38 comments/ 126014 views/ 147 favorites The Deflorist By: Nameless_Rose The ad was in the yellow pages, small and discrete. Jake Lewis and Company Escorts. Men and women welcome. Deflorations our specialty. Reasonable rates. Call 1-800-926-8739. That was all it said, sandwiched into the adult services section of the phonebook between a gay escort company and an S&M phone sex hotline. At first I couldn't believe that it was what it sounded like. Maybe the name was just a clever way of talking about something else. I called the number. The phone was picked up on the second ring by a woman who sounded like a cross between a secretary and a porn star. "Jake Lewis and Company, Deflorists, this is Kristie speaking, how may I help you?" I hung up the phone without saying anything. What was I going to say? Hi, I was wondering if you could send someone over to my apartment? I'm tired of being a virgin. Yeah right. The ad had to have been some kind of joke anyway. It was probably an escort company that specialized in the domination and submission dynamic. Did I really feel like I needed to pay someone to have sex with me? I liked to think that I was at least decently attractive. I had nice hair, long, shiny and chestnut brown. My eyes were light grey and I had clear skin. My body might have been a little bit plumper than that of a super model, but when I looked at myself in the mirror I never felt the urge to shudder and turn away. I wasn't any more socially awkward than the next girl either. I got along well with pretty much everyone. I just happened to grow up in a strict Roman-Catholic family. My education had been made up of two all-girls boarding schools, followed by two years at an all-girls liberal arts college. These circumstances had combined with my disinclination towards lesbianism to leave me a twenty year old virgin. I'd never even kissed a boy before. An epiphany had come to me early the previous year when I'd flunked out of the non-coed college my parents had insisted I attend. I couldn't sleep that last semester because I had been constantly bombarded by dreams of sex. I would wake up in my dorm room, trying not to rouse my roommate with a cry, soaking in sweat, trembling, with my pussy throbbing and wet inside my virginal schoolgirl pajamas. It got so that I couldn't concentrate on anything, couldn't stay awake in class. I tried touching myself to alleviate the tension, but that just made things worse because I could never get myself to come. I had always been a lot more liberal about sexuality than most of my classmates, so I didn't really find anything wrong with masturbating, but I had still never been able to get myself off. I even bought one of those back massagers that vibrate when you push a button, thinking that that would do the trick, but it made no difference. It felt amazing but after forty-five minutes of holding the thing to my erect clit and rubbing back and forth in as many ways I could think of, I still couldn't bring myself to orgasm. Eventually, I started using it to ease the tension from my shoulders after a long day. The night after I called the escort company and hung up I had the most vivid sex dream I could remember, lying in my narrow bed on the second floor of my parent's house. I dreamed that I was sitting in my old college dorm room reading a book at my desk. The door burst open and through it stepped three men, all of them wearing black clothes with black silk masks to hide their eyes. Without saying a word to me they came over to where I sat and took hold of me. They lifted me, stripped me of my clothes, laid me down on the desk, and proceeded to do to me everything you could ever imagine a man doing to a woman. Their hands skimmed over my body, touching me in places that no one else had ever touched, grabbing at my breasts and kneading them, weighing them, pinching the nipples until I cried out in pain and pleasure. Two heads at my breasts, two hungry mouths sucking at my nipples, two tongues stroking and tasting, two sets of teeth nipping and teasing. Then a mouth fastened upon my pussy, a tongue broached my opening and licked at my secret flesh, tasting the hot wetness of me. A blur of ecstasy, of building pleasure and tension, but the more these masked men teased me with their hands and tongues the more frustrated I became. I couldn't orgasm. They lifted me from the desk and threw me onto my bed. One of them lifted my legs high in the air and spread them wide. Another positioned himself between them while the third pushed his cock into my eager, gasping mouth. I felt the head of a cock brushing against my slit, and then it pushed in. I screamed in pleasure against the cock driving into my mouth, I writhed in ecstasy beneath the enormous shaft driving in and out of my dripping pussy. They took me in every position I could imagine, moving me as easily as if I were a figure made out of clay, taking it in turns to hold me in place, to fuck my pussy, to drive themselves in and out of my mouth. I felt their climaxes approaching, felt their pleasure peak and then explode. I felt them shoot themselves inside of me. I was on the verge of the biggest climax in the history of the planet. I closed my eyes, readying myself for the explosion, and then everything stopped. The pleasure ceased abruptly and I felt my impending orgasm dwindle down to nothing. I opened my eyes. My lovers had disappeared. I was alone. I woke up with tears drying on my cheeks and my pussy throbbing like a bruise. The next day I called the company in the phone book again. The phone was answered by the same woman who had spoken when I had called before. "Jake Lewis and Company Deflorists, this is Kristie speaking, how may I help you?" "Uh, hi," I said. "I saw your ad in the yellow pages, and I was just wondering...what is it exactly that your company does?" "We're billed as an escort service whose employees specialize in the companionship of sexually inexperienced men and women. Would you be interested in hiring one of our escorts? There are actually several appointments free in the next few days." How should I respond to that? Yes please, send someone over right away? I said, "How much do you charge?" "Well, for the first session it's five hundred dollars. For every session after that it's three hundred." "Why does