Chapter 1

Rachael Ross 1982 - 2012

Erotica Sex Story: Chapter 1 - A man lives out his fantasy after buying a transgendered escort for the evening.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Consensual   Romantic   TransGender   Oral Sex   Anal Sex   Masturbation   Petting   Prostitution  

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."

I'd begun by licking around her rosy anus and kissing the soft, puckered skin, holding her ass with both hands and spreading Jessica's cheeks with my thumbs. She smelled clean and sweet and that almost disappointed me as I would have worshipped her asshole just as eagerly had she been damp and musky with sweat. The idea of tasting her inside, of sating her desires, filled me with adrenaline and we were very much in agreement that way. Jessica reached back with her hand to pull my face against her as I stiffened my tongue. The previous aches were forgotten in the heat of this new experience and I wiggled the tip of my tongue to worm my way past her sphincter.

"Uh-huh," she sighed. "Uh-huh ... Oh yeah ... Uh-huh ... Eat me, baby ... Love my ass ... Fuck me with your tongue."

Her panted words filled the room and Jessica pushed against my tongue as if using a toilet, contracting the rubbery ring of her anus and relaxing, opening for me as my tongue slipped past the opening. I couldn't get very deep, of course, but I was inside her and she didn't object when I let go of her ass with my right hand to find her still swollen cock. I jerked her off, sliding my fist along the shaft while I made love to her shemale cunt. I wanted to bring her off, remembering her threat to cut short our evening if I came before her. My balls seethed with the need for release and the slightest touch would have pushed me over the edge.

"That's enough," she breathed, pushing me away as she stood up and she must have been close.

I'd felt her cock throbbing, spilling large dollops of precum from the tip.

"Let's relax a little," she suggested. "I need a massage, I think. Are you any good at that?"

"I don't know," I admitted. "But I'll try."

"Spoil me, John," she said, smiling over her shoulder as she got on the bed.

It may sound strange, paying so much money for the privilege of giving a beautiful shemale a massage, but this was exactly what I wanted. Jessica gave herself to me in that chaste, but wanton way. She allowed me to explore every inch of her and whatever small imperfections I might have found as I licked and kissed and caressed her body, they only added to her sublime beauty. I removed her shoes and rubbed her feet, kissing and suckling upon her toes. I teased the back of her knees and ran my tongue along her spine. We had no ointments or oils, only the beads of sweat rising like dew from her pores. I tasted her sultry and exotic, breathed in the unique aroma of Jessica's pleasure.

She let me do her front, but I could hardly be as serious as she deserved. I found her breasts with my mouth and I ate her nipples with my gentle teeth until they'd turned dark and puffy. I might have bruised them, but Jessica stopped me before I could give her any sort of love bite to remember me by. I kissed her tummy and around her cock and soon enough she had me sucking her once more. Until this night, I'd only done such a thing in my dreams and the size of Jessica's erection frustrated me as I couldn't take more than half of it into my mouth, and even that wasn't so easy as I'd imagined it would be.

"Nice," she breathed, propped against the pillows as I bobbed up and down, spilling our juices down the shaft. "Watch your teeth, baby ... That's a good boy. You like sucking my cock, don't you?"

"Ummph-hmmph..." I agreed, giving her my eyes.

"You're a good little cocksucker," she teased me. "I bet you've done this before, haven't you, John?"

I would have denied it given the chance, but I'm sure Jessica recognized my inexperience for what it was. I'd spent my life straight as an arrow, but always with this guilty desire sleeping fitfully in my soul. That's how it felt, like something deeper than a mere desire. I nursed on Jessica's cock with a genuine passion and I wanted to make her cum. I wanted to feel her cock spurting in my mouth and wallow in shemale sperm as I swallowed it down. But once again, just as I had her close to orgasm, she denied me the fruits of my labor.

"Take off your pants," Jessica commanded, stepping back and leaning against a cheap, pressboard wardrobe.

Her cock bobbed up and down with a hypnotic rhythm, dropping clear fluid onto the carpet. I knew I could suck her to completion and my mouth literally watered with the anticipation of tasting her cum. Jessica's erection seemed larger than ever, the foreskin pulled completely back to expose the smooth ridge that crowned her beautiful penis. Her balls hung low, filling her pink scrotum and drawing that sexy sack tight as it must have fallen some for or five inches below her upright cock. I'd never seen anything like it and I wanted to lick her balls and nibble the silky skin that covered them. I wanted to do everything, but I could only do as she demanded.

"It's after eight-thirty already," she told me, shaking her head at her watch and I blinked at that.

"Really?" I kicked off my shoes and unbuckled my belt, wondering where those ninety minutes had gone. It seemed as if we'd barely started.

"Really," she replied, looking up and smiling. "You've got a great mouth, John."

"You're beautiful," I replied, unable to think of anything else.

