The Legend Of The Free Sitter

Anonymous said: ... Jennifer, I had an idea that I think only you could crush. "The legend of the Free sitter" It would be about a black man in primarily white community. Who babysits for "free", and only the wives of the community know about him.

*

Today was the day I'd been waiting all week for. It was my turn to have Josiah, the local babysitter watch my children for the evening. As a married woman, I knew that I shouldn't be doing what I was about to do. The problem was that I couldn't seem to stop myself. My husband had no idea what Josiah really was and he had no idea how I had been up texting with him every night that week leading up to today.

"You about ready?" Carter asked, adjusting his tie in the mirror. He was about 5′9 with reddish-blonde hair and striking green eyes. He had a smattering of freckles on his cheeks that made him look a few years younger than forty, which was his age.

"I just need about five more minutes," I turned my back to him and he could sense what I needed without me having to ask. Wordlessly, he zipped up my red flapper-style dress. The doorbell rang and we both jumped a bit.

"Can you get that while I finish up?" I asked Carter and he nodded and headed out to grab the door. I was a bit nervous about Carter and Josiah being alone together for too long and so I sped through my makeup process, careful to take my time on my lipstick so it didn't bleed into the wrinkles above my lips. I was forty-two and I wasn't loving it the way everyone had said I would. I was tired most days and nothing seemed to satisfy me anymore.

I walked out into the living room, where Josiah and Carter were talking animatedly about sports, something I knew nothing about. I continued to get things ready for our son, Rolan to make it easy for Josiah to care for him while we were gone.

"Any instructions for my for the babysitting gig?" Josiah smoothly transitioned from talking to Carter and turned to me.

"He's pretty easy. His dinner is actually here you just need to heat it up."

"I'm good at heating things up," he said and the way he said it made my pussy instantly horny. I was hoping that I could get a piece of that dark chocolate later after we got home from babysitting. I had my plans and I'd been working on them for weeks.

"Well isn't that just steamy," I said quietly, so only he would hear me. Carter was on the phone anyway, like always. It had been a long time since he had looked at me the way Josiah was looking at me now.

"It certainly can be. You look fucking hot," Josiah's voice was filled with the promise of passion and orgasms and his muscles were stretching out his simple t-shirt in ways most men's didn't.

I made sure my secret weapon was in my purse.

"You look hot too. I'll see you when we get back."

"Do you think you might need any additional services?" he asked, his voice low and flirty. His dark skin was the perfect shade of naughty and I knew that I had to have him. All of my friends had talked about him like he was the best thing that had ever happened to them. This was my chance to find out and I wasn't going to let Carter get in the way.

"You ready?" Carter suddenly appeared his phone still in his hand.

"Yes, our reservation is for eight. We better get going. Let me say goodbye to Rolan!" I hugged my son goodbye as he watched his favorite movie for the millionth time.

"Good evening! Have fun tonight!"

"Thank you for watching Rolan for us."

"It's my pleasure. I love children."

"You also love hot wives," I thought to myself but I could never say such a thing out loud with Carter right there.

We rode to the restaurant in silence and Carter picked up a work call as soon as we arrived. He was still rudely discussing a merger as we were shown to our table and when he finally got off the phone to talk, I could tell that Carter would rather be anywhere else but with me. It was always like this and I was sick of it.

"I need to use the restroom," Carter excused himself. The waiter brought our dessert while Carter was gone and I couldn't help but think that this was my chance to carry out the plan I had concocted. I pulled the vial of liquid from my purse and poured a bit of it into his cup of coffee and a bit into the sundae he had ordered for dessert. I tried my best to get it all in the hot fudge.

"What are you doing to my sundae?" Carter was standing over me.

"I want some, but I'm trying to resist. I gave up sweets," I lied.

"Then explain why you ordered creme brulee!"

"You're right, I'm a fraud. I was going to have a bite of your sundae, but I don't deserve it."

"You know you can always have some. What's mine is yours."

"That's okay. I changed my mind," I moved my spoon back and watched as Carter sat down and ate his entire sundae, following it up with his warm coffee. I knew I didn't have much time to get him home. By the time he paid the check, he was getting woozy.

