Charlene

This is part 5 of the Charlene series. If you have read the prior parts, thanks! If you haven't read them, this chapter will make more sense if you read the prior chapters first. This story depicts consensual but explicitly described sex acts. All characters are fictional and over 18.

Michael had a short business trip the next Wednesday through Saturday, and I took Wednesday off to drive him to the airport in the morning. I met Judith for lunch at her house afterwards, our first contact since the threesome.

"Well, Erin, how did I do?"

"You were fantastic, of course. Michael loved it. We even have an anal sex date for Sunday after he returns." (My period started the night of the threesome, so we put off sex until Sunday.)

"Glad I could help with that," laughing at the date part. "So, you remember that part about accepting a big job if I was good with Michael, right?"

I certainly had remembered. In fact, the anticipation of what this large job could be, and my already-determined obligation to accept it, were, since Saturday, the main sources of the nervous excitement that I sought to maintain as often as possible.

"I remember, and you were great for him, so I am pretty certain I am going to accept no matter what it is."

A little smile from Judith, she holding the advantage again, but still, in the grand arc of our relationship, she was now a little less socially dominant over me in general.

"OK, well, there is a guy I have know for awhile named Kip. Nice guy, pretty rich, owns a yacht. A week from Friday he and two friends are going to sail it from Santa Barbara harbor to the Channel Islands and stay overnight anchored at the islands. Leave on Friday afternoon, return Saturday night. And, well, they want to hire you as the entertainment."

This did the trick in terms of nervous excitement. I had never been with two men, let alone three. Small goosebumps appeared on my arms and I felt my pussy lubricate.

"Oh boy."

"There's more. They are looking for a kind-of free use type of situation. Very few limits, pretty much on-demand sex for all three holes." She said that line a little impishly, seeming to relish it. "I'm not sure if they want to do this, but it might include double penetration. I'm guessing you haven't done that?"

Nope, seen it in porn, but never anything close to it in real life.

"I don't know the other two guys, but Kip is very well-reviewed and like I said, I know him, and he vouches for them. Kip's about my age, one of the others is a little older, maybe early 60s, and the other one a little younger, late 30s or so. It's a big job, overnight and everything, but they are offering $20,000."

"Wow, that's real money. I do owe you, but Michael is in town that weekend, that's the thing..."

"Yeah, I thought you could tell him you need to take a business consulting trip. And in fact, for a payment this large, I can help you set up a consulting agreement with NDAs and also a special bank account, and they can wire the money to the account and provide receipts for the consulting. It should be something related to your expertise so that it all checks out if necessary. If you can take Friday off, you can tell Michael that you have a business trip this time."

She had thought it out pretty well. I did have more personal days and could take that Friday off, drive down in the morning, probably drive back Sunday morning if I stayed in a hotel on Saturday in Santa Barbara. Michael offering to take a day off to come with me might be the biggest risk to the plan, but I might be able to talk my way out of it if it came to that.

"I need to try to make the arrangements with work and Michael tomorrow, but if I can, yes, I'm in. But I think after this one, you will be back to owing me."

She gave me the seductive smile again. "My butt was a little sore last time, but sure, tell Michael he can saddle up on me again."

In the meantime, Judith had one other possible job for me, on Friday night. Her recommendation for this guy was more ambiguous than the others; some of the girls found him creepy, but nothing sketchy or dangerous. And he had a particular fetish: no intercourse, just a continuous blowjob for the entire hour, cum in mouth. They had a standing $600 arrangement for this, which seemed fair enough.

I decided to decline the job, however. Creepy was a sufficient red flag for something that was essentially a hobby for me, and in addition the drive would have been over an hour, one way. Judith wasn't too put out by this, probably because I had already accepted the yacht orgy job. But I told her that I was still open to other good opportunities before Sunday, though Thursday and Friday would have to be after work.

I texted Judith the next day to say that I could do the yacht job: Michael was OK with my business trip (he had a work event that Friday, too, which precluded him from joining me), and I was able to take the day off from work. I was excited about the trip, and had already spent an evening shopping online for a new bikini.

Judith texted back on Thursday evening, saying that she was happy about the yacht job (sure, $5,000 for her!), but that she also recently received a new request for me on Friday night.

