Charlene

This is part 3 of the Charlene series. This part describes highly explicit sex acts. All characters and events are fictional; all sex acts are by characters over 18 and are consensual.

Michael and an ex-boyfriend were my only two prior partners for sexual intercourse, though I had also given blowjobs to one other ex-boyfriend. Thus, in one weekend, I had increased to three intercourse partners and five total cocks in my mouth. Stopping now after one weekend adventure would have been a reasonable and prudent course of action, but I knew at some level that I wanted to continue. No more college students, I resolved, but still an unmistakable urge to pursue further sexual adventures.

Judith invited me to dinner on Wednesday night, but otherwise no weeknight engagements. I maintained the sense of excitement through online shopping as a clear sign of commitment via the execution of concrete planning. I ordered three new lingerie sets, two stand-alone thongs, four pairs of different-colored stockings, a set of butt plugs, additional lube, another package of variously sized condoms, additional enemas, and a dildo for practicing deepthroating. Only the less disreputable items came from Amazon, the others from speciality websites, but always with express shipping to ensure quick arrival. Each order produced another hit of the nervous excitement, each promising future events that were made more plausible and likely by the actual events of the prior weekend.

I set aside $525 in cash for Judith. I deposited $400 in cash to my checking account, placed $250 into my wallet with a plan to break the two hundreds where possible, and then tucked $925 in cash into an envelope that was then tucked securely into the back of a box in the back of my closet. Dealing with the money was an issue. Too many cash deposits into bank accounts could raise tax issues if audited, and it was not easy to spend large bills. Maybe a topic to discuss with Judith.

Judith had ordered Thai food, which paired nicely with her usual assortment of white wines. There was the typical small talk lubricated with wine, before she initiated a debriefing.

"You didn't tell me he had a horse cock."

Judith giggling, "I'm not sure I knew that. I'm actually not sure he's our largest."

"I think he bruised my cervix."

"Oh no, what about your butt?"

"He came early, so we never made it to anal. That raised some issues regarding contractual obligations, refunds, and such. Though I did suck him off a second time when he was showing me out the door, and swallowed two loads, so I thought that was kind of partial compensation."

Judith with a seductive smile at me. "I knew you would be good at this."

"Remind me, when is Michael getting back?"

"Saturday morning."

"Oh, because I have a good opportunity for Saturday night."

"I don't know, I was going to spend Saturday with Michael. I think I owe him that."

"I know, but this is a special request and a really good job. It is a couple, offering $5,000 for two hours."

I hadn't really considered a couple, and the prospect of the new experience had primed that same jolt of nervous excitement the pursuit of which was becoming a new addiction for me.

"Have you been with a woman before?"

"No, never."

"Like I said, new adventures. This is a pretty important client and they thought you would be perfect. You could tell Michael that you are coming to a girls' night here, and I could vouch for it. Just 2-3 hours out of the house and then right back home, since they live in my neighborhood. I would really owe you one if you can do it for me. Here, let me show you a picture."

He appeared to be in his 50s, thinning hair, a bit pudgy, but not unattractive. She was tall, about my age, slightly dark complexion (Peruvian), long dark hair with grey streaks, large facial features but still pretty and feminine in an exotic way. I definitely spent more time looking at her, increasingly curious about what it would be like to have sex with her.

"Let me ask Michael if it is OK to go out for a few hours that night. I can get back to you tomorrow."

Predictably, Michael was fine with it. I promised to spend all day Sunday with him.

"I really do owe you one!" via Signal text. "Also, all standard extras, if that is OK. Plus one more..." dots in the text box, a long delay. "Well, two. They are requesting kissing, and a new one: rimming. I hope that is OK. It is reasonable given the price."

This set my heart racing again, the reaction I couldn't resist, and that I started to suspect that Judith was manipulating.

"OK, but you do owe me!"

I spent Thursday night playing with well-lubed butt plugs. The intermediate size was too painful to insert, though still smaller than many penises, which had me worried. But I found that by holding the smallest one in for a while, I could manage the next largest size, and I gradually worked my way up to penis-sized plugs. Once I had them in, I would move them back and forth, slowly, which actually felt really good. Figuring out a way to stretch myself right before the date was a challenge that I needed to consider.

