that I wasn’t with him, and he strolled back to me.

“What are you waiting for?” he asked in a patronizing tone.

“I’m waiting for you to behave like a gentleman and treat me like a lady,” I told him.

He shot me a condescending look, then sneered, “You’re not a lady, you’re a whore that my father purchased for me for my birthday.”

I inwardly cringed. Snide little fucking prick. Then I looked him straight in the eyes. “Yes, I am a prostitute, but for the record I prefer the term escort. Despite that, for this date, in public you’re going to treat me like a lady, and I expect you to show me proper respect.”

He had the grace to look embarrassed. “Sorry,” he mumbled. His heart wasn’t really in that apology, I thought, but it’s a start. He extended his elbow, I put my arm into it, and we walked together toward the restaurant. When we got there, I waited until he figured out that he should open the door for me, and when he did I said “Thank you” and walked ahead of him to the maître d’s stand.

“May I help you?” the hostess asked.

“Reservation for Foster,” Ed answered in an annoyed tone.

She hit a couple of keys on her iPad. “Certainly, Sir, this way, please.” She grabbed a couple of menus and led us to what could have been a four-top table but was set for two people next to one corner of it. He didn’t assist me; he just pulled out a chair and sat down with a scowl on his face. A male server hustled over and pulled out my chair. I sat down and shot him a grateful smile, which didn’t improve Ed’s mood in the slightest.

“What’s your problem?” I asked him.

The server reappeared before he could reply. “May I offer you a beverage?”

“I wanna Coke,” Ed said in a loud voice, much too loud given the quiet ambiance of the restaurant, and some of the other patrons looked over at us.

The server ignored him and looked at me. “For you, Miss?”

It’s time for Ed to learn a bit more. “I’ll have a Virgin Mary, please.”

“Of course, Miss, and the young gentleman will have a Coke.” He bowed slightly in my direction, then turned and left us.

“What was that all about?” he snickered. “Virgin Mary, huh?”

“Are you this way on all your dates?” I asked sweetly.

“What way ... what are you talking about?” The boorish tone in his voice wasn’t lost on me.

“You’re rude and arrogant, a little 16-year-old boy who’s not even pretending to be a man,” I said bluntly.

“I wasn’t rude,” he protested. “That’s his job, to get us drinks.”

“That doesn’t mean you have to be demeaning to him. A little courtesy goes a long way.” He looked away from me. “You deflected my questions, both of them.”

“My problem,” he said defiantly, “is that this is a gigantic waste of time. We both know why you’re here, we both know what’s going to happen, so why are we wasting time having dinner when we should be upstairs fucking?”

I took a deep breath and attempted to get my temper under control. He was two seconds away from getting slapped. Only my promise to his father to give him a chance kept me from getting up and walking out of the restaurant.

“The reason we’re having dinner,” I responded coolly, “is the same reason you can’t get to first base on your dates. My drink order was a subtle dig at the fact that you’re the only virgin sitting at this table, and if you don’t begin the process of changing your behavior you’re going to stay one for a long time.”

“That’s bullshit,” he replied hotly, “if you want the money we’re going to be fucking and this is just a big waste of my time.”

My blood was now boiling and I took another deep breath. “Let me explain something to you. Your father is spending a lot of money for this date we’re having, and he wants you to have a good time and learn some things. But nothing is guaranteed to happen, do you understand that?” I said coolly. I stopped talking and waited for everything I’d said to sink in.

A look of shock broke over his face. “What ... ummm ... what do you mean?” He thought for a moment, then added, “Just how much money is he paying you?”

“Your father told me how you were likely to act, and that he also hoped I’d be able to change your behavior.” I paused again so he could digest everything I was telling him. “We also made an agreement concerning what I can do if I’m unsuccessful in getting you to modify your behavior. I paused a moment, creating a little dramatic effect. You’re an intelligent young man, do I really need to spell that out for you?” I said icily.

