The Hot Bitch

Chapter Two of Semi-Pro

I do not know for sure why I said yes to Simon when he asked me out. Was I trying to find a new John?

In the year and a half or so since I was hired by Gerald that first time, I had dated a bunch of guys I found attractive, and had slept with two of them, one of whom officially became my boyfriend for a few months. But I longed for the combination of arousal and ego trip I got whenever Gerald had been able to scrape together $468.64, which he had only been able to do three times during that period. The last time was while I had a boyfriend, which is why I broke it off. I did not want to be a cheater, and I could not resist the thrill of getting paid.

But finding men to pay me for sex was not as easy as I would have expected. The problem was that I could not bring myself to fuck someone who I did not know and did not feel safe around, but I also could not reveal to people I knew about my kink because they would be judgemental, or let knowledge of my kink slip to other friends (or family) who would be judgemental.

I actually did reach out to an escort agency. I attached a picture of myself in a bikini and they responded almost immediately. In an online interview, they assured me that I could choose my clients and I could leave at any time no questions asked. But I could not go through with it. For one, I had no way of knowing if I could trust the agency. Beyond that, it seems obvious to me that screening a client who is calling for sex is very different from getting to know a guy who is not expecting sex, and walking out on a client is very different from not offering my services to the guy to begin with.

Thus I had a conundrum. The only people that I felt comfortable enough with to offer them sex for money were the people who I least wanted to know I was a whore. I knew I needed to find a guy I knew who I was not normally attracted to, because otherwise I would just want to date him, but who I felt comfortable enough with to have sex with if he offered me a lot of money, and then somehow convince him to offer me a lot of money for sex before he knows for sure that I would actually do that sort of thing.

I do not remember thinking about any of that between the time Simon asked me out and a few minutes later when I said yes. Simon was slightly taller than me and scrawny, with unkempt brown hair. He was not ugly, but there was something asymmetrical about his eyes that made him look slightly weird. He was polite and intelligent, but he often seemed uninterested in whatever conversation was going on around him, or when I was talking with him. Actually, I think one of the reasons I might have said yes was because I was surprised he was interested in me. The other reason may have been the endearing expression of hope and fear on his face when he asked me and then waited for my reply.

I knew fairly quickly that I would probably say yes, but I pretended to think about it for a bit and he offered me compliments and told me how compatible we were. I do not play games with guys, but I do try to send signals. Saying yes immediately will make it look like you are interested in him, and make it feel like you are interested in more than just a date, whether that be a relationship or a roll in the hay. If that is the truth, I do not mind a guy knowing it, and I will say yes right away. But if all I want for now is a date, taking time to say yes indicates that. It is about managing expectations. "Okay," I finally said, "one date.". The shock and confusion on his face almost made it worthwhile on its own.

But as soon as he walked away, I realized that he was a good prospect to be my next John. I had no interest in dating him long-term, but I could see myself getting hot for him for the right price. And I had a feeling that he might be desperate enough to fuck a hot chick like me that he might be willing to make me a good offer. All I needed to do was figure out how to get him to make an offer without knowing for sure that I was for sale.

I dressed to show as much skin as possible without making it look like I was trying to dress slutty. I did not want him to think "love" or "relationship", I wanted him to think "sex". I wore a skirt that ended halfway down my thighs, just slightly too long to be called a miniskirt, a V-neck crop top that showed my cleavage and abdomen, and a loose short-sleeved bolero shrug. The skirt and top were a matching beige and white pebble pattern, and the shrug was white. I also carried a gold clutch and wore white two-inch platform heels. If I was a real call girl I would have worn at least three-inch heels, and they would not be platform, but I did not have enough practice to wear such footwear without stumbling.

Simon showed up in black slacks, a white dress shirt, a gray patterned dress jacket, and a shiny brown bow tie. He brought me flowers that would look lovely in my dorm room and a box of chocolates I would have to give away if I wanted to charge top dollar for my pussy.

He took me to a restaurant where we could have some privacy in a half-circle booth. I sat slightly closer to him than would normally be appropriate on a first date and made sure he could see down my top.

After we ordered, he said, "I hope you don't mind, I am obviously not good at this, so..."

"Not good at what?" I interrupted.

"Talking. To... people."

"You seem to do okay."

"Yes, well, I brought something to help me."