"Your first repeat customer."

"Really, who?"

"Jake. He is asking for an overnight, too, $4,000, anal included."

Oh. I called her back on the phone.

"I have a little hesitation about this job. I'm worried that he's getting sweet on me."

"Maybe, but guys getting sweet on girls is half our business model."

"I guess so, that makes sense. Still, with the age difference and all. And are we sure he can afford this?"

"I know that he has a big trust fund, so I wouldn't worry about that. Plus, maybe he just really liked your ass."

"He told me as much. Damn, though, I should probably line up a proctologist just in case."

In the end, I accepted the job. The thought of letting him use me overnight was intensely arousing, but I would try to be careful about him getting any expectations about us. It would also let me try out an overnight on a day when Michael wasn't home.

To my surprise, Judith texted again later that same night. She had just gotten a request for me on Saturday night, too. A former regular client who was in town on business and staying at a hotel downtown near my company. My reputation was spreading and he specifically requested me.

"Totally fine if it is too much with the overnight the night before."

It might be a bit much. I knew I should refuse, but accepting the back-to-back jobs was the most arousal-inducing response, and so I accepted this job, also. Just one hour in his hotel room, no information about extras. Mid-forties, a reliable client when he lived in town.

Friday was a hectic day at work and I started to doubt whether I would have the energy for the weekend sex marathon. I was a bit distracted by the upcoming jobs and found myself behind on completing various tasks. I planned to go home a little early and prepare for the overnight, but wasn't able to leave until 5.

I was supposed to be at Jake's at 8 PM, and had hoped to eat early, rest, shower, and do some stretching. Traffic wasn't too bad and so I was able to eat some leftovers around 6, but really needed to just sit and close my eyes for a bit before any further preparation. A night of television watching plus a hot bath sounded really good at the moment, and I thought I would have to rely on adrenaline to get through the overnight.

I finally forced myself off the sofa and began pressing butt plugs into myself. There was always an excitement associated with this previously, but this time it just felt like a task I had to finish, kind of like of doing dishes when they had piled up for a while. Except this hurt a little and I felt like the stretching wasn't quite taking effect enough to be fully prepared. I followed this up with an enema and a shower. By the time I packed an overnight bag and put on lingerie, make-up, and a short dress, it was already time to go.

"Hi Charlene."

"Hi Jake," walking in, giving him a hug.

"I'm really glad you could come tonight."

"Sure, I was excited to hear that you requested me."

"I couldn't stop thinking about last time with you."

"That is sweet. I'm glad I ran into you that day."

We continued standing awkwardly near the front door, HCB being generally deficient as a host and not inviting me in further. I thought briefly that maybe I should just drop to my knees to move things along.

"I was going to have a beer if you want one."

There we go, finally. I followed him into the kitchen and we cracked open a couple of IPAs in cans. I hadn't had any wine at home for fear of getting too sleepy, but this was hitting the spot, a little relaxant to help me through what might be a long night.

"So, do you have big plans for me for our sleepover tonight?" I decided to be a little seductive, again to move things along, since the prior 30 seconds were filled with silent beer sipping. I thought I could handle the sex, but the time between erections might get pretty painful (in a different way!) given his awkwardness, and I started to second-guess an overnight with him. Thinking about it later, I realized that preferences for an overnight were much more aligned with preferences for a long-term mate instead of for a short-term sex partner: ideally, he would be funny and a good conversationalist, someone you enjoyed passing time with; and the whole evening would be much more comfortable if he had means and taste, a nicely furnished house with comfortable linens, good music, good alcohol, maybe a stylish outdoor space with a nice hot tub. I had seen HCB's messy bedroom and less than spotless bathroom, which were not close to the ideal.

"I mostly want to have as much sex as we can. I didn't want it to end last time."

"Aw, that is sweet," I caressed his arm with my fingers and moved closer to him. "Do you want to start the sex right away or would you like to talk a little first?"

He opted for talking and we moved to the sofa where I had gagged on him during our first date. I asked him about his major as we finished the beers. Business accounting, one year left. That was the main conversation topic that I had planned for the overnight, and it was essentially exhausted after 30 seconds. He remembered my donation at that point, and I went to the bathroom to freshen up and count it.

