Linda, The Babysitter Ch. 03

So by now I knew that Linda was willing to take my dick and satisfy me whenever she was over doing chores at my house, which was two-three days per week. I also knew that at this point in my summer, my brothers were going to be in school for another couple of weeks. This left me with 2-3 days per week where I had Linda and her hot body all to myself between the hours of 8:00 and 2:00, and I was going to take full advantage of it while it lasted.

Needless to say, all I could think about over the weekend was how I had scored with Linda twice the previous week, and that I had experienced her sweet, mature pussy. If she had let me go that far with her, I would almost definitely be able to go back and take more. Visions of her beautiful head bobbing up and down on my cock and of her naked, glistening body moaning in sexual ecstasy in the back seat of my car filled my head. I could see her turning into my summertime sex slut, and a hot blonde one with a tight body at that. The subsequent week could not come fast enough!

When she arrived on Tuesday, there was no motivation for me to sleep late as I usually did during the summer months. I was up (in more ways than one) when she came into our house. However, my mother was still home, so I either had to wait for her to leave or figure out a way to get out of the house with Linda. While fucking her while my mom was home would be particularly hot, I wasn't quite ready to take that risk yet. I did not want to lose a fuck toy as hot as Linda just as the summer was starting.

Now it was fairly standard for Linda to spend time doing things with any of the kids who happened to be home when she was working, in addition to the chores and cleaning she did around the house. Being a house full of boys, most of these activities typically revolved around sports. I figured that if I could get her to go somewhere with me outside to play a sport, that would give me a good opportunity to make a move and get my dick wet. When I brought this idea up to here, she suggested going up the street to play tennis at some courts at a local private high school. Knowing the number of pornos I had seen that started off as tennis lessons, this was fine with me!

With me still in love with my newly acquired car, and the history that existed between Linda and I in that particular vehicle, I was more than happy to drive. The courts were not very far away, and she and I just made small talk as we made our way up there and began to casually volley back and forth. I was not sure what I wanted to sexually do with her or how I was going to go about doing it yet, but there was no doubt in my mind that I would get there. In the meantime, I enjoyed the show of her boobs bouncing up and down as she ran, and the nice short jeans she was wearing. I thought of having her get down on her knees to blow me on the court, or maybe bending her over the net in the center, but other people who were also playing put a damper on my plans of taking her in public (at least for the time being).

As the day progressed and the hot summer sun began to beat down upon us, we both began sweating due to the heat and humidity. This brought back sweet memories of our sweaty sex session in the back seat of my car the week before. My concentration quickly began to wane from tennis, as all I could think about was cumming in her MILF body once again.

It was not long after that point that I expressed my desire to head back. She agreed that it was getting rather hot out, so we collected the balls and the rackets and headed back to my car. As we both got in, I turned the key in the ignition, pulled out of the parking space, and began to slowly role down the little side road that connected the parking lot to the main road. Once we were out of site of the courts and were in the cover of some trees, I put on the brakes, glanced at Linda out of the corner of my eye, and took a deep breath

"Since I drove, how about you give me a little payment," I said as I pulled my athletic shorts down to expose my semi-hard cock. I quickly gave it a few strokes to bring it to full mast.

She nervously glanced around and started stammering, "But Marc, this isn't a good place, somebody might see us, and ..."

At which point I interrupted her by saying, "Look, I'm going to have you one way or another, so you might as well make this easier on yourself. No one can see you if you put your head down; don't worry about it and just do it."

"But Marc, I've been meaning to talk to about what happened last week. You know I'm married, and I can't be doing this all the time. I know it happened, but it's not right for it to be a regular thing."

"Listen, after you let me go all the way with you there is no going back now. You gave me a taste, and there is no way you can stop me from going back for more you little cock tease. At least not if you still want to be working for my parents when all is said and done."

I calmly took my hand and placed it on hers, and then moved her sweaty palm right up against my bulging shaft. I closed her fingers around my meat, and she picked up where I had left of stroking it. My cockhead was bulging in no time, and then her head moved down for a taste.