"Something to help you talk to me?"

"Yes."

"What is it?"

"These." He reached into his jacket and pulled out four decks of cards. "They're conversation cards. They each have a question on them. You pick one at random and both people answer the question. If it leads to a conversation, you go with it. When you are done, you pick another card."

"Why are there four decks?"

"They each have a theme. You mix together whichever decks you want for whatever kind of conversation you want."

"What are the themes?"

"Is this something that you want to do?"

"Yes, it sounds fun. What are the themes?"

"Well, actually the first is called "Fun", what is your favorite book, what do you like to do on Saturdays, that sort of thing. The second one is "Deep". An example question is "Who do you miss the most who has died?" The third one is called "Danger". Those are mostly questions about religion and politics. The last one is "Spicy". Those are mostly questions about sex, although I think some might be about drugs or alcohol."

Recognizing the opportunity, I said, "I think we should have a fun and spicy conversation."

"Really? You want to include the Spicy deck?"

"Why not?" I said with a mischievous grin.

"Okay," he said, almost sounding reluctant. His hands, which had been steady, began to shake slightly as he opened the Fun and Spicy decks and shuffled them together. He set the combined deck on the table and drew the first one.

"What is the most uncomfortable place where you have had sex?" he read. "Um," he said nervously, "we don't have to..."

"It's okay," I said, giving his hand a squeeze intended to be both comforting and suggestive, "I'll go first."

"Oh, no, that wouldn't be fair."

"Why not?"

"Because," he was very nervous, "l... I'm a virgin. So if you told me something, I wouldn't have something to tell you. And that wouldn't be fair."

Desperate for sex? Check. "But you did just tell me something. Something important." I gave his hand another ambiguous squeeze. "The least I can do is answer the question." This will make him think about me having sex.

"Okay."

"The most uncomfortable place I've had sex? Hmm..." The longer I pretend to think about it, the more sex it makes me appear to have had. "Let's see, I think I would have to say, in the butt."

He laughed heartily, and I felt good about my joke. It broke the tension and made him think about me having anal sex.

But then he said, "Like The Newlywed Game."

"The what?"

"The Newlywed Game. That's what you were referring to, right?"

"No, what's The Newlywed Game?"

"Oh. It was an old game show. Recently married couples would answer questions about each other to see which couple knew each other the best. Probably the most famous answer someone gave was when they asked, 'Where was the strangest place you ever made whoopee?' and one woman said, 'In the ass.'"

"They called sex 'making whoopee'?"

"Yeah. It was an old show."

"Well darn, I thought I invented that joke."

"Oh no, you did invent it. You didn't know about The Newlywed Game. It's just that someone else invented it first. Like calculus." Damn, now he was comforting me. I wanted to be the sophisticated woman offering comfort. Sure, being comforted can make you endearing to the person who is comforting you, but in a "helpless damsel I want to protect" way, whereas I was going for "hooker with a heart of gold".

"So I'm like Leibniz?"

"Exactly. Except you're like Leibniz if Newton was an idiot who just accidentally discovered calculus. Because the lady on The Newlywed Game wasn't joking. She thought that answer was what the question was looking for."

"So I guess I still owe you a real answer."

"Not if your answer was true. I know you were joking, but if the answer was accurate, then you don't have to say anymore."

I thought about it. "Actually that probably was the most uncomfortable place." After a beat, I added, "At least at first. After a few times, it became enjoyable." That addition was a lie. I had only done anal twice, and although it was better the second time, it was still uncomfortable. But I wanted this virgin to know that his date was a whore.

Simon sat in silence staring at me for a few seconds. I could almost see his mind thinking about how many dicks I have had up my ass. "Okay," he finally said, "should we go to the next card?"

"Sure."

Simon pulled the next card and read, "What is your dream vacation destination?"

"I want to go to Mondragon, Spain," I said. "It's a city in the Basque region. It has a lot of beautiful hiking, and I could visit and study the Mondragon Corporation."

"Your dream vacation is to study a company?"

"The Mondragon Corporation is the world's largest worker-owned cooperative. Well, technically it's a federation of worker co-ops."

"Worker co-ops are important to you?"

"They're basically socialist companies operating in the capitalist system. They subordinate capital and are democratically controlled by the workers."

