My First Client

Discussion in 'Erotic Literature' started by Caitlain, Apr 12, 2008.

  1. Caitlain

    Caitlain Banned

    Nov 17, 2006
    Likes Received:
    Fort Lauderdale, FL
    This will be the last story I post here, and follows the "Transition" story I posted earlier. I will be posting future escapades to a new blog I created to allow people to keep up with what takes place. PM me for the link if you're interested.

    I went home and took a quick shower, sat down in front of the TV and went back to reading my e-mails. Three months later I was still getting random, spurious e-mails from guys who’d responded to my original Craigslist ad. Most of them were just shots in the dark as far as I could tell. Other than explaining to them I’d found someone to take care of the original facial request, I hadn’t said a word to the majority of them, and I couldn’t figure out why they kept sending me the e-mails. As luck would have it, though, one had come in between the time I’d blown the guy this afternoon and the time I sat back down. It is an excellent example of what I am referring to.

    “After that discussion about the facials, I want random sex. Let’s just meet and let me pull down your panties, lick your pussy till you cum, then turn you around, bend you over and fuck you until I cum. Which cheeks would you like to feel my warm cum splash on?”

    I had done nothing more that respond to this guy’s original query about the ad with “I’ve already found someone to take care of this. Thanks.” He’d taken the liberty of sending photos of himself and his erect cock with his first e-mail, though. I went back and looked, and he was quite attractive – a middle aged guy in his late 30s, perhaps. I thought for a few minutes, and then typed out a quick reply. “Are you willing to pay for it?” I actually figured he’d reply that he didn’t want to pay for sex. But, this was Craigslist of course.

    “Well now, that’s an interesting question. I know that everything I value comes with a price. What do you have in mind?”

    Shock. What do I say to him now that my bluff has been called?

    I had already kind of entertaining the idea of experimenting with some guys before I began my “official” work as an escort in San Francisco. I didn’t want to go into it in a strange place without any experience doing anything like this before. Sure, the facials and blowing the last guy was one thing, but actually going to meet someone to fuck them for money was the ultimate first step as I saw it. And up to this point, I’d only really thought about finding a guy who propositioned me at work. That happened quite a bit, and I really didn’t know if I’d actually go through with it until it happened.

    I figured I may as well play this one out, though, to see what might come of it. I replied, “Well, guys have been paying $100 to cum on my face lately, so if you want to actually fuck, I think $200 seems reasonable, don’t you?” I attached a couple of photographs so he’d have some idea what I looked like.

    “Well, I like what I’ve seen, but for that I’d like to be able to take my time and enjoy you. You are a very lovely woman and I’d like to seriously enjoy your body. Can we talk an hour or so for that price?”

    “I don’t have a problem with that. What part of town are you in? You want me to come to you or you wanna meet me somewhere? And what do you mean by “enjoy”?”

    “Enjoy… I really love a fit woman’s body. You look to have a very nice figure and soft skin, so I want to touch and taste and enjoy it. If you can’t host me, we’ll need to meet somewhere.”

    “What part of town are you in, and do you know a good, inexpensive hotel near you that we can use? If we go that route, you might get a bit more than an hour. I won’t be a clock watcher.”

    “I’d enjoy that. I’m in Pembroke Pines, so I’ll have to see what I can find. Can this be a GFE and can I pop more than once?”

    “Sure. If you want to add $100 to it, you can have a PSE - anal, rough face fucking, etc. Your call. Just let me know so I can plan accordingly.”

    “You’re too pretty. I just want to touch, lick, suck and fuck you and have you do the same to me. I have meetings all day tomorrow. How does late afternoon on Thursday work for you?”

    “Haha! Okay, whatever works for you.” I explained that I have classes on Thursday afternoons, and that we’d need to find a day next week for the rendezvous. He indicated that he’d get back to me, which he did a few hours later.

