Charlene

This is chapter 2 of the Charlene series. Please read chapter 1 ("Event Horizon") before this one. All characters and events are (very) fictional. The story includes explicit descriptions of sex acts, all by characters above the age of 18 and all consensual.

"Arrived!"

I pulled into a shady spot on the long driveway next to a large, ranch-style house. 2:53 PM. I knew I was committed now. My sense of conscientiousness and professionalism would not allow me to cancel this late, especially since my car may already have been spotted. The indeterminancy having been resolved--Schrodinger's pussy--I became much calmer. There was still trepidation, to be sure, but with the decision behind me, my focus shifted to doing a good job. I removed my sneakers and strapped on my heels.

The walk to the door was much more relaxed than that to the car. Heels clicking, approaching quickly. It was a heavy, ornate, wooden door with stylish metal fixtures, the kind often found on expensive, rustic, California homes. I located the door bell and rang.

Paul answered quickly, "Charlene, helloo" in a friendly, casual, disarming voice. He was early to mid-50s but with slightly boyish facial features, tousled, light brown hair, groomed stubble on his face, a beach shirt buttoned halfway that left visible equally tousled chest chair mixing brown and grey strands, and long, turquoise, casual shorts that extended just past his knees. It was true, he did look friendly.

I stepped in with a casual confidence that slightly surprised myself, essentially adopting my typical demeanor for a first-encounter business meeting at work.

"Paul, so nice to meet you," extending my hand. Except rather than print-outs and technical reports in a briefcase, I carried condoms and lube in an oversized purse.

"Would you like a drink?" walking across the large living room to a small home-bar, the area bathed in a soft, afternoon glow from a skylight above it. "I was just pouring some martinis."

"I would love one," following over, slowly, reminding myself to be sexual, but not quite having the intuitive script for that within a business transaction with a stranger. Taking the martini glass, trying to grasp it elegantly, making full eye contact at the handover, and then feeling the gin fill my mouth with a pleasant coolness.

"This is for you," pointing to a white envelope on a bar table.

"Oh, uh, is there a bathroom where..."

"Yep, just down the hall there, count it up," again, in a casual, friendly voice.

I walked into the bathroom, opened the envelope and counted out 8 fresh $100 bills. Drawing the inference, no anal, relieved since on the walk to the door I resolved to politely decline this during our negotiations. He did, however, want to thrust in my mouth and perhaps cum on my face. This sent a jolt of sexual excitement through me, my heart starting to beat faster. I remembered my plan to remove my clothes and come out to him in only my stockings, but decided against it on the grounds that he might want to chat over drinks first, and coming out mostly naked could upend his plans. I did, however, remove my bra and stuff it into my purse to allow easy access to my tits once my blouse was unbuttoned. Doing so caused an increased increment of arousal, excitement, and nervousness, all of which I thought might in fact help me to perform.

I looked deeply into the mirror, noticing small wrinkles on my face, and took a deep breath. 'This is it,' I sub-vocalized under my breath.

The door handle seemed to make a loud noise upon opening, followed by what felt like a reverberating echo from the clicking of my heels. Paul was sitting on a sofa near the bar sipping his drink, and I sat close next to him, prying off my heels and crossing my legs, cognizant that beneath my skirt were no panties.

So, are you a kissing girl?" he asked, with a playful casualness.

"No, sorry, but I am sure we can find other fun things to do." Reaching forward and running my left hand through his chest hair as I said this. Feeling like this was a decent opening for me, tempering disappointment with a potentially seductive touch.

"Maybe I can get more comfortable," I said, unbuttoning my blouse and then peeling it off, revealing my upright, perky tits with erect nipples. The sight of my own tits out was exciting to me. Paul reached over, rolling my right nipple between his thumb and index finger, and then leaned down and began to suck the same nipple. I moaned lightly as he sucked it, watching his lips on me. Wedging my hands into my skirt, I pried it down over my legs as Paul continued to suck my tits, leaving only my stockings on. Naked in front of a strange man, being touched sexually by a man other than Michael for the first time in over 20 years. I closed my eyes for a moment, and heard come out of me what was now a deep, slow, involuntary moan.