the first one cost more?" "The first session usually involves a greater amount of effort on the escort's part. First time customers tend to have more needs than returning ones. Subsequent sessions are much more relaxed and less demanding for our escorts." She paused, and then continued enthusiastically, "See, we don't charge an hourly rate, just a flat fee, so your experience isn't over until you're tired of it--if you catch my drift." I did catch her drift, and I felt myself blushing. I'd been saving up for about a year to try and buy a car, but what did I want more, a man in my bed or a car in my driveway? "I'd like to schedule a session please." I said, pleased that my voice came out without a tremble. "Awesome!" said Kristie. There was the shuffling of paper and then she continued, "Alright, I'm just going to need a little bit of information from you." She asked me my name, age, credit card number (I wouldn't be charged until after the session), and sexual preference. Then she asked me to rate, on a scale of one to ten, with one being the least and ten the most, how sexually experienced I considered myself to be. "Think nun for one, and Hollywood gutter slut for ten," Kristie said cheerily. I answered that I was probably a two. "Alright then." There was no positive or negative inflection in her voice. She had been well trained. "I have appointments available Thursday, Friday, and Saturday evenings of this week at eight o'clock." "I guess any time would work," I said. "Does it matter which one I choose?" "Technically no," Kristie replied, and then she lowered her voice to a conspirator's whisper. "But Mr. Lewis himself is working on Friday night. He's the company's founder, so needless to say, he's quite...professional. He'll take very good care of you, I promise." I hesitated only for a moment before saying, "Then I guess you'd better sign me up for Friday." "Excellent choice, Miss," Kristie said, all business again. "Alright, it looks like everything is all set. Mr. Lewis will be waiting for you at the Enchanted Hunters Motel, room twelve. Just knock on the door at eight and show him your ID. He'll show you his company badge and then you two can get to know each other." "Is there anything else I should know?" I ask. There wasn't. I bantered back and forth with Kristie for another moment and then said goodbye and hung up the phone. I flopped back on my bed, giving a huge sigh and covering my eyes with my hands. Had I really just done that? Had I just paid for an appointment with a male hooker who specialized in the taking of virginity? I guessed so. Friday was only two days from now. I spent the next two days in a state of extreme agitation. At the clothing store where I worked I was only half there, chatting with the customers, but barely paying attention to what they said to me in response. I dreamed that night and the night after of being fucked ragged by a masked stranger. He told me that he didn't care how long he had to fuck me. He wouldn't stop until I came. Unfortunately I was always awoken from these dreams not by an orgasm but by my alarm clock. The harsh electronic beeping had the same effect as a bucket of cold water. Friday went by as if someone had poured molasses into all of the clocks. Seconds ticked by like minutes, minutes like hours. When darkness finally fell around six o' clock I began making myself ready. I took a long hot shower. I scrubbed every inch of myself with perfumed soap, washed and conditioned my hair until it was soft and fragrant. I shaved all of my body hair, paying special attention to the hair of my pussy, being very careful not to nick the tender skin with my razor. By the time I was done, my body was free of hair and redolent of rose and myrrh body wash. I agonized over my choice of underwear. I thought about wearing the black lace lingerie set I had bought on a hopeful whim a couple years ago, but in the end I settled on a pair of plain white cotton panties. I had bought them yesterday in the discount bin of the Victoria's Secret in the mall near my house. The cloth was finely made and rested soft against my newly shaved skin. Virgins were supposed to wear white weren't they? I wore no bra, only a loose sun dress of coral colored linen with the white panties underneath. At seven forty-five I was waiting in my parent's borrowed car in the Enchanted Hunters Motel's parking lot. I had thought about turning around and going home at least a dozen times, had even backed out of my parking space at one point only to loop once around the parking lot and come right back. I stared at the gleaming number on the door in front of me. Room twelve. Was he already in there, I wondered? Had he been there for a long time preparing for our meeting or would he show up right at eight? Would I perhaps have to wait outside the door until he showed up? If I had to do that, I would just leave. I pulled down the sun-visor above me and used the mirror on it to check my makeup. I didn't usually wear it, but when I did I wanted it to look nice, not caked on and trashy. I had dusted a thin coat of grey-blue shadow on my eyelids, lined my eyes with black kohl, thickened my lashes with mascara. My lips, I had painted a deep scarlet, applying a thin layer of gloss over top, to make them look wet and pouting. My hair was all in place, hanging loose down my back. I looked at the clock. Seven Fifty. I forced myself to wait for seven more minutes before I got out of the car. My hands were shaking so bad that I dropped my keys when I went to lock the car door. As I walked the few paces towards the door with the number twelve on it, I dried the palms of my hands on the sides of my dress. When I reached the door I raised my fist and rapped on it very softly. I think that I was half-hoping that no one would answer, but the door opened only a few seconds later. The man standing in front of me was very tall and lean, with ropes of muscle twinning up his tanned arms. He wore clean, new-looking jeans and a black shirt buttoned down just enough to reveal the shallow furrow in the center of his chest. His hair was dark brown and longer than most men wore it, but it looked good on him, tumbling across his forehead and emphasizing his green eyes. He looked like he was in his early thirties. He was the handsomest man I had