The Babysitter

This story contains depictions of sex between consenting adults 18 and older.

My name is Paul, and I'm a single guy with a 12-year-old son. My wife had a mid-life crisis a few years ago and it ended up with us getting divorced, and now it's just me and Steven. We live in a pretty nice suburban neighborhood and we're a pretty friendly bunch. I know all of my neighbors and when we need help, we help each other out. When Covid came around, I started working from home full time, which was fine when Steven was in school, but not so fine when the summer rolled around.

My neighbor, Sarah, who lived a couple of doors down, who was also divorced, had a babysitter for her son, John, who is the same age as Steven. That seemed to work out well because Sarah was always at work and her babysitter did a great job watching John. I decided to give her a call and see if we could share. I picked up my phone and called her and on the second ring she picked up, "Hi Paul, how are things?"

"Great Sarah, how are things with you?"

"They're good, just busy as usual. What can I do for you?"

"Well, I'm still working from home, but now that summer is here, I'm having some difficulty juggling work and Steven. I was hoping that I might be able to share your babysitter with you."

"You mean Jennifer? I think that would be fine. Look, John is home most of the summer but he's going to some camps where Jennifer will take him and pick him up. You're welcome to talk with her about watching Steven as well. Then we could split the cost fifty-fifty for the summer if that works for you?"

"That would be perfect Sarah."

"Great, I'll text you her contact information. Talk to you later!" And she hung up. I got her information a few minutes later and gave her a call.

"Hi Jennifer, this is Paul and we don't know each other well, but you've watched my son Steven, who plays with John a few times."

"Oh sure, hi Paul, what can I do for you?"

"I hope you don't mind, but Sarah gave me your contact information because I need someone to watch Steven over the summer. I work from home so I'm around, I'm just too busy to do both. Sarah said it would be okay with her if we sort of 'shared you'. Would that be okay with you?"

"Completely okay with me Paul. That would be great as I'm saving up money before I head to college. What kind of pay arrangement were you and Sarah thinking?"

"Well, I was thinking that we could increase your pay by 50% and then Sarah and I would split it. Would that be okay?"

"That would be great Paul. Do you have any special instructions or needs?"

"No, not really. We have a pool and you're welcome to use it with the kids as much as you like. Both boys know how to swim so it's just some easy laying out by the pool and doing whatever while they swim. I'm always around if you have questions, I just may be on calls but that's it. John doesn't have any summer camp this year as he's studying for an advanced math placement class next year but that's it."

"That sounds great, I would love to work on my tan. How does starting this coming Monday sound?"

"Perfect. I'll send Steven over to Sarah's house Monday morning. He generally works on his math online from one to three."

"That sounds good. How about on days where I take John to a camp, do you want me to just hang around so I'm there if needed?"

"That would be amazing Jennifer, and you can always just hang out at the pool or stay cool inside or whatever."

"Great, thank you Paul. I'll see you on Monday."

Monday morning came around and I sent Steven over to Sarah's at nine o'clock and went back to my office to work. At around 11 or so, the pool security cam chimed. My ex-wife was always worried about a break-in, so I have cameras around the house. I turned on the camera and took a look. Both boys were jumping in the pool and Jennifer was walking over to a lounge chair. She was wearing shorts and a sweatshirt which was weird on such a hot day. I didn't really know what she looked like because I had seen her around, but never talked with her.

She pulled her shorts down to reveal a bikini bottom and an incredible, round ass that was amazing. Then she stood up and unzipped her sweatshirt to reveal the most fantastic set of tits I have been lucky enough to lay eyes on. She must have been a double-D or larger cup. She had just a little bit of meat on her stomach and her tits stuck out perfectly. I was getting hard just looking at her on the monitor. I zoomed in so I could look at this perfect body more. She started putting suntan oil on her body and I just watched her rub it all over her thighs, up to her bottom and then she moved up to her stomach and tits and I was mesmerized watching her hands roam her body. She put her hands in her cups and made sure to put lotion all over her tits. Fuck.