I now had his complete attention. “To answer your other question, how much I’m being paid is between me and your father. If you really want to know, you’ll have to ask him.” I hesitated, then added a little sweetener. “If our date goes well, and I tell him how much I enjoyed being with you, he may just decide to tell you.”

Our drinks arrived, and we sipped in silence for a minute or so. Then he opened up to me a little. “Every one of my dates have sucked,” he admitted woefully, “and I definitely haven’t been successful, to use your word. I can’t even get a second date with any of the girls I’ve taken out.”

The tone of his voice had changed. He was being much more thoughtful and respectful now, and I knew what I’d said had made an impact. “Do you have any idea why that’s the case?” I offered gently. He’d softened his tone and I wanted to do the same.

Again we were interrupted by the server who returned to our table, and our conversation was put on hold. “Have you decided on your dinners?” the server asked. Ed was looking at me, and I was pleased to see that he reacted much more appropriately than he had before. He said politely, “What will you have, Elisa?”

I shot him a radiant smile. He’s learning. “I’d like a half Caesar salad followed by the Scottish salmon.”

“Excellent choices, Miss. For you, Sir?” There was a new note of respect in the server’s tone, and I hoped my dinner companion noticed it also. He apparently did, because his tone was much more civil than it had been earlier. Despite all the succulent entrées on the menu, though, his choice reflected that of a typical teenager. “I’ll have a shrimp cocktail and then the burger and fries.”

“Thank you, Sir.” The server maintained a steady facial expression, but I could see him holding back an eye roll. He collected the menus and scurried away to put in our order.

“Now where were we? Yes ... tell me about those dates,” I prompted, and he winced.

“I don’t get it,” he whined. “All my friends say girls let them make out with them, even on first dates, but they don’t let me do shit or they walk out on me.”

“Think back to how you treated me when we first met. You were rude, arrogant, and condescending, not only to me but to our server. If you treat the girls you date like you treated me when we first met, it’s no wonder you can’t get anywhere with them.”

Again, I had his attention.

“You’re a good-looking guy, and I’m sure the girls you take out know your father has money. Girls love to date a guy with money, but when you act entitled and expect things from them you’re not going to get anywhere, does that make sense?”

He looked down into his drink. It was pretty obvious that what I was saying was getting through to him and I actually started to feel sorry for the poor kid. I reached down and gently rubbed his thigh under the table in an attempt to stroke his bruised ego.

“It’s a game, and you have to learn how to play by the rules, and the girls make the rules.” I’m certainly not going to tell him that sometimes the guys make the rules; that’s the last thing he needs to hear right now. “It’s called seduction,” I told him. “You have to persuade your date that she’s going to enjoy doing things with you.”

He shook his head, obviously at a loss. “I ... I don’t know how to do that,” he said softly. “I saw how my dad treated my mom before they divorced, and I see how he treats his new wife now, and ... I ... I don’t know how to be any other way.”

His statement shocked me a little. Edward had been nothing but a perfect gentleman with me and I’d enjoyed my time with him immensely. But I put those somewhat disturbing thoughts out of my mind and concentrated on the task at hand. At least he’s admitted he has a problem, I thought to myself. That’s a really good first step. Let’s see where we can go from here.

“Would you like to learn how to do things differently?” I asked him quietly.

He hesitated, then our eyes met. “Yes, I would, I really would,” he whispered.

“Okay, I think I can give you some ideas, and you can practice with me. How does that sound?”

My salad and his appetizer arrived, and we ate in silence for a few seconds before he answered my question. “That sounds great,” he said with a big grin. “I’d really like that.” But just as I thought I was getting somewhere with this young man he took a step backwards.

Instead of engaging me in conversation, he pulled out his cell phone and started scrolling through it between bites of shrimp. I cleared my throat to get his attention, which brought his focus back on me. When he looked up, I glared at his phone.

“What?” he said irritably.

“When you’re out on a date, the girl likes to be the center of attention,” I somewhat politely scolded. Time to appeal to his base instincts. “Are you more likely to get laid by me or that cell phone?”

