Elena My Story Pt 01

This is my first submission. It's mostly a true story, but to protect myself and others, names and some other stuff has been changed.

Everyone's at least 18.

----------------------------------------------------------------------------

In Pretty Woman, Julia Roberts plays Vivian Ward, a streetwalker who's hired by Richard Gere's character, Edward Lewis. Edward's a wealthy corporate raider who gets lost in a bad part of town and asks for directions from Vivian, and she gives him tips on how to drive his car. Taken by Vivian, he decides to hire her as arm candy. Despite some rough patches, they end up falling in love. I'd read somewhere that it was originally going to be a realistic look at prostitution, but somewhere along the line, it got turned into a romantic comedy.

Bleccch!

I've known a couple of girls who have gotten into relationships with clients. Both of them were disasters. Jealousy, mistrust, the guys worrying about her past coming back to haunt them. Occasionally you hear about one lasting, but they're rare.

I began working in the "world's oldest profession" primarily to pay off my student loans and other bills. Getting laid was great, too, but it was mostly about the money. I had a college degree, but it was next to worthless because I couldn't find a job in my field.

It was aggravating.

I began stripping first. I figured I was blessed with an attractive face and a nice body and I've been told I'm pretty hot plenty of times. I'm about five-six and 130 pounds, I've got 34-C breasts, long light brown hair and blue eyes. I never really had a problem showing it off -- within reason that is. I found I was pretty comfortable being stark naked in front of a bunch of strange hormoned-up guys. But I had no ability for exotic dancing. Other girls made it look so damn easy, but I quickly learned that it's not. I quit within two weeks and got a job at a convenience store called the Happy Driver. It was near my old school and less than half-a-mile from my crappy apartment.

A few months later, we got the bad news that the store would be shut down when the company's lease on the property was expiring a couple of months later.

I began resubmitting applications and got a few interviews, but no callbacks.

One day, a horndog named Van was jogging past my apartment building. He'd been in the Happy Driver a bunch of times with a girl or one buddies. He was six-one or so and an athletic 190 pounds. With his dark hair and blue eyes, I think Van looked a bit like a young Christopher Reeve. And he looked pretty hung in those shorts! I would've gladly fucked Van, but I didn't want him blabbing about it all over town. I'd heard him brag to his buddies about nailing this girl or that girl. I didn't need a reputation as a slut. Van drove a Mercedes, which I guessed was a high school graduation gift from mommy and daddy. I would've killed to have any car that ran because my piece of junk Honda's engine went kaput. I didn't have the money for repairs much less a new car, so I sold it to a junkyard and bought a bike from a garage sale. Thank God I lived near the store.

Little did I know that Van would soon get his wish. I didn't intend to charge money men to fuck me. It started, I suppose, in a weird way.

One of Van's friends, a guy named Gerard, seemed so different than Van. He was quieter and seemed genuinely nice. He was a little taller than Van with blonde hair and grey eyes. I sort of liked him. One night, Gerard was in the store just before quitting time. A thunderstorm moved into the area and it began pouring. My heart sank. Seeing my glum expression, Gerard asked if I was alright.

"No, I'm not alright!" I whined. "I gotta ride a bike home in this!"

"Well, why don't I give you a ride?" Gerard asked.

I about kissed him. He waited around until I cashed out and did my end-of-shift work. Gerard drove a Mustang convertible, and the trunk lid wouldn't close all the way with the bike in it, but he didn't seem to care. The drive didn't take long. I invited Gerard up to my apartment. He looked shocked and very nervous. But the growing hard-on in his jeans looked inviting. I just glanced at it and smiled. It had been almost a month for me and I was horny. Gerard was shaking when I began unbuckling his jeans. I gave him a blowjob and he nervously undressed me and ran his hands over my body and then buried his face in my pussy. I dug a condom out of a drawer and rolled it over his cock. Having a real cock in me sure felt great, but there's actually not a lot to tell. Oh, Gerard was good sized. A little under eight inches and pretty thick. But he was totally lame and came in five minutes. I didn't cum once. Gerard looked disappointed. I didn't bother to hide my disappointment. He apologized and got dressed and left quietly. Thank god for toys and fingers!

About a week later, I was outside the Happy Driver taking a smoke break when Gerard rolled up in his Mustang. He apologized again and asked me out on a date to make it up to me. I turned him down flat. He asked again, and I said no again. He began whining.

God, grow some balls, little boy, I said to myself as Gerard ranted and raved. I snorted in disgust and took a final drag on my Marlboro Light and and stamped it out as I exhaled the smoke sharply.