"Come on," I led him to the valet and placed him safely into the passenger seat. I drove home, my heart pounding. I was craving Josiah's big, black cock more and more with every mile closer I got to home. I pulled into the garage and tried my best to pull Carter out but I was struggling.

"I heard you struggling!" The door from the house that led into the garage opened and Josiah stuck his head in for a look at what was going on. "Let me help."

"Wow, you're so helpful!" He was so strong that he easily slung Carter over his shoulder and headed toward the bedroom, where he gently set Carter onto the bed.

"Anything else you need, Sidney?" The way he said my name made my heart stop.

"Why, yes. Is Rolan asleep?"

"He is."

"You're an excellent babysitter," I praised him. Our eyes locked. I knew he was about to fuck me and yet there was a smidgen of uncertainty that made my craving or Josiah even stronger.

"I'm good at other things too. I'd love to show you. Should I show you here or is there another place that would be better?"

"Do you mind that Carter is passed out? He had too much wine, I think. It would turn me on to fuck right here next to him."

"So that was your plan all along, then? You are a devious wife, my dear."

"No, I'm not devious. He just got drunk."

"Well, let me get you drunk on my cock, Sidney." He grabbed me by the shoulders and pulled me closer to him. I looked up at him and realized how tall and sturdy he truly was. He was so much bigger than Carter and I couldn't wait to see if he was bigger in the cock department too. He kissed me deeply and passionately. I wasn't ready for that, mostly because Carter hadn't kissed me with that kind of passion since we were teenagers. I had been married a long, long time and while this wasn't the first time I had cheated, it was certainly the most exhilarating time.

I gave myself over to the passion that Josiah was bringing to the table, unable to believe that a man could be so fucking sexy and give me what I needed. He pulled my sexy dress off, stopping to tell me how beautiful I had looked in it that evening. It made me wish that Carter was more like Josiah, but I knew that he wasn't and so I was going to enjoy Josiah while he was in front of me. He unhooked my bra and I let him pull it off of me. I waited for him to take off some of his clothes before he slipped his fingers into my panties and began to finger me.

I had never cum from being fingered before and so I was shocked when he was hitting my G-spot with the precision of a man who had fucked many women. I let out some loud screams, unable to silence myself as I came hard on his fingers. I knew that he had fucked every single one of my friends from my book club and now he was making the rounds with all the mothers at school. He posed as a free babysitter and of course, every woman wanted a free sitter. Then he charged for add-ons, which apparently were the best part of the deal. His add-ons were things like pussy licking, massages, and sex.

I had bought "the works," which had come highly recommended by Angie Farley.

"Trust me, Sidney. Get the works! It will make your year!" I could still hear her voice in my head as Josiah laid me back onto the bed next to Carter and pulled down my panties. He parted my legs and buried his face between them. He had a system, a way of licking pussy that can only be explained as thorough. He started slowly, teasing and licking my pussy but not touching my clit. He would tease me by getting close to my clit and then backing away. He would work me slowly until I was practically begging him to lick it, lifting my hips up to meet his tongue and wriggling myself into the position that would get me closer to getting his tongue where I wanted it.

"You like this?" he asked, but it was a rhetorical question. He knew I loved it and I was cumming for him. I screamed as he licked the tiny bead of flesh that was the gatekeeper to my satisfaction. Carter had never done anything like what Josiah was doing and I couldn't help but continue to cum for what felt like hours. He finally came to a stop.

"You ready for this dick in your pussy?"

"Is that part of the works?" I asked.

"Yes, it is. Condom?"

"Oh, of course," I fumbled in my drawer and found an old condom and waited for him to get it on. He climbed between my legs and looked at Carter. "Poor guy is missing all the fun. I wonder what he would think about me being this deep in you?" He plunged his cock into my pussy and I let out a strange sound. I had never had a cock so thick and long inside of me before. In fact, Carter was one of two guys I had fucked in twenty years. It was so sad.

"Oh my God! That feels so good!" Josiah had a magic cock. That was the only explanation for the orgasms he gave me. Carter still struggled to make me cum and I struggled to make myself cum. Josiah didn't have any trouble figuring out my body. He worked me with his cock, feeling my insides with the kind of empathy that only a man-whore could possess. It was like his cock could read my pussy and he was able to give me exactly what I needed.

