Chapter 2: Tabitha

"Hi! This is Jessica. I can't come to the phone right now. Please leave your name and number and I'll get back to you as soon as possible..."

I waited for the voice mail connection and promptly forgot what I wanted to say.

"Uh, hi. It's John, from last Thursday? Anyway, I was wondering if you'd be free this evening. Not free, uh ... I mean, available? For a date? Um ... Maybe I'll email you. Shoot. But if you want to call me back, my number is..."

I hung up the phone feeling like a high school kid. I wanted to open Jessica's web page, just to see her again as much as anything else. She'd been on my mind for a week, like a growing infatuation pushing everything else aside, and I held her panties in my lap. I'd washed them by hand after our first and only "date" and kept the flimsy souvenir in my desk at work. It was the only place I knew my wife wouldn't find them; she hated coming by the office.

Between the lacy, feminine underwear now in my pocket and my celphone sitting silently on my desk, it wasn't easy concentrating on work. The computer distracted me as well. Jessica's beautiful face haunted me and I could find her right there on the internet, but everything went through the server and got logged. Even a vice-president would have to explain himself and surfing transsexual escort sites, well ... That would be unexplainable.

When my phone rang, shortly after lunch, I jerked upright and stared at the noise, getting a shot of adrenaline that wasn't going to help me very much. On the third ring, I caught it in my hands like a wounded bird, cupping the phone and glancing at my closed door. I half-expected my secretary to walk in, catching me in the act of ... What? My nerves were playing tricks on me. It rang twice more before I answered.

Hi John," Jessica purred. "I was at my aerobics class this morning. How are you?"

"I'm great," I replied. "Really, um ... good."

"Good."

She laughed lightly when I didn't say anything else and plainly I should have. I'd called her after all.

"Are you at work," Jessica wondered, "or playing hooky? It's a nice day for it."

"Working," I said. "Stuck in the office."

"Ohhh..." she pouted. "That's too bad."

"Yeah," I agreed, clearing my throat and looking at the blue sky through my window. I had a nice view of the river, but I barely noticed it anymore.

"What were you calling me about, John?" she prompted after another awkward silence.

She obviously wasn't going to ask me on a date, although I wasn't exactly sure what the rules were for this kind of thing. I'd arranged our first meeting through email.

"Oh. Well, I'd like to, um ... see you again," I said. "Tonight? Maybe? If you're not, uh ... busy?"

"Ohhh ... That's sweet of you," she said, "but I've already made plans."

"You did?" I swallowed hard. "That's okay. I understand, um ... Maybe another time then."

"I really need a little more time," Jessica explained. "I'm sure you understand. Maybe we can get together on Wednesday or Thursday?"

"No," I sighed. "I'll have to, uh ... See, my wife..."

"Ahhh..."

" ... she has a thing tonight, some sort of fundraiser, and..."

"I see."

" ... I just thought maybe I could see you again."

"I wish I could," Jessica said. "I had a lot of fun on our first date. I'd love to do it again."

"But you're busy."

"But I'm busy," she agreed, letting the disappointing truth hang between us for several seconds. "If you like, I do have a friend you might like to meet. I can give her a call and..."

"A friend?" I licked my lips. "You mean, like you. Right?"

"Very much like me," Jessica said. "You'd like her a lot, I think, and I know she'd just love to meet you."

"Uh, maybe..." I'd had my heart set on Jessica.

"She's a little younger though," she said. "Is that a problem?"

"How old is she?"

"Don't worry, John," Jessica laughed lightly at the suspicion in my voice. "She's eighteen, but ... Not by much. That's what I'm saying. She's going to college."

"Really?"

"I wouldn't lie about that," she teased me. "What do you think? Should I call her?"

"What does she look like?" I asked, knowing how shallow that made me sound, but Jessica didn't seem to mind. On reflection, she probably understood my interest completely, since this was a business.