Paul followed my lead and wedged his shorts and underwear down in one motion, revealing a thick but mostly soft penis above large, somehow casual-looking balls. Seriously, his balls looked laid back, with similar tousled brown and grey hairs as on his chest. I felt like if in a line-up of scrotums one were asked to pick the one from a relaxed, surfing, middle-aged California business owner, I would pick his nine times out of ten.

He was shaking his cock with his hand, trying to motion it into hardness, when I made what may have been my first mistake as a prostitute. All of the nervous excitement and energy of the past week had crested as Paul sucked my tits, and I was filled with an overwhelming desire to perform slutty sex acts, sliding off the sofa onto my knees in front of him, gently placing my fingers around the base of his penis, and then wrapping my lips over the head of his cock. I began sucking, fully expecting that he would harden in my mouth, that I would feel him grow and fill me, even struggle to keep all of it in without gagging, but instead I found that my tongue was swirling around an increasingly soft, spongy head that was shrinking in size. There was something surprisingly intimate and personal about having a man's soft penis in my mouth, and it brought me out of my intense sexual desire and made me worry that I was falling short in my performance. Paul lifted his cock out of my mouth, and began a rapid up and down motion with his hand shaped into a claw. Trying to help, I wedged my head down and began to lick his left scrotum, tracing a large, oblong left testicle, thinking that he did, in fact, have really sexy balls. After a few seconds of this, he started to stand, "Sorry, that feels really good but I think I need to go get myself up, be right back," said in his characteristic laid-back style, no hint of reproach or disappointment.

I was left sitting in an awkward pose, my legs sideways so that I could wedge my head down into his crotch, my body weight sitting on my upper right thigh. I climbed up on the sofa, second-guessing my decision to take him into my mouth before he was ready, thinking that maybe he wanted to continue sucking my tits or to lick my pussy. I reached for the martini and took a small sip, anxious about whether I could please him. My legs looked sexy in my stockings, crossing them, kicking the right one up and down with nervous energy as it bounced over the fulcrum of my left knee.

After a few minutes, he emerged from a hallway behind the bar, standing, his cock now mostly erect and sticking straight out from his body. "Do you think you could help me out with this?" said again in a disarming and playful tone, making him, as Judith had intuited, the perfect starter cock.

I quickly walked over and dropped to my knees in front of him. Placing his cock into my mouth, I began moving my lips forward over the shaft, dragging my tongue over it as I moved back and forth, eagerly sucking his cock. I looked up at him, seeing him look down at my face with his dick in my mouth, a wife, mother, successful professional woman now sucking a dick on my knees for money, the thought of this sending a surge of excitement through me, making my pussy lubricate fully.

Continuing to suck, I felt his cock buckle slightly, and maybe responding to this, he placed his hand on my head lightly, just guiding it gently into place, and started to thrust into my mouth. He pushed his hips forward and back, thrusting fast but pulling so far back that his cock did not return too far into my mouth, the head almost coming fully out of my lips and then quickly pushing back in to about the depth of my mouth, his goal seemingly more about fast friction than full insertion into my mouth and throat. I tried to cradle the underside of his shaft with my tongue as he thrust in fast, Paul starting to moan as he kept pumping his dick in and nearly all the way out of my mouth, the head coming back in at different angles as he thrust fast, sometimes striking the roof of my mouth, other times just quickly jabbing against the opening to my throat.

He began breathing heavily, vocalizing more rhythmically, staccato grunt-moans, all suggesting that he was building quickly toward climax. He pulled out and started to jerk his cock with his hand right in front of my face. I turned my face up, opened my mouth, stuck out my tongue, ready to receive my first ever facial, looking at the opening of his penis, hoping to see the semen propel out of him. He moaned very loudly, his body spasming, but at first what looked like mostly clear, small drops of liquid flew out at odd angles, only one or two drops lightly hitting my face, his body still convulsing, pausing, then a glob of thicker white cum finally flying out and landing mostly on my upper right cheek, some of it dripping down toward my chin, before more clear drops flew out, mostly missing me, some falling on the floor in front of me.