ever seen. "Hi," he said, giving me a crooked smile that made my heart give a weird lurch in my chest. "Are you Elise?" I had to clear my throat before answering. "Yes." "I'm Jake." He reached into his back pocket and pulled out a leather wallet. He flipped it open and held it out to me, displaying a card in a little laminated window. It looked almost like a driver's license except that it bore the legend, "Jake Lewis and Company Escort Service." A small photo of the man in front of me was in the center of the card. Underneath of it was the legend "Jake Lewis: Deflorist." I gulped, nodded and gave the wallet back to him. Then I began to fumble in my purse for my own wallet. I extracted it and pulled my ID out, handing it to Jake and hoping that he wouldn't notice how badly I was shaking. I was completely tongue-tied. Now that it had gotten to the point when I would actually have to do it, actually have to go inside of a motel room with a strange man and make love to him, I felt utterly terrified. I wasn't ready for this. I had been stupid to think I was. The closest I'd ever been to a boy had been a slow dance with my friend's date at one of the few mixers my all-girls high school had allowed us to have. What the hell was I going to do with a real man, a gorgeous, solid, and incredibly intimidating man like the one in front of me? What would he think when he found out that all I was capable of were croaking attempts at speech and of staring at him like an idiot? He handed me back my ID and I shoved it back into my purse, not even bothering with the wallet. "It's nice to meet you Elise." He held out his hand and for a moment I couldn't think why he had done so. Then I realized that he wanted to shake hands and hastily laid my palm in his. We clasped hands, his grip firm but not crushing, the handshake of a man who didn't have anything to prove. I reflected for a moment upon the absurdity of the gesture. Why bother with something as informal as a handshake? We had just met, but sometime in the very near future we were going to be making each other's acquaintances in a much more intimate way. When the handshake ended he said, "Would you like to come inside? I can make us some drinks." This was the last chance I would have to bitch out gracefully. If I went into that room I wasn't going to come out the same, no matter what happened. "Sure," I said, and stepped over the threshold. The room was definitely a step above your average Motel 6 accommodations. The Enchanted Hunters motel favored dark green wallpaper and chestnut colored wainscoting, thick green pile carpet etched with a pattern of leaves, and antique-looking furniture. There was a TV stand, a desk, a table and chairs, and a single enormous bed, still scrupulously made. I tried not to look at the bed. I looked at the tray of drinks on the little round table instead. "I'm not twenty-one," I said, staring doubtfully at the glasses. "I won't tell if you don't." Jake went over to the table and poured a measure of some Jack Daniels into a glass. He added a couple of ice cubes and then topped it up with coke he poured out of a can obviously gotten from the motel vending machine. "Sorry about the Jack and coke. I usually try to bring something a bit classier, but I was running late and I didn't have a chance to drop by the liquor store. I just happen to always keep a fifth of Jack in the trunk of my car in case of emergencies." I realized that there was a bit of a southern twang in his voice. It reminded me a little of the way the cowboys had always talked in those westerns my mom was so obsessed with when I was a kid. "I don't really drink very much," I said as he handed me the glass and then poured one for himself. I took a sip. It tasted good, strange, but good. Like coke mixed with wood smoke. He grins at me. "Then now's as good a time to start as any. Drink up." He toasts me with his glass and drains half the contents in one smooth swallow. I imitate him, embarrassed that I have to cough a little as the liquid sears its way down my throat. It was a little stronger than I thought. There was a short silence, and then he said in a gentle voice, "Would you like to talk business now Elise, or do you just want to chit-chat for a few minutes?" I felt myself beginning to blush and I put down my glass so that he wouldn't hear the ice cubes inside of it rattling around. I said, "I guess we might as well talk business now." He got up from his chair and said, "Then why don't you go ahead and finish that drink? Then we'll have a seat on the bed." My stomach clenched but I nodded and gulped down the rest of my drink. He watched me with approval and then walked over to the bed and sank down on it, sitting on top of the covers with his back propped up against the headboard. I just stood there staring at him, my empty glass clutched so hard in my hand that my knuckles turned white. "Well come on over, Elise. I don't bite, I promise." He cocked an eyebrow at me. "At least not unless you want me to." My face, already red, achieved a depth of color usually only seen on traffic lights. I forced myself to put the drink down and then walk over to the bed. I sat down next to him, imitating his posture but spacing myself about two feet apart from him. He turned to me, cocking himself up on one elbow. "So, the first thing I always like to ask is: what brings you here today?" "What?" "Why did you call the agency?" I felt a little annoyed. He knew damn well why I had called the agency. Was this some kind of macho head game? Did he just want to hear me say, I'm too pathetic to get laid on my own so I thought I'd just get a hooker instead? I gave him my best haughty look, although the effect was probably ruined by the way my voice cracked when I said, "I would have thought that was obvious." He laughed. "I'm sorry, I didn't mean to ruffle your feathers. I was just curious if this is a fantasy of yours. Willingly losing your virginity to a stranger is something that not a lot of people would do." "I know that," I said. "I guess I just saw your ad and thought, 'You know what, I'm tired of waiting.' Then I called your agency. I almost didn't come today." "You'd be surprised how many no-shows I get every week. You're one of the brave ones." "Brave?" I said, giving a bitter laugh. "More like