Rachael Ross Archives - For Internal Use Only

Jessica

Chapter One - Tabitha


Copyright 2010 Rachael Ross all rights reserved.

Synopsis: When John can't arrange a date with his favorite transsexual escort,
Jessica suggests he try friend of hers instead.
Codes: M/tg, Teen, Oral, Anal


=-=-=-=-=-=-=-=-=-=


"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."

"Have you ever been to the circus?"

"You're kidding right?"

"Nope." I grinned at the girl and started the car.

Cirque du Soleil lived up to its reputation, but I'd seen it before. I spent much of the evening watching Tabitha's happy reactions to the performance. I had thoughts of putting my arm around her shoulders, but I didn't. Several times, when the acrobats thrilled the crowd with especially daring feats high above the stage, she clutched my arm, hiding her face against me until she had to peek and see that everything had turned out just fine. I rather enjoyed that, although it did constantly remind me of her youth and innocence.

"That was amazing! God! Did you see those guys? The one with the blue feathers? I should have brought my camera."

Tabitha talked a mile a minute and I pointed at a concession stand near the exit.

"Do you want a souvenir?" I asked and she rewarded me with a knee buckling smile. I bought her a poster and the girl could have had anything she wanted.

"This is all I want," Tabitha sighed. "It's awesome. I've got the perfect spot for it too."

"Really?" I smiled down at her, although she wasn't very short. Perhaps an inch or two shorter than my five foot nine and hardly that in her heels.

"In my bedroom," she told me, taking my hand in hers. "Right above my bed."

"That's a good spot," I agreed, feeling my heart quicken and praying my palms wouldn't start sweating. I hadn't felt like this since I'd started dating my wife.

"Hey. How do you know Jessie anyway?" Tabitha wondered and I got the feeling she'd been curious about that for awhile.

"I was going to ask you the same thing," I replied. I couldn't see the connection between a high priced escort and this lower-middle class girl, except...

"We met at the clinic," she said. "A couple years ago. So, I dunno...We're just friends."

"Which clinic is that?"

"Ummm..." She gave me a sidelong look.

"I mean, if it's not too personal," I said. "I'm just interested in you, that's all."

"Did she tell you about me?" Tabitha asked, slapping her poster against her thigh as we followed the thinning crowd along the sidewalk.

"You mean..."

"I'm kind of weird," she said. "You can tell right?"

"You're not weird," I said. "You're beautiful."

"Ha!" She stuck her tongue out at me. "I know that!"

"Modest too," I teased her and we both laughed.

"Jessie is beautiful," she said. "I just want to be. I take pills and stuff, so I have to see this doctor."

"Okay."

"And Jess was seeing the same guy, cause there's only like one in the whole city or something," she explained. "So, we were talking and it was nice, cause, you know, I didn't know anybody else like me."

"She seems real nice," I offered.

"Yeah," Tabitha agreed. "She's awesome. Sometimes we hang out and stuff, but mostly she's working, so..."

"What does she do?"

"You don't know?" she asked, giving me a doubtful look. "Or do you just wanna know if I do?"

"I guess...Yeah," I said, offering her a guilty smile. "That one."

"She's an escort," Tabitha said. "Like a call girl? You took her on a date, huh?"

"Ummm..."

"It's cool," she sighed. "So that's why you figured I was like her. I get it."

"She didn't really say you were," I said, "but she did tell me you're eighteen and going to college."

"God!" Tabitha giggled. "She does that."

"Does what?"

"Tries to hook me up."

"Oh." I frowned at that, but I supposed I wasn't the first guy Jessica had pointed in her young friend's direction. I wouldn't say I understood it though.

"Mostly with dorky little brothers of her friends or something," she said with a squeeze of her fingers. "This is way better, you know?"

"It is?" I smiled back at her, but as usual I felt kind of lost.

"Uh-huh. Where are we going now?"

"I made reservations for dinner." I looked at my watch. "It's after ten. What time do you have to be home?"