I left the security camera feed up so I could watch and went back to work. Jennifer was distracting so I kept glancing over at her. Just looking at her was getting me turned on so I pulled up some big tit porn and put it up next to the security camera footage. I took my cock out and started slowly jacking it off. I had been watching it for about 15 minutes and suddenly I heard a voice behind me.

"That looks so hot Paul."

FUUUCCCKKK. Jennifer was right behind me and there was pretty much nothing I could do to cover myself. She saw my screen, she saw my cock, she saw the security camera feed and the porn and I froze. "I'm so sorry Jennifer! Oh my god, I don't even know what to say." I hadn't seen her get up from the lounge chair.

"You don't have to apologize Paul. I spoke to Sarah, I know you've been single for a while. It's only natural. Were you looking at my tits?" She asked as she glanced down at my cock. I gulped. I hadn't been able to take my eyes off of her tits since I turned toward the door. My cock twitched, my hand still wrapped around it in mid-stroke and her right hand was tracing the triangles of her bikini. She stepped closer to me.

"I'm going to take that as a yes," and she slowly sank to her knees on the floor of my office. She laid her arms on my legs and slowly took my cock into her mouth. I thought my eyes would roll up into my head. She was like fifteen years younger than me, and she was in my office, sucking my cock. I watched her lips slowly move down my shaft and then slowly slide back up. She pulled her mouth off me and ran her tongue over my head and looked up at me. "Do you want to see my tits?" I nodded my head, my mouth dry with anticipation.

She reached up and pulled the string behind her neck and her top fell forward, dropping her breasts a few inches and exposing large, pale, areolas and small, perky, nipples. "Do you want to fuck them?" I nodded again. She slobbered all over my cock and put it between her tits. She squeezed her tits around my cock and they went fully around me. My cockhead was sticking up between her tits even after being fully surrounded by her tits. "Oh, Paul, you're fucking huge. I can suck your cock and tit fuck you at the same time." And she proceeded to do just that.

She slid her tits up and down my shaft while sucking on my cockhead the whole time. Slobber was running down my shaft and making her tits even slicker. She shifted her hands so that one arm and hand was holding both of her tits around my cock and the other hand moved down to her pussy which she started rubbing herself over her bottoms. I put my hands on the back and top of her head and pressed her head down further on my cock. She started moaning around my cock taking me to the brink.

I looked down and saw her fingers now pumping in and out of her pussy, her bottoms pushed to the side to expose her shaved pussy. She kept this up for a few more minutes and then she moaned hard and loud around my cock, and I pulled her head off my cock and started cumming. My first shot hit her face which caused her to jerk her head back, then the bottom of her chin and then my cum started raining down on her tits. Soon she was covered in cum and it was dripping everywhere.

She lifted her tits up to her mouth and started licking my cum off her tits and sucking it off her nipples. "I have to go clean up and watch the boys. Maybe we can do this again sometime later Paul." She stood up, fixed her bottoms, and went to the bathroom to finish cleaning off her tits. A few minutes later I saw her on the lounge again on the monitor.

To say that Jennifer started taking over my fantasies was an understatement. I was only 14 years older than her. I still didn't think a long-term relationship was going to happen, but I was happy to get a release I had really been missing since my wife left. Up until now it had been all porn online without any real hook ups or relationships. I hoped she was going to come back later in the week for more pool time. Looking at the weather, I thought she might show up again on Thursday, but who knew? And I didn't want to be proactive about asking at this point.

Thursday rolled around and she did indeed show up, only this time it was just her and Steven, John was nowhere to be seen. Of course, I had the security camera feed from the pool up again. This time she was playing it up for the camera. John was in the pool already and she was oiling herself up, but she made sure to linger on her tits, under her top. One hand managed to snake its way down under her bottoms and I knew she was fingering herself for my benefit. I was getting hard just watching her. About an hour later I saw Steven come in and I realized it was time for him to work on his math work.