The bathroom looked cleaner, which I attributed to a likely cleaning service, but I appreciated it given the more extended stay. The envelope contained $4,000 in cash, which I counted a couple of times to make sure it was correct. I peed, washed hands, and touched up my make-up.

I came back out, took my heels off, and sat close to him, light blue stockings on my legs, which extended out of the short blue dress. Had he managed to conjure up a conversation topic?

"Are you OK with kissing this time?"

Oh, on to the sex.

"In general I avoid kissing, mostly because I want to limit the risk of viruses. I mean, if I kiss enough people, eventually I'm going to catch something."

I processed the possible negative implications of that statement and immediately regretted it. First, that I was sleeping with a lot of men (not just him), and second, that I wasn't all that into kissing him. My reflexive impulse anytime I sensed possible disappointment in a client was to ramp things up to rectify it, and I came up with something very quickly here.

"I'll tell you what, though. I will do kissing on one condition," rubbing his leg as I said it.

"What?"

"That you try to make me cum during one of the times we have sex. I can give you some instructions."

In a moment of over-inflated self-congratulation, I thought that this was a pretty ingenious save. He would get the kissing he wanted, but could also get the self-esteem boost associated with pleasuring me. Prostitute of the Year, or something.

While still internally congratulating myself, HCB nodded, leaned in, and put his tongue in my mouth. No sign of pickle smells, but I still didn't really like kissing him, his tongue being a little too long and wet. My arousal in response to HCB really followed from the kinkiness of the age gap, and also, of course, his enormous novelty cock. Still, I kissed him back and placed my left leg over his lap as I leaned in closer to him.

We kissed for a couple of minutes before I stood up and took my dress off. I was wearing a light blue bustier that connected to the stockings with garters, but with no panties in order to show off my ass and pussy.

"I bought this set for you, Jake." (Only technically true in the sense that I had bought it for clients in general.)

Jake immediately unzipped his pants and pulled out his huge cock and started jerking it. He was clearly excited by the sight of me in lingerie.

I sat next to him again, resumed kissing, and started rubbing him with my hand.

"I love your big cock," whispered into his left ear, licking his earlobe after I said it.

"I want you to suck it."

I got onto my knees in front of the sofa and starting sucking straight down onto him. I pictured myself at work earlier that day, visualizing a specific spreadsheet I was working with, the business suit I was wearing, and then thought of the contrast with myself now, on my knees in lingerie, sucking off a college student. My pussy was soaking wet and the fatigue from after work had evaporated from the adrenaline rush.

I was excited and wanted to ramp up the intensity even further. I went for the kinkiest thing I could think of.

"Stand up," looking up at him as I said it.

After he stood, I put his dick back in my mouth and sucked him hard for a few seconds. Then, the real kinkiness.

"Turn around."

He hesitated, but I repeated it.

HCB turned around, standing in front of me as I continued kneeling. I quickly put one hand on each skinny butt cheek and pried them open. I leaned in and started to lick his butthole.

"Uggghh, fuck."

I could see his elbow moving back and forth fast as he jerked his cock. I licked more firmly, running my tongue all over his anus. Presumably, Herb and Maria had cleaned themselves well back there, knowing that they had requested rimming, but I was definitely taking a chance with HCB's hygiene. But my heart was racing, my pussy dripping, and the nervous excitement had moved like a wave across my entire body. I was basically a junkie, and escalating kinkiness was my drug.

I ate his ass for maybe a minute or so before I stood up, reached around him, jerked his huge cock, and whispered in his right ear, "I wanted you to know what I slut I can be for you."

"Uggh, I'm going to fuck you."

He grabbed a condom he had left near the sofa and started rolling it on. He was rock hard and extended out beyond his body at a ridiculous length.

Jake got the condom on quickly this time, grabbed my left wrist, then told me to turn around. Fair enough, I had just said the same to him. He helped to spin me around by my left arm, then pushed me forward a little at the small of my back and told me to bend over. I liked his new assertiveness and obeyed him, hands on my knees, but thought that I might be too tight for an initial rear entry. He jabbed his cock against me a few times until he found the right angle, and to my surprise, he pushed in pretty easily, aided I imagine by how wet I was.