"Whenever," Tabitha said with a careless shrug. "Don't take me home yet, I'm pretty hungry."

"Me too."

=-=-=-=-=-=-=-=-=-=-=-=-=

"You know, um...When I said I didn't even make out on a first date?"

"I remember," I said, sitting at a red light after leaving the restaurant.

We'd eaten Chinese and I'd barely tasted the food while Tabitha talked about everything and nothing. It didn't matter what she said, I just wanted to listen.

"I kinda lied," she confessed, putting her left hand on my thigh and leaning closer against her seatbelt.

"We don't have to do anything," I told her. "I had a great time tonight."

"Me too," she agreed, sliding her hand back and forth, getting a little higher every time. "I don't want it to end yet."

"Me neither," I said, "but it's almost midnight."

"My mom's working all night."

"Yeah?" I adjusted my position as the light turned green and I had to start driving again. Tabitha's small hand very nearly reached the lump in my trousers and I'd been hard for much of the night.

"She's a nurse, so..." She shrugged. "You can take me someplace."

"Uhhh..." I cleared my throat and glanced at her.

"Do you like me?" She bit her bottom lip and moved her hand those last few inches, pressing against the erection I couldn't hide.

"You know I do," I said. "I don't want to hurt you, Tabitha."

"Then don't," she whispered, seeing the turn onto her street approaching quickly. "Take me someplace else instead. Please?"

"Alright, um..." I swallowed hard and tried to think of a place I might bring a sixteen year old girl. The Four Seasons was definitely out of the question.

"There's a motel that way," she said. "It's kinda nice."

"You've been there?" I asked with a sharp look.

"I told you I'm not a slut, John." She pursed her lips and squeezed my cock. "But I didn't say anything about being a virgin, did I?"

"No," I replied. "I guess you didn't."

"You're cute when you're jealous," Tabitha sighed. "I like that."

We didn't say anything else as I turned left instead of right. I felt the rush of excitement, that nervous energy coursing through my blood. My mouth felt dry and my stomach knotted up. She was just a kid, I reminded myself; I should have taken her home and given her a kiss on the cheek maybe. I hadn't done anything wrong yet, but I wanted to and it confused me. Only my cock seemed to know exactly what it was doing, throbbing beneath Tabitha's fingers as she refused to move her hand.

"Ummmph..." Tabitha sighed into my mouth and I found her warm and wet, and tasting like all the sugar she'd put in her iced tea at the restaurant.

I held her shoulders, so soft and slender as I pushed her leather jacket down her arms. We were in one of the older motels on the edge of downtown. It wasn't as sleazy as I might have expected, but low rent all the same, and not the kind of place I'd risk running into anyone who knew me. The financial community was a small one at my level and even in that out of the way place, I felt much better behind the locked door. The night clerk had taken my cash with barely a glance and I'd written my name as 'John Smith' while Tabitha hung from my shoulder and giggled. The guy had definitely looked at her.

"Do you wanna see it?" she asked, stepping back after our first, deep kiss and giving me that perfect, impish smile I'd fallen in love with.

"Yeah," I said. "Christ, you're beautiful."

"Liar," she said with a giggle, pushing her palms across the front of her skirt, tightening the patchwork cotton to reveal a noticeable bulge beneath it.

When Tabitha's hands came back up, the hem of her skirt came with them. She wore white bikini panties, loose enough that her erection had pushed out the left side and it pointed upward, stiff and slightly curved with a pink head and pale shaft. Jessica hadn't lied about that, at least, Tabitha was a very healthy girl and for being thin like she was, her cock looked fat and something like seven inches long, if I had to guess. Bigger than mine, for certain, but slightly smaller than Jessica's probably. I'd have liked to see them side-by-side, but I wasn't complaining as I sank to my knees in front of the teenage transsexual.

"Yeah," she breathed, reaching for my head. "You like it, huh? Kiss my cocky. Tell her you love her."