"Like a sexy tomboy," she answered. "Dark hair, long legs, pretty in the face. She's very natural and, uh ... very healthy."

"Healthy?"

"Like me ... Don't you remember, John?" Jessica lowered her voice to a sexy whisper. "My cock remembers you perfectly."

"Uhhh..." I nodded into the phone.

"She's not shy either ... I'm almost home. Do you want me to call her for you?"

"Okay, um ... Sure," I said, deciding it wouldn't hurt to at least talk to this other girl. "What's her name?"

"Tabitha," Jessica said. "I'll call her right now. Okay?"

"Yeah," I replied, detecting a hint of impatience and I'd probably wasted enough of her time. "Thanks. I, uh ... appreciate it."

"You owe me a favor now," she said with another laugh. "Bye, John."

"Bye."

She disconnected and my phone went dark.

"Fuck." I'd really wanted to spend the evening with Jessica and it didn't seem fair to find her unavailable.

What did I expect though? She was an escort, a transsexual prostitute, and the best looking one in the city probably. None of the other shemales who advertised online had come close to matching Jessica's beauty. It's why I'd picked her in the first place and she hadn't disappointed me in the least. The idea of meeting her friend had sounded good at the time, but as I sat at my desk, I began to have doubts.

An eighteen year old college student? I should have asked how much this Tabitha charged. I wasn't worried about the money, I had enough of that, but it might have given me a better idea of what to expect. Jessica had been the most expensive shemale escort as well and I suppose I'm a natural born capitalist, believing the more something costs the more it's worth. Of course, being an investment banker I knew the truth about such things, or so I liked to tell myself.

"A sexy tomboy?" I muttered to myself. What did that mean?

Probably that she looked more like a man in drag than a real woman, which wasn't going to do anything for me. Transvestites didn't turn me on at all. I didn't have a fetish for clothes, although I could certainly appreciate a well dressed, or undressed, woman. I wasn't gay either. Men didn't excite me and I'd never had any experience that way, not even as a curious teenager growing up with my friends. I couldn't think of Jessica as a male, it's that simple. She was a woman with a penis, that's all, and I loved her for that.

We don't get to pick our fetish, it picks us; all we can do is rationalize it. Being with Jessica didn't make me queer, it only made me normal. I mean, look at her! She was one of the most beautiful women I'd ever seen. How could a man not be infatuated with her? Her cock only made her ... What? Perfect. It made her dominant and reversed our roles, putting me on my knees with the overwhelming submissive desire to please her. The psychology wasn't lost on me, but it didn't make me homosexual either ... Just desperate.

I'd removed my cock from my pants, wrapping Jessica's panties around the swollen shaft while I remembered the things we'd done together. I wasn't jerking off exactly, but definitely masturbating and I'd told my secretary to hold my calls. I had to be crazy and if I got caught it would probably mean the end of my career. Stroking off behind my desk in the middle of the afternoon? Yeah. I'd lose everything because this business was built on reputation, but those satin panties felt so good...

"Ow! Shit." I winced as my celphone rang and I banged my right knee against my mahogany desk with a loud, painful thud.

My watch showed 3:35 in the afternoon and it had been over two hours since I'd spoken with Jessica. I hoped it wasn't my wife calling and when I saw the words "New Number" glowing on the screen I felt my stomach tighten.

"Hello?"

"John? Hey! It's Tabitha, um ... Jessie said I should give you a call. What's up?"

I almost smiled as the girl made it sound like we were old friends. She really did sound like a girl too. Not a woman and certainly not a man, but a teenage girl and I hadn't spoken to one of those in a long time. That made an awkward situation even worse, considering the reason. How does one go about asking a perfect stranger for sex? At least with Jessica, she'd had a professional website and had taken much of the responsibility off my shoulders, but this girl ... I'd never even seen her picture.

I began thinking this hadn't been such a good idea.

"Hi, um ... I was, um ... I just got into town and..."