I smiled up at him as he breathed hard, looking down at me and appearing happy and sated. I dragged my index finger over some of the cum that had dripped toward my chin and then put it into my mouth, vocalizing, mmm in response to this. He patted me on the head in a way that was friendly but not patronizing, then excused himself to clean off.

I walked back over to the sofa to sit down, leaving the cum on my upper cheek in case he wanted to see it there when he returned. I leaned back, looking at the large great room bathed in the pleasant, golden light from the windows, mostly silent except for the muffled sound of a sink running in another room. I reasoned that Paul had sensed that he might lose his hard on again and so decided to cum when he could instead of holding out for intercourse. He was taking a few minutes to clean up and since the semen was drying anyway, I found a tissue and wiped it off.

3:27, still a lot of time in the session. I should definitely stay naked, I thought, in case he wants to do anything else. He came out in only his boxer shorts, sitting next to me, hand on my thigh.

"That was nice," his voice rising in pitch, giving it a friendly tone.

"Very nice," I said. "Would you like a massage or something?"

"That's OK, actually, I have a Zoom for work a little after 4 and I don't think I can go for round two before then, so we could wrap up a little early."

I was still quite calm as I dressed in the bathroom, resolved to debrief myself only once in the car on the way home. At the door, I kissed him on the cheek and told him I really hoped he would hire me again. "I'll give Judith a ring sometime about it," the same easy, casual, non-threatening voice tone that characterized all of his speech. "Ciao."

I was uncertain what I would feel after the first event. It ranged speculatively from crushing guilt, anxiety, regret, and panic, to intense desire and enhanced craving, but at least at first my main reaction was relief and calmness. I had gotten through it, nothing really bad had happened, and now I had the rest of the weekend to relax and pamper myself. The perfect weather only added to this sense of repose.

I tried to analyze where the urges that had led to this had originated. I knew that the near-miss affair with David (not that David) a few years ago had kindled an upsurge in sexual desire that had led to fantasy and pornography and erotic literature consumption, and that many of those fantasies had persisted, including some themes related to submission or being the object of others' intense desire. I had real feelings for David--a self-effacing, witty, boyishly handsome former co-worker--and had correctly rejected the risk to my family by declining romantic entanglements with him. But it didn't feel like this was a sufficient explanation. My attraction in that case was to David, the person (and body), whereas the escort fantasy was centered on me, my body, my desirability as a sex object, and not at all on the men, whose main role was to desire me, to give me orders, to make me act out the intensely arousing, kinky behaviors that were not a part of my normal life, to do these secretly and illicitly, for money, all of which escalated the intensity of experience specifically because it was so forbidden. Why that particular urge had taken hold, I really couldn't say.

But, at the moment at least, I wanted more. Judith had had a point, the convenient scheduling in my case might allow me to compartmentalize this, to explore sexual fantasies that would be impossible otherwise, all without disrupting the rest of my life much, given Michael's frequent trips. I was already curious about who Judith might suggest next, though it felt safe to merely muse about this as a hypothetical given what I thought was the buffer of relaxation that awaited me for the rest of the weekend.

And it started relaxing enough. Coffee at my favorite cafe, another beautiful morning, then a workout at the gym, followed by lunch with a friend. Lunch was the first full conversation with someone since the appointment with Paul, and as such posed a first test of compartmentalization. But it felt entirely natural, and never at any point did the events of the prior day lead me to state or imply or leak cues that I had begun a new hobby as a prostitute.

At home, late afternoon, phone lights up, Judith. This seemed to be a lowering of security from Signal chat, but I was home alone.

"So, how it did it go with Paul?"

"Fine, I think. You were right, he was nice."

"I told you. He said he liked you."

"Um, that's good. I owe you $200, by the way."

"Oh, no anal, eh?"

I snorted a quick laugh, "No, not yet at least."

"Just whenever you see me next for the money. So what are your thoughts going forward, do you want to try it again?"

Pausing, considering for a moment, but already knowing the answer. "Yeah, I think I do." This causing my heart to accelerate, the decision moving back out of the hypothetical to not only the real, but also to a consciously chosen pattern.

"Anything this week would have to be at night, though, since I am working all of the weekdays."