desperate." "No," he said looking at me with complete seriousness. "You're brave. The desperate ones dress up like whores and go to a club. They get drunk and give themselves up to the first guy who's asshole enough to take advantage of them." "Well isn't that more normal than this? I'm paying someone to take my virginity." My voice wavered close to tears and I clamped my mouth shut, swallowing hard. "You could have found someone. I have no doubt you could. You're a very beautiful girl, Elise." I snorted and he reached across the bed and cupped my chin in his palm and looked directly into my eyes. "I don't lie about things like that." This was the first time he had touched me since we shook hands and the sensation sent a shudder through me. I felt my pulse beginning to quicken. "You made this decision of your own free will didn't you?" He stroked my cheek once and then let his hand drop back to the bedspread. The Deflorist I forced myself to speak. "Yes, I did." "Then what was it that made you do it? And don't give me the lack of self-confidence answer. You wanted this to happen on your own terms. Why?" I realized that I'd begun to twist and knot the bed sheet in my hands and I forced myself to stop it. I glanced over at him and then away. He was staring intently at me. "I did it because..." I paused, trying to figure out what I was going to say next. Because I'm horny all the time and I don't seem to be able to do anything about it by myself. Because I can't sleep at night due to the maddening dreams of sex and pleasure that bombard me all night long. How could I say something like that to him? "I did it because I can't stand it anymore!" I said, my voice choked. "I've been dreaming about sex ever since I found out what it was when I was in the seventh grade! I've never even gotten close to a guy and lately I've been having these dreams every night. It's gotten so I can't sleep, can't think about anything but sex. I had to drop out of school last semester, and it was basically because of chronic insomnia due to sexual frustration!" I shut up then. My insides began to shrivel up in embarrassment. "So you called me because you want to fix it and move on with your life?" He was still perfectly unruffled. His voice gave none of his thoughts away. "Yes." Let him make of my logic what he would. I was the one paying for this, so it didn't really matter what my motives were did it? "You think that will work? Do you think that by having sex with me your life will suddenly change?" I shrugged. "Maybe it will and maybe it won't, but at least something about me will be different. That's really all I want. I want to feel like something about me has changed. Sex is an essential part of what it is to be a grown-up human being. I want to know what that's like. Maybe then I can clear my head to concentrate on other things." "You've thought this out a lot." "Of course I have," I said a little crossly. "I'm not the type of person who would usually think of hiring a hooker." He chuckled at that. "I like to think of myself as a little bit more than a hooker." "Really," I snapped, still annoyed at having bared myself to him so completely. "And why is that?" "Because I have actually received my training from a vocational school." He looked at me pointedly. "And my specialty is the taking of virginity, so I prefer the term deflorist." "What kind of school teaches people how to have sex?" I asked, fascinated in spite of myself. "I've never heard of something like that." "They exist, believe me," he said. "But they're the sort of thing where you have to invited to attend. I was brought into the profession by an old lady friend of mine. She referred me to the school when I was just a year or two older than you." He winked at me. "Personally, I can't think of a more rewarding career path." I laughed a little bit, unable to help myself, but then I saw him looking at me, making no attempt to be discrete about it, his eyes slowly tracing the curves of my body, and the laugh died in my throat. I opened my mouth to say something, anything to fill the suddenly electric pause which had engulfed us, but then he leaned over and fastened his lips over mine. My first kiss. He was gentle at first, sucking lightly, drawing on my lips as if he were tasting me. Then he began to stroke my lower lip with his tongue and my mouth opened of its own accord. His tongue slipped inside easily. The feeling was incredible to me. Never before had I been this close to another human being, never had I been allowed to actually taste another person. Jake tasted wonderful, like coke and whiskey and some other flavor that was all his own. As his tongue explored my mouth, memorizing its topography, I began tentatively to kiss him back, my tongue darting out to lap at his and then retreating when he responded. He began to kiss me with more intensity and I realized that now his arms were around me. One hand was twinned through my hair and the other was stroking up and down my back, tracing the protruding ridge of the zipper at the back of my sundress. Then I felt him take hold of the zipper, felt him tug it slowly downward, and I froze. He pulled his mouth away from mine and then began to trail hot kisses over my cheeks and throat as he pulled the straps of my dress off one arm and then the other. My heart was thudding almost painfully in my chest when he backed away from me. I stared at him, dazed, my dress not quite falling off of me and my lips swollen with his kisses. "What is it?" I asked. My speech was slow, almost drugged. "Will you undress for me?" I glanced at him and then away. I gave a nervous little laugh. "I'm already half there," I said. He laughed too. "I know, but I'd like to see you do the rest. Very slow, sensual. You have a beautiful body." He bent forward and gave me another lingering kiss, his tongue flickering briefly into my mouth and then retreating once more. I got up from the bed, pushing the straps of my dress back up my shoulders. For some reason, I didn't feel afraid. A little shy yes, but nowhere near mortified. His kisses had drugged me. "You're just saying that because I'm paying you," I said. He smiled. "I told you, I don't lie about things like that. I wouldn't ask you to strip for me if I didn't want to see you naked." I blushed hard at that but I