"You did?" She giggled softly. "I thought she said you're at work."

"Oh."

"Don't worry, I'm not gonna say anything," she said, reading my mind it seemed. "Jess told me you're married too."

"She did?"

"Yeah," Tabitha sighed. "Bummer, huh?"

"Uhhh..."

"I mean, not that you're married," she added quickly. "That's cool. Good for you, right? But she said you're pretty cute, so..."

"Jessica said that?"

"Uh-huh." She laughed again. "I'm kinda in the market."

"Okay, um ... For what?"

"A boyfriend!" she said. "God. You must think I'm really retarded. Never mind. Forget I said that, okay?"

"I'll try," I said, teasing her as I smiled into the phone.

"Can we start again? I'm Tabitha."

"I'm John," I said. "It's nice to meet you."

"You sound nice," she decided. "So, um ... Where do you work?"

"Huh?"

"I just got home from school," she sighed. "It sucks. I can't wait to get out of here, you know?"

"Sure," I agreed, wondering what we were talking about.

"So, um ... Jessie said you're really sweet. How old are you?"

"Me? I'm thirty," I admitted with an inward wince.

"On the button?" Tabitha asked with a giggle.

"Well..." I cleared my throat. "I turned thirty-one last May."

"Cool," she said. "I hate all the guys I know."

"You do?"

"They're totally boys," she sighed. "Like little boys, you know? So boring."

"I guess college can be like that," I offered, frowning at a rapping on my door.

I looked up to see Janice, my secretary, peeking around it. I had no choice but to wave her in.

"I'm sure once you assess the market more carefully and allow your investments to mature..."

"What are you talking about?" Tabitha asked, laughing again and I wasn't going to get tired of that sound.

"Peterson sent these down," Janice said softly, laying a thick routing folder on the corner of my desk.

"Thanks," I mouthed, giving her a shrug and a bored look as I took a deep breath. My secretary would think it was just another client wasting my time, but Tabitha nearly spoiled my one act play.

"I'm still in high school," the girl told me. "So it's kinda awkward sometimes, like meeting guys..."

"Right," I breathed, watching Janice close the door behind her as she left.

" ... that I can get into, you know?" Tabitha continued with a sigh. "College would be cool though. Yeah."

"What? How old are you?"

"Seventeen..." she replied, " ... almost, but everybody says I act way more older than that."

"Fuck," I breathed.

"Huh?"

"Oh. Nothing, um ... Yeah, you sound, um ... older."

"Thank you!" Tabitha said and I could hear her smile. "So ... Do you wanna like hook up or something?"

"Uh..."

"Like ask me on a date?" she asked, teasing me with a soft laugh. "Or did I totally scare you away?"

Child prostitution? My mind reeled in seven different directions. Tabitha sounded cute as hell, even sexy, but ... Sixteen? That's the age of consent where we live, but if I got caught what would it matter? She still went to high school and I admired teenage girls, some of them, like every other man on the planet, I'm sure. I didn't fantasize about them though. I wasn't some perverted child molester stalking playgrounds. Why did she have to be sixteen? Jessica had told me she went to college and Tabitha was so open and outgoing, I seriously doubted Jessica didn't know the truth about her friend.

I felt rather manipulated, even angry, but Jesus, she had a sexy voice. She had a cock, that's what I mean. Listening to Tabitha talk, hearing her sound exactly like her age and knowing she had a penis ... The girl had to be as cute as she sounded. Sixteen wasn't that bad, was it? I wasn't twice her age, at least, but that didn't make me feel any better. I was still old enough to be Tabitha's father, technically, and she wanted to hook up with an older man. I understood that much and she sounded serious about it, but I suppose being a teenage escort gave her a perspective beyond her years.

Fuck!

"How, um ... much do you think, um ... that would be?" I stammered softly, barely getting the words out. "For, uh ... all night."

I just had to hear her say it, you know? I wanted to hear the proof from her lips, that Tabitha wasn't an innocent high school girl rushing headlong into life.