On the monitor, I saw Jennifer looking right at the monitor and she untied her bikini top and pulled it down. Her tits came into view and she grabbed her right breast and brought her nipple to her mouth and started sucking. Her other hand went down to her pussy, pushed the fabric aside and she slipped a finger insider. Long live high definition security cameras. She did this for a few minutes and then rolled over onto her stomach. She got up on her hands and knees and started fingering her pussy faster which I could only tell because of the movement of her arm. Her tits were hanging down and swinging back and forth and it was erotic and mesmerizing. Her hand came up from between her legs and grasped her breast and squeezed her nipple and was clearly moaning.

She gently started to relax after having what looked like a great orgasm, stood up and fixed her bathing suit and then headed into the house. This time I was ready but I still had my cock in my hand because I had been jerking off for the last half an hour. "I was just going to take a quick shower to get the chlorine and lotion off me. Do you mind if I use your shower?"

"Not at all. Do you need any help washing?"

"I thought you'd never ask. Do you have the time?"

"Not for a long shower, but maybe I can help get those hard-to-reach places." I got up and followed her to the guest bathroom which had a shower just for people who got out of the pool. We went in and I closed the door.

She turned around and kissed me passionately, pressing up against me so my cock was sandwiched between our stomachs. "Did you like my show?"

"Fuck yes, you are so hot."

"Did you stroke your big cock the whole time thinking about me?"

"You know I did." I leaned forward and kissed her again. Then I picked her up and put her on the bathroom counter. I turned the shower on to let it get warm and came back to her. "My turn," and I leaned down, pushed her back against the vanity mirror and started licking her pussy. She was still wet from her earlier orgasm. I kissed the inside of her thighs, ran my tongue lightly over her lips and kissed and licked my way up to her stomach. I took first one nipple then the other into my mouth and tongued and sucked on each one. I moved back down to her pussy and licked her top to bottom, found her clit and sucked it into my mouth. I ran my tongue over her clit while it was sucked into my mouth. I felt her hands on the back of my head pulling me in tighter to her pussy. Her body shook and I felt her get wetter.

She pulled my head up and said, "I want to feel that monster in me. Fill my pussy with your cock."

I stood up and put the head of my cock at the entrance to her pussy. I grabbed it and ran the head up and down her slit. Then I slowly pushed my head into her pussy. She was already soaking, and I was able to slide almost all of the way into her. I slowly pulled out and pushed back in. She grabbed on breast to suck on her nipple and used her other hand to rub her clit while I slid in and out of her. She was looking down at my cock, just entranced by watching me penetrate her. Her breathing became heavier, and I leaned down to kiss her. It was sensual, our tongues touching each other, licking each other's lips. We both licked her nipple and kissed each other again and again. I moved down to her ear lobe and down to her neck and back to her lips. I was getting close to cumming and feeling her hand on her pussy while I slid in and out was getting me closer.

"That's it Paul. Fuck me harder. I want to feel you all of the way in me." I stood up and grabbed her hips and slowly pushed myself all the way in until I hit her cervix and she gently cried out. "Fuck me. Pound me."

I pulled almost all of the way out and then slammed into her again and again and she came all over my cock. I pulled my cock out and stroked it and came from her stomach to her hair. I came on both tits, her stomach and all over her pussy. She leaned forward and sucked my cock into her mouth and sucked out the rest of my cum off my cock and tasted herself on me. "Go on, get back to work. I have to take a shower before Steven finishes his math."

"Thank you, Jennifer. That was amazing."

"Why are you thanking me?"

"Well, you don't have to do anything except watch the kids. I don't want you to feel like you have to do anything else."

"Oh Paul. First, I'm 18, I can do what I want. Second, I like you. I think you're hot and you aren't too much older than me. I don't know what will happen, but I like you. And I really enjoyed those orgasms." She sat up and kissed me hard on the lips. "Go on and I'll get cleaned up. We can talk more later."

This was going to be a good summer...