I then felt her subtle lips wrap around the tip of my meat, and her moist tongue licked the tender underside. Her mouth felt amazing on my eager member, and I let out a huge breath of sensual relief. I instinctively pushed my hips up and fed her more of my cock, which she willingly accepted as she started to suck on my meaty shaft. I moved some of her long, blonde hair out of the way so that I could see her gorgeous face as she made sensual love to my manhood, and then put my hand on the back of her neck to help guide her up and down.

With my other hand on the wheel, I took my foot off the break and put it back on the gas so that we could get back out onto the main road and head back to my house. This happened just in the nick of time, as another car that was leaving the tennis courts was just coming behind us. As we stopped before turning onto the main road, Linda tried to lift her head up and off of my meat, but I kept her down on it with my hand and proceed to feed even more of my cock into her mouth in order to keep her busy. I'll bet that she was nervous about performing a sex act on a teenage boy in a car on a main road in the middle of the day, but there was no way that I was letting her up off of my penis until I came. I was actually pretty nervous too, as I had never done anything like this before. But the risk made it even hotter than her blowing me already was, and she felt way too good to let her off my meat.

As I pulled out onto the main road and my eyes anxiously glanced around to survey the environment, Linda started taking me deeper into her mouth. The bobbing of her head became faster as she was getting into a nice, steady rhythm. She did not even really need the assistance of my off-hand anymore. As she continued to bob and suck, her hand tugged and churned on the base of my cock, seemingly begging me to shoot my load into her. I think she had succumbed to the fact that she was going to be blowing me one way or another, and the sooner that she got to it, the sooner I would explode in her mouth and she would be off the hook for the time being.

Since we were relatively close to my house, I was in no rush to get home. I needed to take my time in order to make sure that she wasn't still sucking me off when I pulled into my driveway at home. As we rolled through the first of two traffic lights, she moved her petite hand onto my pubic area and then cupped my balls in her hand. She then started to really go down on my bulging dick, engulfing about 80% of my 7-inch rod with every descent into my crotch. Every time she went down, the tip of my cock would touch the back of her throat and she would consequently swirl her tongue around my entire length. This felt incredible, and was certainly better than anything I had gotten from any little teenage skank that I had been with up to that point in my life. It certainly paid to have a MILF who knew what she was doing, a real woman with experience.

Just as we came to a stop at the second traffic light on the road home, I began to feel my cockhead start to bulge and that very definitive tingling in my balls, so I knew that I was going to explode soon. She must have sensed it too, as she quickened up her pace and made sure that she was going nice and deep on my cock. My breathing started to quicken as the light turned green and the cars in front of me went, but I did not want to go until she had made me cum. The car behind me honked, at which point she tried to pull up off of my penis. But I held her head down with both hands and whispered to her, "We're not going to move until you take my load."

She fearfully moaned, and then feverishly went back to work on my cock. She tightly gripped the base with one hand and then threw her head all the way down on the rest of my meat, where she quickly began to both lick and suck me like her life depended on it. I then pressed her head a bit farther down on me until I felt my tip go right into the back of her throat. That is all I needed to send me over the edge, as I let out a moan of hedonistic relief and then erupted into her mouth. I took my foot off the break and started rolling forward just as I held her head in place to ensure that she took my entire, massive load. I had not beaten off in several days in anticipation of doing something with Linda, and she was receiving the complete results of that action right then. I could hear her gagging and feel the dribble of a mixture of saliva and cum dripping from her mouth as we pulled onto my street, but I continued to hold her there and told her to swallow it all.

Once I was satisfied, I let her head off of my cock, and she came up gasping for air. However as she did so, I noticed that she licked her lips. I put my manhood back in my shorts and pulled into my driveway, very satisfied with what had just transpired.