"See ya around, Gerard," I sneered as I headed to the store entrance.

"Aw, jeez. I'm sorry, Elena. Please wait. I'm really, really sorry. I'm just tired, alright?" pleaded Gerard as he followed me. I ignored him as he implored to me again. "Elena? Please? Wait! I really need to tell you something."

I stopped and turned around and snapped at him. "Okay. What, Gerard?"

"Honestly, Elena, I really tried to do my best, but I couldn't help myself. I... I..." he began to say,. He looked around nervously. He walked closer to me, leaned in and said something I couldn't understand because a truck with a bad muffler passed the store and drowned him out.

"What?" I asked, when the noisy truck got further down the road.

"I was a virgin, dammit!" he said a little louder through his teeth. "You took my virginity, Elena!"

I gasped and my hand flew to my mouth. How was that possible?

"Ohmigod, Gerard! Are you fucking serious?" I blurted in shock.

He nodded meekly and shrugged his shoulders slightly.

"So, I'm really sorry, Elena. I really, really like you a lot," he said. "You're hot. You're a fun girl. I tried to impress you. But doing it is a hell of a lot harder than watching it."

Then it all began to make sense. Gerard must've tried to pick up on how to have sex with a woman from Internet pornos. I saw his eyes well up. Suddenly, I felt for him.

"Oh, God. Oh, Gerard... I..." I said softly, not sure what to say next. I was totally bewildered at how a hot college guy with a big dick could've still been a virgin at his age. And his fraternity, Phi Omi, was notorious for the girls members attracted.

"I haven't done it since then," he said shyly. "I know you were disappointed, but..."

He shrugged sadly.

"I was kinda hoping that maybe you'd give me a another chance I guess," Gerard asked nervously.

I was totally convinced it wasn't an act. I'd taken the virginity of one other guy in my life, and Gerard reminded me of him. But that guy had told me before we had sex. Somehow I didn't pick up on Gerard being a virgin.

"It's okay, Gerard," I said with a little smile. "Apology accepted."

I leaned in and kissed him on the cheek to comfort him. I was about to say tell him I'd go on another date when his Mustang caught my eye. I remembered Gerard telling me that his dad was a exec with a major corporation. I forget which company Gerard said he worked for, and I don't really give a damn. Now you're probably going to think I took advantage of a distraught guy. Maybe I did. But as harsh as it sounds, I gave more of a damn about my situation than Gerard's feelings.

Phi Omi is a really exclusive fraternity on campus. I'd heard that if a prospect's parents made under two million a year, they just laughed at them. I already knew Gerard was Phi Omi, so I doubted he was on scholarship. Add it all up and it meant that he probably had money.

Then an idea hit me.

"Say, Gerard," I asked. "What if...?"

I looked around to see if anyone else was around. It was 2:00 am on a Tuesday. Of course there wasn't anyone around.

"Yeah, Elena?" Gerard asked with a hopeful tone.

I took a deep breath.

"Well, I was thinking that maybe we can help each other out," I said. "Now, don't get the wrong idea about me, but..."

Gerard looked at me in total confusion. I tried to remain calm even though my heart was pounding.

"But," I continued. "You know how much tuition and stuff is, right? Especially for a farm girl like me? I only had a partial scholarship."

The farm girl bit wasn't exactly a lie, but it wasn't the total truth either. I was raised in a small town in the midwest, and my house was near a farm. Hell, I'd even sucked my first cock in a barn.

But calling myself a farm girl was a stretch.

Gerard shrugged. "I guess so, Elena. I'm not on scholarship."

"Yeah. Didn't think so," I replied quickly. "So, Gerard, if you were to maybe, uh... compensate me for helping you, I'd love to do it for a while."

"Elena, whaddaya talk..." he stopped and his eyes opened wide and his jaw dropped.

I smiled.

"Oh, shit! You mean pay y..." he yelled.

I angrily slapped my hand over his mouth.

"Don't fucking broadcast it, goddammit! Shit, Gerard! Just listen, huh?!" I told him in exasperation.

"Got me?" I said as menacingly as I could.

Gerard nodded.

"Alright then," I said, removing my hand. "Yeah. You'll be... you know? But I'm no hooker! Got it? Okay, technically it's prostitution I guess. But I'm no hooker. And we've got to keep this between us -- right?"

Gerard just nodded again.

"Great. So we'll meet when I'm available. It'll usually be the weekends," I said. "We sure as hell can't meet at your place, so we'll do it at mine."

"Okay," Gerard gulped. "But why not my place? No offense, Elena, but it's a lot nicer than yours."

