Fucking Every Wife in the Neighborhood: Part 2, Charity [MF]

I zipped up my pants and blew a kiss at Casi before leaving her and her husband's bedroom, my cum still dripping off her wedding ring buttplug. I went home, showered, and watched a little college basketball before heading over to pick up Charity for our Valentine's Day date.

You might be wondering how I ended up in this position, because Charity like many women of the neighborhood was married and most of them would be spending the evening with their husbands. It all started only a few nights earlier when we were at a weekly board game night, both of us again going it alone as her husband was in Bangkok on a business trip. She had straightened her hair in the past few weeks, maybe to look more like Casi and catch my eye, but it was still just as obvious that she was a brunette dying her hair blond. She had almost a whole bottle of wine to drink that night, and her short curvy figure was just perfect as always. She had a nose piercing that she sometimes wore (more often than she wore her wedding ring) and her face was freckled. The light blue dress she was wearing showed she had an amazingly round ass. Her waist was small, but her hips were wide, and I can tell you that, having seen her ass up naked, it is one of the most perfect I have ever seen. You would think it was Ai generated if it wasn't so real.

"Do you have plans for Valentine's Day?" Charity asked. She looked almost directly up at me when we talked.

"Maybe I'll convince our lovely hosts to take me in." I replied, motioning to Casi and Josh. I think just about everyone knew at this point that I was fucking Casi, and it was almost a joke that Josh was clueless.

Charity told me that her husband's trip had been delayed and he wouldn't make it home in time. They were supposed to go out to dinner at one of the nicest restaurants in the city, "but now I just have a reservation and no one to go with me. Even Alivia got a date that night. Most people here tonight are married so I probably should just give the reservations away to one of them."

"No, that's nonsense, let me take you to dinner." I told her.

"Oh. That sounds nice." Charity winked as she started texting. "I'll tell my husband I found a friend to take me out."

I went to dinners with some of my company's high powered clients before, so I knew most of the nice restaurants around town, and this one was one of the hardest to get reservations at. Dinner and quite a few expensive cocktails later, I realized the bill was probably more than her husband's plane ticket back from Thailand. But Charity gave me a look the whole night that told me she would make it worth my while. We stepped outside and I ordered a rideshare, one of the expensive ones, because the drivers are more discrete. She sat on my lap because she said she wanted to "look out at the riverfront," but I could feel her grind up against my cock as she stared out the window. There was a tinted partition between us and the front seat, and the driver either did not see that she was basically riding me reverse cowgirl, or he didn't care. I kept my hands on her waist and the sides of her ass the whole drive home while my cock bulged through my pants. We pulled up at her house and I got out there too.

"Come inside. There's a little wine left in that bottle from the other night." She held the front door open, motioning for me to enter. Before I knew it I was on her couch and she was pouring me a half glass of wine. We touched the glasses together.

"You know I was hoping my husband would be home tonight." She said. "I had it all planned out in my head but then his trip was extended."

"I think I played a pretty convincing husband at dinner." I replied, sipping my wine while looking at her.

"You felt a lot bigger than my husband in the car." She countered right back.

I didn't say anything in response. My blood was in my dick and my brain went blank so nothing clever came up.

"So," she started, smiling a bit as she spoke, "I think I'm going to get ready for my husband to come home." She started to get up. "You can stand in for more than just dinner tonight." She began walking down the hall towards the bedroom. I saw her take off her top and then her skirt before walking out of view. I quickly got up and followed her to bed.

As I entered the bedroom, I saw her set down a bottle of lube and a bottle of oil on the nightstand. There were towels on the bed and she got on top of them face down and completely naked. There were rose petals too, probably left over from the plans she had to cancel. Her ass was in full view and it looked even more amazing than I pictured.

"Can I get a massage honey?" She asked, without turning her head. Now I was quick to act.

I covered her body in oil and began massaging from her shoulders down her back and soon down to her ass. It was toned but not muscular, still very fat and round. Her body looked amazing covered in oil, shining like an angel in heaven. As I spread her cheeks I could see a red heart shaped buttplug in her ass.