- - - - - - - - - - - - - - - - - - - - - - - - -

When Linda came over the next morning, I was once again ready and waiting. I'm sure that by this point, she knew what was waiting for her as well. I once again was not exactly sure how I was going to get with her on that particular day, but there was no doubt in my mind that I would do so.

Once again, my mother was still home when Linda arrived, so fucking her in the house was out of the question for the time being. I could potentially wait until my mom left later on, but I did not know when that would be and I wanted to get inside Linda's smoking body as soon as possible.

Considering that we had enjoyed our little endeavor to the local tennis courts the other day, I figured that we might as well make a return trip. Upon arriving downstairs, I proposed the option to Linda. She nervously glanced over at my mother, bit her lower lip, and then politely agreed. She may have only been willing to go again since she did not want to appear suspicious in front of my mother, but no matter what the reasoning was, she definitely knew what she was in for this time.

After gathering the tennis equipment, we once again took my car up to the courts. My mind was already racing as to how I was going to get with her today. All types of scenarios were running through my head, to the point that I already was getting visibly hard on the short ride up.

"Getting excited, are we, Marc?" Linda asked rhetorically, as she glanced over at my bulging crotch.

"I guess that you could say that, but I'll show you more about that later" I replied, as I began to slowly caress my growing hard-on through my pants with my right hand.

Before long, we pulled into the parking lot of the tennis courts, and proceeded to get out of the car to play. The entire time, I could not take my eyes off of Linda and her beautiful back side. From the moment she stepped out of the car to when she was loosening up on the court, all I could think about was putting it in her from behind. As we began to play, it is needless to say that my tennis game was a little off that day due to the fact that my mind was elsewhere.

The weather was once again hot and sunny, similar to the day before. However, the weather grew hot enough as the morning progressed that all of the other players on that particular day were driven off for the time being, and Linda and I had the court to ourselves. That is when an idea popped into my head.

By this point we were both relatively tired and sweaty, so I suggested that we call it quits for the today. Linda agreed, and we both began to pick up stray balls around the court. As we placed all of our equipment back into my car, I mentioned that I had noticed some tennis balls that were lying in the tall shrubs that surrounded the fence that formed the perimeter of the court, and that I wanted to go collect them.

At this point I grabbed her hand and led her over to the tall bushes. Since no one else was around the courts, this was a perfect opportunity for me to fuck her in public, which had always been a major fantasy of mine. And given the way that the tall bushes/small trees surrounded the fence, I could very well still get away with nailing her between the plants and the fence even if someone showed up. The tennis courts extended for quite a ways, as there were six courts in all. And in between each court, the chain link fence jutted out into the tall bushes, creating a small area that could not be easily seen from all of the courts. In this relatively secluded area between the plants and the fence, we could not be seen from the road and would be at least partially hidden from some of the courts.

Once I grabbed her hand and began leading her to the far off, more secluded section of the courts, I think Linda knew what I had in mind. While she was proceeding rather slowly, she wasn't putting up that much of a fight. I think that she had now resigned herself to the fact that I was going to fuck her at every opportunity I had over the course of the summer, and there was not a lot she could do about it if she wanted to keep her job.

As I led her through a small break in the trees and into the little gap of space near the fence, I directed her up against the chain links. I proceeded to come right up behind her, wrapping my arm around her waist with one hand while I moved her flowing blonde hair to the side with the other. I pulled her hips back towards me and started to slowly grind my pelvic area on her tight little ass. As I leaned forward and began to kiss her neck while I felt her up, she began to whimper and moan in arousal.

After initially succumbing to my advances, she began to pull away as she at the thought of getting it on in such a public place. "People play here all the time; anybody could see us. We could get arrested for this! Let's just go back home, please!" she complained.

"I know that you love getting fucked by a young cock. Don't pretend like you don't want it. We're not going anywhere," I muttered into her ear. "Anyways," I added, "the quicker you make me cum, the quicker we can get out of here."