“I ... ummm ... I didn’t know what else to say to you,” he said defensively.

I thought for a moment. “What did I choose to wear for you this evening?”

“A very sexy little black dress,” he admitted shyly.

That brought a smile to my face. “Do you like the way it looks on me?”

“You’re ... you know ... you’re beautiful.”

I gently rubbed his thigh again. “That’s an excellent start, and no more cell phones during dinner, okay?”

“Okay,” he said sheepishly.

“Complimenting me on how I look in this dress is the quickest way to get me out of it ... okay?”

A big smile broke over his face. “Okay.”

While we continued our meal I led our conversation into various subjects that were dinner-table appropriate. I asked him about school and I described my current classes at UNLV. He told me about a girl he wanted to ask out but was reluctant because of all the rejections he’d experienced.

“She looks a lot like you, actually,” he said as we were finishing our entrées. “You’re prettier, of course, but she’s blonde with great tits.”

“The first part of that last sentence was a lovely compliment, and I thank you for it.” He beamed, so I quickly cut him down. “The second part was rude, crude, and obnoxious.”

“Oh,” he said. “I meant ... well, shit ... I mean, shoot ... I mean, damn it ... what should I have said, then?”

At least he’s asking for help, I told myself. I know how teens talk, but he’s got to learn to be more sophisticated. “I know you intended to say something nice about her, but you have to be careful how you describe a girl you’d like to be with.” I paused for a moment, “If you spoke about me that way and I found out about it, your chances of doing something with me would be non-existent.”

He looked down, so I softened my tone. “I know guys talk like that when they’re with their friends, but that word had better not come out of your mouth again when you’re describing a girl you’d like to be with. You could’ve said, ‘she’s blonde and she has a nice figure.’ I know young boys don’t talk like that, but men who want to get laid do.”

“I ... ummm ... I’m sorry.”

“I was very flattered when you said I’m pretty.”

He looked surprised, so I elaborated. “That’s the kind of thing we like to hear. Telling a girl you think she’s pretty and giving her lots of compliments makes her want to be with you.”

“Really?”

“Of course. You haven’t talked that way with the girls you’ve taken out, have you?”

He looked down sheepishly. “Ummm ... no ... I haven’t.”

I knew that was a lie, but I’d made my point and I decided to let it slide. “We definitely need to work on your game.”

“Yes ... ummm ... I guess we do.”

“Do you want dessert?” I asked.

“No, I’m stuffed. Let’s get the check and head upstairs.”

He seemed to be unsure how to get the waiter’s attention, so I gave him a hint. “Raise your hand and the server will come over,” I suggested.

He raised his arm and the server immediately appeared. “We won’t be having dessert, may I get the check, please?”

Hearing the words ‘may’ and ‘please’ come out of his mouth was gratifying. He’s learning and maybe this won’t be as bad as I thought.

The server brought the check in a leather folder that also contained a pen. “My dad said to charge dinner to the room, but I don’t know how much I should tip.”

“Subtract the tax, then figure twenty-five percent,” I told him. “That’s a little generous, but he did a very good job taking care of us.”

“Okay.” He worked out the math, wrote in the room number, and signed the tab. Then he stood, walked around the table, and pulled back my chair so I could rise.

I smiled, leaned in, and whispered in his ear, “That was very nice, you’ve been paying attention, and I think that entitles you to a nice reward.”

He extended his arm again for me to take and we headed out of the restaurant. After stopping at the bell stand to retrieve my overnight bag we strolled across the lobby to the large bank of elevators.

When we got to the room he opened the door, gestured for me to enter, and then followed me. I wasn’t surprised to learn that his father had gotten another Octavious mini-suite with an open door that led to the bedroom; there was a couch, with a coffee table in front of it and a table at either end, and a matching wing chair next to one of the end tables. After he closed and locked the door, we turned to face each other. I tilted my face up to kiss him, and suddenly he was all over me. He put one hand on my ass to pull me closer, his other hand moved to my breast, which he roughly pawed, and then he leaned in and attempted to jab his tongue into my mouth.