smiled back at him. Even if he was just flattering me it still felt good. I was coasting on a wave of self-confidence. Maybe it was illusory, but even though I knew that this man was a hooker, I felt like he really did find me attractive. He really did want me. I could tell by the way he looked at me with hungry eyes, waiting for me to show myself to him. He would be the first man to ever see me naked. I took a deep breath and slipped the straps of my dress from my shoulders once again. I shrugged and gave my body a little shimmy and the garment fell from my body in one smooth swish of cloth, baring all of me but what was concealed by my panties. I dropped my eyes to the floor and crossed my arms across my chest. "Don't cover yourself," Jake said from the bed. It was almost an order. "I want to see you. Your body is so sexy." I felt like my entire body was blushing but I dropped my arms to my sides and raised my eyes to look at him. He was staring at me, drinking me in with his eyes. "Turn around," he said, "Slowly. Twirl for me." I spun in a slow circle, feeling slightly ridiculous. By the time I got back to my original position he had risen from the bed and was standing right in front of me, so close that I could smell his cologne. Both my heartbeat and breathing rate accelerated at his nearness. I felt like a rabbit when it stares eye to eye with a fox. "Was that what you wanted?" I asked, my voice coming out as a breathy whisper. "Yes it was," Jake says, and he grabs one of my hands. He kisses it and then lays it against the crotch of his jeans. I feel something hard and hot beneath the fabric, something huge and straining against the cloth. I gasp and move to pull my hand away, but he holds it there. "You did this to me." He pushed my hand more firmly against him, filling my palm with the stiffness of his erection. "You still think I'm saying that you're sexy just because you're paying me?" It took me a second to find my voice. "No," I whispered. He began to guide my hand in a back and forth stroking motion over top of him, and pretty soon I began doing it on my own. He began to run his hands over my body as I stroked him through his jeans, cupping my breasts and running his fingers back and forth over the nipples, squeezing the cheeks of my ass through my panties, caressing my thighs. He lowered his mouth to mine again and began to feed off of my lips, his tongue finding its way inside of my mouth and ravishing me once more. After a few minutes he broke the kiss and then asked, "Would you like to go to the bed now?" He tweaked one of my nipples gently. "Yes," I gasped. I made to crawl up on to the bed, but he suddenly bent down and scooped me into his arms. He put me down on top of the covers and then crawled in beside me. He began to kiss me, starting with my lips and moving ever lower, to my neck, my breasts, where he paused to suck and lap at my nipples with ever sign of great enjoyment. He kissed my belly, then the outsides of my thighs. Then he grasped my knees in both of his hands and spread my legs gently apart. I made a sound then, something between a gasp and a yelp. He began to kiss my inner thighs while his hands caressed my breasts and pinched my swollen nipples. "What's wrong?" he asked between kisses. "Nothing," I said, trying not to gasp as his mouth worked its way steadily nearer to the bottom hem of my panties. I sat up, pushing ineffectually at Jake's head. "I just—I've never-" I seemed to have lost my ability for speech. "I know, honey." he said, allowing himself to be pushed away. His hands left my breasts and he hooked his fingers into the waistband of my panties. "I'm a pro at this remember? Just relax." I took a deep breath. "Ok," I said, and allowed myself to sink back into the pillows again. Jake began to kiss my thighs once more, and then he began to draw my panties slowly downward. I gasped when the air-conditioned atmosphere of the motel room made contact with the heat of my pussy. He pulled my panties down my legs and flung them aside. Then he took a moment to divest himself of his shirt, shoes, socks, and pants. All he wore now was a pair of form-fitting boxer-briefs. I couldn't stop myself from staring at him. He was amazingly sexy, all tanned skin, rippling muscles and enormous, straining erection topped by tousled brown hair and startlingly green eyes. He let me look at him for awhile and then he knelt between my legs. He began to kiss my thighs again, but this time he didn't stop when he reached the place my panties had been. He began to run his tongue slowly up and down my slit, coaxing out the moisture which had already begun to overflow there. Then, very gently he used his hands to spread my pussy lips wide, exposing my stiff little clit to his questing tongue. He began to lick me, alternating his attentions between my engorged labia and my aching clit. He flicked the sensitive bud back and forth with the very tip of his tongue, then laved it with great, slow strokes, back and forth, that had me writhing and twisting on the blankets. At one point my hands had tangled themselves into his hair, but I couldn't remember when. I was on the verge of coming. I could feel the orgasm building like a storm surge behind a dam. His tongue started on some new dance, circling my clit in languorous arches and then returning to flick rapidly at it once more. I groaned and clutched at his hair. I had never experienced pleasure so intense. I should have been exploding, should have been coming so hard that my body fractured into a thousand pieces, but I couldn't. I arched my hips, grinding myself against him, and he responded by increasing the ferocity of his attentions. It was hard for me to believe that anyone's tongue could move so fast. But still it didn't send me over the edge, just added even more pressure to the tumult building behind the dam. I cried out then, a cry of frustration and agony, and desperate desire. His tongue suddenly stopped and that made me moan in disappointment. Jake sat up and looked at me. "What's the matter, Elise?" he asked. "That didn't sound like a happy cry." My breathing was as ragged as if I had just gotten done running a triathlon. "I'm sorry," I said, trying to breathe normally again. "It's not your fault." He stroked my thigh with one hand. "What is it?" "I