Chapter 1

I'd been waiting for her to knock on the motel room door, but it still surprised me and I nearly fell off the edge of the bed. I'd been sitting for some thirty minutes and suffering the temptation to change my mind. There are always doubts, I suppose, but I'd come this far and I didn't want to feel the regret of knowing I'd been so close.

"Hello," she said, smiling and looking even more attractive than her pictures had suggested. "I'm Jessica."

"Hi." I breathed, licking my dry lips and feeling my heart pound with fight or flight instinct.

"John, right?" Her dark eyes widened with humor. "Do you want me to come in?"

"What? Oh! Yeah. Sorry." I nodded quickly and stood aside the open door. "I'm just, um ... nervous."

"It's okay," she said as a breeze laced with sweet perfume washed over me.

I took a deep breath and closed the door while she looked around the room. There wasn't much to see and her gaze settled on my flushed face.

"You look like a little boy on his first date," she teased me. "Have you been with a girl like me before?"

"No," I answered. "My wife's out of town and, um..."

I frowned and chided myself for saying that. Why would I bring up my wife at a time like this? I'd been playing with my wedding ring, turning it around my finger, and I felt my cheeks redden.

"Don't worry," Jessica said with a sexy-cute scrunch of her nose. "We're going to have a lot of fun, but first ... Shouldn't we get the boring part out of the way?"

"What's that?" I asked dumbly, lifting my eyes from her obviously perfect body to the young woman's equally beautiful face.

She'd dressed nicely, even conservatively in a long, navy-blue summer dress, but it couldn't hide her round hips, long legs, or ripe breasts. Jessica looked amazing to me as she tilted her head and brushed aside a lock of golden brown hair, tucking it behind her left ear with a smile.

"The money part," she explained, opening her purse. "It's five hundred for the first hour and three-fifty for every hour after that."

"Oh. Right," I said. "Sorry, um ... Sure."

"I'm available until nine," she told me with a glance at her watch, "and it's seven-oh-one right now. Do you want me for the extra hour?"

"Yeah," I decided, although I'd only asked for one hour in my email. "That would be great."

"Hmmm..." She smiled as she removed a credit card receipt from a thin pocketbook. "I thought you might. Do you need a pen?"

"I have one," I said, reaching into my suit. She put the paper on the cheap desk and I walked towards her on rubbery knees.

I saw that she was billing me for eight hundred and fifty dollars, minus the non-refundable deposit I'd made when I'd arranged our date. That had been two-fifty, just to make sure I wasn't wasting her valuable time, presumably.

"You charge as much as my lawyer does," I joked, but of course it fell flat being overly blunt and somewhat callous.

Jessica gave me a petulant look.

"Sorry." I cleared my throat and signed my name. "I say stupid things when I'm nervous."

"All men do," she told me with a forgiving smile. "That's perfect. Thank you. Now let's put this away and..."

She tucked the receipt safely into her purse.

" ... why don't you get on your knees, John," Jessica said, not asking a question at all. "I really want to see you sucking my cock."

"Yeah, um ... alright," I agreed, dropping to the carpet in front of her.

"Go ahead," she told me with a smile. "The buttons are in the front."

She stood patiently, watching as my fingers fumbled with the small buttons running the length of her dress. There must have been two dozen of them and I started at the bottom. I'd picked Jessica because she'd been the most attractive shemale escort on the website for one thing, but she also advertised herself as a natural Top, someone who prefers the dominant role during sex. That's what I wanted, to worship a beautiful transsexual without playing all the BDSM pain games that I knew nothing about.

I just wanted Jessica to take charge. She'd promised in her emailed reply that she understood completely and now I believed her.

"Do you like my legs?" she teased me, shifting her hips and widening her feet in patent leather heels. "You can touch me, John. Feel how smooth they are ... Use your mouth."

I had no choice as my hands were busy with her buttons and each one that I loosed exposed another inch of creamy thigh. Jessica pinched the skirt, pulling it open for me as I kissed her just above the left knee. She had wonderfully soft skin, moist and smelling of some tropical body lotion that complimented her perfume. As my hands went higher, so did my mouth and when I saw her lace panties, my fingers were frozen as my dreams came true. I'd honestly had the child-like doubt that I'd be denied at the last moment, wondering how this stunning young woman could have a real penis and sperm filled balls.

"Kiss it," she whispered. "I know you want to."

I could see her semi-hard cock trapped beneath the lace and it formed a pronounced, inviting bulge. I touched my lips to her panties and felt the warmth of her on my skin. Jessica's buttons were forgotten as I brought my hands to the top of her thighs and under the dress to find her hips. She didn't stop me, but only put her fingers in my hair. I found her panty clad ass, reaching around her and keeping the dress open with my arms. Better than advertised, she seemed perfect to me and utterly feminine but for the male penis coiled in her sexy underwear.