As I pulled her ass back towards me with one hand, I guided each of her hands up onto the fence with the other. "Grab hold of this," I commanded. I then proceeded to unbutton her jean shorts and let them drop around her ankles, which revealed her skimpy blue and pink underwear and her sweet as cheeks. Chomping at the bit to get inside of her, I pulled her panties down to her ankles as well while I dropped my own shorts and stepped out of them.

With my cock just about ready for action, I stepped back up against her. Placing my hands on top of hers and holding them in place, I started to grind my meat on her bare ass and slowly dry-hump her while I passionately kissed her neck. I was fully erect in no time, but before I proceeded I had one more surprise in store for her.

I brought my hands down to her butt cheeks and gently parted them, and she stuck her hips back in preparation for entry. But instead of sticking my penis in her pussy, I started rubbed my cockhead around her tight little anus.

While still gripping the fence tightly with both hands, she glanced back at me with a look of shock and fear on her face. "No Marc! You can't fuck me there! It is gonna hurt so much! No way, no way!" she proclaimed.

Expecting something like this to happen, I calmly replied, "Look honey, if you want to keep your nice little job and you want to keep getting paid, then you'll let me fuck you there and you'll take it like a good little slut. Now do we have an understanding?"

Taking a big gulp of air, she nervously stammered, "Yes...okay, but just don't go too hard. You've got to take it easy."

"Don't worry, I know what I'm doing," I replied, as a devious smile came across my face. With my cock resting up against her butt cheeks, I put my right hand in front of her face and stuck out my index finger. "Now go ahead and lick this," I commanded.

Doing as she was told, she took my finger in her mouth and lathered it up with a nice coating of saliva. Once she was done, I brought my finger down to her puckered asshole and stuck it in, two knuckles deep. She instantly started moaning.

"Yeah, that feels good, doesn't it baby," I whispered in her ear as I started to slide my finger back and forth, in and out of her mature asshole. After a minute of using just one finger, I pulled it out and brought my middle finger up in front of her face. "Now lick that one too," I instructed. After doing what she was told, I brought my hand back down behind her and placed two of my fingers up into her tight rear end. After she moaned again, I said "You like that baby, don't you? I knew you would," as I continued to get her ready for the real thing.

After another minute of sliding my fingers in and out of her, she was definitely wider and looser than she was before. Her asshole was finally ready to go. And we were both certainly horny enough to proceed to the next level. Removing my fingers from her ass once again, I cupped my hand and placed it in front of her face. "Spit in that," I instructed her. After she did so, I brought my hand back and I spit in it as well. Now with it full of saliva, I began to rub it all over my bulging cock in order to lube it up the best I could.

Once it was all lathered up, I grabbed her hips firmly with both of my hands. Knowing what was about to come, she reached back and grabbed my hips as well in order to help guide my thrusts. Then with one fateful plunge I pressed my cockhead against her asshole, and after a moment of resistance, it popped right in. I exhaled deeply in euphoric relief, as her tight ass felt amazing around my young cock. I had never felt anything like it before. After enjoying the feeling for a moment, I then began to slowly press upwards, furthering myself into her rear end, as she slowly began to accept my advances. Soon, about two inches of my manhood was inside her rear hole, and I began to gently slide it in and out of her. Linda's hands helped guide my pace as her face pressed up against the fence and her whimpers of sexual pleasure began to get louder.

As I began to get into a rhythm, I removed one of my hands from her hips and reached around in order to feel up her body. My hand crawled under her loose-fitting white shirt and soon found its' way up to her breasts. She was not wearing a sports bra, so I grasped her sweaty boobs as they swung to the rhythm of my fucking. Her entire body was glistening and moist from the summer heat, and was ready to truly be ravaged and enjoyed.

She then bent over a little more, arching her back and forcing a little more of her body down onto my cock. I began thrusting into her a little harder, causing her hedonistic cries to get even louder. I know that she wanted to be as quite as possible because we were in a public place, but she could not seem to help herself.