I put both of my hands on his chest and pushed him away, then took a step back. “What the fuck was that?”

“I ... ummm...”

“That is not how you treat a woman you’re about to sleep with, I said angrily.

In all honesty, his clumsy attempt was turning me on, and I could feel the wetness begin to build between my legs, but that wasn’t the lesson he needed to learn. “Most girls, and especially young girls your age, feel like they’re giving a guy they care about a gift when they have sex with them.”

He shot me a dumbfounded look and I tried to think of another way to proceed. “Let me put it another way: most women are like ovens, they need time to heat up. On the other hand, men are like microwaves, in thirty seconds they’re ready to go. Does that make sense?”

“Yeah ... ummm ... I think so.”

“Think of it like this, patience is a virtue,” I said sharply.

I’d put him on the defensive, and he responded aggressively. “You said most girls–”

I interrupted him. “If a girl wants a guy to play rough with her she’ll let him know that. I’m willing to bet you acted that way on your dates and that’s why you got rejected; do you think I’m right?”

“Yeah, you probably are,” he said resignedly.

“You’ll get a lot further by playing nice until a girl tells you she wants something different.”

“Can you show me what you mean by playing nice?”

I thought for a moment. “I’d love to teach you how to kiss; would you like that?” I said seductively.

That brightened his disposition considerably. I took his hand and led him over to the couch. After we sat down, we turned and faced each other, and I put my hand on his cheek.

“Now remember, the key is to have patience and respect. Let the girl signal when she’s ready to move forward. The more respect you show for her boundaries, the more likely she is to relax those boundaries and let you go further, okay?”

He nodded and I put my closed lips against his. He pressed against them, but only lightly, and I was glad to see he kept his hands to himself. After about ten seconds, I parted my lips slightly.

“Was that a signal?” he asked anxiously.

“Yes, it was,” I replied. “You can respond if you’d like to, and you can put your hands on me lightly, but only at my waist, not in any intimate areas.”

“Okay,” he whispered.

I kissed him again, this time with my lips parted, and he responded by very gently sliding his tongue past them and into my mouth. When I let my tongue greet his, he became a little more assertive, but not in a bad way, and he put his hands on my back and began to gently rub. After about thirty seconds I pulled back.

“That was really nice.”

“It was fuckin’ awesome, I love kissing you,” he said exuberantly.

“I’m glad you liked it, but remember to watch your language, okay?” I said gently.

“Oh ... yeah ... I’m sorry.”

“It’s okay; are you ready for the next step?”

“Oh, yeah,” he said eagerly. “What’s next?”

“You need to learn to read a girl’s other signals. You let her lead and you respond, okay?”

“I think so.”

“Let’s try,” I said. “Kiss me and we’ll go from there.”

I let him initiate the next kiss, and he did well, waiting until I opened my lips before slid his tongue forward. I reached up and put my hand behind his head to pull his mouth tighter against mine, and he responded by putting his hands directly on my hips and moving them around. I leaned forward and pressed my breasts against his chest, and he again responded appropriately, moving his hands from my hips to my butt and pulling me closer to him. By that time we were both breathing more heavily, but I waited until he ended the kiss.

“God, that was amazing,” he exclaimed. “Thanks, Elisa.”

“You’re welcome, and I liked that, you thanking me; a girl likes to be appreciated.”

“So do I get another reward?” he said with a devilish grin.

“Yes, you do; are you ready for the next signal?”

“You bet.”

I loved how his confidence was building as we progressed. “Okay, practice will help you remember what you’ve learned, so we’re going to repeat what you’ve already done and then move on from there.”

He initiated another kiss and we went through the initial motions we’d practiced together. Then I moved my other hand and started caressing his chest, first holding it still and then moving it in slow circles centered on the slight swelling around his nipple. He hesitated, then slowly moved one hand from my hip and put it on my breast. I felt his fingers close gently around it and he stayed in that position, not mimicking my hand’s movements.