I glanced upward with a self-conscious smile, feeling my face redden with some small embarrassment maybe. Was I so obvious that a girl like Tabitha could read my desires immediately? Maybe Jessica had given her some advice about me, I had no way of knowing, and it didn't matter anyway. I'd already discovered something important - If being dominated by a woman like Jessica turned me on, having a teenage girl take charge was even better.

Tabitha pulled me close, turning on her hips so that her heavy penis slapped my cheeks. I tried to catch it in my mouth while my hands went to her legs. I held her smooth calves and slid my palms upward, finding the girl's thighs soft and luxurious to the touch. She felt like butter and if I had one complaint, one wish that would have made everything perfect, it would have been to see a pair of breasts pushing against her t-shirt.

The girl had a flat chest with only her swollen nipples to tease me, but to say such a thing is like taking issue with a rose because it has thorns. When she pulled her t-shirt over her head, I could appreciate Tabitha's modest charms just fine. Her nipples looked like over-ripe cherries begging to be eaten. She wanted me to taste something else first, however, and I kissed the head of her penis tenderly.

"I love your cock," I whispered, kissing it again and this time using my tongue to gather a dollop of thin precum from the tip.

She stood with her legs spread and her skirt falling like a plaid avalanche around her erection. I admired the way she lifted her arms almost casually, shoulders back and elbows out as she frisked her brown hair with stiff fingers. My hands went to her ass, inside her panties, and I found her firm and supple, round and a perfect fit as I squeezed Tabitha's cheeks. She didn't help or hinder me, but stood there like a goddess and that's how I wanted to imagine her. Aloof and amused, letting me worship her and accepting the pleasure as her right.

"More," Tabitha urged softly, licking her fingers and rubbing the saliva around her nipples. "Suck it for me. Use your tongue. Mmmm...That feels so good."

Her cock filled my mouth and I had to relearn everything Jessica had taught me, but the lessons came back quickly. I slid up and down easily, taking only half of Tabitha's penis and finding I had enough room to wriggle my tongue beneath the shaft. Much like a real bikini, her panties were held together with strings tied at the hips and I found them with my fingers. A moment later the white nylon fell away to reveal her loose scrotum covered with a thin fuzz of brown pubic hair. She had a fine nest around the base of her cock as well. I kissed her there, pulling my mouth off Tabitha's cock and dragging my tongue along the underside.

"Oh! You like my balls?" she teased me, pinching both nipples and smiling as I buried my face in her crotch.

I kissed her ball sack and felt Tabitha's erection sliding across my face. Her swollen muscle had grown wet with spit and precum and it seemed to pulse with a life all its own. My fingers dug into the teen's sexy ass, pulling her cheeks apart until my fingers discovered her tight sphincter. Much like I had with Jessica, my one and only previous experience with a shemale, I must have spent fifteen or twenty minutes fully dressed and doing nothing but worshipping Tabitha's cock and balls. I could have spent all night doing that, believe me, but she had other ideas.

"Let's get naked," she decided with a grin, pushing me away gently. "You ever sixty-nine?"

"Not with a girl like you," I replied, smiling and flushed, wiping around my mouth with my fingers.

"You want to?" she asked. "It's kind of my favorite thing, you know?"

"Oh yeah," I said. "I want to do everything."

"Shut-up." She giggled and thought I was teasing, but I'd completely forgotten about our earlier misunderstanding.

With Tabitha's help, I undressed at record speed. I didn't even undo my tie or unbutton my shirt. She pulled my clothes off me, smiling and laughing all the while. Somewhere along the way her skirt had gotten lost and we were both completely naked when we found each other on the bed. My cock strained against hers as we kissed. I wrapped the slender girl in my arms and fed her my tongue, feeling her puffy nipples scratching at my chest. They were hard as proverbial pebbles and I didn't mind her flat chest at all just then.