Tall and slender, the shemale felt supple as silk beneath my hands. Her ass seemed as firm and round as any girl's I'd ever known. She filled my hands and I squeezed Jessica's cheeks while I kissed and licked at her lace covered cock in earnest. She murmured encouragement and played with my hair, scratching at my scalp with her red fingernails and pulling me against her. Jessica's cock grew noticeably with my attentions. She became thick and long, straining against her panties as if aching for my mouth.

"Use your teeth," Jessica told me. "Pull my panties down."

I did precisely that, plucking at the satin with a dread of biting the woman accidentally. I'd never done anything so carefully in my life and I tugged her panties down slowly, not wishing to lose my grip or tear Jessica's delicate undies. I cheated and used my hands as well, inching the satin down her butt. It seemed a wonderful tease as my nose pressed against the skin of her soft, hairless pubic mound. Her stiff cock offered some resistance, but I managed to stretch her panties over that sexy obstacle and it suddenly sprang free to slap my face.

Jessica had promised " ... eight functional inches of shemale cock..." on her webpage and that description had excited me to masturbation many times, but it couldn't compare to reality. She had a much larger penis than mine, being longer and thicker and uncircumcised. The shaft was darker than her peaches and cream complexion, and heavily veined with a large, smooth glans already wet with precum. Her foreskin had been pulled back, not completely, but enough that I could admire the pinkish head and generous piss slit that gaped open and wet like a tiny vagina. I kissed her, I used my tongue to gather clear precum and explore that small hole.

"Mmmm ... Good boy," Jessica whispered. "You're reading my mind. Love my cock, baby ... Kiss it nice."

I pulled her panties all the way down, but concentrated on her incredibly stiff erection. Like an iron rod, Jessica's cock had no give to it whatsoever. It jutted upward at an angle, moving this way and that as I would kiss and lick around the head and along the shaft. My own manhood throbbed beneath my pants, but I'd never been as hard as this shemale obviously was. She had a real cock, a man's cock, but the rest of her was defiantly female in every possible way. Jessica proved it by undressing while I toyed with her erection, smiling down at me as she undid the remaining buttons of her dress and let it fall off her shoulders.

She wore a bra matching her panties, white and made of satin and lace. She didn't unclasp it, but only pulled the straps off her slender shoulders and the cups beneath her ripe breasts. They were snow white with long, dark nipples pointing out and up. Her tits were immaculate and full as they were put on display above her bra. I stared up at her, helplessly infatuated while her cock slid across my face and my mouth found her hairless scrotum and heavy balls.

"Open your mouth," she said. "Wider ... Get your tongue out of the way."

Jessica fed her balls between my lips, one and then the other filling my mouth completely as she pushed them with her fingers. Her other hand gripped my hair in a tight fist, keeping my face tilted upward with her erection stretching along my nose, across my left eye, and past my forehead. She dominated me completely and I understood my role as I knelt still dressed in my suit and tie. This was about Jessica and her pleasure more than mine. She would use me as she desired and the shemale laughed lightly as she slapped my flushed face with her cock, enjoying my muffled groans as I wiggled my tongue beneath her balls.

"No!" she said. "Don't touch yourself. Get your hands on my ass, I like that. If you cum before I do, I'll leave. Understand?"

"Hmmph mmph," I agreed, nodding carefully as I moved my hands away from the tent in my trousers and to her ass like she wanted.

She continued to tease me with her cock and I wondered where her patience came from. I felt desperate with the need to orgasm, but Jessica only rubbed her cock across my face, occasionally slapping me with it while I nursed on her balls. My inexperienced tongue tired quickly and the tendons in my jaws were aching after only a few minutes. Swallowing the saliva overflowing my mouth became a struggle as had a real fear of nipping the woman's tender flesh with my teeth. I couldn't imagine hurting her in even the smallest, most incidental way, and so I forced myself to keep my mouth open as wide as possible.

"Are you getting tired yet?" Jessica teased me and it seemed plain that she knew exactly how subtle this torture could be.

"Mmmph..." I groaned, trying to agree and I gave her ass a squeeze to make the point.

"We'll have to work on that for next time, won't we?" she wondered with a sweet giggle. "Open wide ... There ... Kiss my balls. Thank them for being so pretty, John."

"Thank you," I breathed, kissing her wet balls as Jessica held her cock out of the way. "Your balls are beautiful."

"I know," she sighed, stroking my face with her fingernails. "Now I want you to try something else for me."

Jessica turned around, presenting me with her ass, and she didn't have to tell me what to do. She braced herself comfortably on the desk, bending at the waist to rest on her arms, and spreading her legs wider. I remained on my knees, of course, and found her pink, perfumed asshole to be in the perfect position. I'd never given anyone a rimjob before in my life, but I buried my face between Jessica's milky cheeks as if I'd been starving for her.

"That's it, John," she cooed, rocking her hips and pressing her ass against my face. "Eat my shemale pussy ... Use your tongue ... Fuck me with it. Get inside my asshole, bitch ... Deeper."