"Oh, fuck, that is big."

He then reached forward, grabbed my wrists, and pulled my hands behind my back. He held me up by my arms and made short, fast thrusts into my pussy. It was more of a jabbing than anything and didn't feel too deep. But what he did next was much more intense.

Jake let go of my arms, then reached his arms around my sides and underneath my chest, extending them forward far enough to grab my shoulders with his palms up and fingers curled back toward him. Leaning this far forward, his smooth chest was partly pressed against my back and his thin legs were pressed close around my own legs. He bent his knees, and with the force of his body making me bend forward in a way that opened me up more, he found a new angle that allowed him to press what felt like his entire cock into me. He began thrusting into me at this angle, pulling back maybe three inches or so before thrusting back in, repeating this, producing the combination of deep pressure with thrusting friction that started to overwhelm me.

"Ummmmh, uhhh, oh God, oooh," flowing out of me in a soft, deep moan.

Jake was skinny but still much stronger than me, especially with his height, and I was completely pinned under him, unable to move, and held up by his arms under my chest, his legs effectively supporting both of us in a standing position. The depth of penetration was completely under his control and I just closed my eyes and felt it.

"Oohh, Jake, hold me like this, don't stop," in a breathy, moaning whisper.

"I love fucking you, Charlene."

He kept pounding his cock into me, the head hitting spots deep in my vagina, making me pant and moan and groan, an escalating intensity building in me with a desire to rub my clitoris but being unable to do so with my arms restricted by his grip on my shoulders.

"Fuck me, Jake, fuck me,...oh, keep fucking it."

Jake started to moan very loudly, pulled up off my back, grabbed my hips, and began thrusting in wildly, pounding me hard, seemingly losing control.

"Ahhhh, ahhhh, fuck!" Jake shouting the words, then holding still in me, a last hard thrust as he came into the rubber while fully inserted in my pussy. Then breathing hard, holding himself inside me.

"Mmm, did you give me all that cum, Jake?"

"God, so much," panting.

"You fucked me so good," turning back, reaching to his face and patting it with my hand.

Jake pulled his dick out, the tip of the condom visibly filled with white semen. I stood straight up, turned toward him and kissed him deeply as he breathed hard through his nose.

"You get me so excited," looking at me as he said it.

"Mmm, I'm glad. Maybe we should cuddle."

He went to the bathroom to clean off first. I grabbed a water bottle and checked the time from my phone; 8:32, barely a dent in the overnight, and also a missed call from Michael. A pang of guilt about missing his call because I was being railed hard by another man at that moment.

I had to admit to myself, the sex was fantastic. The deep vaginal penetration might have produced an orgasm even without clitoral stimulation if only Jake had held out a little longer. The overnight, which had seemed impossibly interminable during the early awkwardness, now held out much better potential.

Once Jake was out of the bathroom, we went to his bedroom, laid side-by-side on his bed, and resumed kissing. I felt like I was kind of committed to the full girlfriend/kissing experience at this point, and I enjoyed it a bit more after the pleasurable sex. I ran my hands over his thin, smooth body, and he did the same to me, caressing my side, stomach, and legs. Having his tongue in my mouth carried the side benefit of not having to attempt awkward conversation.

After a few minutes of kiss-cuddling, I did tell him that I was pretty tired from my day job and might want to rest my eyes a little. The fatigue had hit me again after coming down from the sexual arousal. Jake was fine with it, and I gave into the sleepiness, closing my eyes while lying on my back.

I woke up surprised that I had fallen into what felt like a pretty deep sleep. Jake had left the room. I spotted a clock: 9:49, meaning I had dozed for about an hour. I felt fully awake now but thought I could, in principle, kill more time by just lying there awhile longer. But my sense of conscientiousness compelled me to get up and look for him, trying to make sure he got his money's worth.

I found him in a second bedroom that I had not seen before, which was down a short hallway off of the living room. Jake was sitting in a tall-backed gaming chair with a headset on, holding a game-controller, and facing a large-screen TV that was displaying some type of video game. So this is what he did when he wasn't banging escorts.