"I dunno," she said with a verbal shrug. "I guess it depends on what you wanna do, right?"

"Yeah," I coughed lightly. "How about ... everything?"

"Everything?" She really laughed at that. "You mean like dinner and a movie or something?"

"Uh..."

"I like to dance, but it's kind of hard getting into the cool clubs sometimes," she said. "I kinda know the bouncer at Blue Lagoon. I'm on the cheer team with his sister, so we can probably get in there."

"Dancing?"

"Or a movie's cool too," Tabitha said and then, "Oh."

"What?" I narrowed my eyes.

"You probably wanna check me out first, huh?"

"Well..."

"Don't worry," she said. "I can look good when I want to."

"I'm sure you do."

"I mean, really good," she insisted. "Did Jessie tell you about me?"

"She said you're a, uh ... sexy tomboy," I admitted slowly, holding my breath until she giggled.

"Yeah! Sorta, I dunno ... I'm cute, though. I promise. I'm not gonna like totally embarrass you."

"You sound cute," I agreed. "I wasn't thinking about that."

"Good," she said. "Cause you don't have to. When you see me your eyes are gonna pop!"

"They are?"

"Uh-huh! I'm gonna start getting ready right now," Tabitha said. "What time are you going to pick me up?"

"Pick you up?"

"Well ... You're the man, silly!"

I smiled at her laughter and tried to figure out how this had happened.

"I don't know where you live," I said. "Do you want me to meet you somewhere or..."

"Just come to my house," she said. "It's cool. You got a pen?"

I wrote down Tabitha's address and already had her phone number now that she'd called me. I promised to pick her up at seven, but I honestly didn't know if I would or not. She'd given me a lot of time to come to my senses.

Did I really want to leave my car on the street? This wasn't exactly the bad part of town, but my BMW stuck out like a sore thumb amidst the rusted Fords and Toyotas that littered the street. Some black kids, young men really, were sitting on the steps of a brownstone opposite the address Tabitha had given me. They were smoking and sharing a brown bag with something in it. Beer, I supposed, and I almost didn't get out of the car.

My suit didn't help either. I'd thought about wearing something more casual, some slacks and a nice polo maybe, but I still hadn't made up my mind at that point. I liked my suits anyway. I'd been wearing them for years and barely thought about it in my normal day-to-day life. Seeing those guys in their t-shirts and sweat pants, however; I felt very uncomfortable.

"Yo! What you lookin' for, man?" one of them called out as I turned on the alarm with a sharp beep.

Tabitha lived in a brownstone like all the other buildings on this street and I ignored the guy, walking towards the steps and her front door.

"Lookin' for Tabby?" another boy asked. "She don't live there, homes."

"Excuse me?" I stopped and turned my head to look at them.

"She wanted to check you out first, man." The first guy jerked his head as the door opened behind him.

"Be nice," a girl said, Tabitha, as she stepped between them. "God! Look out. I'm trying to walk here!"

"Shit. We're nice," one of them said and they were all talking.

"He looks like the mayor,"

"You the fuckin' mayor, yo?" The first boy grinned at me. "When you gonna fix the fuckin' lights, man?"

"Just shut-up," Tabitha sighed, coming down the steps in a plaid skirt and black t-shirt. "You guys are so retarded."

She wore a red leather jacket over her shoulders, matching her purse and high heel shoes. It was a good look for her and with her short brown hair and narrow hips, her obviously flat chest ... Yeah. I could see sexy tomboy there. Not beautiful, not stunning like Jessica, but cute and even adorable wouldn't be an exaggeration. She looked like a sixteen year old girl, struggling between puberty and adulthood, which is a secret beauty all its own.

"Tabitha?" I stood frozen as her heels clicked on the asphalt and she offered me an impish smile and apologetic shrug.

"Sorry. I just wanted to see you first," she said. "I live across the street."