"Oh," he said slowly, sounding slightly confused, "That's interesting..."

Okay, yes, I lost the plot here. I should have said the French Riviera so he would think about me lying on a beach topless. But sometimes I just cannot help myself. "So what's your dream vacation destination?" I asked.

"Mars."

"Mars?" Now I was the one unsure how to respond.

"I mean, I know they're not booking flights quite yet, but that is the dream."

"Well then, I guess unconventional vacation desires is something we have in common. Although I will concede that interplanetary exploration is inherently more interesting than socialist accounting." He laughed. Good, I am back on track. "Shall we draw the next card?" I asked, reaching for the deck.

"Go ahead," he said.

I pulled the next card and read, "What's one place you've visited that you never want to return to?" I laughed. "Oh I know my answer to that," I said.

"Ugh," said Simon with a sigh and a pained expression, "so do I."

"Oh." I stopped laughing. "What's your answer?"

"My Aunt Lynn's house."

"Your aunt's house?"

"Yeah. We went to meet her new husband who she had just married in Vegas. He was a jerk, but it wasn't a total disaster until he found out my Dad is Jewish. Dude then started interrogating my Dad about how often he goes to temple, how well he knows the Torah, whether he keeps kosher, etc. Dude wasn't Jewish himself, mind you, and I honestly don't know how religious he was. But when my Dad said he was an atheist, the dude blows up, starts yelling at my aunt, 'How come you didn't warn me that he was one of those secular Jews?' etc. Then he starts rattling off all of the standard Jewish conspiracy bullshit, only for some reason he keeps just talking about 'secular Jews'."

"That's horrible," I said.

"Yeah," said Simon. "So Dude and my Dad start yelling at each other. Then my Mom asked her sister, 'Did you know he was an antisemite when you married him?' And my aunt is like, 'How can you dare call him an antisemite? He's only talking about *secular* Jews. He has nothing against the religion.' And *they* start yelling at each other.

"So we left, and Mom and her sister haven't spoken since."

"That's insane," I said.

"Yes, it is," he agreed.

"Shit," I said, "now I have to change my answer."

"Why?"

"Well, I was going to say South Of The Border, but now I realize the real answer is my grandparents' house, my Mom's parents."

"What's South Of The Border?"

"Oh, you're from up north, right?"

"Philadelphia."

"Yeah, well South Of The Border is like the biggest and worst roadside tourist trap in America. It's on the South Carolina side of the border between the Carolinas. If you ever take I-95 to Myrtle Beach, ignore all the billboards and just drive right past it, trust me. But I'm not going to go into that story, because after what you said, I realize, yeah, I would rather go back to South Of The Border than to my grandparents' house."

"What happened?"

"Somewhat similar to your story, that's why you reminded me of it. When my brother transitioned near the beginning of high school, we knew Mom's parents would freak. My parents thought there was a possibility that they might handle it better if they found out from my brother in person, you know, maybe they would not be as mean to his face, or maybe seeing the grandchild they love in front of them would make them more tolerant, that sort of thing. Of course, we also knew that a blow-up in person would be much worse. It was a high-risk, high-reward strategy, and when we went to their house, we crapped out.

"My grandparents refused to accept him as a boy, wouldn't use his pronouns or correct name, and kept referring to all of us as 'woke zombies' without even an ironic acknowledgment of the mixed metaphor. Then they asked about medical treatment, and when they found out that he was on puberty blockers, they threatened to report my parents to Child Protective Services unless they agreed to take him off of the meds. So we left and haven't been back."

"Well that was horrible," said Simon.

"These cards are certainly helping us get to know each other," I said, "but I don't really think they qualify as 'Fun'. Let me draw another one."

I pulled the next card and read, "What kink or fetish of yours do you least want your family to find out about?" Perfect! I smiled mischievously. "Oh, I've got a good one. How about you?"

Simon's face looked nervous. He shifted in his seat and his voice quivered a little. "I, I don't think so."

My smile got bigger and more mischievous. If I could get him to admit something perverted enough, I could safely tell him I'm for sale. "Oh, no. You're hiding something," I said. "You're thinking about something that turns you on that you're afraid to tell me, aren't you?"

"Umm..." He couldn't look at me.

"Come on," I said, "I promise I won't tell anyone."

"It's... I don't know. It's... Why don't you go first?"