"A frat house? Ohmigod are you kidding me? No fucking way!" I said through my teeth.

"But..." he began to say, but I gave him a stern look.

"Okay..." Gerard relented. "Your place."

"Alright. And let's get this straight: We're not boyfriend and girlfriend and we're not gonna date. We're just going to fuck," I told him quietly but firmly. "No barebacking either! I'm not going to have your baby. You bring the condoms."

I was dead serious about no barebacking. I'd had a pregnancy scare right after I graduated high school. This super-hot guy hit on me and I fell for it hook, line and sinker. But neither of us had money for condoms and I wasn't on the pill. But I wanted to fuck this guy badly. My libido got the best of me and I made him promise to not cum inside me. Of course, he broke that promise. I was so pissed! When I began feeling weird a little while later, I borrowed some money from my sister and bought a home pregnancy test. It came back negative. I worried that the test was faulty, but then I began feeling normal and had my period. I guess I had a stomach virus or something. But ever since, I always made the guys wear condoms and I was always on the pill.

"Sure, Elena," Gerard said. It was fairly cool, but he was sweating like it was a hundred degrees outside. And then he looked at me oddly.

"What?" I asked after a few moments of staring at each other.

"How much?" Gerard asked quietly.

I winced. What a fool! Here I was propositioning a guy and I'd forgotten all about the money!

"Uh..." I said, trying to think quickly. I had no clue about how much hookers normally charged. I finally asked, "Three hundred out of your reach?"

"Nah," replied a smiling Gerard immediately. "Not a problem."

"Okay," I said. "Be at my place Saturday at 3:00 pm. You busy?"

"No," he shook his head.

"Great," I said. "I'll see you on Saturday. Oh, and give me your phone number."

I pulled out my iPhone and punched in the number he gave me and saved it. I began walking into the store when I suddenly remembered something else. I turned around.

"Oh, and don't waste it anymore. Okay, Gerard?" I warned.

"Huh?" asked Gerard.

I walked up to him and whispered: "Don't cum when you jerk off to those movies. I want it all for myself. What I want you to do is jerk off until feel you're about to cum, then stop. Do it a few times a day."

"But wh...?" he started to ask. I ignored him and kissed him on the cheek and gave him a swat on the ass.

"Don't cum until I say to cum. That's lesson number one," I warned. "Now go home. You look tired. See you on Saturday."

"Okay, Elena. Thank you," said Gerard. He kissed me on the cheek and walked to his car. The V-8 roared to life. I watched the taillights of his Mustang as he turned left out of the parking lot. The engine's roar disappeared a few seconds later.

I didn't see Gerard again until Saturday, although I had teased him daily by sending him suggestive photos to his cell phone. A little leg one day, my tummy the next, my lower back the next, cleavage the next. Nothing explicit. Just suggestive. And all with the admonition that he was to not cum until I wanted him to.

Saturday came. Gerard showed up a little early. I was dressed in a red pullover nightgown which ended right above my knees. I didn't have anything on underneath. I crossed my arms over my chest to hide my very erect nipples.

I ignored his nervous hello.

"Have you been doing what I told you to do?" I asked him sternly. He nodded.

"God, Elena, you look beautiful and I'm about to go crazy," he said anxiously as he reached out for me. "Can't wait until..."

"And you're gonna keep waiting until I'm ready," I said, pushing him away and holding out my hand. "So?"

"Oh, yeah," Gerard said. He reached into his pocket and pulled out a wad of money and nervously handed it to me.

I later learned this was a major no-no.

"Stay right there, Gerard," I said. "And don't take off a thing."

I counted the money. Six fifty dollar bills. I smiled. I walked to my bedroom and put the money in my purse and walked back out and pulled out the sleeper sofa.

"Come here, Gerard," I said. He complied.

I kissed him on the lips and lifted my arms above my head.

"Take it off, Gerard," I commanded.

He reached down and lifted the gown up. Bit by bit my naked body was revealed to him. He was breathing hard. When I was totally nude before him, I commanded him to sit on the bed.

I lifted my breasts and pinched my nipples and rubbed my clit. Then I turned around and bent over and spread my ass and rocked my hips. But I didn't let him touch me. Gerard was nearly hyperventilating.

God, torturing him is so much fun, I thought.

"Okay, Gerard," I said after five or so minutes. "Now you can strip."

He broke the record for undressing. He was already rock hard.

"Now just lie back and enjoy," I said with a grin.

As hard as Gerard was, a blowjob was probably unnecessary. But I like it. No... check that. I love giving head. He loudly moaned as I brought him to the edge of orgasm a couple of times, only to stop. Yeah, I was torturing the poor boy, but there was a second reason for it. I'd read on a men's sexual health board that it helps some guys with their stamina.