can't come!" I wailed. "Everything feels so good and I can feel myself getting all tense and coiled, ready to burst, but I can never do it! I've been trying for years!" "You've never had an orgasm?" He sounded completely unfazed, just curious. "No!" I punched a pillow viciously. He caught my hand and kissed it. "Don't worry," he said, pressing gently against my chest so that I was lying back against the pillows once more. "Different women need different things in order to achieve orgasm. Once we find what turns your switch, it'll be easier." "You think you can give me one?" I asked. He laughed. "I guarantee it. Now, spread your legs nice and wide for me, hon. I want to try something." I did as he asked. He began rubbing my clit with two fingers. Then he curved those two fingers upwards and pushed them gently but firmly into my dripping pussy. It was a tight fit, but I was so wet that I almost sucked him inside. I jerked, gasping, and then he put one hand on my belly just above my pubis and began to pump the hand inside of me gently up and down. As I relaxed against him, he increased the strength and speed of his movements until he was working me to a hard and steady rhythm. The fingers inside of me were touching a spot that made heat fill my entire abdomen. The pleasure was of a deeper timbre than that which he had elicited from my clit, and somehow it was huger, more awe-inspiring. I realized that I was groaning and crying out and writhing against him now. His fingers continued to press hard against that spot inside of me, making me want to crush myself against them. He kept this up for a long time and the pleasure continued to escalate, but then his fingers were gone. I lay there panting, every limb flushed and quivering. I still hadn't come. "Damn," Jake said, kneeling in between my spread legs and shaking his wrist a few times. "You're wearing me out." When he saw my look of consternation he smiled and kissed me. "I'm kidding honey. My hand just needs a little break. How did that feel?" "Incredible. But I still couldn't come." I felt like there was something wrong with me. Jake had done things to me that had made me feel pleasure in ways which I could never have imagined only a few hours ago. He must have seen something of my thoughts in my face because he said, "Don't worry Elise. I'm going to make you come, I promise." He sounded determined. As if I had set him an important challenge. "I think that maybe you need something a little different to set you off. A combination of external stimulation," he reached down and began to work my clit back forth between two fingers, making it swell and sending a rush of moisture down between my legs, "and deep penetration designed to stimulate the g-spot." He winked and placed his hands inside the waistband of his boxers. "Are you ready?" I stared at him for one long moment and then I nodded. "I think so." "Good. Because as you can see, I most certainly am." He pulled his boxers down and stepped out of them, tossing them to the floor to join my own clothes. Then he put his hands on his hips and stood looking at me, his feet spread apart and his hips angled slightly forward. It was as if he wanted to display himself for me and to see what my reaction would be. His cock was enormous, even bigger than I had imagined it to be. Never having seen a naked man in the flesh before, I found myself fascinated by him. I wanted to run my hands over his golden skin, to suck on his nipples, to stroke his cock with my fingers and then take it deep into my mouth. "Can I suck it?" I asked, half-appalled by the boldness of my words, half-elated. Jake looked taken aback. "Well sure, sweetie, but I was thinking you were ready to move on to the main event." "I am ready, but I want you in my mouth first. I want you to tell me what feels good. You've been doing so much for me and I haven't given you anything back." "That's very sweet of you Elise, but you are the one paying me. You don't have to do anything you don't really want to do. A lot of ladies just like to focus on actual intercourse the first session." "I want it," I said, shocked at how much I had changed since I had entered this room. I would never have said anything like that a few hours ago. "But I have no idea what I'm doing. You're going to have to tell me how." He was looking at me with a strange expression on his face. It seemed to be a cross between puzzlement, admiration and blatant lust. After a few moments of silence he spoke. "I'll walk you through it. It will probably be better if I lie down. More maneuverability for you." He laid back against the pillows, his cock pointing towards the ceiling. "Are you ready for your lesson, Elise?" he asked. "Yes," I said, and I crawled towards him. "Touch me with your hands first. Any way you want to." I reached for him, but he grabbed my hand before I could get there. "Is this going to be the first cock you've ever touched?" "Yes," I murmured, looking down at my lap. He made a noise of satisfaction and then released my hand. "Then I want you to explore it. Get an idea of what to expect inside of you in the next few minutes." When he said those last words I felt like the bottom had dropped out of my stomach, but I reached for him anyway. I closed my hands around his shaft, noticing with some apprehension that they only just managed to close around the circumference of him. I ran one hand up and the other went down, gently weighing his balls. I used one finger to trace the outline of his cock head, the slight indentation that ran down his shaft. Jake moaned. "Alright honey, are you ready to put this in your mouth?" "Yes," I said. "Then I want you to open nice and wide. Flatten your lips against your teeth. That's good. Now just fold those pretty lips of yours around the first couple inches and we'll go from there." I did as he asked, opening my mouth and flattening my lips so that they formed a protective barrier against my teeth. Then I took a deep breath and took the first few inches of him into my mouth. He tasted of musk and salt and faintly of spice. It made my mouth water. I began to suck at the head of his cock as I would suck at a lollipop, drawing on him using the muscles of my mouth and throat. Jake grunted and his hips jerked spasmodically, sending the next few inches of him sliding