"Well, that is part of why I'm calling. I actually have someone interested for tomorrow morning."

This was unexpected, my plans for Sunday were more relaxation, a little work to prepare for the week, an evening call with Michael and the kids.

"Oh, I wasn't expecting so soon. Who is he?"

"His name is Jake, he lives pretty close to you, and uh,... so convenient travel. He is, actually, he's a college student."

A college student. This left me a little upset at first, starting to doubt Judith. Her carefully curated list of upstanding men of means, pillars of the community, had collapsed into any dick that could pay, and after only one client. Maybe this wasn't so safe after all.

"A college student?" likely a confrontational edge to my voice.

"I know, but he has good reviews from the girls. A trust fund kid, I think, he has money. I put out feelers, thinking you would prefer weekend days given your job, and he was the only one who responded with interest in Sunday. I described you and he was excited. I think he likes the idea of an Asian milf."

She described the apartment complex, one I knew, reasonably nice, and barely 15 minutes away.

"Are you sure about him?" the annoyance in my voice dropping, starting to be intrigued by the novelty of sex with such a young man.

"Yes, yes, we have never had any complaints at all.... What do you say? Since it is soon, I have to get back to him right away."

It was a convenient day and I had already resolved to continue trying this. Nervous excitement rising again (something I felt that I was now hunting, starting to crave), I responded, "Yeah, I guess so."

"Great, great, really glad. Oh, and one more thing: He says that he wants all of the standard extras."

My verbal agreement to the standard extras had sent my heart racing, my face flush, goosebumps on my skin. I knew I was driven by pursuit of that feeling now, which in the back of my mind presented dangers. I had just agreed to be fucked in the ass tomorrow by a college student I have never met, what might I agree to to get the same adrenaline high three months from now?

Throughout the rest of the day I would spontaneously picture an attractive, tanned penis (hey, it was my fantasy) attached to a handsome young man, turning my head to see the well-formed head pressing against my anus presented back to him, a feeling of pressure, but ultimately no pain and a building, intense pleasure. I had no realistic grounds for the specific parameters of that fantasy. My only experience with anal sex had been with my ex-boyfriend before Michael, who had only pressed the head into me, a slightly painful stretching to get it in (but not too bad), then asked me if it hurt and when I replied 'a little,' removed himself, never to try again. And yet, I had agreed to tomorrow.

I put on the same outfit, making a note that shopping was highly necessary if I were to continue this. I had slept fitfully, waking frequently, each time fantasizing about being fucked by a younger man in various positions, rubbing myself while half asleep, but then drifting back out before orgasm. My face looked tired in the mirror, attributed to this night of incomplete fantasies, and I tried to cover this up with more makeup than usual. I had actually woken up late from the poor sleep and was taking more time dressing than usual, to the point that there was some risk of being late for the 11 AM appointment. Given this, I decided to forgo the enema and rinse that internet searches suggested might offer some peace of mind regarding cleanliness, instead just hoping for the best. I did spend some time looking at my ass in the bathroom mirror, reaching back at times to spread the cheeks open and inspect my asshole.

Being in a hurry had reduced time to think much about my possibly ill-considered decision to accept this job, as I was focused on making it to the specific apartment on time. I found it, but had to park a few units down in the next open spot on the street, and had earlier gone straight to my heels in my rush to get out the door. Hence, a walk in heels, skirt, blouse, heavier than usual make-up, and sexual accessory bag past respectable apartments on a Sunday morning. It was an overcast day, as well, making the atmosphere seem less relaxed relative to the golden light that suffused the house in my encounter with Paul.

11:04 when I reached the door, damnit. Wringing the bell. A tall, lanky, thin-faced, pale, young man in T-shirt and jeans answered, everything about him seeming vertical (maybe 6 ft 2 to my 5 ft 5), beckoning me in with a quiet 'come in' delivered with fairly flat affect.

"Thank you," stepping in, good posture, then offering my hand once the door shut. His fingers were long and felt a little damp, his handshake somewhat limp. He was certainly not charming or outgoing, minimal eye contact, maybe a little shy about being with an older woman.