I held her ass while Tabitha spread her legs, lifting the left over both of mine as we lay side-by-side. We were both moving and her penis stood trapped between our bodies while mine slid beneath her balls. I could feel her scrotum teasing me as I fucked the space between her balls and thigh. We were stained and sweating, breathless as our tongues chased each other back and forth between our open mouths. It was the sort of sex I'd enjoyed only a few times previously. The hungry sex of desire without the responsibility of emotion. I'd forgotten what that felt like after five years of marriage, which is a poor admission, but a truthful one. I made love with my wife, but we rarely fucked with such abandon as I experienced with Tabitha.

By silent agreement, with our lips bruised and our breath coming in gasps and groans, we untangled ourselves. I enveloped Tabitha's cock as she began exploring mine. Her mouth and hands were a wonderful distraction as I worked my taut lips along her shaft. I swallowed the juices filling my mouth and caught her cockhead mid-swallow, stretching my throat with pleasure rather than discomfort. I was getting better at sucking shemale cock and soon felt the sexy transsexual doing the same with my aching organ.

Tabitha would deep throat my cock and hold me there, shaking her head as if searching for more than I had to give. She'd pull off with a loud gasp, drinking cool air and sparing her own pleasure a few precious seconds as she'd fuck my mouth with a push of her hips. Her fingers played with my asshole, imitating whatever I did to her. When I paused to wet my middle finger and press it against her anus, Tabitha did the same. We finger fucked each other while we suckled noisily, filling the otherwise silent room with the wet, sloppy sounds of oral sex the way I'd only dreamt of it.

"I'm going to cum," she whispered, rolling her body and pushing us over. "Make me cum, John...I'm so close."

I went onto my back for her, not resisting at all, and she fucked me that way. She lay on my stomach, ignoring my drooling cock and hunching her hips. Her cock pointed straight down, the smooth glans making me choke and gag as it would run out of room. I couldn't open my throat, or if I did the angle was all wrong, but Tabitha didn't notice or care. Her sperm filled balls fell onto my nose over and over, her cock stretched my mouth and when she came, her semen flew out quickly. The salty cream spurted across my tongue and I swallowed, coughed, and swallowed again. I wrapped my arms around her waist and held her against me, keeping her jerking cock in my mouth even as I fought the irrational panic of drowning in cum.

Tabitha's orgasm spilled from my lips and down my cheeks, but I swallowed as much as I could. I regained my composure and forced myself to relax, finding I could breathe through my nose. The realization that I was truly a cocksucker now didn't bother me in the least. I'd made the girl cum, that's all. I washed her cock clean and when Tabitha pulled out of my mouth, I licked and kissed her balls as well. She sat on my face, literally, and I couldn't see her smile, but I could hear it as my tongue circled her asshole.

"That felt good," she sighed. "I came a lot, huh? God! I hardly ever cum like that anymore."

"Ummph-hmmph," I agreed, trapped with my nose between her cheeks and my lungs begging for air. I loved eating her ass, but it was hard to catch my breath.

She took pity on me, giggling as she lifted her right leg and fell to the left as if dismounting a horse. I grinned at the ceiling, licking my lips and filling my lungs with cool air. I reached for her stomach and slid my hand upward to tease her nipples. We needed to take a break, despite the urgency of my erection. I'd been close to cumming as well.

"Do you have any condoms?" she asked. "I wanna fuck you so bad."

"Um..." I shook my head. "No. I didn't bring any."

"I don't really do it bareback," Tabitha sighed and I didn't say anything.

I only wondered if she wanted to fuck me with her cock or with her ass. Either one would be good for me, although I did feel a little nervous about losing my virginity.

"You're okay, right?" she asked a minute later. "I mean, you're married and everything, so...You're clean?"

"Yeah," I said.

"Me too," Tabitha said with a nod, making up her mind. "My mom's a nurse, so...you know."

"Okay," I agreed, telling myself it would be okay to have unprotected sex with a transsexual. I didn't have any facts, but common sense told me I should be much more careful than I wanted to be.