I spent Friday night practicing deep throating. The life-sized dildo was too difficult, but again I found an incremental approach helpful. I was able to gradually ease the longer and thinner butt plugs into my throat and control my gag reflex, and I found that I started to habituate to the sensation of swallowing cylindrical objects. The dildo had a suction cup that I attached to a wall in the bedroom, and in my best attempt I was able to move my lips within an inch of the wall.

I was genuinely happy to see Michael at the airport on Saturday morning. My main concern was being affectionate to an extent that might raise suspicion. I definitely kissed him a bit more fully than our standard greeting.

"I missed you."

He laughed a little, "Oh, that was nice. I missed you too. Maybe I can start to suggest shorter trips ..." a slight hint of guilt in his voice, as though taking my statement as a mild criticism.

I was definitely open to having sex with him--actually craving it much more than usual--but he had taken a red-eye and so after having a brunch at one of our favorite places, he fell into a deep sleep. This gave me some opportunities to prepare for the date. A couple of hours after eating, and after a bowel movement, I gave myself an enema and follow-up rinse, which came out looking clean. I packed a sex bag and placed it into the trunk of my car, knowing that I would have to leave the house in regular clothes. The final step would be to stretch myself with some butt plugs, which I hoped to do around 6 PM given that the date was set for 7.

I was making an early dinner for him when he came out of the bedroom looking groggy. I caught a glimpse of my laptop open in the adjacent study, probably some pop-up notice having taken the screen out of hibernation. I could see the word "Charlene" (or maybe filled it in knowing that it was there) on a Word document and realized that I needed to get in there to close the screen. Discovery of that document by Michael would have triggered an awkward conversation, to say the least. Fortunately, he left the kitchen for a minute, and I quickly popped in to close it up.

I parked in the driveway of a fairly large house, wearing jeans, a stylish T-shirt, and casual shoes, the walk to the door more relaxed given the outfit. Herb answered the door, looking a little heavier than in the photo I had seen. Judith had received payment by Venmo and so I didn't need to worry about counting money. Maria walked over as soon as I came in, wearing a blue dress that came down to her knees, tall and elegant, dark pink toenail polish contrasting nicely with the dark complexion of her skin. She walked right up to me and offered her hand, "Charlene, I am Maria."

"Maria, you are so lovely. It is really great to meet both of you."

There was jazz playing over a built-in sound system within the large living room that contained various art pieces; paintings on the wall, small metal statues of human-like figures, and an assortment of vases, other pottery, and ceremonial masks. They clearly had disposable income, and the entire environment felt relaxed and comfortable. Both of them looked me up and down and seemed to approve of my general appearance. My gaze drifted naturally to Maria, excited and a bit nervous to touch a woman sexually.

"We were just having some champagne, if you would like some."

"That would be lovely." They handed me a flute of champagne and led me to a large, leather sofa.

"Maybe you could sit between us so we can get to know you a little." I was happy to oblige, sitting in the middle of the long sofa, the two of them sitting on opposite ends. The ensuing conversation was in fact a get-to-know-you session, perhaps intended to make the sex more exciting when occurring with a three-dimensional person instead of just a borrowed body. Maria was Herb's second wife, two grown kids with his first wife. For Maria, also a second marriage, but no kids. Herb had apparently sold some type of a business and was now semi-retired, and Maria was running an art gallery that specialized in South American indigenous art. I gave the broad outlines of my biography while careful to conceal identifying details; two kids in college, a successful job at a tech company, degrees from prestigious universities. They seemed to eat it all up, excited to have sex with someone with a profile atypical of most sex workers. They were especially intrigued that I was taking the risky step to live out a secret fantasy.

"This is really nice chatting, Charlene, but with the time constraints, maybe we should get started. Could you strip for us?" Herb sounded excited saying these words.

A little tipsy from the champagne, which I had drunk quickly, "Sure, no problem."