"Oh."

"Do I look okay?" she wondered, widening her sky-blue eyes and she had a pretty face full of expression. "Are you gonna change your mind?"

"Huh?" I blinked at her and woke up. "No. I'm not, uh ... You look great."

"So do you," she said, breaking into a sudden smile and she had small, sexy dimples that could come and go in a heartbeat. "Wow! What a great car. Is it yours?"

"Uhhh..." I shrugged, smiling helplessly. "I leased it."

"You rented it?"

"No. It's mine, I just ... I'm John."

"I know!" She laughed and stood close enough that we could shake hands, which we did. "I'm Tabitha."

"Yeah," I agreed, holding her warm fingers and I'm sure it must have seemed strange to her, but maybe not. I really didn't know what we were doing.

"You be cool, man," the boys told me, calling out across the otherwise quiet street.

"We got your back, Tabby." and "Be waitin' right here, girl."

"Don't mind those guys," she told me with a scrunch of her nose. "They think they're my brothers or something."

"Well, I guess it's nice they care," I said, for lack of anything better. Tabitha looked a little brown maybe, like she had some Hispanic blood, but she definitely wasn't black.

"That's how it is around here," she said. "Are you ready to go?"

"Sure. Yeah. Let me, um..." I pushed the button on my keychain and she laughed.

"That's so cool. Thank you," she said as I opened the passenger door for her.

"You're welcome," I replied, taking in her smooth thighs as the skirt rode upward for a second. Tabitha caught me with a smile, smoothing the pleats while I blushed and closed the door.

She looked good, but I knew her secret too and I can't lie about it. The idea that this girl had a cock and balls tucked away in her panties excited me far more than anything else. Passing Tabitha on the street or at the mall, I would have noticed and admired her, but that's all. It wouldn't have occurred to me to try and speak with her. As I said, teenage girls were nice to look at, but by themselves held no real sexual interest for me. But this girl, on the other hand, had already made up my mind and I wanted her badly.

"Maybe we should take care of the boring part first," I suggested before turning the ignition, remembering what Jessica had said to me.

I thought I could make it easier on Tabitha, maybe impress her with my experience in such things, but she gave me a blank look.

"What's the boring part?" she asked.

"Uh ... The money?" I shrugged as she turned towards me in the seat. "How much do you charge?"

"What?" Tabitha's eyes narrowed and her full, red lips turned down. I realized I'd just made a serious mistake, but I didn't know exactly how or why.

"For our date," I explained, my voice weakening with every syllable I uttered. "You mean, you're not a..."

"Whore?" she spat. "Thanks a lot! Wow! I feel special now. Let me out of here."

"Wait. Hold on a second," I said as she looked for the handle. "I didn't know. I thought ... I'm sorry. I really am."

"You're a jerk," she said, holding the door handle in her fingers but not pulling it yet. "I don't even make out on a first date, I'll have you know."

"I believe you," I told her. "Please. It's a mistake. It's my mistake, okay?"

"Oh yeah!" Tabitha snorted. "Now I get it. You want to do everything, huh? All night long. I remember what you said."

"That was different," I explained. "That was ... before, not now."

"Yeah?" She stared at me. "So what now then?"

"I just want to..."

"I'm not gonna let you fuck me!"

" ... get to know you," I finished, blinking as her words caught up with me.

"So you can forget that," she said. "Just because I ain't rich or whatever, I'm not a slut."

"I didn't say that."

"Jessie said you're a nice guy." She rolled her eyes. "What a jerk!"

"I'm sorry."

"I heard you the first time."

"Well, I'm still sorry."

We looked at each other for several seconds and they passed slowly.

"Do you want to start again?" I asked and when Tabitha made a face at me. "Hey, I gave you a do over."

"A do over?" She smiled for the first time since she'd gotten in the car.

"I'm John."

"Tabitha," she said, taking a deep breath. "This better be an excellent date, John."