    “I thought about it this morning and I’d like to offer you a different proposal. Let’s look at the little rougher and nastier sex, but let’s go ahead and make this a true play date that you just happen to get paid for. Let’s say $250 for a couple of hours of play, but let’s make it something that you really enjoy, too. I like being dominant sexually and you seem to like to be submissive, so let’s just play in a way that gets us both off. As an example, we could play that you are my new slave just being delivered and I need to inspect you and try out, punish you if you don’t do as you are told, etc. I’m open to any scenario that turns you on. What do you say?”

    “$250 for two hours is a bit too low for two hours of sex play, I’m thinking. I’m certainly open to that kind of scenario, but for two hours, you’re going to need to come up with some more money!” I may be becoming a whore, but I’m not going to be a cheap one. He countered with $300.

    “I can live with that, I guess. You’ll need to bring some condoms - don’t forget those. Let me know how you want me to dress, too.”

    “How I would like you to dress? I love the school girl dress with the white button blouse look, and I love the really short skirt with a tight see through top. Let me know what you have. I’ll bring condoms. I hope oral is bareback, though.”

    This was to be the first significant decision I was going to have to make as a new hooker – oral with or without condoms? It didn’t make sense to use condoms for vaginal or anal sex and not oral, since anything you had would likely be transmitted orally anyway. Still, the thought of sucking a latex covered anything was…less than appealing. I knew I’d have to get over that for my own safety, but I elected to forego it this one time. “Bareback is fine with oral. Did you decide if you wanted the GFE, or the PSE?”

    “As far as rough or GFE, I’ll like to know from you what really turns you on. It would give me the most pleasure if you were aroused by what we did. That’s the biggest turn on for me.”

    “Well, it’s your money, so you’re the one who makes the call on what you want. I’ll be aroused regardless. If you want the softer, sensual GFE, then that’s what you get. If you want the hardcore PSE, then you can have that as well. You get what you pay for.” I had already decided that, for the time being, I wasn’t going to have many hard limits. Nothing involving shit, animals, or anything patently illegal, but unlike some women, I wasn’t going to say no to anal or water sports, no kissing, no this, no that, etc. I am there to service the client, and he or she had purchased my time, so I was going to do what they wanted to do, by and large. At this point in my journey I didn’t see any need to put limits on anyone, and I enjoyed anal sex, rough sex and even watersports to a degree. That may change; we’ll see.

    We continued to work out the finer details of where, when and what he’d want do to specifically. He wavered back and forth between soft, sensual girlfriend experiences to the hardcore, rough fucking -star experience. I explained that it was his money and he’d get whatever he wanted to pay for, regardless. He finally settled on a fantasy, stripper/lap dance, GFE-kind of fantasy. So we set it up for a nearby hourly hotel not too far from the house.

    “You do realize you’re going to be my first, right? I’ve let guys cum on my face for money, but I’ve never actually fucked someone for money before. ”

    “Actually I kind of guessed that, and I’m really looking forward to it. I think you will be wonderfully fresh. Thanks for doing this for me.”

    I spent the next several days running through all kinds of scenarios in my head – how things might play out, would he do this, would he do that, would I be turned on or not, etc. While I knew superficially that I felt comfortable with doing this, it was still an inner struggle with myself fighting against that societally-ingrained image of how “wrong” it is to be fucking someone for money. I had done tons of research on it, read every book I could get my hands on about it, and written all kinds of papers supporting the legalization of prostitution. And of course I’d even been relatively comfortable taking money from guys who wanted to cum on my face. But it was still tough to overcome what 20+ years of indoctrination had taught me about it when I was going to be spreading my legs and allowing someone to penetrate my inner sanctum. That was one reason, I decided, that I needed this trial run – I needed to make sure I was going to feel comfortable taking a stranger’s cock before I actually started putting myself out there as a professional.