In front of the sofa was a large, very soft, animal fur rug. I stood up, took a couple of steps onto it, and turned to face them. I peeled the T-shirt over my head, revealing a lacy, light blue bra. I slowly unzipped the jeans, then pulled each leg down, stepping out of them, revealing a matching, light blue, thong panty. My heart starting beating faster, feeling both of them looking at me. I turned around, showing them my ass, only the thin string of the thong between the cheeks. I turned back around slowly, unclasping my bra and then letting it fall, first covering my breasts with my hands, then dropping them to my sides. I paused for a moment, then pushed the panty down and stepped out of it, tossing the clothes to the side of the rug. Herb had started rubbing himself through his pants; Maria's gaze traveled slowly up and down over my naked body.

"Charlene, I would like to see you kiss my husband," said in a slow, slightly husky voice.

I walked to Herb and slowly positioned my legs over his lap, then pressed my pubic hair against the bulge in his soft pants. Maria would be able to see the sides of our faces clearly in this position. I placed my tongue in his mouth, a minty taste but overlain with the distinct smell of alcohol on his breath. He caressed my breasts as we rubbed tongues, me closing my eyes, feeling myself getting wetter. I looked over at Maria to see that she had pulled up her dress and was reaching into her panties to rub herself. Herb licked my neck as I looked straight at Maria, maintaining eye contact with her while I moaned a little.

"My turn, honey," Maria said to Herb.

I climbed off of him and walked slowly to Maria's side of the sofa. I sat next to her on a side such that Herb could see our faces when she turned to her left to kiss me. We began rubbing tongues, a strange feeling for me that I had trouble categorizing, but that was not unpleasant. Maria seemed to have a long tongue, which she reached into my mouth and rubbed around and over my tongue and cheeks. I placed my left leg over her lap as she explored my mouth with her tongue, feeling myself becoming increasingly aroused. I heard jazz in the otherwise quiet room, then the sound of clothes being removed from Herb.

When I opened my eyes, I saw Herb standing on the rug, naked, stroking his erect penis.

"Let's go suck my husband's cock," smiling as she said it.

Maria removed her dress and panties, and we walked over to Herb, both of us completely naked. We both dropped to our knees. Maria began licking the left side of his shaft, and following her lead, I licked the right side. Herb put his hands on his hips in a type of Superman pose. I looked up at him as he looked down at two naked women licking his cock, seeing how excited he was. I thought to myself that Michael deserves this feeling, and in that moment, I hatched a plan for him.

Maria pointed the head of Herb's cock toward me, and I moved a little to my right and began sucking it. She stood up and rubbed his chest, the two of them looking down at me. I held it at the base with my right hand while trying to work him deep into my mouth. He was average size, maybe a little under six inches, and by pressing the head into the back corner of my mouth, I was able to get most of him in without gagging. I was slurping like this, back and forth, and was even able to slowly ease some of the head into my throat, holding it there for a few seconds with my lips close to the base of his cock. He moaned from this, both of them staring at me, Maria cooing, "Ooh, she is a good cocksucker."

I started sucking faster, using a lot of spit, bobbing my head back and forth on him, Maria stroking my head a little with her left hand. "Unngh, yes, suck me," Herb turning his head up toward the ceiling while feeling this, and Maria then kissing him deeply. It was a little romantic to see them kiss as I sucked him, knowing how good I was making them feel.

I sucked him like that for a couple of more minutes, before Maria knelt back down next to me. "Why don't you move around to the back, Charlene," which she said a bit mischievously.

Oh, fuck, here we go, I thought. His ass was a little large and I had to exert some force with my hands to pry the cheeks open enough to clearly expose his anus, but doing so, I leaned in and extended my tongue to touch it to his asshole. On the other side of him, I heard Maria slurping on his cock. I was just flicking my tongue lightly when he reached back with his hand and pushed my head forward so that my tongue pressed more fully against his anus, my nose pressing deeper between his cheeks. I couldn't see what I was doing pressed in like that, and so just flailed my tongue, trying to lick firmly against his butthole. The tactile sensation made it difficult to say exactly what I was licking, but he began moaning loudly, which was my indication that I was hitting an acceptable spot. I heard myself making little grunt-like noises as I rubbed my tongue around blindly, thinking that he was getting his money's worth. I reached up between his legs and fondled his balls a little to add another sensation, impressing myself with the spontaneous innovation.