into my throat. I coughed against him, gagging slightly at the sensation of being so deeply filled. "I'm sorry, honey," Jake said, and for the first time his voice was slightly unsteady. "I got a little carried away." He made to pull out of me, but I just backed off a bit and then tried again. This time I managed to swallow a little over half his length before I gagged. I began to move my mouth up and down on his shaft steadily. "Goddamn!" Jake gasped, his hands gathering my hair and pulling it back so that he could see my face. "Elise I really don't think you need my help on this. Ah!" He cried out as I suddenly managed to take the entire massive length of him into my throat. My mouth was pressed briefly against his pubis and then I had to pull away, my throat contracting wildly. I gasped for air when I surfaced like a diver whose oxygen had run out. My cheeks were flushed and my eyes had begun to water. "Honey," Jake said, stroking my hair as I got my breath back. "You don't have to work yourself so hard. Why don't I—" I took him into my mouth again, almost as deep this time, making his words trail off into one long moan. I bobbed my head up and down over his cock, lapping at his shaft with my tongue and every now and again taking him all the way down my throat. I felt ecstatic. Just the taste of him was arousing, and the feel of him sliding in and out between my lips, the sounds of his quickly muffled cries, his soft moans when I took him particularly deep, made me feel euphoric. After several minutes of this treatment he groaned and put his hands on either side of my head, pulling me gently away from him. "Elise, as amazing as this feels, I'm going to have to stop you now or we're going to have to take a break before we move on to the next phase." The Deflorist "What do you mean?" I asked, dazed. My lips felt swollen and slightly raw, but I relished the feeling. I could still taste him on me. "I mean that you're such a good little cock sucker that I almost came right in your mouth." His voice was harsh, but I realized that it was ragged with desire, not anger or annoyance. I blushed. "What now?" I asked, a little apprehensively. I was kneeling beside him where he lay, looking down into his face. "Now," he said, turning and grabbing me around the waist, "I'm going to make you come so hard that the whole world's going to shake." He pulled me on top of him, positioning one leg on either side of my waist. His cock lay trapped between us, pressed against his belly. "Are you ready?" he asked. "God yes," I said, raising myself up so that his cock brushed against my slick opening. I wriggled back and forth for a few moments, loving the feeling of the head of his cock sliding up and down my slit. He put a hand between us, gripping himself at the base of the shaft and guiding his cock into the right position. "I want you to lower yourself down on me. Go slow. Give yourself time to adjust." I nodded, swallowed hard and then began to lower myself onto him. The head of his cock parted the wet lips of my labia easily but then I felt a sort of tension, of not quite pain, as he came up against my opening. Frowning in concentration, I lowered my hips a little further and he began to slip inside of me. There was a sense of stretching, of discomfort maybe, but not of pain. I was so wet and so ready to feel him inside of me that my body had opened itself to him as completely as it could. I sank lower, taking all of him into me until my buttocks came to rest against his pelvis. I felt unbelievably full, unbelievably whole. I could feel the rise and fall of his rapid breathing, sense the quivering of his limbs as he fought to hold his movements in check. I fancied that I could even feel his pulse hammering within me. I cried out in pleasure and brilliant satisfaction. I was a virgin no longer. "What should I do now?" I asked. Having him so deeply inside of me was intoxicating but it was stretching me to the utmost. I needed to move. "Start riding me. Move your hips back and forth so that my cock slides in and out of you. Go as slow as you want." His voice was steady but strained. I could sense that he wanted to do the moving himself, to thrust in and out of me until I screamed, but he held himself in check. I began to do as he had instructed, using the muscles of my legs and thighs to work myself on his cock. I moved slowly at first, my tight pussy seeming barely able to contain him at times, but as I began to open further I started to move faster. In a few minutes I was bouncing up and down on top of him, my buttocks and thighs smacking rhythmically against him. I had begun to moan and cry out as I rode him, unable to control myself. The pleasure that came from having him inside of me was entirely different from anything I had yet experienced. It was a sensation that bordered on pain but it was sweet. It was so sweet. As I rode him I felt like I was chasing something, that I was pursuing some great secret and that the only way I could find it was by guiding Jake's cock to that one secret part inside of me that could trigger my release. But I couldn't do it myself. I needed Jake. I needed his experience and his knowledge. Despite that I had been a woman for twenty years, I felt like he knew more about the female body than I did. He knew where to touch, where to lick, where to be gentle and where to be firm. This knowledge was in my grasp, I knew, but I didn't have it yet, and Jake was the one who could help me find it. "Jake," I said, leaning forward as I rode him so that my lips nearly touched his ear when I spoke. "Will you fuck me?" I raised myself up until only the tip of his cock inside of me. "I want you to make me come," I whispered. I let my legs collapse and I slammed back down on him. The force of his cock ramming back into me made me cry out helplessly. My voice rang off of the ceiling and I wondered briefly if the occupants of the next room could hear me. The thought didn't really concern me. Jake, who had barely moved beneath me this entire time, jerked in response, a groan tearing out of his throat. Suddenly, we were rolling sideways and I was face down on the bed. Jake was on top of me, straddling my legs, his cock pressed up against my ass. "You want me to fuck you?" Jake asked, his lips buzzing into the cup of my