"Yeah, get me ready for it," she breathed a few minutes later, laying face down on the bed with a pillow under her tummy.

Her ass was elevated nicely and the girl's cock was hard and pointing down against it. I jerked her off while I licked and kissed her asshole, getting Tabitha ready for my cock. We didn't have anything but spit and precum for lubricant and I wasn't much more than average, like six inches long and not too fat, but her puckered anus looked positively tiny. It looked sexy too, I have to admit, and I'd developed something of a fetish for all things oral. I loved using my mouth on her, much as I had with Jessica. I could even ignore my own eager erection so long as I could spend my attentions on some part of Tabitha's beautiful body.

I'd fallen in love with her imperfect physical form as much as I had with Jessica's sublime femininity. They were very different physically, but I could appreciate both of them and if I had to choose...I would have taken them both. I'd become addicted to transsexuals. My long secret fetish consumed me and with my tongue worming into the tight recess of Tabitha's ass, I'd already begun planning for my next experience. Perhaps with Jessica, possibly another date with the nubile teen squirming against my mouth, it didn't make any difference to me. I wanted both of them and I wouldn't be able to last a week before my next fix.

"Ummm...Oh! Slowly...Yeah, like that," Tabitha breathed, nodding her head as she watched me over her shoulder.

"You're so tight," I groaned, wincing as her asshole fought the intrusion of my aching cock. "Maybe we should stop."

"No! Noooo..." she smiled at me. "It's okay. I like it. Push. I want you inside me. Just fuck me. Shove that cock inside my ass."

I did push, covering her body with mine and holding the girl's shoulders. I forced her asshole wide and felt the strange, distinct pop of my cockhead slipping past her anus. Another thrust and another, grunting as I forced the tender walls of her rectum apart. She felt amazing inside, like the tightest place I'd ever been. I'd thought my wife had a small pussy, but not like this. Tabitha's ass seemed to grab my cock and squeeze, pulling me inside until my balls were rubbing against hers. I could reach down with my hand and hold our soft sacks together, her male orbs caressing mine. I massaged our balls while I held my cock deep, savoring the moment.

We began fucking soon enough. I kissed her fine brown hair and the back of her neck, licked her salty skin and finally found Tabitha's open mouth. We kissed while I pumped her sexy shemale cunt hard and fast, unwilling and unable to hold myself back any longer. We'd been in that motel room for hours and I was finally going to cum. I could feel her hot inside and growing moist with my precum. If I hurt the girl, Tabitha didn't show it. Her tongue teased my lips and her breathless voice urged me to fill her with my orgasm.

"Do it," she panted across my open mouth. "Cum inside me. I wanna feel it."

I didn't last long, only a few minutes, and when I came it was my best orgasm ever. I know they all seem that way, but this was even better than cumming for Jessica had been. I drove my cock as deeply as possible and held myself inside Tabitha's ass while my balls emptied with a rush of pleasure. The contractions seemed to begin in my toes, every muscle in my body grown tense with the effort of cumming inside a transsexual for the first time in my life. I was so glad Tabitha had talked herself into letting me fuck her bareback and she seemed pretty pleased herself.

"I feel it," she whispered as I caught my breath. "I haven't been fucked like that since I was twelve."

"Really?" I smiled into her shining blue eyes.

"The first time I ever did it, he didn't have a rubber," she said.. "It felt weird."

"It feels good for me," I told her with a chuckle, enjoying the strange euphoria that cumming brings.

"Me too," she agreed. "I love the way it feels."

We stayed like that, not saying anything for a minute, and I didn't pull my cock out of her.

"I think it's still hard," I said, giving Tabitha a small push of my hips.

"Definitely," she said with a giggle. "Are you gonna fuck me again?"

"I think so."

"Good," Tabitha sighed, dropping her smiling face to the mattress. "I want a nice long one this time."

I couldn't have agreed with her more.

 

Chapter Two