"Oh no," I said, "you have to go first. Mine's much worse than yours."

"I doubt that."

"Oh, it is. But I promise to tell you," I hesitated. I was going to say "if", but instead I said, "when you tell me." I was not going to let this opportunity go by.

"Yours can't be worse," he said, "I mean, it can, but even if it is, it's not, not really."

"What does that mean? I don't understand."

"Well, it's like, a hot girl with a kinky sexual fetish is even hotter, but a geeky guy with a kinky sexual fetish is just a pervert."

I considered this. He had a point.

"Is yours illegal?" I asked.

"I... don't think so," Simon said.

"Then I win," I announced. "Mine is. So you'll just be admitting to being a pervert. I will be admitting to being a criminal. So you go first."

Simon steadied himself. "I like... to be... insulated and humiliated by hot women," he said.

I had rushed into convincing him to tell me, but I forgot to emotionally steel myself for whatever he might say. I actually laughed. "What?" I asked, "I don't understand. What do you mean?"

He sunk back in his seat, "I'm sorry, never mind," he said.

"No, *I'm* sorry," I said, "I wasn't laughing at you. That was a laugh of surprise. That's just something I have never heard of before. It was wrong of me to laugh." I grabbed his hand. "Please tell me more. Is this like a masochism or submissive thing?"

"I don't know. Maybe." He seemed understandably conflicted about opening up to me again. I needed a way back into this that was not direct

"When did you discover that it turns you on?"

"In high school."

"What happened?" I kept holding his hand.

"I did the stupid cliche geek thing and asked out the hottest girl in school."

"I take it that didn't go well."

"No. It was the nightmare. She laughed at me, called me a pathetic loser, then yelled across the hall to tell her friends that the pathetic loser asked her out."

"What a bitch."

"Yeah, she was." He almost looked wistful.

"But it turned you on when she did that?"

He looked at his hands. "Yes, it did."

I leaned close and lowered my voice to almost a whisper. "Did you get a hard-on?"

He hesitated, still looking down. "Yes."

I leaned closer and dropped my voice all the way to a whisper. "Did you jerk off at home thinking about her laughing at you and calling you a pathetic loser?"

He sheepishly looked up at me. "Yes. See, it's perverted, right?"

"Actually I think it's funny, and kind of cool."

"Cool? In what universe is that cool?"

"Well, here this bitch was, being mean and trying to make you feel bad, and all she ended up doing was helping you get off. You were enjoying it. Joke's on her."

"That... is... an amazingly interesting way to look at it." Simon was not convinced.

"Have you explored this kink since then?"

"Well yeah, that's why I only ask out hot girls who are way out of my league."

The look on his face told me that Simon did not realize what he was admitting to me until immediately after he said it.

"So you thought I was a stuck-up bitch who would turn you down and laugh at you?"

"No, I don't, I mean, not necessarily." Seeing the expression on my face he continued, "Look, it's just, like, there's no downside to asking out girls who are out of my league. Either you let me down easy, which is disappointing but not horrible, or you insult me and ridicule me, in which case I get my perverted thrill, or you say yes, in which case, jackpot."

"Well, it sounds to me like you are seeing the same upside I did."

"I guess that's true," he said.

"And face it, tiger," I said seductively, "you just hit the jackpot!"

"Like Peter Parker."

"Yep." A thought occurred to me. "Hey, why did you ask out that first stuck-up bitch?"

"Well... because she was hot."

"No," I said dismissively, "that's not enough. I'm sure there were plenty of other pretty or hot girls in your school."

"Well, I had a crush on her."

"Yes, but why did you have a thing for her? Had she been nice to you before you asked her out, had she just never noticed you before, or had she been mean or rude to you before?"

"Well, actually she had been kind of rude to me before I asked her out."

"And was that why you had a crush on her?"

Simon looked distressed. "I... had not thought of that. It might be. Probably. God, I am a sick pervert."

"No," I insisted, "The heart wants what the heart wants. You just have certain things that turn you on. Everyone does. You just have to make sure you don't let it get you into trouble. It's how you go about exploring it or controlling it that matters. Even 'normal' turn-ons like big boobs or a big ass have gotten plenty of guys into trouble when they acted like idiots while exploring them. I certainly have to be careful when I'm exploring my perverted turn-on."