    I spent Wednesday randomly exchanging e-mails with him about the upcoming festivities. He was nice to chat with, and that made me feel a bit more comfortable about it. Still, I was a bit anxious – a perfectly normal reaction as I saw it. As the afternoon wore on, I was surprised that I was already getting wet in anticipation of what was to come. I took a shower, fixed myself up, got dressed, collected my music and prepared myself mentally for what was to come.

    At the appointed time, I drove to the hotel. It looked for all the world like the archetypal “hourly motel” you see associated with prostitution on the news and in the movies – a sort of run down, one-story U-shaped structure with a facade that looked like attention to detail on the part of the maintenance staff had long since been fogotten. I wondered to myself if he’d patronized this place before. It dawned on me that this wasn’t exactly an auspicious beginning to my career as a paid sex provider – certainly not the glamorous five-star hotel that I had in mind when I first gave serious consideration to doing it. But, I told myself, this is a trial run, not the real deal. I pulled into the parking lot and found the room number he’d texted me. His truck was sitting in the parking lot so I figured he’d already be in the room waiting for me. I knocked and he opened the door. “Hey.”

    “I honestly thought you wouldn’t show up.”

    “Why’s that?”

    “I just figured you were too hot to really be doing this kind of work. Don’t get me wrong, I’m glad you did. God, you’re gorgeous.”

    I laughed. “Thanks.” We bullshitted for a few minutes, and then I suggested he get comfortable in a chair that was situated next to the cheap little table they had in the room. As he took his clothes off, my first thought was that it’d be nice to be bent over that table while being fucked. But I had serious doubts about whether or not the table was going to hold my 120 pounds up with someone pounding away at me. He sat down as I found an electrical outlet to plug my boom box into for the dance.

    I popped the CD into the boom box and set it to play one of my favorite pieces to dance to, NIN’s Closer. As the music started, I walked over and began dancing in front of him, slowly disrobing one little piece of clothing at a time. I’d worn my school girl outfit – a thin white button-up and a very short mini-skirt, and had my hair up in pig tails just as he’d requested. I turned around and wiggled my ass about 4 inches from his face – close enough that he’d be able to smell my scent. He licked and lightly bit my ass and then slapped me on the right butt cheek rather smartly.

    As the song wore on, I continued taking clothes off and dancing around him, occasionally grinding on his lap. Once I had my top off, I put my tits right in his face and let him suck and bite my nipples for a few seconds. I grabbed his head and gave him a long, sensual kiss.

    I got back up and danced on, teasingly removing the little wrap that I called a skirt. I slowly slid my thong down around my ankles, and kicked it off into his lap. “You can keep that when I leave.” I put my right foot up on the back of the chair behind his head and began masturbating less than a foot from his face just as those infamous words came out of the box, “…I want to fuck you like an animal.” A couple of years of using Closer as a favorite lap dance song had allowed me to time that just right. He started to move toward me, but I pulled back. “Un, unh. Not yet, my horny friend.”

    After a few more minutes of dancing as the song wore down, I finally leaned back on the table, spread my legs apart and reached down and started masturbating myself again. He observantly took this as a sign to move in, and got out of the chair onto his knees and moved over to where his face was even with my pussy. I took my index and middle finger and used them to pull my hood back to expose my clit. “Eat my pussy, baby.” He moved in and began softly licking and nibbling my little clit. I took my other hand and grabbed his hair and pulled his face into my cunt. I was so aroused by what I was doing that within two minutes he’d brought me to a powerful orgasm. I’m not sure if that spoke to the level of arousal or his ability to eat pussy. Not that it mattered.

    I was surprised at how fluidly this seemed to be going, and decided it was time to take that ultimate step. “I need your cock in me. Now.” He pulled away from my pussy, stood up and grabbed the condom package off the bed and began tearing it open. He pulled it out and rolled it onto his erect cock, and walked over to position his rod at my entrance. He placed the head of his cock into the opening of my pussy and reached up and grabbed both of my tits with his hands. As he kneaded them and twisted my nipples between his fingers, he began working his cock into my cunt, slowly, back and forth, back and forth, increasing his depth each time he thrust. Finally he got it in all the way. “Oh, yeah. Fuck me. Hard.”