Jessica filled the room just standing there. Her long legs gave way to those wonderfully soft hips, her thin waist and flat tummy led to her upturned breasts and swollen nipples. She had the shoulders and graceful neck of a woman, not a man, and I could see nothing of her Adam's apple. Her voice sounded as delicate and sweet and natural as any woman's I'd ever spoken to. The shemale's dark eyes taunted me with their sultry brilliance; her high cheeks and luscious mouth; the pert shape of her nose ... All of those things conspired against me.

My erection pointed straight and true, glistening with arousal above a tight, hairy ballsack. I had an average penis, no more and no less, but I felt foolish and weak as I stood there in my argyle socks, still wearing my pressed shirt and tie, even my suit coat which I'd never considered removing for some reason. In another place and time, I was an important man, the vice-president of a local bank. I had a large house and a fancy car, a beautiful wife and good fortune at every turn, but as I stood in front of Jessica, I felt worthy of only one thing – worshipping her like a Goddess.

"Pick up my panties," she told me, wagging her finger playfully. "Put them on."

"Yes," I agreed quickly, bending to retrieve the flimsy lingerie.

"Careful..." Jessica sang, reaching for her cock and stroking it slowly. "Don't make a mess, John ... Not yet."

"I won't," I promised, praying I could hold my orgasm back.

Of course, I'd never worn women's clothing or even wanted to, but these were Jessica's panties and I pulled them up my legs slowly. The lace tickled my skin, bringing the short curling hairs on my legs to life. I had goosebumps and my erection bounced with a sharp spasm. The undies were a tight fit and I winced as I had to stretch the satin to the point of tearing to get them completely up. I feared trying to press my cock down and tuck it safely away beneath the lace, but I had no choice and Jessica stepped closer as I pushed my penis down to my balls. It still pushed the front of the panties outward, the waistband struggling in vain to close around my waist, but that suited the beautiful shemale perfectly.

"Jerk me off," she whispered. "Into your panties, John ... Make me cum all over your hard cock."

A ragged breath escaped my lips, that's as close to speaking as I could get. I took Jessica's penis in my right hand and widened the gap in my panties with my left thumb. She watched my face while I watched my hand traveling back and forth, pointing her cockhead down and nearly touching my stomach. She stroked my neck and face, played with my hair and soon gasped, putting her chin on my shoulder and hugging me as her ejaculate sprayed onto my cock.

"Mmmm..." she tickled my ear with her humid breath.

I kept stroking her until the spasms slowed and the last of her orgasm clung to the head of her cock. I rubbed the wet glans against my stomach, smearing Jessica's sperm on my skin. She'd given me a lot of cum, much more than I'd ever produced at one time, and the inside of my panties had become a milky mess of hot semen. It covered my erection and seeped downward, around my balls. My pubic hair shone with large drops of pearly dew.

"You're turn," Jessica whispered, bringing her hand lower to cup my cock and balls through the satin.

She rubbed me off the way I might have played with a girl, using her fingers to pet my erection. The texture of her panties added to the pleasure, as well as the sticky warmth of her semen. I held her hips and watched her eyes, wanting to kiss her more than I'd wanted anything in my life, but I didn't dare without an invitation. I could only struggle with my ragged breathing and thrust my hips in search of more pressure. I fucked myself against her fingers and it only took a minute or so before she brought me off with a shuddering climax.

"Yessss..." she breathed. "Cum for me, baby ... Cum in your panties, John. That's a good boy."

It was an orgasm like no other and the only comparison would be the first time I'd masturbated as a boy barely in my teens. I felt that confusing sensation of painful pleasure as the effort to expel my load proved too much for my penis to handle. The pressure put me on my tip-toes, it really did, and Jessica rewarded me with a light giggle and kiss on the temple. I'd pleased her greatly, I knew that much at least, and I smiled dumbly as I tried to regain my senses. I felt light headed and happy, but disappointed as well.

Jessica used the bathroom briefly, letting me watch her though the open doorway while I sat on the bed. I kept her panties on, now soaked and leaking our combined semen. My cock remained stiff while she washed hers in the sink, using a towel to dry herself a moment later. She hadn't gone very soft either, but she ignored whatever desire she felt and leaned close to the mirror, giving me her incredible ass while she repaired her make-up. I could have watched her do that for hours, but it only took minutes. She brushed out her chestnut hair and fixed her bra, and unfortunately began putting on her dress.

"I had a really good time," she told me as I helped her into her shoes. "Thank you."

"Me too," I said from my knees, but only because I wanted to be there. "Can we do this again? I mean, not now, uh ... Sometime?"

"Of course," Jessica said, looking up from her buttons with a smile. "You've got my number, John; all you have to do is use it."

"Yeah." I nodded. "I will. This was the best thing ... Wow!"

We both laughed at that and I felt fifteen years younger inside, like a teenager again. I started to stand up as Jessica retrieved her purse. She pushed me back down though, kissing me lightly on the cheek.

"I'm jealous of your wife," she whispered and I wanted to believe her, but as I watched the beautiful shemale slip out of the room, I knew she was only being nice.

A woman like Jessica would never be jealous of anyone, I thought.

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