"Has that been there all night?" I asked.

"I know we were going to save this for our anniversary, but I just couldn't wait. Valentine's Day seemed more appropriate anyways, right?"

I played along, pulling the buttplug out slightly and pouring lube around her asshole that was just starting to stretch out. I pulled the plug in and out of her ass, watching how tightly her ass gripped the metal. It was obvious she was extremely tight, probably never fucked before. It was also obvious that she had been preparing for this night for a while. I lubed my fingers up, sliding my index finger in first, and then my middle finger. Her tight hole resisted, but started to stretch out as I continued to finger her. "That ass is soooo tight." I said, almost moaning.

"I'm ready for your thick cock honey," she begged. I knew she wanted it from the moment she started grinding on me in the car. I pulled out my big white cock, precum already dripping from the head, and shoved it inside her ass, all the way inside on the first thrust, pressing my balls up against her wet pussy. I grabbed ahold of her shoulders, which was easy to do as she was so short, and instead of fucking her, I pulled her body back up against me repeatedly so that her whole body was moving back and forth on the bed to get fucked by my big cock. My balls made a loud clap as they slammed up against her, each time it was followed by a loud moan.

"I want your cum so bad," she moaned. I straightened my legs out so that I was no longer power fucking her on my knees and I put my feet between her legs and spread her legs wide, opening her ass even more. I wish I had put a camera behind us, the view must've been amazing. My balls kept slapping up against her pussy. "Please cum in my ass," she begged again, this time so loud that my dick immediately tensed up and I could feel my cum shooting inside her. Even though I had had sex with Casi earlier that day, Charity managed to get a huge anal creampie. My balls quivered as they emptied inside her, and I kept my cock inside for almost a minute before pulling it out. I saw a stream of cum pour out as I did that, and it poured from her ass down to her pussy, running along her thick labia and into her dark black pubic hair. She rubbed her pussy while the warm cum coated her fingers. Even though I thought her moans were loud before, she started moaning so loud that I'm sure it probably stopped several of the neighbors' Valentine's Day evenings. I watched for a few minutes, but after a point it seemed like she forgot I was there, she just kept cumming over and over again, even as I walked out of the house. Clearly she had been waiting for something like that for months. I couldn't even remember her husband's name, but I appreciated that he didn't fuck her for so long, it made our experience even better.

Charity's husband seemed to have more and more out of town trips over the next few weeks. Maybe it had something to do with me calling in a favor with his supervisor, a long time friend from school who owed me. My friend made a lot of the decisions about overseas travel and transfers, and this power would come in handy more and more over the next few months, as just about every guy in the neighborhood was subject to his decisions. Charity's husband didn't complain, especially when the company kept sending him to Thailand. Something told me he was getting fucked in the ass just as much as his wife. Charity, just like Casi, was an absolute slut at heart. Sometimes she would just text me a heart emoji, and I knew immediately what she meant--she wanted the Valentine's Day treatment all over again. The front door to their house would be unlocked, and she would be face down ass up with her hands spreading her ass wide open for me, her face looking directly ahead. Sometimes I left the front door wide open while I fucked her ass senseless.

Charity's ass wasn't the only thing about her I used, but it was what I went to most often. She could also suck me off without hardly bending over, she was that short, and when she got down on her knees I practically had to crouch down to get my balls to teabag her forehead. But it made her the perfect height to get thick facials. She didn't do that thing that many girls do when they are about to get a cumshot and they start to move their face up higher to avoid it getting in their eyes. Charity took it straight to the face and looked up at me with her beautiful blue eyes, sometimes with ropes of cum hanging off her eyelashes, always ready for more.

Soon Casi and Charity would give each other dirty looks at weekly game nights. Mostly because I started fucking Charity on those nights instead of Casi. It wasn't my fault; Charity would often text me something like "could you grab another bottle of wine from the garage?" and as soon as I would go out there I would see her bent over the hood of Casi's car, pants down with her ass spread. Her ass was so tight I knew it would only take two minutes to finish. How could I resist?