    He began pounding my pussy with his cock. It wasn’t huge, probably 7 inches long, but with a pretty substantial girth. He started fucking me furiously and I was honestly concerned that the table was going to give way under the force of my weight and his pounding – what a sight that’d be. I don’t want my first job to be that embarrassing. After a few minutes of this, he wanted me to turn over so he could fuck me in a doggy position. I rotated my body around so I was lying face down across the top of the table which, miraculously, was just the right height for me to bend over while keeping my feet on the ground. The wood veneer on the cheap table was warm from where my body had been lying on it, and it felt good to my stomach and tits.

    I spread my legs a bit and felt his cock at the entrance to my pussy. He guided his cock in and began fucking me again. The feeling of being fucked so intensely was a warm welcome to someone who hadn’t had a live cock in her in a good two years. “Slam it in there. fuck that cunt. Yes. Oh, god. Fuck, yeah.” The feeling of a live cock in me once again was intoxicating. Being fucked with a strap-on penis feels great, but it just simply can’t hold a candle to being deeply penetrated by a cock attached to someone who can experience the feedback loop inherent in the fucking of another erotically charged soul.
  2. Caitlain

    Caitlain Banned

    Nov 17, 2006
    Likes Received:
    Fort Lauderdale, FL
    Up to this point he’d been holding my hips with his hands. He finally got emboldened enough to let go and grab a handful of my hair with one of his hands. His pull was somewhat weak, though. I thought to myself that he’s trying not to hurt me, and I appreciated that. “Pull my hair like you mean it.” He adjusted his hand so as to grab more hair and pulled it hard enough to force my head back as he continued furiously pounding away at my cunt. I was trying to squeeze my pussy muscles in rhythm with his penetrations, but that’s hard to do when you’re being fucked as rapidly as I was at that point.

    I felt a finger from his other hand begin to play with my asshole. Anal penetration isn’t included with the typical GFE fantasy, so I hoped in the back of my mind that he wasn’t going to go that route – we’d already had this conversation. Of course, I have to suspect that most guys, when they have a woman in the doggy position and they see that little puckered rosebud, are kind of inexplicably drawn to it, so I didn’t blame him for teasing it. It is forbidden territory in many cases. I didn’t say anything – I wanted to see if he was going to respect the boundaries we set at the beginning of this transaction. I may be a whore, but I expect to be treated with respect. In the end he just played with it a bit. Perhaps he’d pay the extra to go there if/when there’s a next appointment. He stopped fucking me for a minute and pulled back. He slapped my ass with his open hand twice. It stung, but it was one of those pains that cause the juices to flow even more.

    He stuck his cock back in me and I continued fucking it. After a few more minutes, he indicated that he was about ready to cum, and wanted me to finish him off orally. He pulled out, and took the condom off as I turned and got down on my knees. I grabbed the towel and wiped his cock off in a hurry and took him in my mouth again. I worked my way down on it, and as I bottomed out, I could smell my fuck scent on his crotch. When two bodies get together for sex, the pheromones and musky scents that are released can be pretty intense. Anyone who’s walked into a room where two people just got done fucking knows what I am talking about – you can smell the scent of sex in the air. This was no different but was the first time I’d actually noticed how strong it was on someone I was fucking.

    I had just enough time to go down on him a couple more times when he took his cock out of my mouth and began jerking himself off. “I want to plaster that gorgeous face of yours.”

    “Grab my hair and hold my face where you want it.”

    He took his free hand, grabbed the hair on the back of my head, and positioned his cock right in front of my face, jerking himself furiously. “Cum on my face, baby. Splatter me with that shit.” I could see the orgasm building in his facial expression, so I knew he was about ready to explode. And explode he did. He cried out as the first shot left his cock and splattered all over my mouth. It felt almost like a bullet hitting me, it hit so hard. My head instinctually tried to jerk back but his tight hold on me prevented me from moving much at all.