Herb let go of my head and asked me to get on all fours in front of him. I dropped down, the furry carpet perfect for this, arching up in a position that always made me feel sexy. Maria was stretching a condom over him when I looked back at them, me feeling aroused by the knowledge that my ass and pussy were on display. She used her hand to guide his cock into my pussy, a couple of thrusts necessary before it slid completely in, but the entry mainly smooth given how wet I was. "Uuuuumpf," emitting a light, pleasant moan as I felt him fill me, not too large, just a comfortable sense of fullness.

Herb began thrusting into me as Maria stood next to him.

"What a nice little pussy," in a smooth, deep voice from her.

I stayed arched, my head upright, feeling the thrusts push into me. Maria walked slowly around in front of me, looking down into my eyes as I was being fucked.

"Your husband has a great cock."

She moved down onto the rug and spread her long legs wide open in front of me. She had a large, dark labia and what appeared to be a bulbous clitoris. I moved my head down toward the rug, my ass still up as Herb continued stroking into me, and Maria inched forward to put her pussy right beneath my mouth. I moved down and was struck with a pungent, mostly unpleasant odor, but suppressed any reaction to this and began to run the tip of my tongue over her outer pussy lips. Peeling its hood back with an index finger, I began to lick her clitoris, but had difficulty maintaining contact since my head was shaking from being fucked from behind.

"Fuck her hard, honey."

Herb responding with harder and deeper strokes, this triggering moaning from me but also pushing my mouth off Maria's clit. Maria placed her hand over my head to hold my mouth in position, which helped me keep my tongue on her clitoris as Herb pounded his cock into me.

I was starting to habituate to the smell, but was still pretty uncertain about what I needed to do down there, just trying to push and swirl my tongue over her clitoris, but not knowing the ideal pressure or pace. There was a slightly acidic taste but the gustatory sensation was far weaker than the associated odor.

Maria stood up again, me wondering if that meant I was offering substandard cunnilingus. I propped back up on my hands to give Herb a good arch, and he fucked hard into me, moaning "Fuck, that's good."

"Do you like that tight Asian pussy?" excited to hear those words come out of me, looking back at him, seeing him exert himself, beads of sweat on his face.

"Fuck, yes, uggh."

Maria pried my ass cheeks open as I continued to get fucked, then rubbed her index finger against my anus.

"Do you want to fuck her ass, babe?"

I felt myself lubricate even more upon hearing those words.

Herb had good cum control and was staying fully erect, so I knew that I was going to get a proper buttfucking this time. He pulled out and Maria starting to rub lube first on his cock, then over my anus, the gel feeling thick and cold. I stayed very still, fully arched, aroused by the thought of being used by them in whatever way they wanted.

Without any verbal warning (no countdown or 'ready, set, go'), I felt an intense pressure from the head of his cock against my anus. He was thicker than my butt plugs and it felt too large to fit, feeling some pain as I stretched open, but trying to relax and take deep breaths. I would have stopped if I were pressing a toy into myself but he kept pushing and once past the seal the stretching at the point of entry felt less painful. But now a sense of intense pressure that felt too deep as he pushed in, me emitting small, clenched-teeth groans, my deep breaths turning into audible, fast-paced, in-and-out panting.

Maria caressed my back a little, "Almost in, you are doing great."

He was pushing in slowly but steadily, seeming to push up into my guts, the pressure definitely uncomfortable. I remembered a phrase from an internet search about anal sex, the poster having characterized it as 'gnarly at first' (but better over time), trying to stay strong and keep my composure. Herb held still for a few seconds, which seemed to help me accommodate to the depth.

"Mmm, he is balls deep in you now, Charlene."

Herb leaned onto my back, cupped my breasts, and kissed the back of my neck.

"It's so deep," I managed to groan out, tremulously.

He reared back up, held my hips, and began to pull back. It felt like I was slowly pooping him out of me, the friction a little pleasurable. He pushed back in slowly, then gradually built some speed, with small thrusts back and forth in my ass.

"Look at her tight little ass gripping you," Maria still standing behind me. "Good girl, Charlene."

Herb started thrusting in faster and harder, each thrust in eliciting a quick, deep grunt from me, a quality of sound I had not heard myself produce before. I was starting to relax and get more aroused, the thrusts combining pleasurable friction with uncomfortable pressure, the two together feeling incredibly intense.