Now he’s nervous, I thought to myself, so I’ve got to help him. I brought my other hand down and placed it over his, then started pushing his hand around on my breast. It was an unusual situation, teaching a guy how to touch a girl. Nonetheless, my body reacted and my nipple hardened under my dress as his palm slid over it.

I lifted my mouth away from him just far enough to whisper, “Did you feel that?”

“Oh, God, yes,” he whispered back.

“You did great and my body responded to you. How do you feel right now.”

“I feel like I’ve died and gone to heaven,” he answered sincerely. “I can’t believe it; you feel so ... amazing ... you’re beautiful, and you’re a great teacher, and ... it’s just ... the greatest feeling in the world.”

I had to smile at that. “Thank you again, baby. You don’t really know what amazing is yet, but if you keep progressing like this you’re going to find out.”

“I sure hope so,” he said with a smile.

He really was a thoughtful kid when he made the effort, and I was beginning to have more difficulty keeping my own sexual desires under control as his lessons progressed. But I had to bring more reality into the conversation.

“Just understand we’re moving fast here. Everything you’re learning from me isn’t going to happen on a first date, or even a second date. Remember what I said about needing to be patient. You have to build up a girl’s confidence in your respect for her and also your discretion; you can’t brag about how far you’ve gotten with a girl or you’ll never get that far again, with her or any other girl she knows.”

“Maybe so ... but the guys at school all talk about which girls put out and that kinda stuff.”

I knew he was right and I knew high school guys talked like that about girls because I was one of the girls they used to talk about.

“That’s true, but if you’re smart you’ll just listen to them and smile knowingly. Pay attention to how many of them actually have steady girlfriends, how long it takes them to start bragging about how far they got, and how many dates they have with that girl after they start revealing that personal information about her.”

That got him to stop and think before he responded. “I never paid any attention to any of that,” he said slowly. “But you’re right; some of them start dating a different girl right after they brag about scoring.”

“Now you know why,” I told him. “A girl finds out a guy’s been talking behind her back and she stops going out with him.”

“I see that now,” he said.

“Along with patience, discretion is another virtue you should cultivate. If you do, you’re going to be very happy with some girl after a few dates.”

“I’m sure you’re right about that,” he replied with another grin. “Now how about some more lessons?”

I reached over and toyed with the first button on his polo that wasn’t already open. I slowly opened it and ran my forefinger down the gap in his shirt until it hit the next button. I opened that one also, and then I leaned in and kissed his bare chest, letting my tongue slide lightly over his skin. Next I used my lips to push his shirt aside so I could lick his nipple, and he inhaled deeply. I pressed my lips to his and he kissed me back with enthusiasm.

“Did you get a new signal?” I cooed.

“I think so,” he whispered back. “But I’m really nervous, I’ve never touched a girl’s ... ummm ... breast before.”

He’s learning. It was refreshing to not hear him use the ‘T’ word again. “There’s a first time for everything,” I said softly. “Go ahead.”

He slipped his hand inside the top of my dress and gently cupped my breast. Gradually, his fingers moved to my nipple, which produced a delicious little tingle when his palm slid across it. He stayed still, apparently just enjoying the sensation, and I decided to help him along. I dipped my shoulder and moved closer to him so the strap of my dress fell down my arm and my breast was exposed. He stayed in that position, so I put my hands on his chest and moved them around in circles, hoping he would take the hint, and after a few seconds he did. He moved his hand in slow circles on my breast and then pushed the other shoulder strap so the top of my dress fell around my waist and my breasts were fully exposed.

“God, you’re beautiful,” he gushed. “You look just like a girl from one of my ... you know ... magazines.”