    This was followed by a series of another half dozen spurts. He must’ve been saving this up for a few days, just based on the volume alone. My entire face was covered in white sticky juice when he was done. I reached up and wiped the pools of cum from my eyes and looked at him just as he sank back onto the bed, drained. I crawled over and took his cock into my mouth to clean him up. He moaned as I once again took him deep into my throat and used my tongue and lips to draw the remaining cum out of his still hard cock.

    When I was done, I grabbed the towel and began wiping my face off. Gary continued to lie on the bed for a few more minutes as I began to get dressed. “Did that meet your expectations?”

    “Oh, fuck, yeah. God, I’ve looked forward to that for the past week. I didn’t get to spend much time exploring your gorgeous body, though.”

    “You seemed pretty worked up, especially after that dance.”

    “Yeah, but I would have liked to have spent a bit more time fucking you.”

    We spent the next half hour or so talking about a variety of things, including why I had decided to start working as an escort. I had to be careful not to share too much information with him, but I explained my reasoning behind the decision I’d made and why I made it. We talked about the services I’d be providing and I explained that I had few hard limits.

    “Would you mind sucking my cock some more? You did that so well and I only got to enjoy it for a couple of minutes. My wife doesn’t really enjoy doing it, and she sure won’t let me cum on her face.”

    I moved over to him and took his semi-erect cock in my mouth and began getting him hard again. Within a few seconds he was once again standing at attention, and I lavished some tongue-loving on it. His hips started bucking to meet the rhythmic up and down of my face, and I started letting him penetrate my mouth deeper each time, finally allowing him all the way into my throat. After ten minutes or so, I could tell he was on the verge of another orgasm and began working the bottom of his cock with my tongue. “I’m going to cum again.”

    He exploded in my mouth, with a strong pulse of cum shooting into the back of my throat. I was able to keep my mouth closed around his cock and continue going bottoming down into his balls as his ejaculations continued, and didn’t spill a drop. I slowly withdrew my mouth from his cock and showed him his load in my mouth, and then swallowed the whole thing in one motion. He just dropped his head back onto the pillow. “You’re fucking incredible. You definitely earned your money.”

    As I started to get dressed, we discussed the possibility of future meetings. Though it wasn’t my original intent to begin my escorting work while I was still in Florida, if this guy wanted to continue paying me to fuck him, I’d certainly consider it. He was intelligent, nice, clean, and treated me well. We agreed to meet next week for another date. He wanted to face fuck me and do me anally, he said, and I agreed to that for $500.00.

    “Well, I’m glad to hear that you enjoyed me. Let me know what time and where you want to meet this weekend. You know how to reach me.” I finished getting dressed, picked up the envelope with my $300 in it, my keys, walked out to the car and began to drive home. I had just turned my first official trick and it had only taken about 45 minutes. I was elated – I had actually gone through it and, apparently, done a good job. I felt as though I was bouncing off the walls inside my head. I don’t know if it would always feel this good when I was done, but it sure as hell was a good start.

    That night, as I explained how things had gone down to Nikki, I began crying. I couldn’t figure out why – I hadn’t thought anything I’d done was dirty or debasing or anything like that. My sense was that the sensory overload had just caught up with me. I had been so anxious and unsure about what would happen and had run through so many scenarios in my head that when the reality finally set in and it went off without a hitch, it was just one big release to be able to let it all out.

    I had taken that first step and had my first client. And, apparently, earned a repeat client at that. I decided to invest my newly earned money in the development of a web site to advertise my services in California. That seemed like a reasonable way to invest the first money I made from my new line of work.
  3. igor

    Gold Member

    Jan 13, 2006
    Likes Received:
    Chicago area
    Very well done!
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