That doesn't mean I wasn't still fucking Casi, I was. Charity didn't want her husband to find out about us, Casi didn't care if Josh found out. On the rare occasions that Charity's husband was back in town, I would go back to Casi as a reliable fuck. Often after work I would walk up to her front door rather than my own, let myself in, usually finding her in the kitchen making dinner, and I would grab her by the hair, put her on her knees, and fuck her face. I loved slapping my balls on her chin and shoving my cock down her throat because I know it made her pussy wet and I know she wanted nothing more than to have my cock inside her, but I was going to make her wait.

Casi didn't stop texting me (and sexting me). She complained daily about Josh, about how he was playing porn too loud and they couldn't have guests over, or how he was always filling up their dishwasher with his sex toys. His dick barely worked, and the only times he was able to cum was into a pocket pussy (or as I later found out, Casi sometimes made him cum on his own face to humiliate him. She was submissive with me, but a fucking dominatrix when it came to her husband).

Casi really wanted to get pregnant. It sounded like her work from home job was boring, she needed a break, and she was worried about the fact that she was nearing 30 with no kids. Her parents were elites, living in New York, and were constantly pressuring her to have a baby so that they could have a grandchild to visit. Casi told me that her and Josh had a prenup (her aristocratic parents once again helping her make good decisions), and it said that he couldn't ask for a paternity test unless they got divorced, which was never going to happen because he would get almost nothing due to the prenup, so really anyone's cum would do to get her pregnant. She said she was thinking of trying to empty one of his masterbaters after he finished inside, pouring it into her pussy, because she had no better options.

"Don't do that," I said. "I'll take care of you, but on one condition."

It was a Friday night, and I had recently asked to have Josh sent out of town. He probably wouldn't have bothered us anyways, but given what I was about to do to his wife, I did not want to take any chances. I made sure to wait three days without having sex beforehand, as I've found that makes me have plenty of cum. I opened the door and there Casi was, in her wedding dress (my one condition).

"Welcome in," she said. Casi at this point knew what turned me on, and it was having all the small details in place. She had done her makeup just like it was her wedding day, probably spending several hours doing it, and she was playing classical wedding songs on the speaker. I walked over to her, running my hands up and down her body. She was ready to get bred.

She turned and began walking up toward the bedroom. I held her dress up so that it didn't touch the stairs. As soon as she entered the bedroom though, I stopped being a gentleman and started being the bull I knew she needed. I threw her on the bed, her dress flew up above her head, leaving her shaved pussy wide open for me. She even put a leg garter on, probably the one from her wedding, which I thought was a nice touch. I took control and fucked her in any position I wanted, but this time she was talking dirtier than ever before, and it was all about how bad she wanted me to get her pregnant.

"I'm not on birth control anymore," she moaned. "And I need you to put a baby inside me pleaseeeeee." She begged again and again for me to cum. "Cum inside me, I need it so bad. I have to have that big load. Please creampie my slutty little pussy. I'm such a whore for you daddy." I pumped away at her wet pussy, it was dripping with my precum and her juices. I flipped her over so that she was laying flat on her stomach in a prone bone position, the perfect position to get a slut pregnant. "You want this baby in you, you little whore?" I asked. "Or should I pull out?" She turned her head to look at me as if I had just insulted her. "Please don't pull out," she begged. "Pleaseeeeee. I'm just a cumdumpster. I'm just a sloppy hole for you to fill," she moaned again and I couldn't hold it in any longer. I emptied my balls inside her, filling her with a gallon of cum. I kept my dick inside her for what felt like an hour. Every time she moved slightly my dick twitched and seemed to shoot another rope inside, adding to the pool that was overflowing out of her.