That brought a little smile to my face. I moved in and sucked lightly on his nipple, and again he took the hint. When I backed away, he leaned forward, took one of my nipples between his lips, and played with the other one. I let out a little moan and put my hand behind his head, pulling his mouth into my breast to encourage him further. He swirled his tongue around my nipple and I let out a little moan. This extended foreplay was definitely turning me on. Even though I knew this was supposed to be all for his benefit I was starting to want things to move along more quickly. I moved my fingers along his thigh and up to the bulge in his pants and I gently began to rub.

“Well ... what have we here?” I said playfully.

His face turned into a bright red ember. “It’s ... ummm ... my ... ummm...”

I gave him another slow open-mouth kiss. “Don’t be embarrassed, baby, it’s a natural reaction to everything we’ve been doing.”

“This is the ... ummm ... the furthest I’ve ... ummm ... ever ... ummm ... gotten ... you know ... and it just feels so good.”

“You’re making me feel good too and you’re reading my signals perfectly.”

“Thank you, but it’s ... ummm ... really hard to be patient.”

“It’s hard, all right,” I said with a little giggle. “Do you need relief? Do you masturbate?”

He blushed again. “I do ... you know ... jerk off sometimes, after a frustrating date, and yes, it’s becoming pretty ... ummm ... uncomfortable.”

I felt sorry for the poor guy. He’d been really good about going slowly with me. “Would you like me to help you relieve some of the stress?”

His eyes got wide. “What do you mean?”

“I mean I’m offering to help relieve some of that pressure, if you want me to.”

“Oh,” he said, and suddenly he looked shy.

“When you’ve been polite and respectful to a girl she may want to do this for you.” I unzipped his pants, reached into his boxers, and pulled out his cock. I noted that he wasn’t quite as long and thick as his father, but he was still way above average. He had a nice big mushroom-shaped head that already had a little pre-cum coating oozing out of the tip. “This is nice... very nice,” I cooed, which seemed to relax him a bit.

I gripped him firmly at the base and stroked his length. Immediately, he tensed up. “I’m kind of ... close, Elisa.”

“Okay, let’s not make a mess on your clothes,” I replied. “Lift your bottom up and let’s get you out of these pants.”

Once I got his pants and boxers off I began stroking him again. Instantly, his cocked twitched in my hand. Teaching him, kissing him, and feeling him was really turning me on. My pussy was already very wet and I knew I’d soaked my little thong all the way through. I stroked him with one hand and cupped his balls with my other hand, and that’s all it took.

“Oh, God,” he moaned, and then thick ropes of semen shot up like a fountain. Spurt after thick spurt landed all over his belly and a couple shots at the end covered my hand. I really wanted to take his cock into my mouth, to taste his cum and swallow it, but I knew it was too soon for that. So when he finished coming I took my hands off of him and headed for the bathroom.

“I’ll be right back,” I said over my shoulder. “Just relax and wait for me.”

“Okay,” he said meekly, and he slumped back into the cushions on the couch.

In the bathroom, I turned on the hot water, and then I couldn’t resist; I licked some of his cum off my palm and then stuck my sticky fingers in my mouth so I could taste more of it. He tasted so good; my pussy tingled again and I knew I was going to have him come in my mouth before his training was over. Then I washed my hand and wet a washcloth to take back to the bedroom and clean him up.

I knelt on the floor between his open legs. “Did you like that?” I asked as I wiped up the cum from his cock and balls.

“Oh, yeah,” he said exuberantly. “That was fantastic; it was great to not have to do it myself.”

“I’m glad you enjoyed it.” As I wiped the remaining semen from his chest, I said, “Now it’s time for you to learn how to give pleasure, not just get it, okay?”

His face broke into a big smile. “Okay.”

When I finished cleaning him up I told him to finish getting undressed. He quickly took off his shirt, shoes, and socks. Once he was naked, I took his hand and led him into the bedroom. When we got there, I took off my dress and lay on the bed face up wearing only my thong and my heels. His eyes lustfully roamed up and down my body.

“God ... you look ... just amazing,” he gushed.

I seductively ran my hand over my breasts, teasing him a little. “Not too bad, huh?” I said in my best sex-kitten voice.