I moved up and squatted over his mouth and spread my meaty labia and began rubbing my clit.

"Okay, Gerard. This is my clit," I said. "Lick it."

I shuddered when his tongue touched it.

"Oh, yeah... Up and down and all around... Oh, yeah... Mmmm... That's it," I said with a sigh as a wave of euphoria hit me. "A little faster now."

And within a couple of minutes, I came screaming, coating his face.

"Very good," I said breathlessly over him. I reached behind me and lightly jerked his large, iron-hard cock. "Got the condoms, big boy?"

"Oh, yeah," said Gerard as he got off the bed. He picked his jeans off the floor and pulled one of out of a pocket. I tore the package open with my teeth. I rolled the condom over his cock and got on top of him cowgirl and put it at my pussy entrance. I moaned as I slowly slid down, feeling practically every vein as inch after inch of Gerard's glorious manhood filled me.

"Oh, fuck..." I gasped. "Oh, God! Mmmm!"

Finally it was all the way in my pussy and I was relishing the feeling of fullness.

"Oh, fuck," I smiled and moaned. "Whew! Such a fat cock."

After riding him, slowly at first, Gerard finally gave me the hard fucking I so needed and deserved. And he lasted longer, although he had to stop a few times. I told him to fuck me doggie style, which is my favorite position. After telling him how to do it, he pounded and pounded away as I came... God, I forget how many times. But it was a lot. Gerard was a quick learner, I thought.

"Okay, Gerard," I said. "Now you're gonna give me every drop."

I pushed him down on the bed and knelt over him and pulled off the slick condom. I wrapped my mouth around his quivering cock. I felt the pulsing. I blew him hard porn-style, spitting on it and occasionally flicking the head of his cock with my tongue, and then I deep throated him. It took a few minutes, but Gerard finally started coming. The look on his face and his shuddering jaw were priceless.

"Ohhh, fuck! Ohhh... Ohhh... Ohhh, shit, Elena! I... can't..." Gerard groaned as his hips rose and he began shaking.

"Ohhh damn!" he growled as he came. His dick began spurting a gigantic load of delicious cum. I'd never seen a guy cum so hard or so much! I was barely able to get it all.

"Oh fuck fuck fuck fuck fuck!" Gerard moaned as I swallowed greedily. "Oh my God! Oh... Oh, Elena! Damn!"

He laid on the bed panting. It took a few minutes for him to begin to breathe normally. He was sweating buckets. He was hard again in no time and we fucked again. We met a once or twice a week for a little over a month, and Gerard really improved. I was fairly proud of myself. I began seeing him with a cute little blonde with perky tits and a great ass. I didn't know her name. I wondered if Gerard was putting what I taught him to good use.

And I'd be lying if I said I wasn't a little hot for her myself.

One night, Gerard was with me again. In the middle of a blowjob, I brought her up.

"So... You fuck her yet?" I asked.

"Who?" asked Gerard. "Mandy?"

"Mmm-hmm," I grunted with his cock buried in my throat.

"Yeah," he said. "A few times."

"She's really cute," I said, and after a little more sucking, I stopped and playfully told him I'd like a piece of her, too.

"I think she's straight, Elena," Gerard protested with a tinge of anger and frustration.

"Oh, I think I can cure that," I purred happily as I jacked him slowly. "I swear I'm gonna turn her lez, Gerard! Imagine Mandy's mouth full of my pussy. I'm betting her kitty gets really, really wet, huh? I bet she cums hard. Hey, wouldn't you like to get in on that action, huh? A threesome with two hot girls? Every man's dream!"

"You... bitch!" grunted a shuddering Gerard through gritted teeth. I could tell he was thinking about it because his cock got a little harder. I just chuckled.

"Gerard, babe. I was just joking," I insisted. But I really wasn't. To make things better, I let him fuck my ass. I'd begun doing anal about six months earlier and I was surprised that I liked it. Gerard did a pretty good job. He came over the Saturday before the Happy Driver closed. I'd been putting in applications all over the place, but no one had called me for an interview. I was needing a shoulder to cry on and was going to ask him to stay the whole night. But then Gerard said something which stunned me.

"Listen, Elena," said Gerard. "I have an idea, but you're probably not going to like it."

"Gerard, I'm nearly broke, I'm in debt up to my eyeballs, I don't have a car, and I'm not even going to have a fucking job in a couple of days," I ranted. "I don't get a job, I might end up homeless. I don't like that! Believe me, I'm open to damn near anything right now."