The first time was so hot that we had to repeat it a few more times over the weekend. I was turned on by the idea of getting her pregnant and getting to fuck her in her wedding dress, and Casi just wanted to make sure she actually got pregnant, so we fucked six or s seven more times, each ending with a sloppy creampie in her pussy. After two days, I didn't think my balls could produce any more cum, and I told her I should head home. But then she asked if I wanted to cum all over her in her dress. I couldn't resist an offer like that, so she jerked me off for almost two hours while we watched porn together on the flatscreen TV in the living room (something her husband would never be allowed to do) until I was finally ready to bust one more time, covering her body and staining her dress with my cum.

Almost a month later, Casi texted me a single emoji, it was the white blond pregnant woman. I smiled as I texted back, "how did that happen?" She responded a few seconds later "Josh thinks it is from the time I fucked him missionary with a strapon and he came up in the air. I told him it must've slid down into my pussy," she followed that text up with a facepalm emoji and a finger shush.

The weekend of multiple creampies was not the last time I would fuck Casi, but more on that later. For now, I wanted to slut out Charity like never before.

One night I came home from work and looked at my phone to see that I missed a call from Charity around an hour earlier. Since her husband had been out of town for almost a week, I knew instantly what it was about. "On my way over," I texted. "Ok," she said, "I'll tell my friend to hurry up and leave."

I walked up to her front door and as soon as I reached for the handle, Kate opened it up. "Oh hey..." she said, looking a little surprised but also a little mischievous. She wiped her lips as she walked past me, usually she wore red lipstick but I could see her lips looked pink and whatever lipstick she applied earlier was wiped down across her chin as if she had just been drunk french kissing. She quickly walked past me, letting me in the door without another word. Was that the friend that Charity mentioned?

I went into the kitchen and saw Charity bent over the counter, naked from the waist down, waiting for me. I laughed a little, thinking to myself, "did she really just kick her friend out and take off her pants on a moments notice?" Without another word I spread her ass open and started to stick my fingers inside. Her asshole was wet and ready to go. I pulled out my cock to jam it into her asshole but it slid right in.

"What was Kate doing here? And why is your ass so wet?" I asked as I began pumping my cock inside her.

"You aren't the only one who has friends with benefits in this neighborhood," she said, turning to smile at me as she said it. "And to answer your second question, that would be from her tongue."

I looked down and saw the red lipstick marks around Charity's asshole. Charity would later reveal that she and Kate hooked up frequently. Kate loved to eat ass and get tongue deep, and Charity enjoyed anything being inside her ass, so it was a perfect match. Not to mention Kate's husband, Caleb, was very conservative and didn't enjoy anything like getting rimmed. So her and Charity had to make up for it.

Knowing that my cock was fucking an asshole where Kate's tongue had just been made me even harder. I kept pounding away at Charity's ass until I was about to cum. "Please cum on my face daddy. I love when you paint my little slut face." She was on her knees, begging. It had been a few days since I blew my load, so I completely painted her face, covering her forehead, eyes, cheeks and chin. Cum dripped off her. "Can you please fuck my ass a little longer?" She stretched her words out as she begged, knowing that she could keep me hard. By this point we had fucked so many times that she knew my secret talent, I can stay hard for several minutes after cumming. I thought her face does look really hot when it is glazed, so I kept fucking her.

As I was fucking Charity's ass while her face was covered in cum, her moans got louder and louder, and she kept begging for it even harder than before. Before I knew it, I heard a voice from the doorway to the kitchen.

"What are you doing honey?" Her husband was standing there, wearing khaki shorts and a polo, with a suitcase at his side. It wouldn't be the first time I got caught with a guy's wife, it wasn't the last time that I would get caught fucking one of the wives in this neighborhood, and Charity seemed like she didn't care either. She looked over at him but she didn't stop pushing her ass back up against me. He looked and I think for the first time realized that I was inside her asshole rather than her pussy.

"I thought we were saving that for our anniversary..." He sounded disappointed as his voice trailed off. After a few months of getting fucked in the ass, her butthole was much looser than it was back on Valentine's Day. If his dick was as small as Charity said, her ass probably wouldn't even grip it.

"Sorry bro," I replied as I kept on fucking.