ear. He seized my earlobe between his teeth and worried it back and forth for a moment. I gasped. "Yes," I moaned, my hands finding his buttocks and squeezing hard. He slipped back inside of me, easily as if we had been doing this for years. At the same time he pushed my torso up so that I stood on hands and knees with my ass angled upwards. The change in angle made his cock press against that special place inside of me, that thing which I guess was called the g-spot, something I had heard of but never found before tonight. As his cock began to move in me, sliding in and out, slowly, but with ever increasing rapidity, Jake reached down and pressed two fingers against my clit. He rotated them in a circle, pressing hard. That, added to his cock thrusting into me, pointed directly at my g-spot, was enough to start me moaning and crying out and thrashing my hips against him like an animal in heat. Years of sexual frustration were pent up behind this dam inside of me and the sensation of being fucked so damn good was bringing it all to the front. The flood waters were surging against the dam, but still the block held firm. "Elise," Jake said, his own voice raw with passion. "Take it easy hon. Just ride it, ride it to the finish." He began to thrust harder, one hand still massaging my swollen clit, the other grasping my shoulder and pulling me, making me arch my back. The movement pressed my g-spot more firmly against his cock. "Come for me Elise," he gasped, driving into me, his hand stroking me in just the right way. I moaned. I was bathed in sweat. My breathing was ragged. My entire body was flushed and my nipples felt like two hard stones attached to my chest. "I can't." I groaned, pushing myself desperately against him. "I don't know how!" "Yes you do," he murmured fiercely, punctuating his words with a series of hard, rhythmic thrusts. "You're almost there, I can feel it. You're shaking all over. You're flushed, you're sweating." He gave my clit a sharp pinch and I almost shrieked. "Your pussy is squeezing me so hard that I feel like I'm going to go crazy." He turned my face towards him and bent forward. He kissed me hard, his mouth devouring mine. "Come for me," he breathed in my ear. "Let it all go. I want to feel you come on me." I fought to clear my mind, to not think about coming and to just think about arriving. I felt Jake inside of me, sliding in and out, driving against my-g-spot with every thrust. I felt the sharper more ecstatic pleasure of his fingers on my clit. I heard the sounds our bodies made as we joined, the smack of flesh against flesh, the sweet kissing sound of his cock slipping in and out of my wet pussy. I smelled the mingling of our scents. I let myself go. I forgot who I was and why I was here and rode the wave of pleasure that I could feel cresting within me. "Come on, Elise," Jake said. "I'm almost there too. Come with me." His thrusts grew frenzied, almost too much for me to contain. He gave my clit another hard pinch and whispered "Come," in my ear. It was a command, pitched so low that I could barely hear it. The word seemed to penetrate into my brain without bothering to travel via my ears. And just like that I felt myself beginning to come. The world stopped for a moment. But it was more than a moment. It was an eternity. I could see all of the colors in the room brighter than they could ever be, could feel every nerve in my body on fire and singing with release. I felt the muscles of my pussy spasming, felt the hard staff of his cock spending deep within me. I cried out over and over as the orgasm rocked through me in mind-numbing waves, and I heard as if from a long distance Jake crying out along with me in his own pleasure. Then I was circling down and down into a sated, hazy stupor. When I came back to myself I realized that I had collapsed onto the bed and that Jake was lying full on top of me, breathing hard, his cock still inside of me. I didn't mind his weight and when he rolled off of me I sighed, missing his warmth. We lay side my side on our backs, our bodies glistening with sweat, waiting for our breathing to return back to the normal rate. After several minutes Jake said, "Wow." I laughed. "Likewise." He propped himself up on one elbow and looked down at me, a half-incredulous smile on his face. "I've been a lot of peoples' first times," he said, kissing my forehead. "But I've never met anyone like you before." "Should I take that as a compliment?" I asked. "Oh yes," he said. He got up from the bed and naked, walked over to where he had thrown his pants. He pulled a business card out of one the pockets. He wrote down a number on the back and put the card down on the bedside table. "My private number is on that card. I don't give it to everyone. I do more than deflorations. Call me anytime. I'll give you a discount." "How much?" I asked. "Well, that depends." "On what?" "On what you want." "What else do you do?" He smiled at me mischievously. "Oh, all kinds of things. Anything you could imagine. All of your fantasies." Images of everything that ever made me feel weak at the knees with desire floated in front of my brain. I imagined being tied to a bed. I imagined tying Jake to a bed. I imagined a thousand other things we could do together. I realized that now every fantasy was open to me. I had broken the routine. I wasn't a virgin anymore. "I think that you can expect to hear from me," I said, "Once I get enough money saved up to afford your services again." He laughed and fell back down onto the bed next to me. "I'll tell you what," he said. "I haven't come that hard in a long time. Next session is on me." Excitement began to build in me again and I smiled. I ducked my head, suddenly shy. "Jake?" I asked. "Yeah, hon?" "Can we do it again?" "What?" He sounded shocked. "I'm sorry," I said quickly. "If it would cost extra I don't want to—" He leaned over and kissed me hard. "Honey, I'd love to do it again, but you're going to have to give me a few minutes. Why don't we have a drink in the mean time?" I smiled, "Ok. I'd like a drink." I could feel the hunger building inside of me as I looked at Jake's naked body. But I could wait for a little while. I was good at waiting. "It looks like I'm going to be in for a long night," Jake said. He was. I intended to get my money's worth.