I screamed as the first of many orgasms filled up my existence. I had never cum so hard and I held onto the bed, bracing myself as he moved faster and faster. No one had ever dared to fuck me as hard as Josiah was fucking me, but apparently, this was what my pussy needed and craved. This was what I had needed in my life. Carter was nothing. Josiah was everything. I was in love with him, instantly giving him the parts of my body and soul that I had never given to anyone, not even Carter.

He didn't stop. He kept right on fucking me as orgasm after orgasm was unearthed from deep inside of me. It was like a lifetime of orgasms had built up inside of me and Josiah had finally found the doorway that would allow them to escape. I screamed, clawed and cried as he continued to pound every orgasm out of me. Then, he stopped.

I was crying, my body wet with sweat from cumming so hard. I looked up at him, unable to believe that he was the one who was doing this to me.

"You okay? You need a break? Because I'm not done with you. Flip over. Doggy-style time." Josiah indicated with his hands that it was time for me to flip over and so I did so, sticking my ass in the air and hoping that I could handle the rest of this fuck. Carter continued to sleep peacefully next to me. I doubted I would ever tell him about this.

Josiah pushed his cock into my pussy from behind. His cock was so thick that my pussy could barely accommodate it. I knew that it wasn't going to fit lengthwise either but Josiah seemed to think that he could make it fit. He went slowly at first, feeling me out. His hands traced paths all over my back and when they reached my ass he would give me a tiny spank. His cock began to pump faster and harder and his spankings got increasingly harder as well.

"Fuck!" I screamed, hoping that my son would sleep through all the commotion.

"Take my big, black dick, Sidney! Take it!" He reached up and gripped me by the neck, using it as a handle to pull my body back onto his cock. He was working my body now, using it to get his own dick off. I came hard, again, shocked by how many orgasms I was actually capable of. With Carter, I was lucky if I had one, but I had definitely cum more than ten times with Josiah. He was a sex god, just like all of the other women had said.

"I'm going to cum!" he announced and he pulled his cock from me and pulled off the condom. His cum sprayed all over my ass and I could feel the warmth as it dripped down the back of my legs. I began to rub my hands in it, spreading it all over my butt like lotion. I wanted his cum all over me, inside of me, a part of me. I had it bad for Josiah, already crushing on him harder than I had ever crushed on my own husband.

"Well, I'll take my payment now and be on my way, Sidney. I'll be happy to babysit again sometime."

"Yes, put me on the list. It was quite a wait this time. Hopefully I don't have to wait two months to get back on that cock. You gave me the best orgasms of my life." I couldn't seem to wipe the smile off of my face and I didn't care. Carter was asleep and so was Rolan. They would never know what a slut I had just been.

"Sorry, I do get busy but if you do weeknights it's faster."

"How about Wednesday then?"

"Let me see," he grabbed his phone as my heart pounded. He checked the date and smiled.

"Wednesday it is. The works again?"

"Yes, the works. I love those orgasms! How do you do that?"

"I'm just in tune with a woman's body. It's a gift."

"It sure is!" I agreed. He got up and began to walk to the door.

"You don't have to go!" I told him. "I mean, we could fuck again."

"I have to go. I have another appointment."

"Damn."

"Don't worry, I'll see you Wednesday."

"Do you ever fall for your clients? Has it ever happened?" I asked, curious. I opened the front door for him.

"It's never happened. I won't let it. I'm strong up here," he pointed to his head. "And down here," he pointed to his dick.

"Yes, you are! I'll see you Wednesday!"

"See you then." He hugged me deeply and kissed my cheek. I knew I was already in love with him as he got into his car and drove away. Wednesday seemed so far away, and yet I was going to get to see him soon. I couldn't wait. Carter was already out on Wednesday nights for work. That meant I could fuck around with Josiah for a few hours. I knew I had just cum a ton but I grabbed my vibrator and went to work on myself anyway. I wondered if I could somehow do what Josiah had done to me. I had never felt anything like it!